WO2012102498A2 - Composition de résine pouvant durcir par effet photochimique destinée à une lithographie d'impression - Google Patents

Composition de résine pouvant durcir par effet photochimique destinée à une lithographie d'impression Download PDF

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Publication number
WO2012102498A2
WO2012102498A2 PCT/KR2012/000230 KR2012000230W WO2012102498A2 WO 2012102498 A2 WO2012102498 A2 WO 2012102498A2 KR 2012000230 W KR2012000230 W KR 2012000230W WO 2012102498 A2 WO2012102498 A2 WO 2012102498A2
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WO
WIPO (PCT)
Prior art keywords
group
methacrylate
weight
acrylate
resin composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/KR2012/000230
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English (en)
Korean (ko)
Other versions
WO2012102498A3 (fr
Inventor
유재원
김병욱
김두식
한태환
남동진
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dongjin Semichem Co Ltd
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Dongjin Semichem Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dongjin Semichem Co Ltd filed Critical Dongjin Semichem Co Ltd
Publication of WO2012102498A2 publication Critical patent/WO2012102498A2/fr
Publication of WO2012102498A3 publication Critical patent/WO2012102498A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C08K5/541—Silicon-containing compounds containing oxygen
    • C08K5/5415—Silicon-containing compounds containing oxygen containing at least one Si—O bond
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C33/00—Moulds or cores; Details thereof or accessories therefor
    • B29C33/38—Moulds or cores; Details thereof or accessories therefor characterised by the material or the manufacturing process
    • B29C33/3842—Manufacturing moulds, e.g. shaping the mould surface by machining
    • B29C33/3857—Manufacturing moulds, e.g. shaping the mould surface by machining by making impressions of one or more parts of models, e.g. shaped articles and including possible subsequent assembly of the parts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
    • B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
    • B29C33/00—Moulds or cores; Details thereof or accessories therefor
    • B29C33/42—Moulds or cores; Details thereof or accessories therefor characterised by the shape of the moulding surface, e.g. ribs or grooves
    • B29C33/424—Moulding surfaces provided with means for marking or patterning
    • 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
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes

Definitions

  • the present invention relates to a photocurable resin composition for imprint lithography, wherein the composition is excellent in wettability against not only an organic solvent but also a thermosetting or photocurable resin for pattern formation, and particularly to a thermosetting or photocurable resin for pattern formation. In addition to excellent releasability, and excellent chemical resistance, it is useful for the production of molds for imprint lithography.
  • a pattern forming target material is formed into a thin film on a semiconductor wafer or a glass substrate, the photoresist is applied thereon, the mask on which the desired pattern is formed is covered, the photoresist is exposed to light and then exposed.
  • a photoresist pattern is formed on the substrate in the shape of a designed mask pattern by removing the photoresist of the exposed portion (positive photoresist) or the unexposed portion (negative photoresist) using a developer, and then the photoresist pattern is formed.
  • a pattern of the initial deposition material is formed by finally removing the photoresist that used as a mask for the etching solution using a stripper.
  • a photoresist method has a problem in that manufacturing cost increases and productivity decreases due to the limitation of resolution, many processes, long process time, and expensive equipment used in the process.
  • the imprint lithography method is a method of transferring a polymer thin film pattern of a substrate using a mold composed of Si in which a pattern is initially formed. While the imprint lithography method has the advantage of being able to realize an ultra fine pattern, there is a risk of mold or substrate damage due to the use of high temperature and high pressure processes, and large size due to the use of fluidity of a polymer material heated to a high temperature. There is a problem that it takes a considerable time to implement the pattern of.
  • the mold using PDMS Polydimethylsiloxane
  • PDMS Polydimethylsiloxane
  • the mold using PDMS is a polymer elastomer and has a high release property between the mold and the substrate surface due to its uniform contact with the substrate and low surface energy, but due to low mechanical strength and chemical resistance It is easy to deform and there is a problem that swelling phenomenon occurs easily by a general organic solvent.
  • an object of the present invention is to provide a photocurable resin composition for imprint lithography useful in the production of a mold for imprint lithography by exhibiting excellent chemical resistance and mold release property with excellent wettability.
  • the present invention also provides a method for manufacturing an imprint mold using the photocurable resin composition and an imprint manufactured by the method, which can stably and easily form micropatterns necessary for various electronic device industrial processes including semiconductors, displays, and the like. It is an object to provide a mold.
  • photocurable resin composition comprising:
  • R One To R 4 Each independently represents a hydrogen atom, and C 2-20 Of ethylenically unsaturated groups or C 6-20 Unsubstituted or substituted with an aromatic group 1-20 of An alkyl group or an alkoxy group, where R One To R 4 At least one of the ethylenically unsaturated groups or aromatic groups,
  • n is an integer from 1-30,
  • R 5 to R 8 are each independently a hydrogen atom, an alkyl group of C 1-20 or an alkoxy group.
  • R 9 is selected from the group consisting of a phenyl group, an amino group, a (meth) acryl group, a vinyl group, an epoxy group and combinations thereof,
  • R ' is an alkyl group of C 1-6 ,
  • Q is a C 2-6 alkylene group or C 2-6 alkyleneoxy group
  • n is an integer from 0 to 4,
  • the present invention also provides a cured polymer resin to which the pattern of the disc mold is transferred by coating and curing the photocurable resin mold composition on one surface of the disc mold on which the pattern is formed, and the cured polymer resin on which the pattern is transferred to the disc mold. It provides a method of manufacturing an imprint mold comprising the step of releasing from.
  • the photocurable resin mold composition according to the present invention is excellent in wettability for not only an organic solvent but also a thermosetting or photocurable resin for pattern formation, and in particular, not only an excellent releasability for thermosetting or photocurable resin for pattern formation. With excellent chemical resistance, it is possible to quickly and stably produce fine patterns required for manufacturing various electronic devices including semiconductors and displays.
  • FIG. 1 is a cross-sectional view schematically showing a method for producing a resin mold according to the present invention.
  • the photocurable silicone resin mold composition for imprint lithography according to the present invention
  • the polyaliphatic aromatic silsesquioxane comprising an ethylenically unsaturated group usable in the photocurable silicone resin mold composition of the present invention preferably has at least one ethylenically unsaturated group, at least one aliphatic and at least one aromatic, and has a weight average It may be a compound having a ladder to cage structure having a molecular weight of 1,000 to 200,000.
  • polyaliphatic aromatic silsesquioxane comprising the ethylenically unsaturated group is represented by the following general formula (1):
  • R 1 to R 8 and n are as defined above.
  • the polyaliphatic aromatic silsesquioxane having an ethylenically unsaturated group of Chemical Formula 1 is contained in 30 to 80% by weight in the silicone resin composition.
