WO2014024836A1 - レジスト下層膜形成組成物 - Google Patents
レジスト下層膜形成組成物 Download PDFInfo
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- WO2014024836A1 WO2014024836A1 PCT/JP2013/071134 JP2013071134W WO2014024836A1 WO 2014024836 A1 WO2014024836 A1 WO 2014024836A1 JP 2013071134 W JP2013071134 W JP 2013071134W WO 2014024836 A1 WO2014024836 A1 WO 2014024836A1
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Images
Classifications
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- 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
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- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
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- 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
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- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09D161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
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- 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
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- G03F7/16—Coating processes; Apparatus therefor
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- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
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- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
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- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
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- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
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- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
- H01L21/3083—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their size, orientation, disposition, behaviour, shape, in horizontal or vertical plane
- H01L21/3086—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their size, orientation, disposition, behaviour, shape, in horizontal or vertical plane characterised by the process involved to create the mask, e.g. lift-off masks, sidewalls, or to modify the mask, e.g. pre-treatment, post-treatment
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- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3205—Deposition of non-insulating-, e.g. conductive- or resistive-, layers on insulating layers; After-treatment of these layers
- H01L21/321—After treatment
- H01L21/3213—Physical or chemical etching of the layers, e.g. to produce a patterned layer from a pre-deposited extensive layer
- H01L21/32139—Physical or chemical etching of the layers, e.g. to produce a patterned layer from a pre-deposited extensive layer using masks
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/0271—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers
- H01L21/0273—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising organic layers characterised by the treatment of photoresist layers
- H01L21/0274—Photolithographic processes
Definitions
- the present invention relates to a resist underlayer film forming composition for a lithography process.
- the present invention relates to a composition for forming a resist underlayer film having etching resistance when used as a mask material and having a surface embedding property with a step, a concave portion and / or a convex portion.
- fine processing is performed by a lithography process.
- the lithography process when the resist layer on the substrate is exposed with an ultraviolet laser such as a KrF excimer laser or an ArF excimer laser, the desired effect is caused by the standing wave generated by the reflection of the ultraviolet laser on the substrate surface.
- an ultraviolet laser such as a KrF excimer laser or an ArF excimer laser
- the desired effect is caused by the standing wave generated by the reflection of the ultraviolet laser on the substrate surface.
- a resist pattern having a shape is not formed.
- it is adopted to provide a resist underlayer film (antireflection film) between the substrate and the resist layer.
- a novolak resin as a composition for forming a resist underlayer film.
- Patent Document 1 and Patent Document 2 disclose a photoresist underlayer film forming material containing a resin having a repeating unit obtained by novolakizing a compound having a bisphenol group.
- Patent Document 3 discloses a spin-coatable antireflection film composition containing a polymer having an aromatic ring condensed in three or more in the main chain of the polymer.
- Patent Documents 1 to 3 neither describe nor suggest a resist underlayer film forming composition containing a polymer having the condensed aromatic ring in the side chain.
- a lithography process is also known in which at least two resist underlayer films are formed and the resist underlayer films are used as a mask material in order to reduce the thickness of the resist layer required in accordance with the miniaturization of the resist pattern.
- the material forming the at least two layers include organic resins (for example, acrylic resins and novolac resins), silicon resins (for example, organopolysiloxane), and inorganic silicon compounds (for example, SiON, SiO 2 ).
- an etching gas for example, fluorocarbon
- Patent Document 4 discloses a composition containing a polymer containing a heterocyclic aromatic moiety.
- An object of the present invention is to provide a composition for forming a resist underlayer film having etching resistance against an etching gas such as fluorocarbon and having a surface embedding property having a step, a concave portion and / or a convex portion. That is.
- the first aspect of the present invention is the following formula (1a), formula (1b) and formula (1c): Wherein two R 1 is independently an alkyl group containing 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aromatic hydrocarbon group, a halogen atom, a nitro group or an amino group, 2 Each R 2 independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an acetal group, an acyl group, or a glycidyl group, and R 3 has a substituent.
- R 4 represents a hydrogen atom, a phenyl group or a naphthyl group, and when R 3 and R 4 bonded to the same carbon atom each represent a phenyl group, they are bonded to each other to form a fluorene ring.
- the group represented by two R 3 and the atom or group represented by two R 4 may be different from each other, and two k each independently represents 0 or 1, m 3no Represents an integer of 500, n, n 1 and n 2 represents an integer of 2 to 500, p represents an integer of 3 to 500, the following X represents a single bond or a hetero atom, each independently two Q Formula (2): (In the formula, two R 1 , two R 2 , two R 3 , two R 4 , two k, n 1 , n 2 and X are as defined in formula (1b), and two Q 1 are Each independently represents a structural unit represented by the formula (2).) Represents a structural unit represented by ] It is the resist underlayer film forming composition containing the polymer which has any one or 2 or more among the repeating structural units represented by these, and a solvent.
- X represents a single bond
- a biphenyl structure in which the two benzene rings of formula (1a), formula (1b) and formula (1c) are directly connected by a single bond is formed.
- the heteroatom is an atom other than a carbon atom and a hydrogen atom and can form a divalent group, and examples thereof include a sulfur atom and an oxygen atom.
- R 1 represents a halogen atom
- examples of the halogen atom include a chlorine atom and a bromine atom.
- the aromatic ring of the aromatic hydrocarbon group may be monocyclic, polycyclic (including bicyclic), or heterocyclic, for example, phenyl group, biphenyl group, naphthyl group, anthryl group, pyrenyl group, thienyl group, pyridyl group. Is mentioned.
- the aromatic hydrocarbon group which may have a substituent represented by R 3 a phenyl group, a naphthyl group, an anthryl group and a pyrenyl group are preferable from the viewpoint of etching resistance and embedding property.
- a substituent of an aromatic hydrocarbon group a methoxy group and an aldehyde group are mentioned, for example.
- the resist underlayer film forming composition of the present invention may further contain at least one of a crosslinking agent, an acidic compound, a thermal acid generator and a surfactant as an optional component.
- Etching the lower layer film, etching the first resist lower layer film using the second resist lower layer pattern after etching as a mask, and using the first resist lower layer pattern after etching as a mask It is a manufacturing method of a semiconductor device including the process of etching the surface which has the level
- the resist underlayer film formed by using the resist underlayer film forming composition of the present invention has etching resistance against an etching gas such as fluorocarbon, and is excellent in embedding of a surface having a concave portion and / or a convex portion.
- FIG. 1 is a cross-sectional SEM photograph showing the results of an embedding test using the resist underlayer film forming composition prepared in Example 1.
- FIG. 2 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 2.
- FIG. 3 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 3.
- FIG. 4 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 4.
- FIG. 5 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 5.
- FIG. 5 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 5.
- FIG. 6 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 6.
- FIG. 7 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 7.
- FIG. 8 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 8.
- FIG. 9 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 9.
- FIG. 10 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 10.
- FIG. 11 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 11.
- FIG. 12 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 12.
- FIG. 13 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 13.
