Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
  • C09J183/04—Polysiloxanes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
  • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
  • C08G18/622—Polymers of esters of alpha-beta ethylenically unsaturated carboxylic acids
  • C08G18/6225—Polymers of esters of acrylic or methacrylic acid
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/72—Polyisocyanates or polyisothiocyanates
  • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
  • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
  • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
  • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
  • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
  • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
  • C08G18/81—Unsaturated isocyanates or isothiocyanates
  • C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
  • C08G18/8116—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group esters of acrylic or alkylacrylic acid having only one isocyanate or isothiocyanate group
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
  • C09J133/04—Homopolymers or copolymers of esters
  • C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
  • C09J133/08—Homopolymers or copolymers of acrylic acid esters
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
  • C09J175/04—Polyurethanes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
  • C09J183/02—Polysilicates
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J7/00—Adhesives in the form of films or foils
  • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
  • C09J7/22—Plastics; Metallised plastics
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J7/00—Adhesives in the form of films or foils
  • C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
• • 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
  • H01L21/67—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere
  • H01L21/683—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping
  • H01L21/6835—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
  • H01L21/6836—Wafer tapes, e.g. grinding or dicing support tapes
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
  • H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
  • H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
  • H01L24/27—Manufacturing methods
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L24/00—Arrangements for connecting or disconnecting semiconductor or solid-state bodies; Methods or apparatus related thereto
  • H01L24/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
  • H01L24/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
  • H01L24/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
  • H01L24/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G2170/00—Compositions for adhesives
  • C08G2170/40—Compositions for pressure-sensitive adhesives
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
  • C08G77/04—Polysiloxanes
  • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
  • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
  • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
• • 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
  • H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the groups H01L21/18 - H01L21/326 or H10D48/04 - H10D48/07 e.g. sealing of a cap to a base of a container
  • H01L21/60—Attaching or detaching leads or other conductive members, to be used for carrying current to or from the device in operation
  • H01L2021/60007—Attaching or detaching leads or other conductive members, to be used for carrying current to or from the device in operation involving a soldering or an alloying process
• • 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
  • H01L21/50—Assembly of semiconductor devices using processes or apparatus not provided for in a single one of the groups H01L21/18 - H01L21/326 or H10D48/04 - H10D48/07 e.g. sealing of a cap to a base of a container
  • H01L21/60—Attaching or detaching leads or other conductive members, to be used for carrying current to or from the device in operation
  • H01L2021/60277—Attaching or detaching leads or other conductive members, to be used for carrying current to or from the device in operation involving the use of conductive adhesives
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L2221/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof covered by H01L21/00
  • H01L2221/67—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere
  • H01L2221/683—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping
  • H01L2221/68304—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support
  • H01L2221/68327—Apparatus for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components; Apparatus not specifically provided for elsewhere for supporting or gripping using temporarily an auxiliary support used during dicing or grinding
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
  • H01L2224/00—Indexing scheme for arrangements for connecting or disconnecting semiconductor or solid-state bodies and methods related thereto as covered by H01L24/00
  • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
  • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
  • H01L2224/27—Manufacturing methods
  • H01L2224/274—Manufacturing methods by blanket deposition of the material of the layer connector
  • H01L2224/2743—Manufacturing methods by blanket deposition of the material of the layer connector in solid form
  • H01L2224/27436—Lamination of a preform, e.g. foil, sheet or layer
• • H—ELECTRICITY
