KR20180093783A - Cleaning solution composition - Google Patents
Cleaning solution composition Download PDFInfo
- Publication number
- KR20180093783A KR20180093783A KR1020170149388A KR20170149388A KR20180093783A KR 20180093783 A KR20180093783 A KR 20180093783A KR 1020170149388 A KR1020170149388 A KR 1020170149388A KR 20170149388 A KR20170149388 A KR 20170149388A KR 20180093783 A KR20180093783 A KR 20180093783A
- Authority
- KR
- South Korea
- Prior art keywords
- minutes
- mask
- polar solvent
- cleaning
- cleaning liquid
- Prior art date
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- 238000004140 cleaning Methods 0.000 title claims abstract description 75
- 239000000203 mixture Substances 0.000 title claims abstract description 42
- 239000000126 substance Substances 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 17
- 230000008569 process Effects 0.000 claims abstract description 11
- 150000001408 amides Chemical class 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 239000007788 liquid Substances 0.000 claims description 37
- 239000002798 polar solvent Substances 0.000 claims description 28
- -1 amide compound Chemical class 0.000 claims description 22
- 239000011368 organic material Substances 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 10
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- LBVMWHCOFMFPEG-UHFFFAOYSA-N 3-methoxy-n,n-dimethylpropanamide Chemical compound COCCC(=O)N(C)C LBVMWHCOFMFPEG-UHFFFAOYSA-N 0.000 claims description 3
- GXMIHVHJTLPVKL-UHFFFAOYSA-N n,n,2-trimethylpropanamide Chemical compound CC(C)C(=O)N(C)C GXMIHVHJTLPVKL-UHFFFAOYSA-N 0.000 claims description 3
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 claims description 3
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 claims description 3
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 claims description 3
- LVYXPOCADCXMLP-UHFFFAOYSA-N 3-butoxy-n,n-dimethylpropanamide Chemical compound CCCCOCCC(=O)N(C)C LVYXPOCADCXMLP-UHFFFAOYSA-N 0.000 claims description 2
- YKOQQFDCCBKROY-UHFFFAOYSA-N n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)CC YKOQQFDCCBKROY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 claims 1
- 238000001771 vacuum deposition Methods 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 45
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 26
- 239000000463 material Substances 0.000 description 22
- 239000011521 glass Substances 0.000 description 20
- 239000010410 layer Substances 0.000 description 14
- 150000002430 hydrocarbons Chemical group 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 230000006866 deterioration Effects 0.000 description 9
- 238000005406 washing Methods 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 6
- 101100269850 Caenorhabditis elegans mask-1 gene Proteins 0.000 description 5
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 5
- 239000003463 adsorbent Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 230000008901 benefit Effects 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000007613 environmental effect Effects 0.000 description 4
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- 229910001374 Invar Inorganic materials 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000005137 deposition process Methods 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 238000004506 ultrasonic cleaning Methods 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- NGQSLSMAEVWNPU-YTEMWHBBSA-N 1,2-bis[(e)-2-phenylethenyl]benzene Chemical compound C=1C=CC=CC=1/C=C/C1=CC=CC=C1\C=C\C1=CC=CC=C1 NGQSLSMAEVWNPU-YTEMWHBBSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- CRFWCCGPRXKZSM-UHFFFAOYSA-N 3,4-methylenedioxy-n-methylphentermine Chemical compound CNC(C)(C)CC1=CC=C2OCOC2=C1 CRFWCCGPRXKZSM-UHFFFAOYSA-N 0.000 description 2
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 102100021792 Gamma-sarcoglycan Human genes 0.000 description 2
- 101000616435 Homo sapiens Gamma-sarcoglycan Proteins 0.000 description 2
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
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- 238000000926 separation method Methods 0.000 description 2
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- 231100000167 toxic agent Toxicity 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- BOHGAOWOIJMTPZ-UHFFFAOYSA-N 1,3-dioxolan-4-ylmethanol Chemical compound OCC1COCO1 BOHGAOWOIJMTPZ-UHFFFAOYSA-N 0.000 description 1
- VERMWGQSKPXSPZ-BUHFOSPRSA-N 1-[(e)-2-phenylethenyl]anthracene Chemical class C=1C=CC2=CC3=CC=CC=C3C=C2C=1\C=C\C1=CC=CC=C1 VERMWGQSKPXSPZ-BUHFOSPRSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- VBQVHWHWZOUENI-UHFFFAOYSA-N 1-phenyl-2H-quinoline Chemical compound C1C=CC2=CC=CC=C2N1C1=CC=CC=C1 VBQVHWHWZOUENI-UHFFFAOYSA-N 0.000 description 1
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 1
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 1
- YYEZYENJAMOWHW-UHFFFAOYSA-N 2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethanol Chemical compound CC1(C)OCC(CCO)O1 YYEZYENJAMOWHW-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- HRWADRITRNUCIY-UHFFFAOYSA-N 2-(2-propan-2-yloxyethoxy)ethanol Chemical compound CC(C)OCCOCCO HRWADRITRNUCIY-UHFFFAOYSA-N 0.000 description 1
- COBPKKZHLDDMTB-UHFFFAOYSA-N 2-[2-(2-butoxyethoxy)ethoxy]ethanol Chemical compound CCCCOCCOCCOCCO COBPKKZHLDDMTB-UHFFFAOYSA-N 0.000 description 1
- WFSMVVDJSNMRAR-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethanol Chemical compound CCOCCOCCOCCO WFSMVVDJSNMRAR-UHFFFAOYSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- FETMDPWILVCFLL-UHFFFAOYSA-N 2-[2-(2-propan-2-yloxyethoxy)ethoxy]ethanol Chemical compound CC(C)OCCOCCOCCO FETMDPWILVCFLL-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- ZPHQFGUXWQWWAA-UHFFFAOYSA-N 9-(2-phenylphenyl)carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 ZPHQFGUXWQWWAA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
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- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents ; Methods for using cleaning compositions
- C11D11/0005—Special cleaning or washing methods
- C11D11/0011—Special cleaning or washing methods characterised by the objects to be cleaned
- C11D11/0023—"Hard" surfaces
- C11D11/0047—Electronic devices, e.g. PCBs or semiconductors
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/32—Organic compounds containing nitrogen
- C11D7/3263—Amides or imides
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
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- C11D2111/22—
Abstract
Description
본 발명은 마스크 세정액 조성물, 구체적으로 증착 공정에서 사용되는 마스크 상의 각종 유기물을 제거하는 마스크 세정액 조성물에 관한 것이다.The present invention relates to a mask cleaning liquid composition, and more particularly, to a mask cleaning liquid composition for removing various organic substances on a mask used in a deposition process.
평판 디스플레이(flat panel display, FPD)는 표시장치로서 주목받고 있으며, 그 중에서도 액정표시장치와 OLED(Organic Light Emitting Diode)가 관심의 대상이 되고 있다.Flat panel displays (FPDs) are attracting attention as display devices, and liquid crystal displays and organic light emitting diodes (OLEDs) are of particular interest.
