Japan Synthetic Rubber Co., Ltd.

Takao Miura

Yoshiji Yumoto

Toshiyuki Ota

Toru Kajita

Makoto Murata

Eiichi Kobayashi

Hiroaki Nemoto

Ikuo Nozue

Mikio Yamachika

Akihiro Yamanouchi

Satoshi Miyashita

Hidetoshi Miyamoto

Shinji Shiraki

Chozo Okuda

Tsutomu Shimokawa

Yasumasa Takeuchi

Yoshinori Yoshida

Yoshiyuki Harita

Masayuki Endo

Yoichi Kamoshida

Hiroshi Oka

Takayoshi Tanabe

Takahiro Tsunoda

Taro Okumura

Toshihiko Takahashi

Mitsuo Ichikawa

Mitsuru Tashiro

Tatsusuke Chikatsu

Shinichi Shimokawa

A radiation-sensitive resin composition comprising an alkali-soluble novolak resin and a 1,2-quinonediazide compound, wherein the alakli-soluble novolak resin comprises a mixture of: 95-50 parts by weight of Resin A having a standard polystyrene-reduced weight-average molecular weight of 2,000-20,000 �Resin A is at least one resin selected from the group consisting of a resin obtained by polycondensation of m-cresol and at least one phenol represented by the structural formula (I) or (I'): ##STR1## wherein m is 2 or 3, with at least one aldehyde and a resin obtained by polycondensation of m-cresol, p-cresol and at least one phenol represented by the above structural formula (I) or (I') with at least one aldehyde! and 5-50 parts by weight of Resin B having a standard polystyrene-reduced weight-average molecular weight of 200-2,000 �Resin B is a resin obtained by polycondensation of at least one phenol represented by the structural formula (II): ##STR2## wherein n is 0, 1, 2 or 3, with at least one aldehyde!. In the resin composition, the mixture of Resin A and Resin B may further contain Resin C which is an ester of Resin B with a 1,2-quinonediazidesulfonic acid.

Radiation-sensitive resin composition

A radiation sensitive resin composition useful as a negative type resist which can form a resist pattern having a good shape, has so high acid resistance as not to be affected by an etchant and a high adhesion to the substrate, and is endowed with so high a strippability as to be easily dissolved in a stripping solution consisting of an organoalkali. Said composition comprises (1) 100 parts by weight of an alkali-soluble novolak resin having a polystyrene reduced weight average molecular weight of 1,000 to 10,000, (2) 1 to 10 parts by weight of a compound having a methylol group and/or an alkoxymethyl group and being capable of cross-linking the alkali-soluble novolak resin (1) in the presence of an acid, and (3) 0.01 to 5 parts by weight of a radiation sensitive acid-generating agent represented by formula (I): ##STR1##

Radiation sensitive resin composition

A chemically amplified resist comprising an alkali-soluble resin or a resin having at least one acid-dissociable group which is alkali-insoluble or -sprairingly soluble but becomes alkali-soluble upon dissociation of said acid dissociable group due to an acid; a radiation-sensitive, acid-generating agent; and an optional component in which resist, the radiation-sensitive, acid-generating agent generates an acid upon irradiation with a radiation in the irradiated portion and the solubility of the resin component and optional component in a developing solution is varied in the irradiated portion by a chemical reaction caused by the catalytic action of the acid, whereby a pattern is formed, characterized in that a compound having a nitrogen-containing basic group is contained in the resist. Said resist is superior in developability, pattern form, resolution, focus tolerance and yield of residual film thickness, has good process stability, and can be suitably used even in irradiation with, in particular, a radiation having a wavelength equal to or smaller than far ultraviolet rays, for example, an excimer laser or the like.

