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WO2010091045A2 - Composition ne contenant pas de fluorure pour l'élimination de polymères et autres matières organiques à partir d'une surface - Google Patents

Composition ne contenant pas de fluorure pour l'élimination de polymères et autres matières organiques à partir d'une surface Download PDF

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Publication number
WO2010091045A2
WO2010091045A2 PCT/US2010/022987 US2010022987W WO2010091045A2 WO 2010091045 A2 WO2010091045 A2 WO 2010091045A2 US 2010022987 W US2010022987 W US 2010022987W WO 2010091045 A2 WO2010091045 A2 WO 2010091045A2
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WIPO (PCT)
Prior art keywords
composition
acid
removal
removal composition
group
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PCT/US2010/022987
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WO2010091045A3 (fr
Inventor
Michael B. Korzenski
Ping Jiang
John Warner
Ted Mendum
Michelle Lugus
Justin Whitfield
Helen Vanbenschoten
Makonnen Payne
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Advanced Technology Materials Inc
Warner Babcock Institute for Green Chemistry LLC
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Advanced Technology Materials Inc
Warner Babcock Institute for Green Chemistry LLC
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Publication of WO2010091045A2 publication Critical patent/WO2010091045A2/fr
Publication of WO2010091045A3 publication Critical patent/WO2010091045A3/fr
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
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G03F7/426—Stripping or agents therefor using liquids only containing organic halogen compounds; containing organic sulfonic acids or salts thereof; containing sulfoxides

Definitions

  • the present invention relates generally to removal compositions that are substantially devoid or devoid of fluoride species and that are useful for the removal of polymers and/or other organic materials (e.g., waxes, oils, and paints) from a surface having same thereon.
  • polymers and/or other organic materials e.g., waxes, oils, and paints
  • Numerous materials containing polymers are used in the manufacture of electronic devices, such as circuits, disk drives, storage media devices and the like. Such polymeric materials are found in photoresists, solder masks, antireflective coatings, and the like.
  • modern technology utilizes positive-type resist materials for lithographically delineating patterns onto a substrate so that the patterns can be subsequently etched or otherwise defined into the substrate material.
  • the resist material is deposited as a film and the desired pattern is defined by exposing the resist film to energetic radiation. Thereafter the exposed regions are subject to dissolution by a suitable developer liquid. After the pattern has been thus defined in the substrate the resist material must be completely removed from the substrate to avoid adversely affecting or hindering subsequent operations or processing steps.
  • resist removal compositions include fluoride. Such compositions have the disadvantage of requiring special handling and disposal requirements due to incompatibility with common solvent waste streams, as well as high viscosity which prohibits spray tool processes.
  • known stripping compositions have numerous drawbacks including, undesirable flammability, toxicity, volatility, odor, necessity for use at elevated temperatures such as up to 100 0 C, and high cost due to handling regulated materials.
  • a particular problem with advanced next generation microelectronic devices is that known removal compositions are incompatible with a variety of thin films in such devices, specifically copper and low-k dielectric material present in such devices.
  • the present invention relates to removal compositions useful for removing polymeric and/or other organic materials from a surface.
  • a removal composition comprising at least one polymer dissolution accelerator, at least one organic solvent, and water, wherein the composition is substantially devoid of fluoride species.
  • the composition is substantially devoid of amine species as well.
  • a removal composition consisting essentially of at least one polymer dissolution accelerator, at least one organic solvent, and water, wherein the composition is substantially devoid of fluoride species.
  • the composition is substantially devoid of amine species as well.
  • a removal composition consisting of at least one polymer dissolution accelerator, at least one organic solvent, and water, wherein the composition is substantially devoid of fluoride species.
  • the composition is substantially devoid of amine species as well.
  • a removal composition comprising at least one polymer dissolution accelerator, at least one organic solvent, at least one complexing agent, and water, wherein the composition is substantially devoid of fluoride species.
  • the composition is substantially devoid of amine species as well.
  • Another aspect relates to a removal composition, said removal composition consisting essentially of at least one polymer dissolution accelerator, at least one organic solvent, at least one complexing agent, and water, wherein the composition is substantially devoid of fluoride species.
  • the composition is substantially devoid of amine species as well.
  • Still another aspect relates to a removal composition, said removal composition consisting of at least one polymer dissolution accelerator, at least one organic solvent, at least one complexing agent, and water, wherein the composition is substantially devoid of fluoride species.