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  • H01L2224/01—Means for bonding being attached to, or being formed on, the surface to be connected, e.g. chip-to-package, die-attach, "first-level" interconnects; Manufacturing methods related thereto
  • H01L2224/26—Layer connectors, e.g. plate connectors, solder or adhesive layers; Manufacturing methods related thereto
  • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
  • H01L2224/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
  • H01L2224/29001—Core members of the layer connector
  • H01L2224/29099—Material
  • H01L2224/2919—Material with a principal constituent of the material being a polymer, e.g. polyester, phenolic based polymer, epoxy
• • H—ELECTRICITY
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  • H01L2224/80—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected
  • H01L2224/83—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected using a layer connector
  • H01L2224/8319—Arrangement of the layer connectors prior to mounting
  • H01L2224/83191—Arrangement of the layer connectors prior to mounting wherein the layer connectors are disposed only on the semiconductor or solid-state body
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  • H01L24/80—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected
  • H01L24/83—Methods for connecting semiconductor or other solid state bodies using means for bonding being attached to, or being formed on, the surface to be connected using a layer connector
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  • H01L2924/01—Chemical elements
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  • H01L2924/10—Details of semiconductor or other solid state devices to be connected
  • H01L2924/102—Material of the semiconductor or solid state bodies
  • H01L2924/1025—Semiconducting materials
  • H01L2924/10251—Elemental semiconductors, i.e. Group IV
  • H01L2924/10253—Silicon [Si]
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  • H01L2924/10—Details of semiconductor or other solid state devices to be connected
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  • H01L2924/1026—Compound semiconductors
  • H01L2924/1032—III-V
  • H01L2924/10329—Gallium arsenide [GaAs]

Definitions

• This invention relates to a photocurable pressure sensitive adhesive coated on a polyolefin base film that is used in the manufacture of semiconductor devices.
• a semiconductor wafer such as one prepared from silicon or gallium arsenide, is initially manufactured in a size larger than is used for the individual semiconductors.
• the wafer is typically thinned by grinding, and cut into small individual semiconductor dies, which are then transferred and adhered to the desired substrates.
• the wafer is adhered to a support tape that has a die bonding adhesive layer and a pressure sensitive adhesive layer, with the pressure sensitive adhesive layer situated between the adhesive layer and the support tape.
• the pressure sensitive adhesive layer is cured and hardened by UV irradiation so that it releases from the adhesive layer that will be used for die bonding.
• controlling the adhesion of the pressure sensitive adhesive so that it adheres tightly before photocure and releases cleanly and easily after photocure is important.
• the capability of releasing cleanly after cure is particularly important for subsequent fabrication steps.
• Conventional UV curable pressure sensitive adhesives do not always achieve a clean separation, thus creating a need for adhesives for use in semiconductor fabrication with improved release performance.
• This invention is a pressure sensitive adhesive composition
• a pressure sensitive adhesive composition comprising (A) pressure sensitive adhesive polymers having pendant carbon-carbon unsaturation and (B) hydrophobic polymers terminated with carbon-carbon unsaturation.
• the hydrophobic polymers are vinyl terminated siloxane polymers and/or vinyl terminated fluoropolymers.
• the pressure sensitive adhesive further comprises a polyisocyanate, in an amount effective to partially crosslink the composition.
• the high hydrophobicity of siloxane polymers and fluoropolymers reduces the interaction of the pressure sensitive adhesive with adherends and provides excellent release of the pressure sensitive adhesive after cure.
• hydrophobic component (B) is reacted with the pressure sensitive adhesive polymers (A) having pendant carbon-carbon unsaturation. If only one end of the hydrophobic polymer chain is unsaturated, the possibility of any unreacted hydrophobic polymer migrating to the surface of the adherend (substrate) and causing contamination is increased.
• the pressure sensitive polymers (A) having pendant carbon- carbon unsaturation are polymers having a polyethylenic backbone and at least one pendant acryloyl urethane group.
• the pendant acryloyl urethane group reacts upon exposure to actinic radiation, and/or chemical initiation.
• the polyethylenic backbone is a hydrocarbon chain that results from the addition polymerization of ethylenically unsaturated monomers.
• the pressure sensitive adhesive polymers (A) of the present invention are prepared by (1) polymerizing an isocyanate monomer with ethylenic unsaturation singularly or in combination with other ethylenically unsaturated monomer(s) under conditions sufficient to cause the addition polymerization of the ethylenically unsaturated groups, thereby forming a precursor polymer with a polyethylenic chain and pendant isocyanate groups, and (2) reacting the isocyanato group(s) pendant to the polyethylenic chain of the precursor polymer with an active hydrogen compound containing an acryloyl group.
