US20110207645A1 - Non-aqueous, non-corrosive microelectronic cleaning compositions containing polymeric corrosion inhibitors - Google Patents
Non-aqueous, non-corrosive microelectronic cleaning compositions containing polymeric corrosion inhibitors Download PDFInfo
- Publication number
- US20110207645A1 US20110207645A1 US13/066,889 US201113066889A US2011207645A1 US 20110207645 A1 US20110207645 A1 US 20110207645A1 US 201113066889 A US201113066889 A US 201113066889A US 2011207645 A1 US2011207645 A1 US 2011207645A1
- Authority
- US
- United States
- Prior art keywords
- substrate
- cleaning
- photoresist
- cleaning composition
- residue
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 103
- 238000004140 cleaning Methods 0.000 title claims abstract description 60
- 238000005260 corrosion Methods 0.000 title claims abstract description 26
- 230000007797 corrosion Effects 0.000 title claims abstract description 25
- 239000003112 inhibitor Substances 0.000 title claims abstract description 14
- 238000004377 microelectronic Methods 0.000 title claims description 23
- 230000009972 noncorrosive effect Effects 0.000 title abstract description 11
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 36
- 239000010949 copper Substances 0.000 claims abstract description 26
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052802 copper Inorganic materials 0.000 claims abstract description 24
- 229920000642 polymer Polymers 0.000 claims abstract description 22
- 239000003495 polar organic solvent Substances 0.000 claims abstract description 5
- 239000000758 substrate Substances 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 18
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 229920002873 Polyethylenimine Polymers 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 8
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 claims description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 7
- 238000001465 metallisation Methods 0.000 claims description 7
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 5
- CMJLMPKFQPJDKP-UHFFFAOYSA-N 3-methylthiolane 1,1-dioxide Chemical compound CC1CCS(=O)(=O)C1 CMJLMPKFQPJDKP-UHFFFAOYSA-N 0.000 claims description 4
- -1 diethanolamone Chemical compound 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 3
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims description 3
- RJLKIAGOYBARJG-UHFFFAOYSA-N 1,3-dimethylpiperidin-2-one Chemical compound CC1CCCN(C)C1=O RJLKIAGOYBARJG-UHFFFAOYSA-N 0.000 claims description 2
- WDQFELCEOPFLCZ-UHFFFAOYSA-N 1-(2-hydroxyethyl)pyrrolidin-2-one Chemical compound OCCN1CCCC1=O WDQFELCEOPFLCZ-UHFFFAOYSA-N 0.000 claims description 2
- AIDFJGKWTOULTC-UHFFFAOYSA-N 1-butylsulfonylbutane Chemical compound CCCCS(=O)(=O)CCCC AIDFJGKWTOULTC-UHFFFAOYSA-N 0.000 claims description 2
- JEXYCADTAFPULN-UHFFFAOYSA-N 1-propylsulfonylpropane Chemical compound CCCS(=O)(=O)CCC JEXYCADTAFPULN-UHFFFAOYSA-N 0.000 claims description 2
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 claims description 2
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims 1
- SZZYAOCSMNDGPI-UHFFFAOYSA-N methylsulfinylmethane;thiolane 1,1-dioxide Chemical compound CS(C)=O.O=S1(=O)CCCC1 SZZYAOCSMNDGPI-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 abstract description 12
- 229910052782 aluminium Inorganic materials 0.000 abstract description 8
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- 239000000463 material Substances 0.000 description 10
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- 239000002738 chelating agent Substances 0.000 description 5
- 239000008139 complexing agent Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 239000006117 anti-reflective coating Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
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- 239000006184 cosolvent Substances 0.000 description 4
- 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 description 4
- 239000012085 test solution Substances 0.000 description 4
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- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical group NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- 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
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 2
- 239000011358 absorbing material Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000000637 aluminium metallisation Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 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
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
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- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- AGGCEDYMGLPKNS-UHFFFAOYSA-N 5,5,6-trimethylundec-3-yne-2,2-diol Chemical class CCCCCC(C)C(C)(C)C#CC(C)(O)O AGGCEDYMGLPKNS-UHFFFAOYSA-N 0.000 description 1
- FCKYPQBAHLOOJQ-UHFFFAOYSA-N Cyclohexane-1,2-diaminetetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)C1CCCCC1N(CC(O)=O)CC(O)=O FCKYPQBAHLOOJQ-UHFFFAOYSA-N 0.000 description 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 description 1
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- 239000004386 Erythritol Substances 0.000 description 1
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 1
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- 150000007824 aliphatic compounds Chemical class 0.000 description 1
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- 239000004020 conductor Substances 0.000 description 1
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- DUYCTCQXNHFCSJ-UHFFFAOYSA-N dtpmp Chemical compound OP(=O)(O)CN(CP(O)(O)=O)CCN(CP(O)(=O)O)CCN(CP(O)(O)=O)CP(O)(O)=O DUYCTCQXNHFCSJ-UHFFFAOYSA-N 0.000 description 1
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- 239000011521 glass Substances 0.000 description 1
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- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
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Classifications
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/30—Amines; Substituted amines ; Quaternized amines
-
- 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
- G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/0073—Anticorrosion compositions
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3723—Polyamines or polyalkyleneimines
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3753—Polyvinylalcohol; Ethers or esters thereof
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/43—Solvents
-
- 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
- G03F7/426—Stripping or agents therefor using liquids only containing organic halogen compounds; containing organic sulfonic acids or salts thereof; containing sulfoxides
-
- C11D2111/22—
Definitions
- This invention relates to methods and non-aqueous, essentially non-corrosive, cleaning compositions for cleaning microelectronic substrates, and particularly to such cleaning compositions useful with and having improved compatibility with microelectronic substrates characterized by copper metallization as well as substrates characterized by aluminum metallization.
