Central Glass Company, Limited

Masashi Nagamori

Satoru Narizuka

Yuji Hagiwara

Masaki Fujiwara

Jonathan Joachim Jodry

Kazuhiro Yamanaka

Kazunori Mori

Kazuhiko Maeda

Takashi Kume

Yoshimi Isono

Kazumasa Funabiki

Masaki Matsui

Takashi Masubuchi

Susumu Inoue

Hitoshi Yamamoto

A fluorine-containing sulfonic acid salt or a compound having a fluorine-containing sulfonic acid group, either of which having a structure represented by the following general formula (1), is provided. Such a salt or compound can act as a suitable photo-acid generator, and can form a resist pattern having excellent sensitivity, resolution and mask-dependence.  [In general formula (1), R represents a substituted or unsubstituted linear or branched monovalent hydrocarbon group having 1 to 30 carbon atoms, a substituted or unsubstituted monovalent hydrocarbon group having 3 to 30 carbon atoms and a cyclic or a partially cyclic structure, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monovalent heterocyclic organic group having 4 to 30 carbon atoms.]

Sulfonic acid salt and derivative thereof, photo-acid generator, and process for production of sulfonic acid salt

When sulfinating a carboxylic acid bromofluoroalkyl ester by using a sulfinating agent, an organic base is used, thereby obtaining a fluoroalkanesulfinic acid ammonium salt. This is oxidized to obtain a fluoroalkanesulfonic acid ammonium salt. This is used as the raw material and is converted to an onium salt or is converted to an onium salt by going through saponification and esterification, thereby obtaining a fluoroalkanesulfonic acid onium salt. This fluoroalkanesulfonic acid onium salt is useful as a photoacid generator used for chemically amplified resist materials, etc.

Fluoroalkanesulfonic acid ammonium salts and method for producing same

By using an organic base when a carboxylic acid bromodifluoroethyl ester is sulfinated by using a sulfinating agent, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt. By oxidizing the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfinic acid ammonium salt, there is obtained 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt. By using the 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid ammonium salt as a raw material and exchanging it into an onium salt directly or through saponification/esterification, there can be obtained a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid onium salt.

2-(alkylcarbonyloxy)-1, 1-difluoroethanesulfonic acid salt and method for producing the same

A fluorine-containing polymer of the present invention contains a repeating unit (a) of the general formula (2) and has a mass-average molecular weight of 1,000 to 1,000,000. This polymer is suitably used in a resist composition for pattern formation by high energy ray radiation of 300 nm or less wavelength or electron beam radiation or a top coat composition for liquid immersion lithography and is characterized as having high water repellency, notably high receding contact angle. In the formula, Rrepresents a polymerizable double bond-containing group; Rrepresents a fluorine atom or a fluorine-containing alkyl group; Rrepresents a substituted or unsubstituted alkyl group or the like; and Wrepresents a single bond, a substituted or unsubstituted methylene group or the like.

Fluorine-containing compound, fluorine-containing polymer compound, resist composition, top coat composition and pattern formation method

There is provided an acid having a fluorine-containing carbanion structure or a salt having a fluorine-containing carbanion structure, which is represented by the following general formula (1). By using a photoacid generator for chemically amplified resist materials that generates this acid, it is possible to provide a photoacid generator which has a high sensitivity to the ArF excimer laser light or the like, of which acid (photo generated acid) to be generated has a sufficiently high acidity, and which has a high dissolution in resist solvent and a superior compatibility with resin, and a resist material containing such a photoacid generator.

Salt having fluorine-containing carbanion structure, derivative thereof, photoacid generator, resist material using the photoacid generator, and pattern forming method

A fluorine-containing dicarboxylic acid represented by formula (1), wherein n represents an integer of 1-4, and the two carboxylic groups are not adjacent to each other on the aromatic ring. It is possible to obtain a linear polymer compound by reacting the fluorine-containing dicarboxylic acid with a comonomer (e.g., diaminodiol). By thermal cyclization, this linear polymer compound can be converted into another polymer compound having superior characteristics.

Fluorine-containing dicarboxylic acids and their novel polymer compounds

Disclosed is a process for producing 2-bromo-2,2-difluoroethanol, which comprises reducing a bromodifluoroacetic acid derivative represented by the formula [1] by using an ate hydride complex as a reducing agent. 2-Bromo-2,2-difluoroethanol thus produced can be used as the starting material to carry out the esterification step, the sulfination step and the oxidation step in this order, thereby producing a 2-alkylcarbonyloxy-1,1-difluoroethanesulfonic acid salt, wherein A represents a substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 15 carbon atoms, a heteroaryloxy group having 4 to 15 carbon atoms, or a halogen atom.

Processes for production of 2-bromo-2,2-difluoroethanol and 2-(alkylcarbonyloxy)-1, 1-difluoroethanesulfonic acid salt

Processes for production of 2-bromo-2,2-difluoroethanol and 2-(alkylcarbonyloxy)-1,1-difluoroethanesulfonic acid salt

Disclosed is a fluorine-containing dicarboxylic acid represented by formula (1), wherein n represents an integer of 1-4, and the two carboxylic groups are not adjacent to each other on the aromatic ring. It is possible to obtain a linear polymer compound by reacting the fluorine-containing dicarboxylic acid with a comonomer (e.g., diaminodiol). By thermal cyclization, this linear polymer compound can be converted into another polymer compound having superior characteristics.

The present invention provides a process for producing an optically active &#x3b2;-trifluoromethyl-&#x3b2;-hydroxycarbonyl compound represented by formula (3):comprising a step of reacting a fluoral equivalent represented by formula (1):with a carbonyl compound represented by formula (2):in the presence of an optically active amino acid or a derivative thereof.

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Fujimino, Japan

Masashi Nagamori