US20020007042A1 - Die attach adhesives for use in microelectronic devices - Google Patents
Die attach adhesives for use in microelectronic devices Download PDFInfo
- Publication number
- US20020007042A1 US20020007042A1 US09/773,800 US77380001A US2002007042A1 US 20020007042 A1 US20020007042 A1 US 20020007042A1 US 77380001 A US77380001 A US 77380001A US 2002007042 A1 US2002007042 A1 US 2002007042A1
- Authority
- US
- United States
- Prior art keywords
- chain
- alkyl
- aryl
- independently
- adhesive 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.)
- Abandoned
Links
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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
- H01L24/29—Structure, shape, material or disposition of the layer connectors prior to the connecting process of an individual layer connector
-
- 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
- C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/065—Polyamides; Polyesteramides; Polyimides
-
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
-
- 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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/285—Nitrogen containing compounds
- C08G18/2875—Monohydroxy compounds containing tertiary amino groups
-
- 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
-
- 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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
-
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- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/01—Chemical elements
- H01L2924/01082—Lead [Pb]
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- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/06—Polymers
- H01L2924/0665—Epoxy resin
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- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/06—Polymers
- H01L2924/078—Adhesive characteristics other than chemical
- H01L2924/0781—Adhesive characteristics other than chemical being an ohmic electrical conductor
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- 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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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/10—Details of semiconductor or other solid state devices to be connected
- H01L2924/11—Device type
- H01L2924/14—Integrated circuits
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/15—Details of package parts other than the semiconductor or other solid state devices to be connected
- H01L2924/151—Die mounting substrate
- H01L2924/156—Material
- 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
- H01L2924/15738—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
- H01L2924/15747—Copper [Cu] as principal constituent
Definitions
- This invention relates to compositions that are suitable for use as adhesives in microelectronic devices or semiconductor packages.
- Adhesive compositions are used for a variety of purposes in the fabrication and assembly of semiconductor packages and microelectronic devices. The more prominent uses are the bonding of integrated circuit chips to lead frames or other substrates, and the bonding of circuit packages or assemblies to printed wire boards.
- Another important aspect of an adhesive bonding or interconnection technology is the ability to rework the bond.
- a failed chip can be discarded without significant loss.
- it becomes expensive to discard multi-chip packages with only one failed chip consequently, the ability to rework the failed chip would be a manufacturing advantage.
- Today, one of the primary thrusts within the semiconductor industry is to develop adhesives that will meet all the requirements for adhesive strength and flexibility, but that will also be reworkable, that is, will be capable of being removed without destroying the substrate.
- This invention is an adhesive composition for use in electronic devices that comprises one or more mono- or polyfunctional maleimide compounds, or one or more mono- or polyfunctional vinyl compounds other than maleimide compounds, or a combination of maleimide and vinyl compounds, a curing initiator, and optionally, one or more fillers.
- the composition can be designed to be reworkable.
- this invention is the cured adhesive that results from the just described curable adhesive composition.
- this invention is a microelectronic assembly comprising an electronic component bonded to a substrate with a cured adhesive composition prepared from a composition comprising one or more mono- or polyfunctional maleimide compounds, or one or more mono- or polyfunctional vinyl compounds, or a combination of maleimide and vinyl compounds, a curing initiator, and optionally one or more fillers.
- the maleimide and vinyl compounds used in the adhesive compositions of this invention are curable compounds, meaning that they are capable of polymerization, with or without crosslinking.
- to cure will mean to polymerize, with or without crosslinking.
- Cross-linking as is understood in the art, is the attachment of two polymer chains by bridges of an element, a molecular group, or a compound, and in general will take place upon heating. As cross-linking density is increased, the properties of a material can be changed from thermoplastic to thermosetting.
- polymers of a wide range of cross-link density by the judicious choice and amount of mono- or polyfunctional compounds.
- the adhesive compositions can be prepared from mono-functional compounds to limit the cross-link density.
- a minor amount of poly-functional compounds can be added to provide some cross-linking and strength to the composition, provided the amount of poly-functional compounds is limited to an amount that does not diminish the desired thermoplastic properties.
- the strength and elasticity of individual adhesives can be tailored to a particular end-use application.
- the electronic component can be pried off the substrate, and any residue adhesive can be heated until it softens and is easily removed.
- the cross-link density can also be controlled to give a wide range of glass transition temperatures in the cured adhesive to withstand subsequent processing and operation temperatures.
- the maleimide compounds and the vinyl compounds may be used independently, or in combination.
- the maleimide or vinyl compounds, or both, will be present in the curable package adhesive compositions in an amount from 2 to 98 weight percent based on the organic components present (excluding any fillers).
- the adhesive compositions will further comprise at least one free-radical initiator, which is defined to be a chemical species that decomposes to a molecular fragment having one or more unpaired electrons, highly reactive and usually short-lived, which is capable of initiating a chemical reaction by means of a chain mechanism.
- the free-radical initiator will be present in an amount of 0.1 to 10 percent, preferably 0.1 to 3.0 percent, by weight of the organic compounds (excluding any filler).
- the free radical curing mechanism gives a fast cure and provides the composition with a long shelf life before cure.
- Preferred free-radical 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-butanenitrile).
- the adhesive compositions may contain a photoinitiator in lieu of the free-radical initiator, and the curing process may then be initiated by UV radiation.
- the photoinitiator will be present in an amount of 0.1 to 10 percent, preferably 1 to 5.0 percent, by weight of the organic compounds (excluding any filler). In some cases, both photoinitiation and thermal initiation may be desirable.
- the curing process can be started by UV irradiation, and in a later processing step, curing can be completed by the application of heat to accomplish a free-radical cure.
- these compositions will cure within a temperature range of 80-200° C., and curing will be effected within a length of time of less than 1 minute to 60 minutes.
- the time and temperature curing profile for each adhesive composition will vary, and different compositions can be designed to provide the curing profile that will be suited to the particular industrial manufacturing process.
- Suitable conductive fillers for the adhesives are silver, copper, gold, palladium, platinum. In some circumstances, nonconductive fillers may be needed, for example to adjust rheology, such as, alumina, silica, and teflon.
- the maleimide compounds suitable for use in the adhesive compositions of this invention have a structure represented by the formula: [M ⁇ X m ] n ⁇ Q, or by the formula: [M ⁇ Z m ] n —K.
- the compound when lower case “n” is the integer 1, the compound will be a mono-functional compound; and when lower case “n” is an integer 2 to 6, the compound will be a poly-functional compound.
- M is a maleimide moiety having the structure
- R 1 is H or C 1 to C 5 alkyl
- each X independently is an aromatic group selected from the aromatic groups having the structures (I) through (IV):
- Q is a linear or branched chain alkyl, alkyloxy, alkylene, alkyleneoxy, aryl, or aryloxy alkyl amine, alkyl sulfide, alkylene amine, alkylene sulfide, aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the backbone in the chain, and in which any heteroatom present may or may not be directly attached to X;
- each R 2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms
- R 3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents
- X is O, S, N, or P
- v is 0 to 50;
- R 3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents;
- Q is a siloxane having the structure: —(CR 1 2 ) e —[SiR 4 —O] f —SiR 4 2 —(CR 1 2 ) 0 — in which the R 1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms and the R 4 substituent independently for each position is H, an alkyl group having 1 to 5 carbon atoms or an aryl group, and e and g are independently 1 to 10 and f is 1 to 50; and
- m is 0 or 1
- n is 1 to 6.
- compositions are aliphatic bismaleimides in which the maleimide functionality is linked to the backbone through urethane or urea linkages, such as in the following preferred compounds:
- M is a maleimide moiety having the structure
- R 1 is H or C 1 to C 5 alkyl
- Z is a linear or branched chain alkyl, alkyloxy, alkyl amine, alkyl sulfide, alkylene, alkyleneoxy, alkylene amine, alkylene sulfide, aryl, aryloxy, or aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the backbone in the chain, and in which any heteroatom present may or may not be directly attached to K;
- each R 2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms
- R 3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents, and v is 0 to 50;
- Z is a siloxane having the structure: —(CR 1 2 ) e —[SiR 4 2 —O] f —SiR 4 2 —(CR 1 2 ) g — in which the R 1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms and the R 4 substituent independently for each position is H, an alkyl group having 1 to 5 carbon atoms or an aryl group, and e and g are independently 1 to 10 and f is 1 to 50;
- K is an aromatic group selected from the aromatic groups having the structures (VI) through (XIII) (although only one bond may be shown to represent connection to the aromatic group K, this will be deemed to represent any number of additional bonds as described and defined by n):
- R 5 , R 6 , and R 7 are a linear or branched chain alkyl, alkyloxy, alkyl amine, alkyl sulfide, alkylene, alkyleneoxy, alkylene amine, alkylene sulfide, aryl, aryloxy, or aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the backbone in the chain, and in which any heteroatom present may or may not be directly attached to the aromatic ring; or R 5 , R 6 , and R 7 are a siloxane having the structure —(CR 1 2 ) e —[SiR 4 2 —O] f —SiR 4 2 —(CH 3 ) g — in which the R 1 substituent is H or an alkyl group having 1 to 5 carbon atoms and the R 4 substituent independently for each position is an alkyl group having 1 to 5 carbon
- n is 1 to 6.
- Preferred maleimide compounds are N-butyphenyl malemide and N-ethylpenyl maleimide.
