WO2008115711A1 - Dicing and die attach adhesive - Google Patents

Dicing and die attach adhesive Download PDF

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Publication number
WO2008115711A1
WO2008115711A1 PCT/US2008/056178 US2008056178W WO2008115711A1 WO 2008115711 A1 WO2008115711 A1 WO 2008115711A1 US 2008056178 W US2008056178 W US 2008056178W WO 2008115711 A1 WO2008115711 A1 WO 2008115711A1
Authority
WO
WIPO (PCT)
Prior art keywords
acrylate ester
functional
adhesive
thermosetting resin
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2008/056178
Other languages
English (en)
French (fr)
Inventor
Eric G. Larson
Michael A. Kropp
David J. Plaut
Cheryl L. Moore
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
3M Innovative Properties Co
Original Assignee
3M Innovative Properties Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 3M Innovative Properties Co filed Critical 3M Innovative Properties Co
Priority to US12/530,692 priority Critical patent/US8022145B2/en
Priority to EP08731642A priority patent/EP2134800A4/en
Priority to CN2008800086804A priority patent/CN101636462B/zh
Priority to JP2009553701A priority patent/JP2010521555A/ja
Publication of WO2008115711A1 publication Critical patent/WO2008115711A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10PGENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P72/00Handling or holding of wafers, substrates or devices during manufacture or treatment thereof
    • H10P72/70Handling or holding of wafers, substrates or devices during manufacture or treatment thereof for supporting or gripping
    • H10P72/74Handling or holding of wafers, substrates or devices during manufacture or treatment thereof for supporting or gripping using temporarily an auxiliary support
    • H10P72/7402Wafer tapes, e.g. grinding or dicing support tapes
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00Adhesives 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
    • C09J133/04Homopolymers or copolymers of esters
    • C09J133/06Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
    • C09J133/08Homopolymers or copolymers of acrylic acid esters
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00Adhesives in the form of films or foils
    • C09J7/20Adhesives in the form of films or foils characterised by their carriers
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10PGENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P95/00Generic processes or apparatus for manufacture or treatments not covered by the other groups of this subclass
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2666/00Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
    • C08L2666/02Organic macromolecular compounds, natural resins, waxes or and bituminous materials
    • C08L2666/14Macromolecular compounds according to C08L59/00 - C08L87/00; Derivatives thereof
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08LCOMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326Applications 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
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2433/00Presence of (meth)acrylic polymer
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09JADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2463/00Presence of epoxy resin
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10PGENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P72/00Handling or holding of wafers, substrates or devices during manufacture or treatment thereof
    • H10P72/70Handling or holding of wafers, substrates or devices during manufacture or treatment thereof for supporting or gripping
    • H10P72/74Handling or holding of wafers, substrates or devices during manufacture or treatment thereof for supporting or gripping using temporarily an auxiliary support
    • H10P72/7416Handling or holding of wafers, substrates or devices during manufacture or treatment thereof for supporting or gripping using temporarily an auxiliary support used during dicing or grinding
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10WGENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W72/00Interconnections or connectors in packages
    • H10W72/01Manufacture or treatment
    • H10W72/013Manufacture or treatment of die-attach connectors
    • H10W72/01331Manufacture or treatment of die-attach connectors using blanket deposition
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10WGENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W72/00Interconnections or connectors in packages
    • H10W72/071Connecting or disconnecting
    • H10W72/073Connecting or disconnecting of die-attach connectors
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10WGENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W72/00Interconnections or connectors in packages
    • H10W72/071Connecting or disconnecting
    • H10W72/073Connecting or disconnecting of die-attach connectors
    • H10W72/07331Connecting techniques
    • H10W72/07337Connecting techniques using a polymer adhesive, e.g. an adhesive based on silicone or epoxy
    • H10W72/07338Connecting techniques using a polymer adhesive, e.g. an adhesive based on silicone or epoxy hardening the adhesive by curing, e.g. thermosetting
    • HELECTRICITY
    • H10SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10WGENERIC PACKAGES, INTERCONNECTIONS, CONNECTORS OR OTHER CONSTRUCTIONAL DETAILS OF DEVICES COVERED BY CLASS H10
    • H10W72/00Interconnections or connectors in packages
    • H10W72/30Die-attach connectors
    • H10W72/351Materials of die-attach connectors
    • H10W72/353Materials of die-attach connectors not comprising solid metals or solid metalloids, e.g. ceramics
    • H10W72/354Materials of die-attach connectors not comprising solid metals or solid metalloids, e.g. ceramics comprising polymers
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/28Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2852Adhesive compositions
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/28Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2852Adhesive compositions
    • Y10T428/287Adhesive compositions including epoxy group or epoxy polymer
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/28Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2852Adhesive compositions
    • Y10T428/2878Adhesive compositions including addition polymer from unsaturated monomer
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/28Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2852Adhesive compositions
    • Y10T428/2878Adhesive compositions including addition polymer from unsaturated monomer
    • Y10T428/2891Adhesive compositions including addition polymer from unsaturated monomer including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof

