Onium compounds and methods of synthesis thereof

Patent metadata

Field	Value
Publication number	US-9703192-B2
Application number	US-201314027361-A
Country	US
Kind code	B2
Filing date	Sep 16, 2013
Priority date	Sep 15, 2012
Publication date	Jul 11, 2017
Grant date	Jul 11, 2017

Abstract

New onium salt compounds and methods for synthesis of such compounds are provided. Preferred methods of the invention include (a) providing an onium salt compound comprising a sulfonate component having an electron withdrawing group; and (b) treating the onium salt compound with a halide salt to form a distinct salt of the onium compound. The present onium compounds are useful as an acid generator component of a photoresist composition.

First claim

What is claimed is:

1. A method for preparing an onium salt compound for use as an acid generator, the method comprising:
(a) providing an onium salt compound for use as an acid generator comprising a sultanate component, wherein the sulfonate component comprises an electron withdrawing group; and
(b) washing the onium salt compound with a fluid composition comprising a halide salt to form a distinct salt of the onium compound; and
(c) admixing the distinct salt of the onium compound with a polymer to provide a photoresist composition.

2. The method of claim 1 wherein the one or more electron withdrawing groups comprise one or more halogen atoms.

3. The method of claim 1 wherein the sulfonate component is a triflate.

4. The method of claim 1 wherein the sulfonate component is of the following general formula (I);

wherein R 1 and R 3 are independently selected from hydrogen, halogen, cyano, nitro, optionally substituted alkyl, and optionally substituted carbocyclic aryl;
R 2 is the same or different than R 1 and R 3 and is selected from a linker moiety, hydrogen, halogen, cyano, nitro, optionally substituted alkyl, and optionally substituted carbocyclic aryl,
wherein at least one R 1 , R 2 and R 3 is an electron withdrawing group.

5. The method of claim 4 wherein (i) the onium salt compound is treated with a halide salt of the onium compound and (ii) the halide alt of the onium compound is treated to provide the distinct salt of the onium compound.

6. The method of claim 5 wherein one or more of R 1 , R 2 and R 3 are halogen or halogenated alkyl.

7. The method of claim 1 wherein the sulfonate component is of the following general formula (II):

wherein each R is the same or different and is an electron-withdrawing group, optionally substituted alkyl, or optionally substituted carbocyclic aryl, with at least one R being an electron-withdrawing moiety; and m is an integer of from 1 to 5.

8. The method of claim 7 wherein R is halogen or halogenated alkyl.

9. The method of claim 1 wherein the onium salt compound is treated with an iodide salt to form a distinct salt of the onium compound.

10. The method of claim 9 wherein the onium salt compound is washed with a fluid solution of the iodide salt.

11. The method of claim 1 wherein the onium salt compound is a sulfonium compound.

12. The method of claim 11 wherein a sulfonium cation component of the sulfonium compound comprises a non-cyclic sulfonium moiety with a sulfonium atom substituted by non-aromatic or aromatic groups.

13. The method of claim 11 wherein a sulfonium cation component of the sulfonium compound comprises a cyclic sulfonium moiety.

14. The method of claim 11 wherein a sulfonium cation component of the sulfonium compound comprises a thioxanthone group.

15. The method of claim 11 wherein a sulfonium cation component of the sulfonium compound comprises a moiety of the following formula:

wherein X is C═O, S(O), SO 2 , C(═O)O, C(═O)NH, C(═O)—C(═O)—, or —O—; and R is a non-hydrogen substituent.

16. The method of claim 1 wherein the onium salt compound is an iodonium compound.

17. A method for preparing an onium salt compound, the method comprising:
(a) providing a sulfonium salt compound comprising a sulfonate component, wherein the sulfonate component comprises an electron withdrawing group; and
(b) treating the sulfonium salt compound with a halide salt to permit displacement of the sulfonate component with the halide salt anion to provide a distinct salt of the onium compound.

18. The method of claim 17 wherein treating the onium salt with a halide salt provides a halide salt of the onium compound which undergoes an anion displacement reaction to provide the distinct salt of the onium compound.

19. The method of claim 18 further comprising admixing the distinct salt of the onium compound with a polymer to provide a photoresist composition.

20. A method for preparing an onium salt compound, the method comprising:
(a) providing a sulfonium salt compound comprising a sulfonate component, wherein 1) the sulfonate component comprises an electron withdrawing group and 2) a sulfonium cation component of the sulfonium compound comprises a cyclic sulfonium moiety; and
(b) treating the sulfonium salt compound with a halide salt to form a distinct salt of the onium compound.

21. The method of claim 20 wherein a sulfonium cation component of the sulfonium compound comprises a thioxanthone group.

22. The method of claim 20 wherein a sulfonium cation component of the sulfonium compound comprises a moiety of the following formula:

wherein X is C═O, S(O), SO 2 , C(═O)O, C(═O)NH, C(═O)—C(═O)—, or —O—; and R is a non-hydrogen substituent.

23. A method for preparing an onium salt compound, the method comprising:
(a) providing an onium salt compound comprising a sulfonate component, wherein the sulfonate component comprises an electron withdrawing group;
(b) treating the onium salt compound with a halide salt to permit displacement of the sulfonate component with the halide salt anion to provide a distinct salt of the onium compound;
(c) admixing the distinct salt of the onium compound with a polymer to provide a photoresist composition.

Assignees

• Rohm & Haas Elect Mat

Inventors

• Labeaume Paul J

Classifications

• G03F7/38

  Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)} · CPC title

• C07C2603/74

  Adamantanes · CPC title

• C07D335/16 Primary

  Oxygen atoms, e.g. thioxanthones · CPC title

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/0392

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