CN111679549B - Adhesive suitable for pellicle for EUV lithography and pellicle using the adhesive - Google Patents
Adhesive suitable for pellicle for EUV lithography and pellicle using the adhesive Download PDFInfo
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- CN111679549B CN111679549B CN202010637924.8A CN202010637924A CN111679549B CN 111679549 B CN111679549 B CN 111679549B CN 202010637924 A CN202010637924 A CN 202010637924A CN 111679549 B CN111679549 B CN 111679549B
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- adhesive
- hardness
- adhesive layer
- pellicle
- dustproof film
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- 239000000853 adhesive Substances 0.000 title claims abstract description 133
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 124
- 238000001900 extreme ultraviolet lithography Methods 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 239000012298 atmosphere Substances 0.000 claims abstract description 12
- 239000012790 adhesive layer Substances 0.000 claims description 34
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 12
- 239000010703 silicon Substances 0.000 claims description 12
- 239000004593 Epoxy Substances 0.000 claims description 9
- 239000004973 liquid crystal related substance Substances 0.000 claims description 9
- 239000004065 semiconductor Substances 0.000 claims description 8
- 239000011231 conductive filler Substances 0.000 claims 6
- 238000010438 heat treatment Methods 0.000 claims 4
- 230000000052 comparative effect Effects 0.000 description 10
- 238000001723 curing Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 229920002120 photoresistant polymer Polymers 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000428 dust Substances 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000007687 exposure technique Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000712 assembly Effects 0.000 description 3
- 238000000429 assembly Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- -1 polyethylene Polymers 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 229910000531 Co alloy Inorganic materials 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000000020 Nitrocellulose Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006332 epoxy adhesive Polymers 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910021421 monocrystalline silicon Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920001220 nitrocellulos Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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
- 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
-
- 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
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
- G03F1/22—Masks or mask blanks for imaging by radiation of 100nm or shorter wavelength, e.g. X-ray masks, extreme ultraviolet [EUV] masks; Preparation thereof
-
- 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
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/312—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier parameters being the characterizing feature
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Preparing Plates And Mask In Photomechanical Process (AREA)
- Paints Or Removers (AREA)
Abstract
Provided are an adhesive agent suitable for an EUV lithography pellicle, a pellicle using the same, a method for manufacturing the pellicle, and a method for selecting an adhesive agent suitable for an EUV lithography pellicle. The adhesive of the present invention has a hardness change rate of + -50% expressed by the following formula when the cured product of the adhesive is allowed to stand in an atmosphere at 300 ℃ for 7 days. The formula: the rate of change in hardness (%) = { (hardness after the rest) - (hardness before the rest) } is ≡ (hardness before the rest) ×100.
Description
The present application is filed by day 2016, 10 and 25 and entitled "suitable adhesive in pellicle for EUV lithography and pellicle Using the same", and filed by patent application of the invention with application number 201610937977.5.
Technical Field
The present invention relates to an adhesive agent suitable for use in a pellicle for EUV lithography and a pellicle using the same, and more particularly, to an adhesive agent suitable for use in a pellicle and a pellicle using the same, for example, when performing lithography using EUV (Extreme ultraviolet) light having a dominant wavelength of 13.5 nm.
Background
In the manufacture of LSI, ultra LSI, or the like, or in the manufacture of a liquid crystal panel, a semiconductor wafer or a liquid crystal mother panel is irradiated with light to produce a pattern, and in this case, if dust adheres to a photomask or a reticle (hereinafter, collectively referred to as a "photomask") used, the dust blocks and reflects the irradiated light, and the edges of the transferred pattern become uneven, and the substrate becomes black, or the like, which causes damage to the size, quality, appearance, or the like.
Thus, such an operation is performed in a normal clean room, but even then, it is difficult to keep the photomask clean, and therefore, exposure is performed after attaching a pellicle serving as a dust guard to the surface of the photomask. Thus, the foreign matter such as dust is not attached to the surface of the photomask, but attached to the pellicle, so that the image of the foreign matter does not appear in the transfer pattern when the pattern of the photomask is aligned with the focus of the photolithography, and the above problem can be avoided.
