Cyclic sulfonate compounds as photoacid generators in resist applications
Novel photoacid generator compounds are provided. Compositions that include the novel photoacid generator compounds are also provided. The present disclosure further provides methods of making and using the photoacid generator compounds and compositions disclosed herein. The compounds and compositions are useful as photoactive components in chemically amplified resist compositions for various microfabrication applications.
1. A sulfonic acid derivative compound represented by Formula (I):
wherein
X is either H or —OH; and
Y is a cation selected from either Formula A or B:
wherein
R 1 , R 2 , and R 3 are each independently selected from the group consisting of a vinyl group, an allyl group, optionally substituted (C 1 -C 20 )alkyl group, and an optionally substituted (C 6 -C 15 )aralkyl group, wherein R 1 and R 2 may be joined together along with the sulfur to which they are attached to form a ring; and
n is an integer from 1 to 10.
2. The sulfonic acid derivative compound of claim 1 wherein R 1 , R 2 , and R 3 are each independently an optionally substituted (C 6 -C 15 )aralkyl group; and X is H.
3. The sulfonic acid derivative compound of claim 1 wherein R 1 , R 2 , and R 3 are each independently an optionally substituted (C 6 -C 15 )aralkyl group; and X is —OH.
4. The sulfonic acid derivative compound of claim 1 wherein R 1 and R 2 are joined together along with the sulfur to which they are attached to form a ring; R 3 is an optionally substituted (C 6 -C 15 )aralkyl group; and X is H.
5. The sulfonic acid derivative compound of claim 1 wherein R 1 and R 2 are joined together along with the sulfur to which they are attached to form a ring; R 3 is an optionally substituted (C 6 -C 15 )aralkyl group; and X is —OH.
6. The sulfonic acid derivative compound of claim 1 selected from the group consisting of
7. The sulfonic acid derivative compound of claim 1 selected from the group consisting of
8. The sulfonic acid derivative compound of claim 1 selected from the group consisting of
9. A composition comprising:
(i) at least one photoacid generator compound represented by Formula (I):
wherein
X is either H or —OH; and
Y is a cation selected from either Formula A or B:
wherein
R 1 , R 2 , and R 3 are each independently selected from the group consisting of a vinyl group, an allyl group, optionally substituted (C 1 -C 20 )alkyl group, and an optionally substituted (C 6 -C 15 )aralkyl group, wherein R 1 and R 2 may be joined together along with the sulfur to which they are attached to form a ring; and
n is an integer from 1 to 10;
(ii) at least one photoresist polymer or copolymer;
(iii) an organic solvent; and, optionally,
(iv) an additive.
10. The composition of claim 9 wherein R 1 , R 2 , and R 3 are each independently an optionally substituted (C 6 -C 15 )aralkyl group; and X is H.
11. The composition of claim 9 wherein R 1 , R 2 , and R 3 are each independently an optionally substituted (C 6 -C 15 )aralkyl group; and X is —OH.
12. The composition of claim 9 wherein R 1 and R 2 are joined together along with the sulfur to which they are attached to form a ring; R 3 is an optionally substituted (C 6 -C 15 )aralkyl group; and X is H.
13. The composition of claim 9 wherein R 1 and R 2 are joined together along with the sulfur to which they are attached to form a ring; R 3 is an optionally substituted (C 6 -C 15 )aralkyl group; and X is —OH.
14. The composition of claim 9 wherein R 1 and R 2 are each independently an optionally substituted (C 6 -C 15 )aralkyl group; and X is H.
15. The composition of claim 9 wherein R 1 and R 2 are each independently an optionally substituted (C 6 -C 15 )aralkyl group; and X is —OH.
16. The composition of claim 9 wherein the photoacid generator compound is selected from the group consisting of
17. The composition of claim 9 wherein the photoacid generator compound is selected from the group consisting of
18. The composition of claim 9 wherein the photoacid generator compound is selected from the group consisting of
19. The composition of claim 9 wherein the solvent is a glycol ether selected from the group consisting of 2-methoxyethyl ether (diglyme), ethylene glycol monomethyl ether, and propylene glycol monomethyl ether.
20. The composition of claim 9 wherein the photoacid generator compound is present in the composition at from about 1 to about 10 wt. %; the at least one photoresist polymer or copolymer is present at from about 10 to about 40 wt. %; and the remainder of the composition is the organic solvent.