Acetal/alicyclic polymers and photoresist compositions

• US 20030232273A1
• Filed: 10/09/2002
• Published: 12/18/2003
• Est. Priority Date: 10/09/2001
• Status: Abandoned Application

• Current Assignee: Shipley Company, LLC (Dow, Inc.)
• Original Assignee: Shipley Company, LLC (Dow, Inc.)
• Inventors: Coley, Suzanne, Adams, Timothy G.
• Application Number:
  US10/268,063
• Publication Number:
  US 20030232273A1
• Time in Patent Office: Days
• US Class Current: 430/270.1
• CPC Class Codes: G03F 7/0397 the macromolecular compound having an alicyclic moiety in a side chain

Abstract

The invention includes polymers that contain an alicyclic group (cage group) and acetal group which can undergo a deblocking reaction in the presence of photogenerated acid. The invention also provides photoresists that contain such polymers, particularly for imaging at short wavelengths such as sub-300 nm and sub-200 nm.

Claims

1. A photoresist composition comprising a photoactive component and a polymer that comprises an alicyclic unit and a photoacid-labile acetal unit.

2. The photoresist of claim 1 wherein the alicyclic unit is a substituent of the acetal unit.

3. The photoresist of claims 1 or 2 wherein the alicylic unit is a carbon alicyclic unit.

4. The photoresist of claims 1 or 2 wherein the alicyclic unit is a hetero alicylic unit.

5. The photoresist of claim 1 wherein the acetal unit is a polymer unit separate from the alicyclic unit.

6. The photoresist of any one of claims 1 through 4 wherein the polymer comprises a polymerized acrylate that comprises an acetal group and an alicyclic group.

7. The photoresist of any one of claims 1 through 6 wherein the polymer comprises phenyl groups with one or more acetal ring substituents.

8. The photoresist of any one of claims 1 through 7 wherein the polymer comprises aromatic units.

9. The photoresist of any one of claims 1 through 8 wherein the polymer comprises phenyl units.

10. The photoresist of any one of claims 1 through 6 wherein the polymer is substantially free of aromatic units.

11. The photoresist of any one of claims 1 through 10 wherein the polymer further comprises lactone, anhydride, or nitrile units.

12. The photoresist of any one of claims 1 through 11 wherein the polymer is a terpolymer, tetrapolymer or a pentapolymer.

13. A method of forming a positive photoresist relief image, comprising:

(a) applying a coating layer of a photoresist of any one of claims 1 through 12 on a substrate; and

(b) exposing and developing the photoresist layer to yield a relief image.

14. The method of claim 13 wherein the photoresist layer is exposed with radiation having a wavelength of less than about 300 nm.

15. The method of claim 13 wherein the photoresist layer is exposed with radiation having a wavelength of less than about 200 nm.

16. The method of claim 13 wherein the photoresist layer is exposed with radiation having a wavelength of about 248 nm, 193 nm or 157 mm.

17. An article of manufacture comprising a microelectronic wafer substrate having coated thereon a layer of the photoresist composition of any one of claims 1 through 12.

18. A polymer that comprises an alicyclic unit and a photoacid-labile acetal unit.

19. A polymer of claim 18 wherein the alicyclic unit is a substituent of the acetal unit.

20. The polymer of claim 18 wherein the acetal unit is a polymer unit separate from the alicyclic unit.

21. The polymer of claims 18, 19 or 20 wherein the alicylic unit is a carbon alicyclic unit.

22. The polymer of claims 18, 19 or 20 wherein the alicyclic unit is a hetero alicylic unit.

23. The polymer of any one of claims 18 through 22 wherein the polymer comprises a polymerized acrylate that comprises an acetal group and an alicyclic group.

24. The polymer of any one of claims 18 through 23 wherein the polymer comprises phenyl groups with one or more acetal ring substituents.

25. The polymer of any one of claims 18 through 24 wherein the polymer comprises aromatic units.

26. The polymer of any one of claims 18 through 24 wherein the polymer comprises phenyl units.

27. The polymer of any one of claims 18 through 24 wherein the polymer is substantially free of aromatic units.

28. The polymer of any one of claims 18 through 27 wherein the polymer further comprises lactone, anhydride, or nitrile units.

29. The polymer of any one of claims 18 through 28 wherein the polymer is a terpolymer, tetrapolymer or a pentapolymer.