현재 디스플레이로서 가장 많이 사용되고 있는 액정표시장치는, 기존의 CRT (Cathode ray tube; 음극선관)에 비해 가볍고 부피가 작으며 저전력 등의 장점을 가지고 있다. 그러나 자체발광이 아니기 때문에 후면광(Backlight)을 사용하여야 하며, 액정을 사용하여 시야각이 제한을 받는 단점이 있다.Liquid crystal display devices, which are currently used as displays, are lighter, smaller in volume, and have lower power than conventional CRTs (cathode ray tubes). However, since it is not self-luminous, it is necessary to use a backlight, and a viewing angle is limited by using a liquid crystal.
이에 비해 OLED 소자는 저전압구동, 높은 발광 효율, 넓은 시야각, 빠른 응답속도 등의 장점이 있으며, 무엇보다도 자체발광형이기 때문에 후면광 등이 필요하지 않은 장점이 있다. 이러한 OLED 소자는 자체발광을 하는 발광 유기물을 사용하여 음극과 양극으로부터 공급된 전자와 정공이 재결합되면서 발광이 일어나게 된다.In contrast, OLED devices have advantages such as low voltage driving, high luminous efficiency, wide viewing angle, and fast response speed. Such an OLED device emits light by recombining electrons and holes supplied from a cathode and an anode using a luminescent organic material that emits light.
이런 OLED와 같은 반도체 디바이스 또는 평판 디스플레이는 제조 공정 중 각종 발광층, 정공 주입층, 정공 수송층, 전자 수송층, 전자 주입층 등과 같은 유기물층을 형성하기 위하여 마스크를 이용하여 유기물의 증착을 수행하게 된다. 이때, 마스크의 표면에도 유기물이 부착되게 되며, 이렇게 부착된 유기물로 인하여 마스크로 형성된 패턴의 형상이 변형될 수 있다. 이는, 증착공정의 효율 저하를 야기하며, 제조되는 반도체 디바이스 또는 평판 디스플레이의 성능에도 영향을 미칠 수 있으므로, 마스크에 증착된 유기물을 제거해야 할 필요가 있다.A semiconductor device such as an OLED or a flat panel display performs deposition of an organic material using a mask in order to form organic layers such as various light emitting layers, hole injecting layers, hole transporting layers, electron transporting layers, and electron injecting layers in the manufacturing process. At this time, the organic material adheres to the surface of the mask, and the shape of the pattern formed by the mask can be deformed due to the attached organic material. This causes a reduction in the efficiency of the deposition process and may also affect the performance of the semiconductor device or the flat panel display to be produced, so that it is necessary to remove the organic substances deposited on the mask.
대한민국 공개특허 제2011-0095814호는 증착 재료 세정액 조성물 및 이를 이용한 세정 방법에 관한 것으로서, N-메틸-2-피롤리돈(N-Methyl-2-pyrrolidone); 및 1,3-디메틸-2-이미다졸리디논(1,3-Dimethyl-2-imidazolidinone)을 포함하는 증착 재료 세정액 조성물에 관한 내용을 개시하고 있다.Korean Patent Laid-Open Publication No. 2011-0095814 relates to an evaporation material cleaning liquid composition and a cleaning method using the same, wherein N-methyl-2-pyrrolidone; And 1, 3-dimethyl-2-imidazolidinone. The present invention relates to a detergent cleaning liquid composition containing 1,3-dimethyl-2-imidazolidinone.
대한민국 등록특허 제1388283호는 마스크 세정장치에 관한 것으로서, 초음파를 발생시켜 세정액에 잠겨있는 마스크를 세정하는 초음파 세정부; 상기 초음파 세정부의 세정액 배출과 공급을 위한 세정액 순환부를 포함하고, 상기 초음파 세정부에서의 초음파는 주파수가 75KHz이상 90KHz이하이며, 세기가 800W이상 1100W이하이고, 상기 세정액은 NMP(N-Methyl Pyrrolidinone; N-메틸피롤리딘온) 혼합물인 것을 특징으로 하는 마스크 세정장치에 관한 내용을 개시하고 있다.KOKAI Publication No. 1388283 relates to a mask cleaning apparatus, which comprises an ultrasonic cleaning unit for generating ultrasonic waves to clean a mask immersed in a cleaning liquid; And a cleaning liquid circulating part for discharging and supplying the cleaning liquid of the ultrasonic cleaning part, wherein the ultrasonic wave in the ultrasonic cleaning part has a frequency of 75 KHz to 90 KHz, an intensity of 800 W to 1100 W, and the cleaning liquid contains N-methyl pyrrolidinone ; N-methylpyrrolidinone) mixture. The present invention relates to a mask cleaning apparatus.
그러나, 종래 마스크 세정액에 사용되던 N-메틸-2-피롤리돈(NMP)은 유독물질로서, 구체적으로 국립환경과학원 제2014-25호에 따르면 0.3 중량% 이상 함유시 유독물로 분류되는 물질이다. NMP가 포함된 마스크 세정액을 사용할 경우 인체에 유해할 뿐만 아니라 환경적인 측면에서도 좋지 않다.However, N-methyl-2-pyrrolidone (NMP) which has been conventionally used as a mask cleaning liquid is a toxic substance, and is classified as a toxic substance when it is contained in an amount of 0.3% by weight or more according to National Institute of Environmental Research No. 2014-25. The use of a mask cleaning liquid containing NMP is not only harmful to the human body but also environmentally unfavorable.
또한, 마스크 세정 공정은 제조 공정 상황에 따라 가동 시간이 결정 되는 관계로 대기 상태에서 장기 보관 후 성능 저하가 발생 하지 않아야 한다. 특히 대기 중에 노출 되는 관계로 수분 흡수에 대하여 성능 저하가 발생 하지 않아야 한다. In addition, since the operation time is determined according to the manufacturing process conditions, the mask cleaning process should not cause deterioration in performance after long-term storage in the standby state. In particular, it should not cause deterioration in performance against moisture absorption due to exposure to air.
그러므로, NMP와 같은 환경규제물질을 포함하지 않으면서도, 세정력이 우수하고 수분 흡수에 따른 성능 저하가 발생하지 않으며, 공정 운전에 용이한 마스크 세정액의 개발이 요구되고 있다.Therefore, development of a mask cleaning liquid which is excellent in cleaning power and does not cause deterioration in performance due to moisture absorption, and which is easy to operate in a process, is demanded, even if it does not contain environmental control substances such as NMP.
본 발명의 목적은 환경규제물질을 포함하지 않고도 양호한 세정력을 나타내는 세정액 조성물을 제공하는 데 있다.It is an object of the present invention to provide a cleaning liquid composition which exhibits good cleaning power without containing environmentally regulating substances.
또한, 본 발명의 목적은 초음파 및 전해 세정이 불필요하며 안정성이 우수하여 공정 운전에 용이한 세정액 조성물을 제공하는 데 있다. Another object of the present invention is to provide a cleaning liquid composition which is free from ultrasonic waves and electrolytic cleaning and is excellent in stability and is easy to operate in a process.
