US20020013238A1 - Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures - Google Patents

Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures Download PDF

Info

Publication number
US20020013238A1
US20020013238A1 US09/732,370 US73237000A US2002013238A1 US 20020013238 A1 US20020013238 A1 US 20020013238A1 US 73237000 A US73237000 A US 73237000A US 2002013238 A1 US2002013238 A1 US 2002013238A1
Authority
US
United States
Prior art keywords
group
chelating agent
compound selected
nitrogen
cleaning formulation
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
Application number
US09/732,370
Other versions
US6344432B1 (en
Inventor
William Wojtczak
Ma. Seijo
David Bernhard
Long Nguyen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Advanced Technology Materials Inc
Original Assignee
Advanced Technology Materials Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from US09/331,537 external-priority patent/US6211126B1/en
Application filed by Advanced Technology Materials Inc filed Critical Advanced Technology Materials Inc
Priority to US09/732,370 priority Critical patent/US6344432B1/en
Assigned to ADVANCED TECHNOLOGY MATERIALS, INC. reassignment ADVANCED TECHNOLOGY MATERIALS, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: NGUYEN, LONG, BERNHARD, DAVID, SEIJO, MA. FATIMA, WOJTCZAK, WILLIAM A.
Priority to US10/003,373 priority patent/US6660700B2/en
Priority to PCT/US2001/047289 priority patent/WO2002057513A1/en
Priority to CNB018213561A priority patent/CN1244719C/en
Priority to AT01990020T priority patent/ATE367460T1/en
Priority to KR1020037007701A priority patent/KR100890418B1/en
Priority to DE60129465T priority patent/DE60129465T2/en
Priority to EP01990020A priority patent/EP1349969B1/en
Priority to JP2002558561A priority patent/JP4091433B2/en
Priority to US10/007,490 priority patent/US6566315B2/en
Priority to TW090130319A priority patent/TWI243861B/en
Publication of US20020013238A1 publication Critical patent/US20020013238A1/en
Publication of US6344432B1 publication Critical patent/US6344432B1/en
Application granted granted Critical
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Images

Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02041—Cleaning
    • H01L21/02057—Cleaning during device manufacture
    • H01L21/02068—Cleaning during device manufacture during, before or after processing of conductive layers, e.g. polysilicon or amorphous silicon layers
    • H01L21/02071—Cleaning during device manufacture during, before or after processing of conductive layers, e.g. polysilicon or amorphous silicon layers the processing being a delineation, e.g. RIE, of conductive layers
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2072—Aldehydes-ketones
    • 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
    • C11D7/02—Inorganic compounds
    • 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
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/261—Alcohols; Phenols
    • 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
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/264—Aldehydes; Ketones; Acetals or ketals
    • 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
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/265—Carboxylic acids or salts 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/266—Esters or carbonates
    • 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
    • C11D7/3209—Amines or imines with one to four nitrogen atoms; Quaternized amines
    • 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
    • C11D7/3218—Alkanolamines or alkanolimines
    • 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
    • C11D7/3245—Aminoacids
    • 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
    • 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
    • C11D7/3272—Urea, guanidine or derivatives 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
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22—Organic compounds
    • C11D7/32—Organic compounds containing nitrogen
    • C11D7/3281—Heterocyclic compounds
    • 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
    • C11D7/5004—Organic solvents
    • C11D7/5009—Organic solvents containing phosphorus, sulfur or silicon, e.g. dimethylsulfoxide
    • 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
    • C11D7/5004—Organic solvents
    • C11D7/5013—Organic solvents containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic 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
    • G03F7/425—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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02041—Cleaning
    • H01L21/02057—Cleaning during device manufacture
    • H01L21/0206—Cleaning during device manufacture during, before or after processing of insulating layers
    • H01L21/02063—Cleaning during device manufacture during, before or after processing of insulating layers the processing being the formation of vias or contact holes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic System or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/3105—After-treatment
    • H01L21/311—Etching the insulating layers by chemical or physical means
    • H01L21/31127—Etching organic layers
    • H01L21/31133—Etching organic layers by chemical means
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic System or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/3105—After-treatment
    • H01L21/311—Etching the insulating layers by chemical or physical means
    • H01L21/31127—Etching organic layers
    • H01L21/31133—Etching organic layers by chemical means
    • H01L21/31138—Etching organic layers by chemical means by dry-etching
    • C11D2111/22—
    • 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
    • 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
    • C11D7/34—Organic compounds containing sulfur
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02041—Cleaning
    • H01L21/02043—Cleaning before device manufacture, i.e. Begin-Of-Line process
    • H01L21/02052—Wet cleaning only

