WO2002039187A1 - Compositions pour film sub-resist et leurs procedes de preparation, et films sub-resist et leurs procedes de production - Google Patents

Compositions pour film sub-resist et leurs procedes de preparation, et films sub-resist et leurs procedes de production Download PDF

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Publication number
WO2002039187A1
WO2002039187A1 PCT/JP2001/009722 JP0109722W WO0239187A1 WO 2002039187 A1 WO2002039187 A1 WO 2002039187A1 JP 0109722 W JP0109722 W JP 0109722W WO 0239187 A1 WO0239187 A1 WO 0239187A1
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Prior art keywords
film
resist underlayer
composition
underlayer film
silane compound
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PCT/JP2001/009722
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English (en)
Japanese (ja)
Inventor
Keiji Konno
Kazuo Kawaguchi
Masato Tanaka
Yasutaka Kobayashi
Akihiro Hayashi
Hikaru Sugita
Yuichi Hashiguchi
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Jsr Corporation
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers

Definitions

  • composition for resist underlayer film and method for producing the same, and
  • the present invention relates to a composition for a resist underlayer film for forming a lower layer film serving as a base when a resist pattern is formed on a substrate to be processed, a method for producing the same, and a resist underlayer film and a method for producing the same.
  • the required microfabrication of substrates to be processed made of organic and inorganic materials is performed by pattern transfer methods that apply lithography technology, resist development process, and etching technology. It is being done.
  • a resist pattern is used as a mask in the process of processing a substrate to be processed on which a silicon oxide film or an inorganic interlayer insulating film has been formed.
  • the pattern becomes finer, the thickness of the resist film is reduced. Therefore, it is not possible to obtain sufficient mask performance on the gate film, and as a result, it becomes difficult to perform required fine processing without damaging the substrate to be processed.
  • an oxide film / interlayer insulating film processing lower layer film is formed on an oxide film of a substrate to be processed, a resist pattern is transferred to the lower layer film, and the processing lower layer film is used as a mask to form an oxide film or an oxide film.
  • a process of dry-etching the interlayer insulating film is performed.
  • the lower layer film for karoe is a film that also functions as a lower antireflection film or a film formed below the antireflection film.
  • a mask for processing the processing lower layer film itself is provided between the resist film and the processing lower layer film. It has been proposed to form a layer. Specifically, for example, there has been proposed a method of forming a multilayer film structure in which a processing lower layer film, a lower layer film processing mask, and a resist film are laminated in this order on an oxide film.
  • the process of forming a pattern on each layer in a multilayer film structure having such a configuration is generally an etching process using a developing solution for a surface resist film, and an etching gas for a layer below a lower layer for force processing.
  • the lower layer 11 is usually an alkyl fluorine-based gas in order to form the lower processing mask pattern.
  • a seed is used, and in order to form a pattern of the processing lower layer film, ashing using oxygen gas is performed by changing an etching gas type.
  • the lower film processing mask may be broken, and it is difficult to accurately form a fine pattern.
  • the cause was clarified, it was found that the reason was that the lower processing mask) had a high density and did not have sufficient gas permeability.
  • the mask for processing the lower layer film other characteristics such as a good resist pattern without tailing, excellent adhesion with the resist, and It is required that the mask for processing has sufficient mask performance, and that the solution forming the mask for processing the underlayer film has excellent storage stability, but a material satisfying all of these is not known. Disclosure of the invention
  • the present invention has been made in view of the above circumstances, and has as its object to have good gas permeability, excellent adhesion to a resist film,
  • An object of the present invention is to provide a composition for a resist underlayer film having excellent resistance to a developing solution used for development, and a method for producing the same.
  • Another object of the present invention is to provide a resist underlayer film having good gas permeability, excellent adhesion to a resist film, and excellent resistance to a developing solution used for developing the resist film, and a method for producing the same. To provide.
  • the first composition for a resist underlayer film of the present invention comprises a film-forming component comprising a hydrolyzate of a silane compound (A) represented by the following general formula (A) and / or a condensate thereof; It contains a heat-volatile substance that gasifies,
  • the film is characterized in that a film-forming component is hardened by heating, and a heat-volatile substance is gasified to form pores, thereby forming a porous silicon film.
  • a film-forming component is hardened by heating, and a heat-volatile substance is gasified to form pores, thereby forming a porous silicon film.
  • R 1 represents a hydrogen atom, a fluorine atom or a monovalent organic group
  • R 2 represents a monovalent organic group
  • a represents an integer of 0 to 3.
  • the silane compound (A) related to the film-forming component is preferably a silane compound in which a is 0 or 1 in the general formula (A).
  • the heating volatile substance is preferably a substance having a boiling point or a decomposition temperature of 200 to 450 ° C, and the heating volatile substance may be poly (meth) acrylate, having 2 to 1 carbon atoms.
  • the aliphatic polyether compound is a polyalkylene oxide having a repeating unit containing an aethenole group, and is at least one selected from compounds having a naphthoquinonediazide structure.
  • the first resist underlayer film composition preferably further contains an acid-generating compound that generates an acid by at least one of irradiation with ultraviolet light and heating.
  • the first resist underlayer jj trillions of the present invention a thin film formed by the resist underlayer film composition is formed by curing by heating, the density is 0.7 to 1. In 8 / cm 3 It is characterized by comprising a certain porous silica film.
  • a thin film is formed from the composition for a resist underlayer film described above, and the thin film is heated to a temperature equal to or higher than the boiling point or the decomposition temperature of the heat-volatile substance contained in the composition. By heating, the film-forming component is cured, and the volatile material is gasified to form pores, thereby forming a porous silicon film.
  • the first composition for a resist underlayer film is used for forming an underlayer of a resist film formed on a substrate to be processed, and the composition is a film formed by hydrolysis and partial condensation of a silane compound. Since the film-forming component contains a heating volatile component together with the forming component, when the film-forming component is hardened by heating, the heating volatile component gasifies and volatilizes, resulting in a relatively low density in which many or innumerable pores are formed. Thus, a porous silica film having the following characteristics is formed. As a result, a resist underlayer film having an appropriate gas permeability is formed. Therefore, the resist underlayer film can reliably and easily attain the required gas etching with respect to the lower processing lower layer film by sufficiently transmitting the etching gas.
