Central Glass Company, Limited

Shin-Etsu Chemical Co., Ltd.

Matsushita Electric Industrial Co., Ltd.

Other

Panasonic Corporation

Michitaka Ootani

Kazuhiko Maeda

Jun Hatakeyama

Yoshio Kawai

Yuji Harada

Masaru Sasago

Masayuki Endo

Haruhiko Komoriya

Shinji Kishimura

Satoru Miyazawa

Kentaro Tsutsumi

Jun Watanabe

Shinichi Sumida

Takeo Komata

Akihiro Ishii

Mikihiro Takahashi

Fuyuhiko Sakyu

Takashi Ootsuka

Hideyuki Tsuruta

Takako Yamazaki

Kanako Osafune

Masataka Fujimoto

One of the problems is to provide a solvent composition which has a little adverse effect on the global environment and has excellent stability when a compound having a perfluoropolyether (PFPE) group is in a solution state. In an embodiment, the problem is solved by providing a solvent composition for dissolving a compound having a perfluoropolyether (PFPE) group includes Z-1,2-dichloro-3,3,3-trifluoropropene (1223xd(Z)) as a main component.

Solvent composition

According to the present invention, there is provided a production process of a 2-fluoroacrylic ester including: a bromination step of converting a 2-fluoropropionic ester to a 2-bromo-2-fluoropropionic ester by reaction of the 2-fluoropropionic ester with a nitrogen-bromine bond-containing brominating agent in the presence of a radical initiator; and a dehydrobromination step of reacting the 2-bromo-2-fluoropropionic ester with a base. It is not necessary in this process to adopt very-low-temperature conditions and to use a stoichiometric amount of expensive reagent. The target 2-fluoroacrylic ester can be thus produced at low cost.

Process for preparation of 2-fluoroacrylic esters

The present invention relates to a fluorine-containing cyclic compound of formula (5): wherein R-Rand R-Rare independently a hydrogen atom, a halogen atom, or a C-Cstraight-chain, branched or cyclic alkyl group, and may contain fluorine atom, oxygen atom, sulfur atom, or nitrogen atom. Rand R, Rand R, or Rand Rmay be bonded together to form a ring. In such a case, it is a C-Calkylene group that may contain a hetero atom such as oxygen, sulfur and nitrogen, 'a' is 0 or 1, 'b' is an integer of 0-2 and &#x201c;c&#x201d; is an integer of 0-2.

Fluorine-containing cyclic compound, fluorine-containing polymer compound, resist material using same and method for forming pattern

The present invention relates to, for example, a fluorine-containing cyclic compound represented by the following general formula (1). In the general formula (1), R1a is a C-Ccyclic alkyl group, cyclic alkenyl group or cyclic alkynyl group; each of R2 and R3 is independently a hydrogen atom, a halogen atom, or a C-Cstraight-chain, branched or cyclic alkyl group; and each of R1a, R2 and R3 may contain fluorine atom, oxygen atom, sulfur atom, nitrogen atom or an atomic group containing a carbon-carbon double bond.

A polymer comprising recurring units (2) obtained through polymerization of an ester compound of formula (1) is used to form a resist composition. Ris F or C-Cfluoroalkyl, Ris H or C-Calkyl, Ris O or C-Calkylene, Rand Reach are H or C-Calkyl or fluoroalkyl, and Ris H or an acid labile group. The resist composition, when processed by ArF lithography, has advantages including improved resolution, transparency, minimal line edge roughness, and etch resistance. The resist composition exhibits better performance when processed by ArF immersion lithography with liquid interposed between a projection lens and a wafer. 

Ester compound, polymer, resist composition, and patterning process

A resist protective coating material is provided comprising an &#x3b1;-trifluoromethylacrylic acid/norbornene copolymer having cyclic perfluoroalkyl groups as pendant. In a pattern-forming process, the material forms on a resist film a protective coating which is water-insoluble, dissolvable in alkaline developer and immiscible with the resist film, allowing for effective implementation of immersion lithography.

Resist protective coating material and patterning process

A polymer comprising recurring units of formula (1) wherein Ris F or fluoroalkyl, Ris alkylene or fluoroalkylene, and Ris an acid labile group and having a Mw of 1,000-500,000 is used to formulate a resist composition, which is processed by the lithography involving ArF exposure and offers many advantages including resolution, minimal line edge roughness, etch resistance, and minimal surface roughness after etching. The composition performs well when processed by the ArF immersion lithography with liquid interposed between the projection lens and the wafer. 

Polymer, resist composition and patterning process

The present invention relates to a top coat composition, which is characterized in that it is applied to a photoresist top surface by using a polymer containing at least one structure represented by the formula [1], [2] or [3]. It is possible to produce a top coat composition solution by dissolving this top coat composition in an organic solvent. These top coat composition and top coat composition solution can be used in immersion lithography.

Top coat composition

A fluorinated polymer comprising recurring units of formulae (1a) to (1d) and having a Mw of 1,000-500,000 is provided. Ris an acid labile group, Ris a single bond or methylene, a1, a2, a3, and a4 are numbers from more than 0 to less than 1, and 0&#x3c;a1+a2+a3+a4&#x2266;1, b is 1 or 2, and c is 0 or 1. A resist composition comprising the polymer, when processed by the lithography involving ArF exposure, has many advantages including resolution, line edge roughness, etch resistance 

In an immersion lithography process, a pattern is formed by forming a photoresist layer on a wafer, forming a protective coating on the photoresist layer from an overlay material, exposing the layer structure to light in water, and developing. A water-insoluble, alkali-soluble material is used as the overlay material.

Polymer, resist protective coating material, and patterning process

Ester compounds having formula (1) wherein Ris fluorine or C-Cfluoroalkyl, Ris C-Calkylene or fluoroalkylene, and Ris an acid labile group are novel. They can be polymerized into polymers which are used to formulate resist compositions, which are processed by the lithography involving ArF exposure, offering many advantages including improved resolution and transparency, minimal line edge roughness, improved etch resistance, and especially minimal surface roughness after etching. 

Polymerizable ester compounds

A resist composition comprising a polymer containing vinyl sulfonate units having fluorinated hydrophilic groups as a base resin has excellent transparency, substrate adhesion and developer penetrability as well as plasma etching resistance, and is suited for lithographic microprocessing.

Polymers, resist compositions and patterning process

A ternary copolymer comprising units of &#x3b1;-trifluoromethylacrylic carboxylate having acid labile groups substituted thereon, units of &#x3b1;-trifluoromethylacrylic carboxylate having adhesive groups substituted thereon, and units of styrene having hexafluoroalcohol pendants is highly transparent to VUV radiation and resistant to plasma etching. A resist composition using the polymer as a base resin is sensitive to high-energy radiation below 200 nm, has excellent sensitivity, and is suited for lithographic microprocessing.

A copolymer of an acrylate monomer containing fluorine at &#x3b1;-position with a fluorinated hydroxystyrene derivative is highly transparent to VUV radiation and resistant to plasma etching. A resist composition using the polymer as a base resin is sensitive to high-energy radiation below 200 nm, has excellent sensitivity, resolution, transparency, substrate adhesion and plasma etching resistance, and is suited for lithographic microprocessing.

Growing community of inventors

Kawagoe, Japan

Michitaka Ootani