Method of manufacturing sulfonium salt

Patent metadata

Field	Value
Publication number	US-9469604-B2
Application number	US-201514847950-A
Country	US
Kind code	B2
Filing date	Sep 8, 2015
Priority date	Sep 8, 2014
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

Abstract

Provided is a sulfonium salt manufacturing method which can reduce the production of a monosulfonium salt. A method of manufacturing a sulfonium salt includes preparing a first sulfonium salt containing a sulfonium cation and a first anion, preparing a second sulfonium salt by exchanging the first anion for a halide ion, and preparing a third sulfonium salt by exchanging the halide ion for a second anion.

First claim

What is claimed is:

1. A method of manufacturing a sulfonium salt, comprising:
preparing a first sulfonium salt containing a sulfonium cation and a first anion;
preparing a second sulfonium salt by exchanging the first anion for a halide ion; and
preparing a third sulfonium salt by exchanging the halide ion for a second anion;
wherein the first sulfonium salt is prepared by condensing a sulfoxide compound and an aryl compound in the presence of an acid;
the sulfoxide compound is selected from the group consisting of dimethyl sulfoxide, methylethylsulfoxide, tetramethylenesulfoxide, diphenyl sulfoxide, dibenzothiophene-S-oxide, (4-methylphenyl)phenyl sulfoxide, 4,4′-dimethyldiphenylsulfoxide, 4,4′-dimethoxydiphenylsulfoxide, 4-methylthiodiphenylsulfoxide, (4-phenylthiophenyl)phenyl sulfoxide, 4,4′-dihydroxydiphenylsulfoxide, 4,4′-difluorodiphenylsulfoxide, 4,4′-dichlorodiphenylsulfoxide, 4,4′-dinitrodiphenylsulfoxide, 4-benzoyldiphenylsulfoxide, and 4,4′-carboxydiphenylsulfoxide; and
the aryl compound is selected from the group consisting of benzene, naphthalene, anthracene, phenanthrene, naphthacene, pyrene, toluene, cumene, tert-butylbenzene, xylene, ethylbenzene, dodecylbenzene, 1-methylnaphthalene, 1H-indene, biphenyl, biphenylene, 1,2′-binaphthyl, 2-phenylnaphthalene, anisole, ethoxybenzene, 1-methoxynaphthalene, benzylphenylether, benzofuran, diphenylether, 2-ethoxynaphthalene, 4-phenoxyphenol, xanthene, methylphenylsulfone, diphenylsulfone, thioanisole, ethylthiobenzene, benzothiophene, benzyl phenyl sulfide, phenacyl phenyl sulfide, diphenyl sulfide, dibenzothiophene, 2-methylphenyl)phenyl sulfide, (4-methylphenyl)phenyl sulfide, 2,2′-ditolyl sulfide, 2,3′-ditolyl sulfide, 2-phenylthionaphthalene, 9-phenylthioanthracene, (3-chlorophenyl)phenyl sulfide, (4-chlorophenyl)phenyl sulfide, 3,3′-dichlorodiphenyl sulfide, (3-bromophenyl)phenyl sulfide, 2,2′-dibromodiphenyl sulfide, 3,3′-dibromodiphenyl sulfide, (2-methoxyphenyl)phenyl sulfide, phenoxathiin, thioxanthone, 2-isopropylthioxanthone, 2-methoxythioxanthone, 4,4′-diphenyl thiobenzophenone, 4,4′-diphenylthiodiphenylether, 4,4′-diphenylthiobiphenyl, (4-phenylthiophenyl)phenyl sulfide, (4-benzoylphenyl)phenyl sulfide, (2-chloro-4-benzoylphenyl)phenyl sulfide, and (2-methylthio benzoylphenyl)phenyl sulfide.

2. The method of claim 1 , wherein the sulfonium cation contains at least one aryl group.

3. The method of claim 1 , wherein: the sulfoxide compound is a diaryl sulfoxide compound; and the diaryl sulfoxide compound is optionally substituted.

4. The method of claim 1 , wherein: the aryl compound is a diaryl sulfide compound; and the diaryl sulfide compound is optionally substituted.

5. The method of claim 1 , wherein the acid is sulfuric acid or a sulfonic acid compound.

6. The method of claim 1 , wherein the second sulfonium salt is prepared by causing a halide containing the halide ion to react with the first sulfonium salt.

7. The method of claim 1 , wherein the third sulfonium salt is prepared by causing a metal salt containing the second anion to react with the second sulfonium salt.

8. The method of claim 1 , wherein the second anion contains at least one fluorine atom.

9. The method of claim 1 , wherein the second anion is one anion selected from the group consisting of CF 3 SO 3 − , CF 3 CF 2 CF 2 CF 2 SO 3 − , AsF 6 − , PF 6 − , SbF 6 − , BF 4 − , and B(C 6 F 5 ) 4 − .

10. The method of claim 3 , wherein the aryl compound is a diaryl sulfide compound; and the diaryl sulfide compound is optionally substituted.

11. The method of claim 3 , wherein the acid is sulfuric acid or a sulfonic acid compound.

12. The method of claim 4 , wherein the acid is sulfuric acid or a sulfonic acid compound.

13. The method of claim 2 , wherein the second sulfonium salt is prepared by causing a halide containing the halide ion to react with the first sulfonium salt.

14. The method of claim 1 , wherein the second sulfonium salt is prepared by causing a halide containing the halide ion to react with the first sulfonium salt.

15. The method of claim 3 , wherein the second sulfonium salt is prepared by causing a halide containing the halide ion to react with the first sulfonium salt.

16. The method of claim 4 , wherein the second sulfonium salt is prepared by causing a halide containing the halide ion to react with the first sulfonium salt.

17. The method of claim 5 , wherein the second sulfonium salt is prepared by causing a halide containing the halide ion to react with the first sulfonium salt.

18. The method of claim 2 , wherein the third sulfonium salt is prepared by causing a metal salt containing the second anion to react with the second sulfonium salt.

19. A method of manufacturing a device, comprising a process of an electrolytic plating using a photoresist containing the sulfonium salt manufactured by the method of claim 1 .

Assignees

• Toyo Gosei Co Ltd

Inventors

• Enomoto Satoshi

Classifications

• C07C309/06

  containing halogen atoms, or nitro or nitroso groups bound to the carbon skeleton · CPC title

• C07C303/32 Primary

  of salts of sulfonic acids · CPC title

• C07C381/12

  Sulfonium compounds · CPC title

• G03F7/0045

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

• G03F7/0046

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