WO2016047345A1 - マスクブランク、マスクブランクの製造方法及び転写用マスクの製造方法 - Google Patents
マスクブランク、マスクブランクの製造方法及び転写用マスクの製造方法 Download PDFInfo
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- WO2016047345A1 WO2016047345A1 PCT/JP2015/073892 JP2015073892W WO2016047345A1 WO 2016047345 A1 WO2016047345 A1 WO 2016047345A1 JP 2015073892 W JP2015073892 W JP 2015073892W WO 2016047345 A1 WO2016047345 A1 WO 2016047345A1
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Images
Classifications
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- 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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/162—Coating on a rotating support, e.g. using a whirler or a spinner
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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
- G03F7/16—Coating processes; Apparatus therefor
- G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking
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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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2004—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light
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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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
- G03F7/322—Aqueous alkaline compositions
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- 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
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- 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
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- 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
- H01L21/04—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
- H01L21/302—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to change their surface-physical characteristics or shape, e.g. etching, polishing, cutting
- H01L21/306—Chemical or electrical treatment, e.g. electrolytic etching
- H01L21/308—Chemical or electrical treatment, e.g. electrolytic etching using masks
- H01L21/3081—Chemical or electrical treatment, e.g. electrolytic etching using masks characterised by their composition, e.g. multilayer masks, materials
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- 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
- H01L21/04—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
- H01L21/3105—After-treatment
- H01L21/311—Etching the insulating layers by chemical or physical means
- H01L21/31105—Etching inorganic layers
- H01L21/31111—Etching inorganic layers by chemical means
- H01L21/31116—Etching inorganic layers by chemical means by dry-etching
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/281—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate
Definitions
- the present invention relates to a mask blank, a method for manufacturing a mask blank, and a method for manufacturing a transfer mask.
- a semiconductor pattern is formed using a photolithography method.
- a transfer mask is used in the pattern transfer process when the photolithography method is performed.
- the transfer mask is obtained by forming a predetermined transfer pattern on a thin film (for example, a light-shielding film or a hard mask film) provided on a substrate.
- the transfer pattern is formed by forming a resist film on the thin film, developing the resist film, and then patterning the thin film using the resist pattern obtained by development as a mask.
- a chemically amplified resist suitable for a fine processing technique is used.
- a chemically amplified resist generates an acid upon exposure, and the acid reacts with a functional group or a functional substance that controls the solubility of the polymer as a catalyst, thereby forming a positive or negative resist film. Since the chemically amplified resist has high sensitivity and resolution due to the acid-catalyzed reaction, a fine resist pattern can be formed.
- the acid generated in the resist film at the time of exposure is deactivated by inhibiting the reaction as a catalyst by the base component or diffusing to the thin film side.
- This tendency is particularly strong in the case of a thin film using chromium as a transition metal.
- the acid cannot sufficiently react when the resist film is exposed, so that the resolution of the resist pattern is lowered when the resist film is developed.
- a resist pattern is formed by removing a predetermined region of the resist film.
- a resist base film is provided, a region where the resist base film is removed and the resist base film is exposed, that is, the resist
- the resist film may remain in the space area of the pattern without being removed.
- the residue of the removed resist film is washed away with the cleaning liquid. If the cleaning liquid droplets remain in the space region, the residue may be deposited and reattached to the space region. . Residue of the resist film and re-deposition of the residue is caused by the high affinity between the resist film component and the resist underlayer film component and the high adhesion between them.
- an object of the present invention is to provide a mask blank in which foreign matter derived from a resist film hardly remains when developed and has few foreign matter defects, and a transfer mask having excellent pattern accuracy.
- the first configuration of the present invention is as follows. On the board A thin film for forming a transfer pattern; A resist underlayer film formed from a resist underlayer composition provided on the thin film and containing a polymer containing a unit structure having a lactone ring and a unit structure having a hydroxyl group; A resist film provided on the resist base film and formed from a resist composition; A mask blank provided with a mixed film which is provided so as to be interposed between the resist base film and the resist film and is formed from a mixed component including the resist base composition and the resist composition.
- the second configuration of the present invention is as follows: The mask blank according to the first configuration, wherein the polymer further includes a unit structure having an aryl group or an arylalkyl group.
- the third configuration of the present invention is: The mask blank of the 1st or 2nd structure obtained by copolymerizing the said polymer containing lactone (meth) acrylate and hydroxyalkyl (meth) acrylate.
- the fourth configuration of the present invention is as follows.
- the fifth configuration of the present invention is:
- the polymer is a polymer represented by the formula (1) including a unit structure of the formula (1-1) and a unit structure of the formula (1-2), or a unit structure of the formula (2-1) and the formula (2-
- R 1 , R 2 , R 3 , R 4 , and R 5 each represent a hydrogen atom or a methyl group
- L 2 and L 4 each represent a hydroxyalkyl group having 1 to 10 carbon atoms
- L 5 Represents a phenyl group or a benzyl group
- L 1 and L 3 represent the formula (L1-1) or the formula (L1-2), respectively.
- a dotted line shows the coupling
- the sixth configuration of the present invention is as follows.
- the polynuclear phenol is at least one of a compound represented by the formula (b-1), a compound represented by the formula (b-2), or a compound represented by the formula (b-3). It is a mask blank.
- each of R 11 is a hydrogen atom substituent of the benzene ring, and is a hydroxyl group, a halogen group, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
- arylalkyl groups having 7 to 25 carbon atoms alkylcarbonyl groups having 2 to 10 carbon atoms, alkylcarbonyloxy groups having 2 to 10 carbon atoms, alkylcarbonylamino groups having 2 to 10 carbon atoms, carbon atoms It is an organic group consisting of an aryloxyalkyl group having 7 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms or a combination thereof, and R 12 may be a single bond or a divalent to tetravalent group and substituted with a halogen atom.
- -M6 is an integer, and t is an integer of 1 to 4.
- the eighth configuration of the present invention is: The mask blank of any one of the first to seventh configurations, wherein the resist base composition further contains a crosslinkable compound.
- the ninth configuration of the present invention is: The mask blank according to any one of the first to eighth configurations, wherein the resist underlayer composition further contains an acid compound.
- the tenth configuration of the present invention is A thin film forming step of forming a thin film for forming a transfer pattern on the substrate; On the thin film, a resist base film forming step of forming a resist base film by applying and heating a resist base composition containing a polymer including a unit structure having a lactone ring and a unit structure having a hydroxyl group; A resist film forming step of forming a resist film by applying and heating a resist composition on the resist base film, and In the resist film forming step, A component in which the resist undercoat film is dissolved at the interface between the resist undercoat film and the applied resist composition by dissolving the surface layer portion of the resist undercoat film by applying the resist composition onto the resist undercoat film. And a mixed component in which the resist composition is mixed, It is a method for manufacturing a mask blank, in which the mixed component is heated together with the resist composition to form a mixed film interposed between the resist film and the resist base film and the resist film.
- the eleventh configuration of the present invention is A resist pattern forming step of forming a resist pattern by exposing and developing the resist film and the mixed film of the mask blank manufactured by the mask blank manufacturing method of the tenth configuration;
- the transfer mask manufacturing method includes a transfer pattern forming step of forming a transfer pattern on the substrate by etching the resist base film and the thin film using the resist pattern as a mask.
- a foreign substance derived from a resist film hardly remains when developed, and a mask blank with few foreign substance defects and a transfer mask with excellent pattern accuracy can be obtained.
- FIG. 2 is an electron micrograph of a resist pattern in a mask blank of Example 1.
- FIG. 2 is a pixel histogram of a mask blank of Example 1.
- FIG. 10 is a pixel histogram of a mask blank of Comparative Example 1.
- the present inventors have studied a technique for suppressing foreign matter defects that occur when a mask blank is developed. As a result, they have found that the resist underlayer film should be configured to be soluble in the resist composition.
- the resist underlayer should be difficult to dissolve in the resist composition. This is because if the resist underlayer easily dissolves in the resist composition, when the resist composition is applied onto the resist undercoat, the resist undercoat dissolves in the resist composition, and the dissolved components are dissolved in the resist composition. This is because intermixing (mixing) occurs. When intermixing occurs, the characteristics (for example, resolution) of the resulting resist film may be deteriorated.
- the resist underlayer film should be appropriately intermixed with the resist composition from the viewpoint of suppressing the remaining of foreign matters derived from the resist film.
- a mixed component in which a component in which the resist underlayer is dissolved and the resist composition can be formed at the interface between the resist underlayer and the resist composition.
- a mixed film composed of mixed components can be formed between the resist underlayer film and the resist film together with the resist film. That is, the mask blank can be configured by laminating a thin film, a resist underlayer film, a mixed film and a resist film in this order on the substrate.
- this mixed film contains the components of the resist film, it exhibits the same solubility as the resist film in the developer upon exposure. Further, since the mixed film contains a resist underlayer component that is insoluble in the developer, the mixed film has a slower elution rate (development rate) than the resist film.
- development rate elution rate
- the resist film is first eluted into the developer, and then the mixed film is eluted. As a result, even if the resist film does not elute and remains on the mixed film, or even if the residue from the resist film reattaches on the mixed film, the mixed film is located below the resist film.
- the residue of the resist film is washed away together. Therefore, in the mask blank provided with the mixed film, when the resist film is developed, it is possible to suppress the foreign matter remaining due to the residue of the resist film and to suppress the foreign matter defect in the resist pattern.
- the resist underlayer is made soluble in the resist composition in order to form a mixed film and foreign matter defects are suppressed, if the solubility of the resist underlayer in the resist composition is too high, Mixing occurs excessively and the resolution of the resist film is lowered. From this, it can be seen that, in order to suppress both the foreign substance defect and the decrease in resolution, it is preferable to configure the resist underlayer so as not to be excessively dissolved although it is soluble in the resist composition. Therefore, the present inventors have examined a resist underlayer composition that can form such a resist underlayer film.
- a resist base composition containing a polymer having a unit structure having a lactone ring and a unit structure having a hydroxyl group is preferable as the polymer.
- the present invention has been made based on the above findings.
- FIG. 1 is a schematic cross-sectional view of a mask blank according to an embodiment of the present invention.
- a binary mask blank that is a transmissive mask blank will be described as a mask blank.
- the mask blank 1 includes a thin film 11, a resist base film 12, and a resist film 13 on a substrate 10, and a space between the resist base film 12 and the resist film 13.
- a mixed film 14 is formed so as to intervene.
- a transparent substrate made of a material having translucency with respect to exposure light for example, synthetic quartz glass is used.
- the thin film 11 is for forming a transfer pattern.
