KR20160033023A - A resist stripper composition, a method of manufacturing flat panel displays, and flat panel displays manufactured by the same - Google Patents
A resist stripper composition, a method of manufacturing flat panel displays, and flat panel displays manufactured by the same Download PDFInfo
- Publication number
- KR20160033023A KR20160033023A KR1020150095667A KR20150095667A KR20160033023A KR 20160033023 A KR20160033023 A KR 20160033023A KR 1020150095667 A KR1020150095667 A KR 1020150095667A KR 20150095667 A KR20150095667 A KR 20150095667A KR 20160033023 A KR20160033023 A KR 20160033023A
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- KR
- South Korea
- Prior art keywords
- resist
- weight
- primary
- compound
- flat panel
- Prior art date
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- 238000007598 dipping method Methods 0.000 description 1
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- 238000004090 dissolution Methods 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000004299 exfoliation Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- GTFMAONWNTUZEW-UHFFFAOYSA-N glutaramic acid Chemical class NC(=O)CCCC(O)=O GTFMAONWNTUZEW-UHFFFAOYSA-N 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000002706 hydrostatic effect Effects 0.000 description 1
- 150000008624 imidazolidinones Chemical class 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical class CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- CGJMROBVSBIBKP-UHFFFAOYSA-N malonamic acid Chemical class NC(=O)CC(O)=O CGJMROBVSBIBKP-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical class NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
- H01L21/04—Manufacture 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
- H01L21/18—Manufacture 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
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment 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
- H01L21/3105—After-treatment
- H01L21/311—Etching the insulating layers by chemical or physical means
- H01L21/31127—Etching organic layers
- H01L21/31133—Etching organic layers by chemical means
Landscapes
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Chemical & Material Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Abstract
Description
본 발명은 레지스트 박리액 조성물에 관한 것으로, 보다 상세하게는 레지스트 박리 공정에서 금속 배선의 부식을 최소화하고, 뛰어난 박리 능력을 갖는 레지스트 박리액 조성물, 상기 조성물을 사용하는 플랫 패널 디스플레이 기판의 제조방법, 및 상기 제조방법으로 제조된 플랫 패널 디스플레이 기판에 관한 것이다.The present invention relates to a resist stripper composition, and more particularly, to a resist stripper composition that minimizes corrosion of a metal wiring in a resist stripping process and has excellent stripping ability, a method of manufacturing a flat panel display substrate using the composition, And a flat panel display substrate manufactured by the manufacturing method.
최근 평판표시장치의 고해상도 구현에 대한 요구가 증가함에 따라 단위면적당의 화소수를 증가시키기 위한 노력이 계속되고 있다. 이러한 추세에 따라 배선 폭의 감소도 요구되고 있으며, 그에 대응하기 위해서 건식 식각 공정이 도입되는 등 공정 조건도 갈수록 가혹해지고 있다. 또한, 평판표시장치의 대형화로 인해 배선에서의 신호 속도 증가도 요구되고 있으며, 그에 따라 알루미늄에 비해 비저항이 낮은 구리가 배선재료로 실용화되고 있다. 이에 발맞추어 레지스트 제거 공정인 박리공정에 사용되는 박리액에 대한 요구 성능도 높아지고 있다.In recent years, efforts have been made to increase the number of pixels per unit area as the demand for high-resolution implementation of flat panel displays increases. In accordance with this tendency, reduction of the wiring width is also required, and in order to cope with this, the dry etching process has been introduced, and the process conditions have become increasingly severe. In addition, due to the enlargement of the flat panel display device, an increase in the signal speed in the wiring is also required, and copper having a lower resistivity than aluminum is now being used as a wiring material. Accordingly, the required performance of the stripping solution used in the stripping process, which is a resist stripping process, is increasing.
구체적으로 건식 식각 공정 이후에 발생하는 식각 잔사에 대한 제거력 및 금속배선에 대한 부식 억제력 등에 대하여 상당한 수준의 박리특성이 요구되고 있다. 특히 알루미늄뿐만 아니라 구리에 대한 부식억제력도 요구되고 있으며, 가격 경쟁력 확보를 위해, 기판의 처리매수 증대와 같은 경제성도 요구되고 있다.Specifically, a considerable level of exfoliation characteristics is required for the removal power against etch residue generated after the dry etching process and the corrosion inhibiting ability against metal wiring. In particular, corrosion resistance to copper as well as aluminum is required, and in order to secure price competitiveness, economic efficiency such as increase in the number of processed substrates is also required.
일반적으로 레지스트를 제거하기 위하여 모노에탄올아민, 모노이소프로판올아민 등의 수용성 유기 아민, 감마 부틸락톤 및 DMSO 등의 유기 용매 등이 사용되고 있다. 또한, 아민에 의해 발생되는 금속의 부식을 억제하기 위하여 일반적으로 카테콜, 레소시놀, 벤조트리아졸 등 다양한 형태의 부식방지제를 사용하고 있으며, 이를 포함하는 포토레지스트 박리액 조성물이 제안되고 있다.Generally, water-soluble organic amines such as monoethanolamine, monoisopropanolamine, and organic solvents such as gamma-butyllactone and DMSO are used to remove the resist. In addition, various types of corrosion inhibitors such as catechol, resorcinol, and benzotriazole are generally used to inhibit metal corrosion caused by amines, and a photoresist stripper composition containing the same has been proposed.
그러나, 종래의 포토레지스트 박리액 조성물은 부식성능, 처리매수, 공정 또는 장기 보관에 있어서의 낮은 안정성 등의 문제가 알려져 있다. 예를 들어, 대한민국 공개특허 제10-2006-0117666호는 본 발명의 화학식 1과 동일한 화합물과 유기 아민 화합물 등을 유효성분으로 함유하는 포토레지스트 박리액 조성물을 개시하고 있으나, 금속 배선의 부식 방지를 위해 2종 이상의 부식 방지제를 필수로 요구한다. 그러므로, 부식 방지제가 박리공정 후 배선에 잔류할 가능성이 높을 뿐만 아니라, 장기 보관 시 박리액의 변색 발생 및 레지스트 박리액 조성물의 박리 시간이 길어지는 등 박리액의 성능을 감소시키는 문제점이 있다.However, conventional photoresist stripper liquid compositions are known to have problems such as corrosion performance, the number of treatments, and low stability in process or long-term storage. For example, Korean Patent Laid-Open Publication No. 10-2006-0117666 discloses a photoresist stripping liquid composition containing the same compound as Chemical Formula 1 of the present invention and an organic amine compound as an active ingredient, Two or more kinds of corrosion inhibitors are required as a requisite. Therefore, there is a problem that the corrosion inhibitor is likely to remain in the wiring after the peeling process, and also deteriorates the performance of the peeling solution, such as the occurrence of discoloration of the peeling solution and the peeling time of the resist stripping solution composition.
이에, 상기와 같은 종래기술의 문제점을 해결하고, 우수한 방식 효과뿐만 아니라, 신속하고 우수한 박리 특성을 갖는 레지스트 박리액 조성물의 개발이 필요하다. Accordingly, there is a need to develop a resist stripping liquid composition that solves the above-described problems of the prior art and has not only excellent system effect but also quick and excellent stripping properties.