- FIG. 14 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 14.
- FIG. 15 is a cross-sectional SEM photograph showing the result of a burying test using the resist underlayer film forming composition prepared in Example 15.
- FIG. 15 is a cross-sectional SEM photograph showing the result of a burying test using the resist underlayer film forming composition prepared in Example 15.
- FIG. 16 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 16.
- FIG. 17 is a cross-sectional SEM photograph showing the result of an embedding test using the resist underlayer film forming composition prepared in Example 17.
- 18 is a cross-sectional SEM photograph showing the result of a burying test using the resist underlayer film forming composition prepared in Example 18.
- FIG. FIG. 19 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Example 19.
- FIG. 20 is a cross-sectional SEM photograph showing the result of an embedding test using the resist underlayer film forming composition prepared in Example 20.
- FIG. 21 is a cross-sectional SEM photograph showing the results of a burying test using the resist underlayer film forming composition prepared in Comparative Example 3.
- Examples of the structural unit of the polymer having a repeating structural unit represented by the above formula (1a) contained in the resist underlayer film forming composition of the present invention are represented by the following formulas (1-1) to (1-36).
- Examples of the structural unit of the polymer having the repeating structural unit represented by the above formula (1b) include the structural units represented by the following formulas (1-37) to (1-72).
- Examples of the structural unit of the polymer having a repeating structural unit represented by the above formula (1c) include structural units represented by the following formulas (1-73) to (1-108).
- two Q, n 1 and n 2 have the same meanings as the formula (1b).
- the weight average molecular weight of the polymer contained in the resist underlayer film forming composition of the present invention is, for example, 1000 to 5000 in terms of standard polystyrene.
- the polymer is synthesized by polymerizing a biphenol compound or bisphenol compound having two hydroxyphenyl groups and an aromatic aldehyde or aromatic ketone in the presence of an acid catalyst such as a sulfonic acid compound.
- an acid catalyst such as a sulfonic acid compound.
- the biphenol compound or bisphenol compound having two hydroxyphenyl groups include 4,4′-biphenol, 2,2′-biphenol, 2,4′-biphenol, 4,4′-thiodiphenol, and 4,4 ′. -Oxydiphenol.
- aromatic aldehyde used for the synthesis of the polymer examples include furfural, pyridinecarboxaldehyde, benzaldehyde, naphthylaldehyde, anthrylaldehyde, phenanthrylaldehyde, salicylaldehyde, phenylacetaldehyde, 3-phenylpropionaldehyde, tolylaldehyde, (N, N-dimethylamino) benzaldehyde, acetoxybenzaldehyde, 1-pyrenecarboxaldehyde, anisaldehyde are mentioned, and aromatic aldehydes excluding aldehydes having an aromatic heterocycle such as furfural and pyridinecarboxaldehyde are preferably used.
- the aromatic ketone used in the synthesis of the polymer is a diaryl ketone, and examples thereof include diphenyl ketone, phenyl naphthyl ketone, dinaphthyl ketone, phenyl tolyl ketone, ditolyl ketone, and 9-fluorenone.
- the biphenol compound or bisphenol compound used in the synthesis of the polymer is not limited to one type of compound and may be used in two or more types, and the aromatic aldehyde or aromatic ketone is not limited to one type of compound and is used in two or more types. May be.
- 4,4-biphenol can be used as the biphenol compound
- benzaldehyde and naphthylaldehyde can be used as the aromatic aldehyde.
- the resist underlayer film forming composition of the present invention can further contain a crosslinking agent.
- a cross-linkable compound having at least two cross-linking substituents is preferably used.
- examples thereof include melamine compounds, substituted urea compounds and phenolic compounds having a crosslink forming substituent such as a methylol group or a methoxymethyl group.
- Specific examples include compounds such as methoxymethylated glycoluril and methoxymethylated melamine, and examples include tetramethoxymethylglycoluril, tetrabutoxymethylglycoluril, and hexamethoxymethylmelamine.
- examples of the substituted urea compound include tetramethoxymethylurea and tetrabutoxymethylurea.
- examples of phenolic compounds include tetrahydroxymethyl biphenol, tetramethoxymethyl biphenol (TMOM-BP), and tetramethoxymethyl bisphenol.
- TMOM-BP tetramethoxymethyl biphenol
- TMOM-BP tetramethoxymethyl biphenol
- TMOM-BP tetramethoxymethyl bisphenol
- cross-linking agent a compound having at least two epoxy groups can also be used.
- Examples of such compounds include tris (2,3-epoxypropyl) isocyanurate, 1,4-butanediol diglycidyl ether, 1,2-epoxy-4- (epoxyethyl) cyclohexane, glycerol triglycidyl ether, diethylene glycol Diglycidyl ether, 2,6-diglycidylphenyl glycidyl ether, 1,1,3-tris [p- (2,3-epoxypropoxy) phenyl] propane, 1,2-cyclohexanedicarboxylic acid diglycidyl ester, 4,4 '-Methylenebis (N, N-diglycidylaniline), 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, trimethylolethane triglycidyl ether, bisphenol-A-diglycidyl ether, Epolide [registered trademark] GT-401
- epoxy resins examples include YH-434 and YH-434L (manufactured by Nippon Kasei Epoxy Manufacturing Co., Ltd. (formerly Toto Kasei Co., Ltd.)).
- crosslinking agent a compound having at least two blocked isocyanate groups can also be used. Examples of such compounds include Takenate (registered trademark) B-830 and B-870N manufactured by Mitsui Chemicals, Inc. and VESTANAT (registered trademark) B1358 / 100 manufactured by Evonik Degussa.
- a compound having at least two vinyl ether groups can also be used.
- Examples of such compounds include bis (4- (vinyloxymethyl) cyclohexylmethyl) glutarate, tri (ethylene glycol) divinyl ether, adipic acid divinyl ester, diethylene glycol divinyl ether, 1,2,4-tris (4-vinyl).
- One kind selected from these various crosslinking agents may be added, or two or more kinds may be added in combination.
- the content of the crosslinking agent is, for example, 2% by mass to 60% by mass with respect to the solid content excluding the solvent described later from the resist underlayer film forming composition of the present invention.
- the resist underlayer film forming composition of the present invention can further contain an acidic compound.
- the acidic compound serves as a catalyst for promoting the cross-linking reaction.
- p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium-p-toluenesulfonate, salicylic acid, camphorsulfonic acid, 5-sulfosalicylic acid, 4-chlorobenzenesulfonic acid examples include 4-hydroxybenzenesulfonic acid, benzenedisulfonic acid, 1-naphthalenesulfonic acid, citric acid, benzoic acid, sulfonic acid compounds such as hydroxybenzoic acid, and carboxylic acid compounds, and inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, and phosphoric acid.
- a thermal acid generator can be contained.
- the thermal acid generator also serves as a catalyst for promoting the crosslinking reaction, and examples thereof include quaternary ammonium salts of trifluoromethanesulfonic acid.
