WO2009125806A1 - Resin composition for energy ray-curable layer and sheet for forming through hole - Google Patents

Resin composition for energy ray-curable layer and sheet for forming through hole Download PDF

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Publication number
WO2009125806A1
WO2009125806A1 PCT/JP2009/057233 JP2009057233W WO2009125806A1 WO 2009125806 A1 WO2009125806 A1 WO 2009125806A1 JP 2009057233 W JP2009057233 W JP 2009057233W WO 2009125806 A1 WO2009125806 A1 WO 2009125806A1
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energy ray
hole
sheet
curable layer
curable
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PCT/JP2009/057233
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French (fr)
Japanese (ja)
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近藤 健
達夫 福田
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リンテック株式会社
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Priority to JP2008-102696 priority
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Publication of WO2009125806A1 publication Critical patent/WO2009125806A1/en

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    • GPHYSICS
    • G11INFORMATION STORAGE
    • G11BINFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
    • G11B7/00Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
    • G11B7/24Record carriers characterised by shape, structure or physical properties, or by the selection of the material
    • G11B7/26Apparatus or processes specially adapted for the manufacture of record carriers
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/038Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0388Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer

Abstract

Disclosed is a sheet (1) for forming a through hole, which is composed of an energy ray-curable layer (11) and releasing sheets (12, 12') arranged on both sides of the energy ray-curable layer (11). The energy ray-curable layer (11) is composed of a resin composition containing an energy ray-curable compound having a mass average molecular weight of 200-10,000 and an energy ray-curable group. The energy ray-curable compound has a [mass average molecular weight]/[number of energy ray-curable groups] ratio of 80-300. This sheet (1) for forming a through hole enables formation of a though hole by development using a general-purpose solvent as well as formation of a recessed and projected pattern at room temperature.

Description

Energy ray-curable layer resin composition and the through-hole forming sheet

The present invention, through-holes or the resin composition for the energy ray-curable layer for the purpose of forming the through-hole-convex pattern, the through-hole or the through for forming the through-hole-convex pattern hole forming sheet, and through a method for producing a sheet having holes or through holes, uneven pattern.

Conventionally, for a single sheet, to form a concavo-convex pattern is not known to form through holes by development. A related technique, a dry photohardenable film for optical disks (for example, Patent Document 1), nanoimprint photocurable transfer film (for example, Patent Document 2), and a photoresist film (for example, Patent Document 3).

Patent No. 2956989 Publication JP 2007-73696 JP Patent No. 2847720 Publication

However, the light dry photohardenable film disks and nanoimprinting photocurable transfer film, since the uncured dissolved in a solvent, is dissolved in or swells or partially solvent with a solvent even after curing, solvent those that can not be developed by. On the other hand, a commercially available photoresist film is very hard, the transferred the uneven pattern on the photoresist film is required pressurization at a high temperature and / or pressure, also in the developing dedicated developing solution (water gender) is required. Furthermore, when considering the optical applications, there is a problem of poor transparency in the photoresist film.

The present invention has been made in view of such circumstances, development with the formation of the through-hole, the resin composition forming the concavo-convex pattern and uses a sheet and its possible at room temperature using a general-purpose solvent, and an object thereof is to provide a method for manufacturing a sheet having a through-hole or through-holes and uneven pattern.

To achieve the above object, the present invention first includes (weight average) has a molecular weight of 200 to 10,000, having an energy ray-curable groups, the ratio of (weight-average) molecular weight / energy ray-curable groups There 80, characterized in that it contains the energy ray-curable compound is ~ 300, provides a through-hole or the resin composition for the energy ray-curable layer for the purpose of forming the through-hole-convex pattern (invention 1 ).

Incidentally, "the through-hole-convex pattern" herein means means "through-hole and the concavo-convex pattern", thus "through hole or through hole, concavo-convex pattern" is "through-hole or through-holes and uneven pattern," to. Also, "(weight average) molecular weight" herein, "weight average molecular weight" when the compound is a polymer or oligomer, in the case of monomers is intended to mean "molecular weight".

Above invention (invention 1) Energy ray-curable compound in the the amount of the energy ray-curable groups to the molecular weight of the size (the amount of the base resin) is large and is there are many cross-linking points, solvent after curing sex is characterized in that particularly high. Further, the energy ray-curable compound, before curing for easily dissolved in general purpose solvents, by providing the cured portion and uncured portion, thereby enabling development with universal solvent. Furthermore, the energy ray-curable compound comprises a possible formation of the uneven pattern at room temperature properties (storage modulus). Therefore, according to the resin composition containing the energy ray-curable compound, the formation of the uneven pattern at room temperature, it is possible the formation of through holes by development using a general-purpose solvent.

In the above invention (invention 1), the energy ray-curable compound is preferably a polyfunctional (meth) acrylic acid ester (invention 2).

In the above invention (invention 1), it is preferable that weight average molecular weight of further contains from 50,000 to 1,200,000, Compound (invention 3). By containing such compounds, the resin composition was formed and held in sheet form, and it is possible to form an uneven pattern on the sheet at room temperature. Further, such compounds do not inhibit the solubility in general purpose solvents of the resin composition before curing.

In the above invention (invention 3), wherein the compound is (meth) may be an acrylic acid ester polymer (Invention 4), also having an energy ray-curable groups in the side chain (meth) acrylic acid ester be copolymers good (invention 5).

In the above invention (invention 3-5), the amount of said compound, the total amount of said compound with said energy ray-curable compound is 100 wt%, preferably 20 to 60 mass% (invention 6).

