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WO2010041626A1 - Composition permettant de former une pellicule de sous-couche de réserve destinée à une lithographie et comprenant une résine contenant du fluorène - Google Patents

Composition permettant de former une pellicule de sous-couche de réserve destinée à une lithographie et comprenant une résine contenant du fluorène Download PDF

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Publication number
WO2010041626A1
WO2010041626A1 PCT/JP2009/067338 JP2009067338W WO2010041626A1 WO 2010041626 A1 WO2010041626 A1 WO 2010041626A1 JP 2009067338 W JP2009067338 W JP 2009067338W WO 2010041626 A1 WO2010041626 A1 WO 2010041626A1
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WIPO (PCT)
Prior art keywords
underlayer film
group
resist
resist underlayer
integer
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Ceased
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PCT/JP2009/067338
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English (en)
Japanese (ja)
Inventor
徹也 新城
軍 孫
圭祐 橋本
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Nissan Chemical Corp
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Nissan Chemical Corp
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Priority to JP2010532903A priority Critical patent/JPWO2010041626A1/ja
Publication of WO2010041626A1 publication Critical patent/WO2010041626A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/40—Hydrazines having nitrogen atoms of hydrazine groups being quaternised
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G10/00—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only
    • C08G10/02—Condensation polymers of aldehydes or ketones with aromatic hydrocarbons or halogenated aromatic hydrocarbons only of aldehydes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof
    • C08G59/423—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof containing an atom other than oxygen belonging to a functional groups to C08G59/42, carbon and hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
    • 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
    • G03F7/092—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by backside coating or layers, by lubricating-slip layers or means, by oxygen barrier layers or by stripping-release layers or means
    • 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
    • G03F7/094—Multilayer resist systems, e.g. planarising layers
    • 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

  • the present invention relates to a resist underlayer film forming composition for lithography effective at the time of processing a semiconductor substrate, and a resist underlayer film for lithography formed therefrom.
  • the present invention also relates to a resist pattern forming method including the resist underlayer film forming composition, and a semiconductor device manufacturing method including a step of processing a semiconductor substrate with the resist pattern.
  • the fine processing is, for example, forming a thin film made of a photoresist composition on a substrate to be processed such as a silicon wafer, and irradiating the thin film with actinic rays such as ultraviolet rays through a mask pattern in which a pattern of a semiconductor device is drawn.
  • This is a processing method in which a substrate to be processed such as a silicon wafer is subjected to an etching process using a photoresist having a pattern formed by development as a protective film.
  • a resist underlayer film forming composition using a fluorenephenol novolac resin see, for example, Patent Document 1
  • a resist underlayer film forming composition using a fluorene naphthol novolak resin for example, refer patent document 2
  • the resist underlayer film forming composition (for example, refer patent document 3 and patent document 4) containing resin which has fluorene phenol and aryl alkylene as a repeating unit structure is disclosed.
  • these lower layer films also do not satisfy all of the performance as a resist lower layer film as a mask during substrate processing, for example, solvent resistance, heat resistance, light absorbency, and selectivity of etching rate.
  • Another object of the present invention is to provide lithography having performance as an antireflection film that effectively absorbs reflected light from a substrate when fine processing of a resist underlayer film is performed by irradiation light having a wavelength of 248 nm, 193 nm, 157 nm, or the like.
  • An object of the present invention is to provide a resist underlayer film and a composition for forming the same.
  • the subject of this invention is providing the formation method of the resist pattern containing the resist underlayer film formed from a resist underlayer film formation composition. And it is providing the resist underlayer film which also has heat resistance, and the resist underlayer film forming composition for forming it.
  • R 1 and R 2 are substituents on the fluorene ring
  • R 3 , R 4 , OR 5 , OR 6 are substituents on the naphthalene ring.
  • R 1 , R 2 , R 3 , and R 4 is an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a halogen group, a nitro group, or an amino group
  • R 5 and R 6 are a hydrogen atom and 1 carbon atom, respectively.
  • Ar is an arylene group having 6 to 20 carbon atoms
  • n1 and n2 are each an integer of 0 to 4
  • n3 is an integer of 0 to (6-n5)
  • N4 is an integer from 0 to (6-n6)
  • n5 and n6 are each an integer from 1 to 6
  • n3 + n5 is an integer from 1 to 6
  • n4 + n6 is an integer from 1 to 6
  • a resist underlayer film-forming composition comprising
  • the resist underlayer film forming composition according to the first aspect in which Ar represents a substituted or unsubstituted phenylene group, naphthylene group, biphenylene group, anthrylene group, or pyrene group
  • the resist underlayer film forming composition according to the first aspect or the second aspect further containing a crosslinking agent
  • the resist underlayer film forming composition according to the third aspect As a sixth aspect, the resist underlayer film forming composition according to any one of the first aspect to the fifth aspect, which further contains an acid or an acid generator, As a seventh aspect, a resist underlayer film obtained by applying and baking the resist underlayer film forming composition according to any one of the first to sixth aspects on a semiconductor substrate, As an eighth aspect, the resist underlayer film forming composition according to any one of the first to sixth aspects is applied on a semiconductor substrate and baked to form a lower layer film.
