Organic compounds -- part of the class 532-570 series – Organic compounds – Diazooxide or diazotate
Reexamination Certificate
2001-05-08
2002-09-10
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Diazooxide or diazotate
Reexamination Certificate
active
06448383
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a method for producing 1,2-naphthoquinonediazide photosensitive agent used in a positive-type photoresist.
Positive-type photo resists containing an alkali-soluble resin and a 1,2-naphthoquinonediazide photosensitive agent are materials known to have excellent resolution, sensitivity, and etching resistance, and are used for producing semiconductor elements and liquid crystal elements. Generally, the photosensitive agent used in such a positive-type photoresist can be obtained through esterification between a polyhydric phenolic compound having hydroxyl groups and a 1,2-naphthoquinonediazide-sulfonic acid halide. In recent years, miniaturization of semiconductor elements has imposed a requirement for a strict control of the level of impurities in photoresists. Accordingly, there is demand for reducing the impurity level of the 1,2-naphthoquinonediazide photosensitive agent used in the photoresists.
Japanese Patent Application Laid-Open (kokai) No. 8-328247 discloses one previous method for producing a 1,2-naphthoquinonediazide. There, polyhydric phenolic compound and a 1,2-naphthoquinonediazide-sulfonic acid halide are subjected to a condensation reaction in an organic solvent in the presence of an organic amine; the resultant reaction mixture is neutralized; the formed organic amine acid salt is filtered off; and the filtrate is poured into an aqueous acidic solution. However, this method results in the presence of organic amine, acid, or organic amine acid salt which cannot be removed to a satisfactory degree of purity.
A 1,2-naphthoquinonediazide photosensitive agent containing a low level of impurities may be obtained if the aforementioned condensation is performed in an amide solvent serving as a reaction solvent, then neutralizing the resultant reaction mixture, filtering off the formed organic amine acid salt, and pouring the filtrate into an aqueous acidic solution. However, this method is also deficient in that a 1,2-naphthoquinonediazide-sulfonic acid halide is decomposed in amide solvent, and the resulting 1,2-naphthoquinonediazide-sulfonic acid remains as an impurity in the resulting photosensitive agent product.
Accordingly, a continuing need exists for a process which provides 1,2-naphthoquinonediazide photosensitive agent containing very small amounts of impurities such as an organic amine, an acid, or acid salts of the organic amine, and 1,2-naphthoquinonediazide-sulfonic acid.
SUMMARY OF THE INVENTION
The present invention is based on the discovery that a high-purity 1,2-naphthoquinonediazide photosensitive agent containing a low level of impurities can be obtained by condensing, in an organic solvent other than amide, at least one polyhydric phenolic compound and at least one 1,2-naphthoquinonediazide-sulfonic acid halide in the presence of an organic amine; subsequently adding an amide solvent to the resultant reaction mixture; and filtering off the formed organic amine hydrohalide salt.
Accordingly, the present invention provides a method for producing 1,2-naphthoquinonediazide photosensitive agent, comprising condensing, in organic solvent other than amide, at least one polyhydric phenolic compound and at least one 1,2-napthoquinonediazide-sulfonic acid halide in the presence of organic amine; subsequently adding amide solvent to the resultant reaction mixture; and filtering off the formed organic amine acid salt.
In an alternative embodiment of the invention, there is provided a method for producing 1,2-naphthoquinonediazide photosensitive agent, comprising condensing, in organic solvent other than amide, at least one polyhydric phenolic compound and at least one 1,2-naphthoquinonediazide-sulfonic acid halide in the presence of organic amine; subsequently adding amide solvent to the resultant reaction mixture; further adding volatile acid so as to render the resultant reaction mixture acidic; and filtering off the formed organic amine acid salt.
In still another embodiment of the present invention, there is provided a method for producing 1,2-naphthoquinonediazide photosensitive agent, comprising condensing, in organic solvent other than amide, at least one polyhydric phenolic compound and at least one 1,2-naphthoquinonediazide-sulfonic acid halide in the presence of organic amine; subsequently adding amide solvent to the resultant reaction mixture; further adding volatile acid so as to render the resultant reaction mixture acidic; filtering off the formed organic amine acid salt; pouring the resultant filtrate into pure water or an aqueous solution of a volatile acid, to thereby form precipitates; and collecting the precipitates through filtration.
