KR20160017606A - Cleaning composition - Google Patents

Cleaning composition Download PDF

Info

Publication number
KR20160017606A
KR20160017606A KR1020150099076A KR20150099076A KR20160017606A KR 20160017606 A KR20160017606 A KR 20160017606A KR 1020150099076 A KR1020150099076 A KR 1020150099076A KR 20150099076 A KR20150099076 A KR 20150099076A KR 20160017606 A KR20160017606 A KR 20160017606A
Authority
KR
South Korea
Prior art keywords
weight
insulating film
organic insulating
transparent resin
group
Prior art date
Application number
KR1020150099076A
Other languages
Korean (ko)
Inventor
윤효중
최경묵
홍헌표
Original Assignee
동우 화인켐 주식회사
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 동우 화인켐 주식회사 filed Critical 동우 화인켐 주식회사
Priority to CN201510479447.6A priority Critical patent/CN105368611B/en
Publication of KR20160017606A publication Critical patent/KR20160017606A/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/40Monoamines or polyamines; Salts thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/42Amino alcohols or amino ethers
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2003Alcohols; Phenols
    • 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
    • HELECTRICITY
    • H01ELECTRIC ELEMENTS
    • H01LSEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/3105After-treatment
    • H01L21/311Etching the insulating layers by chemical or physical means
    • H01L21/31127Etching organic layers
    • H01L21/31133Etching organic layers by chemical means

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • General Chemical & Material Sciences (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)
  • Detergent Compositions (AREA)

Abstract

(A) 1-10% by weight of a quaternary ammonium salt compound, (b) 40-80% by weight of a polar solvent, (c) 1-20% by weight of an alkoxyalkylamine having a structure represented by the following formula (d) 0.1 to 5% by weight of a hydroxylamine-based compound, (e) 1 to 20% by weight of an amide having a structure represented by the following formula (2), (f) 1-20% by weight of an alkylene glycol dialkyl ether, ) 0.01-2% by weight of an inorganic base or a salt thereof and (h) 1-40% by weight of water. The present invention relates to a cleaning agent composition for removing a color resist, an organic insulating film and a transparent resin.
[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 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.
(2)
Figure pat00006

(Wherein R 4 , R 5 , and R 6 are each independently hydrogen, a C 1 to C 4 chain or cyclic alkyl group, or a phenyl group.)

Description

Cleaning composition

The present invention relates to a color resist, an organic insulating film, and a cleaning agent composition for removing a transparent resin.

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.

On the other hand, the resist can be largely divided into a positive type resist and a negative type resist. Unlike the positive type resist, which is easily removed and removed within one minute at a temperature condition of 40 to 50 DEG C by an organic solvent- Resists have properties of a negative type resist which has a high degree of curing and is hardened by heat treatment and is difficult to peel off. Accordingly, in order to remove the color resist, a time of not less than 5 minutes is required under a temperature condition of 70 占 폚 or more, so that stronger peeling performance is required. In the current flat panel display manufacturing process, when an organic insulating film is used for the coating of a color filter, if RGB coating of the color filter causes coating failure or coating failure of the organic insulating film, the color filter is discarded There is a need for a cleaning composition capable of simultaneously removing the RGB color resist and the organic insulating film for reuse of the color filter because the process yield is improved and the cost is reduced. In addition, in the case of RGBW transparent resist having a four-pixel structure for increasing the light efficiency of an OLED panel, there is a problem that it is more difficult to remove by using a resin having high thermal stability and chemical stability as well as a higher degree of curing than a color resist or an organic insulating film. Accordingly, in order to reuse the defective color filter generated during the color filter manufacturing process, a cleaning agent composition capable of effectively removing both the color resist, the organic insulating film, and the transparent resin is required.