  • the second composition for a resist underlayer film of the present invention comprises a silane compound (A) represented by the following general formula (A) and a silane compound (B) having a thermally decomposable group represented by the following general formula (B). )) And / or a film-forming component comprising a condensate thereof.
  • the film-forming component is cured by heating, and the thermally decomposable group-containing silane compound (B) generates gas to form pores, whereby a porous silica film is formed.
  • CR 1 represents a hydrogen atom, a fluorine atom or a monovalent organic group (however, excluding a thermally decomposable organic group defined as R 3 in the general formula (B) below), and R 2 represents a monovalent organic group.
  • a represents an integer of 0 to 3.
  • General formula (B) R 3 b S i (OR 4 ) 4- b
  • R a represents a monovalent thermally decomposable organic group decomposed at 200 to 400 °
  • R 4 represents a monovalent organic group, and b represents an integer of 1 to 3.
  • (B) are the compounds of formula (B), thermally decomposable containing a thermally decomposable organic group, linear or branched aliphatic group with carbon number 6-2 5 containing R '1 force cycloaliphatic radical
  • a silane compound which is an organic group or a thermophilic organic group containing an aliphatic polyether chain having an ether bond-containing repeating unit having 2 to 12 carbon atoms is preferable.
  • the second resist underlayer film composition preferably further contains an acid generating compound that generates an acid by at least one of irradiation with ultraviolet light and heating.
  • the second method for producing a resist underlayer film composition comprises hydrolyzing the silane compound (A) and the thermally decomposable group-containing silane compound (B) in an organic solvent in the presence of water and a catalyst. And a step of partially condensing.
  • the second resist underlayer film of the present invention a thin film formed by the resist underlayer film composition is formed by curing by heating, the density is 0.7 to 1. In 8 g / cm 3 It is characterized by comprising a certain porous silica film.
  • a thin film is formed from the above-described composition for a resist underlayer film, and the thin film is formed from the thermally decomposable group-containing silane compound (B) contained in the composition.
  • Producing a porous silica film by heating to a temperature equal to or higher than the decomposition temperature of the thermally decomposable organic group, thereby forming film-forming components and generating gas to form pores. I do.
  • the second resist underlayer film composition of the present invention is used for forming an underlayer of a resist film formed on a substrate to be processed, and the composition is obtained by hydrolysis and partial condensation of a silane compound.
  • the film-forming component contains a silane compound (B) containing a thermally decomposable group as a part of the film-forming component
  • the film-forming component is hardened by heating. Gas is generated from the silane compound (B)
  • a relatively low-density, porous silicon film having a large number or a large number of holes is formed, and eventually, a resist underlayer film having an appropriate gas permeability is formed. Therefore, this resist underlayer film can reliably and easily achieve the required gas etching on the lower processing lower layer film by sufficiently transmitting the etching gas.
  • the film-forming component comprises a hydrolyzate and / or condensate of a specific silane compound. Because it is porous, it has high adhesion to resist despite being porous, and has sufficiently large resistance to resist developing solution and oxygen gas for ashes for removing resist, and has high reproducibility in resist film A resist underlayer film on which a resist pattern is formed can be formed, and excellent storage stability can be obtained.
  • composition for a resist underlayer film of the present invention is used for forming a base layer of a resist film formed on a substrate to be processed.
  • the first resist underlayer film composition of the present invention will be described.
  • the first composition for a resist underlayer film of the present invention basically comprises a film-forming component composed of a specific substance, and a heat-volatile substance which is gasified and volatilized by heating.
  • a hydrolyzate of a silane compound (A) represented by the above general formula (A) and / or a condensate thereof is used as a film-forming component as a main component.
  • R ′ is a hydrogen atom, fluorine Is an atom or a monovalent organic group
  • R 2 is a monovalent organic group.
  • the monovalent organic group include aryl, alkyl and glycidyl groups. .
  • alkyl group examples include C1 to C5 alkyl groups such as a methyl group, an ethyl group, a propyl group and a butyl group. These alkyl groups may be linear or branched, and may be a fluorinated alkyl group in which some or all of the hydrogen atoms have been replaced by fluorine atoms.
  • aryl group examples include a phenyl group, a naphthyl group, a tosyl group, an ethylphenyl group, a phenyl group, a bromophenyl group, and a fluorophenyl group.
  • Examples of the silane compound (A) represented by the general formula (A) include the following silane compounds (1) to (5).
  • a force U is a hydrogen atom or a fluorine atom
  • R 1 is a hydrogen atom or a fluorine atom
  • R 2 is an alkyl group or a phenyl group having 1 to 5 carbon atoms.
  • trimethoxysilane triethoxysilane
  • triethoxysilane triethoxysilane
  • N propoxysilane
  • tree iso-propoxysilane
  • tree ⁇ -butoxysilane tri-sec —butoxysilane
  • tri-tert-butoxysilane tri-tert-butoxysilane
  • triphenoxysilane fluorotrimethoxysilane
  • fluorotriethoxysilane fluorotri-n— Examples include propoxysilane, fluorotri-iso-propoxysilane, phenololorin n-butoxysilane, phenololorin sec-butoxysilane, fluororhyl tert-butoxysilane, and fluorotrifluorophenoxysilane.
  • tetramethoxysilane examples include tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-iso-propoxysilane, tetra- Examples thereof include n-butoxysilane, tetra-sec-butoxysilane, tetra-tert-butoxysilane, and tetraphenoxysilane.
  • a force 1 and R 1 are an alkyl group or substituted alkyl group having 1 to 5 carbon atoms, a butyl group or a phenyl group, and R 2 is an alkyl group having 1 to 5 carbon atoms or a phenyl group.
  • methyltrimethoxysilane methyltriethoxysilane, methyl_n-propoxysilane, methinoletri-iso-propoxysilane, methyltri-n-butoxysilane, methyltri-sec-butoxysilane, methyltri-tert-butoxysilane, Methinoletriphenoxysilane, eth ⁇ / trimethyoxysilane, ethithriethoxysilane, ethinoletri- ⁇ -propoxysilane, ethynorietri iso-propoxysilane, ethynoletri-n-butoxysilane, ethinoletrie sec-butoxysilane, ethinoletri Butoxysilane, ethynoletriphenoxysilane, virtrimethoxysilane, bienotriethoxysilane, burtri-n-propoxysilane, burtri-iso Loxy
  • a is 2
  • R ′ is an alkyl group having 1 to 5 carbon atoms or a substituted alkyl group, a Bier group or a phenyl group
  • R 2 is an alkyl group having 1 to 5 carbon atoms or a phenyl group.
