Sumitomo Chemical Company, Limited

Takeshi Hioki

Yasunori Uetani

Jun Tomioka

Ryotaro Hanawa

Haruyoshi Osaki

Yasunori Doi

Fumio Oi

Kiyoteru Kojima

Makoto Hanabata

Ayako Ida

Hiroshi Moriuma

Yukio Hanamoto

Shinji Konishi

Takanori Yamamoto

Haruyoshi Ozaki

Seiko Kurio

Hiroshi Ueda

Hirotoshi Nakanishi

Naoki Takeyama

Akihiro Furuta

Yoshiaki Hayashi

Takehiro Kusumoto

Teijiro Kitao

Koji Kuwana

Taira Fujita

Hiroshi Takagaki

Tooru Tokumaru

Masaru Matsuoka

Kota Tokuhara

Manabu Yahata

Akirhiro Furuta

Koichi Kamemoto

Motomasa Ohsu

Provided are a method of producing a photoresist comprising a process of filtrating a raw resist solution containing resist constituent components and a resist solvent dissolving them, using a filter made of at least one resin selected from fluorine-based resins and polyolefins, wherein this filter has been used for filtration of the same or different kind of other raw resist solution and has been washed with a solvent containing the resist solvent toward the reverse direction to the filtration direction, and a method of sequentially producing two or more photoresists using the same production apparatus, wherein this production apparatus is washed with the resist solvent, a solvent other than this resist solvent capable of dissolving or decomposing the resist constituent components, and the resist solvent, in this order, after production of the photoresist and before production of the subsequent photoresist.

Method of producing photoresist

A positive resist composition which comprises a 1,2-quinone diazide compound and an alkali-soluble resin containing a polyphenol compound (I) of the general formula:

Radiation-sensitive positive resist composition comprising a 1,2-quinone

A positive resist composition comprising 1,2-quinonediazide compound and, as an alkali-soluble resin, an alkali-soluble resin (A) which comprises a resin (I) obtainable through a condensation reaction of a mixture of m-cresol, 2,3,5-trimethylphenol and optionally p-cresol with an aldehyde and a low molecular weight novolak (II) having a weight average molecular weight of 200 to 2000 as converted to polystyrene, an alkali-soluble resin (B) which comprises a resin (I) and a compound of the general formula (III): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are respectively a C.sub.1 -C.sub.5 alkyl group or a C.sub.1 -C.sub.5 alkoxy group, 1, m and n are respectively a number of 0 to 3, R' is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group, or an alkali-soluble resin (C) which comprises a resin (IV) obtainable through a condensation reaction of a mixture of m-methoxyphenol and 2,3,5-trimethylphenol in a molar ratio of 80:20 to 30:70 with an aldehyde, which has good sensitivity, improved resolution and heat resistance.

Radiation-sensitive positive resist composition

A positive resist composition comprising 1,2-quinonediazide compound and, as an alkali-soluble resin, an alkali-soluble resin (A) which comprises a resin (I) obtainable through a condensation reaction of a mixture of m-cresol, 2,3,5-trimethylphenol and optionally p-cresol with an aldehyde and a low molecular weight novolak (II) having a weight average molecular weight of 200 to 2000 as converted to polystyrene, an alkali-soluble resin (B) which comprises a resin (I) and a compound of the general formula (III): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are respectively a C.sub.1 -C.sub.5 alkyl group or a C.sub.1 -C.sub.5 alkoxy group, l, m and n are respectively a number of 0 to 3, R' is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group, or an alkali-soluble resin (C) which comprises a resin (IV) obtainable through a condensation reaction of a mixture of m-methoxyphenol and 2,3,5-trimethylphenol in a molar ratio of 80:20 to 30:70 with an aldehyde, which has good sensitivity, improved resolution and heat resistance.

Radiation-sensitive positive resist composition comprising an alkali

A positive resist composition which comprises, in admixture, a photosensitive 1,2-quinone diazide compound, an alkali-soluble resin to bind ingredients and polyphenol compound to control a dissolution rate in a developer having a molecular weight of not more than 550 and represented by the general formula: ##STR1## wherein a, b, c, d, e, and f are the same or different and a number of 0-3, provided that d+f is not less than 1, and provided that if b, d and f are 1, then at least one of a, c, and e is not 0; R.sub.1, R.sub.2 and R.sub.3 are the same or different and a C.sub.1 -C.sub.18 alkyl group, a C.sub.1 -C.sub.18 alkoxy group, a carboxyl group or a halogen atom; R.sub.4 is a hydrogen atom, a C.sub.1 -C.sub.18 alkyl group or aryl group, wherein an amount of said 1,2-quinone diazide compound is from 5 to 100% by weight and an amount of said polyphenol compound is from 4 to 40% by weight based on the total weight of said alkali-soluble resin, wherein the resist composition is sensitive to radiation and has good balance of sensitivity, resolving power and heat resistance.

A positive resist composition which comprises, in admixture, a photosensitive 1,2-quinone diazide compound, an alkali-soluble resin to bind ingredients and polyphenol compound to control a dissolution rate in a developer represented by the formula: ##STR1## wherein R is C.sub.1-18 or hydrogen, the composition is sensitive to radiation and has good balance of sensitivity, resolving power and heat resistance.

A positive resist composition containing a 1,2-quinone diazide compound and an alkali-soluble resin which constitutes a resin (I) obtainable through a condensation reaction of a phenol mixture containing m-cresol and 2-tert.-butyl-5-methylphenol with an aldehyde., which has well balanced sensitivity, resolution and heat resistance properties.

