WO2004042472A2 - Supercritical carbon dioxide/chemical formulation for removal of photoresists - Google Patents

Supercritical carbon dioxide/chemical formulation for removal of photoresists Download PDF

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Publication number
WO2004042472A2
WO2004042472A2 PCT/US2003/033837 US0333837W WO2004042472A2 WO 2004042472 A2 WO2004042472 A2 WO 2004042472A2 US 0333837 W US0333837 W US 0333837W WO 2004042472 A2 WO2004042472 A2 WO 2004042472A2
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WO
WIPO (PCT)
Prior art keywords
composition
alcohol
photoresist
concentration
ion source
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.)
Ceased
Application number
PCT/US2003/033837
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English (en)
French (fr)
Other versions
WO2004042472B1 (en
WO2004042472A3 (en
Inventor
Michael B. Korzenski
Eliodor G. Ghenciu
Chongying Xu
Thomas H. Baum
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
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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
Application filed by Advanced Technology Materials Inc filed Critical Advanced Technology Materials Inc
Priority to EP03779250A priority Critical patent/EP1592520A2/en
Priority to AU2003284931A priority patent/AU2003284931A1/en
Priority to JP2004550105A priority patent/JP2006505010A/ja
Publication of WO2004042472A2 publication Critical patent/WO2004042472A2/en
Publication of WO2004042472A3 publication Critical patent/WO2004042472A3/en
Publication of WO2004042472B1 publication Critical patent/WO2004042472B1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • 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
    • 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
    • C11D7/02—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
    • 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
    • C11D7/3281—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
    • C11D7/5022—Organic solvents containing oxygen

