WO2013080741A1 - Composition photopolymérisable et procédé de formation de motif l'utilisant - Google Patents

Composition photopolymérisable et procédé de formation de motif l'utilisant Download PDF

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Publication number
WO2013080741A1
WO2013080741A1 PCT/JP2012/078457 JP2012078457W WO2013080741A1 WO 2013080741 A1 WO2013080741 A1 WO 2013080741A1 JP 2012078457 W JP2012078457 W JP 2012078457W WO 2013080741 A1 WO2013080741 A1 WO 2013080741A1
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Prior art keywords
photopolymerizable composition
group
siloxane compound
integer
substrate
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PCT/JP2012/078457
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English (en)
Japanese (ja)
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毅 小川
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セントラル硝子株式会社
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
    • C08G59/306—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen containing silicon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/3254—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen
    • C08G59/3281—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen containing silicon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of 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
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0002—Lithographic processes using patterning methods other than those involving the exposure to radiation, e.g. by stamping
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/075—Silicon-containing compounds
    • G03F7/0755—Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
    • H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
    • H01L21/02123—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon
    • H01L21/02126—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer the material containing silicon the material containing Si, O, and at least one of H, N, C, F, or other non-metal elements, e.g. SiOC, SiOC:H or SiONC
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
    • H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
    • H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
    • H01L21/02288—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating printing, e.g. ink-jet printing
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having at least one potential-jump barrier or surface barrier, e.g. PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic System or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/3105—After-treatment
    • H01L21/311—Etching the insulating layers by chemical or physical means

Definitions

  • the present invention relates to a photopolymerizable composition for nanoimprint applications and a pattern forming method using a nanoimprint process using the same.
  • Nanoimprinting involves directly pressing a master with a microfabricated pattern (hereinafter sometimes referred to simply as a pattern) against a substrate coated with a transfer material such as a resin, so that the pattern of the master (hereinafter referred to as the master pattern) is applied to the substrate.
  • a master pattern called a template, mold or stamp is formed in advance with a finely processed original pattern, which is then transferred to a transfer material such as a resin or resin precursor applied to the substrate.
  • a pattern is obtained on the substrate.
  • a transfer pattern is obtained by applying an original pattern of a template to a resin or resin precursor applied to a substrate.
  • nanoimprinting For nanoimprinting, optical nanoimprinting using a photopolymerizable composition (hereinafter sometimes referred to as nanoimprint lithography), thermal nanoimprinting using a thermoplastic resin as a transfer material, and a highly viscous resin called spin-on-glass (SOG) are used.
  • lithography photopolymerizable composition
  • SOG spin-on-glass
  • room temperature nanoimprint There are various types such as room temperature nanoimprint.
  • Patent Document 1 describes optical nanoimprint
  • Patent Document 2 describes thermal nanoimprint
  • Patent Document 3 describes room temperature nanoimprint.
  • optical nanoimprints are listed as candidates for microfabrication in next-generation semiconductors in the International Semiconductor Technology Roadmap (Non-Patent Document 1) issued by the International Semiconductor Technology Roadmap (ITRS) Committee.
  • the process throughput processing capacity per unit time of the process
  • optical nanoimprint does not require an expensive exposure apparatus and is economically advantageous, unlike extreme ultraviolet light (wavelength: 13.5 nm) lithography, which is a candidate for fine processing in the other next-generation semiconductor.
  • the formation of a transfer pattern by photo-nanoimprinting involves applying a template original pattern to a liquid photopolymerizable composition, which is a transfer material applied to a substrate, and irradiating light through the template to cure the photopolymerizable composition.
  • a transfer pattern is obtained. If an electron beam is used, it is possible to obtain an original pattern on the template with an accuracy of 20 nm or less.
  • quartz or sapphire that transmits light having a wavelength necessary for photopolymerization is used.
  • the photopolymerizable composition includes a film-forming composition containing a polymeric silicon compound that causes a photocuring reaction described in Patent Document 4, a fluorine-based surfactant, a silicone-based surfactant, or fluorine described in Patent Document 5.