Definitions

  • the present invention relates generally to chemical formulations that are useful in semiconductor wafer fabrication and particularly to chemical formulations that are utilized to remove residue from wafers following a resist plasma ashing step. More specifically, the present invention relates to cleaning formulations for removal of inorganic residue from semiconductor wafers containing delicate copper interconnecting structures.
  • Some of such formulations employ corrosion-inhibiting additives to prevent undesirable copper metal corrosion during the cleaning process.
  • conventional corrosion-inhibiting additives typically have detrimental effects on the cleaning process because such additives interact with the residue and inhibit dissolution of such residue in the cleaning fluid.
  • conventional additives do not easily rinse off copper surfaces after completion of the cleaning process and their presence results in contamination of the integrated circuits. Contamination of the integrated circuit will disadvantageously increase the electrical resistance of the contaminated areas and cause unpredictable conducting failures within the circuitry.
  • the present invention relates to semiconductor wafer cleaning formulations having utility for cleaning of semiconductor wafers, e.g., in post plasma ashing semiconductor fabrication.
  • the invention relates to a method of removing residue from a wafer following a resist plasma ashing step on such wafer, comprising contacting the wafer with a cleaning formulation, including (i) an organic amine, (ii) water, (iii) a nitrogen-containing carboxylic acid or an imine, (iv) a 1,3-dicarbonyl chelating compound, (v) a polar organic solvent, and optionally (vi) at least one other metal chelating agent.
  • a cleaning formulation including (i) an organic amine, (ii) water, (iii) a nitrogen-containing carboxylic acid or an imine, (iv) a 1,3-dicarbonyl chelating compound, (v) a polar organic solvent, and optionally (vi) at least one other metal chelating agent.
  • a wafer cleaning formulation including (i) an organic amine, (ii) water, (iii) a nitrogen-containing carboxylic acid or an imine, (iv) a 1,3-dicarbonyl chelating compound, (v) a polar organic solvent, and optionally (vi) at least one other metal chelating agent.
  • the invention relates to a semiconductor wafer cleaning formulation for use in post plasma ashing semiconductor fabrication, comprising the following components in the percentage by weight (based on the total weight of the formulation) ranges shown: organic amine(s) 2-98% water 0-50% 1,3-dicarbonyl compound chelating agent 0.1-60% additional different chelating agent(s) 0-25% nitrogen-containing carboxylic acid or imine 0.5-40% polar organic solvent 2-98% TOTAL 100%
  • the formulations of the present invention effectively remove inorganic residues, especially metal halide and metal oxide residues, following a plasma ashing step. Such formulations also significantly reduce undesirable corrosion or removal of copper metal structures on the semiconductor wafer during their use.
  • the formulations of the present invention additionally leave less contamination after the residue-removal process and therefore improve quality of the resulting microelectronic device products.
  • FIG. 1 is a schematic representation of a copper-specific corrosion inhibitor useful in the broad practice of the present invention, which forms a protective layer on the copper metal to prevent corrosion.
  • FIG. 2 is a schematic representation of the copper-specific corrosion inhibitor being rinsed away from the copper surface by deionized water.
  • the present invention relates to formulations that are suitable for stripping inorganic wafer residues arising from high-density plasma etching followed by ashing with oxygen-containing plasmas.
  • the formulations advantageously contain 1,3-dicarbonyl compounds and/or other metal chelating agents, nitrogen-containing carboxyl acids or imines, amines, and water or other solvent as primary ingredients.
  • the preferred formulations comprise the following components in the percentage by weight (based on the total weight of the formulation) ranges shown: organic amine(s) 2-98% water 0-50% 1,3-dicarbonyl compound chelating agent 0.1-60% additional different chelating agent(s) 0-25% nitrogen-containing carboxylic acid or imine 0.5-40% polar organic solvent 2-98% TOTAL 100%
  • the components of the formulation as described above can be of any suitable type or species, as will be appreciated by those of ordinary skill in the art. Specific illustrative and preferred formulation components for each of the ingredients of the formulation are described below, with specific components being identified with their preferred wt. % concentrations in the formulation, on the total weight basis specified above.
  • Preferred amines include: pentamethyldiethylenetriamine (PMDETA) 5-95% triethanolamine (TEA) 5-95%
  • Specific preferred 1,3-dicarbonyl compound chelating agents include: 2,4-pentanedione 2-90% N,N-Dimethylacetoacetamide 2-90% methyl acetoacetate 15-70% dimethylmalonate 10-48.3%
  • the preferred nitrogen-containing carboxylic acids or imines include: iminodiacetic acid 0.5-2.5% glycine 0.5-2.5% nitrilotriacetic acid 0.5-2.5% 1,1,3,3-tetramethylguanidine 0.5-2.5%
  • the preferred solvents include: water 0-50% ethylene glycol 0-74% N-methylpyrrolidone (NMP) 0-49% sulfolane 0-10%
  • Preferred secondary or alternative chelating agents optionally utilized in some of the formulations of the invention include: ammonium pyrrolidinedithiocarbamate 0-25% ammonium carbamate 0-15% ammonium oxalate 0-15% ammonium thiocyanate 0-15% ammonium thiosulfate 0-15% trifluoroacetic acid 0-12%
  • formulations containing 1,3-dicarbonyl compounds and/or other metal-chelating agents in combination with amines and a solvent enables unique improvements of the art to be realized.
  • inventive formulations provide better stripping performance and less corrosivity than conventional wafer stripping formulations containing catechol, amine, and solvent.
  • the addition of nitrogen-containing carboxylic acids or imines is another advantageous improvement of the present invention.
  • the nitrogen-containing carboxylic acids or imines contain functional groups that are specifically attracted to free copper atoms.
  • the copper-specific corrosion inhibiting agent C which contacts the copper surface during the residue-removal process, will attach to the copper surface and form a protective layer to prevent the copper surface being corroded by cleaning agents A + and X ⁇ .
  • such copper-specific corrosion-inhibiting agent C can be easily rinsed off by deionized water or other rinse media and therefore leaves very little contamination on the copper surface after the cleaning operation is completed.
  • the formulations of the invention may include a wide variety of solvents, organic amines, chelating agents, and nitrogen-containing carboxylic acids or imines, other than those specifically exemplified.
  • Particular 1,3-dicarbonyl compounds and related compounds of suitable character include those of the formula:
  • R is either a hydrogen atom or an aliphatic group, e.g., C 1 -C 8 alkyl, aryl, alkenyl, etc.
  • X and Y are the same as or different from one another, and are functional groups containing multiply-bonded moieties with electron-withdrawing properties, as for example CONH 2 , CONHR′, CONR′R′, CN, NO 2 , SOR′, or SO 2 Z, in which R′ and R′′ are same or different and represent a C 1 -C 8 alkyl group and Z represents another atom or group, e.g., hydrogen, halo or C 1 -C8 alkyl.
  • each of R and R′ is independently selected from the group consisting of hydrogen, alkyl, aryl, and carboxylic acid.
  • Carbamate salts and dialkyldithiocarbamates other than those specifically mentioned hereinabove may be used as chelating agents in the broad practice of the invention.
  • Various other polar organic solvents may be used, e.g., alone or mixed with water.
  • formulations of the invention optionally may also include such components as surfactants, stabilizers, corrosion inhibitors, buffering agents, and co-solvents, as useful or desired in a given end use application of formulations of the invention.
  • the formulations of the present invention are particularly useful on wafers that have been etched with chlorine- or fluorine-containing plasmas followed by oxygen plasma ashing.
  • the residues generated by this type of processing typically contain metal oxides. These residues are often difficult to dissolve completely without causing corrosion of metal features required for effective device performance.
  • Copper-specific corrosion inhibitors including either nitrogen-containing carboxylic acids or imines were tested in two different types of alkaline cleaning formulations, with the following components and characteristics.
  • TABLE 1 Copper Etch Components Temp. pH Rate ( ⁇ /min) Formu- Dimethylacetoacetamide, 70 6.2 17.4 lation 1 Amine, and Water Formu- Ammonium Fluoride, 40 8.6 7.5 lation 2 Triethanolamine, Pentamethdiethylenetriamine, and Water
  • the copper etch rate was determined by a standard four-point probe technique. Addition of corrosion inhibitors in accordance with the present invention significantly slowed down the copper etch rate, as shown by the following table, and effectively prevented undesirable corrosion during the cleaning process: TABLE 2 Copper Reduction Etch of Temp.
  • a contamination test is carried out on formulation 2 containing iminodiacetic acid inhibitor.
  • the semiconductor wafer to be cleaned contained copper and silicon films. After the completion of the cleaning operation, the wafer was rinsed by deionized water at 25° C. for about 15 minutes.
  • the Secondary Ion Mass Spectrometry data (SIMS) obtained are as follows: Cu F C Cu x O (atoms/cm 2 ) (atoms/cm 2 ) (atoms/cm 2 ) ( ⁇ ) Uncleaned Wafer 1.6 ⁇ 10 10 3.3 ⁇ 10 13 7.5 ⁇ 10 13 42 Cleaned Wafer 8.5 ⁇ 10 9 5.1 ⁇ 10 13 1.5 ⁇ 10 13 15

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • General Physics & Mathematics (AREA)
  • Emergency Medicine (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Computer Hardware Design (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Power Engineering (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Cleaning Or Drying Semiconductors (AREA)
  • Detergent Compositions (AREA)
  • Led Devices (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Drying Of Semiconductors (AREA)

Abstract

A semiconductor wafer cleaning formulation, including 2-98% wt. organic amine, 0-50% wt. water, 0.1-60% wt. 1,3-dicarbonyl compound chelating agent, 0-25% wt. of additional different chelating agent(s), 0.5-40% wt. nitrogen-containing carboxylic acid or an imine, and 2-98% wt polar organic solvent. The formulations are useful to remove residue from wafers following a resist plasma ashing step, such as inorganic residue from semiconductor wafers containing delicate copper interconnecting structures.

