WO2007119473A1 - 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、照明装置及びディスプレイ装置 - Google Patents
有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、照明装置及びディスプレイ装置 Download PDFInfo
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Definitions
- ORGANIC ELECTRIC LIGHT EMITTING ELEMENT METHOD FOR PRODUCING ORGANIC ELECTRIC LIGHT EMITTING ELEMENT, LIGHTING DEVICE, AND DISPLAY DEVICE
- the present invention relates to an organic electoluminescence device, a method for manufacturing an organic electroluminescence device, an illumination device, and a display device.
- ELD electoric luminescence display
- inorganic electoluminescence devices and organic electroluminescence devices (hereinafter also referred to as organic EL devices).
- organic EL devices Inorganic eletroluminescence elements have been used as planar light sources, but in order to drive the light emitting elements, an alternating high voltage is required.
- an organic EL element has a configuration in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode.
- excitons Is an element that emits light using the emission of light (fluorescence / phosphorescence) when this exciton is deactivated, and can emit light at a voltage of several volts to several tens of volts. Since it is a self-emitting type, it has a wide viewing angle, and since it is a thin-film type complete solid-state device with high visibility, it is attracting attention from the viewpoints of space saving and portability.
- Patent No. 309379 6 discloses a technique for doping a stilbene derivative, a distyrylarylene derivative or a tristyrylarylene derivative with a trace amount of a phosphor to improve emission luminance and extend the lifetime of the device.
- — 264692 discloses a device having an organic light-emitting layer in which 8-hydroxyquinoline aluminum complex is a host compound and doped with a small amount of phosphor.
- JP-A-3-255190 discloses An element having an organic light-emitting layer in which an 8-hydroxyquinoline aluminum complex is used as a host compound and doped with a quinacridone dye is known. [0005]
- the generation ratio of singlet excitons and triplet excitons is 1: 3, so the generation probability of luminescent excited species Since the force S25% and the light extraction efficiency is about 20%, the limit of the external extraction quantum efficiency ( ⁇ ext) is set to 5%.
- the organic EL element is an all-solid element constituting a film of an organic material of about 1 beta m slight thickness 0.5 between the electrode and the electrode, yet relatively the emission of about 2V ⁇ 20V Because it can be achieved at a low voltage, it is a promising technology for next-generation flat displays and lighting.
- organic EL elements are based on a light-emitting phenomenon that utilizes deactivation of an organic material from an excited state to a ground state, the wavelength of blue or blue-green light, etc.
- a high voltage is required to excite the large gap.
- the excited state itself is located at a high level, the lifetime tends to be shorter than that of green or red light emission, which is greatly damaged when returning to the ground state, and in particular, light emission from the triplet excited state. This tendency becomes remarkable in phosphorescence emission using the.
- a method for example, refer to Patent Document 2
- AIBN azoisoptyronitrile
- a production method in which a polymerization reaction proceeds during film formation see, for example, Patent Document 3
- a production method in which a Diels-Alder reaction occurs between two molecules in the same layer for example, see Patent Document 4.
- Etc. can be mentioned, et al. Are.
- Each of the above techniques is a method for completing the polymerization reaction at the time of film formation or immediately after film formation (before attaching the cathode). From the practical viewpoint of improving the durability of the organic EL device, however, this is insufficient, and further element durability improvement technology is required.
- Patent Document 1 JP-A-5-271166
- Patent Document 2 Japanese Patent Laid-Open No. 2001-297882
- Patent Document 3 Japanese Unexamined Patent Publication No. 2003-73666
- Patent Document 4 Japanese Patent Laid-Open No. 2003-86371
- the present invention has been made in view of the above problems, and an object of the present invention is to provide an organic EL element, a lighting device, and a display device that exhibit high luminous efficiency and have a long lifetime. It is.
- an organic electoluminescence device having at least an anode and a cathode on a support substrate, and having an organic layer containing at least one reactive organic compound between the anode and the cathode.
- the organic electroluminescence is characterized in that the concentration of the reactive organic compound in the organic layer is not uniform at any time from the end of the production process to the start of energization. Sense element.
- the amount of the reactive organic compound present in the vicinity of the joint surface with the lower layer during the formation of the organic layer is greater than the amount of the reactive organic compound present in the vicinity of the other surface of the organic layer.
- an organic EL element a lighting device, and a display device that exhibit high luminous efficiency and have a long lifetime can be provided.
- FIG. 1 is a schematic configuration diagram of an organic EL full-color display device.
- the organic electoluminescence device (also referred to as an organic EL device) of the present invention has the structure described in any one of claims 1 to 10, and the configuration described in item 1. As a result, it was possible to obtain an organic electroluminescence device (organic EL device) with high external quantum efficiency and long device life (improved robustness).
- the present invention succeeded in obtaining a method for producing the organic EL element including a coating process, and a high-luminance display device and an illumination device including the organic EL element.
- the organic EL device of the present invention has at least one organic layer containing a reactive organic compound, and the device may have other organic layers as constituent layers.
- the vapor deposition method or the like using a conventionally known coating method may be used.
- the constituent layers may be formed by a technique in which a coating method and a vapor deposition method are mixed.
- the device performance can be controlled in the direction desired by the present inventors by causing the reaction to proceed by energizing the device. I was convinced that there was a possibility.
- the reactive organic compound is an unreacted polymerizable monomer or the like
- the polymerization reaction is advanced by an active radical or the like generated during use of the device, and the network polymer by the organic molecule is used. It was found that effects such as suppression of device deterioration by adjusting Tg (glass transition point) of the constituent layers were obtained.
- the emission wavelength of the organic EL device can be changed, deterioration of a specific wavelength can be suppressed, etc. I also found that it would be possible.
- the reactive organic compound according to the present invention all of the functional compounds contained in the constituent layers of the organic EL element (described in detail later) can be applied as the core of the reactive compound.
- a compound having a host compound, a light emitting dopant, etc., a hole transport material, an electron transport material, etc. in the light emitting layer described later as a mother nucleus, and a reactive substituent substituted on the mother nucleus. can be used.
- Examples of the reactive substituent include the groups shown below.
- the lower layer is not dissolved in the upper layer coating solution by resinizing the lower layer and degrading the solvent solubility. Can be made possible.
- the lower layer is completely converted into a resin, and the reactive organic compound remains in the lower layer as in the present invention. This is an unforeseeable discovery, and it is preferable not only to have a functional effect on the device, but also to have a reactive compound remaining. Therefore, the device manufacturing process is simplified compared to the conventional manufacturing process. It was also found that there is a merit in the process.
- an organic layer also referred to as an organic compound layer
- an organic compound layer containing at least one reactive organic compound according to the present invention
- concentration of the reactive organic compound in the organic layer is uniform.
- “non-uniform” means that the concentration of the reactive organic compound in the layer is not uniform.
- the amount of the reactive organic compound existing in the vicinity of one surface of the organic layer is A.
- the organic layer When the amount of the reactive organic compound existing in the vicinity of the other surface is B, the absolute value IA—BI of the difference between A and B is divided by A or A1 or B1 Of these, it is preferable that the content is 5% or more, and more preferable is a state where the content is 10% or more.
- in the vicinity of one surface means a position of about 3 from the surface layer of the surface when the thickness of the organic layer is equally divided, more preferably up to about 2 and even more preferably. Indicates positions up to about 1.
- a force that needs to secure an analysis area that can be analyzed by a general micro-region analysis method For that purpose, it is effective to cut a thin film diagonally.
- the area is enlarged by 1 / cos ⁇ ( ⁇ is the value obtained by subtracting the angle of the surface normal force cutting surface) compared to the case where the cross section is made perpendicular to the surface by cutting obliquely.
- the ultra-microtome generally used in the industry is used to incline and cut the blade of a glass knife, or the die-cut Wintes Psycus NN04 type is used to cut obliquely.
- a method for producing a surface can be mentioned.
- the distribution of double bonds is measured, but there are several means for measuring the distribution of double bonds. For example, with a microscopic infrared spectroscopic analysis, Raman spectroscopic analysis, or a labeling reagent that reacts specifically with a double bond and has a specific element.
- Double bonds are labeled, and the labeled elements are separated using an electron probe microanalyzer, X-ray photoelectron spectrometer, Auger electron spectrometer, time-of-flight secondary ion mass spectrometer, etc.
- a method of measuring a cloth or the like is a preferable analysis means.
- the constituent layers of the organic EL device of the present invention will be described.
- preferred specific examples of the layer structure of the organic EL element are shown below, but the present invention is not limited thereto.
