WO2009073588A1 - Décapant pour photorésine contenant un fluorure ou compositions de nettoyage pour élimination de résidus contenant un matériau conjugué oligomère ou polymère d'un composé alpha-hydroxycarbonyl/amine ou une réaction ammonium - Google Patents

Décapant pour photorésine contenant un fluorure ou compositions de nettoyage pour élimination de résidus contenant un matériau conjugué oligomère ou polymère d'un composé alpha-hydroxycarbonyl/amine ou une réaction ammonium Download PDF

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Publication number
WO2009073588A1
WO2009073588A1 PCT/US2008/085094 US2008085094W WO2009073588A1 WO 2009073588 A1 WO2009073588 A1 WO 2009073588A1 US 2008085094 W US2008085094 W US 2008085094W WO 2009073588 A1 WO2009073588 A1 WO 2009073588A1
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Prior art keywords
compound
alpha
fluoride
composition according
oligomeric
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PCT/US2008/085094
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English (en)
Inventor
Seiji Inaoka
William R. Gemmill
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Mallinckrodt Baker, Inc.
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Publication of WO2009073588A1 publication Critical patent/WO2009073588A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/02—Inorganic compounds
    • C11D7/04—Water-soluble compounds
    • C11D7/10—Salts
    • 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
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium 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
    • 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
    • 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
    • C11D7/32—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
    • C11D7/50—Solvents
    • C11D7/5004—Organic solvents
    • C11D7/5009—Organic solvents containing phosphorus, sulfur or silicon, e.g. dimethylsulfoxide
    • 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
    • G03F7/423—Stripping or agents therefor using liquids only containing mineral acids or salts thereof, containing mineral oxidizing substances, e.g. peroxy compounds
    • 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
    • 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
    • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
    • C11D2111/10—Objects to be cleaned
    • C11D2111/14—Hard surfaces
    • C11D2111/22—Electronic devices, e.g. PCBs or semiconductors

Definitions

  • This invention relates to compositions useful for removing photoresist, contaminants, or plasma or etch residue from microelectronic devices, which compositions provide good copper corrosion inhibition or resistance while maintaining cleaning efficiency.
  • the invention provides aqueous or semi-aqueous, highly alkaline, fluoride-containing cleaning compositions having present in the composition 'browned' 1 oligomeric or polymeric conjugate material of alpha-hydroxycarbonyl compounds, especially 'browned" oligomeric or polymeric conjugate material of monosaccharides.
  • the invention also provides method for cleaning microelectronic substrates and devices employing such compositions.
  • Semiconductor devices have been produced by the steps of coating an inorganic substrate with a photoresist; patterning the photoresist film by exposure to light and subsequent development; etching exposed region of the inorganic substrate using the patterned photoresist film as a mask to form minute circuits; and removing the patterned photoresist film from the inorganic substrate Alternatively, after forming minute circuits in the same manner as above, the patterned photoresist film is ashed, and then the remaining resist residues are removed from the inorganic substrate.
  • aqueous alkaline compositions useful in the microelectronics industry for stripping or cleaning semiconductor wafer substrates by removing photoresist residues and other unwanted contaminants.
  • the aqueous compositions typically contain (a) one or more metal ion-free bases at sufficient amounts to produce a pH of about 10-13; (b) about 0.01% to about 5% by weight (expressed as % SiO 2 ) of a water-soluble metal ion-free silicate; (c) about 0.01% to about 10% by weight of one or more metal chelating agents and (d) optionally other ingredients.
  • compositions disclosed in the prior art effectively remove all organic contamination and metal-containing residues remaining after a typical etching process. Silicon containing residues are particularly difficult to remove using these formulations.
  • Such compositions must not corrode the metal features that partially comprise the integrated circuit and should avoid the expense and adverse consequences caused by intermediate rinses. Fluoride is good for Si rich residue, but it corrodes many metal (Al, Cu, etc) and damages many ILDs (e.g., TEOS, CDO, and the like).