Description

    BACKGROUND OF THE INVENTION
  • 1. Field of the Invention [0001]
  • The present invention relates generally to chemical formulations that are useful in semiconductor wafer fabrication and particularly to chemical formulations that are utilized to remove residue from wafers following a resist plasma ashing step. More specifically, the present invention relates to cleaning formulations for removal of inorganic residue from semiconductor wafers containing delicate copper interconnecting structures. [0002]
  • 2. Description of the Prior Art [0003]
  • Various chemical formulations are conventionally employed to remove residue and clean wafers following a resist ashing step. Some of these chemical formulations include akaline compositions containing amines and/or tetraalkyl ammonium hydroxides, water and/or other solvents, and chelating agents. Such formulations have associated drawbacks which include unwanted removal of metal or insulator layers and the promotion of corrosion of desirable metal layers, particularly copper or copper alloys features. [0004]
  • Some of such formulations employ corrosion-inhibiting additives to prevent undesirable copper metal corrosion during the cleaning process. However, conventional corrosion-inhibiting additives typically have detrimental effects on the cleaning process because such additives interact with the residue and inhibit dissolution of such residue in the cleaning fluid. Further, conventional additives do not easily rinse off copper surfaces after completion of the cleaning process and their presence results in contamination of the integrated circuits. Contamination of the integrated circuit will disadvantageously increase the electrical resistance of the contaminated areas and cause unpredictable conducting failures within the circuitry. [0005]
  • It is therefore an object of the present invention to provide chemical formulations that effectively remove residue following a resist ashing step. [0006]
  • It is another object to provide wafer cleaning formulations that do not attack and potentially degrade delicate metal structures that are meant to remain on the wafer. [0007]
  • It is yet another object of the present invention to provide a wafer cleaning formulation including an improved corrosion inhibitor for protection of copper structures on the semiconductor substrate, in a compositional form that is easily rinsed off by water or other rinse media after the completion of the residue-removal process, thereby reducing contamination of the integrated circuitry on the wafer substrate. [0008]
  • Other objects and advantages of the invention will become fully apparent from the ensuing disclosure and appended claims. [0009]
    • SUMMARY OF THE INVENTION
  • The present invention relates to semiconductor wafer cleaning formulations having utility for cleaning of semiconductor wafers, e.g., in post plasma ashing semiconductor fabrication. [0010]
  • In one aspect, the invention relates to a method of removing residue from a wafer following a resist plasma ashing step on such wafer, comprising contacting the wafer with a cleaning formulation, including (i) an organic amine, (ii) water, (iii) a nitrogen-containing carboxylic acid or an imine, (iv) a 1,3-dicarbonyl chelating compound, (v) a polar organic solvent, and optionally (vi) at least one other metal chelating agent. [0011]
  • Another aspect of the invention relates to a wafer cleaning formulation, including (i) an organic amine, (ii) water, (iii) a nitrogen-containing carboxylic acid or an imine, (iv) a 1,3-dicarbonyl chelating compound, (v) a polar organic solvent, and optionally (vi) at least one other metal chelating agent. [0012]
  • In a further aspect, the invention relates to a semiconductor wafer cleaning formulation for use in post plasma ashing semiconductor fabrication, comprising the following components in the percentage by weight (based on the total weight of the formulation) ranges shown: [0013]
    organic amine(s) 2-98%
    water 0-50%
    1,3-dicarbonyl compound chelating agent 0.1-60%
    additional different chelating agent(s) 0-25%
    nitrogen-containing carboxylic acid or imine 0.5-40%
    polar organic solvent 2-98%
    TOTAL 100%
  • The formulations of the present invention effectively remove inorganic residues, especially metal halide and metal oxide residues, following a plasma ashing step. Such formulations also significantly reduce undesirable corrosion or removal of copper metal structures on the semiconductor wafer during their use. [0014]
  • The formulations of the present invention additionally leave less contamination after the residue-removal process and therefore improve quality of the resulting microelectronic device products. [0015]
  • Other features and advantages of the present invention will be from the ensuing disclosure and appended claims.[0016]
    • BRIEF DESCRIPTION OF THE DRAWINGS
  • FIG. 1 is a schematic representation of a copper-specific corrosion inhibitor useful in the broad practice of the present invention, which forms a protective layer on the copper metal to prevent corrosion. [0017]
  • FIG. 2 is a schematic representation of the copper-specific corrosion inhibitor being rinsed away from the copper surface by deionized water.[0018]
    • DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
  • The present invention relates to formulations that are suitable for stripping inorganic wafer residues arising from high-density plasma etching followed by ashing with oxygen-containing plasmas. [0019]
  • The formulations advantageously contain 1,3-dicarbonyl compounds and/or other metal chelating agents, nitrogen-containing carboxyl acids or imines, amines, and water or other solvent as primary ingredients. [0020]
  • The preferred formulations comprise the following components in the percentage by weight (based on the total weight of the formulation) ranges shown: [0021]
    organic amine(s) 2-98%
    water 0-50%
    1,3-dicarbonyl compound chelating agent 0.1-60%
    additional different chelating agent(s) 0-25%
    nitrogen-containing carboxylic acid or imine 0.5-40%
    polar organic solvent 2-98%
    TOTAL 100%
  • The components of the formulation as described above can be of any suitable type or species, as will be appreciated by those of ordinary skill in the art. Specific illustrative and preferred formulation components for each of the ingredients of the formulation are described below, with specific components being identified with their preferred wt. % concentrations in the formulation, on the total weight basis specified above. [0022]
  • Preferred amines include: [0023]
    pentamethyldiethylenetriamine (PMDETA) 5-95%
    triethanolamine (TEA) 5-95%
  • Other amines that are highly advantageous include: [0024]
  • monoethanolamine [0025]
  • diglycolamine [0026]
  • diazabicyclo (2.2.2) octane [0027]
  • diethylenetriamine [0028]
  • 3,3′-iminobis (N,N-dimethylpropylamine) [0029]
  • N-methylimidazole [0030]
  • tetraethylenepentamine [0031]
  • triethylenetetramine [0032]
  • trimethoxyethoxyethylamine [0033]
  • diethanolamine [0034]
  • methyldiethanolamine [0035]
  • tetramethylhexanediamine [0036]
  • N,N-diethylethanolamine [0037]
  • Specific preferred 1,3-dicarbonyl compound chelating agents include: [0038]
    2,4-pentanedione 2-90%
