Photoacid generators and lithographic resists comprising the same
View Patent ↗The present invention relates to photoacid generating compounds, lithographic resists comprising photoacid generating compounds, and to various lithographic processes techniques, and applications. In one embodiment, the present invention provides a photoacid generator of Formula (I):
1. A photoacid generator of Formula (III):
wherein
Y 1 , Y 2 , and Y 3 are independently selected from the group consisting of alkylene, alkenylene, fluoroalkylene, and fluoroalkenylene;
Z 1 , Z 2 , and Z 3 are independently selected from the group consisting of:
and —O—C(O)—O—R 7
wherein R 1 , R 2 , R 3 ,R 4 , R 5 , and R 6 are independently selected from the group consisting of -hydrogen, -alkyl, -alkylene, -fluoroalkyl, -fluoroalkenyl, -aryl, -substituted aryl, —O-alkyl, -halo, -cyano, and -nitro; and
wherein R 7 is selected from the group consisting of -hydrogen, -alkyl, -alkenyl, -fluoroalkyl, -fluoroalkenyl, -pyranyl, and -adamantyl,
L − is selected from the group consisting of a sulfonate compound, BF 4 − , PF 6 − , and SbF 6 − ; and
X + is selected from the group consisting of a sulfonium compound and an ionium compound.
2. The photoacid generator of claim 1 having the structure:
3. The photoacid generator of claim 1 having the structure:
4. The photoacid generator of claim 1 having the structure:
5. The photoacid generator of claim 1 having the structure:
6. The photoacid generator of claim 1 having the structure:
7. A dendrimer of Formula (IV):
wherein R 1 , R 2 , R 3 ,R 4 , R 5 , and R 6 are independently selected from the group consisting of:
and —O—C(O)—O—R 13
wherein R 7 , R 8 , R 9 ,R 10 , R 11 , and R 12 are independently selected from the group consisting of -hydrogen, -alkyl, -alkylene, -fluoroalkyl, -fluoroalkenyl, -aryl, -substituted aryl, —O-alkyl, -halo, -cyano, and -nitro; and
wherein R 13 is selected from the group consisting of -hydrogen, -alkyl, -alkenyl, -fluoroalkyl, -fluoroalkenyl, -pyranyl, and -adamantyl,
L − is selected from the group consisting of a sulfonate compound, BF 4 − , PF 6 − , and SbF 6 − ; and
X + is selected form the group consisting of a sulfonium compound and an ionium compound.
8. The dendrimer of claim 7 , wherein R 1 through R 6 are independently selected from the group consisting of:
and —O—C(O)—O—R 13 .
9. A lithographic resist comprising a photoacid generator selected from the group consisting of:
wherein X + is selected from the group consisting of a sulfonium compound and an ionium compound.
10. The lithographic resist of claim 9 , wherein the photoacid generator is
wherein X + is selected from the group consisting of a sulfonium compound and an ionium compound.
11. The lithographic resist of claim 9 , wherein the photoacid generator is
wherein X + is selected from the group consisting of a sulfonium compound and an ionium compound.
12. The lithographic resist of claim 9 , wherein the photoacid generator is
wherein X + is selected from the group consisting of a sulfonium compound and an ionium compound.
13. The lithographic resist of claim 9 , wherein the photoacid generator is
wherein X + is selected from the group consisting of a sulfonium compound and an ionium compound.
14. The lithographic resist of claim 9 , wherein the photoacid generator is
wherein X + is selected from the group consisting of a sulfonium compound and an ionium compound.
15. The lithographic resist of claim 9 , wherein the photoacid generator is
wherein X + is selected from the group consisting of a sulfonium compound and an ionium compound.
16. The lithographic resist of claim 9 , wherein the photoacid generator is
wherein X + is selected from the group consisting of a sulfonium compound and an ionium compound.
17. A lithographic resist comprising an adamantyl component and a photoacid generating component, wherein the photoacid generating component is selected from the group consisting of:
wherein X + is selected from the group consisting of a sulfonium compound and an ionium compound.