  • a method for manufacturing a semiconductor device As a tenth aspect, a step of forming an underlayer film made of the resist underlayer film forming composition according to any one of the first to sixth aspects on a semiconductor substrate, a step of forming a hard mask on the underlayer film, Further, a step of forming a resist film on the hard mask, a step of forming a resist pattern on the resist film by light and electron beam irradiation and development, a step of etching the hard mask with the resist pattern, the patterned
  • the present invention relates to a method for manufacturing a semiconductor device
  • the resist underlayer film formed from the resist underlayer film forming composition of the present invention can form a good resist pattern shape without causing intermixing with the upper layer portion of the resist underlayer film.
  • the resist underlayer film formed from the resist underlayer film forming composition of the present invention can be provided with the ability to efficiently absorb the reflected light from the substrate, and can also have an effect as an antireflection film. .
  • the resist underlayer film forming composition of the present invention has an excellent dry etching rate selectivity close to that of the resist, a low dry etching rate selectivity compared to the resist, and a low dry etching rate selectivity compared to the semiconductor substrate.
  • a resist underlayer film can be formed.
  • the resist pattern As the resist pattern is miniaturized, the resist is thinned to prevent the resist pattern from falling after development.
  • the resist pattern is transferred to the lower layer film by an etching process, and the substrate processing is performed using the lower layer film to which the pattern is transferred as a mask, or the resist pattern is etched.
  • the process includes transferring the pattern to the lower layer film in the process, and further transferring the pattern transferred to the lower layer film to the lower layer film using a different gas composition, and finally processing the substrate.
  • the resist underlayer film and the composition for forming the same of the present invention are effective as an underlayer film for this process.
  • a processed substrate for example, a thermal silicon oxide film on the substrate). , Silicon nitride film, polysilicon film, and the like).
  • the resist underlayer film of the present invention can be used as a planarizing film, a resist underlayer film, a resist layer antifouling film, or a film having dry etch selectivity. Thereby, by using the resist underlayer film of the present invention, a resist pattern can be easily and accurately formed in the lithography process of semiconductor manufacturing.
  • a resist underlayer film formed from the resist underlayer film forming composition according to the present invention is formed on a substrate, a hard mask is formed thereon, a resist film is formed thereon, and the resist film is exposed and developed by exposure and development.
  • the hard mask used in this process may be formed by applying a composition containing an organic polymer and / or an inorganic polymer and a solvent, or may be formed by vacuum deposition of an inorganic substance.
  • an inorganic substance for example, silicon nitride oxide
  • the temperature of the resist underlayer film surface rises to around 400 ° C. when the deposit is deposited on the resist underlayer film surface. Therefore, the resist underlayer film used in the vacuum deposition method needs heat resistance.
  • the polymer constituting the resist underlayer film forming composition of the present invention is a copolymer containing a repeating unit structure of fluorene naphthol and arylene alkylene. Therefore, the heat resistance is extremely high, and thermal deterioration does not occur when depositing a deposit in the vacuum deposition method.
  • the present invention is a resist underlayer film forming composition for lithography containing a polymer containing a repeating unit structure represented by the formula (1).
  • the said polymer and a solvent are included.
  • a crosslinking agent and an acid can be included, and additives such as an acid generator and a surfactant can be included as necessary.
  • the solid content of the composition is 0.1 to 70% by mass, or 0.1 to 60% by mass. Solid content is the content rate of all the components remove
  • the polymer can be contained in the solid content in a proportion of 1 to 100% by mass, or 1 to 99% by mass, or 50 to 99% by mass.
  • the polymer used in the present invention has a weight average molecular weight of 600 to 1000000, preferably 1000 to 200000. If the average molecular weight is less than 600, sufficient hardness may not be obtained at the time of curing, and if the average molecular weight is greater than 1000000, the viscosity may become high and handling may be difficult.
  • the polymer used in the present invention includes a repeating unit structure represented by the following formula (1).