Such a pellicle is generally a transparent pellicle film made of nitrocellulose, cellulose acetate, fluororesin, or the like, which transmits light well, and is adhered to the upper end surface of a pellicle frame made of aluminum, stainless steel, polyethylene, or the like, which is coated with a good solvent for the pellicle film and air-dried (see patent document 1), or is adhered with an adhesive such as an acrylic resin or an epoxy resin (see patent document 2). The lower end face of the pellicle frame is further provided with an adhesive layer made of a polybutylene resin, a polyvinyl acetate resin, an acrylic resin, a silicone resin, or the like, and a release layer (release film) for protecting the adhesive layer, for attaching the photomask.
However, in recent years, semiconductor devices and liquid crystal panels have been increasingly integrated and miniaturized. At present, a technique of forming a fine pattern of 32nm on a photoresist film is also put into practical use. In the case of a pattern of the order of 32nm, a liquid immersion exposure technique for performing exposure on a photoresist film using ArF excimer laser light and a conventional modified technique using excimer laser light such as multiple exposure can be used to make a correspondence between a semiconductor wafer or a liquid crystal master and a projection lens, which are filled with a liquid such as ultrapure water.
However, although the next-generation semiconductor device and liquid crystal panel are required to have a finer pattern of 10nm or less, the formation of such finer pattern of 10nm or less is not performed by conventional exposure improvement techniques using excimer laser light.
Therefore, as a method of patterning at 10nm or less, an EUV exposure technique using EUV light having a dominant wavelength of 13.5nm is becoming necessary. When such EUV exposure techniques are used to produce fine patterns of 10nm or less on a photoresist film, problems of techniques such as what light source is used, what photoresist is used, and what pellicle is used have been essentially solved, and development of new light sources and new photoresist materials has been advanced for such technical problems, and various proposals have been made.
Among them, regarding pellicle assemblies for the yields of left and right semiconductor devices and liquid crystal panels, for example, patent document 3 describes a pellicle film made of silicon, which is transparent and does not generate optical deformation, and has a thickness of 0.1 to 2.0 μm, as a pellicle film used in pellicle assemblies for EUV lithography, but there is an unresolved problem in practical use, and such a problem becomes a great obstacle to practical use of EUV exposure technology.
Prior art literature
Patent literature
Japanese patent document 1 laid-open No. 58-219023
Patent document 2 Japanese patent publication No. 63-27707
Patent document 3 U.S. Pat. No. 6623893 Specification
In general, the material of the adhesive used for attaching the dustproof film to the dustproof film assembly frame is selected in consideration of the adhesive force from the conventional use of exposure using i line (wavelength 365 nm), exposure using KrF excimer laser light (wavelength 248 nm), and exposure using ArF excimer laser light (wavelength 193 nm).
However, when experiments were performed in an environment where fine patterns of 10nm or less were formed on a photoresist film using EUV lithography, conventionally used adhesives had a problem that the adhesive was peeled off from the pellicle film to the pellicle frame.
Accordingly, the present inventors have found that, as a result of repeated simulation on a PC, there is a possibility that the EUV light is heated to around 500 ℃ in the EUV light-irradiated portion of the silicon pellicle, and that the adhesive for bonding the pellicle and the pellicle frame may reach 200 to 300 ℃ from the calculation. Thus, the cause of the peeling of the dust-proof film in the above-described experiment may be due to the high temperature. That is, the adhesive becomes weak when the hardness changes at high temperature and increases, and thus it is difficult to prevent the dust-proof film from peeling off, while it becomes fluid when the hardness becomes low at high temperature, and thus the dust-proof film cannot be fixed and cannot be prevented from peeling off. Therefore, in the pellicle for EUV lithography, if the adhesive agent is heated with low stability to heat, the adhesive agent is excessively hardened and excessively softened, and the adhesion cannot be maintained.
The present invention has been made in view of the above circumstances, and an object thereof is to provide an adhesive agent suitable for an pellicle for EUV lithography, which is excellent in heat resistance (temperature stability) in a high temperature range generated in EUV lithography, a method for producing the pellicle, and a method for selecting an adhesive agent suitable for an pellicle for EUV lithography.