- the light emitting maximum wavelength of the blue light emitting layer is preferably from 430 nm to 480 nm.
- the green light emitting layer preferably has a light emitting maximum wavelength of 510 nm to 550 nm, and the red light emitting layer has a light emitting maximum wavelength of 600 nm.
- a monochromatic light emitting layer in the range of ⁇ 640 nm is preferred, and a display device using these is preferred.
- a white light emitting layer may be formed by laminating at least three of these light emitting layers.
- a non-light emitting intermediate layer may be provided between the light emitting layers.
- the organic EL element of the present invention is preferably a white light emitting layer and is preferably a lighting device using these.
- the light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer, and the light emitting portion is within the layer of the light emitting layer. May be the interface between the light emitting layer and the adjacent layer.
- the total film thickness of the light emitting layer is not particularly limited, but it is possible to prevent the application of a high voltage unnecessary during the light emission, and the stability of the light emission color with respect to the driving current.
- the viewpoint power is preferably adjusted to a range of 2 nm to 5 / im, more preferably adjusted to a range of 2 nm to 200 nm, and particularly preferably lOnm to:! OOnm.
- a light emitting dopant or a host compound described later is formed by a known thinning method such as a vacuum deposition method, a spin coating method, a casting method, an LB method, or an ink jet method. can do.
- the light-emitting layer of the organic EL device of the present invention may contain a light-emitting host compound and at least one light-emitting dopant (such as a phosphorescent dopant (also referred to as a phosphorescent dopant) or a fluorescent dopant). preferable.
- a light-emitting dopant such as a phosphorescent dopant (also referred to as a phosphorescent dopant) or a fluorescent dopant.
- the host compound used in the present invention will be described.
- the host compound is a compound having a mass ratio of 20% or more in the light-emitting layer and phosphorescence at room temperature (25 ° C).
- Luminescence phosphorescence is defined as a compound with a quantum yield of less than 0.1.
- the phosphorescence quantum yield is less than 0.01.
- the mass ratio in the layer is 20% or more. It is preferable that it is above.
- known host compounds may be used singly or in combination.
- phosphine H compounds it is possible to adjust the movement of electric charges, and the organic EL device can be made highly efficient.
- multiple types of light emitting dopants which will be described later, it becomes possible to mix different types of light emission, thereby obtaining the desired light emission color.
- the light emitting host used in the present invention may be a conventionally known low molecular compound or a high molecular compound having a repeating unit, which may be a low molecular compound having a polymerizable group such as a bur group or an epoxy group.
- a compound (evaporation polymerizable light emitting host) may be used.
- Known host compounds that may be used in combination may have a hole transport ability and an electron transport ability.
- a compound that prevents the emission of light from being increased in wavelength and has a high Tg (glass transition temperature) is preferable.
- the light emitting dopant according to the present invention will be described.
- the light-emitting dopant according to the present invention includes a fluorescent dopant (also referred to as a fluorescent compound), phosphorus From the standpoint of obtaining an organic EL device having a higher power S and a higher luminous efficiency, the ability to use a light dopant (also referred to as a phosphorescent emitter, a phosphorescent compound, or a phosphorescent compound).
- a light emitting dopant sometimes simply referred to as a light emitting material used in a light emitting layer or a light emitting unit of an EL device, it is preferable to contain a phosphorescent dopant at the same time as containing the above host compound.
- the phosphorescent dopant according to the present invention will be described.
- the phosphorescent dopant according to the present invention is a compound in which light emission from an excited triplet is observed. Specifically, it is a compound that emits phosphorescence at room temperature (25 ° C). Although the yield is defined to be a compound of 0.01 or more at 25 ° C, the preferred phosphorescence quantum yield is 0.1 or more.
- the phosphorescence quantum yield can be measured by the method described in the fourth edition of Experimental Chemistry Course 7, Spectroscopy II, page 398 (1992 edition, Maruzen). Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence dopant according to the present invention achieves the above phosphorescence quantum yield (0.01 or more) in any solvent. Just do it.
- emission of phosphorescent dopants there are two types of emission of phosphorescent dopants in principle.
- One is the recombination of carriers on the host-rich compound in which carriers are transported, and the excited state of the host compound is generated.
- the energy transfer type is to obtain light emission from the phosphorescent dopant by transferring energy to the phosphorescent dopant, and the other is that the phosphorescent dopant becomes a carrier trap, and recombination of carriers occurs on the phosphorescent dopant and phosphorescence occurs.
- the carrier trap type in which light emission from the dopant can be obtained. In either case, the excited state energy of the phosphorescent dopant must be lower than the excited state energy of the host compound.
- the phosphorescent dopant can be appropriately selected and used as a known medium used for the light emitting layer of the organic EL device.
- the phosphorescent dopant according to the present invention is preferably a complex compound containing a group 8 to 10 metal in the periodic table of elements, more preferably an iridium compound, an osmium compound, or a platinum compound ( Platinum complex compounds), rare earth complexes, and most preferred are iridium compounds.
- a complex compound containing a group 8 to 10 metal in the periodic table of elements more preferably an iridium compound, an osmium compound, or a platinum compound ( Platinum complex compounds), rare earth complexes, and most preferred are iridium compounds.
- Platinum complex compounds Platinum complex compounds
- rare earth complexes rare earth complexes
- Fluorescent dopants include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylenes And dyes based on dyes, stilbene dyes, polythiophene dyes, and rare earth complex phosphors.
- the injection layer is provided as necessary, and includes an electron injection layer and a hole injection layer, and as described above, exists between the anode and the light emitting layer or hole transport layer and between the cathode and the light emitting layer or electron transport layer. May be.
- the injection layer is a layer provided between the electrode and the organic layer to reduce the driving voltage and improve the light emission luminance.
- the organic EL element and the forefront of its industrialization June 30, 1998) 2) Chapter 2 “Electrode Materials” (pages 123 to 166) of “The Company”), the hole injection layer (anode buffer layer) and the electron injection layer (cathode buffer layer). There is.
- anode buffer layer (hole injection layer)
- Examples include a phthalocyanine buffer layer represented by talocyanine, an oxide buffer layer represented by vanadium oxide, an amorphous carbon buffer layer, and a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene.
- cathode buffer layer (electron injection layer) The details of the cathode buffer layer (electron injection layer) are also described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium Metal buffer layer typified by aluminum, alkali metal compound buffer layer typified by lithium fluoride, alkaline earth metal compound buffer layer typified by magnesium fluoride, oxide buffer layer typified by aluminum oxide Etc.
- the thickness of the buffer layer (injection layer) is preferably in the range of 0.1 nm to 5 zm, although it depends on the material desired to be a very thin film.
- Blocking layer hole blocking layer, electron blocking layer>
- the blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above.
- Japanese Patent Application Laid-Open Nos. 11-204258 and 11 204359, and “The Forefront of Organic EL Devices and Their Industrialization” (published by NTS Corporation on November 30, 1998)
- the hole blocking layer has a function of an electron transport layer, and is composed of a hole blocking material having a function of transporting electrons and having a remarkably small ability to transport holes, and transports electrons. By blocking holes, the recombination probability of electrons and holes can be improved.
- the structure of the electron transport layer described later can be used as a hole blocking layer according to the present invention as required.
- the hole blocking layer of the organic EL device of the present invention is preferably provided adjacent to the light emitting layer.
- the hole blocking layer preferably contains the azacarbazole derivative mentioned as the above-mentioned host compound.
- the light emitting layer having the longest emission maximum wavelength is closest to the anode among all the light emitting layers.
- 50% by mass or more of the compound contained in the hole blocking layer provided at the position has an ionization potential of 0.3 eV or more larger than the host compound of the shortest wave emitting layer. Les.
- the ionization potential is defined by the energy required to emit an electron at the HOMO (highest occupied molecular orbital) level of a compound to the vacuum level, and can be obtained by the following method, for example.
- Gaussian98 (Gaussian98, Revision A. 11.4, MJ Frisch, et ai, Gaussian, Inc., Pitts Durg h PA, 2002.)
- the ionization potential can be obtained by rounding off the second decimal place of the value (eV unit converted value) calculated by structural optimization using B3LYPZ6-31G * as a keyword. The reason why this calculated value is effective is that there is a high correlation between the calculated value obtained by this method and the experimental value.
- the ionization potential can also be determined by a method of direct measurement by photoelectron spectroscopy. For example, a low energy electron spectrometer “Model AC-1” manufactured by Riken Keiki Co., Ltd. or a method known as ultraviolet photoelectron spectroscopy can be suitably used.
