WO2014205285A1 - Method of removing silicone resin from a substrate - Google Patents

Method of removing silicone resin from a substrate Download PDF

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Publication number
WO2014205285A1
WO2014205285A1 PCT/US2014/043281 US2014043281W WO2014205285A1 WO 2014205285 A1 WO2014205285 A1 WO 2014205285A1 US 2014043281 W US2014043281 W US 2014043281W WO 2014205285 A1 WO2014205285 A1 WO 2014205285A1
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WO
WIPO (PCT)
Prior art keywords
sulfuric acid
substrate
resin
resin coating
weight percent
Prior art date
Application number
PCT/US2014/043281
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English (en)
French (fr)
Inventor
Peng-Fei Fu
Ginam Kim
Sheng Wang
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Dow Corning Corporation
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Publication date
Application filed by Dow Corning Corporation filed Critical Dow Corning Corporation
Publication of WO2014205285A1 publication Critical patent/WO2014205285A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D9/00—Chemical paint or ink removers
    • C09D9/005—Chemical paint or ink removers containing organic solvents
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K13/00—Etching, surface-brightening or pickling compositions
    • C09K13/04—Etching, surface-brightening or pickling compositions containing an inorganic acid
    • C09K13/06—Etching, surface-brightening or pickling compositions containing an inorganic acid with organic material
    • 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
    • C11D7/08—Acids
    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/3105—After-treatment
    • H01L21/311—Etching the insulating layers by chemical or physical means
    • H01L21/31105—Etching inorganic layers
    • H01L21/31111—Etching inorganic layers by chemical means
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
    • C08K2003/309—Sulfur containing acids
    • 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

  • the amount of any residue remaining on the cleaned substrate is from 0 to less than 0.20 weight percent in embodiments of the method where the resin-coated substrate is soaked in the (i) concentrated sulfuric acid and from 0 to less than 0.26 weight percent in embodiments of the method where the resin-coated substrate is soaked in the (ii) a mixture of concentrated sulfuric acid mixed with one or more organic compounds.
  • the methods disclosed herein provide high throughput and speed of removal of the cured resin coating from the substrate using chemicals that do not damage the substrate.
  • Silicone resin materials have been widely used in the microelectronics packaging industry due to their excellent thermal stability, hydrophobicity, good adhesion, and excellent elastic properties.
  • the cured silicone coating or layer on the substrate be removed for reclaiming of the substrate, e.g., if the cured silicone layer is used as a sacrificial layer or material, or for reworkability of a device substrate.
  • Methods which can readily facilitate removal of a cured silicone resin from a substrate for substrate reclaim or from a device substrate are desired. Theoretically, silicone resin can be degraded under acid and basic conditions. However, removal of silicone resin is very challenging.
  • the sulfuric acid of the aqueous, concentrated sulfuric acid is at a concentration that is effective for producing a degraded resin coating and, ultimately, completely removing any resin residue from the resin-coated substrate or removing resin residue from the resin-coated substrate such that any silicone residue remaining on the substrate is from 0 to less than 0.20 weight percent (wt.%).
  • the sulfuric acid of the (i) aqueous, concentrated sulfuric acid is at a concentration of at least 95 wt.% and, in some embodiments, at a concentration of at least 96 wt.%.
  • the concentration level of the sulfuric acid of the (i) aqueous, concentrated sulfuric acid is determined by dilution of commercially available concentrated sulfuric acid with the appropriate amount of water to reach the desired sulfuric acid concentration level (for example, dilution of 99.999 wt.% commercially available concentrated sulfuric acid to reach a desired 95% wt.% concentration).
  • the aqueous, concentrated sulfuric acid levels detailed herein may be prepared by any suitable method such as methods known for preparing same and, alternatively, may be purchased from a commercial supplier thereof such as Sigma- Aldrich Chemical Company (St. Louis, MO) (product no. 339741 ) and used as supplied or by diluting to the sulfuric acid concentration level.
  • the concentration of sulfuric acid of the (i) aqueous, concentrated sulfuric acid may be 96 wt.%, 97 wt.%, 98 wt.%, 99 wt.%, or 99.9 wt.%.
  • the concentration of sulfuric acid of the (i) aqueous, concentrated sulfuric acid may alternatively be 96 wt.%, 97 wt.%, 98 wt.%, 99 wt.%, or 99.9 wt.% except wherein any one of the concentrations 96 wt.%, 97 wt.%, 98 wt.%, 99 wt.%, and 99.9 wt.% is excluded therefrom.
  • the sulfuric acid of the (i) aqueous, concentrated sulfuric acid is at a concentration of 95 to ⁇ 100 wt.%; alternatively, at a concentration of 96 to ⁇ 100 wt.%; alternatively, at a concentration of 97 to ⁇ 100 wt.%; alternatively, at a concentration of 97 to ⁇ 100 wt.%; alternatively, at a concentration of 98 to ⁇ 100 wt.%; and alternatively, at a concentration of 99 to ⁇ 100 wt.%.
  • the sulfuric acid of the (i) aqueous, concentrated sulfuric acid may be at most 99.999 wt.%. In yet other embodiments, the sulfuric acid of the concentrated sulfuric acid may be 100 wt.%.
  • the (ii) a mixture of concentrated sulfuric acid mixed with one or more organic compounds may be used.
  • the mixture may be a solution, a suspension, or a colloid.
  • the mixture (ii) may be just a solution, alternatively just a suspension, or alternatively just a colloid.
