Central Glass Company, Limited

Jsr Corporation

Jonathan Joachim Jodry

Kazuhiko Maeda

Masaki Fujiwara

Satoru Narizuka

Yoshimi Isono

Yuji Hagiwara

Masashi Nagamori

Kazuhiro Yamanaka

Tomoki Nagai

Makoto Shimizu

Takuma Ebata

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 polymerizable fluorine-containing compound represented by formula (1), wherein Rrepresents a polymerizable double-bond containing group, Rrepresents an acid-labile protecting group, Rrepresents a fluorine atom or fluorine-containing alkyl group, and W represents a bivalent linking group. This compound can provide a fluorine-containing polymer compound that has a weight-average molecular weight of 1,000-1,000,000 and contains a repeating unit represented by formula (2), wherein R, Rand W are defined as above, each of R, Rand Rindependently represents a hydrogen atom, fluorine atom or monovalent organic group, at least two of R, Rand Rmay be combined to form a ring. This polymer compound can provide a resist composition capable of forming a pattern that is transparent to exposure light and superior in rectangularity.

Polymerizable fluorine-containing compound

A fluorine-containing unsaturated carboxylic acid represented by formula (1), wherein Rrepresents a polymerizable double-bond containing group, Rrepresents a fluorine atom or fluorine-containing alkyl group, and W represents a bivalent linking group. This compound can provide a fluorine-containing polymer compound that has a weight-average molecular weight of 1,000-1,000,000 and contains a repeating unit represented by formula (2), wherein Rand W are defined as above, each of R, Rand Rindependently represents a hydrogen atom, fluorine atom or monovalent organic group, at least two of R, Rand Rmay be combined to form a ring. This polymer compound can provide a chemically amplified resist composition that is transparent to KrF or ArF excimer laser light and has a high resolution and is capable of forming a pattern having a rectangular section with no swelling.

Fluorine-containing compound, fluorine-containing polymer, negative-type resist composition, and patterning process using same

A sulfonic acid onium salt represented by the following formula (1) can be used as a superior radiosensitive acid generator for resist compositions. It is possible to form a good pattern by using a resist composition containing this sulfonic acid onium salt. In formula (1), Rrepresents a monovalent organic group, and Qrepresents a sulfonium cation or iodonium cation.

Compound for photoacid generator, resist composition using the same, and pattern-forming method

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

Disclosed is a fluorine-containing unsaturated carboxylic acid represented by formula (1), wherein Rrepresents a polymerizable double-bond containing group, Rrepresents a fluorine atom or fluorine-containing alkyl group, and W represents a bivalent linking group. This compound can provide a fluorine-containing polymer compound that has a weight-average molecular weight of 1,000-1,000,000 and contains a repeating unit represented by formula (2), wherein Rand W are defined as above, each of R, Rand Rindependently represents a hydrogen atom, fluorine atom or monovalent organic group, at least two of R, Rand Rmay be combined to form a ring. This polymer compound can provide a chemically amplified resist composition that is transparent to KrF or ArF excimer laser light and has a high resolution and is capable of forming a pattern having a rectangular section with no swelling.

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

A resin that includes a repeating unit shown by the following formula (10) has an excellent performance as a radiation sensitive acid generator, and exhibits only a small adverse effect on the environment and a human body. wherein Rrepresents a hydrogen atom or the like, Mrepresents a specific cation, and n is an integer from 1 to 5.

Polymerizable sulfonic acid onium salt and resin

Disclosed is a fluorine-containing polymer compound containing first and second repeating units respectively represented by formulas (a-1) and (a-2), wherein Rrepresents a fluorine atom or fluorine-containing alkyl group, each of W and Windependently represents a bivalent linking group, Rrepresents an acid-labile protecting group, each of R, Rand Rindependently represents a hydrogen atom, fluorine atom or monovalent organic group, and at least two of R, R, Rand W or Wmay be combined to form a cyclic structure in formula (a-1) or (a-2). This polymer compound has a weight-average molecular weight of 1,000 to 1,000,000 and can provide a resist composition capable of forming a pattern with no swelling and no pattern falling down.

Positive-type resist composition

Disclosed is a fluorine-containing compound represented by formula (1), wherein Rrepresents a polymerizable double-bond containing group, Rrepresents an acid-labile protecting group, Rrepresents a fluorine atom or fluorine-containing alkyl group, and W represents a bivalent linking group. This compound can provide a fluorine-containing polymer compound that has a weight-average molecular weight of 1,000-1,000,000 and contains a repeating unit represented by formula (2), wherein R, Rand W are defined as above, each of R, Rand Rindependently represents a hydrogen atom, fluorine atom or monovalent organic group, at least two of R, Rand Rmay be combined to form a ring. This polymer compound can provide a resist composition capable of forming a pattern that is transparent to exposure light and superior in rectangularity.

Fluorine-containing compound, fluorine-containing polymer, postive-type resist composition, and patterning process using same

A process for producing an alkoxycarbonylfluoroalkanesulfonate represented by the formula [1] is provided. This process includes the steps of (a) reacting a halofluoroalkanoate represented by the formula [2], with a sulfinating agent, thereby obtaining an alkoxycarbonylfluoroalkanesulfinate represented by the formula [3]; and (b) reacting the alkoxycarbonylfluoroalkanesulfinate with an oxidizing agent, thereby obtaining the target alkoxycarbonylfluoroalkanesulfonate. Furthermore, it is possible to react the obtained alkoxycarbonylfluoroalkanesulfonate with a monovalent onium salt to conduct a salt exchange, thereby obtaining a alkoxycarbonylfluoroalkanesulfonic acid onium salt represented by the formula [4]. 

Growing community of inventors

Kawagoe, Japan

Jonathan Joachim Jodry