- the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material that has a function of transporting holes and a very small ability to transport electrons, and transports holes.
- the probability of recombination of electrons and holes can be improved.
- the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed.
- the film thickness of the hole blocking layer and the electron transporting layer according to the present invention is preferably 3 nm to:! OOnm, and more preferably 5 nm to 30 nm.
- the hole transport layer is made of a hole transport material having a function of transporting holes.
- a hole injection layer and an electron blocking layer are also included in the hole transport layer.
- the hole transport layer can be provided as a single layer or a plurality of layers.
- the hole transport material has any of the power of hole injection or transport and electron barrier property, and may be either organic or inorganic.
- triazole derivatives oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, virazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives
- Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
- Typical examples of aromatic tertiary amine compounds and styrylamine compounds include N, N, N ', N r —tetraphenyl _4, 4 ; — diaminophenyl; Bis (3-methylphenyl) -1- [1,1'-biphenyl] -1,4-diamin (TPD); 2, 2 bis (4 di-l-triaminophenyl) propane; 1,1-bis (4 di-l-triaminophenyl) cyclohexane; N, N, N ', N' -tetra-l-tri-yl 4, 4'-diaminobiphenyl; 1,1-bis (4-di-triarylaminophenyl) 4-phenyl hexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-) —P tolylaminophenyl) phenylmethane; N,
- a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
- Inorganic compounds such as p-type Si and p-type SiC can also be used as the hole injecting material and hole transporting material.
- the hole transport layer is formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. Can be formed.
- the thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 xm, preferably 5 nm to 200 nm.
- the hole transport layer may have a single layer structure composed of one or more of the above materials.
- a hole transport layer having a high p property doped with impurities may be used. Examples thereof are described in JP-A-4-297076, JP-A-2000-196140, 2001-102175, J. Appl. Phys., 95, 5773 (2004), etc. Can be listed.
- the electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer.
- the electron transport layer can be provided as a single layer or a plurality of layers.
- an electron transport material also serving as a hole blocking material
- Any material having a function of transmitting electrons injected from the electrode to the light-emitting layer may be used as the material, and any conventional compound known in the art can be selected and used.
- a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material.
- a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
- metal complexes of 8_quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-l-quinolinol) aluminum, tris (5,7-dive mouth_) 8_quinolinol) aluminum, tris (2-methyl_8_quinolinol) aluminum, tris (5-methyl_8_quinolinol) aluminum, bis (8-quinolinol) zinc (Znq) etc., and the central metal of these metal complexes Metal complexes replacing In, Mg, Cu, Ca, Sn, Ga or Pb can also be used as electron transport materials.
- methanolyl or metal phthalocyanine, or the terminal of them is an alkyl group or a sulfonic acid group.
- Those substituted with can also be preferably used as the electron transporting material.
- the distyrylvirazine derivative exemplified as the material for the light-emitting layer can also be used as an electron transport material.
- inorganic semiconductors such as n-type Si and n-type SiC can also be used. It can be used as an electron transport material.
- the electron transport layer is formed by thinning the electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. can do.
- a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. can do.
- the electron transport layer may have a single layer structure composed of one or more of the above materials.
- an electron transport layer having a high n property doped with impurities can be used.
- examples thereof include JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J. Appl. Phys., 95, 5773 (2004), etc. The one described in.
- an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
- electrode materials include metals such as Au, conductive transparent materials such as Cul, indium tinoxide (IT 0), SnO, and ZnO. IDIXO (In O Zn ⁇ )
- a material such as 2 2 3 that is amorphous and capable of producing a transparent conductive film may be used.
- these electrode materials can be formed into a thin film by vapor deposition or sputtering, and a pattern of the desired shape can be formed by a single photolithography method.
- a pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered.
- wet film-forming methods such as a printing system and a coating system, can also be used.
- the sheet resistance as the anode is preferably several hundred ⁇ or less.
- the film thickness Force depending on the material Usually selected in the range of 10 nm to 1000 nm, preferably 10 nm to 200 nm.
- a cathode having a work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof is used.
- electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium Z indium mixture, aluminum Z aluminum oxide. (A10) mixture, indium, lithium / aluminum mixture, rare earth metal, etc.
- a mixture of an electron injectable metal and a second metal which is a stable metal having a larger work function value than this, for example, a magnesium / silver mixture.
- a magnesium / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al 2 O 3) mixture, a lithium / aluminum mixture, aluminum and the like are suitable.
- the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. Further, the sheet resistance as the cathode is preferably several hundred ⁇ / mouth or less. The film thickness is usually selected from the range of 10 ⁇ to 5 ⁇ m, preferably 50 nm to 200 nm. In order to transmit the emitted light, if either one of the anode or the cathode of the organic EL element is transparent or translucent, the light emission luminance is advantageously improved.
- a transparent or translucent cathode can be manufactured by forming the above metal on the cathode with a film thickness of lnm to 20nm and then forming the conductive transparent material mentioned in the description of the anode thereon. By applying this, it is possible to produce a device in which both the anode and the cathode are transparent.
- a support substrate (hereinafter also referred to as a substrate, substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention, there is no particular limitation on the type of glass, plastic, etc., and it is transparent. Or opaque. In the case where light is extracted from the support substrate side, the support substrate is preferably transparent.
- a transparent support substrate preferably used, glass , Quartz, and transparent resin film.
- a particularly preferable support substrate is a resin film capable of giving flexibility to the organic EL element.
- polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellose diacetate, cenorelose triacetate, cenorelose acetate butyrate, and cenolate extract.
- Cellulose esters such as acetate propionate (CAP), cellulose acetate phthalate (TAC), cellulose nitrate, or their derivatives, polyvinylidene chloride, polybutyl alcohol, polyethylene butol alcohol, syndiotactic polystyrene, polycarbonate, Norbornene resin, polymethylpentene, polyether ketone, polyimide, polyethersulfone (PES), polyphenylene sulfide, polysulfones, polyether Luimide, polyether ketone imide, polyamide, fluororesin, nylon, polymethyl methacrylate, acrylic or polyarylates, Arton (trade name, made by JSR) or Apenole (trade name, made by Mitsui Chemicals) And cycloolefin-based resins.
- CAP acetate propionate
- TAC cellulose acetate phthalate
- cellulose nitrate or their derivatives
- polyvinylidene chloride poly
- an inorganic film, an organic film, or a hybrid film of the both may be formed on the surface of the resin film.
- the oxygen permeability measured by this method is 10 _3 ml / (m 2 '24h'MPa) or less, and the water vapor permeability is 10_ 5 g / (m 2 ' 24h) or less. Is preferred.
- any material may be used as long as it has a function of suppressing the intrusion of elements such as moisture and oxygen.
- silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.
- the method for forming the barrier film is not particularly limited.
- Force S described in JP-A-2004-68143 Particularly preferred is an atmospheric pressure plasma polymerization method.
- Examples of the opaque support substrate include metal plates such as aluminum and stainless steel, non-transparent resin substrates, ceramic substrates, and the like.
- the external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, more preferably 5% or more.
- the external extraction quantum efficiency (Q / o) the number of photons emitted outside the organic EL element / the number of electrons X I 00 flowed into the organic EL element.
- a hue improvement filter such as a color filter may be used in combination, or a color conversion filter that converts the emission color from the organic EL element into multiple colors using a phosphor may be used in combination.
- a color conversion filter When a color conversion filter is used, the maximum light emission of the organic EL element is preferably 480 nm or less.
- sealing means used in the present invention include a method of bonding a sealing member, an electrode, and a support substrate with an adhesive.
- the sealing member may be a concave plate shape or a flat plate shape as long as it is disposed so as to cover the display region of the organic EL element. Further, transparency and electrical insulation are not particularly limited.
- Specific examples include a glass plate, a polymer plate 'film, a metal plate' film, and the like.
- the glass plate include soda lime glass, barium strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, borosilicate glass, and quartz.
- the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
- the metal plate include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, anoleminium, magnesium, nickelo, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.
- a polymer film and a metal film can be preferably used because the device can be formed into a thin film.
- the polymer film is JIS K 7126-19 Oxygen permeability measured by a method according to 87 is 1 X 10 _3 ml / (m 2 '24h'MPa) or less, water vapor permeability measured by a method according to JIS K 7129-1992 (25 ⁇ 0 5 ° C, relative humidity (90 ⁇ 2)% RH) force 1 X 10 3 g / (m 2 '24h) or less.