    N,N-Dimethylacetoacetamide 2-90%
    methyl acetoacetate 15-70%
    dimethylmalonate 10-48.3%
  • Other 1,3-dicarbonyl compounds that are highly advantageous include: [0039]
  • N-methylacetoacetamide [0040]
  • acetoacetamide [0041]
  • malonamide [0042]
  • The preferred nitrogen-containing carboxylic acids or imines include: [0043]
    iminodiacetic acid 0.5-2.5%
    glycine 0.5-2.5%
    nitrilotriacetic acid 0.5-2.5%
    1,1,3,3-tetramethylguanidine 0.5-2.5%
  • Other nitrogen-containing carboxylic acids or imines that are highly advantageous include: [0044]
  • CH[0045] 3C(═NCH2CH2OH)CH2C(O)N(CH3)2
  • CH[0046] 3C(═NCH2CH2OCH2CH2OH)CH2C(O)N(CH3)2
  • CH[0047] 3C(═NH)CH2C(O)CH3
  • (CH[0048] 3CH2)2NC(═NH)N(CH3CH2)2
  • HOOCCH[0049] 2N(CH3)2
  • HOOCCH[0050] 2N(CH3)CH2COOH
  • The preferred solvents include: [0051]
    water 0-50%
    ethylene glycol 0-74%
    N-methylpyrrolidone (NMP) 0-49%
    sulfolane 0-10%
  • Preferred secondary or alternative chelating agents optionally utilized in some of the formulations of the invention include: [0052]
    ammonium pyrrolidinedithiocarbamate 0-25%
    ammonium carbamate 0-15%
    ammonium oxalate 0-15%
    ammonium thiocyanate 0-15%
    ammonium thiosulfate 0-15%
    trifluoroacetic acid 0-12%
  • The utilization of formulations containing 1,3-dicarbonyl compounds and/or other metal-chelating agents in combination with amines and a solvent enables unique improvements of the art to be realized. The inventive formulations provide better stripping performance and less corrosivity than conventional wafer stripping formulations containing catechol, amine, and solvent. [0053]
  • The addition of nitrogen-containing carboxylic acids or imines is another advantageous improvement of the present invention. The nitrogen-containing carboxylic acids or imines contain functional groups that are specifically attracted to free copper atoms. As shown by FIG. 1, the copper-specific corrosion inhibiting agent C, which contacts the copper surface during the residue-removal process, will attach to the copper surface and form a protective layer to prevent the copper surface being corroded by cleaning agents A[0054] + and X−. Moreover, as shown by FIG. 2, such copper-specific corrosion-inhibiting agent C can be easily rinsed off by deionized water or other rinse media and therefore leaves very little contamination on the copper surface after the cleaning operation is completed.
  • The formulations of the invention may include a wide variety of solvents, organic amines, chelating agents, and nitrogen-containing carboxylic acids or imines, other than those specifically exemplified. Particular 1,3-dicarbonyl compounds and related compounds of suitable character include those of the formula: [0055]
  • X—CHR—Y
  • wherein R is either a hydrogen atom or an aliphatic group, e.g., C[0056] 1-C8 alkyl, aryl, alkenyl, etc., X and Y are the same as or different from one another, and are functional groups containing multiply-bonded moieties with electron-withdrawing properties, as for example CONH2, CONHR′, CONR′R′, CN, NO2, SOR′, or SO2Z, in which R′ and R″ are same or different and represent a C1-C8 alkyl group and Z represents another atom or group, e.g., hydrogen, halo or C1-C8 alkyl.
  • Additional nitrogen-containing carboxylic acids having utility in the broad practice of the invention include those of the formula: [0057]
  • COOH—CH2—NRR′
  • wherein each of R and R′ is independently selected from the group consisting of hydrogen, alkyl, aryl, and carboxylic acid. [0058]
  • Carbamate salts and dialkyldithiocarbamates other than those specifically mentioned hereinabove may be used as chelating agents in the broad practice of the invention. [0059]
  • Various other polar organic solvents may be used, e.g., alone or mixed with water. [0060]
  • The formulations of the invention optionally may also include such components as surfactants, stabilizers, corrosion inhibitors, buffering agents, and co-solvents, as useful or desired in a given end use application of formulations of the invention. [0061]
  • The formulations of the present invention are particularly useful on wafers that have been etched with chlorine- or fluorine-containing plasmas followed by oxygen plasma ashing. The residues generated by this type of processing typically contain metal oxides. These residues are often difficult to dissolve completely without causing corrosion of metal features required for effective device performance. [0062]
  • The features and advantages of the invention are more fully shown by the following non-limiting examples. [0063]
    • EXAMPLE 1
  • Copper-specific corrosion inhibitors including either nitrogen-containing carboxylic acids or imines were tested in two different types of alkaline cleaning formulations, with the following components and characteristics. [0064]
    TABLE 1
    Copper Etch
    Components Temp. pH Rate (Å/min)
    Formu- Dimethylacetoacetamide, 70 6.2 17.4
    lation 1 Amine, and Water
    Formu- Ammonium Fluoride, 40 8.6 7.5
    lation 2 Triethanolamine,
    Pentamethdiethylenetriamine, and
    Water
  • The copper etch rate was determined by a standard four-point probe technique. Addition of corrosion inhibitors in accordance with the present invention significantly slowed down the copper etch rate, as shown by the following table, and effectively prevented undesirable corrosion during the cleaning process: [0065]
    TABLE 2
    Copper Reduction
    Etch of
    Temp. Formulation Concentration pH of Rate Etch Rate
    Corrosion Inhibitor (° C.) Used (%) solution (Å/min) (%)
    Iminodiacetic Acid 40 2 1.5 8.0 1-2 −73.3˜86.7
    Glycine 40 2 1.5 9.2 3.6 −52.0
    Nitrilotriacetic Acid 40 2 1.5 8.2 3.6 −52.0
    1,1,3,3-tetramethylguanidine 40 2 1.5 8.7 3.4 −54.7
    CH3C(═NCH2CH2OH)CH2 70 1 24 10.9 6.2 −64.4
    C(O)N(CH3)2
    CH3C(═NCH2CH2OCH2CH2OH) 70 1 36 10.7 0.32 −98.2
    CH2C(O)N(CH3)2
    CH3C(═NH)CH2C(O)CH3 40 2 13.68 7.9 4.4 −41.3
    • EXAMPLE 2
  • A contamination test is carried out on formulation 2 containing iminodiacetic acid inhibitor. The semiconductor wafer to be cleaned contained copper and silicon films. After the completion of the cleaning operation, the wafer was rinsed by deionized water at 25° C. for about 15 minutes. The Secondary Ion Mass Spectrometry data (SIMS) obtained are as follows: [0066]
    Cu F C CuxO
    (atoms/cm2) (atoms/cm2) (atoms/cm2) (Å)
    Uncleaned Wafer 1.6 × 1010 3.3 × 1013 7.5 × 1013 42
    Cleaned Wafer 8.5 × 109  5.1 × 1013 1.5 × 1013 15
  • The foregoing results show that the copper oxide Cu[0067] xO has been effectively removed by the cleaning process, while carbon contamination, which is mainly caused by the organic corrosion inhibitors in the cleaning formulation, has been greatly reduced.
  • While the invention has been described herein with reference to specific features, aspects, and embodiments, it will be appreciated that the invention is not thus limited. The invention therefore may correspondingly embodied in a wide variety of compositions, with corresponding variations of ingredients, and end-use applications. The invention therefore is to be understood as encompassing all such variations, modifications and alternative embodiments, within the spirit and scope of the invention as hereafter claimed. [0068]

