KR101847229B1 - Light curable resin composition for donor film and donor film - Google Patents

Light curable resin composition for donor film and donor film Download PDF

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KR101847229B1
KR101847229B1 KR1020130115418A KR20130115418A KR101847229B1 KR 101847229 B1 KR101847229 B1 KR 101847229B1 KR 1020130115418 A KR1020130115418 A KR 1020130115418A KR 20130115418 A KR20130115418 A KR 20130115418A KR 101847229 B1 KR101847229 B1 KR 101847229B1
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acrylate
donor film
resin composition
photocurable resin
layer
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KR20150035648A (en
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최태이
조명현
김장순
배효대
윤경준
고유리
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주식회사 엘지화학
엘지디스플레이 주식회사
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Priority to KR1020130115418A priority Critical patent/KR101847229B1/en
Priority to PCT/KR2014/007161 priority patent/WO2015046741A1/en
Priority to TW103132155A priority patent/TWI634129B/en
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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
    • 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
    • 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
    • B32B27/16—Layered products comprising a layer of synthetic resin specially treated, e.g. irradiated
    • 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
    • B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
    • B32B27/308—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising acrylic (co)polymers
    • 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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • 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

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  • Electroluminescent Light Sources (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
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Abstract

The cured product of the composition has a glass transition temperature of from about 75 캜 to about 100 캜 and a storage modulus of from about 3.5 to about 5.5 GPa at about 25 캜 and from about 0.01 to about 0.1 GPa at about 200 캜. / RTI >

Description

TECHNICAL FIELD [0001] The present invention relates to a photocurable resin composition for a donor film and a donor film for a donor film,

To a photo-curing resin composition and a donor film for a donor film.

Recently, the development trend of the display device technology is required to develop a technology having a high visibility while using less energy. Accordingly, the development of a display device using an organic light emitting diode (OLED), which is known to have a lower energy consumption compared to the conventional light emitting mode, has been competitive.

In order to realize full color of a display device using such an OLED, it is very important to pattern the color of the light emitting device. As a result, it is necessary to form an organic film layer of the OLED for determining the color of the light emitting device There are differences in implementation effect depending on the method. Methods for forming an organic film layer in an OLED include a vapor deposition method, an ink jet method, and a laser thermal transfer method (LITI).

When an organic film layer composition containing an additive or a surfactant is coated on a substrate having a relatively low surface energy to form an organic film layer in an OLED, the wettability is poor and the coating property is low. In addition, when the conventional thermal curing method is used to form the organic layer in the OLED, thermal damage to the organic layer may be caused, and phase difference of the organic layer may be caused by post-curing.

An 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 comprising an intermediate layer formed from a photocurable resin composition for a donor film excellent in patterning reliability and transfer quality.

In one embodiment of the present invention, there is provided a photocurable resin composition for a donor film, wherein the cured product of the composition has a glass transition temperature of from about 75 캜 to about 100 캜 and a storage modulus of from about 3.5 to about 5.5 GPa And may be from about 0.01 to about 0.1 GPa at about 200 < 0 > C.

The composition may comprise at least one acrylate-based monomer selected from the group consisting of urethane acrylate-based, epoxy acrylate-based, ester acrylate-based, cardo-based acrylate-based and combinations thereof, acrylate- An acrylate-based prepolymer, or a combination thereof, a crosslinkable acrylate-based monomer, and a photoinitiator.

The urethane acrylate is formed by polymerization of an isocyanate-based monomer with a polyol. The isocyanate-based compound includes at least one or more selected from an aliphatic isocyanate compound, an aromatic isocyanate compound, and a combination thereof. ) Acrylic acid hydroxyalkyl ester compound.

The epoxy acrylate may include at least one or more selected from the group consisting of bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, (meth) acrylic acid adduct of phenol novolak epoxy resin, and combinations thereof .

The ester acrylate may include a polyfunctional polyester acrylate compound of a polyhydric alcohol.

The cadmium acrylate may be a compound imparted with photo-curable acrylate by reacting at least one selected from the group consisting of a dianhydride compound, a diol compound, diacrylic acid, and a combination thereof, .

[Chemical Formula 1]

Figure 112013087938610-pat00001

In this formula,

R 1 and R 2 are each independently -OH, -NH 2 , -O-CH 2 -CH 2 -OH or -COOH.