Chemically amplified resist

A reflection preventing film for forming a resist pattern and a process for forming the resist pattern using the film. The film comprises a copolymer was copolymerized of monomers which comprise at least one unsaturated carboxylic acid monomer, at least one epoxy group-containing unsaturated monomer, and at least one cinnamoylphenyl group-containing unsaturated monomer. The reflection preventing film exhibits a high halation preventing effect, involves no sublimation of radiation absorbing components contained therein, is free from occurrence of intermixing, possesses excellent heat resistance, exhibits a superb dry etching performance and storage stability, and produces resist patterns with excellent resolution and precision. The resist pattern forming process comprises forming the reflection preventing film on a substrate, forming a resist coating film on said reflection preventing film, irradiating the resist film with a radiation, and developing the resist coating film.

Reflection preventing film and process for forming resist pattern using

A radiation sensitive resin composition which can be suitably used as a negative type resist having a high sensitivity, a high resolution, a high yield of residual film thickness and high thermal resistance, and which comprises (A) an alkali-soluble novolak resin, (B) a phenolic compound having a standard polystyrene-reduced weight average molecular weight of 10,000 or less such as polyvinylphenol, (C) a compound capable of cross-linking the component (A) and/or the component (B) in the presence of an acid, and (D) a radiation sensitive acid generator such as a triazine compound having a halomethyl group.

A radiation-sensitive composition comprising (A) a polymer having a recurring unit represented by formula (1): ##STR1## wherein R.sup.1 represents a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.2 represents --OR.sup.3 or --NR.sup.4 R.sup.5 in which R.sup.3 is a hydrogen atom, a straight-chain alkyl group, a cyclic alkyl group, an aryl group, an aralkyl group, a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.4 and R.sup.5, which may be the same or different, are hydrogen atoms, straight-chain alkyl groups, cyclic alkyl groups, aralkyl groups or aryl groups, and (B) a radiation-sensitive acid forming agent. Said radiation-sensitive composition can be suitably used as a resist composition which enables reliable fine processing, which has high sensitivity and high resolution degree, and which is superior in dry etching resistance, develop-ability, adhesiveness, heat resistance and yield of residual film thickness.

Radiation-sensitive composition

A radiation-sensitive resin composition comprising an alkali-soluble novolak resin and a 1,2-quinonediazide compound, wherein the alakli-soluble novolak resin comprises a mixture of:

An i-ray sensitive positive resist composition: which (A) comprises an alkali-soluble novolak resin obtained by subjecting (a) a phenolic mixture of B to 95 mol % of 2,3-xylenol with 95 to 5 mol % of a phenol selected from mono-, di- and tri-methyl phenols other than 2,3-xylenol or (b) a phenolic mixture of 5 to 50 mol % of 8,4-xylenol with 95 to 50 mol % of a phenol selected from mono-, di- and tri-methyl phenols other than 3,4-xylenol to polycondensation together with an aldehyde, and a 1,2-quinonediazide compound, and (B) which has sensitivity to i-ray. There is also provided a method of forming a pattern, which comprises: (1) applying the i-ray sensitive positive resist composition to a wafer to form a photosensitive layer, (2) irradiating the photosensitive layer with i-ray through a predetermined pattern, and (3) developing the pattern with a developer.

I-ray sensitive positive resist composition

A reflection preventing film comprising a copolymer, its salt or both of them, the copolymer having at least one recurring unit selected from the group consisting of recurring units represented by formulas (1) and (2) and at least one recurring unit represented by formula (3): ##STR1## wherein R.sup.1 -R.sup.4 which may be the same as or different from one another, represent hydrogen atoms or organic groups and X represents a carboxyl group or a sulfo group, ##STR2## wherein R.sup.5 represents a hydrogen atom or an organic group, A represents a fluoroalkyl group and Y represents an alkylene group or a fluoroalkylene group. The reflection preventing film is formed on a resist film before irradiation in the formation of a resist pattern, thereby preventing the radiation reflected on the substrate from re-reflecting at the upper interface of the resist film to provide a resist pattern excellent in resolution, developability and pattern form.