  • R 1 and R 2 represent substituents on the fluorene ring
  • R 3 , R 4 , OR 5 , and OR 6 represent substituents on the naphthalene ring.
  • R 1 , R 2 , R 3 , and R 4 each represent an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, a halogen group, a nitro group, or an amino group
  • R 5 , R 6 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or a glycidyl group
  • Ar represents an arylene group having 6 to 20 carbon atoms
  • n1 and n2 are each an integer of 0 to 4
  • n3 is an integer from 0 to (6-n5)
  • n4 is an integer from 0 to (6-n6)
  • n5 and n6 are each an integer from 1 to 6
  • n3 + n5 is an integer from 1 to 6 N4 + n6 is an integer from 1 to 6.
  • alkyl group having 1 to 10 carbon atoms examples include methyl group, ethyl group, n-propyl group, i-propyl group, cyclopropyl group, n-butyl group, i-butyl group, s-butyl group, t- Butyl, cyclobutyl, 1-methyl-cyclopropyl, 2-methyl-cyclopropyl, n-pentyl, 1-methyl-n-butyl, 2-methyl-n-butyl, 3-methyl-n -Butyl group, 1,1-dimethyl-n-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n-propyl group, cyclopentyl group, 1 -Methyl-cyclobutyl group, 2-methyl-cyclobutyl group, 3-methyl-cyclobutyl group, 1,2-dimethyl-cyclopropyl group, 2,3
  • Examples of the aryl group having 6 to 20 carbon atoms include phenyl group, o-methylphenyl group, m-methylphenyl group, p-methylphenyl group, o-chlorophenyl group, m-chlorophenyl group, and p-chlorophenyl group.
  • the halogen group includes fluorine, chlorine, bromine, iodine and the like.
  • Examples of the arylene group having 6 to 20 carbon atoms include phenylene group, naphthylene group, biphenylene group, anthrylene group, pyrene group and derivatives thereof.
  • Examples of the arylene group derivative include arylene group derivatives substituted with an alkyl group having 1 to 10 carbon atoms, a halogen group, a nitro group, or an amino group.
  • the polymer containing the repeating unit structure represented by the formula (1) is prepared by reacting, for example, a fluorene compound having a naphthol group and dimethoxymethylbenzene in the presence of an acid catalyst (for example, paratoluenesulfonic acid) at a temperature of about 130 to 180 ° C. For 1 to 10 hours.
  • an acid catalyst for example, paratoluenesulfonic acid
  • Particularly preferred polymers containing a repeating unit structure represented by the formula (1) are obtained by reacting 9,9-bis [(poly) hydroxynaphthyl] fluorenes, bisalkoxyalkylbenzenes, or dihalogenated methylanthracenes. And polymers that can be used.
  • 9,9-bis [(poly) hydroxynaphthyl] fluorenes include 9,9-bis (hydroxynaphthyl) fluorenes such as 9,9-bis [6- (2-hydroxynaphthyl)] fluorene (6, 6- (9-fluorenylidene) -di (2-naphthol)), 9,9-bis [1- (5-hydroxynaphthyl)] fluorene (5,5- (9-fluorenylidene) -di (1-naphthol)) Etc.
  • bisalkoxyalkylbenzenes include 1,4-bismethoxymethylbenzene.
  • dihalogenated methylanthracenes include 9,10-bis (chloromethyl) anthracene.
  • Polymers that can be mixed include polyacrylic acid ester compounds, polymethacrylic acid ester compounds, polyacrylamide compounds, polymethacrylamide compounds, polyvinyl compounds, polystyrene compounds, polymaleimide compounds, polymaleic anhydrides, and polyacrylonitrile compounds. Can be mentioned.
  • Examples of the raw material monomer for the polyacrylate compound include methyl acrylate, ethyl acrylate, isopropyl acrylate, benzyl acrylate, naphthyl acrylate, anthryl acrylate, anthryl methyl acrylate, phenyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2,2,2-trifluoroethyl acrylate, 4-hydroxybutyl acrylate, isobutyl acrylate, tert-butyl acrylate, cyclohexyl acrylate, isobornyl acrylate, 2-methoxyethyl acrylate, methoxytriethylene glycol acrylate, 2-ethoxyethyl acrylate , Tetrahydrofurfuryl acrylate, 3-methoxybutyl acrylate 2-methyl-2-adamantyl acrylate, 2-ethyl-2-adamantyl acrylate, 2-propyl-2
  • the raw material monomers for the polymethacrylic acid ester compound include ethyl methacrylate, normal propyl methacrylate, normal pentyl methacrylate, cyclohexyl methacrylate, benzyl methacrylate, naphthyl methacrylate, anthryl methacrylate, anthryl methyl methacrylate, phenyl methacrylate, 2-phenylethyl methacrylate, 2 -Hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, 2,2,2-trifluoroethyl methacrylate, 2,2,2-trichloroethyl methacrylate, methyl acrylate, isobutyl methacrylate, 2-ethylhexyl methacrylate, isodecyl methacrylate, normal lauryl methacrylate Normal stearyl methacrylate Methoxydiethylene glycol methacrylate, methoxypolyethylene glycol
  • Examples of the raw material monomer for the polyvinyl compound include vinyl ether, methyl vinyl ether, benzyl vinyl ether, 2-hydroxyethyl vinyl ether, phenyl vinyl ether, and propyl vinyl ether.
