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WO2018199706A1 - Composition de matériau d'encapsulation - Google Patents

Composition de matériau d'encapsulation Download PDF

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Publication number
WO2018199706A1
WO2018199706A1 PCT/KR2018/004985 KR2018004985W WO2018199706A1 WO 2018199706 A1 WO2018199706 A1 WO 2018199706A1 KR 2018004985 W KR2018004985 W KR 2018004985W WO 2018199706 A1 WO2018199706 A1 WO 2018199706A1
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WO
WIPO (PCT)
Prior art keywords
electronic device
weight
organic electronic
parts
composition
Prior art date
Application number
PCT/KR2018/004985
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English (en)
Korean (ko)
Inventor
최국현
김준형
우유진
유미림
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
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Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to JP2019558657A priority Critical patent/JP7318851B2/ja
Priority to CN201880027997.6A priority patent/CN110574183B/zh
Publication of WO2018199706A1 publication Critical patent/WO2018199706A1/fr
Priority to JP2022030015A priority patent/JP7582574B2/ja

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
    • C08J3/241—Preventing premature crosslinking by physical separation of components, e.g. encapsulation
    • 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

Definitions

  • the present application relates to a sealing material composition, a method for manufacturing the same, an organic electronic device including the same, and a method for manufacturing the organic electronic device.
  • 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.
  • the present application provides a sealing material composition and a method of manufacturing the same that can effectively block moisture or oxygen introduced into the organic electronic device from the outside to secure the life of the organic electronic device.
  • the present application relates to a sealant composition and a method of manufacturing the same.
  • the sealing material composition may be prepared by a sealing material manufacturing method described below.
  • the sealant composition may be, for example, an encapsulant applied to encapsulating or encapsulating an organic electronic device such as an OLED.
  • the sealant composition of the present application may be applied to encapsulating or encapsulating the entire surface of the organic electronic device. Therefore, after the sealant composition is applied to the encapsulation, it may exist in the form of an organic layer that seals the entire surface of the organic electronic device.
  • the organic layer may be stacked on the organic electronic device together with an inorganic protective film and / or an inorganic layer to be described later to form an encapsulation structure.
  • the present application relates to a sealing material composition for sealing an organic electronic device applicable to an inkjet process and a method for manufacturing the same, wherein the composition is discharged to a substrate using inkjet printing that can be patterned in a non-contact manner, It can be designed to have.
  • 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.
  • Exemplary methods of preparing the sealant composition may include a water removal step.
  • the sealant composition may be subjected to distribution and storage before being applied to the organic electronic device encapsulation described above. When moisture is present in the composition or in the container for storing the composition, the sealing function may be lost. . Therefore, the sealant composition of the present application may be a sealant composition that has undergone a water removal step.
  • the water removal step is 20 to 5000 lpm (liter per minute), 30 to 4300 lpm, 46 to 3200 lpm, 58 to 2800 lpm, 68 to 1900 lpm, 80 to 1800 lpm, 120 to 1700 lpm relative to the sealant composition in the container.
  • the inert gas may be N 2 , through which nitrogen sparging may be performed, but is not limited thereto.
  • the process of removing moisture removes moisture by injecting inert gas, repeating temperature rising and cooling using a circulator with respect to the sealing material composition.
  • some of the sealant composition may be volatilized or partially cured during the temperature raising and cooling process, and in this case, the curing proceeds to a composition different from the desired composition, resulting in poor reliability of the product.
  • the present application can provide a sealant composition with excellent reliability by adjusting the injection flow rate of the inert gas, by removing the water present in the sealant composition without raising the temperature or cooling.
  • the water removal step is not limited to the above, and may further include passing a water adsorbent to the sealant composition.
  • the passing method is not particularly limited and may include contacting the sealant composition with the moisture absorbent.
  • the water removal step may be performed at a constant temperature.
  • the constant temperature state may refer to a state in which a step of temperature raising or cooling is excluded.
  • the constant temperature state may mean a state in which there is substantially no temperature change, and a state in which the temperature does not substantially change may have an error range of ⁇ 5 ° C. to 5 ° C. or ⁇ 3 ° C. to 3 ° C. with respect to the set temperature.
  • the set temperature may be any one of 20 °C to 48 °C.
  • the set temperature may be 21 ° C to 45 ° C, 22 ° C to 43 ° C, 23 ° C to 38 ° C, or 24 ° C to 32 ° C.
  • the method of manufacturing the sealant composition of the present application may prevent partial curing or partial volatilization by maintaining the moisture removal step at a constant temperature, and thus may maintain a desired composition of the sealant composition to provide a reliable product.