Claims (28)

What is claimed is:
1. A semiconductor wafer cleaning formulation for use in post plasma ashing semiconductor fabrication, comprising the following components in the percentage by weight (based on the total weight of the formulation) ranges shown:
organic amine(s) 2-98% water 0-50% 1,3-dicarbonyl compound chelating agent 0.1-60%   additional different chelating agent(s) 0-25% nitrogen-containing carboxylic acid or imine 0.5-40%   polar organic solvent 2-98% TOTAL 100%.
2. The cleaning formulation as described in claim 1 wherein said organic amine(s) comprise a compound selected from the group consisting of:
pentamethyldiethylenetriamine (PMDETA) 5-95% triethanolamine (TEA)  5-95%.
3. The cleaning formulation of claim 1 wherein said 1,3-dicarbonyl compound chelating agent comprises a compound selected from the group consisting of:
2,4-Pentanedione 2-90% N,N-Dimethylacetoacetamide 2-90% methyl acetoacetate 15-70%  dimethylmalonate  10-48.3%.
4. The cleaning formulation of claim 1 wherein said nitrogen-containing carboxylic acid or imine comprises a compound selected from the group consisting of:
iminodiacetic acid (IDA) 0.5-2.5% glycine 0.5-2.5% nitrilotriacetic acid (NTA) 0.5-2.5% 1,1,3,3-tetramethylguanidine (TMG)  0.5-2.5%.
5. The cleaning formulation of claim 1 wherein said polar organic solvent comprises a solvent species selected from the group consisting of:
ethylene glycol 0-74% N-methylpyrrolodone (NMP) 0-49% sulfolane 0-10%
6. The cleaning formulation of claim 1 wherein said additional different chelating agent(s) comprise a species selected from the group consisting of:
ammonium pyrrolidinedithiocarbamate 0-25% ammonium carbamate 0-15% ammonium oxalate 0-15% ammonium thiocyanate 0-15% ammonium thiosulfate 0-15% trifluoroacetic acid  0-12%.
7. The cleaning formulation of claim 1 wherein said organic amine(s) comprise a species selected from the group consisting of:
monoethanolamine
diglycolamine
pentamethyldiethylenetriamine (PMDETA)
triethanolamine (TEA)
diazabicyclo (2.2.2) octane
diethylenetriamine
3,3′-iminobis (N,N-dimethylpropylamine)
N-methylimidazole
tetraethylenepentamine
Triethylenetetramine
trimethoxyethoxyethylamine
diethanolamine
methyldiethanolamine
tetramethylhexanediamine
N,N-diethylethanolamine.
8. The cleaning formulation of claim 1 wherein said 1,3-dicarbonyl compound chelating agent comprises a compound selected from the group consisting of:
2,4-pentanedione
methyl acetoacetate
dimethylmalonate
N-methylacetoacetamide
N,N-Dimethylacetoacetamide
acetoacetamide
malonamide.
9. The cleaning formulation of claim 1, wherein said nitrogen-containing carboxyl acid or imine is selected from the group consisting of:
iminodiacetic acid (IDA)
glycine
nitrilotriacetic acid (NTA)
1,1,3,-tetramethylguanidine (TMG)
CH3C(═NCH2CH2OH)CH2C(O)N(CH3)2
CH3C(═NCH2CH2OCH2CH2OH)CH2C(O)N(CH3)2
CH3C(═NH)CH2C(O)CH3
(CH3CH2)2NC(═NH)N(CH3CH2)2
HOOCCH2N(CH3)2
HOOCCH2N(CH3)CH2COOH.
10. The cleaning formulation of claim 1 wherein said organic amine(s) comprise a compound selected from the group consisting of:
pentamethyldiethylenetriamine (PMDETA) 5-95% triethanolamine (TEA) 5-95%
said 1,3-dicarbonyl compound chelating agent comprises a compound selected from the group consisting of:
2,4-pentanedione 2-90% N,N-Dimethylacetoacetamide 2-90% methyl acetoacetate 15-70%  dimethylmalonate   0-48.3%
said nitrogen-containing carboxylic acid or imine comprises a compound selected from the group consisting of:
iminodiacetic acid (IDA) 0.5-2.5% glycine 0.5-2.5% nitrilotriacetic acid (NTA) 0.5-2.5% 1,1,3,3-tetramethylguanidine (TMG) 0.5-2.5%
and said polar organic solvent comprises a solvent species selected from the group consisting of:
ethylene glycol 0-74% N-methylpyrrolodone (NMP) 0-49% sulfolane  0-10%.
11. The cleaning formulation of claim 1 comprising a chelating agent having the formula:
X—CHR—Y
in which
R is either hydrogen or an aliphatic group and
X and Y are functional groups containing multiply bonded moieties having electron-withdrawing properties.
12. The cleaning formulation of claim 11 wherein each of X and Y is independently selected from CONH2, CONHR′, CONR′R″, CN, NO2, SOR′, and SO2Z in which R′ and R″ are alkyl and Z is hydrogen, halo, or alkyl.
13. The cleaning formulation of claim 1, wherein said nitrogen-containing carboxylic acid has the formula:
COOH—CH2—NRR′
wherein each of R and R′ is independently selected from the group consisting of hydrogen, alkyl, aryl, and carboxylic acids.
14. A method for fabricating a semiconductor wafer including the steps comprising:
plasma etching a metalized layer from a surface of the wafer;
plasma ashing a resist from the surface of the wafer;
cleaning the wafer with a semiconductor wafer cleaning formulation comprising the following components in the percentage by weight (based on the total weight of the formulation) ranges shown:
organic amine(s) 2-98% water 0-50% 1,3-dicarbonyl compound chelating agent 0.1-60%   additional different chelating agent(s) 0-25% nitrogen-containing carboxylic acid or imine 0.5-40%   polar organic solvent 2-98% TOTAL 100%.
15. The method of claim 14 wherein said organic amine(s) comprises a compound selected from the group consisting of:
Pentamethyldiethylenetriamine (PMDETA) 5-95%  Triethanolamine (TEA) 5-95%.
16. The method of claim 14 wherein said 1,3-dicarbonyl compound chelating agent comprises a compound selected from the group consisting of:
2,4-pentanedione 2-90% N,N-Dimethylacetoacetamide 2-90% methyl acetoacetate 15-70%  dimethylmalonate  10-48.3%.
17. The method of claim 14 wherein said nitrogen-containing carboxylic acid or imine comprises a compound selected from the group consisting of:
iminodiacetic acid (IDA) 0.5-2.5% glycine 0.5-2.5% nitrilotriacetic acid (NTA) 0.5-2.5% 1,1,3,3-tetramethylguanidine (TMG)  0.5-2.5%.
18. The method of claim 14 wherein said polar organic solvent comprises a solvent species selected from the group consisting of:
ethylene glycol 0-74% N-methylpyrrolodone (NMP) 0-49% sulfolane  0-10%.