- the thin film 11 is provided on the substrate 10.
- a light shielding film is formed as the thin film 11.
- the light shielding film is formed from, for example, a material containing chromium (Cr), a material containing transition metal and silicon (Si), or a material containing tantalum (Ta).
- the material containing a transition metal and silicon (Si) include a material containing at least one element of nitrogen, oxygen and carbon in addition to the transition metal and silicon in addition to the material containing the transition metal and silicon. .
- a transition metal silicide or a material containing a transition metal silicide nitride, oxide, carbide, oxynitride, carbonate, or carbonitride is preferable.
- the transition metal molybdenum, tantalum, tungsten, titanium, chromium, hafnium, nickel, vanadium, zirconium, ruthenium, rhodium, niobium, and the like are applicable. Of these, molybdenum is particularly preferred.
- the light shielding film may be a single layer or a plurality of layers (for example, a laminated structure of a light shielding layer and an antireflection layer). Further, when the light shielding film has a laminated structure of a light shielding layer and an antireflection layer, the light shielding layer may be composed of a plurality of layers.
- the resist base film 12 is provided on the thin film 11 and is a film for reducing the influence of a transition metal compound contained in the thin film 11, particularly chromium oxide, and suppressing the deactivation of the resist film 13. is there.
- the resist underlayer film 12 is formed from a resist underlayer composition containing a polymer including a unit structure having a lactone ring and a unit structure having a hydroxyl group.
- the resist underlayer film 12 formed from a predetermined resist underlayer composition is soluble in a resist composition described later and is configured not to cause excessive intermixing.
- the thickness of the resist underlayer 12 is, for example, not less than 1 nm and not more than 50 nm. Preferably they are 5 nm or more and 30 nm or less, More preferably, they are 8 nm or more and 20 nm or less.
- the resist film 13 has a predetermined resist pattern formed by development, and serves as a mask when the thin film 11 is etched and patterned.
- the resist film 13 is formed from a resist composition.
- the resist composition either a negative type or a positive type can be used.
- the resist composition includes, for example, a chemically amplified resist comprising a binder having a group that decomposes with an acid generator and an acid to change the alkali dissolution rate, an alkali-soluble binder, an acid generator, and an acid.
- Chemically amplified resist consisting of low-molecular compounds that change the dissolution rate, low-molecules that change the alkali dissolution rate of the resist by decomposition with an acid generator and acid and a binder having a group that changes the alkali dissolution rate by changing with an acid
- Chemically amplified resist composed of a compound, non-chemically amplified resist composed of a binder having a group that is decomposed by an electron beam to change the alkali dissolution rate, and non-bonded composed of a binder having a site that is cut by an electron beam to change the alkali dissolution rate A chemically amplified resist or the like can be used.
- the mixed film 14 is formed of a mixed component including a resist base composition that forms the resist base film 12 and a resist composition that forms the resist film 13.
- the mixed component is obtained by dissolving the surface layer portion 12a of the resist underlayer 12 with the resist composition, and the dissolved component (resist underlayer composition) and the resist composition.
- the mixed component is formed at the interface. Therefore, the mixed film 14 formed by heating the mixed component is formed so as to be interposed between the resist base film 12 and the resist film 13.
- the resist underlayer film 12 and the resist film 13 are integrally formed. That is, the resist film 13 is fixed on the resist base film 12 via the mixed film 14. Therefore, high adhesion between the resist base film 12 and the resist film 13 can be obtained.
- the mixed film 14 contains a component of the resist base film 12 (resist base composition) that is difficult to dissolve in the developer, the speed of elution into the developer (development speed) is lower than that of the resist film 13. It is configured.
- the mixed film 14 contains the components of the resist film 13, it exhibits the same solubility as the resist film 13 in the developer upon exposure.
- the mixed film 14 contains a positive resist component.
- This mixed film 14 has the same solubility as the positive resist in the developer, and the unexposed area becomes insoluble in the developer, and the exposed area becomes soluble in the developer.
- the mixed film 14 contains a negative resist component, so that the unexposed region of the mixed film 14 becomes soluble in the developer and is exposed. The area becomes insoluble in the developer.
- the mixed film 14 is formed so as to be thin because the resist base film 12 is formed of a polymer that does not excessively dissolve in the resist composition. That is, the resist underlayer 12 is not excessively dissolved when the resist composition is applied, and the mixed component is formed thin at the interface, so that the thickness of the mixed film 14 is reduced.
- the thickness of the mixed film 14 is preferably 0.1 nm or more and 10 nm or less, more preferably 0.1 nm or more and 5 nm or less.
- the resist underlayer composition for forming the resist underlayer 12 is obtained by dissolving a polymer containing a unit structure having a lactone ring and a unit structure having a hydroxyl group in a solvent.
- the resist underlayer composition may further contain a polynuclear phenol, a crosslinkable compound, an acid compound, an acid generator, other additives and the like as a crosslinking catalyst, if necessary.
- the resist underlayer composition is configured so that the solid content is 0.01% by mass to 50% by mass, preferably 0.1% by mass to 20% by mass, more preferably 0.1% by mass to 10% by mass. .
- solid content removes a solvent component from a resist base composition.
- each component will be described.
- the polymer includes a unit structure having a lactone ring and a unit structure having a hydroxyl group.
- Examples of the unit structure having a lactone ring include a unit structure having a ⁇ (gamma) butyrolactone ring having a five-membered ring structure and a unit structure having a ⁇ (delta) valerolactone ring having a six-membered ring structure.
- Preferred examples of the unit structure having a hydroxyl group include a hydroxyalkyl group.
- the alkyl group include straight-chain or branched alkyl groups having 1 to 10 carbon atoms. Examples thereof include straight chain alkyl groups such as methyl, ethyl, normal propyl, and normal butyl, branched alkyl groups such as isopropyl, isobutyl, and 2-ethylhexyl, and alicyclic alkyl groups such as cyclopentyl and cyclohexyl.
- hydroxyalkyl group examples include a hydroxymethyl group, a hydroxyethyl group, a hydroxynormalpropyl group, a hydroxynormalbutyl group, a hydroxyisopropyl group, a hydroxyisobutyl group, a hydroxy-2-ethylhexyl group, a hydroxycyclopentyl group, and a hydroxycyclohexyl group.
- a hydroxymethyl group a hydroxyethyl group, a hydroxynormalpropyl group, a hydroxynormalbutyl group, a hydroxyisopropyl group, a hydroxyisobutyl group, a hydroxy-2-ethylhexyl group, a hydroxycyclopentyl group, and a hydroxycyclohexyl group.
- the polymer preferably further includes a unit structure having an aryl group or an arylalkyl group.
- the aryl group is an aromatic group having 6 to 40 carbon atoms, and examples thereof include a phenyl group, a naphthyl group, and an anthryl group, and also includes a heterocyclic aromatic group such as a pyridyl, quinolinyl, and quinoxalinyl group.
- the arylalkyl group is an organic group in which the aryl group and the alkyl group are combined, and examples thereof include a benzyl group and an ethylphenyl group.
- a polymer containing a unit structure having a lactone ring and a unit structure having a hydroxyl group can be obtained, for example, by copolymerizing a lactone (meth) acrylate and a hydroxyalkyl (meth) acrylate.
- the polymer further including a unit structure having an aryl group or an arylalkyl group is obtained by copolymerizing, for example, lactone (meth) acrylate, hydroxyalkyl (meth) acrylate, and phenyl (meth) acrylate or benzyl (meth) acrylate. can get.
- the polymer is, for example, a polymer of the formula (1) including a unit structure of the formula (1-1) and a unit structure of the formula (1-2), or a unit structure of the formula (2-1) and the formula (2-2). And a polymer of the formula (2) containing a unit structure of the formula (2-3).
- R 1 , R 2 , R 3 , R 4 , and R 5 each represent a hydrogen atom or a methyl group, and L 2 and L 4 each have 1 to 10 carbon atoms.
- L 1 and L 3 represent formula (L1-1) or formula (L1-2), respectively.
- a dotted line represents a chemical bond with the ester group represented by the formula (1-1) and the formula (2-1).
- the molecular weight of the polymer varies depending on the coating solvent to be used, the solution viscosity, the film shape, etc., but the weight average molecular weight is 1,000 to 1,000,000, preferably 1,000 to 200,000, more preferably 1,000 to 100,000.
- the ⁇ -lactone used in the polymer is a lactone having a five-membered ring structure, and examples thereof include substituted and unsubstituted ⁇ -lactones such as ⁇ -butyrolactone and ⁇ -valerolactone.
- ⁇ -lactone is a lactone having a six-membered ring structure, and examples thereof include substituted and unsubstituted ⁇ -lactones such as ⁇ -valerolactone and ⁇ -caprolactone.
- the unit structure of formula (1-1) and the unit structure of formula (2-1) used for the polymer of formula (1), the polymer of formula (2) are, for example, acrylic acid, halogenated acrylic acid, methacrylic acid, etc. It can be produced by reacting an acrylic monomer with a lactone such as ⁇ -bromo- ⁇ -butyrolactone and ⁇ -bromo- ⁇ -valerolactone. Alternatively, it can be produced by reacting an acrylic polymer such as acrylic acid, halogenated acrylic acid or methacrylic acid with a lactone such as ⁇ -bromo- ⁇ -butyrolactone or ⁇ -bromo- ⁇ -valerolactone.
- Examples of the polymer of the formula (2) used in the present invention include a copolymer of ⁇ -butyrolactone methacrylate, hydroxyethyl methacrylate, and benzyl methacrylate.
- the polymer of the formula (1) has a unit structure of the formula (1-1) and a unit structure of the formula (1-2) in a total unit structure of 5 to 45:25 in the polymer of the formula (1). It can be contained in a proportion of ⁇ 60 mol%.
- the polymer of the formula (2) includes the unit structure of the formula (2-1), the unit structure of the formula (2-2), and the unit structure of the formula (2-3) in the polymer of the formula (2).
- the total unit structure may contain 5 to 45:25 to 60:10 to 45 mol%.
- the polymer of the formula (1) or the formula (2) is 20% by mass or more, for example, 20 to 100% by mass, or 30 to 100% by mass, or 50 to 99% by mass in the solid content in the resist base composition, or 60 to 98% by mass, or 80 to 98% by mass.
- the polymers of the formulas (1) and (2) may be random copolymers, block copolymers, or graft copolymers.
- the polymer contained in the resist underlayer composition can be synthesized by a method such as radical polymerization, anionic polymerization, or cationic polymerization.
- the form can be various methods such as solution polymerization, suspension polymerization, emulsion polymerization and bulk polymerization.
