WO2022059740A1 - 表示素子用封止剤、その硬化物および表示装置 - Google Patents

表示素子用封止剤、その硬化物および表示装置 Download PDF

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Publication number
WO2022059740A1
WO2022059740A1 PCT/JP2021/034151 JP2021034151W WO2022059740A1 WO 2022059740 A1 WO2022059740 A1 WO 2022059740A1 JP 2021034151 W JP2021034151 W JP 2021034151W WO 2022059740 A1 WO2022059740 A1 WO 2022059740A1
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Prior art keywords
mass
meth
acrylate
display element
parts
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PCT/JP2021/034151
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English (en)
French (fr)
Japanese (ja)
Inventor
裕介 富田
航太郎 舘野
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Mitsui Chemicals Inc
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Mitsui Chemicals Inc
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Priority to KR1020237000656A priority Critical patent/KR102734885B1/ko
Priority to CN202180049407.1A priority patent/CN115804245B/zh
Priority to JP2022550606A priority patent/JP7761574B2/ja
Publication of WO2022059740A1 publication Critical patent/WO2022059740A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/02—Details
    • H05B33/04—Sealing arrangements, e.g. against humidity
    • 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
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/844—Encapsulations
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/87—Passivation; Containers; Encapsulations
    • H10K59/871—Self-supporting sealing arrangements
    • H10K59/8722—Peripheral sealing arrangements, e.g. adhesives, sealants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/80—Constructional details
    • H10K59/87—Passivation; Containers; Encapsulations
    • H10K59/873—Encapsulations

Definitions

  • the present invention relates to a sealant for a display element, a cured product thereof, and a display device.
  • Organic EL elements are being used in displays, lighting devices, and the like because they consume less power. Since organic EL elements are easily deteriorated by moisture and oxygen in the atmosphere, they are used by being sealed with various sealing members, and the durability of moisture and oxygen of various sealing members will be improved for practical use. It is desired.
  • a method for sealing the organic EL for example, a method is used in which a resin layer is formed on an organic EL element coated with a first layer of an inorganic material film, and then a second layer of the inorganic material film is coated. ing.
  • the method of coating with the inorganic material film include a method of forming an inorganic material film made of silicon nitride or silicon oxide by a sputtering method, an electron cyclotron resonance (ECR) plasma CVD method, or the like.
  • ECR electron cyclotron resonance
  • the encapsulant for an organic electroluminescence display element includes an acyclic alkanediol di (meth) acrylate having 6 or more carbon atoms, and a cyclic monofunctional (meth) acrylate and a cyclic bifunctional (meth) acrylate. It is described that it is used in combination with a cyclic monomer containing. According to the same document, it is said that a sealing agent having excellent ejection properties when using an inkjet and having excellent reliability of the obtained organic EL element can be obtained.
  • the present invention provides a sealant for a display element, which has excellent plasma resistance and has both a viscosity and a low dielectric constant that can be stably applied by an inkjet method.
  • a sealant for a display element containing a polymerizable compound and a curing agent contains the following components (A) and (B): (A) (meth) acrylate having a bifunctional or higher alicyclic structure (B) containing (meth) acrylate having a bifunctional chain structure.
  • the content of the component (A) is 60 parts by mass or less with respect to a total of 100 parts by mass of the components (A) and (B).
  • Component (C) in the sealant for a display element A sealant for a display element, wherein the content of the monofunctional (meth) acrylate is 1 part by mass or less with respect to 100 parts by mass of the polymerizable compound.
  • the component (B) is 1,12-dodecanediol di (meth) acrylate, 1,9-nonanediol di (meth) acrylate, triethylene glycol di (meth) acrylate and tripropylene glycol di (meth).
  • a sealing agent for a display element which is excellent in plasma resistance and has both a viscosity and a low dielectric constant that can be stably applied by an inkjet method.