• This method and resultant compounds are disclosed in US Patent 4,343,919.
• Isocyanate monomers suitable for use in the above reaction are those having an isocyanate group and an ethylenically unsaturated group capable of undergoing free radical initiated addition polymerization.
• Representative isocyanates are the isocyanato alkyl esters of ⁇ , ⁇ -ethylenically unsaturated carboxylic acids, monovinylidene aryl isocyanates and monovinylidene arylmethyl isocyanates.
• Exemplary isocyanatoalkyl esters include 2-isocyanatoethyl methacrylate, 2- isocyanatoethyl acrylate, 3-isocyanatopropyl methacrylate, l-methyl-2-isocyanatoethyl methacrylate and l ,l-dimethyl-2-isocyanatoethyl acrylate.
• Exemplary monovinylidene aromatic isocyanates and monovinylidene arylmethyl isocyanates include styrene isocyanate and vinylbenzyl isocyanate.
• Suitable ethylenically unsaturated monomers for polymerizing with the isocyanate compounds are any ethylenically unsaturated monomers inert to the isocyanate groups.
• Exemplary ethylenically unsaturated monomers include aliphatic conjugated dienes, such as, butadiene and isoprene; monovinylidene aromatic monomers such as styrene, a-methyl styrene, (t-butyl)styrene, chlorostyrene, cyanostyrene and bromostyrene; alkyl esters of ⁇ , ⁇ -ethylenically unsaturated carboxylic acids, such as, methyl methacrylate, ethyl acrylate, butyl acrylate; ⁇ , ⁇ - ethylenically unsaturated nitriles, anhydrides and amides, such as, acrylonitrile,
• ethacrylonitrile maleic anhydride
• acrylamide methacrylamide, methacrylamide, N,N-dimethyl acrylamide, N- (dimethylaminomethyl) acrylamide
• vinyl esters such as, vinyl acetate; vinyl ethers; vinyl ketones; vinyl and vinylidene halides.
• ethylenically unsaturated monomers are recited further in this specification.
• the ethylenically unsaturated monomers are selected from the group consisting of styrene, butyl acrylate and methyl methacrylate.
• the relative proportions of isocyanate monomer to other monomers is not particularly critical provided that there is at least one isocyanate group, preferably at least two isocyanate groups, on the precursor polymer. Typically there is about 10 to about 50 mole percent isocyanate monomer and from about 50 to about 90 mole percent of other monomers, based on total monomers.
• the reaction of the polymer precursor with an active hydrogen acryloyl compound is carried out in the presence of a urethane catalyst, for example, an amine or an organometallic catalyst such as stannous octoate or dibutyltin dilaurate.
• a urethane catalyst for example, an amine or an organometallic catalyst such as stannous octoate or dibutyltin dilaurate.
• the conditions employed for carrying out the urethane reaction are known to those skilled in the art.
• the amount of the isocyanate groups of the polymer precursor is preferably stoichiometric or slightly in excess of the active hydrogen groups of the active hydrogen compound.
• the active hydrogen acryloyl compound can be any containing an acryloyl group and an active hydrogen moiety.
• active hydrogen moieties are— COOH,—OH,— NH 2 , — NH— ,— CONH 2 ,— SH and— CONH— .
• Exemplary active hydrogen monomers include aminohydrocarbyl and hydroxyhydrocarbyl esters of acrylic acid, such as, hydroxyethyl acrylate, hydroxypropyl acrylate, aminoethyl acrylate, N-(methyl)acrylamide, N-(methylol)acrylamide and N-(aminomethyl)acrylamide; acrylic acid; and mercaptoalkyl esters of acrylic acid such as mercaptoethyl acrylate.
