Pretreatment compositions

Abstract

A pretreatment composition of: (a) at least one compound having structure VI V 1 —Y—V 2   VI in which each of Y, V 1 , and V 2 is defined in the specification; (b) at least one organic solvent, and optionally, (c) at least one adhesion promoter; in which the amount of the compound of Structure VI present in the composition is effective to inhibit residue from forming when the photosensitive composition is coated on a substrate and the coated substrate is processed to form an image thereon.

1 . A pretreatment composition, comprising:
 (a) at least one compound of structure VI
   V 1 —Y—V 2   VI 
   
     wherein
 Y is selected from the group consisting of S, O, NR 2 , (HOCH) p , and 
 
     
       
         
         
             
             
         
       
     
     in which p is an integer of from 1 to 4; each R 1  is independently selected from the group consisting of H, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, and a halogen; and each R 2  is independently selected from the group consisting of H, SH, CH 3 , C 2 H 5 , and a linear or branched C 1 -C 4  alkyl group containing a thiol group; and
 V 1  and V 2  are independently selected from the group consisting of 
 
     
       
         
         
             
             
         
       
     
     in which m is independently an integer from 0 to 4 with the proviso that m=0 only when 
     
       
         
         
             
             
         
       
     
     and n is an integer from 1 to 5; and
 (b) at least one organic solvent selected from the group consisting of ketones, non-cyclic esters, cyclic esters, and alcohols 
 wherein an amount of the compound of Structure VI present in the composition is effective to inhibit residue from forming when a photosensitive composition is coated on a substrate that is treated with the pretreatment composition and the resulting coated substrate is subsequently processed to form an image on the substrate. 
 
   
   
       2 . The pretreatment composition of  claim 1 , wherein the compound of structure VI is selected from the group consisting of 
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
   
   
       3 . The pretreatment composition of  claim 1 , wherein the compound of structure VI is selected from the group consisting of 
     
       
         
         
             
             
         
       
     
   
   
       4 . The pretreatment composition of  claim 1 , wherein the compound of structure VI is selected from the group consisting of 
     
       
         
         
             
             
         
       
     
   
   
       5 . The pretreatment composition of  claim 1 , further comprising an adhesion promoter. 
   
   
       6 . The pretreatment composition of  claim 5 , wherein the adhesion promoter is a compound of structure XIV: 
     
       
         
         
             
             
         
       
     
     in which each R 14  is independently selected from the group consisting of a C 1 -C 4  alkyl group and a C 5 -C 7  cycloalkyl group, each R 15  is independently selected from the group consisting of a C 1 -C 4  alkyl group, a C 1 -C 4  alkoxy group, a C 5 -C 7  cycloalkyl group and a C 5 -C 7  cycloalkoxy group, d is an integer from 0 to 3, q is an integer from 1 to about 6, and R 16  is selected from the group consisting of 
     
       
         
         
             
             
         
       
     
     in which R 17  and R 18  are each independently a C 1 -C 4  alkyl group or a C 5 -C 7  cycloalkyl group, and R 19  is a C 1 -C 4  alkyl group or a C 5 -C 7  cycloalkyl group. 
   
   
       7 . The pretreatment composition of  claim 6 , wherein the compound of structure VI is selected from the group consisting of 
     
       
         
         
             
             
         
       
     
     and 
     
       
         
         
             
             
         
       
     
   
   
       8 . The pretreatment composition of  claim 5 , wherein the adhesion promoter is a compound selected from the group consisting of 
     
       
         
         
             
             
         
       
     
   
   
       9 . The pretreatment composition of  claim 1 , wherein the organic solvent is gamma-butyrolactone, 2-pentanone, cyclopentanone, 2-hexanone, 2-heptanone, propylene glycol monomethyl ether acetate, ethyl acetate, methyl methoxypropionate, ethyoxyethyl propionate, ethyl lactate, 1-methoxy-2-propanol, 1-pentanol, or a mixture thereof. 
   
   
       10 . The pretreatment composition of  claim 1 , wherein the compound of structure VI is from about 0.2 wt % to about 25 wt % of the total weight of the composition. 
   
   
       11 . The pretreatment composition of  claim 1 , wherein the compound of structure VI is from about 0.75 wt % to about 18 wt % of the total weight of the composition. 
   
   
       12 . The pretreatment composition of  claim 1 , wherein the compound of structure VI is from about 1.0 wt % to about 15 wt % of the total weight of the composition. 
   