- the vinyl compounds (other than the maleimdes herein) suitable for use in the adhesive compositions of this invention will have the structure:
- R 1 and R 2 are H or an alkyl having 1 to 5 carbon atoms, or together form a 5 to 9 membered ring with the carbons forming the vinyl group;
- B is C, S, N, O, C(O), O—C(O), C(O)—O, C(O)NH or C(O)N(R 8 ), in which R 8 is C 1 to C 5 alkyl;
- m is 0 or 1;
- n is 1-6; and
- X, Q, Z, and K are as described above.
- B is O, C(O), C(O)—O, C(O)NH or C(O)N(R 8 ); more preferably B is O, C(O), O—C(O), C(O)—O, or C(O)N(R 8 ).
- Preferred vinyl compounds for use as adhesives are vinyl ethers or alkenyl sufides.
- suitable vinyl compounds are the following:
- the adhesive may also contain a coupling agent.
- a coupling agent as used herein is a chemical species containing a polymerizable functional group for reaction with the maleimide and other vinyl compound, and a functional group capable of condensing with metal hydroxides present on the surface of the substrate.
- Such coupling agents and the preferred amounts for use in compositions for particular substrates are known in the art.
- Suitable coupling agents are silanes, silicate esters, metal acrylates or methacrylates, titanates, and compounds containing a chelating ligand, such as phosphine, mercaptan, and acetoacetate.
- coupling agents typically will be in amounts up to 10 percent by weight, and preferably in amounts of 0.1-3.0 percent by weight, of the maleimide and other monofunctional vinyl compound.
- the adhesive compositions may contain compounds that lend additional flexibility and toughness to the resultant cured adhesive.
- Such compounds may be any thermoset or thermoplastic material having a Tg of 50° C. or less, and typically will be a polymeric material characterized by free rotation about the chemical bonds, the presence of ether groups, and the absence of ring structures.
- Suitable such modifiers include polyacrylates, poly(butadiene), polyTHF ( polymerized tetrahydrofuran), CTBN (carboxy-terminated butadiene-acrylonitrile) rubber, and polypropylene glycol.
- toughening compounds may be in an amount up to about 15 percent by weight of the maleimide and other monofunctional vinyl compound.
- siloxanes can be added to the package formulations to impart elastomeric properties. Suitable siloxanes are the methacryloxypropyl-terminated polydimethyl siloxanes, and the aminopropyl-terminated polydimethylsiloxanes, available from United Chemical Technologies and others.
- additives such as adhesion promoters, in types and amounts known in the art, may also be added.
- compositions will perform within the commercially acceptable range for die attach adhesives.
- Commercially acceptable values for die shear for the adhesives on a 80 ⁇ 80 mil 2 silicon die are in the range of greater than or equal to 1 kg at room temperature, and greater than or equal to 0.5 kg at 240° C., and for warpage for a 500 ⁇ 500 mil 2 die are in the range of less than or equal to 70 ⁇ m at room temperature.
- the coefficient of thermal expansion is the change in dimension per unit change in temperature for a given material. Different materials will have different rates of expansion. If the CTE is very different for elements attached together, thermal cycling can cause the attached elements to bend, crack, or delaminate.
- the CTE of the chip is in the range of 2 or 3 ppm/° C.; for organic circuit board substrate, the CTE is greater than 30 ppm/° C.; therefore, the CTE of the adhesive is best between that of the substrate and die.
- the glass transition region When a polymer is subjected to the application of heat, it will move through a transition region between a hard, glassy state to a soft, rubbery state. This region is known as the glass transition region or Tg. If a graph of expansion of the polymer versus temperature is plotted, the glass transition region is the intersection between the lower temperature/glassy region coefficient of thermal expansion and the higher temperature/rubbery region coefficient of thermal expansion. Above this region, the rate of expansion increases significantly. Consequently, it is preferred that the glass transition of the polymer be higher than normal operating temperatures experienced during the application, and if reworkability is needed, that the glass transition be lower than any rework temperature.
- Another embodiment of this invention includes the maleimides having the formulae [M ⁇ X m ] n ⁇ Q and [M ⁇ Z m ] n ⁇ K as described herein in which Q and Z can be an ester having the structure
- each R 3 can independently be an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents, or
- a siloxane having the structure —(CR 1 2 ) e —[SiR 4 2 —O] f —SiR 4 2 —(CR 1 2 —) g in which the R 1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R 4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10 and f is 1 to 50.
- Another embodiment of this invention includes the vinyl compounds having the structures
- B is C, S, N, O, C(O), C(O)NH or C(O)N(R 8 ), in which R 8 is C 1 to C 5 alkyl.
- Another embodiment of this invention includes the vinyl compounds having the structures
- each R 3 can independently be an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents,
- Another embodiment of this invention includes the curable adhesive composition as described herein containing an anionic or cationic curing initiator.
- an anionic or cationic curing initiator is well known in the art.
- compositions were investigated for viscosity and thixotropic index for the uncured composition, and for curing profile, glass transition temperature, coefficient of thermal expansion, thermal mechanical analysis, and in some cases reworkability for the cured composition.
- Tris(epoxypropyl)isocyanurate (99.0 g, 0.33 mol) is dissolved in THF (500 mL) in a 2 L three-necked flask equipped with mechanical stirrer, internal temperature probe and nitrogen inlet/outlet.
- hyroxyphenylmaleimide (189.2 g, 1 mol)
- benzyldimethylamine 1. g, 0.05 wt. %).
- the solution is heated to 80° C. for 7 hours.
- the reaction then is allowed to cool to room temperature, is filtered, and the filtrant washed with 5% HCl aq (500 mL) and distilled H 2 O (1 L).
- the resulting solid, triazinetris(maleimide) is vacuum dried at room temperature.
- Palmitoyl chloride (274.9 g, 1 mol) is dissolved in Et 2 O (500 mL) in a 2 L three-necked flask equipped with mechanical stirrer, internal temperature probe, addition funnel and nitrogen inlet/outlet.
- NaHCO 3 (84.0 g, 1 mol) in distilled H 2 O (500 mL) is added with vigorous stirring and the solution cooled on an ice bath under nitrogen.
- the addition funnel is charged with hydroxyethylmaleimide (141 g, 1 mol) in Et 2 O (100 mL) and this solution added to the reaction over a period of 30 minutes, maintaining an internal T ⁇ 10° C. during the addition.
- the reaction is stirred for another 30 minutes on ice, then allowed to warm to room temperature and stirred for 4 hours.
- the reaction is transferred to a separatory funnel and the isolated organic layer washed with distilled H 2 O (500 mL), 5% HCl aq (500 mL) and distilled H 2 O (2 ⁇ 500 mL).
- the organics are isolated, dried over MgSO 4 anhyd., filtered and solvent removed in vacuo to yield the aliphatic maleimide.
- the addition funnel is charged with hydroxyethylmaleimide (141 g, 1 mol) dissolved in THF (100 mL). This solution is added to the isocyanate solution over 30 minutes, and the resulting mixture heated for an additional 4 hours at 70° C. The reaction is allowed to cool to room temperature and solvent removed in vacuo. The remaining oil is dissolved in CH 2 Cl 2 (1 L) and washed with 10% HCl aq (1 L) and distilled H 2 O (2 ⁇ 1 L). The isolated organics are dried over MgSO 4 , filtered and the solvent removed in vacuo to yield the maleimide.
- a dimer diol (sold as Pripol 2033 by Unichema, 284.4 g, 500 mmol) is dissolved in dry acetone (500 mL) in a 1 L three-necked flask equipped with mechanical stirrer, addition funnel and internal temperature probe under nitrogen. Triethylamine (101.2 g, 1 mol) is added to this solution and the solution cooled to 4° C. on an ice bath. Acryloyl chloride (90.5 g, 1 mol) solvated in dry acetone (100 mL) is charged into the addition funnel and added to the stirred reaction solution over the course of 60 minutes, maintaining an internal temperature ⁇ 10° C.
- Dimer acid (sold under the trademark Empol 1024 by Unichema) (574.6 g, 1 mol) and propargyl alcohol (112.1 g, 2 mol) are solvated in toluene (1 L) in a 3 L three-necked flask equipped with mechanical stirring and a Dean-Stark distillation apparatus. Concentrated H 2 SO 4 (6 mL) is added and the solution refluxed for 6 hours until 36 mL of H 2 O is azeotropically distilled. The solution is allowed to cool to room temperature, is washed with H 2 O (2 ⁇ 1L), dried over MgSO 4 anhyd, and the solvent removed in vacuo to yield the propargyl ester intermediate as an oil.
- This ester intermediate (650.7 g, 1 mol) is solvated in THF (200 mL) in a 1 L three-necked flask equipped with reflux condensor, mechanical stirrer and internal temperature probe under nitrogen.
- Lauryl mercaptan 404.8 g, 2 mol
- 2,2′-azobis(2,4-dimethylpentanenitrile) (sold under the trademark Vazo 52 by DuPont) (11 g) are added and the resulting mixture heated to 70° C. on an oil bath with stirring for 7 hours. The reaction is allowed to cool to room temperature and solvent removed in vacuo to yield the alkenyl sulfide as an oil.
- the acid functional maleimide, 6-maleimidocaproic acid was synthesized using known methodology.
- 1 Aminocaproic acid (100 g, 7.6 ⁇ 10 ⁇ 1 mols) was dissolved in glacial acetic acid (50 mL) in a 500 mL four-necked flask equipped with mechanical stirring, an internal temperature probe and an addition funnel.