- Sand blasting, chemical etching, or the like is used to process the sealing member into a concave shape.
- adhesives include photocuring and thermosetting adhesives having a reactive bur group of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanacrylic acid esters. Can be mentioned.
- adhesive-based heat and chemical curing types two-component mixing
- hot-melt type polyamide, polyester, and polyolefin can be mentioned.
- a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
- the adhesive can be cured from room temperature to 80 ° C.
- a desiccant may be dispersed in the adhesive.
- a commercially available dispenser may be used to apply the adhesive to the sealing part, or it may be printed like screen printing.
- the electrode and the organic layer may be coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer may be formed in contact with the support substrate to form a sealing film.
- a material for forming the film any material may be used as long as it has a function of suppressing intrusion of elements that cause deterioration of elements such as moisture and oxygen.
- silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.
- the method for forming these films is not particularly limited, for example, vacuum deposition, sputtering, reactive sputtering, molecular beam epitaxy, cluster single ion beam, ion plating, plasma polymerization, atmospheric pressure plasma weighting.
- a combination method, a plasma CVD method, a laser C VD method, a thermal CVD method, a coating method, or the like can be used.
- an inert gas such as nitrogen or argon, or an inert liquid such as fluorocarbon or silicon oil is used in the gas phase or liquid phase. Injection It is preferable to do. A vacuum is also possible. Also, it can seal hygroscopic compounds inside.
- Examples of the hygroscopic compound include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide), sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate).
- metal oxides for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
- sulfates for example, sodium sulfate, calcium sulfate, magnesium sulfate.
- metal halides eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide, etc.
- perchloric acids For example, barium perchlorate, magnesium perchlorate, etc. can be used, and anhydrous salts are preferably used in sulfates, metal halides and perchloric acids.
- a protective film or a protective plate may be provided on the outer side of the sealing film or the sealing film on the side facing the support substrate with the organic layer interposed therebetween in order to increase the mechanical strength of the element.
- the mechanical strength is not necessarily high. Therefore, it is preferable to provide such a protective film and a protective plate.
- a material that can be used for this the same glass plate, polymer plate 'film, metal plate' film, etc. that are used for the sealing can be used. It is preferable to use a single film.
- the organic EL element emits light inside a layer with a higher refractive index than air (refractive index of about 1.7 to 2.1), and only 15% to 20% of the light generated in the light emitting layer can be extracted. It is generally said that there is nothing. This is because light incident on the interface (transparent substrate-air interface) at an angle ⁇ greater than the critical angle causes total reflection and cannot be extracted outside the device. This is because the light undergoes total reflection between the light and the light, and the light is guided through the transparent electrode or the light emitting layer.
- a technique for improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate to prevent total reflection at the interface between the transparent substrate and the air (US Pat. No. 4,774,435) ), A method of improving the efficiency by giving the substrate a light condensing property (Japanese Patent Laid-Open No. 63-31 4795), a method of forming a reflective surface on the side surface of the element (Japanese Patent Laid-Open No. 1220394) ), A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the substrate and the light emitter (Japanese Patent Laid-Open No.
- these methods can be used in combination with the organic EL device of the present invention, but a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter.
- a method of forming a diffraction grating between any one of the substrate, the transparent electrode layer, and the light emitting layer (including between the substrate and the outside) can be suitably used.
- the low refractive index layer examples include air-mouth gel, porous silica, magnesium fluoride, and fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to about 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Further, it is preferably 1.35 or less.
- the thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave exuded by evanescent enters the substrate.
- the method of introducing a diffraction grating into an interface or any medium that causes total reflection is characterized by a high effect of improving light extraction efficiency.
- This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction.
- Light that cannot be emitted due to total internal reflection between layers is diffracted by introducing a diffraction grating into any layer or medium (inside the transparent substrate or transparent electrode). Is going to be taken out.
- the introduced diffraction grating desirably has a two-dimensional periodic refractive index.
- the position where the diffraction grating is introduced may be in any one of the layers or in the medium (in the transparent substrate or transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated. .
- the period of the diffraction grating is preferably about 1Z2 to about 3 times the wavelength of light in the medium.
- the arrangement of the diffraction gratings is preferably two-dimensionally repeated, such as a square lattice, a triangular lattice, or a honeycomb lattice.
- the organic EL device of the present invention can be processed on a light extraction side of a substrate, for example, by providing a microlens array-like structure, or combined with a so-called condensing sheet, in a specific direction, for example, on the device light emitting surface.
- a specific direction for example, on the device light emitting surface.
- the brightness in a specific direction can be increased.
- a quadrangular pyramid with a side of 30 / im and an apex angle of 90 degrees is arranged two-dimensionally on the light extraction side of the substrate.
- One side is preferably 10 ⁇ m to 100 ⁇ m. If it is smaller than this, the effect of diffraction is generated, and if the color is too large, the thickness becomes thick, which is not preferable.
- the condensing sheet for example, a sheet that has been put to practical use in an LED backlight of a liquid crystal display device can be used.
- a brightness enhancement film (BEF) manufactured by Sumitomo 3M Corporation can be used.
- BEF brightness enhancement film
- the shape of the prism sheet for example, the apex angle is 90 degrees and the pitch is 50! ! ! The shape may be an octagonal stripe, or a shape with a rounded apex, a shape with a randomly changed pitch, or any other shape.
- the light diffusing plate 'film is attached to the condensing sheet. May be used in combination with For example, a diffusion film (light-up) manufactured by Kimoto Co., Ltd. can be used.
- a desired electrode material for example, a thin film made of an anode material is formed on a suitable substrate by a method such as vapor deposition or sputtering so as to have a thickness of 1 ⁇ m or less, preferably 10 nm to 200 nm.
- a method such as vapor deposition or sputtering so as to have a thickness of 1 ⁇ m or less, preferably 10 nm to 200 nm.
- an organic EL thin film of an organic EL element material ie, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a hole blocking layer, is formed thereon.
- a method for forming each of these layers there are a vapor deposition method, a wet process (spin coating method, casting method, ink jet method, printing method) and the like as described above.
- a coating method such as a spin coating method, an ink jet method, or a printing method.
- liquid medium for dissolving or dispersing the organic EL material according to the present invention examples include ketones such as methyl ethyl ketone and cyclohexanone, fatty acid esters such as ethyl acetate, and halogenated carbonization such as dichlorobenzene.
- Hydrogen, aromatic hydrocarbons such as toluene, xylene, mesitylene and cyclohexylbenzene, aliphatic hydrocarbons such as cyclohexane, decalin and dodecane, and organic solvents such as DMF and DMSO can be used.
- a dispersion method it can disperse
- a thin film made of a cathode material is formed thereon with a thickness of 1 ⁇ m or less, preferably in the range of 50 nm to 200 nm, for example, by a method such as vapor deposition or sputtering.
- a method such as vapor deposition or sputtering.
- the organic EL element of the present invention can be used as a display device, a display, and various light sources.
- light sources include lighting devices (home lighting, interior lighting), clock and liquid crystal backlights, billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, Examples include, but are not limited to, a light source of an optical sensor, and can be effectively used particularly as a backlight of a liquid crystal display device and a light source for illumination.
- patterning may be performed by a metal mask, an ink jet printing method, or the like as needed during film formation.
- a metal mask In the case of patterning, only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or in the fabrication of an element that may be patterned on the entire element layer, a conventionally known method may be used. Can be used.
- the organic EL element of the present invention is a white element
- white means that in the CIE1931 color system at 1000 Cd / m 2 when the 2 ° viewing angle front luminance is measured by the above method.
- a glass substrate (NA Techno Glass NA45) was attached to a commercially available spin coater, and a solution prepared by dissolving the exemplified compound 4_ 8 (60 mg) in 1,2-dichloroethane 10 ml was used for 10 seconds, lOOOrpm for 30 seconds. Then, spin coating (film thickness: about 40 nm) was performed, and vacuum drying was performed at 25 ° C. for 1 hour, and an organic layer 1 containing the exemplified compound 418, which is a reactive organic compound, was produced on a glass substrate.
- the concentration distribution of Exemplified Compound 48 in the organic layer was determined by a method of measuring the vinyl group distribution of Exemplified Compound 48.
- the distribution of vinyl group double bonds was determined by the following means.
- the concentration of the reactive organic compound 4-8 in the depth direction is the atomic concentration% in the depth direction, the surface of the organic layer 1 (95%), the center of the organic layer 1 (97%), compared to the lower layer of organic layer 1 (99%), the concentration of reactive organic compound 4-8 in the depth direction is higher in organic layer 2 according to the present invention.