  • fluoride-containing microelectronic cleaning composition that: (1) Is compatible with essentially all metals used in semiconductor devices (Ai, Cu, Mo, and the like), i.e., that produces essentially no corrosion of such metals;
  • aqueous or semi-aqueous fluoride-containing microelectronics cleaning composition or formulations comprising (a) at least one fluoride compound providing fluoride ions, (b) at least one "browned" alpha-hydroxycarbonyl conjugate that is a oligomeric or polymeric conjugate of a alpha- hydroxycarbonyl compound with an amine or an ammonium compound, and (c) water.
  • the alpha-hydroxy carbonyl compound is of the general formula R 1 CH(OH)COR 2 , where R 1 and R 2 are independently selected from H, an aliphatic group, or a cyclic group, which aliphatic or cyclic groups may contain one or more substituents .
  • substituents include, but are not limited to, a group selected from an aromatic group, a heteroaromatic group, an hydroxy! group (- OH group, an ether group (-C-O-C), an amide group (-C(O)NH), a sulfoxide group (-C-S(O)-C), an amine (-NR 3 R 4 ) where R 3 and R A are H or alkyi of from 1 to 10 carbon atoms, and a ketone group (-C(O)).
  • R 1 and R 2 are preferably an group selected from H and an alkyl group, more preferably from H, CHs, and (CH2) ⁇ CH3 where n is an integer of from O to 20, preferably 1 to 10 and more preferably 1 to 6.
  • suitable alpha-hydroxycarbonyl compounds include, but are not limited to, 1- hydroxy-2-propanone (CH 3 COCH 2 OH) CAS#119-09-6, 1,3-dihydroxyacetone (HOCH 2 COCH 2 OH) CAS#62147-49-3, and monosaccharides, including particularly glucose, fructose or galactose, fit the above generic structure.
  • the reaction of an amine and an alpha-hydroxy carbony! compound is known to proceed first by nucleophilic addition of the amine at the carbonyl carbon then continue via the Maillard reaction (Yaylayan, V. A.; Harty-Majors, S.; Ismail, A. A,; J. Agric. Food Chem. 1999, 47, 2335-2340).
  • the Maillard reaction is actually a complex series of reactions and details can be found in (Dills, W. L; Am. J. Clin. Nutr. 1993, 58, 779S-787S.
  • the cleaning compositions of the invention may optionally contain other ingredients such as (d) at least one polar, water miscible organic solvent.
  • the pH of the composition can be of any suitable pH, from acidic to basic pH.
  • the composition may also contain (e) at least one meta! ion-free base at sufficient amounts to produce a final composition of pH, 7 or above, preferably a pH of about 9.5 to about 10.8.
  • the compositions of this invention may also include and one or more of (f) a polyhydric alcohol and (g) a surfactant.
  • the browned oligomeric or polymeric conjugate of a alpha-hydroxycarbonyl compound employed in the compositions of this invention are those oligomeric or polymeric conjugates having an absorbance peak at about 300 to 330 nm with the absorbance peak beginning at a wavelength of from about 600 to 800 nm.
  • These browned ologomeric or polymeric conjugates can be formed by the known "Maillard Reaction"-... C. Maillard, Compt Rend. 154, 66 (1912); Ann. Chim.9, 5, 258 (1916).
  • the "browned" conjugates that are oligomeric or polymeric conjugates of a alpha-hydroxycarbonyl compound with an amine or an ammonium compound that are employed in the compositions of this invention are distinguished from merely "yellowed” conjugates of alpha-hydroxycarbonyl compounds that are the reaction product oligomeric or polymeric conjugates of a alpha-hydroxycarbonyl compound with an amine or an ammonium compound as the "yellowed" alpha-hydroxycarbonyl conjugates do not work in the formulations of this invention since such formulations containing the "yellowed" alpha-hydroxycarbonyl conjugates do not provide adequate Cu etch rate protection.