상기 목적을 달성하기 위한 본 발명의 세정액 조성물은 하기 화학식 1로 표시되는 아미드계 화합물을 포함하는 것을 특징으로 한다.In order to achieve the above object, the cleaning liquid composition of the present invention comprises an amide compound represented by the following general formula (1).
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
R1 및 R2는 각각 독립적으로 메틸기 또는 에틸기이고,R1 and R2 are each independently a methyl group or an ethyl group,
R3는 수소; 또는 C1 내지 C4의 알콕시기로 치환 또는 비치환된 C1 내지 C4의 포화 또는 불포화 탄화수소기;이며,R3 is hydrogen; Or a C1 to C4 saturated or unsaturated hydrocarbon group substituted or unsubstituted with C1 to C4 alkoxy groups,
단, R1 및 R2가 메틸기인 경우,Provided that when R1 and R2 are methyl groups,
R3는 C1 내지 C4의 알콕시기로 치환 또는 비치환된 C2 내지 C4의 포화 또는 C1 내지 C4의 불포화 탄화수소기이다.R3 is a C2 to C4 saturated or C1 to C4 unsaturated hydrocarbon group substituted or unsubstituted with an alkoxy group of C1 to C4.
본 발명에 따른 마스크 세정액 조성물은 NMP와 같은 환경규제물질을 포함하지 않고도 양호한 세정력을 나타낼 수 있어 공정 운전에 용이한 이점이 있다.The cleaning composition according to the present invention can exhibit a good washing power without containing an environmental control substance such as NMP, which is advantageous in operation of the process.
또한, 본 발명에 따른 마스크 세정액 조성물은 수분 흡수에 따른 성능 저하가 억제되는 이점이 있다.In addition, the cleaning composition for a mask according to the present invention has an advantage that performance deterioration due to moisture absorption is suppressed.
또한, 본 발명에 따른 마스크 세정액 조성물을 이용하여 마스크를 세정할 경우 초음파 및 전해 세정이 불필요한 이점이 있다.Further, when the mask is cleaned using the mask cleaning liquid composition according to the present invention, ultrasonic waves and electrolytic washing are not necessary.
도 1 및 2는 마스크 세정액 흡습율 및 저장 안정성 평가에 따른 글래스를 예시한 도이다.1 and 2 are diagrams illustrating glass according to evaluation of moisture absorption rate and storage stability of a mask cleaning liquid.
이하, 본 발명에 대하여 더욱 상세히 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명에서 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.When a member is referred to as being " on "another member in the present invention, this includes not only when a member is in contact with another member but also when another member exists between the two members.
본 발명에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성요소를 더 포함할 수 있는 것을 의미한다.Whenever a part is referred to as "including " an element in the present invention, it is to be understood that it may include other elements as well, without departing from the other elements unless specifically stated otherwise.
본 발명의 한 양태는, 하기 화학식 1로 표시되는 아미드계 화합물을 포함하는 마스크 세정액 조성물에 관한 것이다.One aspect of the present invention relates to a mask cleaning liquid composition comprising an amide compound represented by the following general formula (1).
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
R1 및 R2는 각각 독립적으로 메틸기 또는 에틸기이고,R1 and R2 are each independently a methyl group or an ethyl group,
R3는 수소; 또는 C1 내지 C4의 알콕시기로 치환 또는 비치환된 C1 내지 C4의 포화 또는 불포화 탄화수소기;이며,R3 is hydrogen; Or a C1 to C4 saturated or unsaturated hydrocarbon group substituted or unsubstituted with C1 to C4 alkoxy groups,
단, R1 및 R2가 메틸기인 경우,Provided that when R1 and R2 are methyl groups,
R3는 C1 내지 C4의 알콕시기로 치환 또는 비치환된 C2 내지 C4의 포화 또는 C1 내지 C4의 불포화 탄화수소기이다.R3 is a C2 to C4 saturated or C1 to C4 unsaturated hydrocarbon group substituted or unsubstituted with an alkoxy group of C1 to C4.
본 발명에서 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 4인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present invention, the alkoxy group may be linear, branched or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 4 carbon atoms. Specific examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy and the like.
본 발명에서 포화 탄화수소기는 상기 탄소수를 만족하는 직쇄 또는 분지쇄 및 환상의 어느 것일 수 있다. In the present invention, the saturated hydrocarbon group may be any one of straight chain, branched chain and cyclic groups satisfying the above-mentioned carbon number.
상기 직쇄 또는 분지쇄의 포화 탄화수소기로는, 메틸기, 에틸기, 프로필기, 부틸기 등의 직쇄상 알킬기; 이소프로필기, 이소부틸기 등의 분지쇄상 알킬기 등을 들 수 있다. 상기 포화 탄화수소기는 바람직하게는 탄소수 1 내지 4이며, 더욱 바람직하게는 탄소수 1 내지 3이다. 단, R1 및 R2가 모두 메틸기인 경우, 상기 포화 탄화수소기의 탄소수는 2 내지 4이다.Examples of the linear or branched saturated hydrocarbon group include straight chain alkyl groups such as methyl, ethyl, propyl and butyl; And branched alkyl groups such as isopropyl and isobutyl groups. The saturated hydrocarbon group preferably has 1 to 4 carbon atoms, more preferably 1 to 3 carbon atoms. Provided that when R1 and R2 are all methyl groups, the number of carbon atoms in the saturated hydrocarbon group is 2 to 4;
상기 환상의 포화 탄화수소기로는 시클로프로필기, 시클로부틸기 등을 들 수 있다.Examples of the cyclic saturated hydrocarbon group include a cyclopropyl group and a cyclobutyl group.
본 발명에서 불포화 탄화수소기는 말단에 불포화기를 갖는 것으로, 탄소수 1 내지 4의 직쇄형 지방족 불포화 탄화수소기, 분지쇄형 지방족 탄화수소기일 수 있다. 상기 직쇄형 지방족 불포화 탄화수소기는 예컨대 비닐기, 프로페닐기(알릴기), 부티닐기 등을 들 수 있으며, 상기 분지쇄형 불포화 탄화수소기로는 예컨대, 1-메틸프로페닐기, 2-메틸프로페닐기 등을 들 수 있으나 이에 한정되지는 않는다.In the present invention, the unsaturated hydrocarbon group having an unsaturated group at the terminal thereof may be a straight chain aliphatic unsaturated hydrocarbon group having 1 to 4 carbon atoms, or a branched chain aliphatic hydrocarbon group. The straight chain aliphatic unsaturated hydrocarbon group includes, for example, a vinyl group, a propenyl group (allyl group), and a butyryl group. Examples of the branched chain unsaturated hydrocarbon group include 1-methylpropenyl group and 2-methylpropenyl group But is not limited thereto.
본 발명에 따른 마스크 세정액 조성물은 상기 화학식 1로 표시되는 아미드계 화합물 단독(neat) 상태일 수 있다. 요컨대, 본 발명에 따른 마스크 세정액 조성물은 상기 화학식 1로 표시되는 아미드계 화합물로 이루어질 수 있다.The cleaning composition for a mask according to the present invention may be in the neat state of the amide compound represented by the general formula (1). In short, the cleaning composition for a mask according to the present invention may be composed of the amide compound represented by the general formula (1).