- it is clear that it has a concentration distribution, changing to the surface of organic layer 2 (0%), the center of organic layer 2 (62%), and the lower layer of organic layer 2 (97%).
- This ITO transparent electrode is provided after patterning on a substrate (NH45 manufactured by NH Techno Glass Co., Ltd.) made of ITO (indium tin oxide) on lOOnm on a 100mm X 100mm X 1.1mm glass substrate as an anode.
- the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
- This substrate was attached to a commercially available spin coater, and a solution obtained by dissolving PVK (60 mg) in 1, 2 dichloroethane in 1 Oml was used.
- Spin coating (film thickness: about 40 nm), 60 ° C under lOOOrpm for 30 seconds. And dried in a vacuum for 1 hour to form a hole transport layer.
- this substrate was fixed to the substrate holder of the vacuum deposition apparatus, while 200 mg of bathocuproine (BCP) was placed in a molybdenum resistance heating boat, and 200 mg of Alq was placed in another molybdenum resistance heating boat, followed by vacuum deposition. Attached to the device. Reduction in the vacuum tank to 4 X 10- 4 Pa
- the heating boat containing BCP was heated by energization, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide a 10 nm thick hole blocking layer.
- the heating boat containing Alq is energized and heated, and the electrons are deposited at a deposition rate of 0.1 nm / sec.
- An electron transport layer having a thickness of 40 nm was further formed by vapor deposition on the transport layer.
- the substrate temperature during vapor deposition was room temperature.
- lithium fluoride 0.5 nm and aluminum lOnm were deposited to form a cathode, and an organic EL device 1-1 was produced.
- This substrate was attached to a commercially available spin coater, and a solution obtained by dissolving Exemplified Compound 4-7 (60 mg) in 1,2-dichloroethane in 10 ml was used for spin coating (film thickness) at 1000 rpm for 30 seconds. (Approx. 40 nm), irradiated with ultraviolet light for 30 seconds, vacuum dried at 60 ° C for 1 hour to form a hole transport layer
- this substrate is fixed to the substrate holder of the vacuum deposition apparatus, while 200 mg of bathocuproine (BCP) is placed in a molybdenum resistance heating boat, and 200 mg of Alq is placed in another molybdenum resistance heating boat, and vacuum deposition is performed. Attached to the device. Reduction in the vacuum tank to 4 X 10- 4 Pa
- the heating boat containing BCP was heated by energization, and deposited on the light emitting layer at a deposition rate of 0.1 nm / second to provide a 10 nm thick hole blocking layer.
- the heating boat containing Alq was further heated by energization, and the deposition rate was 0.1 nm.
- An electron transport layer having a film thickness of 40 nm was further deposited on the electron transport layer at a rate of / sec.
- the substrate temperature at the time of vapor deposition was room temperature.
- lithium fluoride 0.5 nm and aluminum lOnm were vapor-deposited to form a cathode, and organic EL devices 1-2 were produced.
- the organic EL device 1 _ 3 was prepared in the same manner as in Example 1 except that the example compounds used in the light emitting layer preparation 1 1 1 ⁇ lr _ 1 were replaced as shown in Table 1. ⁇ 1_5 Each was produced.
- the obtained organic EL devices 11 to 15 were evaluated for external extraction quantum efficiency and lifetime.
- the external extraction quantum efficiency (%) was measured when a constant current of 2.5 mA / cm 2 was applied in a dry nitrogen gas atmosphere at 23 ° C.
- a spectral radiance meter CS-1000 manufactured by Konica Minolta was used in the same manner.
- organic EL element 2-1 was produced in the same manner as in the production of the organic EL element 11 of Example 2, except that Ir 1 used for producing the light emitting layer was changed to Ir 9.
- Organic EL elements 1 In the production of 2 organic EL elements 2-2 to 25 were produced in the same manner except that Exemplified Compound 11 and Ir 1 were replaced as shown in Table 2 below, and the method described in Example 1 Were similarly evaluated. Table 2 shows the results obtained.
- the organic EL device of the present invention has a high external quantum efficiency and a long lifetime.
- An organic EL device 3-1 was produced in the same manner as in the production of the organic EL device 11 of Example 2, except that Ir 1 used for producing the light emitting layer was changed to Ir 12. Further, in the production of the organic EL device 1-2, the organic compound 1-1 and the organic compound 1-2 were similarly prepared except that the exemplified compounds 1-1 and Ir-1 were replaced as shown in Table 3. Each of ⁇ 3-5 was prepared and evaluated in the same manner using the method described in Example 2. The results obtained are shown in Table 3.
- the organic EL device of the present invention has a high external quantum efficiency and a long lifetime.
- This ITO transparent electrode is provided after patterning on a substrate (NH45 manufactured by NH Techno Glass Co., Ltd.) made of ITO (indium tin oxide) on lOOnm on a 100mm X 100mm X 1.1mm glass substrate as an anode.
- the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
- This substrate was attached to a commercially available spin coater, and a solution obtained by dissolving Exemplified Compound 4_1 (60 mg) in 10 ml of toluene was spin-coated (film thickness: about 40 nm) at 1000 rpm for 30 seconds. After irradiating with ultraviolet light for 30 seconds, it was vacuum-dried at 60 ° C for 1 hour to form a hole transport layer.
- the solution dissolved in 6 ml of solution is spin-coated under the condition of lOOOrpm for 30 seconds (film thickness of about 6 Onm), irradiated with ultraviolet light for 30 seconds, and then vacuum-dried at 60 ° C for 1 hour to produce a light-emitting layer It was.
- Exemplified Compound 3-1 (20 mg) was dissolved in 10 ml of toluene was used.
- Spin coating (film thickness: about 10 nm) and ultraviolet light were irradiated for 30 seconds under the conditions of lOOOOrp m for 30 seconds. Thereafter, it was vacuum-dried at 60 ° C for 1 hour to provide a hole blocking layer.
- This substrate was fixed to a substrate holder of a vacuum deposition apparatus, and 200 mg of Alq was placed in a molybdenum resistance heating boat and attached to the vacuum deposition apparatus. Pressure in the vacuum tank was reduced to 4 X 10- 4 Pa
- the heating boat containing Alq is further energized and heated, and the deposition rate is 0.
- Evaporation was performed on the electron transport layer at lnm / second, and an electron transport layer having a thickness of 40 nm was further provided.
- the substrate temperature at the time of vapor deposition was room temperature.
- This element was driven at a constant current of 2000 cd / m 2 , and blue light emission was confirmed.
- Figure 1 shows a schematic configuration diagram of an organic EL full-color display device.
- a glass substrate 101 as an anode was patterned on an ITO transparent electrode (102) on a lOOnm film (NH Techno Glass NH 45) with a pitch of 100 ⁇ m, and then it was transparent on this glass substrate.
- a non-photosensitive polyimide partition wall 103 (width: 20 am, thickness: 2.0 ⁇ m) was formed between the electrodes by a photolithographic layer.
- the hole injection layer composition having the following composition is ejected and injected between the polyimide barriers on the IT ⁇ electrode using an inkjet head (manufactured by Epson; MJ800C), irradiated with ultraviolet light for 30 seconds, 60 ° C for 10 minutes
- a hole injection layer 104 with a film thickness of 40 nm was produced by the drying process.
- each light emitting layer (105B, 105G, 105R).
- A1 (106) was vacuum-deposited as a cathode so as to cover the light emitting layer 105, and an organic EL device was produced.
- the fabricated organic EL devices showed blue, green, and red light emission by applying voltage to each electrode, indicating that they can be used as full-color display devices.
- ITO indium tin oxide
- NH Techno Glass NA45 NH Techno Glass NA45
- This ITO transparent electrode was provided.
- the transparent support substrate was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
- This substrate was attached to a commercially available spin coater, and a solution of compound 48 (60 mg) dissolved in 10 ml of toluene was used.
- Spin coating film thickness of about 40 nm
- ultraviolet light irradiation for 30 seconds under the condition of 1000 rpm for 30 seconds. And dried under vacuum at 60 ° C. for 1 hour to form a hole transport layer.
- this substrate was fixed to a substrate holder of a vacuum vapor deposition apparatus, and 200 mg of Alq was put into a molybdenum resistance heating boat and attached to the vacuum vapor deposition apparatus.
- Set the vacuum chamber to 4 X 10— 4 Pa.
- the heating boat containing Alq is energized and heated to a deposition rate of 0.1 nm /
- the film was deposited on the electron transport layer in seconds, and an electron transport layer having a thickness of 40 nm was further provided.
