WO2014021696A1 - Film adhésif et produit servant à encapsuler un dispositif électronique organique utilisant celui-ci - Google Patents

Film adhésif et produit servant à encapsuler un dispositif électronique organique utilisant celui-ci Download PDF

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Publication number
WO2014021696A1
WO2014021696A1 PCT/KR2013/007053 KR2013007053W WO2014021696A1 WO 2014021696 A1 WO2014021696 A1 WO 2014021696A1 KR 2013007053 W KR2013007053 W KR 2013007053W WO 2014021696 A1 WO2014021696 A1 WO 2014021696A1
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Prior art keywords
adhesive film
weight
adhesive
electronic device
moisture
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PCT/KR2013/007053
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English (en)
Korean (ko)
Inventor
이승민
유현지
장석기
심정섭
조윤경
배경열
Original Assignee
주식회사 엘지화학
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Priority to CN201380038677.8A priority Critical patent/CN104508065B/zh
Priority to JP2015524197A priority patent/JP6105063B2/ja
Priority claimed from KR1020130092537A external-priority patent/KR101435338B1/ko
Publication of WO2014021696A1 publication Critical patent/WO2014021696A1/fr
Priority to US14/519,901 priority patent/US10125292B2/en

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/10—Adhesives in the form of films or foils without carriers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/32—Phosphorus-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2301/00—Additional features of adhesives in the form of films or foils
    • C09J2301/40—Additional features of adhesives in the form of films or foils characterized by the presence of essential components
    • C09J2301/408—Additional features of adhesives in the form of films or foils characterized by the presence of essential components additives as essential feature of the adhesive layer

Definitions

  • Embodiments of the present invention relate to an adhesive film and an encapsulation product of an organic electronic device using the same.
  • An organic electronic device refers to a device including an organic material layer that generates an exchange of electric charges using holes and electrons, and examples thereof include a photovoltaic device, a rectifier, Transmitters and organic light emitting diodes (OLEDs); and the like.
  • organic light emitting diodes have low power consumption, fast response speed, and are advantageous for thinning a display device or lighting, as compared with conventional light sources.
  • OLED has excellent space utilization, and is expected to be applied in various fields including various portable devices, monitors, notebooks, and TVs.
  • Embodiments of the present invention provide an adhesive film, and an organic electronic device encapsulation product using the same.
  • the present invention provides an adhesive film for encapsulating an organic electronic device, wherein the adhesive film includes a curable adhesive layer including a curable resin and a moisture adsorbent, and the content of the hydration reaction product of the moisture adsorbent and the moisture adsorbent is represented by the following general formula (1). It is related with the satisfied adhesive film.
  • X is the weight of the water adsorbent
  • X 0 is the weight of the product generated by the water adsorbent hydrating with water.
  • the invention according to another embodiment of the present invention provides an adhesive film having a change over time of the moisture blocking ability of the adhesive film is less than 1%.
  • the substrate An organic electronic device formed on the substrate; And the adhesive film encapsulating the organic electronic device, wherein the adhesive film covers the entire organic electronic device.
  • the adhesive film according to the embodiments of the present invention prevents the movement of moisture in the matrix resin to maintain moisture blocking ability to effectively block moisture or oxygen introduced into the organic electronic device from the outside, and also to thin the organic electronic device panel. Over time stability, life and durability are improved to ensure long-term reliability.
  • 1 is an XRD graph showing the change over time of the water absorbent of the adhesive film according to the Examples and Comparative Examples of the present invention.
  • the adhesive film according to one embodiment of the present invention includes a curable adhesive layer including a curable resin and a moisture adsorbent, and the content of the hydration reaction product of the moisture adsorbent and the moisture adsorbent satisfies the following general formula (1).
  • X is the weight of the water adsorbent
  • X 0 is the weight of the product generated by the water adsorbent hydrating with water.
  • organic electronic device means an article or device having a structure including an organic material layer that generates an exchange of electric charge using holes and electrons between a pair of electrodes facing each other.
  • the photovoltaic device, a rectifier, a transmitter, and an organic light emitting diode (OLED) may be mentioned, but is not limited thereto.
  • the organic electronic device may be an OLED.
  • the curable adhesive can maintain a solid or semi-solid at room temperature, and when heated, flow can be generated to attach a flat plate without bubbles, and when the curing reaction is finished, the object is hardened with an adhesive. It may be an adhesive in the form of fixing.
  • the adhesive film is important to ensure long-term reliability when encapsulating the organic electronic device.
  • conventional adhesive films in particular adhesive films using latent curing agents, they have generally been stored in a temperature range of around 4 ° C.
  • the adhesive film according to embodiments of the present invention is stored at a storage temperature of 0 ° C. or lower, so that moisture that may exist from the time of manufacture of the adhesive film, that is, moisture that the adhesive film is moistened, moves in the matrix during the storage period, thereby adsorbing the moisture adsorbent.
  • the moisture barrier ability from being lowered as the storage period becomes longer than the initial moisture barrier ability of the adhesive film. This is one of the factors that inhibits the movement of moisture in the matrix due to the storage temperature below zero.
  • the storage temperature below 0 ° C may be, for example, -10 ° C to -4 ° C, it is possible to prevent a decrease in the moisture barrier ability when maintaining this storage temperature within the above range.
  • the tack time (aging) to room temperature becomes long (long time), the productivity of the process may be reduced.
  • the change over time of the moisture blocking ability of the adhesive film according to embodiments of the present invention may be less than 1%.
  • the life of the organic electronic device can be maintained long, and the durability can be improved, and the adhesion strength due to excessive moisture adsorption can be prevented to reduce the The interfacial peeling phenomenon can be prevented.