본 발명의 일 실시형태에 있어서, 상기 화학식 1로 표시되는 아미드계 화합물은 N,N-디메틸프로피온아미드, N,N-디메틸이소부틸아미드, N,N-디메틸아크릴아미드, N,N-디메틸메타크릴아미드, N,N-디에틸포름아미드, N,N-디에틸아세트아미드, N,N-디에틸프로피온아미드, N,N-디에틸이소부틸아미드, N,N-디에틸아크릴아미드, N,N-디에틸메타크릴아미드, 3-메톡시-N,N-디메틸프로피온아미드 및 3-부톡시-N,N-디메틸프로피온아미드로 이루어진 군에서 선택되는 1 이상일 수 있으며, 예컨대, 단독으로 또는 2종 이상을 혼합하여 사용할 수 있다.In one embodiment of the present invention, the amide compound represented by Formula 1 is at least one selected from the group consisting of N, N-dimethylpropionamide, N, N-dimethylisobutylamide, N, N-dimethylacrylamide, N, N-diethylacetamide, N, N-diethylacetamide, N, N-diethylpropionamide, N, N-diethylisobutylamide, N, , N-diethylmethacrylamide, 3-methoxy-N, N-dimethylpropionamide and 3-butoxy-N, N-dimethylpropionamide, Two or more species may be used in combination.
본 발명에 따른 마스크 세정액 조성물은 상기 화학식 1로 표시되는 아미드계 화합물을 포함하기 때문에 마스크 세정력이 우수하고, 마스크, 예컨대 마스크를 이루고 있는 SUS, Invar 등의 물질에는 데미지를 입히지 않는 이점이 있으며, NMP와 같은 환경유해물질 대신 이용될 수 있기 때문에 환경적인 측면에서도 우수하고 공정적인 측면에서도 용이한 이점이 있다. 구체적으로, 본 발명에 따른 마스크 세정액 조성물은 유기발광소자의 패턴 형성에 사용되는 Invar 재질의 마스크 및 상기 마스크를 지지하는 스테인레스(SUS 304, 316, 420 등) 기재 등에 부식 등과 같은 데미지를 주지 않는 이점이 있다.Since the mask cleaning liquid composition according to the present invention contains the amide-based compound represented by Formula 1, it has an excellent mask cleaning power and has an advantage of not damaging materials such as SUS, Invar, It can be used in place of environmentally harmful substances such as water. Therefore, it is excellent in terms of environment and easy in terms of process. Specifically, the mask cleaning liquid composition according to the present invention has advantages such as a mask of Invar material used for forming a pattern of an organic light emitting element and a stainless steel (SUS 304, 316, 420, etc.) .
요컨대, 본 발명에 따른 마스크 세정액 조성물은 상기 마스크에 부착되어 있는 각종 유기 물질에 대한 세정력이 우수하다.In short, the cleaning composition for a mask according to the present invention is excellent in cleaning ability against various organic materials attached to the mask.
상기 유기 물질은 예컨대, 적색, 녹색 및/또는 청색을 발광하는 발광층, 정공수송층(HTL), 정공주입층(HIL) 등을 이루는 물질일 수 있다. 상기 발광층은 적색, 녹색 및/또는 청색을 발광할 수 있으며 인광 물질 또는 형광 물질로 이루어질 수 있다. 이때 상기 발광 호스트 재료로는 CBP((carbazole-9-yl)biphenyl) 또는 mCP(1,3-bis(carbazol-9-yl)이 사용될 수 있으나, 이에만 한정된 것은 아니다.The organic material may be, for example, a material forming a light emitting layer, a hole transporting layer (HTL), a hole injecting layer (HIL), or the like which emits red, green and / or blue light. The light emitting layer may emit red, green, and / or blue light, and may be formed of a phosphor or a fluorescent material. As the light emitting host material, CBP (carbazole-9-yl) biphenyl or mCP (1,3-bis (carbazol-9-yl) may be used.
적색 발광 도펀트로는 PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum)와 같은 인광 물질이나, Alq3(tris-(8-hydroxyquinoline)aluminum)와 같은 형광 물질 등이 사용될 수 있다.Examples of the red light-emitting dopant include bis (1-phenylisoquinoline) acetylacetonate iridium, PQIr (acac) bis (1-phenylquinoline) acetylacetonate iridium, PQIr (tris (1-phenylquinoline) iridium), PtOEP (octaethylporphyrin platinum ), Or a fluorescent material such as Alq3 (tris- (8-hydroxyquinoline) aluminum) may be used.
녹색 발광 도펀트로는 Ir(ppy)3(fac tris(2-phenylpyridine)iridium)와 같은 인광 물질이나, Alq3(tris-(8-hydroxyquinoline)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. As the green luminescent dopant, a phosphorescent material such as Ir (ppy) 3 (fac tris (2-phenylpyridine) iridium) or a fluorescent material such as Alq3 (tris- (8-hydroxyquinoline) aluminum) may be used. no.
청색 발광 도펀트로는 (4,6-F2ppy)2Irpic와 같은 인광 물질이나, spiro-DPVBi, spiro-6P, 디스틸벤젠(DSB), 디스트릴아릴렌(DSA), PFO계 고분자, PPV계 고분자와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다.Examples of the blue light emitting dopant include phosphors such as (4,6-F 2 ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA) Based polymer may be used, but the present invention is not limited thereto.
정공수송층은 NPD(N,N'-Di(1-naphthyl)-N,N′'-diphenyl-(1,1'-biphenyl)-4,4'-diamine), TPD(N,N'-bis-(3-methylphenyl)-N,N'-bis-(phenyl)-benzidine), s-TAD 및 MTDATA(4,4',4"- Tris(N-3-methylphenyl-N-phenyl-amino)-triphenylamine)로 이루어진 군에서 선택된 어느 하나 이상으로 이루어질 수 있으나 이에 한정되지 않는다. 예컨대 정공수송층 재료로서 트라이아졸 유도체, 옥사다이아졸 유도체, 이미다졸 유도체, 폴리아릴알케인 유도체, 피라졸린 유도체 및 피라졸론 유도체, 페닐렌다이아민 유도체, 아릴아민 유도체, 아미노 치환 칼콘 유도체, 옥사졸 유도체, 스타이릴안트라센 유도체, 플루오렌온 유도체, 하이드라존 유도체, 스틸벤 유도체, 실라제인 유도체, 폴리실레인계, 아닐린계 공중합체, 도전성 고분자 올리고머(특히 싸이오펜 올리고머) 등을 들 수 있다.The hole transport layer may be formed by a combination of NPD (N, N'-Di (1-naphthyl) -N, N''- diphenyl- (1,1'- biphenyl) -4,4'- diamine), TPD - (3-methylphenyl) -N, N'-bis- (phenyl) -benzidine, s-TAD and MTDATA (4,4 ' triphenylamine), but is not limited thereto. For example, as the hole transport layer material, a triazole derivative, an oxadiazole derivative, an imidazole derivative, a polyarylalkane derivative, a pyrazoline derivative, and a pyrazolone derivative , Phenylene diamine derivatives, arylamine derivatives, amino substituted chalcone derivatives, oxazole derivatives, styryl anthracene derivatives, fluorene derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, polysilanes, And conductive polymer oligomers (especially thiophenol oligomers).