- the substrate temperature during vapor deposition was room temperature.
Description
Claims
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EP07739279A EP2003710A4 (en) | 2006-03-30 | 2007-03-22 | ORGANIC ELECTROLUMINESCENE ELEMENT, METHOD FOR PRODUCING AN ORGANIC ELECTROLUMINESCENT ELEMENT, LIGHTING ARRANGEMENT AND DISPLAY ARRANGEMENT |
US12/294,824 US8426846B2 (en) | 2006-03-30 | 2007-03-22 | Organic electroluminescent element, method of manufacturing organic electroluminescent element, lighting device, and display device |
JP2008510835A JPWO2007119473A1 (ja) | 2006-03-30 | 2007-03-22 | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、照明装置及びディスプレイ装置 |
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US (1) | US8426846B2 (ja) |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010021221A1 (ja) * | 2008-08-19 | 2010-02-25 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネセンス素子の製造方法 |
JP2010098223A (ja) * | 2008-10-20 | 2010-04-30 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス材料、表示装置および照明装置 |
WO2011111860A1 (en) * | 2010-03-12 | 2011-09-15 | Fujifilm Corporation | Organic electroluminescence device and method for producing the same |
WO2018198975A1 (ja) * | 2017-04-27 | 2018-11-01 | 住友化学株式会社 | 発光素子 |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2011065943A (ja) * | 2009-09-18 | 2011-03-31 | Fujifilm Corp | 有機電界発光素子 |
JP5506475B2 (ja) * | 2010-03-15 | 2014-05-28 | ユー・ディー・シー アイルランド リミテッド | 有機電界発光素子の製造方法 |
KR101188747B1 (ko) * | 2012-07-18 | 2012-10-10 | 지스마트 주식회사 | 투명전광판 및 그 제조방법 |
EP3547384B1 (en) * | 2016-11-23 | 2022-10-05 | Guangzhou Chinaray Optoelectronic Materials Ltd. | High polymer, mixture containing same, composition, organic electronic component, and monomer for polymerization |
KR102547153B1 (ko) * | 2022-03-04 | 2023-06-26 | 한양대학교 산학협력단 | 유기 발광 복합체 및 이를 포함하는 유기 발광 박막의 패터닝 방법, 이를 포함하는 유기 발광 조성물, 이를 포함하는 유기 발광 소자 |
Citations (66)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62172691A (ja) | 1986-01-24 | 1987-07-29 | 株式会社小松製作所 | 薄膜el素子 |
US4774435A (en) | 1987-12-22 | 1988-09-27 | Gte Laboratories Incorporated | Thin film electroluminescent device |
JPS63264692A (ja) | 1987-03-02 | 1988-11-01 | イーストマン・コダック・カンパニー | 改良薄膜発光帯をもつ電場発光デバイス |
JPS63314795A (ja) | 1987-06-18 | 1988-12-22 | Komatsu Ltd | 薄膜el素子 |
JPH01220394A (ja) | 1988-02-29 | 1989-09-04 | Hitachi Ltd | 高輝度el素子 |
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
JPH03255190A (ja) | 1990-01-22 | 1991-11-14 | Pioneer Electron Corp | 電界発光素子 |
JPH04297076A (ja) | 1991-01-31 | 1992-10-21 | Toshiba Corp | 有機el素子 |
JPH04308688A (ja) | 1991-04-08 | 1992-10-30 | Pioneer Electron Corp | 有機エレクトロルミネッセンス素子 |
JPH05271166A (ja) | 1992-03-25 | 1993-10-19 | Toppan Printing Co Ltd | テトラアリールジアミン化合物 |
JPH06325871A (ja) | 1993-05-18 | 1994-11-25 | Mitsubishi Kasei Corp | 有機電界発光素子 |
JPH08288069A (ja) | 1995-04-07 | 1996-11-01 | Sanyo Electric Co Ltd | 有機エレクトロルミネッセンス素子 |
JPH0917574A (ja) | 1995-04-27 | 1997-01-17 | Pioneer Electron Corp | 有機エレクトロルミネッセンス素子 |
JPH0945479A (ja) | 1995-07-27 | 1997-02-14 | Hewlett Packard Co <Hp> | 有機エレクトロルミネセンス装置及び有機エレクトロルミネセンス装置の製造方法 |
JPH09260062A (ja) | 1996-03-25 | 1997-10-03 | Tdk Corp | 有機エレクトロルミネセンス素子 |
JPH1074586A (ja) | 1996-07-29 | 1998-03-17 | Eastman Kodak Co | エレクトロルミネセンスデバイスで用いられる二層電子注入電極 |
JPH10270172A (ja) | 1997-01-27 | 1998-10-09 | Junji Kido | 有機エレクトロルミネッセント素子 |
JPH11204258A (ja) | 1998-01-09 | 1999-07-30 | Sony Corp | 電界発光素子及びその製造方法 |
JPH11204359A (ja) | 1998-01-14 | 1999-07-30 | Tokin Corp | 圧粉磁芯の製造方法と製造装置 |
JPH11251067A (ja) | 1998-03-02 | 1999-09-17 | Junji Kido | 有機エレクトロルミネッセント素子 |
JPH11283751A (ja) | 1998-03-27 | 1999-10-15 | Nec Corp | 有機エレクトロルミネッセンス素子 |
JP2000196140A (ja) | 1998-12-28 | 2000-07-14 | Sharp Corp | 有機エレクトロルミネッセンス素子とその製造法 |
US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
JP3093796B2 (ja) | 1992-08-28 | 2000-10-03 | 出光興産株式会社 | 電荷注入補助材及びそれを含有する有機エレクトロルミネッセンス素子 |
JP2001102175A (ja) | 1999-09-29 | 2001-04-13 | Junji Kido | 有機エレクトロルミネッセント素子、有機エレクトロルミネッセント素子群及びその発光スペクトルの制御方法 |
JP2001202827A (ja) | 1999-11-10 | 2001-07-27 | Matsushita Electric Works Ltd | 透明導電性基板、発光素子、平面発光板、平面発光板の製造方法、平面蛍光ランプ、プラズマディスプレイ |
JP2001257076A (ja) | 2000-03-13 | 2001-09-21 | Tdk Corp | 有機el素子 |
JP2001297882A (ja) | 2000-04-14 | 2001-10-26 | Canon Inc | 有機発光素子およびその製造方法 |
JP2001313179A (ja) | 2000-05-01 | 2001-11-09 | Mitsubishi Chemicals Corp | 有機電界発光素子 |
JP2001357977A (ja) | 2000-06-12 | 2001-12-26 | Fuji Photo Film Co Ltd | 有機電界発光素子 |
JP2002008860A (ja) | 2000-04-18 | 2002-01-11 | Mitsubishi Chemicals Corp | 有機電界発光素子 |
JP2002015871A (ja) | 2000-04-27 | 2002-01-18 | Toray Ind Inc | 発光素子 |
JP2002043056A (ja) | 2000-07-19 | 2002-02-08 | Canon Inc | 発光素子 |
JP2002075645A (ja) | 2000-08-29 | 2002-03-15 | Semiconductor Energy Lab Co Ltd | 発光装置 |
JP2002105445A (ja) | 2000-09-29 | 2002-04-10 | Fuji Photo Film Co Ltd | 有機発光素子材料及びそれを用いた有機発光素子 |
JP2002141173A (ja) | 2000-08-22 | 2002-05-17 | Semiconductor Energy Lab Co Ltd | 発光装置 |
JP2002203683A (ja) | 2000-10-30 | 2002-07-19 | Toyota Central Res & Dev Lab Inc | 有機電界発光素子 |
JP2002231453A (ja) | 2000-11-30 | 2002-08-16 | Mitsubishi Chemicals Corp | 有機電界発光素子 |
JP2002234888A (ja) | 2001-02-09 | 2002-08-23 | Mitsui Chemicals Inc | アミン化合物および該化合物を含有する有機電界発光素子 |
JP2002255934A (ja) | 2000-12-25 | 2002-09-11 | Fuji Photo Film Co Ltd | 新規化合物、その重合体、それらを利用した発光素子材料およびその発光素子 |
JP2002260861A (ja) | 2001-01-02 | 2002-09-13 | Eastman Kodak Co | 有機発光デバイス |
