WO2020213661A1 - ペリクル用粘着剤、ペリクル、ペリクル付露光原版、半導体装置の製造方法、液晶表示板の製造方法、露光原版の再生方法及び剥離残渣低減方法 - Google Patents
ペリクル用粘着剤、ペリクル、ペリクル付露光原版、半導体装置の製造方法、液晶表示板の製造方法、露光原版の再生方法及び剥離残渣低減方法 Download PDFInfo
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- WO2020213661A1 WO2020213661A1 PCT/JP2020/016626 JP2020016626W WO2020213661A1 WO 2020213661 A1 WO2020213661 A1 WO 2020213661A1 JP 2020016626 W JP2020016626 W JP 2020016626W WO 2020213661 A1 WO2020213661 A1 WO 2020213661A1
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- pellicle
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
- C09J7/38—Pressure-sensitive adhesives [PSA]
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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
- G03F1/00—Originals for photomechanical production of textured or patterned surfaces, e.g., masks, photo-masks, reticles; Mask blanks or pellicles therefor; Containers specially adapted therefor; Preparation thereof
- G03F1/62—Pellicles, e.g. pellicle assemblies, e.g. having membrane on support frame; Preparation thereof
- G03F1/64—Pellicles, e.g. pellicle assemblies, e.g. having membrane on support frame; Preparation thereof characterised by the frames, e.g. structure or material, including bonding means therefor
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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
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J129/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Adhesives based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Adhesives based on derivatives of such polymers
- C09J129/10—Homopolymers or copolymers of unsaturated ethers
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
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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
- G03F1/00—Originals for photomechanical production of textured or patterned surfaces, e.g., masks, photo-masks, reticles; Mask blanks or pellicles therefor; Containers specially adapted therefor; Preparation thereof
- G03F1/26—Phase shift masks [PSM]; PSM blanks; Preparation thereof
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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
- G03F1/00—Originals for photomechanical production of textured or patterned surfaces, e.g., masks, photo-masks, reticles; Mask blanks or pellicles therefor; Containers specially adapted therefor; Preparation thereof
- G03F1/62—Pellicles, e.g. pellicle assemblies, e.g. having membrane on support frame; Preparation thereof
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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
- G03F1/00—Originals for photomechanical production of textured or patterned surfaces, e.g., masks, photo-masks, reticles; Mask blanks or pellicles therefor; Containers specially adapted therefor; Preparation thereof
- G03F1/66—Containers specially adapted for masks, mask blanks or pellicles; Preparation thereof
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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
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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
- G03F7/70—Microphotolithographic exposure; Apparatus therefor
- G03F7/708—Construction of apparatus, e.g. environment aspects, hygiene aspects or materials
- G03F7/70983—Optical system protection, e.g. pellicles or removable covers for protection of mask
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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
- H01L21/67—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere
- H01L21/683—Apparatus specially adapted for handling semiconductor or electric solid state devices during manufacture or treatment thereof; Apparatus specially adapted for handling wafers during manufacture or treatment of semiconductor or electric solid state devices or components ; Apparatus not specifically provided for elsewhere for supporting or gripping
Definitions
- the present invention relates to an adhesive for pellicle, a pellicle, an exposure original plate with a pellicle, a method for manufacturing a semiconductor device, a method for manufacturing a liquid crystal display plate, a method for regenerating an exposure original plate, and a method for reducing peeling residue.
- the "exposure original plate” is a general term for a mask for lithography and a reticle.
- the basic structure of the pellicle consists of a pellicle frame and a pellicle membrane stretched on the pellicle frame.
- the pellicle film is made of nitrocellulose, cellulose acetate, a fluorine-based polymer, or the like that well transmits light used for exposure (g-line, i-line, 248 nm, 193 nm, 157 nm, etc.).
- the pellicle frame is made of an aluminum alloy such as A7075, A6061, A5052, which has been subjected to black alumite treatment or the like, stainless steel, polyethylene, or the like.
- a good solvent for the pellicle film is applied to the upper part of the pellicle frame, and the pellicle film is air-dried and adhered, or adhered with an adhesive such as acrylic resin, epoxy resin, or fluororesin. Further, since the exposure original plate is mounted on the lower part of the pellicle frame, it is used for protection for the purpose of protecting the pressure-sensitive adhesive layer obtained from polybutene resin, polyvinyl acetate resin, acrylic resin, silicone resin, etc., and the pressure-sensitive adhesive layer. Provide a liner.
- the pellicle is installed so as to surround the pattern area formed on the surface of the exposure original plate. Since the pellicle is provided to prevent dust from adhering to the exposure original plate, the pattern region and the outside of the pellicle are separated from each other so that dust outside the pellicle does not adhere to the pattern surface.
- phase shift film As the mask substrate film used in recent years, a phase shift film has come to be generally adopted in order to cope with the miniaturization of design rules.
- the phase shift film is very delicate, and mask cleaning under excessive conditions may damage the phase shift film such as corrosion and scraping. Therefore, in recent years, the chemical solution used for mask cleaning has been reexamined. Or tend to weaken the cleaning conditions.
- the mask pattern of advanced products has changed from the positive type mask pattern, which has been the mainstream until now, to the negative type mask pattern, and along with this, there is no light-shielding layer in the part where the pellicle is attached. There are many. Without the light-shielding layer, the pellicle adhesive may be exposed to light through the mask substrate. Then, when the pellicle is peeled off, more residue of the adhesive layer may remain on the mask substrate.
- repelicle When the pellicle is used by attaching it to the mask, if foreign matter or haze is generated or the pellicle film is damaged, it is necessary to peel off the pellicle, re-clean the mask, and replace it with a new pellicle. (Hereafter referred to as "repellicle"). The most important thing in the repelicle is to re-clean the mask so that it is in a highly clean state, but in order to re-clean the mask under weak cleaning conditions in recent years, when the pellicle is peeled off, It is important how to reduce the residue remaining on the mask substrate.
- Fuctional water is generally an aqueous solution that has been given reproducible and useful functions by artificial treatment, and the scientific basis for treatment and function has been clarified, and is about to be clarified. It is defined as what is. Specific examples include fine bubble water such as ozone water, hydrogen water, microbubble water, and nanobubble water, electrolyzed water, supercritical water, and subcritical water. Ozone water and hydrogen are used to clean the photomask. A lot of water is used. In addition, the detergency can be improved by adding a small amount of ammonia.
- a lithographic pellicle in which a pellicle film is attached to the upper end surface of the pellicle frame via an adhesive layer for attaching a pellicle film, and an adhesive layer for attaching a mask is provided on the other end surface, such as an ArF excimer laser (193 nm).
- Patent Document 1 and Patent Document 2 As a technique for reducing the residue, attempts have been made to add a surface modifier or the like to the pressure-sensitive adhesive (Patent Document 1 and Patent Document 2). Further, as a technique for reducing the residue, a large pellicle having an adhesive layer having a cohesive breaking strength of 20 g / mm 2 or more (Patent Document 3), and a ratio of peel strength to tensile strength of 0.10 or more is 0. A pellicle having a pellicle adhesive of 33 or less is disclosed (Patent Document 4).