- the polymer can be further copolymerized with a non-crosslinkable monomer, which allows fine adjustment of the dry etching rate, reflectance, and the like.
- a copolymerization monomer include the following.
- it has one addition polymerizable unsaturated bond selected from acrylic acid esters, acrylamides, methacrylic acid esters, methacrylamides, allyl compounds, vinyl ethers, vinyl esters, styrenes, crotonic acid esters, etc.
- a compound is one addition polymerizable unsaturated bond selected from acrylic acid esters, acrylamides, methacrylic acid esters, methacrylamides, allyl compounds, vinyl ethers, vinyl esters, styrenes, crotonic acid esters, etc.
- acrylic acid esters examples include alkyl acrylates having 1 to 10 carbon atoms in the alkyl group.
- methacrylic acid esters examples include alkyl methacrylates having 1 to 10 carbon atoms in the alkyl group.
- Acrylamides include acrylamide, N-alkyl acrylamide, N-aryl acrylamide, N, N-dialkyl acrylamide, N, N-diaryl acrylamide, N-methyl-N-phenyl acrylamide, N-2-acetamide ethyl-N-. Examples include acetylacrylamide.
- methacrylamides include methacrylamide, N-alkylmethacrylamide, N-arylmethacrylamide, N, N-dialkylmethacrylamide, N, N-diarylmethacrylamide, N-methyl-N-phenylmethacrylamide, N- And ethyl-N-phenylmethacrylamide.
- vinyl ethers include alkyl vinyl ethers and vinyl aryl ethers.
- vinyl esters include vinyl butyrate, vinyl isobutyrate, and vinyl trimethyl acetate.
- styrenes examples include styrene, alkyl styrene, alkoxy styrene, halogenated styrene, and carboxy styrene.
- crotonic acid esters examples include alkyl crotonates such as butyl crotonate, hexyl crotonate, and glycerin monocrotonate.
- dialkyl itaconates, dialkyl esters or monoalkyl esters of maleic acid or fumaric acid, crotonic acid, itaconic acid, maleic anhydride, acrylonitrile, methacrylonitrile, maleilonitrile and the like can be mentioned.
- the resist base composition may contain a crosslinkable compound as a crosslinker.
- a crosslinkable compound By containing a crosslinkable compound, the polymer contained in the resist underlayer composition can be crosslinked.
- the resist underlayer 12 can be sufficiently polymerized, and the proportion of low molecular weight components that are easily dissolved in the resist composition in the resist underlayer 12 can be reduced. That is, the solubility of the resist underlayer 12 in the resist composition can be lowered, and excessive intermixing can be further suppressed.
- the mixed film 14 can be formed to a thin thickness of, for example, 10 nm or less, preferably 5 nm or less.
- the crosslinkable compound examples include melamine compounds and substituted urea compounds having a crosslink forming substituent such as a methylol group and a methoxymethyl group, and polymer compounds containing an epoxy group.
- it is a crosslinkable compound having at least two crosslink-forming substituents, such as methoxymethylated glycouril or methoxymethylated melamine, particularly preferably tetramethoxymethylglycoluril or hexamethoxymethylolmelamine It is.
- the addition amount of the crosslinkable compound varies depending on the solvent used, the substrate 10 used, the required solution viscosity, the required film shape, etc., but is 0.001 to 40% by mass or 0 based on the solid content.
- crosslinkable compounds may cause a crosslinking reaction by self-condensation, but if a crosslinking forming substituent is present in the polymer used in the resist underlayer composition, it may cause a crosslinking reaction with these crosslinking forming substituents. it can.
- the resist underlayer composition may contain polynuclear phenol.
- Polynuclear phenol may cause a crosslinking reaction by self-condensation, but reacts with a crosslinkable functional group (for example, hydroxyl group) in the polymer of formula (1) or formula (2) to form a three-dimensional crosslinked structure. To do. Therefore, by containing polynuclear phenol, the solubility of the resist underlayer 12 in the resist composition can be lowered, and excessive intermixing can be further suppressed.
- the polynuclear phenol has a phenol group, and the phenol group has at least one phenolic hydroxyl group.
- the polynuclear phenol is a compound having 2 to 30 phenolic hydroxyl groups, preferably 2 to 10 phenol groups in the molecule.
- Polynuclear phenol can be comprised from the part which has a phenol group, and can also be comprised from the combination of the part which has a phenol group, and parts other than a phenol group.
- the amount of polynuclear phenol added varies depending on the solvent used, the substrate 10 used, the required solution viscosity, the required film shape, etc., but is preferably 0.001 to 40% by mass relative to the solid content, or 0.01 to 30% by mass, or 0.1 to 25% by mass, or 0.1 to 10% by mass.
- polynuclear phenol for example, at least one of the formulas (b-1), (b-2) or (b-3) shown above can be used.
- each of R 11 is a hydrogen atom substituent of the benzene ring, and is a hydroxyl group, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, carbon Arylalkyl group having 7 to 25 atoms, alkylcarbonyl group having 2 to 10 carbon atoms, alkylcarbonyloxy group having 2 to 10 carbon atoms, alkylcarbonylamino group having 2 to 10 carbon atoms, 7 to 7 carbon atoms An organic group composed of 10 aryloxyalkyl groups, an alkoxy group having 1 to 6 carbon atoms, or a combination thereof.
- R 12 is a single bond, or a divalent to tetravalent hydrocarbon group having 1 to 10 carbon atoms that may be substituted with a halogen atom, and a divalent to tetravalent group that has 7 to 7 carbon atoms that may be substituted with a halogen atom.
- halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- halogen group examples include a fluorine group, a chlorine group, a bromine group, and an iodine group.
- alkyl group 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 group, cyclobutyl group, 1- Methyl-cyclopropyl group, 2-methyl-cyclopropyl group, n-pentyl group, 1-methyl-n-butyl group, 2-methyl-n-butyl group, 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-di
- the hydrocarbon group used for R 12 , R 15 , R 19 and R 20 is an organic group in which the alkyl group has a bivalent, divalent to tetravalent, or divalent to hexavalent valence.
- aryl group a phenyl group, o-methylphenyl group, m-methylphenyl group, p-methylphenyl group, o-chlorophenyl group, m-chlorophenyl group, p-chlorophenyl group, o-fluorophenyl group, p-fluorophenyl group, o-methoxyphenyl group, p-methoxyphenyl group, p-nitrophenyl group, p-cyanophenyl group, ⁇ -naphthyl group, ⁇ -naphthyl group, o-biphenylyl group, m-biphenylyl group, Examples thereof include p-biphenylyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group and 9-phenanthryl group.
- the arylalkyl group includes a benzyl group, o-methylbenzyl group, m-methylbenzyl group, p-methylbenzyl group, o-chlorobenzyl group, m-chlorobenzyl group, p-chlorobenzyl group, o-fluorobenzyl group.
- P-fluorobenzyl group o-methoxybenzyl group, p-methoxybenzyl group, p-nitrobenzyl group, p-cyanobenzyl group, phenethyl group, o-methylphenethyl group, m-methylphenethyl group, p-methylphenethyl group Group, o-chlorophenethyl group, m-chlorophenethyl group, p-chlorophenethyl group, o-fluorophenethyl group, p-fluorophenethyl group, o-methoxyphenethyl group, p-methoxyphenethyl group, p-nitrophenethyl group, p-cyanophenethyl group, 3-phenylpropyl group, 4-phenylbutyl 5-phenylpentyl group, 6-phenylhexyl group, ⁇ -naphthylmethyl group
- the arylalkyl group used for R 12 , R 15 , R 19 , and R 20 is an organic group in which the arylalkyl group has a bivalent, divalent to tetravalent, or divalent to hexavalent valence.
- alkylcarbonyl group examples include methylcarbonyl group, ethylcarbonyl group, n-propylcarbonyl group, i-propylcarbonyl group, cyclopropylcarbonyl group, n-butylcarbonyl group, i-butylcarbonyl group, s-butylcarbonyl group, t -Butylcarbonyl group, cyclobutylcarbonyl group, 1-methyl-cyclopropylcarbonyl group, 2-methyl-cyclopropylcarbonyl group, n-pentylcarbonyl group, 1-methyl-n-butylcarbonyl group, 2-methyl-n- Butylcarbonyl group, 3-methyl-n-butylcarbonyl group, 1,1-dimethyl-n-propylcarbonyl group, 1,2-dimethyl-n-propylcarbonyl group, 2,2-dimethyl-n-propylcarbonyl group, 1-ethyl-n-propylcarbony
- alkylcarbonyloxy group examples include a methylcarbonyloxy group, an ethylcarbonyloxy group, an n-propylcarbonyloxy group, an i-propylcarbonyloxy group, a cyclopropylcarbonyloxy group, an n-butylcarbonyloxy group, and an i-butylcarbonyloxy group.
- alkylcarbonylamino group examples include a methylcarbonylamino group, an ethylcarbonylamino group, an n-propylcarbonylamino group, an i-propylcarbonylamino group, a cyclopropylcarbonylamino group, an n-butylcarbonylamino group, and an i-butylcarbonylamino group.
- the aryloxyalkyl group includes phenyloxymethyl group, o-methylphenyloxyethyl group, m-methylphenyloxymethyl group, p-methylphenyloxypropyl group, o-chlorophenyloxymethyl group, m-chlorophenyloxyethyl group.
- Alkoxy groups include methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, 1-methyl- n-butoxy group, 2-methyl-n-butoxy group, 3-methyl-n-butoxy group, 1,1-dimethyl-n-propoxy group, 1,2-dimethyl-n-propoxy group, 2,2-dimethyl -N-propoxy group, 1-ethyl-n-propoxy group, n-hexyloxy group, 1-methyl-n-pentyloxy group, 2-methyl-n-pentyloxy group, 3-methyl-n-pentyloxy group 4-methyl-n-pentyloxy group, 1,1-dimethyl-n-butoxy group, 1,2-dimethyl-n-butoxy group, 1,3-dimethyl-n-butoxy group, 2,2-dimethyl- -Butoxy group, 2,3-dimethyl-n-butoxy group
- Examples of the compound of the formula (b-1) include the following.
- R 13 and R 14 in formula (b-2) are the same as R 11 in formula (b-1), respectively, and R 15 is a single bond or a carbon atom that is divalent to hexavalent and optionally substituted with a halogen atom.
- Examples of the compound of the formula (b-2) include the following compounds.
- R 16 , R 17 and R 18 in formula (b-3) are the same as R 11 in formula (b-1), respectively, and R 19 and R 20 are each a single bond or a divalent halogen atom.