  • the sealing material composition according to the present application has a specific composition formulation to be described later, when heated or cooled, some side reactions proceed or phase separation occurs, the coating properties (inkjetting) is deteriorated, and accordingly applied to the device to emit light Dark spots may occur, resulting in deterioration of reliability.
  • the water removal step may include adjusting the pressure in the vessel within the range of 600 to 760 mmHg, 610 mmHg to 720 mmHg, 630 mmHg to 710 mmHg or 640 mmHg to 690 mmHg.
  • the present application can effectively remove the water to the desired level by adjusting the pressure range in the water removal step.
  • the sealing material manufacturing method of the present application may include storing the sealing material composition in a pouch after the water removal step.
  • the pouch may be an aluminum pouch, but is not limited thereto.
  • the present application can store the sealant composition in a pouch, thereby preventing the moisture in the air from infiltrating into the sealant composition during distribution and storage.
  • Exemplary sealant compositions may include an epoxy compound.
  • the sealant composition may be in solventless form.
  • Solvent-free form may mean a composition of a form that does not contain an organic solvent.
  • the sealant composition may be 1000ppm or less, 500ppm or less, or 100ppm or less according to the Karl Fischer total titration method.
  • the measurement may be measured for the composition 100mg, but is not limited thereto.
  • the lower limit is not particularly limited and may be 0 ppm or 10 ppm.
  • the moisture measurement is carried out at an operating temperature of 25 ° C., proceeds in a closed container, and can be adjusted to an equivalent point of 50 mV within an appropriate speed range of 0.3 to 2240 ⁇ g / min.
  • Iodine is electrically generated from the generating electrode and reacts with water.
  • the amount of water in the sample is calculated from the number of moles of electrons used to produce iodine.
  • the measurement can be measured using Karl fischer titrators-831 KF Coulometer-coulometric from Metrohm.
  • the present application by controlling the moisture content before curing of the sealing material composition as described above, to prevent chemical damage to the device even when applied directly to the organic electronic device, and to generate and grow a dark spot (dark spot) of the organic electronic device Can be suppressed.
  • the sealant composition of the present application may have an amount of less than 100 ppm of volatile organic compounds measured after curing.
  • the lower limit is not particularly limited and may be 0 ppm or 10 ppm.
  • the volatile organic compound may be expressed as an out gas.
  • the volatile organic compound may be measured after curing the sealant composition, and then holding the cured product sample at 110 ° C. for 30 minutes using Purge & Trap-gas chromatography / mass spectrometry. The measurement may be measured using a Purge & Trap sampler (JAI JTD-505III) -GC / MS (Agilent 7890b / 5977a).
  • the application can be prevented from chemical damage to the device even if applied directly to the organic electronic device.
  • the sealant composition is in the range of 45 parts by weight to 145 parts by weight based on 100 parts by weight of the epoxy compound, and may include a compound having an oxetane group.
  • the epoxy compound may be a photocurable or thermosetting compound, and in an embodiment of the present application may be a photocurable compound.
  • the compound having an oxetane group may be included in the range of 45 parts by weight to 145 parts by weight, 48 parts by weight to 144 parts by weight, 63 parts by weight to 143 parts by weight, or 68 parts by weight to 142 parts by weight based on 100 parts by weight of the epoxy compound. have.
  • the term "parts by weight” may mean a weight ratio between components.
  • the present application is capable of forming an organic layer in an inkjet method on an organic electronic device by controlling the specific composition and the content range described above, and the applied sealant composition has excellent spreadability within a short time and has excellent curing strength after curing.
  • the sealant composition of the present application may have a contact angle to glass of 30 ° or less, 25 ° or less, 20 ° or less, or 12 ° or less.
  • the lower limit is not particularly limited, but may be 1 ° or 3 ° or more.
  • the present application can secure the spreadability within a short time in the inkjet coating by adjusting the contact angle to 30 ° or less, thereby forming an organic layer of a thin film.
  • the contact angle may be measured by applying a drop of the sealant composition on glass using a method of measuring the Sessile Drop, and measuring the average value after five application.
  • the epoxy compound and / or the compound having an oxetane group may be included in at least 70wt%, at least 75wt%, at least 80wt% or at least 85wt% or at least 89wt% in the total component of the sealant composition.
  • the upper limit is not particularly limited and may be 99 wt% or less, 95 wt% or less, or 93 wt% or less.