  • Specific examples thereof include, for example, dimethyldimethoxysilane, dimethyljetoxysilane, dimethinoledi-n-propoxysilane, dimethylzie iso-propoxysilane, dimethinolezie n-butoxysilane, dimethylzie sec-butoxysilane.
  • a is 3
  • R 1 is an alkyl group having 1 to 5 carbon atoms or a substituted alkyl group, a vinyl group or a fuel group
  • R 2 is an alkyl group having 1 to 5 carbon atoms or a fuel.
  • silane compound (2) preferred as the silane compound (2) are tetramethoxysilane, tetraethoxysilane, tetra- ⁇ -propoxysilane, tetra-is0-propoxysilane and tetraphenoxysilane.
  • Preferred as the silane compound (3) are methyltrimethoxysilane, methyltriethoxysilane, methyltri-n-propoxysilane, methyltri-iso-propoxysilane, ethyltrimethoxysilane, ethyltriethoxysilane, butyltrimethoxysilane, vinyltriethoxysilane, isotrimethylsilane.
  • silane compound (4) are dimethydimethoxysilane, dimethylethylethoxysilane, getyldimethoxysilane, getyljetoxysilane, diphenyldimethoxysilane and diphenylethoxysilane.
  • silane compound (5) are trimethyl monomethoxy silane, trimethyl monoethoxy silane, triethyl monomethoxy silane, triethyl monoethoxy silane, triphenyl monomethoxy silane and triphenyl monoethyl. It is toxic silane.
  • the above silane compound (A) may be used alone or in combination of two or more.
  • monoalkoxysilane in which the value of a in the general formula (A) is a silane compound (A) having a value of 2 or dianolekoxysilane in which the value of a is a silane compound (A) having a value of 3 In order to obtain a composition having excellent curability, it is preferable to use one or more of tetraalkoxysilanes and trialkoxysilanes, which are silane compounds (A) having a value of 0 to 1. .
  • the proportion of the monoalkoxysilane or dialkoxysilane is in the range of 1 to 50% by mass of the entire silane compound (A).
  • silane compounds (A) other than the above are used, their relative proportions are not particularly limited.
  • a catalyst is used to hydrolyze and / or condense the silane compound (A).
  • Examples of the catalyst include metal chelate compounds, organic acids, inorganic acids, organic bases, and inorganic bases.
  • Metal chelate compounds used as catalysts include, for example, triethoxy mono (acetyl acetonato) titanium, tri-n-propoxy.mono (acetyl acetonato) titanium, tree iso-propoxy 'mono (acetinol acetonate) Titanium, tri-n-butoxy.mono (acetinolecetate) titanium, tri-sec-butoxy'mono (acetyl acetatetonate) titanium, tri-tert-butoxy * mono (acetylacetonate) titanium, Diethoxy bis (acetylacetonate) Titanium, di-n-propoxy 'bis (acetyacetonate) titanium, di-iso-propoxy' bis (acetylaceto " ⁇ ") titanium, g-butoxy bis (acetylacetonate) Titanium, G sec-butoxy bis
  • Diethoxy 'bis (acetylacetonato) zirconium Gam, G n-propoxy 'bis (acetyl acetate) zirconium, di-iso-propoxy' bis (acetacetonate) dinoreconidum, di- ⁇ -butoxy bis (acetia acetate) dinoreco-pam, di- sec —butoxy bis (acety ⁇ acetonato) dinoreconidum, g-tert-butoxy 'bis (acetyl acetatenato) zirconium, monoethoxy.
  • Aluminum chelate compounds such as tris (acetyl acetateton) anoreminium, tris (ethinoleacetoacetate) aluminum;
  • Organic acids include, for example, carboxylic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, oxalic acid, maleic acid, methylmalonic acid, adipic acid, sebacic acid , Gallic acid, butyric acid, melitic acid, arachidonic acid, mykimic acid, 2-ethylhexanoic acid, oleic acid, stearic acid, linoleic acid, linoleic acid, salicylic acid, benzoic acid, p-aminobenzoic acid, p — Toluenesulfonic acid, benzenesulfonic acid, monochloroacetic acid, dichloroacetic acid, trifluoroacetic acid, trifluoroacetic acid, formic acid, malonic acid, sulfonic acid,
  • inorganic acid examples include hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, phosphoric acid and the like.
  • organic base examples include pyridine, pyrrole, piperazine, pyrrolidine, piperidine, picoline, trimethylamine, triethylamine, monoethanolamine, diethanolamine, dimethylmonoethanolamine, monomethylethanolanolamine, and triethanolamine.
  • Min diazabicyclooctane, diazabicyclononane, diazabicycloundecene, tetramethylammonium hydroxide, and the like.
  • the inorganic base for example, ammonia, sodium hydroxide, potassium hydroxide, hydroxypropyl parium, calcium hydroxide and the like can be mentioned.
  • catalysts preferred are a metal chelate compound, an organic acid and an inorganic acid, and more preferred are a titanium chelate compound and an organic acid. These catalysts can be used alone or in combination of two or more. Wear.
  • the amount of the catalyst to be used is usually 0.01 to 10 parts by mass, preferably 0.00 parts by mass, per 100 parts by mass of the silane compound (A) (converted as a complete hydrolysis condensate). It is in the range of 1 to 10 parts by mass.
  • the coating film formed by the obtained composition for a resist underlayer film has high uniformity, and the composition surely has high storage stability.
  • water may be added intermittently or continuously to an organic solvent in which the silane compound (A) is dissolved.
  • the catalyst may be added to an organic solvent in advance, or may be dissolved or dispersed in water to be added.
  • the reaction temperature of the hydrolysis and the partial condensation is usually 0 to: L00 °, preferably 15 to 80 ° C.
  • the heating volatile substance which is blended with the above film-forming components to form the first resist underlayer film composition has a boiling point or decomposition temperature of 200 to 450 ° C and is heated to such a temperature. It is a compound that gasifies and volatilizes when it is burned.