Disclosure of Invention
The present inventors have conducted intensive studies to solve the above problems, and have found that an adhesive having a hardness change rate within a range of ±50% when continuously left standing for 7 days in an atmosphere at 300 ℃ is suitable for EUV exposure technology among a plurality of types of adhesives, and completed the present invention.
Specifically, the adhesive of the present invention is an adhesive suitable for a pellicle for EUV lithography for attaching a pellicle to a pellicle frame, and is characterized in that the rate of change of the hardness represented by the following formula is within ±50% when the cured product of the adhesive is allowed to stand continuously for 7 days in an atmosphere at 300 ℃.
The formula: rate of change in hardness (%) = { (hardness after the rest) - (hardness before the rest) } ∈ (hardness before the rest) ×100
The present invention also provides a pellicle for EUV lithography, comprising a pellicle and a pellicle frame, and an adhesive for bonding the pellicle and the frame to each other, wherein the adhesive of the present invention is used as the adhesive.
The method for producing a pellicle for EUV lithography, which comprises a pellicle, a pellicle frame and an adhesive that adheres the pellicle frame to each other, is characterized by comprising a step of applying the adhesive of the present invention to the pellicle frame.
Further, the method for selecting an adhesive according to the present invention is a method for selecting an adhesive suitable for use in an EUV pellicle for EUV lithography in order to adhere a pellicle of an EUV lithography pellicle to a pellicle frame, and is characterized in that an adhesive having a hardness change rate expressed by the following formula satisfying a condition within ±50% when a cured product of the adhesive to be tested is allowed to stand continuously in an atmosphere at 300 ℃ for 7 days is selected as an adhesive suitable for use in an EUV lithography pellicle.
The formula: rate of change in hardness (%) = { (hardness after the rest) - (hardness before the rest) } ∈ (hardness before the rest) ×100
ADVANTAGEOUS EFFECTS OF INVENTION
The adhesive of the present invention has stability in the high temperature field in the EUV exposure technique, so that the adhesion between the pellicle and the pellicle frame can be maintained in EUV lithography. Therefore, by bonding the pellicle and the pellicle frame with the adhesive of the present invention, a fine pattern of 10nm or less can be formed in the resist film using EUV light.
Drawings
FIG. 1 is a longitudinal cross-sectional view of a dustproof film assembly using the adhesive of the present invention.
Fig. 2 is a schematic explanatory view of an adhesive applying apparatus used in the production of the dustproof film assembly of the present invention.
Detailed Description
Hereinafter, embodiments of the present invention will be described in detail with reference to the accompanying drawings, but the present invention is not limited thereto.
Fig. 1 is a longitudinal sectional view of an embodiment of a dustproof film assembly 1 of the present invention using an adhesive 13 of the present invention. The pellicle 1 has a pellicle 11, a pellicle frame 12, and an adhesive 13 for bonding them to each other. In the pellicle 1, a pellicle 11 is stretched by an adhesive 13 on an upper end surface of a pellicle frame 12 having a generally rectangular frame shape (rectangular frame shape or square frame shape) corresponding to a shape of a substrate (photomask or glass substrate portion: not shown) to be attached to the pellicle 1.
The materials of the dustproof film 11 and the dustproof film module frame 12 are not particularly limited, and known ones can be used.
The material of the dustproof film 11 is monocrystalline silicon, polycrystalline silicon, amorphous silicon, or the like, but is preferably highly transmissive to EUV light. Further, siC, siO may be used for protecting the dust-proof film 11 2 ，Si 3 N 4 ，SiON，Y 2 O 3 And a protective film made of YN, mo, ru, rh, etc.
The material of the pellicle frame 12 is preferably glass or metal having a small linear expansion coefficient, but is more preferably metal from the viewpoints of heat release, workability, and strength.