  • the epoxy compound may be at least bifunctional. That is, one or more epoxy functional groups may be present in the compound, and the upper limit is not particularly limited but may be 10 or less.
  • the epoxy compound implements an appropriate degree of crosslinking in the adhesive to achieve excellent heat resistance at high temperature and high humidity.
  • the epoxy compound may include a compound having a cyclic structure in the molecular structure and / or a linear or branched aliphatic compound. That is, the sealant composition of the present application may include at least one of a compound having a cyclic structure and a linear or branched aliphatic compound in the molecular structure as an epoxy compound, may be included together.
  • the compound having a cyclic structure in the molecular structure may have a ring constituent atom in the range of 3 to 10, 4 to 8 or 5 to 7 in the molecular structure and the cyclic structure in the compound at least 1 or at least 2, 10 It may be present below.
  • the linear or branched aliphatic compound is 20 parts by weight or more, less than 205 parts by weight, based on 100 parts by weight of the compound having a cyclic structure.
  • Sealant composition within the range of parts by weight to 204 parts by weight, 30 parts by weight to 203 parts by weight, 34 parts by weight to 202 parts by weight, 40 parts by weight to 201 parts by weight, 60 parts by weight to 200 parts by weight or 100 parts by weight to 173 parts by weight.
  • the present application by controlling the content range, the sealing material composition to have a suitable physical properties in the front seal the organic electronic device, to have a good curing strength after curing, and also to implement a good moisture barrier properties together.
  • the epoxy compound may have an epoxy equivalent in the range of 50 to 350 g / eq, 73 to 332 g / eq, 94 to 318 g / eq, or 123 to 298 g / eq.
  • the compound having an oxetane group may have a weight average molecular weight in the range of 150 to 1,000 g / mol, 173 to 980 g / mol, 188 to 860 g / mol, 210 to 823 g / mol or 330 to 780 g / mol.
  • the present application is to control the epoxy equivalent of the epoxy compound low, or by adjusting the weight average molecular weight of the compound having the oxetane group low, the viscosity of the composition is too high while improving the degree of completion of curing after curing of the sealing material so that the inkjet process is impossible Can be prevented and at the same time can provide moisture barrier properties and excellent curing sensitivity.
  • the weight average molecular weight means a converted value with respect to standard polystyrene measured by gel permeation chromatography (GPC).
  • GPC gel permeation chromatography
  • a column consisting of a metal tube having a length of 250 to 300 mm and an inner diameter of 4.5 to 7.5 mm is filled with 3 to 20 mm Polystyrene bead.
  • the weight average molecular weight can be indirectly measured according to the outflow time.
  • the amount separated from the column by size can be detected by plotting it with time.
  • the epoxy equivalent in this specification is the number of grams (g / eq) of resin containing 1 gram equivalent of epoxy group, and can be measured according to the method prescribed
  • the compound having an oxetane group may have a boiling point in the range of 90 to 300 ° C, 98 to 270 ° C, 110 to 258 ° C or 138 to 237 ° C.
  • the present application is to control the boiling point of the compound in the above range, to realize excellent printability even at high temperatures in the inkjet process, while excellent in water barrier property, the sealing material that can prevent damage to the device is suppressed out gas is suppressed It is possible to provide.
  • the boiling point may be measured at 1 atmosphere unless otherwise specified.
  • compounds having a cyclic structure in the molecular structure include 3,4-epoxycyclohexylmethyl 3 ', 4'-epoxycyclohexanecarboxylate (EEC) and derivatives, dicyclopentadiene dioxides and derivatives, vinylcyclohexene Dioxides and derivatives, 1,4-cyclohexanedimethanol bis (3,4-epoxycyclohexanecarboxylate) and derivatives may be exemplified, but is not limited thereto.
  • EEC 3,4-epoxycyclohexylmethyl 3 ', 4'-epoxycyclohexanecarboxylate
  • dicyclopentadiene dioxides and derivatives vinylcyclohexene Dioxides and derivatives
  • 1,4-cyclohexanedimethanol bis (3,4-epoxycyclohexanecarboxylate) and derivatives
  • the compound containing the oxetane group is not limited in structure as long as it has the functional group, for example, OXT-221, CHOX, OX-SC, OXT101, OXT121, OXT221 or OXT212, manufactured by TOAGOSEI, or EHO, OXBP, OXTP or OXMA from ETERNACOLL can be exemplified.
  • linear or branched aliphatic epoxy compounds include aliphatic glycidyl ether, 1,4-butanediol diglycidyl ether, ethylene glycol diglycidyl ether, 1,6-hexanediol digly Include cylyl ether, propylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, butyl glycidyl ether, 2-ethylhexyl glycidyl ether or neopentylglycol diglycidyl ether It may be, but is not limited thereto.
