IP Library Granted Patent US 11,505,565
Granted Patent B2
US 11,505,565 · App. 16/204,960 · Granted Nov 22, 2022

Zwitterion compounds and photoresists comprising same

Inventors: Emad Aqad (Marlborough, MA); James F. Cameron (Marlborough, MA); James W. Thackeray (Marlborough, MA)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
C07F11/00G03F7/0042G03F7/0045G03F7/027G03F7/0397G03F7/16G03F7/70033
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Quick Facts
Patent No.
US 11,505,565
App. No.
16/204,960
Granted
Nov 22, 2022
Kind
B2
Abstract

New Te-zwitterion compounds are provided, including photoactive tellurium salt compounds useful for Extreme Ultraviolet Lithography.

Claims (49)

1. A photoresist composition comprising 1) a resin and 2) a zwitterion that comprises one or more Te atoms, wherein the zwitterion corresponds to Formula (I):

wherein,

R 1 , R 2 and R 3 are each the same or different non-hydrogen substituent;

two or more of R 1 , R 2 and R 3 are optionally taken together to form a ring;

Y is a single bond or a linker group; and

Z is an anionic group.

2. The photoresist composition of claim 1 wherein the zwitterion corresponds to Formula (II):

wherein in Formula (II):

R 4 , R 5 and each R 6 are the same or different non-hydrogen substituent;

p is an integer of 0 to 5;

Y is a single bond or a linker group,

Z is an anionic group; and

q is 0 or 1, and a sum of p and q does not exceed 5, and

if q is 0 then R 4 and/or R 5 comprise an anionic group.

3. The photoresist composition of claim 2 wherein R 4 and/or R 5 comprise an anionic group.

4. The photoresist composition of claim 1 wherein the zwitterion corresponds to Formula (IIIA):

wherein:

R 8 is a non-hydrogen substituent;

R 9 and R 10 are the same or different non-hydrogen ring substituent;

J a single bond or a connecting group;

s and s′ are each independently an integer of 0, 1, 2, 3, and 4;

Y is a single bond or a linker group;

Z is an anionic group;

each m and n is 0 or 1, and a sum of m and n does not exceed 1; and

if each of m and n is 0 then R 8 comprises an anionic group.

5. The photoresist composition of claim 4 wherein R 8 comprises an anionic group.

6. The photoresist composition of claim 1 wherein the zwitterion comprises a polymerizable group.

7. The photoresist composition of claim 1 wherein the photoresist composition comprises one or more acid generator compounds that are distinct from the one or more zwitterions.

8. A method for providing a photoresist relief image comprising:

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

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

9. The photoresist composition of claim 1 wherein the zwitterion comprises 1) one or more tellurium (Te) atoms and 2) anion and cation groups with both 1) and 2) both covalently bound to a single compound component.

10. The photoresist composition of claim 1 wherein the zwitterion has an equal number of cationic and anionic moieties.

11. The method of claim 8 wherein the zwitterion comprises 1) one or more tellurium (Te) atoms and 2) anion and cation groups with both 1) and 2) both covalently bound to a single compound component.

12. The method of claim 8 wherein the photoresist composition layer is exposed to radiation having a wavelength of 193 nm.

13. The method of claim 11 wherein the photoresist composition layer is exposed to radiation having a wavelength of 193 nm.

14. The photoresist composition of claim 1 wherein the zwitterion comprises one or more acid labile groups.

15. The photoresist composition of claim 1 , wherein the zwitterion corresponds to the following Formula (III):

wherein:

X is a single bond or a connecting group that together with the Te atom forms a single ring group or a multiple fused or linked ring structure;

R 7 is a non-hydrogen substituent;

each R 7′ is the same or different non-hydrogen ring substituent;

Y is a single bond or a linker group;

Z is an anionic group;

p is an integer from 0 to a maximum valance permitted by ring members;

q is 0 or a positive integer, and

if q is 0 then R 7 comprises an anionic group.

16. The photoresist composition of claim 15 , wherein R 7 comprises an anionic group.

17. The photoresist composition of claim 15 , wherein the zwitterion is part of the resin.

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 Nov 29, 2018
From: AQAD, EMAD, MR.; CAMERON, JAMES F., MR.; THACKERAY, JAMES W., MR.
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 047628/0961 →
Continuity (2)
Provisional Application 62593240 · Nov 30, 2017
Related Publication 20190161509A1 · May 30, 2019