The adhesive 13 of the present invention is applied to the entire periphery of the upper end surface of the pellicle frame 12, and is intended to attach the pellicle 11 to the pellicle frame 12. The adhesive 13 of the present invention uses an adhesive whose cured product has a hardness change rate of + -50% in the following formula when allowed to stand continuously for 7 days in an atmosphere at 300 ℃. Such an adhesive is particularly suitable for a pellicle for EUV lithography because of its high heat resistance (temperature stability) in EUV lithography. Further, in the present specification and claims, the term "hardness" of a cured product such as an adhesive means "hardness" according to JIS K6249: 2003, in particular, hardness values obtained in hardness tests using a Durro rebound durometer type A apparatus.
The formula: rate of change in hardness (%) = { (hardness after the rest) - (hardness before the rest) } ∈ (hardness before the rest) ×100
In order to obtain the adhesive 13 of the present invention, for example, a commercially available adhesive may be purchased first, and the adhesive may be selected so long as the condition that the rate of change in hardness expressed by the above formula is within ±50% when the cured product of the adhesive is allowed to stand in an atmosphere at 300 ℃ for 7 days. Thus, an adhesive suitable for a pellicle for EUV lithography can be easily obtained without requiring a complicated manufacturing process.
Specific examples of the adhesive 13 satisfying such conditions include commercially available silicon adhesives KE-1803 and KE-1854 (both manufactured by Xinyue chemical industries Co., ltd.: product name), and Epoxy adhesives EK2000 (Epoxy Technology, inc. product name). They have high heat resistance at 300 ℃ or lower and are suitable for use. KE-1803, which is three-part room temperature hardening according to the product description, has a short time to heat hardening. KE-1854 is one-pack heat-curable and EK2000 is two-pack heat-curable.
The adhesive 13 of the present invention is not limited to any curing method, and may be one-pack room temperature curing, one-pack heat curing, two-pack room temperature curing, two-pack heat curing, three-pack room temperature curing, ultraviolet curing, or the like.
The adhesive 13 of the present invention is suitable for adhering a pellicle to a pellicle frame, particularly in a pellicle for EUV lithography. As described above, the energy of the exposure light at the EUV exposure may partially expose the pellicle to high temperatures of up to 500 ℃ and the adhesive used to bond the pellicle and pellicle frame may be exposed to temperatures of up to 200 to 300 ℃.
Therefore, the adhesive 13 of the present invention is required to have sufficient heat resistance in such a high temperature range, and in the heat resistance test of the pellicle assembly using the adhesive 13 of the present invention (the pellicle assembly 1 is allowed to stand continuously in an oven at 250 ℃ for 7 days and then cooled to room temperature), when the adhesive 13 satisfying the above-described conditions of the present invention is used, it can be confirmed that the stretched state of the pellicle 11 at a high temperature of 250 ℃ is well maintained (see examples described later). This is considered to be because the adhesive 13 of the present invention can maintain a sufficient adhesive force even at a high temperature of 250 c, which suggests that the adhesive 13 of the present invention has heat resistance not only at 200 c but also in a high temperature region up to 300 c.
When the adhesive 13 having high heat resistance is applied to the pellicle frame 12, it can be applied by, for example, an adhesive applying apparatus shown in fig. 2. Fig. 2 is a schematic diagram of an example of a suitable adhesive applying apparatus in the application of the adhesive 3. The adhesive applying apparatus 2 is a 3-axis robot 22 configured by combining a fixed rail and a movable rail that are movable in XYZ axis directions, and has an injection cylinder 23 mounted above a mount 21. The tip of the syringe 23 has a needle 25, and the syringe 23 filled with the adhesive 13 is connected to an air pressurizing dispenser (not shown), and both the robot operation and the discharge of the coating liquid are controlled by a control unit (not shown) of the 3-axis robot 22.
Then, the needle 25 moves the adhesive while dropping the adhesive on the pellicle frame 24 mounted on the mount 21 of the adhesive applying apparatus 2, and thereby the adhesive 13 is applied to the pellicle frame 24. In this case, the transfer device (not shown) for the adhesive 13 is not limited to air pressurization, gas pressurization such as nitrogen pressurization, syringe pump, reciprocating pump, tube pump, and the like, and various transfer devices that can control the supply amount and discharge/stop can be used.