  • a curable composition for optical nanoimprint lithography containing a silicone type surfactant and the ultraviolet curable resin material in which pattern transfer of patent document 6 is possible are mentioned.
  • transfer material to the substrate in optical nanoimprinting
  • precise transferability and alignment accuracy of fine structures are important, transfer pattern accuracy is excellent in in-plane uniformity and throughput is improved.
  • the ink jet method is often adopted because the reduction of pattern defects can be achieved.
  • the ink jet method is a film in which the photopolymerizable composition is sprayed as droplets on a substrate with a nozzle, and the composition is cured by irradiating light in a state where the template pattern on the template is applied to the coated surface. Get on the substrate.
  • the volume of droplets to be sprayed is on the order of picoliter, and the photopolymerizable composition is required to be a liquid having low viscosity and vapor pressure.
  • the filling of the template of the photopolymerizable composition into the original plate pattern is performed spontaneously by capillary action when the template is applied to the coating film of the photopolymerizable composition on the substrate, so it is necessary to pressurize the template. There is no.
  • the transfer pattern is often used as a mask pattern for a metal thin film or the like formed in the lower layer of the pattern.
  • a thin film to which the original pattern is transferred is obtained by etching the thin film after nanoimprinting.
  • Inkjet optical nanoimprinting equipment includes the product name IMPLO of US Molecular Imprints, which employs step-and-flash imprint lithography, and uses a drop-on-demand system that controls the amount of coating by inkjet based on the accuracy of the template original pattern. Adopted to improve the flatness and throughput of the transfer pattern and reduce pattern defects.
  • a photopolymerizable composition composed of various polymerizable acrylate compounds and a photopolymerization initiator is generally used.
  • the chemical structure or composition of the photopolymerizable composition is adjusted, the cured product after photopolymerization can be used as a permanent member.
  • the resulting cured product of the siloxane resin is excellent in durability, such as insulation, mechanical strength, and acid / alkaline resistance.
  • a polymerizable acrylate compound it can be used as a permanent member, for example, an insulating film.
  • the physical property required for the photopolymerizable composition containing the siloxane compound is a liquid having a low viscosity and a low vapor pressure. It is also important that it can be used in industry, such as easy synthesis and easy handling.
  • Optical nanoimprint may be referred to as a low dielectric constant interlayer insulating film (hereinafter referred to as Low-k film) in a back-end process (hereinafter sometimes referred to as BEOL) for forming a multilayer wiring structure of a state-of-the-art logic semiconductor or memory. ),
  • BEOL back-end process
  • the number of steps can be reduced.
  • the first problem is that the liquid photopolymerizable composition has a high viscosity and is difficult to apply to the substrate by the ink jet method.
  • the viscosity of the composition that can be applied by inkjet is 30 m ⁇ Pa ⁇ s or less at 25 ° C. If it exceeds 30 m ⁇ Pa ⁇ s, it is difficult to apply a uniform film thickness by the ink jet method, and the ink jet nozzle may be blocked.
  • an organic solvent is added to the photopolymerizable composition to reduce the viscosity, the vapor pressure increases, and a coating film with a smooth surface cannot be obtained due to volatilization of droplets ejected by inkjet onto the substrate. The accuracy of the transfer pattern on the substrate is reduced. Moreover, adding a large amount of an organic solvent may cause a decrease in physical properties of the cured product.
  • the second problem is that it is difficult to synthesize a photopolymerizable composition.
  • the following polysubstituted cage-type silsesquioxane can introduce a substituent at each apex, has a wide range of molecular design, and has been studied for use in photopolymerizable compositions of photonanoimprint.
  • X represents two or more kinds of polymerizable substituents
  • the multi-substituted cage-type silsesquioxane is the same when a plurality of polymerizable substituents X are introduced into one molecule except when a polymerizable substituent X is introduced at a specific ratio. Things are hard to get.
  • X is an acryloyl group and a maleimide group, each represented by a molar ratio of 50:50, and introduced into one molecule
  • the resulting product can be seen at the molecular level and the acryloyl group and the maleimide group can be obtained.