The present invention secondly, characterized by comprising an energy ray-curable layer comprising the resin composition (inventions 1 to 6), through holes formed for forming a through-hole or through-hole-convex pattern to provide a sheet (invention 7). In this specification, the concept of the "sheet" film, and "film" is intended to include the concept of sheet.

In the above invention (Invention 7), it preferably has a storage modulus at 25 ° C. before curing of the energy ray-curable layer is 1 × 10 3 ~ 1 × 10 6 Pa ( invention 8).

In the above invention (invention 7, 8), it is preferable total light transmittance after curing of the energy ray-curable layer is 85% or more (Invention 9).

The invention in a third, provided with a concavo-convex pattern, the portion to be formed a through hole in the sheet the energy ray shielding portion, the other portion providing a stamper that is the energy ray transmissive portion, the through hole forming the stamper is pressed against the energy ray-curable layer of use sheet (invention 7-9), and irradiated with an energy beam to the energy ray-curable layer from the stamper side in this state, the stamper to the energy ray-curable layer along with transferring the concavo-convex pattern, the portion corresponding to the energy-ray transmitting portion of the stamper in the energy ray-curable layer is cured, a portion corresponding to the energy-ray shielding portion of the stamper is the uncured state, then, and forming a through hole uncured portions of the energy ray-curable layer is removed by a solvent, through hole & To provide a method for manufacturing a sheet having a convex pattern (invention 10).

In the above invention (Invention 10), it is preferable to perform compression of the stamper with respect to the energy ray-curable layer at room temperature (invention 11).

In the above invention (Invention 10, 11), wherein the solvent is ethyl acetate, methyl ethyl ketone, is preferably at least one selected from the group consisting of acetone and toluene (invention 12).

The invention in a (invention 10-12) is the removal of the uncured portion of the energy ray-curable layer, wherein a through hole forming sheet is immersed in a solvent be performed by ultrasonic cleaning is preferable (invention 13 ).

The present invention fourthly, part to be formed a through hole in the sheet the energy ray shielding portion, the other portion providing a mask that is the energy ray transmissive portion, the through hole forming sheet (invention 7 ~ to energy ray-curable layer 9), is irradiated with energy rays through the mask, the portion corresponding to the energy-ray transmitting portion of the mask in the energy ray-curable layer is cured, the energy ray shielding of the mask portions corresponding to the parts are the uncured state, then, and forming a through hole uncured portions of the energy ray-curable layer is removed by a solvent, a method for manufacturing a sheet having a through hole to provide (invention 14).

In the above invention (invention 14), wherein the solvent is ethyl acetate, methyl ethyl ketone, is preferably at least one selected from the group consisting of acetone and toluene (invention 15).

The invention in a (invention 14, 15) is the removal of uncured portions of the energy ray-curable layer, wherein a through hole forming sheet is immersed in a solvent be performed by ultrasonic cleaning is preferable (invention 16 ).

The resin composition according to the present invention, according a method of manufacturing a sheet or sheets, it is possible the formation of through holes by development using a general-purpose solvent, and formation of the concavo-convex pattern in the normal temperature is.

It is a cross-sectional view of the through hole forming sheet according to an embodiment of the present invention. Using a through hole forming sheet according to the embodiment, a diagram showing an example of a method for manufacturing a sheet having a through-hole-convex pattern.

Hereinafter, embodiments of the present invention will be described.
[Resin Composition]
The resin composition according to the present embodiment is a resin composition for the energy ray-curable layer for the purpose of forming the through-hole or through-hole-convex pattern, the following energy ray-curable compound (I) essential components to.

Energy ray-curable compound (I), (weight average) molecular weight of 200 to 10,000, having an energy ray-curable groups, (mass average) molecular weight / ratio of the energy ray-curable groups is 80-300 it is a certain thing. The energy ray-curable compound (I), the monomers may be any of oligomers and polymers.

The condition is satisfied energy ray-curable compound of (I), the amount of the energy ray-curable groups to the molecular weight of the size (the amount of the base resin) is large and thus has become a frequently crosslinking points. Therefore, the energy ray-curable compound (I) is characterized in that a particularly high solvent resistance after curing. The energy ray-curable compound (I), for easily soluble in general-purpose solvents before curing, by providing the cured portions and uncured portions, developable by a general purpose solvent, and formation of through holes by the development to become. Furthermore, the energy ray-curable compound (I) is provided with a possible formation of the uneven pattern at room temperature properties (storage modulus).

(Weight average) molecular weight of the energy ray-curable compound (I) is preferably preferably 220 to 5000, in particular 250 to 3,000. Further, (weight average) molecular weight / energy ray ratio of the curable groups is preferably 100 to 250. Incidentally, (weight average) molecular weight / ratio of the energy ray-curable groups is energy ray-curable compound is less than 80 (I) is obtained, production is extremely difficult.

The energy ray-curable group, an epoxy group, a vinyl group, and a (meth) acryloyl group, and among them (meth) acryloyl group is preferred.

The energy ray-curable compound as described above (I), for example, be mentioned (meth) acrylic acid ester or (meth) acrylate oligomer. (Meth) acrylic acid ester, a polyfunctional (meth) acrylate are preferable, specifically, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, neopentyl glycol adipate closed (meth) acrylate, hydroxypivalic acid neopentyl glycol di (meth) acrylate, dicyclopentenyl di (meth) acrylate, caprolactone-modified di cyclopentenyl di (meth) acrylate, ethylene oxide-modified phosphoric acid di (meth) acrylate, allylated cyclohexyl di (meth) acrylate, isocyanuric acid di (meth) acrylate, dimethylol tricyclodecane di (meth) acrylate, trimethylol Ropantori (meth) acrylate, dipentaerythritol tri (meth) acrylate, propionic acid-modified dipentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, propylene oxide-modified trimethylolpropane tri (meth) acrylate, isocyanuric acid tris (acryloxyethyl), propionic acid-modified dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tri erythritol hepta (meth) acrylate, caprolactone-modified dipentaerythritol hexa (meth) acrylate, caprolactone-modified tris ( acryloxyethyl) isocyanurate. Among them, dimethylol tricyclodecane di (meth) acrylate are particularly preferred.

