WO1996008122A1 - Procede d'enrobage d'un element electroluminescent organique et d'un autre element electroluminescent organique - Google Patents
Procede d'enrobage d'un element electroluminescent organique et d'un autre element electroluminescent organique Download PDFInfo
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- WO1996008122A1 WO1996008122A1 PCT/JP1995/001764 JP9501764W WO9608122A1 WO 1996008122 A1 WO1996008122 A1 WO 1996008122A1 JP 9501764 W JP9501764 W JP 9501764W WO 9608122 A1 WO9608122 A1 WO 9608122A1
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- organic
- inert liquid
- adsorbent
- layer
- sealed
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/02—Details
- H05B33/04—Sealing arrangements, e.g. against humidity
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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
-
- 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
- H10K50/842—Containers
- H10K50/8426—Peripheral sealing arrangements, e.g. adhesives, sealants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/846—Passivation; Containers; Encapsulations comprising getter material or desiccants
Definitions
- the present invention relates to a method for sealing an organic electroluminescent device (hereinafter, abbreviated as “EL”), and a sealed organic EL device (hereinafter referred to as a “sealed organic EL device”).
- EL organic electroluminescent device
- sealed organic EL device hereinafter referred to as a “sealed organic EL device”.
- the EL element has high visibility due to self-emission, and has excellent impact resistance because it is a completely solid state element.
- various inorganic EL devices using inorganic compound ⁇ / as a light emitting material and organic compounds (hereinafter referred to as “organic light emitting material”) as a light emitting material because of having such a compound.
- organic light emitting material organic compounds
- Various organic EL devices using) have been proposed, and practical use has been attempted. Above all, organic EL devices can greatly reduce the applied E compared to inorganic EL devices, and the development of organic EL devices with higher performance is being actively pursued.
- the basic structure of an organic EL device is a structure in which an anode, a light-emitting layer, and a cathode are sequentially laminated. This organic EL device is often formed on a substrate. At this time, the positions of the anode and the cathode may be reversed. To improve the performance, a hole transport layer may be provided between the anode and the light emitting layer, or an electron injection layer may be provided between the cathode and the light emitting layer.
- the light-emitting layer is usually formed of one or more kinds of organic light-emitting materials, but may be formed of a mixture of the organic light-emitting material and a hole transport material and / or an electron injection material.
- the one located on the light extraction surface side is transparent in order to improve light extraction efficiency and because of the structure as a surface emitting element. Or a translucent thin film.
- the electrode located on the side opposite to the light extraction surface (hereinafter sometimes referred to as “opposite m3 ⁇ 4i”) It consists of a film (a thin film of metal, metal, metal, etc.).
- the organic EL device having the above structure is a current-driven light emitting device, and a high current must be passed between the anode and the cathode to emit light.
- the element generates heat during light emission, and if there is oxygen or moisture around the element, the oxidation of the element constituent material by the oxygen or moisture is accelerated, and the element is deteriorated.
- a typical example of deterioration of the device due to oxidation or water is the generation and growth of dark sbots.
- the dark spot is a light emission defect point.
- the organic EL element is driven, the oxidation of the component of the element proceeds, so that the existing dark spot grows, and eventually the dark spot spreads over the entire light emitting surface.
- JP-A-4-1363890 discloses that an organic EL element is held in an inert liquid compound made of liquid fluorinated carbon in order to effectively remove heat generated from the element when the element emits light.
- Japanese Patent Application Laid-Open No. 5-41281 discloses liquid fluorinated carbon as a method for removing water which is one of the causes of deterioration.
- a method for retaining an organic EL element in an inert liquefied liquid ⁇ containing a ⁇ 1 ⁇ 2 ⁇ agent such as synthetic zeolite in the same manner as the disclosed liquid fluorinated carbon is disclosed.
- JP-A-5-114486 discloses that a fluorocarbon oil (specifically, a liquid fluorinated carbon disclosed in the aforementioned JP-A-4-1363890) is provided on at least one of the anode and 1 ⁇ 1.
- a method is disclosed in which a heat radiation layer enclosing is enclosed is provided, and the heat generated during element driving is radiated from the heat radiation layer to extend the light emission life of the element.
- Deterioration due to moisture also occurs in inorganic EL elements, and as a method of preventing the deterioration in inorganic EL elements, the inorganic EL element is sealed while providing a predetermined gap between a pair of glass sheets. Further, there is a method of filling the gap with a protective liquid.
- U.S. Pat. No. 4,446,399 discloses that silicone oil or silicone grease is used as the protective liquid.
- U.S. Pat. No. 4,810,931 discloses that Perfluorinated inert liquid (specifically, the same as the liquid fluorinated carbon disclosed in the above-mentioned JP-A-4-1363890, Or something similar. ) The liquid temperature about 90 ⁇ : L20. C. It is disclosed that a gas obtained by degassing under an atmosphere pressure of about 10 Torr is used as the protective liquid.
- the heat generated from the organic EL element during light emission can be removed by using liquid fluorinated carbon, or the moisture entering the organic EL element during or after the sealing process of the organic EL element can be achieved.
- Removing ⁇ with an agent is one of the useful means to suppress the formation and growth of dark spots.
- liquid fluorinated carbon and fluorocarbon oil It dissolves gas very well, and the oxygen dissolved in the liquid fluorinated carbon or fluorocarbon oil has a greater effect on the formation and growth of dark spots than the moisture that has entered from outside. .
- the organic EL device is applied by the silicone oil or silicone grease. Is degraded or destroyed. Further, even when a method using a perfluorinated inert liquid degassed under the above specific conditions as the protective liquid was applied, it was difficult to sufficiently suppress generation and growth of dark spots in the organic EL device.
- An object of the present invention is to provide a method for sealing an organic EL element which can strongly suppress the growth of dark spozot in the organic EL element, and to provide a sealed organic EL element in which dark spozot growth is unlikely to occur. Disclosure of the invention
- the method for sealing an organic EL device of the present invention is characterized in that the dissolved oxygen it ⁇ is not more than lpp m on the outer periphery of the organic EL device in which the anode and the cathode are laminated at least via the light emitting layer.
- the inactive liquid layer is provided.