  • An adhesive film having a time-dependent change in the moisture barrier ability of the adhesive film of less than 1% satisfies at least one of the following three conditions. a) the change in purity of the moisture adsorbent over time by less than 10% by weight; b) the change over time in weight increase rate under the durability condition of 85 ° C. and 85% relative humidity.
  • the change in the purity of the water adsorbent over time can be measured by X-ray diffraction (XRD) analysis.
  • XRD X-ray diffraction
  • the metal oxide there is a peak corresponding to the intrinsic value of each particle.
  • the particles are changed and the purity of the metal oxide is reduced.
  • CaO calcium oxide
  • Ca (OH) 2 calcium hydroxide
  • the change in the moisture blocking ability over time can also be measured by the difference in weight increase rate (time change in weight increase rate) after the durability condition of the adhesive film according to the storage time.
  • the change in the moisture blocking ability of the adhesive film is insignificant, when the adhesive film is left for a certain period of time after storage, the moisture absorption ability is excellent and the weight increase rate of the adhesive film will be increased.
  • the weight increase rate of the adhesive film becomes lower than otherwise because of the decrease in the water adsorption capacity.
  • the difference in weight increase rate after the durability condition of the adhesive film according to the storage time becomes large.
  • the temporal change of the weight increase rate after the endurance condition of 85 ° C. and 85% relative humidity of the adhesive film which can give long-term reliability when encapsulating the organic electronic device may be less than 0.2%. That is, for example, the weight increase rate after the endurance conditions of the adhesive film according to the storage time is only less than 3.7% to 3.5%. Therefore, when the adhesive film having a different storage time is left to the endurance conditions, and then the weight increase rate is measured, when the difference in the weight increase rate is less than 0.2%, the time-dependent change in the moisture barrier ability is less than 1%.
  • the weight increase rate after curing the adhesive film of 200 ⁇ m thickness, after cutting to a certain size to prepare a specimen, and record the initial weight of the specimen, the specimen under 85 °C and 85% relative humidity After leaving for 24 hours, the surface moisture can be removed, and then the weight can be calculated to calculate the increase in weight relative to the initial weight. Can be.
  • the change over time of the moisture barrier ability can also be measured by the difference in moisture penetration rate (change in moisture penetration rate over time) after the durability condition of the adhesive film according to the storage time. This can be measured by the Calcium test. Encapsulate the film with 6mm bezel on the coated Ca and measure the rate of water penetration under 85 ° C. and 85% relative humidity. Changes in moisture penetration rate over time may be less than 10%, and in the case of more than 10%, moisture penetrates quickly, thereby degrading moisture blocking ability and causing OLED panel defects.
  • the adhesive film may have a viscosity at room temperature of 10 6 dyne / cm 2 or more or 10 7 dyne / cm 2 or more.
  • room temperature means a natural temperature that is not heated or reduced, for example, about 15 ° C to 35 ° C, more specifically about 20 ° C to 25 ° C, and more specifically about 25 ° C. It can mean the temperature of.
  • the said viscosity can be measured using ARES (Advanced Rheometric Expansion System).
  • the upper limit of the viscosity is not particularly limited.
  • the upper limit of the viscosity is in the range of about 10 9 dyne / cm 2 or less. Can be controlled.
  • the adhesive film structurally enables the substrate and the upper substrate to be bonded together with the moisture barrier property, thereby facilitating the manufacturing process when manufacturing the panel of the organic electronic device and simplifying the manufacturing process by eliminating a separate passivation process.
  • the thickness of the organic electronic device can be reduced, thereby contributing to thinning.
  • Curable resins usable in embodiments of the present invention have a water vapor transmission rate (WVTR) in the cured state of 50 g / m 2 ⁇ day or less, preferably 30 g / m 2 ⁇ day or less, 20 g / m 2 ⁇ day or less or 15 g / m 2 ⁇ day or less.
  • WVTR water vapor transmission rate
  • the term “cured state of the curable resin” refers to a curable resin that is cured or crosslinked through its reaction with other components such as alone or with a curing agent or the like, and when used as an encapsulant, retains components such as moisture adsorbents and fillers, It means the state converted to the state which can exhibit the performance as a structural adhesive.
  • the said water vapor transmission rate is the water vapor transmission rate measured with respect to the thickness direction of the said hardened
  • the moisture permeability is measured according to ASTM F1249.
  • the moisture permeability within the above range, the penetration of moisture, moisture or oxygen into the organic electronic device encapsulation product can be effectively suppressed, and the introduction effect of the moisture reactive adsorbent can be exerted.
  • the water vapor transmission rate in the cured state of the resin is that the lower the numerical value shows the excellent performance of the sealing structure, the lower limit is not particularly limited.
  • thermosetting resin means a resin that can be cured through an appropriate heat application or aging process
  • photocurable resin means a resin that can be cured by irradiation of electromagnetic waves.
  • electromagnetic waves microwaves, infrared (IR), ultraviolet (UV), X-rays and ⁇ -rays, as well as ⁇ -particle beam (proton beam), proton beam (neutron) Particle beams such as neutron beams and electron beams may be included.
  • IR infrared
  • UV ultraviolet
  • X-rays and ⁇ -rays as well as ⁇ -particle beam (proton beam), proton beam (neutron) Particle beams such as neutron beams and electron beams
  • ⁇ -particle beam proton beam
  • neutral Particle beams such as neutron beams and electron beams
  • cationic photocurable resin is mentioned.
