IP Library Granted Patent US 9,499,513
Granted Patent B2
US 9,499,513 · App. 14/611,768 · Granted Nov 22, 2016

Acid generators and photoresists comprising same

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Quick Facts
Patent No.
US 9,499,513
App. No.
14/611,768
Granted
Nov 22, 2016
Kind
B2
Abstract

Acid generator compounds are provided that are particularly useful as photoresist composition components. Preferred acid generators include cyclic sulfonium compounds that comprise a covalently linked acid-labile group.

Claims (20)

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

a) applying a coating layer of a photoresist composition on a substrate, the photoresist composition comprising:

(a) a polymer; and

(b) an acid generator selected from the group consisting of:

(i) 5-(4-(2-(1-ethylcyclopentyloxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium 3-hydroxyadamantane-acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate;

(ii) 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 3-hydroxyadamantane-acetoxy-1,1,2,2-tetrafluorobutane-1-sulfonate;

(iii) 5-(4-(2-(1-ethylcyclopentyl oxy)-2-oxoethoxy)-3,5-dimethylphenyl)-5H-dibenzo[b,d]thiophenium 4-((4R)-4-((8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoyloxy)-1,1,2,2-tetrafluorobutane-1-sulfonate; and

(iv) 5-(3,5-dimethyl-4-(2-oxo-2-(2-phenylpropan-2-yloxy)ethoxy)phenyl)-5H-dibenzo[b,d]thiophenium 44(4R)-44(8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-ylipentanoyloxy)-1, 1,2,2-tetrafluorobutane-1-sulfonate; and

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

2. The method of claim 1 wherein the photoresist composition layer is exposed to EUV radiation.

3. The method of claim 1 wherein the photoresist composition layer is exposed to e beam radiation.

4. An acid generator that comprises a cation component selected from:

5. A photoresist composition comprising:

(a) a polymer; and

(b) an acid generator of claim 4 .

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

a) applying a coating layer of a photoresist composition of claim 5 on a substrate; and

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

7. The method of claim 6 wherein the photoresist composition layer is exposed to EUV radiation.

8. The method of claim 6 wherein the photoresist composition layer is exposed to 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 Apr 26, 2016
From: CAMERON, JAMES F.; JAIN, VIPUL; LABEAUME, PAUL J.; SUNG, JIN WUK; THACKERAY, JAMES W.
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 038380/0929 →