- the addition funnel was charged with a solution of maleic anhydride (74.8 g, 7.6 ⁇ 10 ⁇ 1 mols) dissolved in acetonitrile (75 mL). This solution was added to the aminocaproic acid at room temperature dropwise over 1 hour, maintaining an internal reaction temperature less than 35° C. The reaction was stirred for three hours after the addition was complete.
- Pripol 2033 (“dimer diol”, Uniqema, 92.4 g, 1.69 ⁇ 10 ⁇ 1 mols), 6-maleimidocaproic acid (75.0 g, 3.55 ⁇ 10 ⁇ 1 mols) and H 2 SO 4 (0.50 mL, ⁇ 8.5 ⁇ 10 ⁇ 3 mols) were slurried in toluene (300 mL) in a 1 L four-necked flask equipped with mechanical stirrer, a Dean-Stark trap and an internal temperature probe under nitrogen. The reaction was heated to light reflux for two hours and the water evolved collected in the Dean-Stark trap.
- the trap was drained and ⁇ 50 mL of toluene solvent was distilled off of the reaction to remove trace moisture and drive the esterification equilibrium to completion.
- the reaction was allowed to cool to room temperature, additional toluene (100 mL) was added (on the laboratory scale it is preferable to add diethyl ether in place of toluene at this point), and the solution was washed with saturated NaHCO 3 aq. (300 mL) and distilled water (300 mL).
- the organic layer was isolated and dried over anhydrous MgSO 4 , and the solvent removed in vacuo to yield an orange oil (107.2 g, 68%).
- the material can be further purified by eluting a toluene solution of the resin through a short plug of silica or alumina.
- This liquid bismaleimide resin exhibited acceptable FT-IR, 1 H NMR, and 13 C NMR data. Typical ⁇ ⁇ 2500 cPs.
- Example B The general procedure described in Example B. was applied substituting decane diol (29.5 g, 1.69 ⁇ 10 ⁇ 1 mols) for Pripol 2033. This process yielded a solid, moderately soluble bismaleimide (54.9 g, 58%). The product exhibited satisfactory FT-IR and 1 H NMR data.
- IPDI Isophorone diisocyanate
- m-nitrobenzyl alcohol 137.8 g, 9.0 ⁇ 10 ⁇ 1 mols
- dibutyl tin dilaurate 2.8 g, 4.5 ⁇ 10 ⁇ 3 mols
- the resulting solution was heated to 90° C. for 4 h. No isocyanate band was observed in the IR of the solids portion of the sample.
- the solution was allowed to cool to room temperature and washed with distilled H 2 O (100 mL). The organic layer was isolated and solvent removed in vacuo to yield a yellow liquid which exhibited acceptable FT-IR and 1 H NMR characteristics.
- DDI 1410 (Henkel, “Dimer Diisocyanate”, 99.77 g, 1.65 ⁇ 10 ⁇ 1 mols based on 13.96% NCO), m-nitrobenzyl alcohol (50.8 g, 3.32 ⁇ 10 ⁇ 1 mols) and dibutyltin dilaurate (0.5 mL, 8.3 ⁇ 10 ⁇ 4 mols) were solvated in toluene (150 mL) in a 1 L four-necked flask equipped with mechanical stirrer, reflux condenser and internal temperature probe under nitrogen. The reaction was heated to 85° C. for 2.5 h.
- aqueous layer was isolated and washed with ethyl acetate (100 mL). The organic layers were combined, washed with distilled water (300 mL) and dried over anhydrous MgSO 4 . The slurry was filtered and solvent removed from the filtrate in vacuo to yield yellow, sticky solid (33.8 g, 92%).
- a silver filled die attach adhesive formulation having a viscosity of 9011 cPs (5 rpm, cone and plate) and thixotropic index of 5.36 was produced by combining the following at room temperature using a mechanical mixer: Liquid bismaleimide of Example B: 2.644 g Dimer divinyl ether of Example 5: 2.644 g Ricon 131MA20 (Ricon Resins, Inc.): 0.661 g Silquest A-174 (Witco Corp.): 0.040 g USP-90MD (Witco Corp.): 0.099 XD0026 (NSCC trade secret): 0.119 SF-96 silver flake 23.794
- Example AA 120 ⁇ 120 mil die were attached to leadframes of various compositions utilizing the adhesive composition given in Example AA.
- the bonded die were then cured using “snap cure” (60 s/200° C.) and “fast oven cure” conditions (15 min./175° C.).
- the resulting cured devices were subjected to simulated HAST testing conditions (130° C., 85% RH) for 130 hours.
- the devices exhibited good adhesion as measured by die shear strength (DSS) at both room temperature and elevated temperature as shown in Table 2.
- DSS die shear strength
- Example AA The die attach composition described in Example AA. was used to bond 500 ⁇ 500 mil die to Pd-Cu leadframes. The assembled pieces were “snap cured” and measured for die warpage at several temperatures and times. Typical results are given in Table 3. The performance exhibited by this adhesive qualifies it as a “low stress” material. TABLE 3 Warpage of Maleimide/Vinyl Ether Die Attach Adhesive on 500 ⁇ 500 mil Die Thermal History 1 min/200° C. +1 min/240° C. +4 h/175° C. Warpage ( ⁇ m) 10.4+/ ⁇ 1.3 11.9+/ ⁇ 1.4 14.1+/ ⁇ 1.6
- Example AA The composition of Example AA. was used to produce ⁇ 1 mil films using a drawdown bar.
- the films were “snap cured” (60 s, 200° C.) on a hot plate or oven cured (4 h/75° C.) and characterized by dynamic mechanical analysis (DMA). Results are summarized in Table 4.
- DMA dynamic mechanical analysis
- the materials exhibited moduli below T g typical of a low stress adhesive.
- the materials' moduli at temperatures above T g are sufficient to withstand typical wirebonding conditions without failure.
Abstract
A thermoplastic or thermosetting adhesive for bonding an electronic component to a substrate in which the adhesive is cured in situ from a curable composition comprises one or more poly- or mono-functional maleimide compounds, or one or more poly- or mono-functional vinyl compounds other than maleimide compounds, or a combination of maleimide and vinyl compounds, a curing initiator and optionally, one or more fillers.
Description
- The priority of provisional application 60/091,492, filed Jul. 20, 1998, is claimed under 35 USC 119 (e).
- This invention relates to compositions that are suitable for use as adhesives in microelectronic devices or semiconductor packages.
- Adhesive compositions, particularly conductive adhesives, are used for a variety of purposes in the fabrication and assembly of semiconductor packages and microelectronic devices. The more prominent uses are the bonding of integrated circuit chips to lead frames or other substrates, and the bonding of circuit packages or assemblies to printed wire boards.
- The requirements for conductive adhesives in electronic packaging are that they have good mechanical strength, curing properties that do not affect the component or the carrier, and thixotropic properties compatible with existing application equipment currently used in the industry.
- Another important aspect of an adhesive bonding or interconnection technology is the ability to rework the bond. For single chip packaging involving high volume commodity products, a failed chip can be discarded without significant loss. However, it becomes expensive to discard multi-chip packages with only one failed chip; consequently, the ability to rework the failed chip would be a manufacturing advantage. Today, one of the primary thrusts within the semiconductor industry is to develop adhesives that will meet all the requirements for adhesive strength and flexibility, but that will also be reworkable, that is, will be capable of being removed without destroying the substrate.
- This invention is an adhesive composition for use in electronic devices that comprises one or more mono- or polyfunctional maleimide compounds, or one or more mono- or polyfunctional vinyl compounds other than maleimide compounds, or a combination of maleimide and vinyl compounds, a curing initiator, and optionally, one or more fillers. The composition can be designed to be reworkable.
- In another embodiment, this invention is the cured adhesive that results from the just described curable adhesive composition.
- In another embodiment, this invention is a microelectronic assembly comprising an electronic component bonded to a substrate with a cured adhesive composition prepared from a composition comprising one or more mono- or polyfunctional maleimide compounds, or one or more mono- or polyfunctional vinyl compounds, or a combination of maleimide and vinyl compounds, a curing initiator, and optionally one or more fillers.
- The maleimide and vinyl compounds used in the adhesive compositions of this invention are curable compounds, meaning that they are capable of polymerization, with or without crosslinking. As used in this specification, to cure will mean to polymerize, with or without crosslinking. Cross-linking, as is understood in the art, is the attachment of two polymer chains by bridges of an element, a molecular group, or a compound, and in general will take place upon heating. As cross-linking density is increased, the properties of a material can be changed from thermoplastic to thermosetting.
- It is possible to prepare polymers of a wide range of cross-link density by the judicious choice and amount of mono- or polyfunctional compounds. The greater proportion of polyfunctional compounds reacted, the greater the cross-link density. If thermoplastic properties are desired, the adhesive compositions can be prepared from mono-functional compounds to limit the cross-link density. A minor amount of poly-functional compounds can be added to provide some cross-linking and strength to the composition, provided the amount of poly-functional compounds is limited to an amount that does not diminish the desired thermoplastic properties. Within these parameters, the strength and elasticity of individual adhesives can be tailored to a particular end-use application.
- In those cases where it is necessary to rework the assembly and thermoplastic materials are used, the electronic component can be pried off the substrate, and any residue adhesive can be heated until it softens and is easily removed.
- The cross-link density can also be controlled to give a wide range of glass transition temperatures in the cured adhesive to withstand subsequent processing and operation temperatures.