  • the "yellowed" alpha-hydroxycarbonyl conjugates are those reaction products of a alpha-hydroxycarbonyl compound with an amine or an ammonium compound that have an absorbance peak at about 300 to 330 nm, however the absorbance peak begins at about 500 to 580 nm.
  • the cleaning compositions of this invention are placed in contact with a semiconductor device for a time and at a temperature sufficient to clean unwanted contaminants and/or residues from the substrate surface.
  • the compositions of this invention provide enhanced corrosion resistance, especially copper corrosion resistance, and improved cleaning efficiency.
  • the cleaning compositions of this invention comprise neutral to alkaline, aqueous or semi-aqueous cleaning formulations comprising: (a) at least one fluoride compound providing fluoride ions, (b) at least one "browned" alpha- hydroxycarbonyl conjugate that is a oligomeric or polymeric conjugate of a alpha-hydroxycarbonyl compound with an amine or an ammonium compound, and (c) water.
  • Such formulations may also comprise other optional components, including, but not limited to, (d) at least one polar, water miscible organic solvent, (e) at least one metal ion-free base at sufficient amounts to produce a final composition of pH, 7 or above, preferably a pH of about 9.5 to about 10.8 when an alkaline cleaning composition is desired, and one or more of (f) a polyhydric alcohol and (g) a surfactant.
  • optional components including, but not limited to, (d) at least one polar, water miscible organic solvent, (e) at least one metal ion-free base at sufficient amounts to produce a final composition of pH, 7 or above, preferably a pH of about 9.5 to about 10.8 when an alkaline cleaning composition is desired, and one or more of (f) a polyhydric alcohol and (g) a surfactant.
  • the "browned" alpha-hydroxycarbonyl conjugates used in the compositions of this invention are those oligomeric or polymeric conjugates of a alpha-hydroxycarbonyl compound with an amine or an ammonium compound and having an absorbance peak at about 300 to 330 nm with the absorbance peak beginning at a wavelength of from about 600 to 800 nm.
  • Such browned oligomeric or polymeric conjugates are prepared according to know procedures such as by the previously mentioned "Maillard Reaction". However, any suitable means of obtaining the "browned" alpha-hydroxycarbonyl conjugates may be employed. Additionally, such "browned" alpha-hydroxycarbonyl conjugates may be employed in the form of dark molasses, for example.
  • the reaction of the alpha-hydroxycarbonyl compound and amine or ammonia containing compound may be carried out with the stoichiometric ratio of alpha-hydroxycarbonyl compound to amine or ammonia compound being from about 1 :1 to about 16:1 on the basis of reaction of 1 molecule of alpha-hydroxycarbonyl compound and 1 mol of amine or ammonia compound.
  • the ratio be 1:1 as the presence of less amine or ammonia compound to react with the alpha-hydroxycarbonyl compound results in a diminution of the copper corrosion inhibition capability of the reaction product. Excess amine or ammonia containing compound does not appear to have any significant effect on the copper corrosion inhibition property of the cleaning composition.
  • the reaction can be conducted over a wide range of times and temperatures, it is preferred that the reaction be conducted by heating the alpha-hydroxycarbonyl compound with the amine or ammonia compound to about 70° C or higher for a period of about 3 hours or longer. Any suitable time and temperature may be employed so long as the resulting oligomeric or polymeric conjugate reaction product is a "browned" product, i.e., one having an absorbance peak at about 300 to 330 nm and with that peak beginning at about 600 to 800 nm.
  • the browned alpha-hydroxycarbonyl conjugates preferably employed in this invention are characterized by having a low bandgap of about O. ⁇ eVor less.
  • the browned alpha-hydroxycarbonyl conjugates may be obtained from the reaction of any suitable alpha- hydroxycarbonyl compound with and amine or ammonia compound.