- the invention also relates to the use of such cleaning compositions for stripping photoresists, and cleaning residues from etch and plasma process generated organic, organometallic and inorganic compounds.
- photoresist strippers and residue removers have been proposed for use in the microelectronics field as downstream or back end of the manufacturing-line cleaners.
- a thin film of photoresist is deposited on a wafer substrate, and then circuit design is imaged on the thin film.
- the unpolymerized resist is removed with a photoresist developer.
- the resulting image is then transferred to the underlying material, which is generally a dielectric or metal, by way of reactive plasma etch gases or chemical etchant solutions.
- the etch gases or chemical etchant solutions selectively attack the photoresist-unprotected area of the substrate.
- the resist mask must be removed from the protected area of the wafer so that the final finishing operation can take place. This can be accomplished in a plasma ashing step by the use of suitable plasma ashing gases or wet chemical strippers. Finding a suitable cleaning composition for removal of this resist mask material without adversely affecting, e.g., corroding, dissolving or dulling, the metal circuitry has also proven problematic.
- hydroxylamine based stripper or residue remover compositions are successfully used for cleaning devices with Al metallizations, but are practically unsuitable for those with copper metallizations.
- many copper metallized are not suitable for Al metallized devices unless significant adjustments in the compositions are made.
- photoresist strippers have often contained amines since they generally show superior cleaning performance in attacking hardened photoresist and in the ability to strip such hardened photoresist from the surface of the microelectronic substrates.
- copper is generally also severely attacked by amines and significant metal corrosion can occur if such a conventional photoresist stripper is utilized without modification. Therefore, it is highly desirable to provide a copper compatible photoresist stripper or cleaner for use in the microelectronics industry, particularly for copper metallized materials. It is also highly desirable to is provide a copper compatible photoresist stripper or cleaner for use in the microelectronics industry, particularly for copper metallized materials, that is also compatible for use with aluminum metallized materials. Since the same shift in technology from aluminum to copper metallization is being seen in the development of flat panel displays, it is also desirable to provide a stripper/cleaner that can be use in producing such flat panel displays.
- Back end photoresist strippers and cleaning compositions of this invention are provided by non-aqueous, non-corrosive cleaning compositions that are essentially non-corrosive toward copper as well as aluminum and that comprise at least one polar organic solvent, at least one hydroxylated organic amine, and at least one corrosion inhibitor that is a polymer having multiple functional amino or hydroxyl groups pendant from the polymer backbone.
- the compositions of this invention may also contain a number of other optional components.
- the cleaning compositions of this invention can be used over a wide range of process/operating conditions of pH and temperature, and can be used to effectively remove photoresists, post plasma etch/ash residues, sacrificial light absorbing materials and anti-reflective coatings (ARC).
- the non-aqueous, essentially non-corrosive microelectronic stripper/cleaner compositions of this invention will generally comprise from about 80% or more of the organic polar solvent component, from about 1% to about 15% of the organic hydroxylated amine component, and a corrosion-inhibiting amount of the corrosion inhibitor polymer component, generally from about 0.1% to about 10% of the corrosion inhibitor polymer component with multiple hydroxyl functional groups.
- the wt percentages provided in this specification are based on the total weight of the cleaning composition.
- non-aqueous, essentially non-corrosive stripping/cleaning compositions of this invention can also optionally contain other compatible components, including but not limited to components such as chelating agents, organic hydroxyl-containing co-solvents, stabilizing and metal chelating or complexing agents, other metal corrosion inhibitors, and surfactants.
- compatible components including but not limited to components such as chelating agents, organic hydroxyl-containing co-solvents, stabilizing and metal chelating or complexing agents, other metal corrosion inhibitors, and surfactants.
- Non-aqueous compositions that are essentially non-corrosive toward copper as well as aluminum and that comprise one or more polar organic solvents one or more organic hydroxylated amine, and one or more corrosion inhibitor polymers having multiple hydroxyl or amino groups pendant from the polymer backbone.
- non-aqueous it is meant that the compositions are substantially free of water and will generally only have water present as impurities from the other components, and then will generally amount to no more than about 3% by weight of the composition, and preferably less.
- the cleaning compositions of this invention can be used over a wide range of process/operating conditions of pH and temperature, and can be used to effectively remove photoresists, post plasma etch/ash residues, sacrificial light absorbing materials and anti-reflective coatings (ARC). Additionally, it has been discovered that very difficult to clean samples, such as highly crosslinked or hardened photoresists and structures which contain titanium (such as titanium, titanium oxide and titanium nitride) or tantalums (such as tantalum, tantalum oxide and tantalum nitride), can be readily cleaned with the cleaning compositions of this is invention.
- titanium such as titanium, titanium oxide and titanium nitride
- tantalums such as tantalum, tantalum oxide and tantalum nitride
- the non-aqueous, essentially non-corrosive microelectronic stripper/cleaner compositions of this invention will generally comprise from about 80% or more, preferably from about 85% or more, and most preferably from 90% or more, of the organic polar solvent component; from about 1% to about 15%, preferably from about 2 to about 10%, and more preferably from about 2% to about 5%, of the organic hydroxylated amine component, and a corrosion-inhibiting amount of the corrosion inhibitor polymer component, generally from about 0.1% to about 10%, preferably from about 0.3% to about 5%, and more preferably from about 0.3% to about 3%.
