Tokyo Ohka Kogyo Co., Ltd.

Tokyo Ohka Kogyo Kabushiki Kaisha

Akira Yokota

Hisashi Nakane

Shingo Asaumi

Wataru Ishii

Toshimasa Nakayama

Hidekatsu Kohara

Hatsuyuki Tanaka

Takashi Komine

Shinji Tsuchiya

Yoshiyuki Sato

Shozo Miyazawa

Shirushi Yamamoto

Mitsuo Yabuta

Masakazu Kobayashi

Muneo Nakayama

Masanori Miyabe

Minoru Tsuda

Yoichi Nakamura

Yoshiaki Arai

Koichiro Hashimoto

Noboru Okazaki

A positive-working photoresist composition suitable for fine patterning in the manufacture of semiconductor devices, e.g., VLSIs, with high fidelity is proposed. The composition comprises 100 parts by weight of a cresol novolac resin and 25-60 parts by weight of a naphthoquinone diazide sulfonic acid ester as the photosensitive component while the cresol novolac resin component is prepared from a mixture of cresol isomers composed of 35-43% of m-cresol and 65-57% of p-cresol with substantial absence of o-cresol or composed of 35-43% of m-cresol, 65-57% of p-cresol and 1% or less of o-cresol.

Positive-working photoresist containing o-naphthoquinone diazide

The undercoating composition of the invention, useful for providing an undercoating layer for a top coat of a photosensitive resist layer on a substrate surface, comprises, as a principal ingredient thereof, a condensation product obtained by the condensation reaction between a hydroxy-substituted diphenylamine and a melamine compound substituted on the nitrogen atoms with methylol groups and/or alkoxymethyl groups. The undercoating obtained of the composition is highly resistant against the attack by the overcoating solution applied thereon so that the fidelity of the pattern reproduction by the photolithographic technique is greatly improved by virtue of the absence of any disorder at the interface between the undercoating and top coat layers. The advantage is further increased when the undercoating composition further comprises a photoextinctive agent, e.g. a dye, having absorptivity in the wave length region where the photosensitive resist of the top coat has sensitivity.

Undercoating material for photosensitive resins

The remover solution for photoresist layers comprises: (a) from 30 to 70% by weight of an aromatic hydrocarbon compound or a combination of aromatic hydrocarbon compounds having a flash point of 70.degree. C. or higher containing at least a half amount of a naphthalenic compound selected from the group consisting of naphthalene, methyl naphthalenes and dimethyl naphthalenes; (b) from 5 to 40% by weight of a phenolic compound; and (c) from 10 to 50% by weight of an arylsulfonic acid. The remover solution is effective for a variety of photoresist compositions with less problems in respect to the workers' health and danger of fire and explosion than conventional remover solutions.

Containing an arylsulfonic acid, a phenol and a naphalenic solvent

The aqueous developing solution of the invention for positive-working photoresist compositions contains, in addition to an organic basic compound free from metallic ions, such as tetramethyl ammonium hydroxide and choline, as the principal ingredient, from 50 to 5000 ppm of an acetylene alcohol. In comparison with conventional developing solutions, the inventive developing solution is advantageous in the uniformity of the patterned photoresist layer, higher sensitivity and smaller temperature dependency of development and less drawbacks due to foaming of the solution.

Developing solution for positive-working photoresist comprising tmah and

A dually photosensitive composition useful as a photoresist in the manufacture of ICs and the like electronic devices, which is positively photosensitive by exposure to ultraviolet in a relatively small dose but negatively photosensitive by exposure to ultraviolet in a substantially larger dose than above or by exposure to far ultraviolet light, is obtained by admixing a positive-type photoresist material comprising a novolac resin and an o-naphthoquinone diazide compound with a bisazide compound such as 4,4'-diazidodiphenyl sulfide. The inventive photosensitive composition provides a possibility of developing an ingenious technique for patterning of a photoresist layer on the substrate such as a checkboard-like patterned layer by use of a photomask of a line-and-space pattern.

Method of forming a positive resist pattern in photoresist of

The aqueous developing solution of the invention for positive-working photoresist compositions contains, in addition to an organic basic compound free from metal ions, such as tetramethyl ammonium hydroxide and choline, as the principal ingredient, from 50 to 5000 ppm of an anionic or non-ionic fluorine-containing surface active agent of specific types. In comparison with conventional developing solutions without such a surface active agent, the inventive developing solution is advantageous in the uniformity of the patterned photoresist layer and higher sensitivity and smaller temperature dependency of development.