Korean Patent Laid-Open No. 10-2003-0026664 discloses a color resist stripper composition comprising a hydroxide compound as a main component, and Korean Patent Publication No. 10-2014-0028962 discloses a color resist stripper composition comprising diethylenetriamine, There is disclosed a release liquid composition for removing negative photoresist containing alkyl ammonium hydroxide, dimethyl sulfoxide, and water. However, the above-described conventional techniques have achieved desired results in color resist peeling, but do not show any effect of partially or totally removing the organic insulating film or the transparent resin. In addition, there is a problem that precipitation of inorganic alkali occurs due to volatilization of the exfoliation liquid at the time of the high temperature processing of the hydroxide compound base exfoliating liquid composition, and the effect of removing the resin having increased degree of crosslinking only with diethylenetriamine and polar solvent There is an insufficient problem.

Therefore, it is necessary to develop a cleaning agent composition that has excellent cleaning effect for both color resist, organic insulating film, and transparent resin, and has no deposition problem even in a high-temperature process.

Korean Patent Publication No. 10-2003-0026664 Korean Patent Publication No. 10-2014-0028962

In order to solve the problems of the prior art, the present invention can effectively remove both the color resist of the color filter, the organic insulating film and the transparent resin in a short period of time for reuse of the color filter, The purpose is to provide.

(A) 1-10% by weight of a quaternary ammonium salt compound, (b) 40-80% by weight of a polar solvent, (c) alkoxy having a structure of the formula (1) (E) from 1 to 20% by weight of an amide having the structure of formula (2), (f) from 1 to 20 alkylene glycol dialkyl ethers, (G) 0.01-2% by weight of an inorganic base or a salt thereof, and (h) 1-40% by weight of water. The present invention provides a color resist, an organic insulating film and a detergent composition for removing a transparent resin.

The detergent composition of the present invention can effectively remove both the color resist, the organic insulating film and the transparent resin in a short time, thereby improving the productivity of the color filter reuse. In particular, the cleaning composition of the present invention enables the reuse of a defective substrate by removing a cured color resist, an organic insulating film and a transparent resin having increased crosslinking degree from the substrate in a structure in which a color filter is integrated into an LCD color filter or a TFT substrate. Further, since the detergent composition of the present invention does not use an inorganic alkali hydroxide as an alkali base, there is no problem of precipitation of inorganic alkali due to volatilization of the exfoliating liquid even in a high temperature process.

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

(B) a polar solvent; (c) an alkoxyalkylamine having a structure represented by the following formula (1); (d) a quaternary ammonium salt compound; (E) an amide having a structure of the formula (2), (g) an alkylene glycol dialkyl ether, (g) an inorganic base or a salt thereof, and (h) water.

The detergent composition of the present invention can effectively remove both the color resist, the organic insulating film and the transparent resin in a short time by the composition as described above, thereby improving the productivity of the color filter reuse.

(a) a quaternary ammonium salt compound

The quaternary ammonium salt compound (a) of the present invention releases hydroxide ions, which penetrate into the resist and promote 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) Or more.

The quaternary ammonium salt compound of the present invention is preferably contained in an amount of 1-10% by weight based on the total weight of the composition. When the quaternary ammonium salt compound is contained in the detergent composition of the present invention in an amount of less than 1% by weight, penetration ability into the color resist polymer of the hydroxide ion is decreased. When the quaternary ammonium salt compound is contained in an amount of more than 10% by weight, There is a problem of being reduced.

(b) polar solvent

The polar solvent (b) of the present invention penetrates the resist to increase the swelling property, thereby increasing the peeling force from the substrate surface. Further, the dissolution ability of the resist stripper composition of the present invention in water is improved, and the residue can be easily removed in the subsequent water washing step.

The polar solvent may be at least one member selected from the group consisting of dimethyl sulfoxide, diethyl sulfoxide, dipropyl sulfoxide, sulfolane, n-methylpyrrolidone, pyrrolidone and n-ethylpyrrolidone.

