WO1997003175B1 - Redox reagent-containing post-etch residue cleaning composition - Google Patents
Redox reagent-containing post-etch residue cleaning compositionInfo
- Publication number
- WO1997003175B1 WO1997003175B1 PCT/US1996/010807 US9610807W WO9703175B1 WO 1997003175 B1 WO1997003175 B1 WO 1997003175B1 US 9610807 W US9610807 W US 9610807W WO 9703175 B1 WO9703175 B1 WO 9703175B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cleaner composition
- group
- weight
- redox reagent
- redox
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract 28
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract 13
- 238000004140 cleaning Methods 0.000 title abstract 2
- -1 amine compounds Chemical class 0.000 claims abstract 5
- 150000001413 amino acids Chemical class 0.000 claims abstract 4
- 238000009835 boiling Methods 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000002798 polar solvent Substances 0.000 claims abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 8
- 150000005846 sugar alcohols Chemical class 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims 4
- SEQKRHFRPICQDD-UHFFFAOYSA-N N-tris(hydroxymethyl)methylglycine Chemical compound OCC(CO)(CO)[NH2+]CC([O-])=O SEQKRHFRPICQDD-UHFFFAOYSA-N 0.000 claims 4
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 4
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims 4
- 229950010030 dl-alanine Drugs 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 229940024606 amino acid Drugs 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- HEBKCHPVOIAQTA-NGQZWQHPSA-N D-Arabitol Natural products OC[C@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-NGQZWQHPSA-N 0.000 claims 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 2
- FSVCELGFZIQNCK-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)glycine Chemical compound OCCN(CCO)CC(O)=O FSVCELGFZIQNCK-UHFFFAOYSA-N 0.000 claims 2
- UZMAPBJVXOGOFT-UHFFFAOYSA-N Syringetin Natural products COC1=C(O)C(OC)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UZMAPBJVXOGOFT-UHFFFAOYSA-N 0.000 claims 2
- 239000007997 Tricine buffer Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 239000007998 bicine buffer Substances 0.000 claims 2
- 150000003950 cyclic amides Chemical class 0.000 claims 2
- KCFYHBSOLOXZIF-UHFFFAOYSA-N dihydrochrysin Natural products COC1=C(O)C(OC)=CC(C2OC3=CC(O)=CC(O)=C3C(=O)C2)=C1 KCFYHBSOLOXZIF-UHFFFAOYSA-N 0.000 claims 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims 2
- NHTGHBARYWONDQ-UHFFFAOYSA-N (+-)-α-methyl-tyrosine Chemical compound OC(=O)C(N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-UHFFFAOYSA-N 0.000 claims 1
- LGVJIYCMHMKTPB-BKLSDQPFSA-N (2s)-2-amino-3-hydroxypentanoic acid Chemical compound CCC(O)[C@H](N)C(O)=O LGVJIYCMHMKTPB-BKLSDQPFSA-N 0.000 claims 1
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 claims 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 1
- LJCWONGJFPCTTL-SSDOTTSWSA-N D-4-hydroxyphenylglycine Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC=C(O)C=C1 LJCWONGJFPCTTL-SSDOTTSWSA-N 0.000 claims 1
- AYFVYJQAPQTCCC-PWNYCUMCSA-N D-Allothreonine Chemical compound C[C@@H](O)[C@@H](N)C(O)=O AYFVYJQAPQTCCC-PWNYCUMCSA-N 0.000 claims 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 claims 1
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 claims 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 1
- UKAUYVFTDYCKQA-GSVOUGTGSA-N D-homoserine Chemical compound OC(=O)[C@H](N)CCO UKAUYVFTDYCKQA-GSVOUGTGSA-N 0.000 claims 1
- AYFVYJQAPQTCCC-STHAYSLISA-N D-threonine Chemical compound C[C@H](O)[C@@H](N)C(O)=O AYFVYJQAPQTCCC-STHAYSLISA-N 0.000 claims 1
- 229930182822 D-threonine Natural products 0.000 claims 1
- OUYCCCASQSFEME-MRVPVSSYSA-N D-tyrosine Chemical compound OC(=O)[C@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-MRVPVSSYSA-N 0.000 claims 1
- 229930195709 D-tyrosine Natural products 0.000 claims 1
- QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims 1