   
       13 . A pretreatment composition, consisting of:
 (a) at least one compound of structure VI
   V 1 —Y—V 2   VI 
   
     wherein
 Y is selected from the group consisting of S, O, NR 2 , (HOCH) p , and 
 
     
       
         
         
             
             
         
       
     
     in which p is an integer of from 1 to 4; each R 1  is independently selected from the group consisting of H, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, and a halogen; and each R 2  is independently selected from the group consisting of H, SH, CH 3 , C 2 H 5 , and a linear or branched C 1 -C 4  alkyl group containing a thiol group; and
 V 1  and V 2  are independently selected from the group consisting of 
 
     
       
         
         
             
             
         
       
     
     in which m is independently an integer from 0 to 4 with the proviso that m=0 only when 
     
       
         
         
             
             
         
       
     
     and n is an integer from 1 to 5; and
 (b) at least one organic solvent; 
 wherein the compound of structure VI is from about 0.75 wt % to about 18 wt % of the total weight of the composition. 
 
   
   
       14 . The pretreatment composition of  claim 13 , wherein the compound of structure VI is selected from the group consisting of 
     
       
         
         
             
             
         
       
       
         
         
             
             
         
       
     
   
   
       15 . The pretreatment composition of  claim 13 , wherein the compound of structure VI is selected from the group consisting of SH 
     
       
         
         
             
             
         
       
     
   
   
       16 . The pretreatment composition of  claim 13 , wherein the compound of structure VI is selected from the group consisting of 
     
       
         
         
             
             
         
       
     
   
   
       17 . The pretreatment composition of  claim 13 , wherein the organic solvent is N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, gamma-butyrolactone, N,N-dimethylacetamide, dimethyl-2-piperidone, N,N-dimethylformamide, 2-pentanone, cyclopentanone, 2-hexanone, 2-heptanone, propylene glycol monomethyl ether acetate, ethyl acetate, methyl methoxypropionate, ethoxyethyl propionate, ethyl lactate, 1-methoxy-2-propanol, 1-pentanol, or a mixture thereof. 
   
   
       18 . The pretreatment composition of  claim 13 , wherein the compound of structure VI is from about 1.0 wt % to about 15 wt % of the total weight of the composition. 
   
   
       19 . The pretreatment composition of  claim 13 , wherein an amount of the compound of Structure VI present in the composition is effective to inhibit residue from forming when a photosensitive composition is coated on a substrate that is treated with the pretreatment composition and the resulting coated substrate is subsequently processed to form an image on the substrate. 
   
   
       20 . A pretreatment composition, comprising:
 (a) at least one compound of structure VI
   V 1 —Y—V 2   VI 
   
     wherein
 Y is selected from the group consisting of S, O, NR 2 , (HOCH) p , and 
 
     
       
         
         
             
             
         
       
     
     in which p is an integer of from 1 to 4; each R 1  is independently selected from the group consisting of H, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, and a halogen; and each R 2  is independently selected from the group consisting of H, SH, CH 3 , C 2 H 5 , and a linear or branched C 1 -C 4  alkyl group containing a thiol group; and
 V 1  and V 2  are independently selected from the group consisting of 
 
     
       
         
         
             
             
         
       
     
     in which m is independently an integer from 0 to 4 with the proviso that m=0 only when 
     
       
         
         
             
             
         
       
     
     and n is an integer from 1 to 5; and
 (b) at least one organic solvent; and 
 (c) an adhesion promoter. 
 
   
   
       21 . The pretreatment composition of  claim 20 , wherein the adhesion promoter is a compound of structure XIV: 
     
       
         
         
             
             
         
       
     
     in which each R 14  is independently selected from the group consisting of a C 1 -C 4  alkyl group and a C 5 -C 7  cycloalkyl group, each R 15  is independently selected from the group consisting of a C 1 -C 4  alkyl group, a C 1 -C 4  alkoxy group, a C 5 -C 7  cycloalkyl group and a C 5 -C 7  cycloalkoxy group, d is an integer from 0 to 3, q is an integer from 1 to about 6, and R 16  is selected from the group consisting of 
     
       
         
         
             
             
         
       
     
     in which R 17  and R 18  are each independently a C 1 -C 4  alkyl group or a C 5 -C 7  cycloalkyl group, and R 19  is a C 1 -C 4  alkyl group or a C 5 -C 7  cycloalkyl group. 
   