- In the inventive adhesive compositions, the maleimide compounds and the vinyl compounds may be used independently, or in combination. The maleimide or vinyl compounds, or both, will be present in the curable package adhesive compositions in an amount from 2 to 98 weight percent based on the organic components present (excluding any fillers).
- The adhesive compositions will further comprise at least one free-radical initiator, which is defined to be a chemical species that decomposes to a molecular fragment having one or more unpaired electrons, highly reactive and usually short-lived, which is capable of initiating a chemical reaction by means of a chain mechanism. The free-radical initiator will be present in an amount of 0.1 to 10 percent, preferably 0.1 to 3.0 percent, by weight of the organic compounds (excluding any filler). The free radical curing mechanism gives a fast cure and provides the composition with a long shelf life before cure. Preferred free-radical 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-butanenitrile).
- Alternatively, the adhesive compositions may contain a photoinitiator in lieu of the free-radical initiator, and the curing process may then be initiated by UV radiation. The photoinitiator will be present in an amount of 0.1 to 10 percent, preferably 1 to 5.0 percent, by weight of the organic compounds (excluding any filler). In some cases, both photoinitiation and thermal initiation may be desirable. For example, the curing process can be started by UV irradiation, and in a later processing step, curing can be completed by the application of heat to accomplish a free-radical cure.
- In general, these compositions will cure within a temperature range of 80-200° C., and curing will be effected within a length of time of less than 1 minute to 60 minutes. As will be understood, the time and temperature curing profile for each adhesive composition will vary, and different compositions can be designed to provide the curing profile that will be suited to the particular industrial manufacturing process.
- Suitable conductive fillers for the adhesives are silver, copper, gold, palladium, platinum. In some circumstances, nonconductive fillers may be needed, for example to adjust rheology, such as, alumina, silica, and teflon.
- As used throughout this specification, the notation C(O) refers to a carbonyl group.
- The maleimide compounds suitable for use in the adhesive compositions of this invention have a structure represented by the formula: [M−Xm]n−Q, or by the formula: [M−Zm]n—K. For these specific formulae, when lower case “n” is the integer 1, the compound will be a mono-functional compound; and when lower case “n” is an integer 2 to 6, the compound will be a poly-functional compound.
- [M−Xm]n−Q, or by the formula: [M−Zm]n−K.
- Formula [M−Xm]n−Q represents those compounds in which:
-
- in which R1 is H or C1 to C5 alkyl;
-
- Q is a linear or branched chain alkyl, alkyloxy, alkylene, alkyleneoxy, aryl, or aryloxy alkyl amine, alkyl sulfide, alkylene amine, alkylene sulfide, aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the backbone in the chain, and in which any heteroatom present may or may not be directly attached to X;
-
- in which each R2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms; R3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; X is O, S, N, or P; and v is 0 to 50;
-
- in which R3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents;
- or Q is a siloxane having the structure: —(CR1 2)e—[SiR4—O]f—SiR4 2—(CR1 2)0— in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms and the R4 substituent independently for each position is H, an alkyl group having 1 to 5 carbon atoms or an aryl group, and e and g are independently 1 to 10 and f is 1 to 50; and
- m is 0 or 1, and n is 1 to 6.
-
- Formula [M−Zm]n″K represents those compounds in which
-
- in which R1 is H or C1 to C5 alkyl;
- Z is a linear or branched chain alkyl, alkyloxy, alkyl amine, alkyl sulfide, alkylene, alkyleneoxy, alkylene amine, alkylene sulfide, aryl, aryloxy, or aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the backbone in the chain, and in which any heteroatom present may or may not be directly attached to K;
-
- in which each R2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms, and R3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents, and v is 0 to 50;
- or Z is a siloxane having the structure: —(CR1 2)e—[SiR4 2—O]f—SiR4 2—(CR1 2)g— in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms and the R4 substituent independently for each position is H, an alkyl group having 1 to 5 carbon atoms or an aryl group, and e and g are independently 1 to 10 and f is 1 to 50;
-
-
- and m is 0 or 1, and n is 1 to 6.
- Preferred maleimide compounds, particularly for reworkable compositions, are N-butyphenyl malemide and N-ethylpenyl maleimide.
-
- For these specific structures, when lower case “n” is the integer 1, the compound will be a mono-functional compound; and when lower case “n” is an integer 2 to 6, the compound will be a poly-functional compound.
- In these structures, R1 and R2 are H or an alkyl having 1 to 5 carbon atoms, or together form a 5 to 9 membered ring with the carbons forming the vinyl group; B is C, S, N, O, C(O), O—C(O), C(O)—O, C(O)NH or C(O)N(R8), in which R8 is C1 to C5 alkyl; m is 0 or 1; n is 1-6; and X, Q, Z, and K are as described above.
- Preferably, B is O, C(O), C(O)—O, C(O)NH or C(O)N(R8); more preferably B is O, C(O), O—C(O), C(O)—O, or C(O)N(R8).
-
- Depending on the nature of the substrate to which the adhesive is to be bonded, the adhesive may also contain a coupling agent. A coupling agent as used herein is a chemical species containing a polymerizable functional group for reaction with the maleimide and other vinyl compound, and a functional group capable of condensing with metal hydroxides present on the surface of the substrate. Such coupling agents and the preferred amounts for use in compositions for particular substrates are known in the art. Suitable coupling agents are silanes, silicate esters, metal acrylates or methacrylates, titanates, and compounds containing a chelating ligand, such as phosphine, mercaptan, and acetoacetate. When present, coupling agents typically will be in amounts up to 10 percent by weight, and preferably in amounts of 0.1-3.0 percent by weight, of the maleimide and other monofunctional vinyl compound.
- In addition, the adhesive compositions may contain compounds that lend additional flexibility and toughness to the resultant cured adhesive. Such compounds may be any thermoset or thermoplastic material having a Tg of 50° C. or less, and typically will be a polymeric material characterized by free rotation about the chemical bonds, the presence of ether groups, and the absence of ring structures. Suitable such modifiers include polyacrylates, poly(butadiene), polyTHF ( polymerized tetrahydrofuran), CTBN (carboxy-terminated butadiene-acrylonitrile) rubber, and polypropylene glycol. When present, toughening compounds may be in an amount up to about 15 percent by weight of the maleimide and other monofunctional vinyl compound.
- If siloxane moieties are not part of the maleimide or vinyl compound structure, siloxanes can be added to the package formulations to impart elastomeric properties. Suitable siloxanes are the methacryloxypropyl-terminated polydimethyl siloxanes, and the aminopropyl-terminated polydimethylsiloxanes, available from United Chemical Technologies and others.
- Other additives, such as adhesion promoters, in types and amounts known in the art, may also be added.
- These compositions will perform within the commercially acceptable range for die attach adhesives. Commercially acceptable values for die shear for the adhesives on a 80×80 mil2 silicon die are in the range of greater than or equal to 1 kg at room temperature, and greater than or equal to 0.5 kg at 240° C., and for warpage for a 500×500 mil2 die are in the range of less than or equal to 70 μm at room temperature.
- The coefficient of thermal expansion (CTE) is the change in dimension per unit change in temperature for a given material. Different materials will have different rates of expansion. If the CTE is very different for elements attached together, thermal cycling can cause the attached elements to bend, crack, or delaminate. In a typical semiconductor assembly, the CTE of the chip is in the range of 2 or 3 ppm/° C.; for organic circuit board substrate, the CTE is greater than 30 ppm/° C.; therefore, the CTE of the adhesive is best between that of the substrate and die.
- When a polymer is subjected to the application of heat, it will move through a transition region between a hard, glassy state to a soft, rubbery state. This region is known as the glass transition region or Tg. If a graph of expansion of the polymer versus temperature is plotted, the glass transition region is the intersection between the lower temperature/glassy region coefficient of thermal expansion and the higher temperature/rubbery region coefficient of thermal expansion. Above this region, the rate of expansion increases significantly. Consequently, it is preferred that the glass transition of the polymer be higher than normal operating temperatures experienced during the application, and if reworkability is needed, that the glass transition be lower than any rework temperature.
-
- in which p is 1 to 100,
- each R3 can independently be an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents, or
- a siloxane having the structure —(CR1 2)e—[SiR4 2—O]f—SiR4 2—(CR1 2—)g in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10 and f is 1 to 50.
-
- as described herein in which B is C, S, N, O, C(O), C(O)NH or C(O)N(R8), in which R8 is C1 to C5 alkyl.
-
-
- in which p is 1 to 100,
- each R3 can independently be an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents,
- or a siloxane having the structure
- —(CR1 2)e—[SiR4 2—O]f—SiR4 2—(CR1 2)g— in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50.
- Another embodiment of this invention includes the curable adhesive composition as described herein containing an anionic or cationic curing initiator. The types and useful amounts of such initiators are well known in the art.
- Various maleimide and vinyl compounds were prepared and formulated into adhesive compositions. The compositions were investigated for viscosity and thixotropic index for the uncured composition, and for curing profile, glass transition temperature, coefficient of thermal expansion, thermal mechanical analysis, and in some cases reworkability for the cured composition.