About 30% to about 70% by weight of the photocurable compound.

And from about 20% to about 60% by weight of the crosslinkable acrylate monomer.

The crosslinkable acrylate monomer may be a monomer having two to four acrylate functional groups.

The glass transition temperature (Tg) of the photocurable compound may be about -50 ° C to about 60 ° C.

After the polymer network structure has been formed through the photoinitiator, the glass transition temperature of the cured product may be from about 75 ° C to about 100 ° C.

The photocurable resin composition for a donor film may include a photo-curable compound including an oligomer having a weight average molecular weight of about 500 to about 20000 and a monomer in a ratio of about 1: 4 to about 4: 1.

The adduct monomer may be an aliphatic group-containing monomer, and the oligomer may be an aromatic group-containing oligomer.

In another embodiment of the present invention, there is provided a donor film comprising a base layer, a photo-thermal conversion layer and an intermediate layer, wherein the intermediate layer is a layer prepared by curing the photocurable resin composition for the donor film.

A transfer layer may be laminated on the intermediate layer.

The base film is made of glass; Or a transparent film containing at least one selected from the group consisting of polyester, polycarbonate, polyolefin, polyvinyl, and combinations thereof.

And a primer layer formed on the base film.

The intermediate layer may have a surface energy of about 11 mN / m to about 21 mN / m.

The photocurable resin composition for a donor film is excellent in patterning reliability and transfer quality. One of the factors that determines the transfer quality of patterning is to adjust the modulus of the middle layer so that the thermal expansion occurs well and to adjust the glass transition temperature to optimize the deformation and swelling of the middle layer at the thermal expansion temperature.

1 is a schematic cross-sectional view of a donor film according to one embodiment of the present invention.

Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

In order to clearly illustrate the present invention, parts not related to the description are omitted, and the same or similar components are denoted by the same reference numerals throughout the specification.

In the drawings, the thickness is enlarged to clearly represent the layers and regions. In the drawings, for the convenience of explanation, the thicknesses of some layers and regions are exaggerated.

Hereinafter, the formation of any structure in the "upper (or lower)" or the "upper (or lower)" of the substrate means that any structure is formed in contact with the upper surface (or lower surface) of the substrate However, the present invention is not limited to not including other configurations between the substrate and any structure formed on (or under) the substrate.

The photocurable resin composition for a donor film according to an embodiment of the present invention is characterized in that the cured product formed from the composition has a glass transition temperature of from about 75 캜 to about 100 캜 and a storage modulus of the cured product of the composition is about 25 캜 To about 3.5 GPa to about 5.5 GPa, and from about 0.01 GPa to about 0.1 GPa at about 200 < 0 > C.

The photo-curable resin composition for a donor film is interposed between a photo-thermal conversion layer and a transfer layer of a donor film. The intermediate layer is formed to have the above-described glass transition temperature and storage modulus.

The donor film including the intermediate layer formed from the photo-curable resin composition for a donor film can be used to improve the transfer performance of the organic material in the transfer layer during patterning using laser thermal transfer.

Organic materials are deposited on the donor film to form a transfer layer, and then transferred to a substrate on which organic materials deposited via laser patterning are to be transferred.

If the intermediate layer formed from the photo-curable resin composition for a donor film has a glass transition temperature of less than about 75 캜, the stability and storage stability of the film may be poor at room temperature. If the intermediate layer has a glass transition temperature of more than about 100 캜, The intermediate layer may be maintained in a glassy state during the thermal transfer process, thereby deteriorating the transfer performance.

On the other hand, if the intermediate layer cured from the photo-curable resin composition for a donor film has a storage modulus of less than about 3.5 GPa at about 25 ° C, the transfer of organic materials to a region where patterning should not be performed during laser thermal transfer, And having a storage modulus exceeding about 5.5 GPa at about 25 캜 may cause a problem that thermal expansion due to the laser is difficult to occur in the intermediate layer during laser thermal transfer.

If the intermediate layer cured from the photocurable resin composition for a donor film has a storage modulus of less than about 0.01 GPa at about 200 ° C, there may arise a problem that the intermediate layer is deformed under high temperature conditions where thermal expansion occurs, If the storage modulus exceeds 0.1 GPa, thermal expansion due to the laser may be difficult to occur in the intermediate layer during laser thermal transfer.