The (meth) acrylate oligomer, polyester (meth) acrylate, epoxy (meth) acrylate, urethane (meth) acrylates, polyether (meth) acrylate, polybutadiene (meth) acrylates, and silicone (meth) acrylate.

The resin composition according to the present embodiment, in addition to the energy ray-curable compound (I), further preferably contains a mass-average molecular weight of from 50,000 to 1,200,000 and is compound (II). By weight average molecular weight of 50,000 or more, the compound (II) has a shape retention. By containing such compounds (II), the resin composition according to the present embodiment is formed and retained in a sheet form, and it is possible to form an uneven pattern on the sheet at room temperature. Further, by weight average molecular weight of 1.2 million or less, the resin composition before curing becomes easily soluble in general-purpose solvents.

The weight average molecular weight of the compound (II) is preferably preferably from 60000 to 400000, in particular 70000 to 200000.

The glass transition temperature of the compound (II) (Tg) is preferably -40 ℃ ~ 120 ℃. When the glass transition temperature of the compound (II) is in this range, the resin composition was formed and held in sheet form, and it becomes easy to form an uneven pattern on the sheet at room temperature.

The compounds (II), (meth) acrylic acid ester polymer since transparency is good is preferred. (Meth) acrylic acid ester polymers, (meth) of a homopolymer of acrylic acid ester monomer or a derivative thereof, or (meth) acrylic acid ester monomer or a derivative thereof, a functional group-containing monomer and / or other monomers a copolymer.

(Meth) acrylic acid ester monomers such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, isooctyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate, myristyl (meth) acrylate, palmityl (meth) acrylate, stearyl (meth) acrylates such as alkyl (meth) acrylates, cycloalkyl (meth) acrylate, benzyl (meth) acrylate. These monomers may be used alone or in combination of two or more.

Examples of the functional group-containing monomers, e.g., (meth) acrylic acid, crotonic acid, maleic acid, itaconic, ethylenically unsaturated carboxylic acids such as citraconic acid, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, hydroxyalkyl (meth) acrylate and 4-hydroxybutyl (meth) acrylate, monomethyl aminoethyl ( meth) acrylate, monoethyl aminoethyl (meth) acrylate, monomethyl aminopropyl (meth) acrylate, such as monoethyl aminopropyl (meth) acrylate, monoalkylaminoalkyl (meth) acrylate And the like.

Other monomers include vinyl acetate, styrene, acrylonitrile, tolyl, etc. to Metaakuriro.

As the compound (II), it can be used with an energy ray-curable groups in the side chain (meth) acrylic acid ester copolymer.

Having an energy ray-curable groups in the side chain (meth) acrylic acid ester copolymer has a functional group-containing monomer units and (meth) acrylic acid ester copolymer, a substituent attached to its functional group not obtained by reacting the unsaturated group-containing compound.

Having a functional group-containing monomer units (meth) acrylic acid ester copolymer, a functional group-containing monomer is obtained by copolymerizing a (meth) acrylic acid ester monomer or derivative thereof.

Functional group-containing monomer, a polymerizable double bond, a hydroxyl group, a carboxyl group, an amino group, a substituted amino group, a monomer having a functional group such as epoxy group in the molecule. Examples of the functional group-containing monomers such as 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate acrylate containing a hydroxyl group such as acrylic acid, methacrylic acid, carboxyl and itaconic acid It includes group-containing compound, and these are used singly or in combination of two or more kinds.

The (meth) acrylic acid ester monomers, cycloalkyl (meth) acrylate, benzyl (meth) acrylate, the carbon number of the alkyl group has 1 to 18 (meth) acrylic acid alkyl esters are used. Among these, particularly preferred is the 1 to 18 carbon atoms in the alkyl group (meth) acrylic acid alkyl esters, such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n- butyl (meth ) acrylate, 2-ethylhexyl (meth) acrylate and the like are used.

Substituent unsaturated group-containing compound has can be, appropriately selected depending on the type of the functional group of the functional group-containing monomer units possessed by the (meth) acrylic acid ester copolymer. For example, when the functional group is a hydroxyl group, an amino group or a substituted amino group, preferably an isocyanate group or an epoxy group as a substituent, when the functional group is a carboxyl group, the substituent isocyanate group, aziridinyl group, an epoxy preferably a group or oxazoline group, if the functional group is an epoxy group, an amino group as a substituent, a carboxyl group or an aziridinyl group is preferable. Such substituents are included one by one in every unsaturated group-containing compound 1 molecule.

Specific examples of the unsaturated group-containing compounds, for example, methacryloyloxyethyl isocyanate, meta - isopropenyl-.alpha., alpha-dimethylbenzyl isocyanate, methacryloyl isocyanate, allyl isocyanate; diisocyanate compound or polyisocyanate compound If, acryloyl mono isocyanate compound obtained by reacting hydroxyethyl (meth) acrylate; di and isocyanate compound or polyisocyanate compound, a polyol compound, acryloyl mono isocyanate obtained by reaction of hydroxyethyl (meth) acrylate inert compounds; glycidyl (meth) acrylate; (meth) acrylic acid, 2- (1-aziridinyl) ethyl (meth) acrylate, 2-vinyl-2-oxazoline, 2-isopropoxy Ropeniru-2-oxazoline, and the like.