- the present invention has been made in view of such a situation, and when the pellicle is peeled off from the exposure original plate after using lithography, particularly after using ArF lithography, the pellicle that can reduce the residue sticking to the exposure original plate can be reduced. It is an object of the present invention to provide a pressure-sensitive adhesive, a pellicle, an exposure original plate with a pellicle, a method for regenerating an exposure original plate, and a method for reducing peeling residue. It is an object of the present invention to provide a method for manufacturing a semiconductor device and a liquid crystal display board capable of improving production efficiency.
- An adhesive for pellicle for attaching a pellicle to an exposure original plate A pressure-sensitive adhesive for pellicle based on an acrylic polymer having an SP value of 10.0 or more and 12.0 or less.
- An adhesive for pellicle for attaching a pellicle to an exposure original plate A pressure-sensitive adhesive for pellicle that uses an acrylic polymer having an ether-bonded (meth) acrylic ester as a monomer component as a base material.
- An adhesive for pellicle for attaching a pellicle to an exposure original plate which is an adhesive for pellicle using an acrylic polymer as a base material having a side chain that is selectively deteriorated by irradiation with exposure light.
- the pellicle according to the above [14] which is attached to an exposure original plate having a non-shielded region or a translucent light-shielding region in a portion to which the pressure-sensitive adhesive layer is attached in the exposure original plate.
- the pellicle according to the above [14] which is attached to an exposure original plate having a transparent region in a portion where the pressure-sensitive adhesive layer is attached in the exposure original plate.
- the pellicle according to the above [14] which is attached to a surface containing silicon oxide as a main component.
- the pellicle according to the above [20], wherein the surface containing silicon oxide as a main component is a quartz surface.
- a method for manufacturing a semiconductor device comprising a step of exposing with an exposure original plate with a pellicle according to any one of [23] to [29].
- a method for manufacturing a liquid crystal display board comprising a step of exposing with the exposure original plate with a pellicle according to any one of [23] to [29].
- Exposure to regenerate the exposure original plate by peeling the pellicle from the exposure original plate with pellicle according to any one of [23] to [29] and washing the adhesive residue remaining on the exposure original plate with functional water. How to play the original version.
- An adhesive for attaching the pellicle to the exposure original plate is selected, the adhesive is applied to one end surface of the pellicle frame to form an adhesive layer, and a protective member is detachably attached to the adhesive layer.
- a method for producing a peeling residue-reducing pellicle in which an adhesive is applied to the other end face of the pellicle frame and a pellicle film is attached to the adhesive.
- a method for producing a peeling residue-reducing pellicle which comprises selecting a pressure-sensitive adhesive using an acrylic resin having an SP value of 10.0 or more and 12.0 or less as a base material.
- the pellicle and the pellicle that can reduce the peeling residue of the adhesive layer of the pellicle remaining on the exposure original plate are attached. It is possible to provide an exposure original plate, a method for regenerating an exposure original plate, and a method for reducing peeling residue. In the method for regenerating the pellicle, the exposure original plate with the pellicle, the exposure original plate, and the peeling residue reduction method of the present invention, even if the exposure light is irradiated through the exposure original plate, the peeling residue of the adhesive is generated when the pellicle is peeled from the exposure original plate.
- the type of the pellicle film 12 is not particularly limited, and for example, an amorphous fluoropolymer or the like conventionally used for an excimer laser is used.
- the amorphous fluoropolymer include Cytop (trade name manufactured by Asahi Glass Co., Ltd.), Teflon (registered trademark) AF (trade name manufactured by DuPont) and the like. These polymers may be dissolved in a solvent and used when the pellicle film is produced, and can be appropriately dissolved in, for example, a fluorine-based solvent.
- the base material of the pellicle frame 11 for example, a conventionally used aluminum alloy material, preferably JIS A7075, JIS A6061, JIS A5052 material or the like is used, but when an aluminum alloy material is used, the pellicle frame is used. There is no particular limitation as long as the strength of is secured.
- the surface of the pellicle frame is preferably roughened by sandblasting or chemical polishing, and a polymer film may be provided after the roughening.
- a conventionally known method can be adopted as the method for roughening the frame surface.
- a method is preferable in which the surface of the aluminum alloy material is blasted with stainless steel, carborundum, glass beads or the like, and further chemically polished with NaOH or the like to roughen the surface.
- the first aspect of the pressure-sensitive adhesive for pellicle of the present invention is to use an acrylic polymer having an SP value of 10.0 or more and 12.0 or less as a base material.
- the SP value of the acrylic polymer By setting the SP value of the acrylic polymer to 10.0 or more and 12.0 or less, it is possible to reduce the peeling residue of the pressure-sensitive adhesive layer remaining on the exposure original plate when the pellicle is peeled from the exposure original plate.
- the effect of the present invention may be obtained by improving the hydrophilicity of the acrylic polymer by setting the SP value in a specific range.
- the second aspect of the pressure-sensitive adhesive for pellicle of the present invention is to use an acrylic polymer containing an ether-bonded (meth) acrylic acid ester as a monomer component as a base material.
- an acrylic polymer containing an ether-bonded (meth) acrylic acid ester having an ether bond as a monomer component of the acrylic polymer when the pellicle is peeled from the exposure master plate, the peeling residue of the pressure-sensitive adhesive layer remaining on the exposure master plate is reduced. be able to.
- By introducing an ether bond into the acrylic polymer it becomes easy to control the hydrophilicity of the acrylic polymer. Further, it is presumed that by introducing an ether bond into the side chain of the acrylic polymer, the ether bond suppresses photodegradation of the main chain.
- the third aspect of the pressure-sensitive adhesive for pellicle of the present invention is to use an acrylic polymer having a side chain containing an ether bond as a base material.
- an acrylic polymer having a side chain containing an ether bond as a base material.
- the fourth aspect of the pressure-sensitive adhesive for pellicle of the present invention is to use an acrylic polymer having a side chain having a higher decomposability by irradiation with an exposure light than the main chain as a base material.
- an acrylic polymer having a side chain having a higher decomposability by irradiation with an exposure light than the main chain as a base material.
- the IR chart of the pressure-sensitive adhesive before irradiation with the exposure light and the IR chart of the pressure-sensitive adhesive after irradiation with the exposure light and observing the change in the spectral intensity.
- the fifth aspect of the pressure-sensitive adhesive for pellicle of the present invention is to use an acrylic polymer having a side chain that is selectively deteriorated by irradiation with an exposure light as a base material. Since the side chain of the acrylic polymer is selectively deteriorated by irradiation with the exposure light, it is possible to reduce the peeling residue of the pressure-sensitive adhesive layer remaining on the exposure master when the pellicle is peeled from the exposure master. It is presumed that the side chains are selectively deteriorated by the irradiation of the exposure light, so that the decomposition of the side chains is substantially preceded by the decomposition of the main chain, and the peeling residue can be reduced.