The polar solvent of the present invention is preferably contained in an amount of 40 to 80% by weight based on the total weight of the composition. When the polar solvent is contained in an amount of less than 40% by weight, the solubility of the polymer resin is lowered. When the amount of the polar solvent exceeds 80% by weight, the activity of the ammonium salt compound is impaired.

(c) an alkoxyalkylamine having the structure of formula

The alkoxyalkylamine (c) of the present invention penetrates into the cured resin and breaks bonds to dissolve the polymer.

In the present invention, the alkoxyalkylamine is a compound represented by the following formula (1).

[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.

Specifically, the alkoxyalkylamine represented by the above-mentioned general formula (1) is preferably selected from the group consisting of methoxyethylamine, methoxypropylamine, ethoxypropylamine, propoxyethylamine, isopropoxypropylamine, methoxyethoxypropylamine, oxolane- -Methanamine, (oxolan-2-yl-methyl) butan-l-amine and methyloxolan-2-yl-methanamine.

The alkoxyalkylamine of the present invention is preferably contained in an amount of 1-20% by weight based on the total weight of the composition. When the alkoxyalkylamine is contained in the detergent composition of the present invention in an amount of less than 1% by weight, the strength of breaking the bond by penetration into the cured resin is lowered. When the alkoxyalkylamine is more than 20% by weight, The solubility of the polymer resist is lowered.

(d) Hydroxylamine compound

The hydroxylamine-based compound (d) of the present invention has a low-molecular structure to generate hydroxide ions in a short time, permeates the cured resin to break the bond and dissolve the dye component of the resist.

The hydroxylamine-based compound may be at least one selected from the group consisting of hydroxylamine, dimethylhydroxylamine, and diethylhydroxylamine.

The hydroxylamine-based compound of the present invention is preferably contained in an amount of 0.1-5% by weight based on the total weight of the composition. When the content of the hydroxylamine compound is less than 0.1% by weight, the dye component of the resist is difficult to dissolve sufficiently. When the amount of the hydroxylamine compound exceeds 5% by weight, the effect of increasing the amount of the hydroxylamine compound is not increased. , The content of the quaternary organic ammonium hydroxide and the polar solvent is relatively lowered, so that the solubility of the resist can be reduced.

(e) Amide having the structure of formula (2)

The (e) amide of the present invention promotes the swelling of the transparent resin film to increase the desorption rate in the substrate

In the present invention, the amide is a compound represented by the following formula (2).

(2)

Figure pat00002

In Formula 2, R 4 , R 5 , and R 6 are each independently hydrogen, a C 1 to C 4 chained or cyclic alkyl group, or a phenyl group.

Specifically, the amide represented by the general formula (2) may be selected from the group consisting of formaldehyde, acetamide, benzamide, N-methylpropanamide, propanamide, butanamide, N, N-dimethylacetamide, Dimethylformamide, dimethylpropanamide, N-ethyl-N-methylbenzeneamide, N-phenylbutanamide and N-phenylbenzamide.

The present inventors have experimentally confirmed that when the amide having the structure of Formula 2 is introduced into the cleaning composition of the present invention, the cleaning effect is greatly improved.

The amide of the present invention is preferably contained in an amount of 1-20% by weight based on the total weight of the composition. If the amount of the amide contained in the detergent composition of the present invention is less than 1 wt%, the removal power of the transparent resin is not effective. If the amount of the amide is more than 20 wt%, the removal power is not increased any more.

(f) an alkylene glycol dialkyl ether

The alkylene glycol dialkyl ether (f) of the present invention penetrates into the organic insulating film and swells to facilitate desorption at the substrate.

Examples of the alkylene glycol dialkyl ether include ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol methyl butyl ether, propylene glycol dimethyl ether And dipropylene glycol dimethyl ether.

