IP Library Granted Patent US 9,244,355
Granted Patent B2
US 9,244,355 · App. 11/978,910 · Granted Jan 26, 2016

Compositions and processes for immersion lithography

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Quick Facts
Patent No.
US 9,244,355
App. No.
11/978,910
Granted
Jan 26, 2016
Kind
B2
Abstract

New photoresist compositions are provided that are useful for immersion lithography. Preferred photoresist compositions of the invention comprise one or more materials having a water contact angle that can be changed by treatment with base and/or one or more materials that comprise fluorinated photoacid-labile groups and/or one or more materials that comprise acidic groups spaced from a polymer backbone. Particularly preferred photoresists of the invention can exhibit reduced leaching of resist materials into an immersion fluid contacting the resist layer during immersion lithography processing.

Claims (29)

1. A method for processing a photoresist composition, comprising:

(a) applying on a substrate a photoresist composition comprising:

(i) one or more resins which comprise one or more photoacid-labile groups,

(ii) a photoactive component, and

(iii) one or more materials that comprise fluorinated photoacid-labile groups, where a fluorinated cleavage product is generated during exposure and post-exposure treatment, whereby the (iii) one or more materials migrate toward upper portions of the photoresist composition layer during the applying; and

(b) immersion exposing the applied photoresist composition to radiation activating for the photoresist composition,

wherein the fluorinated cleavage product is selected from the group consisting of:

in which R 2 is CH 2 , CH 2 CF 2 , CH 2 CF 2 CF 2 , CH 2 CF 2 CF 2 CF 2 , or CH(CF 3 ).

2. The method of claim 1 wherein the photoresist composition comprises one or more substantially non-mixable materials.

3. The method of claim 1 wherein the photoresist layer is exposed to radiation having a wavelength of 193 nm activating for the photoresist composition.

4. The method of claim 1 wherein the (iii) one or more materials have a lower surface energy and/or small hydrodynamic volume than the (i) one or more resins.

5. The method of claim 1 wherein the photoresist composition provides a decreased amount of acid or organic material to be detected in immersion fluid following the immersion exposure.

6. The method of claim 1 wherein the photoresist composition as applied as a spin-coated layer provides a receding water contact angle of in excess of 70 degrees.

7. A method for processing a photoresist composition, comprising:

(a) applying on a substrate a photoresist composition layer comprising:

(i) one or more resins which comprise one or more photoacid-labile groups,

(ii) a photoactive component, and

(iii) one or more materials that comprise fluorinated photoacid-labile groups, where a fluorinated cleavage product is generated during exposure and post-exposure treatment, wherein the (iii) one or more materials have a lower surface energy and/or small hydrodynamic volume than the (i) one or more resins; and

(b) immersion exposing the applied photoresist layer to radiation activating for the photoresist composition,

wherein the fluorinated cleavage product is selected from the group consisting of:

in which R 2 is CH 2 , CH 2 CF 2 , CH 2 CF 2 CF 2 , CH 2 CF 2 CF 2 CF 2 , or CH(CF 3 ).

8. The method of claim 1 wherein the (iii) one or more materials have a lower surface energy than the (i) one or more resins.

9. The method of claim 7 wherein the (iii) one or more materials have a lower surface energy than the (i) one or more resins.

10. The method of claim 7 wherein the photoresist composition as applied as a spin-coated layer provides a receding water contact angle of in excess of 70 degrees.

11. The method of claim 7 wherein the photoresist composition provides a decreased amount of acid or organic material to be detected in immersion fluid following the immersion exposure.

12. The method of claim 1 wherein the (iii) one or more materials that comprise fluorinated photoacid-labile groups are present in the photoresist composition in an amount of 0.1 to 20 weight percent based on total weight of the fluid photoresist composition.

13. The method of claim 1 wherein the (iii) one or more materials that comprise fluorinated photoacid-labile groups are present in the photoresist composition in an amount of up to 1 weight percent based on total solids of the photoresist composition.

14. The method of claim 1 wherein the (iii) one or more materials that comprise fluorinated photoacid-labile groups are present in the photoresist composition in an amount of up to 2 weight percent based on total solids of the photoresist composition.

15. The method of claim 1 wherein the (iii) one or more materials that comprise fluorinated photoacid-labile groups are present in the photoresist composition in an amount of up to 3 weight percent based on total solids of the photoresist composition.

Assignments (4)
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
CHANGE OF NAME Recorded Oct 29, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS LLC
To: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC
Reel/Frame 069272/0383 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 21, 2008
From: CAPORALE, STEFAN J.; BARCLAY, GEORGE G.; WANG, DEYAN; JIA, LI
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 020855/0890 →