  • optical imprinting there is a problem in that not only the desired physical properties cannot be obtained in the cured product due to biased substituents, but also the curing condition and physical properties vary between lots.
  • the photopolymerizable composition containing a siloxane compound used in the prior art uses a siloxane compound or a multifunctional cage silsesquioxane produced by a sol-gel method, and these compounds have a desired chemical structure and A synthesis method for obtaining physical properties with good reproducibility has not been established. Therefore, it is difficult to employ in industrial production, and it is difficult to industrially use it as a transfer material for optical nanoimprint.
  • the present invention solves the above problems, has a low viscosity and low vapor pressure at room temperature (25 ° C.), can be suitably used as a transfer material for optical nanoimprint, and is based on an ink jet system even in a state not containing an organic solvent.
  • An object of the present invention is to provide a photopolymerizable composition which can be applied and from which a polymerized cured product as a silicon resin can be obtained with good reproducibility when photopolymerized by irradiation with high energy rays. And it aims at obtaining the pattern formation method by the photo nanoimprint using the said photopolymerizable composition.
  • the present invention comprises the following inventions 1 to 6.
  • a photopolymerizable composition for photo-nanoimprint use comprising a photopolymerization initiator and a siloxane compound, wherein the siloxane compound is a siloxane compound (A) represented by the general formula (1) and the general formula (2)
  • a photopolymerizable composition which is at least one selected from the group consisting of siloxane compounds (B) represented by:
  • group A is a polymerizable group
  • m is an integer of 1 to 10
  • n is an integer of 1 to 10
  • p is an integer of 0 to 5.
  • group B is a polymerizable group
  • q is an integer of 1 to 10
  • r is an integer of 0 to 5).
  • Invention 2 The photopolymerizable composition of Invention 1, wherein the group A and the group B are each independently an acryloyl group, a methacryloyl group, a vinyl group, a vinyl ether group, an epoxy group, or an oxetane group.
  • invention 4 The photopolymerizable composition according to inventions 1 to 3, having a vapor pressure at 25 ° C. of 267 Pa or less.
  • [Invention 5] A step of spraying the photopolymerizable composition of the inventions 1 to 4 on the substrate in the form of droplets with a nozzle, and applying the photopolymerizable composition on the substrate;
  • a substrate comprising: a step of polymerizing and curing the photopolymerizable composition by irradiating the photopolymerizable composition with a high energy light through the template in a state of contact with the photopolymerizable composition applied to the substrate; and a step of separating the template from the substrate.
  • a pattern forming method for transferring a template pattern onto the top
  • invention 6 The method of the invention 5, wherein the high energy light is an electromagnetic wave or an electron beam having a wavelength of 420 nm or less.
  • a photopolymerizable composition containing a photopolymerization initiator and a siloxane compound having a specific branched or cyclic structure can be used as an optical nanoimprint transfer material.
  • the siloxane compound which is a constituent of the photopolymerizable composition of the present invention, is synthesized with good reproducibility and can be polymerized by the action of a photopolymerization initiator irradiated with high energy light.
  • the siloxane compound is a low-viscosity and low vapor pressure liquid around room temperature (around 25 ° C.), and can be applied by an inkjet nozzle.
  • the photopolymerizable composition for nanoimprinting of the present invention and a pattern forming method using the same will be described below.
  • Photopolymerizable composition for nanoimprint The photopolymerizable composition for use in photonanoimprinting of the present invention comprises a photopolymerization initiator and a siloxane compound.
  • the siloxane compound contained in the photopolymerizable composition of the present invention includes a siloxane compound (A) represented by the general formula (1) having a branched chain structure and a general formula (2) having a cyclic structure. And at least one siloxane compound selected from the group consisting of siloxane compounds (B).
  • the group A is a polymerizable group
  • m is an integer of 1 to 10
  • n is an integer of 1 to 10
  • p is an integer of 0 to 5.
  • the group B is a polymerizable group
  • q is an integer of 1 to 10
  • r is an integer of p to 5.