또한, 그 외에도 정공저지층에 포함되는 옥사디졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), 알루미늄 착물 등을 사용할 수 있으며, 정공 주입층에 재료로서 CuPc(copper phthalocyanine), PEDOT(poly(3,4)-ethylenedioxythiophene), PANI(polyaniline) 및 NPD로 이루어진 군에서 선택되는 1 이상이 사용될 수 있다.In addition, oxadiazole derivatives and triazole derivatives, phenanthroline derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, and aluminum complexes, which are included in the hole blocking layer, And one or more selected from the group consisting of CuPc (copper phthalocyanine), PEDOT (poly (3,4) -ethylenedioxythiophene), PANI (polyaniline) and NPD can be used as the material for the hole injection layer.
본 발명의 또 다른 실시형태에 있어서, 상기 마스크 세정액 조성물은 수용성 극성용매를 더 포함할 수 있다.In another embodiment of the present invention, the mask cleaning liquid composition may further comprise a water-soluble polar solvent.
본 발명의 또 다른 실시형태에 있어서, 상기 수용성 극성용매는 양자성 극성용매 및 비양자성 극성용매로 이루어진 군에서 선택되는 1 이상을 포함할 수 있다. In another embodiment of the present invention, the water-soluble polar solvent may include at least one selected from the group consisting of a proton-polar solvent and an aprotic polar solvent.
구체적으로, 본 발명에 따른 수용성 극성용매는 양자성 극성용매와 비양자성 극성용매를 들 수 있으며, 이들을 각각 단독으로 또는 혼합하여 사용할 수 있다.Specifically, the water-soluble polar solvent according to the present invention includes a proton-polar solvent and an aprotic polar solvent, which may be used alone or in combination.
상기 양자성 극성용매는 예컨대 에틸렌글리콜 모노메틸 에테르, 에틸렌글리콜 모노에틸 에테르, 에틸렌글리콜 모노이소프로필 에테르, 에틸렌글리콜 모노부틸 에테르, 디에틸렌글리콜 모노메틸 에테르, 디에틸렌글리콜 모노에틸 에테르, 디에틸렌글리콜 모노이소프로필 에테르, 디에틸렌글리콜 모노부틸 에테르, 트리에틸렌글리콜 모노메틸 에테르, 트리에틸렌글리콜 모노에틸 에테르, 트리에틸렌글리콜 모노이소프로필 에테르, 트리에틸렌글리콜 모노부틸 에테르, 폴리에틸렌글리콜 모노메틸 에테르, 폴리에틸렌글리콜 모노부틸 에테르, 프로필렌글리콜 모노메틸 에테르, 디프로필렌글리콜 모노메틸 에테르, 트리프로필렌글리콜 모노메틸 에테르 등의 알킬렌글리콜 모노알킬 에테르; 및 테트라하이드로퍼푸릴 알코올; 등을 들 수 있으며, 4-하이드록시메틸-1,3-디옥솔란, 4-하이드록시메틸-2,2-디메틸-1,3-디옥솔란, 4-하이드록시에틸-2,2-디메틸-1,3-디옥솔란, 4-하이드록시프로필-2,2-디메틸-1,3-디옥솔란, 4-하이드록시부틸-2,2-디메틸-1,3-디옥솔란, 4-하이드록시메틸-2,2-디에틸-1,3-디옥솔란, 4-하이드록시메틸-2-메틸-2-에틸-1,3-디옥솔란 등의 하이드록시 디옥솔란계 화합물;을 들 수 있으며 이들은 1종 단독으로 또는 2종 이상이 함께 사용될 수 있으나, 이에 한정되지는 않으며 당업계에서 통상적으로 사용되고, 본 발명의 목적을 저해하지 않는 양자성 극성용매를 사용할 수 있다.The protonic polar solvent includes, for example, 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 mono Isopropyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monoisopropyl ether, triethylene glycol monobutyl ether, polyethylene glycol monomethyl ether, polyethylene glycol monobutyl Alkylene glycol monoalkyl ethers such as ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether and tripropylene glycol monomethyl ether; And tetrahydroperfuryl alcohol; 4-hydroxymethyl-2,2-dimethyl-1,3-dioxolane, 4-hydroxyethyl-2,2-dimethyl- 1,3-dioxolane, 4-hydroxypropyl-2,2-dimethyl-1,3-dioxolane, 4-hydroxybutyl-2,2- Hydroxy-2-ethyl-1,3-dioxolane, and the like, which can be represented by the formula May be used singly or in combination of two or more. However, the present invention is not limited thereto, and a protonic polar solvent which is commonly used in the art and which does not hinder the object of the present invention may be used.
상기 비양자성 극성용매는 예컨대 예로는 γ―부티로락톤 등의 락톤 화합물; 디메틸술폭사이드(DMSO), 술폴란 등의 설폭사이드 화합물; 트리에틸포스페이트, 트리부틸포스페이트 등의 포스페이트 화합물; 디메틸카보네이트, 에틸렌카보네이트, 프로필렌카보네이트 등의 카보네이트 화합물을 들 수 있으며, 이들은 단독으로 또는 2종 이상을 혼합하여 사용할 수 있으나, 역시 이에 한정되지 않는다.Examples of the aprotic polar solvent include lactone compounds such as? -Butyrolactone; Sulfoxide compounds such as dimethylsulfoxide (DMSO) and sulfolane; Phosphate compounds such as triethyl phosphate, tributyl phosphate and the like; And carbonate compounds such as dimethyl carbonate, ethylene carbonate and propylene carbonate. These may be used alone or as a mixture of two or more thereof. However, the present invention is not limited thereto.
상기 수용성 극성용매는 상기 화학식 1로 표시되는 아미드계 화합물과 함께 마스크에 잔류하는 유기소재를 용해 시키는 역할을 수행하며, 또한 세정 후 탈이온수의 린스 과정에서 물에 의한 세정액 제거를 수월하게 하여 제거된 유기소재의 재흡착/재부착을 최소화하거나 특정 유기소재의 제거력 향상에 구현할 수 있는 역할을 수행할 수 있다.The water-soluble polar solvent serves to dissolve the organic material remaining in the mask together with the amide compound represented by the formula (1). Further, the water-soluble polar solvent easily removes the cleaning liquid by water during the rinsing of the deionized water after cleaning, It is possible to minimize the re-adsorption / re-adhesion of the organic material or to improve the removing power of the specific organic material.