- the sealed organic EL device of the present invention that achieves the above object has an organic EL device and an inert liquid layer provided on the outer periphery of the organic EL device and having a dissolved oxygen of 1 ppm or less. It is assumed that BRIEF DESCRIPTION OF THE FIGURES
- FIG. 1 is a schematic diagram of a cross section of the sealed organic EL device obtained in Example 1
- FIG. 2 is a schematic diagram of a cross section of the sealed organic EL device obtained in Example 3.
- an inert liquid layer having a dissolved oxygen concentration of 1 ppm or less is provided on the outer periphery of the organic EL element as described above.
- the reason that the dissolved oxygen concentration of the inert liquid layer is limited to lppm or less is that if the dissolved oxygen concentration of the inert liquid layer exceeds lppm, it becomes difficult to strongly suppress the growth of dark spots. is there.
- the dissolved oxygen concentration is preferably as low as possible, but is practically preferably in the range of 0.01 to 1 ppm, particularly preferably 0.1 ppm or less.
- the inert liquid referred to in the method of the present invention is a liquid that is chemically and physically stable, and has, for example, stability such that it does not dissolve or dissolve even when it comes into contact with other substances.
- Specific examples of such an inert liquid include liquid fluorinated carbon such as perfluoroalkane, perfluoroamine and perfluoropolyether.
- Liquid fluorinated carbon is (1) excellent in electrical insulation (for example, the breakdown voltage of Demnum S-20 shown in Table 1 below is 72 kV when the sample thickness is 2.5 mm). (2) Since it has the property of not dissolving in water or oil, it does not substantially dissolve the layers constituting the organic EL element.
- the dissolved oxygen concentration of the inert liquid used in the method of the present invention is limited to 1 ppm or less as described above, and commercially available liquid fluorinated carbon is used. Since the dissolved oxygen concentration is much higher than 1 ppm, it cannot be used as it is in the method of the present invention. Therefore, for inert liquids with dissolved oxygen exceeding 1 ppm, the dissolved oxygen MJg should be reduced to 1 ppm or less by methods such as vacuum degassing at normal temperature, vacuum degassing by freezing, and inert gas replacement. Subject to the method of the invention. The method by which the dissolved oxygen is reduced is appropriately selected according to the type of the inert liquid to be used.
- the process of freezing the object to be dissolved an inert liquid that attempts to reduce the dissolved oxygen
- liquid nitrogen etc.
- a series of operations consisting of a step of evacuating the degassed object at i cr 2 Torr or less and a step of melting the degassed object in the state of evacuation are performed by the dissolved oxygen concentration in the degassed object. Until the value becomes 1 ppm or less.
- the objects to be degassed were Fluorinato FC-72, Fluorinato FC-84, Florinato FC-77, and Fluorinato FC-75 (manufactured by Sumitomo 3LEM).
- the target product can be obtained by repeating the above operation approximately 5 times or more.
- the inert gas replacement method for example, 0.1 to 1 liter / minute of inert gas (argon gas, nitrogen gas , Helium gas, neon gas, etc.) and bubbling for about 4 to 8 hours until the dissolved oxygen concentration in the degassed object becomes 1 ppm or less, to obtain the desired product.
- the freezing and vacuum method is preferred because the dissolved oxygen 3 ⁇ 4jg can be reduced by a relatively short operation.
- PA Full O b vapor pressure at 2 5 ° C in polyether many the following 1 0- 2 Torr, 2 5. From the vapor pressure at C is 1 0- 2 Torr following are Hikushi is evaporation ⁇ JE at room temperature, it and the possible amount of evaporation at room temperature is small, vacuum) ⁇ Datsukiho or inert gas In addition to the replacement method, the dissolved oxygen can also be reduced by a room temperature vacuum method.
- the dissolved oxygen concentration of the inert liquid vapor pressure at ° C is below 1 0- 2 Torr when reduced by atmospheric Yutakashin ⁇ vapor method, for example, degassing the subject held below 1 6 0 ° C things and evacuated below 1 0- 2 Torr until the dissolved oxygen concentration in the degassing object is below lp pm. If the kinematic viscosity of the object to be degassed is 65 cSt or less during the degassing operation, the dissolved oxygen can be degassed relatively easily. If the kinematic viscosity of the object to be degassed during the degassing operation is high, sufficient deaeration becomes difficult because oxygen and moisture are firmly trapped between the molecules.
- the deaeration operation becomes complicated in this case.
- the degassed object may be agitated and / or zeolite may be charged into the degassed object as necessary.
- zeolite it is preferable to use a zeolite made of a porous material such as unfired, glass, polytetrafluoroethylene (Teflon).
- Teflon polytetrafluoroethylene
- Connexion inert liquid which is a ⁇ in Okeru vapor pressure 10- 2 Tarr below, can also reduce the dissolved oxygen ⁇ in a short time of operation of the three methods described above, and degassing operation is simple In view of this, it is preferable to reduce the dissolved oxygen by the room temperature air
- inert liquids whose dissolved oxygen concentration can be easily obtained by a normal temperature vacuum degassing method are 1 ⁇ m or less include various perfluoroboryl ethers shown in Table 1 below.
- Demnum S-20 in Table 1 above has an average molecular weight of 2700, a breakdown voltage of 72 kV for a 2.5 mm thick sample, and a volume resistivity of about 20. It is 10 13 ⁇ cm under C.
- the structural formula is represented by the following formula (1).
- n 10 to 20, average molecular weight 2700
- the structural formula of Fomblin Z03 in Table 1 is expressed by the following formula (2).
- the structural formula of Galden H250 in Table 1 is represented by the following formula (3).
- the above-mentioned inert liquid is used.
- An inert liquid layer with a dissolved oxygen concentration of 1 ppm or less is provided on the outer periphery of the organic EL element.
- the inert liquid has a dissolved oxygen of 1 ppm or less and a water content of 10 ppm or less. It is particularly preferred that the content be less than ppm.
- the dissolved oxygen in the inert liquid is reduced to 1 ppm or less by the vacuum degassing method at room temperature, the dissolved oxygen concentration is reduced to 1 ppm or less by this method, or the deaeration operation is repeated and the dissolved oxygen concentration is increased.