The amount of compound (II), the energy ray-curable compound and the total amount of the compound (I) (II) is 100 wt%, preferably 20 to 60 mass%, in particular 25 to 50 it is preferably mass%. By the amount of the compound (II) is within the above range, shape retention of the resin composition, uneven patterning performance and developing performance is ensured.

The resin composition according to the present embodiment, the energy ray-curable compound (I) and compound other than (II), an energy ray polymerization initiator (III) may further contain. The energy ray polymerization initiator (III), in the case of using ultraviolet rays as the energy rays, using a photopolymerization initiator. The use of the photopolymerization initiator, it is possible to reduce the polymerization curing time and the light irradiation amount.

As the photopolymerization initiator, specifically, benzophenone, acetophenone, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzoin benzoic acid, methyl benzoin benzoate, benzoin dimethyl ketal, 2,4 - diethyl thioxanthone, 1-hydroxycyclohexyl phenyl ketone, benzyl diphenyl sulfide, tetramethylthiuram monosulfide, azobisisobutyronitrile, benzyl, dibenzyl, diacetyl, beta-crawling anthraquinone, (2,4,6-trimethyl benzyl diphenyl) phosphine oxide, 2-benzothiazole -N, N-diethyldithiocarbamate, oligo {2-hydroxy-2-methyl-1 [4- (1-propenyl) phenyl] propanone}, 2-hydroxy-2-methyl-1-phenyl - propane-1-one and the like. These may be used singly or in combination of two or more.

Energy ray polymerization initiator (III), the total amount of the energy ray-curable compound, i.e. the energy ray-curable compound (I), having an energy ray-curable groups in the side chain (meth) acrylate copolymer in a compound (II), 0.1 ~ 50 parts by weight of the total amount of 100 parts by mass of the other energy ray-curable compound, in particular used in an amount ranging from 0.5 to 30 parts by weight it is preferable.

Here, the energy ray-curable compound (I) as an essential component, optionally the compound (II) and the energy ray polymerization initiator (III) a resin composition containing the features of high total light transmittance after curing there is.

The resin composition according to the present embodiment, other UV absorbers, plasticizers, fillers, antioxidants, tackifiers, pigments, dyes, but also contain an additive such as a coupling agent, cross-linking agent preferably does not contain. When the energy ray-curable compound by the crosslinking agent (I) and / or the compound (II) is cross-linked, the uncured portion of the resin composition becomes less soluble in general-purpose solvents, development speed may be lowered. Further, the concavo-convex pattern to be formed is not intended elaboration Contact it also.

The resin composition according to the present embodiment, as described later, it is preferable to use in forming a through hole or sheet of the energy ray-curable layer for the purpose of forming the through hole and the uneven pattern, the present invention is not limited thereto, applying a stamper or the like to the liquid or gel resin composition, the through-hole or through-holes and uneven pattern may be formed.

[Holes forming sheet]
Figure 1 is a cross-sectional view of the through hole forming sheet according to an embodiment of the present invention. The through-hole forming sheet is a sheet for forming a through-hole or through-holes and uneven pattern. Through hole forming sheet 1 according to this embodiment, it consists of an energy ray-curable layer 11, the release sheet 12, 12 which are laminated on both surfaces of the energy ray-curable layer 11 'and. However, the release sheet 12, 12 'is intended to be peeled off when using the through-hole forming sheet 1.

Energy ray-curable layer 11 in this embodiment is composed of a resin composition according to the present embodiment described above. Therefore, the energy ray-curable layer 11 can be formed a concavo-convex pattern at room temperature, and, by providing the cured portion and uncured portion, forming the through holes by development using a general-purpose solvent possible it is.

Storage modulus at 25 ° C. before curing of the energy ray-curable layer 11 is preferably from 1 × 10 3 ~ 1 × 10 6 Pa are preferred, particularly 5 × 10 3 ~ 5 × 10 5 Pa . By storage modulus at 25 ° C. before curing is within the above range, by crimping the stamper to the energy ray-curable layer 11 at room temperature, the uneven pattern is energy ray-curable formed on the stamper layer 11 It can be precisely transferred to.

Also, a storage modulus at 25 ° C. after curing of the energy ray-curable layer 11 is preferably 1 × 10 7 ~ 6 × 10 9 Pa, especially 1 × 10 9 ~ 5.5 × 10 9 Pa there it is preferable. By storage elastic modulus after curing is within the above range, the transferred concavo-convex pattern in the energy ray-curable layer 11 is securely fixed by curing, in separating the stamper and the energy ray-curable layer 11, or uneven pattern is broken, there is no danger or deformed.

When using energy ray-curable layer 11 for light, it is preferable that preferably the total light transmittance after curing of the energy ray-curable layer 11 is 85% or more, preferably 90% or more. Energy ray-curable layer 11 of a resin composition according to the present embodiment, it is possible to achieve a total light transmittance of the above. When the total light transmittance is 85% or more, it can be used in a variety of optical products.

The thickness of the energy ray-curable layer 11, the intended use and the energy ray-curable layer 11, but is appropriately determined according to the depth of the concavo-convex pattern to be formed, it is usually about 1 ~ 2000 .mu.m, preferably it is a 3 ~ 1000μm, more preferably, a 5 ~ 200μm.