  • the sealing agent for a display element (hereinafter, also simply referred to as “sealing agent” as appropriate) is a composition used for sealing an element, and contains a polymerizable compound and a curing agent.
  • the polymerizable compound has the following components (A) and (B): (A) (Meta) acrylate having a bifunctional or higher alicyclic structure (B) Containing (meth) acrylate having a bifunctional chain structure, with respect to a total of 100 parts by mass of the components (A) and (B).
  • the content of the component (A) is 60 parts by mass or less.
  • the content of the component (C): monofunctional (meth) acrylate in the sealant for a display device is 1 part by mass or less with respect to 100 parts by mass of the polymerizable compound.
  • (meth) acrylate means at least one of acrylate and methacrylate.
  • (meth) acrylic means at least one of acrylic and methacrylic.
  • the polymerizable compound may be any compound having a polymerizable functional group, and is preferably a compound having a radically polymerizable functional group.
  • the polymerizable compound contains the above-mentioned components (A) and (B).
  • the component (A) is a (meth) acrylate having a bifunctional or higher alicyclic structure.
  • the component (A) is a (meth) acrylate having an alicyclic structure in the molecular structure and two or more (meth) acrylic groups, and is preferably (meth) from the viewpoint of improving strength. It is a (meth) acrylate having two acrylic groups.
  • the component (A) has an alicyclic hydrocarbon structure in the molecular structure, and the number of carbon atoms in the alicyclic hydrocarbon structure is preferably 4 or more from the viewpoint of improving heat resistance. It is more preferably 5 or more, still more preferably 6 or more, preferably 14 or less, still more preferably 12 or less, still more preferably 10 or less.
  • the alicyclic hydrocarbon structure may be a saturated hydrocarbon structure or an unsaturated hydrocarbon structure. From the viewpoint of improving heat resistance, the alicyclic hydrocarbon structure is preferably a saturated hydrocarbon structure.
  • the alicyclic hydrocarbon structure may be a monocyclic hydrocarbon structure, a fused ring hydrocarbon structure, or a polycyclic hydrocarbon structure having a bridge ring hydrocarbon group structure.
  • the component (A) may contain a group containing these alicyclic hydrocarbon structures in the molecular structure, and preferably contains a divalent group containing the alicyclic hydrocarbon structure.
  • Specific examples of the monocyclic hydrocarbon group include a group having a cycloalkane structure such as a cyclohexylene group and a cyclohexyl group; and a group having a cycloalkene skeleton such as a cyclodecatoriendiyl group and a cyclodecatorien group.
  • polycyclic hydrocarbon group examples include a group having a dicyclopentadiene skeleton such as a tricyclodecandyl group, a dicyclopentanyl group, and a dicyclopentenyl group; a norbornanediyl group, an isobornandyl group, and a norbornyl group.
  • Groups having a norbornane skeleton such as an isobornyl group; groups having an adamantane skeleton such as an adamantane diyl group and an adamantane group can be mentioned.
  • the cyclic hydrocarbon group in the component (A) is preferably a group having a dicyclopentadiene skeleton from the viewpoint of improving plasma resistance and low moisture permeability. Further, the component (A) contains tricyclodecanedimethanol di (meth) acrylate from the viewpoint of improving plasma resistance and low moisture permeability, and is more preferably tricyclodecanedimethanol di (meth) acrylate. ..
  • the content of the component (A) in the encapsulant is preferably 5 parts by mass or more, more preferably 10 parts by mass or more, still more preferably 10 parts by mass or more with respect to 100 parts by mass of the polymerizable compound from the viewpoint of improving heat resistance. It is 15 parts by mass or more, more preferably 20 parts by mass or more, and even more preferably 25 parts by mass or more. Further, from the viewpoint of making the inkjet coatability more preferable, the content of the component (A) in the encapsulant is preferably 60 parts by mass or less, more preferably 58 with respect to 100 parts by mass of the polymerizable compound. It is not more than parts by mass, more preferably 56 parts by mass or less.
