IP Library Granted Patent US 11,932,713
Granted Patent B2
US 11,932,713 · App. 16/236,883 · Granted Mar 19, 2024

Monomers, polymers and lithographic compositions comprising same

Inventors: Emad Aqad (Marlborough, MA); James F. Cameron (Marlborough, MA); James W. Thackeray (Marlborough, MA)
Assignee: ROHM AND HAAS ELECTRONIC MATERIALS LLC
C08F230/04C07F11/00C09D133/04C09D133/14C09D143/00G03F7/0042G03F7/038G03F7/039G03F7/091G03F7/094G03F7/11G03F7/162G03F7/168G03F7/2004G03F7/322G03F7/38
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Quick Facts
Patent No.
US 11,932,713
App. No.
16/236,883
Granted
Mar 19, 2024
Kind
B2
Abstract

New monomer and polymer materials that comprise one or more Te atoms. In one aspect, tellurium-containing monomers and polymers are provided that are useful for Extreme Ultraviolet Lithography.

Claims (56)

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

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

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

wherein: the photoresist composition comprises:

i) one or more polymers that comprise repeating units formed by the polymerization of a tellurium-containing monomer: wherein the tellurium containing monomer

repeating units formed by the polymerization of a tellurium-containing monomer: wherein the tellurium containing monomer comprises a tellurophene heterocycle and one or more ethylenically polymerizable groups, or

the tellurium-containing monomer is of Formula (IIIC); and

ii) one or more acid generator compounds

wherein,

R is hydrogen or an optionally substituted C 1-16 alkyl;

S is a chemical bond or a chain having from 1 to 20 carbon and oxygen atoms that are optionally substituted;

each R 1 is the same or different non-hydrogen substituent;

R 2 is a non-hydrogen substituent; and

n is an integer of 0 to 4,

wherein the tellurium-containing monomer of Formula (IIIC) further comprises one or more acid-cleavable groups.

2. The method of claim 1 , wherein the tellurium-containing monomer comprises one or more optionally substituted acrylate moiety, optionally substituted acrylamide moiety, optionally substituted vinyl ether moiety or a cyclic olefin moiety.

3. The method of claim 1 , wherein the tellurium-containing monomer comprises one more optionally substituted methacrylate, fluoromethacrylate, cyanoacrylate, methylacrylamide, vinyl ether, norbornyl acrylate moiety, optionally substituted acrylamide moiety, optionally substituted lactone, optionally substituted vinyl ether moiety or a cyclic olefin moiety.

4. The method of claim 1 wherein the tellurium-containing monomer comprises one or more alkyl, fluoroalkyl, carbocyclic aryl, heteroaryl, sulfonic ester or sulfonamide.

5. The method of claim 1 , wherein the tellurium-containing monomer is selected from:

6. The method of claim 1 , wherein the tellurium-containing monomer is selected from the group consisting of:

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

a) applying a layer of an underlayer coating composition on a substrate;

b) applying a layer of a photoresist composition above the underlayer coating composition layer, wherein the underlayer coating composition and the photoresist composition are different; and

c) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition layer,

wherein the underlayer coating composition comprises: one or more polymers that comprise repeating units formed by the polymerization of a tellurium-containing monomer: wherein the tellurium containing monomer

repeating units formed by the polymerization of a tellurium-containing monomer: wherein the tellurium containing monomer comprises a tellurophene heterocycle and one or more ethylenically polymerizable groups, or

the tellurium-containing monomer is of Formula (IIIC);

wherein,

R is hydrogen or an optionally substituted C 1-16 alkyl;

S is a chemical bond or a chain having from 1 to 20 carbon and oxygen atoms that are optionally substituted;

each R 1 is the same or different non-hydrogen substituent;

R 2 is a non-hydrogen substituent; and

n is an integer of 0 to 4.

8. The method of claim 7 , wherein the tellurium-containing monomer further comprises one or more acid-cleavable groups, polar groups and/or base reactive groups.

9. The method of claim 7 , wherein tellurium-containing monomer comprises one or more optionally substituted acrylate moiety, optionally substituted acrylamide moiety, optionally substituted vinyl ether moiety or a cyclic olefin moiety.

10. The method of claim 7 , wherein the tellurium-containing monomer comprises one more optionally substituted methacrylate, fluoromethacrylate, cyanoacrylate, methylacrylamide, vinyl ether, norbornyl acrylate moiety, optionally substituted acrylamide moiety, optionally substituted lactone, optionally substituted vinyl ether moiety or a cyclic olefin moiety.

11. The method of claim 7 wherein the tellurium-containing monomer comprises one or more of alkyl, fluoroalkyl, carbocyclic aryl, heteroaryl, sulfonic ester or sulfonamide.

12. The method of claim 7 wherein the tellurium monomer is selected from among:

13. The method of claim 7 , wherein the monomer is selected from the group consisting of:

14. A photoresist composition, comprising:

one or more polymers comprising repeating units formed by the polymerization of a tellurium-containing monomer: wherein the tellurium containing monomer

repeating units formed by the polymerization of a tellurium-containing monomer: wherein the tellurium containing monomer that comprises a tellurophene heterocycle and one or more ethylenically polymerizable groups, or

the tellurium-containing monomer is of Formula (IIIC); and

one or more acid generator compounds,

wherein,

R is hydrogen or an optionally substituted C 1-16 alkyl;

S is a linker;

each R 1 is the same or different non-hydrogen substituent;

R 2 is a non-hydrogen substituent; and

n is an integer of 0 to 4;

wherein the tellurium-containing monomer represented by the formula (IIIC) comprises one or more acid-cleavable groups.

15. The photoresist of claim 14 , wherein the tellurium-containing monomer further comprises one or more polar groups, base reactive groups, or a combination thereof.

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

applying a coating layer of a photoresist composition of claim 14 on a substrate; and

exposing the coating layer to activating radiation and developing the exposed coating layer.

17. The photoresist composition of claim 14 , wherein the tellurium-containing monomer is selected from the group consisting of:

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 Dec 31, 2018
From: AQAD, EMAD, MR.; CAMERON, JAMES F., MR.; THACKERAY, JAMES W., MR.
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 047875/0598 →