In the through hole forming sheet 1 according to this embodiment, since the energy ray-curable layer 11 is easily deformed by the pressure, in order to prevent this, the release sheet 12, 12 on both sides of the energy ray-curable layer 11 ' It is stacked. The release sheet 12, 12 ', can be conventionally used known ones, for example, a resin film such as polyethylene terephthalate or polypropylene, their resin film silicone release agent, long-chain alkyl release agent, an alkyd resin can be used release sheet has been subjected to release treatment with a system release agent or the like.

The thickness of the release sheet 12, 12 'is generally approximately 10 ~ 200 [mu] m, preferably about 20 ~ 100 [mu] m.

The release sheet 12 'is peeled prior to, in the case of peeling the release sheet 12 later, the release sheet 12' and a light release type release sheet, preferably a release sheet 12 and the heavy release type release sheet .

To produce a through-hole forming sheet 1 according to this embodiment, first, a resin composition according to the present embodiment, the coating material for the energy ray-curable layer 11 containing a optionally further solvent to prepare . As the solvent, for example, toluene, ethyl acetate, methyl ethyl ketone, isopropyl alcohol or the like.

Then, after forming an energy ray-curable layer 11 coated dried over coating material of the energy ray curable layer 11 (if present) to release treatment surface of one of the release sheet 12 (12 '), energy on the surface of the line-curable layer 11 bonding the release-treated surface of the other release sheet 12 '(12) (if present). The coating of the coating agent is, for example, can be used a kiss roll coater, reverse roll coater, a knife coater, a roll knife coater, a coating machine such as a die coater.

Or the through holes forming sheet 1 described can either be used for the production of sheets having through holes and uneven pattern will be described later, it can also be used in the manufacture of a sheet having only the through hole.

Production of sheet with a through-hole-convex pattern]
Using a through hole forming sheet 1 described above, an example of a method for manufacturing a sheet 2 having the through-hole-convex pattern. Figure 2 (a) ~ (f) have used the through-hole forming sheet 1 is a diagram showing an example of a method for manufacturing a sheet 2 having the through-hole-convex pattern.

First, as shown in FIG. 2 (a), it is prepared with the through hole forming sheet 1, and a stamper 3. Stamper 3 used in this embodiment is provided with a concavo-convex pattern, the portion to be formed a through hole in the sheet obtained energy ray shielding portion 31, the other part has an energy ray transmitting unit 32. Such stamper 3 is, for example, glass or norbornene resin, and composed of a transparent resin material such as polycarbonate resin, obtained by providing the dot-shaped energy ray shielding material in place. For example, when using ultraviolet rays as the energy rays, or the like are formed in dots chromium and lead for shielding ultraviolet rays, by printing or applying a UV-absorbing material in the form of dots, energy ray shielding section in the stamper 3 31 can be the provision. The surface having the concavo-convex pattern of the stamper 3, a silicone release agent, long-chain alkyl-based release agent may be release-treated by alkyd resin release agent.

Next, as shown in FIG. 2 (b), peeled and attached to the glass substrate 4 one of the release sheet 12 of the through-hole forming sheet 1 '(light release type release sheet), then the other peeling sheet 12 (heavy release type release sheet) was peeled off, crimping the stamper 3 to the energy ray-curable layer 11 exposed. The bonding process may be carried out at room temperature. Pressure during bonding is preferably from 0.01 ~ 5 MPa.

Then, as shown in FIG. 2 (c), in a state in which the energy ray-curable layer 11 was adhered to the stamper 3, the energy ray irradiation apparatus (ultraviolet (UV) lamp L as an example in FIG. 2 (c)) use, irradiating energy rays to the energy ray-curable layer 11 from the stamper 3 side. Thus, the uneven pattern of the stamper 3 are transferred and fixed to the energy ray-curable layer 11. Further, in the energy ray-curable layer 11, the portion corresponding to the energy beam transmitting portion 32 of the stamper 3 is cured, a portion corresponding to the energy-ray shielding portion 31 of the stamper 3 is in the state of the uncured.

As the energy ray, general ultraviolet rays, electron rays or the like is used. Irradiation of energy rays varies depending on the kind of energy rays, for example, in the case of ultraviolet rays is preferably about 100 ~ 500mJ / cm 2 in quantity, in the case of electron rays, is preferably about 10 ~ 1000krad.

As shown in FIG. 2 (d), After separation of the stamper 3 from the energy ray-curable layer 11, as shown in FIG. 2 (e), the uncured portions of the energy ray-curable layer 11 is removed by a general-purpose solvent, forming the through hole 21. Uncured portions of the energy ray-curable layer 11 to dissolve in a general-purpose solvent, it is possible to take a developing process.

As a method for removing the uncured portion, as shown in FIG. 2 (e), a method of performing immersion ultrasonic cleaning through-hole forming sheet 1 (energy ray-curable layer 11) in a general-purpose solvent, energy ray how spraying a universal solvent of the curable layer 11, or immersed in a general-purpose solvent, a method of removing uncured portions swollen with air blowing and the like.

The general-purpose solvent, methyl alcohol, ethyl alcohol, iso- propyl alcohol, n- propyl alcohol, iso- butyl alcohol, n- butyl alcohol, benzyl alcohol, ethyl acetate, esters such as butyl acetate, methyl ethyl ketone, ketones such as acetone, propylene glycol monomethyl ether, methyl cellosolve, ethyl cellosolve, ethylene glycol monobutyl -t- butyl ether, butyl cellosolve, 3-methoxy-3-methyl-1-butanol, ethylene glycol monopropyl ether, triethylene glycol monobutyl ether , glycol ethers such as dipropylene glycol monomethyl ether, and benzene, toluene, and hydrocarbons such as xylene.

