Coating compositions for use with an overcoated photoresist
View Patent ↗Coating compositions for use with an overcoated photoresist are provided where the coating composition comprises a resin containing cyanurate groups and hydrophobic groups. The coating composition can enhance resolution of an overcoated photoresist relief image.
1. A coating composition for use with an overcoated photoresist, the coating composition comprising a resin comprising cyanurate groups and hydrophobic groups,
wherein the resin has halogen substitution.
2. The coating composition of claim 1 wherein the hydrophobic groups are selected from hydroxy and ether.
3. The coating composition of claim 1 wherein the resin is prepared from reagents comprising a cyanurate compound comprising substitution of multiple cyanurate nitrogen ring atoms by distinct carboxy and/or carboxy ester groups.
4. The coating composition of claim 3 wherein the cyanurate compound corresponds to the following Formula I:
wherein at least two of the radicals R 1 OOC(CX 2 ) n —, R 2 — and R 3 OOC(CX 2 ) n — are different acid or ester groups; and
R 1 , R 2 and R 3 and each X are each independently hydrogen or non-hydrogen substituents; and
n and m are the same or different and each a whole number.
5. A coating composition of claim 1 wherein the resin comprises a covalently linked crosslinker group.
6. A coating composition of claim 1 wherein the resin comprises polyester linkages.
7. A coated substrate comprising:
a layer of an antireflective composition of claim 1 ;
a photoresist layer over the coating composition layer.
8. A method of forming a photoresist relief image, comprising:
applying an antireflective coating composition on a substrate, the antireflective coating composition comprising a resin comprising cyanurate groups and hydrophobic groups, wherein the resin has halogen substitution;
applying a photoresist composition above the coating composition layer; and
exposing and developing the photoresist layer to provide a resist relief image.
9. The method of claim 8 wherein the antireflective composition is crosslinked prior to applying the photoresist composition.
10. The coating composition of claim 3 wherein the cyanurate compound corresponds to the following Formula IA:
wherein at least two of the radicals R 1 OOC(CH 2 ) n —, R 2 — and R 3 OOC(CH 2 ) m — are different acid or ester groups;
R 1 , R 2 and R 3 are each independently hydrogen or non-hydrogen substituent; and
n and m are the same or different and each a positive integer.
11. The coating composition of claim 10 wherein in Formula IA:
R 1 , R 2 and R 3 are each optionally substituted C 1-10 alkyl, optionally substituted alkenyl or alkynyl having 2 to 10 carbon atoms, optionally substituted alkanoyl having 1 to 10 carbon atoms;
optionally substituted alkoxy having 1 to 10 carbon atoms; optionally substituted alkylthio having 1 to 10 carbon atoms; optionally substituted alkylsulfinyl 1 to 10 carbon atoms; optionally substituted alkylsulfonyl having 1 to 10 carbon atoms; optionally substituted carboxy have 1 to 10 carbon atoms; optionally substituted alkaryl, optionally substituted carbocyclic aryl; or optionally substituted heteralicyclic or heteroaromatic group; and n and m are each a positive integer.
12. The coating composition of claim 1 wherein the resin has fluorine substitution.
13. The method of claim 8 wherein the resin has fluorine substitution.
14. The method of claim 8 wherein the resin is prepared from reagents comprising a compound corresponding to the following Formula I:
wherein at least two of the radicals R 1 OOC(CX 2 ) n —, R 2 — and R 3 OOC(CX 2 ) n — are different acid or ester groups; and
R 1 , R 2 and R 3 and each X are each independently hydrogen or non-hydrogen substituents; and
n and m are the same or different and each a whole number.
15. The method of claim 8 wherein the resin is prepared from reagents comprising a compound corresponding to the following Formula IA:
wherein at least two of the radicals R 1 OOC(CH 2 ) n —, R 2 — and R 3 OOC(CH 2 ) m — are different acid or ester groups;
R 1 , R 2 and R 3 are each independently hydrogen or non-hydrogen substituent; and
n and m are the same or different and each a positive integer.
16. The method of claim 15 wherein in Formula IA:
R 1 , R 2 and R 3 are each optionally substituted C 1-10 alkyl, optionally substituted alkenyl or alkynyl having 2 to 10 carbon atoms, optionally substituted alkanoyl having 1 to 10 carbon atoms; optionally substituted alkoxy having 1 to 10 carbon atoms; optionally substituted alkylthio having 1 to 10 carbon atoms; optionally substituted alkylsulfinyl 1 to 10 carbon atoms; optionally substituted alkylsulfonyl having 1 to 10 carbon atoms; optionally substituted carboxy have 1 to 10 carbon atoms; optionally substituted alkaryl, optionally substituted carbocyclic aryl; or optionally substituted heteralicyclic or heteroaromatic group; and n and m are each a positive integer.
17. The method of claim 8 wherein the resin comprises polyester linkages.