- the decomposition of the side chain has a relatively small effect on the deterioration of the pressure-sensitive adhesive, and even if the decomposition progresses, it is considered that it is unlikely to remain as a peeling residue at the time of peeling due to the cohesive force of the pressure-sensitive adhesive.
- the photodegradation of the main chain progresses, the molecular weight of the main chain progresses, and it is considered that the low molecular weight adhesive remains on the substrate as a residue.
- the "adhesive using an acrylic polymer as a base material” is a pressure-sensitive adhesive containing the acrylic polymer itself or a pressure-sensitive adhesive containing a reaction product of the acrylic polymer and a curing agent or the like. Means an agent.
- the acrylic polymer is, for example, a polymer containing a (meth) acrylic acid ester as a monomer component, and if necessary, a monomer component copolymerizable with the (meth) acrylic acid ester. It can be copolymerized.
- Examples of the (meth) acrylic acid ester include a (meth) acrylic acid ester having an ether bond, a (meth) acrylic acid alkyl ester, an unsaturated monomer having a carboxyl group or a hydroxyl group, and the like.
- a (meth) acrylic acid ester having an ether bond as a monomer component, an ether bond can be introduced into the side chain of the acrylic polymer.
- Examples of the (meth) acrylic acid ester having an ether bond (component (A)) include a (meth) acrylic acid ester having an alkylene oxide group such as an ethylene oxide group, a propylene oxide group, and a butylene oxide group.
- (meth) acrylic acid ester having an ethylene oxide group (also referred to as ethylene oxide group-containing (meth) acrylate) is preferable, and for example, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2 -Butoxyethyl (meth) acrylate, phenoxyethylene glycol (meth) acrylate, methoxypolyethylene glycol (meth) acrylate such as methoxydiethylene glycol (meth) acrylate, ethoxypolyethylene glycol (meth) acrylate such as ethoxydiethylene glycol (meth) acrylate, butoxydiethylene glycol Examples thereof include butoxypolyethylene glycol (meth) acrylate such as (meth) acrylate and phenoxypolyethylene glycol (meth) acrylate such as phenoxydiethylene glycol (meth) acrylate. These may be used alone or in combination of two or
- Examples of the (meth) acrylic acid alkyl ester (component (B)) include a (meth) acrylic acid alkyl ester having an alkyl group having 1 to 14 carbon atoms. Specifically, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, isoamyl (meth) acrylate, hexyl (meth) acrylate, 2 -Ethylhexyl (meth) acrylate, n-octyl (meth) acrylate, isooctyl (meth) acrylate, isononyl (meth) acrylate, lauryl (meth) acrylate and the like can be mentioned. Among these, (meth) acrylic acid alkyl esters having an alkyl group having 4 or 8 carbon atoms are preferable from the
- the ratio of the component (A) to be used is preferably 30% by mass or more, more preferably 35% by mass or more, and 35 to 98% by mass in the total monomer components. It is particularly preferable that the amount is 40 to 95% by mass, and it is extremely preferable that the content is 40 to 95% by mass.
- the ratio of the component (B) used is preferably 0 to 70% by mass, more preferably 3 to 55% by mass, based on all the monomer components. By setting the ratio of the component (B) to the above range, the adhesiveness can be easily controlled.
- the ratio of the component (C) used is preferably 0 to 10% by mass, more preferably 2 to 8% by mass, based on all the monomer components.
- the acrylic polymer can be produced by appropriately selecting a known production method such as solution polymerization, bulk polymerization, emulsion polymerization, or radical polymerization. Further, the obtained acrylic polymer may be any of a random copolymer, a block copolymer, a graft copolymer and the like.
- the molecular weight of the acrylic polymer is in the range of 700,000 to 2.5 million as the weight average molecular weight, the cohesive force and adhesive force of the pressure-sensitive adhesive layer become appropriate, and it is difficult for adhesive to remain and is sufficient. It is preferable because it is an adhesive having adhesive strength and load resistance.
- the above weight average molecular weight is a value measured by gel permeation chromatography (GPC) analysis and means a standard polystyrene equivalent value. GPC analysis can be performed using tetrahydrofuran (THF) as the solution.
- the pressure-sensitive adhesive in the pressure-sensitive adhesive layer preferably contains a reaction product of an acrylic polymer and a curing agent, but in consideration of softness, an acrylic weight that does not react with the curing agent. It may include coalescence.
- the curing agent is not particularly limited as long as it is a curing material used as an ordinary pressure-sensitive adhesive, and for example, a metal salt, a metal alkoxide, an aldehyde compound, a non-amino resin amino compound, a urea compound, an isocyanate compound, etc.
- a metal salt e.g., a metal salt, a metal alkoxide, an aldehyde compound, a non-amino resin amino compound, a urea compound, an isocyanate compound, etc.
- examples thereof include polyfunctional epoxy compounds, metal chelate compounds, melamine compounds, and isocyanate compounds.
- isocyanate compounds and epoxy compounds are preferable from the viewpoint of reactivity with a carboxyl group or a hydroxyl group.
- isocyanate-based compounds include xylylene diisocyanate, hexamethylene diisocyanate, tolylene diisocyanate, multimers, derivatives, and polymers thereof. These may be used alone or in combination of two or more.
- Examples of the epoxy compound include compounds having two or more epoxy groups in the molecule, and specific examples thereof include ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerin diglycidyl ether, and glycerin triglycidyl ether. 1,6-Hexanediol diglycidyl ether, trimethylpropan triglycidyl ether, diglycidyl aniline, diamine glycidyl amine, N, N, N', N'-tetraglycidyl-m-xylylene diamine, 1,3-bis ( N, N'-diamine glycidyl aminomethyl) and the like. These may be used alone or in combination of two or more.
- the definition of the SP value is as follows. [Calculation method of SP value]
- the SP value is a solubility parameter. This SP value can be obtained by referring to the calculation method of Fedors ["Polymer Engineering and Science", Vol. 14, No. 2 (1974), pp. 148 to 154] and calculating by the following formula 1.
- the unit of the solubility parameter is (cal / mol) 1/2 .
- Table 1 shows the eigenvalues of ⁇ ei and ⁇ vi given to the main atoms or atomic groups with respect to the above formula 1.
- the SP value (solubility parameter) of the acrylic polymer is preferably 10.0 to 12.0, and more preferably 10.0 to 11.0.
- the SP value of the acrylic polymer can be controlled, for example, by changing the concentration of polar groups in the acrylic polymer. For example, when a relatively highly polar bond such as an ether bond is introduced into the side chain, the SP value tends to increase. On the other hand, when a relatively low-polarity bond such as a long-chain alkylene bond is introduced into the side chain, the SP value tends to decrease.
- the pressure-sensitive adhesive in the present invention includes two or more kinds of acrylic polymers having different weight average molecular weights, two or more kinds of acrylic polymers having different monomer components, and two or more kinds of acrylic polymers having different copolymerization ratios.
