WO2015046740A1 - Composition de résine photodurcissable pour film donneur et film donneur - Google Patents

Composition de résine photodurcissable pour film donneur et film donneur Download PDF

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WO2015046740A1
WO2015046740A1 PCT/KR2014/007159 KR2014007159W WO2015046740A1 WO 2015046740 A1 WO2015046740 A1 WO 2015046740A1 KR 2014007159 W KR2014007159 W KR 2014007159W WO 2015046740 A1 WO2015046740 A1 WO 2015046740A1
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Prior art keywords
acrylate
resin composition
photocurable resin
donor
compound
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PCT/KR2014/007159
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English (en)
Korean (ko)
Inventor
최태이
조명현
김장순
배효대
윤경준
김수진
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(주)엘지하우시스
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Publication of WO2015046740A1 publication Critical patent/WO2015046740A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
    • C08L33/08—Homopolymers or copolymers of acrylic acid esters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/32—Layered products comprising a layer of synthetic resin comprising polyolefins
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
    • B32B27/365—Layered products comprising a layer of synthetic resin comprising polyesters comprising polycarbonates
    • 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
    • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
    • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
    • C08F20/10—Esters
    • 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
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/042—Coating with two or more layers, where at least one layer of a composition contains a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C08L75/16—Polyurethanes having carbon-to-carbon unsaturated bonds having terminal carbon-to-carbon unsaturated bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2457/00—Electrical equipment
    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
    • B32B2457/206—Organic displays, e.g. OLED
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
    • C08F220/325—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals containing glycidyl radical, e.g. glycidyl (meth)acrylate
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2475/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2475/04—Polyurethanes
    • C08J2475/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/16—Applications used for films