Further, when the adhesive 13 has a high viscosity and the coating apparatus 2 is difficult to apply, an aromatic compound such as toluene or xylene, an aliphatic solvent such as hexane, isooctane or isoparaffin, a ketone solvent such as methyl ethyl ketone or methyl isobutyl ketone, an ester solvent such as ethyl acetate or butyl acetate, an ether solvent such as diisopropyl ether or 1, 4-dioxane, or a mixed solvent thereof may be added, if necessary.
Examples
Hereinafter, the present invention will be specifically described with reference to examples and comparative examples.
Example 1
First, the pellicle frame 24 made of super permanent steel (super invariable steel; iron, nickel, cobalt alloy) having an outer dimension of 151mm×118mm×1.5mm in height and a thickness of 4mm was carried into a clean room, and was sufficiently washed with neutral detergent and pure water and dried. Thereafter, the dustproof pellicle frame 24 is fixed to the mount 21 of the adhesive applying apparatus 2 shown in fig. 2.
On the other hand, as the adhesive 13 having high heat resistance, a silicon-based KE-1803 (product name: manufactured by Xinyue chemical Co., ltd.) was used. Since KE-1803 is cured in a three-liquid room temperature curing mode, the main component of KE-1803, the curing agent and the catalyst are weighed in a mass ratio of 100/10/10 based on the amount of the curing agent and the catalyst, and the mixture is sufficiently stirred and mixed to prepare the catalyst.
Next, the prepared adhesive 13 was put into a polypropylene (PP) syringe 23 of the adhesive applicator 2 shown in fig. 2, and the syringe 23 was connected to an air-pressurized distributor (not shown in the drawing) manufactured by under-rock engineering). In the adhesive applying apparatus 2, both the robot operation and the application liquid discharge are controlled by a control unit (not shown) of the 3-axis robot 22, and the adhesive 13 is dropped from the needle 25 over the entire circumference of the dustproof film assembly frame 24 to apply the adhesive.
Thereafter, the dustproof film 11 is attached to the adhesive-coated end face side of the dustproof film assembly frame 24, and the unnecessary film on the outside is cut off with a knife. The adhesive 13 was further allowed to stand and harden at room temperature (25 ℃) for 24 hours to obtain the dustproof film assembly 1.
Example 2
A dustproof film module 1 was produced in the same manner as in example 1, except that a silicon-based one-pack heat-curable KE-1854 (product name: manufactured by Xinyue chemical Co., ltd.) was used as the adhesive 13.
Example 3
A dustproof film module 1 was produced in the same manner as in example except that a silicon-based one-pack heat-curable KE-1880 (product name: manufactured by Xinyue chemical Co., ltd.) was used as the adhesive 13.
Example 4
A dustproof film module 1 was produced in the same manner as in example 1, except that an Epoxy-based two-part thermosetting EK2000 (Epoxy Technology, inc. Product name) was used as the adhesive 13.
Comparative example 1
A dustproof film module 1 was produced in the same manner as in example 1, except that an epoxy-based heat-resistant adhesive Araldite AV138M-1 (product name: manufactured by Ciba-Geigy) was used as the adhesive 13.
Comparative example 2
A dust-proof film module 1 was produced in the same manner as in example 1 except that a woven sock was used as the adhesive 13, using an acrylic heat-resistant adhesive metalrock (product name: manufactured by Cemed Co., ltd.).
Comparative example 3
A pellicle 1 was produced in the same manner as in example 1, except that a silicon-based adhesive KE-3490 (product name: manufactured by Xinyue chemical Co., ltd.) was used as the adhesive 13.
Comparative example 4
A dustproof film module 1 was produced in the same manner as in example 1, except that an epoxy-based heat-resistant adhesive Araldite2000 (product name: manufactured by Ciba-Geigy) was used as the adhesive 13.
Heat resistance test of adhesive
The cured products obtained by curing the adhesives 13 used in examples 1 to 4 and comparative examples 1 to 4 were allowed to stand continuously in an oven at 300℃for 7 days, and then cooled to room temperature, and heat resistance was evaluated. The heat resistance evaluation index was compared using the rate of change in hardness represented by the following formula. The results are shown in Table 1.