  • the composition is substantially devoid of amine species as well.
  • a method of removing polymer and/or other organic materials from a surface having same thereon comprising contacting the surface with a semi- aqueous removal composition for sufficient time and under sufficient contacting conditions to at least partially remove said polymer and/or other organic materials from the surface, wherein the removal composition includes at least one polymer dissolution accelerator, at least one organic solvent, and water, wherein the composition is substantially devoid of fluoride species.
  • kits comprising, in one or more containers, one or more of the following reagents for forming a composition, wherein said composition comprises at least one polymer dissolution accelerator, at least one organic solvent, water, and optionally at least one complexing agent, wherein the kit is adapted to form a composition suitable for removing polymeric and/or other organic material from a surface.
  • the present invention relates generally to the field of removal of polymeric and/or other organic materials from a surface. More specifically, a removal composition substantially devoid of fluoride is described for the removal of polymers and other organic materials from surfaces including, but not limited to paints, waxes and oils. Even more specifically, the removal compositions are useful for the removal of polymeric material from a microelectronic device, whereby the compositions described herein are compatible with low-k dielectric and metal-containing materials on said device.
  • a "surface” corresponds to any solid material that the polymer or other organic material may be found on including natural or synthetic materials including, but not limited to, microelectronic devices, metals, plastics, fabrics, fibers, soils, wood, paper, glass, leather and other animal hides, cement, concrete, bricks, drywall, asphalt, keratin-containing substances such as hair and nails, rubber, latex, minerals, mineral crystals, amorphous inorganic materials, and combinations thereof.
  • Microelectronic device corresponds to semiconductor substrates, flat panel displays, phase change memory devices, solar panels and other products including solar substrates, photovoltaics, and microelectromechanical systems (MEMS), manufactured for use in microelectronic, integrated circuit, or computer chip applications.
  • MEMS microelectromechanical systems
  • microelectronic device “microelectronic substrate” and “microelectronic device structure” are not meant to be limiting in any way and include any substrate or structure that will eventually become a microelectronic device or microelectronic assembly.
  • the microelectronic device can be patterned, blanketed, a control and/or a test device.
  • polymers and “polymeric material” correspond to any compound, typically of organic origin, having a large number of monomelic units covalently bonded to each other, wherein the monomelic units may be the same as or different from one another.
  • Polymers may be natural or man-made (synthetic), and for the purpose of the invention described herein may include proteins, polysaccharides, polypeptides, polynucleotides, oligomers, copolymers, terpolymers, photoresists, solder masks, antireflective coatings, resist-containing residues, paints, waxes, oils, contaminants, and combinations thereof.
  • polymers and polymeric material include residues that comprise polymers.
  • Typical synthetic polymer genuses include novolacs, polyacrylates, polyamides, polyesters, polycarbonates, polyimides polystyrenes, polybenzocyclobutenes, polynorborenes, and siloxy-functionalized polymers including, but not limited to, phenol formaldehyde resins, polyhydroxystyrenes, polymethylmethacrylates, includes: acrylonitrile butadiene styrene (ABS), polyacrylonitrile (PAN), polybutadiene, poly(butylene terephthalate) (PBT), poly(ether sulfone) (PES, PES/PEES), poly(ether ether ketone)s (PEEK, PES/PEEK), polyethylene (PE), polyethylene glycol) (PEG), polyethylene terephthalate) (PET), polypropylene (PP), polytetrafluoro
  • “residue” corresponds to particles generated during the manufacture of a microelectronic device including, but not limited to, plasma etching, ashing, chemical mechanical polishing, wet etching, and combinations thereof.
  • post-CMP residue corresponds to particles from the polishing slurry, e.g., silica-containing particles, chemicals present in the slurry, reaction by-products of the polishing slurry, carbon-rich particles, polishing pad particles, brush deloading particles, equipment materials of construction particles, copper, copper oxides, copper-containing materials, aluminum, aluminum oxides, aluminum-containing materials, organic residues, and any other materials that are the byproducts of the CMP process.
  • post-etch residue corresponds to material remaining following gas-phase plasma etching processes, e.g., BEOL dual damascene processing.
  • the post-etch residue may be organic, organometallic, organosilicic, or inorganic in nature, for example, silicon-containing material, carbon-based organic material, and etch gas residue such as oxygen and fluorine.