   
       22 . The pretreatment composition of  claim 20 , wherein the adhesion promoter is a compound selected from the group consisting of 
     
       
         
         
             
             
         
       
     
   
   
       23 . An article, comprising:
 a semiconductor substrate; and   a pretreatment composition supported by the semiconductor substrate, the pretreatment composition comprising at least one compound of structure VI:
   V 1 —Y—V 2   VI 
   
     wherein
 Y is selected from the group consisting of S, O, NR 2 , (HOCH) p , and 
 
     
       
         
         
             
             
         
       
     
     in which p is an integer of from 1 to 4; each R 1  is independently 10 selected from the group consisting of H, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, and a halogen; and each R 2  is independently selected from the group consisting of H, SH, CH 3 , C 2 H 5 , and a linear or branched C 1 -C 4  alkyl group containing a thiol group; and
 V 1  and V 2  are independently selected from the group consisting of 
 
     
       
         
         
             
             
         
       
     
     and 
     
       
         
         
             
             
         
       
     
     in which n is an integer from 1 to 5; and m is independently an integer from 0 to 4 with the proviso that m is 0 only when Y is 
     
       
         
         
             
             
         
       
     
   
   
       24 . The article of  claim 23 , wherein the semiconductor substrate is a wafer. 
   
   
       25 . The article of  claim 24 , wherein the wafer is a silicon wafer, a ceramic wafer, a glass wafer, a metal wafer, or a plastic wafer. 
   
   
       26 . The article of  claim 24 , wherein the wafer is a copper coated wafer. 
   
   
       27 . An article produced according to a process, the process comprising the steps of:
 pretreating a substrate using a pretreatment composition; and   coating on the pretreated substrate a photosensitive composition, thereby forming a coated substrate;   wherein the pretreatment composition comprises:
 (1) at least one compound of structure VI
   V 1 —Y—V 2   VI 
 
   
     wherein
 Y is selected from the group consisting of S, O, NR 2 , (HOCH) p , and 
 
     
       
         
         
             
             
         
       
        in which p is an integer of from 1 to 4; each R 1  is independently selected from the group consisting of H, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, and a halogen; and each R 2  is independently selected from the group consisting of H, SH, CH 3 , C 2 H 5 , and a linear or branched C 1 -C 4  alkyl group containing a thiol group; and 
       V 1  and V 2  are independently selected from the group consisting of 
     
     
       
         
         
             
             
         
       
        in which m is independently an integer from 0 to 4 with the proviso that m=0 only when 
     
     
       
         
         
             
             
         
       
        and n is an integer from 1 to 5; and
 (2) at least one organic solvent. 
 
     
   
   
       28 . The article of  claim 27 , wherein the process further comprises baking the coated substrate to form a baked substrate. 
   
   
       29 . The article of  claim 28 , wherein the process further comprises exposing the baked coated substrate to actinic radiation to form an exposed coated substrate. 
   
   
       30 . The article of  claim 29 , wherein the process further comprises developing the exposed coated substrate with an aqueous developer, thereby forming an uncured relief image on the coated substrate. 
   
   
       31 . The article of  claim 27 , wherein the photosensitive composition comprises:
 (1) at least one polybenzoxazole precursor polymer selected from the group consisting of a positive working polybenzoxazole precursor polymer that does not have at least one acid labile functional group,   a positive working polybenzoxazole precursor polymer that does have at least one acid labile functional group, and   a negative working polybenzoxazole precursor polymer,   wherein when the polybenzoxazole precursor polymer is a positive working polybenzoxazole precursor polymer that does not contain at least one acid labile functional group, the photosensitive composition comprises at least one diazonaphthoquinone photoactive compound; when the polybenzoxazole precursor polymer is a positive working polybenzoxazole precursor polymer that does contain at least one acid labile functional group, the photosensitive composition comprises at least one photoacid generator; and when the polybenzoxazole precursor polymer is a negative working polybenzoxazole precursor polymer, Y cannot be (HOCH) p  in structure VI and the photosensitive composition comprises at least one photoactive compound that releases acid upon radiation and at least one latent crosslinker; and   (2) at least one solvent.   
   
   
       32 . The article of  claim 27 , wherein the organic solvent is N-methyl-2-pyrrolidone, N-ethyl-2-pyrrolidone, gamma-butyrolactone, N,N-dimethylacetamide, dimethyl-2-piperidone, N,N-dimethylformamide, 2-pentanone, cyclopentanone, 2-hexanone, 2-heptanone, propylene glycol monomethyl ether acetate, ethyl acetate, methyl methoxypropionate, ethyoxyethyl propionate, ethyl lactate, 1-methoxy-2-propanol, 1-pentanol, or a mixture thereof.