- One kind selected from these acidic compounds and thermal acid generators may be added, or two or more kinds may be added in combination.
- the content ratio of the acidic compound or thermal acid generator is, for example, 0.1% by mass to 20% by mass with respect to the solid content excluding the solvent described later from the resist underlayer film forming composition of the present invention.
- the resist underlayer film forming composition of the present invention can further contain a surfactant.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene Polyoxyethylene alkyl aryl ethers such as ethylene nonylphenyl ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan Sorbitan fatty acid esters such as tristearate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as rubitan monopalmitate, polyoxyethylene sorbitan monostea
- One kind selected from these surfactants may be added, or two or more kinds may be added in combination.
- the content rate of the said surfactant is 0.01 mass% thru
- the resist underlayer film forming composition of the present invention can be prepared by dissolving each of the above components in an appropriate solvent, and is used in a uniform solution state.
- solvents include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether acetate, propylene glycol.
- the step of applying and baking the resist underlayer film forming composition of the present invention on a surface having a step, a recess and / or a protrusion includes a substrate having a surface having a step, a recess and / or a protrusion (for example, wiring, other structure).
- a silicon wafer on which a body is formed, and the silicon wafer may be coated with a silicon oxide film, a silicon nitride film, a silicon oxynitride film, or a metal film such as aluminum or tungsten).
- the composition is applied by an appropriate application method such as, and then baked using a heating means such as a hot plate. Baking conditions are appropriately selected from a baking temperature of 100 ° C. to 400 ° C. and a baking time of 0.3 minutes to 10 minutes.
- An organopolysiloxane film is formed as a second resist underlayer film on the first resist underlayer film formed by the above process, and a resist pattern is formed thereon.
- a mask reticle
- the exposure source for example, g-line, i-line, KrF excimer laser, ArF excimer laser, EUV, or electron beam can be used.
- post-exposure heating Post Exposure Bake is performed as necessary.
- a developer for example, an aqueous 2.38 mass% tetramethylammonium hydroxide solution
- a rinse solution or pure water to remove the used developer.
- the resist pattern is dried and post-baked in order to improve adhesion to the base.
- the etching process performed after forming the resist pattern is performed by dry etching.
- the etching gas used for dry etching include CHF 3 , CF 4 , and C 2 F 6 for the second resist underlayer film (organopolysiloxane film).
- the resist underlayer film forming composition of the present invention For the formed first resist underlayer film, for example, O 2 , N 2 O, NO 2 can be mentioned, and for the surface having a step or a concave portion and / or a convex portion, for example, CHF 3 , CF 4 , C 2 F 6 is mentioned. Further, argon, nitrogen or carbon dioxide can be mixed with these gases.
- the polymer obtained in this synthesis example has a structural unit represented by the formula (1-4) and a structural unit represented by the formula (1-76).
- the polymer obtained in this synthesis example has a structural unit represented by the formula (1-16) and a structural unit represented by the formula (1-88).
- TDP-Py target polymer
- the weight average molecular weight Mw of TDP-Py measured in terms of polystyrene by GPC was 1010, and the polydispersity Mw / Mn was 1.67.
- the polymer obtained in this synthesis example has a structural unit represented by the formula (1-28) and a structural unit represented by the formula (1-100).
- the mixture was allowed to cool to room temperature and reprecipitated into methanol (1800 g, manufactured by Kanto Chemical Co., Inc.).
- the obtained precipitate was filtered and dried in a vacuum dryer at 50 ° C. for 10 hours to obtain 21.58 g of a target polymer (hereinafter abbreviated as 4,4′-BPOH-Py2 in this specification). It was.
- the weight average molecular weight Mw of the 4,4′-BPOH-Py2 measured in terms of polystyrene by GPC was 2180, and the polydispersity Mw / Mn was 2.11.
- the polymer obtained in this synthesis example has a structural unit represented by the formula (1-40).
- the mixture was allowed to cool to room temperature and reprecipitated in methanol (3000 g, manufactured by Kanto Chemical Co., Inc.).
- methanol 3000 g, manufactured by Kanto Chemical Co., Inc.
- the obtained precipitate was filtered and dried in a vacuum dryer at 50 ° C. for 10 hours to obtain 68.22 g of a target polymer (hereinafter abbreviated as 2,2′-BPOH-Py2 in this specification). It was.
- the weight average molecular weight Mw of 2,2′-BPOH-Py2 measured in terms of polystyrene by GPC was 1270, and the polydispersity Mw / Mn was 1.77.
- the polymer obtained in this synthesis example has a structural unit represented by the formula (1-52).
- TDP-Py2 the target polymer
- the weight average molecular weight Mw of TDP-Py2 measured in terms of polystyrene by GPC was 1100, and the polydispersity Mw / Mn was 1.64.
- the polymer obtained in this synthesis example has a structural unit represented by the formula (1-64).
- the polymer obtained in this synthesis example has a structural unit represented by the formula (1-38).
- the mixture was allowed to cool to room temperature and reprecipitated into methanol (800 g, manufactured by Kanto Chemical Co., Inc.).
- methanol 800 g, manufactured by Kanto Chemical Co., Inc.
- the obtained precipitate was filtered and dried in a vacuum dryer at 50 ° C. for 10 hours to obtain 5.87 g of a target polymer (hereinafter abbreviated as 2,2′-BPOH—Np2). It was.
- the weight average molecular weight Mw of 2,2′-BPOH—Np2 measured in terms of polystyrene by GPC was 1690, and the polydispersity Mw / Mn was 2.27.
- the polymer obtained in this synthesis example has a structural unit represented by the formula (1-50).
- TDP-Np2 a target polymer (hereinafter abbreviated as TDP-Np2) was obtained. Obtained.
- the weight average molecular weight Mw of TDP-Np2 measured in terms of polystyrene by GPC was 1090, and the polydispersity Mw / Mn was 1.49.
- the polymer obtained in this synthesis example has a structural unit represented by the formula (1-62).
- BHPCH-FA a target polymer having a structural unit represented by the following formula (3) (hereinafter abbreviated as BHPCH-FA in the present specification). 4.45 g was obtained.
- BHPCH-FA had a weight average molecular weight Mw measured in terms of polystyrene by GPC of 10700 and a polydispersity Mw / Mn of 3.64.