  • post-ash residue corresponds to material remaining following oxidative or reductive plasma ashing to remove hardened photoresist and/or bottom anti- reflective coating (BARC) materials.
  • BARC bottom anti- reflective coating
  • the post-ash residue may be organic, organometallic, organosilicic, or inorganic in nature.
  • photoresist includes undeveloped photoresist, bulk photoresist, and/or hardened photoresist, whether positive or negative.
  • Bok photoresist corresponds to the non-carbonized photoresist on the microelectronic device surface, specifically adjacent and below the hardened photoresist crust.
  • Hardened photoresist includes, but is not limited to: photoresist that has been plasma etched, e.g., during back-end-of-line (BEOL) dual-damascene processing of integrated circuits; ion implanted, e.g., during front-end-of-line (FEOL) processing to implant dopant species in the appropriate layers of the semiconductor wafer; and/or any other methodology whereby a carbonized or highly cross-linked crust forms on the exposed surface of the bulk photoresist.
  • Doping species include, but are not limited to, boron, arsenic, boron difluoride, indium, antimony, germanium, carbon, and/or phosphorous ions.
  • low-k dielectric material corresponds to any material used as a dielectric material in a layered microelectronic device, wherein the material has a dielectric constant less than about 3.5.
  • the low-k dielectric materials include low-polarity materials such as silicon- containing organic polymers, silicon-containing hybrid organic/inorganic materials, organosilicate glass (OSG), TEOS, fluorinated silicate glass (FSG), silicon dioxide, and carbon-doped oxide (CDO) glass. It is to be appreciated that the low-k dielectric materials may have varying densities and varying porosities.
  • substantially devoid is defined herein as less than 2 wt. %, preferably less than 1 wt. %, more preferably less than 0.5 wt. %, and most preferably less than 0.1 wt. %. "Devoid” corresponds to 0 wt. %.
  • suitable for removing polymers and other organic materials from a surface having same thereon corresponds to at least partial removal of said polymers and other organic materials from the surface. Preferably, between 50 and 85% of the polymers and other organic materials are removed from the surface using the compositions described herein, more preferably at least 90%, even more preferably at least 95%, and most preferably at least 99% of the polymers and other organic materials are removed.
  • metal correspond to: tantalum, tantalum nitride, titanium nitride, titanium, nickel, cobalt, tungsten, and suicides thereof; copper-containing layers; aluminum- containing layers; Al/Cu layers; alloys of Al; alloys of Cu; cobalt-containing layers such as CoWP and CoWBP; gold-containing layers; Au/Pt layers; hafnium oxides; hafnium oxysilicates; zirconium oxides; lanthanide oxides; titanates; nitrogen-doped analogues thereof; ruthenium; iridium; cadmium; lead; indium; selenium; silver; MoTa; and combinations and salts thereof on the microelectronic device.
  • fluoride species correspond to species including an ionic fluoride (F " ) or covalently bonded fluorine. It is to be appreciated that the fluoride species may be included as a fluoride species or generated in situ.
  • amine species include at least one primary, secondary, or tertiary amine, ammonia, and/or quaternary ammonium hydroxide compounds (e.g., ammonium hydroxide, alkylammonium hydroxide, alkylarylammonium hydroxide, etc.), with the proviso that (i) species including an five-membered heterocyclic ring, wherein at least one member of the ring is a nitrogen atom, and (ii) species including both a carboxylic acid group and an amine group, are not considered amines for the purposes of this invention.
  • quaternary ammonium hydroxide compounds e.g., ammonium hydroxide, alkylammonium hydroxide, alkylarylammonium hydroxide, etc.
  • Amines for the purposes of this invention include, but are not limited to: aliphatic primary, secondary, or tertiary amines; 4, 6, 7, 8, 9 or 10-membered saturated or unsaturated amine rings; alkylammonium hydroxide compounds having the general formula R 1 R 2 R3R 4 NOH where Ri, R 2 , R3 and R 4 are the same as or different from one another and are hydrogen and Ci-C 6 alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl or hexyl); alkylarylammonium hydroxide compounds have the general formula R 1 R 2 R3R 4 NOH where Ri, R 2 , R3 and R 4 are the same as or different from one another and are hydrogen, CpC 6 alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl or hexyl) and substituted or unsubstituted C 6 -CiO
  • R may be the same as or different from one another and are selected from the group consisting of hydrogen, C r C 6 alkyls (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl), C r C 6 alcohols (e.g., methanol, ethanol, propanol, butanol, pentanol, hexanol), CpC 6 primary amines, Ci-C 6 secondary amines, and carbonyl groups.
