WO2023182186A1 - Procédé de fabrication d'un cadre de pellicule comportant une couche adhésive sensible à la pression, cadre de pellicule à film protecteur, cadre de pellicule comportant une couche adhésive sensible à la pression, pellicule et photomasque comportant une pellicule - Google Patents

Procédé de fabrication d'un cadre de pellicule comportant une couche adhésive sensible à la pression, cadre de pellicule à film protecteur, cadre de pellicule comportant une couche adhésive sensible à la pression, pellicule et photomasque comportant une pellicule Download PDF

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Publication number
WO2023182186A1
WO2023182186A1 PCT/JP2023/010465 JP2023010465W WO2023182186A1 WO 2023182186 A1 WO2023182186 A1 WO 2023182186A1 JP 2023010465 W JP2023010465 W JP 2023010465W WO 2023182186 A1 WO2023182186 A1 WO 2023182186A1
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WO
WIPO (PCT)
Prior art keywords
adhesive layer
pellicle
pellicle frame
photomask
protective film
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Application number
PCT/JP2023/010465
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English (en)
Japanese (ja)
Inventor
真史 藤村
健 伊藤
陽介 小野
崇 畦崎
Original Assignee
三井化学株式会社
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Application filed by 三井化学株式会社 filed Critical 三井化学株式会社
Publication of WO2023182186A1 publication Critical patent/WO2023182186A1/fr

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Classifications

    • 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
    • C09J201/00—Adhesives based on unspecified macromolecular compounds
    • 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]
    • 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

Definitions

  • the present disclosure relates to a method for manufacturing a pellicle frame with an adhesive layer, a pellicle frame with a protective film, a pellicle frame with an adhesive layer, a pellicle, and a photomask with a pellicle.
  • Photolithography uses a photomask with a pattern formed on one side.
  • a pellicle is used in a photomask to prevent foreign matter such as dust from adhering to the surface of the photomask.
  • the pellicle has an adhesive layer and is attached to the photomask.
  • a photomask to which a pellicle is attached will also be referred to as a "photomask with a pellicle.”
  • the surface flatness of the adhesive layer of a pellicle is inferior to that of a photomask. Therefore, in order to prevent the occurrence of air paths, when attaching a pellicle to a photomask, a load is applied to the pellicle to adhere the adhesive layer to the photomask without any gaps. At this time, the softer the adhesive, the smaller the force required to bring the surface of the photomask and the surface of the adhesive layer into close contact.
  • Patent Document 1 discloses a pellicle using a soft adhesive.
  • the pellicle disclosed in Patent Document 1 has an adhesive layer that can be attached to a photomask with an attachment load of 0.008 kgf to 5 kgf, including its own weight.
  • the adhesive layer has a Young's modulus of 0.01 MPa to 0.10 MPa.
  • the adhesive layer has a tensile adhesive strength of 0.02 N/mm 2 to 0.10 N/mm 2 .
  • the surface flatness of the adhesive layer is 0 ⁇ m to 15 ⁇ m.
  • the adhesive layer of the pellicle disclosed in Patent Document 1 is formed by applying an adhesive to the end face of the pellicle frame using a dispenser and heating the adhesive to harden the adhesive.
  • the resulting pellicle is attached to the photomask by bringing the adhesive layer into contact with the photomask and applying the above-mentioned attachment load.
  • Patent Document 1 Japanese Patent Application Publication No. 2012-230227
  • Patent Document 1 the surface of the adhesive layer of the pellicle is not flattened before being attached to the photomask. Therefore, when a pellicle is attached to a photomask, there is a risk that a large number of air traps will be formed between the surface of the photomask and the surface of the adhesive layer of the pellicle.
  • an air path may be formed.
  • An air path is a local gap that communicates the outside of the pellicle with the inside of the pellicle.
  • An air trap is a local gap that does not communicate the outside of the pellicle with the inside of the pellicle, and expands during exposure, etc., and becomes a cause of an air path.
  • foreign matter outside the pellicle may enter the inside of the pellicle.
  • EUV is used as exposure light. Because EUV has a short wavelength, it is easily absorbed by gases such as oxygen or nitrogen. Therefore, EUV exposure is performed in a vacuum atmosphere.
  • gases such as oxygen or nitrogen. Therefore, EUV exposure is performed in a vacuum atmosphere.
  • air pockets tend to expand. Therefore, if there are a large number of air traps when a pellicle is attached to a photomask in an atmospheric environment, there is a risk that air paths will be more likely to be formed during EUV exposure.
  • the present disclosure has been made in view of the above circumstances. Problems to be solved by an embodiment of the present disclosure are a method for manufacturing a pellicle frame with an adhesive layer that can suppress the number of air bites when a pellicle is attached to a photomask, a pellicle frame with a protective film, and a pellicle frame with a protective film. and to provide a pellicle frame with an adhesive layer.
  • a problem to be solved by other embodiments of the present disclosure is to provide a photomask with a pellicle that can suppress the occurrence of air paths.
  • Means for solving the above problems include the following embodiments. ⁇ 1> A method for manufacturing a pellicle frame with an adhesive layer, which includes a pellicle frame and an adhesive layer formed on the pellicle frame for pasting on a photomask, A step A of preparing a frame precursor comprising the pellicle frame and a precursor layer formed on the pellicle frame and which is a precursor of the adhesive layer; Step B of arranging a protective film on the surface of the precursor layer to form a frame precursor with a protective film; a step C of heat-treating the frame precursor with a protective film to form the adhesive layer with a flattened surface from the precursor layer; A method for producing a pellicle frame with an adhesive layer, wherein the glass transition temperature of the protective film is higher than the heating temperature in step C.
  • ⁇ 2> The method for manufacturing a pellicle frame with an adhesive layer according to ⁇ 1> above, wherein the protective film has a glass transition temperature of over 120°C.
  • ⁇ 3> The method for manufacturing a pellicle frame with an adhesive layer according to ⁇ 1> or ⁇ 2>, wherein in the step C, the heat treatment conditions are 80° C. or higher and 2 hours or longer.
  • the adhesive layer includes at least one selected from the group consisting of an acrylic adhesive, a silicone adhesive, a styrene-butadiene adhesive, a urethane adhesive, and an olefin adhesive.
  • the adhesive layer includes at least one selected from the group consisting of an acrylic adhesive, a silicone adhesive, a styrene-butadiene adhesive, a urethane adhesive, and an olefin adhesive.
  • Pellicle frame with adhesive layer described in . ⁇ 8> A pellicle membrane supported by the pellicle frame, and a pellicle frame with an adhesive layer according to ⁇ 6> or ⁇ 7>, A pellicle, wherein the pellicle film includes at least one selected from the group consisting of carbon nanotubes, metal silicide, and polysilicon.
  • a method for manufacturing a pellicle frame with an adhesive layer, a pellicle frame with a protective film, and a pellicle frame with an adhesive layer which can suppress the number of air bites when a pellicle is attached to a photomask. It is. According to the present disclosure, it is an object of the present disclosure to provide a photomask with a pellicle that can suppress the occurrence of air paths.
  • FIG. 1 is a schematic cross-sectional view showing a cross section of a pellicle frame with a protective film according to Example 1.
  • a numerical range indicated using “ ⁇ ” means a range that includes the numerical values listed before and after " ⁇ " as the minimum and maximum values, respectively.
  • the upper limit or lower limit described in a certain numerical range may be replaced with the upper limit or lower limit of another numerical range described step by step.
  • the upper limit value or lower limit value described in a certain numerical range may be replaced with the value shown in the examples.
  • a combination of two or more preferred embodiments is a more preferred embodiment.
  • the amount of each component means the total amount of the multiple types of substances, unless otherwise specified.
  • step is used not only to refer to an independent step, but also to include a step in this term if the intended purpose of the step is achieved, even if the step cannot be clearly distinguished from other steps. It will be done.
  • (meth)acrylate means acrylate or methacrylate.
  • the method for manufacturing a pellicle frame with an adhesive layer includes a pellicle frame and an adhesive layer formed on the pellicle frame and an adhesive layer for attaching to a photomask.
  • This is a method of manufacturing a pellicle frame with a casing.
  • the manufacturing method includes Step A, Step B, and Step C.
  • step A a frame precursor is prepared.
  • the frame precursor includes the pellicle frame and a precursor layer that is a precursor of the adhesive layer and is formed on the pellicle frame.
  • a protective film is placed on the surface of the precursor layer to form a frame precursor with a protective film.
  • the protective film-attached frame precursor is heat-treated to form the adhesive layer with a flattened surface from the precursor layer.
  • the glass transition temperature of the protective film is higher than the heating temperature in step C.
  • the "adhesive layer precursor" becomes an adhesive layer when subjected to the heat treatment in step C.
  • the "glass transition temperature of a protective film” refers to a layer in which the protective film is a base layer and a layer different from the base layer (for example, a release layer, a layer that facilitates peeling from an adhesive layer, an antistatic layer, etc.). etc.), it indicates the glass transition temperature of the base material layer.