A negative type radiation-sensitive resin composition which comprises (A) an alkali-soluble resin, (B) a compound which generates an acid upon irradiation, and (C) an aromatic compound having, as functional groups, an --OR group and a --CH.sub.2 OX group, both directly bonded to the aromatic ring in which R represents a substituted methyl group, a substituted ethyl group, a silyl group, an alkoxycarbonyl group or an acyl group and in which X represents a hydrogen atom, an alkyl group having 1-5 carbon atoms or an R group which is as defined above, said aromatic compound being capable of cross-linking the alkali-soluble resin (A) in the presence of an acid, and optionally (D) a specific phenolic compound. The negative type radiation-sensitive resin composition is excellent in developability, pattern-formation, resolution and thermal durability.

Negative type radiation-sensitive resin composition

A radiation-sensitive composition comprising (A) a polymer having a recurring unit represented by formula (1): ##STR1## wherein R.sup.1 represents a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.2 represents --OR.sup.3 or --NR.sup.4 R.sup.5 in which R.sup.3 is a hydrogen atom, a straight-chain alkyl group, a cyclic alkyl group, an aryl group, an aralkyl group, a substituted methyl group, a substituted ethyl group, a silyl group, a germyl group or an alkoxycarbonyl group, and R.sup.4 and R.sup.5 which may be the same or different, are hydrogen atoms, straight-chain alkyl groups, cyclic alkyl groups, aralkyl groups or aryl groups, and (B) a radiation-sensitive acid forming agent. Said radiation-sensitive composition can be suitably used as a resist composition which enables reliable fine processing, which has high sensitivity and high resolution degree, and which is superior in dry etching resistance, developability, adhesiveness, heat resistance and yield of residual film thickness.

A radiation-sensitive resin composition containing an alkali-soluble resin, comprising a polyhydroxy compound having the following formula: ##STR1## or a quinonediazidesulfonate of the polyhydroxy compound. The radiation-sensitive resin composition is suitable for use as a positive type photoresist which has such excellent developability as to inhibit effectively the generation of scum in the formation of a photoresist pattern, has high sensitivity and is excellent in heat resistance and remained thickness ratio upon development.

A radiation-sensitive resin composition comprises (a) an alkali-soluble resin, (b) a 1,2-quinone diazide compound, and (c) an aromatic compound having a specified molecular structure, as essential constituents. The composition is extremely useful for forming a positive type photoresist on a substrate having a high reflectance.

I-line radiation-sensitive alkali-soluble resin composition utilizing

A positive type radiation-sensitive resin composition comprising an alkali-soluble novolac resin and a 1,2-quinonediazide compound, characterized in that said alkali-soluble novolac resin is a resin produced by condensing a carbonyl compound and a phenol mixture comprising 6 to 94 mole % of m-cresol and 94 to 6 mole % of at least one compound represented by the formula (I) other than m-cresol: ##STR1## wherein X is --CH.sub.3, --C.sub.2 H.sub.5, --C(CH.sub.3).sub.3, --CO.sub.2 CH.sub.3 or --CO.sub.2 C.sub.2 H.sub.5 ; n is an integer satisfying 3.gtoreq.m.gtoreq.1; and m is an integer satisfying 3.gtoreq.m.gtoreq.1, in which resin when the polystyrene-reduced molecular weight is determined by a gel permeation chromatography using a monodisperse polystyrene as the standard, maximum values a, b and c present, respectively, in the molecular weight ranges of 6,300 to 25,000, 2,500 to 6,000 and 150 to 900 in the molecular weight distribution curve obtained satisfy the following relationships: a/b=0-1.5 and c/b=1.4-2. Said positive type-radiation-sensitive resin composition is excellent in resolution, sensitivity, developability, thermal resistance and adhesion and hence is useful as a positive type resist for producing integrated circuits having a higher integration.

Positive type radiation-sensitive resin composition comprising a

A process for preparing alkali metal dispersions comprises continuously feeding a molten alkali metal, a dispersing agent, and an inactive dispersion liquid to a multipass emulsifier to form an emulsion of the molten alkali metal, and rapidly cooling the emulsion to a temperature at least 10.degree. C lower than the melting point of the alkali metal.

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Yokkaichi, Japan

Takao Miura