  • the component (B) is a (meth) acrylate having a bifunctional chain structure.
  • the component (B) is a (meth) acrylate having a chain structure in the molecular structure and two or more (meth) acrylic groups, and is preferably (meth) from the viewpoint of improving strength. It is a (meth) acrylate having two acrylic groups.
  • Specific examples of the component (B) include di (meth) acrylate of alkanediol and di (meth) acrylate of (poly) alkylene glycol.
  • the chain structure may be a linear structure or a structure having branches.
  • the chain structure preferably contains a divalent hydrocarbon group having a straight chain or a branched chain from the viewpoint of making the inkjet coatability more preferable.
  • the number of carbon atoms of the divalent hydrocarbon group is, for example, 1 or more, preferably 2 or more, and more preferably 4 or more, from the viewpoint of accessibility of the monomer. Further, from the viewpoint of improving heat resistance, the number of carbon atoms of the divalent hydrocarbon group is preferably 20 or less, more preferably 14 or less.
  • 1,6-hexanediol diacrylate for example, A-HD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
  • 1,9-nonanediol diacrylate for example, A-NOD-
  • Polypropylene glycol diacrylate eg A-400, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
  • Polypropylene glycol diacrylate eg APG-400, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
  • Tripropylene glycol diacrylate eg SR306H, Alchema
  • 1,3-Butanediol dimethacrylate eg BG, manufactured by Shin-Nakamura Chemical Industry
  • 1,4-butanediol dimethacrylate eg BD, manufactured by Shin-Nakamura Chemical Industry
  • 1,6-hexanediol Dimethacrylate eg HD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
  • 1,9-Nonandiol dimethacrylate eg NOD-N, manufactured by Shin-Nakamura Chemical Industry Co., Ltd .
  • Light acrylate 1,9-ND-M manufactured by Kyoeisha Chemical
  • the component (B) is 1,12-dodecanediol di (meth) acrylate and 1,9-nonanediol.
  • One or more (meth) acrylates selected from the group consisting of di (meth) acrylates, triethylene glycol di (meth) acrylates and tripropylene glycol di (meth) acrylates.
  • the content of the component (B) in the encapsulant is preferably 5 parts by mass or more, and more preferably 10 parts by mass with respect to 100 parts by mass of the polymerizable compound from the viewpoint of making the inkjet coatability more preferable.
  • the above is more preferably 15 parts by mass or more, further preferably 20 parts by mass or more, still more preferably 25 parts by mass or more, and further preferably 40 parts by mass or more.
  • the content of the component (B) in the encapsulant is, for example, 75 parts by mass or less, preferably 60 parts by mass or less, based on 100 parts by mass of the polymerizable compound. It is more preferably 58 parts by mass or less, still more preferably 56 parts by mass or less.
  • the content of the component (A) with respect to a total of 100 parts by mass of the components (A) and (B) is 60 parts by mass or less, preferably 58 parts by mass or less, from the viewpoint of making the inkjet coatability more preferable. , More preferably 55 parts by mass or less, still more preferably 50 parts by mass or less.
  • the lower limit of the content of the component (A) with respect to a total of 100 parts by mass of the components (A) and (B) is more than 0 parts by mass, preferably 10 parts by mass or more from the viewpoint of improving plasma resistance. It is more preferably 15 parts by mass or more, further preferably 20 parts by mass or more, still more preferably 25 parts by mass or more, still more preferably 30 parts by mass or more, still more preferably 40 parts by mass or more.
  • the component (C) is a monofunctional (meth) acrylate.
  • Specific examples of the component (C) include mono (meth) acrylate having a hydrocarbon group having a linear or branched chain in the molecular structure, and mono (meth) acrylate having an aromatic hydrocarbon group in the molecular structure. ..
  • An example of the former is lauryl methacrylate, and an example of the latter is 3-phenoxybenzyl acrylate.