The alkylene glycol dialkyl ether of the present invention is preferably contained in an amount of 1-20% by weight based on the total weight of the composition. If the content of the alkylene glycol dialkyl ether is less than 1% by weight in the detergent composition of the present invention, the swelling effect of the resist polymer is reduced to decrease penetration into the resist of the hydroxide ion, and if it exceeds 20% by weight, There is no further effect and the solubility of the inorganic salt is reduced.

(g) an inorganic base or salt thereof

The inorganic base or its salt (g) of the present invention has a role of improving the peeling force against the organic insulating film.

The inorganic base or its salt may be at least one selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium nitrate, potassium nitrate, sodium sulfate, potassium sulfate, sodium silicate and potassium silicate.

The inorganic base or salt thereof of the present invention is preferably contained in an amount of 0.01 to 2% by weight based on the total weight of the composition. If the content of the inorganic base or its salt in the detergent composition of the present invention is less than 0.01% by weight, the peeling force against the organic insulating film is poor. If the amount is more than 2% by weight, the effect of increasing the amount is insignificant and not economical.

(h) Water

The water (h) of the present invention is appropriately added to control the overall composition and increase the activity of the hydroxy ion

The water of the present invention may be contained in the remaining amount relative to the other components contained in the composition of the present invention, and specifically may be contained in an amount of 1-40% by weight.

The detergent composition of the present invention is characterized in that it does not contain an alkylene glycol monoalkyl ether. When the alkylene glycol monoalkyl ether is contained in the detergent composition of the present invention, the wettability with the organic film-coated substrate is lowered and the dissolution rate of the resin is lowered, which is undesirable. The cleaning effect on the color resist substrate, Which is very low.

In the most preferred composition, the detergent composition of the present invention,

(A) quaternary organic ammonium hydroxydotetramethylammonium hydroxide (TMAH); (B) dimethyl sulfoxide (DMSO) as the polar solvent, and (c) alkoxyalkylamines as the at least one of methoxyethylamine, methoxypropylamine, ethoxypropylamine and propoxyethylamine; (E) at least one of amide, N, N-dimethylacetamide, N-methylpropanamide, N-methylethanamide and N, N-dimethylpropanamide; (F) an alkylene glycol dialkyl ether, at least one of ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether and propylene glycol dimethyl ether; And a cleaning agent composition for removing a color resist, an organic insulating film and a transparent resin, which comprises at least one of sodium nitrate, sodium hydroxide, potassium hydroxide, sodium bicarbonate, potassium carbonate and sodium carbonate as the inorganic base or salt thereof (g).

The cleaner composition of the present invention exhibits a very excellent cleaning effect for both the color resist, the organic insulating film and the transparent resin, and the color resist may be a negative photosensitive resin, but the present invention is not limited thereto, and the organic insulating film may be a polyacrylate resin But it is not limited thereto. The transparent resin may be a resin having an increased cross-linking property by adding an epoxy functional group to polyacrylate, but is not limited thereto.

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. The following examples can be appropriately modified and changed by those skilled in the art within the scope of the present invention.

Examples and Comparative Examples: Preparation of detergent composition

The cleaning agent compositions of Examples 1 to 10 and Comparative Examples 1 to 8 were prepared by mixing the components shown in the following Table 1 according to the specified composition ratios.

