Photoacid generators and photoresists comprising same

Abstract

New methods are provided for synthesis of photoacid generator compounds (“PAGs”), new photoacid generator compounds and photoresist compositions that comprise such PAG compounds. In a particular aspect, sulfonium-containing (S+) photoacid generators and methods of synthesis of sulfonium photoacid generators are provided.

1 . A method for producing a sulfonium compound comprising cyclizing an alkylthio compound. 
     
     
         2 . The method of claim I wherein the alkyl sulfide has a formula of R—S(CH 2 ) n (CH 2 LG) where:
 R is a non-hydrogen substituent; 
 n is an integer of from 3 to 6; and 
 LG is a leaving group. 
 
     
     
         3 . The method of  claim 1  the sulfonium compound is associated with a fluorinated sulfonic acid. 
     
     
         4 . The method of  claim 3  wherein the fluorinated sulfonic acid has a formula of R(CH 2 ) n (CF 2 ) 2 SO 3 — where n is an integer of from 2 to 8, and R is a non-hydrogen substituent. 
     
     
         5 . The method of  claim 1  wherein a photoacid generator compound is produced that is selected from the following Formulae (I) and (II): 
       
         
           
           
               
               
           
         
         wherein in each of Formulae I and II R is hydrogen or a non-hydrogen substituent such a straight, branched or cyclic C 1-20  alkyl groups. 
       
     
     
         6 . The method of  claim 5  wherein R is tert-butyl. 
     
     
         7 . A photoacid generator compound that comprises an anion component selected from the following: 
       
         
           
           
               
               
           
         
       
     
     
         8 . A photoacid generator compound of  claim 7  that is selected from the following: 
       
         
           
           
               
               
           
         
         wherein R1, R2 and R3 are each independently the same or different non-hydrogen substituent; and 
       
       
         
           
           
               
               
           
         
         wherein R1, R2 and R3 are each independently the same or different non-hydrogen substituent. 
       
     
     
         9 . A photoacid generator compound of  claim 7  that is selected from the following Formulae (I) and (II): 
       
         
           
           
               
               
           
         
         wherein in each of Formulae I and II R is hydrogen or a non-hydrogen substituent such a straight, branched or cyclic C 1-20  alkyl groups. 
       
     
     
         10 . The photoacid generator compound of  claim 8  wherein R is tert-butyl. 
     
     
         11 . A photoacid generator compound obtainable by a method of  claim 1  wherein the compound is selected from the following Formula (I) and (II): 
       
         
           
           
               
               
           
         
         wherein in each of Formulae I and II R is hydrogen or a non-hydrogen substituent such a straight, branched or cyclic C 1-20  alkyl groups. 
       
     
     
         12 . The photoacid generator compound of  claim 11  wherein R is tert-butyl. 
     
     
         13 . A photoresist composition comprising a resin component and a photoacid generator compound of  claim 7 . 
     
     
         14 . A method for forming a photoresist relief image comprising:
 a) applying a coating layer of a photoresist composition of  claim 13  on a substrate;   (b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.