Definitions

  • This relates generally to a single layer adhesive which functions as a dicing tape and also as a die attach adhesive for dicing thinned wafers and subsequent die attach operations of the diced chips in semiconductor device fabrication.
  • Wafers of semiconductor material such as silicon and gallium-arsenide with integrated circuits formed thereon have a relatively large diameter.
  • IC integrated circuits
  • a wafer is adhered to a pressure sensitive adhesive tape, sometimes called a dicing tape, and diced into IC chips.
  • the IC chips die or dice
  • the IC chips are then removed from the dicing tape, an adhesive is applied to the chip or to a substrate, the chip is placed on the substrate and the adhesive is cured to attach the die to the substrate.
  • Dicing tapes must provide strong adhesion to a semiconductor wafer during the step of dicing the wafer into individual chips.
  • the dicing tape also should subsequently provide a sufficiently low adhesion to the die to allow the individual chips to be removed from the tape quickly, cleanly, and easily. That is, it is useful for the dicing tape to have a reduced adhesion when the chip is removed, and there should be no residue from the dicing tape on the chip. Therefore dicing tapes have been prepared that have a balance of adhesion to the wafer to adhere strongly during the dicing step, but the tape also releases from the individual chips without leaving a residue on the chip when the chip is removed from the tape. Some dicing tapes have been prepared which may be detackified upon exposure to ultraviolet light to improve the clean removal of individual chips.
  • a second adhesive subsequently must be placed between the chip and the substrate to hold the chip securely in place on a substrate.
  • the second adhesive often referred to as a die attach adhesive, can be applied to the surface of a chip that is opposite the circuits or it may be applied directly to the substrate to which the chip will be bonded.
  • Using a separate die attach adhesive requires additional steps and equipment to place the adhesive either on the chip or the substrate.
  • Some separate die attach adhesives have been epoxy resins that can be cured once the chip has been placed on the substrate.
  • the present disclosure relates to an adhesive composition
  • an adhesive composition comprising an acrylate ester polymer having a functional group, a multifunctional thermosetting resin, a multi-functional acrylate ester, an acrylate ester polymerization catalyst or curing agent, a thermally-latent catalyst suitable for curing the multi-functional thermosetting resin, and an acrylic acid salt, wherein the acrylate ester polymer and the thermosetting resin are capable of reacting with each other.
  • the terms acrylate and acrylic include derivatives of both acrylic and methacrylic acid. References to an acrylate ester polymer having a functional group are to be understood as describing a moiety having at least one functional group other than an acryl or methacryl group.
  • the present disclosure relates to an adhesive comprising at least about 50 weight percent (wt%) of a functional group containing acrylate ester polymer, from about 20 wt% to about 40 wt% of a multi-functional thermosetting resin, an effective amount of a multi-functional acrylate ester, a catalyst for curing the acrylate ester polymer, a thermally latent catalyst or curing agent for curing the multi-functional thermosetting resin, and an acrylic acid salt, wherein the acrylate ester polymer and the thermosetting resin are capable of forming an adhesive reaction product.
  • the present disclosure relates to a method of making an adhesive comprising providing an acrylate ester polymer having a functional group, providing a multi-functional thermosetting resin, wherein the acrylate ester polymer and the thermosetting resin are capable of reacting with each other, providing a multifunctional acrylate ester, providing an acrylate ester polymerization catalyst or curing agent, providing a thermally-latent catalyst suitable for curing the multi-functional thermosetting resin, providing an acrylic acid salt, optionally a metal salt, mixing the polymer, thermosetting resin, multi-functional acrylate ester, thermally-latent catalyst, and an acrylic salt to form a mixture, and optionally degassing the mixture.