  • the cationic photocurable resin means a resin that can be cured by cationic polymerization or cation curing reaction induced by irradiation of electromagnetic waves.
  • the curable resin may be a dual curable resin including both thermosetting and photocuring properties.
  • the specific kind of the curable resin is not particularly limited as long as it has the aforementioned characteristics.
  • it may be cured to exhibit adhesive properties, and may include one or more thermosetting functional groups such as glycidyl group, isocyanate group, hydroxy group, carboxyl group or amide group, or may be an epoxide group or a cyclic ether. and resins containing at least one functional group curable by irradiation of electromagnetic waves such as a (cyclic ether) group, a sulfide group, an acetal group, or a lactone group.
  • specific types of the resin may include an acrylic resin, a polyester resin, an isocyanate resin, an epoxy resin, and the like, but is not limited thereto.
  • Aromatic or aliphatic; Or an epoxy resin of linear or branched chain type can be used.
  • an epoxy resin having an epoxy equivalent of 180 g / eq to 1,000 g / eq may be used.
  • an epoxy resin having an epoxy equivalent in the above range properties such as adhesion performance and glass transition temperature of the cured product can be effectively maintained.
  • examples of such epoxy resins include cresol novolac epoxy resins, bisphenol A epoxy resins, bisphenol A novolac epoxy resins, phenol novolac epoxy resins, tetrafunctional epoxy resins, biphenyl epoxy resins, and triphenol methane types.
  • a kind or mixture of an epoxy resin, an alkyl modified triphenol methane epoxy resin, a naphthalene type epoxy resin, a dicyclopentadiene type epoxy resin, or a dicyclopentadiene modified phenol type epoxy resin is mentioned.
  • the epoxy resin which contains a cyclic structure in molecular structure can be used as an example, More specifically, the epoxy resin containing an aromatic group (for example, a phenyl group) can be used.
  • the epoxy resin contains an aromatic group the cured product may have excellent thermal and chemical stability while exhibiting low moisture absorption, thereby improving reliability of the organic electronic device encapsulation structure.
  • aromatic group-containing epoxy resin examples include biphenyl type epoxy resin, dicyclopentadiene type epoxy resin, naphthalene type epoxy resin, dicyclopentadiene modified phenol type epoxy resin, cresol type epoxy resin, Bisphenol-based epoxy resins, xylox-based epoxy resins, polyfunctional epoxy resins, phenol novolac epoxy resins, triphenol methane-type epoxy resins and alkyl-modified triphenol methane epoxy resins, such as one or a mixture of two or more, but is not limited thereto. no.
  • a silane-modified epoxy resin for example, a silane-modified epoxy resin having an aromatic group can be used.
  • silane-modified epoxy resin for example, a reactant of at least one of the epoxy resins described above with the silane compound can be used.
  • silane compound in the above for example, the compound represented by the following formula (1) can be exemplified.
  • D is a vinyl group, an epoxy group, an amino group, an acryl group, a methacryl group, a mercapto group, an alkoxy group or an isocyanate group, or an alkyl group substituted with any one of the above functional groups
  • X is hydrogen or an alkyl group.
  • n is a number of 1 to 3.
  • functional group “D” may react with a functional group included in the epoxy resin to form a silane-modified epoxy resin.
  • the silane compound may be introduced into the epoxy group while the amino group reacts with the epoxy group of the epoxy resin to form a "-CH (OH) -CH 2 -NH-" bond.
  • an epoxy resin containing a hydroxy group for example, a bisphenol F type epoxy resin, a bisphenol F type novolac epoxy resin, a bisphenol A type epoxy resin or a bisphenol A silane compound may also be introduced by reacting with a bisphenol-type epoxy resin such as an A-type novolac epoxy resin.
  • alkyl group in Chemical Formula 1 an alkyl group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms, or 1 to 4 carbon atoms may be exemplified.
  • the alkyl group may be a straight chain, branched chain or cyclic alkyl group.
  • fluorine (F), chlorine (Cl), bromine (Br) or iodine (I) may be exemplified.
  • alkoxy group in Formula 1 an alkoxy group having 1 to 20 carbon atoms, 1 to 12 carbon atoms, 1 to 8 carbon atoms or 1 to 4 carbon atoms may be exemplified.
  • the alkoxy group may be linear, branched or cyclic.
  • aryl group included in the aryl group or the aryloxy group in the formula (1), as well as the aryl group, so-called aralkyl group (aralkyl group) or arylalkyl group may be included.
  • the aryl group may mean a monovalent moiety derived from a compound or derivative thereof including one or more benzene rings or a structure in which two or more benzene rings are linked or condensed.
  • the aryl group may be, for example, an aryl group having 6 to 25 carbon atoms, 6 to 21 carbon atoms, 6 to 18 carbon atoms, or 6 to 12 carbon atoms.
  • aryl group for example, a phenyl group, dichlorophenyl, chlorophenyl, phenylethyl group, phenylpropyl group, benzyl group, tolyl group, xylyl group (xylyl group) or naphthyl group and the like can be exemplified. Phenyl groups can be exemplified.
  • an acyloxy group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, or 1 to 12 carbon atoms may be exemplified.
  • an alkylthio group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, or 1 to 8 carbon atoms or 1 to 4 carbon atoms may be exemplified, and an alkyleneoxythio group.
  • an alkyleneoxythio group having 1 to 20 carbon atoms, 1 to 16 carbon atoms, 1 to 12 carbon atoms, or 1 to 8 carbon atoms or 1 to 4 carbon atoms may be exemplified, and an alkyleneoxythio group.
  • the alkyl group, alkoxy group, aryl group, acyloxy group, alkylthio group or alkyleneoxythio group may be optionally substituted with one or more substituents.