The photocurable resin composition for a donor film may be specifically at least one selected from the group consisting of urethane acrylate-based, epoxyacrylate-based, ester acrylate-based, cardo-based acrylate-based, An acrylate-based monomer, an acrylate-based oligomer, an acrylate-based prepolymer, or a combination thereof, and an additive such as a crosslinkable acrylate-based monomer and a photoinitiator.

The acrylate oligomer of the photocurable compound may have a weight average molecular weight of about 500 to about 20,000.

For example, the photocurable resin composition for a donor film may contain about 20 to about 60 wt% of the acrylate oligomer as the photocurable compound.

The above-mentioned urethane acrylate is a general term for a compound having an urethane bond and an acrylate group, which can be photocured by adding an acrylate group to a urethane compound. For example, the urethane acrylate-based photo-curable oligomer may be formed by reacting an isocyanate-based monomer with a polyol to form a urethane bond, which is formed by reacting an isocyanate-based compound with a (meth) acrylic acid hydroxyalkyl ester- And an oligomer formed by polymerization with a weight average molecular weight of about 500 to about 20,000.

Specific examples of the isocyanate compound include aliphatic isocyanate compounds such as hexamethylene diisocyanate (HMDI), isophorone diisocyanate (IPDI), or aliphatic isocyanate compounds such as toluene diisocyanate (TDI), methylene diphenyl diisocyanate And aromatic isocyanate compounds such as methylene diphenyl diisocyanate (MDI). These may be used singly or in combination of two or more.

 Specific examples of the (meth) acrylate hydroxyalkyl ester compound include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4- hydroxybutyl (Meth) acrylate, 2-hydroxypropyleneglycol (meth) acrylate, 2-hydroxypropyleneglycol (meth) acrylate, Can be used.

The epoxy acrylate is a compound to which an acrylate group is added to an epoxy group-containing epoxy compound as a photo-curable compound, and specific examples thereof include bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether or phenol novolac epoxy resin (Meth) acrylic acid adducts, and the like.

The ester acrylate is a compound having an acrylate group added to an ester compound as a photo-curable compound, and specific examples thereof include polyhydric alcohols such as trimethylolpropane triacrylate, pentaerythritol tetraacrylate and dipentaerythritol hexaacrylate Of a polyfunctional polyester acrylate-based compound.

The cadmium acrylate (or fluorene acrylate) is a photo-curable compound. Specifically, the cadmium acrylate (or fluorene acrylate) is at least one selected from the group consisting of a dianhydride compound, a diol compound, a diacrylic acid, May be a compound having one photopolymerizable acrylate attached thereto.

[Chemical Formula 1]

Figure 112013087938610-pat00002

In this formula,

R 1 and R 2 are each independently -OH, -NH 2 , -O-CH 2 -CH 2 -OH or -COOH.

The photocurable composition for the donor film may comprise about 30 to about 70 wt% of the photocurable compound.

The crosslinkable acrylate monomers may be various photocurable monomers, for example, 2 to 4 acrylate functional group-containing monomers. Specific examples of the crosslinkable acrylate monomers include 1,2-ethylene glycol diacrylate, 1,12-dodecanediol acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol Acrylates such as di (meth) acrylate, neopentyl glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, neopentylglycol adipate di (meth) acrylate, hydroxyl puivalic acid (Meth) acrylate, dicyclopentanyl di (meth) acrylate, caprolactone modified dicyclopentenyl di (meth) acrylate, ethylene oxide modified di (meth) acrylate, di (Meth) acrylates such as (meth) acryloxyethyl isocyanurate, allyl cyclohexyl di (meth) acrylate, tricyclodecane dimethanol (meth) acrylate, dimethylol dicyclopentanedi (Meth) acrylate, neopentyl glycol modified trimethylpropane di (meth) acrylate, adamantane di (meth) acrylate, ethylene oxide modified hexahydrophthalic acid di (meth) acrylate, tricyclodecane dimethanol Bifunctional acrylates such as acrylate or 9,9-bis [4- (2-acryloyloxyethoxy) phenyl] fluorine; (Meth) acrylates such as trimethylolpropane tri (meth) acrylate, dipentaerythritol tri (meth) acrylate, propionic acid modified dipentaerythritol tri (meth) acrylate, pentaerythritol tri Trifunctional acrylates such as modified trimethylolpropane tri (meth) acrylate, trifunctional urethane (meth) acrylate or tris (meth) acryloxyethylisocyanurate; Tetrafunctional acrylates such as diglycerin tetra (meth) acrylate or pentaerythritol tetra (meth) acrylate; Pentafunctional acrylates such as propionic acid-modified dipentaerythritol penta (meth) acrylate; And dipentaerythritol hexa (meth) acrylate, caprolactone-modified dipentaerythritol hexa (meth) acrylate or urethane (meth) acrylate (e.g., an isocyanate monomer and trimethylolpropane tri And hexafunctional acrylates such as a reaction product, but are not limited thereto.

