Coating compositions for use with an overcoated photoresist
View Patent ↗Organic coating compositions, particularly antireflective coating compositions for use with an overcoated photoresist, are provided that comprise that comprise a surface agent of the Formula (I). where A and B are each independently hydrogen, optionally substituted alkyl or optionally substituted aryl; X and Y are each independently hydrogen, optionally substituted alkyl or optionally substituted carbocyclic aryl; and n is a positive integer. Preferred coating compositions can provide improved pattern collapse margin of an overcoated photoresist layer.
1. A method for forming a photoresist relief image, comprising:
a) applying on a substrate a layer of a coating composition comprising 1) a matrix polymer that comprises polyester linkages; 2) a surface energy control agent; 3) a crosslinking agent; and 4) a thermal acid generator, wherein the coating composition does not comprise fluorine;
b) thermally treating the applied coating composition layer; and thereafter
c) applying a layer of a photoresist composition above the coating composition layer,
wherein the surface energy control agent comprises a structure corresponding to the following Formula (I):
wherein A and B are each independently hydrogen, or optionally substituted alkyl, provided that at least one or A and B is not hydrogen;
X and Y are each independently hydrogen, optionally substituted alkyl or optionally substituted carbocyclic aryl; and
n is a positive integer, and the surface energy control agent has a number average molecule weight of 300 to 1,000.
2. The method of claim 1 wherein the photoresist composition is imaged with activating radiation and the imaged photoresist composition layer is developed to provide a photoresist relief image.
3. The method of claim 2 wherein a developer is applied to the imaged photoresist composition layer and unexposed portions of the photoresist layer are removed by the developer.
4. The method of claim 1 wherein the coating composition comprises the surface energy control agent in an amount of 1 weight percent to 10 weight percent based on total solid content of the coating composition.
5. The method of claim 1 wherein the surface energy control agent is a poly(ethylene glycol)methyl ether.
6. The method of claim 1 wherein the matrix polymer further comprises cyanurate groups.
7. The method of claim 1 further comprising imaging the photoresist composition layer with 193 nm activating radiation.
8. The method of claim 1 further comprising imaging the photoresist composition layer with EUV radiation.
9. The method of claim 1 wherein substituents of the substituted alkyl of A and B are selected from the group consisting of halogen, nitro, hydroxy, amino, alkyl, alkenyl, alkylamino, and carbocyclic aryl.
10. A coated substrate comprising:
a substrate having thereon:
1) a coating composition comprising a) a matrix polymer that comprises polyester linkages; b) a surface energy control agent, c) a crosslinking agent; and d) a thermal acid generator, wherein the coating composition does not comprise fluorine; and
2) a layer of a photoresist composition above the coating composition layer, wherein the surface energy control agent comprises a structure corresponding to the following Formula (I):
wherein A and B are each independently hydrogen, or optionally substituted alkyl, provided that at least one or A and B is not hydrogen, and wherein substituents of the substituted alkyl of A and B are selected from the group consisting of halogen, nitro, hydroxy, amino, alkyl, alkenyl, alkylamino, and carbocyclic aryl;
X and Y are each independently hydrogen, optionally substituted alkyl or optionally substituted carbocyclic aryl; and
n is a positive integer, and the surface energy control agent has a number average molecular weight of 300 to 1,000.
11. The substrate of claim 10 wherein the matrix polymer further comprises cyanurate groups.
12. A coating composition for use with an overcoated photoresist composition layer, the coating composition comprising:
1) a crosslinker agent;
2) a matrix polymer comprising polyester linkages;
3) a surface energy control agent which is distinct from the matrix polymer and comprising a structure corresponding to the following Formula (I):
wherein A and B are each independently hydrogen, or optionally substituted alkyl, provided that at least one or A and B is not hydrogen, and wherein substituents of the substituted alkyl of A and B are selected from the group consisting of halogen, nitro, hydroxy, amino, alkyl, alkenyl, alkylamino, and carbocyclic aryl;
X and Y are each independently hydrogen, optionally substituted alkyl or optionally substituted carbocyclic aryl; and
n is a positive integer,
the surface energy control agent has a number average molecular weight of 300 to 1,000, and
4) a thermal acid generator.
wherein the coating composition does not comprise fluorine.
13. The coating composition of claim 12 wherein the coating composition is formulated with a solvent carrier.
14. The coating composition of claim 12 wherein the surface energy control agent is a poly(ethylene glycol)methyl ether.
15. The composition of claim 12 wherein the matrix polymer comprises cyanurate groups.