- M4 and m6 are each an integer of 1 to 5, n5 is 0 ⁇ n5 ⁇ 4-m5, n4 and n6 are 0 ⁇ n4 ⁇ 5-m4 and 0 ⁇ n6 ⁇ 5-m6, respectively. It is an integer, and t represents an integer of 1 to 4.
- Examples of the compound of the formula (b-3) include the following compounds.
- cyclic compounds can also be used as polynuclear phenols.
- the polynuclear phenol is preferably the formula (b-2), and for example, bisphenol S represented by the formula (b-2-11) can be preferably exemplified.
- the resist underlayer composition may contain an acid compound as a catalyst for promoting the crosslinking reaction.
- Acid compounds include acidic compounds such as p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, sulfosalicylic acid, citric acid, benzoic acid, hydroxybenzoic acid and / or 2,4,4 Thermal acid generators such as 1,6-tetrabromocyclohexadienone, benzoin tosylate, and 2-nitrobenzyl tosylate can be used.
- the compounding amount of the acid compound is 0.02 to 10% by mass, preferably 0.04 to 5% by mass, based on the solid content.
- acid generator In order to make the resist underlayer composition have the same acidity as the resist film 13 coated on the upper layer in the lithography process, it is preferable to contain an acid generator that generates an acid by electron beam irradiation.
- Preferred acid generators include, for example, onium salt acid generators such as bis (4-tert-butylphenyl) iodonium trifluoromethanesulfonate, triphenylsulfonium trifluoromethanesulfonate, and phenyl-bis (trichloromethyl) -s-triazine.
- halogen-containing compound acid generators such as benzoin tosylate and sulfonic acid acid generators such as N-hydroxysuccinimide trifluoromethanesulfonate.
- the amount of the acid generator added is 0.02 to 3% by mass, preferably 0.04 to 2% by mass, based on the solid content.
- solvent A solvent will not be limited if a polymer can be dissolved and a resist base composition can be formed.
- the solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol.
- a high boiling point solvent such as propylene glycol monobutyl ether or propylene glycol monobutyl ether acetate can be mixed and used.
- a high boiling point solvent such as propylene glycol monobutyl ether or propylene glycol monobutyl ether acetate
- propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, ethyl lactate, butyl lactate, and cyclohexanone are preferable for improving the leveling property.
- the resist base composition may contain a rheology adjuster, an adhesion aid, a surfactant and the like as other additives.
- the rheology adjusting agent is added mainly for the purpose of improving the fluidity of the resist underlayer composition, and in particular for enhancing the filling property of the resist underlayer composition into the holes of the substrate 10 in the heating (baking) step.
- Specific examples include phthalic acid derivatives such as dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dihexyl phthalate, butyl isodecyl phthalate, adipic acid derivatives such as dinormal butyl adipate, diisobutyl adipate, diisooctyl adipate, octyl decyl adipate, Mention may be made of maleic acid derivatives such as normal butyl maleate, diethyl maleate and dinonyl maleate, oleic acid derivatives such as methyl oleate, butyl oleate and tetrahydrofurfuryl oleate, or stearic
- the adhesion aid is added mainly for the purpose of improving the adhesion between the resist underlayer film 12 and the substrate 10 or the resist film 13 and preventing the resist film 13 from being peeled off particularly during development.
- chlorosilanes such as trimethylchlorosilane, dimethylvinylchlorosilane, methyldiphenylchlorosilane, chloromethyldimethylchlorosilane, trimethylmethoxysilane, dimethyldiethoxysilane, methyldimethoxysilane, dimethylvinylethoxysilane, diphenyldimethoxysilane, Alkoxysilanes such as enyltriethoxysilane, hexamethyldisilazane, N, N′-bis (trimethylsilyl) urea, silazanes such as dimethyltrimethylsilylamine, trimethylsilylimidazole, vinyltrichlorosilane, ⁇ -chloropropyltrime
- a surfactant in order to further improve the applicability to surface unevenness without generating pinholes or installations.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, polyoxyethylene nonyl Polyoxyethylene alkyl allyl ethers such as phenol ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate Sorbitan fatty acid esters such as rate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sol
- Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as tan
- FIGS. 2 (a) to 2 (e) are cross-sectional views showing a manufacturing process of a mask blank according to an embodiment of the present invention.
- the thin film 11 for forming the transfer pattern 30 is formed on the substrate 10 by sputtering, for example.
- a resist base composition 12 ′ containing a polymer containing a unit structure having a lactone ring and a unit structure having a hydroxyl group is applied onto the thin film 11 by, for example, spin coating. .
- the resist base film 12 is formed by heating the resist base composition 12 '. Specifically, the resist base film 12 is formed by volatilizing the solvent contained in the resist base composition and crosslinking the polymer by heating. Since the resist underlayer 12 is formed of a polymer including a unit structure having a lactone ring and a unit structure having a hydroxyl group, it is soluble in the resist composition 13 ′ and does not cause excessive intermixing. It is configured.
- the resist underlayer composition 12 ′ is used. It is recommended that the temperature be raised from a low temperature to a high temperature and heated gently. Specifically, the temperature is raised from a temperature lower than the boiling point of the solvent contained in the resist base composition 12 '(for example, room temperature 23 ° C) to a temperature higher than the crosslinking start temperature at which the resist base composition 12' starts to crosslink. And heating at a high temperature. From the viewpoint of heating gently, the rate of temperature rise is preferably 80 ° C./min or less, more preferably 50 ° C./min or less.
- a resist composition 13 ′ is applied on the resist base film 12 by, for example, spin coating. Since the resist underlayer 12 is configured to be soluble in the resist composition 13 ′, the surface layer portion 12 a of the resist underlayer 12 is dissolved by the resist composition 13 ′. Thereby, at the interface between the resist underlayer film 12 and the resist composition 13 ′, a mixed component 14 ′ in which the component in which the surface layer portion 12a of the resist underlayer 12 is dissolved and the resist composition 13 ′ is mixed is formed. Become.
- the resist composition 13 ′ is heated to form a resist film 13.
- the mixed component 14 ′ is also heated and cross-linked at the same time to form the mixed film 14.
- the resist film 13 is formed integrally with the resist base film 12.
- the mask blank 1 of the present embodiment is obtained.
- FIGS. 3A to 3D are cross-sectional views showing the manufacturing process of the transfer mask 100 according to one embodiment of the present invention.
- the resist film 13 contains a positive resist component
- the resist film 13 and the mixed film 14 of the mask blank 1 are exposed so as to correspond to a predetermined transfer pattern 30.
- an exposed area (exposed area) becomes soluble in the developer, and an unexposed area (unexposed area) becomes insoluble in the developer.
- the exposed area becomes soluble in the developer and the unexposed area becomes insoluble in the developer.
- the resist film 13 is developed using a predetermined developer.
- the exposed area of the resist film 13 is eluted and removed, and the unexposed area of the resist film 13 remains without being eluted.
- the resist pattern 20 is formed.
- the mixed film 14 is also developed in the same manner as the resist film 13. That is, the space region T 1 of the mixed layer 14 is removed, the line region T 2 of the mixture film 14 remains without being removed.
- the resist film 13 is eluted into the developer.
- the resist base film 12 which is in the lower layer of the resist film 13 and has a slower elution rate into the developer than the resist film 13 is eluted into the developer. Therefore, in the space area T 1, or remaining on the mixed film 14 without the resist film 13 is dissolved, even when the omission scum of the resist film 13 or reattached onto the mixture film 14, the resist film
- the residue (foreign matter) of the resist film 13 is washed away together. That is, in the space area T 1, it is possible to suppress the remaining of foreign matter. As a result, it is possible to form a resist pattern 20 having a small line edge roughness and excellent pattern accuracy.
- Examples of the developer for the resist film 13 include inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, and aqueous ammonia, primary amines such as ethylamine and n-propylamine, and diethylamine.
- inorganic alkalis such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, and aqueous ammonia
- primary amines such as ethylamine and n-propylamine, and diethylamine.
- Secondary amines such as di-n-butylamine, tertiary amines such as triethylamine and methyldiethylamine, alcohol amines such as dimethylethanolamine and triethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide and choline
- An aqueous solution of an alkali such as a quaternary ammonium hydroxide, a cyclic amine such as pyrrole or piperidine, or the like can be used.
- an alcohol such as isopropyl alcohol or a nonionic surfactant may be added to the alkaline aqueous solution.
- preferred developers are quaternary ammonium hydroxides, more preferably tetramethylammonium hydroxide and choline.
- the resist base film 12 and the thin film 11 are etched using the predetermined resist pattern 20 as a mask.
- the thin film 11 is patterned by etching to form a predetermined transfer pattern 30. Since the transfer pattern 30 is formed using the resist pattern 20 having a small amount of foreign matter and having excellent pattern accuracy as a mask, there are few foreign matter defects. Therefore, the line edge roughness of the transfer pattern 30 is small and the pattern accuracy is excellent.
- the present invention is not limited to this. Even if the resist film 13 contains a negative resist component, the same effect can be obtained.
- the resist underlayer film 12 is formed from a resist underlayer composition containing a polymer including a unit structure having a lactone ring and a unit structure having a hydroxyl group. 12 and the resist film 13 are provided with a mixed film 14 formed of a mixed component 14 ′ including a resist underlayer composition and a resist composition. Since the mixed film 14 contains the component (resist composition) of the resist film 13, the mixed film 14 exhibits the same solubility as the resist film 13 in the developing solution upon exposure. Further, since the mixed film 14 includes the component of the resist underlayer film 12 (resist underlayer composition), the mixed film 14 is configured so that the rate of elution into the developer (development rate) is slower than that of the resist film 13.
- the space area T 1 when developing the resist film 13, the space area T 1, first, the resist film 13 is eluted, then mixed film 14 is to be eluted.
- the space area T 1 or remaining on the mixed film 14 resist film 13 without elution, even if omission scum of the resist film 13 as or redeposited on the mixed film 14
- the residue of the resist film 13 is washed away together. Therefore, by providing the mixed film 14, when the resist film 13 is developed, it is possible to suppress foreign matters derived from the resist film 13 from remaining in the space region T 1, and foreign matter defects in the resist pattern 20 can be suppressed.
- the resist film 13 and the resist base film 12 can be integrally formed. That is, the resist film 13 can be fixed on the resist base film 12 via the mixed film 14. Therefore, the adhesion between the resist base film 12 and the resist film 13 can be improved. Thereby, when the resist film 13 is developed and the resist pattern 20 is formed, the fall of the resist pattern 20 can be suppressed. More specifically, as shown in FIG. 3 (b), in the resist pattern 20, the width of the line region T 2 is narrowed due to the miniaturization, the width of the height of the line region T 2 (thickness) Therefore, the resist pattern 20 tends to fall down. In this respect, in this embodiment, since the resist film 13 is fixed to the resist base film 12 by the mixed film 14, the adhesion between the resist pattern 20 and the resist base film 12 is improved, and the resist pattern 20 is prevented from falling. Can be suppressed.