-
- Amino-terminated butadiene-acrylonitrile (sold as Hycar resin 1300 X42 ATBN by BF Goodrich, in which the m and n depicted in the structure are integers to provide a number average molecular weight of 3600) (450 g, 500 mmol based on amine equivalent weight AEW=450 g) was dissolved in CHCl3 (1000 mL) in a 3 L four-necked flask equipped with addition funnel, mechanical stirrer, internal temperature probe and nitrogen inlet/outlet. The stirred solution was placed under nitrogen and cooled on an ice bath. The addition funnel was charged with maleic anhydride (98.1 g, 1 mol) in CHCl3 (50 mL) and this solution was added to the reaction over 30 minutes, maintaining the internal reaction temperature below 10° C. This mixture was stirred for 30 minutes on ice, then allowed to warm to room temperature and stirred for an additional 4 hours. To the resulting slurry was added acetic anhydride (Ac2O) (653.4 g, 6 mol), triethylamine (Et3N) (64.8 g, 0.64 mol) and sodium acetate (NaOAc) (62.3 g, 0.76 mol). The reaction was heated to mild reflux for 5 hours, allowed to cool to room temperature, and subsequently extracted with H2O (1 L), satd. NaHCO3 (1 L) and H2O (2×1 L). Solvent was removed in vacuo to yield the maleimide terminated butadiene acrylonitrile.
-
- Tris(epoxypropyl)isocyanurate (99.0 g, 0.33 mol) is dissolved in THF (500 mL) in a 2 L three-necked flask equipped with mechanical stirrer, internal temperature probe and nitrogen inlet/outlet. To this solution is added hyroxyphenylmaleimide (189.2 g, 1 mol) and benzyldimethylamine (1.4 g, 0.05 wt. %). The solution is heated to 80° C. for 7 hours. The reaction then is allowed to cool to room temperature, is filtered, and the filtrant washed with 5% HClaq (500 mL) and distilled H2O (1 L). The resulting solid, triazinetris(maleimide), is vacuum dried at room temperature.
-
- Palmitoyl chloride (274.9 g, 1 mol) is dissolved in Et2O (500 mL) in a 2 L three-necked flask equipped with mechanical stirrer, internal temperature probe, addition funnel and nitrogen inlet/outlet. NaHCO3 (84.0 g, 1 mol) in distilled H2O (500 mL) is added with vigorous stirring and the solution cooled on an ice bath under nitrogen. The addition funnel is charged with hydroxyethylmaleimide (141 g, 1 mol) in Et2O (100 mL) and this solution added to the reaction over a period of 30 minutes, maintaining an internal T<10° C. during the addition. The reaction is stirred for another 30 minutes on ice, then allowed to warm to room temperature and stirred for 4 hours. The reaction is transferred to a separatory funnel and the isolated organic layer washed with distilled H2O (500 mL), 5% HClaq (500 mL) and distilled H2O (2×500 mL). The organics are isolated, dried over MgSO4 anhyd., filtered and solvent removed in vacuo to yield the aliphatic maleimide.
-
- 5-Isocyanato-1-(isocyanatomethyl )-1, 3, 3-trimethylcyclohexane 111.15 g, 0.5 mol) is solvated in THF (500 mL) in a 1 L three-necked flask equipped with mechanical stirrer, addition funnel and nitrogen inlet/outlet. The reaction is placed under nitrogen, and dibutyltin dilaurate (cat. SnII) (6.31 g, 10 mmol) and hydroxyethylmaleimide (141 g, 1 mol) are added with stirring, and the resulting mixture heated for four hours at 70° C. The addition funnel is charged with hydroxyethylmaleimide (141 g, 1 mol) dissolved in THF (100 mL). This solution is added to the isocyanate solution over 30 minutes, and the resulting mixture heated for an additional 4 hours at 70° C. The reaction is allowed to cool to room temperature and solvent removed in vacuo. The remaining oil is dissolved in CH2Cl2 (1 L) and washed with 10% HClaq (1 L) and distilled H2O (2×1 L). The isolated organics are dried over MgSO4, filtered and the solvent removed in vacuo to yield the maleimide.
-
- Bis(1, 10-phenanthroline)Pd(OAc)2 (0.21 g, 0.54 mmol) was dissolved in a mixture of butyl vinyl ether (8.18 g, 81.7 mmols), heptane (100 mL) and “dimer diol” (sold as Pripol 2033 by Unichema, 15.4 g, 27.2 mmol) in 2 L three-necked flask equipped with a mechanical stirrer under nitrogen. This solution was heated to light reflux for 6 h. The solution was allowed to cool to room temperature and subsequently poured onto activated carbon (20 g) and stirred for 1 hour. The resulting slurry was filtered, and excess butyl vinyl ether and heptane were removed in vacuo to yield the divinyl ether as a yellow oil. The product exhibited acceptable 1H NMR, FT-IR and 13C NMR spectral characteristics. Typical viscosity ˜100 cPs.
-
- A dimer diol (sold as Pripol 2033 by Unichema, 284.4 g, 500 mmol) is dissolved in dry acetone (500 mL) in a 1 L three-necked flask equipped with mechanical stirrer, addition funnel and internal temperature probe under nitrogen. Triethylamine (101.2 g, 1 mol) is added to this solution and the solution cooled to 4° C. on an ice bath. Acryloyl chloride (90.5 g, 1 mol) solvated in dry acetone (100 mL) is charged into the addition funnel and added to the stirred reaction solution over the course of 60 minutes, maintaining an internal temperature <10° C. This solution is stirred on ice for an additional 2 hours, then allowed to warm to room temperature and stirred for 4 hours. Bulk solvent is removed via a rotary evaporator, and the remaining residue solvated in CH2Cl2 (1 L). This solution is washed with 5% HClaq (800 mL), and H2O (2×800mL). The isolated organics are dried over MgSO4 anhyd. and filtered, and the solvent removed in vacuo to yield the diacrylate as an oil.
- 4-Ethyl aniline (12.12 g) was dissolved in 50 ml of anhydrous ethyl ether and slowly added to a stirred solution of 9.81 g of maleic anhydride in 100 ml of anhydrous ethyl ether chilled in an ice bath. After completion of the addition, the reaction mixture was stirred for 30 minutes. The light yellow crystals were filtered and dried. Acetic anhydride (200 ml) was used to dissolve the maleamic acid and 20 g of sodium acetate. The reaction mixture was heated in an oil bath at 1 60° C. After 3 hours of reflux, the solution was cooled to room temperature, placed in a 1 L beaker in ice water and stirred vigorously for 1 hour. The product was suction-filtered and recrystallized in hexane. The collected crystalline material was dried at 50° C. in a vacuum oven overnight. FTIR and NMR analysis showed the characteristics of ethyl maleimide.
-
- Dimer acid (sold under the trademark Empol 1024 by Unichema) (574.6 g, 1 mol) and propargyl alcohol (112.1 g, 2 mol) are solvated in toluene (1 L) in a 3 L three-necked flask equipped with mechanical stirring and a Dean-Stark distillation apparatus. Concentrated H2SO4 (6 mL) is added and the solution refluxed for 6 hours until 36 mL of H2O is azeotropically distilled. The solution is allowed to cool to room temperature, is washed with H2O (2×1L), dried over MgSO4 anhyd, and the solvent removed in vacuo to yield the propargyl ester intermediate as an oil.
- This ester intermediate (650.7 g, 1 mol) is solvated in THF (200 mL) in a 1 L three-necked flask equipped with reflux condensor, mechanical stirrer and internal temperature probe under nitrogen. Lauryl mercaptan (404.8 g, 2 mol) and 2,2′-azobis(2,4-dimethylpentanenitrile) (sold under the trademark Vazo 52 by DuPont) (11 g) are added and the resulting mixture heated to 70° C. on an oil bath with stirring for 7 hours. The reaction is allowed to cool to room temperature and solvent removed in vacuo to yield the alkenyl sulfide as an oil.
-
- The acid functional maleimide, 6-maleimidocaproic acid, was synthesized using known methodology.1 Aminocaproic acid (100 g, 7.6×10−1 mols) was dissolved in glacial acetic acid (50 mL) in a 500 mL four-necked flask equipped with mechanical stirring, an internal temperature probe and an addition funnel. The addition funnel was charged with a solution of maleic anhydride (74.8 g, 7.6×10−1 mols) dissolved in acetonitrile (75 mL). This solution was added to the aminocaproic acid at room temperature dropwise over 1 hour, maintaining an internal reaction temperature less than 35° C. The reaction was stirred for three hours after the addition was complete. The reaction slurry was filtered, and the isolated filtrate was dried in a vacuum oven (P˜25 T) overnight at 70° C. to yield 166 g of off white solid (95%). The product amic acid exhibited FT-IR and 1H NMR spectral characteristics consistent with literature data.
- The amic acid described above (166 g, 7.2×10−1 mols) was solvated in a solution of toluene (200 mL), benzene (200 mL) and triethylamine (211 mL, 1.51 mol) in a 1 L three-necked flask equipped with mechanical stirring and a Dean-Stark trap under nitrogen. This solution was heated to reflux for 4 h and the water produced collected in the Dean-Stark trap. Distilled water (400 mL) was added to the reaction flask to dissolve the triethylammonium salt of the product which largely separated from the bulk solution during the reaction. This aqueous layer was isolated, acidified to pH˜1 with 50% HCl, and extracted with ethyl acetate (600 mL). This organic layer was washed with distilled water (400 mL). The isolated organic layer was dried over MgSO4, followed by solvent removal in vacuo to yield an off white solid (76.2 g, 50%). The product 6-maleimidocaproic acid was spectrographically identical to literature material by FT-IR and 1H NMR.