The formula: rate of change in hardness (%) = { (hardness after the rest) - (hardness before the rest) } ∈ (hardness before the rest) ×100
Heat resistance test of dustproof film assembly
The dust-proof film assemblies 1 produced in examples 1 to 4 and comparative examples 1 to 4 were allowed to stand in an oven at 250℃for 7 days, and then cooled to room temperature, and the state of tightening of the dust-proof film 11 was confirmed. The results are shown in Table 1.
TABLE 1
From the results of table 1, the adhesive used in examples 1 to 4 had a hardness change rate of +40%, +50%, +30%, +50% after the heat resistance test at 300 ℃ and was low, and the adhesive used in examples 1 to 4 had a good state of tightening the dustproof film in the heat resistance test of the dustproof film assembly used in the adhesive, and the adhesive used in the adhesive was not deteriorated in adhesion at high temperature, and was confirmed to have high heat resistance.
On the other hand, the adhesives used in comparative examples 1 to 3 had hardness change rates of +350%, +400%, +200%, respectively, after a heat resistance test at 300℃and were large, and the state (property) of the adhesive was also fragile. Furthermore, the adhesive of comparative example 4 had a hardness change rate of-100% after a heat resistance test at 300℃and a state (property) of the adhesive was soft. In the heat resistance test of the pellicle, peeling of the pellicle film from the pellicle frame was observed, and it was confirmed that the adhesives used in comparative examples 1 to 4 were poor in heat resistance.
Thus, KE-1803, KE-1854, KE-1880 and EK2000 of the silicon-based adhesive used in examples 1 to 4 are excellent in heat resistance, and particularly, they are suitable as an adhesive for a pellicle used in EUV exposure.
Description of symbols
1. Dustproof film assembly
2. Adhesive coating device
11. Dustproof film
12. Dustproof film assembly frame
13. Adhesive agent
21. Stand for stand
22 3-axis robot
23. Injection tube
24. Dustproof film assembly frame
25. Needle
Claims (10)
1. A pellicle comprising a pellicle frame and a pellicle film adhered to the frame by an adhesive layer, wherein the adhesive layer does not include a thermally conductive filler, and wherein the adhesive layer is used as the adhesive layer, wherein the adhesive layer is used in such a manner that the rate of change of the hardness of the cured product of the adhesive is within + -50% when the cured product is continuously left standing in an atmosphere at 300 ℃ for 7 days, and wherein the adhesive layer is used in heating of the EUV lithography so as to maintain the adhesion between the pellicle film and the pellicle frame without excessive curing and excessive softening,
the formula: the rate of change in hardness (%) = { (hardness after the rest) - (hardness before the rest) } is ≡ (hardness before the rest) ×100.
2. The use according to claim 1, wherein the adhesive is a silicon-based adhesive or an epoxy-based adhesive.
3. The application of a dustproof film assembly formed by adhering a dustproof film to a dustproof film assembly frame through an adhesive layer is characterized in that the adhesive layer does not comprise a heat conductive filler, the adhesive layer is used as the adhesive layer, the change rate of the hardness of a hardening object of the adhesive is within a range of +/-50% when the hardening object is continuously kept in an atmosphere of 300 ℃ for 7 days, the adhesive layer is used at the temperature of 200-300 ℃ so as to maintain the adhesive force between the dustproof film and the dustproof film assembly frame, and the adhesive layer is not excessively hardened and excessively softened,
the formula: the rate of change in hardness (%) = { (hardness after the rest) - (hardness before the rest) } is ≡ (hardness before the rest) ×100.