The photocurable resin composition for a donor film may contain about 20 to about 60 wt% of the crosslinkable acrylate monomer.

Examples of the photoinitiator include benzoin methyl ether, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide,?,? -Methoxy-? Benzoyl-2- (dimethylamino) -1- [4- (4-morpholyl) phenyl] -1-butanone, 2,2-dimethoxy-2-phenylacetophenone, oxime ester And the like. The photocurable resin composition for a donor film may contain about 0.1 to about 10% by weight of the photoinitiator.

The photocurable resin composition for the donor film is prepared so that the glass transition temperature (Tg) of the photocurable compound is in the range of -50 ° C to 60 ° C in order to realize the above-mentioned glass transition temperature range, And the glass transition temperature of the intermediate layer when cured is from 75 ° C to 100 ° C.

That is, when the cured product of the photocurable resin composition for a donor film is exemplified by one method in order to realize the glass transition temperature within the above-mentioned range, the glass transition temperature of the oligomer raw material of the photocurable compound is about- Lt; RTI ID = 0.0 > 50 C < / RTI > to about 60 C and has a polymer network structure cured through a photoinitiator. In order to limit the glass transition temperature of the oligomer raw material, for example, in the case of the urethane acrylate oligomer, the isocyanate and the (meth) acrylic acid hydroxyalkyl ester include an aromatic group to have a hard repeating unit, The glass transition temperature can be increased.

The photo-curable resin composition for a donor film may contain various kinds of monomers constituting a repeating unit of the photo-curing compound to realize the storage modulus within the above-mentioned numerical range at about 25 ° C and about 200 ° C, Molecular weight, content, and the like. For example, if the repeating units are composed of aromatics of a hard type, the storage modulus is increased. On the other hand, the storage modulus can be controlled through the molecular weight. If the molecular weight is large, the interval between the curing sites becomes long, the crosslinking density becomes low, and the storage modulus decreases. The content of the aliphatic group-containing monomer and the aromatic group-containing monomer is controlled so that the content of the component having a large molecular weight and the content of the small component are controlled so that the cured product of the photocurable resin composition for the donor film has a storage modulus Can be implemented.

In one embodiment, the photocurable resin composition for a donor film may comprise such that the ratio of the oligomer having a weight average molecular weight of about 500 to about 20000 and the monomer is about 1: 4 to about 4: 1, Containing monomer may be an aliphatic group-containing monomer, and the oligomer may be an aromatic group-containing oligomer.

In other embodiments, the aliphatic monomer and the aromatic monomer may not be included at the same time.

Given one illustrative method for setting the modulus to about 0.1 GPa or less at a high temperature of about 200 DEG C as described above, the glass transition temperature of the oligomeric raw material of the photocurable compound can be increased from about -50 DEG C to about 60 DEG C , The cured product is allowed to have a glass transition temperature of from about 75 캜 to about 100 캜, and at about 200 캜 higher than the glass transition temperature, the photocurable resin composition for a donor film has a viscous state And the storage modulus is rapidly lowered, so that a value of about 0.01 to about 0.1 GPa can be realized.

When the high temperature modulus in the above range is realized at such a high temperature, when the thermal expansion occurs after the laser irradiation, the intermediate layer sufficiently swells and exhibits excellent transfer performance.

In one embodiment, the photocurable resin composition for a donor film may comprise such that the ratio of the oligomer having a weight average molecular weight of about 500 to about 20000 and the monomer is about 1: 4 to about 4: 1, Containing monomer may be an aliphatic group-containing monomer, and the oligomer may be an aromatic group-containing oligomer.

