Organic insulating material, varnish for resin film using the same, resin film and semiconductor device

Abstract

The invention provides useful organic insulating materials exhibiting low permittivity, high heat resistance and high mechanical strength, as well as resin films and semiconductor devices employing them. The organic insulating materials of the invention comprise prepolymers of adamantane structure compounds having polymerizable unsaturated bond-containing groups. The prepolymers have number-average molecular weights of between 2,000 and 500,000 based on polystyrene, as measured by gel permeation chromatography. The polymerizable unsaturated bond-containing groups are preferably groups that contain carbon-carbon triple bonds. The resin films of the invention are obtained by crosslinking reaction of the organic insulating materials or varnishes for resin film containing them, by heating and/or active irradiation, and condensation reaction.

1 . An organic insulating material comprising a prepolymer of a cage structure compound having a polymerizable unsaturated bond-containing group and a cage structure with an adamantane structure as the minimal unit, wherein the prepolymer has a number-average molecular weight of between 2,000 and 500,000 based on polystyrene and measured by gel permeation chromatography. 
   
   
       2 . An organic insulating material according to  claim 1 , wherein the cage structure with an adamantane structure as the minimal unit is an adamantane structure, polyamantane structure, poly(polyamantane) structure or polyadamantane structure. 
   
   
       3 . An organic insulating material according to  claim 1 , wherein the prepolymer comprises unsaturated bonds produced by reaction between the polymerizable unsaturated bonds in the cage structure compound, or unsaturated bonds produced by reaction between the polymerizable unsaturated bonds, and the unreacted polymerizable unsaturated bonds. 
   
   
       4 . An organic insulating material according to  claim 3 , wherein the prepolymer has a residue rate of unreacted polymerizable unsaturated bonds of between 20% and 80%. 
   
   
       5 . An organic insulating material according to  claim 1 , wherein the cage structure compound is a compound represented by the following formula (1). 
     
       
         
         
             
             
         
       
       (In formula (1), X and Y represent one or more groups each comprising the same or different polymerizable unsaturated bonds. W and Z each represent a group having an adamantane or polyamantane structure, and they may be the same or different. The symbol n represents an integer of 0 or greater.) 
     
   
   
       6 . An organic insulating material according to  claim 1 , wherein the cage structure compound is a compound represented by the following formula (2). 
     
       
         
         
             
             
         
       
       (wherein X 1  and Y 1  each represent one or more groups containing polymerizable unsaturated bonds, and they may be the same or different from each other. R 1 -R 4  each independently represent hydrogen or an organic group, and they may be the same or different from each other. The symbol n 1  represents an integer of 0 or greater.) 
     
   
   
       7 . An organic insulating material according to  claim 1 , wherein the polymerizable unsaturated bond is a carbon-carbon triple bond. 
   
   
       8 . An organic insulating material according to  claim 1 , wherein at least one of the polymerizable unsaturated bond-containing groups is a group represented by formula (3) or a group represented by formula (4). 
     
       
         
         
             
             
         
       
       (In the formula, R 5  and R 6  each independently represent hydrogen or an organic group. The symbol m is an integer of 1-5.) 
     
   
   
       9 . A varnish for resin film comprising an organic insulating material according to  claim 1 , and an organic solvent. 
   
   
       10 . A resin film obtained by using an organic insulating material according to  claim 1 , for crosslinking reaction by heating, active energy beam irradiation, or heating and active energy beam irradiation. 
   
   
       11 . A semiconductor device provided with a resin film according to  claim 10 .