- the polymer contained in the resist underlayer composition further includes a unit structure having an aryl group or an arylalkyl group.
- the resist base composition contains polynuclear phenol. Thereby, a three-dimensional cross-linking structure is introduced into the resist underlayer 12, and excessive intermixing between the resist underlayer 12 and the resist composition can be further suppressed.
- the resist base composition contains a crosslinkable compound as a crosslinker.
- the resist underlayer 12 can be crosslinked to reduce the proportion of low molecular weight components in the resist underlayer 12. Thereby, the solubility with respect to the resist composition of the resist base film 12 can be lowered, and excessive intermixing can be further suppressed.
- the binary mask blank that is a transmissive mask blank has been described, but the present invention is not limited to this.
- a phase shift mask blank that is a transmission mask blank can be configured.
- the phase shift film is formed of a material containing silicon (Si) or a material containing a transition metal and silicon (Si).
- the phase shift film may be composed of a single layer or a plurality of layers.
- a substrate-engraved Levenson phase shift mask blank can be configured.
- a chromium-less type phase shift mask blank or a nanoimprint mold can be configured.
- an etching mask film may be provided on the light shielding film.
- the material of the etching mask film is selected from materials that are resistant to the etchant used when patterning the light shielding film.
- the material of the light shielding film is a material containing chromium (Cr)
- the material containing silicon (Si) is selected as the material of the etching mask film.
- the material of the light shielding film is a material containing silicon (Si) or a material containing a transition metal and silicon (Si)
- the material containing chromium (Cr) is used as the material of the etching mask film. Selected.
- the etching mask film may be composed of a single layer or a plurality of layers.
- a reflective mask blank for EUV exposure or the like can also be configured.
- a substrate made of a material having low thermal expansion is used as the substrate 10.
- SiO 2 —TiO 2 glass binary system (SiO 2 —TiO 2 ) and ternary system (SiO 2 —TiO 2 —SnO 2 etc.)
- SiO 2 —Al 2 O 3 —Li 2 O A substrate made of a crystallized glass of the system can be used.
- the multilayer reflective film used in the EUV light region includes a Ru / Si periodic multilayer film, a Mo / Be periodic multilayer film, a Mo compound / Si compound periodic multilayer film, and a Si / Nb film.
- Examples include periodic multilayer films, Si / Mo / Ru periodic multilayer films, Si / Mo / Ru / Mo periodic multilayer films, and Si / Ru / Mo / Ru periodic multilayer reflective films.
- Examples of the material for the protective film include Ru, Ru— (Nb, Zr, Y, B, Ti, La, Mo), Si— (Ru, Rh, Cr, B), Si, Zr, Nb, La. , B and the like. Among these, when a material containing Ru is applied, the reflectance characteristics of the multilayer reflective film become better.
- the material of the absorber film for example, Ta alone or a material mainly composed of Ta is used. The material mainly composed of Ta is usually an alloy of Ta.
- Such an absorber film preferably has an amorphous or microcrystalline structure in terms of smoothness and flatness.
- the material containing Ta as a main component include a material containing Ta and B, a material containing Ta and N, a material containing Ta and B, and further containing at least one of O and N, and a material containing Ta and Si.
- a material containing Ta, Si and N, a material containing Ta and Ge, a material containing Ta, Ge and N can be used.
- B, Si, Ge or the like an amorphous structure can be easily obtained and the smoothness can be improved.
- N and O are added to Ta, the resistance to oxidation is improved, so that the stability over time can be improved.
- the absorber film may be composed of a single layer or a plurality of layers.
- a resist underlayer composition was prepared using the polymer obtained in the synthesis example, and a mask blank and a transfer mask were prepared using the resist underlayer composition.
- Example 1> (Preparation of resist underlayer composition) 1 g of the resin obtained in Synthesis Example 1, 0.05 g of tetramethoxymethylglycoluril as a crosslinking agent, 0.003 g of pyridinium paratoluenesulfonic acid as a crosslinking catalyst, and 0.006 g of bis (4-hydroxyphenyl) sulfone as a pattern shape modifier Then, it was dissolved in 88.96 g of propylene glycol monomethyl ether and 10 g of propylene glycol monomethyl ether acetate as a solvent to obtain a resist base composition.
- a light semi-transmissive film, a light-shielding film, and a hard mask were formed as thin films on a light-transmitting substrate made of synthetic quartz glass by sputtering. Specifically, a single-layer MoSiN film (thickness: 69 nm) was formed as a light semi-transmissive film on a transparent substrate.
- a chromium (Cr) target is used as a sputtering target, and a mixed gas atmosphere of argon (Ar), carbon dioxide (CO 2 ), nitrogen (N 2 ), and helium (He) (gas pressure 0.2 Pa, gas flow rate)
- Ar argon
- CO 2 carbon dioxide
- N 2 nitrogen
- He helium
- the power of the DC power source is 1.7 kW
- a CrOCN layer having a film thickness of 14 nm is formed by reactive sputtering (DC sputtering).
- a chromium-based light shielding film was formed.
- This light-shielding film has a laminated structure with the light semi-transmissive film and is adjusted so that the optical density (OD) is 3.0 at a wavelength of 193 nm of ArF excimer laser exposure light.
- the surface reflectance of the light shielding film with respect to the wavelength of the exposure light was 20%.
- the HMDS process was performed on the surface of the formed thin film on predetermined conditions.
- the resist base composition prepared on the thin film was applied by spin coating. Thereafter, the resist underlayer composition (thickness 10 nm) was formed by heat-crosslinking the resist underlayer composition under predetermined conditions. Heating took 4 minutes to raise the temperature from room temperature (20 ° C.) to 200 ° C., followed by 6 minutes of heat treatment.
- Example 1 a chemically amplified resist (“SLV12M negative resist” manufactured by Fuji Film Electronics Materials Co., Ltd.) was applied on the resist underlayer by a spin coating method. Then, the resist film (thickness 160nm) was formed by heating at 130 degreeC for 10 minute (s). Simultaneously with the formation of the resist film, a mixed film interposed between the resist underlayer film and the resist film was formed. Thereby, the mask blank of Example 1 was obtained.
- SLV12M negative resist manufactured by Fuji Film Electronics Materials Co., Ltd.
- TMAH tetramethylamino hydride
- a thin film pattern was formed.
- the chromium-based light-shielding film was dry-etched with a mixed gas of chlorine and oxygen.
- the phase shift mask film was dry-etched with a fluorine-based gas (SF 6 gas).
- SF 6 gas fluorine-based gas
- ⁇ Resist pattern evaluation 2 Foreign matter defect> The foreign matter defect was determined by measuring a pixel histogram of the mask blank after formation of the resist pattern by an optical measurement method and checking for a defect (pixel) of 200 nm or more. In this example, as shown in FIG. 5, it was found that although the pixels due to the foreign substance defects were slightly confirmed, the density was very low.
- Example 2 to 6 the resist undercoat was obtained in the same manner as in Example 1 except that 1 g of the resin obtained in Synthesis Examples 2 to 6 was used instead of 1 g of the resin obtained in Synthesis Example 1.
- the composition was prepared to prepare a mask blank and a transfer mask.
- resolution was confirmed by setting the target line width to 100 nm line and space (L / S), and it was confirmed that the same results as in Example 1 were obtained.
- the foreign matter was confirmed using the pixel histogram, as in Example 1, only the low-density defect dispersion was confirmed.
- the boundary portion between the resist base film and the resist film of the mask blank with resist was examined, there was no clear boundary at the interface between the resist base film and the resist film, and a mixed region having a thickness of about 5 nm or less was confirmed.
- Comparative Example 1 a resist underlayer composition was prepared in the same manner as in Example 1 except that 1 g of the resin obtained in Comparative Synthesis Example 1 was used instead of 1 g of the resin obtained in Synthesis Example 1. Then, a mask blank and a transfer mask were produced. When the boundary between the resist base film and the resist film in the mask blank with resist was examined, a clear boundary was confirmed at the interface between the resist base film and the resist film. That is, in Comparative Example 1, it was confirmed that no mixed region was formed at the interface. Pattern collapse occurred in a line and space (L / S) with a target line width of 100 nm, and a clear pattern could not be formed. Further, when the foreign matter was confirmed using the pixel histogram, as shown in FIG. 6, a high-density defect was confirmed such that a defect that appears to be a foreign matter due to the resist residue continued on the streak.