  • Examples of the raw material monomer for the polystyrene compound include styrene, methylstyrene, chlorostyrene, bromostyrene, and hydroxystyrene.
  • Examples of the raw material monomer of the polymaleimide compound include maleimide, N-methylmaleimide, N-phenylmaleimide, and N-cyclohexylmaleimide.
  • the above polymer dissolves an addition polymerizable monomer and a chain transfer agent added as necessary in an organic solvent, and then adds a polymerization initiator to conduct a polymerization reaction, and then adds a polymerization terminator to stop the polymerization reaction.
  • the addition amount of the chain transfer agent is 10% or less with respect to the mass of the monomer
  • the addition amount of the polymerization initiator is 1 to 10% with respect to the mass of the monomer
  • the addition amount of the polymerization terminator is 0. 0.01 to 0.2% by mass.
  • Examples of the organic solvent used include propylene glycol monomethyl ether, propylene glycol monopropyl ether, ethyl lactate, cyclohexanone, methyl ethyl ketone, and dimethylformamide.
  • Examples of the chain transfer agent include dodecane thiol and dodecyl thiol.
  • Examples of the agent include azobisisobutyronitrile and azobiscyclohexanecarbonitrile, and examples of the polymerization terminator include 4-methoxyphenol.
  • the reaction conditions are appropriately selected from a temperature of 30 to 100 ° C. and a reaction time of 1 to 48 hours.
  • a crosslinking agent having high heat resistance As the crosslinking agent having high heat resistance, a compound containing a crosslinking forming substituent having an aromatic ring (for example, a benzene ring or a naphthalene ring) in the molecule can be used. Examples thereof include a compound represented by the following formula (2), or a polymer or oligomer having a repeating unit structure represented by the following formula (3).
  • R 7 and R 8 each represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms
  • n7 is an integer of 1 to 4
  • Is an integer from 1 to (5-n7)
  • n7 + n8 is an integer from 2 to 5.
  • R 9 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • R 10 represents an alkyl group having 1 to 10 carbon atoms
  • n9 is an integer of 1 to 4
  • n9 + n10 is an integer of 1 to 4.
  • the number m of the repeating unit structure of the oligomer and polymer is in the range of 2 to 100, preferably 2 to 50.
  • the amount of the crosslinking agent to be added varies depending on the coating solvent used, the base substrate used, the required solution viscosity, the required film shape, etc., but is 0.001 to 80% by mass with respect to the total solid content, preferably The amount is 0.01 to 50% by mass, more preferably 0.05 to 40% by mass. If the addition amount of the crosslinking agent is less than 0.01% by mass, a sufficient number of crosslinking points may not be generated, and intermixing with the resist layer may occur. Moreover, when the addition amount of a crosslinking agent exceeds 80 mass%, sufficient antireflection effect may not be obtained.
  • cross-linking agents may cause a cross-linking reaction by self-condensation, but when a cross-linkable substituent is present in the polymer of the present invention, it can cause a cross-linking reaction with those cross-linkable substituents.
  • a catalyst for promoting the crosslinking reaction p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid, and naphthalene are used.
  • Mix acidic compounds such as carboxylic acids or thermal acid generators such as 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, and other organic sulfonic acid alkyl esters.
  • the blending amount is 0.0001 to 20% by mass, preferably 0.0005 to 10% by mass, preferably 0.01 to 3% by mass, based on the total solid content.
  • a photoacid generator can be added in order to match the acidity with the photoresist coated on the upper layer in the lithography process.
  • Preferred photoacid generators include, for example, onium salt photoacid generators such as bis (4-t-butylphenyl) iodonium trifluoromethanesulfonate, triphenylsulfonium trifluoromethanesulfonate, and phenyl-bis (trichloromethyl) -s.