4. The method according to claim 3, wherein the adhesive is a silicon-based adhesive or an epoxy-based adhesive.
5. A method for manufacturing a semiconductor, characterized in that EUV exposure is performed using a photomask to which a pellicle for EUV lithography is attached,
the photomask to which the dustproof film component is attached is formed by attaching the dustproof film component to the photomask,
the dustproof film component is formed by adhering the dustproof film to the dustproof film component frame through an adhesive layer,
the adhesive layer does not include a thermally conductive filler, and is used as the adhesive layer, and the adhesive layer is used in which the rate of change of hardness expressed by the following formula is within + -50% when a cured product of the adhesive is continuously left standing in an atmosphere at 300 ℃ for 7 days, and is used to maintain adhesion between the pellicle and the pellicle frame at the time of heating for EUV lithography, without excessive hardening and excessive softening of the adhesive layer,
the formula: the rate of change in hardness (%) = { (hardness after the rest) - (hardness before the rest) } is ≡ (hardness before the rest) ×100.
6. A method for manufacturing a semiconductor, characterized in that exposure is performed in a temperature environment of 200-300 ℃ using a photomask to which a pellicle is attached,
the photomask to which the dustproof film component is attached is formed by attaching the dustproof film component to the photomask,
the dustproof film component is formed by adhering the dustproof film to the dustproof film component frame through an adhesive,
the adhesive layer does not include a heat conductive filler, and the adhesive layer is used as the adhesive layer, wherein the adhesive layer has a hardness change rate of + -50% expressed by the following formula when a cured product of the adhesive is continuously left standing in an atmosphere at 300 ℃ for 7 days, and the adhesive layer is used at a temperature of 200-300 ℃ to maintain adhesion between the dustproof film and the dustproof film assembly frame without excessive hardening and excessive softening,
the formula: the rate of change in hardness (%) = { (hardness after the rest) - (hardness before the rest) } is ≡ (hardness before the rest) ×100.
7. The method of manufacturing a semiconductor according to claim 6, wherein the adhesive is a silicon-based adhesive or an epoxy-based adhesive.
8. A method for manufacturing a liquid crystal panel, characterized in that EUV exposure is performed using a photomask to which a pellicle for EUV lithography is attached,
the photomask to which the dustproof film component is attached is formed by attaching the dustproof film component to the photomask,
the dustproof film component is formed by adhering the dustproof film to the dustproof film component frame through an adhesive layer,
the adhesive layer does not include a thermally conductive filler, and is used as the adhesive layer, and the adhesive layer is used in which the rate of change of hardness expressed by the following formula is within + -50% when a cured product of the adhesive is continuously left standing in an atmosphere at 300 ℃ for 7 days, and is used to maintain adhesion between the pellicle and the pellicle frame at the time of heating for EUV lithography, without excessive hardening and excessive softening of the adhesive layer,
the formula: the rate of change in hardness (%) = { (hardness after the rest) - (hardness before the rest) } is ≡ (hardness before the rest) ×100.
9. A method for manufacturing a liquid crystal panel, characterized in that exposure is performed in a temperature environment of 200-300 ℃ by using a photomask to which a dustproof film component is attached,
the photomask to which the dustproof film component is attached is formed by attaching the dustproof film component to the photomask,
the dustproof film component is formed by adhering the dustproof film to the dustproof film component frame through an adhesive layer,
the adhesive layer does not include a thermally conductive filler, and is used as the adhesive layer, and the adhesive layer is used in which the rate of change of hardness expressed by the following formula is within + -50% when a cured product of the adhesive is continuously left standing in an atmosphere at 300 ℃ for 7 days, and is used to maintain adhesion between the pellicle and the pellicle frame at the time of heating for EUV lithography, without excessive hardening and excessive softening of the adhesive layer,
the formula: the rate of change in hardness (%) = { (hardness after the rest) - (hardness before the rest) } is ≡ (hardness before the rest) ×100.