  • suitable alpha-hydroxycarbonyl compounds include, but are not limited to, 1-hydroxy-2-pro ⁇ anone, CH3COCH2OH and 1 ,3-dihydroxyacetone, HOCH2COCH2OH, and all of monosaccharides incfuding arabinose, lyxose, ribose, deoxyribose, xylose, ribulose, xylulose, allose, altrose, galactose, glucose, gulose, idose, mannose, fructose, psicose, sorbose, tagatose, mannoheptulose, sedoheptulose, octulose, 2-keto-3-deoxy-manno-octonate and sialose. Particularly preferred is fructose.
  • Any suitable amine or ammonia containing compound may be reacted with the alpha-hydroxycarbonyl compounds of this invention to produce the browned oligomeric or polymeric conjugate of a alpha-hydroxycarbonyl compound with an amine or an ammonium compound.
  • suitable amines are amines, diamines, triaamines, alkanolamines, amino acids particularly primary and secondary amines and alkanolamines.
  • Ammonia is suitable just like amines described above.
  • Suitable amine compounds include, but are not limited to monoethanolamine, diethanolamine, triethanolamine, monoisopropanolamine, diethylenetriamine, aminoacetic acid. Especially preferred is monoethnolamine.
  • the preferred browned alpha-hydroxycarbonyl compound is obtained from reaction of fructose with monoethanolamine.
  • Any suitable fluoride compound providing fluoride ions may be employed in the compositions of this invention.
  • Suitable fluoride compounds include HF, ammonium fluoride, tetraalkylammonium fluorides, especially those wherein the alkyl groups contain from 1 to 4 carbon atoms, fluoride salts such as ammonium fluoride.
  • fluoride compounds that are especially useful there may be mentioned tetramethylammonium fluoride, tetrabutylammonium fluoride, and ammonium fluoride, preferably ammonium fluoride.
  • the amount of fluoride compound in the cleaning compositions of this invention will generally range from about 0.0001 to about 10 wt.%, preferably from about 0.01 to about 5 wt.%, and more preferably from about 0.5 to about 1 wt.%.
  • the "browned" oligomeric or polymeric alpha-hydroxycarbonyl compound will generally be present in the cleaning composition of this invention in an amount of from about 0.1 to about 20 wt.%, preferably from about 1 to about 10 wt.%, and more preferably from about 3 to about 7 wt.%.
  • Water will be present in the compositions of this invention in an amount of from about 10 to about 99.9 wt.%, preferably from about 60 to about 99 wt.%, and more preferably from about 85 to about 96.5 wt.%. All percentages are based on the total weight of the cleaning composition.
  • the pH of the cleaning compositions will acidic or alkaline, but preferably will be 7 or above, preferably from about pH 7 to about 10.8, more preferably from pH of about 9.5 to about 10.8.
  • a metal ion-free base may optionally be added to the cleaning composition. Any suitable metal ion- free base may be employed.
  • suitable metal ion-free bases that may be employed in the cleaning compositions there may be quaternary ammonium hydroxides, such as tetraalkyl ammonium hydroxides (including hydroxy- and alkoxy-containing alkyl groups generally of from 1 to 4 carbon atoms in the alkyl or alkoxy group).
  • alkaline materials are tetramethyi ammonium hydroxide and trimethyl-2-hydroxyethyl ammonium hydroxide (choline).