Definitions

  • the present invention relates to supercritical carbon dioxide-based compositions useful in semiconductor manufacturing for the removal of photoresists, including photoresists per se and ion- implanted photoresists, from substrates having such photoresists thereon, and to methods of using such compositions for removal of photoresists and ion-implanted photoresists from semiconductor substrates.
  • Semiconductor manufacturing involves the use of photoresists that are applied to wafer substrates and subsequently developed to produce specific patterned regions and structures on the wafer.
  • This processing may include exposure of the photoresist to deep UN light and/or to high-dose ion implant, and the resulting photoresist materials and their residues are difficult to satisfactorily remove with conventional stripping and cleaning methods such as plasma etching and wet-bench cleaning.
  • High-dose ion implant processing usually results in the formation of a tough, carbonized crust, which protects the underlying bulk photoresist from the cleaning process and reagents. Similar crusts are formed after reactive ion etching (RIE) of patterned photoresists, especially in microelectronic device structures with low-k dielectric films.
  • RIE reactive ion etching
  • the present invention relates to supercritical carbon dioxide-based compositions useful in semiconductor manufacturing for the removal of photoresists and ion-implanted photoresists from substrates including same, and methods of using such compositions for removal of photoresists and ion-implanted photoresists from semiconductor substrates.
  • the invention relates to a photoresist cleaning composition, comprising SCC02 and alcohol.
  • the invention relates to a photoresist cleaning composition, comprising SCC02 and alcohol, wherein the alcohol is selected from the group consisting of C
  • -C 4 alcohols e.g., methanol, ethanol, propanol and butanol
  • a further aspect of the invention relates to a photoresist cleaning composition, comprising SCC02, alcohol and a fluorine ion source, wherein the alcohol is selected from the group consisting of CrC alcohols, wherein the fluorine ion source is present at a concentration of from about 0.01 to about 2 wt.%, based on the total weight of the composition, wherein the alcohol is present at a concentration of from about 5 to about 20 wt.%, based on the total weight of the cleaning composition, and wherein SCC02 is present at a concentration of from about 79 to about 94.99 wt.%, based on the total weight of the cleaning composition.
  • a still further aspect of the invention relates to a method of removing photoresist from a substrate having same thereon, said method comprising contacting the photoresist with a cleaning composition comprising SCC02 and alcohol, for sufficient time and under sufficient contacting conditions to remove the photoresist from the substrate.
  • Yet another aspect of the invention relates to a method of removing photoresist from a substrate having same thereon, said method comprising contacting the photoresist with a cleaning composition comprising SCC02 and alcohol, to remove the photoresist from the substrate, wherein the alcohol is selected from the group consisting of C C alcohols, and the alcohol is present at a concentration of from about 5 to about 20 wt.%, based on the total weight of the composition, and said contacting is carried out under conditions including pressure in a range of from about 1000 to about 7500 psi, temperature in a range of from about 35°C to about 100°C, for sufficient time to remove the photoresist from the substrate.
  • the invention in another aspect, relates to a method of removing ion implanted photoresist from a substrate having same thereon, said method comprising contacting the photoresist with a cleaning composition comprising SCC02, alcohol and a fluorine ion source, for sufficient time and under sufficient contacting conditions to remove the ion implanted photoresist from the substrate.
  • a further aspect of the invention relates to a method of removing ion implanted photoresist from a substrate having same thereon, said method comprising contacting the ion implanted photoresist with a cleaning composition comprising SCC02, alcohol and fluorine ion source, to remove the ion implanted photoresist from the substrate, wherein the alcohol is selected from the group consisting of C C 4 alcohols, the alcohol is present at a concentration of from about 5 to about 20 wt.%, based on the total weight of the composition, said fluorine ion source is present at a concentration of from about 0.01 to about 2 wt.%, based on the total weight of the composition, and said contacting is carried out under conditions including pressure in a range of from about 1000 to about 7500 psi, temperature in a range of from about 35°C to about 100°C, for sufficient time to remove the photoresist from the substrate.
  • a cleaning composition comprising SCC02, alcohol and fluorine i
  • Figure 1 is a scanning electron microscope (SEM) image at 50K magnification of a photoresist-bearing control wafer.
  • Figure 2 is a scanning electron microscope (SEM) image at 50K magnification of a corresponding post-cleaned sample, which was cleaned of photoresist by contact of the photoresist- bearing substrate with a cleaning composition containing SCC02/methanol, at 35°C (the image exhibits a weak line pattern due to over-etch of the metal surface prior to SCC02 cleaning).
  • Figure 3 is optical microscope image at 60K magnification of an ion-implanted photoresist-bearing control wafer.
  • Figure 4 is a corresponding scanning electron microscope (SEM) image of the ion- implanted photoresist-bearing control wafer of Figure 3, after cleaning for 15 minutes with an SCC02/methanol/NH 4 F solution at 55°C and 4000 psi pressure.
  • SEM scanning electron microscope