- L / S line and space
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Abstract
Description
本発明の第1の構成は、
基板上に、
転写パターンを形成するための薄膜と、
前記薄膜上に設けられ、ラクトン環を有する単位構造及び水酸基を有する単位構造を含むポリマーを含有するレジスト下地組成物から形成されるレジスト下地膜と、
前記レジスト下地膜上に設けられ、レジスト組成物から形成されるレジスト膜と、
前記レジスト下地膜とレジスト膜との間に介在するように設けられ、前記レジスト下地組成物と前記レジスト組成物とを含む混合成分から形成される混合膜と、を備えるマスクブランクである。
本発明の第2の構成は、
前記ポリマーが、更にアリール基又はアリールアルキル基を有する単位構造を含む、第1の構成のマスクブランクである。
本発明の第3の構成は、
前記ポリマーが、ラクトン(メタ)アクリレート及びヒドロキシアルキル(メタ)アクリレートを含み共重合して得られる、第1または2の構成のマスクブランクである。
本発明の第4の構成は、
前記ポリマーが、ラクトン(メタ)アクリレート、ヒドロキシアルキル(メタ)アクリレート、及びフェニル(メタ)アクリレート又はベンジル(メタ)アクリレートを含み共重合して得られる、第1~3の構成のいずれかのマスクブランクである。
本発明の第5の構成は、
前記ポリマーが、式(1-1)の単位構造と式(1-2)の単位構造とを含む式(1)で示されるポリマー、又は式(2-1)の単位構造と式(2-2)の単位構造と式(2-3)の単位構造とを含む式(2)で示されるポリマーである、第1~4の構成のいずれかのマスクブランクである。
〔式中、R1、R2、R3、R4、及びR5はそれぞれ水素原子又はメチル基を示し、L2及びL4はそれぞれ炭素数1~10のヒドロキシアルキル基を示し、L5はフェニル基又はベンジル基を示し、L1及びL3はそれぞれ式(L1-1)又は式(L1-2)を示す。〕
〔式中、点線はポリマーの単位構造との結合を示す。〕
本発明の第6の構成は、
前記レジスト下地組成物が、更に多核フェノールを含有する、第1~5の構成のいずれかのマスクブランクである。
本発明の第7の構成は、
前記多核フェノールが、式(b-1)で示される化合物、式(b-2)で示される化合物、又は式(b-3)で示される化合物の少なくとも1つである、第6の構成のマスクブランクである。
(ただし、式(b-1)中でR11はそれぞれベンゼン環の水素原子の置換基であって、水酸基、ハロゲン基、炭素原子数1~10のアルキル基、炭素原子数6~18のアリール基、炭素原子数7~25のアリールアルキル基、炭素原子数2~10のアルキルカルボニル基、炭素原子数2~10のアルキルカルボニルオキシ基、炭素原子数2~10のアルキルカルボニルアミノ基、炭素原子数7~10のアリールオキシアルキル基、炭素数1~6のアルコキシ基又はそれらの組み合わせからなる有機基であり、R12は単結合、又は2~4価でハロゲン原子で置換されていても良い炭素原子数1~10の炭化水素基、2~4価でハロゲン原子で置換されていても良い炭素原子数7~25のアリールアルキル基、若しくはスルホニル基を示し、m1は1~5の整数であり、n1は0≦n1≦5-m1の整数であり、qは2~4の整数を示す。)
(ただし、式(b-2)中のR13及びR14はそれぞれ式(b-1)中のR11と同じあり、R15は単結合、又は2~6価でハロゲン原子で置換されていても良い炭素原子数1~10の炭化水素基、2~6価でハロゲン原子で置換されていても良い炭素原子数7~25のアリールアルキル基、若しくはスルホニル基を示し、m2及びm3はそれぞれ1~5の整数であり、n2及びn3は0≦n2≦5-m2、0≦n3≦5-m3の整数であり、k及びsはそれぞれ1~3の整数を示す。)
(ただし、式(b-3)中のR16、R17及びR18はそれぞれ式(b-1)中のR11と同じであり、R19及びR20はそれぞれ単結合、又は2価でハロゲン原子で置換されていても良い炭素原子数1~10の炭化水素基、2価でハロゲン原子で置換されていても良い炭素原子数7~25のアリールアルキル基、若しくはスルホニル基であり、m5は1~4の整数であり、m4及びm6はそれぞれ1~5の整数であり、n5は0≦n5≦4-m5、n4及びn6はそれぞれ0≦n4≦5-m4、0≦n6≦5-m6の整数であり、tは1~4の整数を示す。)
本発明の第8の構成は、
前記レジスト下地組成物が、更に架橋性化合物を含有する、第1~7の構成のいずれかのマスクブランクである。
本発明の第9の構成は、
前記レジスト下地組成物が、更に酸化合物を含有する、第1~8の構成のいずれかのマスクブランクである。
本発明の第10の構成は、
基板上に、転写パターンを形成するための薄膜を形成する薄膜形成工程と、
前記薄膜上に、ラクトン環を有する単位構造及び水酸基を有する単位構造を含むポリマーを含有するレジスト下地組成物を塗布し、加熱することにより、レジスト下地膜を形成するレジスト下地膜形成工程と、
前記レジスト下地膜上にレジスト組成物を塗布し、加熱することにより、レジスト膜を形成するレジスト膜形成工程と、を有し、
前記レジスト膜形成工程では、
前記レジスト下地膜上に前記レジスト組成物を塗布することで前記レジスト下地膜の表層部を溶解させ、前記レジスト下地膜と塗布した前記レジスト組成物との界面に、前記レジスト下地膜が溶解した成分と前記レジスト組成物とが混合した混合成分を形成し、
前記レジスト組成物と共に前記混合成分を加熱することにより、前記レジスト膜と、前記レジスト下地膜と前記レジスト膜との間に介在する混合膜を形成する、マスクブランクの製造方法である。
本発明の第11の構成は、
第10の構成のマスクブランクの製造方法によって製造されたマスクブランクの前記レジスト膜および前記混合膜を露光・現像することによりレジストパターンを形成するレジストパターン形成工程と、
前記レジストパターンをマスクとして前記レジスト下地膜および前記薄膜をエッチングすることにより前記基板上に転写パターンを形成する転写パターン形成工程を有する、転写用マスクの製造方法である。
本実施形態のマスクブランクについて、図1を用いて説明する。図1は、本発明の一実施形態に係るマスクブランクの概略断面図である。なお、以下では、マスクブランクとして、透過型マスクブランクであるバイナリマスクブランクについて説明する。
基板10としては、バイナリマスクブランクの場合、露光光に対して透光性を有する材料、例えば合成石英ガラスからなる透明基板が用いられる。
薄膜11は、転写パターンを形成するためのものである。薄膜11は、基板10上に設けられている。バイナリマスクブランクの場合、薄膜11として遮光膜が形成される。遮光膜は、例えば、クロム(Cr)を含有する材料、遷移金属とケイ素(Si)を含有する材料、タンタル(Ta)を含有する材料から形成される。遷移金属とケイ素(Si)を含有する材料としては、遷移金属とケイ素を含有する材料のほかに、遷移金属及びケイ素に、さらに窒素、酸素及び炭素のうち少なくとも1つの元素を含む材料が挙げられる。具体的には、遷移金属シリサイド、または遷移金属シリサイドの窒化物、酸化物、炭化物、酸窒化物、炭酸化物、あるいは炭酸窒化物を含む材料が好適である。遷移金属には、モリブデン、タンタル、タングステン、チタン、クロム、ハフニウム、ニッケル、バナジウム、ジルコニウム、ルテニウム、ロジウム、ニオブ等が適用可能である。この中でも特にモリブデンが好適である。なお、遮光膜は、単層でも複数層(例えば遮光層と反射防止層との積層構造)としてもよい。また、遮光膜を遮光層と反射防止層との積層構造とする場合、この遮光層を複数層からなる構造としてもよい。
レジスト下地膜12は、薄膜11上に設けられており、薄膜11に含有される遷移金属化合物、特に、酸化クロム等の影響を低減してレジスト膜13の失活化を抑制するための膜である。レジスト下地膜12は、詳細を後述するように、ラクトン環を有する単位構造及び水酸基を有する単位構造を含むポリマーを含有するレジスト下地組成物から形成されている。所定のレジスト下地組成物から形成されるレジスト下地膜12は、後述するレジスト組成物に対して可溶であり、かつ過度なインターミキシングを起こさないように構成されている。
レジスト膜13は、現像により所定のレジストパターンが形成され、薄膜11をエッチングしてパターニングする際のマスクとなるものである。レジスト膜13は、レジスト組成物から形成されている。
混合膜14は、レジスト下地膜12を形成するレジスト下地組成物と、レジスト膜13を形成するレジスト組成物と、を含む混合成分から形成されている。混合成分は、レジスト下地膜12上にレジスト組成物が塗布されたときに、レジスト下地膜12の表層部12aがレジスト組成物により溶解し、その溶解した成分(レジスト下地組成物)とレジスト組成物とがインターミキシング(混合)することで形成される。この混合はレジスト下地膜12と塗布されたレジスト組成物との界面で生じるため、混合成分は界面に形成される。したがって、混合成分が加熱されて形成される混合膜14は、レジスト下地膜12とレジスト膜13との間に介在するように形成されることになる。
レジスト下地膜12を形成するレジスト下地組成物は、ラクトン環を有する単位構造及び水酸基を有する単位構造を含むポリマーが溶剤に溶解されたものである。レジスト下地組成物は、必要に応じて、多核フェノールや架橋性化合物、架橋触媒として酸化合物、酸発生剤、その他添加剤等を更に含有してもよい。レジスト下地組成物は、固形分が0.01質量%~50質量%、好ましくは0.1質量%~20質量%、より好ましくは0.1質量%~10質量%となるように構成される。なお、固形分とは、レジスト下地組成物から溶剤成分を取り除いたものである。以下、各成分について説明する。
ポリマーは、ラクトン環を有する単位構造及び水酸基を有する単位構造を含む。
式(2)のポリマーは、式(2-1)の単位構造と式(2-2)の単位構造と式(2-3)の単位構造とを、式(2)のポリマー中に含まれる全単位構造中で5~45:25~60:10~45のモル%の割合で含有することができる。
レジスト下地組成物には、架橋剤として架橋性化合物を含有させるとよい。架橋性化合物を含有させることで、レジスト下地組成物に含まれるポリマーを架橋させることができる。これによりレジスト下地膜12を十分に重合させることができ、レジスト下地膜12において、レジスト組成物に溶解しやすい低分子量成分の割合を低減することができる。つまり、レジスト下地膜12のレジスト組成物に対する溶解性を低くし、過度なインターミキシングをさらに抑制できる。このようにレジスト下地膜12を架橋することによって、混合膜14を、例えば10nm以下、好ましくは5nm以下の薄い厚さに形成することができる。
レジスト下地組成物には、多核フェノールを含有させるとよい。多核フェノールは、自己縮合による架橋反応を起こすこともあるが、式(1)又は式(2)のポリマー中の架橋性官能基(例えば、水酸基)に反応し、三次元的な架橋構造を形成する。そのため、多核フェノールを含有させることで、レジスト下地膜12のレジスト組成物に対する溶解性を低くし、過度なインターミキシングをさらに抑制できる。