- Example 1 To 20 g of the polymer obtained in Synthesis Example 1, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Megafac R-30 manufactured by DIC Corporation
- Example 2 2.0 g of TMOM-BP (manufactured by Honshu Chemical Industry Co., Ltd., 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl) as a crosslinking agent was added to 20 g of the polymer obtained in Synthesis Example 1. 0.10 g of thermal acid generator TAG-2589 (manufactured by King Corp., quaternary ammonium salt of trifluoromethanesulfonic acid) as a catalyst, and 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant. The solution was mixed and dissolved in 88 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- TAG-2589
- Example 3 To 20 g of the polymer obtained in Synthesis Example 2, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Megafac R-30 manufactured by DIC Corporation
- Example 4 To 20 g of the polymer obtained in Synthesis Example 2, 2.0 g of TMOM-BP (manufactured by Honshu Chemical Industry Co., Ltd., 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl) was used as a crosslinking agent. 0.10 g of thermal acid generator TAG-2589 (manufactured by King Corp., quaternary ammonium salt of trifluoromethanesulfonic acid) as a catalyst, and 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant. The solution was mixed and dissolved in 88 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Example 5 To 20 g of the polymer obtained in Synthesis Example 3, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Megafac R-30 manufactured by DIC Corporation
- Example 6 To 20 g of the polymer obtained in Synthesis Example 3, 2.0 g of TMOM-BP (manufactured by Honshu Chemical Industry Co., Ltd., 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl) was used as a crosslinking agent. 0.10 g of a thermal acid generator TAG-2589 (manufactured by King, quaternary ammonium salt of trifluoromethanesulfonic acid) as a catalyst and 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant. The solution was mixed and dissolved in 88 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- TAG-2589
- Example 7 To 20 g of the polymer obtained in Synthesis Example 4, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) was mixed as a surfactant and dissolved in 80 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Megafac R-30 manufactured by DIC Corporation
- Example 8 To 20 g of the polymer obtained in Synthesis Example 4, 2.0 g of TMOM-BP (manufactured by Honshu Chemical Industry Co., Ltd., 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl) was used as a crosslinking agent. 0.10 g of thermal acid generator TAG-2589 (manufactured by King Corp., quaternary ammonium salt of trifluoromethanesulfonic acid) as a catalyst, and 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant. The solution was mixed and dissolved in 88 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Example 9 To 20 g of the polymer obtained in Synthesis Example 5, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Megafac R-30 manufactured by DIC Corporation
- Example 10 2.0 g of TMOM-BP (manufactured by Honshu Chemical Industry Co., Ltd., 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl) as a crosslinking agent was added to 20 g of the polymer obtained in Synthesis Example 5. 0.10 g of thermal acid generator TAG-2589 (manufactured by King Corp., quaternary ammonium salt of trifluoromethanesulfonic acid) as a catalyst, and 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant. The solution was mixed and dissolved in 88 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- TAG-2589
- Example 11 To 20 g of the polymer obtained in Synthesis Example 6, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Megafac R-30 manufactured by DIC Corporation
- Example 12 To 20 g of the polymer obtained in Synthesis Example 6, 2.0 g of TMOM-BP (manufactured by Honshu Chemical Industry Co., Ltd., 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl) was used as a crosslinking agent. 0.10 g of thermal acid generator TAG-2589 (manufactured by King Corp., quaternary ammonium salt of trifluoromethanesulfonic acid) as a catalyst, and 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant. The solution was mixed and dissolved in 88 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Example 13 To 20 g of the polymer obtained in Synthesis Example 7, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Megafac R-30 manufactured by DIC Corporation
- Example 14 2.0 g of TMOM-BP (manufactured by Honshu Chemical Industry Co., Ltd., 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl) as a crosslinking agent was added to 20 g of the polymer obtained in Synthesis Example 7. 0.10 g of thermal acid generator TAG-2589 (manufactured by King Corp., quaternary ammonium salt of trifluoromethanesulfonic acid) as a catalyst, and 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant. The solution was mixed and dissolved in 88 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- TAG-2589
- Example 15 To 20 g of the polymer obtained in Synthesis Example 8, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Megafac R-30 manufactured by DIC Corporation
- Example 16 To 20 g of the polymer obtained in Synthesis Example 8, 2.0 g of TMOM-BP (manufactured by Honshu Chemical Industry Co., Ltd., 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl) as a crosslinking agent 0.10 g of thermal acid generator TAG-2688 (manufactured by King, component is quaternary ammonium salt of trifluoromethanesulfonic acid) as a catalyst, and Megafac R-30 (manufactured by DIC Corporation) as a surfactant. 06 g was mixed and dissolved in 88 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- TAG-2688 thermal acid generator
- Example 17 To 20 g of the polymer obtained in Synthesis Example 9, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Megafac R-30 manufactured by DIC Corporation
- Example 18 2.0 g of TMOM-BP (manufactured by Honshu Chemical Industry Co., Ltd., 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl) as a crosslinking agent was added to 20 g of the polymer obtained in Synthesis Example 9. 0.10 g of thermal acid generator TAG-2589 (manufactured by King Corp., quaternary ammonium salt of trifluoromethanesulfonic acid) as a catalyst, and 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant. The solution was mixed and dissolved in 88 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- TAG-2589
- Example 19 To 20 g of the polymer obtained in Synthesis Example 10, 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant was mixed and dissolved in 80 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Megafac R-30 manufactured by DIC Corporation
- Example 20 To 20 g of the polymer obtained in Synthesis Example 10, 2.0 g of TMOM-BP (manufactured by Honshu Chemical Industry Co., Ltd., 3,3 ′, 5,5′-tetramethoxymethyl-4,4′-dihydroxybiphenyl) was used as a crosslinking agent. 0.10 g of thermal acid generator TAG-2589 (manufactured by King Corp., quaternary ammonium salt of trifluoromethanesulfonic acid) as a catalyst, and 0.06 g of Megafac R-30 (manufactured by DIC Corporation) as a surfactant. The solution was mixed and dissolved in 88 g of cyclohexanone to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Comparative Example 2 As a surfactant, 20 g of the polymer obtained in Comparative Synthesis Example 1 was mixed with 0.06 g of Megafac R-30 (manufactured by DIC Corporation) and dissolved in 80 g of propylene glycol monomethyl ether acetate to obtain a solution. Then, it filtered using the polyethylene micro filter with a hole diameter of 0.10 micrometer, and also filtered using the polyethylene micro filter with the hole diameter of 0.05 micrometer, and prepared the resist underlayer film forming composition used for a lithography process.
- Megafac R-30 manufactured by DIC Corporation
- the etcher and etching gas used for the measurement of the dry etching rate are as follows.
- Etching gas: CF 4 The resist underlayer film forming compositions prepared in Examples 1 to 20, Comparative Example 1 and Comparative Example 2 were each applied onto a silicon wafer using a spin coater. Baking was performed on a hot plate at 240 ° C. for 1 minute or 400 ° C. for 2 minutes to form a resist underlayer film (film thickness: 0.25 ⁇ m). Using CF 4 gas as an etching gas, the dry etching rate of these resist underlayer films was measured.
- a phenol-novolak resin (commercial product, weight average molecular weight Mw measured by polystyrene conversion by GPC is 2000, polydispersity Mw / Mn is 2.5) is applied onto a silicon wafer using a spin coater. Then, it was baked on a hot plate at 205 ° C. for 1 minute to form a phenol novolac resin film (film thickness: 0.25 ⁇ m). Using CF 4 gas as an etching gas, the dry etching rate of the phenol novolac resin film was measured.
- the resist underlayer film forming compositions prepared in Examples 1 to 20 and Comparative Example 3 were each applied onto a hole wafer using a spin coater.