  • Heating temperature in step C indicates the set temperature of the heating device when a heating device (for example, an oven, a hot plate, etc.) is used to perform the heat treatment.
  • the "heating temperature of process C” is the set temperature in the oven
  • the "heating temperature of process C” is the setting of the hot plate. It's temperature.
  • process A will also be referred to as a "preparation process.”
  • process B will also be referred to as a "placement process.”
  • process C will also be referred to as a "flattening process”.
  • glass transition temperature will also be referred to as "Tg”.
  • the manufacturing method of the present disclosure has the above configuration, it is possible to suppress the number of air bites when a pellicle is attached to a photomask. This effect is presumed to be due to the following reasons, but is not limited thereto.
  • the glass transition temperature of the protective film is higher than the heating temperature in step C. In other words, the occurrence of distortion in the protective film due to heating in step C is suppressed. Therefore, in Step C, the distortion of the protective film is unlikely to be transferred to the surface of the adhesive layer in the present disclosure.
  • the surface of the adhesive layer according to the present disclosure tends to be more flat than when using a protective film whose Tg is equal to or lower than the heating temperature in step C.
  • the number of local steps on the surface of the adhesive layer in the present disclosure is smaller than that in the case of using a protective film with Tg equal to or lower than the heating temperature in step C in an atmospheric environment.
  • the manufacturing method of the present disclosure can suppress the number of air traps when a pellicle is attached to a photomask. Therefore, if the pellicle frame with an adhesive layer obtained by the manufacturing method of the present disclosure is used as a pellicle component, air paths are less likely to occur during exposure. Furthermore, since there is little air entrapment, the adhesive surface to the photomask becomes uniform. Therefore, distortion of the photomask can be suppressed.
  • the method for measuring the number of local steps on the surface of the adhesive layer is the same as the method described in Examples.
  • the preparation process, placement process, and planarization process are performed in this order.
  • the manufacturing method of the present disclosure is a method of manufacturing a pellicle frame with an adhesive layer.
  • the pellicle frame with an adhesive layer is a component of a pellicle, and includes a pellicle frame and an adhesive layer for attaching to a photomask.
  • the adhesive layer is formed on the pellicle frame. The pellicle will be described later.
  • the pellicle frame is a rectangular frame. Specifically, the pellicle frame is a rectangular cylindrical object.
  • the pellicle frame has a through hole.
  • the through hole indicates a space through which light transmitted through the pellicle film passes to reach the photomask.
  • the pellicle film will be described later.
  • the pellicle frame has one end surface on which the adhesive layer is provided and the other end surface that directs the pellicle membrane.
  • the pellicle frame may have a vent with a filter.
  • the ventilation hole communicates the interior space of the pellicle with the exterior space of the pellicle when the pellicle frame is attached to the photomask.
  • Internal space of the pellicle refers to a space surrounded by the pellicle and the photomask.
  • Space outside the pellicle refers to a space that is not surrounded by the pellicle and the photomask.
  • the filter is arranged between the interior space of the pellicle and the exterior space of the pellicle to prevent foreign matter from passing through.
  • the rectangular shape may be a square or a rectangle.
  • Rectangle refers to a right-angled quadrilateral.
  • a “square” refers to a rectangular shape in which all four sides are equal in length. “Rectangle” refers to a rectangle excluding a square.
  • one end surface of the pellicle frame on which the adhesive layer is provided is also referred to as the "exposed substrate end surface”
  • the other end surface of the pellicle frame that supports the pellicle film is also referred to as the "pellicle film end surface”.
  • the material of the pellicle frame is not particularly limited, and examples include metal, resin, and ceramic materials.
  • the metal may be a pure metal or an alloy. Pure metals consist of a single metallic element. Examples of pure metals include aluminum, titanium, and the like.
  • An alloy consists of a plurality of metal elements or a metal element and a non-metal element. Examples of the alloy include stainless steel, magnesium alloy, steel, carbon steel, and invar.
  • Examples of the resin include polyethylene.
  • ceramic materials include silicon nitride (SiN), silicon carbide (SiC), alumina (Al 2 O 3 ), and the like.
  • the pellicle frame may be a single piece or an assembled piece.
  • a single product is obtained by cutting out one raw material board.
  • An "assembly" is one that integrates multiple members. Examples of methods for integrating a plurality of members include a method using a known adhesive and a method using fastening parts. Fastening parts include bolts, nuts, screws, rivets, or pins. When the pellicle frame is an assembled product, the materials of the plurality of members may be different.
  • the Young's modulus of the member constituting the photomask end face is 60 GPa or less
  • the Young's modulus of the member constituting the pellicle membrane end face (hereinafter referred to as "membrane support frame member”) is preferably 90 GPa or more.
  • the pellicle frame assembly can suppress deformation of the pellicle frame due to distortion of the membrane support frame member due to the tension of the pellicle membrane.
  • materials having a Young's modulus of 60 GPa or less include magnesium, magnesium alloys, polyethylene terephthalate (PET) resins, resins, and the like.
  • Examples of materials having a Young's modulus of 90 GPa or more include titanium, titanium alloy, silicon, and the like.
  • the Young's modulus was measured using a tensile test (JIS G0567J). However, if the material of the pellicle frame is resin, the value is measured by a three-point bending test (JIS K7171). Whether the material of the pellicle frame is resin or not is determined by whether it thermally decomposes at 550°C.
  • Adhesive layer is formed on the pellicle frame. Specifically, the adhesive layer is formed on the exposed substrate end surface of the pellicle frame.
  • the adhesive layer is a gel-like viscoelastic body. It is preferable that the adhesive layer has viscosity and cohesive force. "Viscosity” refers to the property of a liquid that comes into contact with and wets the photomask that is the adherend. “Cohesion” refers to solid-like properties that resist peeling from the photomask.
  • the Tg of the adhesive layer is preferably greater than -25°C and less than 10°C.
  • the adhesive layer has adhesive strength in the operating temperature range of the pellicle (for example, 20° C. or higher), and is more difficult to peel off from the photomask even when exposed to a high-temperature environment.
  • the lower limit of the Tg of the adhesive layer is preferably higher than -25°C, more preferably higher than -22°C, still more preferably higher than -20°C, Most preferably the temperature is -18°C or higher.
  • the upper limit of Tg of the adhesive layer is preferably less than 10°C, more preferably 5°C or less, and still more preferably 0°C or less.
  • the method for measuring Tg of the adhesive layer is based on JIS K7112. Specifically, the Tg of the adhesive layer is measured using a differential scanning calorimetry (DSC) at a temperature increase rate of 20° C./min under nitrogen conditions.
  • DSC differential scanning calorimetry
  • the adhesive layer is made of an adhesive composition.
  • the adhesive composition constituting the adhesive layer is not particularly limited, and examples thereof include acrylic adhesives, silicone adhesives, styrene-butadiene adhesives, urethane adhesives, olefin adhesives, and the like. Among them, from the viewpoint of reducing the amount of outgas generated from the pellicle, the adhesive layer is made of an acrylic adhesive, a silicone adhesive, a styrene-butadiene adhesive, a urethane adhesive, and an olefin adhesive.
  • the adhesive preferably contains at least one selected from the group, more preferably an acrylic adhesive, and even more preferably an acrylic adhesive. Details of the acrylic adhesive will be described later.
  • the thickness of the adhesive layer is not particularly limited, and is preferably 10 ⁇ m to 500 ⁇ m, more preferably 100 ⁇ m to 400 ⁇ m, and still more preferably 200 ⁇ m to 300 ⁇ m. If the thickness of the adhesive layer is within the above range, the amount of outgas from the adhesive layer will have less influence.
  • the method for measuring the thickness of the adhesive layer is the same as in the examples.
  • the manufacturing method of the present disclosure includes a preparation process.
  • a frame precursor is prepared.
  • the frame precursor includes a pellicle frame and a precursor layer that is a precursor of an adhesive layer.
  • a precursor layer is formed on the pellicle frame. Specifically, the precursor layer is formed on the exposed substrate end surface of the pellicle frame.
  • the method for preparing the frame precursor is not particularly limited, and examples thereof include a method of applying a coating composition to a pellicle frame to form a precursor layer on the photomask end surface of the pellicle frame.
  • the coating composition includes a composition containing a compound selected from various polymers, solvents, crosslinking agents, catalysts, initiators, etc., depending on the type of adhesive layer.
  • the coating composition is a precursor to the adhesive composition. That is, when the coating composition is cured, it becomes the adhesive composition described above.
  • the method of applying the coating composition to the photomask end face of the pellicle frame is not particularly limited, and examples include a method using a dispenser.
  • the area to which the coating composition is applied is not the entire surface of the photomask end surface, but only the center portion of each side between the four corners of the photomask end surface.
  • the area to which the coating composition is applied preferably does not include the edge of the pellicle frame on the through-hole side of each side between the four corners and the edge of the pellicle frame on the opposite side from the through-hole side.