  • C r C 6 alkyls e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl
  • C r C 6 alcohols e.g., methanol, ethanol, propanol, butanol, pentanol, hexanol
  • CpC 6 primary amines e.g., ethanol, ethanol, propanol, butanol, pent
  • complexing agent includes those compounds that are understood by one skilled in the art to be complexing agents, chelating agents, sequestering agents, and combinations thereof. Complexing agents will chemically combine with or physically hold the metal atom and/or metal ion to be removed using the compositions described herein.
  • contaminants correspond to chemicals, excluding residue and the components of the removal compositions, present on the surface of the microelectronic device subsequent to the plasma etching, ashing, wet etching, or chemical mechanical polishing process, reaction and chemical by-products, and any other materials that are the by-products of said processes.
  • contaminants will be organic in nature.
  • paint will be understood to refer to coatings such as epoxies, enamels, latexes, primers, basecoats, clearcoats, lacquers, varnishes, shellacs and polyurethane finishes which are used to protect and/or beautify surfaces.
  • “Paints” may be fresh, dried, and/or aged.
  • paint removal refers to compositions which remove or facilitate the removal of paint from a surface.
  • Waaxes are defined as substances that are plastic solids at ambient temperatures and, on being subjected to moderately elevated temperatures, become low viscosity liquids.
  • One type of wax is wax
  • paraffin wax is a petroleum wax which occurs naturally in many types of crude oil around the world. Chemically, paraffins, and by extension paraffin waxes occurring naturally in petroleum, are usually mixtures of straight carbon chain alkanes. The physical properties of the paraffin waxes, including melting point, congealing point, and plastic flow properties, vary with the "carbon chain length" of the wax or waxes present in the petroleum.
  • Oil includes non-polar compounds that are viscous at room temperature and are immiscible with water. Oils may be classified as mineral oils, originating from biomass, or organic oils, which are produced by plants, animals and other organisms through organic processes. Organic oils include, but are not limited to, lipids such as oils, fats, waxes, cholesterol and other oily substances found in living things.
  • si-aqueous refers to a mixture of water and organic components.
  • compositions may be embodied in a wide variety of specific formulations, as hereinafter more fully described.
  • specific components of the composition are discussed in reference to weight percentage ranges including a zero lower limit, it will be understood that such components may be present or absent in various specific embodiments of the composition, and that in instances where such components are present, they may be present at concentrations as low as 0.001 weight percent, based on the total weight of the composition in which such components are employed.
  • the semi-aqueous compositions include at least one polymer dissolution accelerator, at least one organic solvent, water, and optionally at least one complexing agent, wherein the composition is useful for the removal of polymers and other organic materials from a surface having same thereon.
  • the compositions are preferably substantially devoid of fluoride species.
  • a composition comprising, consisting of or consisting essentially of at least one organic solvent, at least one polymer dissolution accelerator, and water is described, wherein the composition is substantially devoid of fluoride and amine species and wherein the composition is useful for the removal of polymer and other organic material from a surface having same thereon.
  • a composition comprising, consisting of or consisting essentially of at least one complexing agent, at least one organic solvent, at least one polymer dissolution accelerator, and water is described, wherein the composition is substantially devoid of fluoride and amine species.
  • a composition comprising, consisting of or consisting essentially of at least one organic solvent, at least one imidazole compound, and water is described, wherein the composition is substantially devoid of fluoride and amine species.
  • a composition comprising, consisting of or consisting essentially of at least one complexing agent, at least one organic solvent, at least one imidazole compound, and water is described, wherein the composition is substantially devoid of fluoride species and amine species.
  • the specific proportions and amounts of components, in relation to each other, may be suitably varied to provide the desired removal action of the composition for polymer, other organic materials and/or processing equipment, as readily determinable within the skill of the art without undue effort.
  • the water is preferably deionized.
  • the complexing agents preferably have a high affinity for aluminum-containing residues.