  • the present invention is based on the discovery of a supercritical carbon dioxide-based cleaning composition that is highly efficacious for the removal of photoresists, including photoresists per se as well as ion-implanted photoresists, from semiconductor substrates on which same are present.
  • Supercritical carbon dioxide SCC02
  • SCC02 Supercritical carbon dioxide
  • supercritical C0 2 has the characteristics of both a liquid and a gas. Like a gas, it diffuses rapidly, has low viscosity, near-zero surface tension, and penetrates easily into deep trenches and vias. Like a liquid, it has bulk flow capability as a "wash" medium.
  • the present invention provides a photoresist cleaning composition including SCC02 and alcohol.
  • the SCC02 and alcohol form a co-solvent composition that is highly effective for photoresist removal.
  • the present invention provides a cleaning composition including SCC02, alcohol and a fluoride ion source compound, which is highly effective for the removal of the ion implant hardened photoresist.
  • the alcohol used in the SCC02/alcohol cleaning compositions of the invention may be of any suitable type.
  • such alcohol comprises a C C 4 alcohol (e.g., methanol, ethanol, isopropanol, or butanol), or a mixture of two or more of such alcohol species.
  • the alcohol is methanol, ethanol or isopropanol.
  • the presence of the alcoholic co-solvent with the SCC02 serves to increase the solubility of the composition for photoresist material, including inorganic salts and polar organic compounds present therein, in a manner providing a striking improvement in removal ability of the composition for photoresists, relative to SCC02 alone.
  • the specific proportions and amounts of SCC02 and alcohol in relation to each other may be suitably varied to provide the desired solubilizing (solvating) action of the SCC02/alcohol solution for the specific photoresist material, including inorganic salts and polar organic compounds therein, to be cleaned from the substrate.
  • Such specific proportions and amounts are readily determinable by simple experiment within the skill of the art without undue effort.
  • the SCC02 and alcohol are formulated so that the resulting solution contains from about 5 to about 20 wt.% of alcohol.
  • the removal efficiency of the SCC02 and alcohol composition may be enhanced by use of elevated temperature conditions in the contacting of the composition containing the photoresist to be removed.
  • Figure 1 is a scanning electron microscope (SEM) image at 50K magnification of a photoresist-bearing control wafer.
  • Figure 2 is a scanning electron microscope (SEM) image at 50K. magnification of a corresponding post-cleaned sample, which was cleaned of photoresist by contact of the photoresist-bearing substrate with a cleaning composition of SCC02/methanol, at 35°C. As observed in Figure 2, the photoresist was completely removed under these conditions.
  • SEM scanning electron microscope
  • the process conditions other than temperature may be selected and optimal or otherwise advantageous conditions determined within the skill of the art, including the superatmospheric pressure at which the supercritical fluid composition is contacted with the photoresist to be removed from the substrate, the flow and/or static character of the cleaning composition contacting, and the duration of the contacting.
  • compositions of the invention may optionally be formulated with additional components to further enhance the removal capability of the composition, or to otherwise improve the character of the composition. Accordingly, the composition may be formulated with stabilizers, chelating agents, oxidation inhibitors, complexing agents, surfactants, etc.
  • oxidation inhibitor may be incorporated in the SCC02/alcohol compositions, such as for example boric acid, malonic acid, etc.
  • the cleaning composition comprises SCC02 and alcohol, e.g., methanol, ethanol or isopropanol, wherein the alcohol is present in an amount of from about 5 to about 20 wt.%, based on the total weight of the composition (SCC02 and alcohol).
  • alcohol e.g., methanol, ethanol or isopropanol
  • This composition has been demonstrated to successfully remove 100% of non-implanted photoresist on aluminum while completely maintaining the structural integrity of the underlying aluminum layer.
  • the cleaning composition is advantageously contacted with the photoresist at a temperature in a range of from about 35°C to about 100°C, at a pressure in a range of from about 1000 to about 7500 psi, for a contacting duration in a range of from about 1 to about 30 minutes, to effectively dissolve and carry away photoresist without damaging the underlying aluminum structure.
  • the ion implanted photoresist is advantageously removed from the substrate by a cleaning composition including SCC02, alcohol and a fluoride ion source compound.
  • the SCC02 and the alcohol may be formulated for such purpose as previously described in respect of cleaning compositions for non-ion implanted photoresists, with the additional fluoride ion source compound being added to the solution in an effective concentration, as readily determinable within the skill of the art, by the simple expedient of contacting the ion implant hardened photoresist with cleaning compositions of varying concentrations of the fluoride ion source compound, and determining the corresponding respective removal levels for the photoresist.
  • the fluoride ion source compound may be of any suitable type that is effective in the supercritical fluid composition under contacting conditions (with the ion implanted photoresist), to generate fluorine ions that enhance the removal capability of the cleaning composition, e.g., by reacting and complexing with the implanted cations such as boron, phosphorous and arsenic, to form SCC02-soluble species that subsequently aid in the dissolution of the photoresist.
  • a particularly preferred fluorine ion source is ammonium fluoride, NH 4 F, although any other suitable fluorine ion source material may be usefully employed.