  • the sealant for a display element preferably does not contain the component (C). That is, the content of the component (C) in the sealant for a display device is preferably 0 parts by mass with respect to 100 parts by mass of the polymerizable compound.
  • the content of the component (C) in the sealant for display elements exceeds 0 parts by mass with respect to 100 parts by mass of the polymerizable compound. It is 1 part by mass or less, preferably 0.5 part by mass or less, more preferably 0.1 part by mass or less, and further preferably 0.01 part by mass or less.
  • the content of the polymerizable compound in the sealant for a display element is preferably 70% by mass or more, more preferably 80% by mass, based on the total composition of the sealant from the viewpoint of improving the strength of the cured product. As mentioned above, it is more preferably 85% by mass or more, still more preferably 90% by mass or more, and even more preferably 93% by mass or more. Further, from the viewpoint of improving the weather resistance of the encapsulant, the content of the polymerizable compound in the encapsulant is preferably 99.9% by mass or less, more preferably 99.9% by mass or less, based on the total composition of the encapsulant. It is 99.5% by mass or less, more preferably 99% by mass or less, and even more preferably 98% by mass or less.
  • the curing agent include a polymerization initiator.
  • the polymerization initiator is preferably a photopolymerization initiator which is a compound that generates radicals or acids by irradiation with ultraviolet rays or visible light from the viewpoint of stably forming a cured product at a low temperature.
  • the photopolymerization initiator include an acylphosphine oxide-based initiator, an oxyphenylacetic acid ester-based initiator, a benzoylformic acid-based initiator, a hydroxyphenylketone-based initiator, and the like.
  • photopolymerization initiator examples include benzophenone, Michler's ketone, 4,4'-bis (diethylamino) benzophenone, xanthone, thioxanthone, isopropylxanthone, 2,4-diethylthioxanthone, 2-ethylanthraquinone, acetophenone, and 2-hydroxy-.
  • the photopolymerization initiator is preferably 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenyl-1-propanol, 1- [4- ( 2-Hydroxyethoxy) -phenyl] -2-hydroxy-2-methyl-1-propanone, 2-hydroxy-1- ⁇ 4- [4- (2-hydroxy-2-methyl-propionyl) -benzyl] phenyl ⁇ - 2-Methyl-1-propanol, 2,2-dimethoxy-2-phenylacetophenone, oxy-phenyl-acetic acid 2- [2-oxo-2-phenyl-acetoxy-ethoxy] -ethyl ester, oxy-phenyl-acetic acid 2- [2-Hydroxy-ethoxy] -ethyl ester, methyl benzoylate, bis (2,4,6-trimethylbenzoyl) phenylphosphine oxide, 2,4,6-
  • Irgacure184 As commercial products of the photopolymerization initiator, Irgacure184, Irgacure651, Irgacure127, Irgacure1173, Irgacure500, Irgacure2959, Irgacure754, IrgacureMBF, IrgacureMBF, IrgacureMBF, IrgacureTPO (above, BASF), etc.
  • the content of the polymerization initiator in the encapsulant is preferably 0.1% by mass or more, more preferably 0.5% by mass or more, based on the total composition of the encapsulant, from the viewpoint of improving the curability. , More preferably 1% by mass or more, still more preferably 2% by mass or more. Further, from the viewpoint of suppressing the coloring of the encapsulant, the content of the polymerization initiator in the encapsulant is preferably 10% by mass or less, more preferably 8% by mass, based on the total composition of the encapsulant. Below, it is more preferably 7% by mass or less, still more preferably 6% by mass or less, and even more preferably 5% by mass or less.
  • the encapsulant may be composed of a polymerizable compound and a curing agent, or may contain components other than these. Specific examples of other components include tackifiers, fillers, curing accelerators, plasticizers, surfactants, heat stabilizers, flame retardants, antistatic agents, defoamers, leveling agents and UV absorbers. 1 or 2 or more additives selected from.