  • examples of other usable quaternary ammonium hydroxides include: trimethyl-3- hydroxypropyl ammonium hydroxide, trimethyl-3-hydroxybutyl ammonium hydroxide, trimethyl-4-hyd roxybuty I ammonium hydroxide, triethyl-2-hydroxyethyl ammonium hydroxide, tripropyl-2-hydroxyethyi ammonium hydroxide, tributyl-2-hydroxyethyl ammonium hydroxide, dimethylethyl-2-hydroxyethyi ammonium hydroxide, dimethyldi(2- hydroxyethyl) ammonium hydroxide, monomethyltri(2-hydroxyethyl) ammonium hydroxide, tetraethyl ammonium hydroxide, tetrapropyl ammonium hydroxide
  • bases that will function in the present invention include ammonium hydroxide, organic amines particularly alkanolamines such as 2- aminoethanol, 1-amino-2-propanol, 1-amino-3-propanol, 2-(2-aminoethoxy)ethanol, 2-(2-aminoethy!amino)ethanol, 2-(2-aminoethylamino)ethylamine and the like, and other strong organic bases such as guanidine, 1,3- pentanediamine, 4-aminomethyl-1,8-octanediamine, aminoethylpiperazine, 4-(3-aminopropyl)morpholine, 1,2- diaminocyclohexane, tris(2-aminoethyl)amine, 2-methyl-1,5-pentanediamine and hydroxy lamine.
  • organic amines particularly alkanolamines such as 2- aminoethanol, 1-amino-2-propanol, 1-amino-3-propanol, 2-(2-
  • the amount of such bases employed in the composition will be an amount to give a desired pH to the composition and will generally be an amount of from about 0 to about 15 wt.%, preferably from about 0.5 to about 5 wt.%, and more preferably an amount of from about 1 to about 2 wt.%.
  • the formulations of this invention may be aqueous based but may also be semi-aqueous. That is, the formulations may optionally contain at least one polar, water miscible organic solvent. Any suitable polar, water miscible organic solvent may be employed in the formulation. Such suitable polar, water miscible organic solvent, include, but are not limited to 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-butyi sulfone, 3-methylsutfolane, amides such as 1 -(2-hydroxyethyl) -2-pyrrolidone (HEP), dimethylpiperidone (DMPD), N-methyl-2-pyrraiidone (NMP), dimethylacetamide (DMAc), and dimethylformamide (DMF) and mixtures thereof.
  • organic polar solvents such as sulfolane (tetrahydrothiopene-1,1 -dioxide), 3- methylsulfolane, n-propyl sulfone, dimethyl sulfoxide (DMSO), methyl sulfone
  • organic polar solvent Especially preferred as the organic polar solvent are N-methylpyrrol idone, sulfolane, and DMSO. if present the polar, water miscible organic solvent will generally be employed in an amount of from about more than O to about 50 wt %, preferably from about 5 to about 30 wt %, and more preferably from about 10 to about 20 wt %.
  • the formulation of this invention may also optionally contain any suitable polyhydric alcohol component.
  • suitable polyhydric alcohols include, but are not limited to sorbitol, xylitol, glycerol, ethylene glycol, butane-1,4- diol.
  • the polyhydric alcohol employed is, preferably D-sorbitol.
  • the amount of polyhydric alcohol present in the composition, if present, can range from about more than 0 to about 10 wt%, preferably from about more than 0 to about 7 wt %, and more preferably from about more than 0 to about 5 wt %.
  • the formulations of this invention may also contain optional ingredients that are not harmful to the effectiveness of the cleaning composition, such as for example, surfactants.
  • the compositions of the present invention may also contain any suitable water-soluble amphoteric, non-ionic, cationic or anionic surfactant.
  • a surfactant will reduce the surface tension of the formulation and improve the wetting of the surface to be cleaned and therefore improve the cleaning action of the composition.
  • Amphoteric surfactants useful in the compositions of the present invention include betaines and sulfobetaines such as alkyl betaines, amidoalky!
  • betaines alkyl sulfobetaines and amidoalkyl sulfobetaines
  • aminocarboxylic acid derivatives such as amphoglycinates, amphopropionates, amphodiglycinates, and amphodipropionates
  • iminodiacids such as alkoxyalkyl iminodiacids
  • amine oxides such as alkyl amine oxides and alkylamido alkylamine oxides
  • fluoroalkyl sulfonates and fluorinated alkyl amphoterics and mixtures thereof.