- Two or more kinds of acrylic polymers such as coalescing may be combined as a base material.
- the SP value of only one type of acrylic polymer may be within the range as long as the effect of the present invention is exhibited, or the SP value of all acrylic polymers is out of the range.
- the SP value of the entire acrylic polymer component may be within the range.
- the SP value of the entire acrylic polymer component is calculated by proportionally dividing the SP value of each of the two or more kinds of acrylic polymers according to the respective blending amounts.
- the shape of the pressure-sensitive adhesive layer 14 is preferably flattened with little deformation when the pellicle is attached, in order to reduce the influence of distortion and the like on the mask substrate to be attached and to suppress the residual stress due to the pellicle attachment.
- this pressure-sensitive adhesive layer contains a polyvinyl ether compound, more favorable results tend to be obtained. Specifically, when the vinyl ether groups were mixed in the pressure-sensitive adhesive layer so as to diffuse uniformly throughout, the peelability of the pressure-sensitive adhesive was further improved, and almost no residue was generated in the visual inspection.
- the pressure-sensitive adhesive layer in which vinyl ether groups are uniformly dispersed and mixed is less likely to generate dust even when exposed to ultraviolet rays of 193 nm after being attached to the mask substrate, and is good without leaving a peeling residue on the mask substrate. The probability of exfoliation was significantly improved.
- the pellicle uses an acrylic polymer having an SP value of 10.0 or more and 12.0 or less as a base material constituting the mask pressure-sensitive adhesive layer, and contains a polyvinyl ether compound. Therefore, even if the exposed light beam is irradiated through the mask substrate, the deterioration of the surface is reduced, and when the pellicle is peeled off from the mask substrate, the fine particulate residue is also reduced. As a result, not only the regenerative cleaning of the mask substrate from which the pellicle has been peeled off proceeds satisfactorily, but also the cleaning conditions can be relaxed, which is advantageous in reducing damage to the mask surface during cleaning.
- polyvinyl ether compound examples include copolymers of vinyl ethers such as methyl vinyl ether, ethyl vinyl ether, butyl vinyl ether, isobutyl vinyl ether, and (2-methoxyethyl) vinyl ether, and two or more kinds of vinyl ethers. Examples thereof include copolymers of the above, copolymers of these vinyl ethers and other monomers, and the like. Among these, a polyvinyl ether compound containing methyl vinyl ether as a raw material monomer is preferable from the viewpoint of controlling the peeling residue.
- the blending ratio of the acrylic polymer and the polyvinyl ether compound is 90:10 to 99: 1, preferably 92: 8 to, on a mass basis, from the viewpoint of reducing the peeling residue.
- 98: 2 particularly preferably 94: 6 to 96: 4.
- the pressure-sensitive adhesive forming the pressure-sensitive adhesive layer of the pellicle includes a cross-linking agent, a pressure-sensitive adhesive, a plasticizer, a stabilizer, a viscosity modifier, and an antistatic agent as long as the characteristics of the present invention are not impaired.
- Lubricants conductivity-imparting agents, flame-retardant-imparting agents, thermal conductivity-improving agents, heat-resistant improving agents, weather-resistant improving agents, thixo-imparting agents, antioxidants, antibacterial agents, fungicides, coloring agents, etc.
- Other ingredients may be blended.
- a liquid or paste-like pressure-sensitive adhesive in an uncured state is applied to the lower end surface of the pellicle frame 11 and then cured to form a pressure-sensitive adhesive layer.
- the pressure-sensitive adhesive may be applied once, or may be applied several times in order to obtain a predetermined thickness of the pressure-sensitive adhesive layer. In this case, it is preferable to allow the adhesive to stand as appropriate between each round until the shape of the adhesive after application is stable.
- the adhesive may be appropriately diluted with an organic solvent, alcohol, water or the like to reduce the viscosity of the adhesive before application.
- the adhesive can be applied by, for example, a dip, a spray, a brush coating, a coating device using a dispenser, or the like, but the coating using the coating device using a dispenser has stability, workability, yield, and the like. It is preferable from the point of view.
- the pellicle of the present invention By using the pellicle of the present invention having the configuration described above, it is possible to reduce the amount of adhesive residue when the pellicle is peeled off from the exposure original plate after using lithography. Further, according to the present invention, there is provided a method for reducing the peeling residue of the pressure-sensitive adhesive layer of the pellicle by using the pellicle of the present invention. Therefore, the pellicle of the present invention is useful as a phase shift photomask having the above-mentioned delicate phase shift film or a pellicle to be attached to a surface containing silicon oxide as a main component such as quartz.
- exposure light adheres to a negative type exposure original plate, an exposure original plate having a non-light-shielded area or a semi-transparent light-shielding area on the adhesive sticking portion, an exposure original plate having a transparent region on the adhesive sticking portion, and the like. It is also useful as a pellicle applied to an exposure original plate that irradiates the agent layer.
- the pressure-sensitive adhesive layer of the pellicle used for such an exposure original plate is exposed to an exposure ray through the exposure original plate from a surface opposite to the surface on which the pellicle of the exposure original plate is provided.
- the pellicle of the present invention is used not only as a protective member for suppressing foreign matter from adhering to the exposure master plate in the exposure apparatus, but also for protecting the exposure master plate during storage of the exposure master plate and transportation of the exposure master plate. It may be used as a protective member.
- an exposure original plate such as a photomask
- an exposure original plate with a pellicle can be manufactured.
- the method for manufacturing a semiconductor device or a liquid crystal display plate according to the present embodiment includes a step of exposing a substrate (semiconductor wafer or liquid crystal original plate) with the above-mentioned exposure original plate with a pellicle.
- a substrate semiconductor wafer or liquid crystal original plate
- the above exposure master plate with a pellicle is installed on a stepper in order to form a photoresist pattern corresponding to an integrated circuit or the like on a substrate. To expose.
- the yield in the lithography process can be improved by using the exposure original plate with a pellicle.
- the pellicle may be peeled off from the exposure original plate to perform regenerative cleaning of the exposure original plate.
- Example 1 After precision cleaning of an aluminum alloy pellicle frame (external size 149 mm x 115 mm x 3.5 mm, wall thickness 2 mm, flatness on the end face side coated with adhesive for mask application: 15 um), the flatness is reinforced on the end face on the 15 um side.
- Acrylic adhesive manufactured by Kagaku Co., Ltd. (Product name: SK Dyne SN-70A, SP of the base material containing an acrylic polymer in which 95% by mass of the monomer component is an ethylene oxide group-containing (meth) acrylate as the base material. A value of 10.2) was applied, and the mixture was allowed to stand at room temperature for 60 minutes.
- a separator was placed on an aluminum plate having a flatness of 5 um, and a pellicle frame coated with an adhesive was placed so that the adhesive was facing downward. As a result, the adhesive was brought into contact with the flat separator and flattened. Next, the pellicle on the aluminum plate was placed in an oven at 60 ° C. for 60 minutes to cure the adhesive. Then, after taking out the pellicle together with the aluminum plate, the separator was peeled off.
