Film adhesives containing maleimide compounds and methods for use thereof

Abstract

In accordance with the present invention, there are provided film adhesive compositions comprising at least one macromonomer having at least one unit of ethylenic unsaturation, at least one thermoplastic elastomer co-curable with the macromonomer, and at least one cure initiator, and methods for use thereof. Invention compositions are useful as adhesives in the microelectronics industry. In particular, invention film adhesives may be used to produce microelectronic assemblies with very thin bond lines without compromising adhesive strength.

1 - 15 . (canceled)  
     
     
         16 . A thermally curable film adhesive composition comprising a curable component comprising at least one macromonomer having at least one unit of ethylenic unsaturation, wherein said macromonomer is a maleimide, 
 in the range of about 20-90 wt % of at least one thermoplastic elastomer co-curable with said at least one macromonomer, and    at least one free radical cure initiator,    wherein wt % is based on total weight of the composition; and    wherein said free radical cure initiator is present in the range of about 0.5 wt % up to 2.0 wt %; and    wherein said macromonomer is present in the range of about 10 wt % up to about 80 wt %, wherein wt % is based on total weight of the composition.    
     
     
         17 . An adhesive composition according to  claim 16 , wherein said cure initiator is a free-radical cure initiator.  
     
     
         18 - 21 . (canceled)  
     
     
         22 . An adhesive composition according to  claim 16 , further comprising a filler.  
     
     
         23 . An adhesive composition according to  claim 22 , wherein said filler is conductive.  
     
     
         24 . An adhesive composition according to  claim 23 , wherein said filler is electrically conductive.  
     
     
         25 . An adhesive composition according to  claim 23 , wherein said filler is thermally conductive.  
     
     
         26 . An adhesive composition according to  claim 22 , wherein said filler is non-conductive.  
     
     
         27 . An adhesive composition according to  claim 26 , wherein said filler is a perfluorinated hydrocarbon polymer.  
     
     
         28 . An adhesive composition according to  claim 22 , wherein said filler is present in the range of about 1 wt % up to about 95 wt %, wherein wt % is based on total weight of the composition.  
     
     
         29 . (canceled)  
     
     
         30 . An adhesive composition comprising at least one thermoplastic elastomer, at least one macromonomer having at least one unit of ethylenic unsaturation, and at least one cure initiator, 
 wherein said macromonomer is selected from the group consisting of maleimides, allylated amides, and vinyl compounds.    
     
     
         31 . An adhesive composition according to  claim 30 , wherein said composition is capable of curing at a temperature in the range of about 150° C. up to about 200° C. in a period of time of about 0.25 minutes up to about 2 minutes.  
     
     
         32 - 34 . (canceled)  
     
     
         35 . An adhesive composition according to  claim 30 , wherein said macromonomer is a vinyl compound.  
     
     
         36 . An adhesive composition according to  claim 35 , wherein said vinyl compound has the following structure:  
       
         
           
           
               
               
           
         
       
       wherein: 
 q is 1, 2 or 3,  
 each R is independently selected from hydrogen or lower alkyl,  
 each Q is independently selected from —O—, —O—C(O)—, —C(O)— or —C(O)—O—, and  
 Y is a monovalent moiety or a multivalent linking moiety.  
 
     
     
         37 . An adhesive composition according to  claim 36 , wherein Y is selected from: 
 (I) straight or branched chain alkyl, alkylene, oxyalkylene, alkenyl, alkenylene, oxyalkenylene, ester, or polyester, optionally containing substituents selected from hydroxy, alkoxy, carboxy, nitrile, cycloalkyl or cycloalkenyl,    (II) siloxanes having the structure:      —(CR 2 ) m′ —[Si(R′) 2 —O] q′ —Si(R′) 2 —(CR 2 ) n′ — or  (CR 2 ) m′ —[Si(R′) 2 —O] q′ —Si (R′) 2 —(CR 2 ) n′ —   wherein     each R is independently defined as above, and each R′ is independently selected from hydrogen, lower alkyl or aryl, m′ falls in the range of 1 up to 10, n′ falls in the range of 1 up to 10, and q′ falls in the range of 1 up to 50,    (III) polyalkylene oxides having the structure:      —[(CR 2 ) r —O—] q′ —(CR 2 ) s — or      (CR 2 ) r —O—] q′ —(CR 2 ) s —   wherein each R is independently as defined above, r falls in the range of 1 up to 10, s falls in the range of 1 up to 10, and q′ is as defined above,    (IV) aromatic moieties having the structure:                          wherein each R is independently as defined above, t falls in the range of 2 up to 10, u is 1, 2 or 3, and Ar is as defined above, or                          wherein Z is O or NR, wherein R is hydrogen or lower alkyl,    (V) urethanes having the structure                          wherein:     each R 1  is independently hydrogen or lower alkyl,     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 about 100 atoms in the chain, which chain may contain aryl substituents;     X is O, S, N, or P; and     v is 0 to 50,    (VI) aromatic moieties having the structure:                          wherein     each Ar is a monosubstituted, disubstituted or trisubstituted aromatic or heteroaromatic ring having in the range of 3 up to about 10 carbon atoms,     n is 1 up to about 50, and     Z is selected from: 
 straight or branched chain alkyl, alkylene, oxyalkylene, alkenyl, alkenylene, oxyalkenylene, ester, or polyester, optionally containing substituents selected from hydroxy, alkoxy, carboxy, nitrile, cycloalkyl or cycloalkenyl,  
 siloxanes having the structure:  
   —(CR 2 ) m′ —[Si(R′) 2 —O] q′ —Si(R′) 2 —(CR 2 ) n′ — 
 wherein  
  each R is independently defined as above, and each R′ is independently selected from hydrogen, lower alkyl or aryl, m′ falls in the range of 1 up to 10, n′ falls in the range of 1 up to 10, and q′ falls in the range of 1 up to 50,  
  polyalkylene oxides having the structure:  
   —[(CR 2 ) r —O—] q′ —(CR 2 ) s — 
 wherein each R is independently as defined above, r falls in the range of 1 up to 10, s falls in the range of 1 up to 10, and q′ is as defined above, aromatic moieties having the structure:  
                     
