IP Library Granted Patent US 8,088,547
Granted Patent B2
US 8,088,547 · App. 11/665,506 · Granted Jan 3, 2012

Resist composition

Assignee: Dow Corning Corporation
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Quick Facts
Patent No.
US 8,088,547
App. No.
11/665,506
Granted
Jan 3, 2012
Kind
B2
Abstract

A resist composition comprising (A) a hydrogen silsesquioxane resin, (B) an acid dissociable group-containing compound, (C) a photo-acid generator, (D) an organic solvent and optionally (E) additives. The resist composition has improved lithographic properties (such as high etch-resistance, transparency, resolution, sensitivity, focus latitude, line edge roughness, and adhesion) suitable as a photoresist.

Claims (40)

1. A resist composition consisting of (A) a hydrogen silsesquioxane resin having the formula

(HSi(OH)O 2/2 ) w (HSi(OR 1 )O 2/2 ) x (HSiO 3/2 ) y ((SiO 4/2 ) z ,

where R 1 is a linear or branched C 1 to C 6 alkyl or alkoxy group; w=0 to 1, x=0 to 1, y is >0 to 1,z is 0 to 1 and w+x+y+z≈1,

(B) an acid dissociable group-containing compound, (C) a photo-acid generator, (D) an organic solvent, and optionally (E) an additive.

2. The resist composition as claimed in claim 1 wherein the hydrogen silsesquioxane resin has a molecular weight of 1,000 to 50,000.

3. The resist composition as claimed in claim 1 wherein the acid dissociable groups in (B) have the formula

wherein each R 3 are independently a linking group;

R 4 a second linking group;

L is selected from the group consisting of linear or branch alkylene groups having 1 to 10 carbon atoms, fluoroalkylene groups having 2 to 20 carbon atoms, substituted and unsubstituted arylene groups, substituted and unsubstituted cycloalkylene groups, and substituted and unsubstituted alkarylene groups;

R 5 is hydrogen, linear or branched alkyl or fluoroalkyl;

R 6 is alkyl or fluoroalkyl;

Z is an acid-cleavable group; and

g may have a value of 0 or 1 and

h may have the value of 0 or 1; and

k may have the value of 0 or 1.

4. The resist composition as claimed in claim 3 wherein Z is selected from —OH, —COOH, esters of the formula —COOR 7 , carbonates of the formula —OCOOR 8 , ethers of the formula —OR 9 , wherein R 7 , R 8 and R 9 are selected to render Z acid-cleavable.

5. The resist composition as claimed in claim 3 wherein Z is an ester of the formula —COOR 7 and R 7 is a tertiary alkyl group.

6. The resist composition as claimed in claim 1 wherein (B) is poly(t-butylmethacrylate).

7. The resist composition as claimed in claim 1 wherein (B) is poly(t-butoxycarbonyl norbornyl silsesquioxane).

8. The resist composition as claimed in claim 1 wherein (B) is poly (methyl-co-t-butoxycarbonyl norbornyl)silsesquioxane.

9. The resist composition as claimed in claim 1 wherein (B) is present in an amount in a range of 20 to 50 parts by weight based on 100 parts by weight of (A).

10. The resist composition as claimed in claim 1 wherein (C) is selected from onium salts, halogen-containing compounds, diazoketone compounds, sulfone compounds, sulfonate compounds.

11. The resist composition as claimed in claim 10 wherein the acid generator is a sulfonate compound.

12. The resist composition as claimed in claim 1 wherein the photo-acid generator is present in an amount in a range of 2 to 5 parts by weight based on 100 parts by weight of (B).

13. The resist composition as claimed in claim 1 wherein there is additionally present (E) at least one additive selected from acid-diffusion controllers, surfactants, dissolution inhibitors, cross-linking agents, sensitizers, halation inhibitors, adhesion promoters, storage stabilizers, anti-foaming agents, coating aids, and plasticizers.

14. The resist composition as claimed in claim 13 wherein (E) is present in amount of less than 20 wt % based on solids.

15. The resist composition as claimed in claim 1 wherein (D) is selected from ether-, ester-, hydroxyl- and ketone-containing compounds.

16. The resist composition as claimed in claim 15 wherein (D) is present in an amount of 80 to 90 wt % based on the weight of the total photoresist composition.

17. A process for generating a resist image on a substrate comprising

(a) coating a substrate with a film comprising the resist composition as claimed in claim 1 ;

(b) imagewise exposing the film to radiation to produce an exposed film; and

(c) developing the exposed film to produce an image.

18. The process as claimed in claim 17 wherein the film is coated on the substrate by spin-coating.

19. The process as claimed in claim 17 wherein the film is dried before exposure to the radiation.

20. The process as claimed in claim 17 wherein the exposed film has a thickness of 0.01 to 5 microns.

21. The process as claimed in claim 17 wherein the radiation is selected from UV, X-ray, e-beam and EUV.

22. The process as claimed in claim 17 wherein the radiation has a wavelength in the range of 157 nm to 365 nm.

23. The process as claimed in claim 17 wherein the radiation has a wavelength in the range of 157 nm to 193 nm.

24. The process as claimed in claim 17 wherein the exposed film is heated at a temperature of 30° C. to 200° C. prior to being developed.

25. The process as claimed in claim 17 wherein the exposed film is developed by contacting the exposed film with an aqueous base solution.

Continuity (2)
Provisional Application 60624319 · Nov 2, 2004
Related Publication 20070264587A1 · Nov 15, 2007