Definitions

  • It relates to a photocurable resin composition for donor films and a donor film.
  • OLED organic light emitting display device
  • the method of forming an organic film layer on an OLED includes a deposition method, an inkjet method, a laser thermal transfer method (LITI), and the like.
  • the organic film layer composition including an additive or a surfactant is coated on a substrate having a relatively low surface energy in order to form an organic film layer in the OLED, there is a problem in that the wettability is poor and the coating property is low.
  • it may cause thermal damage to the organic film layer there is a problem that the phase difference of the organic film layer due to post-curing.
  • One embodiment of the present invention provides a photocurable resin composition for a donor film excellent in patterning reliability and transfer quality.
  • Another embodiment of the present invention provides a donor film including an intermediate layer formed from a photocurable resin composition for a donor film having excellent patterning reliability and transfer quality.
  • a photocurable resin composition for a donor film the glass transition temperature of the cured product of the composition is about 40 °C to about 180 °C, storage modulus is from about 3.5 to about 5.5 GPa at 25 °C Can be.
  • the composition is at least one acrylate monomer selected from the group consisting of urethane acrylates, epoxy acrylates, ester acrylates, cardo-based acrylates, and combinations thereof, acrylate oligomers, It may include a photocurable compound, a crosslinkable acrylate monomer and a photoinitiator including an acrylate prepolymer or a combination thereof.
  • the urethane acrylate is formed by polymerization of an isocyanate monomer and a polyol, and the isocyanate compound includes at least one or more selected from aliphatic isocyanate compounds, aromatic isocyanate compounds, and combinations thereof, and the polyol (meth) ) Acrylic acid hydroxyalkyl ester compound.
  • the epoxy acrylate may include at least one or more selected from bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, (meth) acrylic acid adducts of phenol novolac epoxy resins, and combinations thereof. .
  • the ester acrylate may include a polyfunctional polyester acrylate compound of a polyhydric alcohol.
  • the cardo-based acrylate may be a compound to which photocurable acrylate is given by reacting a cardo-based compound of Formula 1 with at least one selected from the group consisting of dianhydride compounds, diol compounds, diacrylic acid, and combinations thereof.
  • R 1 and R 2 are each independently —OH, —NH 2 , —O—CH 2 —CH 2 —OH, or —COOH.
  • the photocurable compound may include about 30 to about 70% by weight.
  • It may include about 20 to about 60% by weight of the crosslinkable acrylate monomer.
  • the crosslinkable acrylate monomer may be two to four acrylate functional group-containing monomers.
  • the glass transition temperature (Tg) of the photocurable compound may be about -50 °C to about 60 °C.
  • the glass transition temperature of the cured product may be prepared to be about 40 ° C to about 180 ° C.
  • the photocurable resin composition for a donor film may include a photocurable compound comprising a weight average molecular weight of about 500 to about 20000 of an oligomer and a monomer in a ratio of about 1: 4 to about 4: 1.
  • the monomer may be an aliphatic group-containing monomer
  • the oligomer may be an aromatic group-containing oligomer
  • a substrate layer, a photothermal conversion layer and an intermediate layer provides a donor film which is a layer prepared by curing the photocurable resin composition for a donor film.
  • a transfer layer may be stacked on the intermediate layer.
  • the base film is glass; Or a transparent film including at least one selected from the group consisting of polyester, polycarbonate, polyolefin, polyvinyl, and combinations thereof.
  • the intermediate layer may have a surface energy of about 11 mN / m to about 21 mN / m.
  • the photocurable resin composition for donor film is excellent in patterning reliability and transfer quality.
  • the thermal expansion occurs well by adjusting the modulus of the intermediate layer, and the glass transition temperature is adjusted to optimize the deformation and swelling of the intermediate layer at the thermal expansion temperature.
  • FIG. 1 is a schematic cross-sectional view of a donor film according to an embodiment of the present invention.
  • any configuration is formed on the “top (or bottom)" of the substrate or “top (or bottom)” of the substrate means that any configuration is formed in contact with the top (or bottom) of the substrate.
  • it is not limited to not including other configurations between the substrate and any configuration formed on (or under) the substrate.
  • the photocurable resin composition for a donor film has a glass transition temperature of about 40 ° C to about 180 ° C of the cured product formed from the composition, and a storage modulus of the cured product of the composition is about 25 ° C. At about 3.5 to about 5.5 GPa.
  • the photocurable resin composition for a donor film is a composition for forming an intermediate layer interposed between a photothermal conversion layer and a transfer layer of a donor film, and the intermediate layer is formed to have the above-described glass transition temperature and storage modulus characteristics.
  • a donor film including an intermediate layer formed from the photocurable resin composition for donor film By using a donor film including an intermediate layer formed from the photocurable resin composition for donor film, it is possible to improve the performance of transferring the organic material of the transfer layer during patterning using laser thermal transfer.
