US2002007042A1PendingUtilityA1

Die attach adhesives for use in microelectronic devices

Priority: Jul 2, 1998Filed: Feb 1, 2001Published: Jan 17, 2002
Est. expiryJul 2, 2018(expired)· nominal 20-yr term from priority
H10W 72/07331H10W 72/354H10W 72/353H10W 72/352H10W 72/325H10W 72/073H10W 72/30C08F 290/06C09J 4/00C09J 179/08H05K 3/30C08G 18/282C08G 18/75C09J 183/10C09J 4/06C09J 177/00C08G 77/42C08F 290/065C08G 18/2875
38
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Claims

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.

Claims

exact text as granted — not AI-modified
What is claimed is:  
     
         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−X m ] 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 R 1 is 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 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; and v is 0 to 50.  
     
     
         5 . The curable adhesive composition according to  claim 1  in which Q is an ester having the structure:  
       
         
           
           
               
               
           
         
       
       in which R 3  is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents.  
     
     
         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 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  
 each R 3  can independently be 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.  
 
     
     
         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 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  
 each R 3  can independently be 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.  
 
     
     
         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−Z m ] 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 R 1  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 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 heteratom 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 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 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; and v is 0 to 50.  
     
     
         12 . The curable adhesive composition according to  claim 8  in which Z is an ester having the structure:  
       
         
           
           
               
               
           
         
       
       in which R 3  is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents.  
     
     
         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 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  
 each R 3  can independently be 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.  
 
     
     
         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 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  
 each R 3  can independently be 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.  
 
     
     
         15 . The curable adhesive composition according to any one of  claims 8  to  14  in which K is  
       
         
           
           
               
               
           
         
       
       in which p is 1 to 100.  
     
     
         16 . The curable adhesive composition according to any one of  claims 8  to  14  in which K is  
       
         
           
           
               
               
           
         
       
       in which 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 chain, and in which any heteroatom present may or may not be directly attached to the aromatic ring.  
     
     
         17 . The curable adhesive composition according to any one of  claims 8  to  14  in which K is  
       
         
           
           
               
               
           
         
       
     
     
         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) R 1  and R 2  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(R 8 ), in which R 8  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 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; and v is 0 to 50.  
     
     
         22 . The curable adhesive composition according to  claim 18  in which Q is an ester having the structure:  
       
         
           
           
               
               
           
         
       
       in which R 3  is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents.  
     
     
         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 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  
 each R 3  can independently be 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.  
 
     
     
         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 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  
 each R 3  can independently be 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.  
 
     
     
         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) R 1 and R 2  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(R 8 ), in which R 8  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 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 heteratom 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 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 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; and v is 0 to 50.  
     
     
         29 . The curable adhesive composition according to  claim 25  in which Z is an ester having the structure:  
       
         
           
           
               
               
           
         
       
       in which R 3  is an alkyl or alkyloxy chain having up to 100 atoms in the chain, which chain may contain aryl substituents.  
     
     
         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 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  
 each R 3  can independently be 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.  
 
     
     
         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 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 each R 3  can independently be 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.  
 
     
     
         32 . The curable adhesive composition according to any one of  claims 25  to  31  in which K is  
       
         
           
           
               
               
           
         
       
       when p is 1 to 100.  
     
     
         33 . The curable adhesive composition according to any one of  claims 25  to  31  in which K is  
       
         
           
           
               
               
           
         
       
       in which 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 chain, and in which any heteroatom present may or may not be directly attached to the aromatic ring.  
     
     
         34 . The curable adhesive composition according to any one of  claims 25  to  31  in which K is  
       
         
           
           
               
               
           
         
       
     
     
         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.

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