  • amphoteric surfactants are cocoamidopropyl betaine, cocoamidopropyi dimethyl betaine, cocoamidopropyl hydroxy sultaine, capryloamphodi propionate, cocoamidodipropionate, cocoamphopropionate, cocoamphohydroxyethyl propionate, isodecyloxypropylimino dipropionic acid, laury ⁇ mino dipropionate, cocoamidopropylamine oxide and cocoamine oxide and fluorinated alkyl amphoterics.
  • Non-ionic surfactants useful in the compositions of the present invention include acetylenic diols, ethoxylated acetylenic diols, fluorinated alkyl alkoxylates, fluorinated alkylesters, fluorinated polyoxyethylene alkanols, aliphatic acid esters of polyhydric alcohols, polyoxyethyle ⁇ e monoalkyl ethers, polyoxyethylene diols, siloxane type surfactants, and alkylene glycol monoalkyl ethers.
  • the non-ionic surfactants are acetylenic diols or ethoxylated acetylenic diols.
  • Anionic surfactants useful in the compositions of the present invention include carboxylates, N-acylsarcosinates, sulfonates, sulfates, and mono and diesters of orthophosphoric acid such as decyl phosphate.
  • the anionic surfactants are metal-free surfactants.
  • Cationic surfactants useful in the compositions of the present invention include amine ethoxylates, dialkyldimethylammonium salts, dialkylmorpholinium salts, alkylbenzyldimethylammonium salts, alkyltrimethylammonium salts, and alkylpyridi ⁇ ium salts.
  • the cationic surfactants are halogen-free surfactants.
  • the surfactants, if employed in the compositions of this invention will generally be present in an amount of from about more than O to about 1 wt.%, preferably from about 0.05 to about 0.2 wt.%.
  • the formulations of the present invention may also be formulated with one or more metal suitable chelating agents to increase the capacity of the formulation to retain metals in solution and to enhance the dissolution of metallic residues on the wafer substrate.
  • metal suitable chelating agents useful for this purpose are the following organic acids and their isomers and salts: (ethylenedinitrilo)tetraacetic acid (EDTA), butylenediaminetetraacetic acid, cyclohexane-1,2-diaminetetraacetic acid (CyDTA), diethylenetriaminepentaacetic acid (DETPA), ethylenediaminetetrapropionic acid, (hydroxyethy!ethylenediaminetriacetic acid (HEDTA), N,N,N',N'- ethylenediaminetetra(methylenephosphonic) acid (EDTMP), triethylenetetraminehexaacetic acid (TTHA) 1 1,3- diamino-2-hydroxypropane-N,N,N',N'
  • the metal chelating agents are aminocarboxylic acids such as cyc!ohexane-1 ,2-diaminetetraacetic acid (CyDTA).
  • the at least one metal chelating agent may be present in the formulation in an amount from about more than 0 to about 1 wt. % by weight, preferably in an amount from about 0.05 to about 0.2wt. %.
  • the cleaning compositions of this invention are used to clean photoresist or plasma or etch residue from microelectronic devices by contacting the microelectronic devise with the cleaning compositions of this invention for a suitable time and at a suitable temperature to remove the photoresist or plasma or etch residue from the microelectronic device.
  • the invention is illustrated by, but limited to, the following illustrative examples.
  • the following are examples of "browned" alpha-hydroxycarbonyl conjugated oligomers or polymers useful in the compositions of this invention.
  • Browned Component A 100g of a 50:50 wt. mixture of fructose and water was reacted with 5Og monoethanolamine at a temperature of 70° C for about 3 hr.
  • Browned Component B 100g of a 50:50 wt. mixture of fructose and water was reacted with 16g monoethanolamine at a temperature of 70° C for about 3 hr.
  • Browned Component C 10Og of a 50:50 wt. mixture of fructose and water was reacted with 5g monoethanolamine at a temperature of 70° C for about 3 hr.