19. The method of claim 14 wherein said additional different chelating agent(s) comprises a compound selected from the group consisting of:
ammonium pyrrolidinedithiocarbamate 0-25% ammonium carbamate 0-15% ammonium oxalate 0-15% ammonium thiocyanate 0-15% ammonium thiosulfate 0-15% trifluoroacetic acid  0-12%.
20. The method of claim 14 wherein said organic amine(s) comprises a compound selected from the group consisting of:
pentamethyldiethylenetriamine (PMDETA)
monoethanolamine
diglycolamine
triethanolamine (TEA)
diazabicyclo (2.2.2) octane
diethylenetriamine
3,3′-iminobis (N,N-dimethylpropylamine)
N-methylimidazole
tetraethylenepentamine
triethylenetetramine
trimethoxyethoxyethylamine
diethanolamine
methyldiethanolamine
tetramethylhexanediamine
N,N-diethylethanolamine.
21. The method of claim 14 wherein said 1,3-dicarbonyl compound chelating agent comprises a compound selected from the group consisting of:
2,4-pentanedione
N,N-Dimethylacetoacetamide
methyl acetoacetate
dimethylmalonate
N-methyl a acetoacetamide
acetoacetamide
malonamide.
22. The method of claim 14, wherein said nitrogen-containing carboxyl acid or imine comprises a compound selected from the group consisting of:
iminodiacetic acid (IDA)
glycine
nitrilotriacetic acid (NTA)
1,1,3,-tetramethylguanidine (TMG)
CH3C(═NCH2CH2OH)CH2C(O)N(CH3)2
CH3C(═NCH2CH2OCH2CH2OH)CH2C(O)N(CH3)2
CH3C(═NH)CH2C(O)CH3
(CH3CH2)2NC(═NH)N(CH3CH2)2
HOOCCH2N(CH3)2
HOOCCH2N(CH3)CH2COOH.
23. The method of claim 14 wherein said organic amine(s) comprises a compound selected from the group consisting of:
pentamethyldiethylenetriamine (PMDETA) 5-95% triethanolamine (TEA)  5-95%.
said 1,3-dicarbonyl compound chelating comprises a compound selected from the group consisting of:
2,4-pentanedione 2-90% N,N-Dimethylacetoacetamide 2-90% methyl acetoacetate 15-70%  dimethylmalonate  10-48.3%
said nitrogen-containing carboxylic acid or imine comprises a compound selected from the group consisting of:
iminodiacetic acid (IDA) 0.5-2.5% glycine 0.5-2.5% nitrilotriacetic acid (NTA) 0.5-2.5% 1,1,3,3-tetramethylguanidine (TMG) 0.5-2.5%
and said polar organic solvent comprises a compound selected from the group consisting of:
ethylene glycol 0-74% N-methylpyrrolodone (NMP) 0-49% sulfolane  0-10%.
24. The method of claim 14 wherein the formulation comprises a chelating agent having the formula:
X—CHR—Y
in which
R is either hydrogen or an aliphatic group and
X and Y are functional groups containing multiply bonded moieties having electron-withdrawing properties.
25. The method of claim 24 wherein each of X and Y is independently selected from CONH2, CONHR′, CONR′R″, CN, NO2, SOR′, and SO2Z in which R′ and R″ are alkyl and Z is hydrogen, halo, or alkyl.
26. The method of claim 14, comprising a nitrogen-containing carboxylic acid having the formula:
COOH—CH2—NRR′
wherein each of R and R′ is independently selected from the group consisting of hydrogen, alkyl, aryl, and carboxylic acids.
27. A method of removing residue from a wafer following a resist plasma ashing step on said wafer, comprising contacting the wafer with a cleaning formulation, including (i) organic amine(s), (ii) water, (iii) 1,3-dicarbonyl compound chelating agent, (iv) nitrogen-containing carboxylic acid or imine, (v) polar organic solvent, and optionally (vi) additional different chelating agent(s).
28. A wafer cleaning formulation, including (i) organic amine(s), (ii) water, (iii) 1,3-dicarbonyl compound chelating agent, (iv) nitrogen-containing carboxylic acid or imine, (v) polar organic solvent, and optionally (vi) additional different chelating agent(s).
US09/732,370 1999-08-20 2000-12-08 Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures Expired - Fee Related US6344432B1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US09/732,370 US6344432B1 (en) 1999-08-20 2000-12-08 Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
US10/003,373 US6660700B2 (en) 1999-08-20 2001-11-15 Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
CNB018213561A CN1244719C (en) 2000-12-08 2001-12-04 Semiconductor stripping composition containing 1,3-dicarbonyl compounds
KR1020037007701A KR100890418B1 (en) 2000-12-08 2001-12-04 Semiconductor stripping composition containing 1,3-dicarbonyl compounds
JP2002558561A JP4091433B2 (en) 2000-12-08 2001-12-04 Semiconductor stripping composition comprising a 1,3-dicarbonyl compound
AT01990020T ATE367460T1 (en) 2000-12-08 2001-12-04 SEMICONDUCTOR STRIP COMPOSITION CONTAINING 1,3-DICARBONYL COMPOUNDS
PCT/US2001/047289 WO2002057513A1 (en) 2000-12-08 2001-12-04 Semiconductor stripping composition containing 1,3-dicarbonyl compounds
DE60129465T DE60129465T2 (en) 2000-12-08 2001-12-04 1,3-DICARBONYL COMPOUNDS CONTAINING SEMICONDUCTOR STRIP COMPOSITION
EP01990020A EP1349969B1 (en) 2000-12-08 2001-12-04 Semiconductor stripping composition containing 1,3-dicarbonyl compounds
US10/007,490 US6566315B2 (en) 2000-12-08 2001-12-05 Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
TW090130319A TWI243861B (en) 2000-12-08 2001-12-07 Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/331,537 US6211126B1 (en) 1997-12-23 1997-12-23 Formulations including a 1, 3-dicarbonyl compound chelating agent for stripping residues from semiconductor substrates
US09/732,370 US6344432B1 (en) 1999-08-20 2000-12-08 Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US09/331,537 Continuation-In-Part US6211126B1 (en) 1997-12-23 1997-12-23 Formulations including a 1, 3-dicarbonyl compound chelating agent for stripping residues from semiconductor substrates

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US10/003,373 Division US6660700B2 (en) 1999-08-20 2001-11-15 Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
US10/007,490 Continuation-In-Part US6566315B2 (en) 2000-12-08 2001-12-05 Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures

Publications (2)

Publication Number Publication Date
US20020013238A1 true US20020013238A1 (en) 2002-01-31
US6344432B1 US6344432B1 (en) 2002-02-05