  • Complexing agents contemplated include, but are not limited to, aminocarboxylic acids, organic acids and derivatives thereof, phosphonic acids and derivatives thereof, and combinations thereof including: (ethylenedinitrilo)tetraacetic acid (EDTA), butylenediaminetetraacetic acid, (1,2- cyclohexylenedinitrilo)tetraacetic acid (CyDTA), diethylenetriaminepentaacetic acid (DTPA), ethylenediaminetetrapropionic acid, (hydroxyethyl)ethylenediaminetriacetic acid (HEDTA), N,N,N',N'-ethylenediaminetetra(methylenephosphonic)acid (EDTMP), triethylenetetraminehexaacetic acid (TTHA), l,3-diamino-2-hydroxypropane-N,N,N',N'-tetraacetic acid (DHPTA), methyliminodiacetic acid, propylenediaminetetraacetic acid,
  • the complexing agents have solubility in water (in a solution including just the complexing agent and water) greater than or equal to about 0.5 wt.%, based on the total weight of the composition.
  • Particularly preferred complexing agents include 2,3-hydroxybenzoic acid, salicylic acid, sulfosalicylic acid, HEDP, and combinations thereof.
  • compositions of this aspect include, but are not limited to, sulfones, lactones, tetrahydrofurans and esters including, but not limited to, dimethylsulfoxide (DMSO), tetramethylene sulfone (sulfolane), dimethyl sulfone, diethyl sulfone, bis(2-hydroxyethyl) sulfone, methyl sulfolane, ethyl sulfolane, gamma-butyrolactone, delta- valerolactone, epsilon-caprolactone, alpha-acetylbutyrolactone, tetrahydro-2-furanmethanol, tetrahydro-2-furoic acid, 3-hydroxytetra
  • the polymer dissolution accelerators include five-membered heterocyclic rings having at least one member of the ring being a nitrogen atom are best described by referring to the following structures:
  • R may be the same as or different from one another and are selected from the group consisting of hydrogen, CpC 6 alkyls (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl), Ci-C 6 alcohols (e.g., methanol, ethanol, propanol, butanol, pentanol, hexanol), CpC 6 primary amines, Q-C 6 secondary amines, and carbonyl groups.
  • CpC 6 alkyls e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl
  • Ci-C 6 alcohols e.g., methanol, ethanol, propanol, butanol, pentanol, hexanol
  • CpC 6 primary amines e.g., methyl, ethyl, propyl, butyl, pentyl,
  • Examples include, but are not limited to, l-(3-aminopropyl)-imidazole (API), imidazole, 1 ,2-hydroxyethylimidazole (HEI), histamine (neutral or protonated), hydantoin, 1,3- dimethyl-2-imidazolidinone, N-methylpyrrolidinone, l-ethyl-3-methylimidazolium salt (e.g., halide or methane sulfonate), l-ethyl-2,3-dimethylimidazolium salt (e.g., halide), and combinations thereof.
  • Particularly preferred polymer dissolution accelerators include HEI, API, or a combination of HEI and API.
  • compositions described herein have pH in a range from about 1 to about 14, and preferably about 6 to about 8.
  • compositions are initially substantially devoid of fluoride, amines (with the proviso that (i) species including an five-membered heterocyclic ring, wherein at least one member of the ring is a nitrogen atom, and (ii) species including both a carboxylic acid group and an amine group, are not considered amines for the purposes of this invention), abrasive material, oxidants such as H 2 O 2 , vinyl imidazole (and polyvinyl imidazole), antibacterial additives, copper, mannanase enzymes, fluorinated solvents, catalysts having at least one imine linkage and combinations thereof.
  • oxidants such as H 2 O 2 , vinyl imidazole (and polyvinyl imidazole)
  • antibacterial additives copper, mannanase enzymes, fluorinated solvents, catalysts having at least one imine linkage and combinations thereof.
  • compositions must be in one distinct phase (i.e., all of the components are miscible) and the compositions must not be polymerizable (e.g., the composition should be substantially devoid of monomers and resins that are typically found in polymer-deposition solutions).
  • initially devoid corresponds to a composition that has not yet been in contact with a surface having polymer and other organic materials thereon.
  • the composition has a pH in a range from about 10 to about 14, wherein the composition comprises, consists of or consists essentially of at least one organic solvent, at least one polymer dissolution accelerator, and water.
