JP2004536181A5 - - Google Patents
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- Publication number
- JP2004536181A5 JP2004536181A5 JP2003512356A JP2003512356A JP2004536181A5 JP 2004536181 A5 JP2004536181 A5 JP 2004536181A5 JP 2003512356 A JP2003512356 A JP 2003512356A JP 2003512356 A JP2003512356 A JP 2003512356A JP 2004536181 A5 JP2004536181 A5 JP 2004536181A5
- Authority
- JP
- Japan
- Prior art keywords
- cleaning composition
- dimethyl
- group
- pyrrolidinone
- sterically hindered
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004140 cleaning Methods 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 50
- 239000002904 solvent Substances 0.000 claims description 29
- 150000001408 amides Chemical class 0.000 claims description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 claims description 14
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 13
- 229910021529 ammonia Inorganic materials 0.000 claims description 11
- 239000006184 cosolvent Substances 0.000 claims description 11
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 10
- LTACQVCHVAUOKN-UHFFFAOYSA-N 3-(diethylamino)propane-1,2-diol Chemical compound CCN(CC)CC(O)CO LTACQVCHVAUOKN-UHFFFAOYSA-N 0.000 claims description 9
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 claims description 9
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 230000000269 nucleophilic effect Effects 0.000 claims description 7
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims description 7
- 150000002500 ions Chemical class 0.000 claims description 6
- -1 silicate compound Chemical class 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 0.000 claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 4
- 239000010949 copper Substances 0.000 claims description 4
- 238000001465 metallisation Methods 0.000 claims description 4
- 239000004094 surface-active agent Substances 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 239000002738 chelating agent Substances 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 60
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 40
- 238000000034 method Methods 0.000 claims 29
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- RJLKIAGOYBARJG-UHFFFAOYSA-N 1,3-dimethylpiperidin-2-one Chemical compound CC1CCCN(C)C1=O RJLKIAGOYBARJG-UHFFFAOYSA-N 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 12
- YXHVIDNQBMVYHQ-UHFFFAOYSA-N 1,5-dimethylpiperidin-2-one Chemical compound CC1CCC(=O)N(C)C1 YXHVIDNQBMVYHQ-UHFFFAOYSA-N 0.000 claims 10
- FILVIKOEJGORQS-UHFFFAOYSA-N 1,5-dimethylpyrrolidin-2-one Chemical compound CC1CCC(=O)N1C FILVIKOEJGORQS-UHFFFAOYSA-N 0.000 claims 10
- WDQFELCEOPFLCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound OCCN1CCCC1=O WDQFELCEOPFLCZ-UHFFFAOYSA-N 0.000 claims 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 4
- 239000000758 substrate Substances 0.000 claims 4
- FCKYPQBAHLOOJQ-UWVGGRQHSA-N 2-[[(1s,2s)-2-[bis(carboxymethyl)amino]cyclohexyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)[C@H]1CCCC[C@@H]1N(CC(O)=O)CC(O)=O FCKYPQBAHLOOJQ-UWVGGRQHSA-N 0.000 claims 2
- NFDRPXJGHKJRLJ-UHFFFAOYSA-N edtmp Chemical compound OP(O)(=O)CN(CP(O)(O)=O)CCN(CP(O)(O)=O)CP(O)(O)=O NFDRPXJGHKJRLJ-UHFFFAOYSA-N 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 238000004377 microelectronic Methods 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 2
- 239000006117 anti-reflective coating Substances 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BPUBBGLMJRNUCC-UHFFFAOYSA-N oxygen(2-);tantalum(5+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Ta+5].[Ta+5] BPUBBGLMJRNUCC-UHFFFAOYSA-N 0.000 description 2