  • the boiling point or the ⁇ temperature indicates the temperature at 1 atm.
  • Heat-volatile substances include ether bonds, ester bonds, amide bonds, carbonate bonds, urea bonds, sulfide bonds, sulfol bonds, amino bonds, carboyl bonds, hydroxyl groups, thiol groups, amino groups, etc. It is preferably a hydrocarbon organic compound containing a group. Carbon dihydrogen compounds containing no such bond or group have a low compatibility with the film-forming component, so that a transparent coating film cannot be obtained, and large pores tend to be formed in the film. In addition, the resist pattern Jung performance may be deteriorated.
  • the heating volatile substance include, for example, a compound having a polyalkylene oxide compound, a compound having a naphthoquinonediazide structure, a compound having a sugar chain structure, a vinylamide polymer, a (meth) acrylate polymer, and a lipophilic compound.
  • examples include a combination of a compound and a dispersant, and ultrafine particles.
  • the mixing ratio of the heat-volatile substance in the composition for a resist underlayer film varies depending on the type of the film-forming component and the type of the heat-volatile substance, but is usually 100 parts by mass of the film-forming component.
  • the range is 0.1 to 80 parts by mass, preferably 1 to 50 parts by mass. If the proportion of the heat-volatile substance is too large, the strength of the obtained resist underlayer film will be low, while if it is too small, it is difficult to form the desired porous silicon film. .
  • polyalkylene oxide structure in this compound examples include a polyethylene oxide structure, a polypropylene oxide structure, a polytetramethylene oxide structure, and a polybutylene oxide structure.
  • the compounds include, for example, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene sterol ether, polyoxyethylene lanolin derivative, ethylene oxide derivative of alkylphenol formalin condensate, Ether-type compounds such as polyoxyethylene polyoxypropylene block copolymer, polyoxyethylene polyoxypropylene alkyl ether, polyoxyethylene glycerin fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sonorebitol fatty acid ester , Ester type compounds such as polyoxyethylene fatty acid alcohol amide sulfate, polyethylene glycol fatty acid ester, ethylene glycol fat Esters, fatty Monoguriseri de, Poridariserin fatty acid esters, sorbitan tail fatty Esuteru, propylene glycol fatty acid Esuteru, sucrose fatty acid E Examples thereof include ether ester type compounds such as stell.
  • Examples of the compound having a naphthoquinonediazide structure include naphthoquinone-1,1,2-diazido-5-sulfonic acid ester of a compound having a phenol structure.
  • Compounds having a phenol structure include phenol, methylphenol, dimethylphenol, trimethylphenol, tetramethylphenol, pentamethylphenylphenol, resorcinol, catechol, hydroquinone, bisphenolenole A, dihydroxybenzophenone, dihydroxydiphenylsulfone, dihydro Examples thereof include xyldiphenyl ether, dihydroxydiphenylmethane, resorcinol allene compound, phyllixallene compound, and the following compounds (2-1) to (2-12) and others.
  • Compounds having a sugar chain structure include cyclodextrin, sucrose ester, oligosaccharide, glucose, fructose, mannitol, starch sugar, D-sorbitol, dextra, xanthan gum, curdlan, pullulan, cycloamylose, isomerized sugar, multi Examples thereof include tall, cellulose acetate, cellulose, carboxymethyl cellulose, hydroxyxethylesenorelose, hydroxypropinoresenorelose, methinoresenololose, ethylhydroxyethyl cellulose, chitin, chitosan and the like.
  • cyclodextrin is represented by the following formula (1), wherein n is 6 (hypercyclodextrin), 7 cyclodextrin) or 8 ( ⁇ -cyclodextrin).
  • the compound having a sugar chain structure used as a heat-volatile substance is preferably a compound in which a part or all of a hydroxyl group or an amino group is modified.
  • Examples of the chemical modification of the hydroxyl group include etherification, esterification, modification including a trialkylsilinole bond and a urethane bond.
  • Examples of the chemical modification of an amino group include introduction of an amide bond, a urea bond, and an imide bond.
  • cyclodextrin is preferred as a heat-volatile substance because the pores formed in the coating film have a small diameter and the pore diameter can be controlled.
  • trialkylsilyl modification or ⁇ It is preferable to be modified by rethanization, and particularly preferable to be modified by trimethylsilinole.
  • a compound having a sugar chain structure may be reacted with a trimethylsilylating agent such as trimethylchlorosilane or trimethylsilyl acetamide, which usually has a sugar chain structure. What is necessary is just to substitute 5 to 100% of the hydroxyl groups of the compound.
  • a compound having a sugar chain structure may be reacted with a urethanizing agent such as pheninoleisocyanate or hexinoleisocyanate. Usually, 5 to 100% of the hydroxyl groups of the compound having a sugar chain structure may be substituted.
  • vinylamide polymer examples include poly (N-vinylacetamide), poly (N-bininolepyrrolidone, poly (2-methyl-2-oxazoline), and poly (N, N-dimethylacrylamide).
  • (Meth) acrylate polymers include (meth) methyl acrylate, (meth) ethyl acrylate, (meth) butyl acrylate, (meth) benzyl acrylate, (meth) tetrahydrofurfuryl acrylate, (meth) ) Glycidyl acrylate, hydroxyxetinole (meth) acrylate, (meth) acrylamide, hydroxypropyl (meth) acrylate, etc. Radical polymerizable monomer polymer or copolymer with (meth) acrylate ester be able to.
  • lipophilic compounds and dispersants do not have sufficient compatibility with the film-forming components when used alone.However, when combined with a dispersant, sufficient compatibility can be obtained. It can be used as a volatile substance.
  • lipophilic compound examples include didecyl phthalate, didecinolephthalate, didodecino phthalate, ditridecyl phthalate, tris (2-ethylhexyl) trimellitate, tridecyl trimellitate, tridodecyl trimellitate
  • Polycarboxylates such as, tetraptinolepyromellitate, tetrahexyl trimellitate, tetraoctyl pyromellitate, bis (2-ethylhexyl) dodecandioate, bisdecyldecanedioate, and the like.
  • Dispersants that can be combined with these lipophilic compounds include higher alcohols such as octanol, lauryl alcohol, decyl alcohol, and decyl alcohol.
