IP Library Granted Patent US 9,696,629
Granted Patent B2
US 9,696,629 · App. 14/971,087 · Granted Jul 4, 2017

Photoresist pattern trimming compositions and methods

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Quick Facts
Patent No.
US 9,696,629
App. No.
14/971,087
Granted
Jul 4, 2017
Kind
B2
Abstract

Photoresist pattern trimming compositions are provided. The compositions comprise: a matrix polymer, an aromatic sulfonic acid and a solvent, wherein the aromatic sulfonic acid comprises one or more fluorinated alcohol group. Also provided are methods of trimming a photoresist pattern using the trimming compositions. The compositions and methods find particular applicability in the manufacture of semiconductor devices.

Claims (28)

1. A photoresist pattern trimming composition, comprising: a matrix polymer, an aromatic sulfonic acid and a solvent, wherein the aromatic sulfonic acid comprises one or more fluorinated alcohol group.

2. The photoresist pattern trimming composition of claim 1 , wherein the fluorinated alcohol group comprises a fluorine atom bonded to a carbon at the alpha position of the alcohol hydroxyl.

3. The photoresist pattern trimming composition of claim 1 , wherein the fluorinated alcohol group comprises a fluorinated group bonded pendant to a carbon at the alpha position of the alcohol hydroxyl.

4. The photoresist pattern trimming composition of claim 1 , wherein the aromatic sulfonic acid comprises a hexafluoroalcohol group.

5. The photoresist pattern trimming composition of claim 1 , wherein the aromatic sulfonic acid comprises a plurality of fluorinated alcohol groups.

6. The photoresist pattern trimming composition of claim 1 , wherein the fluorinated alcohol group is bonded to an aromatic ring of the aromatic sulfonic acid through an ester group.

7. The photoresist pattern trimming composition of claim 1 , wherein the aromatic sulfonic acid is chosen from the following acids:

8. The photoresist pattern trimming composition of claim 1 , wherein the matrix polymer is a poly(meth)acrylate polymer.

9. A method of trimming a photoresist pattern, comprising:

(a) providing a semiconductor substrate;

(b) forming a photoresist pattern on the substrate, wherein the photoresist pattern is formed from a photoresist composition comprising: a matrix polymer comprising an acid labile group, a photoacid generator, and a solvent;

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

(d) heating the coated substrate, thereby causing a change in polarity of the photoresist matrix polymer in a surface region of the photoresist pattern; and

(e) contacting the photoresist pattern with a rinsing agent to remove the surface region of the photoresist pattern, thereby forming a trimmed photoresist pattern.

10. The method of claim 9 , wherein the photoresist pattern is formed in an immersion lithography process.

11. The method of claim 9 , wherein the fluorinated alcohol group comprises a fluorine atom bonded to a carbon at the alpha position of the alcohol hydroxyl.

12. The method of claim 9 , wherein the fluorinated alcohol group comprises a fluorinated group bonded pendant to a carbon at the alpha position of the alcohol hydroxyl.

13. The method of claim 9 , wherein the aromatic sulfonic acid comprises a hexafluoroalcohol group.

14. The method of claim 9 , wherein the aromatic sulfonic acid comprises a plurality of fluorinated alcohol groups.

15. The method of claim 9 , wherein the fluorinated alcohol group is bonded to an aromatic ring of the aromatic sulfonic acid through an ester group.

16. The method of claim 9 , wherein the aromatic sulfonic acid is chosen from the following acids:

17. The method of claim 9 , wherein the matrix polymer is a poly(meth)acrylate polymer.

18. The photoresist pattern trimming composition of claim 1 , wherein the aromatic sulfonic acid is represented by the following general formula (I):

wherein Ar 1 represents an optionally substituted aromatic group; R 1 independently represents a group chosen from carboxyl, hydroxy, nitro, cyano, C1-5 alkoxy and formyl; Y independently represents a linking group; Z independently represents a group chosen from fluorinated alcohols, fluorinated esters, substituted or unsubstituted alkyl, C5 or higher monocyclic, polycyclic, fused polycyclic cycloaliphatic, or aryl, which may optionally comprise a heteroatom, provided at least one occurrence of Z is a fluorinated alcohol group; a is an integer of 0 or greater; b is an integer of 1 or greater; c is an integer of 1 or greater; and a+ b+ c is at least 2 and not greater than the total number of available aromatic carbon atoms of Ar 1.

19. The photoresist pattern trimming composition of claim 1 , wherein the aromatic acid is present in an amount of from 0.01 to 20 wt% based on total solids of the trimming composition.

20. The method of claim 9 , wherein the aromatic sulfonic acid is represented by the following general formula (I):

wherein Ar 3 represents an optionally substituted aromatic group; R 1 independently represents a group chosen from carboxyl, hydroxy, nitro, cyano, C1-5 alkoxy and formyl; Y independently represents a linking group; Z independently represents a group chosen from fluorinated alcohols, fluorinated esters, substituted or unsubstituted alkyl, C5 or higher monocyclic, polycyclic, fused polycyclic cycloaliphatic, or aryl, which may optionally comprise a heteroatom, provided at least one occurrence of Z is a fluorinated alcohol group; a is an integer of 0 or greater; b is an integer of 1 or greater; c is an integer of 1 or greater; and a+ b+ c is at least 2 and not greater than the total number of available aromatic carbon atoms of Ar 1.

21. The method of claim 9 , wherein the aromatic acid is present in an amount of from 0.01 to 20 wt% based on total solids of the trimming 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 Oct 27, 2016
From: KAUR, IRVINDER; LIU, CONG; ROWELL, KEVIN
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 040149/0858 →