WO1993017059A1 - Adhesif a duricssement rapide et procede - Google Patents

Adhesif a duricssement rapide et procede Download PDF

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Publication number
WO1993017059A1
WO1993017059A1 PCT/US1993/002217 US9302217W WO9317059A1 WO 1993017059 A1 WO1993017059 A1 WO 1993017059A1 US 9302217 W US9302217 W US 9302217W WO 9317059 A1 WO9317059 A1 WO 9317059A1
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WIPO (PCT)
Prior art keywords
silver
adhesive
amount
flake
particles
Prior art date
Application number
PCT/US1993/002217
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English (en)
Inventor
Mr. N. Nguyen
Original Assignee
Johnson Matthey Inc.
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Filing date
Publication date
Application filed by Johnson Matthey Inc. filed Critical Johnson Matthey Inc.
Publication of WO1993017059A1 publication Critical patent/WO1993017059A1/fr

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    • 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
    • H01L24/80—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
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
    • C08G73/065—Preparatory processes
    • C08G73/0655—Preparatory processes from polycyanurates
    • C08G73/0661—Preparatory processes from polycyanurates characterised by the catalyst used
    • 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
    • C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; 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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    • 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
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    • 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
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    • 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
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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
    • H01L2224/83855—Hardening the adhesive by curing, i.e. thermosetting
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    • H01L2924/01—Chemical elements
    • H01L2924/01005—Boron [B]
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    • H01L2924/078—Adhesive characteristics other than chemical
    • H01L2924/07802—Adhesive characteristics other than chemical not being an ohmic electrical conductor