  • an adhesive composition comprising an acrylate ester polymer having a functional group, a multi-functional thermosetting resin, together a multi-functional acrylate ester, an acrylate ester polymer catalyst or curing agent, a thermally-latent catalyst suitable for curing the multi-functional thermosetting resin, and an acrylic acid salt, wherein the acrylate ester polymer and the thermosetting resin are capable of reacting with each other.
  • Suitable acrylate ester polymers having a functional group include, for example, copolymers of linear or branched mono functional unsaturated acrylates or methacrylates of non-tertiary alkyl alcohols, the alkyl groups of which have from 1 to 14 and, in particular, from 4 to 12 carbon atoms with one or more (meth)acrylate functional monomers bearing an additional functional group.
  • mono functional monomers include butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, ethyl (meth)acrylate, methyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, isononyl (meth)acrylate and 2-ethylbutyl (meth)acrylate.
  • (Meth)acrylate functional monomers bearing an additional functional group include the monomers above wherein the (meth)acrylate ester also bears one or more substituents selected from a carboxylic acid group, a hydroxy 1 group, a glycidyl group, an amide group, and an anhydride group.
  • (meth)acrylic ester monomers having an additional functional group that may be one or more of acrylic acid, methacrylic acid, hydroxy ethyl acrylate, hydroxy ethyl methacrylate, hydroxy propyl acrylate, hydroxy propyl methacrylate, hydroxy butyl acrylate, hydroxy butyl methacrylate, glycidyl acrylate, or glycidyl methacrylate, and N-methylol acrylamide.
  • Suitable multi-functional thermosetting resins include, for example, polyepoxy functional resins and their aziridine analogs.
  • the multifunctional glycidyl ether epoxy resin is present in the adhesive compositions of the invention at an amount from about
  • the multifunctional glycidyl ether epoxy resin is present in the adhesive compositions from about 23 wt% to about 37 wt%.
  • Other adhesive compositions of the invention may contain any amount or any range of amount between 15 wt% and 40 wt% of multifunctional glycidyl ether epoxy.
  • Preferred multifunctional glycidyl ether epoxy resins include those epoxy resins having more than two glycidyl groups on average within a molecule.
  • glycidyl ether epoxy resin examples include multifunctional phenol novolak-type epoxy resins (synthesized by reacting phenol novolak with epichlorohydrin) cresol novolak epoxy resin, and bisphenol A novolak epoxy resins.
  • Examples of commercially available multifunctional glycidyl ether epoxy resins include those epoxy resins having the trade designations Epon 1050, Epon 160, Epon 164, Epon 1031, Epon SU-2.5, Epon SU-3, And Epon SU-8, available from Hexion Specialty Chemicals, Columbus, OH; the "DEN” series of epoxy resins, available from Dow Chemical Co., Midland MI; and Tactix 756, and Tactix 556 epoxy resin, available from Huntsman Chemical, East Lansing, MI.
  • useful multifunctional glycidyl ether epoxy resins that are diglycidyl ethers of bisphenol A include, but are not limited to, those having the trade designations Epon Resins 825, 826, and 828, available from Hexion Specialty Chemicals; D. E. R. 330, 331, and 332 resins, available from Dow Chemical Co.; and Araldite GY 6008, GY 6010, and GY 2600 resins, available from Ciba Specialty Chemicals, Tarrytown, NY.
  • Examples of useful multifunctional glycidyl ether epoxy resins that are diglycidyl ethers of bisphenol F include, but are not limited to those having the trade designations EPON Resin 862 resin, available from Hexion Specialty Chemicals; and Araldite GY 281, GY 282, GY 285, PY 306, and PY 307 resins, available from Ciba Specialty Chemicals.