• the active hydrogen compound is hydroxyethyl acrylate.
• the pressure sensitive adhesive polymers (A) of the present invention are prepared by (1) polymerizing a monomer containing both hydroxyl groups and ethylenic unsaturation singularly or in combination with other ethylenically unsaturated monomer(s) under conditions sufficient to cause the addition polymerization of the ethylenically unsaturated groups, thereby forming a precursor polymer with a polyethylenic chain and pendant hydroxyl groups, and (2) reacting the hydroxyl group(s) pendant to the polyethylenic backbone of the precursor polymer with one or more ethylenically unsaturated isocyanates.
• This method and resultant compounds are disclosed in PCT Patent Application WO 95/00573.
• Hydroxyl-containing monomers suitable for use in the above reaction are those having an hydroxyl group and an ethylenically unsaturated group capable of undergoing free radical initiated addition polymerization.
• Representative hydroxyl-containing monomers are the hydroxyalkyl esters of ⁇ , ⁇ -ethylenically unsaturated carboxylic acids, such as hydroxyalkyl acrylates and hydroxyalkyl methacrylates.
• the hydroxyl-containing monomers are 2-hydroxyethyl acrylate (HEA) and hydroxypropyl acrylate (HP A).
• Suitable hydroxyl-containing compounds are the ethylene oxide and propylene derivatives of HEA and HP A, containing from 1 to about 20 moles of the alkylene oxide;
• caprolactone acrylates and methacrylates which are epsilon-caprolactone derivatives of HEA and HP A containing from 1 to about 6 moles of epsilon-caprolactone; and carboxylic acid terminated adducts of HEA and HP A.
• Suitable ethylenically unsaturated monomers for polymerizing with the hydroxyl- containing compounds are any ethylenically unsaturated monomers inert to the hydroxyl groups. These include the ethylenically unsaturated compounds mentioned above in this specification for reacting with the isocyanate containing compounds.
• Other exemplary compounds include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, nonyl
• the precursor polymers are prepared by conventional techniques known to those skilled in the art of polymerization.
• the relative proportions of hydroxyl monomer to other monomers is not particularly critical provided that there is at least one hydroxyl group, preferably at least two hydroxyl groups, on the precursor polymer.
• Other functional groups, such as carboxyl and amine may also be present in the hydroxyl functional precursor polymers.
• the isocyanate compound for reacting with the precursor polymer can be any containing an ethylenically unsaturated group and an isocyanate group.
• Illustrative of the ethylenically unsaturated isocyanates that can be used to react with the precursor polymer are the isocyanato alkyl (meth)acrylates, such as, 2-isocyanatoethyl methacrylate, 3-isocyanatopropyl methacrylate, and the like; monoisocyanates prepared from diolefins, such as, 1-(1- isocyanato- 1-methyl ethyl)-3-(l -methyl ethenyl) benzene (p-TMI), l-(l-isocyanato-l -methyl ethyl)-4-(l- methyl ethenyl) benzene (m-TMI), 1-(1 - isocyanato- 1 -methyl propyl)-3-(l)
• a stoichiometric deficiency of the ethylenically unsaturated isocyanate may be employed in order to leave some hydroxyl functionality in the polymer.
• Excess isocyanate is generally avoided since it introduces residual unpolymerized monomer. At least about 0.5% of the ethylenically unsaturated isocyanate, based on the weight of the polymer, is used. Based on the hydroxyl content of the precursor polymer, typically at least about 5% of the hydroxyl functionality is consumed by reaction with the ethylenically unsaturated isocyanate, and that amount can be as high as 90%.
• the polyisocyanate is added to the composition just prior to use. Suitable
• polyisocyanates include diisophorone, toluene diisocyanate (TDI), diphenylmethane diisocyanate (MDI), and 1,5 -naphthalene diisocyanate (NDI).
• Suitable hydrophobic polymers for reacting with the pressure sensitive adhesive polymers include vinyl terminated polydimethoxyl siloxane polymers and vinyl terminated fluoropolymers.