- An inert liquid having an oxygen iUt of 1 ppm or less and a water content of 10 ppm or less can be obtained.
- the dissolved oxygen concentration in the inert liquid is reduced to 1 ppm or less by the inert gas replacement method, the dissolved oxygen concentration should be reduced to 1 ppm or less by this method and the publishing time should be slightly longer.
- an inert liquid having a dissolved oxygen concentration of 1 ppm or less and a water content of 10 ppm or less can be obtained. If the dissolved oxygen in the inert liquid is to be reduced to 1 ppm or less by the freezing vacuum method, the dissolved oxygen concentration should be reduced to 1 ppm or less or 1 ppm or less by this method. Is distilled in a vacuum to separate it into first, main, and last fractions, and by removing the first and last fractions, an inert liquid with a dissolved oxygen iUg of lppm or less and a water content of 1 Oppm or less is obtained. be able to.
- an inert liquid having a dissolved oxygen concentration of 1 PPm or less and a water content of 10 ppm or less it is possible to further suppress the growth of dark spots.
- the entirety of the organic EL element is immersed in an inert liquid filled in a container to form the inert liquid layer on the outer periphery of the organic EL element.
- the inert liquid layer it may be provided, when the organic EL element is formed on the substrate, it is more preferable to provide the inert liquid layer as follows.
- a housing material is formed outside the organic EL element formed above to cover the organic EL element in cooperation with the substrate while forming a gap between the organic EL element and the organic EL element.
- an inert liquid layer is provided by filling an inert liquid into a space formed by the substrate and the housing material. The filling of the inert liquid is performed by injecting the inert liquid into the space from a housing material or an injection port provided in advance, and the injection port is sealed after the injection of the inert liquid.
- the housing material is a cap-like material, a plate-like material (for example, counterbore), a sheet-like material, or a film having a concave portion having a large outer size and a larger inner size of the organic EL element to be sealed.
- the housing member is fixed on the substrate so as to form a practically closed space in cooperation with the above-mentioned member.
- the organic EL element to be sealed is in a state of being placed in the recess.
- the above-described packaging material may be provided for each organic EL element, or only one common element for all organic EL elements may be provided.
- the recess formed in the housing material may be one corresponding to each organic EL element, or one having a size capable of accommodating all the organic EL elements, It may be of a size that can accommodate a plurality of organic EL elements.
- the fixing of the housing material on the substrate can be performed using various adhesives such as an epoxy resin-based adhesive and an acrylate resin-based adhesive. Above all, those which hardly dissolve water and oxygen are preferable, and specific examples thereof include ARARDITE AR-R30 (a trade name of an epoxy resin-based adhesive manufactured by CHIPAGIGI CORPORATION). Also, various resins such as thermosetting resin and light-curing resin can be used in place of the above adhesive.
- the material of the housing material is preferably an electrically insulating material such as glass or polymer, and specific examples thereof include soda-lime glass, borosilicate glass, silicate glass, silica glass, and non-fluorescent glass.
- the organic EL element to be sealed is one that uses an insulated electrode wire for removing the m3 ⁇ 4l, or when the housing material is fixed to the upper surface, an electrically insulating adhesive or an electrically insulating resin is used.
- a housing made of a conductive metal such as stainless steel or an aluminum alloy may be used.
- an inert liquid layer is provided by filling an inert liquid in a space formed by a counterpart of the housing where the organic EL element is provided and the above-mentioned housing village
- the injection of the inert liquid may be performed in the atmosphere, but in order to prevent oxygen and moisture from dissolving in the inert liquid during the injection operation, use an inert gas such as a nitrogen gas atmosphere or an argon gas atmosphere. It is more preferable to carry out in an atmosphere. Moreover, you may perform by what is called a vacuum injection method.
- the above-mentioned vacuum injection method means that a space into which a liquid to be injected (hereinafter referred to as “injection liquid”) is to be injected is degassed, and liquid is injected into the space under this state. Or by degassing the space in which the infusate is to be injected, and reducing the difference between the pressure in the space and the pressure of the atmosphere surrounding the infusate (the former is lower.) It means a method of injecting an injection solution into the space by utilizing the same. Specific examples include the following methods (i) to (iii).
- an object (the whole thing having a space into which an injection liquid is to be injected) is put in an uncovered container, and this is placed in a vacuum container to depressurize the vacuum container. At this time, the object is placed so that the injection port for the injection liquid provided in the object is located near the bottom of the open container. Next, an infusion liquid is introduced into the uncovered container from outside the vacuum container, and the infusion liquid is poured into the container until the injection port is sufficiently immersed.
- the injection liquid is injected into the space by utilizing the difference between the pressure and the pressure in the space into which the liquid is to be injected (Japanese Unexamined Patent Publication (Kokai) No. 64-5759 / 1990, page 2, lower left, line 4 to line 3). The upper left corner of the page, see line 9.)
- the inert liquid When injecting the inert liquid, the inert liquid may be heated to increase its fluidity regardless of the type of injection method.
- the sealing of the injection port performed after the injection of the inert liquid is more preferably performed in an inert gas atmosphere such as a nitrogen gas atmosphere or an argon gas atmosphere than in the air.
- the injection port can be sealed by closing the injection port with the above-mentioned adhesive or the resin exemplified as used when the housing material is fixed to the substrate.
- the intended sealing of the present invention can be performed.
- the intended sealed organic EL device of the present invention can be obtained.
- sealing with a higher sealing effect can be performed, and a lower sealing effect can be obtained.
- a sealed organic EL element sealed in the above manner can be obtained.
- the adsorbent is for preventing oxygen and moisture from entering the organic EL element from the outside during or after the sealing of the organic EL element.
- the adsorbent is not particularly limited as long as it adsorbs oxygen and water. It is desirable that the material has properties that make it difficult to release oxygen and water once adsorbed.
- the shape of the adsorbent is not particularly limited, but a powdery adsorbent is preferred because the adsorbed area becomes larger.