DETAILED DESCRIPTION OF THE INVENTION
According to the present invention, a 1,2-naphthoquinonediazide photosensitive agent can be obtained by condensing, in organic solvent other than amide, at least one polyhydric phenolic compound and at least one 1,2-naphthoquinonediazide-sulfonic acid halide in the presence of organic amine; subsequently adding amide solvent to the resultant reaction mixture; and filtering off the formed organic amine acid salt.
Representative polyhydric phenolic compounds which can be used in the instant process include benzophenones such as 2,3,4-trihydroxybenzophenone, 2,3,4,4′-tetrahydroxybenzophenone, 2,2′,4,4′-tetrahydroxybenzophenone, 2,2′,3,4,4′-pentahydroxybenzophenone, and 2,3,3′,4,4′-pentahydroxybenzophenone; gallic acid alkyl esters; bis((poly)hydroxyphenyl)alkanes such as bis(4-hydroxy-2-methylphenyl)methane, bis(2,6-dimethyl-4-hydroxyphenyl)methane, 1,1-bis(4-hydroxyphenyl)cyclohexane, bis(2,4-dihydroxyphenyl)methane, 2,2-bis(2,4-dihydroxyphenyl)propane, bis (2,4-dimethyl-3-hydroxyphenyl)methane, (4-hydroxyphenyl)(2,3,4-hydroxyphenyl)methane, and 2-(4-hydroxyphenyl)-2-(2,3,4-hydroxyphenyl)propane; polyhydroxytriphenylalkanes disclosed, for example, in Japanese Patent Application Laid-Open (kokai) Nos. 3-142468, 3-158856, 4-29242, and 4-282454; polyhydroxybenzopyrans disclosed in Japanese Patent Application Laid-Open (kokai) No. 3-215863; polyhydroxyindanes disclosed, for example, in Japanese Patent Application Laid-Open (kokai) Nos. 3-215862 and 6-95374; polyhydroxycoumarones disclosed in Japanese Patent Application Laid-Open (kokai) Nos. 3-185447 and 7-56331; polyhydroxyphthalides disclosed in Japanese Patent Application Laid-Open (kokai) No. 5-27429; polyhydroxycoumarins disclosed in Japanese Patent Application Laid-Open (kokai) No. 5-27428; and polynuclear phenols disclosed, for example, in Japanese Patent Publication (kokoku) No. 4-502519 and Japanese Patent Application Laid-Open (kokai) Nos. 3-48249, 6-167805, 7-104465, 7-104467, 7-159989, 7-159990, 7-168355, 7-175213, 7-219920, 7-225476, 7-230166, 8-29978, 8-202031, 8-245461, and 8-320558. These polyhydric phenolic compounds can be used in reaction singly or in combination of two or more species.
Examples of 1,2-naphthoquinonediazide-sulfonic acid halides which can be used in the instant process include 1,2-naphthoquinonediazide-4-sulfonyl chloride, 1,2-naphthoquinonediazide-5-sulfonyl chloride, and 1,2-naphthoquinonediazide-6-sulfonyl chloride. These 1,2-naphthoquinonediazide-sulfonic acid halides can be used singly or in combination of two or more.
Examples of organic amines which can be used in the instant process include ethylamine, diethylamine, triethylamine, diisopropylamine, tripropylamine, triisobutylamine, triethanolamine, monomethyldicyclohexylamine, N-methylpiperidine, N-methylmorpholine, N-methylpyrrolidine, 1,4-dimethylpiperazine, pyridine, N,N-dimethylaniline, and N,N-dimethylaminopyridine. These amines can be used singly or in combination of two or more.
The reaction solvent used in the present invention is an organic solvent other than amide. Examples of preferred organic solvents include acetone, 1,4-dioxane, 1,3-dioxolane, tetrahydrofuran (THF), &ggr;-butyrolactone, and propylene carbonate. These specific solvents are preferred. These solvents can be used singly or in combination of two or more.
Aft
Hayakawa Masamichi
Yamanaka Tomotaka
Huntley & Associates
Powers Fiona T.
Toyo Gosei Kogyo Co. Ltd.
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