  • the adhesive layer is less likely to overflow to the inner and outer peripheral walls of the pellicle frame than when the coating composition is applied to the entire end face of the photomask. Therefore, the adhesive layer is less likely to be exposed. As a result, the amount of outgas generated can be further reduced.
  • the thickness of the precursor layer may be such that the thickness of the adhesive layer falls within the above-mentioned range.
  • the manufacturing method of the present disclosure may include a drying process.
  • the preparation process, drying process, placement process, and flattening process are performed in this order.
  • the frame precursor is subjected to a drying process.
  • the coating composition may contain a solvent.
  • the drying step most of the solvent contained in the precursor layer of the frame precursor evaporates before performing the planarization step. As a result, it becomes easier to obtain an adhesive layer with a flattened surface.
  • the heating temperature for the drying treatment is preferably lower than the heating temperature for the flattening step, and is appropriately selected depending on the type of coating composition, and is preferably 40°C to 120°C, more preferably 50°C to 110°C, More preferably the temperature is 60°C to 100°C.
  • the heating time of the drying treatment is appropriately selected depending on the heating temperature of the drying treatment, the type of coating composition, etc., and is preferably 10 minutes to 5 hours, more preferably 20 minutes to 4 hours, and even more preferably 30 minutes to 3 hours. It's time.
  • the method for drying the precursor layer is not particularly limited, and examples thereof include a method using an oven.
  • the precursor layer is dried by placing the precursor frame inside the oven and drying the body frame itself.
  • the set temperature in the oven is the same as the temperature range exemplified as the heating temperature for the drying process described above.
  • the set temperature inside the oven indicates the internal temperature of the oven.
  • the time range for heating the precursor layer using the oven is the same as the time range exemplified as the heating time for the drying treatment described above.
  • the manufacturing method of the present disclosure includes a placement step.
  • a protective film is placed on the surface of the precursor layer of the frame precursor to form a frame precursor with a protective film.
  • the shape of the protective film is not particularly limited, and may be any shape that follows the shape of the pellicle frame.
  • the protective film may have an opening like the pellicle frame.
  • the thickness of the protective film is not particularly limited, and is preferably 5 ⁇ m to 500 ⁇ m, more preferably 30 ⁇ m to 200 ⁇ m.
  • the protective film preferably includes a base layer and a release layer, and may include other layers (for example, an antistatic layer, etc.) different from the base layer and the release layer, if necessary. good.
  • the layer structure of the protective film is not particularly limited, and may have two or more layers.
  • the base material layer contains a resin whose glass transition temperature is higher than the heating temperature in the flattening step.
  • the resin constituting the base layer is appropriately selected depending on the heating temperature in the flattening step, and includes, for example, polyester resins (e.g., polyethylene naphthalate (PEN), polybutylene terephthalate (PBT), etc.), olefin resins, etc.
  • polyvinyl chloride vinyl acetate resin
  • polycarbonate polyphenylene sulfide
  • amide resin e.g. polyamide (nylon), fully aromatic polyamide (aramid), etc.
  • polyimide resin polyether ether ketone (PEEK)
  • fluorine resin examples include resin.
  • ⁇ -olefin for example, polyethylene (PE), polypropylene (PP), polymethylpentene (PMP), ethylene-propylene copolymer, ethylene-vinyl acetate copolymer (EVA), etc.
  • the mold release layer consists of a mold release agent. Examples of the mold release agent include silicone mold release agents, fluorine mold release agents, and the like.
  • the Tg of the protective film (that is, the Tg of the base layer) is preferably higher than 120°C.
  • the Tg of commonly used protective films made of polyethylene terephthalate (PET) is less than 100°C.
  • PET protective film generally includes a base layer made of PET and a release layer formed on one surface of the base layer.
  • protective films whose Tg is over 120°C include PEN protective films, polyamide (aramid), polyimide, polyamideimide, polyetheretherketone resin (PEEK), polyphenylene sulfide, polyethersulfine, polycarbonate, and polyamide. Examples include arylate, polysulfone, polytetrafluoroethylene, and the like.
  • the PEN protective film has a base layer made of PEN.
  • the lower limit of Tg of the protective film is more preferably 130° C. or higher, still more preferably 140° C. or higher, particularly preferably 140° C. or higher, from the viewpoint of both volatilizing the residue of the precursor layer in a short time and reducing the number of air traps.
  • the temperature is 150°C or higher.
  • the upper limit of Tg of the protective film is not particularly limited, but is preferably 200°C or less, more preferably 180°C or less. From these viewpoints, the Tg of the protective film is preferably 130°C or more and 200°C or less, more preferably 140°C or more and 200°C or less, and still more preferably 150°C or more and 180°C or less.
  • Examples of the material for the base layer of the protective film having a Tg of 120° C. to 200° C. include PEN, polyamide (aramid), PEEK, polyphenylene sulfide, polycarbonate, polyarylate, polysulfone, polytetrafluoroethylene, and the like.
  • Examples of the material for the base layer of the protective film having a Tg of 140° C. to 200° C. include PEN, PEEK, polycarbonate, polyarylate, polysulfone, and the like.
  • the method for measuring Tg of the protective film is the same as the method described in Examples.
  • the temperature difference between the Tg of the protective film and the heating temperature in the flattening step is more than 0°C, preferably 5°C or more, more preferably 10°C or more, even more preferably 20°C or more. If the temperature difference is 5° C. or more, it is possible to more reliably suppress the occurrence of distortion in the protective film due to heating in the flattening step.
  • the "temperature difference between the Tg of the protective film and the heating temperature in the flattening step" is the value obtained by subtracting the heating temperature (° C.) in the flattening step from the Tg (° C.) of the protective film.
  • the method of disposing the protective film on the surface of the precursor layer of the frame precursor is not particularly limited.
  • the method of disposing the protective film on the surface of the precursor layer of the frame precursor is Another method is to leave the protective film still. After the protective film is placed on the surface of the precursor layer of the frame precursor, pressure (load) may be applied uniformly to the entire precursor layer.
  • the manufacturing method of the present disclosure includes a planarization process.
  • the protective film-attached frame precursor is heat-treated to form an adhesive layer with a flattened surface from the precursor layer of the precursor frame.
  • a pellicle frame with a protective film is obtained.
  • the conditions for the heat treatment in the flattening step are appropriately selected depending on the type of coating composition, etc., as long as the heating temperature is lower than the Tg of the protective film, and is preferably 80° C. or higher and 2 hours or longer.
  • the heating temperature of the heat treatment is more preferably 80°C to 200°C, still more preferably 90°C to 190°C, particularly preferably 100°C to 180°C, from the viewpoint of volatilizing the residue of the precursor layer.
  • the heating time of the heat treatment is appropriately selected depending on the heating temperature of the heat treatment, the type of coating composition, etc., and is preferably 2 hours to 48 hours, more preferably 3 hours to 36 hours, and even more preferably 4 hours to 24 hours. The duration is preferably 10 hours or more and 24 hours.
  • the thickness of the precursor layer immediately after the coating composition is applied usually varies depending on the region of the precursor layer.
  • the surface of the adhesive layer can be made even more flat.
  • a product in which a flattening article is brought into contact with a precursor frame with a protective film will be referred to as a "first contact article.”
  • the method of bringing the precursor layer of the precursor frame with a protective film into contact with the flat surface of the flattening article via the protective film is not particularly limited, and examples thereof include an upside down method, a mounting method, and the like.
  • a frame precursor with a protective film is placed on the flat surface of the flattening article.
  • a flattening article is placed on a frame precursor with a protective film.
  • a flattening article may be further brought into contact with the pellicle membrane end surface of the pellicle frame of the precursor frame with a protective film.
  • the mounting method is preferred from the viewpoint of making it easier to heat the precursor layer when heating with a hot plate.
  • the pressure (load) applied uniformly to the entire precursor layer is not particularly limited, but from the viewpoint of reducing distortion of the pellicle frame, it is preferably 10 g/cm 2 to 1000 g/cm 2 , more preferably 100 g/cm 2 . cm 2 to 800 g/cm 2 , more preferably 300 g/cm 2 to 600 g/cm 2 .
  • the TIR value of the flat surface of the planarization article is less than 10 ⁇ m. This allows the TIR value of the adhesive layer to be less than 10 ⁇ m. In other words, the number of local steps on the surface of the adhesive layer is reduced.
  • the TIR value of the flat surface of the flattening article is preferably 5 ⁇ m or less, more preferably 3 ⁇ m or less, and the closer it is to 0 ⁇ m, the more preferable it is.
  • the flattening article include a glass substrate.
  • the heat treatment is preferably performed while the flat surface of the glass substrate is in contact with the surface of the precursor layer via a protective film.
  • the method of heat-treating the precursor frame with the protective film while the precursor layer is in contact with the flat surface via the protective film is not particularly limited, and examples include a method using an oven, a method using a hot plate, and a method using heating.
  • Examples include a method of bringing a flattening article into contact with the flattening material.