  • the sulfuric acid-organic compound mixture includes (1 ) concentrated sulfuric acid having a starting concentration (i.e., the concentration prior to mixing the concentrated sulfuric acid ingredient with the one or more organic compounds to form the sulfuric acid- organic compound mixture) of at least 95 wt.% and, in some embodiments, at a concentration of at least 96 wt.%, (2) an alkane solvent having 5 or more carbons and combination(s) thereof, and (3) optionally, an aromatic sulfonic acid, an aromatic sulfonic acid salt, an aliphatic sulfonic acid, an aliphatic sulfonic acid salt, a carboxylic acid, a carboxylic acid salt, or any combination(s) thereof (i.e., a combination of any two or more of an aromatic s
  • the total concentration of the sulfuric acid in the sulfuric acid-organic compound mixture is at least 20 wt.% and, in some embodiments, the total concentration of the sulfuric acid is at least 30 wt.%. In some embodiments, the total concentration of the sulfuric acid in the sulfuric acid- organic compound mixture is at least 20 wt.% to 80 wt.%.
  • the total concentration of the sulfuric acid in the sulfuric acid-organic compound mixture is calculated by measuring the weight of concentrated sulfuric acid divided by the total weight of the mixture, expressed as a percent.
  • the sulfuric acid of the sulfuric acid-organic compound mixture is at a concentration that is effective for producing a degraded resin coating and, ultimately, completely removing any resin residue from the resin-coated substrate or removing resin residue from the resin-coated substrate such that any silicone residue remaining on the substrate is less than 0.26 wt.% (that is, from 0 to less than 0.26 wt.%).
  • the starting concentration of sulfuric acid used to prepare the (ii) sulfuric acid-organic compound mixture may be 96 wt.%, 97 wt.%, 98 wt.%, 99 wt.%, or 99.9 wt.%.
  • the starting concentration of sulfuric acid used to prepare the (ii) sulfuric acid-organic compound mixture may alternatively be 96 wt.%, 97 wt.%, 98 wt.%, 99 wt.%, or 99.9 wt.% except wherein any one of the starting concentrations 96 wt.%, 97 wt.%, 98 wt.%, 99 wt.%, and 99.9 wt.% is excluded therefrom.
  • the sulfuric acid used to prepare the (ii) sulfuric acid- organic compound mixture is at a starting concentration of 95 to ⁇ 100 wt.%; alternatively, at a starting concentration of 96 to ⁇ 100 wt.%; alternatively, at a starting concentration of 97 to ⁇ 100 wt.%; alternatively, at a starting concentration of 97 to ⁇ 100 wt.%; alternatively, at a starting concentration of 98 to ⁇ 100 wt.%; and alternatively, at a starting concentration of 99 to ⁇ 100 wt.%.
  • the sulfuric acid used to prepare the (ii) sulfuric acid-organic compound mixture may be at a starting concentration of at most 99.999 wt.%. In yet other embodiments, the sulfuric acid of the (ii) sulfuric acid-organic compound mixture may be at a starting concentration of 100 wt.%.
  • the total concentration of sulfuric acid used to prepare the (ii) sulfuric acid-organic compound mixture may be at least 20 wt.%, 21 wt.%, 22 wt.%, 23 wt.%, 24 wt.%, 25 wt.%, 26 wt.%, 27 wt.%, 28 wt.%, 29 wt.% or 30 wt.%.
  • the total concentration of sulfuric acid of the (ii) sulfuric acid-organic compound mixture may be at least 31 wt.%, 32 wt.%, 33 wt.%, 34 wt.%, 35 wt.%, 36 wt.%, 37 wt.%, 38 wt.%, 39 wt.% or 40 wt.%.
  • the total concentration of sulfuric acid in the (ii) sulfuric acid-organic compound mixture may alternatively be 31 wt.%, 32 wt.%, 33 wt.%, 34 wt.%, 35 wt.%, 36 wt.%, 37 wt.%, 38 wt.%, 39 wt.% or 40 wt.% except wherein any one of the starting concentrations 31 wt.%, 32 wt.%, 33 wt.%, 34 wt.%, 35 wt.%, 36 wt.%, 37 wt.%, 38 wt.%, 39 wt.% or 40 wt.% is excluded therefrom.
  • the sulfuric acid of the (ii) sulfuric acid-organic compound mixture is at a total concentration of at least 30.5 wt.%; alternatively, at least 31.5 wt.% in other embodiments; alternatively, at least 32.5 wt.% in further embodiments; alternatively, at least 33.5 wt.% in still further embodiments; alternatively, at least 34.5 wt.% in yet further embodiments; alternatively, at least 35.5 wt.% in still further embodiments; alternatively, at least 36.5 wt.% in yet further embodiments; alternatively, at least 37.5 wt.% in still further embodiments; alternatively, at least 38.5 wt.% in yet further embodiments; and alternatively, at least 39.5 wt.% in still further embodiments.
  • the degraded resin coating resulting from the soaking step is washed away with a first organic solvent or mixtures thereof.
  • the washed substrate may optionally be further washed with a second organic solvent or mixtures thereof following the washing with the first organic solvent or mixtures thereof.
  • the substrate resulting from the organic solvent washing step(s) is then washed with water to remove the first organic solvent(s) (and, if used, the second organic solvent(s)) and form a cleaned substrate substantially lacking the cured resin coating (or a reaction product thereof) and substantially lacking the degraded resin coating (or a reaction product thereof). Contaminants present on the substrate will also be removed from the organic solvent(s) washing and water washing steps.
  • the substrate substantially lacking the cured resin coating and substantially lacking the degraded resin coating may be dried with air, argon, nitrogen or mixtures thereof. Upon drying, the substrate may also lack the organic solvent(s).