- an adhesive product name: Cytop CTX-A manufactured by Asahi Glass Co., Ltd. was applied to the end face on the opposite side of the adhesive application. Then, the pellicle frame was heated at 130 ° C. to cure the adhesive. Finally, the adhesive-coated end face side of the pellicle frame was attached to a pellicle film formed on an aluminum frame larger than the pellicle frame, and the portion outside the pellicle frame was removed to complete the pellicle.
- the 6025 mask substrate (6 inches) and the pellicle prepared earlier were set in the affixing device, and the pellicle was affixed to the mask substrate by pressurizing with a sticking load of 50 N and a load time of 30 seconds.
- Example 2 As the pressure-sensitive adhesive, an acrylic pressure-sensitive adhesive manufactured by Soken Kagaku Co., Ltd. (product name: SN-25B, a mother material containing an acrylic polymer in which 40% by mass of the monomer component is an ethylene oxide group-containing (meth) acrylate as a base material.
- the pellicle was completed by the same method and material as in Example 1 except that the SP value of the material was 10.5). Further, the pellicle was attached to the mask substrate and peeled off under the same conditions as in Example 1.
- Example 3 The pellicle was completed by the same method and material as in Example 1 except that 3 parts by mass of the polyvinyl ether compound was contained in 100 parts by mass of SK Dyne SN-70A as the pressure-sensitive adhesive. Further, the pellicle was attached to the mask substrate and peeled off under the same conditions as in Example 1.
- Example 1 As the pressure-sensitive adhesive, an acrylic pressure-sensitive adhesive manufactured by Soken Kagaku Co., Ltd. (product name: SK Dyne SK-1425S, an acrylic polymer containing no (meth) acrylic acid ester having an ether bond as a monomer component is contained as a base material.
- the pellicle was completed by the same method and material as in Example 1 except that the SP value of the base material was 9.8). Further, the pellicle was attached to the mask substrate and peeled off under the same conditions as in Example 1.
- Example 2 As the pressure-sensitive adhesive, an acrylic pressure-sensitive adhesive manufactured by Soken Kagaku Co., Ltd. (product name: SK Dyne SK-1495S, an acrylic polymer containing no (meth) acrylic acid ester having an ether bond as a monomer component is contained as a base material.
- the pellicle was completed by the same method and material as in Example 1 except that the SP value of the base material was 9.2). Further, the pellicle was attached to the mask substrate and peeled off under the same conditions as in Example 1.
- Examples 4 to 8 A pellicle was prepared in the same manner as in Example 1 except that the adhesives obtained in Synthesis Examples 1 to 5 were used as the adhesive, and a peeling test was conducted. As a result, in the pellicle using any of the adhesives, the peeling residue was reduced and the cleaning removability was improved as compared with the comparative example.
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Abstract
Description
この場合、ゴミは露光原版の表面上には直接付着せず、ペリクル膜上に付着するため、リソグラフィ時に焦点を露光原版のパターン上に合わせておけば、ペリクル膜上のゴミは転写に無関係となる。
この再生洗浄は一般的に硫酸過水、アンモニア過水等の薬剤による洗浄や、ブラシ、スポンジ等の物理的な洗浄が使用されている。しかしながら、フォトマスクへのダメージや硫酸イオンのフォトマスクへの残存を抑制するために、機能水による再生洗浄が検討されている。
[1]露光原版にペリクルを貼り付けるためのペリクル用粘着剤であって、