- 229910001936 tantalum oxide Inorganic materials 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- OSNIIMCBVLBNGS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-(dimethylamino)propan-1-one Chemical compound CN(C)C(C)C(=O)C1=CC=C2OCOC2=C1 OSNIIMCBVLBNGS-UHFFFAOYSA-N 0.000 description 1
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 238000004380 ashing Methods 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 229940075419 choline hydroxide Drugs 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- WJZPIORVERXPPR-UHFFFAOYSA-L tetramethylazanium;carbonate Chemical compound [O-]C([O-])=O.C[N+](C)(C)C.C[N+](C)(C)C WJZPIORVERXPPR-UHFFFAOYSA-L 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30431201P | 2001-07-09 | 2001-07-09 | |
| PCT/US2002/021374 WO2003006597A1 (en) | 2001-07-09 | 2002-07-08 | Ammonia-free alkaline microelectronic cleaning compositions with improved substrate compatibility |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004536181A JP2004536181A (ja) | 2004-12-02 |
| JP2004536181A5 true JP2004536181A5 (enExample) | 2006-07-13 |
| JP4177758B2 JP4177758B2 (ja) | 2008-11-05 |
Family
ID=23175967
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003512356A Expired - Fee Related JP4177758B2 (ja) | 2001-07-09 | 2002-07-08 | 基板適合性が改善されたアンモニア不含アルカリ性マイクロエレクトロニクス洗浄組成物 |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1404796B1 (enExample) |
| JP (1) | JP4177758B2 (enExample) |
| KR (2) | KR100944444B1 (enExample) |
| CN (2) | CN102399651A (enExample) |
| AT (1) | ATE545695T1 (enExample) |
| AU (1) | AU2002320305A1 (enExample) |
| BR (1) | BR0211054A (enExample) |
| CA (1) | CA2452884C (enExample) |
| IL (2) | IL159761A0 (enExample) |
| IN (1) | IN2004CH00042A (enExample) |
| MY (1) | MY139607A (enExample) |
| NO (1) | NO20040067L (enExample) |
| PL (1) | PL199501B1 (enExample) |
| RS (1) | RS904A (enExample) |
| TW (1) | TWI292437B (enExample) |
| WO (1) | WO2003006597A1 (enExample) |
| ZA (1) | ZA200400064B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040192938A1 (en) * | 2003-03-24 | 2004-09-30 | Manzer Leo Ernest | Production of 5-mehyl-N-aryl-2-pyrrolidone and 5-methyl-N-alkyl-2-pyrrolidone by reductive of levulinic acid esters with aryl and alkyl amines |
| CN1839355B (zh) | 2003-08-19 | 2012-07-11 | 安万托特性材料股份有限公司 | 用于微电子设备的剥离和清洁组合物 |
| WO2006081406A1 (en) * | 2005-01-27 | 2006-08-03 | Advanced Technology Materials, Inc. | Compositions for processing of semiconductor substrates |
| US7632796B2 (en) | 2005-10-28 | 2009-12-15 | Dynaloy, Llc | Dynamic multi-purpose composition for the removal of photoresists and method for its use |
| US9329486B2 (en) | 2005-10-28 | 2016-05-03 | Dynaloy, Llc | Dynamic multi-purpose composition for the removal of photoresists and method for its use |
| US8263539B2 (en) | 2005-10-28 | 2012-09-11 | Dynaloy, Llc | Dynamic multi-purpose composition for the removal of photoresists and methods for its use |
| ES2356109T3 (es) | 2007-02-14 | 2011-04-05 | Mallinckrodt Baker, Inc. | Formulaciones basadas en oxometalato activadas por peróxido para la eliminación de residuos de grabado. |
| WO2010042457A1 (en) * | 2008-10-09 | 2010-04-15 | Mallinckrodt Baker, Inc. | Aqueous acidic formulations for copper oxide etch residue removal and prevention of copper electrodeposition |
| US8298751B2 (en) | 2009-11-02 | 2012-10-30 | International Business Machines Corporation | Alkaline rinse agents for use in lithographic patterning |