  • the resin-coated substrate is formed by coating a curable Si-O-Si containing silicone resin onto the substrate to a resin coating thickness of from greater than 0 millimeter up to about 1 millimeter (mm) to form a curable resin-coated substrate.
  • the curable Si-O-Si containing silicone resin of the coating is cured to yield a cured form of the resin-coated substrate.
  • the curable resin including the curable Si-O-Si containing silicone resin used for coating the substrate to form the curable resin-coated substrate may be partially cured prior to application onto the substrate and/or cured after or upon application onto the substrate.
  • the curable Si-O-Si containing silicone resin is cured prior to soaking the resin-coated substrate in the concentrated sulfuric acid-based reagent.
  • the curable resin used for coating the substrate to form the curable resin-coated substrate may be partially cured prior to application onto the substrate and/or cured after or upon application onto the substrate.
  • a resin is coated onto a substrate to a resin thickness of from greater than 0 mm up to about 1 mm.
  • the resin is a curable resin.
  • the resin is coated onto the substrate to a resin thickness of from greater than 0 mm up to about 500 microns.
  • the resin is coated onto the substrate to a resin thickness from about 2 microns to about 500 microns.
  • the resin is coated onto the substrate from about 5 microns to about 200 microns.
  • the curable resin may contain the following structural unit:
  • the substrate used in the inventive methods can be a silicon wafer, a silicon plate, a glass wafer, a glass plate, a silicon carbide wafer, a silicon carbide plate, a patterned silicon wafer, a patterned glass wafer, a patterned silicon carbide wafer, a device wafer, a device plate, or any other suitable substrate.
  • silicon wafer also referred to as a slice or substrate refers to a thin slice of semiconductor material, such as a silicon crystal, used in the fabrication of integrated circuits and other microdevices; the "silicon wafer” serves as the substrate for microelectronic devices built in and over the wafer and undergoes a number of microfabrication process steps such as doping or ion implantation, etching, deposition of various materials, and photolithographic patterning.
  • silicon plate refers to a thin slice of semiconductor material with shapes, e.g., rectangle, square and other shapes other than a circle, such as a silicon crystal, used in the fabrication of integrated circuits and other microdevices; the “silicon plate” serves as the substrate for microelectronic devices built in and over the plate and undergoes a number of microfabrication process steps such as doping or ion implantation, etching, deposition of various materials, and photolithographic patterning.
  • the substrate can be a bare substrate (a substrate without any coating thereon or any treatment on its surface) or a substrate coated with one or more protective coatings.
  • the substrate can be a patterned device substrate.
  • suitable substrates include bare silicon wafers, bare glass wafers, patterned silicon wafers, patterned glass wafers and patterned silicon carbide wafers.
  • the surface of the substrate which is directly in contact with the concentrated sulfuric acid should be highly non-reactive with the concentrated sulfuric acid (or, if used, the sulfuric acid-organic compound mixture) within a time frame of about 10 to about 60 minutes.
  • the substrate may be coated with a protective layer that is highly non-reactive with the concentrated sulfuric acid (or, if used, the sulfuric acid-organic compound mixture).
  • the surface of the substrate or the protective layer/coating on the substrate will not be damaged by the sulfuric acid within 1 or 2 hours (e.g., ⁇ 120 minutes, alternatively ⁇ 90 minutes, and alternatively ⁇ 60 minutes) during the silicone stripping process.
  • the protective layer is coated onto a patterned wafer of silicon, glass or silicon carbide or a patterned plate of silicon, glass or silicon carbide prior to coating the silicone resin. This protects the pattern of the patterned wafer or plate from corrosion and/or deterioration caused by the concentrated sulfuric acid.
  • the protective layer is in direct physical contact with the substrate. In alternative embodiments, the protective layer is in direct physical contact with the cured resin coating of the Si-O-Si containing silicone resin. In still further embodiments, the protective layer is in direct physical contact with both the substrate and the Si-O-Si containing silicone resin. In some embodiments, the protective layer is disposed between the substrate and the Si-O-Si containing silicone resin of the cured resin coating.
  • the protective layer can be made from a variety of materials such as, but not limited to, polyimide, silicon nitride, etc.
  • the coated resin on the substrate is cured.
  • the curing may be, for example, a thermal cure or a photochemical cure.
  • the curing mechanism may include condensation cure or addition cure.
  • condensation curing may be catalyzed by a variety of things such as titanium or tin compounds.
  • addition curing may include hydrosilylation cure, often with a platinum- or rhodium-based catalyst, or free radical cure, often with a free radical initiator/photo radical initiator, or a thermal acid generator/photo acid generator. Any suitable curing technique which results in suitable crosslinking may be employed.
  • the curing occurs prior to soaking the resin-coated substrate in the concentrated sulfuric acid-based reagent.
  • the resin-coated substrate is soaked in a concentrated sulfuric acid-based reagent (that is, the (i) an aqueous, concentrated sulfuric acid or the (ii) a mixture (e.g., solution) of concentrated sulfuric acid mixed with one or more organic compounds as detailed below).
  • a concentrated sulfuric acid-based reagent that is, the (i) an aqueous, concentrated sulfuric acid or the (ii) a mixture (e.g., solution) of concentrated sulfuric acid mixed with one or more organic compounds as detailed below.
  • the aqueous, concentrated sulfuric acid is at a concentration of at least 95 weight percent (wt.%). In some embodiments, where the aqueous, concentrated sulfuric acid is used, the aqueous, concentrated sulfuric acid is at a concentration of at least 96 wt.%. In further embodiments, where the aqueous, concentrated sulfuric acid is used, the aqueous, concentrated sulfuric acid is at a concentration of at least 97 wt.%. In still further embodiments, where the aqueous, concentrated sulfuric acid is used, the aqueous, concentrated sulfuric acid is at a concentration of at least 98 wt.%.