In other embodiments, the aliphatic monomer and the aromatic monomer may not be included at the same time.

The photo-curing resin composition for a donor film may be prepared from the group consisting of a crosslinking agent, a UV stabilizer, an antioxidant, a colorant, a reinforcing agent, a filler, a defoamer, a surfactant, a plasticizer and a combination thereof, And may further comprise one or more selected additives.

In another embodiment of the present invention, there is provided a donor film comprising a substrate layer, a photo-thermal conversion layer, an intermediate layer and a transfer layer. The intermediate layer is prepared by curing the photocurable resin composition for the donor film described above.

The donor film can improve the transfer performance of organic materials in the transfer layer during patterning using laser thermal transfer.

Patterning is one of the factors that determine the transfer quality. It modulates the storage modulus of the intermediate layer formed from the photocurable resin composition for a donor film so that the thermal expansion can be well performed, and the glass transition temperature is controlled to cause deformation and swelling .

The donor film may be useful for manufacturing a display device such as an organic light emitting display.

1 is a cross-sectional view of a donor film 10; 1, the donor film 10 includes a base layer 11, a photo-thermal conversion layer 12 formed on the base layer 11, and an intermediate layer 13 formed on the photo-thermal conversion layer 12 do.

As shown in FIG. 1, a transfer layer 14 formed on the intermediate layer 13 may be formed.

The base film 11 is made of glass; Or a transparent film containing at least one selected from the group consisting of polyester, polycarbonate, polyolefin, polyvinyl, and combinations thereof.

Specifically, the base film 11 is a polyethylene terephthalate (PET) film or a polyethylene naphthalate (PEN) film, and the base film of the material is the most preferable in terms of processability, thermal stability and transparency Do.

The surface of the base film 11 may be modified by a surface treatment such as a corona or plasma known to those skilled in the art to control the adhesion, surface tension, and the like when the photothermal conversion layer 12 is laminated in a subsequent step It is also possible.

The donor film 10 may further include a primer layer (not shown) formed on the base film 11. For example, a primer layer may be formed between the base film 11 and the photo-thermal conversion layer 12.

The primer layer is for controlling the temperature transfer between the base film and the adjacent layer, improving the adhesion between the base film 11 and the adjacent layer, and controlling the image forming radiation transmission to the photo-thermal conversion layer 12 , When the primer layer is not formed, the base film 11 and the photo-thermal conversion layer 12 may be separated from each other in a transfer process using a laser.

As a material suitable for such a primer layer, at least one selected from the group consisting of an acrylic resin, a polyurethane resin, a polyester resin, and a combination thereof may be used.

If the heat-resistant adhesion between the primer layer and the base film 11 or between the primer layer and the photo-thermal conversion layer 12 is poor, the base film 11 and the photo-thermal conversion layer 12 can be separated in a transfer process using a laser.

The light-to-heat conversion layer 12 is a layer that absorbs light in the infrared-visible light region and converts a part of the light into heat, and is composed of a resin composition including a thermosetting resin and a photo-thermal conversion material.

The intermediate layer 13 may be formed by coating the photocurable resin composition for a donor film and thermally curing or photo-curing the intermediate layer 13. The intermediate layer 13 may be formed by transferring the transfer layer by heat generated in the photo- The heat generated in the photo-thermal conversion layer 12 is prevented from being transferred to the transfer layer and burned by the heat, in order to prevent the photo-thermal conversion material existing in the photo-thermal conversion layer 12 from being transferred together, . In addition, the intermediate layer 13 has excellent 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, organic materials can be easily transferred even in a small thermal expansion.

Specifically, 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 a thickness of, for example, about 1 탆 to about 5 탆. When the thickness of the intermediate layer 13 is less than 1 탆, the organic material in the transfer layer may be damaged due to heat generated in the photo-thermal conversion layer. If the thickness is more than 5 탆, the intermediate layer 13 may not be sufficiently swollen.

The transfer layer 14 typically comprises at least one layer for transfer to a receptor. For example, organic, inorganic, organometallic and other materials including electroluminescent materials or electrically active materials. Specific examples of the polymer include poly (phenylene vinylene), poly-para-phenylene, polyfluorene, polydialkyl fluorene, polythiophene, poly (9- vinylcarbazole) Alcohol) copolymer, triarylamine, polynorbornene, polyaniline, polyarylpolyamine, triphenylamine-polyether ketone, and the like.