18. The lithographic resist of claim 17 further comprising a hydroxystyrene component.
19. The lithographic resist of claim 17 further comprising a γ-butyrolactone component.
20. A lithographic resist comprising a photoacid generator of Formula (III):
wherein
Y 1 , Y 2 , and Y 3 are independently selected from the group consisting of alkylene, alkenylene, fluoroalkylene, and fluoroalkenylene;
Z 1 , Z 2 , and Z 3 are independently selected from the group consisting of:
and —O—C(O)—O—R 7
wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of -hydrogen, -alkyl, -alkylene, -fluoroalkyl, -fluoroalkenyl, -aryl, -substituted aryl, —O-alkyl, -halo, -cyano, and -nitro; and
wherein R 7 is selected from the group consisting of -hydrogen, -alkyl, -alkenyl, -fluoroalkyl, -fluoroalkenyl, -pyranyl, and -adamantyl;
L − is selected from the group consisting of a sulfonate compound, BF 4− , PF 6 − , and SbF 6 − ; and
X + is selected from the group consisting of a sulfonium compound and an ionium compound, wherein the lithographic resist does not comprise a polymeric component.
21. The lithographic resist of claim 20 , wherein the photoacid generator is selected from the group consisting of:
22. The lithographic resist of claim 20 further comprising an adamantyl component.
23. The lithographic resist of claim 22 further comprising a hydroxystyrene component.
24. The lithographic resist of claim 22 further comprising a γ-butyrolactone component.
25. A lithographic resist comprising a dendrimer of Formula (IV):
wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from the group consisting of:
and —O—C(O)—O—R 13
wherein R 7 , R 8 , R 9 ,R 10 , R 11 , and R 12 are independently selected from the group consisting of -hydrogen, -alkyl, -alkylene, -fluoroalkyl, -fluoroalkenyl, -aryl, -substituted aryl, —O-alkyl, -halo, -cyano, and -nitro; and
wherein R 13 is selected from the group consisting of -hydrogen, -alkyl, -alkenyl, -fluoroalkyl, -fluoroalkenyl, -pyranyl, and -adamantyl,
L − is selected from the group consisting of a sulfonate compound, BF 4 − , PF 6 − , and SbF 6 − ; and
X + is selected form the group consisting of a sulfonium compound and an ionium compound.
26. The lithographic resist of claim 25 , wherein R 1 through R 6 are independently selected from the group consisting of:
and —O—C(O)—O—R 13 .
27. The lithographic resist of claim 25 further comprising an adamantyl component.
28. The lithographic resist of claim 27 further comprising a hydroxystyrene component.
29. The lithographic resist of claim 27 further comprising a y-butyrolactone component.
30. A method for producing a lithographic resist comprising:
blending a photoacid generating component with a first component, wherein the photoacid generating component is selected from the group consisting of:
wherein X + is selected from the group consisting of a sulfonium compound and an ionium compound.
31. The method of claim 30 , wherein the first component comprises an adamantyl component.
32. A method for producing a lithographic resist comprising:
copolymerizing a first component and a photoacid generating component, wherein the photoacid generating component is selected from the group consisting of:
wherein X + is selected from the group consisting of a sulfonium compound and an ionium compound.
33. The method of claim 32 , wherein the first component comprises a first monomer, first oligomer, or a first polymer.
34. A photoacid generator having the structure:
35. A photoacid generator having the structure:
36. A photoacid generator having the structure:
37. A photoacid generator having the structure:
38. A photoacid generator having the structure:
39. A photoacid generator having the structure:
40. A photoacid generator having the structure:
41. A photoacid generator having the structure:
42. A lithographic resist comprising a photoacid generator having the structure:
wherein
X + is selected from the group consisting of a sulfonium compound and an ionium compound.
43. A method of producing a lithographic resist comprising:
blending a photoacid generating component with a first component, wherein the photoacid generating component comprises a photoacid generator having the structure:
wherein
X + is selected from the group consisting of a sulfonium compound and an ionium compound.
44. A method of producing a lithographic resist comprising:
copolymerizing a first component and a photoacid generating component, wherein the photoacid generating component comprises a photoacid generator having the structure:
wherein
X + is selected from the group consisting of a sulfonium compound and an ionium compound.