The solvent, it is necessary to use a dissolving or swelling the uncured portions of the energy ray-curable layer 11 may be appropriately selected depending on the method of removing the uncured portions. For example, to remove an uncured portion performs immersed in a ultrasonic cleaning through-hole forming sheet 1 in a general-purpose solvent, preferably hydrocarbons, removing uncured portions swollen immersed in a general-purpose solvent air blow or the like If you are alcohols or glycol ethers are preferred. The above solvents may be used by mixing singly or two or more.

As described above, as shown in FIG. 2 (f), the sheet 2 is obtained having a through-hole 21 and convex pattern. The sheet 2 can also be used by peeling off from the glass substrate 4.

It varies depending on the use of the sheet 2, the diameter of the through-hole 21 is preferably from 0.1 ~ 1000 .mu.m. Further, the pore density of the through holes 21 is preferably 1 to 1,000 / 100 cm 2.

The sheet 2, for example, can be used through-hole wiring board, PDP (Plasma Display Panel) display of the partition forming member such as a spacer, the optical lenses and the like.

Production of sheet having through-holes]
Using a through hole forming sheet 1 described above, an example of a method for manufacturing a sheet having a through hole. Is basically the same as the method for producing a sheet having a through-hole-convex pattern described above, instead of the stamper 3, the portion to be formed a through hole in the sheet obtained energy ray shielding portion, the other portion using a mask of the flat which is an energy ray transmitting part (both surfaces planar).

As the mask, for example, dot-like energy ray shielding material in place in position those provided dot-shaped energy ray shielding material, or in the production of glass or resin plate glass plate or a transparent resin plate it can be used such as those embedded. The surface of the energy ray-curable layer side of the mask, silicone release agent, long-chain alkyl-based release agent may be release-treated by alkyd resin release agent.

Upon irradiation with the energy beam, the mask is preferably used in close contact to the energy ray-curable layer 11 of the through-hole forming sheet 1, but is not limited thereto.

Obtained as described above, a sheet having a through hole, for example, can be used through-hole wiring board, the display of the partition forming member such as a PDP, a spacer or the like.

Above-described embodiment provides those described in order to facilitate understanding of the present invention and were not described to limit the present invention. Accordingly, respective elements disclosed in the above embodiments are intended to embrace all design changes and equivalents belonging to the technical scope of the present invention.

For example, the release sheet 12 or the release sheet 12 in the through hole forming sheet 1 'may be omitted.

Hereinafter, a more detailed description of the present invention through examples and so, the scope of the present invention is not limited to these examples.

Example 1
Energy ray-curable compound (I) as dimethylol tricyclodecane diacrylate (bifunctional, molecular weight (Mw): 304, Mw / energy ray-curable groups ratio: 152, solid concentration 100 wt%) and 200 parts by weight , compound (II) as polymethyl methacrylate and (Mw:: 11 million in, Tg 105 ° C., solid concentration 100 wt%) 100 parts by mass as the photopolymerization initiator 2-hydroxy-2-methyl-1-phenyl - propane 1-one (manufactured by Ciba Specialty Chemicals, Darocure 1173, solid concentration 100 wt%) was mixed with 3 parts by weight, and methyl ethyl ketone was added to adjust the solid content concentration to 55 mass% as a solvent, an energy and a coating agent for the line-curable layer.

On the other hand, a polyethylene terephthalate film heavy release type release sheet on one side has been subjected to release treatment with a silicone resin (manufactured by LINTEC Corporation, PET38C, thickness: 38 [mu] m), and polyethylene terephthalate one side of the light release type release sheet was peeled treated with a silicone resin film (manufactured by Lintec Corporation, PET3801, thickness: 38μm) were prepared two types of release sheet.

The coating agent for the resulting energy ray-curable layer above was applied to one surface of the heavy release type release sheet by a knife coater and dried for 1 minute at 90 ° C., to form an energy ray-curable layer having a thickness of 25 [mu] m, as the surface of the energy ray-curable layer laminated to release treatment surface of the light release type release sheet, which was used as a through-hole forming sheet.

Example 2
As the compound (II), 95 of methyl methacrylate and 2-hydroxyethyl methacrylate: copolymerised styrenesulfonate at a weight ratio of 5 (Mw: 11 million in, Tg: 102 ° C., solid concentration 100 wt%) of except for using to prepare a through hole forming sheet in the same manner as in example 1.

Example 3
As the compound (II), 95 of methyl methacrylate and 2-hydroxyethyl methacrylate: copolymerised styrenesulfonate at a weight ratio of 5 (Mw: 30 million in, Tg: 102 ° C., solid concentration 100 wt%) of except for using to prepare a through hole forming sheet in the same manner as in example 1.

Example 4
It was added methyl methacrylate and 2-hydroxyethyl methacrylate and the like becomes 80 mole hydroxyl units 100 moles of the obtained methacrylic acid ester copolymer by copolymerizing at 80:20 2-methacryloyloxyethyl isocyanate , by 48 hours at 40 ° C., methacrylic acid ester copolymer having energy ray-curable groups in the side chain (Mw: 8 million in, Tg: 94 ° C.) was prepared.

As the compound (II), except for using methacrylic acid ester copolymer having energy ray-curable groups in the side chain, to produce a through-hole forming sheet in the same manner as in Example 1.

[Example 5]
As Compound (I), dipentaerythritol hexaacrylate (hexafunctional, Mw: 578, Mw / energy ray-curable groups ratio: 96.3, solid content concentration: 100 mass%) except for using 200 parts by weight, Example to prepare a through hole forming sheet in the same manner as 1.