Family

ID=24943259

Family Applications (2)

Application Number Title Priority Date Filing Date
US09/732,370 Expired - Fee Related US6344432B1 (en) 1999-08-20 2000-12-08 Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
US10/003,373 Expired - Lifetime US6660700B2 (en) 1999-08-20 2001-11-15 Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures

Family Applications After (1)

Application Number Title Priority Date Filing Date
US10/003,373 Expired - Lifetime US6660700B2 (en) 1999-08-20 2001-11-15 Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures

Country Status (9)

Country Link
US (2) US6344432B1 (en)
EP (1) EP1349969B1 (en)
JP (1) JP4091433B2 (en)
KR (1) KR100890418B1 (en)
CN (1) CN1244719C (en)
AT (1) ATE367460T1 (en)
DE (1) DE60129465T2 (en)
TW (1) TWI243861B (en)
WO (1) WO2002057513A1 (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1551936A1 (en) * 2002-07-23 2005-07-13 Advanced Technology Materials, Inc. Composition and process for wet stripping removal of sacrificial anti-reflective material
US20060141157A1 (en) * 2003-05-27 2006-06-29 Masahiko Sekimoto Plating apparatus and plating method
US20100203735A1 (en) * 2007-08-22 2010-08-12 Daikin Industries, Ltd. Solution for removing residue after semiconductor dry process and method of removing the residue using the same
US9957469B2 (en) 2014-07-14 2018-05-01 Versum Materials Us, Llc Copper corrosion inhibition system

Families Citing this family (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6755989B2 (en) * 1997-01-09 2004-06-29 Advanced Technology Materials, Inc. Aqueous cleaning composition containing copper-specific corrosion inhibitor for cleaning inorganic residues on semiconductor substrate
US6896826B2 (en) * 1997-01-09 2005-05-24 Advanced Technology Materials, Inc. Aqueous cleaning composition containing copper-specific corrosion inhibitor for cleaning inorganic residues on semiconductor substrate
US6344432B1 (en) 1999-08-20 2002-02-05 Advanced Technology Materials, Inc. Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
US6566315B2 (en) * 2000-12-08 2003-05-20 Advanced Technology Materials, Inc. Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
US20030119692A1 (en) * 2001-12-07 2003-06-26 So Joseph K. Copper polishing cleaning solution
GB2401604A (en) * 2003-05-10 2004-11-17 Reckitt Benckiser Nv Water-softening product
US7241725B2 (en) * 2003-09-25 2007-07-10 Rohm And Haas Electronic Materials Cmp Holdings, Inc. Barrier polishing fluid
US7205235B2 (en) * 2003-12-15 2007-04-17 Freescale Semiconductor, Inc. Method for reducing corrosion of metal surfaces during semiconductor processing
US7819981B2 (en) * 2004-10-26 2010-10-26 Advanced Technology Materials, Inc. Methods for cleaning ion implanter components
US20060196525A1 (en) * 2005-03-03 2006-09-07 Vrtis Raymond N Method for removing a residue from a chamber
WO2006133253A1 (en) 2005-06-07 2006-12-14 Advanced Technology Materials, Inc. Metal and dielectric compatible sacrificial anti-reflective coating cleaning and removal composition
US8387824B2 (en) * 2005-07-02 2013-03-05 Syngenta Participations Ag Apparatuses and methods for bulk dispensing
CN101366107B (en) * 2005-10-05 2011-08-24 高级技术材料公司 Oxidizing aqueous cleaner for the removal of post-etch residues
US8603252B2 (en) * 2006-04-26 2013-12-10 Advanced Technology Materials, Inc. Cleaning of semiconductor processing systems
US20080142039A1 (en) * 2006-12-13 2008-06-19 Advanced Technology Materials, Inc. Removal of nitride deposits
TWI611047B (en) * 2006-12-21 2018-01-11 恩特葛瑞斯股份有限公司 Liquid cleaner for the removal of post-etch residues
US20100112728A1 (en) * 2007-03-31 2010-05-06 Advanced Technology Materials, Inc. Methods for stripping material for wafer reclamation
WO2009032322A1 (en) * 2007-09-06 2009-03-12 Ekc Technology, Inc. Compositions and method for treating a copper surface
KR101822779B1 (en) 2008-02-11 2018-01-26 엔테그리스, 아이엔씨. Ion source cleaning in semiconductor processing systems
CN102044407B (en) * 2009-10-20 2012-04-18 中芯国际集成电路制造(上海)有限公司 Cleaning method of chip
US8101561B2 (en) * 2009-11-17 2012-01-24 Wai Mun Lee Composition and method for treating semiconductor substrate surface
US8128755B2 (en) 2010-03-03 2012-03-06 L'air Liquide Societe Anonyme Pour L'etude Et L'exploitation Des Procedes Georges Claude Cleaning solvent and cleaning method for metallic compound
JP2012021151A (en) * 2010-06-16 2012-02-02 Sanyo Chem Ind Ltd Cleaning agent for copper wiring semiconductor
TWI548738B (en) 2010-07-16 2016-09-11 安堤格里斯公司 Aqueous cleaner for the removal of post-etch residues
JP6101421B2 (en) 2010-08-16 2017-03-22 インテグリス・インコーポレーテッド Etching solution for copper or copper alloy
CN103154321B (en) 2010-10-06 2015-11-25 安格斯公司 The composition of selective etch metal nitride and method
JP5933950B2 (en) 2011-09-30 2016-06-15 アドバンスド テクノロジー マテリアルズ，インコーポレイテッド Etching solution for copper or copper alloy
SG10201605172RA (en) 2011-12-28 2016-08-30 Entegris Inc Compositions and methods for selectively etching titanium nitride
EP2814895A4 (en) 2012-02-15 2015-10-07 Entegris Inc Post-cmp removal using compositions and method of use
JP2015517691A (en) 2012-05-18 2015-06-22 インテグリス，インコーポレイテッド Composition and process for stripping photoresist from a surface comprising titanium nitride
WO2014089196A1 (en) 2012-12-05 2014-06-12 Advanced Technology Materials, Inc. Compositions for cleaning iii-v semiconductor materials and methods of using same
US10472567B2 (en) 2013-03-04 2019-11-12 Entegris, Inc. Compositions and methods for selectively etching titanium nitride
SG10201708364XA (en) 2013-06-06 2017-11-29 Entegris Inc Compositions and methods for selectively etching titanium nitride
CN112442374A (en) 2013-07-31 2021-03-05 恩特格里斯公司 Aqueous formulations with Cu/W compatibility for removal of metal hardmask and post-etch residues
CN105492576B (en) 2013-08-30 2019-01-04 恩特格里斯公司 The composition and method of selective etch titanium nitride
KR102261638B1 (en) 2013-11-15 2021-06-08 삼성디스플레이 주식회사 Cleaner Composition and method of manufacturing metal line using the same
US10340150B2 (en) 2013-12-16 2019-07-02 Entegris, Inc. Ni:NiGe:Ge selective etch formulations and method of using same
TWI662379B (en) 2013-12-20 2019-06-11 美商恩特葛瑞斯股份有限公司 Use of non-oxidizing strong acids for the removal of ion-implanted resist
US10475658B2 (en) 2013-12-31 2019-11-12 Entegris, Inc. Formulations to selectively etch silicon and germanium
WO2015116818A1 (en) 2014-01-29 2015-08-06 Advanced Technology Materials, Inc. Post chemical mechanical polishing formulations and method of use
US11127587B2 (en) 2014-02-05 2021-09-21 Entegris, Inc. Non-amine post-CMP compositions and method of use
KR101669772B1 (en) * 2015-11-19 2016-10-27 오씨아이 주식회사 Composition for etching copper
WO2017086758A1 (en) * 2015-11-19 2017-05-26 오씨아이 주식회사 Composition for etching copper, and hydrogen peroxide-based composition for etching metal
CN109920729B (en) * 2019-03-27 2022-12-02 合肥鑫晟光电科技有限公司 Preparation method of display substrate and display device
CN113736574A (en) * 2021-09-27 2021-12-03 北京中铁富红企业管理有限责任公司 Cleaning agent for cleaning bullet train, preparation method of cleaning agent and bullet train cleaning method