- the wt percentages provided in this specification are based on the total weight of the cleaning composition.
- compositions of this invention can contain one or more of any suitable organic polar solvent, preferably organic polar solvents that includes amides, sulfones, sulfoxides, saturated alcohols and the like.
- organic polar solvents include, but are not limited to, organic polar solvents such as sulfolane (tetrahydrothiopene-1,1-dioxide), 3-methylsulfolane, n-propyl sulfone, dimethyl sulfoxide (DMSO), methyl sulfone, n-butyl sulfone, 3-methylsulfolane, amides such as 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), dimethylpiperidone (DMPD), N-methyl-2-pyrrolidone (NMP), dimethylacetamide (DMAc), and dimethylformamide (DMF) and mixtures thereof.
- organic polar solvents such as sulfolane (tetrahydrothiopene-1,
- the organic hydroxylated amine component may be one or more of any suitable hydroxylated amines, preferably hydroxylamine or an alkanolamine, preferably an alkanolamine.
- suitable organic hydroxylated amine useful in the compositions of this invention include, but are not limited to hydroxylamine, monoethanolamine, diethanolamone, triethanolamine, and particularly 2-aminoethanol, 1-amino-2-propanol, 1-amino-3-propanol, 2-(2-aminoethoxy)ethanol, diethanolamine, 2-(2-aminoethylamino)ethanol, 2-(2-aminoethylamino)ethylamine and the like, and mixtures thereof.
- the organic hydroxylated amine component is monoethanolamine, diethanolamine, triethanolamine, 2-(2-aminoethylamino)ethanol, and 1-amino-2-propanol and mixtures thereof.
- the corrosion inhibiting compounds in the cleaning compositions of this invention are polymers having multiple pendant hydroxyl or amine geoups pendant from the polymer backbone.
- suitable corrosion inhibitor polymers include, but are not limited to, polyethyleneimine polymers and copolymers, polyvinyl alcohol polymers and copolymers, polystyrene polymers and copolymers, poly (hydroxyl alkyl acrylate or methacrylate) polymers and copolymers, and the like.
- the polymers are preferably polyethyleneimine polymers, polyvinyl alcohol polymers, and polyvinyl alcohol-ethylene copolymers.
- compositions of this invention may also optionally contain one or more of any suitable organic hydroxyl- or polyhydroxyl-containing aliphatic compounds as a co-solvent. Any suitable organic hydroxyl-containing co-solvent may be employed in the compositions of this invention.
- suitable organic hydroxyl-containing co-solvents include, but are not limited to,
- suitable corrosion inhibitors include, but are not limited to: arabitol, erythritol, xylitol, mannitol, sorbitol, ethylene dlycol, glycerol, 1,4-butane diol, 1,2-cyclopentanediol, 1,2-cyclohexanediol, and methylpentanediol, fructose, mono- and dialkyl ethers of diethylene glycol, known as Carbitol (2-(2-ethoxyethoxy)ethanol) and Carbitol derivatives, and saturated alcohols such as ethanol, propanol, butanol, hexanol, and hexafluoroisopropanol, and mixtures thereof.
- a co-solvent is 2-(2-ethoxyethoxy)ethanol (Carbitol).
- a co-solvent may be present in the compositions of this invention in an amount, based on the total weight of the composition, of from 0 to about 10 wt %, preferably from about 0.1 to about 10 wt %, most preferably from about 0.5 to about 5 wt %, based on the weight of the composition.
- compositions of this invention may also contain one or more of any suitable other corrosion-inhibiting agents, preferably aryl compounds containing two or more OH, OR 6 , and/or SO 2 R 6 R 7 groups bonded directly to the aromatic ring, where R 6 , R 7 and R 8 are each independently alkyl, preferably alkyl of from 1 to 6 carbon atoms, or aryl, preferably aryl of from 6 to 14 carbon atoms.
- any suitable other corrosion-inhibiting agents preferably aryl compounds containing two or more OH, OR 6 , and/or SO 2 R 6 R 7 groups bonded directly to the aromatic ring, where R 6 , R 7 and R 8 are each independently alkyl, preferably alkyl of from 1 to 6 carbon atoms, or aryl, preferably aryl of from 6 to 14 carbon atoms.
- Such preferred corrosion-inhibiting agents there may be mentioned catechol, pyrogallol, gallic acid, resorcinol and the like.
- Such other corrosion-inhibiting agents may be present in an amount of from 0 to about 10 wt %, preferably from about 0.1 to about 10 wt %,, most preferably from about 0.5 to about 5 wt % based on the weight of the composition.
- Organic or inorganic chelating or metal complexing agents are not required, but offer substantial benefits, such as for example, improved product stability.
- One or more of such inorganic chelating or metal complexing agents may be employed in the compositions of this invention.
- suitable chelating or complexing agents include but are not limited to trans-1,2-cyclohexanediamine tetraacetic acid (CyDTA), ethylenediamine tetraacetic acid (EDTA), stannates, pyrophosphates, alkylidene-diphosphonic acid derivatives (e.g.
- ethane-1-hydroxy-1,1-diphosphonate phosphonates containing ethylenediamine, diethylenetriamine or triethylenetetramine functional moieties e,g., ethylenediamine tetra(methylene phosphonic acid) (EDTMP), diethylenetriamine penta(methylene phosphonic acid), and triethylenetetramine hexa(methylene phosphonic acid), and mixtures thereof.