  • the higher alcohol as a dispersant is used in an amount of 0.1 to 10 times the mass of the lipophilic compound.
  • Ultrafine particles are polymer particles having a particle diameter of 100 nm or less.
  • the particle size is controlled by regulating conditions such as the type of precipitating agent, emulsifier concentration, and stirring speed.
  • (meth) atalylate compounds are used as monomers and Some are prepared using a crosslinkable monomer for controlling the particle size.
  • the first resist underlayer film composition is prepared by dissolving or dispersing the above film-forming component and the heat-volatile substance in an appropriate solvent.
  • the solvent is not particularly limited as long as it is an organic solvent used for this kind of application.
  • propylene glycol monoethyl ether, propylene glycol monomethyl monomethyl ether ether, propylene glycol Rikonoremonopropinoleter and the like are preferably used.
  • An acid generator can be added to the first resist underlayer film composition.
  • an acid is generated in the resist underlayer film by the action of heat or light.
  • the reproducibility of a good mask pattern and the rectangularity of the cross-sectional contour are high! This is preferable because a resist pattern can be formed.
  • Acid generators include latent thermal acid generators or latent acid generators.
  • the latent thermal acid generator is a compound that generates an acid when heated to usually 50 to 450 ° C., preferably 200 to 350 ° C., and includes a sulfo- ⁇ salt and a benzothiazolyte. Salts such as sodium salt, ammonium salt and phosphonium salt are used.
  • the sulfonium salt used as the latent thermal acid generator include 4-acetopheno-noresimetinoles / lefonium hexafenoleoantimonate, 4-acetoxyphenyldimethylsulfonium hexafluoroarsenate, Dimethinole-4-(benzinoleoxycarbonyloxy) phenylsolephonium hexafenoleantimonate, dimethyl 41- (benzoinoleoxy) phenyls ⁇ lefonium hexafenoleoantimonate, dimethy ⁇ — 41- (Benzoinoleoxy) phenylsnorefonium hexafluorene arsenate, dimethyl-3-chloro-1,4-acetoxyphenyl-sulfonium hexolefluoronormonone such as hexafluoroantimonate Pum salt;
  • Dibenzyl-4-hydroxyphenylsulfonium hexafluoroantimonate dipendinoleate 4-hydroxyphenylenolesolenium hexafenoleophosphate, 4-acetoxyphenyldibenzylsulfonium hexafluoroantimonate, Dibenzyl-4-methoxyphenylsnorrefuium hexafluo mouth antimonate, dipendinole 3-chloro-1,4-hydroxyhydroxyphenylsnolefonium hexafenoleoloarsenate, dibenzyl-3-methyl-4-hydroxy 1-5-tert-Butylphenylenosulfonium hexafluoroantimonate, benzizole-4-methoxybenzinole-4-dihydroxyphenylenolesnorefonium dibenzylsulfonate such as hexafluorophosphate Salt;
  • Benzinole 4 Hydroxypheninolemethinoresnorethoyum hexaforenoantimonate, p-Nitrobenzyl-4-hydroxyphenylmethylsnolehonemexafluoroantimonate, p—Cro mouth Benzyl 4-hydroxyphenyl methinolesnorefonium hexafenoleophosphate, p-nitrobenzyl-3-methyl-4-hydroxyhydroxymethylsulfonium hexafluorate antimonate, 3,5-dichloro Oral Benzinole 4-Hydroxyphenylmethinole Snorrefonium Hexafenoleo Antimonate, o-Chlorovenezynole 3 -Chloro mouth _ 4-Hydroxyphenylemethinoresnorrefoam Hexafenoleo Antimonate Substituted benzylinolesulfo-pium salt
  • benzothiazonium salts include 3-benzylbenzothiazolium hexafluoroantimonate, 3-benzinobenzobenzothiazolym hexafluorophosphate, and 3-benzoylbenzo.
  • Benzyl benzothiazolym salts such as benzothiazolym hexafluoroantimonate can be mentioned.
  • thermal acid generators other than the above include 2, 4, 4, 6-tetrabromocyclo Xixenone can be exemplified.
  • the latent photoacid generator is usually a compound that generates an acid by irradiation of an energy of 1 to: L00 mJ, preferably 10 to 50 mJ, with ultraviolet light.
  • Latent photoacid generators include, for example, diphenyleododium trifluoromethanesulfonate, diphenyleodoniumpyrenesulfonate, diphenylidenodium dodecamedodecylbenzenesulfonate, diphenyleodomium nononaphnoate N-butanesulfonate, bis (4-tert-butynolephenyl) eodonium trifluoromethanesulfonate, bis (4-tert-butynolephenyl) iodonium dodecylbenzenesulfonate, bis (4-tert-butylphenyl) eodonium Naphthalenesulfonate, bis (4-tert-butylphenyl) eodoniumhexafluoroantimonate, bis (4-tert-butynolephenyl) eodoniumnonafluoro n-butanesulf
  • Sulfonic acid compound-based photoacid generators benzoin tosylate, pyrogallol tristrifluoromethanesulfonate, nitro benzyl-9,10-jetoxyanthracene_2-sulfonate, triflorenomethanesulfonylbicyclo [2,2,1] Heptaw 5 — 2, 3, 3-dical positimide, N — hydro Shisukushinimi de triflate Ruo b methanesulfonate, 1, and the like 8 _ naphthalene dicarboxylic acid imide triflate Ruo b sulfonic acid compound-based photoacid generator such as methanesulfonate.
  • the above acid generator is usually used in an amount of 100 parts by mass (converted as a complete hydrolysis condensate) of the film-forming component. It is 1 to 30 parts by mass.
  • Auxiliary components such as colloidal silica, colloidal alumina, and a surfactant 14 may be further added to the first resist underlayer film composition.
  • Colloidal silica is, for example, an average of high-purity silica anhydride dispersed in an organic solvent.
  • the particle size is 5 to 30 ⁇ m, preferably the average particle size is 10 to 20 ⁇ , and the solid concentration is about 10 to 40% by weight.
  • Examples of such colloidal silica include methanol silica sol, isopropanol silica sol (all manufactured by Nissan Chemical Industry Co., Ltd.), and Oscar (manufactured by Catalyst Chemical Industry Co., Ltd.).