  • -Halogen-containing compound photoacid generators such as triazine, and sulfonic acid photoacid generators such as benzoin tosylate and N-hydroxysuccinimide trifluoromethanesulfonate.
  • the amount of the photoacid generator is 0.2 to 10% by weight, preferably 0.4 to 5% by weight, based on the total solid content.
  • a light absorber a rheology modifier, an adhesion aid, a surfactant, and the like can be further added to the resist underlayer film forming composition of the present invention as necessary.
  • the light absorber is added mainly for the purpose of further improving the light absorbency of the resist underlayer film and further enhancing the effect as an antireflection film.
  • Examples of the light absorber include commercially available light absorbers described in “Technical Dye Technology and Market” (published by CMC) or “Dye Handbook” (edited by the Society of Synthetic Organic Chemistry), for example, C.I. I. Disperse Yellow 1, 3, 4, 5, 7, 8, 13, 23, 31, 49, 50, 51, 54, 60, 64, 66, 68, 79, 82, 88, 90, 93, 102, 114 and 124; C.I. I. Disperse Orange 1, 5, 13, 25, 29, 30, 31, 44, 57, 72 and 73; C.I. I.
  • the above light-absorbing agent is usually blended at a ratio of 10% by mass or less, preferably 5% by mass or less, based on the total solid content of the resist underlayer film forming composition for lithography.
  • phthalic acid derivatives such as dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dihexyl phthalate, and butyl isodecyl phthalate; adipic acid derivatives such as dinormal butyl adipate, diisobutyl adipate, diisooctyl adipate, and octyl decyl adipate , Maleic acid derivatives such as dinormal butyl maleate, diethyl maleate, and dinonyl maleate, oleic acid derivatives such as methyl oleate, butyl oleate, and tetrahydrofurfuryl oleate, and stearic acid derivatives such as normal butyl stearate and glyceryl stearate Can be mentioned. These rheology modifiers are usually blended at a ratio of less than 30% by mass with respect to the total solid content of the resist underlayer film forming
  • the adhesion auxiliary agent is added mainly for the purpose of improving the adhesion between the substrate or resist and the resist underlayer film, and for preventing the resist from peeling particularly during the development process.
  • Specific examples include chlorosilanes such as trimethylchlorosilane, dimethylvinylchlorosilane, methyldiphenylchlorosilane, and chloromethyldimethylchlorosilane, trimethylmethoxysilane, dimethyldiethoxysilane, methyldimethoxysilane, dimethylvinylethoxysilane, diphenyldimethoxysilane, And alkoxysilanes such as phenyltriethoxysilane, hexamethyldisilazane, N, N′-bis (trimethylsilyl) urea, silazanes such as dimethyltrimethylsilylamine, and trimethylsilylimidazole, vinyltrichlorosilane, ⁇ -chloropropyl
  • a surfactant can be blended in order to further improve the coating property against surface unevenness.
  • the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, and polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octyl phenol ether, and polyoxyethylene Polyoxyethylene alkyl allyl ethers such as ethylene nonylphenol ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, and Sorbitan fatty acid esters such as sorbitan tristearate, polyoxyethylene sorbitan monolaurate, polyoxy Nonionic surfactants such as polyoxyethylene sorbititit
  • the compounding amount of these surfactants is usually 2.0% by mass or less, preferably 1.0% by mass or less, based on the total solid content of the resist underlayer film forming composition for lithography of the present invention.
  • These surfactants may be added alone or in combination of two or more.
  • the solvent for dissolving the polymer, the crosslinking agent component, the crosslinking formation catalyst and the like include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether.
  • a high boiling point solvent can be mixed and used as a solvent.
  • examples thereof include propylene glycol monobutyl ether, propylene glycol monobutyl ether acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, ethyl lactate, butyl lactate, and cyclohexanone.
  • Use of these high-boiling solvents is preferable for improving the leveling property.
  • the resist used in the present invention is a photoresist or an electron beam resist.
  • a positive type photoresist composed of novolak resin and 1,2-naphthoquinonediazide sulfonic acid ester, acid
  • a chemically amplified photoresist comprising a binder having a group that increases the alkali dissolution rate by decomposition by a photoacid generator, a low molecular weight compound that increases the alkali dissolution rate of the photoresist by decomposition with an alkali-soluble binder and acid, and light
  • Chemically amplified photoresist comprising an acid generator, a binder having a group that is decomposed by an acid to increase the alkali dissolution rate, and a low molecular weight compound and a photoacid generator that are decomposed by an acid to increase the alkali dissolution rate of the photoresist Chemically amplified photoresist and bone Photoresist or
  • composition for forming an electron beam resist formed on the upper layer of the resist underlayer film for lithography in the present invention includes, for example, irradiation with a resin containing a Si—Si bond in the main chain and an aromatic ring at the terminal and an electron beam.