- a metal selected from the group consisting of lithium, beryllium, potassium, sodium, magnesium, rubidium, strontium and calcium;
- activation i3 ⁇ 4L3 ⁇ 4j The activation process of the adsorbent differs depending on the type of adsorbent. Heating, vacuuming the adsorbent, leaving the adsorbent in an inert gas stream, cutting off the surface of the adsorbent, or a combination of two or more of these methods Can be.
- the activation treatment of the adsorbent is preferably performed while isolating the adsorbent from the outside air.
- the adsorbent in order to prevent the activity of the adsorbent after the activation treatment from being reduced, the adsorbent is isolated from the outside air until it is used to form a target inert liquid layer (containing the adsorbent). It is preferable to keep it.
- activation treatment by heating or vacuum bowing is performed with the adsorbent stored in a container that can block outside air, such as m with a vacuum cock. It is preferable to close the adsorbent after the activation treatment until it is used in a closed state with the outside air shut off. Good.
- the amount of the adsorbent can be appropriately selected according to the type. In general, the higher the amount of adsorbent used, the higher the adsorption effect.However, if the amount of adsorbent used is too large, (a) when the adsorbent is contained in the above-mentioned inert liquid to prepare a mixed solution, The fluidity is significantly reduced, making it difficult to form a target inert liquid layer (containing an adsorbent), or (b) the adsorbent may damage the organic EL device. When the mixture is prepared using an adsorbent having a small particle size, the mixture is prepared more than when the mixture is prepared using an adsorbent having the same weight and a larger particle size.
- the formation of the target inert liquid layer (containing adsorbent) becomes more difficult, but the smaller the particle size, the larger the adsorbent Since the effective surface area is larger than that of the agent, the adsorption amount is also large. Therefore, just because the amount (weight) of the adsorbent used is small does not necessarily mean that the sealing effect is small.
- the preferred amount of the adsorbent used depends on the type and particle size of the adsorbent, but is within the range of 1 mg to 10 g of the inert liquid described above, more preferably 1 mg to 10 g of Wi. It is generally in the range of 30 mg to 3 g per milliliter of inert liquid.
- the inert liquid used when forming the target inert liquid layer using the inert liquid containing the adsorbent has a dissolved oxygen concentration higher than 1 ppm before the adsorbent is contained.
- the dissolved oxygen concentration may be reduced to 1 ppm or less due to the inclusion of the adsorbent.However, in order to provide an inert liquid layer with a higher sealing effect, It is preferable that the dissolved oxygen concentration at the stage is already 1 ppm or less.
- the inert liquid used in this case a liquid in which the dissolved oxygen iiig has been reduced to 1 ppm or less by the above-described methods such as the normal temperature vacuum degassing method, the freeze vacuum degassing method, and the inert gas replacement method is used. Is preferred.
- an inert liquid layer When an inert liquid layer is formed around the organic EL element using an inert liquid containing an adsorbent, the entire organic EL element must be placed in an inert liquid (containing the adsorbent) filled in a container.
- An inert liquid layer may be provided on the outer periphery of the organic EL device by immersion, but when the organic EL device is formed on S
- a nodding material is formed to cover the organic EL element in cooperation with one's own while forming a gap between the organic EL element and the organic EL element. It is preferable to provide an inert liquid layer by, for example, filling an inert liquid (containing an adsorbent) into a space formed by the above-mentioned counterpart and the above-mentioned housing material.
- the following methods (A) and (B) are specific examples of the method of providing the above-mentioned inert liquid layer on the outer periphery of the organic EL element using a housing material.
- the mixed solution After preparing a mixed solution by mixing an adsorbent and an inert liquid, the mixed solution is mixed with an organic EL element and a housing material for covering the organic EL element above the organic EL element.
- an inert liquid layer When an inert liquid layer is provided by this method, the above mixed solution should not be prepared in the atmosphere, but in a dry inert gas atmosphere (nitrogen gas atmosphere, argon gas atmosphere, etc.). It is preferable to perform the treatment in a glove box whose atmosphere has been replaced with an active gas.
- an inert liquid (containing no adsorbent) may be poured into the container containing the adsorbent, or an inert liquid (containing no adsorbent) may be poured into the container containing the adsorbent.
- the adsorbent may be put in the container that contains it.
- a separate container for preparing the mixed solution is prepared separately, and the container is filled with the adsorbent.
- the adhesive and the inert liquid may be added simultaneously or separately.
- the formation of the target inert liquid layer using the above-mentioned mixed liquid is performed from the above-mentioned substrate on which the organic EL element is provided or the injection port provided in advance on the housing material covering the organic EL element on the substrate.
- the method can be carried out by filling the above-mentioned mixed liquid into the above-mentioned space, and sealing the above-mentioned inlet after filling.
- the formation of the inert liquid layer is also preferably performed in a dry inert gas atmosphere.
- This method uses a highly fluid mixture (an inert liquid containing an adsorbent). It is suitable for providing an active liquid layer.
- the method further below (bl) ⁇ (b3) of it can be divided into three, the formation of any your Some inert liquid layer is preferably carried out in a dry inert gas atmosphere c (bl)
- a housing material is provided on the substrate, and the substrate or the substrate is provided.
- An inert liquid layer (not containing an adsorbent) is filled into the above-mentioned space from an injection port provided in advance in the housing material to provide an intended inert liquid layer.
- the inlet is sealed after filling with an inert liquid (containing no adsorbent).
- An adsorbent is placed in a concave part of the housing material that is involved in the formation of the space, and after the housing material is provided on the substrate on which the organic EL element is provided, the substrate or the housing is provided.
- the intended inert liquid layer is provided by filling the above space with an inert liquid (containing no adsorbent) from an injection port provided in advance in the material. The inlet is sealed after filling with an inert liquid (containing no adsorbent).
- a housing material is provided on the substrate on which the organic EL element is provided to form the above-described space, and the adsorbent and the inert liquid (adsorbed from the inlet provided in advance in the housing material or from the inlet provided above).
- the desired inert liquid layer is provided by placing the desired inert liquid layer in the above space in any order. The inlet is sealed after filling with the adsorbent and inert liquid (containing no adsorbent).
- the device configuration of the organic EL device to be sealed in the method of the present invention is not particularly limited, and organic EL devices having various device configurations can be used. Therefore, the organic EL device of the present invention also has various device configurations.