상기 수용성 극성용매는 추후 세정 공정에서 요구되는 성능에 따라 선택될 수 있으며, 상기 수용성 극성용매는 적당한 세정력 및 공정의 안정적 운영을 위해 비점이 낮지 않은 것이 바람직하다. 예컨대 150 내지 290 ℃의 비점을 가지는 것이 바람직하다. 상기 범위 내의 비점을 가지는 수용성 극성 용매를 사용하는 경우 환경적, 공정적인 측면에서 바람직할 수 있다. The water-soluble polar solvent may be selected according to the performance required in a subsequent washing process, and it is preferable that the water-soluble polar solvent has a low boiling point for proper washing power and stable operation of the process. It is preferable to have a boiling point of 150 to 290 deg. When a water-soluble polar solvent having a boiling point within the above range is used, it may be preferable from the viewpoint of environmental and processability.
상기 수용성 용매의 비점이 낮은 경우 세정 공정에서 휘발되어 공정 사용량이 많아 지고 작업 환경에 악영향을 미칠 수 있으므로 상기 범위 내의 비점을 가지는 수용성 극성 용매를 사용하는 것이 바람직하다.If the boiling point of the water-soluble solvent is low, it may be volatilized in the cleaning process to increase the amount of the process used and adversely affect the working environment. Therefore, it is preferable to use a water-soluble polar solvent having a boiling point within the above range.
본 발명의 또 다른 실시형태에 있어서, 상기 수용성 극성용매는 상기 세정액 조성물 전체 100 중량부에 대하여 1 내지 50 중량부, 바람직하게는 5 내지 40 중량부, 더욱 바람직하게는 5 내지 30 중량부로 포함될 수 있다. 상기 수용성 극성용매가 상기 범위 내로 포함될 경우 세정력이 우수하면서도, 세정 후 탈이온스의 린스 과정에서 제거가 용이한 세정액 조성물을 제조할 수 있는 이점이 있으므로 바람직하다.In another embodiment of the present invention, the water-soluble polar solvent may be contained in an amount of 1 to 50 parts by weight, preferably 5 to 40 parts by weight, more preferably 5 to 30 parts by weight, based on 100 parts by weight of the total of the cleaning liquid composition have. When the water-soluble polar solvent is contained within the above-mentioned range, the cleaning liquid composition having an excellent detergency and being easy to remove during the rinse of the deionized water after cleaning is advantageous.
본 발명에 따른 세정액 조성물은 상기 화학식 1로 표시되는 아미드계 화합물을 포함하여 우수한 세정력을 가지기 때문에 초음파 및 전해 세정 등이 불필요한 이점이 있다.The cleaning liquid composition according to the present invention has an excellent cleaning power including the amide compound represented by the above formula (1), so that it is advantageous that ultrasonic waves and electrolytic washing are not necessary.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 들어 상세히 설명한다. 그러나, 본 명세서에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되지는 않는다. 본 명세서의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다. 또한, 이하에서 함유량을 나타내는 "%" 및 "부"는 특별히 언급하지 않는 한 중량 기준이다.Hereinafter, the present invention will be described in detail by way of examples to illustrate the present invention. However, the embodiments according to the present disclosure can be modified in various other forms, and the scope of the present specification is not construed as being limited to the above-described embodiments. Embodiments of the present disclosure are provided to more fully describe the present disclosure to those of ordinary skill in the art. In the following, "%" and "part" representing the content are by weight unless otherwise specified.
실시예Example 및 And 비교예Comparative Example : 세정액 조성물의 제조: Preparation of Cleaning Solution Composition
하기 표 1의 구성 및 조성에 따라 실시예 및 비교예에 따른 세정액 조성물을 제조하였다.The cleaning liquid compositions according to Examples and Comparative Examples were prepared according to the compositions and compositions shown in Table 1 below.
DMIB: N,N-디메틸이소부틸아미드
DMAR: N,N-디메틸아크릴아미드
DEAC: N,N-디에틸아세트아미드
MDMP: 3-메톡시-N,N-디메틸프로피온아미드
EDG: 디에틸렌글리콜 모노에틸 에테르
HMD: 4-하이드록시메틸-1,3-디옥솔란
PC: 프로필렌카보네이트
NMF: N-메틸포름아미드
NEF: N-에틸포름아미드
NMPA: N-메틸프로피온아미드
DMDA: N,N-디메틸데칸아미드
DMF: N,N-디메틸포름아미드
DMAC: N, N-디메틸아세트아미드
NMP: N-메틸-2-피롤리돈
DMI: 1,3-디메틸-2-이미다조리디논
DMSO: 디메틸 설폭사이드DMPA: N, N-dimethylpropionamide
DMIB: N, N-dimethylisobutylamide
DMAR: N, N-dimethylacrylamide
DEAC: N, N-diethylacetamide
MDMP: 3-methoxy-N, N-dimethylpropionamide
EDG: diethylene glycol monoethyl ether
HMD: 4-hydroxymethyl-1,3-dioxolane
PC: propylene carbonate
NMF: N-methylformamide
NEF: N-ethylformamide
NMPA: N-methylpropionamide
DMDA: N, N-Dimethyldecanamide
DMF: N, N-dimethylformamide
DMAC: N, N-dimethylacetamide
NMP: N-methyl-2-pyrrolidone
DMI: 1,3-dimethyl-2-imidazolidinone
DMSO: dimethylsulfoxide
실험예Experimental Example 1: 유기소재 흡착 마스크 세정력 평가 1: Evaluation of organic material adsorption mask cleaning force
실시예 및 비교예에 따른 마스크 세정액 조성물의 세정 효과를 확인하기 위하여 통상적인 방법에 따라 유기발광소자에 포함되는 발광층 및 전자/정공 수송층으로 사용되는 물질이 각각 별도로 흡착된 5종의 마스크(재질: Invar)에 대한 세정력 평가를 실시하였다. 제조한 마스크 세정액 조성물을 항온조를 이용하여 50 ℃로 승온 후 마스크 세정액 조성물(약액)을 교반하였다. 교반되고 있는 마스크 세정액 조성물에 2×2 cm 사이즈로 절단된 유기소재가 흡착된 마스크를 침적후 탈이온수로 1분 세정하여 SEM(주사현미경, Hitachi-4800) 을 이용하여 마스크 표면에 유기소재의 잔류 유무를 판단하여 세정력을 평가하였다. 마스크 세정액 침적 시간은 5분 단위로 진행되었으며, 마스크 표면에 잔류물이 잔류하지 않는 시간을 표시하여 세정력을 평가하였으며, 그 결과를 하기 표 2에 나타내었다.In order to confirm the cleaning effect of the mask cleaning liquid composition according to Examples and Comparative Examples, five kinds of masks (material: Invar). After the temperature of the prepared mask cleaning composition was raised to 50 캜 by using a thermostat, the mask cleaning composition (chemical solution) was stirred. A mask having an organic material adsorbed to a size of 2 x 2 cm was immersed in the agitated mask cleaning liquid composition and washed with deionized water for 1 minute, and the organic material remained on the mask surface using an SEM (Scanning Microscope, Hitachi-4800) And the detergency was evaluated. The immersion time of the washing liquid for the mask was measured in units of 5 minutes, and the washing time was measured by indicating the time when no residues remained on the surface of the mask. The results are shown in Table 2 below.
