Adamantane derivatives and process for producing the same

Abstract

The present invention provides an adamantane derivative (I) having a structure represented by the general formula (I); an adamantane derivative (II) having a structure represented by the general formula (II); and a process for producing those adamantane derivatives. An alcohol form of an adamantane compound is reacted with a sulfonyl compound to obtain the adamantane derivative (II), which is then reacted with an alcohol to obtain the adamantane derivative (I). The adamantane derivative (I) and adamantane derivative (II) each having the structure represented by the general formula (I) and general formula (II), respectively, is a novel adamantyl (meth)acrylate compound and useful as a monomer for functional resins such as a photosensitive resin in the field of photolithography.

1 . An adamantane derivative, characterized by comprising a structure represented by a general formula (I): 
     
       
         
         
             
             
         
       
       where R represents a hydrogen atom, a methyl group, or a CF 3  group, Ys each represent an alkyl group having 1 to 10 carbon atoms, a halogen atom, or a hydroxyl group, or two Ys are coupled to form ═O, and multiple Ys may be identical to or different from each other, R1 represents an alkyl group or a cycloalkyl group having 1 to 10 carbon atoms, and may contain a hetero atom and/or a nitrile group in part of its structure, k represents an integer of 0 to 14, and m and n each independently represent an integer of 0 to 4. 
     
   
   
       2 . The adamantane derivative according to  claim 1 , wherein a substituent except Ys is present at a bridge head position. 
   
   
       3 . The adamantane derivative according to  claim 1 , wherein R 1  represents a group having tertiary carbon adjacent to O. 
   
   
       4 - 10 . (canceled) 
   
   
       11 . A process for producing an adamantane derivative represented by the general formula (I): 
     
       
         
         
             
             
         
       
       where R represents a hydrogen atom, a methyl group, or a CF 3  group, Ys each represent an alkyl group having 1 to 10 carbon atoms, a halogen atom, or a hydroxyl group, or two Ys are coupled to form ═O, and multiple Ys may be identical to or different from each other, R 1  represents an alkyl group or a cycloalkyl group having 1 to 10 carbon atoms, and may contain a hetero atom and/or a nitrile group in part of its structure, k represents an integer of 0 to 14, and m and n each independently represent an integer of 0 to 4, the process being characterized by comprising reacting an adamantane derivative represented by the general formula (II): 
     
     
       
         
         
             
             
         
       
       where R 2  represents an alkyl group having 1 to 10 carbon atoms, a phenyl group, an alkylphenyl group, or a CF 3  group, R, Ys, k, m, and n each have the same meaning as that described above, with an alcohol. 
     
   
   
       12 . The process for producing an adamantane derivative according to  claim 11 , wherein 3-methanesulfonyloxy-1-adamantyl (meth)acrylate is reacted with the alcohol. 
   
   
       13 . The process for producing an adamantane derivative according to  claim 11 , wherein the alcohol comprises a tertiary alcohol.