  • the amount of organic solvent is about 20 to about 80 wt%
  • the amount of water is in a range from about 10 to about 70 wt%, based on the total weight of the composition.
  • the composition has a pH in a range from about 6 to about 8, wherein the composition comprises, consists of or consists essentially of at least one complexing agent, at least one organic solvent, at least one polymer dissolution accelerator, and water.
  • the amount of organic solvent is about 20 to about 80 wt%
  • the amount of polymer dissolution accelerator in about 1 to about 20 wt%
  • the amount of complexing agent is about 1 to about 15 wt%
  • the amount of water is in a range from about 10 to about 70 wt%, based on the total weight of the composition.
  • compositions are formulated in the following Formulations A-L and wherein all percentages are by weight, based on the total weight of the formulation:
  • Formulation A 20-80 wt% DMSO, 1-20 wt% API, 10-70 wt% water
  • Formulation B 20-80 wt% gamma-butyrolactone, 1-20 wt% API, 10-70 wt% water
  • Formulation C 20-80 wt% DMSO, 1-20 wt% API, 1-15 wt% salicylic acid, 10-70 wt% water
  • Formulation D 20-80 wt% gamma-butyrolactone, 1-20 wt% API, 1-15 wt% salicylic acid, 10-70 wt% water
  • Formulation E 20-80 wt% DMSO, 1-20 wt% HEI, 1-15 wt% salicylic acid, 10-70 wt% water
  • Formulation F 20-80 wt% gamma-butyrolactone, 1-20 wt% HEI, 1-15 wt% salicylic acid, 10-70 wt% water
  • Formulation G 20-80 wt% DMSO, 1-20 wt% API, 1-15 wt% sulfosalicylic acid, 10-70 wt% water
  • Formulation H 20-80 wt% gamma-butyrolactone, 1-20 wt% API, 1-15 wt% sulfosalicylic acid, 10-
  • Formulation I 20-80 wt% DMSO, 1-20 wt% HEI, 1-15 wt% sulfosalicylic acid, 10-70 wt% water
  • Formulation J 20-80 wt% gamma-butyrolactone, 1-20 wt% HEI, 1-15 wt% sulfosalicylic acid, 10-
  • Formulation K 72 wt% gamma-butyrolactone, 6 wt% API, 5 wt% sulfosalicylic acid, 17 wt% water
  • Formulation L 80 wt% DMSO, 10 wt% API, 10 wt% water
  • the removal composition can comprise, consist of or consist essentially of: DMSO, salicylic acid or a salicylic acid derivative and water; gamma-butyrolactone, salicylic acid or a salicylic acid derivative and water; DMSO, API, salicylic acid or a salicylic acid derivative and water; or DMSO, HEI, salicylic acid or a salicylic acid derivative and water.
  • the aforementioned compositions further include polymeric and/or other organic materials.
  • the composition may include at least one complexing agent, at least one organic solvent, at least one polymer dissolution accelerator, water and polymeric and/or organic material.
  • the composition may include at least one organic solvent, at least one polymer dissolution accelerator, water, and polymeric and/or organic material. The polymeric and/or organic material may be dissolved and/or suspended in the removal composition described herein.
  • compositions described herein are compatible with low-k dielectric and metal-containing materials on the surface.
  • low-k dielectrics and metals are not damaged using the removal compositions described herein
  • the compositions are water soluble, non-corrosive, nonflammable and of low toxicity.
  • the compositions described herein may be used in single wafer (as well as batch wafer) tool sets which is a significant advance over the amine-containing cleaners in the art.
  • the compositions described herein are easily formulated by simple addition of the respective ingredients and mixing to homogeneous condition.
  • compositions may be readily formulated as single-package formulations or multi-part formulations that are mixed at or before the point of use, e.g., the individual parts of the multi-part formulation may be mixed at the tool or in a storage tank upstream of the tool.
  • concentrations of the respective ingredients may be widely varied in specific multiples of the composition, i.e., more dilute or more concentrated, and it will be appreciated that the compositions described herein can variously and alternatively comprise, consist or consist essentially of any combination of ingredients consistent with the disclosure herein.
  • another aspect relates to a kit including, in one or more containers, one or more components adapted to form the compositions described herein.
  • the kit may include, in one or more containers, at least one complexing agent, at least one organic solvent, at least one polymer dissolution accelerator and optionally water, for combining with additional solvent, e.g., water and/or organic solvent, at the fab or the point of use.
