Tokyo Ohka Kogyo Co., Ltd.

Tokyo Ohka Kogyo Kabushiki Kaisha

Shingo Asaumi

Hatsuyuki Tanaka

Toshimasa Nakayama

Hidekatsu Kohara

Hisashi Nakane

Akira Yokota

Masanori Miyabe

Yoshiaki Arai

Masakazu Kobayashi

Yoshiyuki Sato

Takashi Komine

Muneo Nakayama

Nobuo Tokutake

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

A positive-working photoresist composition suitable for fine patterning in the manufacturing of semiconductor devices such as VLSIs with high fidelity is proposed. The composition comprises: (A) 100 parts by weight of a phenolic novolac resin prepared by the condensation reaction of a specific ternary mixture of three kinds of phenolic compounds and formaldehyde; and (B) 20-60 parts by weight of a photosensitizer which is preferably an ester of naphthoquinone diazidesulfonic acid and a hydroxylated benzophenone compound. The phenolic mixture is composed of 10-45% by weight of m-cresol, 35-88% by weight of p-cresol and 2-30% by weight of a substituted phenol represented by the general formula R.C.sub.6 H.sub.4.OH, in which R is a monovalent aliphatic hydrocarbon group having 2-6 carbon atoms selected from alkyl and alkenyl groups.

Positive-working photoresist composition with quinone diazide sulfonic

The photosensitive composition, which is suitable as a photoresist material in fine patterning works for the manufacture of semiconductor devices, contains, as a photoextinctive agent, a combination of an alkali-insoluble dye and an alkali-soluble dye each having absorptivity of light in the wavelength region from 230 to 500 nm in a specified amount and in a specified ratio between them. By virtue of the formulation of combined dyes, the undesirable phenomenon of halation by the underlying aluminum coating layer on the substrate surface is greatly decreased so that patterned resist layer obtained with the composition is a high-fidelity reproduction of the original pattern even in a submicron range of fineness with good rectangularity of the cross sectional form of the patterned lines.

Positive-working photosensitive quinone diazide composition with alkali

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

The improvement of the invention consists in the use of a specific ether compound, e.g., diethyleneglycol monomethyl, monoethyl and monobutyl ethers, dipropyleneglycol monomethyl and monoethyl ethers, triethyleneglycol monomethyl and monoethyl ethers and tripropyleneglycol monomethyl ether, as a rinse solvent for a substrate from which the pattern photoresist layer has been removed with a remover solution in the photolithographic processing of semiconductor devices. The rinse solvent is free from the problems in the toxicity to human body and environment pollution relative to waste disposal as well as the danger of fire. The rinse solvent is versatile to be applicable to both of the negative- and positive-working photoresist compositions. Further advantages are obtained by adding an aliphatic amine compound to the rinse solvent.

Method for rinse treatment of a substrate

Although the positive-working photoresist composition comprises a phenolic novolac resin as the film-forming component and a known photosensitizing compound as in conventional compositions, the novolac resin is prepared from a specific mixture of two classes of phenolic compounds including, one, phenol, cresols and/or resorcinol and, the other, one or more of the phenolic compounds having a nucleus-substituting group selected from allyloxy, allyloxymethyl, allyl dimethyl silyl, 2-(allyl dimethyl silyl) ethoxy, cinnamoyl, acryloyl and methacryloyl groups. By virtue of this unique combination to give the phenolic moiety in the novolac resin, the photoresist composition has markedly improved heat resistance as well as stability against plasma in dry etching so that the composition can give a patterned photoresist layer with extreme fineness having high fidelity to the mask pattern.

Highly heat-resistant positive-working o-quinone diazide containing

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

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 a cresol novolac resin and a naphthoquinone diazide sulfonic acid ester as the photosensitive component while the cresol novolac resin component is characteristically a combination of two different cresol novolac resins differentiated in respects of the weight-average molecular weight, one large and the other small, and the weight proportion of the m- and p-isomers of cresol, one rich in the m-isomer and the other rich in the p-isomer, used in the preparation of the novolac and the overall weight ratio of the m-cresol and p-cresol moieties in the thus combined cresol novolac resins also should be in a specified range.

Positive-working naphthoquinone diazide photoresist composition with two

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.

Growing community of inventors

Fujisawa, Japan

Shingo Asaumi