Central Glass Company, Limited

International Business Machines Corporation

Jsr Corporation

Satoru Narizuka

Yoshimi Isono

Kazuhiko Maeda

Masaki Fujiwara

Takashi Kume

Kazuhiro Yamanaka

Rudy J Wojtecki

Ratnam Sooriyakumaran

Hoa D Truong

Takashi Mori

Yuji Hagiwara

Jonathan Joachim Jodry

Masashi Nagamori

Kazunori Mori

Daniel Sanders

Hiroshi Saegusa

Takehisa Ishimaru

Ryozo Takihana

Michio Ishida

Makoto Koide

Eri Tsukada

Fumihiro Amemiya

Takashi Masubuchi

Gregory Michael Wallraff

Bryan D McCloskey

Yuzuru Morino

Seok J Kang

Haruhiko Komoriya

Tomoki Nagai

Koichi Mikami

Manabu Yasumoto

Masahiro Terada

Makoto Shimizu

Hidehisa Nanai

Yutaka Katsuhara

Takamasa Kitamoto

Takuma Ebata

Seiji Hasegawa

Mikio Ujiie

Takahiro Koizumi

Masanori Fushimi

Susumu Inoue

Misugi Kato

Manabu Hatano

Shozo Kaneda

Seiji Takasaki

Magashi Nagamori

A battery employing lithium-oxygen chemistry may include an anode comprising lithium, an electrolyte, and a porous cathode. The electrolyte may include a lithium-containing salt; a partially fluorinated ether, such as 2,2-bis(trifluoromethyl)-1,3-dioxolane; and a co-solvent selected from the group consisting of ethers, amides, nitriles, and combinations thereof. In some examples, the electrolyte does not include a cyclic carbonate ester, a sulfolane, or a sulfolane derivative. The porous cathode allows oxygen to come into contact with the electrolyte.

Lithium oxygen battery and electrolyte composition

Non-ionic photo-acid generating (PAG) compounds were prepared that contain an aryl ketone group having a perfluorinated substituent alpha to the ketone carbonyl. The non-polymeric PAGs release a sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100&#xb0; C. to 150&#xb0; C., resulting in formation of good line patterns after development. At higher temperatures, the PAGs can also undergo a thermal reaction to form a sulfonic acid. The perfluorinated substituent provides improved thermal stability and hydrolytic/nucleophilic stability.

Fluorinated sulfonate esters of aryl ketones for non-ionic photo-acid generators

Non-ionic photo-acid generating (PAG) polymerizable monomers were prepared that contain a side chain sulfonate ester of an alpha-hydroxy aryl ketone. The aryl ketone group has a perfluorinated substituent alpha to the ketone carbonyl. The sulfur of the sulfonate ester is also directly linked to a fluorinated group. PAG polymers prepared from the PAG monomers release a strong sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100&#xb0; C. to 150&#xb0; C., resulting in formation of good line patterns after development.

Non-ionic aryl ketone based polymeric photo-acid generators

Non-ionic photo-acid generating (PAG) compounds were prepared that contain an aryl ketone group. The disclosed non-polymeric PAGs release a strong sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100&#xb0; C. to 150&#xb0; C., resulting in formation of good line patterns after development. At higher temperatures, the PAGs undergo a thermal reaction to form a sulfonic acid.

Non-ionic low diffusing photo-acid generators

Disclosed is a fluorine-containing sulfonic acid salt resin having a repeating unit represented by the following general formula (3). In the formula, each A independently represents a hydrogen atom, a fluorine atom or a trifluoromethyl group, and n represents an integer of 1-10. W represents a bivalent linking group, Rrepresents a hydrogen atom or a monovalent organic group, and Mrepresents a monovalent cation. A resist composition containing this resin is further superior in sensitivity, resolution and reproducibility of mask pattern and is capable of forming a pattern with a low LER. 

Fluorine-containing sulfonic acid salt, fluorine-containing sulfonic acid salt resin, resist composition, and pattern forming method using same

Photo-acid generating vinyl polymerizable monomers (PAG monomers) were prepared comprising sulfonate ester groups of N-hydroxide imides. The photo-acid generating portion of the PAG monomer is linked to a polymerizable portion of the monomer by an amide linking group. Photo-acid generating polymers (PAG polymers) of the PAG monomers show high sensitivity to extreme ultraviolet radiation (13.5 nm) and much less sensitivity to far ultraviolet wavelengths (193 nm, 248 nm). The PAG polymers also exhibit thermal and chemical amplification properties useful for forming high resolution positive tone or negative tone lithographic resist patterns.

Non-ionic photo-acid generating polymers for resist applications

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

A sulfonate resin having a repeating unit of the following general formula (3): where X each independently represents a hydrogen atom or a fluorine atom; n represents an integer of 1 to 10; Rrepresents a hydrogen atom, a halogen atom, a C-Calkyl group or a C-Cfluorine-containing alkyl group; Rrepresents either RO or RRN; and Mrepresents a monovalent cation. The sulfonate resin has an onium sulfonate incorporated in a side chain thereof with an anion moiety of the sulfonate salt fixed to the resin and can suitably be used as a resist resin having a high solubility in propylene glycol monomethyl ether acetate.

Polymerizable fluorine-containing sulfonate, fluorine-containing sulfonate resin, resist composition and pattern-forming method using same

According to the present invention, there is provided a fluorine-containing sulfonate resin having a repeating unit of the following general formula (3).  In order to prevent deficiency such as roughness after pattern formation or failure in pattern formation, the fluorine-containing sulfonate resin incorporates therein a photoacid generating function and serves as a resist resin in which 'a moiety capable of changing its developer solubility by the action of an acid' and 'a moiety having a photoacid generating function' are arranged with regularity.

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

An ammonium hydroxyfluoroalkanesulfinate is obtained by using an organic base while sulfinating a bromofluoroalcohol with a sulfinating agent. An ammonium hydroxyfluoroalkanesulfonate is obtained by oxidizing the ammonium hydroxyfluoroalkanesulfinate. An onium fluoroalkanesulfonate is obtained by converting the ammonium hydroxyfluoroalkanesulfonate into an onium salt through esterification. This onium fluoroalkanesulfonate is useful as a photoacid generator in chemically amplified resists and the like.

Ammonium fluoroalkanesulfonates and a synthesis method therefor

A resist composition according to the present invention includes at least a base resin, a photoacid generator and a solvent, wherein the photoacid generator comprises a fluorine-containing sulfonic acid salt of the following general formula (4). In the formula, X independently represents a hydrogen atom or a fluorine atom; n represents an integer of 1 to 6; Rrepresents a hydrogen atom, or an alkyl, alkenyl, oxoalkyl, aryl or aralkyl group; any of hydrogen atoms on carbons in Rmay be substituted with a substituent; Rrepresents RO or RRN; and A represents a divalent group. This fluorine-containing sulfonic acid salt can serve as a photoacid generator having high solubility in a resist solvent and thus can suitably be used for a resist composition such that the resist composition shows high resolution, wide DOF, small LER and high sensitivity to form a good pattern shape in lithographic processes.

Fluorine-containing sulfonic acid salts, photo-acid generator and resist composition and pattern formation method utilizing same

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

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

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Saitama, Japan

Satoru Narizuka