Stabilization of vinyl ether materials

Abstract

A stable viscosity coating composition, a method of forming the stable viscosity coating composition and a method for using the stable viscosity coating composition in a micro-molding imprint lithographic process, such as Step and Flash Imprint Lithography is disclosed. The stable viscosity coating composition may include at least one vinyl ether having at least one vinyl ether group (—OCR═CR 2 ), and a stabilizer, wherein the stabilizer may be 9-anthracenemethanol, a substituted 9-anthracenemethanol, phenothiazine, or a substituted phenothiazine. The coating composition may include a radiation sensitive photoacid generator (PAG). The method of forming the coating composition comprises combining at least one vinyl ether having at least one vinyl ether group (—OCR═CR 2 ), and at least one stabilizer.

We claim: 
     
         1 . A stable viscosity coating composition, comprising:
 at least one vinyl ether having at least one vinyl ether group (CR2=CRO—);   a stabilizer selected from the group consisting of:   
       
         
           
           
               
               
           
         
         wherein each R 70 , R 71 , R 72 , R 73 , R 74 , R 75 , R 76 , R 77 , R 78 , R 79 , R 80 , R 81 , R 82 , R 83 , R 84 , R 85 , R 86  and R 87  (R 70 -R 87 ) comprises independently at each occurrence a hydrogen atom, a fluorine atom or a hydrocarbyl substituent with a primary, a secondary or a tertiary carbon attachment point. 
       
     
     
         2 . The stable viscosity coating composition of  claim 1 , wherein the at least one vinyl ether has the structure:
   C(R 1 )(R 2 )═C(R 3 )OC n (R 4 )(R 5 )(D)(R 6 )(R 7 )(R 8 )  (I);
   wherein D is a carbon atom or a silicon atom;   wherein n is an integer from 0 to 6; and   wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8  are independently a hydrogen atom, a fluorine atom or a hydrocarbyl substituent with a primary, a secondary or a tertiary carbon attachment point.   
     
     
         3 . The stable viscosity coating composition of  claim 1 , wherein the at least one vinyl ether has the structure:
   C(R 9 )(R 10 )═C(R 11 )OC o (R 12 )(R 13 )C p (R 14 )(R 15 )(R 16 )(R 17 )(R 18 )  (II);
   wherein E is a carbon atom or a silicon atom;   wherein o and p are independently integers from 0 to 6 and a sum of o and p is less than or equal to 6; and   wherein R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17  and R 18  are independently a hydrogen atom, a fluorine atom or a hydrocarbyl substituent with a primary, a secondary or a tertiary carbon attachment point.   
     
     
         4 . The stable viscosity coating composition of  claim 1 , wherein the at least one vinyl ether has the structure:
   C(R 19 )(R 20 )═C(R 21 )OC q (R 22 )(R 87 )(F)(R 23 )(R 24 )C r (R 25 )(R 26 )OC(R 27 )═C(R 28 )(R 29 )  (III)
   wherein F is a carbon atom or a silicon atom;   wherein q and r are 1 are independently integers from 0 to 6 and a sum of q and r is less than or equal to 6; and   wherein R 19 , R 20 , R 21 , R 22 , R 23 , R 24 R 25 , R 26 , R 27 R 28  and R 29  are independently a hydrogen atom, a fluorine atom or a hydrocarbyl substituent with a primary, a secondary or a tertiary carbon attachment point.   
     
     
         5 . The stable viscosity coating composition of  claim 1 , wherein the at least one vinyl ether has the structure: 
       
         
           
           
               
               
           
         
         wherein G and J are independently a silicon atom or a carbon atom; 
         wherein s and t are 1 are independently integers from 0 to 6 and a sum of s and t is less than or equal to 6; and 
         wherein R 30 , R 31 , R 32 , R 28 , R 29 , R 34 R 35 , R 36 , R 37 , R 38 R 39 , R 40 , R 41 , R 42  and R 43  are independently a hydrogen atom, a fluorine atom or a hydrocarbyl substituent with a primary, a secondary or a tertiary carbon attachment points. 
       
     
     
         6 . The stable viscosity coating composition of  claim 1 , wherein the at least one vinyl ether has the structure: 
       
         
           
           
               
               
           
         
         wherein K is a silicon atom or a carbon atom; 
         wherein q and r are 1 are independently integers from 0 to 6 and a sum of q and r is less than or equal to 6; and; 
         wherein R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 , R 54 , R 55 , R 56 , R 57 , R 58  and R 59  are independently a hydrogen atom, a fluorine atom or a hydrocarbyl substituent with a primary, a secondary or a tertiary carbon attachment points. 
       
     
     
         7 . The stable viscosity coating composition of  claim 1 , wherein said at least one vinyl ether is selected from the group consisting of:
   CH 2 ═CHOCH 2 Si(CH 3 ) 3   (IA),
     CH 2 ═CHOCH 2 CH 2 Si(CH 3 ) 3   (IIA),
     CH 2 ═CHOCH 2 Si(CH 3 ) 2 CH 2 OCH═CH 2   (IIIA),
     CH 2 ═CHOCH 2 C(CH 3 ) 2 CH 2 OCH═CH 2   (IIIB),
     CH(CH 3 )═CHOCH 2 Si(CH 3 )(CH 2 OCH═CH(CH 3 ))CH 2 OCH═CH(CH 3 )  (IIIC),
     CH 2 ═CHOCH 2 Si(CH 3 ) 2 OSi(CH 3 ) 2 CH 2 OCH═CH 2   (IVA),
     CH 2 ═CHOCH 2 CH 2 Si(CH 3 ) 2 CH 2 CH 2 OCH═CH 2   (VA), and
     CH 2 ═CHOCH 2 CH 2 Si(CH 3 ) 2 CH 2 CH 2 OCH═CH 2   (VB).
   