  • the organic material After depositing an organic material on the donor film to form a transfer layer, the organic material is transferred to a substrate to be transferred by laser patterning.
  • the intermediate layer formed from the photocurable resin composition for the donor film has a glass transition temperature of less than about 40 ° C., a problem may occur that the stability and storage properties of the film are deteriorated at room temperature, and when the glass transition temperature exceeds about 180 ° C., the laser When the thermal transfer is performed, the intermediate layer may be maintained in a glassy state, which may cause a problem in that transfer performance is degraded.
  • the cured intermediate layer from the UV-curable resin composition for the donor film has a storage modulus of less than about 3.5 GPa, organic transfer may occur to areas that should not be patterned when performing laser thermal transfer, thereby causing a problem of lowering patterning reliability. If the storage modulus exceeds about 5.5 GPa, thermal expansion by the laser in the intermediate layer may be difficult to occur during laser thermal transfer.
  • the photocurable resin composition for a donor film is specifically, at least one selected from the group consisting of urethane acrylates, epoxy acrylates, ester acrylates, cardo-based acrylates, and combinations thereof.
  • a photocurable compound including an acrylate monomer, an acrylate oligomer, an acrylate prepolymer, or a combination thereof may further include additives such as a crosslinkable acrylate monomer and a photoinitiator.
  • the acrylate oligomer of the photocurable compound may have a weight average molecular weight of about 500 to about 20000.
  • the photocurable resin composition for a donor film may include about 20 to about 60 wt% of the aforementioned acrylate oligomer as the photocurable compound.
  • the urethane acrylate is to give an acrylate group to the urethane compound to be UV cured, it is a generic name of a compound having a urethane bond and an acrylate group.
  • the urethane bond may be formed by polymerizing an isocyanate monomer and a polyol.
  • the urethane acrylate photocurable oligomer may be a urethane bond formed by reacting an isocyanate compound with a (meth) acrylic acid hydroxyalkyl ester compound. It may include an oligomer formed by polymerizing a weight average molecular weight of about 500 to about 20000.
  • isocyanate compounds include aliphatic isocyanate compounds such as hexamethylene diisocyanate (HMDI), isophorone diisocyanate (IPDI), or toluene diisocyanate (TDI), and methylene diphenyl diisocyanate.
  • HMDI hexamethylene diisocyanate
  • IPDI isophorone diisocyanate
  • TDI toluene diisocyanate
  • methylene diphenyl diisocyanate methylene diphenyl diisocyanate
  • Aromatic isocyanate compounds such as isocyanate (methylene diphenyl diisocyanate, MDI), etc. are mentioned, These can be used individually or in mixture of 2 or more types.
  • (meth) acrylic acid hydroxyalkyl ester compound examples include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 6- Hydroxyhexyl (meth) acrylate, 8-hydroxyoctyl (meth) acrylate, 2-hydroxyethylene glycol (meth) acrylate or 2-hydroxypropylene glycol (meth) acrylate, and the like, and combinations thereof This can be used.
  • the epoxy acrylate is a compound in which an acrylate group is given to an epoxy group-containing epoxy group compound as a photocurable compound, and specific examples thereof include bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, or a phenol novolak epoxy resin. Epoxy acrylate type compounds etc. which are the (meth) acrylic acid addition products of these are mentioned.
  • the ester acrylate is a compound in which an acrylate group is added to an ester compound as a photocurable compound, and specific examples thereof include polyhydric alcohols such as trimethylolpropane triacrylate, pentaerythritol tetraacrylate, or dipentaerythritol hexaacrylate. It may be a polyfunctional polyester acrylate compound.
  • the cardo-based acrylate (or fluorene-based acrylate) is a photocurable compound, specifically, at least one selected from the group consisting of a cardo-based compound of Formula 1, a dianhydride compound, a diol compound, diacrylic acid, and a combination thereof It may be a compound endowed with a photocurable acrylate by reacting one.
  • R 1 and R 2 are each independently —OH, —NH 2 , —O—CH 2 —CH 2 —OH, or —COOH.
  • the photocurable composition for a donor film may include about 30 to about 70% by weight of the photocurable compound.
  • crosslinkable acrylate monomer various photocurable monomers may be used, for example, 2 to 4 acrylate functional group-containing monomers.
  • specific examples of the crosslinkable acrylate monomer include 1,2-ethylene glycol diacrylate, 1,12-dodecanediol acrylate, 1,4-butanediol di (meth) acrylate, and 1,6-hexanediol Di (meth) acrylate, neopentyl glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, neopentyl glycol adipate di (meth) acrylate, hydroxypivalic acid ) Neopentylglycol di (meth) acrylate, dicyclopentanyl di (meth) acrylate, caprolactone modified dicyclopentenyl di (meth) acrylate, ethylene oxide modified di (meth) acrylate, di (Meth) acryloxy ethyl is
  • the photocurable resin composition for a donor film may include about 20 to about 60 wt% of the crosslinkable acrylate monomer.
  • the photoinitiator examples include benzoin methyl ether, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, ⁇ , ⁇ -methoxy- ⁇ -hydro Roxacytophenone, 2-benzoyl-2- (dimethylamino) -1- [4- (4-morphonyl) phenyl] -1-butanone, 2,2-dimethoxy-2-phenylacetophenone, oxime ester system And one or more selected from the group consisting of.
