Central Glass Company, Limited

Yoshimi Isono

Satoru Narizuka

Jonathan Joachim Jodry

Kazuhiko Maeda

Kazuhiro Yamanaka

Kazunori Mori

Yuji Hagiwara

Ryozo Takihana

Haruhiko Komoriya

Mikihiro Takahashi

Hidehisa Nanai

Shoichi Tsujioka

Masashi Nagamori

Takamasa Kitamoto

Hironari Takase

Masanori Fushimi

Misugi Kato

Syoichi Tsujioka

A fluorine-containing sulfonate salt resin or fluorine-containing sulfonate ester resin having a structure of the following general formula (A) and a fluorine-containing N-sulfonyloxyimide resin having a repeating unit of the general formula (17). And a resist composition using the above resin such that the resist composition can attain high resolution, wide DOF, small LER and high sensitivity and form a good pattern shape.

Fluorine-containing sulfonate resin, fluorine-containing N-sulfonyloxyimide resin, resist composition and pattern formation method

In the present invention, a target alkoxycarbonylfluoroalkanesulfonic acid salt is obtained by using a halofluoroalkanoic acid ester as a starting raw material, sulfinating the halofluoroalkanoic acid ester in the presence of an amine (as a first step), and then, oxidizing the resulting sulfination product (as a second step). Further, an alkoxycarbonylfluoroalkanesulfinic acid onium salt, which is useful as a photoacid generator, is obtained by salt exchange reaction of the alkoxycarbonylfluoroalkanesulfonic acid salt.

Method for producing alkoxycarbonylfluoroalkanesulfonic acid salt

According to the present invention, a polymer is obtained by polycondensation of a fluorinated dicarboxylic acid derivative of the general formula (M-1) or an acid anhydride of the fluorinated dicarboxylic acid with a polyfunctional compound having two to four reactive groups corresponding in reactivity to carbonyl moieties of the fluorinated dicarboxylic acid derivative or acid anhydride.

Fluorinated dicarboxylic acid derivative and polymer obtained therefrom

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

Disclosed is a top coating composition formed on a resist film, for protecting the resist film, the top coating composition being a top coating composition for photoresist, characterized by containing a fluorine-containing polymer having a repeating unit represented by the following general formula (1). This composition is capable of controlling developing solution solubility and has a high water repellency. [In the formula, Rrepresents a hydrogen atom, fluorine atom, methyl group or trifluoromethyl group, Rrepresents a heat-labile protecting group, Rrepresents a fluorine atom or fluorine-containing alkyl group, and W is a bivalent linking group.]

Top coating composition

There is disclosed a fluorine-containing polymer compound comprising a repeating unit (a) of the following general formula (2) and having a weight-average molecular weight of 1000 to 1000000 where Rrepresents a polymerizable double bond-containing group; Rrepresents a fluorine atom or a fluorine-containing alkyl group; Rrepresents a hydrogen atom, an acid labile group, a cross-linking site or the other monovalent organic group; and Wrepresents a linking moiety. When the fluorine-containing polymer compound is used in a resist compound for pattern formation by high energy radiation of 300 nm or less wavelength or electron beam radiation, it is possible to form a resist pattern with a good rectangular profile.

Fluorine-containing compound, fluorine-containing polymer compound, resist composition and patterning method using 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

Disclosed is a fluorinated sulfonic acid salt or fluorinated sulfonic acid group-containing compound having a structure represented by the following general formula (A). In the formula, n indicates an integer of 1 to 10; R indicates a substituted or unsubstituted C-Clinear, branched or cyclic alkyl group, a substituted or unsubstituted C-Clinear, branched or cyclic alkenyl group, a substituted or unsubstituted C-Caryl group, or a C-Cheteroaryl group; and a indicates 1 or 0. A photoacid generator containing the above fluorinated sulfonic acid salt or fluorinated sulfonic acid group-containing compound shows high sensitivity to an ArF excimer laser or the like, presents no concerns about human body accumulation, can generate an acid (photoacid) of sufficiently high acidity, and exhibits high solubility in a resist solvent and good compatibility with a resist resin.

Sulfonic acid salt and derivative thereof, photoacid generator agent, and resist material and pattern formation method using the photoacid generator agent

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.

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 method of synthesizing an ionic metal complex corresponding to formula (1) in which a compound of formula (2) and/or a compound of formula (3)E-O&#x2014;R&#x2003;&#x2003;(3)is reacted with a halogen containing compound in an organic solvent in the presence of a compound containing an element of group 1, group 2, group 13 or group 14 of the periodic table as a reaction aid.

Method for synthesizing ionic complex

The invention relates to a process for synthesizing an ionic metal complex represented by the general formula (1) or (5). This process includes reacting in an organic solvent a compound (corresponding to ligand of the complex) represented by the general formula (2) or (6) with a halogen-containing compound represented by the general formula (3) or (4), in the presence of a reaction aid containing an element selected from the group consisting of elements of groups 1-4 and 11-14 of the periodic table. It is possible by this process to easily and efficiently synthesize the ionic metal complex, which can be used as a supporting electrolyte for electrochemical devices, a polymerization catalyst of polyolefins and so forth, or a catalyst for organic synthesis.

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Kawagoe, Japan

Yoshimi Isono