Photoimageable composition

Abstract

Disclosed are photoimageable compositions containing silsesquioxane binder polymers and photoactive compounds, methods of forming relief images using such compositions and methods of manufacturing electronic devices using such compositions. Such compositions are useful as photoresists and in the manufacture of optoelectronic devices.

1 - 24 . (cancelled)  
     
     
         25 . A photoimageable composition comprising a binder polymer and a photoactive component, wherein the binder polymer comprises as polymerized units one or more monomers of formula I and one or more monomers of formula II 
         (R 1 SiO 3/2 )  (I)                    
       wherein R 1  is selected from (C 1 -C 12 )alkyl, substituted (C 1 -C 12 )alkyl, (C 2 -C 6 )alkenyl, substituted (C 2 -C 6 )alkenyl, phenyl, C 6 (R 7 ) 5 , (C 1 -C 5 )alkyl(C 6 (R 7 ) 4 ), (C 1 -C 5 )alkyl(C 6 H 4 OZ), vinyl and substituted vinyl; Z is selected from (C 1 -C 6 )alkylsulfonate ester or arylsulfonate ester; each R 7  is independently selected from H, F, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkyl, hydroxy-halo(C 1 -C 6 )alkyl or halo(C 1 -C 6 )alkoxy; each R 4  is independently selected from R 7  and OH; each R 5  is independently selected from H or F; each R 6  is independently selected from H, F, CH 3 , CF 3 , CHF 2 , and CH 2 F; and m=0-2.  
     
     
         26 . The composition of  claim 25  wherein R 1  is selected from methyl, ethyl, trifluoromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, phenyl, benzyl, phenethyl, tolyl, trifluoromethylphenyl, trifluoromethoxyphenyl, norbornyl, cyclohexyl, 1,2,2-trifluorovinyl, phenylsulfonatobenzyl, phenylsulfonatophenylethyl, methylsulfonatobenzyl, ethylsulfonatobenzyl, propylsulfonatobenzyl, trifluoromethylsulfonatobenzyl, methylsulfonatophenylethyl, tolylsulfonatobenzyl, tolylsulfonatophenylethyl, camphorsulfonatobenzyl, camphorsulfonatophenylethyl, phenylsulfonatophenyl, methylsulfonatophenyl, tolylsulfonatophenyl, camphorsulfonatophenyl, ethylsulfonatophenyl, propylsulfonatophenyl, trifluoromethylsulfonatophenyl, ethylsulfonatophenylethyl, propylsulfonatophenylethyl, or trifluoromethylsulfonatophenylethyl.  
     
     
         27 . The composition of  claim 25  wherein m=1.  
     
     
         28 . The composition of  claim 25  wherein the photoactive component comprises a photoacid generator.  
     
     
         29 . The composition of  claim 25  wherein the composition is negative-acting.  
     
     
         30 . The composition of  claim 25  further comprising one or more cross-linking agents.  
     
     
         31 - 32 . (cancelled)  
     
     
         33 . The composition of  claim 25  wherein the binder polymer further comprises as polymerized units one or more monomers of formula III  
       
         
           
           
               
               
           
         
       
       wherein R 2  is an acid cleavable group; each R is independently selected from H, F, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkyl, hydroxy-halo(C 1 -C 6 )alkyl or halo(C 1 -C 6 )alkoxy; each R 9  is independently selected from H or F; each R 10  is independently selected from H, F, CH 3 , CF 3 , CHF 2 , and CH 2 F; and p=0-2.  
     
     
         34 - 38 . (cancelled)  
     
     
         39 . A method of forming a relief image comprising the steps of depositing a photoimageable composition on a substrate and imaging the photoimageable composition through a mask to provide a relief image, wherein the photoimageable composition comprises a binder polymer and a photoactive component, wherein the binder polymer comprises as polymerized units one or more monomers of formula I and one or more monomers of formula II 
         (R 1 SiO 3/2 )  (I)                    
       wherein R 1  is selected from (C 1 -C 12 )alkyl, substituted (C 1 -C 12 )alkyl, (C 2 -C 6 )alkenyl, substituted (C 2 -C 6 )alkenyl, phenyl, C 6 (R 7 ) 5 , (C 1 -C 5 )alkyl(C 6 (R 7 ) 4 ), (C 1 -C 5 )alkyl(C 6 H 4 OZ), vinyl and substituted vinyl; Z is selected from (C 1 -C 6 )alkylsulfonate ester or arylsulfonate ester; each R 7  is independently selected from H, F, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkyl, hydroxy-halo(C 1 -C 6 )alkyl or halo(C 1 -C 6 )alkoxy; each R 4  is independently selected from R 7  and OH; each R 5  is independently selected from H or F; each R 6  is independently selected from H, F, CH 3 , CF 3 , CHF 2 , and CH 2 F; and m=0-2.  
     