-
- Pripol 2033 (“dimer diol”, Uniqema, 92.4 g, 1.69×10−1 mols), 6-maleimidocaproic acid (75.0 g, 3.55×10−1 mols) and H2SO4 (0.50 mL, ˜8.5×10−3 mols) were slurried in toluene (300 mL) in a 1 L four-necked flask equipped with mechanical stirrer, a Dean-Stark trap and an internal temperature probe under nitrogen. The reaction was heated to light reflux for two hours and the water evolved collected in the Dean-Stark trap. The trap was drained and ˜50 mL of toluene solvent was distilled off of the reaction to remove trace moisture and drive the esterification equilibrium to completion. The reaction was allowed to cool to room temperature, additional toluene (100 mL) was added (on the laboratory scale it is preferable to add diethyl ether in place of toluene at this point), and the solution was washed with saturated NaHCO3 aq. (300 mL) and distilled water (300 mL). The organic layer was isolated and dried over anhydrous MgSO4, and the solvent removed in vacuo to yield an orange oil (107.2 g, 68%). The material can be further purified by eluting a toluene solution of the resin through a short plug of silica or alumina. This liquid bismaleimide resin exhibited acceptable FT-IR, 1H NMR, and 13C NMR data. Typical η˜2500 cPs.
-
- The general procedure described in Example B. was applied substituting decane diol (29.5 g, 1.69×10−1 mols) for Pripol 2033. This process yielded a solid, moderately soluble bismaleimide (54.9 g, 58%). The product exhibited satisfactory FT-IR and 1H NMR data.
-
- The protocol outlined in example B. was utilized substituting glycerol (10.4 g, 1.13×10−1 mol) for Pripol 2033. The product was a viscous liquid which exhibited acceptable FT-IR and 1H NMR data.
-
- Isophorone diisocyanate (“IPDI”, 100.0 g, 4.5×10−1 mols), m-nitrobenzyl alcohol (137.8 g, 9.0×10−1 mols) and dibutyl tin dilaurate (2.8 g, 4.5×10−3 mols) were solvated in dry toluene (1500 mL) in a 2 L three-necked flask equipped with mechanical stirrer, reflux condensor and internal temperature probe under nitrogen. The resulting solution was heated to 90° C. for 4 h. No isocyanate band was observed in the IR of the solids portion of the sample. The solution was allowed to cool to room temperature and washed with distilled H2O (100 mL). The organic layer was isolated and solvent removed in vacuo to yield a yellow liquid which exhibited acceptable FT-IR and 1H NMR characteristics.
-
- The dinitro compound from Example E. (8.28 g, 1.57×10−2 mols) was dissolved in ethanol (100 mL) in a 500 mL three-necked round bottom flask equipped with magnetic stirring under nitrogen. Cyclohexene (28.6 mL, 2.82×10−1 mols) was added, followed by 5% Pd/C (4.14 g). The resulting slurry was refluxed lightly for 6.5 h. The FT-IR of a filtered aliquot of this solution exhibited no nitro stretching bands at 1529 cm−1 and 1352 cm−1. The bulk solution was allowed to cool to room temperature and filtered. Solvent was removed in vacuo to yield a yellow semisolid (6.6 g, 90%) which exhibited acceptable FT-IR and 1H NMR spectral characteristics.
-
- The diamine from Example F (6.6 g, 1.41×1−2 mols) was solvated in acetone (60 mL) in a 250 mL four-necked flask equipped with magnetic stirrer and addition funnel under nitrogen and cooled to 4° C. Maleic anhydride (2.76 g, 2.82×10−2 mols) dissloved in acetone (20 mL) was added over the course of 30 minutes. The resulting solution was stirred at 4° C. for for 1 h, and subsequently was allowed to warm to room temperature and stirred overnight. FT-IR analysis indicated no maleic anhydride remained as judged by the absence of the anhydride stretching band at ˜1810 cm−1.
- To the above amic acid solution was added acetic anhydride (8.5 mL, 9.0×10−2 mols), triethylamine (1.26 mL, 9.0×10−3 mols) and sodium acetate (0.88 g, 1.1×10−2 mols). The resulting solution was refluxed lightly for 4 h under nitrogen. The reaction was allowed to cool to room temperature and bulk solvent was removed in vacuo. The resulting viscous liquid was resolvated in methylene chloride (200 mL) and extracted with distilled water (3×200 mL). The organics were then dried over MgSO4 anhyd., filtered and solvent removed in vacuo to yield a light brown solid (6.75 g, 76%). This material exhibited acceptable FT-IR and 1H NMR spectral features.
-
- DDI 1410 (Henkel, “Dimer Diisocyanate”, 99.77 g, 1.65×10−1 mols based on 13.96% NCO), m-nitrobenzyl alcohol (50.8 g, 3.32×10−1 mols) and dibutyltin dilaurate (0.5 mL, 8.3×10−4 mols) were solvated in toluene (150 mL) in a 1 L four-necked flask equipped with mechanical stirrer, reflux condenser and internal temperature probe under nitrogen. The reaction was heated to 85° C. for 2.5 h. FT-IR analysis of an aliquot of the reaction indicated complete comsumption of isocyanate functionality as judged by the lack of a band at 2272 cm−1. Solvent was removed from the reaction in vacuo to yield a yellow oil which solidified upon standing at room temperature (152.4 g, 102% (trace toluene)). This solid exhibited satisfactory FT-IR and 1H NMR spectral features.
-
- The diamine product of Example H (39.6 g, 4.32×10−2 mols) and stannous chloride dihydrate (97.55 g, 4.32×10−1 mols) were slurried in ethyl acetate (300 mL) in a 1 L three-necked flask equipped with mechanical stirrer and a reflux condensor under nitrogen. The reaction was heated to light reflux and stirred vigorously for 3 h. The solution was allowed to cool to room temperature and brought to pH 7-8 with a solution of saturated sodium bicarbonate. The mixture was pushed through a 25 micron filter to yield a mixture which separated into a cloudy aqueous layer and a moderately clear organic layer. The aqueous layer was isolated and washed with ethyl acetate (100 mL). The organic layers were combined, washed with distilled water (300 mL) and dried over anhydrous MgSO4. The slurry was filtered and solvent removed from the filtrate in vacuo to yield yellow, sticky solid (33.8 g, 92%).
-
- Maleic anhydride (15.4 g, 1.57×10−2 mols) was dissolved in acetone (300 mL) in a 2 L four-necked flask equipped with mechanical stirrer, internal temperature probe and addition funnel under nitrogen. This solution was cooled to ˜4° C. on an ice bath. A solution of the diamine prepared in Example I (63.4 g, 7.48×10−2 mols) in acetone (70 mL) was charged to the addition funnel and added to the maleic anhydride solution over a period of 30 minutes maintaining an internal temperature of <10° C. The resulting solution was stirred for 1 h and subsequently allowed to warm to room temperature and stir for 2 h.
- To this solution of amic acid was added acetic anhydride (24.7 mL, 2.62×10−1 mols), triethylamine (6.25 mL, 4.48×10−2 mols) and manganese acetate tetrahydrate (0.37 g, 1.50×10−3 mols). This solution was heated to light reflux for 6.5 h, then allowed to cool to room temperature. Bulk solvent was removed in vacuo, and the resulting dark liquid was dissolved in diethyl ether (500 mL). This solution was washed with dist. H2O (500 mL). The isolated organic layer was then washed with saturated NaHCO3 aq. (500 mL) and again with dist. H2O (500 mL). The organics were isolated, dried over anhyd. MgSO4, and solvent removed in vacuo to yield a viscous orange oil. This material exhibited FT-IR, 1H NMR and 13C NMR spectral features consistent with the expected bismaleimide product.
- A silver filled die attach adhesive formulation having a viscosity of 9011 cPs (5 rpm, cone and plate) and thixotropic index of 5.36 was produced by combining the following at room temperature using a mechanical mixer:
Liquid bismaleimide of Example B: 2.644 g Dimer divinyl ether of Example 5: 2.644 g Ricon 131MA20 (Ricon Resins, Inc.): 0.661 g Silquest A-174 (Witco Corp.): 0.040 g USP-90MD (Witco Corp.): 0.099 XD0026 (NSCC trade secret): 0.119 SF-96 silver flake 23.794 - The resulting paste was dispensed onto various metal leadframes as detailed below, and 120×120 mil silicon die were placed onto the adhesive bead to produce an approximately 1 mil bondline. Samples were “snap cured” at 200° C. for 60 seconds, and die shear strengths at room temperature and 240° C. were measured. These samples were then subjected to elevated temperature and humidity (85° C./85% RH) for 48 hours. Die shear strengths were then again measured at room temperature and 240° C. Results are tabulated in Table 1.
TABLE 1 Die Shear Strengths (DSS) of Maleimide/Vinyl Ether Die Attach Adhesive After Moisture Exposure No Moisture Exposure (48 h/85° C./85 RH) Cure Profile 60 s/200° C. 60 s/200° C. Test 25° C. 240° C. 25° C. 240° C. Temperature Cu leadframe 4.88+/− 1.46+/− 6.54+/−0.82 1.84+/−0.76 DSS (kg) 0.25 0.35 Ag-Cu 5.29+/− 2.17+/− 9.50+/−1.88 1.56+/−0.72 leadframe 0.34 0.43 DSS (kg) Pd-Cu 5.52+/− 1.99+/− 11.9+/−1.3 3.53+/−0.66 DSS (kg) 0.39 0.44 - Similarly to Example AA, 120×120 mil die were attached to leadframes of various compositions utilizing the adhesive composition given in Example AA. The bonded die were then cured using “snap cure” (60 s/200° C.) and “fast oven cure” conditions (15 min./175° C.). The resulting cured devices were subjected to simulated HAST testing conditions (130° C., 85% RH) for 130 hours. The devices exhibited good adhesion as measured by die shear strength (DSS) at both room temperature and elevated temperature as shown in Table 2.