  • the amount of the silsesquioxane compound is less than 30% by weight, the chemical resistance and releasability of the silicone resin mold composition may be reduced. The wettability may be reduced.
  • the reactive monomer containing at least one unsaturated group in the molecule usable in the photocurable silicone resin mold composition of the present invention may be at least one of unsaturated carboxylic acid, unsaturated carboxylic anhydride and acrylic unsaturated compound containing at least one unsaturated group in the molecule, preferably Preferably, a reactive monomer comprising a fluorine group, a (meth) acryl group, or an epoxy group together with one or more unsaturated groups can be used.
  • Examples of the reactive monomer containing the fluorine group include perfluorohexylethylene, 1,4-divinyldodecafluorohexane, 3-perfluorobutylhydroxypropyl methacrylate and 3-perfluorohexylhydroxypropyl Methacrylate, trifluoroethyl methacrylate, tetrafluoropropyl methacrylate, 2-perfluorohexylethyl acrylate, 3-perfluoromethylbutyl-2-hydroxypropyl acrylate, and derivatives thereof. Can be.
  • Examples of the reactive monomer containing the epoxy group include glycidyl acrylate, glycidyl methacrylate, glycidyl ⁇ -ethyl acrylate, glycidyl ⁇ -n-propyl acrylate, glycidyl ⁇ -n-butyl acrylate, and acrylic acid.
  • Such reactive monomers may be used alone or in combination of two or more thereof.
  • the reactive monomer is preferably included in the resin mold composition 5 to 50% by weight, more preferably 10 to 45% by weight.
  • the amount of the reactive monomer used is less than 5% by weight, the viscosity is high, which makes it difficult to manufacture a resin mold.
  • the amount is more than 50% by weight, chemical resistance and mechanical strength may be lowered.
  • organic silane compound usable in the photocurable resin mold composition of the present invention an organic silane compound including a phenyl group, an amino group, a (meth) acryl group, a vinyl group or an epoxy group can be used.
  • the organosilane compound is a compound having a structure of Formula 2:
  • R 10 , m and p are as defined above.
  • such an organosilane compound is included in the resin mold composition at 5 to 50% by weight. If the content of the organosilane compound is less than 5% by weight, the effect of using the organosilane compound is insignificant. If the content of the organosilane compound is more than 50% by weight, the viscosity decreases, making it difficult to manufacture, and there is a concern that cracking may occur during the production of the resin mold. .
  • photoinitiator examples include Irgacure 369 (hereinafter, manufactured by Ciba Specialty Chemical Co., Ltd.), Irgacure 651, Irgacure 907, Irgacure 819, Diphenyl- (2,4,6-trimethylbenzoyl) phosphine oxide, methylbenzoylformate, ethyl (2, 4,6-trimethylbenzoyl) phenylphosphinate, 2,4-bistrichloromethyl-6-p-methoxystyryl-s-triazine, 2-p-methoxystyryl-4,6-bistriclo Rhomethyl-s-triazine, 2,4-trichloromethyl-6-triazine, 2,4-trichloromethyl-4-methylnaphthyl-6-triazine, benzophenone, p- (diethylamino) Benzophenone, 2,2-dichloro-4-phenoxyacetophenone,
  • the photocurable resin mold composition according to the present invention comprising the components of (1) to (4) as described above may further include a surfactant in order to improve applicability and to further improve releasability when removing the original mold and stripping.
  • surfactants examples include polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, F171 (hereinafter referred to as Nippon Ink Co., Ltd.), F172, F173 FC430 (hereinafter referred to as Sumitomo Trim Corporation), FC431, KP341 (Shin-Etsu Chemical Co., Ltd.). And the like, and the content thereof is preferably contained in an amount of 0.01-2 parts by weight based on 100 parts by weight of the total amount of the components (1), (2) and (3).
  • the present invention also provides a method for producing a mold using the photocurable resin mold composition and a mold prepared by the method.
  • FIG. 1 is a cross-sectional view schematically showing a method for manufacturing a mold according to the present invention.
  • the pattern of the disc mold 101 to be manufactured is turned upward, and then the photocurable resin mold composition 102a according to the present invention is applied (step 1).
  • the coating process may be performed by a method commonly used in the art, for example, spin coating, slit coating, or the like, and the photocurable resin mold composition 102a to have a thickness of 5-60 ⁇ m in a disc mold. ) Is preferably applied.
  • the photocurable resin mold composition 102a is cured by irradiating with nitrogen or an atmosphere in an atmosphere (step) 2).
  • the back support 103 is a transparent glass plate (bare glass), ITO (indium tin oxide) substrate, COC (cyclic olefin copolymer), PAC (polyacrylate), PC ( polycarbonate), PE (polyethylene), PEEK (polyetheretherketone), PEI (polyetherimide), PEN (polyethylenenaphthalate), PES (polyethersulfone), PET (polyethyleneterephtalate), PI (polyimide), PO (polyolefin), PMMA (polymethylmethacrylate), PSF ( polysulfone), PVA (polyvinylalcohol), PVCi (polyvinylcinnamate), TAC (triacetylcellulose), polysilicone (polysilicone), polyurethane (polyurethane), epoxy resin (epoxy Resin) and the like can be used.
  • the transmittance is 97-99.9% in the light source of 500 nm
  • a pattern transferred from the disc mold 101 is formed on one surface of the release cured polymer resin 102b.
  • the molding mold 104 is completed by selectively aging the cured polymer resin 102b mold having the pattern formed (step 4).