  • substituents a hydroxy group, an epoxy group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an acyl group, a thiol group, an acryloyl group, a methacryloyl group, an aryl group or an isocyanate group may be exemplified, but is not limited thereto. It is not.
  • the functional group “D” may be, for example, an alkoxy group, an amino group or an isocyanate group.
  • At least one, two or more, or three of the functional groups "X" in Formula 1 may be, for example, a halogen atom, an alkoxy group, an aryloxy group, an acyloxy group, an alkylthio group, or an alkyleneoxythio group, or the like. Or an alkoxy group.
  • Examples of the silane-modified epoxy resin include about 0.1 part by weight to about 10 parts by weight, about 0.1 part by weight to about 9 parts by weight, about 0.1 part by weight to about 8 parts by weight, and about 0.1 part by weight based on 100 parts by weight of the epoxy resin. To about 7 parts by weight, about 0.1 to about 6 parts by weight, about 0.1 to about 5 parts by weight, about 0.1 to about 4 parts by weight, about 0.1 to about 3 parts by weight, about 0.3 Epoxy resins in which parts by weight to 2 parts by weight or about 0.5 parts by weight to about 2 parts by weight of the silane compound are introduced may be used.
  • the epoxy resin into which the silane compound is introduced may be an aromatic epoxy resin.
  • the aromatic epoxy resins include bisphenol epoxy resins such as bisphenol F epoxy resins, bisphenol F novolac epoxy resins, bisphenol A epoxy resins, and bisphenol A novolac epoxy resins.
  • the adhesion of the organic electronic device to the glass substrate or the substrate inorganic material can be maximized, and the moisture barrier property, durability and reliability can be improved.
  • the specific kind of the epoxy resin is not particularly limited, and such a resin can be easily obtained from a place of purchase such as, for example, Kukdo Chemical.
  • the curable resin may also include styrene resin, polyolefin resin, thermoplastic elastomer, polyoxyalkylene resin, polyester resin, polyvinyl chloride resin, polycarbonate resin, polyphenylene sulfide resin, and hydrocarbons.
  • styrene resin polyolefin resin
  • thermoplastic elastomer polyoxyalkylene resin
  • polyester resin polyvinyl chloride resin
  • polycarbonate resin polycarbonate resin
  • polyphenylene sulfide resin polyphenylene sulfide resin
  • hydrocarbons hydrocarbons.
  • a mixture, a polyamide resin, an acrylate resin, an epoxy resin, a silicone resin, a fluorine resin, or a mixture thereof may be exemplified.
  • styrene resin for example, styrene-ethylene-butadiene-styrene block copolymer (SEBS), styrene-isoprene-styrene block copolymer (SIS), acrylonitrile-butadiene-styrene block copolymer (ABS ), Acrylonitrile-styrene-acrylate block copolymers (ASA), styrene-butadiene-styrene block copolymers (SBS), styrene-based homopolymers or mixtures thereof.
  • SEBS styrene-ethylene-butadiene-styrene block copolymer
  • SIS styrene-isoprene-styrene block copolymer
  • ABS acrylonitrile-butadiene-styrene block copolymer
  • ASA Acrylonitrile-styrene-acrylate block cop
  • the olefin resin for example, a high density polyethylene resin, a low density polyethylene resin, a polypropylene resin or a mixture thereof may be exemplified.
  • the thermoplastic elastomer for example, an ester thermoplastic elastomer, an olefin thermoplastic elastomer, a mixture thereof, or the like can be used.
  • polybutadiene resin or polyisobutene resin may be used as the olefinic thermoplastic elastomer.
  • the polyoxyalkylene resins include polyoxymethylene resins, polyoxyethylene resins, and mixtures thereof.
  • polyester resins examples include polyethylene terephthalate resins, polybutylene terephthalate resins, and mixtures thereof.
  • polyvinyl chloride-based resin for example, polyvinylidene chloride and the like can be exemplified.
  • mixture of the hydrocarbons for example, hexatriacotane or paraffin may be exemplified.
  • polyamide resin nylon etc. can be illustrated, for example.
  • acrylate resin polybutyl (meth) acrylate etc. can be illustrated, for example.
  • Bisphenol-type such as bisphenol A type, bisphenol F type, bisphenol S type, and these hydrogenated substances
  • Novolak types such as phenol novolak type and cresol novolak type
  • Nitrogen-containing cyclic types such as triglycidyl isocyanurate type and hydantoin type
  • Alicyclic type Aliphatic type
  • Aromatic types such as naphthalene type and biphenyl type
  • Glycidyl types such as glycidyl ether type, glycidyl amine type and glycidyl ester type
  • Dicyclo types such as dicyclopentadiene type; Ester type; Ether ester type or mixtures thereof and the like can be exemplified.
  • silicone resins examples include polydimethylsiloxane and the like.
  • fluorine-type resin polytrifluoroethylene resin, polytetrafluoroethylene resin, polychlorotrifluoroethylene resin, polyhexafluoropropylene resin, polyvinylidene fluoride, polyvinylidene fluoride, polyfluoro Ethylene propylene propylene or mixtures thereof and the like can be exemplified.
  • the above-listed resins may be used, for example, by grafting with maleic anhydride, or the like, or may be used after being copolymerized with other listed resins or monomers for preparing the resins, or may be modified with other compounds.
  • the other compounds include carboxyl-terminated butadiene-acrylonitrile copolymers.