  • the UV curable resin composition for a donor film may include about 0.1 to about 10% by weight of the photoinitiator.
  • an oligomeric raw material prepared as the photocurable compound
  • the glass transition temperature of the range of about -50 °C to about 60 °C, and after forming a cured polymer network structure through a photoinitiator can be prepared so that the glass transition temperature of the cured product is about 40 °C to about 180 °C.
  • isocyanate and (meth) acrylic acid hydroxyalkyl ester include an aromatic group to give a hard repeating unit
  • the glass transition temperature can be raised.
  • the photocurable resin composition for a donor film can be adjusted by changing the type, molecular weight, content, etc. of the monomer constituting a repeat unit of the photocurable compound in order to implement the storage modulus of the above-described numerical range have.
  • the storage modulus increases if the repeating unit consists of an aromatic of hard type.
  • it is also possible to control the storage modulus through the molecular weight when the molecular weight is large, the interval between the curing sites (site) is long and the crosslinking density (crosslinking density) is lowered, which results in a decrease in the storage modulus.
  • the photocurable resin composition for a donor film may include a content ratio of oligomer and monomer having a weight average molecular weight of about 500 to about 20000 to about 1: 4 to about 4: 1, specifically, the monomer It may be an aliphatic group-containing monomer, the oligomer may be an aromatic group-containing oligomer.
  • the aliphatic monomer and the aromatic monomer may not be included at the same time.
  • the photocurable resin composition for a donor film is from the group consisting of a crosslinking agent, an ultraviolet stabilizer, an antioxidant, a colorant, a reinforcing agent, a filler, an antifoaming agent, a surfactant, a plasticizer, and combinations thereof in a range that does not affect the effect of the invention. It may further comprise one or more additives selected.
  • a donor film including a substrate layer, a photothermal conversion layer, an intermediate layer, and a transfer layer.
  • middle layer is manufactured by hardening
  • the donor film may improve the performance of transferring the organic material of the transfer layer during patterning using laser thermal transfer.
  • Patterning is one of the factors that determine the transfer quality, so that thermal expansion occurs well by adjusting the storage modulus of the intermediate layer formed from the photocurable resin composition for a donor film described above, and controlling the glass transition temperature to deform and swell the intermediate layer at the thermal expansion temperature.
  • the donor film may be usefully used for manufacturing a display device such as an organic light emitting display device.
  • the donor film 10 includes a base layer 11, a photothermal conversion layer 12 formed on the base layer 11, and an intermediate layer 13 formed on the photothermal conversion layer 12. do.
  • a transfer layer 14 formed on the intermediate layer 13 may be formed.
  • the base film 11 is glass; Or a transparent film including at least one selected from the group consisting of polyester, polycarbonate, polyolefin, polyvinyl, and combinations thereof.
  • the base film 11 is specifically, a polyethylene terephthalate (PET) film or a polyethylene naphthalate (PEN) film, and the base film of the material is most preferable in view of processability, thermal stability and transparency. Do.
  • PET polyethylene terephthalate
  • PEN polyethylene naphthalate
  • the surface of the base film 11 is modified by a surface treatment known to those skilled in the art, for example, a surface treatment such as corona, plasma, and the like to control adhesion, surface tension, etc. when the photothermal conversion layer 12 is laminated in a subsequent process. It is also possible.
  • the donor film 10 may further include a primer layer (not shown) formed on the base film 11.
  • a primer layer may be formed between the base film 11 and the photothermal conversion layer 12.
  • the primer layer is to control the temperature transfer between the base film and the adjacent layer, to improve the adhesion between the base film 11 and the adjacent layer, and to control the image forming radiation transfer to the photothermal conversion layer 12. If the primer layer is not formed, a phenomenon in which the base film 11 and the photothermal conversion layer 12 are separated in a transfer process using a laser may occur.
  • At least one selected from the group consisting of acrylic resins, polyurethane resins, polyester resins, and combinations thereof may be used.
  • the base film 11 and the photothermal conversion layer 12 may be separated in a transfer process using a laser.
  • the photothermal conversion layer 12 is a layer that absorbs light in the infrared-visible ray region and converts a part of the light into heat, and is made of a resin composition including a thermosetting resin and a photothermal conversion material.
  • the intermediate layer 13 may be formed by coating the above-mentioned photocurable resin composition for a donor film and thermosetting or photocuring, wherein the intermediate layer 13 is transferred by a heat generated in the photothermal conversion layer 12.
  • the intermediate layer 13 is excellent in patterning reliability as described above.
  • the intermediate layer 13 preferably has a low surface energy. Since the intermediate layer 13 has a low surface energy, there is an advantage in that the organic material is easily transferred even in a small thermal expansion.