  • siloxane compound (A) and the siloxane compound (B) contained in the photopolymerizable composition of the present invention are cured after photopolymerization, they become a silicon resin having a siloxane bond, and have excellent heat resistance and low water absorption. Showing gender. Since the siloxane compound (A) and the siloxane compound (B) are molecular chain or cyclic, they are less viscous in the same temperature range than the linear siloxane compound having the same molecular weight.
  • the siloxane compound (A) is a liquid having a low viscosity and a low vapor pressure at room temperature (25 ° C.).
  • the cured product after photopolymerization has a low dielectric constant, and the shrinkage rate upon photocuring is low, so that a precise transfer pattern can be obtained.
  • the siloxane compound (B) is a liquid having a low viscosity and a low vapor pressure at room temperature (25 ° C.). Furthermore, since it has the functional group B radially from the cyclic structure, the cured product after photopolymerization has a high crosslinking density, no glass transition temperature, no crystallinity, and is amorphous, and has excellent mechanical properties.
  • the polymerizable groups A and B of the siloxane compound (A) and the siloxane compound (B) that are constituents of the photopolymerizable composition of the present invention are each independently an acryloyl group, a methacryloyl group, a vinyl group, a vinyl ether group, It is preferably an epoxy group or an oxetane group.
  • These photopolymerizable groups may be directly bonded to the silicon atom of the siloxane compound (A) and the siloxane compound (B), or may be bonded via an alkylene group.
  • the siloxane compound (A) and the siloxane compound (B) used in the photopolymerizable composition of the present invention can be used either alone or as a mixture.
  • the ratio is not particularly limited and can be mixed at an arbitrary ratio. For example, when it is desired to reduce the relative dielectric constant of the cured product after photopolymerization, the ratio of the siloxane compound (A) is increased, and when the mechanical strength of the cured product after photopolymerization is desired to be increased, the siloxane compound (B ) Is easy to control the physical properties of the resulting cured product.
  • the photopolymerization initiator used in the photopolymerizable composition of the present invention is a polymerizable group that the siloxane compound (A) has by generating radicals or acids by irradiation with high-energy light. It acts on the polymerizable group B of A or the siloxane compound (B) to polymerize the siloxane compound (A) or the siloxane compound (B).
  • Specific examples include a photo radical polymerization initiator and a photo cationic polymerization initiator.
  • Photoradical polymerization initiators include an intramolecular cleavage type in which intramolecular bonds are cleaved to generate radicals, and a hydrogen abstraction type in which hydrogen donors such as tertiary amines and ethers are used in combination to generate radicals. Any of them can be used in the present invention.
  • the intramolecular cleavage type 2-hydroxy-2-methyl-1-phenylpropan-1-one (Ciba Specialty Chemicals Co., Ltd., trade name Darocur 1173)
  • the carbon-carbon bond is cleaved by light irradiation. To generate radicals.
  • Examples of the hydrogen abstraction type include benzophenone, methyl orthobenzoin benzoate, 4-benzoyl-4'-methyldiphenyl sulfide, and the like, and generate radicals by a bimolecular reaction with a hydrogen donor by light irradiation.
  • radicals the double bond of acryloyl group, methacryloyl group or vinyl group is cleaved, and siloxane compound (A) or siloxane compound (B) is polymerized.
  • the photoradical polymerization generator is not particularly limited as long as it is a compound that generates radicals by absorbing light, and a commercially available photopolymerization initiator can be used, for example, manufactured by Ciba Specialty Chemicals Co., Ltd. From the photopolymerization initiator Darocur series, the trade names Irgacure 127, Irgacure 184, Irgacure 2959, Irgacure 369, Irgacure 379, Irgacure 907, Irgacure 1700, Irgacure 1800, Irgacure 1850, Irgacure 1265 or Irgacure 1265 can be used.
  • a commercially available photopolymerization initiator can be used, for example, manufactured by Ciba Specialty Chemicals Co., Ltd. From the photopolymerization initiator Darocur series, the trade names Irgacure 127, Irgacure 184,
  • Examples of the cationic photopolymerization initiator include onium salt compounds such as diazonium salts, iodonium salts, sulfonium salts, and phosphonium salts. These compounds generate acids after being excited by irradiation with light.