  • the multifunctional glycidyl ether epoxy resin usually has an epoxy equivalent weight of from about 170 to about 500, in other embodiments, from about 170 to about 350, and in other embodiments from about 170 to about 250. Ranges for the average epoxy functionality include from 1.5 to 10.
  • Suitable multi-functional acrylate esters include, for example, (meth)acrylate esters of di-, tri-, and tetra-hydroxy compounds such as ethylene glycol diacrylate, polyethylene glycol diacrylate, ethylene glycol dimethacrylate, hexanediol diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, glycerol triacrylate, pentaerthyitol triacrylate, pentaerythritol trimethacrylate, pentaerythritol tetraacrylate and pentaerythritol tetramethacrylate.
  • Trimethylolpropane triacrylate is particularly suitable for reducing tack of the adhesive by photochemically induced polymerization.
  • Suitable acrylate ester polymerization catalysts include, for example, photoinitiators and thermal initiators with photoinitiators being generally preferred in applications where extended shelf-life is particularly desirable.
  • photoinitiators include, for example, photoinitiators and thermal initiators with photoinitiators being generally preferred in applications where extended shelf-life is particularly desirable.
  • suitable ultraviolet-activated photoinitiators available as IrgacureTM 651, Irgacure 184, Irgacure 369 and Irgacure 819, and DarocurTM 1173, all products of Ciba Specialty Chemicals Co., and LucirinTM TPO-L, a product of BASF Corp.
  • thermal initiators may be used.
  • Thermal initiators include organic peroxides (e.g., benzoyl peroxide), azo compounds, quinones, nitroso compounds, acyl halides, hydrazones, mercapto compounds, pyrylium compounds, imidazoles, chlorotriazines, benzoin, benzoin alkyl ethers, diketones, phenones, and mixtures thereof.
  • organic peroxides e.g., benzoyl peroxide
  • azo compounds e.g., benzyl peroxide
  • quinones quinones
  • nitroso compounds e.g., acyl halides
  • hydrazones e.g., mercapto compounds
  • pyrylium compounds e.g., imidazoles, chlorotriazines
  • benzoin benzoin alkyl ethers
  • diketones phenones
  • phenones e.g., phenones
  • Suitable thermally-latent catalyst suitable for curing the multi-functional thermosetting resin include, for example, latent catalysts useful in one part epoxy adhesives.
  • Illustrative catalysts include blocked imidazoles MZ-A, MA-OK and PHZ-S (Air Products) and polymer bound imidazoles such as Intelimer 7004 (Landec Inc.)
  • imidazole catalysts, especially solids, such as 1,3 dialkylimidiazolium salts, imidiazole derivative - transition metal complexes, 2-ethyl-4-methylimidiazole, 2- phenyl-4-methylimidiazole, 2,4-diamino-6-[2'-methylimidazolyl-(l)']ethyl-s-triazine, and the like may be used.
  • the catalyst if present in an embodiment, comprises at least about 0.01 wt%, preferably at least about 0.1 wt% of the composition. In other embodiments, the catalyst can comprise no more than about 5 wt% of the composition, preferably no more than about 10 wt%.
  • Suitable acrylic acid salts include, for example, (meth) acrylic acid containing oligomer units joined by one or more polyvalent metal salt bridges. Such salt bridges may dissociate at higher than ambient temperatures thereby improving flow of the adhesive composition.
  • Suitable acrylic acid salts include Sartomer CN2404, a polyester acrylate oligomer, and CN2405, a urethane acrylate oligomer.
  • the multi-functional thermosetting resin is an epoxy resin.
  • the acrylate ester polymer is a copolymer of butylacrylate and glycidyl methacrylate.
  • the multi-functional acrylate ester comprises trimethylolpropanetriacrylate.
  • the polymer catalyst or curing agent is a photo-initiated free radical curing agent.
  • the thermally-latent catalyst is an imidazole accelerator.
  • the acrylic acid salt is a metal salt of acrylic acid.
  • the semiconductor wafer has an active surface, a substrate surface, and a layer of the adhesive that is adjacent the substrate surface. The active surface of the semiconductor wafer is the region having integrated circuits whereas the substrate surface does not have integrated circuits.
  • the semiconductor chip has an active surface, a substrate surface, and a region of cured adhesive that is adjacent the substrate surface.