  • the first contact article is placed in the oven and the first contact article itself is heated, thereby applying heat treatment to the precursor frame with the protective film.
  • the first contact article is placed on a hot plate such that the flattening article that contacts the precursor layer of the first contact article via the protective film contacts the plate of the hot plate.
  • the precursor frame with the protective film is subjected to heat treatment by heating the precursor layer through the flattening article.
  • a heated flattening article is prepared, a first contact article is placed on the flattening article, and the precursor layer is heated, thereby forming a precursor frame with a protective film. is subjected to heat treatment.
  • the set temperature in the oven is the same as the temperature range exemplified as the heating temperature for the heat treatment described above.
  • the set temperature inside the oven indicates the internal temperature of the oven.
  • the time range for heating the precursor layer using the oven is the same as the time range exemplified as the heating time for the heat treatment described above.
  • the set temperature of the hot plate is the same as the temperature range exemplified as the heating temperature for the heat treatment described above.
  • the set temperature of the hot plate indicates the surface temperature of the hot plate.
  • the time range for heating the precursor layer using the hot plate is the same as the time range exemplified as the heating time for the heat treatment described above.
  • the precursor layer of the precursor frame with a protective film is placed on the heated flat surface through the protective film. May be brought into contact.
  • the method of bringing the precursor layer of the precursor frame with a protective film into contact with the heated flat surface via the protective film is not particularly limited, and examples include hot pressing and the like.
  • the heating temperature of the heated flat surface is the same as the temperature range exemplified as the heating temperature of the heat treatment described above in order to facilitate flattening, and the heating time can be 10 seconds or more.
  • the manufacturing method of the present disclosure generally includes a peeling process.
  • the peeling process is performed after the planarization process is performed.
  • the protective film is peeled off from the pellicle frame with the protective film.
  • a pellicle frame with an adhesive layer is obtained.
  • Examples of the method for peeling the protective film from the pellicle frame with the protective film include a method of peeling it off by applying mechanical force in the direction of peeling from the pellicle frame.
  • Acrylic adhesive which is an example of the adhesive composition, will be described below.
  • the acrylic adhesive contains a copolymer (hereinafter referred to as "(meth)acrylic acid alkyl ester copolymer").
  • the (meth)acrylic acid alkyl ester copolymer is (meth)acrylic acid alkyl ester monomer, It is preferable to include a copolymer with a monomer having a functional group that is reactive with at least one of an isocyanate group, an epoxy group, and an acid anhydride (hereinafter referred to as a "functional group-containing monomer").
  • the pellicle does not peel off from the photomask even when exposed to a high temperature environment (e.g., 60°C or higher than 60°C). It is possible to suppress the occurrence of adhesive residue.
  • Adhesive residue indicates that at least a portion of the adhesive layer remains on the photomask after the pellicle is peeled off from the photomask.
  • the weight average molecular weight (Mw) of the (meth)acrylic acid alkyl ester copolymer is preferably 30,000 to 2,500,000, more preferably 50,000 to 1,500,000, and still more preferably 70,000 to 1,200,000. If the upper limit of the weight average molecular weight (Mw) of the (meth)acrylic acid alkyl ester copolymer is 2.5 million or less, the solution viscosity can be controlled within a range that is easy to process even if the solid content concentration of the coating composition is increased. .
  • the upper limit of the weight average molecular weight (Mw) of the (meth)acrylic acid alkyl ester copolymer is preferably 2.5 million or less, more preferably 1.5 million or less, and even more preferably 1.2 million or less.
  • the lower limit of the weight average molecular weight (Mw) of the (meth)acrylic acid alkyl ester copolymer is 30,000 or more, the pellicle will be more difficult to peel off from the photomask even when exposed to a high temperature environment (e.g. 60°C). , the occurrence of adhesive residue can be suppressed.
  • the lower limit of the weight average molecular weight (Mw) of the (meth)acrylic acid alkyl ester copolymer is preferably 30,000 or more, more preferably 50,000 or more, and still more preferably 70,000 or more.
  • the method for measuring the weight average molecular weight (Mw) of the (meth)acrylic acid alkyl ester copolymer is GPC (gel permeation chromatography).
  • GPC gel permeation chromatography
  • the number average molecular weight (Mn) of the (meth)acrylic acid alkyl ester copolymer is preferably 05,000 to 500,000, more preferably 08,000 to 300,000, still more preferably 10,000 to 200,000, and most preferably Preferably it is 20,000 to 200,000. If the upper limit of the number average molecular weight (Mn) of the (meth)acrylic acid alkyl ester copolymer is 500,000 or less, the solution viscosity can be controlled within a range that is easy to process even if the solid content concentration of the coating composition is increased. .
  • the upper limit of the number average molecular weight (Mn) of the (meth)acrylic acid alkyl ester copolymer is preferably 500,000 or less, more preferably 300,000 or less, and still more preferably 200,000 or less. If the lower limit of the number average molecular weight (Mn) of the (meth)acrylic acid alkyl ester copolymer is 0.5 million or more, the pellicle will peel more easily from the photomask even when exposed to a high temperature environment (e.g. 60°C). Therefore, the occurrence of adhesive residue can be suppressed.
  • a high temperature environment e.g. 60°C
  • the lower limit of the number average molecular weight (Mn) of the (meth)acrylic acid alkyl ester copolymer is preferably 0.5 million or more, more preferably 0.8 million or more, still more preferably 10,000 or more, and most preferably 20,000 or more. That's all.
  • the method for measuring the number average molecular weight (Mn) of the (meth)acrylic acid alkyl ester copolymer is the same as the method for measuring the weight average molecular weight (Mw) of the (meth)acrylic acid alkyl ester copolymer described above.
  • the "weight average molecular weight (Mw)/number average molecular weight (Mn)" (hereinafter referred to as "Mw/Mn") of the (meth)acrylic acid alkyl ester copolymer is preferably 1.0 to 10.0, more preferably is from 2.5 to 9.0, more preferably from 2.5 to 8.0, most preferably from 3.0 to 7.0.
  • Mw/Mn is within the above range, the copolymer can be easily produced and the generation of adhesive residue can be suppressed. If the upper limit of Mw/Mn is 10.0 or less, the occurrence of adhesive residue can be suppressed.
  • the upper limit of Mw/Mn is preferably 10.0 or less, more preferably 9.0 or less, still more preferably 8.0 or less, and most preferably 7.0 or less. If the lower limit of Mw/Mn is 1.0 or more, the copolymer can be easily produced.
  • the lower limit of Mw/Mn is preferably 1.0 or more, more preferably 2.0 or more, even more preferably 2.5 or more, and most preferably 3.0 or more.
  • the (meth)acrylic acid alkyl ester monomer preferably contains a (meth)acrylic acid alkyl ester monomer having an alkyl group having 1 to 14 carbon atoms.
  • Examples of (meth)acrylic acid alkyl ester monomers having an alkyl group having 1 to 14 carbon atoms include (meth)acrylic ester monomers of linear aliphatic alcohols and (meth)acrylic ester monomers of branched chain aliphatic alcohols. etc.
  • Examples of (meth)acrylic acid ester monomers of linear aliphatic alcohols include methyl (meth)acrylate, ethyl (meth)acrylate, butyl (meth)acrylate, propyl (meth)acrylate, and (meth)acrylate. Examples include hexyl acid, octyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, and lauryl (meth)acrylate.
  • Examples of (meth)acrylic acid ester monomers of branched chain aliphatic alcohols include isobutyl (meth)acrylate, isoamyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, isooctyl (meth)acrylate, and (meth)acrylate. ) Isononyl acrylate and the like. These may be used alone or in combination of two or more.
  • the (meth)acrylic acid alkyl ester monomer preferably has at least one of an alkyl group having 1 to 3 carbon atoms and an alicyclic alkyl group.
  • a (meth)acrylic acid alkyl ester monomer having at least one of an alkyl group and an alicyclic alkyl group having 1 to 3 carbon atoms is referred to as a "high Tg monomer.”
  • Tg refers to glass transition temperature.
  • the (meth)acrylic acid alkyl ester monomer is preferably an acrylic acid alkyl ester monomer having an alkyl group having 1 or more and 3 or less carbon atoms, or an alicyclic alkyl group. More preferably, the monomer is an acrylic acid alkyl ester monomer having an alkyl group having 1 or more and 3 or less carbon atoms. In the case of an acrylic acid alkyl ester monomer having an alicyclic alkyl group, the number of carbon atoms in the alicyclic alkyl group is preferably 5 or more and 10 or less from the viewpoint of availability.
  • high Tg monomers include methyl acrylate, ethyl acrylate, propyl acrylate, isopropyl acrylate, cyclohexyl acrylate, dicyclopentanyl acrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, and methacrylate. Examples include isopropyl acid, cyclohexyl methacrylate, dicyclopentanyl methacrylate, and the like.