  • the aqueous, concentrated sulfuric acid is at a concentration of at least 99 wt.%. In still further embodiments, where the aqueous, concentrated sulfuric acid is used, the aqueous, concentrated sulfuric acid is at a concentration of at least 100 wt.%.
  • the sulfuric acid-organic compound mixture includes (1 ) concentrated sulfuric acid having a starting concentration of at least 95 wt.%, (2) an alkane solvent having 5 or more carbons and combination(s) thereof, and (3) optionally, an aromatic sulfonic acid, an aromatic sulfonic acid salt, an aliphatic sulfonic acid, an aliphatic sulfonic acid salt, a carboxylic acid, a carboxylic acid salt, or any combination thereof.
  • the concentrated sulfuric acid in the sulfuric acid-organic compound mixture is at a starting concentration of at least 96 wt.%. In yet further embodiments, the concentrated sulfuric acid in the sulfuric acid-organic compound mixture is at a starting concentration of at least 97 wt.%. In still further embodiments, the concentrated sulfuric acid in the sulfuric acid-organic compound mixture is at a starting concentration of at least 98 wt.%. In yet further embodiments, the concentrated sulfuric acid in the sulfuric acid-organic compound mixture is at a starting concentration of at least 99 wt.%. In some embodiments, the concentrated sulfuric acid in the sulfuric acid-organic compound mixture is at a starting concentration of at most ⁇ 100 wt.%, alternatively ⁇ 99.99 wt.%, alternatively ⁇ 99.9 wt.%.
  • the total concentration of the sulfuric acid in the mixture is at least 20 wt.%. In yet further embodiments, the total concentration of the sulfuric acid in the mixture (e.g., solution) is at least 30 wt.%. In still further embodiments, the total concentration of the sulfuric acid in the mixture (e.g., solution) is at least 40 wt.%. In yet further embodiments, the total concentration of the sulfuric acid in the mixture (e.g., solution) is at least 50 wt.%.
  • the total concentration of the sulfuric acid in the mixture is at most 90 wt.%, alternatively, at most 80 wt.%, alternatively at most ⁇ 70 wt.%. In some embodiments, the total concentration of the sulfuric acid in the mixture (e.g., solution) is at least 20 wt.% to 80 wt.%.
  • the sulfuric acid-organic compound mixture includes (2) an alkane solvent having 5 or more carbons.
  • alkane solvents having 5 or more carbons include, but are not limited to, heptanes, octanes, nonanes, decanes, undecanes, dodecanes, tetradecanes, and cyclic alkanes (such as cyclohexane).
  • the sulfuric acid- organic compound mixture may include more than one alkane solvent(s) having 5 or more carbons.
  • Each alkane solvent independently may have 30 carbons or fewer, alternatively 25 carbons or fewer, alternatively 20 carbons or fewer, alternatively 15 carbons or fewer.
  • the number of carbon atoms in the alkane solvent(s) is on average per molecule.
  • the alkane solvent(s) may be described by its boiling point or, for mixtures of alkane solvents, boiling point range.
  • the alkane solvent(s) may have a boiling point of at least 36 degrees Celsius (°C), alternatively at least 100°C, alternatively at least 150°C.
  • the alkane solvent(s) may have a boiling point of at most 400°C, alternatively at most 350°C, alternatively at most 300°C, alternatively at most 250°C.
  • the sulfuric acid-organic compound mixture optionally includes (3) an aromatic sulfonic acid, an aromatic sulfonic acid salt, an aliphatic sulfonic acid, an aliphatic sulfonic acid salt, a carboxylic acid, a carboxylic acid salt, or any combination(s) thereof.
  • aromatic sulfonic acids include, but are not limited to, dodecyl benzenesulfonic acid, benzenesulfonic acid, toluene sulfonic acid, decyl benzyl sulfonic acid, 4-dodecyl benzyl sulfonic acid (DBSA), and salts thereof.
  • aliphatic sulfonic acids include, but are not limited to, methane sulfonic acid, ethane sulfonic acid, butane sulfonic acid, decane sulfonic acid, dodecanesulfonic acid, and salts thereof.
  • carboxylic acids include, but are not limited to, formic acid, acetic acid, propionic acid, butanoic acid, and salts thereof.
  • sulfuric acid-organic compound mixture where the sulfuric acid-organic compound mixture is used, commercially available materials containing an alkane solvent(s) having 5 or more carbons and, optionally, aromatic sulfonic acid(s), aliphatic sulfonic acid(s), and/or carboxylic acid(s) and/or salts thereof may be used.
  • suitable commercially available materials include DIGESIL® NC Xtra and DYNASOLVE.
  • DIGESIL® NC Xtra contains mid petroleum distillates and dodecylbenzene sulfonic acid.
  • Petroleum distillates other than DIGESIL® NC Xtra may be used, particularly middle petroleum distillates (for example, fuel oils, gas oils) containing paraffins with a distillation range of between 150°C and 450°C (using ASTM D 86-67 titled "Standard Test Method for Distillation of Petroleum Products at Atmospheric Pressure").
  • the petroleum distillates contemplated for use herein have a distillation range from an initial boiling point of between 160°C and 190°C to a cut point of between 350°C and 390°C.
  • DYNASOLVE contains synthetic isoparaffinic hydrocarbon or hydrogenated petroleum naphtha and dodecylbenzene sulfonic acid.