  • aging means that the surface of the cured polymer resin mold on which the pattern is formed is excessively exposed to ultraviolet rays to improve the hardness of the mold and to completely extinguish the remaining reactors against ultraviolet rays or to extinguish the remaining reactors through heat treatment and at the same time, surface flatness And it means a process for further improving the adhesion with the support.
  • the aging step is preferably a process of improving the hardness of the mold by excessively exposing the surface of the mold to ultraviolet rays, may be carried out by selecting one of the exposure and the heat treatment, or both may be carried out step by step.
  • a mold having a high degree of completeness can be produced by the method according to the present invention.
  • the imprint lithography process using the mold replaces the conventional photolithography process for forming a fine pattern, thereby simplifying various steps such as exposure, development, and cleaning of the existing photolithography process, and also a manufacturing time (tact time). ), The manufacturing cost can be reduced and the productivity can be improved.
  • the pattern of the disc mold 101 was turned upward, and the photocurable resin mold composition 102a prepared above was slit-coated so that the thickness might be 100 micrometers.
  • the back support 103 is bonded onto the disc mold to which the photocurable resin mold composition is applied, and then irradiated with ultraviolet rays in a nitrogen atmosphere to cure, and the back side to which the cured polymer resin 102b to which the pattern of the disc mold 101 is transferred is attached.
  • the support 103 was released from the disc mold 101. Ultraviolet rays were irradiated for complete curing of the adhered cured polymer resin 102b.
  • polyaliphatic aromatic silsesquioxane (1a) containing ethylenically unsaturated groups obtained in Synthesis Example 1-a 40 parts by weight of glycidyl methacrylate and (3-glycidoxyoxy) trimeth 10 parts by weight of oxysilane and 1 part by weight of ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate as a photoinitiator were added and stirred uniformly at 300-400 rpm for 20 hours at room temperature to give a transparent liquid resin solution (102a).
  • a polymer resin mold was prepared in the same manner as in Example 1, except that () was prepared.
  • polyaliphatic aromatic silsesquioxane (1a) containing ethylenically unsaturated groups obtained in ⁇ Synthesis Example 1-a> 50 parts by weight of polyaliphatic aromatic silsesquioxane (1a) containing ethylenically unsaturated groups obtained in ⁇ Synthesis Example 1-a>, 10 parts by weight of glycidyl methacrylate and (3-glycidoxyoxy) trimeth 40 parts by weight of oxysilane, 1 part by weight of ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate as a photoinitiator, and uniformly stirred at 300-400 rpm at room temperature for 20 hours to give a transparent liquid solution (102a) Except that was prepared, a polymer resin mold was prepared in the same manner as in Example 1.
  • polyaliphatic aromatic silsesquioxane (1b) containing ethylenically unsaturated group obtained in ⁇ Synthesis Example 1-b> 10 parts by weight of glycidyl methacrylate and (3-glycidoxyoxy) trimeth 40 parts by weight of oxysilane and 1 part by weight of ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate as a photoinitiator were added, and stirred uniformly at 300-400 rpm for 20 hours at room temperature to provide a transparent liquid resin solution (102a).
  • a polymer resin mold was prepared in the same manner as in Example 1, except that () was prepared.
  • 35 parts by weight of oxysilane and 1 part by weight of ethyl (2,4,6-trimethylbenzoyl) phenylphosphinate as a photoinitiator were added and stirred uniformly for 20 hours at 300-400 rpm at room temperature to provide a transparent liquid resin solution (102a).
  • a polymer resin mold was prepared in the same manner as in Example 1, except that () was prepared.
  • a polymer resin mold was prepared in the same manner as in Example 1, except that the transparent liquid solution 102a was prepared by uniformly stirring at 300-400 rpm for 20 hours.
  • the polymer resin molds prepared in Examples 1 to 10 and Comparative Examples 1 to 3 were completely deposited in acetone and left for 7 days, and then the weight change of the resin mold was measured.
  • the light absorption spectra of visible light were measured about the polymer resin molds prepared in Examples 1 to 10 and Comparative Examples 1 to 3, and the light transmittance was measured and described at 400 nm.
  • Example 1 Contact angle Dysplasia Chemical resistance Light transmittance
  • Example 2 89 ⁇ ⁇ 95.1
  • Example 3 91 ⁇ ⁇ 95.5
  • Example 4 88 ⁇ ⁇ 95.0
  • Example 5 95 ⁇ ⁇ 95.8
  • Example 6 91 ⁇ ⁇ 95.4
  • Example 7 89 ⁇ ⁇ 95.3
  • Example 8 90 ⁇ ⁇ 95.2
  • Example 9 88 ⁇ ⁇ 95.0
  • Example 10 97 ⁇ ⁇ 95.9 Comparative Example 1 86 X X 96.7 Comparative Example 2 93 ⁇ ⁇ 96.0 Comparative Example 3 93 X X 95.3
  • the polymer resin molds of Examples 1 to 10 prepared by using the photocurable resin mold composition of the present invention showed a transmittance equivalent to or higher than that of Comparative Examples 1 to 3.
  • the polymer resin molds of Examples 1 to 10 had more excellent chemical resistance and exhibited superior release properties while exhibiting equivalent contact angles with better chemical resistance.
  • the photocurable resin mold composition according to the present invention is excellent in wettability for not only an organic solvent but also a thermosetting or photocurable resin for pattern formation, and in particular, not only an excellent releasability for thermosetting or photocurable resin for pattern formation. With excellent chemical resistance, it is possible to quickly and stably produce fine patterns required for manufacturing various electronic devices including semiconductors and displays.

