Shin-Etsu Chemical Co., Ltd.

Katsuhiro Kobayashi

Youichi Ohsawa

Takeshi Kinsho

Takeru Watanabe

Tsunehiro Nishi

Kazunori Maeda

Koji Hasegawa

Satoshi Watanabe

Seiichiro Tachibana

Katsuya Takemura

Tomohiro Kobayashi

Yoshitaka Yanagi

Jun Hatakeyama

Masaki Ohashi

Kazuhiro Katayama

Tatsushi Kaneko

Ryosuke Taniguchi

Kazumi Noda

Toshihiko Fujii

Kenji Funatsu

Akihiro Seki

Junji Tsuchiya

Takao Yoshihara

Satoshi Shinachi

Shigeo Tanaka

Eiji Fukuda

There is disclosed a positive resist composition comprising (A) a resin having repeating units shown by the following general formulae (1) and (2) as repeating units that contain acid labile groups and being capable of increasing its alkaline solubility by an acid, (B) a photoacid generator, (C) a compound shown by the following general formula (3), and (D) a solvent. There can be a positive resist composition having high resolution, and at the same time giving an excellent pattern profile; and a patterning process in which an immersion lithography is carried out using a formed top coat. 

Positive resist composition and patterning process

A pattern is formed by applying a first positive resist composition comprising a polymer comprising recurring units which become alkali soluble under the action of acid onto a substrate to form a first resist coating, heat treating, exposing, heat treating, developing to form a first resist pattern, applying a pattern surface coating composition comprising a hydroxyl-containing crosslinkable polymer onto the first resist pattern and crosslinking, thereby covering the first resist pattern with a crosslinked polymer film, applying a second positive resist composition thereon, heat treating, exposing, heat treating, and developing to form a second resist pattern.

Patterning process and pattern surface coating composition

Sulfonate salts have the formula: HOCHCHCFCFSOMwherein Mis a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oxime sulfonates and sulfonyloxyimides derived from these salts are effective photoacid generators in chemically amplified resist compositions.

Sulfonate salts and derivatives, photoacid generators, resist compositions, and patterning process

Fluorinated monomers of formula (1) are useful in producing polymers for the formulation of radiation-sensitive resist compositions. Ris H or monovalent C-Chydrocarbon group, Ris H, F, methyl or trifluoromethyl, Rand Rare H or a monovalent C-Chydrocarbon group, or Rand Rmay form an aliphatic hydrocarbon ring, and A is a divalent C-Chydrocarbon group 

Fluorinated monomer, fluorinated polymer, resist composition and patterning process

Sulfonate salts have the formula: CF&#x2014;CH(OCOR)&#x2014;CFSOMwherein R is C-Calkyl or C-Caryl, and Mis a lithium, sodium, potassium, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.

Lactone-containing compounds having formula (1) are novel wherein Ris H, F, methyl or trifluoromethyl, Rand Rare H or monovalent hydrocarbon groups, or Rand Rmay together form an aliphatic hydrocarbon ring, Ris H or COR, Ris a monovalent hydrocarbon group, W is CH, O or S, and kis 3, 4 or 5. They are useful as monomers to produce polymers which are transparent to radiation &#x2266;500 nm. Radiation-sensitive resist compositions comprising the polymers as base resin exhibit excellent properties including resolution, LER, pattern density dependency and exposure margin. 

Lactone-containing compound, polymer, resist composition, and patterning process

A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid, and (B) an acid generator which is a specific sulfonium salt compound. The resin (A) is a polymer comprising tertiary alkyl protective group units having a hydrophobic tetracyclo[4.4.0.10.1]dodecane structure, di- or trihydroxyadamantyl units, and monocyclic lactone units.

Sulfonate salts have the formula: RCOOCHCHCFCFSOMwherein Ris alkyl, aryl or hetero-aryl, Mis a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oxime sulfonates and sulfonyloxyimides derived from these salts are effective photoacid generators in chemically amplified resist compositions.

Sulfonate salts have the formula: CF&#x2014;CH(OH)&#x2014;CFSOMwherein Mis a Li, Na, K, ammonium or tetramethylammonium ion. Because of inclusion within the molecule of a hydroxyl group which is a polar group, the sulfonic acids are effective for restraining the length of acid diffusion through hydrogen bond or the like. The photoacid generators that generate these sulfonic acids perform well during the device fabrication process including coating, pre-baking, exposure, post-exposure baking, and developing steps. The photoacid generators are little affected by water left on the wafer during the ArF immersion lithography.

A positive resist composition comprises (A) a resin component which becomes soluble in an alkaline developer under the action of an acid, and (B) an acid generator. The resin (A) is a polymer comprising tertiary alkyl protective group units having a hydrophobic tetracyclo[4.4.0.10.1]-dodecane structure, hydroxyadamantane units, monocyclic lactone units, and carboxylic acid units. The acid generator (B) is a specific sulfonium salt compound.

Sulfonate salts have the formula:RSO&#x2014;CH(Rf)&#x2014;CFSOMwherein Ris alkyl or aryl, Rf is H or trifluoromethyl, and Mis a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oximesulfonates and sulfonyloxyimides and other compounds derived from these sulfonate salts are effective photoacid generators in chemically amplified resist compositions.

Provided are sulfonyldiazomethane compounds and photoacid generators suited for resist materials which generate less foreign matters after application, development and peeling, and in particular, are excellent in the pattern profile after the development; and resist materials and patterning process using them. Provided are sulfonyldiazomethane compounds represented by formula (1): Also provides are photoacid generators containing the sulfonyldiazomethane compounds, and a chemical amplification resist material comprising (A) a resin which changes its solubility in an alkali developer by action of an acid, and (B) a sulfonyldiazomethane compound of formula (1) capable of generating an acid by exposure to radiation. Provided is a patterning process comprising steps of applying the above-described resist material onto a substrate to form a coating, heating the coating, exposing the coating, and developing the exposed coating in a developer after an optional heat treatment.

Sulfonyldiazomethane compounds, photoacid generator, resist materials and patterning using the same

Chemically amplified resist compositions comprising nitrogen-containing organic compounds having an aromatic carboxylic acid ester structure have an excellent resolution and provide a precise pattern profile and are useful in microfabrication using electron beams or deep-UV light.

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Joetsu, Japan

Katsuhiro Kobayashi