- the resist was baked on a hot plate at 400 ° C. for 2 minutes to form a resist underlayer film (thickness of the hole pattern non-formed portion 0.25 ⁇ m).
- As the hole wafer a wafer on which a hole pattern with a diameter of 100 nm and a height of 400 nm was formed was used.
- the resist underlayer film forming composition prepared in Example 1 to Example 20 was applied as described above, and the cross section of each hole wafer after baking was observed with a scanning electron microscope (SEM). From the cross-sectional SEM photograph shown in FIG.
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Abstract
Description
[式中、2つのR1はそれぞれ独立に炭素原子数1乃至10のアルキル基、炭素原子数2乃至6のアルケニル基、芳香族炭化水素基、ハロゲン原子、ニトロ基又はアミノ基を表し、2つのR2はそれぞれ独立に水素原子、炭素原子数1乃至10のアルキル基、炭素原子数2乃至6のアルケニル基、アセタール基、アシル基又はグリシジル基を表し、R3は置換基を有してもよい芳香族炭化水素基を表し、R4は水素原子、フェニル基又はナフチル基を表し、同一の炭素原子と結合するR3とR4がそれぞれフェニル基を表すとき互いに結合してフルオレン環を形成してもよく、式(1b)において2つのR3が表す基及び2つのR4が表す原子又は基は互いに異なっていてもよく、2つのkはそれぞれ独立に0又は1を表し、mは3乃至500の整数を表し、n、n1及びn2は2乃至500の整数を表し、pは3乃至500の整数を表し、Xは単結合又はヘテロ原子を表し、2つのQはそれぞれ独立に下記式(2):
(式中、2つのR1、2つのR2、2つのR3、2つのR4、2つのk、n1、n2及びXは式(1b)と同義であり、2つのQ1はそれぞれ独立に前記式(2)で表される構造単位を表す。)
で表される構造単位を表す。]
で表される繰り返し構造単位のうちいずれか1つ又は2つ以上を有するポリマー及び溶剤を含むレジスト下層膜形成組成物である。
前記架橋剤としては、また、少なくとも二つのエポキシ基を有する化合物を用いることもできる。このような化合物として、例えば、トリス(2,3-エポキシプロピル)イソシアヌレート、1,4-ブタンジオールジグリシジルエーテル、1,2-エポキシ-4-(エポキシエチル)シクロヘキサン、グリセロールトリグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、2,6-ジグリシジルフェニルグリシジルエーテル、1,1,3-トリス[p-(2,3-エポキシプロポキシ)フェニル]プロパン、1,2-シクロヘキサンジカルボン酸ジグリシジルエステル、4,4’-メチレンビス(N,N-ジグリシジルアニリン)、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキサンカルボキシレート、トリメチロールエタントリグリシジルエーテル、ビスフェノール-A-ジグリシジルエーテル、(株)ダイセル製のエポリード〔登録商標〕GT-401、同GT-403、同GT-301、同GT-302、セロキサイド〔登録商標〕2021、同3000、三菱化学(株)製の1001、1002、1003、1004、1007、1009、1010、828、807、152、154、180S75、871、872、日本化薬(株)製のEPPN201、同202、EOCN-102、同103S、同104S、同1020、同1025、同1027、ナガセケムテックス(株)製のデナコール〔登録商標〕EX-252、同EX-611、同EX-612、同EX-614、同EX-622、同EX-411、同EX-512、同EX-522、同EX-421、同EX-313、同EX-314、同EX-321、BASFジャパン(株)製のCY175、CY177、CY179、CY182、CY184、CY192、DIC(株)製のエピクロン200、同400、同7015、同835LV、同850CRPを挙げることができる。前記少なくとも二つのエポキシ基を有する化合物としては、また、アミノ基を有するエポキシ樹脂を使用することもできる。このようなエポキシ樹脂として、例えば、YH-434、YH-434L(新日化エポキシ製造(株)(旧東都化成(株))製)が挙げられる。
前記架橋剤としては、また、少なくとも2つのブロックイソシアネート基を有する化合物を使用することもできる。このような化合物として、例えば、三井化学(株)製のタケネート〔登録商標〕B-830、同B-870N、エボニックデグサ社製のVESTANAT〔登録商標〕B1358/100が挙げられる。
前記架橋剤としては、また、少なくとも2つのビニルエーテル基を有する化合物を使用することもできる。このような化合物として、例えば、ビス(4-(ビニルオキシメチル)シクロヘキシルメチル)グルタレート、トリ(エチレングリコール)ジビニルエーテル、アジピン酸ジビニルエステル、ジエチレングリコールジビニルエーテル、1,2,4-トリス(4-ビニルオキシブチル)トリメリテート、1,3,5-トリス(4-ビニルオキシブチル)トリメリテート、ビス(4-(ビニルオキシ)ブチル)テレフタレート、ビス(4-(ビニルオキシ)ブチル)イソフタレート、エチレングリコールジビニルエーテル、1,4-ブタンジオールジビニルエーテル、テトラメチレングリコールジビニルエーテル、テトラエチレングリコールジビニルエーテル、ネオペンチルグリコールジビニルエーテル、トリメチロールプロパントリビニルエーテル、トリメチロールエタントリビニルエーテル、ヘキサンジオールジビニルエーテル、1,4-シクロヘキサンジオールジビニルエーテル、テトラエチレングリコールジビニルエーテル、ペンタエリスリトールジビニルエーテル、ペンタエリスリトールトリビニルエーテル及びシクロヘキサンジメタノールジビニルエーテルを挙げることができる。
これらの各種架橋剤から選択された1種類を添加してもよいし、2種以上を組合せて添加することもできる。前記架橋剤の含有割合は、本発明のレジスト下層膜形成組成物から後述する溶剤を除いた固形分に対して、例えば2質量%乃至60質量%である。
GPCカラム:TSKgel SuperMultipore〔登録商標〕Hz-N(東ソー(株))
カラム温度:40℃
溶媒:テトラヒドロフラン(THF)
流量:0.35ml/分
標準試料:ポリスチレン(東ソー(株))
窒素下、300mL四口フラスコに4,4’-ビフェノール(15.00g、0.0806mol、東京化成工業(株)製)、1-ピレンカルボキシアルデヒド(18.548g、0.0806mol、アルドリッチ社製)及びパラトルエンスルホン酸一水和物(33.2096g、0.0161mol、東京化成工業(株)製)を加え、さらにプロピレングリコールモノメチルエーテル(44.93g、関東化学(株)製)を仕込み、撹拌し、120℃まで昇温して溶解させ、重合を開始した。24時間後室温まで放冷し、メタノール(1800g、関東化学(株)製)中へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間乾燥し、目的とするポリマー(以下、本明細書では4,4’-BPOH-Pyと略称する。)19.08gを得た。4,4’-BPOH-Pyの、GPCによるポリスチレン換算で測定される重量平均分子量Mwは2200、多分散度Mw/Mnは2.10であった。本合成例で得られたポリマーは、式(1-4)で表される構造単位と式(1-76)で表される構造単位を有する。