     
         40 - 45 . (cancelled)  
     
     
         46 . The method of  claim 39  wherein the binder polymer further comprises as polymerized units one or more monomers of formula III  
       
         
           
           
               
               
           
         
       
       wherein R 2  is an acid cleavable group; each R 8  is independently selected from H, F, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkyl, hydroxy-halo(C 1 -C 6 )alkyl or halo(C 1 -C 6 )alkoxy; each R 9  is independently selected from H or F; each R 10  is independently selected from H, F, CH 3 , CF 3 , CHF 2 , and CH 2 F; and p=0-2.  
     
     
         47 - 49 . (cancelled)  
     
     
         50 . The method of  claim 39  wherein the composition is positive-acting.  
     
     
         51 - 58 . (cancelled)  
     
     
         59 . A method of manufacturing an electronic device comprising the steps of disposing on an electronic device substrate a photoimageable composition comprising a binder polymer and a photoactive component, wherein the binder polymer comprises as polymerized units one or more monomers of formula I and one or more monomers of formula II 
         (R 1 SiO 3/2 )  (I)                    
       wherein R 1  is selected from (C 1 -C 12 )alkyl, substituted (C 1 -C 12 )alkyl, (C 2 -C 6 )alkenyl, substituted (C 2 -C 6 )alkenyl, phenyl, C 6 (R 7 ) 5 , (C 1 -C 5 )alkyl(C 6 (R 7 ) 4 ), (C 1 -C 5 )alkyl(C 6 H 4 OZ), vinyl and substituted vinyl; Z is selected from (C 1 -C 6 )alkylsulfonate ester or arylsulfonate ester; each R 7  is independently selected from H, F, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkyl, hydroxy-halo(C 1 -C 6 )alkyl or halo(C 1 -C 6 )alkoxy; each R 4  is independently selected from R 7  and OH; each R 5  is independently selected from H or F; each R 6  is independently selected from H, F, CH 3 , CF 3 , CHF 2 , and CH 2 F; and m=0-2; imaging the photoimageable composition through a mask; and developing the photoimageable composition.  
     
     
         60 - 61 . (cancelled)  
     
     
         62 . The method of  claim 59  wherein the binder polymer further comprises as polymerized units one or more monomers of formula III  
       
         
           
           
               
               
           
         
       
       wherein R 2  is an acid cleavable group; each R 8  is independently selected from H, F, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkyl, hydroxy-halo(C 1 -C 6 )alkyl or halo(C 1 -C 6 )alkoxy; each R 9  is independently selected from H or F; each R 10  is independently selected from H, F, CH 3 , CF 3 , CHF 2 , and CH 2 F; and p=0-2.  
     
     
         63 - 70 . (cancelled)  
     
     
         71 . A photoimageable composition comprising a binder polymer and a photoactive component, wherein the binder polymer comprises as polymerized units one or more monomers of formula I, one or more monomers of formula II and one or more monomers of formula III 
         (R 1 SiO 3/2 )  (I)                    
       wherein R 1  is selected from (C 1 -C 12 )alkyl, substituted (C 1 -C 12 )alkyl, (C 2 -C 6 )alkenyl, substituted (C 2 -C 6 )alkenyl, phenyl, C 6 (R 7 ) 5 , (C 1 -C 5 )alkyl(C 6 (R 7 ) 4 ), (C 1 -C 5 )alkyl(C 6 H 4 OZ), vinyl and substituted vinyl; Z is selected from (C1-C 6 )alkylsulfonate ester or arylsulfonate ester; R 2  is an acid cleavable group; each R 7  and R 8  is independently selected from H, F, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkyl, hydroxy-halo(C 1 -C 6 )alkyl or halo(C 1 -C 6 )alkoxy; each R 4  is independently selected from R 7  and OH; each R 5  and R 9  is independently selected from H or F; each R 6  and R 10  is independently selected from H, F, CH 3 , CF 3 , CHF 2 , and CH 2 F; m=0-2; and p=0-2.  
     
