Photoactive Compounds

Abstract

The present invention relates to novel photoactive compounds that can be used in formulating photoresist compositions.

1 . A process for imaging a photoresist comprising the steps of:
 a) coating a substrate with the composition of comprising:
 a polymer containing an acid labile group; and, 
 a compound of the formula
   Y—Ar 
 
 where Ar is selected from 
   
       
         
           
           
               
               
           
         
         
           
             naphthyl, or anthryl; 
           
           Y is selected from 
         
       
       
         
           
           
               
               
           
         
         
           where W is selected from 
         
       
       
         
           
           
               
               
           
         
         
           where R 1A , R 1B , R 1C , R 2A , R 2B , R 2C , R 2D , R 3A , R 3B , R 3C , R 3D , R 4A , R 4B , R 4C , R 4D , R 5A , R 5B  and R 5C , are each independently selected from Z, hydrogen, C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, C 5-50  cyclic alkylcarbonyl group, C 5-50  aryl group, C 5-50  aralkyl group, arylcarbonylmethylene group, C 1-20  straight or branched alkoxy chain, nitro, cyano, tresyl, or hydroxyl; either (i) one of R 1D  or R 5D  is nitro with the other being selected from hydrogen, C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, C 5-50  cyclic alkylcarbonyl group, C 5-50  aryl group, C 5-50  aralkyl group, arylcarbonylmethylene group, cyano, or hydroxyl or (ii) both of R 1D  and R 5D  are nitro; R 6  and R 7  are each independently selected from C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, C 5-50  cyclic alkylcarbonyl group, C 5-50  aryl group, C 5-50  aralkyl group, arylcarbonylmethylene group, nitro, cyano, or hydroxyl or R 6  and R 7  together with the S atom to which they are attached form a 5-, 6-, or 7-membered saturated or unsaturated ring optionally containing one or more O atoms; T is a direct bond, a divalent C 1-20  straight or branched alkyl group optionally containing one or more O atoms, divalent C 5-50  aryl group, divalent C 5-50  aralkyl group, or divalent C 5-50  monocyclic, bicyclic or tricyclic alkyl group; Z is —(V) j —(C(X11)(X12)) n -O—C(═O)—R 8 , where either (i) one of X11 or X12 is C 1-20  straight or branched alkyl chain containing at least one fluorine atom and the other is hydrogen, halogen, or C 1-20  straight or branched alkyl chain or (ii) both of X11 and X12 are C 1-20  straight or branched alkyl chain containing at least one fluorine atom; V is a linkage group selected from a direct bond, a divalent C 1-20  straight or branched alkyl group optionally containing one or more O atoms, divalent C 5-50  aryl group, divalent C 5-50  aralkyl group, or divalent C 5-50  monocyclic, bicyclic or tricyclic alkyl group; X2 is hydrogen, halogen, or C 1-20  straight or branched alkyl chain optionally containing one or more O atoms; R 8  is a C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, a C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, or a C 5-50  aryl group; X3 is hydrogen, C 1-20  straight or branched alkyl chain, halogen, cyano, or —C(═O)—R 50  where R 50  is selected from C 1-20  straight or branched alkyl chain optionally containing one or more O atoms or —O—R 51  where R 51  is hydrogen or C 1-20  straight or branched alkyl chain; j is 0 to 10; m is 0 to 10; and n is 0 to 10, 
           the C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, C 1-20  straight or branched alkyl chain, C 1-20  straight or branched alkoxy chain, C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, C 5-50  cyclic alkylcarbonyl group, C 5-50  aralkyl group, C 5-50  aryl group, naphthyl, anthryl, 5-, 6-, or 7-membered saturated or unsaturated ring optionally containing one or more O atoms, or arylcarbonylmethylene group being unsubstituted or substituted by one or more groups selected from the group consisting of Z, halogen, C 1-20  alkyl, C 3-20  cyclic alkyl, C 1-20  alkoxy, C 3-20  cyclic alkoxy, di C 1-20  alkylamino, dicyclic di C 1-20  alkylamino, hydroxyl, cyano, nitro, tresyl, oxo, aryl, aralkyl, oxygen atom, CF 3 SO 3 , aryloxy, arylthio, and groups of formulae (II) to (VI): 
         
       
       
         
           
           
               
               
           