窒素下、1000mL四口フラスコに2,2’-ビフェノール(70.00g、0.3759mol、東京化成工業(株)製)、1-ピレンカルボキシアルデヒド(86.559g、0.3759mol、アルドリッチ社製)及びメタンスルホン酸(10.8389g、0.1126mol、東京化成工業(株)製)を加え、さらにプロピレングリコールモノメチルエーテル(167.40g、関東化学(株)製)を仕込み、撹拌し、120℃まで昇温して溶解させ、重合を開始した。24時間後室温まで放冷し、メタノール(3000g、関東化学(株)製)中へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間乾燥し、目的とするポリマー(以下、本明細書では2,2’-BPOH-Pyと略称する。)84.1gを得た。2,2’-BPOH-Pyの、GPCによるポリスチレン換算で測定される重量平均分子量Mwは1400、多分散度Mw/Mnは1.49であった。本合成例で得られたポリマーは、式(1-16)で表される構造単位と式(1-88)で表される構造単位を有する。
窒素下、200mL四口フラスコに4,4’-チオジフェノール(12.50g、0.0573mol、東京化成工業(株)製)、1-ピレンカルボキシアルデヒド(13.19g、0.0573mol、東京化成工業(株)製)及びメタンスルホン酸(1.1008g、0.0115mol、関東化学(株)製)を加え、さらにプロピレングリコールモノメチルエーテル(32.74g、関東化学(株)製)を仕込み、撹拌し、120℃まで昇温して溶解させ、重合を開始した。24時間後室温まで放冷し、メタノール(1000g、関東化学(株)製)中へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間さらに120℃、24時間乾燥し、目的とするポリマー(以下、本明細書ではTDP-Pyと略称する。)11.6gを得た。TDP-Pyの、GPCによるポリスチレン換算で測定される重量平均分子量Mwは1010、多分散度Mw/Mnは1.67であった。本合成例で得られたポリマーは、式(1-28)で表される構造単位と式(1-100)で表される構造単位を有する。
窒素下、300mL四口フラスコに4,4’-ビフェノール(10.00g、0.0537mol、東京化成工業(株)製)、1-ピレンカルボキシアルデヒド(24.731g、0.1074mol、アルドリッチ社製)及びパラトルエンスルホン酸一水和物(4.2795g、0.0215mol、東京化成工業(株)製)を加え、さらにプロピレングリコールモノメチルエーテル(47.68g、関東化学(株)製)を仕込み、撹拌し、120℃まで昇温して溶解させ、重合を開始した。24時間後室温まで放冷し、メタノール(1800g、関東化学(株)製)中へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間乾燥し、目的とするポリマー(以下、本明細書では4,4’-BPOH-Py2と略称する。)21.58gを得た。4,4’-BPOH-Py2の、GPCによるポリスチレン換算で測定される重量平均分子量Mwは2180、多分散度Mw/Mnは2.11であった。本合成例で得られたポリマーは、式(1-40)で表される構造単位を有する。
窒素下、1000mL四口フラスコに2,2’-ビフェノール(25.00g、0.1343mol、東京化成工業(株)製)、1-ピレンカルボキシアルデヒド(61.828g、0.2685mol、アルドリッチ社製)及びメタンスルホン酸(7.7421g、0.0806mol、東京化成工業(株)製)を加え、さらにプロピレングリコールモノメチルエーテル(94.57g、関東化学(株)製)を仕込み、撹拌し、120℃まで昇温して溶解させ、重合を開始した。24時間後室温まで放冷し、メタノール(3000g、関東化学(株)製)中へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間乾燥し、目的とするポリマー(以下、本明細書では2,2’-BPOH-Py2と略称する。)68.22gを得た。2,2’-BPOH-Py2の、GPCによるポリスチレン換算で測定される重量平均分子量Mwは1270、多分散度Mw/Mnは1.77であった。本合成例で得られたポリマーは、式(1-52)で表される構造単位を有する。
窒素下、200mL四口フラスコに4,4’-チオジフェノール(8.00g、0.0367mol、東京化成工業(株)製)、1-ピレンカルボキシアルデヒド(16.88g、0.0773mol、東京化成工業(株)製)及びメタンスルホン酸(1.4090g、0.0147mol、関東化学(株)製)を加え、さらにプロピレングリコールモノメチルエーテル(32.13g、関東化学(株)製)を仕込み、撹拌し、120℃まで昇温して溶解させ、重合を開始した。24時間後室温まで放冷し、メタノール(1000g、関東化学(株)製)中へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間さらに120℃、24時間乾燥し、目的とするポリマー(以下、本明細書ではTDP-Py2と略称する。)13.2gを得た。TDP-Py2の、GPCによるポリスチレン換算で測定される重量平均分子量Mwは1100、多分散度Mw/Mnは1.64であった。本合成例で得られたポリマーは、式(1-64)で表される構造単位を有する。
窒素下、500mL四口フラスコに4,4’-ビフェノール(30.00g、0.1611mol、東京化成工業(株)製)、1-ナフトアルデヒド(50.324g、0.3222mol、アルドリッチ社製)及びパラトルエンスルホン酸一水和物(12.8384g、0.0644mol、東京化成工業(株)製)を加え、さらにプロピレングリコールモノメチルエーテル(113.87g、関東化学(株)製)を仕込み、撹拌し、120℃まで昇温して溶解させ、重合を開始した。24時間後室温まで放冷し、メタノール/純水=80/20(3000g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間乾燥し、目的とするポリマー(以下、本明細書では4,4’-BPOH-Np2と略称する。)21.08gを得た。4,4’-BPOH-Np2の、GPCによるポリスチレン換算で測定される重量平均分子量Mwは2450、多分散度Mw/Mnは2.03であった。本合成例で得られたポリマーは、式(1-38)で表される構造単位を有する。
窒素下、100mL四口フラスコに2,2’-ビフェノール(7.50g、0.0403mol、東京化成工業(株)製)、1-ナフトアルデヒド(12.581g、0.0806mol、アルドリッチ社製)及びメタンスルホン酸(1.5484g、0.0161mol、東京化成工業(株)製)を加え、さらにプロピレングリコールモノメチルエーテル(26.43g、関東化学(株)製)を仕込み、撹拌し、120℃まで昇温して溶解させ、重合を開始した。24時間後室温まで放冷し、メタノール(800g、関東化学(株)製)中へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間乾燥し、目的とするポリマー(以下、本明細書では2,2’-BPOH-Np2と略称する。)5.87gを得た。2,2’-BPOH-Np2の、GPCによるポリスチレン換算で測定される重量平均分子量Mwは1690、多分散度Mw/Mnは2.27であった。本合成例で得られたポリマーは、式(1-50)で表される構造単位を有する。
窒素下、200mL四口フラスコに4,4’-チオジフェノール(10.00g、0.0458mol、東京化成工業(株)製)、1-ナフトアルデヒド(14.311g、0.0916mol、東京化成工業(株)製)及びメタンスルホン酸(1.7613g、0.0183mol、関東化学(株)製)を加え、さらにプロピレングリコールモノメチルエーテル(31.87g、関東化学(株)製)を仕込み、撹拌し、120℃まで昇温して溶解させ、重合を開始した。24時間後室温まで放冷し、メタノール(1000g、関東化学(株)製)中へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間さらに120℃、24時間乾燥し、目的とするポリマー(以下、本明細書ではTDP-Np2と略称する。)6.13gを得た。TDP-Np2の、GPCによるポリスチレン換算で測定される重量平均分子量Mwは1090、多分散度Mw/Mnは1.49であった。本合成例で得られたポリマーは、式(1-62)で表される構造単位を有する。