     
         72 . A method of forming a relief image comprising the steps of depositing a photoimageable composition on a substrate and imaging the photoimageable composition through a mask to provide a relief image, wherein the photoimageable composition comprises a binder polymer and a photoactive component, wherein the binder polymer comprises as polymerized units one or more monomers of formula I, one or more monomers of formula II and one or more monomers of formula III 
         (R 1 SiO 3/2 )  (I)                    
       wherein R 1  is selected from (C 1 -C 12 )alkyl, substituted (C 1 -C 12 )alkyl, (C 2 -C 6 )alkenyl, substituted (C 2 -C 6 )alkenyl, phenyl, C 6 (R 7 ) 5 , (C 1 -C 5 )alkyl(C 6 (R 7 ) 4 ), (C 1 -C 5 )alkyl(C 6 H 4 OZ), vinyl and substituted vinyl; Z is selected from (C1-C6)alkylsulfonate ester or arylsulfonate ester; R 2  is an acid cleavable group; each R 7  and R 8  is independently selected from H, F, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkyl, hydroxy-halo(C 1 -C 6 )alkyl or halo(C 1 -C 6 )alkoxy; each R 4  is independently selected from R 7  and OH; each R 5  and R 9  is independently selected from H or F; each R 6  and R 10  is independently selected from H, F, CH 3 , CF 3 , CHF 2 , and CH 2 F; m=0-2; and p=0-2.  
     
     
         73 . A method of manufacturing an electronic device comprising the steps of disposing on an electronic device substrate a photoimageable composition comprising a binder polymer and a photoactive component, wherein the binder polymer comprises as polymerized units one or more monomers of formula I, one or more monomers of formula II and one or more monomers of formula III 
         (R 1 SiO 3/2 )  (I)                    
       wherein R 1  is selected from (C 1 -C 12 )alkyl, substituted (C 1 -C 12 )alkyl, (C 2 -C 6 )alkenyl, substituted (C 2 -C 6 )alkenyl, phenyl, C 6 (R 7 ) 5 , (C 1 -C 5 )alkyl(C 6 (R 7 ) 4 ), (C 1 -C 5 )alkyl(C 6 H 4 OZ), vinyl and substituted vinyl; Z is selected from (C1-C6)alkylsulfonate ester or arylsulfonate ester; R 2  is an acid cleavable group; each R 7  and R 8  is independently selected from H, F, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkyl, hydroxy-halo(C 1 -C 6 )alkyl or halo(C 1 -C 6 )alkoxy; each R 4  is independently selected from R 7  and OH; each R 5  and R 9  is independently selected from H or F; each R 6  and R 10  is independently selected from H, F, CH 3 , CF 3 , CHF 2 , and CH 2 F; m=0-2; and p=0-2; imaging the photoimageable composition through a mask; and developing the photoimageable composition.  
     
     
         74 - 75 . (cancelled)  
     
     
         76 . A polymer comprising as polymerized units one or more monomers of formula I and one or more monomers of formula II 
         (R 1 SiO 3/2 )  (I)                    
       wherein R 1  is selected from (C 1 -C 12 )alkyl, substituted (C 1 -C 12 )alkyl, (C 2 -C 6 )alkenyl, substituted (C 2 -C 6 )alkenyl, phenyl, C 6 (R 7 ) 5 , (C 1 -C 5 )alkyl(C 6 (R 7 ) 4 ), (C 1 -C 5 )alkyl(C 6 H 4 OZ), vinyl and substituted vinyl; Z is selected from (C 1 -C 6 )alkylsulfonate ester or arylsulfonate ester; each R 7  is independently selected from H, F, (C 1 -C 6 )alkyl, (C 1 -C 6 )alkoxy, halo(C 1 -C 6 )alkyl, hydroxy-halo(C 1 -C 6 )alkyl or halo(C 1 -C 6 )alkoxy; each R 4  is independently selected from R 7  and OH; each R 5  is independently selected from H or F; each R 6  is independently selected from H, F, CH 3 , CF 3 , CHF 2 , and CH 2 F; and m=0-2.  
     
     
         77 . (cancelled)