- the chelating agent will be present in the composition in an amount of from 0 to about 5 wt %, preferably from about 0.1 to about 2 wt %, based on the weight of the composition.
- Metal chelating or complexing agents of various phosphonates such as ethylenediamine tetra(methylene phosphonic acid) (EDTMP) offer much improved stabilization of the cleaning compositions of the cleaning compositions of this invention containing oxidizing agents at acidic and alkaline conditions and thus are generally preferred.
- ETMP ethylenediamine tetra(methylene phosphonic acid)
- other different metal corrosion inhibitors such as benzotriazole
- benzotriazole may be employed in an amount of from 0 to about 5 wt %, preferably from about 0.1 to 2 wt %, based on the weight of the composition.
- the cleaning compositions optionally may also contain one or more suitable surfactants, such as for example dimethyl hexynol (Surfynol-61), ethoxylated tetramethyl decynediol (Surfynol-465), polytetrafluoroethylene cetoxypropylbetaine (Zonyl FSK), Zonyl FSH and the like.
- suitable surfactants such as for example dimethyl hexynol (Surfynol-61), ethoxylated tetramethyl decynediol (Surfynol-465), polytetrafluoroethylene cetoxypropylbetaine (Zonyl FSK), Zonyl FSH and the like.
- the surfactant will generally be present in an amount of from 0 to about 5 wt %, preferably 0.1 to about 3 wt %, based on the weight of the composition.
- Example of cleaning compositions of this invention include, but are not limited to, the compositions set forth in the following Table 1 and comparative compositions without the polymeric corrosion inhibitors are set forth in Table 2.
- Tables 1 and 2 the abbreviations employed are as follows:
- NMP N-methyl pyrolidinone
- PEI polyethyleneimine, anhydrous, high molecular weight-Aldrich 2003-2004 catalogue # 40,872-7
- PVA-E poly(vinyl alcohol-co-ethylene), ethylene content 445-Aldrich 2003-2004 catalogue # 41,407-7
- a piece of copper-coated silicon wafer (approximately 20 ⁇ 20 mm) was prepared for the experiment.
- the piece was cleaned in a buffered oxide etch (which contains 35 w/w % NH4F and 6 w/w % HF for 1 minute, followed by rinsing in deionized water for 1 minute, and dried in nitrogen spray.
- the wafer piece was immersed in a 150 mL beaker that has 100 g of test solution in it, and the solution was heated at 60° C., stirred with a magnetic stirrer at 200 rpm and, 62 or 63 minutes later, the piece was removed from the test solution, rinsed with deionized water for 1 minute, and dried with nitrogen spray.
- the thickness of copper layer (before and after the experiment) was determined by the ResMap (manufactured by Creative Design Engineering, Sunnyvale, Calif.) 4-point probe system.
- test solutions were the Invention Compositions 1 and 2 of Table 1 and the comparison compositions were Compositions A and B of Table 2.
- the comparison compositions were similar to compositions of the invention but not containing the corrosion inhibiting polymers of the invention.
- the same test compositions of this invention are used at the same temperature (60° C.) with the same stirring rate (200 rpm).
- a piece of glass having a positive photoresist layer (ca. 1000 angstroms) deposited thereon is immersed in the test solution to determine that photoresist is removed by the compositions of the invention.
- compositions of this invention being essentially non-corrosive to copper metallized microelctronic substrates and capable of cleaning photoresist, plasma and etch residues from such substrates, such compositions are also able to similarly clean aluminum metallized microelectonic substrates in a similar non-corrosive manner.
Abstract
Description
- This application is a divisional patent application of co-pending U.S. patent application Ser. No. 11/719,690, filed may 18, 2007 as the US National Stage of PCT Application No. PCT/US2005/002849, filed Fe. 1, 2005, claiming priority from U.S. Provisional Patent application No. 60/634,945, filed Dec. 10, 2004, priority of which is claimed.
- This invention relates to methods and non-aqueous, essentially non-corrosive, cleaning compositions for cleaning microelectronic substrates, and particularly to such cleaning compositions useful with and having improved compatibility with microelectronic substrates characterized by copper metallization as well as substrates characterized by aluminum metallization. The invention also relates to the use of such cleaning compositions for stripping photoresists, and cleaning residues from etch and plasma process generated organic, organometallic and inorganic compounds.
- Many photoresist strippers and residue removers have been proposed for use in the microelectronics field as downstream or back end of the manufacturing-line cleaners. In the manufacturing process a thin film of photoresist is deposited on a wafer substrate, and then circuit design is imaged on the thin film. Following baking, the unpolymerized resist is removed with a photoresist developer. The resulting image is then transferred to the underlying material, which is generally a dielectric or metal, by way of reactive plasma etch gases or chemical etchant solutions. The etch gases or chemical etchant solutions selectively attack the photoresist-unprotected area of the substrate.
- Additionally, following the termination of the etching step, the resist mask must be removed from the protected area of the wafer so that the final finishing operation can take place. This can be accomplished in a plasma ashing step by the use of suitable plasma ashing gases or wet chemical strippers. Finding a suitable cleaning composition for removal of this resist mask material without adversely affecting, e.g., corroding, dissolving or dulling, the metal circuitry has also proven problematic.