  • the siloxane compound (A) or (B) is polymerized by cleavage of the epoxy group or oxetane group or cleavage of the double bond of the vinyl ether group by these acids.
  • the cationic photopolymerization initiator is not particularly limited as long as it is a compound that generates an acid by absorbing light, and a commercially available photopolymerization initiator can be used, for example, a light produced by Ciba Specialty Chemicals Co., Ltd. From polymerization initiator Irgacure series, trade name, Irgacure261, or photopolymerization initiator of Midori Chemical Co., Ltd., trade names BBI-103, MPI-103, TPS-103, MDS-103, DTS-103, NAT-103 or NDS-103 can be used.
  • the proportion of the photopolymerization initiator used as a constituent of the photopolymerizable composition of the present invention is in the range of 0.1% by mass to 7% by mass based on the total mass of the photopolymerizable composition.
  • the content is less than 0.1% by mass, it is difficult to obtain a cured product by a photopolymerization reaction.
  • it exceeds 7 mass% the physical property of the hardened
  • the photopolymerizable composition of the present invention has a low viscosity of 30 m ⁇ Pa ⁇ s or less at 25 ° C. When the viscosity exceeds 30 m ⁇ Pa ⁇ s, it becomes difficult to control the volume of the droplets ejected by the ink jet. In some cases, the inkjet nozzle is blocked.
  • the photopolymerizable composition of the present invention has a low vapor pressure of 267 Pa or less at 25 ° C. If the vapor pressure exceeds 267 Pa, volatilization of droplets cannot be ignored when ejected onto a substrate by inkjet, and it is difficult to form a film with a uniform film thickness. As a result, the reproducibility of the original pattern becomes difficult in the transfer pattern by optical nanoimprint.
  • the photopolymerizable composition of the present invention undergoes a polymerization reaction by the action of a photopolymerization initiator when irradiated with high energy light, and becomes a cured product.
  • High energy light used for light irradiation is ultraviolet light including a near ultraviolet region, specifically, ultraviolet light of 420 nm or less. Practically, ultraviolet light having a wavelength of 200 nm or more and 420 nm or less is easy to use, and light sources that emit ultraviolet light in these wavelength ranges include high pressure mercury lamps, ultrahigh pressure mercury lamps, medium pressure mercury lamps, low pressure mercury lamps, metal halide lamps, xenon.
  • a flash lamp or an ultraviolet light emitting diode (LED) can be mentioned and can be used for curing the photopolymerizable composition of the present invention.
  • the template used in the nanoimprint of the present invention needs to be made of a material that transmits wavelengths below the ultraviolet light region, and specifically includes quartz and sapphire.
  • the pattern forming method of the present invention comprises a step of spraying the photopolymerizable composition of the inventions 1 to 4 on a substrate in a droplet state with a nozzle, and applying the photopolymerizable composition on the substrate; A step of polymerizing and curing the photopolymerizable composition by irradiating the photopolymerizable composition through the template with the template on which the original pattern is formed in contact with the photopolymerizable composition applied on the substrate; A pattern forming method for transferring a pattern of the template onto the substrate.
  • the photopolymerizable composition of the inventions 1 to 4 is sprayed onto a substrate in the form of droplets from an inkjet nozzle, and a template on which an original pattern is formed is applied to the substrate in accordance with optical nanoimprint.
  • the photopolymerizable composition is cured, and the template is separated from the cured body to form a transfer pattern on the substrate.
  • the high energy light is preferably an electromagnetic wave or an electron beam having a wavelength of 420 nm or less, having an energy for polymerizing a siloxane compound by acting on a photopolymerization initiator to generate radicals or acids.
  • the transfer pattern formed by photo-nanoimprinting and polymerizing the photopolymerizable composition of the present invention is used as a low dielectric constant interlayer insulating film used in a semiconductor device.
  • the semiconductor device includes a logic semiconductor such as a microprocessor, a volatile memory such as a DRAM (Dynamic Random Access Memory), or a flash memory.