Definitions

  • the present invention relates to a rapidly curing adhesive for bonding a semiconductor device to a substrate, more particularly, to a cyanate ester-containing adhesive and to a method of reducing the curing time of a cyanate ester-containing adhesive.
  • a rapidly curing adhesive for bonding a semiconductor device to a substrate-
  • One embodiment comprises a cyanate ester vehicle, an alkylphenol, a metal-containing curing catalyst and a small but effective amount of silver to act as co-catalyst to impart the property of rapid curability to the adhesive.
  • the silver in this embodiment is present in an amount of not greater than about 20% by weight and is selected from the group consisting of uncoated flake and powder silver particles and flake and powder silver particles coated with a surfactant.
  • a rapidly curing adhesive comprising a cyanate ester vehicle and silver but without a curing co-catalyst. In the latter embodiment 20% to 90% silver will impart rapid curing capability to the cyanate ester containing adhesive-
  • the silver particles used in accordance with the invention have a particle size within the range of 0-1 to 50 ⁇ m, a surface area of 0.1 to 2 m 2 /g and tap density of 2 to 5 g/cc.
  • adding a small but effective amount of a commercially pure silver in an amount not greater than about 20 wt. % to a cyanate ester-containing adhesive comprising 10 to 40 wt.% cyanate ester vehicle, 0.1 to 2 wt.% alkylphenol, and 0.01 to 0.1 wt.% of a metal-containing curing catalyst will reduce the formulation curing time.
  • the silver catalyst is selected from the group consisting of uncoated flake and powder particles and flake and powder particles coated with a surfactant, said particles having a particle size within the range of 0.1 to 50 ⁇ , a surface area of 0.1 to 2 m 2 /g and a tap density of 2 to 5 g/cc.
  • FIG. 1 is a diagram describing the cyanate ester curing reactions
  • FIG. 2 is a graph showing the isothermal polymerization of bisphenol adicyanate (uncatalyzed);
  • FIGs. 3, 4 and 5 are graphs showing the weight loss of die attach adhesive examples described in the application.
  • FIGs. 6 and 7 are graphs showing cure characteristics for examples disclosed in the application.
  • the prepolymer resin is cured by a cyclotr ⁇ merization to produce a polycyanurate thermoset plastic.
  • the trimerization rates of uncatalyzed liquid or molten commercial dicyanates are impractically slow, as shown in FIG. 2. This is consistent with what has been known about cyanate ester-containing adhesives prior to my invention as, for example, indicated by Shimp in U.S. Patent 4,604,452.
  • curing of cyanate ester monomers is disclosed using a metal carboxylate catalyst such as copper, tin, lead, manganese, nickel, iron, zinc or cobalt with an active hydrogen compound such as alkylphenol added to catalyze the formation of triazine rings.
  • a metal carboxylate catalyst such as copper, tin, lead, manganese, nickel, iron, zinc or cobalt
  • an active hydrogen compound such as alkylphenol added
  • compositions described in Table I below show various cyanate ester- containing compositions.
  • Examples A-D show compositions of cyanate ester- containing formulations, some of which have 60 to 90 wt.% silver.
  • Example A includes a metal curing catalyst (cobalt acetylacetonate) and alkylphenol with silver whereas Examples C and D include only alkylphenol with silver.
  • Example B excludes both alkylphenol and the metal curing co-catalysts and, thus, only contains silver and cyanate ester.
  • complete cure is defined as the condition achieved at the highest strength.
  • One method used to determine the degree of cure is to measure the adhesive strength of a bonded material. For example, the curing time shown in FIG. 2 is two minutes at 160°C or 30 seconds at 200 °C to achieve maximum adhesion strength. This may be compared with the rate of cure for uncatalyzed cyanate ester monomers which require as much as 30 hours, shown in FIG. 3.
  • the compositions are for thermal conductive package where a small amount of silver is useful as a catalyst to minimize curing time.
  • the silver used has a particle size of less than 50 ⁇ m, a surface area of 0.1-2m 2 /g and tap density of 2.0-5.0 g/cc.
  • Other filler materials such as SiC, Si, and Ni may also be included and, when present, may be in particle size ranges of 50 microns or less.
  • Table II and Table III illustrate the effect of a small but effective amount of silver on the curing time where curing co-catalysts are also included in the adhesive formulation.
  • additional improvement is achieved by the presence of -OH, or NH groups in amounts as little as 0.5 to 6.0 parts per hundred of cyanate ester resin. This addition also achieves complete conversion and maximum adhesive strengths, thus accelerating curing time.
  • Example E-H the silver percentage increases from 0 to 15 wt. % .
  • the adhesive strength of the compositions described in Table II are shown in Table III. Li these examples the curing schedule was 200°C for 30, 60 and 120 seconds, as indicated.
  • full curing as measured by adhesive strength, can be achieved in as little as 30 seconds, although higher strengths are obtained with slightly longer curing time, i.e., 120 sec, but still well in the rapid curing range, i.e., less than 5 minutes at 200 °C, preferably less than 2 minutes at 200°C.
  • Typical properties of the silver co-catalyst added to the cyanate ester- containing adhesive formulation to reduce curing time in accordance with the invention are: particle sizes 0.1 to 50 ⁇ m; surface area 0.1 to 2.0 m 2 /g; tap density 2 to 5 g/cc
  • silver, powder or flake can be blended with other fillers into cyanate ester adhesive formulations to develop the property of being able to be cured rapidly. In such cases from 10 to 20% of silver by weight will be advantageous.
  • the curing time reduction achievable with this modest amount of silver is the same as that achieved by formulations with 60 to 90 wt. % silver.
  • the data in Table IV below shows that the addition of silver alone improves curing efficiency.
  • the gel point, or gelation, shown in Table IV is a measure of curing efficiency because it indicates me time required for onset formation of thermoset material.
  • the addition of from small amounts to large amounts of silver affects the gel point by reducing it significantly below the gel point of a composition devoid of silver.
  • a rapidly curing adhesive for bonding a semiconductor device to a substrate comprising a cyanate ester vehicle, an active hydrogen compound from the group of aromatic amines and alkylphenol, a metal-containing curing catalyst and a small but effective amount of silver to act as a co-catalyst to facilitate the rapid curability of said adhesive, said silver being present in an amount of not greater than about 20 wt.% and selected from the group of uncoated flake and powder particles and flake and powder particles coated with a surfactant, and mixtures thereof, said particles having a particle size within the range of 0.1 to 50 ⁇ m, a surface area of 0.1 to 2 m 2 /g and a tap density of 2 to 5 g/cc.
  • a method of reducing the curing time at a temperature less than its glass transition temperature of cyanate ester-containing adhesives used for bonding a semiconductor device to a substrate said adhesive comprising 10 to 40 wt.% cyanate ester vehicle, 0.1 to 2 wt.% alkylphenol, and 0.01 to 0.1 wt.% of a metal-
  • said method comprising adding to said adhesive a small but effective amount of a co-curing catalyst comprising commercially pure silver in an amount not greater than about 20 wt.%, said silver selected from the group of uncoated flake and powder particles and flake and powder particles coated with a surfactant, said particles having a particle size within the range of 0.1 to 50 ⁇ m, a
  • a rapidly curing adhesive for bonding a semiconductor device to a substrate comprising a cyanate ester vehicle and an amount of silver to act as a co- catalyst to facilitate the rapid curability of said adhesive, said silver being present in
  • a mediod of reducing the curing time at a temperature less than its glass transition temperature of cyanate ester-containing adhesives used for bonding a semiconductor device to a substrate said method comprising adding to said adhesive 60 to 90 wt.% commercially pure silver, said silver selected from the group of
  • a rapidly curing adhesive for bonding a semiconductor device to a substrate comprising 10 to 40 wt.
  • % cyanate ester vehicle and an amount of silver which is effective to facilitate the rapid curability of said adhesive, said silver being present as particles in an amount of not greater than about 90 wt.% and selected from the group of uncoated flake and powder and flake and powder coated with a surfactant, and mixtures thereof, said particles having a particle size within the range of 0.1 to 50 ⁇ m, a surface area of 0.1 to 2 m 2 /g and a tap density of 2 to 5 g/cc.
  • a rapidly curing adhesive for bonding a semiconductor device to a substrate comprising a cyanate ester vehicle and an amount of silver to act as a catalyst to facilitate the rapid curability of said adhesive, said silver being present as particles in an amount of up to 90 wt. % and selected from the group of uncoated flake and powder and flake and powder coated with a surfactant, and mixtures thereof, said particles having a particle size within the range of 0.1 to 50 ⁇ m, a surface area of 0.1 to 2 m 2 /g and a tap density of 2 to 5 g/cc.
  • a method of reducing the curing time at a temperature less than its glass transition temperature of cyanate ester-containing adhesives used for bonding a semiconductor device to a substrate comprising adding to said adhesive up to 90 wt.% commercially pure silver, said silver selected from the group of uncoated flake and powder particles and flake and powder particles coated with a surfactant, said particles having a particle size within the range of 0.1 to 50 ⁇ m, a surface area of 0.1 to 2 m 2 /g and a tap density of 2 to 5 g/cc.