Developing solution for positive-working photoresist comprising a metal

The invention provides an improvement over the conventional positive-working photoresist compositions comprising a novolac resin and an ester compound between 2,3,4-trihydroxybenzophenone and naphthoquinone-1,2-diazido-5-sulfonic acid in respect of scum formation in development and resistance of the patterned photoresist layer against heat and dry etching. The inventive composition comprises, in addition to the novolac resin and the ester compounds, 2,3,4-trihydroxybenzophenone in a specified amount relative to the ester compounds as a part of the photosensitive component which may be a reaction product obtained by the esterification reaction for the synthesis of the ester compounds containing unesterified 2,3,4-trihydroxybenzophenone.

Positive-working O-quinone diazide photoresist composition with

Method of preparing photoresist material with undercoating of

The invention provides an aqueous alkaline developer solution for a positive-type photoresist layer for pattern-wise treatment of the surface of a substrate, e.g., semiconductor wafer. The developer solution contains a tetraalkyl ammonium hydroxide, e.g., tetramethyl ammonium hydroxide, and a trialkyl hydroxyalkyl ammonium hydroxide, e.g., trimethyl hydroxyethyl ammonium hydroxide, as the essential ingredients and the temperature dependency of the development performance thereof is noticeably smaller than that of conventional developer solutions with respect to properties of the sensitivity of the photoresist and the thickness reduction of the photoresist layer in the unexposed areas, by virtue of the compensating temperature dependencies for these properties of these two ingredients for each other.

Aqueous developer solution for positive type photoresists with

A method for high-fidelity fine patterning of a photoresist layer involving a dry-process development by exposure to a plasma gas. Following irradiation in a pattern with actinic rays, a photoresist layer coated on a substrate is heated in an atmosphere at 200.degree. to 500.degree. C. Subsequent exposure of the photoresist layer to a plasma gas gives a finely patterned resist layer with a very high residual film ratio or very small decrease in the film thickness.

Method for fine pattern formation on a photoresist

A method for high fidelity patterning of a photoresist layer involving a dry-process development by exposure to a plasma gas. A photoresist layer which had been irradiated in a pattern with actinic rays is heated at a temperature in the range from 200.degree. to 500.degree. C. by applying heat to the surface of the substrate opposite to the surface bearing the photoresist layer, for example, by placing the substrate on a hot plate with the uncoated surface in contact with the hot plate. Subsequent exposure to plasma gas gives a patterned resist layer with a very high residual film thickness.

An efficient method is proposed for preventing leaching of contaminants from the surface of a solid, such as sodium ions from the surface of soda glass or nickel, chromium or iron from the surface of stainless steel in order to minimize detrimental contamination of highly pure substances in contact with the solid surface. The effect is basically obtained by providing a coating film of oxidized silicon on to the solid surface and the coating film is formed by applying a coating solution containing a hydroxysilane compound to the surface followed by baking of the coating layer at a temperature not lower than 150.degree. C., the coating solution being prepared by the equilibration reaction of an alkoxysilane with a carboxylic acid and an alcohol, of an acyloxysilane with an alcohol, or of an alkoxysilane with water in an alcohol where the molar ratios of the individual reactants are in the specified ranges.

Method for preventing leaching of contaminants from solid surfaces

A gallic acid alkyl ester or a gallic acid aryl ester is reacted in an inert solvent with 3 equivalents of naphthoquinone-(1,2)-diazido-(2)-sulfonyl chloride in the presence of an alkali to effect sulfonylation of 3 hydroxyl groups in the gallic acid moiety whereby a photodecomposable naphthoquinone-(1,2)-diazido-(2)-sulfonic acid ester is obtained. The new naphthoquinonediazido derivative thus obtained is mixed with an alkali-soluble phenol resin such as m-cresol novolac resin or phenol novolac resin to prepare a positive-type photoresist composition having high sensitivity and high resolving power as well as excellent dimensional accuracy and etching-resistance. In addition, this composition forms a good photosensitive film and can be a good ink receptor.

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Yamato, Japan

Akira Yokota