Mask 2 흡착 물질: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline(BCP)
Mask 3 흡착 물질: copper phthalocyanine (CuPc)
Mask 4 흡착 물질: tris-(8-hydroxyquinoline)aluminum (Alq3)
Mask 5 흡착 물질: tris(2-phenylpyridine)iridium [Ir(PPy)3]와 (carbazole-9-yl) biphenyl(CBP) 혼합물Mask 1 Adsorbent material: N, N'-Di (1-naphthyl) -N, N'-diphenyl- (1,1'-biphenyl) -4,4'-
Mask 2 Adsorbent material: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP)
Mask 3 Adsorbent material: copper phthalocyanine (CuPc)
Mask 4 Adsorbent material: tris- (8-hydroxyquinoline) aluminum (Alq3)
Mask 5 Adsorbent material: a mixture of tris (2-phenylpyridine) iridium [Ir (PPy) 3 ] and (carbazole-9-yl) biphenyl
표 2를 살펴 보면 화학식 1로 표시되는 아미드계 화합물, 아미드계 화합물 및 수용성 극성 용매를 혼합한 실시예에서는 Mask 1~5 모두 25분 이내로 세정 가능 함을 확인 할 수 있다. In Table 2, it can be confirmed that Mask 1 to 5 can be cleaned within 25 minutes in the embodiment in which the amide compound represented by Chemical Formula 1, the amide compound, and the water-soluble polar solvent are mixed.
하지만 환경 규제 물질을 포함하는 비교예 1을 제외하고는 한 개 이상의 Mask에서 30분 이상으로 세정력이 저하된 것을 확인 할 수 있다.However, except for Comparative Example 1, which contains the environmentally regulated substance, it can be confirmed that the detergency is lowered by more than 30 minutes in one or more masks.
화학식 1에서 R1 및 R2가 메틸기 또는 에틸기가 아닌 아미드계 물질을 사용한 비교예 2~4에서는 Mask 2와 Mask 3의 세정력이 저하된 것을 확인 할 수 있다.In Comparative Examples 2 to 4 in which an amide-based material in which R 1 and R 2 are not a methyl group or an ethyl group in the general formula (1), the cleaning power of Mask 2 and Mask 3 is lowered.
또한 화학식 1에서 R3가 C4 초과인 아미드계 물질의 비교예 5에서는 Mask 1~5의 모든 Mask에서 세정력 저하를 확인 할 수 있으며 R1 및 R2가 메틸기이며 R3가 수소 혹은 C1인 경우 Mask 2, 3에서의 제거력 저하를 확인 할 수 있다.In Comparative Example 5 of the amide-based material in which R 3 is more than C4 in the formula (1), deterioration in all masks of Mask 1 to 5 can be confirmed. When R1 and R2 are methyl groups and R3 is hydrogen or C1, It is possible to confirm the deterioration of the removal force.
또한 화학식 1로 표시되는 아미드계 화합물을 포함하지 않고, 수용성 극성 용매만을 포함한 비교예 8, 9, 10, 11에서도 Mask 세정력 저하를 확인 할 수 있었며, 화학식 1에 포함되지 않는 아미드계 화합물과 극성 용매 혼합물의 비교예 12, 13에서도 세정력 저하를 확인 할 수 있다.Also, in Comparative Examples 8, 9, 10, and 11, which did not include the amide compound represented by Chemical Formula 1 and contained only a water-soluble polar solvent, deterioration of the Mask cleaning power could be confirmed, and the amide compound, Also in Comparative Examples 12 and 13 of the solvent mixture, deterioration of the washing power can be confirmed.
실험예Experimental Example 2: 유기발광소자 용해 안정성 평가 2: Evaluation of dissolution stability of organic light emitting device
증착 공정 후 마스크로부터 유기소재를 분리한 후, 막자 사발을 이용하여 파우더 형태를 만들고 제조한 마스크 세정액 조성물의 중량으로 0.05%의 유기소재를 60℃에서 1시간 용해 후 유리재질의 투명 50ml 유리병으로 분취 후 상온에서 24시간 방치 후 실시예 1, 2, 4, 5, 6, 8, 10 및 비교예 2, 4, 6, 8, 11, 12 에 따른 마스크 세정액 조성물(약액)의 안정성(탁도 증가 및 침전물)을 평가 하여 하기 표 3에 나타내었다.The organic material was separated from the mask after the deposition process, and powdered using a mortar bowl. The organic cleaning solution composition was prepared by dissolving 0.05% of the organic material at 60 ° C for 1 hour in a glass 50 ml glass bottle The stability of the mask cleaning liquid composition (chemical solution) according to Examples 1, 2, 4, 5, 6, 8 and 10 and Comparative Examples 2, 4, 6, 8, 11 and 12 after leaving for 24 hours at room temperature And precipitates) were evaluated and are shown in Table 3 below.
평가 기준은 하기와 같다.The evaluation criteria are as follows.
육안으로 평가 시 약액의 투명도 변화 없음: ◎No change in transparency of the chemical solution when evaluated by naked eye: ◎
육안으로 평가 시 탁도 약간 증가(투명): ○Turbidity slightly increased when evaluated visually (transparent): ○
육안으로 평가 시 탁도 증가(불투명): △Increased turbidity when evaluated visually (opaque): △
육안으로 평가 시 침전물 발생: ×Sediment occurs when evaluated visually: ×
표3을 살펴 보면 화학식 1의 아미드계 화합물 및 수용성 극성 용매를 혼합한 실시예에서는 유기소재가 용해 후 약액의 투명도 변화가 적은 것으로 보아 세정액 내에서 안정성을 보여 기재(Invar, SUS)에 재흡착이 되지 않은 것을 알 수 있다. 그러나, 비교예 2, 4, 6, 8, 11, 12에서는 24시간 방치 후 Mask 2와 Mask 3에서 분리한 유기소재의 용해 후 안정성이 저하되는 것을 확인 할 수 있었다. 따라서, 반복세정 공정에서 세정 횟 수가 증가될 경우 기재에 재흡착 되어 2차 오염을 야기 시킬 수 있는 것을 확인하였다.As shown in Table 3, in the examples in which the amide compound of formula (1) and the water-soluble polar solvent were mixed, the stability of the cleaning solution was evident in view of the small change in the transparency of the chemical solution after dissolution of the organic material. . However, in Comparative Examples 2, 4, 6, 8, 11, and 12, it was confirmed that stability after dissolution of the organic material separated in Mask 2 and Mask 3 after 24 hours of storage was decreased. Therefore, it was confirmed that when the number of cleaning cycles is increased in the repeated cleaning process, the substrate is reabsorbed on the substrate and can cause secondary contamination.