본 발명은, 상기 종래기술의 상기와 같은 문제를 해결하기 위하여 안출된 것으로서, 우수한 레지스트 제거능을 가질 뿐만 아니라, 알루미늄 및/또는 구리를 포함하는 금속 배선에 대한 부식 방지력이 뛰어나며, 특히, 레지스트가 기판 표면에 잔류하여 탈이온수 접촉시 얼룩을 형성하는 것을 효과적으로 방지하는 레지스트 박리액 조성물을 제공하는 것을 목적으로 한다.The present invention has been conceived in order to solve the above problems of the prior art, and it is an object of the present invention to provide a resist composition which not only has excellent resist removing ability, but also has excellent corrosion resistance against metal wiring including aluminum and / It is an object of the present invention to provide a resist stripper composition that effectively remains on the surface of a substrate and effectively prevents stains from forming upon contact with deionized water.
또한, 본 발명은 상기 조성물을 사용하는 플랫 패널 디스플레이 기판의 제조방법, 및 상기 제조방법으로 제조된 플랫 패널 디스플레이 기판을 제공하는 것을 목적으로 한다.It is another object of the present invention to provide a method of manufacturing a flat panel display substrate using the composition, and a flat panel display substrate manufactured by the method.
본 발명은,According to the present invention,
하기 화학식 1로 표시되는 화합물(A); (A) represented by the following general formula (1);
1차 알칸올아민 및 3차 알칸올아민을 포함하는 알칸올아민류(B);Alkanolamines (B) comprising a primary alkanolamine and a tertiary alkanolamine;
1차 알코올류(C); 및Primary alcohols (C); And
비양자성 극성용매(D)를 포함하는 레지스트 박리액 조성물을 제공한다:A resist stripper composition comprising a non-polar protic solvent (D) is provided:
[화학식 1][Chemical Formula 1]
상기 화학식 1에서, In Formula 1,
R1 내지 R8은 각각 독립적으로 수소 또는 C1 ~C4의 알킬기이다.
R 1 to R 8 are each independently hydrogen or a C 1 to C 4 alkyl group.
또한, 본 발명은 In addition,
상기 레지스트 박리액 조성물을 사용하여 플랫 패널 디스플레이 기판을 세정하는 공정을 포함하는 플랫 패널 디스플레이 기판의 제조방법을 제공한다.And a step of cleaning the flat panel display substrate using the resist stripping liquid composition.
또한, 본 발명은In addition,
상기 제조방법으로 제조된 플랫 패널 디스플레이 기판을 제공한다.
A flat panel display substrate manufactured by the above manufacturing method is provided.
본 발명에 따른 레지스트 박리액 조성물은 우수한 레지스트 제거능을 가지므로 레지스트를 효과적으로 제거하며, 박리 공정에서 알루미늄 및/또는 구리 등의 금속 배선에 대한 부식을 최소화하며, 특히, 레지스트가 기판 표면에 잔류하여 탈이온수 접촉시 얼룩을 형성하는 것을 방지하는 효과를 제공한다.
Since the resist stripper composition according to the present invention has an excellent resist removing ability, it effectively removes the resist and minimizes corrosion of metal wiring such as aluminum and / or copper in the stripping process. Particularly, Thereby providing an effect of preventing stains from forming upon contact with ionized water.
하기 화학식 1로 표시되는 화합물(A); (A) represented by the following general formula (1);
1차 알칸올아민 및 3차 알칸올아민을 포함하는 알칸올아민류(B);Alkanolamines (B) comprising a primary alkanolamine and a tertiary alkanolamine;
1차 알코올류(C); 및Primary alcohols (C); And
비양자성 극성용매(D)를 포함하는 레지스트 박리액 조성물을 제공한다:A resist stripper composition comprising a non-polar protic solvent (D) is provided:
[화학식 1][Chemical Formula 1]
상기 화학식 1에서, In Formula 1,
R1 내지 R8은 각각 독립적으로 수소 또는 C1 ~C4의 알킬기이다.
R 1 to R 8 are each independently hydrogen or a C 1 to C 4 alkyl group.
이하, 각 성분에 대하여 구체적으로 설명한다.
Hereinafter, each component will be described in detail.
(A) 화학식 1로 표시되는 화합물(A) a compound represented by the formula (1)
본 발명의 레지스트 박리액 조성물은 하기 화학식 1로 표시되는 화합물(A)을 포함한다.The resist stripping composition of the present invention comprises a compound (A) represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 화학식 1에서, In Formula 1,
R1 내지 R8은 각각 독립적으로 수소 또는 C1 ~C4의 알킬기이다.
R 1 to R 8 are each independently hydrogen or a C 1 to C 4 alkyl group.
상기 화학식 1로 표시되는 화합물(A)은 레지스트 박리액 조성물에 포함되어, 금속 배선의 방식력을 향상시키는 역할을 한다.The compound (A) represented by the above formula (1) is included in the resist stripping liquid composition and plays a role of improving the damping force of the metal wiring.
상기 화학식 1로 표시되는 화합물로는 예컨대, 4-메틸-4,5,6,7-테트라히드로-1H-벤조[1,2,3]트리아졸, 5-메틸-4,5,6,7-테트라히드로-1H-벤조[1,2,3]트리아졸, 5,6-디메틸-4,5,6,7-테트라히드로-1H-벤조[1,2,3]트리아졸 및 4,6-디메틸-4,5,6,7-테트라히드로-1H-벤조[1,2,3]트리아졸 등을 들 수 있다. 이들은 1종 단독으로 또는 2종 이상을 조합하여 사용할 수 있다.Examples of the compound represented by Formula 1 include 4-methyl-4,5,6,7-tetrahydro-1H-benzo [1,2,3] triazole, 5-methyl-4,5,6,7 -Tetrahydro-1H-benzo [1,2,3] triazole, 5,6-dimethyl-4,5,6,7-tetrahydro-1H- benzo [1,2,3] triazole and 4,6 -Dimethyl-4,5,6,7-tetrahydro-1H-benzo [1,2,3] triazole, and the like. These may be used alone or in combination of two or more.
상기 화학식 1로 표시되는 화합물(A)은 레지스트 박리액 조성물 총 중량에 대하여, 0.0001 내지 0.1중량%로 포함되는 것이 바람직하고, 0.001 내지 0.1 중량%로 포함되는 것이 더 바람직하며, 0.003 내지 0.05 중량%로 포함되는 것이 가장 바람직하다. 상기 화학식 1로 표시되는 화합물 함량이 0.0001 중량% 미만인 경우에는, 금속 배선이 장시간 박리액과 접촉할 때 금속 배선에서 부분적인 부식 현상이 일어날 수 있다. 또한, 0.1 중량%를 초과하는 경우 금속 배선에 잔류하여 2차 오염을 발생 시킬 수 있으며, 조성물 가격이 상승하여 가격 대비 성능 면에서 비효율적이다.
The compound (A) represented by the formula (1) is preferably contained in an amount of 0.0001 to 0.1% by weight, more preferably 0.001 to 0.1% by weight, more preferably 0.003 to 0.05% by weight based on the total weight of the resist stripper composition. Is most preferable. When the content of the compound represented by the above formula (1) is less than 0.0001% by weight, a partial corrosion phenomenon may occur in the metal wiring when the metal wiring is in contact with the peeling liquid for a long time. If it exceeds 0.1% by weight, it may remain in the metal wiring to cause secondary contamination, and the price of the composition increases, which is inefficient in terms of price and performance.
(B) 1차 (B) Primary 알칸올아민Alkanolamine 및 3차 And tertiary 알칸올아민을Alkanolamine 포함하는 Included 알칸올아민류Alkanolamines
상기 알칸올아민류는 박리력 향상 및 얼룩 발생 방지를 위해 사용된다. The alkanolamines are used for improving the peeling force and preventing the occurrence of stains.