• Exemplary vinyl terminated polydimethoxyl siloxane polymers include DMS- V46 and DMS-52 from Gelest.
• Exemplary vinyl terminated fluoropolymers include reaction product of Lumiflon 200 and Lumiflon 552 (Asahi Glass) with MOI. Lumiflon 200 and
• Lumiflon 552 are fluoropolymer having hydroxyl group on the polymer backbone. This hydroxyl group reacts with MOI and unsaturated carbon-carbon double is incorporated to fluoropolymer backbone.
• the hydrophobic polymers are present in an amount up to 5 weight percent (but not 0 wt%) based on the total solid content of the composition. Typically the hydrophobic polymers are blended with the pressure sensitive adhesive polymers in a suitable solvent, such as, ethyl acetate.
• a pressure sensitive adhesive was prepared from the copolymerization of 2- ethylhexyl acrylate (14g), butyl acrylate (63 g), and 2-hydroxyethyl acrylate (23 g) in ethyl acetate (lOOg) with a free radical initiator and heated to 90°C (jacket temperature) until the reaction was complete.
• methacryloyloxyethyl isocyanate 24.10g
• dibutyltin dilaurate 0.065g
• Isophorone diisocyanate (3.27g) was added and the mixture reacted for another 30 minutes at room temperature.
• the resultant PSA polymer was coated on a PET release liner.
• the coated PSA was laminated to polyolefin base film at room temperature to make a dicing tape.
• a die bonding film was laminated to make a combination dicing die bonding film.
• the dicing die bonding film was laminated to a 75um thick silicon wafer and the silicon wafer diced, using a dicing saw having an ultra thin diamond blade at a speed greater than 20,000rpm, into a plurality of individual dies.
• a pressure sensitive adhesive was prepared from the copolymerization of 2- ethylhexyl acrylate (14g), butyl acrylate (63g), and 2-hydroxyethyl acrylate (23g) in ethyl acetate (lOOg) with a free radical initiator and heated to 90°C (jacket temperature) until the reaction was complete.
• a die bonding film was laminated to make a combination dicing die bonding film.
• the dicing die bonding film was laminated to a 75um thick silicon wafer and the silicon wafer diced, using a dicing saw having an ultra thin diamond blade at a speed greater than 20,000rpm, into a plurality of individual dies.
• a pressure sensitive adhesive was prepared from the copolymerization of 2- ethylhexyl acrylate (14g), butyl acrylate (63g), and 2-hydroxyethyl acrylate (23g) in ethyl acetate (1 OOg) with a free radical initiator and heated to 90°C (jacket temperature) until the reaction was complete.
• vinyl terminated fluoropolymer adduct of LF 200 and methacryloyloxyethyl isocyanate (MOI) (24.10g) and dibutyltin dilaurate (0.065g) as catalyst, after which the composition mixture was reacted for eight hours at room temperature.
• the vinyl terminated fluoropolymer was prepared by the reaction of fluoropolymer (lOg) (LF 200) with 1.5g MOI.) (In some samples, toluene or xylene may be used in the composition to help stabilize the hydrophobic polymer ). Isophorone diisocyanate (3.27g) was added and the mixture reacted for another 30 minutes at room temperature.
• the resultant PSA polymer was coated on a PET release liner.
• the coated PSA was laminated to polyolefin base film at room temperature to make a dicing tape.
• a die bonding film was laminated to make a combination dicing die bonding film.
• the dicing die bonding film was laminated to a 75um thick silicon wafer and the silicon wafer diced, using a dicing saw having an ultra thin diamond blade at a speed greater than 20,000rpm, into a plurality of individual dies.

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• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Microelectronics & Electronic Packaging (AREA)
• Computer Hardware Design (AREA)
• Power Engineering (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Health & Medical Sciences (AREA)
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• Adhesives Or Adhesive Processes (AREA)
• Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
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• Adhesive Tapes (AREA)
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