窒素下、100mL四口フラスコに2,2’-ビフェノール(25.00g、0.1343mol、東京化成工業(株)製)、1-ナフトアルデヒド(10.484g、0.0671mol、アルドリッチ社製)、1-ピレンカルボキシアルデヒド(15.457g、0.0671mol、東京化成工業(株)製)及びメタンスルホン酸(3.871g、0.0403mol、東京化成工業(株)製)を加え、さらにプロピレングリコールモノメチルエーテル(54.81g、関東化学(株)製)を仕込み、撹拌し、120℃まで昇温して溶解させ、重合を開始した。24時間後室温まで放冷し、メタノール(2500g、関東化学(株)製)中へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間乾燥し、目的とするポリマー(以下、本明細書では2,2’-BPOH-NpPcAと略称する。)28.02gを得た。2,2’-BPOH-NpPcAの、GPCによるポリスチレン換算で測定される重量平均分子量Mwは2000、多分散度Mw/Mnは2.12であった。本合成例で得られたポリマーは、式(1-14)、(1-16)、(1-86)、(1-88)で表される構造単位を有すると推定される。
窒素下、100mL四口フラスコに1,1-ビス(4-ヒドロキシフェニル)シクロヘキサン(6.00g、0.0224mol、東京化成工業(株)製)、ホルムアルデヒド36%溶液(1.87g、0.0224mol、東京化成工業(株)製)及びメタンスルホン酸(0.1075g、0.0011mol、東京化成工業(株)製)を加え、さらにプロピレングリコールモノメチルエーテル(6.69g、関東化学(株)製)を仕込み、撹拌し、120℃まで昇温して溶解させ、重合を開始した。24時間後60℃まで放冷し、テトラヒドロフラン(13g、関東化学(株)製)を加え希釈し、メタノール(320g、関東化学(株)製)中へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、24時間乾燥し、目的とする下記式(3)で表される構造単位を有するポリマー(以下、本明細書ではBHPCH-FAと略称する。)4.45gを得た。BHPCH-FAの、GPCによるポリスチレン換算で測定される重量平均分子量Mwは10700、多分散度Mw/Mnは3.64であった。
窒素下、100mL四口フラスコにカルバゾール(6.69g、0.040mol、東京化成工業(株)製)、9-フルオレノン(7.28g、0.040mol、東京化成工業(株)製)及びパラトルエンスルホン酸一水和物(0.76g、0.0040mol、東京化成工業(株)製)を加え、さらに1,4-ジオキサン(6.69g、関東化学(株)製)を仕込み、撹拌し、100℃まで昇温して溶解させ、重合を開始した。24時間後60℃まで放冷し、クロロホルム(34g、関東化学(株)製)を加え希釈し、メタノール(168g、関東化学(株)製)中へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で80℃、24時間乾燥し、目的とする下記式(4)で表される構造単位を有するポリマー(以下、本明細書ではPCzFLと略称する。)9.37gを得た。PCzFLの、GPCによるポリスチレン換算で測定される重量平均分子量Mwは2800、多分散度Mw/Mnは1.77であった。
合成例1で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例1で得たポリマー20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、3,3’,5,5’-テトラメトキシメチル-4,4’-ジヒドロキシビフェニル)2.0g、触媒として熱酸発生剤TAG-2689(King社製、トリフルオロメタンスルホン酸の第4級アンモニウム塩)0.10g、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例2で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例2で得たポリマー20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、3,3’,5,5’-テトラメトキシメチル-4,4’-ジヒドロキシビフェニル)2.0g、触媒として熱酸発生剤TAG-2689(King社製、トリフルオロメタンスルホン酸の第4級アンモニウム塩)0.10g、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例3で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例3で得たポリマー20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、3,3’,5,5’-テトラメトキシメチル-4,4’-ジヒドロキシビフェニル)2.0g、触媒として熱酸発生剤TAG-2689(King社製、トリフルオロメタンスルホン酸の第4級アンモニウム塩)0.10g及び界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例4で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例4で得たポリマー20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、3,3’,5,5’-テトラメトキシメチル-4,4’-ジヒドロキシビフェニル)2.0g、触媒として熱酸発生剤TAG-2689(King社製、トリフルオロメタンスルホン酸の第4級アンモニウム塩)0.10g、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例5で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例5で得たポリマー20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、3,3’,5,5’-テトラメトキシメチル-4,4’-ジヒドロキシビフェニル)2.0g、触媒として熱酸発生剤TAG-2689(King社製、トリフルオロメタンスルホン酸の第4級アンモニウム塩)0.10g、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例6で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例6で得たポリマー20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、3,3’,5,5’-テトラメトキシメチル-4,4’-ジヒドロキシビフェニル)2.0g、触媒として熱酸発生剤TAG-2689(King社製、トリフルオロメタンスルホン酸の第4級アンモニウム塩)0.10g、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例7で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例7で得たポリマー20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、3,3’,5,5’-テトラメトキシメチル-4,4’-ジヒドロキシビフェニル)2.0g、触媒として熱酸発生剤TAG-2689(King社製、トリフルオロメタンスルホン酸の第4級アンモニウム塩)0.10g、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例8で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例8で得たポリマー20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、3,3’,5,5’-テトラメトキシメチル-4,4’-ジヒドロキシビフェニル)2.0g、触媒として熱酸発生剤TAG-2689(King社製、成分はトリフルオロメタンスルホン酸の第4級アンモニウム塩)0.10g、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例9で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例9で得たポリマー20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、3,3’,5,5’-テトラメトキシメチル-4,4’-ジヒドロキシビフェニル)2.0g、触媒として熱酸発生剤TAG-2689(King社製、トリフルオロメタンスルホン酸の第4級アンモニウム塩)0.10g、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例10で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