  • the resins listed may include one or more functional groups or moieties that can be cured by heat such as glycidyl group, isocyanate group, hydroxy group, carboxyl group or amide group or the like to be cured and exhibit adhesiveness, or one or more functional groups or moieties that can be cured by irradiation of active energy rays such as (epoxide) groups, cyclic ether groups, sulfide groups, acetal groups, or lactone groups. Can be.
  • one or more functional groups or moieties that can be cured by heat such as glycidyl group, isocyanate group, hydroxy group, carboxyl group or amide group or the like to be cured and exhibit adhesiveness
  • one or more functional groups or moieties that can be cured by irradiation of active energy rays such as (epoxide) groups, cyclic ether groups, sulfide groups, acetal groups, or lactone groups.
  • active energy rays such as
  • the curable resin may include a polyisobutene resin.
  • Polyisobutene resins may have hydrophobicity and exhibit low water vapor permeability and low surface energy.
  • a polyisobutene resin For example, Homopolymer of an isobutylene monomer; Or the copolymer which copolymerized the isobutylene monomer and the other monomer which can superpose
  • the other monomers polymerizable with the isobutylene monomer may include, for example, 1-butene, 2-butene, isoprene or butadiene.
  • the curable adhesive layer contains a moisture adsorbent in addition to the curable resin.
  • moisture adsorbent may be used as a generic term for a moisture reactive adsorbent that is a component capable of adsorbing or removing moisture or moisture introduced from the outside through a chemical reaction or the like.
  • the moisture adsorbent chemically reacts with moisture, moisture or oxygen introduced into the adhesive layer to adsorb moisture or moisture.
  • the specific kind of the moisture adsorbent is not particularly limited, and examples thereof include a metal powder such as alumina, a metal oxide, a metal salt or a mixture of two or more kinds of phosphorus pentoxide (P 2 O 5 ).
  • the metal oxides include phosphorus pentoxide (P 2 O 5 ), lithium oxide (Li 2 O), sodium oxide (Na 2 O), barium oxide (BaO), calcium oxide (CaO) or magnesium oxide (MgO).
  • the metal salts include lithium sulfate (Li 2 SO 4 ), sodium sulfate (Na 2 SO 4 ), calcium sulfate (CaSO 4 ), magnesium sulfate (MgSO 4 ), cobalt sulfate (CoSO 4 ), Sulfates such as gallium sulfate (Ga 2 (SO 4 ) 3 ), titanium sulfate (Ti (SO 4 ) 2 ) or nickel sulfate (NiSO 4 ), calcium chloride (CaCl 2 ), magnesium chloride (MgCl 2 ), strontium chloride (SrCl 2 ), yttrium chloride (YCl 3 ), copper chloride (CuCl 2 ), cesium fluor
  • the metal oxides may be blended into the composition in a state of properly processing the moisture adsorbent.
  • the thickness of the adhesive layer may be a thin film of 30 ⁇ m or less according to the type of organic electronic device to which the adhesive film is to be applied, and in this case, a grinding process of the moisture absorbent may be necessary.
  • a process such as a three roll mill, bead mill or ball mill may be used.
  • the adhesive film of the present invention is used for organic light emitting devices of the top emission type, the permeability of the adhesive layer itself becomes very important, and therefore, the size of the moisture adsorbent needs to be small. Therefore, the grinding process may be required even in such applications.
  • the adhesive layer may include 1 part by weight to 100 parts by weight or 5 parts by weight to 50 parts by weight of a moisture adsorbent based on 100 parts by weight of the curable resin.
  • a moisture adsorbent included in the above range, the volume expansion caused by the reaction between the moisture adsorbent and the moisture can be prevented from causing a crack in the film in the case where the curable resin is used beyond the limit and the organic electronic device is used. It can prevent chemical damage and provide long-term reliability of the adhesive film.
  • a unit “weight part” means the weight ratio between each component.
  • the cured product may exhibit excellent moisture and moisture barrier properties, and may exhibit excellent moisture barrier properties while forming a sealing structure of a thin film.
  • the curable adhesive layer may further include a filler.
  • a filler is a kind of physical moisture adsorbent that can inhibit the penetration by lengthening the movement path of moisture or moisture that penetrates into the encapsulation structure, and blocks the moisture and moisture through interaction with the matrix structure of the curable resin and the moisture adsorbent. You can maximize your sex.
  • the specific kind of filler that can be used in the present invention is not particularly limited, and for example, a mixture of one or more kinds selected from the group consisting of clay, talc, silica, zeolite, zirconia, titania and montmorillonite may be used.
  • a product surface-treated with an organic material may be used as the filler, or a coupling agent may be additionally added.
  • the curable adhesive layer may include 1 part by weight to 50 parts by weight or 1 part by weight to 20 parts by weight of a filler based on 100 parts by weight of the curable resin.
  • a filler based on 100 parts by weight of the curable resin.
  • it is possible to manufacture a film form it may provide a cured product exhibiting excellent moisture barrier properties even when formed into a thin film.
  • the specific kind of hardener which can be used is not specifically limited, It can select suitably according to the kind of curable resin used or the functional group contained in the resin.
  • curing agent for general epoxy resins known in this field can be used as a hardening
  • the curable adhesive layer may include, for example, 1 part by weight to 20 parts by weight or 1 part by weight to 10 parts by weight with respect to 100 parts by weight of the curable resin.
  • the content is only one example of the present invention. That is, in the present invention, the content of the curing agent may be changed according to the type and content of the curable resin or functional group, or the matrix structure or crosslinking density to be implemented.
  • the kind of said initiator which can be used by this invention for example, a cationic photoinitiator, is not specifically limited, For example, an aromatic diazonium salt, an aromatic iodine aluminum salt, an aromatic sulfonium salt, or an iron-arene complex, etc.