- the light-emitting layer is usually formed of one or more kinds of organic light-emitting materials, but may be formed of a mixture of the organic light-emitting material and a hole transport material and / or an electron injection material.
- a protective layer may be provided on the outer periphery of the element having the above-described layer structure so as to cover the element and prevent moisture from entering the element.
- These organic EL elements are usually formed by sequentially laminating each layer including an anode and a cathode on a substrate, but in some cases, a layer is not used.
- the anti-reflective material is made of a substance that gives at least a high property (approximately 80% or more) to the luminescence (EL light) from the organic EL element.
- transparent glass, transparent plastic, and quartz A plate-like material, a sheet-like material, or a film-like material made of such as above is used.
- anode Various materials can be used for the anode, the cathode, the light emitting layer, the hole transporting J1, the electron injecting layer, and the protective layer, respectively.
- a metal, an alloy, an electrically conductive compound having a large work function (for example, 4 eV or more), or a mixture thereof is preferably used as the material.
- Specific examples include metals such as gold and nickel, and dielectric transparent materials such as Cul, ITO, SnOa, and ⁇ .
- the anode SUP depends on the material, but is usually 1 ⁇ ⁇ ! It can be appropriately selected within the range of 1 to 1 zm.
- metals, alloys, conductive materials, or mixtures thereof having a low work function are preferably used.
- Sodium as a specific example, sodium monopotassium ⁇ , magnesium, lithium, alloys or mixed ⁇ !, aluminum with magnetic Shiumu and silver, Al / Als ⁇ 3, indicator ⁇ arm, and rare earth metals such as ytterbium.
- the thickness of the anode depends on the material, but is usually 10 ⁇ ! ⁇ 1; can be selected appropriately within the range of m.
- the sheet resistance of each of the anode and the cathode is preferably several hundred ⁇ / b or less. Note that the size of the work function used as a reference when selecting the anode material and the thigh material is not limited to 4 eV.
- the material of the light-emitting layer is a light-emitting layer for an organic EL device, that is, a hole can be injected from an anode or a hole transport layer when an electric field is applied, and an electron can be injected from a cathode or an electron injection layer.
- Injection function that can perform injection
- transport function that moves injected charge (at least one of electron and hole) by the force of electric field
- light emission that provides a field of recombination of electron and hole and leads to light emission
- Any material can be used as long as it can form a layer having a function and the like.
- benzothiazole-based benzoimidazole-based
- benzoxazole-based fluorescent whitening agents gold-chelated oxinoid compounds
- gold-chelated oxinoid compounds gold-chelated oxinoid compounds
- styrylbenzene-based compounds and distyryl virazine derivatives.
- a polyphenyl compound a 12-phthalopeninone, a 1,4-diphenyl-1,3-butene, a 1,1,4,4-tetraphenyl-1,3-butadiene, a naphthene imide derivative, Metal complexes of perylene derivatives, oxadiazole derivatives, aldazine derivatives, virazirine derivatives, cyclopentene derivatives, pyrrolovirol derivatives, styrylamine derivatives, coumarin-based ⁇ , aromatic dimethylidin compounds, and 8-quinolinol derivatives.
- the thickness of the light emitting layer is not particularly limited, it is usually appropriately selected in the range of 5 nm to 5/1 m.
- the material of the hole transport layer may be any material that has either a hole transport property or an electron barrier property. Specific examples thereof include a triazole derivative, an oxaziazole derivative, an imidazo'l derivative, a polyarylalkane derivative, a pyrazoline-derived villazolone-derived phenylenediamine derivative, an arylamine derivative, an amino-substituted chalcone derivative, and an oxazole.
- the thickness of the hole transport layer is not particularly limited, but is usually in the range of 5 nm to 5 m. 3 ⁇ 4S is selected.
- the hole transport layer may have a single-layer structure composed of one or more of the above-described materials, or may have a multi-layer structure composed of multiple layers of the same yarn or different types.
- the electron injecting layer only needs to have a function of transmitting electrons injected from the cathode to the light emitting layer.
- the material include nitro-substituted fluorenone-derived anthraquinodimethane derivatives and diphene.
- Heterocyclic tetracarboxylic anhydrides such as dilquinone derivatives, thiovirandioxide derivatives, naphthalene perylene, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane derivatives, anthrone derivatives, oxaziazol derivatives, and 8-quinolinol derivatives
- Examples include metal complexes, metal-free phthalocyanines and metal phthalocyanines, those whose terminals are substituted with an alkyl group and a sulfone group, and distyryl virazine derivatives.
- the electron injection layer is not particularly limited, it is usually appropriately selected in the range of 5 nm to 5 m.
- the electron injection layer may have a single-layer structure composed of one or more of the above-mentioned materials, or may have a multilayer structure composed of a plurality of layers of the same or different kinds.
- the ⁇ ! Complex of an 8-quinolinol derivative can be used as a material for the light emitting layer as described above, and can also be used as a material for the electron injection layer.
- Specific examples of the ⁇ ! Complex of the 8-quinolinol derivative include tris (8-quinolinol) aluminum, bis (8-quinolinol) magnesium, bis (ben V-18-quinolinol) ⁇ 1 ⁇ , bis (2-methyl-8- Quinolinyl) aluminium moxide, tris (8-quinolinol) indium, tris (5-methyl-8-quinolinol) aluminum, 8-quinolinol lithium, tris (5-chloro 8-quinolinol) gallium, bis (5-crotinol) 8-quinolinol) calcium, tris (5, 7-dichlorol 8-quinolinol) aluminum, tris
- the material of the protective layer include a copolymer obtained by copolymerizing a monomer mixture containing tetrafluoroethylene and at least one comonomer.
- Copolymer polyethylene, polypropylene, polymethyl methacrylate, polyimide, polyurea, polytetrafluoroethylene, polychlorinated trifluoroethylene, polydichlorodifluoroethylene, chlorotrifluoroethylene and dichlorodifluoroethylene Copolymerization
- the method for forming each layer (including the anode and the cathode) constituting the organic EL element to be sealed is not particularly limited.