  • a photopolymerization initiator was added to obtain a photopolymerizable composition of the present invention.
  • Example 1 the siloxane compound (A-1) belonging to the siloxane compound (A) having a branched structure and the siloxane compound (B-1) belonging to the siloxane compound (B) having a cyclic structure were irradiated with light.
  • a polymerization initiator was added to obtain a photopolymerizable composition (1) of the present invention.
  • Example 2 in order to obtain a cured product with higher strength, a photopolymerization initiator was added to the siloxane compound (B-1) to obtain a photopolymerizable composition (2) of the present invention.
  • the viscosity of the photopolymerizable composition was measured with a vibration viscometer (manufactured by Seconic Corporation, product name, VM-100A). Vapor pressure was determined by sealing the photopolymerizable composition in a stainless steel 10 ml cylinder of Swagelok, USA, and repeating the operation of degassing the dissolved air three times while cooling with liquid nitrogen. was measured with a diaphragm-type pressure gauge (manufactured by Nippon KS Co., Ltd., product name, Baratron 626B).
  • a UV irradiation device manufactured by Moritex Co., Ltd., product name, MUV-351U was used as a light source for polymerizing the photopolymerizable composition to obtain a cured product.
  • the relative permittivity of the cured product is a thin film-shaped cured product, and a metal electrode is created with a conductive paste (made by Fujikura Kasei Co., Ltd., trade name Dotite) on the upper and lower portions thereof. 4294A), the capacitance value at a frequency of 1 MHz was measured and calculated.
  • a 5% mass reduction temperature in a thermal mass curve obtained by a differential thermobalance TG-DTA manufactured by Rigaku Corporation, TG8120
  • the glass transition temperature was measured using a differential scanning calorimeter (manufactured by Seiko Instruments Inc., product name, DSC6200).
  • the mechanical strength was measured by preparing a cured product in the form of a thin film on a silicon substrate and nanoindentation (trade name: Triboindenter, manufactured by Eattron, USA). The water absorption was calculated from the amount of mass change before and after immersion after the cured product was dried in an oven at 120 ° C. overnight, and then the cured product was immersed in pure water for 24 hours.
  • the photocuring shrinkage before and after curing of the photopolymerization composition was calculated by measuring the amount of change in film thickness before and after photocuring on the silicon substrate with an optical interference film thickness meter (manufactured by Sentec Germany, FTP500).
  • Example 1 [Synthesis of photopolymerizable siloxane compound] A siloxane compound (A-1) represented by the formula (3) belonging to the siloxane compound (A) having a branched structure was synthesized according to a known synthesis method (Non-patent Document 3).
  • the siloxane compound (A-1) represented by the formula (3) is available from the University of Texas as the product name Si-12 methacryl.
  • siloxane compound (B-1) represented by the formula (4) belonging to the photopolymerizable siloxane compound (B) having a cyclic structure was synthesized.
  • a photopolymerization initiator represented by the formula (5) was added to the siloxane compound (A-1) and the siloxane compound (B-1) shown above.
  • the photopolymerization initiator is commercially available under the trade name Darocur 1173 from Ciba Specialty Chemicals.
  • the photocurable composition is expressed in terms of mass ratio so that the ratio of siloxane compound (A-1): siloxane compound (B-1): photopolymerization initiator is 49: 49: 2. Prepared.
  • Example 2 The same procedure as in Example 1 was performed, except that only the photopolymerizable siloxane compound (B-1) was used as the photopolymerizable siloxane compound.
  • photopolymerizable composition The photopolymerizable siloxane compound (B-1) having a cyclic structure and the photopolymerization initiator used in Example 1 were represented by a mass ratio, and the siloxane compound (B-1): photopolymerization initiator was 98: 2.
  • the photopolymerizable composition was prepared so that it might become a ratio.
  • Table 1 shows the measurement results of the viscosity and vapor pressure of the photopolymerizable compositions (1) and (2), and Table 2 shows the relative dielectric constant and heat resistance of the cured products (1) and (2) after photopolymerization. The measurement results of properties, glass transition temperature, mechanical strength, photocuring shrinkage and water absorption are shown.
