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WO1993016987A1 - Adhesif de fixation sur matrice souple a basse temperature - Google Patents

Adhesif de fixation sur matrice souple a basse temperature Download PDF

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Publication number
WO1993016987A1
WO1993016987A1 PCT/US1993/001704 US9301704W WO9316987A1 WO 1993016987 A1 WO1993016987 A1 WO 1993016987A1 US 9301704 W US9301704 W US 9301704W WO 9316987 A1 WO9316987 A1 WO 9316987A1
Authority
WO
WIPO (PCT)
Prior art keywords
flexible
adhesive
cyanate ester
silver
group
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/US1993/001704
Other languages
English (en)
Inventor
My N. Nguyen
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.)
JOHNSON MATTHEY Inc
Johnson Matthey Inc
Original Assignee
JOHNSON MATTHEY Inc
Johnson Matthey Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by JOHNSON MATTHEY Inc, Johnson Matthey Inc filed Critical JOHNSON MATTHEY Inc
Publication of WO1993016987A1 publication Critical patent/WO1993016987A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C261/00—Derivatives of cyanic acid
    • C07C261/02—Cyanates
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • 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
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0016—Plasticisers
    • 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
    • C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
    • C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20—Conductive material dispersed in non-conductive organic material
    • H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
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    • H01L23/00—Details of semiconductor or other solid state devices
    • H01L23/48—Arrangements for conducting electric current to or from the solid state body in operation, e.g. leads, terminal arrangements ; Selection of materials therefor
    • H01L23/488—Arrangements for conducting electric current to or from the solid state body in operation, e.g. leads, terminal arrangements ; Selection of materials therefor consisting of soldered or bonded constructions
    • H01L23/498—Leads, i.e. metallisations or lead-frames on insulating substrates, e.g. chip carriers
    • H01L23/49855—Leads, i.e. metallisations or lead-frames on insulating substrates, e.g. chip carriers for flat-cards, e.g. credit cards
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    • H01L2224/28—Structure, shape, material or disposition of the layer connectors prior to the connecting process
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    • H01L2224/29298—Fillers
    • H01L2224/29299—Base material
    • H01L2224/293—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
    • H01L2224/29338—Base material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof the principal constituent melting at a temperature of greater than or equal to 950°C and less than 1550°C
    • H01L2224/29339—Silver [Ag] as principal constituent
    • H—ELECTRICITY
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    • H01L2224/8319—Arrangement of the layer connectors prior to mounting
    • H—ELECTRICITY
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    • H01L2224/838—Bonding techniques
    • H01L2224/8385—Bonding techniques using a polymer adhesive, e.g. an adhesive based on silicone, epoxy, polyimide, polyester
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    • H01L2924/157—Material with a principal constituent of the material being a metal or a metalloid, e.g. boron [B], silicon [Si], germanium [Ge], arsenic [As], antimony [Sb], tellurium [Te] and polonium [Po], and alloys thereof
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    • H01L2924/15747—Copper [Cu] as principal constituent

