IP Library Granted Patent US 8,609,891
Granted Patent B2
US 8,609,891 · App. 13/095,533 · Granted Dec 17, 2013

Photoacid generators and photoresists comprising same

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Quick Facts
Patent No.
US 8,609,891
App. No.
13/095,533
Granted
Dec 17, 2013
Kind
B2
Abstract

New photoacid generator compounds are provided that comprise a nitrogen-base functional component of the structure —C(═O)N<. Photoresist compositions also are provided that comprise one or more PAGs of the invention.

Claims (46)

1. A photoacid generator that comprises a structure of the following formula (I):

RO(C═O)(CXY) p (CF 2 ) n SO 3 − M +   (I)

wherein R is non-hydrogen substituent that comprises a group of the structure —C(═O)N(R 1 )(R 2 ) where R 1 and R 2 are each the same or different and may be hydrogen or a non-hydrogen substituent,

or R 1 and R 2 may be taken together to form a ring with the nitrogen;

X and Y are each independently hydrogen or a non-hydrogen substituent;

p is 0 or a positive integer;

n is a positive integer; and

M+ is a counter ion.

2. The photoacid generator of claim 1 wherein R 1 and R 2 are independently selected from the group consisting of optionally substituted alkyl; optionally substituted C3-30 cycloalkyl, optionally substituted alkoxy, optionally substituted carbocyclic group, optionally substituted heteroalicyclic group that contains 1, 2 or 3 N, O and/or S ring atoms.

3. The photoacid generator of claim 1 wherein R 1 and R 2 are each other than hydrogen.

4. The photoacid generator of claim 1 wherein R is —(CXY) 1-10 C(═O)N(R 1 )(R 2 ) where each occurrence of X and Y is independently hydrogen or a non-hydrogen substituent.

5. A photoresist composition comprising a resin component and a photoacid generator of claim 1 .

6. A photoresist composition comprising a resin component and a photoacid generator of claim 2 .

7. A photoresist composition comprising a resin component and a photoacid generator of claim 3 .

8. A photoresist composition comprising a resin component and a photoacid generator of claim 4 .

9. A method for forming a photoresist relief image comprising:

a) applying a coating layer of a photoresist composition of claim 5 on a substrate;

(b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

10. A method for forming a photoresist relief image comprising:

a) applying a coating layer of a photoresist composition of claim 6 on a substrate;

(b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

11. A method for forming a photoresist relief image comprising:

a) applying a coating layer of a photoresist composition of claim 7 on a substrate;

(b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

12. A method for forming a photoresist relief image comprising:

a) applying a coating layer of a photoresist composition of claim 8 on a substrate;

(b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

13. A photoacid generator that comprises an anion component of any of the following Formula (I) through (XV):

wherein in each of Formulae (I) to (XV):

m, n, o, p, q are independently an integer of 0 to 10;

R 1 is selected from one of (A), (B), (C), (D), (E), or (F) below:

wherein:

R 2 and R 3 are the same or different optionally substituted branched, non-branched or cyclic aliphatic group;

q and r are independently an integer from 0 to 10; and

s is a positive integer from 1 to 10.

14. The photoacid generator of claim 13 , wherein R 2 and R 3 are the same or different and are independently selected from the group consisting of optionally substituted C 1-30 alkyl, optionally substituted C 3-30 cycloalkyl, optionally substituted C 1-30 alkoxy, optionally substituted C 6-30 carbocyclic group, and optionally substituted C 3-30 heteroalicyclic group that contains 1, 2 or 3 N, O and/or S ring atoms.

15. The photoacid generator of claim 13 wherein the anion component is complexed with a sulfonium cation component.

16. The photoacid generator of claim 13 wherein the anion component is complexed with an iodonium cation component.

17. A photoresist composition comprising a resin component and a photoacid generator of claim 13 .

18. A photoresist composition comprising a resin component and a photoacid generator of claim 14 .

19. A method for forming a photoresist relief image comprising:

a) applying a coating layer of a photoresist composition of claim 17 on a substrate;

(b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

20. A method for forming a photoresist relief image comprising:

a) applying a coating layer of a photoresist composition of claim 18 on a substrate;

(b) exposing the photoresist coating layer to patterned activating radiation and developing the exposed photoresist layer to provide a relief image.

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 15, 2013
From: BAE, YOUNG CHEOL; CARDOLACCIA, THOMAS; LIU, YI
To: ROHM AND HAAS ELECTRONIC MATERIALS LLC
Reel/Frame 031610/0020 →