  • colloidal alumina examples include Alumina Zonore 520, 100, and 200 (hereafter, manufactured by Nissan Chemical Industries, Ltd.), Alumina Clear Sol, Alumina Sol 10, and 132 (all, Kawasaki Manufactured by Ken Fine Chemical Co., Ltd.).
  • surfactant examples include a nonionic surfactant, an anionic surfactant, a cationic surfactant, an amphoteric surfactant, a silicone surfactant, a polyalkylene oxide surfactant, and a fluorine-containing surfactant. be able to.
  • the second resist underlayer film composition of the present invention comprises a film-forming component comprising a specific silane compound (A) and a thermally decomposable group-containing silane compound (B) having a thermally decomposable organic group. .
  • the film-forming components include a silane compound (A) represented by the above general formula (A) and a silane compound containing a thermally decomposable group represented by the above general formula (B).
  • a silane compound (A) represented by the above general formula (A) and a silane compound containing a thermally decomposable group represented by the above general formula (B).
  • the hydrolyzate of both (B) and Z or a condensate thereof are used.
  • the silane compound (A) for the second resist underlayer film composition is basically the same as the film-forming component of the first resist underlayer film composition.
  • R 1 is a monovalent organic group in the general formula (A) of the silane compound (A)
  • the organic group is a thermally decomposable organic group defined as in the general formula (B).
  • the monovalent, thermally decomposable organic group that decomposes at 200 to 400 ° C.
  • silane compound (A) Depending on the type of the silane compound containing a thermally decomposable group (B) described below, when a composition having a curability is obtained, it is also possible to use only monoalkoxysilane as the silane compound (A).
  • a thermally decomposable group represented by the general formula (B) is contained in addition to the silane compound (A).
  • a hydrolyzate of the silane compound (B) and / or a condensate thereof are used as essential components.
  • the number of the thermally decomposable organic groups R 3 is 200 to 400.
  • a group containing an aliphatic polyether chain having a unit is shown.
  • silane compound in which R 3 is a group having a decomposition temperature of less than 200 ° C. in the general formula (B) When a silane compound in which R 3 is a group having a decomposition temperature of less than 200 ° C. in the general formula (B) is used, the silane compound generates a gas before the film-forming component is cured. required hole is not formed in the membrane to become, on the other hand, the use of silane compound decomposition temperature of the thermally decomposable organic group exceeds 4 0 0 e C, it is a film-forming components prior to generating gas It is difficult for pores to be formed in the coating film due to the significant progress of curing, and in any case, it is difficult to obtain a resist underlayer film having the required gas permeability.
  • thermally decomposable group-containing silane compound (B) Specific examples of the thermally decomposable group-containing silane compound (B) are shown below. These may be used alone or in combination of two or more.
  • the thermally decomposable organic group R 3 is an alkyl group having 6 to 25 carbon atoms
  • the alkyl group may be linear or branched, and examples thereof include a hexyl group and a heptyl group. Examples include a tyl group, an octyl group, a nor group, a decyl group, a dodecyl group and an octadecyl group.
  • silane compound (B) in this case examples include, for example, hexyltrimethoxysilane, hexinoletriethoxysilane, hexinoletributoxysilane, heptinoletrimethoxysilane, heptyltriethoxysilane, heptyltributoxysilane, and octyltrimethyl.
  • hexinoletrimethoxysilane preferred are hexinoletrimethoxysilane, hexyltriethoxysilane, heptyltrimethoxysilane, heptyltriethoxysilane, octinoletrimethoxysilane, octinoletriethoxysilane, octinoletrimethoxysilane, octyltriethoxysilane, and octyltriethoxysilane.
  • R is a group containing an aliphatic polyester chain having an ether bond-containing repeating unit having 2 to 12 carbon atoms
  • the group may have a functional group at a terminal, and examples thereof include (Polyethyleneoxy) propyl, (polypropyleneoxy) propyl, (polytetramethyleneoxy) propyl, (polyethyleneoxy) ethyl, (polypropyleneoxy) ethyl, (polytetramethyleneoxy) ethyl, (Polyethyleneoxy) methyl group, (polypropyleneoxy) methyl group and (polytetramethyleneoxy) methyl group.
  • silane compound (B) examples include (polyethylene oxypropyl pill) trimethoxy silane, bis (polyethylene oxypropyl) dimethoxy silane, tris (polyethylene oxypropinole) methoxy silane, and (polyethylene).
  • R 3 is a group containing a cycloaliphatic group
  • examples of the group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclopentyl group, a cyclopentagenole group, a cyclohexynole group, and a cyclohexyl group.
  • examples thereof include a pentinole group, a cyclooctynole group, a cyclooctenyl group, a cyclohexenyl group, an adamantyl group, a bicycloheptyl group, and a cis-opened heptyl group.
  • silane compound (B) in this case examples include, for example, cyclopropyl trimethoxy silane, dicyclopropynolemethyxoxysilane, and tricyclopropynolemethoxy silane.
  • cyclopentyltrimethyoxysilane dicyclopentinoresimethyoxysilane, cyclopentinolemethytrimethyoxysilane, bis (cyclopentylmethyl) dimethyoxysilane, and cyclopentenyltrimethysilane.
  • the general range of the relative ratio between the silane compound (A) constituting the film-forming component and the silane compound (B) containing the thermally decomposable group is required. It is sufficient that the composition is such that a composition capable of forming a porous silica film having properties such as gas permeability can be obtained.Therefore, the specific range is a force S that differs depending on the type of each silane compound, for example, a mass. 30 to 95: 10 to 70, 50 to 90: preferably 10 to 50, particularly preferably 70 to 90: 10 to 30.
  • the proportion of the silane compound (A) is too large, the proportion of the thermally decomposable group-containing silane compound (B) will be relatively small, resulting in a resist having insufficient gas permeability. A lower layer film is formed.
  • the proportion of the silane compound (A) is too small, the resulting composition may have a resist underlayer film formed with an excessively high gas permeability and insufficient resistance.
  • At least one of the silane compound (A) and the silane compound (B) containing a thermally decomposable group has at least three alkoxy groups.
  • the value of a in the general formula (A) for the silane compound (A) is 3 or more.
  • a catalyst is used to hydrolyze, Z or condense the silane compound (A) and the thermally decomposable group-containing silane compound (B).