  • a well-known cationic polymerization initiator can be used, It is preferable to use an aromatic sulfonium salt among these, but it is not limited to this.
  • the content of the initiator may be, for example, 0.01 part by weight to 10 parts by weight or 0.1 part by weight to 3 parts by weight based on 100 parts by weight of the curable resin.
  • the content of the cationic photopolymerization initiator when the content of the cationic photopolymerization initiator is too small, there is a fear that sufficient curing does not proceed, and when too large, the content of the ionic substance after curing increases, resulting in poor durability of the adhesive or in view of the nature of the initiator ( conjugate acid) is formed, which is disadvantageous in terms of optical durability, and corrosion may occur depending on the substrate. Therefore, an appropriate content range may be selected in consideration of this point.
  • the curable adhesive layer may further include a high molecular weight resin.
  • the high molecular weight resin may serve to improve moldability, for example, when molding the composition of the present invention into a film or sheet shape. It can also serve as a high temperature viscosity modifier to control flow during the process.
  • high molecular weight resin which can be used above will not be restrict
  • Specific examples of high molecular weight resins that can be used are resins having a weight average molecular weight of 20,000 or more, such as phenoxy resins, acrylate resins, high molecular weight epoxy resins, ultra high molecular weight epoxy resins, high polarity functional group-containing rubbers and high One kind or a mixture of two or more kinds such as a high polarity functional group-containing reactive rubber, but is not limited thereto.
  • the content is not particularly limited to be adjusted according to the desired physical properties.
  • the high molecular weight resin may be included in an amount of about 200 parts by weight or less, 150 parts by weight or less or about 100 parts by weight or less based on 100 parts by weight of the curable resin.
  • the compatibility with each component of the resin composition can be effectively maintained, and can also serve as an adhesive.
  • the adhesive film may further include additives such as additional fillers for improving durability of the cured product, coupling agents for improving mechanical strength, adhesion, plasticizers, UV stabilizers, and antioxidants, without affecting the effects of the invention. Can be.
  • the curable adhesive layer of the adhesive film may have a single layer structure, or may have a multilayer structure having two or more adhesive layers.
  • the adhesive film includes a multilayer adhesive layer, the moisture adsorbent may be contained more in the layer disposed away from the organic electronic device.
  • the structure of the adhesive film of this invention includes the said adhesive bond layer, if it is a thing in particular, it will not restrict
  • a base film or a release film hereinafter a "first film” may be called.
  • it may have a structure including the adhesive layer formed on the base film or a release film.
  • the adhesive film of the present invention may further include a base film or a release film (hereinafter, sometimes referred to as "second film") formed on the adhesive layer.
  • second film a release film
  • the specific kind of the said 1st film which can be used by this invention is not specifically limited.
  • a general polymer film of this field can be used as the first film.
  • Ethylene-vinyl acetate film, ethylene-propylene copolymer film, ethylene-ethyl acrylate copolymer film, ethylene-methyl acrylate copolymer film, polyimide film and the like can be used.
  • an appropriate release treatment may be performed on one side or both sides of the base film or the release film of the present invention.
  • Alkyd-based, silicone-based, fluorine-based, unsaturated ester-based, polyolefin-based, or wax-based may be used as an example of the release agent used in the release treatment of the base film, and among these, it is preferable to use an alkyd-based, silicone-based, or fluorine-based release agent in terms of heat resistance. Preferred, but not limited to.
  • the kind of 2nd film (Hereinafter, a "cover film” may be called.) Which can be used by this invention is not specifically limited, either.
  • the second film the same or different kind as the first film can be used within the range exemplified in the above-described first film.
  • an appropriate release treatment may also be performed on the second film.
  • the thickness of the base film or the release film (first film) as described above is not particularly limited and may be appropriately selected depending on the application to be applied.
  • the thickness of the first film may be about 10 ⁇ m to 500 ⁇ m or about 20 ⁇ m to 200 ⁇ m. In the case of adjusting the thickness of the film in the above range, it is possible to prevent the deformation of the base film and to increase the economics.
  • the thickness of the second film is also not particularly limited. In this invention, you may set the thickness of the said 2nd film similarly to a 1st film, for example. In addition, the thickness of the second film may be set relatively thinner than the first film in consideration of processability and the like.
  • the thickness of the adhesive layer included in the adhesive film is not particularly limited and may be appropriately selected according to the following conditions in consideration of the use to which the film is applied.
  • the method for producing such an adhesive film is not particularly limited. For example, a first step of coating a coating liquid containing the composition of the adhesive layer described above on a base film or a release film; And a second step of drying the coating solution coated in the first step.
  • a third step of additionally compressing the base film or the release film on the coating liquid dried in the second step may be further performed.
  • the first step is to prepare a coating solution by dissolving or dispersing the composition of the adhesive layer described above in a suitable solvent.
  • the content of the epoxy resin and the like contained in the coating liquid may be appropriately controlled according to the desired moisture barrier properties and film formability.
  • the kind of solvent used for the said coating liquid manufacture is not specifically limited. However, when the drying time of the solvent is too long or when drying at a high temperature is necessary, problems may occur in terms of workability or durability of the adhesive film, and it is preferable to use a solvent having a volatilization temperature of 100 ° C. or less. In addition, in consideration of film formability, a small amount of a solvent having a volatilization temperature of the above range or more can be used.
  • solvents examples include methyl ethyl ketone (MEK), acetone, toluene, dimethylformamide (DMF), methyl cellosolve (MCS), tetrahydrofuran (THF) or N- One kind or a mixture of two or more kinds such as methylpyrrolidone (NMP), but is not limited thereto.