TABLE 2 Die Shear Strengths after simulated HAST Testing Cure Profile 60 s/200° C. 15 minutes/175° C. Test 25° C. 240° C. 25° C. 240° C. Temperature Cu leadframe 15.3+/− 1.12+/−0.35 17.2+/− 1.25+/−0.39 DSS (kg) 1.8 Ag—Cu 16.3+/− 2.81+/−0.55 14.8+/− 2.6+/−1.6 leadframe 1.9 1.8 DSS (kg) Pd—Cu 15.7+/ 3.04+/−0.46 14.4+/− 2.96+/−0.90 DSS (kg) 1.7 0.7 - The die attach composition described in Example AA. was used to bond 500×500 mil die to Pd-Cu leadframes. The assembled pieces were “snap cured” and measured for die warpage at several temperatures and times. Typical results are given in Table 3. The performance exhibited by this adhesive qualifies it as a “low stress” material.
TABLE 3 Warpage of Maleimide/Vinyl Ether Die Attach Adhesive on 500 × 500 mil Die Thermal History 1 min/200° C. +1 min/240° C. +4 h/175° C. Warpage (μm) 10.4+/−1.3 11.9+/−1.4 14.1+/−1.6 - The composition of Example AA. was used to produce ˜1 mil films using a drawdown bar. The films were “snap cured” (60 s, 200° C.) on a hot plate or oven cured (4 h/75° C.) and characterized by dynamic mechanical analysis (DMA). Results are summarized in Table 4.
TABLE 4 Thermal Analysis of Maleimide/Vinyl Ether Die Attach Films Cure Profile 60 s/200° C. 4 h/175° C. Tg (° C.) −1 35 Modulus (E′) at −65° C. (psi) 421,300 513,900 Modulus (E′) at 100° C. (psi) 5,864 23,980 - The materials exhibited moduli below Tg typical of a low stress adhesive. The materials' moduli at temperatures above Tg are sufficient to withstand typical wirebonding conditions without failure.
Claims (37)
1. A curable adhesive composition for use in bonding an electronic component to a substrate comprising a maleimide compound and a curing initiator selected from the group consisting of a free-radical initiator, a photoinitiator, and a combination of those, the maleimide compound having the formula [M−Xm]n−Q in which m is 0 or 1 and n is 1 to 6, and
(a) M is a maleimide moiety having the structure:
in which R1is H or an alkyl group having 1 to 5 carbon atoms;
(b) X is an aromatic group selected from the group of aromatic groups having the structures:
and
(c) Q is a linear or branched chain alkyl, alkyloxy, alkyl amine, alkyl sulfide, alkylene, alkyleneoxy, alkylene amine, alkylene sulfide, aryl, aryloxy, or aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain, and in which any heteratom present may or may not be directly attached to X.
2. The curable adhesive composition according to claim 1 in which Q is a linear or branched chain alkyl, alkyloxy, alkylene, or alkyleneoxy species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain.
3. The curable adhesive composition according to claim 2 in which Q is a linear or branched chain alkyl species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain.
4. The curable adhesive composition according to claim 1 in which Q is a urethane having the structure:
in which each R2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms; R3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; X is O, S, N, or P; and v is 0 to 50.
6. The curable adhesive composition according to claim 1 in which Q is an ester having the structure:
in which
p is 1 to 100, and
each R3 can independently be an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; or
each R3 can independently be a siloxane having the structure—(CR1 2)e—[SiR4 2—O]f—SiR4 2—(CR1 2)g— in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50.
7. The curable adhesive composition according to claim 1 in which Q is an ester having the structure:
in which
p is 1 to 100, and
each R3 can independently be an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; or
each R3 can independently be a siloxane having the structure—(CR1 2)e—[SiR4 2—O]f—SiR4 2—(CR1 2)g— in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50.
8. A curable adhesive composition comprising a maleimide compound and a curing initiator selected from the group consisting of a free-radical initiator, a photoinitiator, and a combination of those, the maleimide compound having the formula [M−Zm]n−K in which m is 0 or 1 and n is 1-6, and
(a) M is a maleimide moiety having the structure
in which R1 is H or an alkyl having 1 to 5 carbon atoms;
(b) K is an aromatic group selected from group of aromatic groups having the structures:
in which p is 1 to 100;
in which p is 1 to 100;
in which R5, R6, and R7 are a linear or branched chain alkyl, alkyloxy, alkyl amine, alkyl sulfide, alkylene, alkyleneoxy, alkylene amine, alkylene sulfide, aryl, aryloxy, or aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the backbone in the chain, and in which any heteratom present may or may not be directly attached to the aromatic ring;
or R5, R6, and R7 are a siloxane having the structure —(CR1 2)e—[SiR4 2—O]f—SiR4 2—(CH3)g— in which the R1 substituent is H or an alkyl group having 1 to 5 carbon atoms and the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, and e is 1 to 10 and f is 1 to 50;
and
(c) Z is a linear or branched chain alkyl, alkyloxy, alkyl amine, alkyl sulfide, alkylene, alkyleneoxy, alkylene amine, alkylene sulfide, aryl, aryloxy, or aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain, and in which any heteratom present may or may not be directly attached to K.
9. The curable adhesive composition according to claim 8 in which Z is a linear or branched chain alkyl, alkyloxy, alkylene, or alkyleneoxy species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain.
10. The curable adhesive composition according to claim 8 in which Z is a linear or branched chain alkyl species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain.
11. The curable adhesive composition according to claim 8 in which Z is a urethane having the structure:
in which each R2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms; R3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; X is O, S, N, or P; and v is 0 to 50.
13. The curable adhesive composition according to claim 8 in which Z is an ester having the structure:
in which
p is 1 to 100, and
each R3 can independently be an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; or
each R3 can independently be a siloxane having the structure—(CR1 2)e—[SiR4 2—O]f—SiR4 2—(CR1 2)g—in which the R1substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50.
14. The curable adhesive composition according to claim 8 in which Z is an ester having the structure:
in which
p is 1 to 100, and
each R3 can independently be an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; or
each R3 can independently be a siloxane having the structure—(CR1 2)e—[SiR4 2—O]f—SiR4 2—(CR1 2)g—in which the R1substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50.
16. The curable adhesive composition according to any one of claims 8 to 14 in which K is
in which R5, R6, and R7 are a linear or branched chain alkyl, alkyloxy, alkyl amine, alkyl sulfide, alkylene, alkyleneoxy, alkylene amine, alkylene sulfide, aryl, aryloxy, or aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain, and in which any heteroatom present may or may not be directly attached to the aromatic ring.
18. A curable adhesive composition comprising a vinyl compound and a curing initiator selected from the group consisting of a free-radical initiator, a photoinitiator, and a combination of those, the vinyl compound having the formula
in which m is 0 or 1 and n is 1-6; and
(a) R1 and R2 are H or an alkyl group having 1 to 5 carbon atoms, or together form a 5 to 9 membered ring with the carbons forming the vinyl group;
(b) B is C, S, N, O, C(O), C(O)NH or C(O)N(R8), in which R8 is an alkyl group having 1 to 5 carbon atoms;
(c) X is an aromatic group selected from the group of aromatic groups having the structures:
(d) Q is a linear or branched chain alkyl, alkyloxy, alkyl amine, alkyl sulfide, alkylene, alkyleneoxy, alkylene amine, alkylene sulfide, aryl, aryloxy, or aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain, and in which any heteratom present may or may not be directly attached to X.
19. The curable adhesive composition according to claim 18 in which Q is a linear or branched chain alkyl, alkyloxy, alkylene, or alkyleneoxy species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain.
20. The curable adhesive composition according to claim 19 in which Q is a linear or branched chain alkyl species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain.
21. The curable adhesive composition according to claim 18 in which Q is a urethane having the structure:
in which each R2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms; R3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; X is O, S, N, or P; and v is 0 to 50.
23. The curable adhesive composition according to claim 18 in which Q is an ester having the structure:
in which
p is 1 to 100, and
each R3 can independently be an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; or
each R3 can independently be a siloxane having the structure—(CR1 2)e—[SiR4 2—O]f—SiR4 2—(CR1 2)g—in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50.
24. The curable adhesive composition according to claim 18 in which Q is an ester having the structure:
in which
p is 1 to 100, and
each R3 can independently be an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; or
each R3 can independently be a siloxane having the structure—(CR1 2)e—[SiR4 2—O]f—SiR4 2—(CR1 2)g—in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50.