- As microelectronic fabrication integration levels have increased and patterned microelectonic device dimensions have decreased towards the size of atoms, the heat formed as current passes through the circuits has become a serious problem. It has become increasingly common in the art to employ copper metallizations as the conductor material, instead of aluminum, since copper is more beneficial in reducing the heat formation. These copper containing microelectronic materials have presented additional challenges to find acceptable cleaner compositions. Many process technology compositions that have been previously developed for “traditional” or “conventional” semiconductor devices containing Al/SiO2 or Al (Cu)/SiO2 structures cannot be employed with copper metallized structures. For example, hydroxylamine based stripper or residue remover compositions are successfully used for cleaning devices with Al metallizations, but are practically unsuitable for those with copper metallizations. Similarly, many copper metallized are not suitable for Al metallized devices unless significant adjustments in the compositions are made.
- Removal of these etch and/or ash residues following the plasma etch and/or ashing process for such copper and aluminum metalllized microelectronic structures has proved problematic, particularly for substrates metallized with copper. Failure to completely remove or neutralize these residues can result in the absorption of moisture and the formation of undesirable materials that can cause corrosion to the metal structures. The circuitry materials are corroded by the undesirable materials and produce discontinuances in the circuitry wiring and undesirable increases in electrical resistance.
- Heretofore, photoresist strippers have often contained amines since they generally show superior cleaning performance in attacking hardened photoresist and in the ability to strip such hardened photoresist from the surface of the microelectronic substrates. However, copper is generally also severely attacked by amines and significant metal corrosion can occur if such a conventional photoresist stripper is utilized without modification. Therefore, it is highly desirable to provide a copper compatible photoresist stripper or cleaner for use in the microelectronics industry, particularly for copper metallized materials. It is also highly desirable to is provide a copper compatible photoresist stripper or cleaner for use in the microelectronics industry, particularly for copper metallized materials, that is also compatible for use with aluminum metallized materials. Since the same shift in technology from aluminum to copper metallization is being seen in the development of flat panel displays, it is also desirable to provide a stripper/cleaner that can be use in producing such flat panel displays.
- Back end photoresist strippers and cleaning compositions of this invention are provided by non-aqueous, non-corrosive cleaning compositions that are essentially non-corrosive toward copper as well as aluminum and that comprise at least one polar organic solvent, at least one hydroxylated organic amine, and at least one corrosion inhibitor that is a polymer having multiple functional amino or hydroxyl groups pendant from the polymer backbone. The compositions of this invention may also contain a number of other optional components. The cleaning compositions of this invention can be used over a wide range of process/operating conditions of pH and temperature, and can be used to effectively remove photoresists, post plasma etch/ash residues, sacrificial light absorbing materials and anti-reflective coatings (ARC). Additionally, it has been discovered that very difficult to clean samples, such as highly crosslinked or s hardened photoresists and structures which contain titanium (such as titanium, titanium oxide and titanium nitride) or tantalums (such as tantalum, tantalum oxide and tantalum nitride) can be readily cleaned with the cleaning compositions of this invention.
- The non-aqueous, essentially non-corrosive microelectronic stripper/cleaner compositions of this invention will generally comprise from about 80% or more of the organic polar solvent component, from about 1% to about 15% of the organic hydroxylated amine component, and a corrosion-inhibiting amount of the corrosion inhibitor polymer component, generally from about 0.1% to about 10% of the corrosion inhibitor polymer component with multiple hydroxyl functional groups. The wt percentages provided in this specification are based on the total weight of the cleaning composition.
- The non-aqueous, essentially non-corrosive stripping/cleaning compositions of this invention can also optionally contain other compatible components, including but not limited to components such as chelating agents, organic hydroxyl-containing co-solvents, stabilizing and metal chelating or complexing agents, other metal corrosion inhibitors, and surfactants.
- Back end photoresist strippers and cleaning compositions of this invention are provided by non-aqueous compositions that are essentially non-corrosive toward copper as well as aluminum and that comprise one or more polar organic solvents one or more organic hydroxylated amine, and one or more corrosion inhibitor polymers having multiple hydroxyl or amino groups pendant from the polymer backbone. By “non-aqueous” it is meant that the compositions are substantially free of water and will generally only have water present as impurities from the other components, and then will generally amount to no more than about 3% by weight of the composition, and preferably less.
- The cleaning compositions of this invention can be used over a wide range of process/operating conditions of pH and temperature, and can be used to effectively remove photoresists, post plasma etch/ash residues, sacrificial light absorbing materials and anti-reflective coatings (ARC). Additionally, it has been discovered that very difficult to clean samples, such as highly crosslinked or hardened photoresists and structures which contain titanium (such as titanium, titanium oxide and titanium nitride) or tantalums (such as tantalum, tantalum oxide and tantalum nitride), can be readily cleaned with the cleaning compositions of this is invention.
- The non-aqueous, essentially non-corrosive microelectronic stripper/cleaner compositions of this invention will generally comprise from about 80% or more, preferably from about 85% or more, and most preferably from 90% or more, of the organic polar solvent component; from about 1% to about 15%, preferably from about 2 to about 10%, and more preferably from about 2% to about 5%, of the organic hydroxylated amine component, and a corrosion-inhibiting amount of the corrosion inhibitor polymer component, generally from about 0.1% to about 10%, preferably from about 0.3% to about 5%, and more preferably from about 0.3% to about 3%. The wt percentages provided in this specification are based on the total weight of the cleaning composition.