  • the sealant composition may further include a surfactant.
  • the sealant composition may include a surfactant, thereby providing a liquid ink having improved spreadability.
  • the surfactant may include a polar functional group, and the polar functional group may be present at the terminal of the compound structure of the surfactant.
  • the polar functional group may include, for example, a carboxyl group, a hydroxyl group, a phosphate salt or a sulfonate salt.
  • the surfactant may be a non-silicone-based surfactant or a fluorine-based surfactant.
  • non-silicone surfactant or the fluorine-based surfactant is applied together with the above-described epoxy compound and / or a compound having an oxetane group to provide excellent coating property on the organic electronic device.
  • the surfactant including the polar reactor since the affinity with other components of the sealant composition is high, an excellent effect in terms of adhesion may be realized.
  • hydrophilic fluorine-based surfactants or non-silicone-based surfactants may be used to improve the coating property on the substrate.
  • the surfactant may be a polymeric or oligomeric fluorine-based surfactant.
  • the surfactant may be a commercially available product, for example, Glide 100, Glide 110, Glide 130, Glide 460, Glide 440, Glide450 or RAD2500, Megaface F-251, F-281, of DaiNippon Ink & Chemicals (DIC), F-552, F554, F-560, F-561, F-562, F-563, F-565, F-568, F-570 and F-571 or Surflon S-111, S-112 by Asahi Glass , S-113, S-121, S-131, S-132, S-141 and S-145 or Fluorad FC-93, FC-95, FC-98, FC-129, FC-135 FC-170C, FC-430 and FC-4430 or BYK-350, BYK-354, BYK-355, BYK-356, BYK-358N, BYK from
  • the surfactant may be included in an amount of 0.01 to 10 parts by weight, 0.05 to 10 parts by weight, 0.1 to 10 parts by weight, 0.5 to 8 parts by weight, or 1 to 4 parts by weight based on 100 parts by weight of the epoxy compound. .
  • the present application allows the sealant composition to be applied to an inkjet method to form an organic layer of a thin film.
  • the sealant composition may further include a photosensitizer to compensate for the curability in the long wavelength active energy ray of 300nm or more.
  • the photosensitizer may be a compound that absorbs wavelengths in the range of 200 nm to 400 nm.
  • the photosensitizers include anthracene-based compounds such as anthracene, 9,10-dibutoxyanthracene, 9,10-dimethoxyanthracene, 9,10-diethoxyanthracene and 2-ethyl-9,10-dimethoxyanthracene; Benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, methyl-o-benzoylbenzoate, 3,3 Benzophenone compounds such as dimethyl-4-methoxybenzophenone and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Acetophenone; Ketone compounds such as dimethoxy acetophenone, diethoxy acetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, and propanone; Perylene; Fluorenone compounds
  • the photosensitizer may be included in the range of 28 parts by weight to 40 parts by weight, 31 parts by weight to 38 parts by weight, or 32 parts by weight to 36 parts by weight based on 100 parts by weight of the photoinitiator described later.
  • the present application by adjusting the content of the photosensitizer, while implementing a curing sensitivity synergistic action at the desired wavelength, it is possible to prevent the photosensitizer is not dissolved to reduce the adhesive force.
  • the sealant composition may further include a photoinitiator.
  • the photoinitiator may be an ionic photoinitiator.
  • the photoinitiator may be a compound that absorbs a wavelength in the range of 200nm to 400nm.
  • the photoinitiator may be a cationic photopolymerization initiator. It can be used a known material in the art for cationic photo-polymerization initiator, for example, aromatic sulfonium, aromatic iodonium, aromatic dia cation portion containing jonyum or aromatic ammonium and AsF 6 -, SbF 6 -, PF 6 -, or tetrakis (penta-fluorophenyl) may comprise a compound having an anion portion comprising a borate.
  • aromatic sulfonium, aromatic iodonium, aromatic dia cation portion containing jonyum or aromatic ammonium and AsF 6 -, SbF 6 -, PF 6 -, or tetrakis (penta-fluorophenyl) may comprise a compound having an anion portion comprising a borate.
  • an onium salt or an organometallic salt-based ionization cation initiator or an organosilane or a latent sulfuric acid-based or non-ionized cationic photopolymerization initiator may be used.
  • the onium salt-based initiator include a diaryliodonium salt, a triarylsulfonium salt, an aryldiazonium salt, and the like.