  • the intermediate layer 13 may have a surface energy of about 11 mN / m to about 21 mN / m.
  • the intermediate layer 13 may be formed to have a thickness of, for example, about 1 ⁇ m to about 5 ⁇ m. When the thickness of the intermediate layer 13 is less than about 1 ⁇ m, the organic material of the transfer layer may be damaged due to the heat generated in the photothermal conversion layer. If the thickness of the intermediate layer 13 is greater than about 5 ⁇ m, the transfer performance may not be sufficiently swelled.
  • the transfer layer 14 typically includes one or more layers for transferring to the receptor.
  • it may be formed using organic, inorganic, organometallic and other materials, including electroluminescent materials or electrically active materials.
  • poly (phenylenevinylene), poly-para-phenylene, polyfluorene, polydialkylfluorene, polythiophene, poly (9-vinylcarbazole), poly (N-vinylcarbazole-vinyl Alcohol) copolymers, triarylamine, polynorbornene, polyaniline, polyarylpolyamine, triphenylamine-polyetherketone and the like can be used.
  • the transfer layer 14 may further include one or more materials selected from known light emitting materials, hole transporting organic materials, and electron transporting organic materials so as to match the characteristics of the organic light emitting device to be manufactured. It may include a compound comprising at least one of a non-luminescent low molecular material, a non-luminescent charge transfer polymer material and a curable organic semi-inder material.
  • a photocurable resin composition was prepared by mixing 50 wt% of a photocurable compound (weight average molecular weight 3000) of a cardo-based acrylate having an aromatic group, 45 wt% of a bifunctional acrylate monomer having an aliphatic group, and 5 wt% of a photoinitiator.
  • UV lamp After forming a photothermal conversion layer containing a carbon black photothermal conversion material on the substrate layer of the polyester film to a thickness of 3 ⁇ m, and coating the urethane acrylate-based resin composition prepared above to a thickness of 3 ⁇ m, UV lamp The donor film was manufactured by preparing an intermediate layer by irradiating with UV and curing.
  • the cardo-based acrylate is a hard type oligomer (molecular weight 3000) having a hard structure in which an aromatic 5-membered ring and a 6-membered ring cross each other, and the composition combining the bifunctional monomer in the content ratio may realize a storage modulus within a desired range. .
  • the glass transition temperature and storage modulus of the prepared intermediate layer were measured.
  • the photocurable resin composition was prepared to contain 60 wt% of urethane acrylate (weight average molecular weight 5000) having an aromatic constituent, 35 wt% of the bifunctional acrylate monomer, and 5 wt% of the photoinitiator.
  • a donor film was produced by the method.
  • the photocurable resin composition was the same as in Example 1 except that the photocurable resin composition was prepared to contain 75 wt% of urethane acrylate (weight average molecular weight 6000) having an aromatic constituent, 20 wt% of a bifunctional acrylate monomer, and 5 wt% of a photoinitiator.
  • a donor film was produced by the method.
  • the photocurable resin composition was prepared to contain 80 wt% of urethane acrylate (weight average molecular weight 5000) having an aromatic constituent, 15 wt% of bifunctional acrylate monomer, and 5 wt% of a photoinitiator.
  • the donor film was prepared by the following.
  • the photocurable resin composition was prepared to contain 30 wt% of urethane acrylate (weight average molecular weight 5000) having an aromatic constituent, 65 wt% of bifunctional acrylate monomer, and 5 wt% of a photoinitiator.
  • the donor film was prepared by the following.
  • the photocurable resin composition was prepared to contain 50 wt% of epoxy acrylate (weight average molecular weight 3000) having an aliphatic constituent, 45 wt% of trifunctional acrylate monomer, and 5 wt% of a photoinitiator.
  • the donor film was prepared by the following.
  • Nanoindentation Hysitron TI750: Measured at room temperature in nanoDMA mode to obtain a storage modulus value.
  • the transfer quality was evaluated by the following method.
  • Test pattern substrate preparation A test pattern substrate having a bank structure thickness of 0.5 ⁇ m or less and a Taper Angle of 15 ° or less is prepared.
  • Organic DNTPD N, N'-diphenyl-N, N'-bis- [4- (phenyl-m-tolyl-amino) -phenyl] -biphenyl-4 on a test pattern substrate having a pixel size of 11 ⁇ 78 ⁇ m , 4'-diamine was deposited to 100 mm thick.
  • Example 2 2) TCTA ((N-carbazolyl) -triphenylamine) was deposited on the film surface prepared in Example 1-2 and Comparative Example 1-2 to a thickness of 500 mm 3.
  • a mask is mounted to allow imaging with alignment with the pixel area of the substrate.
  • the laser beam is irradiated with an amount of energy of 1.5 J / cm 2 onto the substrate (PET surface) of the prepared sample and scanned.
  • Example 1-2 After scanning After removal of the donor film in Example 1-2 and Comparative Example 1-2, the organic transfer traces to the substrate surface is evaluated using an optical microscope.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Laminated Bodies (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un composition de résine photodurcissable pour un film donneur, un produit durci obtenu à partir de la composition présentant une température de transition vitreuse d'approximativement 40 à 180°C et un module de conservation d'approximativement 3,5 à approximativement 5,5GPa à approximativement 25°c.
PCT/KR2014/007159 2013-09-27 2014-08-04 Composition de résine photodurcissable pour film donneur et film donneur WO2015046740A1 (fr)