  • the glass transition temperature (Tg) of the cured product of the encapsulant is 50 ° C. or higher, preferably 60 ° C. or higher, and more preferably 70 ° C. or higher from the viewpoint of improving the heat resistance of the encapsulant. Further, from the viewpoint of improving the flexibility, the Tg of the cured product of the encapsulant is less than 200 ° C., preferably 190 ° C. or lower, more preferably 180 ° C. or lower.
  • the Tg of the encapsulant is specifically measured by the following method.
  • a 100 ⁇ m-thick Teflon (registered trademark) sheet is used as a mold, an uncured encapsulant is sandwiched between PET films, and an illuminance of 1000 mW / cm 2 is used with a UV-LED having a wavelength of 395 nm. It is obtained by curing under the condition of an integrated light amount of 1500 mJ / cm 2 .
  • the obtained cured product is cut into a size of 10 mm in width ⁇ 40 mm in length with a cutter to obtain a measurement sample.
  • the Tg of the cured product is heated from room temperature to 250 ° C.
  • the properties of the encapsulant are not limited, and the encapsulant is suitable from the viewpoint of improving the flexibility and plasma resistance of the encapsulating material and being suitable for forming a cured material by a coating method such as an inkjet method. It is preferably liquid.
  • the sealing agent is preferably a sealing agent used for coating, and more preferably a sealing used for coating by an inkjet method. It is a stop agent.
  • the viscosity of the encapsulant measured at 25 ° C. and 20 rpm using an E-type viscometer is preferably 5 mPa ⁇ s or more, more preferably 8 mPa ⁇ s or more, still more preferably, from the viewpoint of improving the inkjet ejection property. Is 10 mPa ⁇ s or more. Further, from the viewpoint of improving the inkjet ejection property, the viscosity of the encapsulant is preferably 30 mPa ⁇ s or less, more preferably less than 30.0 mPa ⁇ s, still more preferably 28.5 mPa ⁇ s or less, still more preferably. Is 27 mPa ⁇ s or less.
  • the dielectric constant of the cured product of the sealant is preferably less than 3.5, more preferably 3.4 or less, still more preferably 3.3 or less, and further, from the viewpoint of improving the sealing characteristics of the sealant. It is more preferably 3.2 or less, and even more preferably 3.1 or less. Further, the dielectric constant of the cured product of the encapsulant can be, for example, 1.0 or more.
  • the dielectric constant of the cured product of the encapsulant is the cured product obtained by curing the curable composition under the conditions of an illuminance of 1000 mW / cm 2 and an integrated light intensity of 1500 mJ / cm 2 with a UV-LED having a wavelength of 395 nm. Permittivity measured at a frequency of 100 kHz.
  • the method for producing the encapsulant is not limited, and includes, for example, mixing a polymerizable compound, a curing agent, and other components as appropriate, for example, various additives to be added as needed.
  • various known kneaders such as a planetary stirrer, a homodisper, a universal mixer, a Banbury mixer, a kneader, two rolls, three rolls, and an extruder are used alone or in combination. Examples thereof include a method of uniformly kneading under conditions such as normal pressure, reduced pressure, pressure, and an inert gas stream under normal temperature or heating.
  • a sealing material can be formed by using the obtained sealing agent.
  • a sealant may be applied onto the substrate and dried.
  • a known method such as an inkjet method, screen printing, or dispenser coating can be used. Further, the drying can be performed, for example, by heating to a temperature at which the polymerizable compound does not polymerize.
  • the shape of the obtained encapsulating material is not limited and may be, for example, a film or a layer.
  • the encapsulating material is, for example, a cured product obtained by curing the encapsulant in the present embodiment, and more specifically, a photocured product of the encapsulant.
  • methods for photocuring the encapsulant include low-pressure mercury lamps, medium-pressure mercury lamps, high-pressure mercury lamps, ultra-high pressure mercury lamps, excima lasers, chemical lamps, black light lamps, microwave-excited mercury lamps, metal halide lamps, sodium lamps, and halogen lamps.
