Methods of making stable and thermally polymerizable vinyl, amino or oligomeric phenoxy benzocyclobutene monomers with improvied curing kinetics

Abstract

The present invention provides methods of making low energy polymerizable monomers and resins for use in making dielectric materials. The methods comprise deprotecting or deacylating an organic alkali cleavable protecting group containing addition polymerizable, amine containing aromatic monomer or oligoaromatic phenol resin containing an organic alkali cleavable protecting group, such as a C2 to C9 alkanoyl group, preferably, an acyl group, by hydrolyzing to remove the protecting group in organic alkali in a polar solvent containing an excess of alkali C1 to C7 alkoxide and form a hydroxyl functional monomer or resin, followed by; reacting via nucleophilic substitution the resulting hydroxyl functional monomer or resin with an alpha-halide (a-halide) or strong acid conjugate leaving group containing arylcyclobutene compound in a polar solvent, to yield a product an arylcyclobutene-containing addition polymerizable or amine containing aromatic monomer or oligoaromatic phenol resin having an ether linkage from the cyclobutene ring to an aromatic group of the addition polymerizable aromatic monomer, aromatic amine or oligoaromatic phenol.

We claim: 
     
         1 . A benzocyclobutene compound selected from the group consisting of: 4-vinyl phenoxy benzocyclobutene, 4-amino phenoxy benzocyclobutene, 
       
         
           
           
               
               
           
         
       
     
     
         2 . The benzocyclobutene compound of  claim 1 , wherein the vinyl benzocyclobutene compound selected from the group consisting of: 4-amino phenoxy benzocyclobutene, 
       
         
           
           
               
               
           
         
       
     
     
         3 . A monomer having the structure 
       
         
           
           
               
               
           
         
       
       wherein K is a divalent group chosen from a divalent aryloxy group having from 1 to 10 aryl or phenol rings, or an oligophenolic group having from 1 to 10 phenol units; M is a divalent aromatic group chosen from a C 1  to C 6  alkyl substituted or unsubstituted aromatic radical group or a C 1  to C 6  alkyl substituted or unsubstituted divalent heteroaromatic radical group; L 1  is a covalent bond; and R 1  through R 6  are each independently selected from a monovalent group chosen from hydrogen, deuterium, halide, hydroxyl, a C 1  to C 6  alkyl group, a C 1  to C 6  alkoxy group, a C 1  to C 6  alkyl substituted hydrocarbon group, a heteroatom containing hydrocarbon group, a C 1  to C 6  alkyl substituted heterohydrocarbon group, a cyano group, or an hydroxyl group. 
     
     
         5 . The monomer of claim  4  wherein each of R 1 , R 2  and R 3  is hydrogen. 
     
     
         6 . The monomer of claim  4  wherein each of R 1  through R 6  is hydrogen.