Applications Claiming Priority (2)

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KR10-2013-0115417 2013-09-27
KR1020130115417A KR101807900B1 (ko) 2013-09-27 2013-09-27 도너 필름용 광경화성 수지 조성물 및 도너 필름

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017179906A1 (fr) * 2016-04-12 2017-10-19 주식회사 엘지화학 Pellicule d'encapsulation

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Publication number Priority date Publication date Assignee Title
KR19980086533A (ko) * 1997-05-23 1998-12-05 손욱 칼라필터용 도너필름
KR100725023B1 (ko) * 2006-10-16 2007-06-07 제일모직주식회사 카도계 수지를 함유한 수지 조성물 및 그에 의한 패턴의 제조방법, 이를 이용한 컬러필터
KR20100020154A (ko) * 2008-08-12 2010-02-22 에스에스씨피 주식회사 광경화형 코팅 조성물
KR20130072573A (ko) * 2011-12-22 2013-07-02 코오롱인더스트리 주식회사 레이저 열전사 방법용 도너필름
KR20130078600A (ko) * 2011-12-30 2013-07-10 제일모직주식회사 열전사 필름

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JP4566525B2 (ja) * 2002-08-22 2010-10-20 リンテック株式会社 ポリカーボネート用表面保護フィルム

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Publication number Priority date Publication date Assignee Title
KR19980086533A (ko) * 1997-05-23 1998-12-05 손욱 칼라필터용 도너필름
KR100725023B1 (ko) * 2006-10-16 2007-06-07 제일모직주식회사 카도계 수지를 함유한 수지 조성물 및 그에 의한 패턴의 제조방법, 이를 이용한 컬러필터
KR20100020154A (ko) * 2008-08-12 2010-02-22 에스에스씨피 주식회사 광경화형 코팅 조성물
KR20130072573A (ko) * 2011-12-22 2013-07-02 코오롱인더스트리 주식회사 레이저 열전사 방법용 도너필름
KR20130078600A (ko) * 2011-12-30 2013-07-10 제일모직주식회사 열전사 필름

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017179906A1 (fr) * 2016-04-12 2017-10-19 주식회사 엘지화학 Pellicule d'encapsulation
US10593908B2 (en) 2016-04-12 2020-03-17 Lg Chem, Ltd. Encapsulation film

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TW201512352A (zh) 2015-04-01
TWI634174B (zh) 2018-09-01
KR20150035647A (ko) 2015-04-07
KR101807900B1 (ko) 2017-12-12

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