 wherein each R is independently as defined above, t falls in the range of 2 up to 10, u is 1, 2 or 3, and Ar is as defined above, as well as mixtures of any two or more thereof.  
   
     
     
         38 . An adhesive composition according to  claim 30 , wherein said macromonomer is an allylated amide.  
     
     
         39 . An adhesive composition according to  claim 38 , wherein said allylated amide has the following structure:  
       
         
           
           
               
               
           
         
       
       wherein: 
 R′ is hydrogen, C 1  up to about C 18  alkyl or oxyalkyl, allyl, aryl, or substituted aryl,  
 m is 1-6, and  
 X is selected from  
 (I) straight or branched chain alkyl, alkylene, oxyalkylene, alkenyl, alkenylene, oxyalkenylene, ester, or polyester, optionally containing substituents selected from hydroxy, alkoxy, carboxy, nitrile, cycloalkyl or cycloalkenyl,  
 (II) siloxanes having the structure:  
   —(CR 2 ) m′ —[Si(R′) 2 —O] q′ —Si(R′) 2 —(CR 2 ) n′ — or  (CR 2 ) m′ —[Si(R′) 2 —O] q′ —Si(R′) 2 —(CR 2 ) n′ — 
 wherein  
  each R is independently defined as above, and each R′ is independently selected from hydrogen, lower alkyl or aryl, m′ falls in the range of 1 up to 10, n′ falls in the range of 1 up to 10, and q′ falls in the range of 1 up to 50,  
 (III) polyalkylene oxides having the structure:  
   —[(CR 2 ) r —O—] q′ —(CR 2 ) s — or  [(CR 2 ) r —O—] q′ —(CR 2 ) s — 
 wherein each R is independently as defined above, r falls in the range of 1 up to 10, s falls in the range of 1 up to 10, and q′ is as defined above,  
 (IV) aromatic moieties having the structure:  
                     
 wherein each R is independently as defined above, t falls in the range of 2 up to 10, u is 1, 2 or 3 and Ar is as defined above, or  
                     
 wherein  
  Z is O or NR, wherein R is hydrogen or lower alkyl,  
 (V) urethanes having the structure  
                     
 wherein:  
  each R 1  is independently hydrogen or lower alkyl,  
  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 about 100 atoms in the chain, which chain may contain aryl substituents;  
  X is O, S, N, or P; and  
  v is 0 to 50,  
 (VI) aromatic moieties having the structure:  
                     
 wherein  
  each Ar is a monosubstituted, disubstituted or trisubstituted aromatic or heteroaromatic ring having in the range of 3 up to about 10 carbon atoms,  
  n is 1 up to about 50, and  
  Z is selected from: 
 straight or branched chain alkyl, alkylene, oxyalkylene, alkenyl, alkenylene, oxyalkenylene, ester, or polyester, optionally containing substituents selected from hydroxy, alkoxy, carboxy, nitrile, cycloalkyl or cycloalkenyl,  
 siloxanes having the structure:  
   (CR 2 ) m′ —[Si(R′) 2 —O] q′ —Si(R′) 2 —(CR 2 ) n′ — 
 wherein  
  each R is independently defined as above, and each R′ is independently selected from hydrogen, lower alkyl or aryl, m′ falls in the range of 1 up to 10, n′ falls in the range of 1 up to 10, and q′ falls in the range of 1 up to 50,  
  polyalkylene oxides having the structure:  
   —[(CR 2 ) r —O—] q′ —(CR 2 ) s — 
 wherein each R is independently as defined above, r falls in the range of 1 up to 10, s falls in the range of 1 up to 10, and q′ is as defined above, aromatic moieties having the structure:  
                     
 wherein each R is independently as defined above, t falls in the range of 2 up to 10, u is 1, 2 or 3, and Ar is as defined above, as well as mixtures of any two or more thereof.  
 
 
     
     
         40 - 45 . (canceled)  
     
     
         46 . An adhesive composition comprising at least one macromonomer having at least one unit of ethylenic unsaturation, at least one thermoplastic elastomer co-curable with said at least one macromonomer, and at least one cure initiator, which when dispensed between a device and a substrate and cured for 2 minutes at 200° C., provides a room temperature die shear of about 90 lbs.  
     
     
         47 . An adhesive composition according to  claim 46 , wherein said macromonomer is a maleimide.