상기 1차 알칸올아민은 건식 또는 습식 식각, 애싱(ashing) 또는 이온주입 공정(ion implant processing) 등의 여러 공정 조건하에서 변질되거나 가교된 레지스트(resist)의 고분자 매트릭스에 강력하게 침투하여 분자 내 또는 분자간에 존재하는 결합을 깨뜨리는 역할을 하며. 기판에 잔류하는 레지스트 내의 구조적으로 취약한 부분에 빈 공간을 형성시켜 레지스트를 무정형의 고분자 겔(gel)덩어리 상태로 변형시킴으로써 기판 상부에 부착된 레지스트가 쉽게 제거될 수 있게 한다.The primary alkanolamine can penetrate strongly into the polymer matrix of the resist or crosslinked resist under various process conditions such as dry or wet etching, ashing or ion implant processing, It serves to break the bond existing between molecules. An empty space is formed in a structurally weak portion in the resist remaining on the substrate, thereby deforming the resist into an amorphous polymer gel mass state so that the resist attached on the substrate can be easily removed.
상기 1차 알칸올아민의 대표적인 예로는 모노에탄올아민, 모노이소프로판올아민, 2-(2-아미노에톡시)에탄올 등을 들을 수 있으나, 이들로 한정되는 것은 아니다. 상기 1차 알칸올아민은 1종 단독으로 또는 2종 이상의 조합으로 사용될 수 있다.Representative examples of the primary alkanolamine include, but are not limited to, monoethanolamine, monoisopropanolamine, 2- (2-aminoethoxy) ethanol, and the like. The primary alkanolamine may be used alone or in combination of two or more.
상기 3차 알칸올아민은 용해된 레지스트가 기판 표면에 잔류하여 탈이온수에 접촉할 때 발생하는 얼룩을 방지하는 역할을 수행한다. 상기 3차 알칸올아민은 하기 화학식 2로 표시될 수 있다:The tertiary alkanolamine serves to prevent stains that are generated when the dissolved resist remains on the surface of the substrate to contact deionized water. The tertiary alkanolamine may be represented by the following Formula 2:
상기 식에서In the above formula
R9, R10 및 R11은 각각 독립적으로 탄소수 1 내지 4의 알킬기 또는 탄소수 1 내지 4의 히드록시알킬기이며, R9, R10 및 R11 중의 하나 이상은 탄소수 1 내지 4의 히드록시알킬기이다.R9, R10 and R11 are each independently an alkyl group having 1 to 4 carbon atoms or a hydroxyalkyl group having 1 to 4 carbon atoms; and at least one of R9, R10 and R11 is a hydroxyalkyl group having 1 to 4 carbon atoms.
상기 화학식 2의 화합물 중 메틸디에탄올아민, 디메틸에탄올아민, 트리에탄올아민 등이 더욱 바람직하게 사용될 수 있다.
Of the compounds of formula (2), methyldiethanolamine, dimethylethanolamine, triethanolamine and the like are more preferably used.
상기 알칸올아민류에서 1차 알칸올아민과 3차 알칸올아민의 함량은 박리력 향상 효과가 더 요구되는 경우에는 1차 알칸올아민의 함량을 높이고, 얼룩 개선효과가 더 요구되는 경우에는 3차 알칸올아민의 함량을 높이는 방식으로 조절될 수 있다.In the alkanolamines, the content of the primary alkanolamine and the tertiary alkanolamine may be increased when the effect of improving the peeling force is further demanded, and the content of the primary alkanolamine should be increased. Can be adjusted in such a way as to increase the content of alkanolamine.
상기 1차 알칸올아민과 3차 알칸올아민은 1:0.1 ~ 0.1:1의 중량비로 포함될 수 있으며, 더욱 바람직하게는, 1:0.2 ~ 0.2:1의 중량비로 포함될 수 있다.The primary alkanolamine and the tertiary alkanolamine may be contained in a weight ratio of 1: 0.1 to 0.1: 1, and more preferably in a weight ratio of 1: 0.2 to 0.2: 1.
상기 알칸올아민류는 레지스트 박리액 조성물 총 중량에 대하여, 0.01 내지 10 중량%로 포함되는 것이 바람직하며, 1내지 8 중량%로 포함되는 것이 더욱 바람직하다. 알칸올아민류의 함량이 0.01 중량% 미만이면 레지스트 박리력 저하로 레지스트 이물이 잔류 하는 문제를 일으킬 수 있으며, 10 중량%를 초과하면 금속배선에 대한 급격한 부식 속도 증가를 유발시킬 수 있다.
The alkanolamines are preferably contained in an amount of 0.01 to 10% by weight, and more preferably 1 to 8% by weight based on the total weight of the resist stripper composition. If the content of the alkanolamines is less than 0.01% by weight, the resist peeling force may cause a problem of foreign matter residues remaining. If the content of alkanolamines is more than 10% by weight, a rapid increase in the corrosion rate to metal wiring may be caused.
(C) 1차 알코올류(C) Primary alcohols
상기 1차 알코올류는 레지스트 박리액 조성물에 포함되어 고형화된 레지스트 고분자를 용해시키는 역할을 하며, 레지스트 박리 이후 탈이온수(DIW)의 린스 공정에서 물에 의한 박리액의 제거를 용이하게 하여, 박리액 내에 용해된 레지스트의 재석출을 최소화 하도록 하는 역할을 수행한다.The primary alcohol serves to dissolve the solidified resist polymer contained in the resist stripper composition and facilitates the removal of the stripper by water in the rinsing process of deionized water (DIW) after resist stripping, Thereby minimizing redeposition of the resist dissolved in the resist.
상기 1차 알코올류는, 에틸렌글라이콜 모노메틸 에테르, 에틸렌글라이콜 모노에틸 에테르, 에틸렌글라이콜 모노이소프로필 에테르, 에틸렌글라이콜 모노부틸 에테르, 디에틸렌글라이콜 모노메틸 에테르, 디에틸렌글라이콜 모노에틸 에테르, 디에틸렌글라이콜 모노이소프로필 에테르, 디에틸렌글라이콜 모노부틸 에테르, 트리에틸렌글라이콜 모노메틸 에테르, 트리에틸렌글라이콜 모노에틸 에테르, 트리에틸렌글라이콜 모노이소프로필 에테르, 트리에틸렌글라이콜 모노부틸 에테르, 폴리에틸렌글라이콜 모노메틸 에테르, 폴리에틸렌글라이콜 모노부틸 에테르, 디에틸렌글라이콜, 트리에틸렌글라이콜, 아이소프로필글라이콜 등을 포함하는 알킬렌글리콜계 1차 알코올 중에서 선택되는 1종 이상; 및The primary alcohols include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, di Ethylene glycol monoethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol Polyethylene glycol monomethyl ether, polyethylene glycol monobutyl ether, diethylene glycol, triethylene glycol, isopropyl glycol, and the like, as well as organic solvents such as ethylene glycol monobutyl ether, ethylene glycol monobutyl ether, Alkylene glycol primary alcohols; And
테트라하이드로퍼퓨릴알코올, 하이드록시메틸싸이클로펜텐, 4-하이드록시메틸-1,3-디옥솔란, 2-메틸-4-하이드록시메틸-1,3-디옥솔란, 2,2-디메틸-1,3-디옥솔란-4-메탄올, 1,3-프로판디올, 1,3-부탄디올, 1,4-부탄디올, 2-메톡시에탄올 등을 포함하는, 알킬렌글리콜계 1차 알코올류를 제외한, 1차 알코올 중에서 선택되는 1종 이상을 포함하는 것이 바람직하다.Tetrahydrofurfuryl alcohol, hydroxymethylcyclopentene, 4-hydroxymethyl-1,3-dioxolane, 2-methyl-4-hydroxymethyl-1,3-dioxolane, 2,2- Except for the alkylene glycol primary alcohols including 3-dioxolane-4-methanol, 1,3-propanediol, 1,3-butanediol, 1,4-butanediol, 2- It is preferable to include at least one member selected from the group consisting of alcohol and alcohols.