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

Abstract

L'invention se rapporte à une formulation d'adhésif à durcissement rapide et à un procédé de réduction du temps de durcissement d'une formulation d'adhésif contenant de l'ester de cyanate.
PCT/US1993/002217 1992-02-28 1993-02-25 Adhesif a duricssement rapide et procede WO1993017059A1 (fr)

Applications Claiming Priority (2)

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US84373992A 1992-02-28 1992-02-28
US07/843,739 1992-02-28

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WO1993017059A1 true WO1993017059A1 (fr) 1993-09-02

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AU (1) AU3802793A (fr)
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Cited By (3)

* 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
WO2003035718A1 (fr) * 2001-10-19 2003-05-01 Lonza Ag Compositions de cyanate durcissables
US8030431B2 (en) 2001-10-19 2011-10-04 Lonza Ag Hardenable cyanate compositions

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US4604452A (en) * 1985-10-21 1986-08-05 Celanese Corporation Metal carboxylate/alkylphenol curing catalyst for polycyanate esters of polyhydric phenols
US4740830A (en) * 1986-06-04 1988-04-26 W. R. Grace & Co. Low temperature single step curing polyimide adhesive
US5037691A (en) * 1986-09-15 1991-08-06 Compositech, Ltd. Reinforced plastic laminates for use in the production of printed circuit boards and process for making such laminates and resulting products

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US4552690A (en) * 1983-06-23 1985-11-12 Mitsubishi Gas Chemical Company, Inc. Electrically conductive resin composition
US4604452A (en) * 1985-10-21 1986-08-05 Celanese Corporation Metal carboxylate/alkylphenol curing catalyst for polycyanate esters of polyhydric phenols
US4740830A (en) * 1986-06-04 1988-04-26 W. R. Grace & Co. Low temperature single step curing polyimide adhesive
US5037691A (en) * 1986-09-15 1991-08-06 Compositech, Ltd. Reinforced plastic laminates for use in the production of printed circuit boards and process for making such laminates and resulting products

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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
WO2003035718A1 (fr) * 2001-10-19 2003-05-01 Lonza Ag Compositions de cyanate durcissables
US8030431B2 (en) 2001-10-19 2011-10-04 Lonza Ag Hardenable cyanate compositions

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AU3802793A (en) 1993-09-13
MX9301091A (es) 1993-09-01

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