Curable polyvinyl benzyl compound and process for producing the same

Abstract

A curable polyvinyl benzyl compound represented by the following general formula (1) wherein R 1 represents a C 2-20 organic group, R 2 represents a hydrogen atom, etc., x is an integer of 0 to 4, and n is an integer of 0 to 2. The compound is obtained by reacting a fluorene compound with a vinylbenzyl halide in the presence of an alkali.

1 . A high-frequency substrate obtained by polymerizing and curing a polymerizable composition, wherein the polymerizable composition comprises a fluorene compound having at least one polymerizable unsaturated group in a molecule, except for a case where all of the polymerizable unsaturated groups are vinylbenzyl groups.  
   
   
       2 . A high-frequency substrate according to  claim 1 , wherein the fluorene compound comprises one of: at least one of an allyl group and a propargyl group as a polymerizable unsaturated group; and at least one polymerizable unsaturated group and a vinylbenzyl group.  
   
   
       3 . A high-frequency substrate obtained by polymerizing and curing a polymerizable composition, wherein the polymerizable composition comprises an indene compound having at least one polymerizable unsaturated group in a molecule.  
   
   
       4 . A high-frequency substrate according to  claim 3 , wherein the polymerizable unsaturated group comprises at least one group selected from a vinylbenzyl group, an allyl group, and a propargyl group.  
   
   
       5 . A high-frequency substrate obtained by polymerizing and curing a polymerizable composition, wherein the polymerizable composition comprises a fluorene compound having at least one polymerizable unsaturated group in a molecule and an indene compound having at least one polymerizable unsaturated group in a molecule.  
   
   
       6 . A high-frequency substrate according to  claim 2 , wherein: the fluorene compound comprises at least one compound represented by the following general formula 6; and the polymerizable composition comprises a compound obtained by reacting the fluorene compound, a halogen compound having at least one polymerizable unsaturated group selected from the group consisting of a vinylbenzyl halide, an allyl halide, and a propargyl halide, and a dihalomethyl compound having 2 to 20 carbon atoms in the presence of an alkali:  
     
       
         
         
             
             
         
       
     
     wherein R 6  represents at least one group selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, alkoxy group, and thioalkoxy group each having 1 to 5 carbon atoms, which may be the same or different, a thioaryloxy group, and an aryl group.  
   
   
       7 . A high-frequency substrate according to  claim 4 , wherein: the indene compound comprises at least one compound represented by the following general formula 5; and the polymerizable composition comprises a compound obtained by reacting the indene compound, a halogen compound having at least one polymerizable unsaturated group selected from the group consisting of a vinylbenzyl halide, an allyl halide, and a propargyl halide, and a dihalomethyl compound having 2 to 20 carbon atoms in the presence of an alkali:  
     
       
         
         
             
             
         
       
     
     wherein R 6  represents at least one group selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, alkoxy group, and thioalkoxy group each having 1 to 5 carbon atoms, which may be the same or different, a thioaryloxy group, and an aryl group.  
   
   
       8 . A high-frequency substrate according to  claim 5 , wherein: the fluorene compound comprises at least one compound represented by the following general formula 6; the indene compound comprises at least one compound represented by the following general formula 5; and the polymerizable composition comprises a compound obtained by reacting the fluorene compound, the indene compound, a halogen compound having at least one polymerizable unsaturated group selected from the group consisting of a vinylbenzyl halide, an allyl halide, and a propargyl halide, and a dihalomethyl compound having 2 to 20 carbon atoms in the presence of an alkali:  
     
       
         
         
             
             
         
       
     
     wherein R 6  represents at least one group selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, alkoxy group, and thioalkoxy group each having 1 to 5 carbon atoms, which may be the same or different, a thioaryloxy group, and an aryl group.  
   
   
       9 . A high-frequency substrate according to any one of  claims 6  to  8 , wherein an equivalent ratio of a halomethyl group of the halogen compound having a polymerizable unsaturated group to a halomethyl group of the dihalomethyl compound having 2 to 20 carbon atoms is 0.9/0.1 to 0.1/0.9.  
   
   
       10 . A high-frequency substrate according to  claim 1 , wherein the polymerizable composition comprises a composition prepared by mixing a fluorene compound having at least one polymerizable unsaturated group in a molecule and a compound which is copolymerizable with the fluorene compound.  
   
   
       11 . A high-frequency substrate according to  claim 3 , wherein the polymerizable composition comprises a composition prepared by mixing an indene compound having at least one polymerizable unsaturated group in a molecule and a compound which is copolymerizable with the indene compound.  
   
   
       12 . A prepreg obtained by impregnating a fiber material with the polymerizable composition according to any one of claims  1 ,  3 ,  5 ,  6 ,  7 ,  8 ,  10 , and  11 .  
   
   
       13 . A prepreg according to  claim 12 , wherein the fiber material comprises a glass cloth.  
   
   
       14 . A high-frequency substrate obtained by heating and pressurizing one of a single prepreg according to  claim 12  and a prepreg laminate.  
   
   
       15 . A metal-lined high-frequency substrate obtained by placing a metal foil onto one of a single prepreg according to  claim 12  and a prepreg laminate, and heating and pressurizing the whole.  
   
   
       16 . A metal foil having a resin obtained by applying the polymerizable composition according to any one of claims  1 ,  3 ,  5 ,  6 ,  7 ,  8 ,  10 , and  11  to a metal foil and integrating the polymerizable composition and the metal foil.  
   
   
       17 . A multi-layer laminate substrate comprising: a cured product prepared by applying the polymerizable composition according to any one of claims  1 ,  3 ,  5 ,  6 ,  7 ,  8 ,  10 , and  11  to a conductive layer, and polymerizing and curing the composition; and a conductive layer provided on the cured product.