상기 알킬렌글리콜계 1차 알코올류 및 상기 알킬렌글리콜계 1차 알코올류를 제외한 1차 알코올은 1:0.1 ~ 0.1:1의 중량비로 포함되는 것이 바람직하며, 1:0.2 ~ 0.2:1의 중량비로 포함되는 것이 더욱 바람직하다. 중량비가 상기 범위일 경우 고형화된 레지스트 고분자의 용해가 용이할 뿐만 아니라 박리 후 세정 공정에서 레지스트 고분자의 재흡착을 방지하여 2차 오염을 감소시키는 장점이 있다.The primary alcohols excluding the alkylene glycol primary alcohols and the alkylene glycol primary alcohols are preferably contained in a weight ratio of 1: 0.1 to 0.1: 1, and a weight ratio of 1: 0.2 to 0.2: 1 More preferably, When the weight ratio is in the above range, solubilization of the solidified resist polymer is easy, and secondary resorption of the resist polymer is prevented in the cleaning step after peeling, thereby reducing secondary contamination.
상기 1차 알코올류는 레지스트 박리액 조성물 총 중량에 대하여, 20 내지 85 중량%로 포함되는 것이 바람직하며, 30 내지 80 중량%로 포함되는 것이 더욱 바람직하다. 상기와 같은 범위로 포함되는 경우 DIW 린스(rinse) 공정에서 물에 의한 박리액 제거가 용이하다.
The primary alcohol is preferably contained in an amount of 20 to 85% by weight based on the total weight of the resist stripper composition, more preferably 30 to 80% by weight. When it is included in the range as described above, it is easy to remove the peeling liquid by water in the DIW rinse process.
(D) (D) 비양자성Magnetostrictive 극성용매 Polar solvent
상기 비양자성 극성용매(D)는 박리액 조성물에서 식각 등에 의해 변질되거나 가교된 고분자의 제거 성능의 발현을 유리하게 하며, 이와 동시에 레지스트 박리액의 처리 매수 증가 효과를 향상시킨다.The aprotic polar solvent (D) advantageously exhibits the removal performance of the polymer degraded or crosslinked by etching or the like in the stripper solution composition, and at the same time, the effect of increasing the number of treatments of the resist stripper solution is improved.
상기 비양자성 극성용매는 상기 알칼리계 화합물에 의해 겔화된 레지스트 고분자를 용해시키는 역할을 하며, 포토레지스트의 분산을 원활하게 하여 용해(solvation)시키는 역할을 한다. 다시 말해, 포토레지스트의 용해에 매우 효과적인 유기 용매로서 고형화된 포토레지스트에 알칼리계 화합물의 침투를 빠르게 하여 박리 성능을 향상시키는 성분이다. 또한 레지스트 박리 이후 탈이온수의 린스 과정에서 물에 의한 박리액의 제거를 수월하게 하여 박리액 및 용해된 레지스트의 재흡착/재부착을 최소화한다. The aprotic polar solvent serves to dissolve the resist polymer gelled by the alkaline compound and smoothly disperses the photoresist to solvation. In other words, as an organic solvent highly effective in dissolving a photoresist, it is a component which accelerates the penetration of an alkaline compound into a solidified photoresist and improves the peeling performance. In addition, it facilitates the removal of the peeling liquid by the water during the rinsing of the deionized water after the peeling of the resist, thereby minimizing the re-adsorption / reattaching of the peeling liquid and the dissolved resist.
상기 비양자성 극성용매는 적당한 박리력을 위해 비점이 너무 높거나 낮지 않은 것이 바람직하게 사용될 수 있으며, 1종 단독은 물론 2종 이상을 혼합하여 사용할 수도 있다. The aprotic polar solvent may preferably be used in which the boiling point is not too high or low for proper peeling force, and may be used alone or in combination of two or more.
상기 비양자성 극성용매의 바람직한 예로는 N-메틸 피롤리돈(NMP), N-에틸 피롤리돈 등의 피롤리돈 화합물; 1,3-디메틸-2-이미다졸리디논, 1,3-디프로필-2-이미다졸리디논 등의 이미다졸리디논 화합물; γ―부티로락톤 등의 락톤 화합물; 디메틸설폭사이드(DMSO), 술폴란 등의 설폭사이드 화합물; 트리에틸포스페이트, 트리부틸포스페이트 등의 포스페이트 화합물; 디메틸카보네이트, 에틸렌카보네이토 등의 카보네이트 화합물; 포름아미드, N-메틸포름아미드, N-에틸포름아미드, N,N-디메틸포름아미드, N,N-디에틸포름아미드, 아세트아미드, N-메틸아세트아미드, N,N-디메틸아세트아미드, N,N-디메틸프로피온아미드, N-(2-히드록시에틸)아세트아미드, 3-메톡시-N,N-디메틸프로피온아미드, 3-(2-에틸헥실옥시)-N,N-디메틸프로피온아미드, 3-부톡시-N,N-디메틸프로피온아미드 등의 아미드 화합물; 등을 들 수 있으며, 이들은 1종 단독으로 또는 2종 이상의 조합으로 사용될 수 있다.Preferable examples of the aprotic polar solvent include pyrrolidone compounds such as N-methylpyrrolidone (NMP) and N-ethylpyrrolidone; Imidazolidinone compounds such as 1,3-dimethyl-2-imidazolidinone and 1,3-dipropyl-2-imidazolidinone; lactone compounds such as? -butyrolactone; Sulfoxide compounds such as dimethyl sulfoxide (DMSO) and sulfolane; Phosphate compounds such as triethyl phosphate, tributyl phosphate and the like; Carbonate compounds such as dimethyl carbonate, ethylene carbonate, and the like; N, N-dimethylacetamide, N, N-dimethylformamide, N, N-diethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, N , N-dimethylpropionamide, N- (2-hydroxyethyl) acetamide, 3-methoxy-N, N-dimethylpropionamide, 3- (2-ethylhexyloxy) -N, Amide compounds such as 3-butoxy-N, N-dimethylpropionamide; These may be used singly or in combination of two or more.
상기 비양자성 극성용매(D)는 레지스트 박리액 조성물 총 중량에 대하여, 5 내지 75 중량%로 포함되는 것이 바람직하며, 10 내지 60 중량%로 포함되는 것이 더욱 바람직하다. 상기와 같은 범위로 포함되는 경우, 식각 등에 의해 변질되거나 가교된 레지스트 고분자의 제거 성능의 발현에도 유리하다.
The amount of the aprotic polar solvent (D) is preferably 5 to 75% by weight, more preferably 10 to 60% by weight based on the total weight of the resist stripper composition. When it is contained in the above-mentioned range, it is advantageous also in manifesting the removal performance of the resist polymer modified or crosslinked by etching or the like.