  • Petroleum naphtha is an intermediate hydrocarbon liquid stream derived from the refining of crude oil.
  • Examples of commercially available DYNASOLVE products suitable for the sulfuric acid-organic compound mixture include, but are not limited to, DYNASOLVE 218, DYNASOLVE 220, DYNASOLVE 225, and DYNASOLVE 230.
  • the soaking of the resin-coated substrate in the concentrated sulfuric acid-based reagent is for from greater than 0 to about 60 minutes.
  • silicone resins are removed from the substrates described herein in a manner suitable for the microelectronics industry at high throughput levels, low cost of ownership levels, and with high surface clean quality in less than two hours.
  • the desired length of the soaking time depends on the thickness of the resin and the crosslink density of the resin. If the film thickness is low, very short soaking time is needed to remove the resin from the resin-coated substrate.
  • the soaking process may be carried out at room temperature or a higher temperature as needed. For example, the soaking process may be carried out at a temperature ranging from about 23°C to about 150°C. Higher temperature may accelerate the silicone resin removal rate.
  • the substrate is soaked in the concentrated sulfuric acid-based reagent, residual resin or residue may remain attached to the substrate.
  • the substrate is washed as detailed below.
  • the degraded resin resulting from the soaking step is washed with a first organic solvent or mixtures thereof.
  • the washing process can be simple flushing, soaking into the first organic solvent(s), or any suitable technique for washing or rinsing away the degraded resin coating from the substrate.
  • the first organic solvent(s) are carbon-based, water miscible liquids that are effective for washing the high dynamic viscosity, limited solubility silicone-based materials.
  • the first organic solvent(s) are polar, organic solvents suitable for removing the degraded resin coating from the substrate selected from isopropyl alcohol (I PA), acetone, 2-butanone, 1-propanol, 2-propanol, 1 -butanol, 2-butanol, dimethyl sulfoxide (DMSO), propylene glycol monomethyl ether, ethylene glycol monomethyl ether, and ethylene glycol dimethyl ether, or mixtures thereof.
  • the first organic solvent is isopropyl alcohol, acetone or a mixture of isopropyl alcohol and acetone.
  • the solvent(s) selected for the first organic solvent(s) should be highly non-reactive with the concentrated sulfuric acid and should not interact with the damaged/decomposed resin.
  • an optional second washing with a second organic solvent or mixtures thereof may be employed to further wash or rinse away the degraded resin coating from the substrate.
  • the washing process can be simple flushing, soaking into the second organic solvent, or any suitable technique for washing or rinsing away the degraded resin coating from the substrate.
  • the second organic solvent(s) is any carbon-based liquid that is effective for washing the first organic solvent.
  • the second organic solvent(s) is an organic solvent selected from alkanes, aromatic hydrocarbons, carboxylic esters, alcohols, ketones, ethers, or mixture(s) of these solvents suitable for removing the degraded coating from the substrate.
  • Suitable representative examples of the optional second organic solvent include I PA, n-butanol, 1 -butanol, 2- butanol, acetone, acetonitrile, 2-methoxy ethanol, 2-ethoxy ethanol, propylene glycol monomethyl ether, propylene glycol methyl ether acetate (PGMEA), 2-butanone, 1 -propanol, 2-propanol, DMSO, ethylene glycol monomethyl ether, ethylene glycol dimethyl ether, and butyl acetate.
  • the resulting washed substrate is further washed with water to remove the first organic solvent(s) (and, if used, the second organic solvent(s)) and form a cleaned substrate substantially lacking the cured resin coating (or a reaction product thereof) and substantially lacking the degraded resin coating (or a reaction product thereof). Contaminants present on the substrate will also be removed from the organic solvent(s) washing and water washing steps.
  • the water may be purified water such as deionized (Dl) water, which is particularly desirable for electronics end uses.
  • a nonpolar (or water immiscible) solvent is used for the second organic solvent washing step
  • the nonpolar solvent is desirably removed prior to washing with water. The removal can be, for example, by drying with air, argon, and/or nitrogen.
  • the amount of resin residue remaining on the wafer following the soaking and washing steps using the sulfuric acid soaking concentration levels described herein is 0.19 wt.% or less; in some embodiments, 0.18 wt.% or less; in other embodiments, 0.17 wt.% or less; in further embodiments, 0.16 wt.% or less; in still further embodiments, 0.15 wt.% or less; in some embodiments, 0.14 wt.% or less; in other embodiments, 0.13 wt.% or less; in further embodiments, 0.12 wt.% or less; in still further embodiments, 0.1 1 wt.% or less; in some embodiments, 0.10 wt.% or less; in other embodiments, 0.09 wt.% or less; in further embodiments, 0.08 wt.% or less; in still further embodiments, 0.07 wt.% or less; in some embodiments, 0.06 wt.% or less; in other embodiments, 0.05 wt.%
  • the amount of resin residue remaining on the wafer following the soaking and washing steps using the sulfuric acid soaking concentration levels described herein is less than 0.26 wt.% and, in many instances, the silicone is completely removed from the wafer.
  • the amount of resin residue remaining on the wafer following the soaking and washing steps using the sulfuric acid soaking concentration levels described herein is 0.25 wt.% or less; in some embodiments, 0.24 wt.% or less; in other embodiments, 0.23 wt.% or less; in some other embodiments, 0.22 wt.% or less; in further embodiments, 0.21 wt.% or less; in still further embodiments, 0.20 wt.% or less; in some embodiments, 0.19 wt.% or less; in some embodiments, 0.18 wt.% or less; in other embodiments, 0.17 wt.% or less; in further embodiments, 0.16 wt.% or less; in still further embodiments, 0.15 wt.% or less; in some embodiments, 0.14 wt.% or less; in other embodiments, 0.13 wt.% or less; in further embodiments, 0.12 wt.% or less; in still further embodiments, 0.1 1 wt.
