IP Library Granted Patent US 11,754,927
Granted Patent B2
US 11,754,927 · App. 16/871,228 · Granted Sep 12, 2023

Photoresist pattern trimming compositions and pattern formation methods

Inventors: Irvinder Kaur (Northborough, MA); Colin Liu (Shrewsbury, MA); Xisen Hou (Lebanon, NH); Kevin Rowell (Salem, MA); Mingqi Li (Shrewsbury, MA); Cheng-Bai Xu (Southborough, MA)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
G03F7/38C07C309/01C07C309/28C07C309/39G03F7/40H01L21/0273H01L21/31138
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Quick Facts
Patent No.
US 11,754,927
App. No.
16/871,228
Granted
Sep 12, 2023
Kind
B2
Abstract

Photoresist pattern trimming compositions comprise a polymer, an aromatic sulfonic acid, and an organic-based solvent system, wherein the aromatic sulfonic acid is of general formula (I): wherein: Ar 1 represents an aromatic group; R 1 independently represents a halogen atom, hydroxy, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted carbocyclic aryl, substituted or unsubstituted heterocyclic aryl, substituted or unsubstituted alkoxy, or a combination thereof, wherein adjacent R 1 groups together optionally form a fused ring structure with Ar 1 ; a represents an integer of 2 or more; and b represents an integer of 1 or more, provided that a+b is at least 3 and is not greater than the total number of available aromatic carbon atoms of Ar 1 , and two or more of R 1 are independently a fluorine atom or a fluoroalkyl group bonded directly to an aromatic ring carbon atom.

Claims (24)

1. A photoresist pattern trimming composition, comprising a polymer, an aromatic sulfonic acid, and an organic-based solvent system, wherein the aromatic sulfonic acid is of general formula (I):

wherein: Ar 1 represents a substituted or unsubstituted aromatic group; R 1 independently represents a fluorine atom or trifluoromethyl, and wherein an R 1 represents trifluoromethyl; a represents an integer of 2 or more; and b represents an integer of 1 or more, provided that a+b is at least 3 and is not greater than the total number of available aromatic carbon atoms of Ar 1 .

2. The photoresist pattern trimming composition of claim 1 , wherein the aromatic sulfonic acid is of general formula II:

wherein: R 1 independently represents a fluorine atom or trifluoromethyl, and wherein an R 1 represents trifluoromethyl and a represents an integer of from 2 to 5.

3. The photoresist pattern trimming composition of claim 1 , wherein the polymer comprises a repeat unit formed from a vinyl aromatic monomer.

4. The photoresist pattern trimming composition of claim 1 , wherein the organic-based solvent comprises a monoether.

5. The photoresist pattern trimming composition of claim 4 , wherein the organic-based solvent further comprises an alcohol and/or an ester.

6. The photoresist pattern trimming composition of claim 1 , wherein the composition is free of polymeric acids and polymeric acid generators.

7. The photoresist pattern trimming composition of claim 1 , wherein a first R 1 represents trifluoromethyl and a second R 1 represents a fluorine atom.

8. A pattern formation method, comprising:

(a) providing a semiconductor substrate;

(b) forming a photoresist pattern over the semiconductor substrate, wherein the photoresist pattern is formed from a photoresist composition comprising: a polymer comprising acid labile groups; and a photoacid generator;

(c) coating a pattern trimming composition of claim 1 over the photoresist pattern;

(d) heating the coated photoresist pattern; and

(e) rinsing the coated and heated photoresist pattern with a rinsing agent to remove residual pattern treatment composition.

9. The method of claim 8 , wherein the rinsing agent is an aqueous tetramethylammonium hydroxide solution.

10. The method of claim 8 , wherein the photoresist pattern is formed by deep-UV or EUV lithography.

11. The method of claim 8 , wherein the aromatic sulfonic acid is of general formula II:

wherein: R 1 independently represents a fluorine atom or trifluoromethyl, and wherein an R 1 represents trifluoromethyl; and a represents an integer of from 2 to 5.

12. The method of claim 8 , wherein the polymer comprises a repeat unit formed from a vinyl aromatic monomer.

13. The method of claim 8 , wherein the organic-based solvent comprises a monoether.

14. The method of claim 13 , wherein the organic-based solvent further comprises an alcohol and/or an ester.

15. The method of claim 8 , wherein the composition is free of polymeric acids and polymeric acid generators.

16. The method of claim 8 , wherein a first R 1 represents trifluoromethyl and a second R 1 represents a fluorine atom.

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 Jan 27, 2022
From: KAUR, IRVINDER; LIU, COLIN; HOU, XISEN; LI, MINGQI; XU, CHENG-BAI; ROWELL, KEVIN
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 058786/0668 →