- NHTGHBARYWONDQ-JTQLQIEISA-N L-α-methyl-Tyrosine Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-JTQLQIEISA-N 0.000 claims 1
- AXDLCFOOGCNDST-UHFFFAOYSA-N N-methyl-DL-tyrosine Natural products CNC(C(O)=O)CC1=CC=C(O)C=C1 AXDLCFOOGCNDST-UHFFFAOYSA-N 0.000 claims 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- 229960003767 alanine Drugs 0.000 claims 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- QXWYKJLNLSIPIN-JGVFFNPUSA-N droxidopa Chemical compound OC(=O)[C@@H](N)[C@H](O)C1=CC=C(O)C(O)=C1 QXWYKJLNLSIPIN-JGVFFNPUSA-N 0.000 claims 1
- 235000019414 erythritol Nutrition 0.000 claims 1
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 claims 1
- UKAUYVFTDYCKQA-UHFFFAOYSA-N homoserine Chemical compound OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 claims 1
- 235000010355 mannitol Nutrition 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 229960002920 sorbitol Drugs 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Chemical compound OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
- 229960004441 tyrosine Drugs 0.000 claims 1
- 230000009972 noncorrosive effect Effects 0.000 abstract 1
Abstract
A noncorrosive post-etch residue cleaning composition containing: (a) 1-70 % by weight of an organic polar solvent having a dipole moment of more than 3.5; (b) 1-70 % by weight of selected amine compounds having at least one hydroxyl group and a boiling point higher than 150 °C at atmospheric pressure; (c) 0.1-10 % by weight of selected amino acid having at least one hydroxyl group; (d) 1-20 % by weight of selected redox reagent having a redox potential in the range between +1.0 V and -2.0 V vs. SHE (at pH=7); and (e) 0.90 % by weight of water.
Claims
23
AMENDED CLAIMS
[received by the International Bureau on 17 January 1997 (17.01.97); original claims 1 and 8 amended; original claims 7, 13, 14 and 24 cancelled; new claim 25 added; remaining claims unchanged (5 pages)]
1. A post-etch residue cleaner composition comprising:
(a) from about 1 to about 70% by weight of an organic polar solvent having a dipole moment of more than 3.5;
(b) from about 1 to about 70% by weight of an alkanolamine compound having a boiling point higher than 150°C at atmospheric pressure;
(c) from about 0.1 to about 10% by weight of an amino acid selected from the group consisting of compounds having the formula (I) :
R1 R3
1 /
HOOC- ■ (-c-) _« -N i 12 P \
R4 (I)
wherein n is an integer ranging from 1-3; R1 and R2 are each independently selected from the group consisting of hydrogen and compounds having the formula (II) :
wherein R5, R6, and R7 are each independently selected from hydrogen, -OH, -CH2OH, alkyl, alkoxy, phenyl, and mono-, di- or tri-hydroxy-substituted phenyl groups; and R3 and R4 are each independently selected from the group consisting of hydroxy and compounds having the formula (III) :
X' 1 -C-Y'
(III)
wherein X', Y', and Z' are each independently selected from hydrogen, -OH, -CH2OH, -CH2CH2OH, alkyl, or alkoxy group, and at least one of them is -OH, -CH2OH or -CH2CH2OH;
(d) from about 1 to about 20% by weight of a redox reagent having a redox potential in the range between +1.0 V and -2.0 V vs. SHE (at pH=7) selected from the group consisting of sugar alcohols, piperidine, aniline, o-phenylenediamine, hydrazine, 1,10-phenanthroline and benzidine; and (e) optionally, from 0% to about 90% by weight of water; all percents based on the total weight of the cleaner composition.
2. The cleaner composition of claim 1 wherein said solvent (a) comprises a cyclic amide.
3. The cleaner composition of claim 2, wherein said cyclic amide is selected from the group consisting of N-alkyl-2-pyrrolidones and 1,3- dialkyl-2-imidazolidinones.
4. The cleaner composition of claim 2, wherein said solvent (a) is an admixture of N-hydroxyethyl- pyrrolididone (HEP) with l,3-dimethyl-2- imidozolidinone (DMI) wherein the ratio of HEP:DMI is from about 95:5% to about 5:95% by weight.