  • catalyst those listed as catalysts for hydrolyzing, Z-condensing, or silane compound (A) in the first resist underlayer film composition can be used.
  • the amount of the catalyst used is usually 0.0 with respect to 100 parts by mass of the silane compound (A) and the thermally decomposable group-containing silane compound (B) (converted as a condensate).
  • the range is from 0.1 to 10 parts by mass, preferably from 0.01 to 10 parts by mass.
  • the second resist underlayer film composition is produced by a method of hydrolyzing and partially condensing both the silane compound (A) and the thermally decomposable group-containing silane compound (B).
  • the composition formed by the obtained resist underlayer film composition has high uniformity, and the composition surely has high storage stability.
  • water may be intermittently or continuously added to an organic solvent in which the silane compound (A) and the thermally decomposable group-containing silane compound (B) are dissolved.
  • the catalyst may be added to an organic solvent in advance, or may be dissolved or dispersed in water to be added.
  • the reaction temperature of this hydrolysis and partial condensation is usually 0 to 100 ° C, preferably 15 to 80 ° C.
  • the solvent is not particularly limited as long as it is an organic solvent used for this kind of use, but in particular, propylene glycol monoethyl ether, propylene glycol monomethyl ether, and propylene glycol monopropyl ether are used. And the like are preferably used.
  • W propylene glycol monoethyl ether, propylene glycol monomethyl ether, and propylene glycol monopropyl ether are used. And the like are preferably used.
  • an acid generator can be added in the same manner as the first resist underlayer film composition, and the acid generator described above can be used. The same effect can be obtained.
  • the second resist underlayer film composition contains, similarly to the first resist underlayer film composition, auxiliary components listed as being added to the first resist underlayer film composition. Can be added.
  • the first resist underlayer film composition and the second resist underlayer film composition of the present invention are used for forming an underlayer of a resist film formed on a substrate to be processed.
  • a solution of the composition is applied to a surface on which a resist underlayer film is to be formed to form a coating film, and the coating film is dried and then cured by heating. Then, by controlling the heating temperature in this curing to an appropriate temperature, in the first resist underlayer film composition, the heating volatile substance is gasified and volatilized, and the second resist underlayer film composition
  • a gas was generated by thermally decomposing the thermally decomposable organic group derived from the thermally decomposable group-containing silane compound (B) in the film-forming component, whereby many or innumerable pores were formed.
  • a resist underlayer film made of a porous silica film is formed. This resist underlayer film usually has a refractive index of 1.2 to 1.6.
  • the surface on which the resist underlayer film of the present invention is formed is not particularly limited as long as the resist film is formed on the resist underlayer film.
  • the resist underlayer film is formed on the surface of the processing underlayer film formed on the oxide film of the substrate to be processed.
  • the resist underlayer film is used as a mask for processing the underlayer film. To form a film.
  • the temperature at which the coating film is heated is a temperature higher than the boiling point or decomposition temperature of the heating volatile substance contained in the composition. Therefore, the temperature is set to 200 ° C. to 450 ° C. or more, but the type of the film forming component actually used, the type of the curing catalyst, etc. The appropriate temperature is selected depending on the type and ratio of the heating volatile substance, the type and ratio of other additives, and other conditions.
  • the temperature at which the coating film is heated depends on the decomposition of the thermally decomposable organic group R 3 of the thermally decomposable group-containing silane compound (B). It is necessary that the temperature be higher than the temperature, so that the force is set to a temperature of 200 to 400 ° C. or higher.
  • the silane conjugate (A) and the thermally decomposable group-containing silicon compound that are actually used An appropriate temperature is selected depending on the type and relative ratio of (B), the type and ratio of the curing catalyst, the type and ratio of other additives, and other conditions.
  • the porous state of the formed resist underlayer film specifically, the average diameter of the formed holes and the degree of distribution were controlled. It can be.
  • the density of the porous silicon film constituting the resist underlayer film thus formed is preferably, for example, 0.7 to 1.8 gZcm 3 .
  • the resist underlayer film itself has good gas permeability, and therefore, by sufficiently transmitting the etching gas, it can be used as a lower layer of the resist underlayer film. The required gas etching can be reliably and easily achieved on the formed processing lower layer film.
  • the composition for a resist underlayer film of the present invention is formed because the film-forming component is composed of a hydrolyzate of a specific silane compound and Z or a condensate.
  • the cured film is porous but has high adhesion to the resist, has sufficiently high resistance to resist developing solution and oxygen gas for ashes for removing the resist, and has high reproducibility in the resist film It is possible to form a resist underlayer film on which a resist pattern is formed, and it is possible to obtain excellent storage stability and strength.
  • Examples A1 to A3 are based on the first resist underlayer film composition. It is.
  • Example A1 the decomposition temperature was 340 in place of polytetrahydrofurfuryl methacrylate as the heat-volatile substance.
  • a composition for a resist underlayer film was obtained in the same manner as in Example 1 except that polystyrene C was used.
  • Example A1 a resist underlayer film was prepared in the same manner as in Example 1 except that poly- ⁇ -methylstyrene having a decomposition temperature of 70 ° C. was used instead of polytetrahydrofurfuryl methacrylate as the heating volatile substance. A composition for use was obtained.
  • a resist underlayer film was formed as follows, and a resist film was further formed to form a resist pattern.
  • NFC B 007 a material for an anti-reflection film “NFC B 007” (manufactured by JSR Corporation) was applied to the surface of a silicon wafer by a spin coater, and 190.
  • An anti-reflection film having a thickness of 300 nm was used as a substrate to be processed by drying on a hot plate of C for 1 minute.
  • a resist underlayer film composition is spin-coated on the surface of the antireflection film of the substrate to be processed. After coating on a hot plate at 200 ° C for 1 minute, the resist was baked on a hot plate at 300 ° C to form a resist underlayer film having a thickness of 7 Onm.
  • a positive photoresist “M20G” (manufactured by JSR Corporation) is applied to the surface of the resist underlayer film, and dried at 130 ° C. for 90 seconds to form a resist coating film having a thickness of 700 nm.
  • a KrF excimer laser (wavelength: 248 nm) with a liner and space pattern of 0.2 // m using a Nikon KrF excimer laser irradiation device
  • the resist coating was irradiated with an energy of 25 mJ through a quartz optical mask.
