Acid generator compounds and photoresists comprising same

Patent metadata

Field	Value
Publication number	US-10274825-B2
Application number	US-201314027375-A
Country	US
Kind code	B2
Filing date	Sep 16, 2013
Priority date	Sep 15, 2012
Publication date	Apr 30, 2019
Grant date	Apr 30, 2019

Abstract

Acid generator compounds are provided that are particularly useful as a photoresist composition component. In one preferred aspect, cyclic sulfonium salt and photoresist compositions that comprise such compounds are provided. In another preferred aspect, acid generator compounds are provided that comprise one or more covalently linked acid-labile moieties, particularly ester-containing acid-labile moieties.

First claim

What is claimed is:

1. A photoresist composition, comprising:
(i) a polymer; and
(ii) an acid generator that corresponds to the following Formula (I):

wherein R 1 corresponds to the formula —(CH 2 ) n′ (C═O)O—ALG, n′ is a positive integer and ALG is a group that results in an acid labile moiety;
A is a hydrogen or non-hydrogen substituent; e is an integer from 0 to 4;
R 2 and R 3 are the same or different non-hydrogen substitutents, and R 2 and R 3 may be taken together to form an aromatic or non-aromatic ring; and
Z is a counter anion.

2. The photoresist composition of claim 1 wherein the acid generator is covalently bonded to the polymer.

3. A method for providing a photoresist relief image, comprising:
a) applying a coating layer of a photoresist composition of claim 1 on a substrate; and
b) exposing the photoresist composition layer to activating radiation and developing the exposed photoresist composition coating layer.

4. The method of claim 3 wherein the photoresist composition layer is exposed to EUV or e-beam radiation.

5. The photoresist composition of claim 1 wherein the acid generator is not covalently linked to a polymer.

6. The photoresist composition of claim 1 wherein the cleavage product of the acid-labile moiety comprises a carboalicyclic or a heteroalicyclic group.

7. The photoresist composition of claim 6 wherein the cleavage product of the acid-labile moiety comprises an optionally substituted adamantyl group.

8. The photoresist composition of claim 6 wherein the cleavage product of the acid-labile moiety comprises an optionally substituted cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl group.

9. The photoresist composition of claim 1 wherein the cleavage product of the acid-labile moiety comprises an aromatic group.

10. A photoresist composition, comprising:
(i) a polymer; and
(ii) an acid generator that corresponds to the following Formula (II):

wherein in Formula II R 1 corresponds to the formula —(CH 2 ) n′ (C═O)O—ALG, n′ is a positive integer and ALG is a group that results in an acid labile moiety;
A, B and C are each independently a hydrogen or non-hydrogen substituent;
D is a single bond; >C═O; >S(O); >S(O) 2 ; —C(═O)O—; —C(═O)NH—; —C(═O)—C(═O)—; —O—; CHOH; CH 2 ; or S;
e, f and g are each independently an integer from 0 to 4; and Z − is a counter anion.

11. The photoresist composition of claim 10 , wherein D is a single bond.

12. The photoresist composition of claim 10 wherein the acid generator is not covalently linked to a polymer.

13. The photoresist composition of claim 10 wherein the cleavage product of the acid-labile moiety comprises an adamantyl group or aromatic group.

14. The photoresist of claim 10 wherein D is >C═O or —CH 2 —.

15. A photoresist composition, comprising:
(i) a polymer; and
(ii) an acid generator that corresponds to the following Formula (III):

wherein R 1 1) provides an acid-labile moiety and 2) comprises an ester linkage;
X and Y are independently hydrogen or a non-hydrogen substituent;
A is a hydrogen or non-hydrogen substituent;
R 2 and R 3 are the same or different non-hydrogen substitutents, and R 2 and R 3 may be taken together to form an aromatic or non-aromatic ring;
n is a positive integer; e is an integer from 0 to 4; and
Z − is a counter anion.

16. The photoresist composition of claim 15 wherein the acid generator is not covalently linked to a polymer.

17. The photoresist composition of claim 15 wherein the cleavage product of the acid-labile moiety comprises a carboalicyclic or a heteroalicyclic group.

18. The photoresist composition of claim 17 wherein the cleavage product of the acid-labile moiety comprises an optionally substituted adamantyl group.

19. The photoresist composition of claim 17 wherein the cleavage product of the acid-labile moiety comprises an optionally substituted cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl group.

20. The photoresist composition of claim 15 wherein R 1 corresponds to the formula —(CH 2 ) n′ (C═O)O—ALG, n′ is a whole number and ALG is a group that results in an acid labile moiety.

21. A photoresist composition, comprising:
(i) a polymer; and
(ii) an acid generator that corresponds to the following Formula (IV):

wherein in Formula (IV) R 1 is a non-hydrogen substituent that provides an acid-labile moiety;
X and Y are independently hydrogen or a non-hydrogen substituent;
A, B and C are each independently a hydrogen or non-hydrogen substituent;
D is a single bond; >C═O; >S(O); >S(O) 2 ; —C(═O)O—; —C(═O)NH—; —C(═O)—C(═O)—; —O—; —CH(OH)—; —CH 2 —; or —S—;
n is a positive integer, e, f and g are the same or different integer from 0 to 4; and
Z − is a counter anion.

22. The photoresist composition of claim 21 wherein the acid generator is not covalently linked to a polymer.

23. The photoresist composition of claim 21 wherein D is a single bond.

24. An acid generator that corresponds to the following Formula (I):

wherein R 1 corresponds to the formula —(CH 2 ) n′ (C═O)O—ALG, n′ is a positive integer and ALG is a group that results in an acid labile moiety;
A is a hydrogen or non-hydrogen substituent; e is an integer from 0 to 4;
R 2 and R 3 are the same or different non-hydrogen substitutents, and R 2 and R 3 may be taken together to form an aromatic or non-aromatic ring; and
Z is a counter anion.

25. A photoresist composition, comprising:
(i) a polymer; and
(ii) an acid generator that comprises a group selected from the following:

Assignees

• Rohm & Haas Elect Mat

Inventors

• Labeaume Paul J

Classifications

• G03F7/0397

  the macromolecular compound having an alicyclic moiety in a side chain · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title

• G03F7/20

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title

• G03F7/0046

  with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence) · CPC title

• G03F7/0382 Primary

  the macromolecular compound being present in a chemically amplified negative photoresist composition · CPC title