(a) quaternary ammonium hydroxide (b) polar solvent (c) an alkoxyalkylamine (d) Hydroxylamine (e) Amide (f) an alkylene glycol dialkyl ether (g) an inorganic base or salt thereof water Kinds weight% Kinds weight% Kinds weight% weight% Kinds weight% Kinds weight% Kinds weight% Example 1 TMAH 3 DMSO 54 AA1 15 2 AM1 10 AGE1 5 Sodium nitrate 0.05 Balance Example 2 TMAH 6 DMSO 42 AA 2 10 0.5 AM2 5 AGE3 10 Sodium hydroxide 0.1 Balance Example 3 TMAH 1.5 DMSO 60 AA 3 5 One AM1 12 AGE1 10 Potassium hydroxide 0.3 Balance Example 4 TMAH 4 DMSO 50 AA 4 5 1.5 AM2 15 AGE2 15 Sodium bicarbonate One Balance Example 5 TMAH 5 DMSO 45 AA 1 16 4 AM3 15 AGE2 10 Potassium carbonate 0.8 Balance Example 6 TMAH 3.5 DMSO 55 AA 2 10 4 AM4 6 AGE4 8 Sodium hydroxide 0.5 Balance Example 7 TMAH 7 DMSO 40 AA 3 7 3.5 AM3 10 AGE3 8 Potassium hydroxide One Balance Example 8 TMAH 2 DMSO 70 AA 4 5 One AM4 8 AGE4 5 Sodium nitrate 0.2 Balance Example 9 TMAH 6.5 DMSO 45 AA 1 10 2 AM2 5 AGE1 5 Sodium carbonate 0.3 Balance Example 10 TMAH 5 DMSO 55 AA 3 5 0.5 AM4 10 AGE3 4 Potassium hydroxide 0.5 Balance Comparative Example 1 TMAH 8 DMSO 40 - - 0.1 AM1 3 AGE2 16 Potassium hydroxide 0.1 Balance Comparative Example 2 TMAH 2.5 DMSO 65 AA 1 10 0.5 - - AGE4 12 Sodium nitrate 0.5 Balance Comparative Example 3 TMAH 10 DMSO 35 AA 2 4 5 AM2 8 - - Potassium hydroxide 1.5 Balance Comparative Example 4 - - DMSO 75 AA 1 8 2 AM3 10 AGE2 4 Potassium hydroxide 0.7 Balance Comparative Example 5 TMAH 6 DMSO 40 AA 3 20 One AM2 5 AGE3 3 Sodium hydroxide 0.2 Balance Comparative Example 6 TEAH One DMSO 70 AA 1 15 - AM1 5 AGE1 8 Sodium carbonate 0.1 Balance Comparative Example 7 TMAH 2 DMSO 87 DETA 3 - - - - - - - Balance Comparative Example 8 TMAH 4 DMSO 60 - - 0.5 AM5 5 AGE2 6 Sodium hydroxide 0.5 Balance Comparative Example 9 TMAH 4 DMSO 50 AA 4 5 1.5 AM2 15 AGE2 /
MDG
7.5 /
7.5
Sodium bicarbonate One Balance
Comparative Example 10 TMAH 4 DMSO 50 AA 4 5 1.5 AM2 15 MDG 15 Sodium bicarbonate One Balance

(a) a quaternary organic ammonium hydroxide

TMAH: tetramethylammonium hydroxide,

TEAH: tetraethylammonium hydroxide

(b) polar solvent

DMSO: dimethylsulfoxide

(c) an alkoxyalkylamine

AA1: Methoxyethylamine

AA2: Methoxypropylamine

AA3: Ethoxypropylamine

AA4: Propoxyethylamine

DETA: Diethylene triamine

(e) Amide

AM1: N, N-dimethylacetamide

AM2: N-methylpropanamide

AM3: N-methylethanamide

AM4: N, N-dimethylpropanamide

AM5: 3-methoxypropyl acrylamide

(f) an alkylene glycol dialkyl ether

AGE1: Ethylene glycol dimethyl ether

AGE2: Diethylene glycol dimethyl ether

AGE3: Diethylene glycol diethyl ether

AGE4: Propylene glycol dimethyl ether

MDG: diethylene glycol monomethyl ether

Experimental Example  One: Color resist  Removal evaluation

In order to evaluate the color resist removal effect of the cleaning composition prepared in Examples and Comparative Examples, a color filter substrate coated with red, green, and blue (hereinafter RGB) was used. The color resist was applied after being prebaked at 90 ° C for 120 seconds after exposure, developed, and then hard baked in an oven at 220 ° C in an oven.

