IP Library Granted Patent US 12,372,867
Granted Patent B2
US 12,372,867 · App. 14/027,400 · Granted Jul 29, 2025

Photoresists comprising multiple acid generator compounds

Inventors: James W. Thackeray (Braintree, MA); Jin Wuk Sung (Worcester, MA); Paul J. LaBeaume (Auburn, MA); Vipul Jain (North Grafton, MA)
Assignee: DUPONT ELECTRONIC MATERIALS INTERNATIONAL, LLC
G03F7/0045G03F7/0046G03F7/0392G03F7/0397G03F7/20
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Quick Facts
Patent No.
US 12,372,867
App. No.
14/027,400
Granted
Jul 29, 2025
Kind
B2
Abstract

The present invention relates to new photoresist compositions that comprise (a) a polymer comprising an acid generator bonded thereto; and (b) an acid generator compound that is not bonded to the polymer and that comprises one or more acid-labile groups.

Claims (20)

1. A photoresist composition comprising:

(a) a polymer comprising an acid generator bonded thereto; and

(b) an acid generator compound that is not bonded to the polymer and that comprises a thioxanthone moiety or a dibenzothiophene moiety, and one or more acid-labile groups,

wherein the (a) bonded acid generator comprises i) a thioxanthone moiety or a dibenzothiophene moiety, and ii) an acid-labile group;

wherein the (a) bonded acid generator and/or the (b) acid generator compound comprise a sulfonium moiety and/or an iodonium moiety;

wherein the (a) bonded acid generator comprises an anion component covalently bonded to the polymer;

wherein the (a) bonded acid generator does not comprise a cation component covalently bonded to the polymer; and

wherein the acid-labile group of the (b) acid generator compound is on a cation component of the acid generator compound.

2. The photoresist composition of claim 1 wherein the (a) bonded acid generator comprises an acid-labile ester group.

3. The photoresist composition of claim 1 wherein the (a) bonded acid generator comprises an acid-labile acetal group.

4. The photoresist composition of claim 1 , wherein the one or more acid-labile groups of the (a) acid generator compound are each independently an optionally substituted ethylcyclopentyl ester, an optionally substituted methyladamantyl ester, an optionally substituted ethyl adamantyl ester, an optionally substituted t-butylester, an optionally substituted phenyl ester, or an optionally substituted naphthyl ester.

5. The photoresist composition of claim 1 , wherein the one or more acid-labile groups of the (a) acid generator compound are each independently 1-ethylcyclopentyl or methyladamantyl.

6. The photoresist composition of claim 1 , wherein the acid-labile group of the (b) acid generator compound is an optionally substituted ethylcyclopentyl ester, an optionally substituted methyladamantyl ester, an optionally substituted ethyl adamantyl ester, an optionally substituted t-butylester, an optionally substituted phenyl ester, or an optionally substituted naphthyl ester.

7. The photoresist composition of claim 1 , wherein the acid-labile group of the (b) acid generator compound is 1-ethylcyclopentyl or methyladamantyl.

8. The photoresist composition of claim 1 , wherein the (b) acid generator compound comprises an acid-labile ester group.

9. The photoresist composition of claim 1 , wherein the (b) acid generator compound comprises an acid-labile acetal group.

10. 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.

11. The method of claim 10 wherein the photoresist composition layer is exposed to EUV or e-beam radiation.

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 Mar 3, 2017
From: THACKERAY, JAMES W.; SUNG, JIN WUK; LABEAUME, PAUL J.; JAIN, VIPUL
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 041457/0090 →