5. The cleaner composition of claim 1, wherein said solvent (a) comprises dimethylsulfoxide.
25
6. The cleaner composition of claim 1, wherein said solvent (a) is an admixture of N-hydroxyethyl- pyrroliidone (HEP) with dimethylsulfoxide (DMSO) wherein the ratio of HEP:DMSO is from about 95:5% to about 5:95% by weight.
8. The cleaner composition of claim 1, wherein said alkanolamine is selected from the group consisting of monoethanolamine, diethanolamine, triethanolamine, 2-(2-aminoethoxy)ethanol and 2-(2- aminoethylamino) ethanol.
9. The cleaner composition of claim 1, wherein said redox reagent (d) is a sugar alcohol.
10. The cleaner composition of claim 9, wherein said sugar alcohol is selected from the group consisting of erythritols, penitols, and hexitols.
11. The cleaner composition of claim 10, wherein said sugar alcohol is a penitol and is selected from the group consisting of D-arabitol and D-xylitol.
12. The cleaner composition of claim 10, wherein said sugar alcohol is a hexitol and is selected from the group consisting of D-sorbitol and D-mannitol.
15. The cleaner composition of claim 1, wherein said redox reagent (d) is piperidine.
16. The cleaner composition of claim 1, wherein said redox reagent (d) is aniline.
26
17. The cleaner composition of claim 1, wherein said redox reagent (d) is o-phenylenediamine.
18. The cleaner composition of claim 1, wherein said redox reagent (d) is hydrazine.
19. The cleaner composition of claim 1, wherein said redox reagent (d) is 1,10-phenanthroline.
20. The cleaner composition of claim 1, wherein said redox reagent (d) is benzidine.
21. The cleaner composition of claim 1, wherein said redox reagent (d) is present from about 3% to about 10% by weight, based on the total weight of said cleaner composition.
22. The cleaner composition of claim 1, wherein said amino acid (c) is selected from the group consisting of tricine, bicine, DL-homoserine, D- homoserine, -homoserine, DL-threonine, D-allo- threonine, L-allo-thronine, D-threonine, L- threonine, DL-3-hydroxy-norvaline, DL- methyltyrosine, D-4-hydroxyphenylglycine, DL- tyrosine, D-tyrosine, L-tyrosine, 3-(3,4- dihydroxypheny1)-DL-alanine, 3-(3,4-dihydroxypheny1- L-alanine, 3-(2,4,5-trihydroxypheny1)-DL-alanine, DL-alpha-methyltyrosine , L-alpha-methyltyrosine, (-)-3-(3,4-phenylserine, and DL-threo-3,4- dihydroxypheny1serine.
23. The cleaner composition of claim 21, wherein said amino acid is selected from the group consisting of tricine, bicine, 3-(3,4- dihydroxypheny1)-DL-alanine, 3-(2 ,4,5
27 trihydroxyphenyl)-DL-alanine, and DL-threo-3,4- dihydroxyphenylserine.
25. The cleaner composition of claim 1, wherein said cleaner composition further comprises water.
28
STATEMENT UNDER ARTICLE19
Applicant's invention, as embodied in Claim 1, is drawn to a post-etch residue cleaner composition, comprising, among other things, from about 1 to about 70% by weight of an alkanolamine compound having a boiling point higher than 150°C at atmospheric pressure; and from about 1 to about 20% by weight of a redox reagent having a redox potential in the range between +1.0 V and -2.0 V vs. SHE (at pH=7) selected from the group consisting of sugar alcohols, piperidine, aniline, o-phenylenediamine, hydrazine, 1,10-phenanthroline and benzidine.