  • the kit may include, in one or more containers, at least one organic solvent, at least one polymer dissolution accelerator, and optionally water, for combining with additional solvent, e.g., water and/or organic solvent, at the fab or the point of use.
  • a method of removing polymer and/or other organic materials from a surface includes contacting a removal composition with the surface having the polymer and/or other organic materials thereon, under sufficient contacting conditions to remove the polymer and/or other organic materials from the surface.
  • the surface corresponds to any solid material that the polymer or other organic material may be found on including, but not limited to, microelectronic devices, metals, plastics, fabrics, fibers, soils, wood, paper, glass, leather and other animal hides, cement, concrete, bricks, drywall, asphalt, keratin-containing substances such as hair and nails, rubber, latex, and combinations thereof.
  • photoresist and/or resist-containing residues may be removed.
  • paint may be removed.
  • wax may be removed.
  • oils may be removed.
  • a removal composition as described herein is contacted in any suitable manner to the surface having polymer and/or other organic material thereon, e.g., by spraying a removal composition on the surface, by dipping (in a volume of a removal composition) of the surface including the polymeric/organic material, by contacting the surface with another material, e.g., a pad, or fibrous sorbent applicator element, that has a removal composition absorbed thereon, by contacting the surface including the polymeric/organic material to be removed with a recirculating removal composition, or by any other suitable means, manner or technique, by which a removal composition is brought into removal contact with the material(s) to be removed.
  • a removal composition is brought into removal contact with the material(s) to be removed.
  • the removal process using a removal composition may include a static clean, a dynamic clean, or sequential processing steps including dynamic cleaning, followed by static cleaning of the surface in a removal composition, with the respective dynamic and static steps being carried out alternatingly and repetitively, in a cycle of such alternating steps.
  • compositions described herein have particular utility in applications including, but not limited to, photoresist removal, post-etch residue removal, post-ash residue removal, surface preparation, post-plating cleaning, post-CMP residue removal, contaminant removal, anti-reflective coating removal, and combinations thereof.
  • the compositions described herein are usefully employed to remove polymers and/or other organic materials from the surface of the microelectronic device.
  • the compositions do not damage low-k dielectric materials or corrode metal interconnects on the device surface.
  • the compositions remove at least 85 % of the polymers and/or other organic materials present on the device prior to removal, more preferably at least 90 %, even more preferably at least 95 %, and most preferably at least 99%.
  • the composition In use of the compositions described herein for removing polymers and/or other organic materials from surfaces having same thereon, the composition typically is contacted with the surface for a time of from about 5 sec to about 60 minutes, preferably about 1 min to 30 min, at temperature in a range of from about 20 0 C to about 60 0 C.
  • Such contacting times and temperatures are illustrative, and any other suitable time and temperature conditions may be employed that are efficacious to at least partially clean the polymers and/or other organic materials from the surface.
  • the composition may be readily removed from the device to which it has previously been applied, as may be desired and efficacious in a given end use application of the compositions described herein.
  • the rinse solution includes deionized water and optionally further includes at least one corrosion inhibitor. Thereafter, the device may be dried using nitrogen or a spin-dry cycle.
  • Preferred corrosion inhibitors include, but are not limited to, ascorbic acid, adenosine, L(+)-ascorbic acid, isoascorbic acid, ascorbic acid derivatives, benzotriazole (BTA), citric acid, ethylenediamine, gallic acid, oxalic acid, tannic acid, ethylenediaminetetraacetic acid (EDTA), uric acid, 1 ,2,4-triazole (TAZ), tolyltriazole, 5-phenyl- benzotriazole, 5-nitro-benzotriazole, 3-amino-5-mercapto-l,2,4-triazole, l-amino-l,2,4-triazole, hydroxybenzotriazole, 2-(5-amino-pentyl)-benzotriazole, l-amino-l,2,3-triazole, l-amino-5-methyl- 1,2,3-triazole, 3-amino-l,2,4-
  • a still further aspect relates to methods of manufacturing an article comprising a microelectronic device, said method comprising contacting the microelectronic device with a composition for sufficient time to remove polymers and/or other organic materials from the microelectronic device having said polymers and/or other organic thereon, and incorporating said microelectronic device into said article.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Detergent Compositions (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention porte sur des compositions d'élimination et des procédés d'élimination de polymères et/ou autres matières organiques à partir d'une surface sur laquelle ils et/ou elles se trouvent. La composition semi-aqueuse est sensiblement exempte d'espèces fluorures.