To confirm the removability of the color resist of the cleaning composition prepared in Examples and Comparative Examples, the color filter substrate coated with the RGB was immersed in a solution at 70 캜 for 5 minutes and 10 minutes, and the resist remained Respectively. The results are shown in Table 2 below.

◎: 100% resist removal

○: Resist 80% or more removed

?: Less than 80% resist removal

X: No resist removal

Experimental Example  2: Organic  Evaluation of removal of insulating film

In order to confirm the removability of the organic insulating film, polyacylate resin (PAC resin) was applied on a glass substrate and prebaked at 90 ° C for 120 seconds. After patterning through exposure and development processes, the substrate was hard baked in an oven at 220 ° C to prepare an organic insulating film resist. A hard-baked substrate was used after application of the organic insulating film.

In order to confirm the removability of the organic insulating film of the detergent composition prepared in Examples and Comparative Examples, the organic insulating film substrate was immersed in a solution at 70 캜 for 5 minutes and 10 minutes, and the organic insulating film remained by optical microscope. The results are shown in Table 2 below.

◎: 100% resist removal

○: Resist 80% or more removed

?: Less than 80% resist removal

X: No resist removal

Experimental Example  3: Transparent resin film  Removal evaluation

In order to confirm the removability of the transparent resin film, a copolymerized transparent resin was coated on the substrate by adding a compound having an epoxy group to the acrylate monomer and then pre-baked at 90 ° C for 120 seconds. After patterning through exposure and development processes, the substrate was hard baked in an oven at 220 ° C to prepare a transparent resin film. A hard-baked substrate was used after applying the transparent resin film.

In order to confirm the removability of the transparent resin film of the cleaner composition prepared in Examples and Comparative Examples, the organic insulating film substrate was immersed in a solution at 70 캜 for 5 minutes and 10 minutes, and the organic insulating film remained by optical microscope. The results are shown in Table 2 below.

◎: 100% resist removal

○: Resist 80% or more removed

?: Less than 80% resist removal

X: No resist removal

RGB substrate Organic insulating film substrate Transparent resin substrate Rework time 5 minutes 10 minutes 5 minutes 10 minutes 5 minutes 10 minutes Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Example 9 Example 10 Comparative Example 1 X X X X Comparative Example 2 X X X X X Comparative Example 3 X X X X X Comparative Example 4 X X X X Comparative Example 5 X X X X X X Comparative Example 6 X X X X Comparative Example 7 X X X X X X Comparative Example 8 X X X Comparative Example 9 X X X X X Comparative Example 10 X X X X X X

As shown in Table 2, the cleaning compositions of Examples 1 to 10 exhibited excellent cleaning effects on both the color resist substrate, the organic insulating film substrate, and the transparent resin substrate.

On the contrary, the compositions of Comparative Examples 1 to 8, which do not include any of the constitution of the present invention or are out of the content range, have a very poor cleaning effect on the color resist substrate, the organic insulating film substrate and the transparent resin substrate. Also, it was experimentally confirmed that the compositions of Comparative Examples 9 to 10 in which the alkylene glycol monoalkyl ether was contained in the detergent composition were also extremely poor in the cleaning effect on the color resist substrate, the organic insulating film substrate, and the transparent resin substrate.

Therefore, the cleaning liquid composition having the composition of the present invention can sufficiently remove the color resist, the organic insulating film, and the transparent resin key plate of the color filter in a short time, thereby improving the productivity of color filter reuse.