Radiation-sensitive positive resist composition comprising an

A positive resist composition comprising a 1,2-quinone diazide compound and an alkali-soluble resin which comprises a resin (I) obtainable through a condensation reaction of an aldehyde with a phenol mixture containing m-cresol and at least one selected from the group consisting of 2-tert.-butyl-4-methylphenol and 2-tert.-butyl-6-methylphenol, which has well balanced properties.

A photoresist composition which includes a sensitizing compound, a resin and, as a light absorber, a styryl compound of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.11 are the same or different and a hydrogen atom, an optionally substituted alkyl, alkenyl or aralkyl group or R.sub.1 and R.sub.2 may form a ring together with the nitrogen atom to which they are bonded, which ring may include at least one hetero atom in addition to said nitrogen atom; R.sub.10 is an optionally substituted alkylene group; R.sub.3 is --OH, --OCOR.sub.5 or --OSi(R.sub.5).sub.3 in which R.sup.5 is an alkyl group; R.sub.12 and R.sub.13 are independently a hydrogen atom, an optionally substituted lower alkyl or alkoxy group, an amide group or a halogen atom; X, Y, W and Z are the same or different and an electron attracting group, and n is a number of 2-15.

Photoresist compositions comprising styryl compound

This invention provides azamethine compounds represented by the formula (I): ##STR1## wherein X represents ##STR2## R.sub.1 to R.sub.4 represent independently a hydrogen atom, an alkyl group, an alkoxyl group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group, ##STR3## R.sub.5 and R.sub.6 represent independently a hydrogen atom or an alkyl group which may be substituted by a hydroxyl group; R.sub.7 represents a hydrogen atom, an alkyl group, an alkyoxyl group, a hydroxyl group, a halogen atom, a nitro group, a cyano group, ##STR4## wherein -A represents ##STR5## and R and R' represent independently a hydrogen atom or an alkyl group; and R.sub.10 to R.sub.12 represent independently a hydrogen atom or an alkyl group, a process for producing such compounds, and a medium for recording optical information using these compounds.

Sulfone-containing azamethide compounds with a nitrogen-containing

A styryl compound of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.11 are the same or different and a hydrogen atom, an optionally substituted alkyl, alkenyl or aralkyl group or R.sub.1 and R.sub.2 may form a ring together with the nitrogen atom to which they are bonded, which ring may include at least one hetero atom in addition to said nitrogen atom; R.sub.10 is an optionally substituted alkylene group; R.sub.3 is --OH, --OCOR.sub.5 or --OSi(R.sub.5).sub.3 in which R.sup.5 is an alkyl group; R.sub.12 and R.sub.13 are independently a hydrogen atom, an optionally substituted lower alkyl or alkoxy group, an amide group or a halogen atom; X, Y, W and Z are the same or different and an electron attracting group, and n is a number of 2-15, which is suitable as a light absorber in a photoresist composition.

Styryl compounds, process for preparing the same and photoresist

A resist composition comprising an alkali-soluble resin, a 1,2-quinone diazide compound and a compound of the general formula (I): ##STR1## wherein Z is an oxygen or sulfur atom or a group of the formula: &gt;N--R.sub.4 in which R.sub.4 is a hydrogen atom or an alkyl group; R.sub.1, R.sub.2 and R.sub.3 are the same or different and independently a hydrogen atom, a substituted or unsubstituted alkyl group, a halogen atom, a hydroxyl group, a cyano group or a group of the formula: --OCOR' in which R' is a substituted or unsubstituted alkyl group; and X and Y are independently a cyano group or a group of the formula: ##STR2## --COOR or --CONHR' in R is an alkyl group and R' is a hydrogen atom or an aryl group, which is suitable for the formation of very fine patterns on a substrate having a high reflectance.

Resist composition containing alkali-soluble resin, 1,2-quinone diazide

A positive resist composition comprising a radiation-sensitive component and an alkali-soluble resin and a phenol compound of the formula: ##STR1## wherein R is a hydrogen atom, a lower alkyl group or a phenyl group, R' is an alkyl group or an alkoxy group, and n is a number of 0 to 3, which has well balanced good properties such as sensitivity, resolution, heat resistance and adhesiveness.

Positive resist composition containing 1,2-quinone diazide compound,

This invention provides azamethine compounds represented by the formula (I): ##STR1## (wherein X represents ##STR2## Y represents C.dbd.O, C.dbd.C(CN).sub.2 or SO.sub.2 ; R.sub.1 to R.sub.4 represent independently a hydrogen atom, an alkyl group which may be substituted, an alkoxyl group which may be substituted, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group which may be substituted, --A--R or ##STR3## R.sub.5 and R.sub.6 represent independently a hydrogen atom, an alkyl group which may be substituted, an aryl group which may be substituted or a cyclohexyl group; R.sub.5 and R.sub.6 may be combined to form a ring or may form a ring with a hetero atom; R.sub.7 and R.sub.8 represent independently a hydrogen atom, an alkyl group which may be substituted, an alkoxyl group which may be substituted, a hydroxyl group, a halogen atom, a nitro group, a cyano group, --A--R or ##STR4## wherein --A represents represents ##STR5## and R and R' represent independently a hydrogen atom, an alkyl group which may be substituted, an aryl group which may be substituted, a heterocyclic group or a cyclohexyl group; R.sub.9 represents a hydrogen atom, an alkyl group which may be substituted, or an aryl or heteroaryl group which may be substituted; and R.sub.10 to R.sub.12 represent independently a hydrogen atom or an alkyl group), a process for producing such compounds, and a medium for recording optical information using these compounds.

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Osaka, Japan

Takeshi Hioki