  • the resist film is heated at 130 ° C for 90 seconds, and then developed for 30 seconds using a 2.38% by weight aqueous solution of tetramethylammonium hydroxide aqueous solution. A pattern was formed.
  • the film density was measured by the X-ray scattering method.
  • the refractive index at 50 points was measured using an optical refractometer “UV-1280 SE” (manufactured by KLA-Tencor), and the average value was determined.
  • the resist pattern was observed with a scanning electron microscope, and the case where the resist film was not peeled from the resist underlayer film was evaluated as “good”, and the case where the resist film was peeled was evaluated as “bad”.
  • the film thickness of the resist underlayer film before immersion in the developing solution is compared with the film thickness of the resist underlayer film after immersion, and when the difference between the two is 2 nm or less, ⁇ good J, A case exceeding 2 nm was evaluated as “poor”. (5) Oxygen ashesing resistance
  • the resist underlayer film was subjected to oxygen ashes at 300 W for 15 seconds using a barrel-type oxygen plasma ashing device “PR-501” (manufactured by Yamato Scientific Co., Ltd.). The case where the difference from the thickness of the resist underlayer film was 5 nm or less was evaluated as “good”, and the case where the difference was more than 5 nm was evaluated as “bad”.
  • the composition for a resist underlayer film was applied to the surface of a silicon wafer using a spin coater at 2000 rpm for 20 seconds, and then 190. Using a hot plate maintained at a temperature of C, the silicon wafer coated with the resist underlayer film composition was heated for 2 minutes. With respect to the obtained resist underlayer film, the film thickness was measured at 50 points using an optical film thickness meter (manufactured by KLA-Tencor, UV-1280SE), and the average film thickness was obtained.
  • a resist underlayer film was formed in the same manner as described above, the film thickness was measured, and the average film thickness was obtained.
  • the average film thickness T of the coating film of the resist underlayer film composition before storage. And the average film thickness T of the coating film of the resist underlayer film composition after storage (T ⁇ T.) was calculated. Is calculated as the film thickness change rate. If the value is 10% or less, it is judged as “good”, and if it exceeds 10%, it is judged as “good”. Poor ".
  • Oxygen assing resistance good (film thickness change width 2.6 nm)
  • Oxygen assing resistance good (film thickness change width: 2.9 nm)
  • Oxygen ashing resistance good (thickness change width 3.2nm)
  • the evaluation method for each of the items (1) to (6) is the same as that for the first resist underlayer film composition.
  • Oxygen ashing resistance good (thickness change width 3.5nm)
  • Oxygen ashing resistance poor (film thickness change width 20 nm)
  • the first resist underlayer film composition of the present invention contains a heat-volatile substance together with a film-forming component formed by hydrolysis and partial condensation of a silane compound, the film-forming component is cured by heating.
  • the volatilizable substance is sometimes gasified and volatilized, resulting in a relatively low-density porous silica film having many or innumerable pores formed, and a resist underlayer film having good gas permeability formed. Is done. Therefore, the resist underlayer film can reliably and easily achieve the required gas etching with respect to the lower processing lower layer film by sufficiently transmitting the etching gas.
  • the second composition for a resist underlayer film of the present invention contains a film-forming component composed of a silane compound obtained by hydrolysis and partial condensation of a silane compound. Contains silane compound (B) W
  • the silane compound (B) When 50 is cured by heating, the silane compound (B) generates a force gas, resulting in the formation of a porous silica film having a relatively low density in which many or innumerable pores are formed.
  • a resist underlayer film having a gas permeability is formed. Accordingly, the resist underlayer film can easily and easily achieve required gas etching with respect to the lower processing lower layer film by sufficiently transmitting the etching gas.
  • composition for a resist underlayer film of the present invention has a film-forming component consisting of a hydrolyzate and Z or a condensate of a specific silane compound, it has a high adhesion to a resist while being porous.
  • the resist underlayer film which has high resistance to resist developing solution and oxygen gas for ashes for removing the resist and has a highly reproducible resist pattern on the resist film, can be formed. Moreover, excellent storage stability can be obtained.

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Abstract

L'invention concerne des compositions sub-résist destinées à former un film sub-résist présentant une perméabilité au gaz satisfaisante, une adhésion élevée aux films de résist et une résistance élevée aux solutions de développement. La première composition comprend un ingrédient de formation de film renfermant un produit de l'hydrolyse et/ou de la condensation d'un composé de silane spécifique, ainsi qu'une substance volatilisable par voie thermique se gazéifiant après une opération de chauffage. La seconde composition comprend un ingrédient de formation de film renfermant un produit de l'hydrolyse et/ou de la condensation d'un composé de silane spécifique avec un autre composé de silane doté d'un groupe organique décomposable par voie thermique. Après une opération de chauffage, l'ingrédient de formation de film de chaque composition se durcit. Parallèlement, un gaz résulte de la gazéification de la substance volatilisable par voie thermique ou des groupes organiques décomposables par voie thermique. Ainsi, ces compositions forment toutes des films de silice poreux.
PCT/JP2001/009722 2000-11-08 2001-11-07 Compositions pour film sub-resist et leurs procedes de preparation, et films sub-resist et leurs procedes de production WO2002039187A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03199043A (ja) * 1989-12-28 1991-08-30 Nippon Sheet Glass Co Ltd 反射防止膜およびその形成方法
US5670298A (en) * 1992-06-17 1997-09-23 Lg Semicon Co., Ltd. Method of forming a metal pattern in manufacturing a semiconductor device
JP2001163906A (ja) * 1999-12-07 2001-06-19 Toppan Printing Co Ltd 低屈折率組成物、低屈折率膜、光学多層膜および反射防止膜

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03199043A (ja) * 1989-12-28 1991-08-30 Nippon Sheet Glass Co Ltd 反射防止膜およびその形成方法
US5670298A (en) * 1992-06-17 1997-09-23 Lg Semicon Co., Ltd. Method of forming a metal pattern in manufacturing a semiconductor device
JP2001163906A (ja) * 1999-12-07 2001-06-19 Toppan Printing Co Ltd 低屈折率組成物、低屈折率膜、光学多層膜および反射防止膜

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