본 발명의 레지스트 박리액 조성물은, 부식 방지제(E) 및 탈이온수(F)로 이루어진 군 가운데 1종 이상을 추가로 포함할 수 있다.The resist stripping composition of the present invention may further comprise at least one member selected from the group consisting of a corrosion inhibitor (E) and deionized water (F).
상기 부식 방지제(E)는 레지스트 박리액 조성물에 추가로 포함되어, 알루미늄 및/또는 구리를 포함하는 금속 배선의 부식 방지 능력을 향상시킨다.The corrosion inhibitor (E) is further included in the resist stripper composition to improve corrosion resistance of metal wiring including aluminum and / or copper.
상기 부식 방지제로는 예컨대, 포름산, 아세트산, 프로피온산과 같은 모노카르복실산, 수산, 말론산, 숙신산, 글루탄산, 아디프산, 피멜산, 말레산, 푸르마산, 글루타코닉산과 같은 디카르복실산, 트리멜리트산, 트리카르발릴산과 같은 트리카르복실산, 그리고 히드록시초산, 젖산, 살리실산, 말산, 주석산, 구연산, 글루콘산 및 옥시카르복실산 등의 유기산 류; Examples of the corrosion inhibitor include monocarboxylic acids such as formic acid, acetic acid and propionic acid, dicarboxylic acids such as malic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimetic acid, maleic acid, fumaric acid and glutaconic acid Tricarboxylic acids such as trimellitic acid, trimellitic acid and tricarvaleric acid, and organic acids such as hydroxyacetic acid, lactic acid, salicylic acid, malic acid, tartaric acid, citric acid, gluconic acid and oxycarboxylic acid;
숙시닉 아미드 에스터, 말릭 아미드 에스터, 말레릭 아미드 에스터, 푸마릭 아미드 에스터, 옥살릭 아미드 에스터, 말로닉 아미드 에스터, 글루타릭 아미드 에스터, 아세틱 아미드 에스터, 락틱 아미드 에스터, 시트릭 아미드 에스터, 타르타릭 아미드 에스터, 글루콜릭 아미드 에스터, 포믹 아미드 에스터 및 우릭 아미드 에스터 등의 유기산 아미드 에스터류;Maleic amide esters, maleic amide esters, maleic amide esters, fumaric amide esters, oxalic amide esters, malonic amide esters, glutaric amide esters, acetic amide esters, lactic amide esters, Organic acid amide esters such as tartaric amide esters, tartaric amide esters, tartaric amide esters, tartaric amide esters, tartaric amide esters, tartaric amide esters, tartaric amide esters, tartaric amide esters,
벤조트리아졸, 톨리트리아졸, 메틸 톨리트리아졸, 2,2’-[[[벤조트리아졸]메틸]이미노]비스에탄올, 2,2’-[[[메틸-1수소-벤조트리아졸-1-일]메틸]이미노]비스메탄올, 2,2’-[[[에틸-1수소-벤조트리아졸-1-일]메틸]이미노]비스에탄올, 2,2’-[[[메틸-1수소-벤조트리아졸-1-일]메틸]이미노]비스에탄올, 2,2’-[[[메틸-1수소-벤조트리아졸-1-일]메틸]이미노]비스카르복시산, 2,2’-[[[메틸-1수소-벤조트리아졸-1-일]메틸]이미노]비스메틸아민 및 2,2’-[[[아민-1수소-벤조트리아졸-1-일]메틸]이미노]비스에탄올 4-메틸-1-수소-벤조트리아졸 및 5-메틸-1-수소-벤조트리아졸 등과 같은 아졸계화합물;2,2 '- [[[[[benzotriazole] methyl] imino] bisethanol, 2,2' - [[[methyl-1-hydrogen-benzotriazole Yl] methyl] imino] bisethanol, 2,2 '- [[[ethyl-1-hydrogen-benzotriazol- Methyl-imino] biscarboxylic acid [methyl-1-hydrogen-benzotriazol-1-yl] methyl] imino] bisethanol and 2,2 '- [[ Methyl] imino] bismethylamine and 2,2 '- [[[amine-1-hydrogen-benzotriazol-1-yl] Methyl] imino] bisethanol 4-methyl-1-hydrogen-benzotriazole and 5-methyl-1-hydrogen-benzotriazole;
2,6-디메틸페놀, 2,4,6-트리메틸페놀, 2,6-디에틸페놀, 2,6-디에틸-4-메틸페놀, 2,6-디프로필페놀, 2,6-트리프로-4-메틸페놀, 2,6-디-t-부틸페놀, 2,4,6-트리-t-부틸페놀 및 2,6-디-t-부틸-4-메틸페놀 등과 같은 대칭형 페놀계 화합물; 등을 들 수 있으나 이에 한정되지 않는다. 이들은 1종 단독으로 또는 2종 이상의 조합으로 사용될 수 있다.2,6-dimethylphenol, 2,4,6-trimethylphenol, 2,6-diethylphenol, 2,6-diethyl-4-methylphenol, 4-methylphenol, 2,6-di-t-butylphenol, 2,4,6-tri-t-butylphenol and 2,6- ; But is not limited thereto. These may be used singly or in combination of two or more.
상기 부식 방지제는 레지스트 박리액 조성물 총 중량에 대하여, 3 중량% 이하로 포함되는 것이 바람직하며, 0.001 내지 2 중량%로 포함되는 것이 보다 바람직하다. 상기와 같은 범위로 포함되는 경우, 박리 혹은 DIW 린스 공정에서 알루미늄 또는 알루미늄 합금 및 구리 또는 구리 합금으로 이루어진 금속배선에 발생하는 부식을 방지할 수 있다.
The corrosion inhibitor is preferably contained in an amount of 3% by weight or less based on the total weight of the resist stripper composition, more preferably 0.001 to 2% by weight. When it is included in the range as described above, it is possible to prevent corrosion occurring in the metal wiring made of aluminum or aluminum alloy and copper or copper alloy in the peeling or DIW rinse process.
상기 탈 이온수(F)는 레지스트 박리액 조성물에 추가로 포함되어, 상기 알칼리계 화합물(B)의 활성화를 촉진시켜 박리 속도를 증가시키며, 탈이온수(DIW, deionized water)에 의한 린스 공정 시 기판상에 잔존하는 유기 오염물 및 레지스트 박리액을 빠르고 완전하게 제거시킬 수 있다. 또한 상기 1차 알코올류와 비양자성 극성용매의 혼합을 용이하게 하여, 박리 공정 후 탈이온수에 의한 린스 공정에서 잔류하지 않고 빠른 시간에 완전하게 제거될 수 있도록 한다. The deionized water (F) is further contained in the resist stripping liquid composition to promote the activation of the alkaline compound (B) to increase the stripping rate. In the rinsing process with deionized water (DIW) It is possible to quickly and completely remove the organic contaminants and the resist stripping solution remaining in the resist film. In addition, the mixing of the primary alcohol with the aprotic polar solvent is facilitated, so that it can be completely removed in a short time without remaining in the rinsing process by deionized water after the peeling process.
상기 탈 이온수는 레지스트 박리액 조성물 총 중량에 대하여, 70 중량% 이하로 포함되는 것이 바람직하며, 1 내지 45 중량%로 포함되는 것이 보다 바람직하다. 70 중량%를 초과하여 포함되면, 레지스트 용해 용량을 감소시켜 처리 매수를 감소시킬 수 있고, 기판이 장시간 침적되는 경우 금속 배선의 부식을 유발시킬 수 있다.The deionized water is preferably contained in an amount of 70% by weight or less based on the total weight of the resist stripper composition, more preferably 1 to 45% by weight. If it is contained in an amount exceeding 70% by weight, the resist dissolution capacity can be reduced to reduce the number of treatments, and corrosion of the metal wiring can be caused when the substrate is immersed for a long time.