  • a composition comprising an acid generator that generates an acid, or a poly (p-hydroxystyrene) having a hydroxyl group substituted with an organic group containing N-carboxyamine and an acid generator that generates an acid upon irradiation with an electron beam Examples thereof include compositions.
  • the site substituted with N-carboxyamine of the polymer side chain by the acid generated from the acid generator by electron beam irradiation becomes a hydroxyl group and exhibits alkali solubility. Therefore, the portion irradiated with the electron beam is dissolved in the alkaline developer to form a resist pattern.
  • Examples of acid generators that generate an acid upon irradiation with this electron beam include 1,1-bis [p-chlorophenyl] -2,2,2-trichloroethane, 1,1-bis [p-methoxyphenyl] -2,2, Halogenated organic compounds such as 2-trichloroethane, 1,1-bis [p-chlorophenyl] -2,2-dichloroethane, and 2-chloro-6- (trichloromethyl) pyridine, triphenylsulfonium salts, and diphenyliodonium Examples thereof include onium salts such as salts, and sulfonic acid esters such as nitrobenzyl tosylate and dinitrobenzyl tosylate.
  • Examples of the developer used in the present invention include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, inorganic alkalis such as aqueous ammonia, ethylamine, and n-propylamine.
  • Primary amines secondary amines such as diethylamine and di-n-butylamine, tertiary amines such as triethylamine and methyldiethylamine, alcohol amines such as dimethylethanolamine and triethanolamine, tetramethylammonium hydroxy
  • An aqueous solution of an alkali such as quaternary ammonium salts such as copper, tetraethylammonium hydroxide and choline, and cyclic amines such as pyrrole and piperidine can be used.
  • an appropriate amount of an alcohol such as isopropyl alcohol or a nonionic surfactant may be added to the alkaline aqueous solution.
  • preferred developers are quaternary ammonium salts, more preferably tetramethylammonium hydroxide and choline.
  • the resist pattern forming method of the present invention will be described.
  • a substrate eg, a transparent substrate such as a silicon / silicon dioxide coating, a glass substrate, an ITO substrate
  • an appropriate coating method such as a spinner or a coater.
  • the thickness of the resist underlayer film is preferably 0.01 to 3.0 ⁇ m.
  • the conditions for baking after coating are 80 to 350 ° C. and 0.5 to 120 minutes.
  • a resist composition is applied and cured to form a resist film.
  • a good resist pattern can be obtained by irradiating the resist with light or an electron beam through a predetermined mask, developing, rinsing and drying. If necessary, post-irradiation heating (PEB: Post Exposure Bake) may be performed. Then, using the resist in which the pattern is formed, the resist underlayer film is removed by dry etching to form a pattern, and using the resist underlayer film in which the pattern is formed, a desired pattern can be formed on the substrate. .
  • PEB Post Exposure Bake
  • a resist underlayer film forming composition is formed on a semiconductor substrate, a resist underlayer film is formed on the resist underlayer film, and a resist pattern is formed on the resist film by light or electron beam irradiation and development.
  • a semiconductor device can be manufactured through a step of etching, a step of etching the resist underlayer film with a resist pattern, and a step of processing a semiconductor substrate with the patterned resist underlayer film.
  • a resist underlayer film for such a process unlike a conventional high etch rate resist underlayer film, a resist underlayer film for lithography having a selectivity of a dry etching rate close to that of a resist, a dry etching rate lower than that of a resist. Therefore, a lithography resist underlayer film having a selection ratio of ## EQU2 ## or a lithography resist underlayer film having a selectivity of a dry etching rate smaller than that of a semiconductor substrate is required. Further, such a resist underlayer film can be provided with an antireflection ability, and can also have a function of a conventional antireflection film.
  • the substrate after forming the resist underlayer film of the present invention on a substrate, one or several coating film materials are applied directly on the resist underlayer film or on the resist underlayer film as necessary. Thereafter, a resist composition can be applied to form a resist.
  • the substrate can be processed by selecting an appropriate etching gas even when the resist is thinly coated to prevent pattern collapse.
  • a step of forming a resist underlayer film composed of a resist underlayer film forming composition on a semiconductor substrate, a step of forming a hard mask with a coating material containing a silicon component or the like thereon, and a resist film formed thereon A step, a step of forming a resist pattern by light and electron beam irradiation and development on the resist film, a step of etching the hard mask with the resist pattern, a step of etching the resist underlayer film with the patterned hard mask
  • a semiconductor device can be manufactured through a step of processing the semiconductor substrate with the patterned resist underlayer film.