レジスト下地組成物には、架橋反応を促進するための触媒として酸化合物を含有させるとよい。酸化合物としては、p-トルエンスルホン酸、トリフルオロメタンスルホン酸、ピリジニウムp-トルエンスルホン酸、サリチル酸、スルホサリチル酸、クエン酸、安息香酸、ヒドロキシ安息香酸などの酸性化合物又は/及び、2,4,4,6-テトラブロモシクロヘキサジエノン、ベンゾイントシラート、2-ニトロベンジルトシラート等の熱酸発生剤を用いることができる。酸化合物の配合量は固形分当たり、0.02~10質量%、好ましくは0.04~5質量%である。
レジスト下地組成物には、リソグラフィー工程で上層に被覆されるレジスト膜13との酸性度を一致させるため、電子線照射により酸を発生する酸発生剤を含有させるとよい。好ましい酸発生剤としては、例えば、ビス(4-tert-ブチルフェニル)ヨードニウムトリフルオロメタンスルホネート、トリフェニルスルホニウムトリフルオロメタンスルホネート等のオニウム塩系酸発生剤類、フェニル-ビス(トリクロロメチル)-s-トリアジン等のハロゲン含有化合物系酸発生剤類、ベンゾイントシレート、N-ヒドロキシスクシンイミドトリフルオロメタンスルホネート等のスルホン酸系酸発生剤類等が挙げられる。上記酸発生剤の添加量は固形分当たり0.02~3質量%、好ましくは0.04~2質量%である。
溶剤は、ポリマーを溶解させ、レジスト下地組成物を形成できるものであれば、限定されない。溶剤としては、例えば、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、メチルセロソルブアセテート、エチルセロソルブアセテート、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、プロピレングリコール、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、プロピレングリコールプロピルエーテルアセテート、トルエン、キシレン、メチルエチルケトン、シクロペンタノン、シクロヘキサノン、2ーヒドロキシプロピオン酸エチル、2ーヒドロキシー2ーメチルプロピオン酸エチル、エトシキ酢酸エチル、ヒドロキシ酢酸エチル、2ーヒドロキシー3ーメチルブタン酸メチル、3ーメトキシプロピオン酸メチル、3ーメトキシプロピオン酸エチル、3ーエトキシプロピオン酸エチル、3ーエトキシプロピオン酸メチル、ピルビン酸メチル、ピルビン酸エチル、酢酸エチル、酢酸ブチル、乳酸エチル、乳酸ブチル、等を用いることができる。これらの有機溶剤は単独で、または2種以上を組合せて使用される。
レジスト下地組成物には、その他の添加剤として、レオロジー調整剤、接着補助剤、界面活性剤などを含有させてもよい。
次に、上述のマスクブランク1の製造方法について図2(a)~(e)を参照しながら説明する。図2(a)~(e)は、本発明の一実施形態に係るマスクブランクの製造工程を示す断面図である。
まず、図2(a)に示すように、例えばスパッタリング法により、基板10上に、転写パターン30を形成するための薄膜11を形成する。
次に、図2(b)に示すように、薄膜11上に、例えばスピンコートにより、ラクトン環を有する単位構造及び水酸基を有する単位構造を含むポリマーを含有するレジスト下地組成物12´を塗布する。
続いて、図2(d)に示すように、レジスト下地膜12上に、例えばスピンコートによりレジスト組成物13´を塗布する。レジスト下地膜12はレジスト組成物13´に可溶となるように構成されているため、レジスト下地膜12の表層部12aがレジスト組成物13´により溶解する。これにより、レジスト下地膜12とレジスト組成物13´との界面において、レジスト下地膜12の表層部12aが溶解した成分とレジスト組成物13´とが混合した混合成分14´が形成されることになる。
次に、本実施形態の転写用マスク100およびその製造方法について図3(a)~(d)を参照しながら説明する。図3(a)~(d)は、本発明の一実施形態に係る転写用マスク100の製造工程を示す断面図である。なお、以下では、レジスト膜13がポジ型のレジスト成分を含有する場合について説明する。
まず、図3(a)に示すように、マスクブランク1のレジスト膜13および混合膜14に対し、所定の転写パターン30に対応するように露光を行う。レジスト膜13は、露光された領域(露光領域)が現像液に対して可溶となり、露光されない領域(未露光領域)が現像液に対して不溶となる。また同様に、レジスト膜13の成分を含む混合膜14は、露光領域が現像液に対して可溶となり、未露光領域が現像液に対して不溶となる。
続いて、所定の現像液を用いてレジスト膜13を現像する。現像により、図3(b)に示すように、レジスト膜13の露光領域が溶出して除去され、レジスト膜13の未露光領域が溶出せずに残存する。これにより、レジストパターン20が形成される。レジストパターン20においては、レジスト膜13が除去された領域がスペース領域T1となり、レジスト膜13が残存した領域がライン領域T2となる。また現像工程では、レジスト膜13と同様に混合膜14も現像される。すなわち、混合膜14のスペース領域T1は除去され、混合膜14のライン領域T2は除去されずに残存する。
続いて、図3(c)に示すように、所定のレジストパターン20をマスクとして、レジスト下地膜12および薄膜11をエッチングする。エッチングにより、薄膜11をパターニングして所定の転写パターン30を形成する。転写パターン30は、異物の残存が少なく、パターン精度に優れるレジストパターン20をマスクとして形成されているので、異物欠陥が少ない。そのため、転写パターン30のラインエッジラフネスは小さく、パターン精度に優れている。
最後に、図3(d)に示すように、レジストパターン20などを剥離除去することにより、本実施形態の転写用マスク100を得る。
本実施形態によれば、以下に示す1つ又は複数の効果を奏する。
上述の実施形態では、透過型マスクブランクであるバイナリマスクブランクについて説明したが、本発明はこれに限定されない。基板10上に、薄膜11として、例えば位相シフト膜、あるいは位相シフト膜および遮光膜を設けることにより、透過型マスクブランクである位相シフト型マスクブランクを構成することもできる。位相シフト膜は、ケイ素(Si)を含有する材料、あるいは遷移金属とケイ素(Si)を含有する材料等により形成される。なお、位相シフト膜は、単層または複数層で構成されてもよい。
EUV光の領域で使用される多層反射膜としては、Mo/Si周期多層膜のほかに、Ru/Si周期多層膜、Mo/Be周期多層膜、Mo化合物/Si化合物周期多層膜、Si/Nb周期多層膜、Si/Mo/Ru周期多層膜、Si/Mo/Ru/Mo周期多層膜、Si/Ru/Mo/Ru周期多層反射膜が挙げられる。
また、保護膜の材料としては、例えば、Ru、Ru-(Nb、Zr、Y、B、Ti、La、Mo)、Si-(Ru、Rh、Cr、B)、Si、Zr、Nb、La、B等の材料から選択される。これらのうち、Ruを含む材料を適用すると、多層反射膜の反射率特性がより良好となる。
また、吸収体膜の材料としては、例えば、Ta単体、Taを主成分とする材料が用いられる。Taを主成分とする材料は、通常、Taの合金である。このような吸収体膜の結晶状態は、平滑性、平坦性の点から、アモルファス状又は微結晶の構造を有しているものが好ましい。Taを主成分とする材料としては、例えば、TaとBを含む材料、TaとNを含む材料、TaとBを含み、更にOとNの少なくともいずれかを含む材料、TaとSiを含む材料、TaとSiとNを含む材料、TaとGeを含む材料、TaとGeとNを含む材料などを用いることができる。また例えば、TaにB、Si、Ge等を加えることにより、アモルファス構造が容易に得られ、平滑性を向上させることができる。さらに、TaにN、Oを加えれば、酸化に対する耐性が向上するため、経時的な安定性を向上させることができる。なお、吸収体膜は、単層または複数層で構成されてもよい。
10g(0.057モル)のベンジルメタクリレート、19.2g(0.133モル)のヒドロキシプロピルメタクリレート、及び10.8g(0.063モル)のガンマーブチロラクトンメタクリレートを、128gのプロピレングリコールモノメチルエーテルに溶解させた後、フラスコ内を窒素で置換し80℃まで昇温した。
その後、1.6gの2,2’-アゾビスイソ酪酸メチルを30.4gのプロピレングリコールモノメチルエーテルに溶解させ、窒素加圧下に添加し、80℃で24時間反応させポリマーを得た。得られたポリマー(樹脂)の重量平均分子量Mwはポリスチレン換算で10000であった。
10g(0.057モル)のベンジルメタクリレート、19.2g(0.133モル)のヒドロキシプロピルメタクリレート、及び10.8g(0.063モル)のガンマーブチロラクトンメタクリレートを、120gのプロピレングリコールモノメチルエーテルに溶解させた後、フラスコ内を窒素で置換し60℃まで昇温した。
その後、0.4gの2,2’-アゾビスイソブチロニトリルを39.6gのプロピレングリコールモノメチルエーテルに溶解させ、窒素加圧下に添加し、60℃で24時間反応させポリマーを得た。得られたポリマー(樹脂)の重量平均分子量Mwはポリスチレン換算で87000であった。
10g(0.057モル)のベンジルメタクリレート、10g(0.069モル)のヒドロキシプロピルメタクリレート、及び10.3g(0.061モル)のガンマーブチルラクトンメタクリレートを、84.848gの乳酸エチルに溶解させた後、フラスコ内を窒素で置換し70℃まで昇温した。
その後、0.364gの2,2’-アゾビスイソブチロニトリルを36gの乳酸エチルに溶解させ、窒素加圧下に添加し、70℃で24時間反応させポリマーを得た。得られたポリマー(樹脂)の重量平均分子量Mwはポリスチレン換算で22000であった。
10g(0.057モル)のベンジルメタクリレート、10g(0.069モル)のヒドロキシプロピルメタクリレート、及び10.3g(0.061モル)のガンマーブチロラクトンメタクリレートを、90.909gの乳酸エチルに溶解させた後、フラスコ内を窒素で置換し70℃まで昇温した。
その後、0.909gの2,2’-アゾビスイソブチロニトリルを29.394gの乳酸エチルに溶解させ、窒素加圧下に添加し、70℃で24時間反応させポリマーを得た。得られたポリマー(樹脂)の重量平均分子量Mwはポリスチレン換算で12000であった。
10g(0.057モル)のベンジルメタクリレート、19.2g(0.133モル)のヒドロキシプロピルメタクリレート、及び10.8g(0.063モル)のガンマーブチロラクトンメタクリレートを、120gの乳酸エチルに溶解させた後、フラスコ内を窒素で置換し60℃まで昇温した。
その後、0.4gの2,2’-アゾビスイソブチロニトリルを39.6gの乳酸エチルに溶解させ、窒素加圧下に添加し、60℃で24時間反応させポリマーを得た。得られたポリマー(樹脂)の重量平均分子量Mwはポリスチレン換算で82000であった。
10g(0.057モル)のベンンジルメタクリレート、27.778g(0.193モル)のヒドロキシプロピルメタクリレート、及び17.778g(0.104モル)のガンマーブチロラクトンメタクリレートを、155.556gの乳酸エチルに溶解させた後、フラスコ内を窒素で置換し70℃まで昇温した。
その後、0.667gの2,2’-アゾビスイソブチロニトリルを66gの乳酸エチルに溶解させ、窒素加圧下に添加し、70℃で24時間反応させポリマーを得た。得られたポリマー(樹脂)の重量平均分子量Mwはポリスチレン換算で25000であった。