  • the zero, iron arene and the like can be exemplified.
  • the organosilane-based initiator include o-nitrobenzyl triaryl silyl ether and triaryl silyl peroxide.
  • the latent sulfuric acid-based initiator may be exemplified by ⁇ -sulfonyloxy ketone or ⁇ -hydroxymethylbenzoin sulfonate and the like, but is not limited thereto. .
  • the sealant composition of the present application may include a photoinitiator including a sulfonium salt as a photoinitiator in the above-described specific composition, so as to be suitable for use in sealing an organic electronic device in an inkjet manner.
  • a photoinitiator including a sulfonium salt as a photoinitiator in the above-described specific composition, so as to be suitable for use in sealing an organic electronic device in an inkjet manner.
  • the sealing material composition according to the composition is directly sealed on the organic electronic device, the amount of outgas generated is small, thereby preventing chemical damage to the device.
  • the photoinitiator containing a sulfonium salt is also excellent in solubility, and may be suitably applied to an inkjet process.
  • the photoinitiator may be included in 1 to 15 parts by weight, 3 to 14 parts by weight, or 7 to 13.5 parts by weight based on 100 parts by weight of the epoxy compound.
  • the sealant composition of the present application may further include a coupling agent.
  • This application can improve the adhesiveness with the to-be-adhered body of the sealing material composition, and the moisture permeability of hardened
  • the coupling agent may include, for example, a titanium coupling agent, an aluminum coupling agent, or a silane coupling agent.
  • the silane coupling agent 3-glycidyloxypropyltrimethoxysilane, 3-glycidyloxypropyltriethoxysilane, 3-glycidyloxypropyl (dimethicone) Epoxy silane coupling agents such as methoxy) methylsilane and 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane; Mercapto silane coupling agents such as 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, 3-mercaptopropylmethyldimethoxysilane, and 11-mercaptodecyltrimethoxysilane; 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropyldimethoxymethylsilane, N-phenyl-3-aminopropyltrimethoxys
  • the coupling agent may be included in an amount of 0.1 parts by weight to 10 parts by weight or 0.5 parts by weight to 5 parts by weight based on 100 parts by weight of the epoxy compound.
  • the present application can implement the effect of improving the adhesion by the coupling agent within the above range.
  • the sealant composition of the present application may include a moisture adsorbent as necessary.
  • moisture adsorbent may be used as a generic term for components that can adsorb or remove moisture or moisture introduced from the outside through physical or chemical reactions. That is, it means a moisture reactive adsorbent or a physical adsorbent, and mixtures thereof may also be used.
  • the specific kind of water adsorbent that can be used in the present application is not particularly limited, and, for example, in the case of the water reactive adsorbent, one kind or a mixture of two or more kinds of metal oxides, metal salts, or phosphorus pentoxide (P 2 O 5 ) may be mentioned.
  • a physical adsorbent zeolite, zirconia or montmorillonite may be mentioned.
  • the sealant composition of the present application may include a moisture adsorbent in an amount of 5 parts by weight to 100 parts by weight, 5 to 80 parts by weight, 5 parts by weight to 70 parts by weight, or 10 to 30 parts by weight with respect to 100 parts by weight of the epoxy compound. have.
  • the sealing material composition of the present application preferably by controlling the content of the moisture adsorbent to 5 parts by weight or more, the sealing material composition or its cured product can be made to exhibit excellent moisture and moisture barrier properties.
  • the present application may control the content of the moisture adsorbent to 100 parts by weight or less, to provide a sealing structure of the thin film.
  • the sealant composition may further include an inorganic filler, as needed.
  • the specific kind of filler that can be used in the present application is not particularly limited, and for example, one kind or a mixture of two or more kinds of clay, talc, alumina, calcium carbonate or silica may be used.
  • the sealant composition of the present application may include 0 to 50 parts by weight, 1 to 40 parts by weight, 1 to 20 parts by weight, or 1 to 10 parts by weight of an inorganic filler based on 100 parts by weight of the epoxy compound. have.
  • the present application by controlling the inorganic filler to preferably 1 part by weight or more, it is possible to provide a sealing structure having excellent moisture or moisture barrier properties and mechanical properties.
  • the present invention can provide a cured product exhibiting excellent moisture barrier properties even when formed into a thin film by controlling the inorganic filler content to 50 parts by weight or less.
  • the sealing material composition according to the present application may include various additives in a range that does not affect the effects of the above-described invention.
  • the sealant composition may include an antifoaming agent, a tackifier, an ultraviolet stabilizer, an antioxidant, or the like in an appropriate range of contents depending on the desired physical properties.