  • MEK methyl ethyl ketone
  • DMF dimethylformamide
  • MCS methyl cellosolve
  • THF tetrahydrofuran
  • NMP methylpyrrolidone
  • the method of applying the coating solution to the base film or the release film in the first step is not particularly limited, for example, knife coat, roll coat, spray coat, gravure coat, curtain coat, comma coat or lip coat, etc.
  • the same known method can be used without limitation.
  • the second step is to dry the coating solution coated in the first step, to form an adhesive layer.
  • the adhesive layer may be formed by heating and removing the solvent by heating the coating solution applied to the film.
  • the drying conditions are not particularly limited, for example, the drying may be performed for 1 to 10 minutes at a temperature of 70 °C to 200 °C.
  • a third step of pressing the additional base film or the release film on the adhesive layer formed on the film may be further performed after the second step.
  • This third step may be carried out by coating an additional release film or base film (cover film or second film) onto the dried adhesive layer by hot roll lamination or press process after it is coated on the film.
  • the third step may be performed by a hot roll lamination method in view of the possibility and efficiency of the continuous process, wherein the process is about 0.1 kgf / cm 2 to 10 kgf / at a temperature of about 10 ° C. to 100 ° C. It can be carried out at a pressure of cm 2 .
  • Another embodiment of the invention is a substrate; An organic electronic device formed on the substrate; And an adhesive film as described above for encapsulating the organic electronic device, wherein the adhesive film covers the entire organic electronic device.
  • the organic electronic device encapsulation product may further include a protective film protecting the organic electronic device between the adhesive film and the organic electronic device.
  • the organic electronic device encapsulation product may further include an encapsulation substrate on the adhesive film, wherein the adhesive film serves to adhere the encapsulation substrate and the substrate.
  • the organic electronic device may be an organic light emitting diode.
  • the organic electronic device encapsulation product has the advantage of simplifying the manufacturing process and reducing the process cost, and can be used regardless of the design method of the organic electronic device, and has the advantage of providing excellent mechanical durability to the organic electronic device. have.
  • Another embodiment of the present invention comprises the steps of applying the adhesive layer of the above-mentioned adhesive film to the substrate on which the organic electronic device is formed to cover the organic electronic device; And a method for encapsulating the organic electronic device, comprising curing the adhesive layer.
  • the applying of the adhesive film to the organic electronic device may be performed by hot roll lamination, hot pressing, or vacuum pressing of the adhesive film, and is not particularly limited.
  • the applying of the adhesive film to the organic electronic device may be performed at a temperature of 50 ° C. to 90 ° C., and the curing step may be performed by heating to a temperature range of 70 ° C. to 110 ° C. or by irradiating UV. have.
  • the step of attaching the other side of the adhesive film abuts on glass or metal, which is an additional encapsulation material, may be added.
  • a transparent electrode is formed on a substrate such as glass or a polymer film by vacuum deposition or sputtering, and an organic material layer is formed on the transparent electrode.
  • the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer and / or an electron transport layer.
  • a second electrode is further formed on the organic material layer.
  • the above-described adhesive film is applied to cover all of the organic electronic devices on the organic electronic device on the substrate.
  • the method of applying the adhesive film is not particularly limited, and for example, a cover substrate (ex.
  • Polymer film can be applied by a method such as heating and pressing.
  • a method such as heating and pressing.
  • a heat, vacuum press or A vacuum laminator or the like may be used to transfer onto the cover substrate.
  • the adhesive force or the adhesive force of the adhesive film may be reduced. Therefore, it is preferable to control the process temperature to about 100 ° C. or less and the process time within 5 minutes.
  • a vacuum press or a vacuum laminator may be used even when the cover substrate on which the adhesive film has been transferred is heat-compressed to the organic electronic device.
  • the temperature conditions at this stage can be set as described above, and the process time is preferably within 10 minutes.
  • an additional curing process may be performed on the adhesive film obtained by compressing the organic electronic device.
  • the curing process (main curing) may be performed in, for example, a heating chamber or a UV chamber. Conditions in the present curing may be appropriately selected in consideration of the stability of the organic electronic device.
  • the above-described manufacturing process is only one example for encapsulating the organic electronic device of the present invention, and the process sequence or process conditions may be freely modified.
  • the order of the transfer and compression processes may be changed by first transferring the adhesive film of the present invention to the organic electronic device on the substrate and then compressing the cover substrate.
  • the protective layer may be formed on the organic electronic device, then the adhesive film may be applied, and then the cover substrate may be omitted and cured.
  • the adhesive solution prepared above was applied to the release surface of the release PET using a comma coater, dried at 130 ° C. for 3 minutes in a dryer to form an adhesive layer having a thickness of 15 ⁇ m, and then the release PET was added on the adhesive layer. Pressed.
  • the adhesive film prepared above was stored frozen for 2 weeks, 4 weeks and 8 weeks at a temperature of -5 °C.
  • An adhesive film was prepared in the same manner as in Examples 1 to 3 except that the storage temperature was refrigerated at a temperature of 4 ° C. in the adhesive film storage process of Example 1.
  • the weight increase rates of the adhesive films of Examples 1 to 3 and Comparative Examples 1 to 3 were investigated. Specifically, the adhesive films of Examples 1 to 3 and Comparative Examples 1 to 3 were prepared in a thickness of 200 ⁇ m, then cured at 100 ° C. for 3 hours in a high temperature dryer, and then cut into 5 cm ⁇ 5 cm Was prepared. After recording the initial weight of the cured specimen, the specimen was left in a constant temperature and humidity chamber at a temperature of 85 ° C. and an environment of 85% R.H. for 24 hours, after which moisture on the surface was removed and weighed. To calculate the weight increase rate of the specimen as shown in Table 2 below.