본 발명의 레지스트 박리액 조성물은 상기에서 언급한 화합물을 일정량으로 유리하게 혼합하여 제조될 수 있으며, 혼합 방법은 특별히 제한되지 않으며 여러 가지 공지 방법을 제한 없이 적용할 수 있다.
The resist stripping solution composition of the present invention can be prepared by mixing the above-mentioned compounds with a certain amount, and the mixing method is not particularly limited and various known methods can be applied without limitation.
본 발명의 플랫 패널 디스플레이용 레지스트 박리액 조성물을 사용하여 레지스트를 제거하는 방법으로는 침지법이 일반적이지만 기타의 방법, 예를 들면 분무법에 의한 방법을 사용할 수도 있다. 본 발명에 의한 조성물로 처리한 후의 세정제로는 알코올과 같은 유기용제를 사용할 필요가 없고 물로 세정하는 것만으로도 충분하다.
As a method for removing the resist using the resist stripping liquid composition for a flat panel display of the present invention, a dipping method is generally used, but other methods such as a spraying method may also be used. As the cleaning agent after treatment with the composition according to the present invention, it is not necessary to use an organic solvent such as alcohol, and it is sufficient to wash with water.
또한, 본 발명은In addition,
본 발명의 레지스트 박리액 조성물을 이용하여 플랫 패널 디스플레이 기판을 세정하는 공정을 포함하는 플랫 패널 디스플레이 기판의 제조방법 및 상기 제조방법으로 제조된 플랫 패널 디스플레이 기판을 제공한다.There is provided a method of manufacturing a flat panel display substrate including a step of cleaning a flat panel display substrate using the resist stripping liquid composition of the present invention and a flat panel display substrate manufactured by the manufacturing method.
본 발명의 레지스트 박리액 조성물은 플랫 패널 디스플레이용 레지스트의 제거 공정에서 유용하게 사용될 수 있으며, 반도체 또는 기타 전자제품에도 사용될 수 있다.
The resist stripping liquid composition of the present invention can be usefully used in a process for removing a resist for a flat panel display, and can also be used for semiconductors or other electronic products.
이하, 본 발명의 실시예 및 비교예를 이용하여 더욱 상세하게 설명한다. 그러나 하기 실시예 및 비교예는 본 발명을 예시하기 위한 것으로서 본 발명의 범위가 하기 실시예 및 비교예에 의해 한정되지 않으며 다양하게 수정 및 변경될 수 있다.
Hereinafter, the present invention will be described in more detail with reference to examples and comparative examples. However, the following examples and comparative examples are provided for illustrating the present invention, and the scope of the present invention is not limited by the following examples and comparative examples, and various modifications and changes may be made.
실시예Example 1 ~10 및 1 to 10 and 비교예Comparative Example 1 ~ 5: 1 to 5: 레지스트Resist 박리액Peeling liquid 조성물의 제조 Preparation of composition
하기 표 1에 기재된 성분과 함량을 혼합하여 레지스트 박리액 조성물을 제조하였다.The ingredients and the contents shown in Table 1 below were mixed to prepare a resist stripper composition.
MDEAAEE
MDEA
35
3
MDEAAEE
MDEA
25
2
EDGMDG
EDG
2020
20
DMEAMEA
DMEA
5One
5
HMDMEDG
HMDM
1050
10
TEAMIPA
TEA
14
One
MDEAAEE
MDEA
23
2
EDGTHFA
EDG
5530
55
MDEAAEE
MDEA
25
2
DMPANMP
DMPA
2022.99
20
MDEAAEE
MDEA
23
2
THFAHMDM
THFA
2010
20
DMEAMIPA
DMEA
55
5
HMDMEDG
HMDM
1050
10
DMEAAEE
DMEA
55
5
HMDMEDG
HMDM
1050
10
tBMPBTA
tBMP
0.010.01
0.01
MDEAAEE
MDEA
3One
3
MDEAAEE
MDEA
35
3
HMDMEDG
HMDM
1050
10
HMDMEDG
HMDM
1050
10
(단위: 중량%)(Unit: wt%)
주)) : MTBT: 4-메틸-4,5,6,7-테트라히드로-1H-벤조[1,2,3]트리아졸: MTBT: 4-methyl-4,5,6,7-tetrahydro-1H-benzo [1,2,3] triazole
DMTBT: 5,6-디메틸-4,5,6,7-테트라히드로-1H-벤조[1,2,3]트리아졸DMTBT: 5,6-Dimethyl-4,5,6,7-tetrahydro-1H-benzo [1,2,3] triazole
MDEA: N-메틸 디에탄올아민MDEA: N-methyldiethanolamine
DMEA: N,N-디메틸에탄올아민DMEA: N, N-dimethylethanolamine
TEA: 트리에탄올아민TEA: triethanolamine
AEE: 2-(2-아미노에톡시)에탄올AEE: 2- (2-aminoethoxy) ethanol
EDG: 디에틸렌글리콜 모노에틸 에테르EDG: diethylene glycol monoethyl ether
MDG: 디에틸렌글리콜 모노메틸 에테르MDG: diethylene glycol monomethyl ether
NMF: N-메틸포름아미드NMF: N-methylformamide
NEF: N-에틸포름아미드NEF: N-ethylformamide
DMPA: N,N-디메틸프로피온아미드DMPA: N, N-dimethylpropionamide
NMP: N-메틸 피롤리돈NMP: N-methylpyrrolidone
THFA: 테트라하이드로퍼푸릴 알코올THFA: tetrahydroperfuryl alcohol
HMDM: 4-하이드록시메틸-2,2-디메틸-1,3-디옥솔란HMDM: 4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane
BTA: 벤조트리아졸BTA: benzotriazole
tBMP: t-부틸-4-메톡시페놀tBMP: t-Butyl-4-methoxyphenol
MIPA: 모노이소프로판올아민
MIPA: Monoisopropanolamine
시험예Test Example : : 레지스트Resist 박리액Peeling liquid 조성물의 특성 평가 Evaluation of composition characteristics
시험예Test Example 1. One. 레지스트Resist 박리액Peeling liquid 조성물의 Of the composition 박리력Peel force 평가 evaluation
상기 실시예 1~10 및 비교예 1~5의 레지스트 박리액 조성물의 박리력을 평가하기 위해 하기의 실험을 진행하였다.In order to evaluate the peeling force of the resist stripping liquid compositions of Examples 1 to 10 and Comparative Examples 1 to 5, the following experiment was conducted.
통상적인 방법에 따라 유리 기판상에 박막 스퍼터링법을 사용하여 Mo/Al/Mo, Cu/Ti층을 형성한 후, 포토 레지스트 패턴을 형성시킨 이후, 습식 식각 및 건식 식각 방식에 의해 금속막을 에칭한 기판을 각각 준비하였다. 상기 실시예 1~10 및 비교예 1~5의 레지스트 박리액 조성물의 온도를 50℃로 일정하게 유지시킨 후, 5분간 대상물을 침적하여 박리력을 평가하였다.After a photoresist pattern is formed after a Mo / Al / Mo or Cu / Ti layer is formed on a glass substrate by a thin film sputtering method according to a conventional method, the metal film is etched by a wet etching method and a dry etching method Respectively. After the temperature of the resist stripping composition of each of Examples 1 to 10 and Comparative Examples 1 to 5 was kept constant at 50 占 폚, the object was immersed for 5 minutes to evaluate the peeling force.