| WO2012161790A1 (en) * | 2011-02-24 | 2012-11-29 | John Moore | Concentrated chemical composition and method for removing photoresist during microelectric fabrication |
| US9158202B2 (en) * | 2012-11-21 | 2015-10-13 | Dynaloy, Llc | Process and composition for removing substances from substrates |
| US10072237B2 (en) * | 2015-08-05 | 2018-09-11 | Versum Materials Us, Llc | Photoresist cleaning composition used in photolithography and a method for treating substrate therewith |
| CN113439324B (zh) * | 2019-02-15 | 2025-03-04 | 日产化学株式会社 | 清洗剂组合物以及清洗方法 |
| CN113454759A (zh) * | 2019-02-15 | 2021-09-28 | 日产化学株式会社 | 清洗剂组合物以及清洗方法 |
| JP7465951B2 (ja) * | 2019-08-30 | 2024-04-11 | ダウ グローバル テクノロジーズ エルエルシー | フォトレジスト剥離組成物 |
| CN111519190B (zh) * | 2020-05-27 | 2022-03-18 | 湖北兴福电子材料有限公司 | 一种铜制程面板中稳定蚀刻锥角的蚀刻液及稳定方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4744834A (en) * | 1986-04-30 | 1988-05-17 | Noor Haq | Photoresist stripper comprising a pyrrolidinone, a diethylene glycol ether, a polyglycol and a quaternary ammonium hydroxide |
| EP0301044A4 (en) * | 1987-02-05 | 1989-03-29 | Macdermid Inc | ETCHING COMPOSITION FOR PHOTORESERVE. |
| US5091103A (en) * | 1990-05-01 | 1992-02-25 | Alicia Dean | Photoresist stripper |
| US6110881A (en) * | 1990-11-05 | 2000-08-29 | Ekc Technology, Inc. | Cleaning solutions including nucleophilic amine compound having reduction and oxidation potentials |
| DE69333877T2 (de) * | 1992-07-09 | 2006-06-14 | Ekc Technology Inc | Reinigungsmittelzusammensetzung, das einem Redox Aminverbindung enthält |
| JPH0959689A (ja) * | 1995-08-29 | 1997-03-04 | Mitsubishi Chem Corp | 研削剤除去用洗浄剤 |
| AU4189599A (en) | 1998-05-18 | 1999-12-06 | Mallinckrodt, Inc. | Silicate-containing alkaline compositions for cleaning microelectronic substrates |
| JP4565741B2 (ja) * | 1998-05-18 | 2010-10-20 | マリンクロッド・ベイカー・インコーポレイテッド | マイクロエレクトロニクス基板洗浄用珪酸塩含有アルカリ組成物 |
| US6558879B1 (en) * | 2000-09-25 | 2003-05-06 | Ashland Inc. | Photoresist stripper/cleaner compositions containing aromatic acid inhibitors |
-
2002
- 2002-07-05 MY MYPI20022558A patent/MY139607A/en unknown
- 2002-07-08 CN CN2010102990065A patent/CN102399651A/zh active Pending
- 2002-07-08 BR BR0211054-7A patent/BR0211054A/pt not_active IP Right Cessation
- 2002-07-08 RS YUP-9/04A patent/RS904A/sr unknown
- 2002-07-08 JP JP2003512356A patent/JP4177758B2/ja not_active Expired - Fee Related
- 2002-07-08 IL IL15976102A patent/IL159761A0/xx active IP Right Grant
- 2002-07-08 PL PL367838A patent/PL199501B1/pl not_active IP Right Cessation
- 2002-07-08 KR KR1020097008556A patent/KR100944444B1/ko not_active Expired - Lifetime
- 2002-07-08 AT AT02749817T patent/ATE545695T1/de active
- 2002-07-08 CA CA2452884A patent/CA2452884C/en not_active Expired - Fee Related
- 2002-07-08 CN CNA028138759A patent/CN1526007A/zh active Pending
- 2002-07-08 AU AU2002320305A patent/AU2002320305A1/en not_active Abandoned
- 2002-07-08 KR KR20047000266A patent/KR20040018437A/ko not_active Ceased
- 2002-07-08 WO PCT/US2002/021374 patent/WO2003006597A1/en not_active Ceased
- 2002-07-08 EP EP02749817A patent/EP1404796B1/en not_active Expired - Lifetime
- 2002-07-09 TW TW091115168A patent/TWI292437B/zh not_active IP Right Cessation
-
2004
- 2004-01-06 ZA ZA200400064A patent/ZA200400064B/en unknown
- 2004-01-07 IL IL159761A patent/IL159761A/en not_active IP Right Cessation
- 2004-01-08 IN IN42CH2004 patent/IN2004CH00042A/en unknown
- 2004-01-08 NO NO20040067A patent/NO20040067L/no not_active Application Discontinuation
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