SP値が10.0以上12.0以下であるアクリル系重合体を母材とするペリクル用粘着剤。
[2]露光原版にペリクルを貼り付けるためのペリクル用粘着剤であって、
エーテル結合を有する(メタ)アクリル酸エステルを単量体成分とするアクリル系重合体を母材とするペリクル用粘着剤。
[3]エーテル結合を有する(メタ)アクリル酸エステルが、アルキレンオキサイド基を有する(メタ)アクリル酸エステルである前記[2]記載のペリクル用粘着剤。
[4]エーテル結合を有する(メタ)アクリル酸エステルが、全単量体成分に対して30質量%以上含まれる前記[3]記載のペリクル用粘着剤。
[5]アルキレンオキサイド基が、エチレンオキサイド基である前記[3]又は[4]記載のペリクル用粘着剤。
[6]単量体成分として、さらにカルボキシル基又はヒドロキシル基を有する不飽和モノマーを含む前記[2]~[5]のいずれかに記載のペリクル用粘着剤。
[7]単量体成分として、さらに(メタ)アクリル酸アルキルエステルを含む前記[2]~[6]のいずれかに記載のペリクル用粘着剤。
[8]露光原版にペリクルを貼り付けるためのペリクル用粘着剤であって、
エーテル結合を含む側鎖を有するアクリル系重合体を母材とするペリクル用粘着剤。
[9]エーテル結合を含む側鎖が、アルキレンオキサイド基を有する前記[8]記載のペリクル用粘着剤。
[10]アルキレンオキサイド基が、エチレンオキサイド基である前記[9]記載のペリクル用粘着剤。
[11]露光原版にペリクルを貼り付けるためのペリクル用粘着剤であって、露光光線の照射による分解性が主鎖よりも高い側鎖を有するアクリル系重合体を母材とするペリクル用粘着剤。
[12]露光原版にペリクルを貼り付けるためのペリクル用粘着剤であって、露光光線の照射により選択的に劣化する側鎖を有するアクリル系重合体を母材とするペリクル用粘着剤。
[13]ペリクルフレームと、該ペリクルフレームの一方の端面に設けられた前記[1]~[12]のいずれかに記載のペリクル用粘着剤から得られる粘着剤層と、を有する粘着剤層付ペリクルフレーム。
[14]ペリクル膜と、該ペリクル膜が一方の端面に設けられたペリクルフレームと、該ペリクルフレームの他方の端面に設けられた前記[1]~[12]のいずれかに記載のペリクル用粘着剤から得られる粘着剤層と、を有するペリクル。
[15]粘着剤層が露光光線に照射される前記[14]記載のペリクル。
[16]位相シフトフォトマスクに貼り付けられる前記[14]記載のペリクル。
[17]ネガタイプの露光原版に貼り付けられる前記[14]記載のペリクル。
[18]露光原版における粘着剤層の貼り付け部分に遮光されていない領域又は半透明遮光領域を有する露光原版に貼り付けられる前記[14]記載のペリクル。
[19]露光原版における粘着剤層の貼り付け部分に透明領域を有する露光原版に貼り付けられる前記[14]記載のペリクル。
[20]酸化ケイ素を主成分とする面に貼り付けられる前記[14]記載のペリクル。
[21]酸化ケイ素を主成分とする面が石英面である前記[20]記載のペリクル。
[22]機能水による再生洗浄に対応した前記[14]記載のペリクル。
[23]露光原版に前記[14]又は[15]記載のペリクルが装着されているペリクル付露光原版。
[24]露光原版が位相シフトフォトマスクである前記[23]記載のペリクル付露光原版。
[25]露光原版がネガタイプである前記[23]記載のペリクル付露光原版。
[26]露光原版の粘着剤層の貼り付け部分が遮光されていない領域又は半透明遮光領域を有する前記[23]記載のペリクル付露光原版。
[27]露光原版の粘着剤層の貼り付け部分が透明領域を有する前記[23]記載のペリクル付露光原版。
[28]露光原版が酸化ケイ素を主成分とする前記[23]記載のペリクル付露光原版。
[29]露光原版が石英基板である前記[23]記載のペリクル付露光原版。
[30]前記[23]~[29]のいずれかに記載のペリクル付露光原版によって露光する工程を備える半導体装置の製造方法。
[31]前記[23]~[29]のいずれかに記載のペリクル付露光原版によって露光する工程を備える液晶表示板の製造方法。
[32]前記[23]~[29]のいずれかに記載のペリクル付露光原版からペリクルを剥離し、機能水により露光原版に残った粘着剤の残渣を洗浄することにより露光原版を再生する露光原版の再生方法。
[33]ペリクルを貼り付けた露光原版からペリクルを剥離した際の、露光原版上に残る前記ペリクルの粘着剤層の剥離残渣低減方法であって、前記ペリクルとして前記[14]~[22]のいずれかに記載のペリクルを用いる、剥離残渣低減方法。
[34]ペリクル膜と、該ペリクル膜が一方の端面に設けられたペリクルフレームと、該ペリクルフレームの他方の端面に設けられた前記ペリクル用粘着剤から得られる粘着剤層と、を有するペリクルの応用であって、粘着剤層が露光光線に照射されるペリクルの応用。
[35]ペリクル膜と、該ペリクル膜が一方の端面に設けられたペリクルフレームと、該ペリクルフレームの他方の端面に設けられた前記ペリクル用粘着剤から得られる粘着剤層と、を有するペリクルの応用であって、位相シフトフォトマスクに貼り付けられるペリクルの応用。
[36]ペリクル膜と、該ペリクル膜が一方の端面に設けられたペリクルフレームと、該ペリクルフレームの他方の端面に設けられた前記ペリクル用粘着剤から得られる粘着剤層と、を有するペリクルの応用であって、ネガタイプの露光原版に貼り付けられるペリクルの応用。
[37]ペリクル膜と、該ペリクル膜が一方の端面に設けられたペリクルフレームと、該ペリクルフレームの他方の端面に設けられた前記ペリクル用粘着剤から得られる粘着剤層と、を有するペリクルの応用であって、露光原版における粘着剤層の貼り付け部分に遮光されていない領域又は半透明遮光領域を有する露光原版に貼り付けられるペリクルの応用。
[38]ペリクル膜と、該ペリクル膜が一方の端面に設けられたペリクルフレームと、該ペリクルフレームの他方の端面に設けられた前記ペリクル用粘着剤から得られる粘着剤層と、を有するペリクルの応用であって、露光原版における粘着剤層の貼り付け部分に透明領域を有する露光原版に貼り付けられるペリクルの応用。
[39]ペリクル膜と、該ペリクル膜が一方の端面に設けられたペリクルフレームと、該ペリクルフレームの他方の端面に設けられた前記ペリクル用粘着剤から得られる粘着剤層と、を有するペリクルの応用であって、酸化ケイ素を主成分とする面(特に石英面)に貼り付けられるペリクルの応用。
[40]ペリクル膜と、該ペリクル膜が一方の端面に設けられたペリクルフレームと、該ペリクルフレームの他方の端面に設けられた前記ペリクル用粘着剤から得られる粘着剤層と、を有するペリクルの応用であって、機能水による再生洗浄に対応したペリクルの応用。
[41]ペリクル膜と、該ペリクル膜がその一方の端面に貼り付けられたペリクルフレームと、該ペリクルフレームの他方の端面に設けられたペリクルを露光原版に貼り付けるための粘着剤層とを含んで構成される剥離残渣低減ペリクルであって、前記粘着剤層が、SP値10.0以上12.0以下であるアクリル樹脂を母材とすることを特徴とする剥離残渣低減ペリクル。
[42]前記粘着剤層は、さらにポリビニルエーテル化合物を含有する、前記[41]記載の剥離残渣低減ペリクル。
[43]前記剥離残渣低減ペリクルが、ArFリソグラフィ用の剥離残渣低減ペリクルである、前記[41]又は[42]記載の剥離残渣低減ペリクル。
[44]ペリクルを露光原版に貼り付けるための粘着剤を選定し、ペリクルフレームの一方の端面に当該粘着剤を塗布して粘着剤層を作り、これに保護部材を剥離可能に貼着し、ペリクルフレームの他方の端面に接着剤を塗布し、これにペリクル膜を貼り付ける、剥離残渣低減ペリクルの製造方法であって、