  • B is the weight of the specimen after moisture absorption and A is the initial weight of the specimen.
  • the change over time in the purity of the moisture adsorbent is less than 10%, and the weight after the endurance conditions.
  • the change over time of the increase rate is 0.2%, it can be confirmed that the change over time of the moisture blocking ability is less than 1%, it can be confirmed that the organic electronic device can be effectively sealed from the moisture.
  • the adhesive film stored at a refrigeration temperature of 4 ° C. as in the conventional adhesive film has a large change in moisture blocking ability as the storage time becomes longer than the initial moisture blocking ability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

La présente invention concerne un film adhésif et un produit qui sert à encapsuler un dispositif électronique organique utilisant celui-ci. La présente invention maintient une capacité à retenir l'humidité en empêchant l'humidité dans une matrice en résine de bouger, ce qui arrête efficacement le déplacement vers le dispositif électronique organique de l'humidité ou de l'oxygène provenant de l'extérieur et augmente la stabilité dans le temps, la durée de vie, et la durabilité dans l'amincissement d'un panneau du dispositif électronique organique, et procure ainsi une fiabilité à long terme.
PCT/KR2013/007053 2012-08-03 2013-08-05 Film adhésif et produit servant à encapsuler un dispositif électronique organique utilisant celui-ci WO2014021696A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CN201380038677.8A CN104508065B (zh) 2012-08-03 2013-08-05 粘合膜和使用该粘合膜的用于封装有机电子装置的产品
JP2015524197A JP6105063B2 (ja) 2012-08-03 2013-08-05 接着フィルム及びこれを利用した有機電子装置の封止製品
US14/519,901 US10125292B2 (en) 2012-08-03 2014-10-21 Adhesive film and product for encapsulating organic electronic device using same

Applications Claiming Priority (4)

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KR10-2012-0085428 2012-08-03
KR20120085428 2012-08-03
KR10-2013-0092537 2013-08-05
KR1020130092537A KR101435338B1 (ko) 2012-08-03 2013-08-05 접착 필름 및 이를 이용한 유기전자장치의 봉지 제품

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Cited By (4)

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JP2019200994A (ja) * 2014-02-18 2019-11-21 エルジー・ケム・リミテッド 封止フィルム及びこれを含む有機電子装置
CN113733696A (zh) * 2020-05-29 2021-12-03 利诺士尖端材料有限公司 有机电子装置用封装材料及包括其的可卷曲有机电子装置
US11267996B2 (en) * 2015-03-24 2022-03-08 Lg Chem, Ltd. Adhesive composition
CN115717041A (zh) * 2022-11-23 2023-02-28 世晨材料技术(上海)有限公司 一种可uv固化的组合物及包含该组合物的胶膜、胶带

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JP2004335208A (ja) * 2003-05-06 2004-11-25 Sumitomo Electric Ind Ltd Ｅｌ素子およびｅｌ素子用封止フィルム
US20050062174A1 (en) * 2003-09-19 2005-03-24 Osram Opto Semiconductors Gmbh Encapsulated organic electronic device
KR100827353B1 (ko) * 2006-10-13 2008-05-06 재단법인서울대학교산학협력재단 2-에톡시프로피온산 유도체 또는 이의 약학적으로허용가능한 염, 이의 제조방법 및 이를 유효성분으로함유하는 당뇨병 예방 및 치료제
KR20120046704A (ko) * 2010-11-02 2012-05-10 주식회사 엘지화학 접착 필름 및 이를 이용한 유기전자장치의 봉지 방법
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JP2004335208A (ja) * 2003-05-06 2004-11-25 Sumitomo Electric Ind Ltd Ｅｌ素子およびｅｌ素子用封止フィルム
US20050062174A1 (en) * 2003-09-19 2005-03-24 Osram Opto Semiconductors Gmbh Encapsulated organic electronic device
KR100827353B1 (ko) * 2006-10-13 2008-05-06 재단법인서울대학교산학협력재단 2-에톡시프로피온산 유도체 또는 이의 약학적으로허용가능한 염, 이의 제조방법 및 이를 유효성분으로함유하는 당뇨병 예방 및 치료제
KR20120046704A (ko) * 2010-11-02 2012-05-10 주식회사 엘지화학 접착 필름 및 이를 이용한 유기전자장치의 봉지 방법
KR20120055487A (ko) * 2010-11-23 2012-05-31 주식회사 엘지화학 접착제 조성물

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2019200994A (ja) * 2014-02-18 2019-11-21 エルジー・ケム・リミテッド 封止フィルム及びこれを含む有機電子装置
US11267996B2 (en) * 2015-03-24 2022-03-08 Lg Chem, Ltd. Adhesive composition
US11267995B2 (en) * 2015-03-24 2022-03-08 Lg Chem, Ltd. Adhesive composition
CN113733696A (zh) * 2020-05-29 2021-12-03 利诺士尖端材料有限公司 有机电子装置用封装材料及包括其的可卷曲有机电子装置
CN115717041A (zh) * 2022-11-23 2023-02-28 世晨材料技术(上海)有限公司 一种可uv固化的组合物及包含该组合物的胶膜、胶带
CN115717041B (zh) * 2022-11-23 2023-12-12 世晨材料技术(上海)有限公司 一种可uv固化的组合物及包含该组合物的胶膜、胶带

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