Comparative Example 1
Energy ray-curable compound (I) as multifunctional urethane acrylate (manufactured by Dainichiseika Color &, 14-29B, Mw: 2300,5 ~ 7 mixture of functional, Mw / energy ray-curable groups ratio: 328 to 460, a solid concentration 80 wt%) 63 parts by weight, compound (II) a butyl methacrylate and acrylic acid obtained by copolymerizing at a weight ratio of 90:10 as a copolymer (Mw: 90 million in, Tg: -44 ° C. , a solid concentration 100 wt%) 100 parts by weight of 2-hydroxy-2-methyl as a photopolymerization initiator 1-phenyl - propane-1-one (manufactured by Ciba Specialty Chemicals, Darocure 1173, solid concentration and 100 mass%) 3 parts by weight, polyisocyanate compound as the thermal crosslinking agent (Toyo Ink Mfg. Co., Oribain BHS-8515, solid concentration 35 wt ) And 2 parts by weight were mixed and methyl ethyl ketone was added to adjust the solid content concentration to 55 mass% as a solvent, was energy ray-curable layer of the coating agent.

Except for using the above coating agent, to prepare a through hole forming sheet in the same manner as in Example 1.

Comparative Example 2
As a through hole forming sheet, a photoresist film (Asahi Kasei Electronics Co., SUNFORT AQ-2558) was prepared.

[Test Example]
(1) such that the thickness after drying of the coating agent storage modulus of Examples 1 to 5 and Comparative Example 1 Measurement of storage modulus (a) the energy ray-curable layer (before curing) is 25 [mu] m, peeling film (Lintec Corporation, PET3801) forming an energy ray-curable layer was coated and dried, by laminating it, thickness of 3 mm, a specimen was produced comprising an energy ray-curable layer having a diameter of 8 mm.

The obtained test piece was measured storage modulus at 25 ° C. by a torsion shear method. Measurements dynamic viscoelasticity measuring device (Rheometric Co., DYNAMIC ANALYZER RDAII) performed at a frequency of 1Hz using a storage elastic modulus at 25 ° C. before curing of the energy ray-curable layer was measured. The results are shown in Table 1.

(B) As the energy ray-curable layer thickness after drying of the coating agent storage modulus of Examples 1 to 5 and Comparative Example 1 (after curing) is 25 [mu] m, a release film (made by Lintec Corporation, PET3801) coating and dried to form an energy ray-curable layer was laminated to a thickness is 100μm to. Then, after curing by irradiation with ultraviolet rays (illuminance 400 mW / cm 2, light quantity 300 mJ / cm 2) for a fusion H bulb as a light source, cut into 5 mm × 30 mm, which was used as a test piece.

The obtained test piece was measured storage modulus at 25 ° C.. Measurements dynamic viscoelasticity measuring apparatus (TA Instruments, Inc., Q800DMA) performed at a frequency 11Hz was used to measure the storage modulus at 25 ° C. of the cured energy ray-curable layer. The results are shown in Table 1.

(2) Measurement Examples 1-5 and Comparative Examples 1-2 through-hole forming sheet of the total light transmittance, ultraviolet (illuminance 400 mW / cm 2, light quantity 300 mJ / cm 2) for a fusion H bulb as a light source after irradiation, the light release type release sheet and heavy release type release sheet was peeled off, in conformity with JIS K7375, a haze meter (Nippon Denshoku Industries Co., NDH2000) was measured for total light transmittance with. The results are shown in Table 1.

Figure JPOXMLDOC01-appb-T000001

(3) a light release type release sheet of the through-hole forming sheet of developing Test Examples 1-5 and Comparative Examples 1 and 2 were peeled off, non-alkali glass substrate (Corning, # 1737) was applied to. Removing the heavy release type release sheet, chromium glass stamper to form a dot-shaped ultraviolet ray shielding portion having a diameter of 200μm by photolithography using a (Cr), a pressure 0.5MPa energy ray-curable layer exposed pressure bonding, the stamper side was irradiated with ultraviolet rays (illuminance 400 mW / cm 2, light quantity 300 mJ / cm 2) for a fusion H bulb as a light source. Peeling off the stamper, the energy ray-curable layer was immersed in toluene, ultrasonic cleaner (manufactured by AS ONE Co., VS-P100) was used to perform development for 45 Hz, 20 sec. The resulting through-hole forming sheet placed on a hot plate, after 5 minutes drying at 130 ° C., observing the state of formation of the through-holes a scanning electron microscope (Hitachi High-Technologies Corporation, S-4700) in did. As a result, those through-holes are formed ○, it was × what through hole is not formed. The results are shown in Table 2.

Further, the through hole forming sheet which through-holes are formed, using the above scanning electron microscope to measure the diameter of the through holes of any 9 points, to calculate the average diameter. The results are shown in Table 2.

(4) irregular pattern formation test Examples 1-5 and Comparative Examples 1 and 2 of the light release type release sheet of the through-hole forming sheet was peeled off, non-alkali glass substrate (Corning, # 1737) was attached to the . Heavy release type removing the release sheet, the concavo-convex pattern height 100 nm, and pressed with a pressure 0.5MPa energy ray-curable layer exposed glass stamper pattern width 10 [mu] m, from the stamper side, a light source fusion H bulb ultraviolet (illuminance 400 mW / cm 2, light quantity 300 mJ / cm 2) was irradiated. Peeling off the stamper, the shape of the uneven scanning electron microscope (Hitachi High-Technologies Corporation, S-4700) was observed with, measures the height of the uneven pattern of arbitrary 9 points, and evaluated according to the following criteria.
{(Average height of the concavo-convex pattern) / (pattern height of the stamper)} × 100
I value those 95 ~ 100% ○, and as × of less than 95%. The results are shown in Table 2.