  • a method of curing by irradiating light using a light source such as a xenon lamp, an LED lamp, a fluorescent lamp, sunlight, or an electron beam irradiator.
  • the polymerizable compound contains the components (A) and (B) in a specific ratio and the content when the component (C) is contained is in a specific range, such a polymerizable compound and curing
  • a sealing agent containing an agent it is possible to obtain a sealing material having excellent plasma resistance and having both a viscosity and a low dielectric constant that can be stably applied by an inkjet method.
  • the resin layer obtained from such a polymerizable compound as a sealing material for example, it is possible to obtain a display device having excellent reliability.
  • the encapsulant obtained in the present embodiment is suitably used for encapsulating a display element, preferably an organic EL display element, for example.
  • a sealing agent having excellent plasma resistance being able to be stably applied by an inkjet method when forming a resin layer, and having an effectively reduced dielectric constant. Therefore, for example, damage to the display element in the manufacturing process of the display device can be effectively suppressed, and the manufacturing stability of the display device can be improved.
  • a configuration example of the display device will be given by taking an organic EL display device as an example.
  • the organic EL display device has a layer made of a cured product of a sealing agent.
  • the organic EL display device may have a top emission structure or a bottom emission structure.
  • the organic EL element is arranged on a substrate and is pre-coated with an inorganic material film so as to cover the region containing the organic EL element before being protected by the resin layer obtained by curing the encapsulant in the present embodiment. It is preferable that it is.
  • FIG. 1 is a cross-sectional view showing a configuration example of an organic EL display device according to the present embodiment.
  • the display device 100 shown in FIG. 1 is an organic EL display device, and covers a substrate (base material layer 50), a display element (light emitting element 10) arranged on the base material layer 50, and a light emitting element 10.
  • the sealing layer 22 (which may be the overcoat layer 22 or the barrier layer 22) is included. Then, for example, the sealing layer 22 is composed of a cured product of the sealing agent in the present embodiment.
  • the light emitting element 10 is an organic EL display element. Further, in FIG.
  • the display device 100 has a barrier layer 21 (may be a touch panel layer 21 or a surface protection layer 21) and a sealing layer 22 (which may be a touch panel layer 21 or a surface protection layer 21) as layers located on the observation side of the light emitting element 10. It has an overcoat layer 22 or a barrier layer 22), a flattening layer 23 (may be a sealing layer 23), and a barrier layer 24.
  • the flattening layer 23 is provided on the base material layer 50 so as to cover the light emitting element 10, and the barrier layer 24 is provided on the surface of the flattening layer 23.
  • the sealing layer 22 is provided on the base material layer 50 so as to cover the flattening layer 23 and the barrier layer 24. Further, a barrier layer 21 is provided on the sealing layer 22.
  • the material of the base material layer 50 is not limited, and various materials such as a glass substrate, a silicon substrate, and a plastic substrate can be used.
  • a TFT substrate having a plurality of TFTs (thin film transistors) and a flattening layer on the substrate can also be used.
  • Examples of the inorganic material constituting the barrier layer 24, that is, the above-mentioned inorganic material film, include silicon nitride (SiN x ), silicon oxide (SiO x ), aluminum oxide (Al 2 O 3 ), and the like.
  • the inorganic material film may be a single layer or a laminated body of a plurality of types of layers.
  • Examples of the method of covering the light emitting element 10 with the inorganic material film include a sputtering method and an electron cyclotron resonance (ECR) plasma CVD method when the inorganic material film is made of silicon nitride or silicon oxide.
  • ECR electron cyclotron resonance
  • the sputtering method can be carried out under the conditions of room temperature, electric power of 50 to 1000 W, and pressure of 0.001 to 0.1 Torr, for example, using a single gas such as argon or nitrogen as a carrier gas or a mixed gas.