- The compositions of this invention can contain one or more of any suitable organic polar solvent, preferably organic polar solvents that includes amides, sulfones, sulfoxides, saturated alcohols and the like. Such organic polar solvents include, but are not limited to, organic polar solvents such as sulfolane (tetrahydrothiopene-1,1-dioxide), 3-methylsulfolane, n-propyl sulfone, dimethyl sulfoxide (DMSO), methyl sulfone, n-butyl sulfone, 3-methylsulfolane, amides such as 1-(2-hydroxyethyl)-2-pyrrolidone (HEP), dimethylpiperidone (DMPD), N-methyl-2-pyrrolidone (NMP), dimethylacetamide (DMAc), and dimethylformamide (DMF) and mixtures thereof. Especially preferred as the organic polar solvent are N-methylpyrrolidone, sulfolane, DMSO and mixtures of two or more of these three solvents.
- The organic hydroxylated amine component may be one or more of any suitable hydroxylated amines, preferably hydroxylamine or an alkanolamine, preferably an alkanolamine. Suitable organic hydroxylated amine useful in the compositions of this invention include, but are not limited to hydroxylamine, monoethanolamine, diethanolamone, triethanolamine, and particularly 2-aminoethanol, 1-amino-2-propanol, 1-amino-3-propanol, 2-(2-aminoethoxy)ethanol, diethanolamine, 2-(2-aminoethylamino)ethanol, 2-(2-aminoethylamino)ethylamine and the like, and mixtures thereof. Most preferably the organic hydroxylated amine component is monoethanolamine, diethanolamine, triethanolamine, 2-(2-aminoethylamino)ethanol, and 1-amino-2-propanol and mixtures thereof.
- The corrosion inhibiting compounds in the cleaning compositions of this invention are polymers having multiple pendant hydroxyl or amine geoups pendant from the polymer backbone. Examples of suitable corrosion inhibitor polymers include, but are not limited to, polyethyleneimine polymers and copolymers, polyvinyl alcohol polymers and copolymers, polystyrene polymers and copolymers, poly (hydroxyl alkyl acrylate or methacrylate) polymers and copolymers, and the like. The polymers are preferably polyethyleneimine polymers, polyvinyl alcohol polymers, and polyvinyl alcohol-ethylene copolymers.
- The compositions of this invention may also optionally contain one or more of any suitable organic hydroxyl- or polyhydroxyl-containing aliphatic compounds as a co-solvent. Any suitable organic hydroxyl-containing co-solvent may be employed in the compositions of this invention. Examples of such suitable organic hydroxyl-containing co-solvents include, but are not limited to, Examples of suitable corrosion inhibitors include, but are not limited to: arabitol, erythritol, xylitol, mannitol, sorbitol, ethylene dlycol, glycerol, 1,4-butane diol, 1,2-cyclopentanediol, 1,2-cyclohexanediol, and methylpentanediol, fructose, mono- and dialkyl ethers of diethylene glycol, known as Carbitol (2-(2-ethoxyethoxy)ethanol) and Carbitol derivatives, and saturated alcohols such as ethanol, propanol, butanol, hexanol, and hexafluoroisopropanol, and mixtures thereof. Especially preferred as a co-solvent is 2-(2-ethoxyethoxy)ethanol (Carbitol). A co-solvent may be present in the compositions of this invention in an amount, based on the total weight of the composition, of from 0 to about 10 wt %, preferably from about 0.1 to about 10 wt %, most preferably from about 0.5 to about 5 wt %, based on the weight of the composition.
- The compositions of this invention may also contain one or more of any suitable other corrosion-inhibiting agents, preferably aryl compounds containing two or more OH, OR6, and/or SO2R6R7 groups bonded directly to the aromatic ring, where R6, R7 and R8 are each independently alkyl, preferably alkyl of from 1 to 6 carbon atoms, or aryl, preferably aryl of from 6 to 14 carbon atoms.
- As examples of such preferred corrosion-inhibiting agents there may be mentioned catechol, pyrogallol, gallic acid, resorcinol and the like. Such other corrosion-inhibiting agents may be present in an amount of from 0 to about 10 wt %, preferably from about 0.1 to about 10 wt %,, most preferably from about 0.5 to about 5 wt % based on the weight of the composition.
- Organic or inorganic chelating or metal complexing agents are not required, but offer substantial benefits, such as for example, improved product stability. One or more of such inorganic chelating or metal complexing agents may be employed in the compositions of this invention. Examples of suitable chelating or complexing agents include but are not limited to trans-1,2-cyclohexanediamine tetraacetic acid (CyDTA), ethylenediamine tetraacetic acid (EDTA), stannates, pyrophosphates, alkylidene-diphosphonic acid derivatives (e.g. ethane-1-hydroxy-1,1-diphosphonate), phosphonates containing ethylenediamine, diethylenetriamine or triethylenetetramine functional moieties e,g., ethylenediamine tetra(methylene phosphonic acid) (EDTMP), diethylenetriamine penta(methylene phosphonic acid), and triethylenetetramine hexa(methylene phosphonic acid), and mixtures thereof. The chelating agent will be present in the composition in an amount of from 0 to about 5 wt %, preferably from about 0.1 to about 2 wt %, based on the weight of the composition. Metal chelating or complexing agents of various phosphonates, such as ethylenediamine tetra(methylene phosphonic acid) (EDTMP) offer much improved stabilization of the cleaning compositions of the cleaning compositions of this invention containing oxidizing agents at acidic and alkaline conditions and thus are generally preferred.
- Optional: other different metal corrosion inhibitors, such as benzotriazole, may be employed in an amount of from 0 to about 5 wt %, preferably from about 0.1 to 2 wt %, based on the weight of the composition.
