Fuji Photo Film Company, Limited

Nippon Telegraph and Telephone Corporation

Tadayoshi Kokubo

Yasumasa Kawabe

Kazuya Uenishi

Shiro Tan

Toshiaki Aoai

Shinji Sakaguchi

Tadashi Ikeda

Tetsuo Yoshida

Keiichi Adachi

Isamu Itoh

Hiroshi Kitaguchi

Yasushi Nozawa

Hiroshi Matsumoto

Masaki Okazaki

Hidetoshi Kobayashi

Akinobu Tanaka

Akira Umehara

Yoshimasa Aotani

Itsuo Fujiwara

Kiyohiko Yamamuro

Hiroshi Ban

Kenichi Kuwabara

Hiroshi Yoshimoto

Wataru Ishii

Atsushi Sakamoto

Nobuaki Matsuda

A positive-working light-sensitive composition which comprises:

Light-sensitive composition

A positive type or negative type light-sensitive composition providing high sensitivity and high resolution in the manufacture of a semiconductor device, and contains:

A novel positive type photoresist composition is provided, comprising an alkali-soluble novolak resin obtained by the condensation of substituted or unsubstituted phenols and aldehydes in the presence of a silica-magnesia solid catalyst and a light-sensitive material containing 1,2-naphthoquinone-diazido-5-(and/or -4-) sulfonate as main component.

Positive type photoresist composition comprising a novolak resin made

A photoresist composition is disclosed containing an alkali-soluble resin and a photosensitive substance obtained by reaction of a polyhydroxy compound and (a) a 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonyl chloride(s), said photosensitive substance being a mixture of photosensitive compounds (1) to (3): (1) a photosensitive compound having at least one hydroxyl group per molecule and having a number ratio of 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonyl chloride sulfonate groups to hydroxyl groups within the range of from 3 to 20, contained in the photosensitive substance in an amount of 50 wt % or more; (2) a photosensitive compound where all the hydroxyl groups in the polyhydroxy compound have been 1,2-naphthoquinonediazidosulfonyl-esterified, contained in the photosensitive substance in an amount of 30 wt % to 0 wt %; and (3) a photosensitive compound having three or more hydroxyl groups which have not been 1,2-naphthoquinonediazidosulfonyl-esterified per molecule, contained in the photosensitive substance in an amount of 20 wt % to 0 wt %. The composition is suitable to exposure with g-ray, i-ray and excimer laser to provide a sharp resist image. The photoresist composition also has high sensitivity, high resolving power, precise reproducibility to provide resist images having good sectional shapes, broad development latitude, high heat resistance and good storage stability.

Positive photoresist composition

A positive photoresist composition comprising an alkali-soluble novolak resin and a 1,2-quinonediazide compound is described, wherein the alkali-soluble novolak resin contains a novolak resin to be obtained by condensing a mixture of (a) at least one phenol represented by the following formula (1) and at least one compound represented by the following formula (2) and (b) at least one aldehyde: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, an aralkyl group, an alkoxycarbonyl group or an arylcarbonyl group; R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are the same or different and each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, a cycloalkyl group, an alkoxy group, an alkenyl group, an aryl group or an aralkyl group; and n represents an integer of from 4 to 7.

Positive photoresist composition comprising a novolak resin having a

The present invention relates to a positive-working photoresist composition comprising at least one of the 1,2-naphthoquinonediazido-5- sulfonic acid ester of a polyhydroxy compound represented by formula (1) and the 1,2-naphthoquinonediazido-4-sulfonic acid ester of a polyhydroxy compound represented by formula (1): ##STR1## wherein R represents a hydrogen atom, a hydroxy group, a halogen atom, a nitro group, an alkyl group having from 1 to 6 carbon atoms, an aryl group, or an alkenyl group; and R.sub.1 to R.sub.15, which may be the same or different, each represents a hydrogen atom, a hydroxy group, a halogen atom, an alkyl group having from 1 to 6 carbon atoms, an alkoxy group, or a substituted or unsubstituted cycloalkyl group, with the proviso that at least one of R.sub.1 to R.sub.15 is a substituted or unsubstituted cycloalkyl group.

Positive working photoresist composition containing naphthoquinone

A resist composition comprising a compound having an active hydrogen and an alkali-soluble siloxane polymer containing in the molecules thereof at least one unit selected from a unit represented by formula (I) and a unit represented by formula (II) ##STR1## wherein the X's are the same or different and each represents one member selected from the group consisting of hydrogen, ##STR2## (where R represents hydrogen, a hydrocarbon group, or a substituted hydrocarbon group); and a carboxyl group;

Resist composition comprising a siloxane or silsesquioxane polymer

A micropattern-forming, light sensitive resin composition is disclosed. The composition comprises (a) a novolak resin comprising a condensate between formaldehyde and a mixture of m-cresol and p-cresol with a m-cresol to p-cresol charging weight ratio of from 45/55 to 60/40, wherein the novolak resin has the following characteristics: (i) a dissolving rate of 20 to 800 .ANG./sec in an aqueous solution of tetramethylammonium hydroxide (TMAH) and an alkali activity of 0.131N, (ii) a weight average molecular weight of 1000 to 6000 calculated as polystyrene equivalent, and (iii) a non-exposed dissolving rate of equal to or more than 100 .ANG./sec in an aqueous solution of TMAH with an alkali activity of 0.262N; (b) a light-sensitive substance of 1,2-naphthoquinonediazide-4-sulfonyl ester, and (c) a solvent capable of dissolving the novolak resin and the light-sensitive substance; wherein the novolak resin, the light-sensitive substance, and the solvent are present in such amounts that a 1.0 micron thick resist formed of the material has an optical density at 382 nm of 0.1 to 0.4 .mu.m.sup.-1. Also described is a micropattern-forming process having the steps of: (1) spin coating a substrate with the light-sensitive resin composition; (2) drying the light-sensitive composition; (3) exposing the dried light-sensitive composition using deep UV having a wavelength not longer than about 320 nm; and (4) developing the exposed light-sensitive composition.