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  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Mechanical Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Shaping Of Tube Ends By Bending Or Straightening (AREA)

Abstract

La présente invention se rapporte à une composition de résine pouvant durcir par effet photochimique destinée à une lithographie d'impression, la composition de résine pouvant durcir par effet photochimique présentant une mouillabilité exceptionnelle par rapport à des résines pouvant durcir par effet thermique ou à des résines pouvant durcir par effet photochimique pour une formation de motifs en plus de solvants organiques et, plus particulièrement, elle présente non seulement des propriétés exceptionnelles de dégagement d'un moule par rapport à des résines pouvant durcir par effet thermique ou à des résines pouvant durcir par effet photochimique pour une formation de motif, mais elle présente également une résistance chimique exceptionnelle et permet de réaliser une production stable et relativement rapide de micromotifs qui sont nécessaires à la réalisation de divers dispositifs électroniques y compris des semi-conducteurs et des affichages.
PCT/KR2012/000230 2011-01-25 2012-01-10 Composition de résine pouvant durcir par effet photochimique destinée à une lithographie d'impression Ceased WO2012102498A2 (fr)

Applications Claiming Priority (2)

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KR1020110007260A KR101808757B1 (ko) 2011-01-25 2011-01-25 임프린트 리소그래피용 광경화형 수지 조성물
KR10-2011-0007260 2011-01-25

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WO2012102498A2 true WO2012102498A2 (fr) 2012-08-02
WO2012102498A3 WO2012102498A3 (fr) 2012-12-06

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KR102225126B1 (ko) * 2019-10-15 2021-03-09 한국세라믹기술원 소수성 3차원 프린팅 잉크 조성물 및 그 제조방법, 그리고 3차원 잉크젯 프린팅 방법.

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JP5092440B2 (ja) 2007-02-16 2012-12-05 Ｊｓｒ株式会社 硬化性組成物、その硬化膜及び積層体
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KR101808757B1 (ko) 2017-12-14
KR20120086049A (ko) 2012-08-02
TW201235416A (en) 2012-09-01
WO2012102498A3 (fr) 2012-12-06

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