Claims (10)

With respect to the total weight of the composition,
(a) 1-10% by weight of a quaternary ammonium salt compound,
(b) 40 to 80% by weight of a polar solvent,
(c) from 1 to 20% by weight of an alkoxyalkylamine having the structure of the formula (1)
(d) 0.1-5% by weight of a hydroxylamine compound,
(e) 1-20% by weight of an amide having the structure of the formula (2)
(f) 1-20% by weight of an alkylene glycol dialkyl ether,
(g) 0.01-2% by weight of an inorganic base or salt thereof and
(h) 1 to 40% by weight of water, and a cleaning agent composition for removing a color resist, an organic insulating film and a transparent resin.
[Chemical Formula 1]
Figure pat00003

(In the formula 1,
R 1 is a C 1 to C 6 chain or cyclic alkoxy group, and the alkoxy group may be substituted with a C 1 to C 6 chain or cyclic alkyl group or a C 1 to C 3 alkoxy group,
R 2 and R 3 are each independently hydrogen or a C 1 to C 6 chained or cyclic alkyl group, and n is an integer of 1 to 4.)
(2)
Figure pat00004

(In the formula (2)
R 4 , R 5 and R 6 are each independently hydrogen, a C 1 to C 4 chained or cyclic alkyl group, or a phenyl group.)
The method according to claim 1,
The quaternary ammonium salt compound (a) is composed of tetramethylammonium hydroxide (TMAH), tetraethylammonium hydroxide (TEAH), tetrapropylammonium hydroxide (TPAH) and tetrabutylammonium hydroxide (TBAH) And a cleaning agent composition for removing a color resist, an organic insulating film, and a transparent resin.
The method according to claim 1,
The polar solvent (b) may be at least one selected from the group consisting of dimethylsulfoxide, diethylsulfoxide, dipropylsulfoxide, sulfolane, n-methylpyrrolidone, pyrrolidone and n- , A color resist, an organic insulating film, and a cleaning agent composition for removing a transparent resin.
The method according to claim 1,
The alkoxyalkylamine having the structure (c) represented by the general formula (1) is preferably a methoxyethylamine, a methoxypropylamine, an ethoxypropylamine, a propoxyethylamine, an isopropoxypropylamine, a methoxyethoxypropylamine, An organic insulating film and a transparent resin film, which are at least one selected from the group consisting of 2-yl-methane amine, (oxolan-2-yl-methyl) butan- A cleaner composition for removing a resin.
The method according to claim 1,
Wherein the hydroxylamine-based compound (d) is at least one selected from the group consisting of hydroxylamine, dimethylhydroxylamine, and diethylhydroxylamine, and a cleaning agent composition for removing a color resist, an organic insulating film, and a transparent resin.
The method according to claim 1,
The amide having the structure of (e) (2) can be prepared by reacting an amide having the structure of the formula (2) with formamide, acetamide, benzamide, N -methylpropanamide, propanamide, butanamide, N, N-dimethylacetamide, A cleaning agent composition for removing a color resist, an organic insulating film and a transparent resin, which is at least one selected from the group consisting of dimethyl propanamide, N-ethyl-N-methylbenzeneamide, N-phenylbutanamide and N-phenylbenzamide.
The method according to claim 1,
The alkylene glycol dialkyl ether (f) is selected from the group consisting of ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol methyl butyl ether, propylene Glycol dimethyl ether, and dipropylene glycol dimethyl ether. The cleaning composition for removing a color resist, an organic insulating film, and a transparent resin.
The method according to claim 1,
Wherein the inorganic base or salt thereof is at least one selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, sodium nitrate, potassium nitrate, sodium sulfate, potassium sulfate, sodium silicate, A color resist, an organic insulating film, and a cleaning agent composition for removing a transparent resin.
The method according to claim 1,
An organic insulating film and a transparent resin, which is free from an alkylene glycol monoalkyl ether.
The method according to claim 1,
(A) quaternary organic ammonium hydroxydotetramethylammonium hydroxide (TMAH);
(B) dimethyl sulfoxide (DMSO) as the polar solvent, and (c) alkoxyalkylamines as the at least one of methoxyethylamine, methoxypropylamine, ethoxypropylamine and propoxyethylamine;
(E) at least one of amide, N, N-dimethylacetamide, N-methylpropanamide, N-methylethanamide and N, N-dimethylpropanamide;
(F) an alkylene glycol dialkyl ether, at least one of ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether and propylene glycol dimethyl ether; And
The cleaning agent composition for removing a color resist, an organic insulating film, and a transparent resin, wherein (g) the inorganic base or salt thereof comprises at least one of sodium nitrate, sodium hydroxide, potassium hydroxide, sodium bicarbonate, potassium carbonate and sodium carbonate.
KR1020150099076A 2014-08-06 2015-07-13 Cleaning composition KR20160017606A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201510479447.6A CN105368611B (en) 2014-08-06 2015-08-03 Cleaning compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20140101060 2014-08-06
KR1020140101060 2014-08-06