Micropattern-forming material having a low molecular weight novolak

There is disclosed a positive type photoresist composition comprising an alkali-soluble resin, a compound having a 1,2-naphthoquinonediazido group, and at least one light absorbing agent selected from the group consisting of the compounds represented by the following formulae [I] and [II], the content of said light absorbing agent being in the range of 0.1 to 10% by weight based on the total solid content of the composition: ##STR1## wherein X represents a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkoxy group, an acyl group, or an aryl group; Y represents a single bond, an alkylene group, --O--, --S--, --SO.sub.2 --or ##STR2## R represents a hydrogen atom, an alkyl group, or an aralkyl group; m represents an integer from 1 to 3; and n represents an integer from 1 to 4. The content of light absorbing agent in said composition is in the range of from 0.3% by weight to 5% by weight, based on the total solid content of the composition.

Positive type 1,2-naphthoquinonediazide photoresist composition

A negative type photoresist composition comprising a light-sensitive s-triazine compound represented by formula (I), an acid-crosslinkable material, and an alkali soluble resin: ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, each represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, a substituted aryl group, a group represented by formula (II) or (III), or R.sub.1 and R.sub.2 may form a heterocyclic group consisting of non-metal atoms bonded to a nitrogen atom; R.sub.3 and R.sub.4 each represent a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group; X and Y, which may be the same or different, each represents a chlorine atom or a bromine atom; and m and n each represents 0, 1 or 2; ##STR2## wherein R.sub.5 represents an alkyl group, a substituted alkyl group, an aryl group, or a substituted aryl group; and R.sub.6 and R.sub.7, which may be the same or different, each represents a hydrogen atom, an alkyl group, a substituted alkyl group, an aryl group, or a substituted aryl group.

Negative type photoresist composition

Disclosed is a novel positive type photoresist composition comprising a 1,2-naphthoquinonediazido-5-(and/or -4-)sulfonic ester of a member selected from the group consisting of the polyhydroxy compounds represented by the following formula (I), (II) or (III) and an alkali-soluble resin: ##STR1## wherein the variables of Formula I are defined in the specification; ##STR2## wherein the variables of Formula II are defined in the specification; ##STR3## wherein the variables of Formula III are defined in the specification.

Positive type photoresist composition

A positive-type photoresist composition is described as including:

Positive-type photoresist composition

A composition, useful for its excellent resolution, sensitivity, development properties, and heat resistance, having an alkali soluble resin and a quinonediazide compound as essential ingredients, and further containing at least one polyhydroxy compound represented by the following formula (I) or (II): ##STR1## wherein R's, which may be the same or different, each represents a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, an alkoxy group or --CH.sub.2 N--(--CH.sub.2 COOH).sub.2 ; X represents a --C(.dbd.O)-- group or an --SO.sub.2 -- group; m is an integer of 1 to 3; and n is an integer of 1 to 4.

Positive quinone diazide photoresist composition containing select

Disclosed is a positive type photoresist composition comprising an alkali-soluble resin, a quinone diazide compound and a compound represented by the following general formula (I): ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 which may be the same or different and in which four groups for each group may be different from each other at the same time, each represents a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, an alkoxy group, a nitro group, an alkenyl group, an aryl group, an aralkyl group, an alkoxycarbonyl group, an arylcarbonyl group, an acyloxy group, an acyl group, an aryloxy group or an aralkoxy group; a, b, d and e each represents 0 or an integer 1 to 3; and c represents 0 or 1, with the proviso that a, b, c, d and e satisfy the relationship (a+b+c+d+e.gtoreq.2), at least one of a and d is 1 or more and at least one of b and e is 1 or more.

Positive type quinonediazide photoresist composition containing select

A positive photoresist composition includes an alkali-soluble resin, a quinonediazide compound and a compound selected from the group consisting of compounds represented by formulae (I), (II) and (III): ##STR1## wherein R.sub.1 to R.sub.27, which may be the same or different, each represents a hydrogen atom, hydroxyl group, halogen atom, alkyl group, alkoxy group, nitro group, alkenyl group, aryl group, aralkyl group, alkoxycarbonyl group, arylcarbonyl group, acyloxy group, acyl group, aryloxy group or aralkoxy group; ##STR2## wherein R.sub.31 represents an organic group, single bond, ##STR3## R.sub.32 represents a hydrogen atom, monovalent organic group or ##STR4## R.sub.33 to R.sub.37, which may be the same or different, and in which not all four groups for each of R.sub.33 to R.sub.37 may be the same at the same time, each represents a hydrogen atom, hydroxyl group, halogen atom, alkyl group, alkoxy group or alkenyl group, with the proviso that at least one of R.sub.33 to R.sub.35 is a hydroxyl group; X represents a divalent organic group; and m represents an integer 0 or 1; ##STR5## wherein R.sub.41 to R.sub.44, which may be the same or different and in which not all four groups for each of R.sub.41 to R.sub.44 may be the same at the same time, each represents a hydrogen atom, hydroxyl group, halogen atom, alkyl group, alkoxy group or alkenyl group; R.sub.45 and R.sub.46 each represents a hydrogen atom, alkyl group or ##STR6## a and c each represents an integer 0 or 1; and b represents an integer from 1 to 4.

Growing community of inventors

Shizuoka, Japan

Tadayoshi Kokubo