     
     
         8 . The stable viscosity coating composition of  claim 1 , wherein said stabilizer is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         9 . The stable viscosity coating composition of  claim 1 , including a radiation sensitive photoacid generator (PAG). 
     
     
         10 . The stable viscosity coating composition of  claim 9 , wherein the PAG is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         11 . A method of using a stable viscosity coating composition, comprising:
 forming a transfer layer on a substrate;   coating said transfer layer with said stable viscosity coating composition to form a coating, said stable viscosity coating composition comprising at least one vinyl ether according to  claim 1 , a stabilizer according to  claim 1 , and a photoacid generator;   contacting said coating with a template having a relief pattern that includes recesses therein so that said coating essentially completely fills the recesses in said relief pattern in said template to transfer said relief pattern to said coating;   exposing said coating to radiation through said template; and   forming a relief image in said coating by releasing the coating from said template, said releasing resulting in voids in said coating, wherein the relief image is a solidified reverse image replica of said relief pattern in said template.   
     
     
         12 . The method of  claim 11  wherein said stable viscosity coating composition comprises from between 70 and 98.8 parts by weight per 100 parts by weight of said stable viscosity coating composition. 
     
     
         13 . The method of  claim 11 , wherein the at least one vinyl ether has the structure:
   C(R 1 )(R 2 )═C(R 3 )OC n (R 4 )(R 5 )(D)(R 6 )(R 7 )(R 8 )  (I);
   wherein D is a carbon atom or a silicon atom;   wherein n is an integer from 0 to 6; and   wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8  are independently a hydrogen atom, a fluorine atom or a hydrocarbyl substituent with a primary, a secondary or a tertiary carbon attachment point.   
     
     
         14 . The method of  claim 11 , wherein the at least one vinyl ether has the structure:
   C(R 9 )(R 10 )═C(R 11 )OC o (R 12 )(R 13 )C p (R 14 )(R 15 )(R 16 )(R 17 )(R 18 )  (II);
   wherein E is a carbon atom or a silicon atom;   wherein o and p are independently integers from 0 to 6 and a sum of o and p is less than or equal to 6; and   wherein R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17  and R 18  are independently a hydrogen atom, a fluorine atom or a hydrocarbyl substituent with a primary, a secondary or a tertiary carbon attachment point.   
     
     
         15 . The method of  claim 11 , wherein the at least one vinyl ether has the structure: 
       
         
           
           
               
               
           
         
         wherein G and J are independently a silicon atom or a carbon atom; 
         wherein s and t are 1 are independently integers from 0 to 6 and a sum of s and t is less than or equal to 6; and 
         wherein R 30 , R 31 , R 32 , R 28 , R 29 , R 34 R 35 , R 36 , R 37 , R 38 R 39 , R 40 , R 41 , R 42  and R 43  are independently a hydrogen atom, a fluorine atom or a hydrocarbyl substituent with a primary, a secondary or a tertiary carbon attachment points. 
       
     
     
         16 . The method of  claim 11 , wherein the at least one vinyl ether has the structure: 
       
         
           
           
               
               
           
         
         wherein K is a silicon atom or a carbon atom; 
         wherein q and r are 1 are independently integers from 0 to 6 and a sum of q and r is less than or equal to 6; and; 
         wherein R 44 , R 45 , R 46 , R 47 , R 48 , R 49 , R 50 , R 51 , R 52 , R 53 , R 54 , R 55 , R 56 , R 57 , R 58  and R 59  are independently a hydrogen atom, a fluorine atom or a hydrocarbyl substituent with a primary, a secondary or a tertiary carbon attachment points. 
       
     
     
         17 . The method of  claim 11 , wherein said at least one vinyl ether is selected from the group consisting of:
   CH 2 ═CHOCH 2 Si(CH 3 ) 3   (IA),
     CH 2 ═CHOCH 2 CH 2 Si(CH 3 ) 3   (IIA),
     CH 2 ═CHOCH 2 Si(CH 3 ) 2 OSi(CH 3 ) 2 CH 2 OCH═CH 2   (IVA),
     CH 2 ═CHOCH 2 CH 2 Si(CH 3 ) 2 CH 2 CH 2 OCH═CH 2   (VA), and
     CH 2 ═CHOCH 2 CH 2 Si(CH 3 ) 2 CH 2 CH 2 OCH═CH 2   (VB).
   
     
     
         18 . The method of  claim 11 , wherein said stabilizer is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         19 . The method of  claim 11 , wherein said PAG is selected from the group consisting of: 
       
         
           
           
               
               
           
         
       
     
     
         20 . The method of  claim 11 , wherein a molar ratio of said stabilizer to said PAG is between 0.01 and 0.2.