10g(0.057モル)のベンジルメタクリレート、及び19.2g(0.133モル)のヒドロキシプロピルメタクリレートを、128gのプロピレングリコールモノメチルエーテルに溶解させた後、フラスコ内を窒素で置換し80℃まで昇温した。
その後、1.6gの2,2’-アゾビスイソ酪酸メチルを30.4gのプロピレングリコールモノメチルエーテルに溶解させ、窒素加圧下に添加し、80℃で24時間反応させポリマーを得た。得られたポリマー(樹脂)の重量平均分子量Mwはポリスチレン換算で20000であった。
(レジスト下地組成物の調合)
合成例1で得られた樹脂1g、架橋剤としてテトラメトキシメチルグリコールウリル0.05g、架橋触媒としてピリジニウムパラトルエンスルホン酸0.003g、パターン形状調整剤としてビス(4-ヒドロキシフェニル)スルホン0.006g、溶剤としてプロピレングリコールモノメチルエーテル88.96gとプロピレングリコールモノメチルエーテルアセテート10gに溶解させレジスト下地組成物を得た。
合成石英ガラスからなる透光性基板上に、薄膜として光半透過膜、遮光性膜およびハードマスクをそれぞれスパッタリング法で形成した。具体的には、透明基板上に、光半透過膜として単層のMoSiN膜(厚さ69nm)を形成した。詳しくは、モリブデン(Mo)とシリコン(Si)との混合ターゲット(Mo:Si=10mol%:90mol%)を用い、アルゴン(Ar)と窒素(N2)とヘリウム(He)との混合ガス雰囲気(ガス流量比 Ar:N2:He=5:49:46)で、ガス圧0.3Pa、DC電源の電力を3.0kWとして、反応性スパッタリング(DCスパッタリング)により、モリブデン、シリコン及び窒素からなるMoSiN膜を69nmの膜厚で形成した。次いで、上記MoSiN膜が形成された透明性基板に対して、加熱炉を用いて、大気中で加熱温度を450℃、加熱時間を1時間として、加熱処理を行った。なお、このMoSiN膜は、ArFエキシマレーザーにおいて、透過率は6.16%、位相差が184.4度となっていた。
この遮光膜は、上記光半透過膜との積層構造で光学濃度(OD)がArFエキシマレーザー露光光の波長193nmにおいて3.0となるように調整されている。また、前記露光光の波長に対する遮光膜の表面反射率は20%であった。
そして、形成された薄膜の表面に対し、HMDS処理を所定の条件で施した。
続いて、得られたマスクブランクに所定の転写パターンを形成し、転写用マスクを作製した。具体的には、マスクブランクに対して、電子線により露光し、露光後に120℃でベーク処理を行った。その後、現像液(テトラメチルアミノハイドライド(TMAH)水溶液)を用いて現像することにより、レジストパターンを形成した。
本実施例のマスクブランクについて、以下の方法により評価した。
前述の手順で転写パターンを形成する際、100nmのラインアンドスペース(L/S)として解像性の確認を行った。電子顕微鏡で観察した像を図4に示す。
図4に示すように、パターン倒れがなく直線的なラインを形成することができた。このことから、本実施例に係るレジスト下地膜によってレジスト膜(レジストパターン)とレジスト下地膜との密着性が十分に確保されていることがわかる。
異物欠陥は、レジストパターン形成後のマスクブランクについて光学測定法によりピクセルヒストグラムを測定し、200nm以上の欠陥(ピクセル)を確認して行った。本実施例では、図5に示すように、異物欠陥によるピクセルがわずかに確認されたものの、非常に低密度であることが分かった。
実施例2~6では、実施例1において、合成例1で得られた樹脂1gの代わりに合成例2~6で得られた樹脂1gをそれぞれ用いた以外は、実施例1と同様にレジスト下地組成物を調合し、マスクブランクおよび転写用マスクを作製した。
実施例2~6では、目標の線幅を100nmのラインアンドスペース(L/S)として解像性の確認を行い、実施例1と同様の結果が得られたことを確認した。
またピクセルヒストグラムを用いて異物の確認を行ったところ、実施例1と同様に、低密度の欠陥の分散が確認されたのみであった。
このレジスト付マスクブランクのレジスト下地膜とレジスト膜の境界部分について調べたところ、レジスト下地膜とレジスト膜の界面には、明確な境界はなく、約5nm以下の厚みの混合領域が確認された。
比較例1では、実施例1において、合成例1で得られた樹脂1gの代わりに比較合成例1で得られた樹脂1gを用いた以外は、実施例1と同様にレジスト下地組成物を調合し、マスクブランクおよび転写用マスクを作製した。
このレジスト付マスクブランクのレジスト下地膜とレジスト膜の境界部分について調べたところ、レジスト下地膜とレジスト膜の界面には、明確な境界が確認された。つまり、比較例1では、界面に混合領域が形成されていないことが確認された。
目標の線幅の100nmのラインアンドスペース(L/S)ではパターン倒れが発生し、鮮明なパターンの形成ができなかった。
またピクセルヒストグラムを用いて異物の確認を行ったところ、図6に示すように、レジスト残渣による異物と思われる欠陥がスジ上に連なるような高密度な欠陥が確認された。
Claims (11)
- 基板上に、
転写パターンを形成するための薄膜と、
前記薄膜上に設けられ、ラクトン環を有する単位構造及び水酸基を有する単位構造を含むポリマーを含有するレジスト下地組成物から形成されるレジスト下地膜と、
前記レジスト下地膜上に設けられ、レジスト組成物から形成されるレジスト膜と、
前記レジスト下地膜とレジスト膜との間に介在するように設けられ、前記レジスト下地組成物と前記レジスト組成物とを含む混合成分から形成される混合膜と、を備えるマスクブランク。 - 前記ポリマーが、更にアリール基又はアリールアルキル基を有する単位構造を含む、請求項1に記載のマスクブランク。
- 前記ポリマーが、ラクトン(メタ)アクリレート及びヒドロキシアルキル(メタ)アクリレートを含み共重合して得られる、請求項1又は2に記載のマスクブランク。
- 前記ポリマーが、ラクトン(メタ)アクリレート、ヒドロキシアルキル(メタ)アクリレート、及びフェニル(メタ)アクリレート又はベンジル(メタ)アクリレートを含み共重合して得られる、請求項1又は請求項2に記載のマスクブランク。
- 前記レジスト下地組成物が、更に多核フェノールを含有する、請求項1乃至請求項5のいずれか1項に記載のマスクブランク。
- 前記多核フェノールが、式(b-1)で示される化合物、式(b-2)で示される化合物、又は式(b-3)で示される化合物の少なくとも1つである、請求項6に記載のマスクブランク。
(ただし、式(b-1)中でR11はそれぞれベンゼン環の水素原子の置換基であって、水酸基、ハロゲン基、炭素原子数1~10のアルキル基、炭素原子数6~18のアリール基、炭素原子数7~25のアリールアルキル基、炭素原子数2~10のアルキルカルボニル基、炭素原子数2~10のアルキルカルボニルオキシ基、炭素原子数2~10のアルキルカルボニルアミノ基、炭素原子数7~10のアリールオキシアルキル基、炭素数1~6のアルコキシ基又はそれらの組み合わせからなる有機基であり、R12は単結合、又は2~4価でハロゲン原子で置換されていても良い炭素原子数1~10の炭化水素基、2~4価でハロゲン原子で置換されていても良い炭素原子数7~25のアリールアルキル基、若しくはスルホニル基を示し、m1は1~5の整数であり、n1は0≦n1≦5-m1の整数であり、qは2~4の整数を示す。)
(ただし、式(b-2)中のR13及びR14はそれぞれ式(b-1)中のR11と同じあり、R15は単結合、又は2~6価でハロゲン原子で置換されていても良い炭素原子数1~10の炭化水素基、2~6価でハロゲン原子で置換されていても良い炭素原子数7~25のアリールアルキル基、若しくはスルホニル基を示し、m2及びm3はそれぞれ1~5の整数であり、n2及びn3は0≦n2≦5-m2、0≦n3≦5-m3の整数であり、k及びsはそれぞれ1~3の整数を示す。)
(ただし、式(b-3)中のR16、R17及びR18はそれぞれ式(b-1)中のR11と同じであり、R19及びR20はそれぞれ単結合、又は2価でハロゲン原子で置換されていても良い炭素原子数1~10の炭化水素基、2価でハロゲン原子で置換されていても良い炭素原子数7~25のアリールアルキル基、若しくはスルホニル基であり、m5は1~4の整数であり、m4及びm6はそれぞれ1~5の整数であり、n5は0≦n5≦4-m5、n4及びn6はそれぞれ0≦n4≦5-m4、0≦n6≦5-m6の整数であり、tは1~4の整数を示す。) - 前記レジスト下地組成物が、更に架橋性化合物を含有する、請求項1乃至請求項7のいずれか1項に記載のマスクブランク。
- 前記レジスト下地組成物が、更に酸化合物を含有する、請求項1乃至請求項8のいずれか1項に記載のマスクブランク。
- 基板上に、転写パターンを形成するための薄膜を形成する薄膜形成工程と、
前記薄膜上に、ラクトン環を有する単位構造及び水酸基を有する単位構造を含むポリマーを含有するレジスト下地組成物を塗布し、加熱することにより、レジスト下地膜を形成するレジスト下地膜形成工程と、
前記レジスト下地膜上にレジスト組成物を塗布し、加熱することにより、レジスト膜を形成するレジスト膜形成工程と、を有し、
前記レジスト膜形成工程では、
前記レジスト下地膜上に前記レジスト組成物を塗布することで前記レジスト下地膜の表層部を溶解させ、前記レジスト下地膜と塗布した前記レジスト組成物との界面に、前記レジスト下地膜が溶解した成分と前記レジスト組成物とが混合した混合成分を形成し、
前記レジスト組成物と共に前記混合成分を加熱することにより、前記レジスト膜と、前記レジスト下地膜と前記レジスト膜との間に介在する混合膜を形成する、マスクブランクの製造方法。 - 請求項10に記載のマスクブランクの製造方法によって製造されたマスクブランクの前記レジスト膜および前記混合膜を露光・現像することによりレジストパターンを形成するレジストパターン形成工程と、
前記レジストパターンをマスクとして前記レジスト下地膜および前記薄膜をエッチングすることにより前記基板上に転写パターンを形成する転写パターン形成工程を有する、転写用マスクの製造方法。
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Also Published As
Publication number | Publication date |
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US10042247B2 (en) | 2018-08-07 |
KR102380067B1 (ko) | 2022-03-28 |
JP6258830B2 (ja) | 2018-01-10 |
KR20170060076A (ko) | 2017-05-31 |
US20170285460A1 (en) | 2017-10-05 |
JP2016066019A (ja) | 2016-04-28 |
TW201614366A (en) | 2016-04-16 |
TWI682235B (zh) | 2020-01-11 |
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