- The cleaning compositions optionally may also contain one or more suitable surfactants, such as for example dimethyl hexynol (Surfynol-61), ethoxylated tetramethyl decynediol (Surfynol-465), polytetrafluoroethylene cetoxypropylbetaine (Zonyl FSK), Zonyl FSH and the like. The surfactant will generally be present in an amount of from 0 to about 5 wt %, preferably 0.1 to about 3 wt %, based on the weight of the composition.
- Example of cleaning compositions of this invention include, but are not limited to, the compositions set forth in the following Table 1 and comparative compositions without the polymeric corrosion inhibitors are set forth in Table 2. In Tables 1 and 2 the abbreviations employed are as follows:
- NMP=N-methyl pyrolidinone
- SFL=sulfolane
- DMSO=dimethyl sulfoxide
- AMP=1-amino-2-propanol
- DEA=diethanolamine
- PEI=polyethyleneimine, anhydrous, high molecular weight-Aldrich 2003-2004 catalogue # 40,872-7
- PVA-E=poly(vinyl alcohol-co-ethylene), ethylene content 445-Aldrich 2003-2004 catalogue # 41,407-7
-
TABLE 1 Compositions/Parts by Weight Components 1 2 NMP 64.67 60 SFL 32.33 15 DMSO 15 AMP 2.7 DEA 5 PEI 0.3 PVA-E 1 -
TABLE 2 Compositions/Parts by Weight Components A B NMP 64.67 60 SFL 32.33 15 DMSO 15 AMP 3 DEA 5 PEI PVA-E - The anti-corrosion results obtained with the corrosion inhibiting polymer-containing cleaning compositions of this invention were obtained in the following test for compositions of this invention
- A piece of copper-coated silicon wafer (approximately 20×20 mm) was prepared for the experiment. The piece was cleaned in a buffered oxide etch (which contains 35 w/w % NH4F and 6 w/w % HF for 1 minute, followed by rinsing in deionized water for 1 minute, and dried in nitrogen spray. Then the wafer piece was immersed in a 150 mL beaker that has 100 g of test solution in it, and the solution was heated at 60° C., stirred with a magnetic stirrer at 200 rpm and, 62 or 63 minutes later, the piece was removed from the test solution, rinsed with deionized water for 1 minute, and dried with nitrogen spray. The thickness of copper layer (before and after the experiment) was determined by the ResMap (manufactured by Creative Design Engineering, Sunnyvale, Calif.) 4-point probe system.
- The test solutions (cleaning compositions) were the Invention Compositions 1 and 2 of Table 1 and the comparison compositions were Compositions A and B of Table 2. The comparison compositions were similar to compositions of the invention but not containing the corrosion inhibiting polymers of the invention.
-
TABLE 3 Treatment time Composition No. minutes Cu Etch Rate (Å/min.) 1 63 7.2 A 63 56.7 2 62 6.5 B 62 12.3 - For the photoresist stripping, the same test compositions of this invention are used at the same temperature (60° C.) with the same stirring rate (200 rpm). A piece of glass having a positive photoresist layer (ca. 1000 angstroms) deposited thereon is immersed in the test solution to determine that photoresist is removed by the compositions of the invention.
- In addition to the cleaning compositions of this invention being essentially non-corrosive to copper metallized microelctronic substrates and capable of cleaning photoresist, plasma and etch residues from such substrates, such compositions are also able to similarly clean aluminum metallized microelectonic substrates in a similar non-corrosive manner.
- While the invention has been described herein with reference to the specific embodiments thereof, it will be appreciated that changes, modification is and variations can be made without departing from the spirit and scope of the inventive concept disclosed herein. Accordingly, it is intended to embrace all such changes, modification and variations that fall with the spirit and scope of the appended claims.
Claims (17)
Priority Applications (1)
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US13/066,889 US20110207645A1 (en) | 2004-12-10 | 2011-04-27 | Non-aqueous, non-corrosive microelectronic cleaning compositions containing polymeric corrosion inhibitors |
Applications Claiming Priority (4)
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US63494504P | 2004-12-10 | 2004-12-10 | |
PCT/US2005/002940 WO2006065256A1 (en) | 2004-12-10 | 2005-02-01 | Non-aqueous, non-corrosive microelectronic cleaning compositions containing polymeric corrosion inhibitors |
US71969007A | 2007-05-18 | 2007-05-18 | |
US13/066,889 US20110207645A1 (en) | 2004-12-10 | 2011-04-27 | Non-aqueous, non-corrosive microelectronic cleaning compositions containing polymeric corrosion inhibitors |
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PCT/US2005/002849 Division WO2005074567A2 (en) | 2004-02-02 | 2005-02-02 | High-scoring game played on a playing field or court by opposing teams |
US71969007A Division | 2004-12-10 | 2007-05-18 |