  • the sealant composition may be liquid at room temperature, for example about 25 ° C.
  • the sealant composition may be a liquid in the form of a solvent.
  • the sealant composition may be applied to encapsulating the organic electronic device, and specifically, may be applied to encapsulating the entire surface of the organic electronic device.
  • the sealing material composition may have a liquid form at room temperature, thereby sealing the device in such a manner that the composition is applied to the side surface of the organic electronic device.
  • the present application has a solvent-free form, it is possible to adjust the volatile organic compound and / or moisture content in the above range.
  • the sealant composition of the present application may be an ink composition.
  • the sealant composition of the present application may be an ink composition capable of an inkjetting process.
  • the sealant composition of the present application may have a specific composition and physical properties to be inkjettable.
  • the sealant composition may have a light transmittance of 90% or more, 92% or more or 95% or more in the visible light region after curing.
  • the present application provides a high resolution, low power consumption, and long life organic electronic device by applying a sealant composition to a top emission organic electronic device.
  • the sealing composition of the present application may have a haze of 3% or less, 2% or less, or 1% or less after curing according to JIS K7105 standard test, and the lower limit is not particularly limited, but may be 0%.
  • the sealant composition may have excellent optical properties after curing.
  • the light transmittance or haze described above may be measured in the state of curing the sealant composition with an organic layer, and may be an optical property measured when the thickness of the organic layer is any one of 2 ⁇ m to 50 ⁇ m. .
  • the aforementioned moisture adsorbent or inorganic filler may not be included.
  • the present application also relates to a sealant composition.
  • the sealant composition may be 1000ppm or less, 500ppm or less, or 100ppm or less according to the Karl Fischer total titration method.
  • the measurement may be measured for the composition 100mg, but is not limited thereto.
  • the lower limit is not particularly limited and may be 0 ppm or 10 ppm.
  • the moisture measurement is carried out at an operating temperature of 25 ° C., proceeds in a closed container, and can be adjusted to an equivalent point of 50 mV within an appropriate speed range of 0.3 to 2240 ⁇ g / min.
  • Iodine is electrically generated from the generating electrode and reacts with water.
  • the amount of water in the sample is calculated from the number of moles of electrons used to produce iodine.
  • the measurement can be measured using Karl fischer titrators-831 KF Coulometer-coulometric from Metrohm.
  • the present application by controlling the moisture content before curing of the sealing material composition as described above, to prevent chemical damage to the device even when applied directly to the organic electronic device, and to generate and grow a dark spot (dark spot) of the organic electronic device Can be suppressed.
  • the sealing material composition may be a sealing material composition for sealing an organic electronic device manufactured by the above-described manufacturing method.
  • An exemplary organic electronic device 3 includes a substrate 31, as shown in FIG. An organic electronic device 32 formed on the substrate 31; And an organic layer 33 that seals the entire surface of the organic electronic device 32 and includes the sealant composition described above.
  • the organic electronic device may include a first electrode layer, an organic layer formed on the first electrode layer and including at least a light emitting layer, and a second electrode layer formed on the organic layer.
  • the first electrode layer may be a transparent electrode layer or a reflective electrode layer
  • the second electrode layer may also be a transparent electrode layer or a reflective electrode layer.
  • the organic electronic device may include a reflective electrode layer formed on the substrate, an organic layer formed on the reflective electrode layer and including at least a light emitting layer, and a transparent electrode layer formed on the organic layer.
  • the organic electronic device 23 may be an organic light emitting diode.
  • the organic electronic device according to the present application may be a top emission type, but is not limited thereto, and may be applied to a bottom emission type.
  • the organic electronic device may further include a protective film 35 that protects the electrode and the light emitting layer of the device.
  • the passivation layer 35 may be an inorganic passivation layer.
  • the protective film may be a protective layer by chemical vapor deposition (CVD), the material may be a known inorganic material, for example, silicon nitride (SiNx) may be used. In one example, silicon nitride (SiNx) used as the protective film may be deposited to a thickness of 0.01 ⁇ m 50 ⁇ m.
  • the organic electronic device 3 may further include an inorganic layer 34 formed on the organic layer 33.
  • the inorganic layer 34 is not limited in its material, and may be the same as or different from the above-described protective film.
  • the inorganic layer may be one or more metal oxides or nitrides selected from the group consisting of Al, Zr, Ti, Hf, Ta, In, Sn, Zn and Si.