Definitions

  • the present invention relates to a flexible die attach adhesive.
  • the flexible die adhesive can be modified to be capable of developing very good adhesive strength at low curing temperatures.
  • One embodiment of the invention relates to flexible card for processing in a computer that includes a semiconductor device enveloped therein adhered to a substrate by the aforementioned adhesive.
  • cards One application employing semiconductor devices which is gaining increasing importance is in the field of cards to be processed in computers where such cards incorporate one or more semiconductor devices and are therefore able to store more information than magnetic cards. Such cards may be useful over a broad spectrum of applications including, for example, credit and telephone cards. These cards, which are referred to as “smart cards", must be thin and must be able to bend without breaking, i.e., the card and card components must be flexible.
  • "smart cards” are constructed of a material such as polyester reinforced with glass fibers and have enveloped within the card one or more semiconductor devices. Desirably, such devices should be secured within the card by a die attach adhesive which is flexible but which provides very good adhesive strength and does not impart stress to the die during curing. It is also important that the adhesive be capable of being cured at relatively low temperatures to facilitate fabrication of the cards without damage .to the card or the semiconductor devices.
  • a die attach adhesive which is flexible but which provides very good adhesive strength and does not impart stress to the die during curing. It is also important that the adhesive be capable of being cured at relatively low temperatures to facilitate fabrication of the cards without damage .to the card or the semiconductor devices.
  • the invention includes adhesive formulation for bonding a semiconductor device to a substrate, which comprises a reaction product of cyanate ester and the elastomeric modifier, as discussed above, having a low glass transition temperature of less than about 25°C.
  • the adhesive may include an alkylphenol, a metal-containing curing catalyst, and/or silver in the form of flake or powder.
  • the alkylphenol is nonylphenol
  • the metal-containing curing catalyst is from the group consisting of cobalt acetylacetonate and copper naphthenate and the silver is present in amounts up to 90 wt.%.
  • the adhesive comprises the reaction product of 6 to 24 wt.% modifier and 4 to 16 wt.% cyanate ester, 0.01 to 0.06 wt. % metal-containing curing catalyst, 0.5 to 2 wt. % alkylphenol and up to 90 wt.% silver flake and/or powder. Where alkylphenol and/or metal containing catalyst are present as little as 4 to 20% silver may be sufficient. Where these curing catalysts are absent 60 to 90 wt. % silver may be needed to impart rapid curability to the adhesive formulation.
  • a novel card in accordance with the invention for processing in a computer, comprises a semiconductor device enveloped within the card and adhered with a flexible adhesive to a substrate.
  • the substrate is advantageously a flexible organic polymeric substrate and/or a lead frame or metal conductor.
  • the adhesive comprises the reaction product of cyanate ester and modifier, as described above, having a glass transition temperature of less than about 25°C, and which may include an alkylphenol, a metal-containing curing catalyst and/or silver in the form of flake and/or powder.
  • Figure 1 is a graph showing the relationship between the percentage of modifier, i.e., flexibilizer and radius of curvature, ("ROC");
  • Figure 2 is a graph of die stress against ROC.
  • Figure 3 is a schematic view partly in section of a card within which one or more semiconductor devices are enveloped and showing such devices bonded to a substrate.
  • a flexible adhesive is needed for a number of applications where semiconductor devices with large surface areas are attached to flexible substrates, particularly where there is a significant difference between the thermal expansion coefficients of the silicon of the semiconductor device and the substrates.
  • a low-stress die attach adhesive is required for maximum performance. This is especially important where the semiconductor device is to be attached to lead frames, such as copper lead frames, and polymeric substrates such as polyester, polyamide films, etc. If a conventional rigid adhesive such as epoxy referred to in the aforementioned Steinegger article is used in the above described applications, the thermally induced tensile stress imparted to the surface of the semiconductor die is so high that it usually results in a silicon fracture.
  • ROC radius of curvature
  • cyanate ester and silver do not give the flexible properties needed for the above applications.
  • flexible properties can be achieved by reacting cyanate esters with at least one elastomeric and thermoplastic modifier from the group of hydroxyl (-OH), amine (NH) or epoxide reactive functional groups, or mixtures thereof by, for example, grafting such group to cyanate ester molecular structures.
  • cyanate ester 15% cyanate ester is needed in the adhesive formulation to provide satisfactory curing in this system.
  • Other elastomeric modifiers containing hydroxyl reactive groups including hydroxyl terminated butadiene and butadiene-acrylonitrile copolymers, such as "HYCAR” sold by B.F. Goodrich and "V_TEL-3600” which is a saturated copolyester resin with a Tg of -11°C, are useful as well as amine functional groups such as polyurethane, elastomer, urethane acrylate, silicone imides, etc.
  • a card 10 usually made of plastic, includes a metal conductor 12 to which is bonded a semiconductor device 14. Glass fiber reinforced polyester pads 16 may be included and the entire device is encapsulated, such as within an epoxy resin 18. The epoxy resin may be ground flat to produce a thin plastic card.
  • the adhesive formulation of the present invention is especially suitable for bonding the semiconductor device to a substrate because it is capable of being cured at comparatively low temperatures of 100 to 130 °C and has very good adhesive strength while imparting low stress on the die. It is highly desirable for smart card application to employ a die attach adhesive capable of being cured at temperatures not substantially greater than about 130 °C.
  • the die may be attached to a lead frame, such as a copper lead frame in which case the low temperature curing adhesive minimizes oxidation of the copper and thereby eliminates the need of nitrogen or other inert atmosphere such as is often used in curing ovens.
  • the following examples are of flexible adhesive compositions used to bond semiconductor devices suitable for smart card manufacture.
  • the cyanate ester Arocy L10 is available from Rhone-Poulenc of Louisville, Kentucky.
  • the modified bisphenol epoxy resin such as XB 4122 or XUGY 376 is a flexible epoxy supplied by Ciba Geigy.
  • the catalyst system is a solution of copper naphthenate or copper acetylacetonate in nonylphenol.
  • the silver flake has the same physical properties described in the previous examples. Adhesive strength results appear in the following table.
  • the catalysts in the foregoing system may be copper naphthenate or copper acetylacetonate, nonylphenol and silver.
  • the formulation in Example III was cured at 100°C for 15 minutes and exhibited an adhesive strength of over 30 Kg for a semiconductor die X150 attached on a copper lead frame.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Computer Hardware Design (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Power Engineering (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Dispersion Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

L'invention se rapporte à une formulation adhésive souple destinée à fixer un dispositif semiconducteur (14) à un substrat souple et à une carte souple contenant un dispositif semiconducteur (14) qui peut être traité dans un ordinateur.
PCT/US1993/001704 1992-02-28 1993-02-25 Adhesif de fixation sur matrice souple a basse temperature Ceased WO1993016987A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US84373892A 1992-02-28 1992-02-28
US07/843,738 1992-02-28

Publications (1)

Publication Number Publication Date
WO1993016987A1 true WO1993016987A1 (fr) 1993-09-02

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1993/001704 Ceased WO1993016987A1 (fr) 1992-02-28 1993-02-25 Adhesif de fixation sur matrice souple a basse temperature

Country Status (3)

Country Link
AU (1) AU3778493A (fr)
MX (1) MX9301074A (fr)
WO (1) WO1993016987A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5489637A (en) * 1992-05-28 1996-02-06 Johnson Matthey Inc Low temperature flexible die attach adhesive and articles using same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4552690A (en) * 1983-06-23 1985-11-12 Mitsubishi Gas Chemical Company, Inc. Electrically conductive resin composition
US5150195A (en) * 1990-10-24 1992-09-22 Johnson Matthey Inc. Rapid-curing adhesive formulation for semiconductor devices

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4552690A (en) * 1983-06-23 1985-11-12 Mitsubishi Gas Chemical Company, Inc. Electrically conductive resin composition
US5150195A (en) * 1990-10-24 1992-09-22 Johnson Matthey Inc. Rapid-curing adhesive formulation for semiconductor devices

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5612403A (en) * 1990-10-24 1997-03-18 Johnson Matthey, Inc. Low temperature flexible die attach adhesive and articles using same
US5489637A (en) * 1992-05-28 1996-02-06 Johnson Matthey Inc Low temperature flexible die attach adhesive and articles using same

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MX9301074A (es) 1993-11-01
AU3778493A (en) 1993-09-13

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