  • the inventive methods of removing silicone resins from various substrates are advantageous in that they provide high throughput and high speed of removal of the cured resin coating (and any reaction product thereof) and the degraded resin coating (and any reaction product thereof) from the substrate as the methods described herein facilitate wafer treating within only 2 or 3 hours, which is particularly desirable for electronics end uses. Additionally, the chemicals deployed in the inventive methods have minimal or no impact on the substrate (as concentrated sulfuric acid does not etch silicon or glass wafers) and are low cost (due to the ready availability of sulfuric acid).
  • the cleaned substrate e.g., the substrate substantially lacking the cured resin coating (or a reaction product thereof) and substantially lacking the degraded resin coating (or a reaction product thereof)
  • a gas such as with air, argon and/or nitrogen. Any other suitable methods used for drying substrate surfaces at a reasonable temperature in the microelectronics industry can also and/or alternatively be employed.
  • the washed, cleaned and dried substrate may be directly used for subsequent processing steps or subjected to further cleaning processes known in the art and adopted in the microelectronics industry such as, but not limited to, RCA clean.
  • the inventive methods readily facilitate removal of a cured silicone resin from a substrate for substrate reclaim.
  • Comparative Examples (CE) 1 a-1 e Film Forming on and Film Removal from Wafers: Effect of Sulfuric Acid Concentration on Silicone Resin Removal
  • a polydimethylsiloxane-based resin with a dynamic viscosity of 5,000 cP was spin coated onto pre-weighed 4" silicon wafers.
  • the thin film materials with thickness of around 50 ⁇ (about 550 mg) were cured at 150°C. All of the wafers were weighed again after cure to calculate the amount of resin coated on the respective wafers for the silicone resin-coated substrates which were formed.
  • W 0 is the weight of the silicon wafer prior to spin coating
  • W- is the weight of the silicon wafer after spin-coating with silicone
  • W 2 is the weight of the silicone-coated silicon wafer upon removal of the silicone.
  • Comparative Example (CE) 2a Film Forming on and Film Removal from a Wafer: Effect of Sulfuric Acid Treatment Time on Silicone Resin Removal
  • a polydimethylsiloxane-based resin with a viscosity of 5,000 cP was spin coated onto a pre-weighed 4" silicon wafer.
  • the thin film material with thickness of around 50 ⁇ (about 550 mg) was cured at 150°C.
  • the wafer was further treated to 250°C for 1 hr as noted in Table 2.
  • the wafer was weighed again after cure to calculate the amount of resin coated on the wafer for the silicone resin-coated substrate which was formed.
  • test results for Invention Examples Ex 2a-2b reveal a silicone removal level at less than 0.20 wt.% following soaking in about 96 wt.% sulfuric acid after 10 and 20 minutes, respectively.
  • the test results for Invention Examples Ex 2c-2d reveal complete (100 wt.%) silicone removal following soaking in about 96 wt.% sulfuric acid after 15 minutes for the silicon wafer (Ex 2c) and after 15 minutes for the glass wafer (Ex 2d) and further treatment to
  • Comparative Examples (CE) 4a-4c Film Forming on and Film Removal from Wafers: Effect of Various Washing Solvents on Silicone Resin Removal
  • a polydimethylsiloxane-based resin with a viscosity of 5,000 cP was spin coated onto pre-weighed 4" silicon wafers.
  • the thin film materials with thickness of around 50 ⁇ (about 550 mg) were cured at 150°C. All of the wafers were weighed again after cure to calculate the amount of resin coated on the respective wafers for the silicone resin-coated substrates which were formed.
  • the silicone resin-coated substrates were soaked in concentrated sulfuric acid (95 wt.% - 98 wt.%) at room temperature for 30 minutes. Afterwards, the silicone resin-coated substrates were washed with ethanol and 1-pentanol or not washed at all and then washed with Dl water, respectively, as shown in Table 4. All of the wafers were weighed again to calculate the percentage of silicone removed from the wafer. The percentage of silicone residue remaining on the wafer was calculated according to the calculation detailed in CE 2 and Ex 2a-2d. The surface appearance of the wafers after solvent washing was noted. The test results are reported later in Table 4.
  • a polydimethylsiloxane-based resin with a viscosity of 5,000 cP was spin coated onto pre-weighed 4" silicon wafers and a glass wafer, respectively.
  • the thin film materials with thickness of around 50 ⁇ (about 550 mg) were cured at 150°C. All of the wafers were weighed again after cure to calculate the amount of resin coated on the respective wafers for the silicone resin-coated substrates which were formed.
  • the silicone resin-coated substrates were soaked in concentrated sulfuric acid (about 96 wt.%) at room temperature for 30 minutes, respectively. Afterwards, the wafers were first thoroughly washed with I PA and then washed with Dl water. All of the wafers were weighed again to calculate the percentage of silicone removed from the wafer.
  • the silicone removal methods in Invention Examples Ex 5a-5c facilitated the reclaimability of the wafers upon subjecting the wafers to multiple silicone removal and cleaning steps. Complete (100 wt.%) silicone removal was observed following soaking in about 96 wt.% sulfuric acid for 30 minutes and washing with I PA even with the three steps of coating the wafer with the silicone. The silicone removal methods did not change the properties of the wafer.