  • the inorganic layer may have a thickness of 0.01 ⁇ m to 50 ⁇ m, or 0.1 ⁇ m to 20 ⁇ m, or 1 ⁇ m to 10 ⁇ m.
  • the inorganic layer of the present application may be an inorganic material without a dopant, or an inorganic material with a dopant.
  • the dopant that can be doped is one or more elements selected from the group consisting of Ga, Si, Ge, Al, Sn, Ge, B, In, Tl, Sc, V, Cr, Mn, Fe, Co, and Ni or the elements It may be an oxide of, but is not limited thereto.
  • the thickness of the organic layer may be in the range of 2 ⁇ m 20 ⁇ m, 2.5 ⁇ m 15 ⁇ m, 2.8 ⁇ m 9 ⁇ m.
  • the present application can provide a thin film of the organic electronic device by providing a thin thickness of the organic layer.
  • the organic electronic device 3 of the present application may include an encapsulation structure including the organic layer 33 and the inorganic layer 34 described above, and the encapsulation structure includes at least one organic layer and at least one inorganic layer.
  • the organic layer and the inorganic layer may be repeatedly stacked.
  • the organic electronic device may have a structure of a substrate / organic electronic device / protective film / (organic layer / inorganic layer) n, and n may be a number in the range of 1 to 100.
  • 1 is a cross-sectional view illustrating an example where n is 1;
  • the organic electronic device 3 of the present application may further include a cover substrate present on the organic layer 33.
  • the material of the substrate and / or the cover substrate is not particularly limited, and materials known in the art may be used.
  • the substrate or cover substrate may be a glass, a metal substrate or a polymer film.
  • the polymer film is, for example, polyethylene terephthalate film, polytetrafluoroethylene film, polyethylene film, polypropylene film, polybutene film, polybutadiene film, vinyl chloride copolymer film, polyurethane 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.
  • the encapsulation film 37 present between the cover substrate 38 and the substrate 31 on which the organic electronic device 32 is formed. It may further include.
  • the encapsulation film 37 may be applied to attach the substrate 31 on which the organic electronic device 32 is formed and the cover substrate 38.
  • the encapsulation film 37 may be an adhesive film or an adhesive film, but is not limited thereto. It is not.
  • the encapsulation film 37 may seal the entire surface of the encapsulation structure 36 of the organic layer and the inorganic layer, which are stacked on the organic electronic device 32.
  • the present application relates to a method for manufacturing an organic electronic device.
  • the manufacturing method comprises the steps of forming the organic layer 33 on the substrate 31 having the organic electronic device 32 formed thereon so that the above-mentioned sealing material composition seals the entire surface of the organic electronic device 32. It may include.
  • the organic electronic device 32 is a substrate 31, for example, to form a reflective electrode or a transparent electrode on the substrate 31, such as glass or a polymer film by vacuum deposition or sputtering, and the It can be prepared by forming an organic material layer on the reflective 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 second electrode may be a transparent electrode or a reflective electrode.
  • the manufacturing method of the present application may further include forming a protective film 35 on the first electrode, the organic material layer, and the second electrode formed on the substrate 31. Thereafter, the above-described organic layer 33 is applied to cover the organic electronic device 32 on the substrate 31. At this time, the step of forming the organic layer 33 is not particularly limited, and the inkjet printing, gravure coating, spin coating, screen printing or reverse offset of the sealant composition described above on the entire surface of the substrate 31. A process such as reverse offset may be used.
  • the manufacturing method also;
  • the method may further include irradiating light to the organic layer.
  • a curing process may be performed on the organic layer encapsulating the organic electronic device.
  • the curing process may be performed in, for example, a heating chamber or a UV chamber, and may be preferably performed in a UV chamber.
  • the composition may be irradiated with light to induce crosslinking.
  • Irradiating the light may include irradiating light having a wavelength range of 250 nm to 450 nm or 300 nm to 450 nm at a light amount of 0.3 to 6 J / cm 2 or a light amount of 0.5 to 5 J / cm 2 .
  • the manufacturing method of the present application may further include forming an inorganic layer 34 on the organic layer 33.
  • Forming the inorganic layer a method known in the art may be used, and may be the same as or different from the above-described protective film forming method.
  • the present application provides a sealing material composition and an organic electronic device including the same that can effectively block the water or oxygen flowing into the organic electronic device from the outside to secure the life of the organic electronic device.
  • 1 and 2 are cross-sectional views illustrating an organic electronic device according to one example of the present invention.
  • the mixing container was prepared using a Planetary mixer (Kurabo, KK-250s) to prepare a uniform sealing composition ink.