前記粘着剤の選定において、SP値10.0以上12.0以下であるアクリル樹脂を母材とするものを選択することを特徴とする、剥離残渣低減ペリクルの製造方法。
[45]前記粘着剤層は、さらにポリビニルエーテル化合物を含有する、前記[44]記載の剥離残渣低減ペリクルの製造方法。
[46]ペリクルを貼り付けた露光原版からペリクルを剥離した際に、露光原版上に残る前記ペリクルの粘着剤層の剥離残渣を低減する方法であって、
前記ペリクルとして、前記[41]~[43]のいずれかに記載のペリクルを用いることを特徴とする方法。
本発明のペリクルは、粘着剤の母材として、特定のアクリル系重合体(アクリル樹脂ともいう)を用いたことにより、粘着剤内部の分子間力が向上し、かつ適正な粘着力を保つことができ、露光原版からの剥離時に大きな残渣はもとより、粒子状の残渣も減少したものと推測される。
すなわち、本発明のペリクル用粘着剤の第一の側面は、SP値が10.0以上12.0以下であるアクリル系重合体を母材とすることである。アクリル系重合体のSP値を10.0以上12.0以下にすることで、露光原版からペリクルを剥離した際、該露光原版上に残る粘着剤層の剥離残渣を少なくすることができる。SP値が10.0以上であることにより、洗浄で除去しにくい残渣を少なくすることができる。一方、SP値が12.0以下であることにより、粘着剤の揮発性を低くすることができヘイズの抑制につながる。SP値を特定範囲とすることによりアクリル系重合体の親水性を向上させたことにより本発明の効果が得られるのではないかと本発明者らは推察する。
なお、本発明において、「アクリル系重合体を母材とする粘着剤」とは、アクリル系重合体それ自体を含む粘着剤、又はアクリル系重合体と硬化剤等との反応生成物を含む粘着剤を意味する。
本発明において、アクリル系重合体は、例えば、(メタ)アクリル酸エステルを単量体成分とする重合体であり、必要に応じて(メタ)アクリル酸エステルと共重合可能な単量体成分を共重合することができる。(メタ)アクリル酸エステルとしては、例えば、エーテル結合を有する(メタ)アクリル酸エステル、(メタ)アクリル酸アルキルエステル、カルボキシル基又はヒドロキシル基を有する不飽和モノマー等が挙げられる。エーテル結合を有する(メタ)アクリル酸エステルを単量体成分として含むことでアクリル系重合体の側鎖にエーテル結合を導入することができる。
アクリル系重合体の分子量は、重量平均分子量として70万~250万の範囲内にあると、粘着剤層の凝集力、接着力が適度な大きさになり、糊残りしにくく、且つ、十分な接着力、耐荷重性を持つ粘着剤となり、好ましい。
なお、本実施形態において、粘着剤層の粘着剤としては、アクリル系重合体と硬化剤との反応生成物を含むことが好ましいが、柔らかさを考慮して、硬化剤と反応させないアクリル系重合体を含んでもよい。
[SP値の算出方法]
本発明においてSP値は、溶解度パラメーター(solubility parameter)である。このSP値は、Fedorsの算出法[「Polymer Engineering and Science」、第14巻、第2号(1974)、148~154ページ]を参照し、下記数式1により算出することで求めることができる。
アクリル系重合体のSP値は、例えば、アクリル系重合体中の極性基濃度を変化させることによって制御することができる。例えば、エーテル結合のような比較的に極性の高い結合を側鎖に導入するとSP値は高くなる方向に進む。一方、長鎖のアルキレン結合のような比較的に極性の低い結合を側鎖に導入するとSP値は低くなる方向に進む。
また、本発明のペリクルを用いることにより、粘着剤層の剥離残渣が低減されることから機能水による洗浄が適用容易となり、位相シフトフォトマスクなどのデリケートな露光原版に対する洗浄性を向上することができる。また、機能水洗浄による環境負荷の低減に貢献できる。
アルミニウム合金製のペリクルフレーム(外形サイズ149mm×115mm×3.5mm、肉厚2mm、マスク貼り付け用粘着剤塗布端面側の平坦度:15um)を精密洗浄後、平坦度が15um側の端面に綜研化学社製のアクリル粘着剤(製品名:SKダイン SN-70A、単量体成分の95質量%がエチレンオキサイド基含有(メタ)アクリレートであるアクリル系重合体を母材として含む、母材のSP値10.2)を塗布し、60分室温で静置した。その後、平坦度が5umのアルミ板上にセパレータを置き、粘着剤を塗布したペリクルフレームを粘着剤が下向きになるように置いた。これにより粘着剤は平坦なセパレータに接触して平坦加工された。
次に、アルミ板上のペリクルを60℃のオーブンに60分入れて粘着剤を硬化させた。
そして、ペリクルをアルミ板ごと取り出した後、セパレータを剥離した。
最後に、上記ペリクルフレームよりも大きなアルミニウム枠にとったペリクル膜に上記ペリクルフレームの接着剤塗布端面側を貼り付け、ペリクルフレームよりも外側の部分を除去し、ペリクルを完成させた。
紫外線照射後1時間室温で放置した後、ペリクルをマスク基板から0.1mm/秒のスピードで上方にゆっくり剥離した。
粘着剤として、綜研化学社製のアクリル粘着剤(製品名:SN-25B、単量体成分の40質量%がエチレンオキサイド基含有(メタ)アクリレートであるアクリル系重合体を母材として含む、母材のSP値 10.5)を使用した以外は実施例1と同じ方法と材料でペリクルを完成した。さらに実施例1と同様の条件でペリクルをマスク基板に貼り付け、かつ剥離した。
粘着剤として、SKダイン SN-70A 100質量部に対してポリビニルエーテル化合物3質量部を含ませたことを除いては、実施例1と同じ方法と材料でペリクルを完成した。さらに実施例1と同様の条件でペリクルをマスク基板に貼り付け、かつ剥離した。
粘着剤として、綜研化学社製のアクリル粘着剤(製品名:SKダイン SK-1425S、エーテル結合を有する(メタ)アクリル酸エステルを単量体成分として含まないアクリル系重合体を母材として含む、母材のSP値 9.8)を使用した以外は実施例1と同じ方法と材料でペリクルを完成した。さらに実施例1と同様の条件でペリクルをマスク基板に貼り付け、かつ剥離した。
粘着剤として、綜研化学社製のアクリル粘着剤(製品名:SKダイン SK-1495S、エーテル結合を有する(メタ)アクリル酸エステルを単量体成分として含まないアクリル系重合体を母材として含む、母材のSP値 9.2)を使用した以外は実施例1と同じ方法と材料でペリクルを完成した。さらに実施例1と同様の条件でペリクルをマスク基板に貼り付け、かつ剥離した。
撹拌機、還流冷却器、温度計及びガス吹き込み口が取り付けられた5L容フラスコに、ブチルアクリレート 320g、2-メトキシエチルアクリレート 550g、アクリル酸 80g、2-ヒドロキシエチルアクリレート 50g、酢酸エチル 1500gおよび重合開始剤であるアゾビスイソブチロニトリル 2gを仕込み、窒素ガス気流中、68℃で8時間溶液重合を行った。 反応終了後、これに酢酸エチル 830gを加え、固形分30%のアクリル系重合体(SP値 10.6)の溶液を得た。得られたアクリル系重合体溶液にポリイソシアネートの溶液を添加し、撹拌混合して粘着剤を得た。
撹拌機、還流冷却器、温度計及びガス吹き込み口が取り付けられた5L容フラスコに、2-エチルヘキシルアクリレート 400g、2-エトキシエチルアクリレート 500g、アクリル酸 100g、酢酸エチル 1200gおよび重合開始剤であるアゾビスイソブチロニトリル 2gを仕込み、窒素ガス気流中、68℃で8時間溶液重合を行った。 反応終了後、これに酢酸エチル 1130gを加え、固形分30%のアクリル系重合体(SP値 10.1)の溶液を得た。得られたアクリル系重合体溶液にポリイソシアネートの溶液を添加し、撹拌混合して粘着剤を得た。