  • a mixed gas of SiH 4 and O 2 or a mixed gas of SiH 4 and N 2 is used, and the temperature is 30 ° C to 100 ° C, the pressure is 10 mTorr to 1Torr, the frequency is 2.45 GHz, and the power is increased. It can be performed under the condition of 10 to 1000 W.
  • the thickness of the inorganic material film formed on the light emitting device 10 is not limited, but is, for example, 0.01 to 10 ⁇ m, preferably 0.1 to 5 ⁇ m from the viewpoint of improving the sealing performance and the flexible performance. ..
  • a sealing layer 22 for example, a method of applying a sealing agent on the light emitting element 10 and curing the light emitting element 10. And so on.
  • a coating method it is preferable to use an inkjet method.
  • the thickness of the resin layer is not limited, but is, for example, 0.1 to 50 ⁇ m, preferably 1 to 20 ⁇ m from the viewpoint of improving the sealing performance and the flexible performance.
  • an inorganic material film (barrier layer 24) on the above-mentioned resin layer.
  • the inorganic material and the forming method for forming the inorganic material film laminated on the resin layer are the same as those for the inorganic material film covering the light emitting element 10 described above.
  • the thickness of the inorganic material film formed on the resin layer is not limited, but is, for example, 0.01 to 10 ⁇ m, preferably 0.1 to 5 ⁇ m from the viewpoint of improving the sealing performance and the flexible performance.
  • the barrier layer 24 and the sealing layer 22 are provided on the light emitting element 10, and the sealing layer 22 is composed of a resin layer obtained by curing the sealing agent in the present embodiment. Therefore, it is possible to obtain a display device 100 having excellent reliability. Specifically, damage to the barrier layer 24 can be suppressed even when the plasma treatment step is performed when the barrier layer 24 is formed on the sealing layer 22. Further, for example, it is possible to suppress the generation of pinholes in the barrier layer 24 which is a SiN x film.
  • (Polymerizable compound) (A) Alicyclic UV curable resin 1: Dimethylol-tricyclodecanediacrylate, light acrylate DCP-A, UV curable resin manufactured by Kyoeisha Chemical Co., Ltd .2: Dimethylol-tricyclodecanedimethacrylate, light acrylate DCP-M, Kyoeisha Chemical Co., Ltd. (B) Chain UV curable resin 3: 1,12-dodecanediol dimethacrylate, SR262, Alchema UV curable resin 4: 1,9-nonanediol diacrylate, light acrylate 1,9ND-A, Kyoeisha Chemical Co., Ltd.
  • UV curable resin 5 1,9-nonanediol dimethacrylate, light acrylate 1,9ND-M
  • UV curable resin 6 Triethylene glycol diacrylate, SR272
  • UV curable resin 7 Tri Propropylene glycol diacrylate, SR306H, manufactured by Alchema
  • (C) -1 Linear monofunctional UV curable resin 8: Lauryl methacrylate, light acrylate L, manufactured by Kyoeisha Chemical Co., Ltd.
  • (C) -2 Aromatic monofunctional UV curable resin 9: 3-phenoxybenzyl acrylate, light acrylate POB -A, manufactured by Kyoeisha Chemical Co., Ltd.
  • UV Radical Initiator 1 2,4,6-trimethylbenzoyl-diphenylphosphine oxide, Omnirad TPO H, manufactured by IGM Resins
  • Example 1 Example 1 to 5, Comparative Examples 1 to 4
  • Each component was blended so as to have the blending composition shown in Table 1 to obtain a liquid curable composition as a sealing agent.
  • the characteristics of the encapsulant or the cured product thereof obtained in each example were measured by the following methods. The measurement results are also shown in Table 1.
  • viscosity The viscosity of the curable composition obtained in each example was measured at 25 ° C. and 20 rpm using an E-type viscometer (LV DV-II + Pro, manufactured by BROOKFIELD). Those having a measured viscosity of less than 30 mPa ⁇ s were regarded as acceptable.
