IP Library Granted Patent US 10,248,020
Granted Patent B2
US 10,248,020 · App. 13/730,273 · Granted Apr 2, 2019

Acid generators and photoresists comprising same

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Quick Facts
Patent No.
US 10,248,020
App. No.
13/730,273
Granted
Apr 2, 2019
Kind
B2
Abstract

Acid generator compounds are provided that are particularly useful as a photoresist composition component. In one preferred aspect, photoresists are provided that comprise (i) a polymer; (ii) a first onium salt acid generator that produces a first acid upon exposure of the photoresist composition to activating radiation; and (iii) a second onium salt acid generator that 1) comprises a covalently bound acid-labile moiety and 2) produces a second acid upon exposure of the photoresist composition to activating radiation, wherein the first acid and second acid have pKa values that differ by at least 0.5.

Claims (29)

1. A photoresist composition, comprising:

(i) a polymer;

(ii) a first non-polymeric onium salt acid generator that produces a first acid upon exposure of the photoresist composition to activating radiation; and

(iii) a second onium salt acid generator that 1) comprises a covalently bound acid-labile moiety and 2) produces a second acid upon exposure of the photoresist composition to activating radiation;

wherein the first acid and second acid have pKa values that differ by at least 1; and

the acid-labile moiety of the second onium salt acid generator is a group of the formula —C(═O)O(CH 2 ) n (C═O)O-ALG, where n is an integer of from 1 to 12 and ALG is a group that results in an acid labile moiety.

2. The photoresist composition of claim 1 wherein the pKa value of the first acid is lower than the pKa value of the second acid.

3. A method for providing a photoresist relief image, comprising:

a) applying a coating layer of a photoresist composition of claim 1 on a substrate; and

b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

4. The method of claim 3 wherein the photoresist composition layer is exposed to EUV or e-beam radiation.

5. The photoresist composition of claim 1 wherein the first onium salt acid generator and the second onium salt acid generator are each not bound to a polymer.

6. The photoresist composition of claim 1 wherein at least one of the first onium salt acid generator and the second onium salt acid generator comprises a thioxanthone moiety.

7. The photoresist composition of claim 1 wherein at least one of the first onium salt acid generator and the second onium salt acid generator comprises a dibenzothiophene moiety.

8. The photoresist composition of claim 1 wherein the first acid and second acid have pKa values that differ by at least 1.5.

9. The photoresist composition of claim 1 wherein the first acid and second acid have pKa values that differ by at least 2.

10. The photoresist composition of claim 1 wherein the first acid and second acid have pKa values that differ by at least 3.

11. The photoresist composition of claim 1 wherein the first acid and second acid have pKa values that differ by at least 4.

12. The photoresist composition of claim 1 wherein both the first onium salt acid generator and the second onium salt acid generator are sulfonium compounds.

13. A photoresist composition of claim 1 further comprising a non-photo-destroyable base.

14. A photoresist composition, comprising:

(i) a polymer;

(ii) a first non-polymeric onium salt acid generator that produces a first acid upon exposure of the photoresist composition to activating radiation; and

(iii) a second onium salt acid generator that 1) comprises a covalently bound acid-labile moiety and 2) produces a second acid upon exposure of the photoresist composition to activating radiation;

wherein the first acid and second acid have pKa values that differ by at least 1;

wherein at least one of the first onium salt acid generator and the second onium salt acid generator comprises a thioxanthone moiety; and

wherein the first onium salt acid generator and the second onium salt acid generator are each not bound to a polymer.

15. A photoresist composition of claim 14 further comprising a non-photo-destroyable.

16. A photoresist composition of claim 14 wherein the acid-labile moiety of the second onium salt acid generator is a group of the formula —C(═O)O(CH 2 ) n (C═O)O-ALG, where n is an integer of from 1 to 12 and ALG is a group that results in an acid labile moiety.

Assignments (5)
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 →
RELEASE OF SECURITY INTEREST Recorded Oct 31, 2014
From: SILICON VALLEY BANK
To: XRS CORPORATION
Reel/Frame 034084/0366 →
FIRST SUPPLEMENT TO INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Mar 26, 2014
From: XRS CORPORATION
To: SILICON VALLEY BANK
Reel/Frame 032527/0121 →
Cited By (1)
US 12,493,241