撹拌機、還流冷却器、温度計及びガス吹き込み口が取り付けられた5L容フラスコに、2-エチルヘキシルアクリレート 350g、2-メトキシエチルアクリレート 550g、メタクリル酸 50g、2-ヒドロキシエチルメタクリレート 50g、酢酸エチル 1400gおよび重合開始剤であるアゾビスイソブチロニトリル 2gを仕込み、窒素ガス気流中、68℃で8時間溶液重合を行った。反応終了後、これに酢酸エチル 930gを加え、固形分30%のアクリル系重合体(SP値 10.2)の溶液を得た。得られたアクリル系重合体溶液にポリイソシアネートの溶液を添加し、撹拌混合して粘着剤を得た。
撹拌機、還流冷却器、温度計及びガス吹き込み口が取り付けられた5L容フラスコに、ブチルアクリレート 300g、2-メトキシエチルアクリレート550g、ビロキシブチルアクリレート 100g、イタコン酸 50g、酢酸エチル1500gおよび重合開始剤であるアゾビスイソブチロニトリル 2gを仕込み、窒素ガス気流中、68℃で8時間溶液重合を行った。 反応終了後、これに酢酸エチル 830gを加え、固形分30%のアクリル系重合体溶液を得た。得られたアクリル系重合体(SP値 約10.7)の溶液にポリイソシアネートの溶液を添加し、撹拌混合して粘着剤を得た。
撹拌機、還流冷却器、温度計及びガス吹き込み口が取り付けられた5L容フラスコに、ブチルアクリレート 300g、メトキシポリエチレングリコールアクリレート 600g、アクリル酸 100g、酢酸エチル 1400gおよび重合開始剤であるアゾビスイソブチロニトリル 2gを仕込み、窒素ガス気流中、68℃で8時間溶液重合を行った。 反応終了後、これに酢酸エチル 930gを加え、固形分30%のアクリル系重合体(SP値 約10)の溶液を得た。得られたアクリル系重合体溶液にポリイソシアネートの溶液を添加し、撹拌混合して粘着剤を得た。
粘着剤として合成例1~5で得られた粘着剤を各々使用した以外は実施例1と同様にしてペリクルを作製し、剥離試験を行った。その結果、いずれの粘着剤を使用したペリクルでも比較例と比較し剥離残渣が低減し、洗浄除去性が改善されていた。
10 ペリクル
11 ペリクルフレーム
12 ペリクル膜
13 ペリクル膜貼り付け用接着剤層
14 粘着剤層
15 気圧調整用穴(通気口)
16 除塵用フィルター
Claims (33)
- 露光原版にペリクルを貼り付けるためのペリクル用粘着剤であって、SP値が10.0以上12.0以下であるアクリル系重合体を母材とするペリクル用粘着剤。
- 露光原版にペリクルを貼り付けるためのペリクル用粘着剤であって、エーテル結合を有する(メタ)アクリル酸エステルを単量体成分とするアクリル系重合体を母材とするペリクル用粘着剤。
- エーテル結合を有する(メタ)アクリル酸エステルが、アルキレンオキサイド基を有する(メタ)アクリル酸エステルである請求項2記載のペリクル用粘着剤。
- エーテル結合を有する(メタ)アクリル酸エステルが、全単量体成分に対して30質量%以上含まれる請求項3記載のペリクル用粘着剤。
- アルキレンオキサイド基が、エチレンオキサイド基である請求項3又は4記載のペリクル用粘着剤。
- 単量体成分として、さらにカルボキシル基又はヒドロキシル基を有する不飽和モノマーを含む請求項2~5いずれか一項記載のペリクル用粘着剤。
- 単量体成分として、さらに(メタ)アクリル酸アルキルエステルを含む請求項2~6いずれか一項記載のペリクル用粘着剤。
- 露光原版にペリクルを貼り付けるためのペリクル用粘着剤であって、エーテル結合を含む側鎖を有するアクリル系重合体を母材とするペリクル用粘着剤。
- エーテル結合を含む側鎖が、アルキレンオキサイド基を有する請求項8記載のペリクル用粘着剤。
- アルキレンオキサイド基が、エチレンオキサイド基である請求項9記載のペリクル用粘着剤。
- 露光原版にペリクルを貼り付けるためのペリクル用粘着剤であって、露光光線の照射による分解性が主鎖よりも高い側鎖を有するアクリル系重合体を母材とするペリクル用粘着剤。
- 露光原版にペリクルを貼り付けるためのペリクル用粘着剤であって、露光光線の照射により選択的に劣化する側鎖を有するアクリル系重合体を母材とするペリクル用粘着剤。
- ペリクルフレームと、該ペリクルフレームの一方の端面に設けられた請求項1~12いずれか一項記載のペリクル用粘着剤から得られる粘着剤層と、を有する粘着剤層付ペリクルフレーム。
- ペリクル膜と、該ペリクル膜が一方の端面に設けられたペリクルフレームと、該ペリクルフレームの他方の端面に設けられた請求項1~12いずれか一項記載のペリクル用粘着剤から得られる粘着剤層と、を有するペリクル。
- 粘着剤層が露光光線に照射される請求項14記載のペリクル。
- 位相シフトフォトマスクに貼り付けられる請求項14記載のペリクル。
- ネガタイプの露光原版に貼り付けられる請求項14記載のペリクル。
- 露光原版における粘着剤層の貼り付け部分に遮光されていない領域又は半透明遮光領域を有する露光原版に貼り付けられる請求項14記載のペリクル。
- 露光原版における粘着剤層の貼り付け部分に透明領域を有する露光原版に貼り付けられる請求項14記載のペリクル。
- 酸化ケイ素を主成分とする面に貼り付けられる請求項14記載のペリクル。
- 酸化ケイ素を主成分とする面が石英面である請求項20記載のペリクル。
- 機能水による再生洗浄に対応した請求項14記載のペリクル。
- 露光原版に請求項14又は15記載のペリクルが装着されているペリクル付露光原版。
- 露光原版が位相シフトフォトマスクである請求項23記載のペリクル付露光原版。
- 露光原版がネガタイプである請求項23記載のペリクル付露光原版。
- 露光原版の粘着剤層の貼り付け部分が遮光されていない領域又は半透明遮光領域を有する請求項23記載のペリクル付露光原版。
- 露光原版の粘着剤層の貼り付け部分が透明領域を有する請求項23記載のペリクル付露光原版。
- 露光原版が酸化ケイ素を主成分とする請求項23記載のペリクル付露光原版。
- 露光原版が石英基板である請求項23記載のペリクル付露光原版。
- 請求項23~29いずれか一項記載のペリクル付露光原版によって露光する工程を備える半導体装置の製造方法。
- 請求項23~29いずれか一項記載のペリクル付露光原版によって露光する工程を備える液晶表示板の製造方法。
- 請求項23~29いずれか一項記載のペリクル付露光原版からペリクルを剥離し、機能水により露光原版に残った粘着剤の残渣を洗浄することにより露光原版を再生する露光原版の再生方法。
- ペリクルを貼り付けた露光原版からペリクルを剥離した際の、露光原版上に残る前記ペリクルの粘着剤層の剥離残渣低減方法であって、前記ペリクルとして請求項14~22いずれか一項記載のペリクルを用いる、剥離残渣低減方法。
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PCT/JP2020/016624 WO2020213659A1 (ja) | 2019-04-16 | 2020-04-15 | ペリクル、ペリクル付露光原版、半導体装置の製造方法、液晶表示板の製造方法、露光原版の再生方法及び剥離残渣低減方法 |
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JP7390226B2 (ja) * | 2020-03-18 | 2023-12-01 | 綜研化学株式会社 | 粘着剤組成物、粘着剤層および粘着シート |
JP7341970B2 (ja) * | 2020-10-14 | 2023-09-11 | 信越化学工業株式会社 | ペリクル用粘着剤、粘着剤層付ペリクルフレーム、ペリクル、ペリクル付露光原版、露光方法、半導体の製造方法及び液晶表示板の製造方法 |
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