  • the resist underlayer film for lithography of the present invention has a high effect as an antireflection film because a light absorption site having sufficient light absorption performance is incorporated into the skeleton. Further, unlike an antireflection film to which a conventional light absorber is added, there is also an advantage that there is no diffused material in the photoresist during heating and drying.
  • the resist underlayer film for lithography of the present invention has high thermal stability, can prevent contamination of the upper layer film by decomposition products during baking, and can provide a margin for the temperature margin of the baking process. is there.
  • the resist underlayer film for lithography has a function of preventing reflection of light depending on process conditions, and further prevents the interaction between the substrate and the photoresist or applies to the material used for the photoresist or the photoresist. It can be used as a film having a function of preventing an adverse effect on a substrate of a substance generated during exposure.
  • Synthesis example 1 Into a reactor equipped with a stirrer, a cooler, and a nitrogen gas introduction tube, 16.6 g (0.1 mol) of 1,4-bis-methoxymethylbenzene and 6,6- (9-fluorenylidene) -di (2-naphthol) 45 0.1 g (0.1 mol) was added and 0.35 g of paratoluenesulfonic acid was added, followed by reaction at 160 ° C. for 5 hours. Methanol produced during the reaction was removed out of the system. After the reaction, it was washed with water and then dried under heating and reduced pressure to remove moisture and unreacted monomers. The residue was dissolved in propylene glycol monomethyl ether acetate and dropped into methanol for reprecipitation to obtain a fluorene resin represented by the following formula (5-1). The weight average molecular weight was 10,000.
  • Synthesis example 2 A reactor equipped with a stirrer, a cooler, and a nitrogen gas inlet tube was charged with 16 g of methyl isobutyl ketone, 27.5 g (0.1 mol) of 9,10-bis (chloromethyl) anthracene and 6,6- (9-fluorenylidene) as solvents. ) -Di (2-naphthol) 45.1 g (0.1 mol) was added, and 4.5 g of 35% hydrochloric acid was added, followed by reaction under reflux for 20 hours with stirring. After the reaction, it was washed with water and then dried under heating and reduced pressure to remove moisture and unreacted monomers. The residue was dissolved in propylene glycol monomethyl ether acetate, dropped into methanol and reprecipitated to obtain a fluorene resin represented by the following formula (5-2). The weight average molecular weight was 4000.
  • Synthesis example 3 To the reactor, 180 g of 4,4 ′-(9H-fluorene-9-ylidene) bisphenol, 75 g of 37% formalin aqueous solution, and 5 g of oxalic acid were added and stirred at 100 ° C. for 24 hours with stirring. After the reaction, the product was dissolved in 500 ml of methyl isobutyl ketone, the catalyst was removed by washing with sufficient water, and the solvent, water and unreacted monomers were removed by drying under reduced pressure to obtain a fluorene resin represented by the following formula (5-3). The weight average molecular weight was 11000.
  • Example 1 To 5 g of the fluorene resin represented by the formula (5-1) obtained in Synthesis Example 1 was mixed 0.015 g of Megafac R-30 (trade name, manufactured by Dainippon Ink & Chemicals, Inc.) as a surfactant. A solution was prepared by dissolving in 58 g of propylene glycol monomethyl ether acetate. Thereafter, the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
  • Megafac R-30 trade name, manufactured by Dainippon Ink & Chemicals, Inc.
  • Example 2 To 5 g of the fluorene resin represented by the formula (5-1) obtained in Synthesis Example 1, a compound represented by the formula (4-21) as a crosslinking agent (manufactured by Asahi Organic Materials Co., Ltd., trade name: TM- BIP-A) 0.5 g, pyridinium p-toluenesulfonate 0.005 g as a catalyst, and MegaFac R-30 (trade name, manufactured by Dainippon Ink Chemical Co., Ltd.) 0.015 g as a surfactant are mixed with propylene glycol. A solution was prepared by dissolving in 58 g of monomethyl ether acetate.
  • the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
  • a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
  • Example 3 To 5 g of the fluorene resin represented by the formula (5-1) obtained in Synthesis Example 1, 0.5 g of tetramethoxymethyl glycoluril (trade name Powder Link 1174, manufactured by Mitsui Cytec Co., Ltd.) as a crosslinking agent and pyridinium as a catalyst 0.005 g of paratoluene sulfonate and 0.015 g of Megafac R-30 (trade name, manufactured by Dainippon Ink Chemical Co., Ltd.) as a surfactant were mixed and dissolved in 58 g of propylene glycol monomethyl ether acetate to obtain a solution.