  • a cured product of the encapsulant was obtained by the following procedure. That is, using a 100 ⁇ m thick Teflon (registered trademark) sheet as a mold, an uncured encapsulant is sandwiched between PET films, and a UV-LED with a wavelength of 395 nm has an illuminance of 1000 mW / cm 2 and an integrated light intensity of 1500 mJ / cm 2 . It was cured under the conditions to obtain a cured product. The obtained cured product was cut into a size of 10 mm in width ⁇ 40 mm in length with a cutter to obtain a measurement sample.
  • Teflon registered trademark
  • the tan ⁇ was measured by the dynamic viscoelasticity measuring device “DMS6100” while applying a frequency of 1 Hz to the measured sample of the cured product in the atmosphere and raising the temperature from room temperature to 250 ° C. at 5 ° C./min.
  • the temperature of the peak top of the obtained tan ⁇ was defined as Tg.
  • a coating film for obtaining a cured product for measuring the dielectric constant was prepared by the following method. That is, the obtained encapsulant was introduced into an inkjet cartridge DMC-11610 (manufactured by FUJIFILM Dimension). The inkjet cartridge was set in an inkjet device DMP-2831 (manufactured by Fujifilm Dimatix), and after adjusting the ejection state, the thickness after curing was increased on a substrate on which aluminum was vapor-deposited to a thickness of 100 nm on non-alkali glass. It was applied in a size of 5 cm ⁇ 5 cm so as to be 10 ⁇ m.
  • the obtained coating film was placed in a box at room temperature (25 ° C.) for 5 minutes to allow nitrogen to flow, and then irradiated with ultraviolet rays having a wavelength of 395 nm under the conditions of an illuminance of 1000 mW / cm 2 and an integrated light intensity of 1500 mJ / cm 2 , and cured. A film was formed. Then, aluminum was deposited on the inkjet coated surface to a thickness of 100 nm, and the dielectric constant was measured with an LCR meter HP4284A (manufactured by Agilent Technologies) under the condition of 100 kHz by an automatic balanced bridge method. Those with a measured dielectric constant of less than 3.5 were considered acceptable.
  • the encapsulant obtained in each example was introduced into an inkjet cartridge DMC-11610 (manufactured by FUJIFILM Dimension).
  • the inkjet cartridge is set in the inkjet device DMP-2831 (manufactured by Fujifilm Dimatic), and after adjusting the ejection state, the glass substrate has a size of 15 mm ⁇ 15 mm so that the cured thickness is 10 ⁇ m. Applied.
  • the obtained coating film was placed in a box at room temperature (25 ° C.) for 5 minutes to allow nitrogen to flow, and then irradiated with ultraviolet rays having a wavelength of 395 nm at 1500 mW / cm 2 for 1 second to form a cured film.
  • the sample on which the cured film was formed was plasma-treated for 1 minute under a pressure condition of 2500 W ICP power supply, 300 W RF power supply, DC bias 200 V, argon (Ar) flow rate 50 sccm, and 10 mtorr. Then, an inorganic sealing layer (SiN x film) having a film thickness of 100 nm was formed by an RF sputtering method using a SiN x target. On the other hand, an OLED element was vapor-deposited on a facing substrate and bonded to a substrate on which an inorganic sealing layer was formed to obtain an evaluation sample.
  • SiN x film SiN x film
  • the reliability test of the samples obtained in each example was carried out under the condition of 85 ° C. Specifically, the emission area ratio (%) after storing the samples obtained in each example at 85 ° C. for 100 hours was determined by the following method. That is, the light emitting area was calculated in the initial state and after storage for 100 hours using Motic Images Plus software (manufactured by Shimadzu Rika Co., Ltd.), and the light emitting area ratio was obtained. Those having a light emitting area ratio of 50% or more were regarded as acceptable.
  • the encapsulants obtained in each example were excellent in the effect of suppressing damage to the organic EL element against plasma irradiation.
  • the sealant obtained in each example had an excellent balance of viscosity, dielectric constant and Tg characteristics.

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