Applicant submits that none of the references cited in the International Search Report teach or suggest a stripper composition that includes a redox reagent having a redox potential in the range between +1.0 V and -2.0 V vs. SHE selected from the group consisting of sugar alcohols, piperidine, aniline, o-phenylenediamine, hydrazine, 1,10-phenanthroline and benzidine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU63392/96A AU6339296A (en) | 1995-07-07 | 1996-06-24 | Redox reagent-containing post-etch residue cleaning composition |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US499,355 | 1995-07-07 | ||
| US08/499,355 US5612304A (en) | 1995-07-07 | 1995-07-07 | Redox reagent-containing post-etch residue cleaning composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1997003175A1 WO1997003175A1 (en) | 1997-01-30 |
| WO1997003175B1 true WO1997003175B1 (en) | 1997-02-13 |
Family
ID=23984951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/010807 WO1997003175A1 (en) | 1995-07-07 | 1996-06-24 | Redox reagent-containing post-etch residue cleaning composition |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US5612304A (en) |
| AU (1) | AU6339296A (en) |
| WO (1) | WO1997003175A1 (en) |
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| US4720332A (en) * | 1986-04-21 | 1988-01-19 | Coffey Barry W | Nickel strip formulation |
| JPH0721638B2 (en) * | 1986-07-18 | 1995-03-08 | 東京応化工業株式会社 | Substrate processing method |
| US4770713A (en) * | 1986-12-10 | 1988-09-13 | Advanced Chemical Technologies, Inc. | Stripping compositions containing an alkylamide and an alkanolamine and use thereof |
| JPS63208043A (en) * | 1987-02-25 | 1988-08-29 | Kanto Kagaku Kk | Water soluble stripping liquid for positive type photoresist |
| JP2553872B2 (en) * | 1987-07-21 | 1996-11-13 | 東京応化工業株式会社 | Stripping solution for photoresist |
| US4824763A (en) * | 1987-07-30 | 1989-04-25 | Ekc Technology, Inc. | Triamine positive photoresist stripping composition and prebaking process |
| JP2591626B2 (en) * | 1987-09-16 | 1997-03-19 | 東京応化工業株式会社 | Stripper for resist |
| JPH0769618B2 (en) * | 1987-09-25 | 1995-07-31 | 旭化成工業株式会社 | Stripping agent for photoresist |
| JP2631849B2 (en) * | 1987-09-30 | 1997-07-16 | ナガセ電子化学 株式会社 | Release agent composition |
| DE3828513A1 (en) * | 1988-08-23 | 1990-03-01 | Merck Patent Gmbh | Photoresist stripper contg. alkanolamine and di:methyl-imidazolidone - or di:methyl-tetra:hydro-pyrimidinone free from toxic hazard |
| DE3923426A1 (en) * | 1989-07-15 | 1991-01-17 | Hoechst Ag | METHOD FOR PRODUCING NOVOLAK RESIN WITH A LOW METAL ION CONTENT |
| JP2527268B2 (en) * | 1990-09-17 | 1996-08-21 | 東京応化工業株式会社 | Release agent composition for resist |
| US5279771A (en) * | 1990-11-05 | 1994-01-18 | Ekc Technology, Inc. | Stripping compositions comprising hydroxylamine and alkanolamine |
| JP3160344B2 (en) * | 1991-01-25 | 2001-04-25 | アシュランド インコーポレーテッド | Organic stripping composition |
| CA2062027C (en) * | 1991-03-04 | 1998-05-19 | William Aldrich | Liquid control system for diagnostic cartridges used in analytical instruments |
| JPH04350660A (en) * | 1991-05-28 | 1992-12-04 | Texas Instr Japan Ltd | Stripping liquid for positive photoresist for semiconductor device manufacturing and semiconductor device manufacturing method |
| US5378802A (en) * | 1991-09-03 | 1995-01-03 | Ocg Microelectronic Materials, Inc. | Method for removing impurities from resist components and novolak resins |
| US5480585A (en) * | 1992-04-02 | 1996-01-02 | Nagase Electronic Chemicals, Ltd. | Stripping liquid compositions |
| US5419779A (en) * | 1993-12-02 | 1995-05-30 | Ashland Inc. | Stripping with aqueous composition containing hydroxylamine and an alkanolamine |
| US5472830A (en) * | 1994-04-18 | 1995-12-05 | Ocg Microelectronic Materials, Inc. | Non-corrosion photoresist stripping composition |
| US5507978A (en) * | 1995-05-08 | 1996-04-16 | Ocg Microelectronic Materials, Inc. | Novolak containing photoresist stripper composition |
-
1995
- 1995-07-07 US US08/499,355 patent/US5612304A/en not_active Expired - Fee Related
-
1996
- 1996-06-24 WO PCT/US1996/010807 patent/WO1997003175A1/en active Application Filing
- 1996-06-24 AU AU63392/96A patent/AU6339296A/en not_active Abandoned
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