  • a polydimethylsiloxane-based resin with a viscosity of 5,000 cP was spin coated onto pre-weighed 4" silicon wafers.
  • the thin film materials with thickness of around 50 ⁇ (about 550 mg) were cured at 150°C. All of the wafers were weighed again after cure to calculate the amount of resin coated on the respective wafers for the silicone resin-coated substrates which were formed.
  • Comparative Examples (CE) 7a-3c Film Forming on and Film Removal from Wafers: Effect of Different Sulfuric Acid-Organic Compound Mixtures on Silicone Resin Removal
  • a polydimethylsiloxane-based resin with a viscosity of 5,000 cP was spin coated onto pre-weighed 4" silicon wafers.
  • the thin film materials with thickness of around 50 ⁇ (about 550 mg) were cured at 150°C. All of the wafers were weighed again after cure to calculate the amount of resin coated on the respective wafers for the silicone resin-coated substrates which were formed.
  • the silicone resin-coated substrates were soaked at room temperature for 30 minutes in mixtures of 96 wt.% sulfuric acid/octane/4-dodecyl benzyl sulfonic acid at varying final concentrations as shown below for CE 7a-7c as listed in Table 7. Afterwards, the wafers were first thoroughly washed with I PA as shown in Table 7 and then washed with Dl water. All of the wafers were weighed again to calculate the percentage of silicone removed from the wafer. The percentage of silicone residue remaining on the wafer was calculated according to the calculation detailed in CE 2 and Ex 2a-2d. The surface appearance of the wafers after solvent washing was noted. The test results are reported later in Table 7.
  • the protocol for CE 7a-7c was replicated to form the respective silicone resin-coated substrates.
  • the silicone resin-coated substrates were soaked at room temperature for 30 minutes in mixtures of 96 wt.% sulfuric acid/octane/4-dodecyl benzyl sulfonic acid at varying final concentrations as shown below for Ex 7a-7d and in mixtures of 96 wt.% sulfuric acid/tetradecane/4-dodecyl benzyl sulfonic acid at varying final concentrations as shown below for Ex 7e-7g in Table 7. Afterwards, the wafers were first thoroughly washed with I PA as shown in Table 7 and then washed with Dl water.
  • Comparative Examples (CE) 8a-8b Film Forming on and Film Removal from Wafers: Effect of Different Commercial Sulfuric Acid-Organic Compounds on Silicone Resin Removal
  • a polydimethylsiloxane-based resin with a viscosity of 5,000 cP was spin coated onto pre-weighed 4" silicon wafers.
  • the thin film materials with thickness of around 50 ⁇ (about 550 mg) were cured at 150°C. All of the wafers were weighed again after cure to calculate the amount of resin coated on the respective wafers for the silicone resin-coated substrates which were formed.
  • a method of removing a cured resin coating from a resin-coated substrate formed of a substrate having the cured resin coating thereon comprising: (a) soaking the resin-coated substrate in a sulfuric acid-based reagent for from greater than 0 to 60 minutes to degrade the cured resin coating on the substrate, wherein the resin of the cured resin coating is an Si-O-Si containing silicone resin and the sulfuric acid-based reagent is (i) an aqueous, concentrated sulfuric acid with a sulfuric acid concentration of at least 95 weight percent or (ii) a mixture of concentrated sulfuric acid mixed with one or more alkanes having 5 or more carbons such that the total sulfuric acid concentration of the mixture is at least 20 weight percent, wherein the concentrated sulfuric acid used to prepare the mixture (ii) has a starting concentration of at least 95 weight percent, (b) washing away the degraded resin coating from step (a) with a first organic solvent selected from isopropyl alcohol, acetone, 2-
  • aromatic sulfonic acid is dodecyl benzenesulfonic acid, dodecyl benzenesulfonic acid salt, benzenesulfonic acid, benzenesulfonic acid salt, toluene sulfonic acid, toluene sulfonic acid salt, decyl benzyl sulfonic acid, decyl benzyl sulfonic acid salt, 4-dodecyl benzyl sulfonic acid, 4-dodecyl benzyl sulfonic acid salt, or any combination thereof.
  • the cured resin coating is a cured Si-O-Si containing silicone resin and the resin-coated substrate is formed prior to step (a) by a method comprising: coating a curable Si-O-Si containing silicone resin onto the substrate to a resin coating thickness from greater than 0 millimeter up to about 1 millimeter to form a curable resin-coated substrate; and curing the curable Si- O-Si containing silicone resin to form a cured form of the resin-coated substrate.
  • step (b) further comprising a second washing step following step (b), wherein the second washing step involves washing with a second organic solvent, the second organic solvent is selected from an alkane, an aromatic hydrocarbon, a carboxylic ester, an alcohol, a ketone, an ether or mixtures thereof, wherein the second organic solvent is removed by drying with a gas prior to the washing step of step (c), wherein the drying involves the use of air, argon, nitrogen, or mixtures thereof.
  • a second washing step involves washing with a second organic solvent
  • the second organic solvent is selected from an alkane, an aromatic hydrocarbon, a carboxylic ester, an alcohol, a ketone, an ether or mixtures thereof, wherein the second organic solvent is removed by drying with a gas prior to the washing step of step (c), wherein the drying involves the use of air, argon, nitrogen, or mixtures thereof.
  • each R is independently an organic group selected from alkyl and aryl substituents.
  • Si-O-Si containing silicone resin of the cured resin coating is a curable polydimethylsiloxane-based resin.
  • step (c) The method according to any one of the preceding aspects, further comprising drying the substrate after step (c) with air, argon, nitrogen, or mixtures thereof.