  • Browned Component D 100g of a 50:50 wt. mixture of fructose and water was reacted with 1g monoethanolamine at a temperature of 70° C for about 3 hr.
  • Browned Component E 5Og of fructose was dissolved in 10g water and the mixture heated to 80° C and then 20.8g monoisopropanolamine was added, the solution heated up by itself and released water under boiling action.
  • Browned Component F 5Og of fructose was dissolved in 1Og water and the mixture heated to 80° C and then 29.2 diethanolamine was added, the solution heated up by itself and released water under boiling action.
  • Browned Component G 5Og of fructose was dissolved in 1Og water and the mixture heated to 80° C and then 41.9 triethanolamine was added, the solution heated up by itself and released water under boiling action.
  • Browned Component H 5Og of fructose was dissolved in 1Og water and the mixture heated to 80° C and then 26.5 g diethylenetriamine was added, the solution heated up by itself and released water under boiling action.
  • Browned Component J 5Og of fructose was dissolved in 10g water and the mixture heated to 80° C and then 20.8g aminoacetic acid (glycine) was addded, the solution heated up by itself and released water under boiling action.
  • glycine aminoacetic acid
  • Browned Component K 50g of glucose was dissolved in 10g water and the mixture heated to 80° C and then 17,Og monoethanolamine was added, the solution heated up by itself and released water under boiling action.
  • Browned Component L 5Og of galactose was dissolved in 10g water and the mixture heated to 80° C and then 20.8g monoethanolamine was added, the solution heated up by itself and released water under boiling action.
  • Browned Component M 50 g of a 50:50 mixture of 1 -hydroxy-2-propanone and water was reacted with 8 g monoethanolamine at 70° C for about 1 hour.
  • Browned Component N 50 g of a 50:50 mixture of dihydroxyacetone and water was reacted with 8 g monoethanolamine at 70° C for about 1 hour.
  • Yellowed Component 1 100g of a 50:50 wt. mixture of fructose and water reacted with 16g monoethanolamine at a temperature of 70° C for about 3 hr and was left overnight at room temperature of about 20° C
  • Yellowed Component 2 100g of a 50:50 wt. mixture of fructose and water was reacted with 5Og monoethanolamine at a temperature of 70° C overnight and was left at room temperature of about 20° C for one week
  • Copper corrosion inhibition for the compositions of this invention and for comparative compositions were tested in the following manner. Copper blanket wafers were placed in a 150 ml beaker containing the test compositions at about 20° C. The compositions were stirred at about 200rpm for 15 minutes, Cu surface away from the stirbar. The test composition were prepared by adding the above described "browned” components, or the above-described “yellowed” comparative components, or just fructose alone to one of the following two Base Solutions.
  • Base Solution # 1 consisted of 3.25 g 40% aqueous NH 4 F solution (1.3g NH 4 F and 1.95 g water), 4.33g 30% aqueous NH 4 OH solution (1.3g NH 4 OH and 3.03g water), 466.82g deionized water; total solution weight 474.4g.
  • Base Solution # 2 consisted of 1.75g 40% aqueous solution of NH 4 F (0.7g NH 4 F and 1.05g water) and deionized water sufficient to make the composition of the invention 10Og total weight . [0027] The compositions and the test results are presented in Table 1.
  • Copper etch rates (A/mm) in DMSO, NMP or mixtures thereof for tested compositions at 70 0 C are set forth in Table 2 All compositions utilized monoethanol amine as the amine reacted with the listed compound at 70 0 C for about three hours
  • compositions of this invention provide cleaning of photoresist or plasma or etch residue from microelectronic devices similar to known fluoride containing microelectronic cleaning compositions but without the significant copper corrosion encountered with the use of those known fluoride containing cleaning compositions.