10. The method of manufacturing a liquid crystal panel according to claim 9, wherein the adhesive is a silicon-based adhesive or an epoxy-based adhesive.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010637924.8A CN111679549B (en) | 2015-10-29 | 2016-10-25 | Adhesive suitable for pellicle for EUV lithography and pellicle using the adhesive |
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| JP2015-212619 | 2015-10-29 | ||
| JP2015212619 | 2015-10-29 | ||
| JP2015245060A JP6516665B2 (en) | 2015-10-29 | 2015-12-16 | Adhesive suitable for pellicle for EUV lithography and pellicle using the same |
| JP2015-245060 | 2015-12-16 | ||
| CN202010637924.8A CN111679549B (en) | 2015-10-29 | 2016-10-25 | Adhesive suitable for pellicle for EUV lithography and pellicle using the adhesive |
| CN201610937977.5A CN106647161B (en) | 2015-10-29 | 2016-10-25 | Adhesive suitable for pellicle for EUV lithography and pellicle using the same |
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| CN201610937977.5A Division CN106647161B (en) | 2015-10-29 | 2016-10-25 | Adhesive suitable for pellicle for EUV lithography and pellicle using the same |
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| CN201610937977.5A Active CN106647161B (en) | 2015-10-29 | 2016-10-25 | Adhesive suitable for pellicle for EUV lithography and pellicle using the same |
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| JP7451442B2 (en) * | 2017-10-10 | 2024-03-18 | 信越化学工業株式会社 | Ventilation structure of EUV pellicle frame, EUV pellicle, exposure master plate with EUV pellicle, exposure method, and semiconductor manufacturing method |
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| JP2015018228A (en) * | 2013-06-10 | 2015-01-29 | 旭化成イーマテリアルズ株式会社 | Pellicle film and pellicle |
| CN106597806A (en) * | 2015-10-19 | 2017-04-26 | 信越化学工业株式会社 | A pellicle for EUV |
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| JPH01278019A (en) * | 1988-04-28 | 1989-11-08 | Canon Inc | Structure of lithography mask |
| JP3449180B2 (en) * | 1997-06-27 | 2003-09-22 | 信越化学工業株式会社 | Pellicle |
| US6492067B1 (en) * | 1999-12-03 | 2002-12-10 | Euv Llc | Removable pellicle for lithographic mask protection and handling |
| US6623893B1 (en) | 2001-01-26 | 2003-09-23 | Advanced Micro Devices, Inc. | Pellicle for use in EUV lithography and a method of making such a pellicle |
| JP5067929B2 (en) * | 2007-06-01 | 2012-11-07 | 信越ポリマー株式会社 | Manufacturing method of fixing roller |
| JP5711703B2 (en) * | 2012-09-03 | 2015-05-07 | 信越化学工業株式会社 | EUV pellicle |
| JP6084681B2 (en) * | 2013-03-15 | 2017-02-22 | 旭化成株式会社 | Pellicle membrane and pellicle |
| US10139725B2 (en) * | 2013-03-27 | 2018-11-27 | Asml Netherlands B.V. | Lithographic apparatus |
| JP6364404B2 (en) * | 2013-05-24 | 2018-07-25 | 三井化学株式会社 | Pellicle and EUV exposure apparatus including the same |
| JP6326056B2 (en) * | 2013-09-30 | 2018-05-16 | 三井化学株式会社 | Pellicle film, pellicle using the same, exposure original plate and exposure apparatus, and method for manufacturing semiconductor device |
| KR102338110B1 (en) * | 2013-12-16 | 2021-12-09 | 모멘티브 파포만스 마테리아루즈 쟈판 고도가이샤 | Addition-curable silicone composition |
| JP6308592B2 (en) * | 2014-04-02 | 2018-04-11 | 信越化学工業株式会社 | EUV pellicle |
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| JP2015018228A (en) * | 2013-06-10 | 2015-01-29 | 旭化成イーマテリアルズ株式会社 | Pellicle film and pellicle |
| CN106597806A (en) * | 2015-10-19 | 2017-04-26 | 信越化学工业株式会社 | A pellicle for EUV |
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| TWI607075B (en) | 2017-12-01 |
| JP2017083806A (en) | 2017-05-18 |
| CN106647161B (en) | 2020-08-18 |
| CN106647161A (en) | 2017-05-10 |
| KR102634999B1 (en) | 2024-02-07 |
| KR20170051226A (en) | 2017-05-11 |
| TW201726875A (en) | 2017-08-01 |
| JP6516665B2 (en) | 2019-05-22 |
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