JP2002280183A (ja) | 2000-12-28 | 2002-09-27 | Toshiba Corp | 有機el素子および表示装置 |
JP2002299060A (ja) | 2001-03-30 | 2002-10-11 | Fuji Photo Film Co Ltd | 有機発光素子 |
JP2002305084A (ja) | 2000-12-25 | 2002-10-18 | Fuji Photo Film Co Ltd | 新規インドール誘導体およびそれを利用した発光素子 |
JP2002305083A (ja) | 2001-04-04 | 2002-10-18 | Mitsubishi Chemicals Corp | 有機電界発光素子 |
JP2002302516A (ja) | 2001-04-03 | 2002-10-18 | Fuji Photo Film Co Ltd | 新規ポリマーおよびそれを用いた発光素子 |
JP2002308855A (ja) | 2001-04-05 | 2002-10-23 | Fuji Photo Film Co Ltd | 新規化合物、およびそれを用いた発光素子 |
JP2002308837A (ja) | 2001-04-05 | 2002-10-23 | Fuji Photo Film Co Ltd | 新規化合物、およびそれを用いた発光素子 |
JP2002319491A (ja) | 2000-08-24 | 2002-10-31 | Fuji Photo Film Co Ltd | 発光素子及び新規重合体子 |
JP2002334787A (ja) | 2001-03-09 | 2002-11-22 | Sony Corp | 有機電界発光素子 |
JP2002334788A (ja) | 2001-03-09 | 2002-11-22 | Sony Corp | 有機電界発光素子 |
JP2002334786A (ja) | 2001-03-09 | 2002-11-22 | Sony Corp | 有機電界発光素子 |
JP2002334789A (ja) | 2001-03-09 | 2002-11-22 | Sony Corp | 有機電界発光素子 |
JP2002338579A (ja) | 2001-03-16 | 2002-11-27 | Fuji Photo Film Co Ltd | ヘテロ環化合物及びそれを用いた発光素子 |
JP2002343568A (ja) | 2001-05-10 | 2002-11-29 | Sony Corp | 有機電界発光素子 |
JP2002352957A (ja) | 2001-05-23 | 2002-12-06 | Honda Motor Co Ltd | 有機エレクトロルミネッセンス素子 |
JP2002363227A (ja) | 2001-04-03 | 2002-12-18 | Fuji Photo Film Co Ltd | 新規ポリマーおよびそれを用いた発光素子 |
JP2003003165A (ja) | 2001-06-25 | 2003-01-08 | Showa Denko Kk | 有機発光素子および発光材料 |
JP2003027048A (ja) | 2001-07-11 | 2003-01-29 | Fuji Photo Film Co Ltd | 発光素子 |
JP2003073666A (ja) | 2001-06-21 | 2003-03-12 | Showa Denko Kk | 有機発光素子および発光材料 |
JP2003086371A (ja) | 2001-09-10 | 2003-03-20 | Fuji Photo Film Co Ltd | 発光素子および発光素子の製造方法 |
JP2004068143A (ja) | 2002-06-10 | 2004-03-04 | Konica Minolta Holdings Inc | 薄膜形成方法並びに該薄膜形成方法により薄膜が形成された基材 |
JP2004103401A (ja) * | 2002-09-10 | 2004-04-02 | Konica Minolta Holdings Inc | 素子および該素子の製造方法 |
JP2006019678A (ja) * | 2004-06-02 | 2006-01-19 | Dainippon Printing Co Ltd | 有機電子デバイス、及び有機電子デバイスの製造方法 |
JP2006210125A (ja) * | 2005-01-27 | 2006-08-10 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子用透明電極、有機エレクトロルミネッセンス素子及びその製造方法 |
WO2006129471A1 (ja) * | 2005-05-31 | 2006-12-07 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、照明装置及び表示装置 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6130001A (en) * | 1997-07-15 | 2000-10-10 | Motorola, Inc. | Organic electroluminescent device with continuous organic medium |
SG138466A1 (en) | 2000-12-28 | 2008-01-28 | Semiconductor Energy Lab | Luminescent device |
JP2003309307A (ja) * | 2002-02-08 | 2003-10-31 | Matsushita Electric Ind Co Ltd | 有機電子デバイスおよびその製造方法 |
US7839075B2 (en) * | 2003-07-23 | 2010-11-23 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, illuminator and display |
US8026510B2 (en) * | 2004-10-20 | 2011-09-27 | Dai Nippon Printing Co., Ltd. | Organic electronic device and method for producing the same |
JP5130606B2 (ja) * | 2005-02-25 | 2013-01-30 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、その製造方法、表示装置及び照明装置 |
-
2007
- 2007-03-22 EP EP07739279A patent/EP2003710A4/en not_active Withdrawn
- 2007-03-22 US US12/294,824 patent/US8426846B2/en not_active Expired - Fee Related
- 2007-03-22 JP JP2008510835A patent/JPWO2007119473A1/ja active Pending
- 2007-03-22 WO PCT/JP2007/055836 patent/WO2007119473A1/ja active Application Filing
-
2014
- 2014-01-27 JP JP2014012389A patent/JP2014099645A/ja active Pending
Patent Citations (66)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS62172691A (ja) | 1986-01-24 | 1987-07-29 | 株式会社小松製作所 | 薄膜el素子 |
JPS63264692A (ja) | 1987-03-02 | 1988-11-01 | イーストマン・コダック・カンパニー | 改良薄膜発光帯をもつ電場発光デバイス |
JPS63314795A (ja) | 1987-06-18 | 1988-12-22 | Komatsu Ltd | 薄膜el素子 |
US4774435A (en) | 1987-12-22 | 1988-09-27 | Gte Laboratories Incorporated | Thin film electroluminescent device |
JPH01220394A (ja) | 1988-02-29 | 1989-09-04 | Hitachi Ltd | 高輝度el素子 |
JPH03255190A (ja) | 1990-01-22 | 1991-11-14 | Pioneer Electron Corp | 電界発光素子 |
US5061569A (en) | 1990-07-26 | 1991-10-29 | Eastman Kodak Company | Electroluminescent device with organic electroluminescent medium |
JPH04297076A (ja) | 1991-01-31 | 1992-10-21 | Toshiba Corp | 有機el素子 |
JPH04308688A (ja) | 1991-04-08 | 1992-10-30 | Pioneer Electron Corp | 有機エレクトロルミネッセンス素子 |
JPH05271166A (ja) | 1992-03-25 | 1993-10-19 | Toppan Printing Co Ltd | テトラアリールジアミン化合物 |
JP3093796B2 (ja) | 1992-08-28 | 2000-10-03 | 出光興産株式会社 | 電荷注入補助材及びそれを含有する有機エレクトロルミネッセンス素子 |
JPH06325871A (ja) | 1993-05-18 | 1994-11-25 | Mitsubishi Kasei Corp | 有機電界発光素子 |
JPH08288069A (ja) | 1995-04-07 | 1996-11-01 | Sanyo Electric Co Ltd | 有機エレクトロルミネッセンス素子 |
JPH0917574A (ja) | 1995-04-27 | 1997-01-17 | Pioneer Electron Corp | 有機エレクトロルミネッセンス素子 |
JPH0945479A (ja) | 1995-07-27 | 1997-02-14 | Hewlett Packard Co <Hp> | 有機エレクトロルミネセンス装置及び有機エレクトロルミネセンス装置の製造方法 |
JPH09260062A (ja) | 1996-03-25 | 1997-10-03 | Tdk Corp | 有機エレクトロルミネセンス素子 |
JPH1074586A (ja) | 1996-07-29 | 1998-03-17 | Eastman Kodak Co | エレクトロルミネセンスデバイスで用いられる二層電子注入電極 |
JPH10270172A (ja) | 1997-01-27 | 1998-10-09 | Junji Kido | 有機エレクトロルミネッセント素子 |
JPH11204258A (ja) | 1998-01-09 | 1999-07-30 | Sony Corp | 電界発光素子及びその製造方法 |
JPH11204359A (ja) | 1998-01-14 | 1999-07-30 | Tokin Corp | 圧粉磁芯の製造方法と製造装置 |
JPH11251067A (ja) | 1998-03-02 | 1999-09-17 | Junji Kido | 有機エレクトロルミネッセント素子 |
JPH11283751A (ja) | 1998-03-27 | 1999-10-15 | Nec Corp | 有機エレクトロルミネッセンス素子 |
US6097147A (en) | 1998-09-14 | 2000-08-01 | The Trustees Of Princeton University | Structure for high efficiency electroluminescent device |