  • Both the photopolymerizable compositions (1) and (2) have a viscosity of 30 m ⁇ Pa ⁇ s (30 cP) or less and a vapor pressure of 267 Pa (2 Torr) or less, and can be applied to a substrate by inkjet in optical nanoimprint. there were. Further, the relative permittivity, heat resistance, glass transition temperature, mechanical strength, photocuring shrinkage, and water absorption of the cured product after photopolymerization were values that could be used as a low dielectric constant interlayer insulating film.
  • a quartz template on which a nano-order master pattern was formed was prepared.
  • a toluene solution containing 1.0% by mass of tridecafluoro-1,1,2,2-tetrahydrooctyldimethylchlorosilane (manufactured by Gelest, USA) was prepared, and the template was immersed in the solution for 1 hour to obtain a surface of the template. Processed.
  • a silicon substrate was prepared, and a coating solution (trade name mr-APS1, manufactured by Microresist Technology, Germany) for forming an adhesion layer corresponding to the lower layer film of the optical nanoimprint was applied onto the silicon substrate at a rotational speed of 5000 rpm. Spin coating was performed for 60 seconds, and heating was performed at 150 ° C. for 60 seconds to form an adhesion layer.
  • the above photopolymerizable compositions (1) and (2) were respectively applied onto such two silicon substrates, and the template was slowly brought into contact therewith from above. Subsequently, the photopolymerizable composition was cured by irradiating ultraviolet light with an intensity of 20 mW / cm 2 for 180 seconds from the upper side of the template. The template was pulled away from the cured product to obtain a transfer pattern by optical nanoimprint on the silicon substrate. When the pattern was observed with an optical microscope and an electron microscope, good transferability was confirmed.
  • Comparative Example 1 Synthesis of photopolymerizable siloxane compound
  • the photopolymerizable siloxane compound (C-1) represented by the formula (6) was synthesized according to a known synthesis method (Non-patent Document 3).
  • the photopolymerizable siloxane compound (C-1) represented by the formula (6) is available as a trade name OMPS from Myatereals, USA. This compound has a cage-type molecular structure formed by a siloxane bond, and is generally called a cage-type silsesquioxane.
  • photopolymerizable composition The photopolymerizable siloxane compound (C-1) and the photopolymerization initiator represented by the formula (5) are represented by mass ratio, and the siloxane compound (C-1): photopolymerization initiator is represented by mass ratio.
  • a photopolymerizable composition was prepared so as to have a ratio of 98: 2.
  • the viscosity of the obtained photopolymerizable composition was as high as 280 m ⁇ Pa ⁇ s at 25 ° C., and the viscosity was too high to be applied to the ink jet optical nanoimprint.

Abstract

La présente composition photopolymérisable contient un initiateur de photopolymérisation et (A) un composé de siloxane représenté par la formule générale (1) ou (B) un composé de siloxane représenté par la formule générale (2). Cette composition photopolymérisable a une viscosité basse et une pression de vapeur basse à température ambiante, et peut être recouverte par un procédé à jet d'encre même dans un état où aucun solvant organique n'est contenu. Quand cette composition photopolymérisable est photopolymérisée, une résine de siloxane, qui est son produit de polymérisation, peut être obtenue avec une bonne reproductibilité. Par conséquent, cette composition photopolymérisable convient à l'utilisation dans un procédé de formation de motif par nanoimpression optique. (Dans la formule (1), le groupe A représente un groupe polymérisable ; m représente un entier compris entre 1 et 10 ; n représente un entier compris entre 1 et 10 ; et p représente un entier compris entre 0 et 5.) (Dans la formule (2), le groupe B représente un groupe polymérisable ; q représente un entier compris entre 1 et 10 ; et r représente un entier compris entre 0 et 5.)
PCT/JP2012/078457 2011-11-30 2012-11-02 Composition photopolymérisable et procédé de formation de motif l'utilisant WO2013080741A1 (fr)

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