  • a water removal step is performed on the composition ink. Nitrogen sparging of 200 lpm is started for the sealant composition prepared in the mixing vessel having an internal pressure of 660 mmHg, and the sparging is continued for 3 hours while maintaining a constant temperature of 25 ° C. The sealing composition after the water removal step is sealed in an aluminum pouch.
  • a sealing material composition was prepared in the same manner as in Example 1 and sealed in an aluminum pouch.
  • a sealing material composition was prepared in the same manner as in Example 1 and sealed in an aluminum pouch.
  • a sealing material composition was prepared in the same manner as in Example 1 and sealed in an aluminum pouch.
  • a sealing material composition was prepared in the same manner as in Example 1 and sealed in an aluminum pouch.
  • the sealing material composition ink was prepared and stored in the same manner as in Example 1 except that the temperature was heated from 25 ° C. to 50 ° C. in the water removal step.
  • the sealing material composition ink was prepared and stored in the same manner as in Example 1 except that the temperature was cooled from 25 ° C. to 10 ° C. in the water removal step.
  • Moisture content was measured using Karl fischer titrators-831 KF Coulometer-coulometric from Metrohm for the sealant compositions prepared in Examples and Comparative Examples. Moisture content was determined using Karl Fischer total titration for 100 mg of the composition. Furthermore, it progressed at the operating temperature of 25 degreeC, it advanced in the airtight container, and adjusted to the equivalence point 50mV within the appropriate speed range of 0.3-2240 microgram / min.
  • the sealant compositions prepared in Examples and Comparative Examples were cured by irradiation of 1 J / cm 2 UV at an intensity of 1000 mW / cm 2 , followed by purge and trap-gas chromatography / mass of 50 mg of cured samples. After holding at 110 ° C. for 30 minutes using the assay, the amount of volatile organic compounds was measured. The measurements were measured using a Purge & Trap sampler (JAI JTD-505III) -GC / MS (Agilent 7890b / 5977a) instrument. If the measured amount is 100ppm or less, it can be classified as good.
  • the viscosity of the sealant composition was measured as follows using DV-3 as a Brookfield viscometer.
  • the sealant composition was measured at 25 ° C., 90% torque and 100 rpm shear rate conditions. Specifically, 0.5 ml of the sample was injected using a Cone / plate method of a Brookfield viscometer to measure the viscosity.
  • the measurement measures the viscosity (V1) immediately before sealing and the viscosity (V2) after 10 days, and measures the rate of change, and is good when the rate of change is within ⁇ 10%, rises above 10%, and rises above -10%. The case was classified as falling.
  • the sealing material composition prepared in the Example and the comparative example was apply

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Analytical Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
  • Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
  • Sealing Material Composition (AREA)
  • Polyethers (AREA)

Abstract

La présente invention concerne une composition de matériau d'encapsulation, un procédé de fabrication de la composition de matériau d'encapsulation, et un dispositif électronique organique comprenant celle-ci, et fournit une composition de matériau d'encapsulation qui bloque efficacement l'humidité ou l'oxygène introduits dans le dispositif électronique organique depuis l'extérieur et peut ainsi assurer une durée de vie du dispositif électronique organique, et son procédé de fabrication.
PCT/KR2018/004985 2017-04-28 2018-04-30 Composition de matériau d'encapsulation WO2018199706A1 (fr)

Priority Applications (3)

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JP2019558657A JP7318851B2 (ja) 2017-04-28 2018-04-30 密封材組成物
CN201880027997.6A CN110574183B (zh) 2017-04-28 2018-04-30 封装组合物
JP2022030015A JP7582574B2 (ja) 2017-04-28 2022-02-28 密封材組成物

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KR10-2017-0055075 2017-04-28
KR1020170055075A KR101891737B1 (ko) 2017-04-28 2017-04-28 밀봉재 조성물

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CN112490384A (zh) * 2019-09-11 2021-03-12 星宸光电股份有限公司 封装结构
WO2023286748A1 (fr) * 2021-07-16 2023-01-19 富士フイルム株式会社 Dispositif électronique et son procédé de fabrication

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KR101891737B1 (ko) 2018-09-28
TWI679786B (zh) 2019-12-11
CN110574183B (zh) 2022-11-15
JP2020523728A (ja) 2020-08-06
JP7318851B2 (ja) 2023-08-01
JP7582574B2 (ja) 2024-11-13
TW201901998A (zh) 2019-01-01
CN110574183A (zh) 2019-12-13
JP2022071055A (ja) 2022-05-13

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