- the method of forming the anode, cathode, light emitting layer, hole transport layer, and electron injection layer depends on the material used to form each layer, for example, vacuum evaporation, spin coating, casting, spaddling, and LB. However, it is preferable to apply a method other than the sputtering method (a vacuum deposition method, a spin coating method, a casting method, an LB method, etc.) for the light emitting layer.
- the light emitting layer is particularly preferably a molecular deposition film.
- the molecular deposition film is a thin film formed by deposition from a material in the m1 ⁇ 2 state ⁇ / or a film formed by solidification from a material compound in a solution state or a liquid phase state. Films can be distinguished from thin films (accumulated molecular films) formed by the LB method by differences in the cohesive structure and higher-order structure, and the resulting functional differences.
- a coating solution is prepared by dissolving a binder such as a resin and a material into a solvent.
- vacuum deposition method spin coating method, sputtering method, casting method, MBE (molecular beam irradiation), cluster ion beam method, ion plating method, plasma polymerization method (high frequency excitation ion plating method) , Reactive A power ring method, a plasma CVD method, a laser CVD method, a thermal CVD method, a gas source CVD method and the like can be applied.
- each layer can be appropriately changed depending on the material used. If a vacuum evaporation method is used to form each layer constituting the organic EL element, the organic EL element can be formed only by the vacuum evaporation method, which is advantageous in simplifying equipment and shortening production time. It is.
- the sealed organic EL device of the present invention which is sealed by providing the above-described inert liquid layer on the outer periphery of the above-described organic EL device to be sealed, dark spots are generated due to the presence of the inert liquid layer. And the life of the device is long because the growth of dark spozot is strongly suppressed.
- a transparent support substrate was prepared by depositing an ITO film with a mff of 100 nm on top of 25 mm x 75 mm x 1.1 mm glass Si by vapor deposition. .
- the light transmittance of this substrate was measured with a UV-31 OOPC manufactured by Shimadzu Corporation and found to be about 80% in the wavelength range of 400 to 600 nm.
- This substrate was subjected to ultrasonic cleaning for 5 minutes in isobrovir alcohol and then for 5 minutes in pure water, and further subjected to UV ozone cleaning for 10 minutes using an apparatus manufactured by Samcoin Yuichi National Laboratory. .
- the hole transport layer having a thickness of 60 nm was formed by vapor deposition on the IT film at a deposition rate of 0.1 to 0.3 nmZs.
- the reaction temperature at this time was room temperature. This without taking out from the vacuum chamber and subsequently, heating the baud bets DP VB i containing up to 240 e C to the hole transporting layer, deposition 3 ⁇ 4 a DPVBi ⁇ 0. 1 ⁇ 0. ItilS at 3 nm / s Evaporated on the hole transport layer to form an il 40 nm light emitting layer.
- the temperature at this time was also room temperature.
- Alq 3 tris (8-quinolinol) aluminum
- the pressure in the vacuum chamber was reduced to lxlO- 4 Pa, and the boat containing Alq 3 was heated to 230 ° C, and Alq 3 was deposited on the light emitting layer at a deposition rate of 0.01 to 0.03 nm / s.
- the electron injection layer of IIP20nm was formed by vapor deposition.
- silver was deposited on the electron injection layer at a deposition rate of 0.1 nm / s at the same time as magnesium, and magnesium was deposited on the electron injection layer at a deposition rate of 1.4 nm / s to mix magnesium and silver.
- a counter electrode made of metal and having a thickness of 150 nm was formed. The reflectivity of the counter electrode was measured by UV-31 OOPC manufactured by Shimadzu Corporation and found to be 80% in the wavelength range of 400 to 600 nm.
- This organic EL device has an ITO film as an anode, a TPD layer as a hole transport layer, a DPVBi layer as a light emitting layer, an Alq 3 layer as an electron injection layer, And a magnesium-silver mixed metal layer as an opposing m3 ⁇ 4 (P-polarized).
- Part of the IT ⁇ film and part of the magnesium-silver mixed metal layer also serve as electrode wires for extracting electrodes, and the size of the light emitting layer in plan view is 6 mm ⁇ 10 mm.
- PA Full O Ropo Riete Le (Daikin Industries Ltd. of Demnum S- 20 (trade name as an inert liquid prior to adjust the dissolved oxygen iij ⁇ ; 25 ° vapor in C pressure 10- 6 Torr, 25 ° C Kinematic viscosity at 53 cSt)), put an appropriate amount of this Demnum S-120 into a glass container with a vacuum coke, and use this sample container and a vacuum pump with a diffusion pump (ULVAC VPC- made by Japan Vacuum Engineering Co., Ltd.). 050) using a flange.
- Demnum S- 20 trade name as an inert liquid prior to adjust the dissolved oxygen iij ⁇ ; 25 ° vapor in C pressure 10- 6 Torr, 25 ° C Kinematic viscosity at 53 cSt
- polytetrafluoroethylene (Teflon) zeolite is inserted into Demnum S-20 in the sample container, and the inside of the sample container is brought to 10 to 4 Torr while stirring at room temperature. Vacuum was applied, and dissolved oxygen was exhausted by the cold air deaeration method for about 30 minutes until foaming disappeared.
- the concentration of dissolved oxygen in the inert liquid thus prepared was 0.05 ppm, and the amount of water in the inert liquid was 5 ppm.
- SUD-1 trade name of the measuring device manufactured by Central Science Co., Ltd.
- an inert liquid on a part of the sensor of the above device in a glove box in which the atmosphere is replaced with nitrogen gas. was flowed at a constant flow rate of 50 milliliters / minute, and after about 20 seconds, the measured value was read after the displayed value had stabilized.
- the amount of water in the inert liquid was measured by Karl Fischer titration.
- This housing material has one recess with an inner dimension of 13 mm x 13 mm x lmm and an outer dimension of 15 mm x 15 mm x 1.8 mm.
- an inlet for injecting an inert liquid is provided at the bottom of the recess of the housing material.
- the organic EL element to be sealed is accommodated in the recess, and the glass member on which the organic EL element is formed and the housing material are bonded with an epoxy resin-based adhesive (Chipagagi Co., Ltd.).
- the organic EL element is located in the space formed by the recessed part and the housing of the housing material, and the organic EL element is not in contact with the housing material. .