  • the content of the (meth)acrylic acid alkyl ester monomer is preferably 80 parts by mass to 99.5 parts by mass, more preferably 85 parts by mass to 100 parts by mass of the total amount of monomers constituting the copolymer. 99.5 parts by weight, more preferably 87 parts to 99.5 parts by weight. If the content of the (meth)acrylic acid alkyl ester monomer is within the range of 80 parts by mass to 99.5 parts by mass, appropriate adhesive strength can be achieved.
  • the functional group-containing monomer is a monomer that can be copolymerized with the (meth)acrylic acid alkyl ester monomer.
  • the functional group-containing monomer has a functional group that is reactive with at least one of an isocyanate group, an epoxy group, and an acid anhydride.
  • Examples of the functional group-containing monomer include carboxy group-containing monomers, hydroxy group-containing monomers, and epoxy group-containing monomers.
  • Examples of the carboxy group-containing monomer include (meth)acrylic acid, itaconic acid, (meth)acrylic acid, itaconic acid, maleic acid, and crotonic acid.
  • hydroxy group-containing monomers examples include 2-hydroxyethyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, and 4-hydroxybutyl (meth)acrylate.
  • examples of the epoxy group-containing monomer include glycidyl (meth)acrylate. These may be used alone or in combination of two or more.
  • functional group-containing monomers include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, ( It is preferable to include a hydroxy group-containing (meth)acrylic acid having a hydroxyalkyl group having 2 to 4 carbon atoms, such as 4-hydroxybutyl meth)acrylate, or glycidyl (meth)acrylate, which is an epoxy group-containing monomer.
  • the content of the functional group-containing monomer is preferably, for example, 0.5 parts by mass to 20 parts by mass, based on 100 parts by mass of the total amount of monomers constituting the copolymer.
  • the lower limit of the content of the functional group-containing monomer is more preferably 1 part by mass per 100 parts by mass of the total amount of monomers constituting the (meth)acrylic acid alkyl ester copolymer. parts or more, more preferably 2 parts or more, particularly preferably 3 parts or more.
  • the upper limit of the content of the functional group-containing monomer is as follows: The amount is more preferably 15 parts by mass or less, and still more preferably 10 parts by mass or less.
  • the method for polymerizing the (meth)acrylic acid alkyl ester copolymer is not particularly limited, and examples include solution polymerization, bulk polymerization, emulsion polymerization, and various radical polymerizations.
  • the (meth)acrylic acid alkyl ester copolymer obtained by these polymerization methods may be a random copolymer, a block copolymer, a graft copolymer, or the like.
  • the reaction solution contains a polymerization solvent.
  • a polymerization solvent for example, propyl acetate, ethyl acetate, toluene, etc.
  • the viscosity of the copolymer solution can be adjusted.
  • the thickness and width of the coating composition can be easily controlled during polymerization.
  • the diluting solvent include propyl acetate, acetone, ethyl acetate, toluene, and the like.
  • the viscosity of the copolymer solution is preferably 1000 Pa ⁇ s or less, more preferably 500 Pa ⁇ s or less, still more preferably 200 Pa ⁇ s or less.
  • the viscosity of the copolymer solution is the viscosity when the temperature of the copolymer solution is 25°C, and can be measured with an E-type viscometer.
  • Solution polymerization As an example of solution polymerization, a polymerization initiator is added to a mixed solution of monomers under a stream of inert gas such as nitrogen, and polymerization is carried out at 50°C to 100°C for 4 hours to 30 hours. Examples include methods of conducting the reaction.
  • polymerization initiator examples include azo polymerization initiators and peroxide polymerization initiators.
  • azo polymerization initiator 2,2'-azobisisobutyronitrile (AIBN), 2,2'-azobis-2-methylbutyronitrile, 2,2'-azobis(2-methylpropionic acid) Examples include dimethyl, 4,4'-azobis-4-cyanovaleric acid, and the like.
  • peroxide-based polymerization initiators include benzoyl peroxide.
  • the content of the polymerization initiator is preferably 0.01 parts by mass to 2.0 parts by mass based on 100 parts by mass of all monomers constituting the alkyl (meth)acrylate copolymer.
  • a chain transfer agent in addition to a polymerization initiator, a chain transfer agent, an emulsifier, etc. may be added to the monomer mixed solution.
  • chain transfer agents emulsifiers, etc., known agents can be selected and used as appropriate.
  • the amount of polymerization initiator remaining in the adhesive layer is preferably small. This makes it possible to reduce the amount of outgas generated during exposure.
  • a method to reduce the amount of polymerization initiator remaining in the adhesive layer there is a method to minimize the amount of polymerization initiator added when polymerizing the (meth)acrylic acid alkyl ester copolymer, and a method that is easy to thermally decompose. Examples include a method using a polymerization initiator, a method in which the adhesive is heated to a high temperature for a long time in the adhesive application and drying process, and the polymerization initiator is decomposed in the drying process.
  • the 10-hour half-life temperature is used as an index representing the thermal decomposition rate of the polymerization initiator. "Half-life" refers to the time it takes for half of the polymerization initiator to decompose.
  • the 10-hour half-life temperature indicates the temperature at which the half-life is 10 hours.
  • As the polymerization initiator it is preferable to use a polymerization initiator with a low 10-hour half-life temperature. The lower the 10-hour half-life temperature, the easier the polymerization initiator is to thermally decompose. As a result, it is difficult to remain on the adhesive layer.
  • the 10-hour half-life temperature of the polymerization initiator is preferably 80°C or lower, more preferably 75°C or lower.
  • Examples of azo polymerization initiators with a low 10-hour half-life temperature include 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) (10-hour half-life temperature: 30°C), 2,2 '-azobisisobutyronitrile (10-hour half-life temperature: 65°C), 2,2-azobis(2,4-dimethylvaleronitrile) (10-hour half-life temperature: 51°C), dimethyl 2,2'- Examples include azobis(2-methylpropionate) (10-hour half-life temperature: 66°C), 2,2'-azobis(2-methylbutyronitrile) (10-hour half-life temperature: 67°C), and the like.
  • the acrylic adhesive preferably contains a reaction product of a (meth)acrylic acid alkyl ester copolymer and a crosslinking agent. This improves the cohesive force of the resulting adhesive layer, suppresses adhesive residue when peeling off the pellicle from the photomask, and improves adhesive strength at high temperatures (e.g., 60°C or temperature environments exceeding 60°C). I can do it.
  • the crosslinking agent has at least one of an isocyanate group, an epoxy group, and an acid anhydride.
  • crosslinking agents include monofunctional epoxy compounds, polyfunctional epoxy compounds, acid anhydride compounds, metal salts, metal alkoxides, aldehyde compounds, non-amino resin amino compounds, urea compounds, isocyanate compounds, Examples include metal chelate compounds, melamine compounds, and aziridine compounds.
  • crosslinking agents include monofunctional epoxy compounds, polyfunctional epoxy compounds, isocyanate compounds, and acid anhydride compounds because of their excellent reactivity with the functional group components of the (meth)acrylic acid alkyl ester copolymer. More preferably, it is at least one of the following, and more preferably an acid anhydride compound.
  • Examples of the monofunctional epoxy compound include glycidyl (meth)acrylate, glycidyl acetate, butyl glycidyl ether, and phenyl glycidyl ether.
  • Examples of the polyfunctional epoxy compound include neopentyl glycol diglycidyl ether, polyethylene glycol diglycidyl ether, bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, phthalic acid diglycidyl ester, dimer acid diglycidyl ester, and triglycidyl isocyanate.
  • acid anhydride compounds include aliphatic dicarboxylic acid anhydrides, aromatic polycarboxylic acid anhydrides, and the like.
  • Examples of aliphatic dicarboxylic anhydrides include maleic anhydride, hexahydrophthalic anhydride, hexahydro-4-methylphthalic anhydride, bicyclo[2.2.1]heptane-2,3-dicarboxylic anhydride, and 2-methylbicyclo [2.2.1] Heptane-2,3-dicarboxylic anhydride, tetrahydrophthalic anhydride, and the like.
  • Examples of aromatic polycarboxylic acid anhydrides include phthalic anhydride and trimellitic anhydride.
  • isocyanate compound examples include xylylene diisocyanate, hexamethylene diisocyanate, tolylene diisocyanate, and polymers, derivatives, and polymers thereof. These may be used alone or in combination of two or more.
  • the crosslinking agent may be a product.
  • Examples of crosslinking agent products include "Rikacid MH-700G” manufactured by New Japan Chemical Co., Ltd.
  • the adhesive layer contains a reaction product of the copolymer and a crosslinking agent, and the content of the crosslinking agent is 0.01 parts by mass to 100 parts by mass of the total amount of monomers constituting the copolymer. Preferably, it is 3.00 parts by mass.
  • the content of the crosslinking agent is preferably 0.01 parts by mass to 3.00 parts by mass with respect to 100 parts by mass of the total amount of monomers constituting the copolymer, to obtain an adhesive that does not easily leave adhesive residue. From this viewpoint, the amount is more preferably 0.10 parts by mass to 3.00 parts by mass, and even more preferably 0.1 parts by mass to 2.00 parts by mass.