The transfer layer 14 may further include at least one material selected from known light emitting materials, hole transporting organic materials, and electron transferring organic materials so as to conform to the characteristics of the organic light emitting device to be manufactured, A non-luminescent low molecular weight material, a non-luminescent low molecular weight material, a non-luminescent low molecular weight material, a non-luminescent charge transporting polymer material and a curable organic semi-insulating material.

Hereinafter, examples and comparative examples of the present invention will be described. The following embodiments are only examples of the present invention, and the present invention is not limited to the following embodiments.

( Example )

Example  One

A photocurable resin composition was prepared by mixing 60 wt% of a photo-curing compound (weight average molecular weight 7000) of cathedral acrylate containing an aromatic group, 35 wt% of a bifunctional acrylate monomer, and 5 wt% of a photoinitiator.

A photothermal conversion layer containing a photothermal conversion material of carbon black was formed on the base layer of the polyester film to a thickness of 3 탆 and the prepared cationic acrylate resin composition was coated to a thickness of 3 탆, An intermediate layer was prepared by irradiating ultraviolet rays using a lamp to cure the donor film.

The cadmium acrylate is a hard type oligomer (molecular weight: 7000) having a rigid structure in which an aromatic five-membered ring and a six-membered ring are crossed. The aliphatic group is reacted with the ring to increase the molecular weight, thereby lowering the glass transition temperature. The glass transition temperature can be set to about 75 to 100 DEG C within a desired range. The intermediate layer prepared from the composition formulated with the above ratio is prepared to have a storage modulus at a desired level of glass transition temperature, room temperature and high temperature. The storage modulus of the prepared intermediate layer was measured at a glass transition temperature and a room temperature and a high temperature.

Comparative Example  One

The photo-curing resin composition was prepared in the same manner as in Example 1 except that the photo-curing resin composition was prepared so as to contain 80 wt% of urethane acrylate having an aromatic structure (weight average molecular weight 5000) and 15 wt% of bifunctional acrylate monomer and 5 wt% To prepare a donor film.

evaluation

The glass transition temperature, storage modulus and glass transition temperature of the intermediate layer of the donor film of Examples 1-2 and 1-2 were evaluated as described below, and the results are shown in Table 1. The transfer characteristics of the donor films of Examples 1-2 and 1-2 were evaluated by the following methods, and the evaluation results are shown in Table 1.

≪ Evaluation of glass transition temperature &

Differential scanning calorimetry (Perkin Elmer DSC8000): Measure the temperature from 20 캜 to 200 캜 at a rate of 10 캜 / min.

≪ Evaluation of storage modulus &

Nanoindentation: Hysitron TI750: The storage modulus value was measured at room temperature (25 ° C) and high temperature (200 ° C) in nanoDMA mode.

<Evaluation of Warrior Quality>

The transfer quality was evaluated by the following method.

1) Preparation of Test Pattern Substrate: Prepare a test pattern substrate having a bank structure thickness of 0.5 μm or less and a taper angle of 15 ° or less. A test pattern substrate having a pixel size of 11 x 78 占 퐉 was coated with an organic substance DNTPD (N, N'-diphenyl-N, N'-bis- [4- (phenylmutolylamino) , 4'-diamine) was deposited to a thickness of 100 Å.

2) TCTA ((N-carbazolyl) -triphenylamine) was deposited on the surface of the film prepared in Example 1 and Comparative Example 1 to a thickness of 500 Å.

3) The DNTPD surface of the test pattern substrate and the TCTA surface of the film of Example 1 and Comparative Example 1 are fixed by adsorption on a laser equipment stage.

4) At the distal end of the laser device, a mask is mounted so that it can be imaged in alignment with the pixel area of the substrate.

5) Scanning is performed by irradiating the laser beam onto the substrate (PET surface) of the prepared sample at an energy amount of 1.5 J / cm 2.