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US20110207645A1 true US20110207645A1 (en) | 2011-08-25 |
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US11/719,690 Expired - Fee Related US7947639B2 (en) | 2004-12-10 | 2005-02-01 | Non-aqueous, non-corrosive microelectronic cleaning compositions containing polymeric corrosion inhibitors |
US13/066,889 Abandoned US20110207645A1 (en) | 2004-12-10 | 2011-04-27 | Non-aqueous, non-corrosive microelectronic cleaning compositions containing polymeric corrosion inhibitors |
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US11/719,690 Expired - Fee Related US7947639B2 (en) | 2004-12-10 | 2005-02-01 | Non-aqueous, non-corrosive microelectronic cleaning compositions containing polymeric corrosion inhibitors |
Country Status (17)
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US (2) | US7947639B2 (en) |
EP (1) | EP1828848B1 (en) |
JP (1) | JP4272677B2 (en) |
KR (1) | KR100744223B1 (en) |
CN (1) | CN101076760B (en) |
AT (1) | ATE463763T1 (en) |
BR (1) | BRPI0518420A2 (en) |
CA (1) | CA2591477A1 (en) |
DE (1) | DE602005020499D1 (en) |
IL (1) | IL183699A (en) |
MY (1) | MY143658A (en) |
NO (1) | NO20073497L (en) |
PL (1) | PL1828848T3 (en) |
PT (1) | PT1828848E (en) |
TW (1) | TWI353380B (en) |
WO (1) | WO2006065256A1 (en) |
ZA (1) | ZA200704704B (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US20100159400A1 (en) * | 2008-12-24 | 2010-06-24 | Samsung Electronics Co., Ltd. | Composition for removing a photoresist pattern and method of forming a metal pattern using the composition |
US20220056383A1 (en) * | 2018-12-14 | 2022-02-24 | Merck Patent Gmbh | Substrate cleaning solution and method for manufacturing device |
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KR20060064441A (en) * | 2004-12-08 | 2006-06-13 | 말린크로트 베이커, 인코포레이티드 | Non-aqueous, non-corrosive microelectronic cleaning compositions |
PT1828848E (en) * | 2004-12-10 | 2010-05-21 | Mallinckrodt Baker Inc | Non-aqueous, non-corrosive microelectronic cleaning compositions containing polymeric corrosion inhibitors |
KR101088568B1 (en) * | 2005-04-19 | 2011-12-05 | 아반토르 퍼포먼스 머티리얼스, 인크. | Non-aqueous photoresist stripper that inhibits galvanic corrosion |
CN101126053A (en) * | 2006-08-17 | 2008-02-20 | 安集微电子(上海)有限公司 | Cleaning liquid composition for plasma etching residues in semi-conductor industry |
BRPI0908905A2 (en) * | 2008-02-29 | 2015-09-22 | Mallinckrodt Baker Inc | microelectronic substrate cleaning compositions |
KR20100123757A (en) * | 2008-03-07 | 2010-11-24 | 어드밴스드 테크놀러지 머티리얼즈, 인코포레이티드 | Non-selective oxide etch wet clean composition and method of use |
JP5305803B2 (en) * | 2008-09-19 | 2013-10-02 | 株式会社カネカ | Method for producing polyethers |
RU2011139104A (en) * | 2009-02-25 | 2013-04-10 | Авантор Перформанс Матириалз, Инк. | CLEANING COMPOSITION FOR MICROELECTRONICS BASED ON MULTI-PURPOSE ACID ORGANIC SOLVENT |
JP6033314B2 (en) | 2011-10-05 | 2016-11-30 | アバンター・パフォーマンス・マテリアルズ・インコーポレイテッド | Microelectronic substrate cleaning composition comprising a copper / azole polymer inhibitor |
CN102618900B (en) * | 2012-04-14 | 2016-12-14 | 烟台恒迪克能源科技有限公司 | A kind of Triode surface treatment liquid and preparation method thereof |
CN109971565B (en) * | 2017-12-27 | 2021-10-22 | 安集微电子(上海)有限公司 | Fluorine-containing cleaning solution |
WO2022093807A1 (en) * | 2020-10-26 | 2022-05-05 | Advanced & Innovative Multifunctional Materials, Llc | Oxygenated hierarchically porous carbon compounds as scaffolds for metal nanoparticles |
CN113201743B (en) * | 2021-04-08 | 2022-06-21 | 浙江工业大学 | Rust remover suitable for electronic devices and preparation method thereof |
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- 2005-02-01 BR BRPI0518420-7A patent/BRPI0518420A2/en not_active IP Right Cessation
- 2005-02-01 EP EP05712395A patent/EP1828848B1/en not_active Not-in-force
- 2005-02-01 DE DE602005020499T patent/DE602005020499D1/en active Active
- 2005-02-01 CN CN200580042541XA patent/CN101076760B/en not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
---|---|
CA2591477A1 (en) | 2006-06-22 |
BRPI0518420A2 (en) | 2008-11-25 |
MY143658A (en) | 2011-06-30 |
JP2007514984A (en) | 2007-06-07 |
EP1828848B1 (en) | 2010-04-07 |
NO20073497L (en) | 2007-07-06 |
PL1828848T3 (en) | 2010-09-30 |
KR100744223B1 (en) | 2007-07-30 |
WO2006065256A1 (en) | 2006-06-22 |
IL183699A0 (en) | 2007-09-20 |
ZA200704704B (en) | 2008-09-25 |
IL183699A (en) | 2012-10-31 |
TWI353380B (en) | 2011-12-01 |
TW200619379A (en) | 2006-06-16 |
PT1828848E (en) | 2010-05-21 |
EP1828848A1 (en) | 2007-09-05 |
CN101076760A (en) | 2007-11-21 |
KR20060065412A (en) | 2006-06-14 |
US7947639B2 (en) | 2011-05-24 |
DE602005020499D1 (en) | 2010-05-20 |
JP4272677B2 (en) | 2009-06-03 |
CN101076760B (en) | 2010-12-22 |
ATE463763T1 (en) | 2010-04-15 |
US20090156453A1 (en) | 2009-06-18 |
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