  • the upper limit of the content of the crosslinking agent is 3.00 parts by mass or less, the crosslinking density of the (meth)acrylic acid alkyl ester copolymer will not become too large. Therefore, it is thought that the adhesive absorbs the stress applied to the photomask, and the influence of the adhesive layer on the flatness of the photomask is alleviated.
  • the upper limit of the content of the crosslinking agent is preferably 2.00 parts by mass or less, more preferably 1.00 parts by mass or less.
  • the lower limit of the content of the crosslinking agent is 0.01 part by mass or more, the crosslinking density will not become too small, so handling properties during the manufacturing process will be maintained, and when peeling the pellicle from the photomask. It is thought that adhesive residue is less likely to occur.
  • the content of the crosslinking agent is within the range of 0.01 parts by mass to 3.00 parts by mass, a pellicle with more suppressed adhesive residue can be obtained.
  • the coating composition may further contain a catalyst.
  • a catalyst thereby, the curing of the (meth)acrylic acid alkyl ester copolymer can be further accelerated.
  • the catalyst include amine catalysts.
  • the amine catalyst include octylate of (1,8-diazabicyclo-(5.4.0)undecene-7), triethylenediamine, and the like.
  • the amine catalyst may be a product of San-Apro Co., Ltd. such as "DBU", “DBN”, “U-CAT”, “U-CAT SA1", “U-CAT SA102", etc.
  • the content of the catalyst is preferably 0.01 parts by mass to 3.00 parts by mass, more preferably 0.10 parts by mass to 1.00 parts by mass, based on 100 parts by mass of the (meth)acrylic acid alkyl ester copolymer. Department.
  • the coating composition preferably does not contain a surface modifier. Thereby, the amount of outgas generated can be suppressed.
  • the coating composition may contain additives such as fillers, pigments, diluents, anti-aging agents, and tackifiers, as necessary. These additives may be used alone or in combination of two or more.
  • the coating composition may contain a diluting solvent. Thereby, the viscosity of the coating composition can be adjusted. As a result, when applying the coating composition to the photomask end face of the pellicle frame, the thickness and width of the coating composition can be easily controlled.
  • the diluting solvent include propyl acetate, acetone, ethyl acetate, toluene, and the like.
  • the viscosity of the coating composition is preferably 50 Pa.s or less, more preferably 10 Pa.s to 40 Pa.s, still more preferably 20 Pa.s to 30 Pa.s.
  • the viscosity of the coating composition is the viscosity when the temperature of the coating composition is 25°C, and can be measured with an E-type viscometer.
  • the pellicle frame with protective film of the present disclosure includes a pellicle frame, an adhesive layer for attaching to a photomask, and a protective film.
  • the adhesive layer is formed on the pellicle frame.
  • the protective film is attached to the surface of the adhesive layer.
  • the glass transition temperature of the protective film is over 120°C.
  • the pellicle frame with a protective film of the present disclosure has the above configuration, it is possible to suppress the number of air traps when a pellicle is attached to a photomask. This effect is presumed to be due to the following reasons, but is not limited thereto.
  • the pellicle frame with a protective film of the present disclosure is suitably manufactured by the method of manufacturing a pellicle frame with an adhesive layer of the present disclosure.
  • the heating temperature in the flattening step of the method for manufacturing a pellicle frame with an adhesive layer according to the present disclosure is usually 120° C. or lower. Therefore, if the glass transition temperature of the protective film exceeds 120° C., distortion of the protective film is unlikely to occur during the manufacturing process.
  • the surface of the adhesive layer tends to be flat when the protective film is peeled off from the pellicle frame with the protective film.
  • the number of local steps on the surface of the adhesive layer is likely to be one or less. Therefore, it is presumed that the number of air traps when a pellicle is attached to a photomask can be suppressed.
  • the pellicle frame, adhesive layer, and protective film of the pellicle frame with a protective film include the same ones as those exemplified as the pellicle frame, adhesive layer, and protective film in the method for producing a pellicle frame with an adhesive layer.
  • the pellicle frame with adhesive layer of the present disclosure includes a pellicle frame and an adhesive layer for attaching to a photomask.
  • the adhesive layer is formed on the pellicle frame.
  • the number of local steps of 3 ⁇ m or more on the surface of the adhesive layer is one or less.
  • the method for measuring "the number of local steps of 3 ⁇ m or more" is the same as the method described in Examples.
  • the pellicle frame with an adhesive layer of the present disclosure has the above configuration, it is possible to suppress the number of air traps when a pellicle is attached to a photomask. This effect is presumed to be due to the following reasons, but is not limited thereto.
  • the fact that the number of local steps of 3 ⁇ m or more on the surface of the adhesive layer is one or less indicates that the surface of the adhesive layer is flat. Therefore, it is estimated that the number of air traps when a pellicle is attached to a photomask is suppressed more than when the number of local steps of 3 ⁇ m or more on the surface of the adhesive layer is two or more.
  • the number of local steps of 3 ⁇ m or more on the surface of the adhesive layer is one or less, and preferably zero from the viewpoint of further reducing the number of air traps when the pellicle is attached to the photomask.
  • Examples of a method for keeping the number of local steps of 3 ⁇ m or more on the surface of the adhesive layer within the above range include a method of manufacturing a pellicle frame with an adhesive layer using the method of manufacturing a pellicle frame with an adhesive layer of the present disclosure.
  • the pellicle frame and the adhesive layer of the pellicle frame with an adhesive layer may be the same as those exemplified as the pellicle frame and the adhesive layer in the method for manufacturing a pellicle frame with an adhesive layer.
  • the adhesive layer is made of, among others, an acrylic adhesive, a silicone adhesive, a styrene-butadiene adhesive, a urethane adhesive, and an olefin adhesive from the viewpoint of reducing the amount of outgas generated from the pellicle.
  • the adhesive preferably contains at least one selected from the group, more preferably an acrylic adhesive, and even more preferably an acrylic adhesive.
  • the pellicle of the present disclosure includes a pellicle membrane supported by the pellicle frame, and a pellicle frame with an adhesive layer of the present disclosure.
  • the pellicle membrane is supported by a pellicle frame.
  • the pellicle membrane is supported by the pellicle membrane end face of the pellicle frame.
  • the pellicle film prevents foreign matter from adhering to the surface of the photomask, and also allows exposure light to pass through during exposure. Foreign matter includes dust.
  • Examples of the exposure light include deep ultraviolet (DUV) light, EUV, and the like. EUV indicates light with a wavelength of 2 nm or more and 30 nm or less.
  • the pellicle membrane covers the entire opening on one end surface (pellicle membrane end surface) of the through hole of the pellicle frame.
  • the pellicle membrane may be supported directly on one end surface of the pellicle frame, or may be supported via a membrane adhesive layer.
  • the film adhesive layer may be a cured product of a known adhesive.
  • the thickness of the pellicle film is preferably 1 nm or more and 400 nm or less, and more preferably 1 nm or more and 70 nm because it is easy to increase the transmittance in EUV exposure.
  • the material of the pellicle film is not particularly limited, and examples include carbon-based materials, SiN, polysilicon, and fluororesin. Carbon-based materials include carbon nanotubes (hereinafter referred to as "CNTs"). Among these, the material of the pellicle film preferably contains at least one selected from the group consisting of CNT, metal silicide, and polysilicon, and more preferably contains CNT, since it is easy to increase the transmittance in EUV exposure. .
  • the CNTs may be single-walled CNTs or multi-walled CNTs.
  • the metal silicide is preferably one of molybdenum silicide nitride (MoSiN) and molybdenum silicide (MoSi).
  • MoSiN molybdenum silicide nitride
  • MoSi molybdenum silicide
  • the pellicle membrane may be a non-woven structure.
  • the nonwoven structure is formed by, for example, CNTs in the form of fibers.
  • the pellicle membrane may be supported indirectly by the pellicle frame via the pellicle membrane adhesive layer, or may be directly supported by the pellicle frame.
  • the adhesive constituting the adhesive layer for the pellicle membrane include acrylic resin adhesive, epoxy resin adhesive, polyimide resin adhesive, silicone resin adhesive, inorganic adhesive, double-sided adhesive tape, polyolefin adhesive, Examples include hydrogenated styrene adhesives.
  • adhesives for pellicle membranes are selected from a group consisting of silicone resin adhesives, acrylic resin adhesives, hydrogenated styrene adhesives, and epoxy resin adhesives from the viewpoint of ease of application and curing processing. Preferably, it is at least one selected from the following.
  • the pellicle membrane adhesive is a concept that includes not only adhesives but also adhesives.
  • the thickness of the adhesive layer for pellicle membrane is not particularly limited.
  • the thickness of the pellicle membrane adhesive layer is, for example, 10 ⁇ m or more and 1 mm or less.
  • Photomask with pellicle includes a photomask and the pellicle of the present disclosure.
  • a pellicle is attached to a photomask.
  • the area of the gap between the adhesive layer and the photomask is 0.25% or less of the area of the adhesive layer that is in contact with the photomask.