6) Scanning After the donor film was removed in Example 1 and Comparative Example 1, traces of organic matter transfer on the substrate surface were evaluated using an optical microscope.

division Example
One Comparative Example
One Glass Transition Temperature [캜] 120 50 Low Temperature Modulus [25 ℃, GPa] 4.3 1.1 High temperature modulus [200 ℃, GPa] 0.061 0.13 Corporate quality evaluation Great Bad

10: Donor film
11: substrate layer
12: Photothermal conversion layer
13: Middle layer
14: transfer layer

Claims (18)

The glass transition temperature of the cured product of the composition is 75 占 폚 to 100 占 폚, the storage modulus is 3.5 to 5.5 GPa at 25 占 폚, 0.01 to 0.1 GPa at 200 占 폚,
The composition may further comprise a photo-curable compound selected from an acrylate-based monomer, an acrylate-based oligomer and an acrylate-based prepolymer containing cardo-based acrylate, or a photocurable mixture containing at least two photo- ; Crosslinkable acrylate-based monomers; And a photoinitiator,
The cadmium acrylate is a compound which is obtained by reacting at least one selected from the group consisting of a dianhydride compound, a diol compound, a diacrylic acid, and a combination thereof, and a photocurable acrylate compound
Photocurable resin composition for donor film:
[Chemical Formula 1]
Figure 112017109293804-pat00005

In this formula,
R 1 and R 2 are each independently -OH, -NH 2 , -O-CH 2 -CH 2 -OH or -COOH.
The method according to claim 1,
Wherein the photocurable mixture further comprises an acrylate-based monomer, an acrylate-based oligomer, an acrylate-based prepolymer, or a combination thereof, comprising at least one of urethane acrylate, epoxy acrylate and ester acrylate
A photocurable resin composition for a donor film.
3. The method of claim 2,
The urethane acrylate is formed by polymerization of an isocyanate-based monomer and a polyol. The isocyanate-based monomer includes at least one or more selected from aliphatic isocyanate-based monomers, aromatic isocyanate-based monomers, and combinations thereof. ) Acrylic acid hydroxyalkyl ester compound
A photocurable resin composition for a donor film.
3. The method of claim 2,
Wherein the epoxy acrylate comprises at least one or more selected from the group consisting of bisphenol A diglycidyl ether, hydrogenated bisphenol A diglycidyl ether, (meth) acrylic acid adduct of phenol novolak epoxy resin, and combinations thereof
A photocurable resin composition for a donor film.
3. The method of claim 2,
The ester acrylate may be a polyfunctional polyester acrylate compound of a polyhydric alcohol
A photocurable resin composition for a donor film.
delete The method according to claim 1,
Wherein the photo-curable compound or the photo-curable mixture is contained in an amount of 30 to 70 wt%
A photocurable resin composition for a donor film.
The method according to claim 1,
And 20 to 60% by weight of the crosslinkable acrylate monomer
A photocurable resin composition for a donor film.
The method according to claim 1,
The crosslinkable acrylate-based monomer is a monomer having two to four acrylate functional groups
A photocurable resin composition for a donor film.
The method according to claim 1,
The glass transition temperature (Tg) of the photo-curable compound or the photo-curable mixture is preferably from -50 ° C to 60 ° C
A photocurable resin composition for a donor film.
11. The method of claim 10,
After forming a cured polymer network structure through a photoinitiator, the glass transition temperature of the cured product was adjusted to 75 to 100 DEG C
A photocurable resin composition for a donor film.
The method according to claim 1,
Wherein the photocurable mixture further comprises a further photocurable mixture comprising a weight ratio of oligomers and monomers having a weight average molecular weight of from 500 to 20 000 in a ratio of from 1: 4 to 4: 1
A photocurable resin composition for a donor film.
13. The method of claim 12,
The monomer is an aliphatic group-containing monomer, and the oligomer is an aromatic group-containing oligomer
A photocurable resin composition for a donor film.
A base layer, a photo-thermal conversion layer and an intermediate layer,
Wherein the intermediate layer is a layer prepared by curing a photocurable resin composition for a donor film according to any one of claims 1 to 5 and 7 to 13
Donor film.
15. The method of claim 14,
A transfer layer is laminated on the intermediate layer
Donor film.
15. The method of claim 14,
The substrate layer is glass; Or a transparent film comprising at least one selected from the group consisting of polyester, polycarbonate, polyolefin, polyvinyl, and combinations thereof
Donor film.
15. The method of claim 14,
Further comprising a primer layer formed on the base layer
Donor film.
15. The method of claim 14,
Wherein the intermediate layer has a surface energy of 11 mN / m to 21 mN / m
Donor film.
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