- After leaving it for 3 hours to solidify the adhesive it was vacuum dried using a vacuum desiccator. After vacuum drying, transfer the atmosphere into a glove box in which the atmosphere has been replaced with nitrogen gas. In this glove box, inject the inert liquid prepared in (1) above from the inlet provided in the housing material.
- the above-mentioned inert liquid was filled in the space formed by the concave portion and the opposite surface of the housing material. After filling with the inert liquid, close the injection port with an epoxy-based adhesive (ARARDITE AR-R30 manufactured by Ciba Geigy) in the above-mentioned glove box, and leave it in the glove box for about 3 hours until the adhesive solidifies. Left.
- an epoxy-based adhesive ARARDITE AR-R30 manufactured by Ciba Geigy
- FIG. 1 shows a schematic cross section of the sealed organic EL device.
- the encapsulated organic EL device 1 of the present invention obtained above is provided on the outer periphery of the organic EL device 10 to be encapsulated by the inert liquid comprising the inert liquid prepared in (1) above.
- An ionic liquid layer 20 is provided.
- the organic EL element 10 to be sealed is composed of an ITO film 12 as an anode, a TPD layer 13 as a hole transport layer, a DPVBi layer 14 as a light emitting layer, and an Alq 3 layer as an electron injection layer on a glass substrate 11 15 and a magnesium-silver mixed ⁇ layer 16 as a counter electrode (P-electrode).
- a part 12a of the ITO film 12 and a part 16a of the magnesium-silver mixed metal layer 16 serve as electrode wires for taking out electrodes.
- the organic EL element 10 to be sealed is located in the space formed by the concave portion of the housing material 18 fixed on the glass substrate 11 by the epoxy resin system 17 and the above-mentioned glass plate 11, and is located in this space. Is filled with the inert liquid prepared in (1) above. As a result, an inert liquid layer 20 is formed on the outer periphery of the organic EL element 10. The inert liquid was injected from an injection port 19 provided in the housing material 18, and the injection port 19 was sealed with an epoxy resin adhesive 1 ⁇ a after the injection of the inert liquid. I have. (3) Evaluation of sealing effect
- a direct current power supply is connected to the sealed organic EL device obtained in (2) above via the two electrode wires of the organic EL device so that the initial luminance becomes 100001 / m 2 at 25 in the atmosphere. Was turned on. At this time, the current value was 0.56 mA and the voltage value was 9 V. The luminance was measured using a color difference meter (trade name: CS-100, manufactured by Minoru Yu Camera).
- non-light-emitting area ratio (Hereinafter referred to as “non-light-emitting area ratio”) was 0.43%. The diameter of one dark spot was found to be 18.4 im.
- the non-light-emitting area ratio was obtained by the same method as described above, and at the same time, the same dark spot diameter as that described above was obtained. Furthermore, the growth of the dark spot was defined as the diameter increase per hour, and the value was obtained. Table 2 shows the results.
- Example 2 sealing was performed under the same conditions as in Example 1 except that an inert liquid layer was formed around the organic EL element to be sealed with this inert liquid, to obtain a sealed organic EL element.
- the sealing effect was evaluated in the same manner as in Example 1 (3).
- the second calculation or measurement of the non-light-emitting area ratio and the diameter of the dark spot was performed 124 hours after the start of energization. The results are shown in Table 2.
- Example 2 the same as in Example 1 except that an inert liquid layer was formed around the organic EL element to be sealed with the inert liquid. Sealing was performed under the conditions to obtain a sealed organic EL device. The sealing effect of this sealed organic EL device was evaluated in the same manner as in mi (3). However, the second calculation or measurement of the non-emission area ratio and the diameter of the dark spot was performed 136 hours after commencement of communication. Table 2 shows the results.
- Example 1 use the perfluoropolyether (Demnum S-20 (trade name) manufactured by Daikin Industries, Ltd.) used in Example 1 without vacuum degassing, and seal with this inert liquid.
- An inert liquid layer was formed around the target organic EL device Sealing was performed under the same conditions as in Example 1 except for -2ti- to obtain a sealed organic EL device.
- the concentration of dissolved oxygen in the above inert liquid was 8.0 ppm, which was out of the range of the present invention.
- the sealing effect of this sealed organic EL device was evaluated in the same manner as in Example 1 (3). However, the second calculation or measurement of the non-light-emitting area ratio and the diameter of the dark spot was performed 115 hours after the start of energization. Table 2 shows the results.
- Non-light area ratio (%) Direct of dark spots (um) Growth rate of dark spots
- Example 1 0.43 0.5 0.5 1 1 8.4 20.1 1.22 X 10 2
- Example 2 0.43 0.59 1 8.4 1 9.1 4.6 1 X 10 3
- Comparative example 1 0.45 3.9 1 8. 3 45.7 2.21 x 1 0
- "'Comparative example 20.42 1 2.3 18.5 1 2 1.9 7.60 x 1 0' Comparative example 30.46 1 2.41 8.8 82.5 5.55 X 10 1
- “after the specified time” means “139 ⁇ * ⁇ i / i] ⁇ ⁇ from the beginning of the communication.
- Time [3 ⁇ 4I 'after rj, and “after a predetermined ⁇ ,' ⁇ u” in Comparative Example 1 usually means that after 12:00 hours from the beginning of fJH, ll / f
- over” means 136 hours after the start of power supply, and “after a predetermined time” in Comparative Example 3 means 115 hours after the start of power supply.
- each of the sealed organic EL devices obtained in ⁇ Example 1 to ⁇ Example 2 had a non-light-emitting area ratio and a dark spot diameter even after 139 hours or 152 hours from the start of energization. Little change from the initial value, dark spot formation: 3 ⁇ 43 ⁇ 43 ⁇ 4 is also slow. From these facts, it can be seen that each inert liquid layer formed in Example 1 and Example 2 strongly suppressed the growth of dark spots.
- Example 1 (1) An inert liquid having a dissolved oxygen content of 0.05 ppm and a water content of 5 ppm was prepared in the same manner as in Example 1 (1).
