Classifications

• • 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
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
  • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
  • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
  • C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
• • 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
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
  • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
  • C08G65/14—Unsaturated oxiranes

Definitions

• This invention relates to compounds that contain both epoxy and styrenic or cinnamyl functionality and that can be used in curable compositions.
• Curable compositions are used in the fabrication and assembly of semiconductor packages and microelectronic devices, such as in the bonding of integrated circuit chips to lead frames or other substrates, in the bonding of circuit packages or assemblies to printed wire boards, or in encapsulants or coating materials.
• electron donor/electron acceptor adhesive systems that are used in the industry, but not all these give as full performance as is needed for all uses.
• the compounds disclosed in this specification add to the spectrum of performance materials for use within the semiconductor fabrication industry.
• this invention relates to compounds that contain both epoxy and styrenic or cinnamyl functionality.
• this invention is a curable composition, such as an adhesive, coating, or encapsulant composition, containing such compounds.
• DETAILED DESCRIPTION OF THE INVENTION [0004]
• this invention is a compound having at least one epoxy group and one styrenic or cinnamyl group per molecule.
• this invention is a curable composition, such as an adhesive, coating, or encapsulant, containing the compound with both epoxy and styrenic or cinnamyl functionality.
• the composition can be a paste, prepared by blending or milling, or can be a film, prepared by standard film making techniques known to those skilled in the art.
• the curable composition will include optionally a curing agent, and optionally a filler.
• These compounds can be the main component in the curable composition or can be added as an adhesion promoter to one or more other curable resins.
• an adhesion promoter the amount used in the curable composition will be an effective amount to promote adhesion and, in general, an effective amount will range from 0.005 to 20.0 percent by weight of the formulation.
• curable resins for use as the main component in the curable compositions include epoxies, vinyl ethers, thiol- enes, compounds derived from cinnamyl and styrenic starting compounds, fumarates, maleates, acrylates, and maleimides.
• Suitable curing agents are thermal initiators and photoinitiators present in an effective amount to cure the composition. In general, those amounts will range from 0.5% to 30%, preferably 1% to 20%, by weight of the total organic material (that is, excluding any inorganic fillers) in the composition.
• Preferred thermal initiators include peroxides, such as butyl peroctoates and dicumyl peroxide, and azo compounds, such as 2,2'- azobis(2-methyl-propanenitrile) and 2,2'-azobis(2-methyl-butanenitriIe).
• a preferred series of photoinitiators is one sold under the trademark Irgacure by Ciba Specialty Chemicals.
• both thermal initiation and photoinitiation may be desirable: the curing process can be started either by irradiation, followed by heat, or can be started by heat, followed by irradiation.
• the curable compositions will cure within a temperature range of 70°C to 250°C, and curing will be effected within a range of ten seconds to three hours.
• the actual cure profile will vary with the components and can be determined without undue experimentation by the practitioner.
• the curable compositions may also comprise nonconductive or thermally or electrically conductive fillers.
• Suitable conductive fillers are carbon black, graphite, gold, silver, copper, platinum, palladium, nickel, aluminum, silicon carbide, boron nitride, diamond, and alumina.
• Suitable nonconductive fillers are particles of vermiculite, mica, wollastonite, calcium carbonate, titania, sand, glass, fused silica, fumed silica, barium sulfate, and halogenated ethylene polymers, such as tetrafluoroethylene, trifluoro- ethylene, vinylidene fluoride, vinyl fluoride, vinylidene chloride, and vinyl chloride. If present, fillers generally will be in amounts of 20% to 90% by weight of the formulation.
• this invention is a curable composition
• a curable composition comprising the compound having at least one epoxy group and at least one styrenic or cinnamyl group per molecule and an epoxy resin.
• the epoxy resin has the structure
• EPICLON EXA-7120 (alcohol) is mixed into triethylamine in dry toluene at 0°C, after which is added one mole equivalent of vinyl silane dissolved in toluene. The mixture is allowed to react for four hours at room temperature. The solvent is evaporated to give a product that is mixed into triethylamine in dry toluene at 0°C. Cinnamyl alcohol in toluene is added and the reaction mixture reacted for four hours at room temperature to give the final product.
• 3-lsopropenyI- ⁇ , ⁇ -dimethylbenzyl isocyanate (m-TMI, 1.91 g, 0.00592 mole) was solvated in 50 mL THF in a 500 mL three-necked flask equipped with a mechanical stirrer, addition funnel and nitrogen inlet/outlet tube. The reaction was placed under nitrogen, and 0.01 equiv. dibutyltin dilaurate (catalyst) was added with stirring as the solution was heated to 80°C. The addition funnel was charged with Kraton liquid polymer L-207 (39.05 g, 0.00592 mole) dissolved in 50 mL THF.
• 3-lsopropenyI- ⁇ , ⁇ -dimethylbenzyI isocyanate (m-TMI, 80.75 g, 0.40 mole) was solvated in 100 mL toluene in a 500 mL three-necked flask equipped with a mechanical stirrer, addition funnel and nitrogen inlet/outlet. The reaction was placed under nitrogen, and 0.01 equiv. dibutyltin dilaurate (catalyst) was added with stirring as the solution was heated to 60°C. The addition funnel was charged with glycidol (29.65 g, 0.40 mole) dissolved in 50 mL toluene.
• EXAMPLE 5 Performance.
• a curable composition was prepared comprising a bismaleimide, a compound with cinnamyl functionality, curing agents, and 75% by weight silver. To this composition was added an epoxy at 1 weight percent, or a compound from Example 2, 3, or 4, at 1 weight percent, or a blend of an epoxy at 1 weight percent and one of the compounds from the examples at 1 weight percent. These compositions were tested for adhesive strength as die attach adhesives.
• the epoxy used in this formulation has the structure:
• the adhesive was dispensed on a copper leadframe (die pad, 650 X 650 mil), a silicon die (500 X 500 mil) placed onto the adhesive, and the adhesive cured in an oven at 175°C for 30 minutes. Ten assemblies for each adhesive composition were prepared. The die was sheared from the leadframe at 90 degrees with a Dage 2400-PC Die Shear Tester at 250°C and the results recorded in Kilogram force. The results were pooled and averaged and are set out in the following table. [0019]

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Epoxy Resins (AREA)
• Adhesives Or Adhesive Processes (AREA)
• Epoxy Compounds (AREA)

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• 2001
  • 2001-09-28 US US09/966,449 patent/US6441121B1/en not_active Expired - Fee Related
• 2002
  • 2002-07-01 JP JP2003532484A patent/JP2005506988A/ja active Pending
  • 2002-07-01 WO PCT/US2002/020652 patent/WO2003029234A1/en not_active Ceased
  • 2002-07-01 KR KR1020047004000A patent/KR100883375B1/ko not_active Expired - Fee Related
  • 2002-09-27 TW TW091122783A patent/TWI304414B/zh not_active IP Right Cessation

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