Figure JPOXMLDOC01-appb-T000002

Table 1 and Table 2, the through-hole forming sheet of Example has excellent developing performance and the uneven pattern formed performance, higher transparency. On the other hand, the through-hole forming sheet of the comparative example, will be swollen with toluene in the developing test, it was not possible to form a through hole.

Through hole forming sheet according to the present invention, it is possible to form a through-hole or through-holes and fine irregularities, the sheet having a through hole or through hole-convex pattern obtained, for example, through-hole wiring board, the display of the partition forming member, such as a PDP, a spacer useful in optical lenses and the like.

1 ... through hole forming sheet 11 ... energy ray-curable layer 12, 12 '... release sheet 2 ... seat 21 ... through hole 3 ... stamper 31 ... energy ray shielding portion 32 ... energy ray transmissive portion having a through-hole-convex pattern 4 ... glass substrate

Claims (16)

  1. (Weight average) molecular weight of 200 to 10,000, having an energy ray-curable groups, (weight average) that the ratio of the molecular weight / energy ray-curable groups contains an energy ray-curable compound is 80-300 wherein the through-hole or through-hole-convex pattern resin composition for the energy ray-curable layer for the purpose of formation of.
  2. The energy ray-curable compound, a polyfunctional (meth) resin composition for the energy ray-curable layer as claimed in claim 1, characterized in that the acrylic acid ester.
  3. Weight average molecular weight of 50,000 to 1,200,000, compound is further characterized by containing claim 1 or 2 resin composition for the energy ray-curable layer according to.
  4. Wherein the compound is (meth) resin composition for the energy ray-curable layer as claimed in claim 3, characterized in that the acrylic acid ester polymer.
  5. The compound has an energy ray-curable groups in the side chain (meth) resin composition for the energy ray-curable layer as claimed in claim 3, characterized in that the acrylic acid ester copolymer.
  6. Amount of the compound, the total amount of said compound with said energy ray-curable compound is 100 wt%, to any one of claims 3-5, characterized in that 20 to 60 wt% the resin composition for the energy ray-curable layer as claimed.
  7. Characterized by comprising an energy ray-curable layer comprising the resin composition according to any one of claims 1 to 6, the through-hole or through hole forming sheet for forming a through-hole-convex pattern.
  8. Through hole forming sheet according to claim 7, wherein the storage modulus at 25 ° C. before curing of the energy ray-curable layer is 1 × 10 3 ~ 1 × 10 6 Pa.
  9. Through hole forming sheet according to claim 7 or 8 total light transmittance after curing of the energy ray-curable layer is equal to or less than 85%.
  10. Provided with a concavo-convex pattern, the portion to be formed a through hole in the sheet the energy ray shielding portion, the other portion providing a stamper that is the energy ray transmitting portion,
    The stamper is pressed against the energy ray-curable layer of the through hole forming sheet according to any one of claims 7-9, irradiating an energy beam to the energy ray-curable layer from the stamper side in this state,
    Thereby transferring an uneven pattern of the stamper to the energy ray-curable layer, the portion corresponding to the energy-ray transmitting portion of the stamper in the energy ray-curable layer is cured, a portion corresponding to the energy-ray shielding portion of said stamper is the state of the uncured,
    Then, and forming a through hole uncured portions of the energy ray-curable layer is removed by a solvent, method for producing a sheet having a through-hole-convex pattern.
  11. Sheet manufacturing method according to claim 10, characterized in that the crimping of the stamper with respect to the energy ray-curable layer at room temperature.
  12. It said solvent is ethyl acetate, methyl ethyl ketone, sheet manufacturing method according to claim 10 or 11, characterized in that at least one selected from the group consisting of acetone and toluene.
  13. Sheet according to any one of claims 10 to 12, characterized in that by the removal of the uncured portion of the energy ray-curable layer, by immersing the through hole forming sheet into a solvent, ultrasonic cleaning the method of production.
  14. Portion to be formed a through hole in the sheet the energy ray shielding portion, the other portion providing a mask that is the energy ray transmitting portion,
    To the energy ray-curable layer of the through hole forming sheet according to any one of claims 7-9, irradiated with energy rays through the mask,
    Portion corresponding to the energy-ray transmitting portion of the mask in the energy ray-curable layer is cured, a portion corresponding to the energy-ray shielding portion of the mask is the uncured state,
    Then, and forming a through hole uncured portions of the energy ray-curable layer is removed by a solvent, method for producing a sheet having a through hole.
  15. It said solvent is ethyl acetate, methyl ethyl ketone, sheet manufacturing method according to claim 14, characterized in that at least one selected from the group consisting of acetone and toluene.
  16. Sheet method as claimed in claim 14 or 15, characterized in that by the removal of the uncured portion of the energy ray-curable layer, by immersing the through hole forming sheet into a solvent, ultrasonic cleaning .
PCT/JP2009/057233 2008-04-10 2009-04-08 Resin composition for energy ray-curable layer and sheet for forming through hole WO2009125806A1 (en)

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JPH0237353A (en) * 1988-07-27 1990-02-07 Oki Electric Ind Co Ltd Method and device for developing resist
JPH0297516A (en) * 1987-09-16 1990-04-10 Canon Inc Active energy ray-curable resin composition
JPH0580530A (en) * 1991-09-24 1993-04-02 Hitachi Ltd Production of thin film pattern
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JPH0237353A (en) * 1988-07-27 1990-02-07 Oki Electric Ind Co Ltd Method and device for developing resist
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JPH07128856A (en) * 1993-04-30 1995-05-19 Japan Synthetic Rubber Co Ltd Photosensitive resin composition and photosensitive resin resist
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