  • tetramethoxymethyl glycoluril trade name Powder Link 1174, manufactured by Mitsui Cytec Co., Ltd.
  • pyridinium pyridinium
  • Megafac R-30 trade name, manufactured by Dainippon Ink Chemical Co., Ltd.
  • the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
  • a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
  • Example 4 To 5 g of the fluorene resin represented by the formula (5-2) obtained in Synthesis Example 2, 0.015 g of Megafac R-30 (trade name, manufactured by Dainippon Ink Chemical Co., Ltd.) as a surfactant was mixed. A solution was prepared by dissolving in 58 g of propylene glycol monomethyl ether acetate. Thereafter, the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
  • Megafac R-30 trade name, manufactured by Dainippon Ink Chemical Co., Ltd.
  • Comparative Example 1 To a mixture of 1 g of phenol novolak resin (weight average molecular weight 15000) represented by the following formula (5-4), 1 g of bisphenol fluorenediglycidyl ether represented by the following formula (5-5), and 0.06 g of triphenylphosphine, 39.14 g of cyclohexanone was added and dissolved to obtain a solution. Thereafter, the solution was filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m to prepare a resist underlayer film forming composition solution used for the lithography process.
  • phenol novolak resin weight average molecular weight 15000
  • 5-5 bisphenol fluorenediglycidyl ether represented by the following formula (5-5)
  • triphenylphosphine 39.14 g of cyclohexanone was added and dissolved to obtain a solution. Thereafter, the solution was
  • the resist underlayer film forming compositions prepared in Examples 1 to 4 and Comparative Example 1 or 2 were each applied onto a silicon wafer using a spinner. Heating was performed at 240 ° C. for 1 minute on a hot plate to form a resist underlayer film (film thickness: 0.25 ⁇ m). Using a spectroscopic ellipsometer, the refractive index (n value) and optical absorption coefficient (k value, also called attenuation coefficient) of these resist underlayer films at a wavelength of 248 nm and a wavelength of 193 nm were measured. The results are shown in Table 1.
  • a phenol novolac resin solution was formed on a silicon wafer using a spinner.
  • the film was heated on a hot plate at 205 ° C. for 1 minute to form a coating film (film thickness: 0.25 ⁇ m).
  • the dry etching rate was measured using CF 4 gas as an etching gas, and the dry etching rates of the resist underlayer films of Examples 1 to 4 and Comparative Examples 1 and 2 were compared. The results are shown in Table 2.
  • the speed ratio (1) is a dry etching speed ratio of (resist underlayer film after heating at 240 ° C. for 1 minute) / (phenol novolac resin film after heating at 205 ° C. for 1 minute).
  • the speed ratio (2) is a dry etching speed ratio of (resist underlayer film after heating at 400 ° C. for 2 minutes) / (phenol novolak resin film after heating at 205 ° C. for 1 minute).
  • the polymers used in the present invention have high heat resistance, and the resist underlayer film forming composition using these polymers has heat stability even in the step of forming a hard mask by vapor deposition on the upper layer in a multilayer lithography process.

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Abstract

La présente invention concerne une composition permettant de former une pellicule de sous-couche de réserve qui possède la résistance à la chaleur nécessaire afin de servir dans un procédé de lithographie pendant la fabrication d'un dispositif à semi-conducteurs. La composition permettant de former une pellicule de sous-couche de réserve comprend un polymère qui contient une structure unitaire représentée par la formule (1). (Dans la formule, R1, R2, R3 et R4 représentent chacun un groupe alkyle comptant de 1 à 10 atomes de carbone, un groupe aryle comptant de 6 à 20 atomes de carbone, un groupe halogène, un groupe nitro ou un groupe amino; R5 et R6 représentent chacun un atome d'hydrogène, un groupe alkyle comptant de 1 à 10 atomes de carbone ou un groupe glycidyle; Ar représente un groupe arylène comptant de 6 à 20 atomes de carbone; et n1 et n2 représentent chacun un entier de 0 à 4, n3 représente un entier de 0 à (6-n5), n4 représente un entier de 0 à (6-n6), et n5 et n6 représentent chacun un entier de 1 à 6, n3 + n5 étant un entier de 1 à 6 et n4 + n6 étant un entier de 1 à 6.)
PCT/JP2009/067338 2008-10-10 2009-10-05 Composition permettant de former une pellicule de sous-couche de réserve destinée à une lithographie et comprenant une résine contenant du fluorène Ceased WO2010041626A1 (fr)

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