25. A curable adhesive composition comprising a vinyl compound and a curing initiator selected from the group consisting of a free-radical initiator, a photoinitiator, and a combination of those, the vinyl compound having the formula
in which m is 0 or 1 and n is 1-6; and
(a) R1and R2 are H or an alkyl group having 1 to 5 carbon atoms, or together form a 5 to 9 membered ring with the carbons forming the vinyl group;
(b) B is C, S, N, O, C(O), C(O)NH or C(O)N(R8), in which R8 is an alkyl group having 1 to 5 carbon atoms;
(c) K is an aromatic group selected from the group of aromatic groups having the structures:
in which p is 1 to 100;
in which p is 1 to 100;
in which R5, R6, and R7 are a linear or branched chain alkyl, alkyloxy, alkyl amine, alkyl sulfide, alkylene, alkyleneoxy, alkylene amine, alkylene sulfide, aryl, aryloxy, or aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the backbone in the chain, and in which any heteratom present may or may not be directly attached to the aromatic ring; or
R5, R6, and R7are a siloxane having the structure —(CR1 2)e—[SiR4 2—O]f—SiR4 2—(CH3)g—in which the R1substituent is H or an alkyl group having 1 to 5 carbon atoms and the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, and e is 1 to 10 and f is 1 to 50;
and
(d) Z is a linear or branched chain alkyl, alkyloxy, alkyl amine, alkyl sulfide, alkylene, alkyleneoxy, alkylene amine, alkylene sulfide, aryl, aryloxy, or aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain, and in which any heteratom present may or may not be directly attached to X.
26. The curable adhesive composition according to claim 25 in which Z is a linear or branched chain alkyl, alkyloxy, alkylene, or alkyleneoxy species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain.
27. The curable adhesive composition according to claim 25 in which Z is a linear or branched chain alkyl species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain.
28. The curable adhesive composition according to claim 25 in which Z is a urethane having the structure:
in which each R2 independently is an alkyl, aryl, or arylalkyl group having 1 to 18 carbon atoms; R3 is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; X is O, S, N, or P; and v is 0 to 50.
30. The curable adhesive composition according to claim 25 in which Z is an ester having the structure:
in which
p is 1 to 100, and
each R3 can independently be an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; or
each R3 can independently be a siloxane having the structure—(CR1 2)e—[SiR4 2—O]f—SiR4 2—(CR1 2)g—in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50.
31. The curable adhesive composition according to claim 25 in which Z is an ester having the structure:
in which p is 1 to 100, and
each R3 can independently be an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents; or each R3 can independently be a siloxane having the structure—(CR1 2)e—[SiR42—O]f—SiR4 2—(CR1 2)g—in which the R1 substituent independently for each position is H or an alkyl group having 1 to 5 carbon atoms, the R4 substituent independently for each position is an alkyl group having 1 to 5 carbon atoms or an aryl group, e and g are independently 1 to 10, and f is 1 to 50.
33. The curable adhesive composition according to any one of claims 25 to 31 in which K is
in which R5, R6, and R7 are a linear or branched chain alkyl, alkyloxy, alkyl amine, alkyl sulfide, alkylene, alkyleneoxy, alkylene amine, alkylene sulfide, aryl, aryloxy, or aryl sulfide species, which may contain saturated or unsaturated cyclic or heterocyclic substituents pendant from the chain or as part of the chain, and in which any heteroatom present may or may not be directly attached to the aromatic ring.
35. A curable adhesive composition comprising a maleimide compound as described in any one of claims 1 to 17 and a vinyl compound as described in any one of claims 18 to 34 , and a curing initiator.
36. A curable adhesive composition comprising a maleimide compound as described in any one of claims 1 to 17 , or a vinyl compound as described in any one of claims 18 to 34 , or a combination of a maleimide compound as described in any one of claims 1 to 17 and a vinyl compound as described in any one of claims 18 to 34 , and an anionic or cationic curing initiator.
37. An electronic assembly comprising an electronic component bonded to a substrate with a cured adhesive composition prepared from a composition according to any one of the preceding claims.
Priority Applications (1)
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US09/773,800 US20020007042A1 (en) | 1998-07-02 | 2001-02-01 | Die attach adhesives for use in microelectronic devices |
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US9149298P | 1998-07-02 | 1998-07-02 | |
US09/336,245 US6265530B1 (en) | 1998-07-02 | 1999-06-18 | Die attach adhesives for use in microelectronic devices |
US09/773,800 US20020007042A1 (en) | 1998-07-02 | 2001-02-01 | Die attach adhesives for use in microelectronic devices |
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US09/336,245 Division US6265530B1 (en) | 1998-07-02 | 1999-06-18 | Die attach adhesives for use in microelectronic devices |
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US09/336,245 Expired - Lifetime US6265530B1 (en) | 1998-07-02 | 1999-06-18 | Die attach adhesives for use in microelectronic devices |
US09/773,800 Abandoned US20020007042A1 (en) | 1998-07-02 | 2001-02-01 | Die attach adhesives for use in microelectronic devices |
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EP (1) | EP0969065B1 (en) |
JP (1) | JP2000044888A (en) |
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CN (1) | CN1145682C (en) |
DE (1) | DE69920813T2 (en) |
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- 1999-06-18 US US09/336,245 patent/US6265530B1/en not_active Expired - Lifetime
- 1999-06-25 SG SG1999003553A patent/SG73662A1/en unknown
- 1999-06-30 CN CNB991113950A patent/CN1145682C/en not_active Expired - Fee Related
- 1999-07-01 DE DE69920813T patent/DE69920813T2/en not_active Expired - Lifetime
- 1999-07-01 EP EP99112734A patent/EP0969065B1/en not_active Expired - Lifetime
- 1999-07-02 JP JP11189198A patent/JP2000044888A/en active Pending
- 1999-07-02 KR KR1019990026638A patent/KR100602887B1/en not_active IP Right Cessation
- 1999-12-20 TW TW088111220A patent/TW496891B/en not_active IP Right Cessation
-
2000
- 2000-09-27 HK HK00106149A patent/HK1028904A1/en not_active IP Right Cessation
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2001
- 2001-02-01 US US09/773,800 patent/US20020007042A1/en not_active Abandoned
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US20080160315A1 (en) * | 2002-11-25 | 2008-07-03 | Henkel Corporation | B-stageable die attach adhesives |
US9278909B2 (en) | 2003-05-05 | 2016-03-08 | Designer Molecules, Inc. | Amide-extended crosslinking compounds and methods for use thereof |
EP1736520A1 (en) * | 2004-03-19 | 2006-12-27 | Sumitomo Bakelite Company, Ltd. | Resin composition and semiconductor devices made by using the same |
EP2647686A3 (en) * | 2004-03-19 | 2013-10-30 | Sumitomo Bakelite Co., Ltd. | Resin Composition And Semiconductor Device Produced By Using The Same |
WO2005090510A1 (en) | 2004-03-19 | 2005-09-29 | Sumitomo Bakelite Company, Ltd. | Resin composition and semiconductor devices made by using the same |
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US8378017B2 (en) * | 2005-12-29 | 2013-02-19 | Designer Molecules, Inc. | Thermosetting adhesive compositions |
US20070155869A1 (en) * | 2005-12-29 | 2007-07-05 | Dershem Stephen M | Mono-functional monomers and methods for use thereof |
US7691475B2 (en) | 2006-07-21 | 2010-04-06 | 3M Innovative Properties Company | Anisotropic conductive adhesives |
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US20080020157A1 (en) * | 2006-07-21 | 2008-01-24 | 3M Innovative Properties Company | Anisotropic Conductive Adhesives |
US20080166543A1 (en) * | 2007-01-10 | 2008-07-10 | Qizhuo Zhuo | Highly conductive composition for wafer coating |
US8124791B2 (en) | 2007-03-29 | 2012-02-28 | Canon Kabushiki Kaisha | Active energy ray curable liquid composition and liquid cartridge |
US8158746B2 (en) * | 2007-03-29 | 2012-04-17 | Canon Kabushiki Kaisha | Active energy ray curable liquid composition and liquid cartridge |
US20100324163A1 (en) * | 2007-03-29 | 2010-12-23 | Canon Kabushiki Kaisha | Active energy ray curable liquid composition and liquid cartridge |
US20100094024A1 (en) * | 2007-03-29 | 2010-04-15 | Canon Kabushiki Kaisha | Active energy ray curable liquid composition and liquid cartridge |
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US20090087591A1 (en) * | 2007-09-13 | 2009-04-02 | Larson Eric G | Low temperature bonding electronic adhesives |
US20110133330A1 (en) * | 2008-08-08 | 2011-06-09 | Henkel Corporation | Low temperature curing compositions |
US8637611B2 (en) | 2008-08-13 | 2014-01-28 | Designer Molecules, Inc. | Amide-extended crosslinking compounds and methods for use thereof |
US20110049731A1 (en) * | 2009-09-03 | 2011-03-03 | Designer Molecules, Inc. | Materials and methods for stress reduction in semiconductor wafer passivation layers |
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US8686162B2 (en) | 2010-08-25 | 2014-04-01 | Designer Molecules Inc, Inc. | Maleimide-functional monomers in amorphous form |
Also Published As
Publication number | Publication date |
---|---|
EP0969065A3 (en) | 2000-02-23 |
DE69920813T2 (en) | 2006-02-23 |
TW496891B (en) | 2002-08-01 |
EP0969065B1 (en) | 2004-10-06 |
DE69920813D1 (en) | 2004-11-11 |
CN1145682C (en) | 2004-04-14 |
HK1028904A1 (en) | 2001-03-09 |
KR100602887B1 (en) | 2006-07-19 |
EP0969065A2 (en) | 2000-01-05 |
CN1248603A (en) | 2000-03-29 |
KR20000011449A (en) | 2000-02-25 |
JP2000044888A (en) | 2000-02-15 |
US6265530B1 (en) | 2001-07-24 |
SG73662A1 (en) | 2000-06-20 |
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