- Activated alumina (produced by Hiroshima Wako Pure Chemical Co., Ltd., particle size: about 300 mesh) is prepared as an adsorbent, and an appropriate amount of this activated alumina is placed in a glass sample container with a vacuum coke. And were connected using a flange.
- a housing material of the same shape as the housing material used in mi (2) was prepared, and this housing material and the organic EL element to be sealed were bonded in the same manner as in Example 1 (2). Thereafter, the product was vacuum-dried using a vacuum desiccator, and the product after the vacuum drying was transferred into a glove box purged with dry nitrogen gas. In addition, the sample container containing the inert liquid prepared in (1) above, The sample container containing the adsorbent activated in (2) was transferred into the above glove box.
- a predetermined amount of the adsorbent was added to the sample container containing the inert liquid, and the mixture was stirred to prepare an inert liquid containing the adsorbent (hereinafter, referred to as a “mixed liquid”).
- This mixture contains 50 Omg of adsorbent per milliliter of inert liquid and its dissolved oxygen concentration is less than 1 ppm.
- the mixed solution was injected from an injection port provided in the housing material, and the space formed by the recesses and the walls of the housing material was filled with the mixed solution.
- the above-mentioned inlet was closed with an epoxy-based adhesive (Araldite AR-R30 manufactured by Ciba-Geigy Co., Ltd.) in the above-mentioned glove box, and left in the glove box for about 3 hours until the adhesive was solidified. .
- an epoxy-based adhesive Aldite AR-R30 manufactured by Ciba-Geigy Co., Ltd.
- FIG. 2 shows a schematic cross section of the sealed organic EL device.
- the sealed organic EL device 30 obtained above is provided around the organic EL device 10 to be sealed with the inert liquid 3 la prepared in (1) above and the above (2).
- An inert liquid layer 31 made of a mixed liquid (an inert liquid containing an adsorbent) with an adsorbent 31b that has been activated with SfLS is provided.
- the same members as those in the sealed organic EL element 1 shown in FIG. 1 are denoted by the same reference numerals as those in FIG.
- Mg powder manufactured by Kojundo Chemical Laboratory Co., Ltd., particle size: 80 mesh or less
- the activation treatment was performed on the Mg powder as follows.
- Mg powder is placed in a beaker, a 1M aqueous hydrochloric acid solution is placed in the beaker, left for a few minutes, then filtered, and the residue (Mg powder) is rinsed with a sufficient amount of anhydrous ethanol. Transfer the residue (Mg powder) after rinsing to a glass sample container equipped with a vacuum cock, and close the container of the container. All operations up to this point are performed in a glove box with dry nitrogen gas flowing.
- Example Vacuum is performed in the same manner as in 1. The evacuation at this time is performed at room temperature without heating the portion of the sample container containing the Mg powder with a heater.
- the organic EL element was sealed in the same manner as in Example 3, except that the Mg powder that had been activated as described above was used as the adsorbent, and at the same time, the intended sealed organic EL element was obtained. .
- the inert liquid layer at this time contains 50 mg of the adsorbent per milliliter of the inert liquid, and the dissolved oxygen concentration is 1 ppm or less.
- the sealing effect of the above sealed organic EL device was evaluated in the same manner as in Example 3 (4). Table 3 shows the results.
- the organic EL was prepared in the same manner as in Example 3, except that perfluoropolyether (Demnam S-20 (trade name) manufactured by Daikin Industries, Ltd.) was used as the inert liquid without being noticed.
- the device was sealed.
- Activated alumina manufactured by Hiroshima Wako Pure Chemical Co., Ltd .: particle size of about 300 mesh
- the device was sealed.
- the dissolved oxygen in the mixture used to form the inert liquid layer is based on the fact that the oxygen adsorbed by the adsorbent has been dissolved into the inert liquid. It was out of the specified range.
- Non-light emitting area ratio (%) Dark spot diameter ( ⁇ m)
- the sealed organic EL device obtained in Reference Example 1 the temporal increase of the non-light-emitting area ratio and the growth of dark spots over time were caused by the sealed organic EL devices obtained in Comparative Examples 4 to 5. Although it is strongly suppressed as compared with the EL element, its sealing effect is low as compared with the sealed organic EL elements obtained in Examples 3 to 5.
- the present invention makes it possible to provide an organic EL device having a long device life.
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69524429T DE69524429T2 (de) | 1994-09-08 | 1995-09-05 | Verfahren zur abdichtung eines organischen elektrolumineszenten elements und organisches elektrolumineszentes element |
US08/793,932 US5962962A (en) | 1994-09-08 | 1995-09-05 | Method of encapsulating organic electroluminescence device and organic electroluminescence device |
EP95930701A EP0781075B1 (en) | 1994-09-08 | 1995-09-05 | Method for sealing organic el element and organic el element |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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JP6/214718 | 1994-09-08 | ||
JP21471894A JP3254335B2 (ja) | 1994-09-08 | 1994-09-08 | 有機el素子の封止方法および有機el素子 |
JP18596895A JP3795556B2 (ja) | 1995-07-21 | 1995-07-21 | 有機el素子の封止方法および有機el素子 |
JP7/185968 | 1995-07-21 |
Publications (1)
Publication Number | Publication Date |
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WO1996008122A1 true WO1996008122A1 (fr) | 1996-03-14 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/JP1995/001764 WO1996008122A1 (fr) | 1994-09-08 | 1995-09-05 | Procede d'enrobage d'un element electroluminescent organique et d'un autre element electroluminescent organique |
Country Status (4)
Country | Link |
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US (1) | US5962962A (ja) |
EP (1) | EP0781075B1 (ja) |
DE (1) | DE69524429T2 (ja) |
WO (1) | WO1996008122A1 (ja) |
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WO1998047189A1 (de) * | 1997-04-11 | 1998-10-22 | Robert Bosch Gmbh | Elektrolumineszierendes bauelement |
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Also Published As
Publication number | Publication date |
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DE69524429T2 (de) | 2002-05-23 |
US5962962A (en) | 1999-10-05 |
DE69524429D1 (de) | 2002-01-17 |
EP0781075A4 (en) | 1997-11-19 |
EP0781075A1 (en) | 1997-06-25 |
EP0781075B1 (en) | 2001-12-05 |
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