이후 기판상에 잔류하는 박리액의 제거를 위해서 순수로 1분간 세정을 실시하였으며, 세정 후 기판 상에 잔류하는 순수를 제거하기 위하여 질소를 이용하여 기판을 완전히 건조시켰다. 상기 기판의 변성, 또는 경화 레지스트 및 건식 식각 잔사의 제거 성능은 주사 전자현미경(SEM, Hitach S-4700)을 이용하여 확인하고, 그 결과를 하기 표 2에 나타내었다.
Then, the substrate was cleaned with pure water for 1 minute to remove the peeling liquid remaining on the substrate, and the substrate was completely dried with nitrogen to remove pure water remaining on the substrate after cleaning. The denaturation of the substrate or the removal performance of the cured resist and the dry etching residue was confirmed using a scanning electron microscope (SEM, Hitachi S-4700), and the results are shown in Table 2 below.
[박리력 평가 기준][Evaluation criteria for peel strength]
◎: 매우 양호◎: Very good
○: 양호 ○: Good
△: 일부 잔류물 존재, 보통 DELTA: presence of some residues, normal
X: 잔류물 제거 불가, 불량
X: Residual irreversible, defective
시험예Test Example 2. 2. 레지스트Resist 박리액Peeling liquid 조성물의 얼룩 개선 평가 Evaluation of stain improvement of composition
박리 공정을 진행한 후 기판 위에 잔류하는 용해된 레지스트 박리액과 탈이온수의 접촉에 의한 얼룩 정도를 평가하기 위하여, 레지스트가 패턴된 기판을 준비하고 50℃ 상기 실시예 1~10 및 비교예 1~5의 레지스트 박리액 조성물에 기판을 5분간 침적시킨 후 꺼내어 액절을 실시한 후 탈이온수를 접촉 시켜 1분간 방치 시킨 후 탈이온수로 1분간 세정을 실시하였다. 세정 후 기판 상에 잔류하는 탈이온수를 제거하기 위해 질소를 이용하여 기판을 완전히 건조시킨 후 할로겐램프를 이용하여 얼룩 정도를 확인 하였다. 그 결과를 하기 표 1에 나타내었다.In order to evaluate the degree of smear caused by the contact between the dissolved resist stripping liquid and the deionized water remaining on the substrate after the stripping process, a resist patterned substrate was prepared and baked at 50 ° C in the same manner as in Examples 1 to 10, The substrate for 5 minutes was immersed in the resist stripper solution composition for 5 minutes, removed, and subjected to decantation, and then contacted with deionized water for 1 minute, followed by washing with deionized water for 1 minute. After cleaning, the substrate was thoroughly dried with nitrogen to remove deionized water remaining on the substrate, and the degree of staining was confirmed using a halogen lamp. The results are shown in Table 1 below.
[얼룩개선 평가 기준][Evaluation criteria for improvement of stain]
◎: 매우 양호◎: Very good
○: 양호 ○: Good
△: 보통 △: Normal
X: 불량
X: Bad
시험예Test Example 3. 3. 레지스트Resist 박리액Peeling liquid 조성물의 금속 배선 The metal wiring of the composition 방식력Revolution 평가 evaluation
상기 실시예 1~10 및 비교예 1~5의 레지스트 박리액 조성물의 금속배선에 대한 부식 방지능력을 평가하기 위해 하기의 실험을 진행하였다.The following experiments were conducted to evaluate the corrosion inhibiting ability of the resist stripper composition of Examples 1 to 10 and Comparative Examples 1 to 5 on the metal wiring.
상기 실시예 1~10 및 비교예 1~5의 레지스트 박리액 조성물의 온도를 50℃로 온도를 일정하게 유지시킨 뒤, Cu 배선이 노출된 기판을 10분간 침적시켰다. 이후, 세정 및 건조를 거쳐 주사 전자현미경(SEM, Hitach S-4700)을 이용하여 방식력을 확인하였고, 그 결과를 하기 표 2에 나타내었다.
The temperature of the resist stripping solution compositions of Examples 1 to 10 and Comparative Examples 1 to 5 was maintained at a constant temperature of 50 占 폚, and then the substrate on which the Cu wiring was exposed was immersed for 10 minutes. Thereafter, washing and drying were carried out, and a hydrostatic force was confirmed using a scanning electron microscope (SEM, Hitach S-4700). The results are shown in Table 2 below.
[방식력 평가 기준][Evaluation Criteria of Fuel Efficiency]
◎: 부식 없음, 매우 양호◎: No corrosion, very good
○: 부식 거의 없음, 양호○: Almost no corrosion, good
△: 일부 부식, 표면 거칠기 변화, 보통?: Partial corrosion, surface roughness change, normal
×: 부식 및 에칭 발생, 불량
X: Corrosion and etching occurrence, bad
상기 표 2의 실험 결과에 나타난 바와 같이, 본 발명의 박리액 조성물인 실시예 1~10의 경우, Mo/Al/Mo 및 Cu/Ti 배선 형성 기판 모두에서 매우 우수한 박리력을 나타냄을 확인하였다. 또한, Cu 및 Al 금속배선에 대한 방식 효과 역시 매우 우수하였다.As shown in the experimental results of Table 2, it was confirmed that the peeling liquid compositions of Examples 1 to 10 exhibited excellent peel strength in both Mo / Al / Mo and Cu / Ti wiring formation substrates. Also, the etching effect on Cu and Al metal wiring was also excellent.
반면 비교예 1~5의 조성물은, 박리 효과는 본원 발명과 유사하였으나, 얼룩개선 효과에서는 현저한 낮은 효과를 나타냈다. 특히, 비교예 4 및 5의 경우는 3차 알칸올아민이 단독으로 사용되었으나, 본 발명의 실시예와 비교하여 얼룩개선 효과가 낮은 것으로 나타났다. 이러한 결과는 1차와 3차 알칸올아민을 혼합하여 사용하는 경우 얼룩개선에 시너지 효과가 얻어지는 것을 나타낸 것으로 보인다. 비교예 1~5의 조성물은 박리력 및 방식력 평가에서도 좋지 않은 효과를 나타내었다. On the other hand, the compositions of Comparative Examples 1 to 5 exhibited a peeling effect similar to that of the present invention, but showed a remarkably low effect in the improvement of stain. In particular, in the case of Comparative Examples 4 and 5, the tertiary alkanolamine was used alone, but the effect of improving the stain was low as compared with the examples of the present invention. These results show that a synergistic effect is obtained in improving the stain when the primary and tertiary alkanolamines are mixed and used. The compositions of Comparative Examples 1 to 5 exhibited a detrimental effect on the peeling force and the evaluation of the damping force.
Claims (12)
1차 알칸올아민 및 3차 알칸올아민을 포함하는 알칸올아민류(B);
1차 알코올류(C); 및
비양자성 극성용매(D)를 포함하는 레지스트 박리액 조성물:
[화학식 1]
상기 화학식 1에서,
R1 내지 R8은 각각 독립적으로 수소 또는 C1 ~C4의 알킬기이다.
(A) represented by the following general formula (1);
Alkanolamines (B) comprising a primary alkanolamine and a tertiary alkanolamine;
Primary alcohols (C); And
Resist stripper liquid composition comprising aprotic polar solvent (D):
[Chemical Formula 1]
In Formula 1,
R 1 to R 8 are each independently hydrogen or a C 1 to C 4 alkyl group.