合成例10で得たポリマー20gに、架橋剤としてTMOM-BP(本州化学工業(株)製、3,3’,5,5’-テトラメトキシメチル-4,4’-ジヒドロキシビフェニル)2.0g、触媒として熱酸発生剤TAG-2689(King社製、トリフルオロメタンスルホン酸の第4級アンモニウム塩)0.10g、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、シクロヘキサノン88gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
市販のクレゾールノボラック樹脂(クレゾールとホルムアルデヒドを用いて得られたノボラック樹脂)20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。本比較例で使用したクレゾールノボラック樹脂の、GPCによるポリスチレン換算で測定される重量平均分子量Mwは4000、多分散度Mw/Mnは2.1であった。
比較合成例1で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
比較合成例2で得たポリマー20gに、界面活性剤としてメガファックR-30(DIC(株)製)0.06gを混合し、プロピレングリコールモノメチルエーテルアセテート80gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、リソグラフィープロセスに用いるレジスト下層膜形成組成物を調製した。
実施例1乃至実施例20及び比較例1で調製したレジスト下層膜形成組成物を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。ホットプレート上で400℃,2分間ベークし、レジスト下層膜(膜厚0.25μm)を形成した。このレジスト下層膜を、レジストに使用する溶剤である乳酸エチル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート及びシクロヘキサノンに浸漬し、それらの溶剤に不溶であることを確認した。
ドライエッチング速度の測定に用いたエッチャー及びエッチングガスは以下のものである。
エッチャー:ES401(日本サイエンティフィック(株)製)
エッチングガス:CF4
実施例1乃至実施例20、比較例1及び比較例2で調製したレジスト下層膜形成組成物を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。ホットプレート上で240℃,1分間、又は400℃,2分間ベークし、レジスト下層膜(膜厚0.25μm)を形成した。エッチングガスとしてCF4ガスを使用して、それらのレジスト下層膜のドライエッチング速度を測定した。また、フェノ-ルノボラック樹脂(市販品、GPCによるポリスチレン換算で測定される重量平均分子量Mwは2000、多分散度Mw/Mnは2.5)溶液を、スピンコーターを用いてシリコンウェハー上に塗布し、ホットプレート上で205℃,1分間ベークしてフェノールノボラック樹脂膜(膜厚0.25μm)を形成した。エッチングガスとしてCF4ガスを使用して、そのフェノールノボラック樹脂膜のドライエッチング速度を測定した。このフェノールノボラック樹脂膜のドライエッチング速度を1.00とした時の、実施例1乃至実施例20、比較例1及び比較例2で調製したレジスト下層膜形成組成物から形成したレジスト下層膜のドライエッチング速度を、ドライエッチング速度比として算出した結果を表1に示す。ドライエッチング速度比が小さいほど、CF4ガスに対する耐エッチング性が高いことを示す。
ドライエッチング速度比=(レジスト下層膜のドライエッチング速度)/(フェノ-ルノボラック樹脂膜のドライエッチング速度)
実施例1乃至実施例20及び比較例3で調製したレジスト下層膜形成組成物を、それぞれスピンコーターを用いてホールウェハー上に塗布した。ホットプレート上で400℃,2分間ベークし、レジスト下層膜(ホールパターン未形成部の膜厚0.25μm)を形成した。前記ホールウェハーとして、直径100nm、高さ400nmのホールパターンが形成されたウェハーを用いた。実施例1乃至実施例20で調製したレジスト下層膜形成組成物を、それぞれ上述のように塗布し、ベークした後の各ホールウェハーの断面を走査型電子顕微鏡(SEM)で観察した図1乃至図20に示す断面SEM写真から、ホール内部まで十分にレジスト下層膜で充填されていることが分かった。一方、比較例3で調製したレジスト下層膜形成組成物を、上述のように塗布し、ベークした後のホールウェハーの断面を走査型電子顕微鏡で観察した図21に示す断面SEM写真から、ホール内部に部分的に空洞が存在していることが分かった。
Claims (5)
- 下記式(1a)、式(1b)及び式(1c):
[式中、2つのR1はそれぞれ独立に炭素原子数1乃至10のアルキル基、炭素原子数2乃至6のアルケニル基、芳香族炭化水素基、ハロゲン原子、ニトロ基又はアミノ基を表し、2つのR2はそれぞれ独立に水素原子、炭素原子数1乃至10のアルキル基、炭素原子数2乃至6のアルケニル基、アセタール基、アシル基又はグリシジル基を表し、R3は置換基を有してもよい芳香族炭化水素基を表し、R4は水素原子、フェニル基又はナフチル基を表し、同一の炭素原子と結合するR3とR4がそれぞれフェニル基を表すとき互いに結合してフルオレン環を形成してもよく、式(1b)において2つのR3が表す基及び2つのR4が表す原子又は基は互いに異なっていてもよく、2つのkはそれぞれ独立に0又は1を表し、mは3乃至500の整数を表し、n、n1及びn2は2乃至500の整数を表し、pは3乃至500の整数を表し、Xは単結合又はヘテロ原子を表し、2つのQはそれぞれ独立に下記式(2):
(式中、2つのR1、2つのR2、2つのR3、2つのR4、2つのk、n1、n2及びXは式(1b)と同義であり、2つのQ1はそれぞれ独立に前記式(2)で表される構造単位を表す。)
で表される構造単位を表す。]
で表される繰り返し構造単位のうちいずれか1つ又は2つ以上を有するポリマー及び溶剤を含むレジスト下層膜形成組成物。 - 前記ポリマーは、少なくとも1種のビフェノール化合物又はビスフェノール化合物と少なくとも1種の芳香族アルデヒド又は芳香族ケトンとを、酸触媒の存在下、重合反応させて合成されるものである請求項1に記載のレジスト下層膜形成組成物。
- 前記R3が表す芳香族炭化水素基はフェニル基、ナフチル基、アントリル基又はピレニル基である請求項1に記載のレジスト下層膜形成組成物。
- 架橋剤、酸性化合物、熱酸発生剤及び界面活性剤のうち少なくとも1つをさらに含有する請求項1乃至請求項3のいずれか一項に記載のレジスト下層膜形成組成物。
- 請求項1乃至請求項4のいずれか一項に記載のレジスト下層膜形成組成物を段差、凹部及び/又は凸部を有する表面に塗布しベークすることにより第1のレジスト下層膜を形成する工程、前記第1のレジスト下層膜上にオルガノポリシロキサン膜を第2のレジスト下層膜として形成する工程、前記第2のレジスト下層膜上にレジストパターンを形成する工程、前記レジストパターンをマスクとして前記第2のレジスト下層膜をエッチングする工程、エッチング後の前記第2のレジスト下層膜のパターンをマスクとして前記第1のレジスト下層膜をエッチングする工程、及びエッチング後の前記第1のレジスト下層膜のパターンをマスクとして前記段差、凹部及び/又は凸部を有する表面をエッチングする工程を含む半導体装置の製造方法。
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Also Published As
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JPWO2014024836A1 (ja) | 2016-07-25 |
US9244353B2 (en) | 2016-01-26 |
KR20150043380A (ko) | 2015-04-22 |
KR101912677B1 (ko) | 2018-10-29 |
JP6191831B2 (ja) | 2017-09-06 |
US20150212418A1 (en) | 2015-07-30 |
TWI595322B (zh) | 2017-08-11 |
CN104508558A (zh) | 2015-04-08 |
TW201413394A (zh) | 2014-04-01 |
CN104508558B (zh) | 2016-07-06 |
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