  • the fluoro species-enhanced SCC02/alcohol composition may contain more than one fluorine ion source component.
  • the fluorine source may be of any suitable type, e.g., a fluorine-containing compound or other fluoro species.
  • Illustrative fluorine source components include hydrogen fluoride (HF), triethylamine trihdyrogen fluoride or other amine trihydrogen fluoride compound of the formula NR 3 (HF) 3 wherein each R is independently selected from hydrogen and lower alkyl (C C 8 alkyl), hydrogen fluoride-pyridine (pyr- HF), ammonium fluorides of the formula R 4 NF, wherein each R is independently selected from hydrogen and lower alkyl (C C 8 alkyl), other quaternary fluorides, xenon difluoride, fluoromethane, etc. etc.
  • HF hydrogen fluoride
  • pyr- HF hydrogen fluoride-pyridine
  • R 4 NF ammonium fluorides of the formula R 4 NF, wherein each R is independently selected from hydrogen and lower alkyl (C C 8 alkyl), other quaternary fluorides, xenon difluoride, fluoromethane, etc. etc.
  • ammonium fluoride (NH 4 F) is employed as the fluorine ion source component
  • such component is utilized at a concentration in a range of from about 0.01 wt.% to about 5 wt.%, and more preferably in a range of from about 0.1 wt.% to about 1 wt.%), based on the total weight of the cleaning composition (i.e., SCC02, alcohol and fluorine ion source).
  • Figure 3 is an optical microscope image at 60K magnification of an ion-implanted photoresist-bearing control wafer.
  • Figure 4 is a corresponding scanning electron microscope (SEM) image of the ion-implanted photoresist-bearing control wafer of Figure 3, after cleaning for 15 minutes with an SCC02/methanol/NH 4 F solution at 55°C and 4000 psi pressure. As observed in Figure 4, the photoresist was completely removed under these conditions by the SCC02/methanol/NH 4 F solution.
  • SEM scanning electron microscope
  • ammonium fluoride is present at a concentration of from about 0.1 to about 1.0 wt.%
  • alcohol is present at a concentration of from about 5 to about 20 wt.%
  • SCC02 is present at a concentration of from about 79 to about 94.9 wt.%, based on the total weight of the cleaning composition (SCC02, alcohol and NH 4 F).
  • Such cleaning composition may be contacted with the ion implanted photoresist under any suitable process conditions.
  • such cleaning composition is contacted with the ion implanted photoresist at a temperature in a range of from about 45°C to about 75°C, at a pressure in a range of from about 2000 to about 4500 psi, for a contacting duration in a range of from about 5 to about 15 minutes, to effectively dissolve and carry away photoresist without damaging the underlying silicon/silicon dioxide structure.
  • the contacting preferably is conducted in a dynamic contacting mode, involving continuous flow of the cleaning composition over the photoresist-bearing surface, to maximize the mass transfer gradient and effect complete removal of the photoresist from the substrate.
  • Cleaning processes of the invention may alternatively be carried out in a static soak mode, wherein the photoresist is contacted with a static volume of the cleaning composition and maintained in contact therewith for a continued (soaking) period of time, or as a still further alternative, the contacting of the cleaning composition with the photoresist may be carried out in sequential processing steps including dynamic flow of the cleaning composition over the substrate having the photoresist thereon, followed by a static soak of the substrate in the cleaning composition, with the respective dynamic flow and static soak steps being carried out alternatingly and repetitively, in a cycle of such successive steps.
  • the cleaning compositions of the present invention are readily formulated by simple mixing of ingredients, e.g., in a mixing vessel under gentle agitation. [0051] Once formulated, such cleaning compositions are applied to the substrate for contacting with the residue thereon, at suitable elevated pressures, e.g., in a pressurized contacting chamber to which the cleaning composition is supplied at suitable volumetric rate and amount to effect the desired contacting operation for removal of the photoresist.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Emergency Medicine (AREA)
  • Health & Medical Sciences (AREA)
  • Cleaning Or Drying Semiconductors (AREA)
  • Detergent Compositions (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
PCT/US2003/033837 2002-10-31 2003-10-27 Supercritical carbon dioxide/chemical formulation for removal of photoresists Ceased WO2004042472A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP03779250A EP1592520A2 (en) 2002-10-31 2003-10-27 Supercritical carbon dioxide/chemical formulation for removal of photoresists
AU2003284931A AU2003284931A1 (en) 2002-10-31 2003-10-27 Supercritical carbon dioxide/chemical formulation for removal of photoresists
JP2004550105A JP2006505010A (ja) 2002-10-31 2003-10-27 フォトレジストを除去するための超臨界二酸化炭素／化学調合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US10/285,146 US6989358B2 (en) 2002-10-31 2002-10-31 Supercritical carbon dioxide/chemical formulation for removal of photoresists
US10/285,146 2002-10-31

Publications (3)

Publication Number Publication Date
WO2004042472A2 true WO2004042472A2 (en) 2004-05-21
WO2004042472A3 WO2004042472A3 (en) 2004-07-15
WO2004042472B1 WO2004042472B1 (en) 2004-09-10

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US (2) US6989358B2 (https=)
EP (1) EP1592520A2 (https=)
JP (1) JP2006505010A (https=)
KR (1) KR20050074511A (https=)
CN (1) CN1708362A (https=)
AU (1) AU2003284931A1 (https=)
TW (1) TW200415239A (https=)
WO (1) WO2004042472A2 (https=)

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TW200415239A (en) 2004-08-16
CN1708362A (zh) 2005-12-14
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US6989358B2 (en) 2006-01-24
US20060040840A1 (en) 2006-02-23

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