상기 화합물(A)은 4-메틸-4,5,6,7-테트라히드로-1H-벤조[1,2,3]트리아졸, 5-메틸-4,5,6,7-테트라히드로-1H-벤조[1,2,3]트리아졸, 5,6-디메틸-4,5,6,7-테트라히드로-1H-벤조[1,2,3]트리아졸 및 4,6-디메틸-4,5,6,7-테트라히드로-1H-벤조[1,2,3]트리아졸로 이루어진 군으로부터 선택되는 1종 또는 2종 이상인 것을 특징으로 하는 레지스트 박리액 조성물.
The method according to claim 1,
The compound (A) can be obtained by reacting 4-methyl-4,5,6,7-tetrahydro-1H-benzo [1,2,3] triazole, 5-methyl-4,5,6,7-tetrahydro-1H -Benzo [1,2,3] triazole, 5,6-dimethyl-4,5,6,7-tetrahydro-1H-benzo [1,2,3] triazole and 4,6- 5,6,7-tetrahydro-1H-benzo [1,2,3] triazole.
조성물 총 중량에 대하여
하기 화학식 1로 표시되는 화합물(A) 0.0001 내지 0.1 중량%; 1차 알칸올아민 및 3차 알칸올아민을 포함하는 알칸올아민류(B) 0.01 내지 10 중량%; 1차 알코올류(C) 20 내지 85 중량%; 및 비양자성 극성용매(D) 5 내지 75 중량%를 포함하는 레지스트 박리액 조성물.
The method according to claim 1,
About the total weight of the composition
0.0001 to 0.1% by weight of a compound (A) represented by the following formula (1); 0.01 to 10% by weight of alkanolamines (B) containing a primary alkanolamine and a tertiary alkanolamine; 20 to 85% by weight of primary alcohols (C); And 5 to 75% by weight of an aprotic polar solvent (D).
상기 알칸올아민류(B)는 1차 알칸올아민과 3차 알칸올아민을 1:0.1 ~ 0.1:1의 중량비로 포함하는 것을 특징으로 하는 레지스트 박리액 조성물.
The method of claim 3,
Wherein the alkanolamines (B) comprise a primary alkanolamine and a tertiary alkanolamine in a weight ratio of 1: 0.1 to 0.1: 1.
상기 1차 알코올류(C)는 알킬렌글리콜계 1차 알코올과 상기 알킬렌글리콜계 1차 알코올류를 제외한 1차 알코올을 1:0.1 ~ 0.1:1의 중량비로 포함하는 것을 특징으로 하는 레지스트 박리액 조성물.
The method of claim 3,
Wherein the primary alcohol (C) comprises an alkylene glycol primary alcohol and a primary alcohol excluding the alkylene glycol primary alcohol at a weight ratio of 1: 0.1 to 0.1: 1. / RTI >
상기 1차 알칸올아민은 모노에탄올아민, 이소프로판올아민, 및 2-(2-아미노에톡시)에탄올로 이루어진 군으로부터 선택되는 1종 이상이며,
상기 3차 알칸올아민은 메틸디에탄올아민, 디메틸에탄올아민, 및 트리에탄올아민으로 이루어진 군으로부터 선택되는 1종 이상인 것을 특징으로 하는 레지스트 박리액 조성물.
The method of claim 4,
The primary alkanolamine is at least one selected from the group consisting of monoethanolamine, isopropanolamine, and 2- (2-aminoethoxy) ethanol,
Wherein the tertiary alkanolamine is at least one selected from the group consisting of methyldiethanolamine, dimethylethanolamine, and triethanolamine.
상기 1차 알코올류(C)는 에틸렌글라이콜 모노메틸 에테르, 에틸렌글라이콜 모노에틸 에테르, 에틸렌글라이콜 모노이소프로필 에테르, 에틸렌글라이콜 모노부틸 에테르, 디에틸렌글라이콜 모노메틸 에테르, 디에틸렌글라이콜 모노에틸 에테르, 디에틸렌글라이콜 모노이소프로필 에테르, 디에틸렌글라이콜 모노부틸 에테르, 트리에틸렌글라이콜 모노메틸 에테르, 트리에틸렌글라이콜 모노에틸 에테르, 트리에틸렌글라이콜 모노이소프로필 에테르, 트리에틸렌글라이콜 모노부틸 에테르, 폴리에틸렌글라이콜 모노메틸 에테르, 폴리에틸렌글라이콜 모노부틸 에테르, 디에틸렌글라이콜, 트리에틸렌글라이콜, 아이소프로필글라이콜, 테트라하이드로퍼퓨릴알코올, 하이드록시메틸싸이클로펜텐, 4-하이드록시메틸-1,3-디옥솔란, 2-메틸-4-하이드록시메틸-1,3-디옥솔란, 2,2-디메틸-1,3-디옥솔란-4-메탄올, 1,3-프로판디올, 1,3-부탄디올 및 1,4-부탄디올, 2-메톡시에탄올로 이루어진 군으로부터 선택되는 1종 이상인 것을 특징으로 하는 레지스트 박리액 조성물.
The method according to claim 1,
The primary alcohol (C) is at least one selected from the group consisting of ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether , Diethylene glycol monoethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol Triethylene glycol monobutyl ether, polyethylene glycol monomethyl ether, polyethylene glycol monobutyl ether, diethylene glycol, triethylene glycol, isopropyl glycol, diethylene glycol, triethylene glycol monobutyl ether, Tetrahydroperfuryl alcohol, hydroxymethylcyclopentene, 4-hydroxymethyl-1,3-dioxolane, 2-methyl-4-hydroxymethyl- Dioxolane-4-methanol, 1,3-propanediol, 1,3-butanediol and 1,4-butanediol, 2-methoxyethanol, Wherein the resist stripping liquid composition comprises at least one type of resist stripping liquid composition.
상기 비양자성 극성용매(D)는 피롤리돈 화합물, 이미다졸리디논 화합물, 락톤 화합물, 설폭사이드 화합물, 포스페이트 화합물, 카보네이트 화합물 및 아미드 화합물로 이루어진 군으로부터 선택되는 1종 또는 2종 이상인 것을 특징으로 하는 레지스트 박리액 조성물.
The method according to claim 1,
The aprotic polar solvent (D) is characterized in that it is at least one selected from the group consisting of a pyrrolidone compound, an imidazolidinone compound, a lactone compound, a sulfoxide compound, a phosphate compound, a carbonate compound and an amide compound The resist stripping liquid composition comprising:
부식 방지제 및 탈이온수로 이루어진 군으로부터 선택되는 1종 이상을 추가로 포함하는 것을 특징으로 하는 레지스트 박리액 조성물.
The method according to claim 1,
Wherein the resist stripping liquid composition further comprises at least one selected from the group consisting of a corrosion inhibitor and deionized water.
상기 부식 방지제는 레지스트 박리액 조성물 총 중량에 대하여 3 중량% 이하로 포함되며;
상기 탈이온수는 레지스트 박리액 조성물 총 중량에 대하여 70 중량% 이하로 포함되는 것을 특징으로 하는 레지스트 박리액 조성물.
The method of claim 9,
The corrosion inhibitor is included in an amount of 3% by weight or less based on the total weight of the resist stripper composition;
Wherein the deionized water is contained in an amount of 70 wt% or less based on the total weight of the resist stripper composition.
A method for manufacturing a flat panel display substrate comprising the step of cleaning a flat panel display substrate using the resist stripping liquid composition according to any one of claims 1 to 10.
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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 |
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