실험예Experimental Example 3: 마스크 세정액 3: Mask cleaning liquid 흡습율Moisture absorption rate 및 저장 안정성 평가 And storage stability evaluation
수분 흡습에 따른 세정 성능 저하를 확인 하기 위해서 마스크 세정액 조성물을 항온조를 이용하여 30 ℃로 승온 후 마스크 세정액 조성물(약액)을 48시간 방치 후 수분 측정기로 수분 함량을 측정 하여 흡습율을 계산 하였으며, 유기소재가 흡착된 Glass를 2×4cm 사이즈로 절단하여 하부의 Glass 부위를 세정액에 침적(Half dip)한 후 탈이온수로 1분 세정 후 UV Lamp(254nm)를 이용하여 육안으로 유기소재의 잔류 유무를 판단하여 세정력을 평가 하였다. 마스크 세정액 침적 기간은 15초 단위로 진행 되었으며, 마스크 표면에 잔류물이 잔류하지 않는 시간을 표시하여 세정력을 평가하였으며, 그 결과를 하기 표 4에 나타내었다. 도 1 및 도 2는 마스크를 UV Lamp 하에서 관찰한 도로, 예컨대, 도 1는 세정액에 침적된 Glass 하부에 유기 증착물이 잔류한 글래스이며, 도 2는 세정액에 침적된 Glass 하부에 유기 증착물이 잔류되지 않는 글래스이다.To ascertain the deterioration of the cleaning performance due to moisture absorption, the mask cleaning composition composition was heated to 30 DEG C using a thermostat, and the moisture content of the mask cleaning composition (chemical solution) was measured by a moisture analyzer for 48 hours. The glass on which the material was adsorbed was cut into a size of 2 × 4 cm and the lower glass part was dipped in the washing liquid. The substrate was rinsed with deionized water for 1 minute, and the residual organic matter was visually observed using a UV lamp (254 nm) And the detergency was evaluated. The duration of the immersion of the cleaning liquid in the mask was 15 seconds, and the cleaning time was measured by indicating the time during which no residues remained on the surface of the mask. The results are shown in Table 4 below. 1 and 2 are views showing a state in which the organic deposition material remains on the lower surface of the glass immersed in the cleaning liquid, and FIG. 2 shows a state in which the organic deposition remains on the glass bottom immersed in the cleaning liquid It is not glass.
(%)Moisture absorption rate
(%)
Glass 2: Green Host와 Dopant가 증착된 Glass
Glass 3: Blue Host와 Dopant가 증착된 Glass
Glass 4: HTL(Hole Transfer Layer)가 증착된 GlassGlass 1: Glass with Red Host and Dopant deposited
Glass 2: Glass with Green Host and Dopant deposited
Glass 3: Glass with Blue Host and Dopant deposited
Glass 4: HTL (Hole Transfer Layer) deposited Glass
상기 표 4를 보면, 화학식 1로 표시되는 아미드계 화합물, 아미드계 화합물 및 수용성 극성 용매를 혼합한 실시예에서는 120초 이내의 빠른 세정력을 보이며, 저장 안정성 평가 후 수분을 2% 미만으로 함유 하고 있으며 세정력 변화를 보이지 않는다.The results are shown in Table 4. In Table 4, the amidic compound, the amide compound and the water-soluble polar solvent represented by the formula (1) showed a rapid cleaning power within 120 seconds and a moisture content of less than 2% No change in cleaning power is seen.
하지만 NMP를 포함한 비교예 1, 8에서는 저장 안정성 평가 후 수분을 7% 이상 함유 하고 있으며 일부 유기 증착물의 제거 속도가 저하됨을 확인 할 수 있었다.However, in Comparative Examples 1 and 8 including NMP, moisture content was 7% or more after storage stability evaluation, and it was confirmed that the removal rate of some organic deposition materials was lowered.
Claims (6)
[화학식 1]
상기 화학식 1에서,
R1 및 R2는 각각 독립적으로 메틸기 또는 에틸기이고,
R3는 수소; 또는 C1 내지 C4의 알콕시기로 치환 또는 비치환된 C1 내지 C4의 포화 또는 불포화 탄화수소기;이며,
단, R1 및 R2가 메틸기인 경우,
R3는 C1 내지 C4의 알콕시기로 치환 또는 비치환된 C2 내지 C4의 포화 또는 C1 내지 C4의 불포화 탄화수소기이다.1. A mask cleaning liquid composition comprising an amide-based compound represented by the following formula (1):
[Chemical Formula 1]
In Formula 1,
R1 and R2 are each independently a methyl group or an ethyl group,
R3 is hydrogen; Or a C1 to C4 saturated or unsaturated hydrocarbon group substituted or unsubstituted with C1 to C4 alkoxy groups,
Provided that when R1 and R2 are methyl groups,
R3 is a C2 to C4 saturated or C1 to C4 unsaturated hydrocarbon group substituted or unsubstituted with an alkoxy group of C1 to C4.
상기 화학식 1로 표시되는 아미드계 화합물은, N,N-디메틸프로피온아미드, N,N-디메틸이소부틸아미드, N,N-디메틸아크릴아미드, N,N-디메틸메타크릴아미드, N,N-디에틸포름아미드, N,N-디에틸아세트아미드, N,N-디에틸프로피온아미드, N,N-디에틸이소부틸아미드, N,N-디에틸아크릴아미드, N,N-디에틸메타크릴아미드, 3-메톡시-N,N-디메틸프로피온아미드 및 3-부톡시-N,N-디메틸프로피온아미드로 이루어진 군에서 선택되는 1 이상인 것인 마스크 세정액 조성물.The method according to claim 1,
The amide compound represented by the general formula (1) may be at least one selected from the group consisting of N, N-dimethylpropionamide, N, N-dimethylisobutylamide, N, N-dimethylacrylamide, N, N-diethylacetamide, N, N-diethylpropionamide, N, N-diethylisobutylamide, N, N-diethylacrylamide, N, , 3-methoxy-N, N-dimethylpropionamide, and 3-butoxy-N, N-dimethylpropionamide.
수용성 극성용매를 더 포함하는 것인 마스크 세정액 조성물.The method according to claim 1,
And a water-soluble polar solvent.
상기 수용성 극성용매는 양자성 극성용매 및 비양자성 극성용매로 이루어진 군에서 선택되는 1 이상을 포함하는 것인 마스크 세정액 조성물.The method of claim 3,
Wherein the water-soluble polar solvent comprises at least one selected from the group consisting of a proton-polar solvent and an aprotic polar solvent.
상기 수용성 극성용매는 상기 세정액 조성물 전체 100 중량부에 대하여 1 내지 50 중량부로 포함되는 것인 마스크 세정액 조성물.The method of claim 3,
Wherein the water-soluble polar solvent is contained in an amount of 1 to 50 parts by weight based on 100 parts by weight of the total of the cleaning liquid composition.
상기 마스크 세정액 조성물은 유기 소재 진공 증착 공정에 사용되는 마스크를 세정하는 것인 마스크 세정액 조성물.The method according to claim 1,
Wherein the mask cleaning liquid composition is used for cleaning a mask used in an organic material vacuum deposition process.
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| KR20240033437A (en) | 2022-09-05 | 2024-03-12 | 재원산업 주식회사 | Composition for cleaning mask with increased stability to decomposition of hydrogen peroxide |
| KR20240033755A (en) | 2022-09-05 | 2024-03-13 | 재원산업 주식회사 | Cleaning composition for orgnic and inorganic materials on deposition mask used in deposition of organic light emitting display device |
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