  • the method for measuring the area of the gap between the adhesive layer and the photomask is the same as the method described in Examples.
  • the area of the gap between the adhesive layer and the photomask is 0.25% or less of the area of the adhesive layer that is in contact with the photomask. ” indicates that there is very little air entrapment. Since the photomask with a pellicle of the present disclosure has the above configuration, it is possible to suppress the occurrence of air paths. Furthermore, since there is little air entrapment, the bonding surface to the photomask becomes uniform, so distortion of the photomask can be suppressed, and since a wide bonding area can be ensured, peeling of the pellicle can be suppressed when the photomask is moved during exposure.
  • the area of the gap between the adhesive layer and the photomask is 0.25% or less of the area of the adhesive layer in contact with the photomask, It is preferably 0% to 0.10%, more preferably 0% to 0.05%, and the lower the content, the more preferable it is.
  • a photomask is an original plate of a circuit pattern.
  • a photomask has a pattern.
  • the pellicle is attached to the patterned side of the photomask.
  • the support substrate, the reflective layer, and the absorber layer do not need to be stacked in this order.
  • a desired image is formed on a sensitive substrate (eg, a semiconductor substrate with a photoresist film) by the absorption layer partially absorbing the light (eg, EUV).
  • the reflective layer include a multilayer film of molybdenum (Mo) and silicon (Si).
  • the material of the absorber layer may be a highly absorbent material such as EUV. Examples of materials with high absorption properties for EUV and the like include chromium (Cr), tantalum nitride, and the like.
  • a photomask with a pellicle according to the present disclosure is used in an exposure apparatus.
  • the exposure apparatus includes a light source, a photomask with a pellicle according to the present disclosure, and an optical system.
  • a light source emits exposure light.
  • the optical system guides exposure light emitted from the light source to the photomask.
  • a photomask with a pellicle is arranged so that exposure light emitted from a light source passes through a pellicle film and is irradiated onto the photomask.
  • finer patterns for example, line widths of 32 nm or less
  • EUV etc. exposure equipment can also prevent resolution defects due to foreign particles even when using EUV, which is prone to resolution defects due to foreign particles. Reduced pattern exposure can be performed.
  • the exposure light is preferably DUV or EUV. Because EUV has a short wavelength, it is easily absorbed by gases such as oxygen or nitrogen. Therefore, exposure with EUV light is performed in a vacuum environment.
  • Example 1 [2.1] Preparation Step The (meth)acrylic acid alkyl ester copolymer was prepared by a well-known method. Specifically, a reaction vessel equipped with a stirrer, a thermometer, a reflux condenser, a dropping device, and a nitrogen introduction tube was prepared. A polymerization solvent (180 parts by mass) was placed in a reaction vessel, and a mixture of EA/4-HBA/HEMA/GMA/polymerization initiator (423.4 parts by mass) was added to the reactor at 378/12.6/21/8.4/3. It was prepared at a mass ratio of 4.
  • This reaction solution was reacted at 85°C for 6 hours and then at 95°C for 2 hours in a nitrogen atmosphere to obtain an acrylic copolymer solution with a nonvolatile content (copolymer) concentration of 70% by mass (weight average molecular weight: 11 .90,000).
  • a crosslinking agent (0.28 parts by mass) and a catalyst (0.93 parts by mass) were added to the obtained acrylic copolymer solution (143 parts by mass) and mixed with stirring to form a coating composition (acrylic adhesive ) was obtained.
  • an anodized aluminum pellicle frame (external dimensions: 149 mm x 115 mm, frame height H: 4.5 mm, frame width W: 2 mm) was prepared as the pellicle frame 11.
  • the prepared coating composition was applied to the photomask end surface S11A of the pellicle frame 11 using a dispenser to form a precursor layer made of the coating composition. As a result, a frame precursor was obtained.
  • a PEN protective film was prepared.
  • the PEN protective film had a two-layer structure including a base layer (material: polyethylene naphthalate) and a release layer (material: silicone type).
  • the thickness of the base material layer was 75 ⁇ m.
  • a glass substrate was prepared as a flat plate.
  • the TIR value of the flat surface of the flat plate was 5 ⁇ m.
  • a protective film 21 was placed on the surface of the precursor layer of the dried frame precursor to obtain a frame precursor with a protective film.
  • a mounting method was performed. Specifically, the pellicle frame with a precursor layer was placed on a flat plate with the precursor layer of the frame precursor with a protective film facing downward (in the direction of gravity). The precursor layer of the frame precursor with a protective film and the flat surface of the flat plate were in contact with each other via the protective film 21. At this time, a pressure (load) of 1.6 g/cm 2 was applied uniformly to the entire precursor layer of the pellicle frame with a precursor layer. As a result, a first contact article was obtained. An oven (“DRC623FB19A” manufactured by ADVANTEC) was prepared as a heating device. The first contact article was placed inside the oven.
  • DRC623FB19A manufactured by ADVANTEC
  • the entire first contact article was heated in an oven under heating conditions of 120°C and 16 hours.
  • the flat surface of the flat plate was transferred to the surface of the precursor layer, and the precursor layer was cured. That is, an adhesive layer 12 with a flattened surface was formed from the precursor layer.
  • the first contact article was then removed from the heating device and the flat plate was removed from the first contact article. Thereby, a pellicle frame 20 with a protective film was obtained.
  • the protective film 21 was removed from the protective film-equipped pellicle frame 20 to obtain the adhesive layer-equipped pellicle frame 10.
  • the thickness of the adhesive layer 12 made of the adhesive composition was 0.2 mm.
  • Example 2 and Example 3 A pellicle frame 10 with an adhesive layer was obtained in the same manner as in Example 1, except that the temperature and time of the heating conditions in the flattening step were changed to those shown in Table 1.
  • Comparative example 1 A pellicle frame 10 with an adhesive layer was obtained in the same manner as in Example 1, except that the PEN protective film was replaced with a PET protective film as the protective film 21.
  • the PET protective film had a two-layer structure including a base layer (material: polyethylene terephthalate) and a release layer (material: silicone type). The thickness of the base material layer was 75 ⁇ m.
  • the height difference at each measurement point on the surface S12 of the adhesive layer 12 was measured as follows.
  • the pellicle frame 10 with an adhesive layer was placed on a surface plate so that the pellicle film end surface S11B of the pellicle frame 10 with an adhesive layer faced the surface plate.
  • the height from the surface plate of each of a total of 204 measurement points on the surface S12 of the adhesive layer 12 was measured using a 3D displacement meter (manufactured by Keyence Corporation, "WI5000", sensor head "WI-004").
  • the 204 measurement points include four points at the four corners of the photomask end surface S11A and 200 points on the four sides between the four corners.
  • the 200 points basically indicate the total of points set at intervals of 2.5 mm from one point of the four corners to another point of the four corners on each side between the four corners. However, among the 200 points, if the distance between one of the four corners (hereinafter referred to as "corner point”) and the point adjacent to the corner point (hereinafter referred to as "corner interval”) is not 2.5 mm , the points adjacent to the corner points are points set so that the corner distance is less than 2.5 mm. If the number of measurement points is not 204 when using the above-mentioned 2.5 mm spacing and corner spacing due to the difference in the size of the pellicle frame 11, the measurement points are determined using the 2.5 mm spacing and the above-mentioned corner spacing concept. did.
  • a least squares plane was derived using the height measurements at 204 points.
  • the height difference between each measurement point and the least squares plane was determined.
  • the positive and negative signs of the height differences of each of the plurality of measurement points located on the opposite side of the surface plate with respect to the least squares plane were set as "plus (+)”.
  • the positive and negative signs of the height difference of each of the plurality of measurement points located on the surface plate side with respect to the least squares plane were set as "minus (-)".
  • the height difference obtained in this manner and marked with a positive or negative value was defined as the height difference at each measurement point on the surface S12 of the adhesive layer 12.
  • the ⁇ height difference is a value obtained by subtracting the height difference of one point adjacent to the arbitrary point in a clockwise direction from the height difference of any one of the 204 points.
  • the number of local steps basically indicates the number of ⁇ height differences where the absolute value of the ⁇ height difference is 3 ⁇ m or more (referred to as " ⁇ height difference (large)”) among the 204 ⁇ height differences.
  • ⁇ height difference (large) the absolute value of the ⁇ height difference
  • the 204 ⁇ height differences are arranged in a line according to the measurement points of the 204 points, if there are two or more consecutive ⁇ height differences (large), multiple consecutive ⁇ height differences (large) ) is counted as one local step.
  • the ⁇ height differences arranged in a line based on the method described above are 2 ⁇ m, ⁇ 4 ⁇ m, 1 ⁇ m, 3 ⁇ m, and 1 ⁇ m
  • the number of local steps is two.
  • the ⁇ height differences arranged in a row are 2 ⁇ m, ⁇ 4 ⁇ m, 5 ⁇ m, 3 ⁇ m, and 1 ⁇ m
  • the number of local steps is one.