PCT/US2010/022987 2009-02-05 2010-02-03 Composition ne contenant pas de fluorure pour l'élimination de polymères et autres matières organiques à partir d'une surface Ceased WO2010091045A2 (fr)

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US9175404B2 (en) 2011-09-30 2015-11-03 Advanced Technology Materials, Inc. Etching agent for copper or copper alloy
FR3023484A1 (fr) * 2014-07-11 2016-01-15 R&D Pharma Preparations antifongiques destinees au traitement local des onychomycoses
US9238850B2 (en) 2010-08-20 2016-01-19 Advanced Technology Materials, Inc. Sustainable process for reclaiming precious metals and base metals from e-waste
WO2016109387A1 (fr) * 2014-12-30 2016-07-07 Fujifilm Electronic Materials U.S.A., Inc. Compositions de décapage pour détacher des photorésines de substrats semi-conducteurs
US9416338B2 (en) 2010-10-13 2016-08-16 Advanced Technology Materials, Inc. Composition for and method of suppressing titanium nitride corrosion
US9546321B2 (en) 2011-12-28 2017-01-17 Advanced Technology Materials, Inc. Compositions and methods for selectively etching titanium nitride
US9678430B2 (en) 2012-05-18 2017-06-13 Entegris, Inc. Composition and process for stripping photoresist from a surface including titanium nitride
US9765288B2 (en) 2012-12-05 2017-09-19 Entegris, Inc. Compositions for cleaning III-V semiconductor materials and methods of using same
US10138117B2 (en) 2013-07-31 2018-11-27 Entegris, Inc. Aqueous formulations for removing metal hard mask and post-etch residue with Cu/W compatibility
US10176979B2 (en) 2012-02-15 2019-01-08 Entegris, Inc. Post-CMP removal using compositions and method of use
US10340150B2 (en) 2013-12-16 2019-07-02 Entegris, Inc. Ni:NiGe:Ge selective etch formulations and method of using same
US10347504B2 (en) 2013-12-20 2019-07-09 Entegris, Inc. Use of non-oxidizing strong acids for the removal of ion-implanted resist
US10428271B2 (en) 2013-08-30 2019-10-01 Entegris, Inc. Compositions and methods for selectively etching titanium nitride
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US10557107B2 (en) 2014-01-29 2020-02-11 Entegris, Inc. Post chemical mechanical polishing formulations and method of use
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US10920141B2 (en) 2013-06-06 2021-02-16 Entegris, Inc. Compositions and methods for selectively etching titanium nitride
US11127587B2 (en) 2014-02-05 2021-09-21 Entegris, Inc. Non-amine post-CMP compositions and method of use
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US9238850B2 (en) 2010-08-20 2016-01-19 Advanced Technology Materials, Inc. Sustainable process for reclaiming precious metals and base metals from e-waste
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US9790600B2 (en) 2011-09-30 2017-10-17 Entegris, Inc. Etching agent for copper or copper alloy
US9175404B2 (en) 2011-09-30 2015-11-03 Advanced Technology Materials, Inc. Etching agent for copper or copper alloy
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US10428271B2 (en) 2013-08-30 2019-10-01 Entegris, Inc. Compositions and methods for selectively etching titanium nitride
US10340150B2 (en) 2013-12-16 2019-07-02 Entegris, Inc. Ni:NiGe:Ge selective etch formulations and method of using same
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US10475658B2 (en) 2013-12-31 2019-11-12 Entegris, Inc. Formulations to selectively etch silicon and germanium
US10557107B2 (en) 2014-01-29 2020-02-11 Entegris, 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
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WO2016109387A1 (fr) * 2014-12-30 2016-07-07 Fujifilm Electronic Materials U.S.A., Inc. Compositions de décapage pour détacher des photorésines de substrats semi-conducteurs
US9914902B2 (en) 2014-12-30 2018-03-13 Fujifilm Electronic Materials U.S.A., Inc. Stripping compositions for removing photoresists from semiconductor substrates
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JPWO2020071261A1 (ja) * 2018-10-03 2021-09-24 富士フイルム株式会社 薬液及び薬液収容体
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