  • a preferred cleaning composition of this invention comprises about 1.74 pars by weight oligomeric or polymeric conjugate of fructose and monoethanolamine, about 0,06 parts by weight ammonium fluoride, and about 98.2 parts by weight water.

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Abstract

Préparations semi-aqueuses de nettoyage pour dispositifs micro-électroniques contenant: (a) au moins un composé fluoruré donnant des ions fluorure, (b) au moins un composé alpha-hydroxycarbonyl 'bruni' qui est un conjugué oligomère ou polymère d'un composé alpha-hydroxycarbonyl avec une amine ou un composé ammonium, et (c) de l'eau. De telles préparations peuvent également comprendre d'autres composants dont: (d) au moins un solvant organique polaire hydromiscible, (e) au moins une base métallique sans ions en quantité suffisante pour produire une composition finale au pH de 7 ou plus, compris de préférence entre 9,5 et 10,8 environ, et (f) un ou plusieurs alcools polyhydriques et (g) un tensioactif. De telles compositions conviennent pour le nettoyage de dispositifs microélectroniques sans corrosion sérieuse du métal et sont compatibles avec les ILD (intercouches diélectriques).
PCT/US2008/085094 2007-12-06 2008-12-01 Décapant pour photorésine contenant un fluorure ou compositions de nettoyage pour élimination de résidus contenant un matériau conjugué oligomère ou polymère d'un composé alpha-hydroxycarbonyl/amine ou une réaction ammonium WO2009073588A1 (fr)

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WO2010102863A1 (fr) * 2009-03-11 2010-09-16 Henkel Ag & Co. Kgaa Adjuvants biodégradables et co-tensioactifs
US9536730B2 (en) 2012-10-23 2017-01-03 Air Products And Chemicals, Inc. Cleaning formulations
WO2017023348A1 (fr) * 2015-08-06 2017-02-09 Kyzen Corporation Solutions tolérant l'eau et procédé pour éliminer des saletés polymères et nettoyer des substrats micro-électroniques
CN110114856A (zh) * 2016-12-22 2019-08-09 花王株式会社 硅晶片用冲洗剂组合物
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JP7235336B2 (ja) * 2017-08-22 2023-03-08 フジフイルム エレクトロニック マテリアルズ ユー．エス．エー．， インコーポレイテッド 洗浄組成物
US11339302B2 (en) * 2019-09-03 2022-05-24 Nch Corporation Composition and method for removing a coating from a surface
KR102192954B1 (ko) * 2020-03-26 2020-12-18 동우 화인켐 주식회사 고분자 세정용 조성물
CN113161234B (zh) * 2021-04-27 2023-02-17 上海新阳半导体材料股份有限公司 一种含氟清洗液组合物的应用

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WO2010102863A1 (fr) * 2009-03-11 2010-09-16 Henkel Ag & Co. Kgaa Adjuvants biodégradables et co-tensioactifs
US9536730B2 (en) 2012-10-23 2017-01-03 Air Products And Chemicals, Inc. Cleaning formulations
WO2017023348A1 (fr) * 2015-08-06 2017-02-09 Kyzen Corporation Solutions tolérant l'eau et procédé pour éliminer des saletés polymères et nettoyer des substrats micro-électroniques
US11397383B2 (en) 2016-06-03 2022-07-26 Fujifilm Corporation Treatment liquid, method for washing substrate, and method for removing resist
US11899369B2 (en) 2016-06-03 2024-02-13 Fujifilm Corporation Treatment liquid, method for washing substrate, and method for removing resist
CN110114856A (zh) * 2016-12-22 2019-08-09 花王株式会社 硅晶片用冲洗剂组合物
US10865368B2 (en) 2016-12-22 2020-12-15 Kao Corporation Rinse agent composition for silicon wafers
CN110114856B (zh) * 2016-12-22 2023-12-05 花王株式会社 硅晶片用冲洗剂组合物

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CN101452227A (zh) 2009-06-10

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