  • the adhesive has a backing.
  • the components of the adhesive are combined and coated onto a release liner to form an adhesive tape precursor.
  • the adhesive tape precursor is heated to form a tape.
  • the adhesive tape precursor is laminated to a suitable backing.
  • the backing if present, may be an elastomer such as ethylene propylene rubber (EPR), an ionomeric polymer, e.g., DuPont's Surlyn®, or the like.
  • EPR ethylene propylene rubber
  • the tape is laminated to a wafer.
  • a 50 ⁇ m thick Surlyn® film was laminated to the adhesive film coating.
  • the film laminate was cut into 25 mm strips.
  • the silicone release liner was removed from the adhesive film strips and the adhesive was laminated to a polished silicone wafer using four passes of a 2.0 kg rubber roller.
  • the silicone wafer had been cleaned by wiping the surface three times with heptane.
  • the force to remove the adhesive film strip from the silicone wafer at an angle of 180 degrees was measured using an I-Mass SP-2000 tester (IMASS Inc., Accord, MA). The force was measured at a peel speed of 30.5 cm/min.
  • the force to remove some samples from the silicone wafer was measured after the sample had been passed once through a Fusion Systems UV Curing Unit (H lamp, 0.5 J/cm 2 ) (Gaithersburg, MD).
  • the modulus of the UV irradiated and thermally cured adhesive film was measured at 25 0 C using a Dynamic Mechanical Analyzer (TA Instruments Inc., New Castle, DE).
  • the peak temperature of the exothermic chemical process when the adhesive film is heated at 1O 0 C / minute was measured with a Differential Scanning Calorimeter (DSC) obtained from TA Instruments, Inc.
  • the glass transition temperature (T g ) of the cured adhesive film was measured with the DSC.
  • An adhesive film sample was laminated to a glass microscope cover slip with a hand held rubber roller.
  • the laminated film sample was treated with UV irradiation (Fusion Systems H lamp, 0.5 J/ cm 2 ).
  • the Surlyn® film was removed from the irradiated adhesive film sample.
  • the glass microscope cover slip with the adhesive film sample was placed on a hot plate heated to 100 0 C, and a second glass microscope cover slip was carefully placed on the adhesive film sample and laminated by hand with a 2.3 kilogram rubber roller.
  • the laminated sample was heated for one hour in an oven set at 16O 0 C. No voids were visible with a microscope set at 30X amplification.
  • the adhesive coating solution was applied to a silicone treated polyethyleneterephthalate (PET) film with a knife coater to produce a 25 ⁇ m thick adhesive after the coating was heated for 7 minutes at 85 0 C in a forced air oven.
  • PET polyethyleneterephthalate
  • Peel Mode The adhesive delaminated from the wafer during the Initial Peel test. Peel Mode - The Surlyn backing delaminated from the adhesive during the Peel test after UV exposure.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Adhesive Tapes (AREA)
  • Die Bonding (AREA)
PCT/US2008/056178 2007-03-16 2008-03-07 Dicing and die attach adhesive Ceased WO2008115711A1 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US12/530,692 US8022145B2 (en) 2007-03-16 2008-03-07 Dicing and die attach adhesive
EP08731642A EP2134800A4 (en) 2007-03-16 2008-03-07 DICING- UDN THE-ATTACH-ADHESIVE
CN2008800086804A CN101636462B (zh) 2007-03-16 2008-03-07 切片和晶片附连粘合剂
JP2009553701A JP2010521555A (ja) 2007-03-16 2008-03-07 ダイシング及びダイアタッチ接着剤

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US89518907P 2007-03-16 2007-03-16
US60/895,189 2007-03-16

Publications (1)

Publication Number Publication Date
WO2008115711A1 true WO2008115711A1 (en) 2008-09-25

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PCT/US2008/056178 Ceased WO2008115711A1 (en) 2007-03-16 2008-03-07 Dicing and die attach adhesive

Country Status (7)

Country Link
US (1) US8022145B2 (https=)
EP (1) EP2134800A4 (https=)
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KR (1) KR20100014539A (https=)
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US20100056725A1 (en) 2010-03-04
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