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2059841A1 (en) 1991-01-24 1992-07-25 Ichiro Hayashida Surface treating solutions and cleaning method
TW274630B (en) 1994-01-28 1996-04-21 Wako Zunyaku Kogyo Kk
JP3074634B2 (en) * 1994-03-28 2000-08-07 三菱瓦斯化学株式会社 Stripping solution for photoresist and method for forming wiring pattern
JP3548237B2 (en) 1994-08-29 2004-07-28 シャープ株式会社 Thin film transistor
WO1997005228A1 (en) 1995-07-27 1997-02-13 Mitsubishi Chemical Corporation Method for treating surface of substrate and surface treatment composition therefor
EP0783034B1 (en) * 1995-12-22 2010-08-18 Mitsubishi Rayon Co., Ltd. Chelating agent and detergent comprising the same
WO1998022568A1 (en) 1996-11-22 1998-05-28 Advanced Chemical Systems International, Inc. Stripping formulation including catechol, hydroxylamine, non-alkanolamine, water for post plasma ashed wafer cleaning
JP4386968B2 (en) 1996-12-24 2009-12-16 アドバンスド テクノロジー マテリアルズ，インコーポレイテッド Formulation comprising a 1,3-dicarbonyl compound chelator for stripping residues from a semiconductor substrate
US6030491A (en) 1997-08-19 2000-02-29 Micron Technology, Inc. Processing compositions and methods of using same
US6211126B1 (en) * 1997-12-23 2001-04-03 Advanced Technology Materials, Inc. Formulations including a 1, 3-dicarbonyl compound chelating agent for stripping residues from semiconductor substrates
EP1125168A1 (en) * 1998-05-18 2001-08-22 Advanced Technology Materials, Inc. Stripping compositions for semiconductor substrates
US6248704B1 (en) * 1999-05-03 2001-06-19 Ekc Technology, Inc. Compositions for cleaning organic and plasma etched residues for semiconductors devices
US6344432B1 (en) 1999-08-20 2002-02-05 Advanced Technology Materials, Inc. Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
US6566315B2 (en) * 2000-12-08 2003-05-20 Advanced Technology Materials, Inc. Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1551936A1 (en) * 2002-07-23 2005-07-13 Advanced Technology Materials, Inc. Composition and process for wet stripping removal of sacrificial anti-reflective material
EP1551936A4 (en) * 2002-07-23 2008-04-16 Advanced Tech Materials Composition and process for wet stripping removal of sacrificial anti-reflective material
US20060141157A1 (en) * 2003-05-27 2006-06-29 Masahiko Sekimoto Plating apparatus and plating method
US20090301395A1 (en) * 2003-05-27 2009-12-10 Masahiko Sekimoto Plating apparatus and plating method
US20100203735A1 (en) * 2007-08-22 2010-08-12 Daikin Industries, Ltd. Solution for removing residue after semiconductor dry process and method of removing the residue using the same
US8822396B2 (en) 2007-08-22 2014-09-02 Daikin Industries, Ltd. Solution for removing residue after semiconductor dry process and method of removing the residue using the same
US9957469B2 (en) 2014-07-14 2018-05-01 Versum Materials Us, Llc Copper corrosion inhibition system

Also Published As

Publication number Publication date
EP1349969B1 (en) 2007-07-18
WO2002057513A1 (en) 2002-07-25
ATE367460T1 (en) 2007-08-15
JP2004527105A (en) 2004-09-02
CN1244719C (en) 2006-03-08
KR100890418B1 (en) 2009-03-26
JP4091433B2 (en) 2008-05-28
CN1483093A (en) 2004-03-17
TWI243861B (en) 2005-11-21
US20020065204A1 (en) 2002-05-30
US6344432B1 (en) 2002-02-05
DE60129465D1 (en) 2007-08-30
EP1349969A4 (en) 2004-07-28
KR20040007422A (en) 2004-01-24
US6660700B2 (en) 2003-12-09
DE60129465T2 (en) 2008-04-17
EP1349969A1 (en) 2003-10-08

Similar Documents

Publication Publication Date Title
US6660700B2 (en) Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
US6566315B2 (en) Formulations including a 1,3-dicarbonyl compound chelating agent and copper corrosion inhibiting agents for stripping residues from semiconductor substrates containing copper structures
US9109188B2 (en) Aqueous cleaning composition containing copper-specific corrosion inhibitor for cleaning inorganic residues on semiconductor substrate
US7662762B2 (en) Aqueous cleaning composition containing copper-specific corrosion inhibitor for cleaning inorganic residues on semiconductor substrates
US6211126B1 (en) Formulations including a 1, 3-dicarbonyl compound chelating agent for stripping residues from semiconductor substrates
JP4498424B2 (en) Aqueous cleaning composition containing copper-specific corrosion inhibitor for cleaning inorganic residues on semiconductor substrates
WO2006093770A1 (en) Method to remove resist, etch residue, and copper oxide from substrates having copper and low-k dielectric material
WO1998028395A1 (en) Formulations including a 1,3-dicarbonyl compound chelating agent for stripping residues from semiconductor substrates

Legal Events

Date Code Title Description
AS Assignment

Owner name: ADVANCED TECHNOLOGY MATERIALS, INC., CONNECTICUT

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:WOJTCZAK, WILLIAM A.;SEIJO, MA. FATIMA;NGUYEN, LONG;AND OTHERS;REEL/FRAME:011646/0236;SIGNING DATES FROM 20010208 TO 20010220

FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

FPAY Fee payment

Year of fee payment: 4

FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

Free format text: PAYER NUMBER DE-ASSIGNED (ORIGINAL EVENT CODE: RMPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

FPAY Fee payment

Year of fee payment: 8

REMI Maintenance fee reminder mailed
LAPS Lapse for failure to pay maintenance fees
STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362

FP Lapsed due to failure to pay maintenance fee

Effective date: 20140205