  • a method of removing a cured resin coating from a resin-coated substrate formed of a substrate having the cured resin coating thereon comprising: (a) coating a curable Si-O-Si containing silicone resin onto the substrate to a resin coating thickness from greater than 0 millimeter up to about 1 millimeter to form a curable resin- coated substrate; (b) curing the curable Si-O-Si containing silicone resin to form a cured form of the resin-coated substrate; (c) soaking the cured form of the resin-coated substrate in a sulfuric acid-based reagent for from greater than 0 to 60 minutes to degrade the cured resin coating on the substrate, wherein the sulfuric acid-based reagent is (i) an aqueous, concentrated sulfuric acid with a sulfuric acid concentration of at least 95 weight percent or (ii) a mixture of concentrated sulfuric acid mixed with one or more alkanes having 5 or more carbons such that the total sulfuric acid concentration of the mixture is
  • a method of removing a cured resin coating from a resin-coated substrate formed of a substrate having the cured resin coating thereon comprising: soaking the resin-coated substrate in a sulfuric acid-based reagent for from greater than 0 to 60 minutes to degrade the cured resin coating on the substrate, wherein the resin of the cured resin coating is a curable polydimethylsiloxane-based resin and wherein the sulfuric acid-based reagent is (i) an aqueous, concentrated sulfuric acid with a sulfuric acid concentration of at least 95 weight percent or (ii) a mixture of concentrated sulfuric acid mixed with one or more alkanes having 5 or more carbons such that the total sulfuric acid concentration of the mixture is at least 20 weight percent, wherein the concentrated sulfuric acid used to prepare the mixture (ii) has a starting concentration of at least 95 weight percent; washing away the degraded resin coating from step (a) with isopropyl alcohol, acetone or a mixture of isoprop
  • the resin- coated substrate is formed by a method comprising: coating a curable polydimethylsiloxane- based resin onto the substrate to a resin coating thickness from greater than 0 millimeter up to about 1 millimeter to form a curable resin-coated substrate; and curing the curable polydimethylsiloxane-based resin to form a cured form of the resin-coated substrate.
  • the substrate is a silicon wafer, a silicon plate, a glass wafer, a glass plate, a silicon carbide wafer, a silicon carbide plate, a patterned silicon wafer, a patterned glass wafer, a patterned silicon carbide wafer, a device wafer, or a device plate.
  • the soaking step (a) comprises soaking the resin-coated substrate in the sulfuric acid-based reagent for from greater than 0 to 60 minutes to degrade the cured resin coating on the substrate, wherein the resin of the cured resin coating is an Si-O-Si containing silicone resin and the sulfuric acid-based reagent is the (i) an aqueous, concentrated sulfuric acid with a sulfuric acid concentration of at least 95 weight percent.
  • the soaking step (a) comprises soaking the resin-coated substrate in the sulfuric acid-based reagent for from greater than 0 to 60 minutes to degrade the cured resin coating on the substrate, wherein the resin of the cured resin coating is an Si-O-Si containing silicone resin and the sulfuric acid-based reagent is the (ii) a mixture of concentrated sulfuric acid mixed with one or more alkanes having 5 or more carbons such that the total sulfuric acid concentration of the mixture is at least 20 weight percent, wherein the concentrated sulfuric acid used to prepare the mixture (ii) has a starting concentration of at least 95 weight percent.

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EP3828228A1 (en) * 2019-11-29 2021-06-02 Borealis AG Method for removing foreign materials from the surface of an article
CN114206514A (zh) * 2019-07-26 2022-03-18 北欧化工公司 从制品表面去除油墨或其他异物的方法
CN116024056A (zh) * 2021-10-25 2023-04-28 中国石油化工股份有限公司 一种乙醛聚合变质产物溶解剂及其制备方法和应用

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US20040115909A1 (en) * 2002-12-17 2004-06-17 Samsung Electronics Co., Ltd. Cleaning solution and method of cleaning a semiconductor device using the same
US20090233827A1 (en) * 2008-03-13 2009-09-17 Air Products And Chemicals, Inc. Semi-Aqueous Stripping and Cleaning Composition Containing Aminobenzenesulfonic Acid
WO2013087510A1 (de) * 2011-12-16 2013-06-20 Wacker Chemie Ag Siliconlöser

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JPH08250400A (ja) * 1995-03-14 1996-09-27 Mitsubishi Electric Corp シリコーン樹脂の除去法
US20040115909A1 (en) * 2002-12-17 2004-06-17 Samsung Electronics Co., Ltd. Cleaning solution and method of cleaning a semiconductor device using the same
US20090233827A1 (en) * 2008-03-13 2009-09-17 Air Products And Chemicals, Inc. Semi-Aqueous Stripping and Cleaning Composition Containing Aminobenzenesulfonic Acid
WO2013087510A1 (de) * 2011-12-16 2013-06-20 Wacker Chemie Ag Siliconlöser

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Publication number Priority date Publication date Assignee Title
CN114206514A (zh) * 2019-07-26 2022-03-18 北欧化工公司 从制品表面去除油墨或其他异物的方法
EP3828228A1 (en) * 2019-11-29 2021-06-02 Borealis AG Method for removing foreign materials from the surface of an article
WO2021104797A1 (en) * 2019-11-29 2021-06-03 Borealis Ag Method for removing foreign materials from the surface of an article
CN114761471A (zh) * 2019-11-29 2022-07-15 北欧化工公司 从制品表面去除异物的方法
CN116024056A (zh) * 2021-10-25 2023-04-28 中国石油化工股份有限公司 一种乙醛聚合变质产物溶解剂及其制备方法和应用

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