         
         
           wherein R 10  and R 11  each independently represent a hydrogen atom, a C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, or a C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, or R 10  and R 11  together can represent an alkylene group to form a five- or six-membered ring, 
           R 12  represents a C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, a C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, or a C 5-50  aralkyl group, or R 10  and R 12  together represent an alkylene group which forms a five- or six-membered ring together with the interposing —C—O— group, the carbon atom in the ring being optionally substituted by an oxygen atom, 
           R 13  represents a C 1-20  straight or branched alkyl chain optionally containing one or more O atoms or a C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, 
           R 14  and R 15  each independently represent a hydrogen atom, a C 1-20  straight or branched alkyl chain optionally containing one or more O atoms or a C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, 
           R 16  represents a C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, a C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, a C 5-50  aryl group, or a C 5-50  aralkyl group, and 
           R 17  represents C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, a C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, a C 5-50  aryl group, a C 5-50  aralkyl group, the group —Si(R 16 ) 2 R 17 , or the group —O—Si(R 16 ) 2 R 17 , the C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, C 5-50  aryl group, and C 5-50  aralkyl group being unsubstituted or substituted as above; and 
           A −  is an anion; 
         
         b) baking the substrate to substantially remove the solvent; 
         c) image-wise exposing the photoresist coating; 
         d) postexposure baking the photoresist coating; and 
         e) developing the photoresist coating with an aqueous alkaline solution. 
       
     
     
         2 . The process according to  claim 1 , where the image-wise exposure wavelength is below 200 nm. 
     
     
         3 . The process according to  claim 1 , where the aqueous alkaline solution comprises tetramethylammonium hydroxide. 
     
     
         4 . The process according to  claim 1 , where the aqueous alkaline solution further comprises a surfactant. 
     
     
         5 . The process according to  claim 1 , where the substrate is selected from a microelectronic device and a liquid crystal display substrate. 
     
     
         6 . The process according to  claim 1  wherein for a), Ar is 
       
         
           
           
               
               
           
         
       
     
     
         7 . The process according to  claim 6  wherein for a), Y is 
       
         
           
           
               
               
           
         
       
     
     
         8 . The process according to  claim 7  wherein for a), R 6  and R 7  are each independently selected from C 1-20  straight or branched alkyl chain optionally containing one or more O atoms or C 5-50  aryl group, and R 3A  is Z. 
     
     
         9 . The process according to  claim 8  wherein for a), each of R 1A , R 2A , R 3A , R 4A , and R 5A  are each independently selected from Z, hydrogen, or C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, the C 1-20  straight or branched alkyl chain optionally containing one or more O atoms or C 5-50  aryl group being unsubstituted or substituted. 
     
     
         10 . The process according to  claim 7  wherein for a), R 6  and R 7  are each independently selected from C 1-20  straight or branched alkyl chain optionally containing one or more O atoms. 
     
     
         11 . The process according to  claim 8  wherein for a), R 6  and R 7  are each independently selected from C 5-50  aryl group. 
     
     
         12 . The process according to  claim 6  wherein for a), Y is 
       
         
           
           
               
               
           
         
       
     
     
         13 . The process according to  claim 12  wherein for a), R 3A  is Z. 
     
     
         14 . The process according to  claim 12  wherein for a), R 3B  is Z or hydrogen. 
     
     
         15 . The process according to  claim 6  wherein for a), Y is 
       
         
           
           
               
               
           
         
       
     
     
         16 . The process according to  claim 15  wherein for a), W is 
       
         
           
           
               
               
           
         
       
     
     
         17 . The process according to  claim 16  wherein for a), X2 is selected from hydrogen, methyl, and perfluoromethyl and m is 1. 
     
     
         18 . The process according to  claim 15  wherein for a), W is 
       
         
           
           
               
               
           
         
       
     
     
         19 . The process according to  claim 18  wherein for a), one of R 1D  or R 5D  is nitro with the other being selected from hydrogen, C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, C 5-50  cyclic alkylcarbonyl group, C 5-50  aryl group, C 5-50  aralkyl group, arylcarbonylmethylene group, cyano, or hydroxyl, the C 1-20  straight or branched alkyl chain optionally containing one or more O atoms, C 5-50  monocyclic, bicyclic, or tricyclic alkyl group, C 5-50  cyclic alkylcarbonyl group, C 5-50  aryl group, C 5-50  aralkyl group, and arylcarbonylmethylene group being unsubstituted or substituted, or both of R 1D  and R 5D  are nitro.