JP2000196140A (ja) | 1998-12-28 | 2000-07-14 | Sharp Corp | 有機エレクトロルミネッセンス素子とその製造法 |
JP2001102175A (ja) | 1999-09-29 | 2001-04-13 | Junji Kido | 有機エレクトロルミネッセント素子、有機エレクトロルミネッセント素子群及びその発光スペクトルの制御方法 |
JP2001202827A (ja) | 1999-11-10 | 2001-07-27 | Matsushita Electric Works Ltd | 透明導電性基板、発光素子、平面発光板、平面発光板の製造方法、平面蛍光ランプ、プラズマディスプレイ |
JP2001257076A (ja) | 2000-03-13 | 2001-09-21 | Tdk Corp | 有機el素子 |
JP2001297882A (ja) | 2000-04-14 | 2001-10-26 | Canon Inc | 有機発光素子およびその製造方法 |
JP2002008860A (ja) | 2000-04-18 | 2002-01-11 | Mitsubishi Chemicals Corp | 有機電界発光素子 |
JP2002015871A (ja) | 2000-04-27 | 2002-01-18 | Toray Ind Inc | 発光素子 |
JP2001313179A (ja) | 2000-05-01 | 2001-11-09 | Mitsubishi Chemicals Corp | 有機電界発光素子 |
JP2001357977A (ja) | 2000-06-12 | 2001-12-26 | Fuji Photo Film Co Ltd | 有機電界発光素子 |
JP2002043056A (ja) | 2000-07-19 | 2002-02-08 | Canon Inc | 発光素子 |
JP2002141173A (ja) | 2000-08-22 | 2002-05-17 | Semiconductor Energy Lab Co Ltd | 発光装置 |
JP2002319491A (ja) | 2000-08-24 | 2002-10-31 | Fuji Photo Film Co Ltd | 発光素子及び新規重合体子 |
JP2002075645A (ja) | 2000-08-29 | 2002-03-15 | Semiconductor Energy Lab Co Ltd | 発光装置 |
JP2002105445A (ja) | 2000-09-29 | 2002-04-10 | Fuji Photo Film Co Ltd | 有機発光素子材料及びそれを用いた有機発光素子 |
JP2002203683A (ja) | 2000-10-30 | 2002-07-19 | Toyota Central Res & Dev Lab Inc | 有機電界発光素子 |
JP2002231453A (ja) | 2000-11-30 | 2002-08-16 | Mitsubishi Chemicals Corp | 有機電界発光素子 |
JP2002255934A (ja) | 2000-12-25 | 2002-09-11 | Fuji Photo Film Co Ltd | 新規化合物、その重合体、それらを利用した発光素子材料およびその発光素子 |
JP2002305084A (ja) | 2000-12-25 | 2002-10-18 | Fuji Photo Film Co Ltd | 新規インドール誘導体およびそれを利用した発光素子 |
JP2002280183A (ja) | 2000-12-28 | 2002-09-27 | Toshiba Corp | 有機el素子および表示装置 |
JP2002260861A (ja) | 2001-01-02 | 2002-09-13 | Eastman Kodak Co | 有機発光デバイス |
JP2002234888A (ja) | 2001-02-09 | 2002-08-23 | Mitsui Chemicals Inc | アミン化合物および該化合物を含有する有機電界発光素子 |
JP2002334787A (ja) | 2001-03-09 | 2002-11-22 | Sony Corp | 有機電界発光素子 |
JP2002334788A (ja) | 2001-03-09 | 2002-11-22 | Sony Corp | 有機電界発光素子 |
JP2002334786A (ja) | 2001-03-09 | 2002-11-22 | Sony Corp | 有機電界発光素子 |
JP2002334789A (ja) | 2001-03-09 | 2002-11-22 | Sony Corp | 有機電界発光素子 |
JP2002338579A (ja) | 2001-03-16 | 2002-11-27 | Fuji Photo Film Co Ltd | ヘテロ環化合物及びそれを用いた発光素子 |
JP2002299060A (ja) | 2001-03-30 | 2002-10-11 | Fuji Photo Film Co Ltd | 有機発光素子 |
JP2002363227A (ja) | 2001-04-03 | 2002-12-18 | Fuji Photo Film Co Ltd | 新規ポリマーおよびそれを用いた発光素子 |
JP2002302516A (ja) | 2001-04-03 | 2002-10-18 | Fuji Photo Film Co Ltd | 新規ポリマーおよびそれを用いた発光素子 |
JP2002305083A (ja) | 2001-04-04 | 2002-10-18 | Mitsubishi Chemicals Corp | 有機電界発光素子 |
JP2002308855A (ja) | 2001-04-05 | 2002-10-23 | Fuji Photo Film Co Ltd | 新規化合物、およびそれを用いた発光素子 |
JP2002308837A (ja) | 2001-04-05 | 2002-10-23 | Fuji Photo Film Co Ltd | 新規化合物、およびそれを用いた発光素子 |
JP2002343568A (ja) | 2001-05-10 | 2002-11-29 | Sony Corp | 有機電界発光素子 |
JP2002352957A (ja) | 2001-05-23 | 2002-12-06 | Honda Motor Co Ltd | 有機エレクトロルミネッセンス素子 |
JP2003073666A (ja) | 2001-06-21 | 2003-03-12 | Showa Denko Kk | 有機発光素子および発光材料 |
JP2003003165A (ja) | 2001-06-25 | 2003-01-08 | Showa Denko Kk | 有機発光素子および発光材料 |
JP2003027048A (ja) | 2001-07-11 | 2003-01-29 | Fuji Photo Film Co Ltd | 発光素子 |
JP2003086371A (ja) | 2001-09-10 | 2003-03-20 | Fuji Photo Film Co Ltd | 発光素子および発光素子の製造方法 |
JP2004068143A (ja) | 2002-06-10 | 2004-03-04 | Konica Minolta Holdings Inc | 薄膜形成方法並びに該薄膜形成方法により薄膜が形成された基材 |
JP2004103401A (ja) * | 2002-09-10 | 2004-04-02 | Konica Minolta Holdings Inc | 素子および該素子の製造方法 |
JP2006019678A (ja) * | 2004-06-02 | 2006-01-19 | Dainippon Printing Co Ltd | 有機電子デバイス、及び有機電子デバイスの製造方法 |
JP2006210125A (ja) * | 2005-01-27 | 2006-08-10 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子用透明電極、有機エレクトロルミネッセンス素子及びその製造方法 |
WO2006129471A1 (ja) * | 2005-05-31 | 2006-12-07 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、照明装置及び表示装置 |
Non-Patent Citations (11)
Title |
---|
"Electrode materials", vol. 2, 30 November 1998, NTS INC., article "Yuuki EL soshi to sono kougyouka saizennsenn", pages: 123 - 166 |
"Shinpen Shikisai Kagaku Handbook", TOKYO UNIVERSITY SHUPPAN KAI |
"Yuki EL Soshi to Sono Kogyoka Saizensen", 30 November 1998, NTS INC. |
BUNKO II: "Jikken Kagaku Koza 7", 1992, MARUZEN, pages: 398 |
INORG. CHEM., vol. 40, pages 1704 - 1711 |
J. APPL. PHYS., vol. 95, 2004, pages 5773 |
J. HUANG ET AL., APPLIED PHYSICS LETTERS, vol. 80, 2002 |
M.A. BALDO ET AL., NATURE, vol. 395, no. 17, 1998, pages 151 - 154 |
M.A. BALDO ET AL., NATURE, vol. 403, no. 17, 2000, pages 750 - 753 |
S. LAMANSKY ET AL., J. AM. CHEM. SOC., vol. 123, no. 4304, 2001 |
See also references of EP2003710A4 |
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WO2018198975A1 (ja) * | 2017-04-27 | 2018-11-01 | 住友化学株式会社 | 発光素子 |
JPWO2018198975A1 (ja) * | 2017-04-27 | 2019-06-27 | 住友化学株式会社 | 発光素子 |
CN110546781A (zh) * | 2017-04-27 | 2019-12-06 | 住友化学株式会社 | 发光元件 |
CN110546781B (zh) * | 2017-04-27 | 2022-05-10 | 住友化学株式会社 | 发光元件 |
US11588119B2 (en) | 2017-04-27 | 2023-02-21 | Sumitomo Chemical Company, Limited | Light emitting device |
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EP2003710A4 (en) | 2012-02-01 |
JP2014099645A (ja) | 2014-05-29 |
EP2003710A2 (en) | 2008-12-17 |
EP2003710A9 (en) | 2009-04-22 |
US8426846B2 (en) | 2013-04-23 |
US20100171101A1 (en) | 2010-07-08 |
JPWO2007119473A1 (ja) | 2009-08-27 |
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