IP Library Granted Patent US 8,790,861
Granted Patent B2
US 8,790,861 · App. 13/723,973 · Granted Jul 29, 2014

Cycloaliphatic monomer, polymer comprising the same, and photoresist composition comprising the polymer

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Quick Facts
Patent No.
US 8,790,861
App. No.
13/723,973
Granted
Jul 29, 2014
Kind
B2
Abstract

A monomer has the Formula I: wherein R 1 , R 2 , and R 3 are each independently a C 1-30 monovalent organic group, and R 1 , R 2 , and R 3 are each independently unsubstituted or include a halogen, nitrile, ether, ester, ketone, alcohol, or a combination comprising at least one of the foregoing functional groups; R 4 includes H, F, C 1-4 alkyl, or C 1-4 fluoroalkyl; A is a single bond or a divalent linker group, wherein A is unsubstituted or substituted to include a halogen, nitrile, ether, ester, ketone, alcohol, or a combination comprising at least one of the foregoing functional groups; m and n are each independently an integer of 1 to 8; and x is 0 to 2n+2, and y is 0 to 2m+2.

Claims (30)

1. A monomer, having the Formula I:

wherein R 1 , R 2 , and R 3 are each independently a C 1-30 monovalent organic group, and R 1 , R 2 , and R 3 are each independently unsubstituted or include a halogen, nitrile, ether, ester, ketone, alcohol, or a combination comprising at least one of the foregoing functional groups;

R 4 includes H, F, C 1-4 alkyl, or C 1-4 fluoroalkyl;

A is a single bond or a divalent linker group, wherein A is unsubstituted or substituted to include a halogen, nitrile, ether, ester, ketone, alcohol, or a combination comprising at least one of the foregoing functional groups;

m is 3, and n is an integer of 1 to 8; and

x is 1 to 2n+2, and y is 0 to 2m+2.

2. The monomer of claim 1 , wherein R 4 is H, F, methyl, or trifluoromethyl.

3. The monomer of claim 1 , wherein R 1 , R 2 , and R 3 are each independently C 1-10 alkyl, C 1-10 fluoroalkyl, C 1-10 alkoxy, C 1-10 fluoroalkoxy, C 1-10 alkanol, or a combination comprising at least one of the foregoing.

4. The monomer of claim 1 , wherein R 1 , R 2 , and R 3 are each independently methyl, ethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, or a combination comprising at least one of the foregoing.

5. The monomer of claim 1 , wherein n is 3 or 4, x is 1 or 2, and y is an integer of from 0 to 2.

6. The monomer of claim 1 , wherein R 1 is methyl or ethyl, n is 3, and y is 0.

7. A polymer, comprising the monomer of claim 1 .

8. A photoresist composition, comprising the polymer of claim 7 and a photoacid generator.

9. A coated substrate, comprising: (a) a substrate having one or more layers to be patterned on a surface thereof; and (b) a layer of a photoresist composition of claim 8 over the one or more layers to be patterned.

10. A patterned layer, formed by patternwise imaging the coated substrate of claim 9 using actinic radiation at 193 nm.

11. A monomer, having the Formula I:

wherein R 1 , R 2 , and R 3 are each independently a C 1-30 monovalent organic group, and R 1 , R 2 , and R 3 are each independently unsubstituted or include a halogen, nitrile, ether, ester, ketone, alcohol, or a combination comprising at least one of the foregoing functional groups;

R 4 includes H, F, C 1-4 alkyl, or C 1-4 fluoro alkyl;

A is —O—CH 2 (C═O)—;

m and n are each independently an integer of 1 to 8; and

x is 0 to 2n+2, and y is 0 to 2m+2.

12. The monomer of claim 11 , wherein R 4 is H, F, methyl, or trifluoromethyl.

13. The monomer of claim 11 , wherein R 1 , R 2 , and R 3 are each independently C 1-10 alkyl, C 1-10 fluoroalkyl, C 1-10 alkoxy, C 1-10 fluoroalkoxy, C 1-10 alkanol, or a combination comprising at least one of the foregoing.

14. The monomer of claim 11 , wherein R 1 , R 2 , and R 3 are each independently methyl, ethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2-hydroxyethyl, or a combination comprising at least one of the foregoing.

15. The monomer of claim 11 , wherein m and n are independently 3 or 4, and x and y are independently an integer of from 0 to 2.

16. The monomer of claim 11 , wherein R 1 is methyl or ethyl, m and n are each 3, and x and y are each 0.

17. A polymer, comprising the monomer of claim 11 .

18. A photoresist composition, comprising the polymer of claim 17 and a photoacid generator.

19. A coated substrate, comprising: (a) a substrate having one or more layers to be patterned on a surface thereof; and (b) a layer of a photoresist composition of claim 18 over the one or more layers to be patterned.

20. A patterned layer, formed by patternwise imaging the coated substrate of claim 19 using actinic radiation at 193 nm.

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 21, 2012
From: LIU, CONG; LI, MINGQI; XU, CHENG-BAI
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 029518/0360 →