  • the thickness of the adhesive layer is determined as follows.
  • the pellicle frame is placed on the surface plate so that the end surface for the pellicle membrane of the pellicle frame with the adhesive layer faces the surface plate.
  • 3D displacement meter manufactured by Keyence Corporation, "WI5000”, sensor head "WI-004"
  • 4 of the 6 measurement points are points where the adhesive layer is applied
  • 2 of the 6 measurement points are the points where the adhesive layer is applied. This is the point where no layer has been applied.
  • the adhesive layer is formed only in the center of each side between the four corners of the photomask end surface, and on the edge of each side between the four corners on the through-hole side of the pellicle frame and on the through-hole side of the pellicle frame. is not formed on the opposite edge. Therefore, in this example, among the six measurement points, four points located at the center of the pellicle in the width direction are positions where the adhesive layer is formed on the photomask end surface. Of the six measurement points, the remaining two points located on both edges of the pellicle in the width direction are positions where no adhesive layer is formed on the photomask end surface.
  • the positive and negative signs of the height differences of each of the plurality of measurement points located on the opposite side of the surface plate with respect to the least squares plane were set as "plus (+)".
  • the positive and negative signs of the height difference of each of the plurality of measurement points located on the surface plate side with respect to the least squares plane were set as "minus (-)”.
  • the height difference obtained in this manner and marked with a positive or negative value was defined as the height difference at each measurement point on the surface S12 of the adhesive layer 12.
  • the difference between the largest height difference and the smallest height difference was defined as the TIR value.
  • a transparent quartz substrate was prepared.
  • the transparent quartz substrate has a first main surface and a second main surface opposite to the first main surface.
  • a pellicle frame 10 with an adhesive layer was placed on the first main surface of a transparent quartz substrate.
  • the adhesive layer 12 of the pellicle frame 10 with an adhesive layer was brought into contact with the first main surface of the transparent quartz substrate. Thereby, a second contact article was obtained.
  • a glass substrate (model: HOYA 6025 quartz substrate, mass: 320 g) was placed on the pellicle membrane end surface S11B of the pellicle frame 11, and a weight (mass: 2 kg) was placed on the glass substrate. After 20 seconds had passed since the weight was placed on the glass substrate, the glass substrate and the weight were removed from the pellicle film end surface S11B of the pellicle frame 11.
  • Air engraving area Using the software "VHX" attached to the optical microscope, the total area of the plurality of air entrapments existing in the contact surface of the adhesive layer 12 with the first main surface of the quartz substrate, and the adhesive The total area of the contact surface of layer 12 with the first main surface of the quartz substrate was measured. The total area of the plurality of air holes present in the contact surface of the adhesive layer 12 with the first main surface of the quartz substrate was defined as the "air trap area.” The ratio of the air entrainment area to the total area of the contact surface of the adhesive layer 12 with the first main surface of the quartz substrate was defined as the "air entrainment ratio". The allowable range of air entrainment ratio is 0.25% or less.
  • acrylic refers to an acrylic adhesive.
  • Tg indicates glass transition temperature.
  • Tg of the protective film refers to the glass transition temperature of the base layer included in the protective film.
  • the method for manufacturing a pellicle frame with an adhesive layer in Examples 1 to 3 includes Step A (that is, a preparation step), Step B (that is, a placement step), and Step C (that is, a flattening step).
  • Step A that is, a preparation step
  • Step B that is, a placement step
  • Step C that is, a flattening step
  • the glass transition temperature (Tg) of the protective film 21 is higher than the heating temperature in the flattening process. Therefore, the number of air traps in Examples 1 to 3 was 3 or less. From these results, it was found that the methods for manufacturing pellicle frames with adhesive layers according to Examples 1 to 3 can suppress the number of air traps when a pellicle is attached to a photomask.
  • the pellicle frame 20 with a protective film of Comparative Example 1 includes a pellicle frame 11, an adhesive layer 12, and a protective film 21.
  • the glass transition temperature of the protective film 21 of Comparative Example 1 was not higher than 120°C. Therefore, the number of air traps in Comparative Example 1 was 13. child
  • the pellicle frames 20 with protective films of Examples 1 to 3 include a pellicle frame 11, an adhesive layer 12, and a protective film 21.
  • the glass transition temperature of the protective films 21 of Examples 1 to 3 was over 120°C. Therefore, the number of air traps in Examples 1 to 3 was 3 or less. From these results, it was found that the pellicle frames 20 with protective films of Examples 1 to 3 can suppress the number of air traps when a pellicle is attached to a photomask.
  • the pellicle frame 10 with an adhesive layer of Comparative Example 1 includes a pellicle frame 11 and an adhesive layer 12.
  • the number of local steps of 3 ⁇ m or more on the surface S12 of the adhesive layer 12 in Comparative Example 1 was not less than one. Therefore, the number of air traps in Comparative Example 1 was 13.
  • the adhesive layer-attached pellicle frame 10 of Examples 1 to 3 includes a pellicle frame 11 and an adhesive layer 12.
  • the number of local steps of 3 ⁇ m or more on the surface S12 of the adhesive layer 12 in Examples 1 to 3 was zero.
  • the fact that the number of local steps of 3 ⁇ m or more on the surface S12 of the adhesive layer 12 is one or less indicates that the surface S12 of the adhesive layer 12 is flat. From these results, it was found that the adhesive layer-attached pellicle frame 10 of Examples 1 to 3 can suppress the number of air traps when a pellicle is attached to a photomask.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Preparing Plates And Mask In Photomechanical Process (AREA)

Abstract

L'invention concerne un procédé de fabrication d'un cadre de pellicule comportant une couche adhésive sensible à la pression qui permet de réduire le nombre de cas de piégeage d'air lors de la fixation d'une pellicule à un photomasque.　Ce procédé de fabrication de cadre de pellicule comportant une couche adhésive sensible à la pression comprend : une étape consistant à préparer un précurseur de cadre pourvu d'un cadre de pellicule (11) et une couche de précurseur qui est un précurseur d'une couche adhésive sensible à la pression (12) formée sur le cadre de pellicule (12) ; une étape consistant à former le précurseur de cadre à film protecteur en disposant sur la surface de la couche de précurseur un film protecteur (21) ayant une température de transition vitreuse qui est supérieure à une température de chauffage de la prochaine étape ; et une étape consistant à former la couche adhésive sensible à la pression (12) avec une surface planarisée à partir de la couche de précurseur en chauffant le précurseur de cadre doté du film protecteur.
PCT/JP2023/010465 2022-03-23 2023-03-16 Procédé de fabrication d'un cadre de pellicule comportant une couche adhésive sensible à la pression, cadre de pellicule à film protecteur, cadre de pellicule comportant une couche adhésive sensible à la pression, pellicule et photomasque comportant une pellicule WO2023182186A1 (fr)

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WO2021018777A1 (fr) * 2019-07-30 2021-02-04 Asml Netherlands B.V. Membrane de pellicule
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JP2021135403A (ja) * 2020-02-27 2021-09-13 凸版印刷株式会社 ペリクル膜、ペリクル、膜、グラフェンシート及びその製造方法
JP2022031882A (ja) * 2015-02-03 2022-02-22 エーエスエムエル ネザーランズ ビー．ブイ． マスクアセンブリ及び関連する方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004157229A (ja) * 2002-11-05 2004-06-03 Shin Etsu Chem Co Ltd リソグラフィ用ペリクル及びその製造方法
JP2009025560A (ja) * 2007-07-19 2009-02-05 Shin Etsu Chem Co Ltd リソグラフィー用ペリクル
JP2012108277A (ja) * 2010-11-17 2012-06-07 Shin Etsu Chem Co Ltd リソグラフィー用ペリクル
JP2015094800A (ja) * 2013-11-11 2015-05-18 信越化学工業株式会社 ペリクルの貼り付け方法及びこの方法に用いる貼り付け装置
JP2016018008A (ja) * 2014-07-04 2016-02-01 旭化成イーマテリアルズ株式会社 ペリクル、ペリクル付フォトマスク、及び半導体素子の製造方法
WO2016079051A2 (fr) * 2014-11-17 2016-05-26 Asml Netherlands B.V. Ensemble masque
JP2016114883A (ja) * 2014-12-17 2016-06-23 信越化学工業株式会社 リソグラフィー用ペリクルの作製方法
JP2022031882A (ja) * 2015-02-03 2022-02-22 エーエスエムエル ネザーランズ ビー．ブイ． マスクアセンブリ及び関連する方法
WO2021018777A1 (fr) * 2019-07-30 2021-02-04 Asml Netherlands B.V. Membrane de pellicule
JP2021056484A (ja) * 2019-09-26 2021-04-08 エスアンドエス テック カンパニー リミテッド 極紫外線リソグラフィ用ペリクル及びその製造方法
JP2021135403A (ja) * 2020-02-27 2021-09-13 凸版印刷株式会社 ペリクル膜、ペリクル、膜、グラフェンシート及びその製造方法

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