Publications (1)

Publication Number Publication Date
KR20160017606A true KR20160017606A (en) 2016-02-16

Family

ID=55448060

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020150099076A KR20160017606A (en) 2014-08-06 2015-07-13 Cleaning composition

Country Status (1)

Country Link
KR (1) KR20160017606A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180035590A (en) * 2016-09-29 2018-04-06 주식회사 엘지화학 Composition for cleaning substrate of display device and preparing method of display device using the same
KR20220104767A (en) 2019-11-20 2022-07-26 닛산 가가쿠 가부시키가이샤 Detergent Compositions and Cleaning Methods

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20030026664A (en) 2001-09-26 2003-04-03 주식회사 동진쎄미켐 A color resist remover composition for tft-lcd preparation
KR20140028962A (en) 2012-08-31 2014-03-10 주식회사 이엔에프테크놀로지 Stripper composition for thick negative photoresist

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20030026664A (en) 2001-09-26 2003-04-03 주식회사 동진쎄미켐 A color resist remover composition for tft-lcd preparation
KR20140028962A (en) 2012-08-31 2014-03-10 주식회사 이엔에프테크놀로지 Stripper composition for thick negative photoresist

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20180035590A (en) * 2016-09-29 2018-04-06 주식회사 엘지화학 Composition for cleaning substrate of display device and preparing method of display device using the same
KR20220104767A (en) 2019-11-20 2022-07-26 닛산 가가쿠 가부시키가이샤 Detergent Compositions and Cleaning Methods
US11732214B2 (en) 2019-11-20 2023-08-22 Nissan Chemical Corporation Cleaning agent composition comprising an alkylamide solvent and a fluorine-containing quaternary ammonium salt

Similar Documents

Publication Publication Date Title
KR20160017477A (en) Cleaning composition
CN105368611A (en) Cleaning composition
KR20140122082A (en) Resist stripper composition
KR20160017606A (en) Cleaning composition
KR20160018210A (en) Cleaning composition
KR101758051B1 (en) Stripping composition for color filter
KR102317153B1 (en) Resist stripper composition
KR20170084578A (en) Liquid composition for stripping a color resist and an organic insulating layer
KR20160016179A (en) Stripper composition for photoresist and organic layer
KR102542260B1 (en) stripping composition FOR COLOR FILTER
KR102009530B1 (en) Liquid composition for stripping a color resist and an organic insulating layer
KR102040066B1 (en) Liquid composition for stripping a color resist and an organic insulating layer
CN106896652B (en) Color resist stripper composition
KR20170076083A (en) Liquid composition for stripping a color resist
KR102010593B1 (en) Liquid composition for stripping a color resist and an organic insulating layer
KR20170076087A (en) Liquid composition for stripping a color resist
KR102091582B1 (en) Resist stripper composition
KR20170076090A (en) Liquid composition for stripping a color resist
KR20160145275A (en) Resist stripper composition and a method of stripping resist using the same
KR102040064B1 (en) color resist stripper composition
CN111596533B (en) Resist stripping liquid composition
KR102540253B1 (en) stripping composition FOR COLOR FILTER
KR20180087820A (en) Resist stripper composition
KR20180102329A (en) Resist stripper composition
KR20150144564A (en) Resist stripper composition