WO2009084413A1 - Dispositif électroluminescent organique et procédé de fabrication de dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique et procédé de fabrication de dispositif électroluminescent organique Download PDF

Info

Publication number
WO2009084413A1
WO2009084413A1 PCT/JP2008/072756 JP2008072756W WO2009084413A1 WO 2009084413 A1 WO2009084413 A1 WO 2009084413A1 JP 2008072756 W JP2008072756 W JP 2008072756W WO 2009084413 A1 WO2009084413 A1 WO 2009084413A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
light emitting
organic
layer
dopant
Prior art date
Application number
PCT/JP2008/072756
Other languages
English (en)
Japanese (ja)
Inventor
Kunimasa Hiyama
Yoshiyuki Suzuri
Original Assignee
Konica Minolta Holdings, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Konica Minolta Holdings, Inc. filed Critical Konica Minolta Holdings, Inc.
Priority to JP2009547981A priority Critical patent/JPWO2009084413A1/ja
Publication of WO2009084413A1 publication Critical patent/WO2009084413A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/125—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one oxygen atom in the ring
    • 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
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
    • H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/22—Molecular weight
    • C08G2261/226—Oligomers, i.e. up to 10 repeat units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3241—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more nitrogen atoms as the only heteroatom, e.g. carbazole
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
    • C08G2261/3242—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more oxygen atoms as the only heteroatom, e.g. benzofuran
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/80—Composition varying spatially, e.g. having a spatial gradient
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to an organic electroluminescence element and a method for producing the organic electroluminescence element. Specifically, the present invention relates to an organic electroluminescent element that can be manufactured by a simple process and has improved light emission efficiency and lifetime, and a method for manufacturing the organic electroluminescent element.
  • ELD electroluminescence display
  • an inorganic electroluminescence element hereinafter also referred to as an inorganic EL element
  • an organic electroluminescence element hereinafter also referred to as an organic EL element
  • Inorganic EL elements have been used as planar light sources, but an alternating high voltage is required to drive the light emitting elements.
  • an organic electroluminescence device has a structure in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and excitons (excitons) by injecting electrons and holes into the light emitting layer and recombining them. Is generated. It 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 V to several tens V, and it is self-luminous. In addition, it is attracting attention from the viewpoints of space saving, portability and the like because it is a thin film type complete solid element with a wide viewing angle and high visibility.
  • the organic electroluminescence element is also a major feature that it is a surface light source, unlike the main light sources that have been used in the past, such as light-emitting diodes and cold-cathode tubes.
  • Applications that can effectively utilize this characteristic include illumination light sources and various display backlights.
  • it is also suitable to be used as a backlight of a liquid crystal full color display whose demand has been increasing in recent years.
  • Improvement of luminous efficiency is mentioned as a problem for putting an organic electroluminescence element into practical use as such a light source for illumination or a backlight of a display.
  • a so-called host / guest structure in which a part of the organic functional layer constituting the organic electroluminescence element is composed of a mixture of materials having different functions. It is becoming.
  • a combination of a host material / a light emitting dopant in the light emitting layer may be mentioned.
  • the ratio of the light-emitting dopant to the light-emitting host in the light-emitting layer is continuously changed in the light-emitting layer, indicating that the lifetime is improved (for example, see Patent Documents 1 and 2).
  • What is clearly shown as the means for changing to is only the control of the deposition rate in the vacuum deposition method, and cannot be said to be a proposal of means suitable for productivity.
  • the present invention has been made in view of the above problems, and an object of the present invention is to provide an organic electroluminescence element that has high luminous efficiency and long life and can be stably produced by a wet process, and a method for producing the organic electroluminescence element Is to provide.
  • the light emitting layer is formed by a wet process
  • the manufacturing method of the organic electroluminescent element characterized by changing continuously the density
  • R 1 represents a substituent.
  • Z represents a group of nonmetallic atoms necessary to form a 5- to 7-membered ring.
  • N1 represents an integer of 0 to 5.
  • B 1 to B 5 represent carbon. Represents an atom, a nitrogen atom, an oxygen atom or a sulfur atom, at least one of B 1 to B 5 represents a nitrogen atom, M 1 represents a group 8 to group 10 metal in the periodic table, and X 1 and X 2 Represents a carbon atom, a nitrogen atom or an oxygen atom, L 1 represents an atomic group forming a bidentate ligand with X 1 and X 2 , m1 represents an integer of 1, 2 or 3, and m2 represents 0 Represents an integer of 1 or 2, and m1 + m2 is 2 or 3.) 4).
  • the light emitting host is a compound having a molecular weight of 700 or more represented by
  • Y 1 and Y 2 represent O, S or NR 0 , and R 0 , R 11 to R 18 and R 21 to R 28 represent a hydrogen atom or a substituent, provided that R 11 At least one of ⁇ R 18 and R 0 is used in connection with X 1, R 21 ⁇ R 28 and at least one .X 1 which is used for connection with the X 1 represented by the following general formula R 0 (3 ) or (4 .n1 that represents a divalent linking group represented by) represents an integer of 1 or more, when n1 is 2 or more, X 1 is may be the same or different.
  • the light emitting dopant / light emitting host ratio of the solution coated on the most anode side is 100 to 10% by mass, and the light emitting dopant / light emitting host of the solution coated on the most cathode side. 8. The method for producing an organic electroluminescent element as described in 7 above, wherein the ratio is 5 to 0% by mass.
  • an organic electroluminescence element that has high luminous efficiency and long life and can be stably produced by a wet process, and a method for producing the organic electroluminescence element.
  • the present invention provides an organic electroluminescent device having at least an anode, a cathode, and a light emitting layer containing a light emitting host and a light emitting dopant sandwiched between the anode and the cathode on a substrate, wherein the light emitting layer is formed by a wet process.
  • concentration of the light emission dopant contained in this light emitting layer changes continuously toward the cathode side from an anode side, It is characterized by the above-mentioned.
  • the concentration of the luminescent dopant decreases from the anode side toward the cathode side.
  • 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 in the layer of the light emitting layer. May be the interface
  • the thickness of the light emitting layer is not particularly limited, but it is 2 to 2 from the viewpoint of the uniformity of the film to be formed and the application of unnecessary high voltage during light emission, and the improvement of the stability of the emission color with respect to the driving current. It is preferable to adjust to a range of 200 nm, more preferably to a range of 5 nm or more and 100 nm or less.
  • the light emitting layer of the organic electroluminescence device of the present invention is formed by a wet process.
  • Known wet process coating methods include spin coating, die coating, casting, inkjet, spraying, printing, etc., but it is easy to obtain a homogeneous film and it is difficult to generate pinholes.
  • film formation by a coating method such as a spin coating method, a die coating method, an ink jet method, a spray method, or a printing method is preferable.
  • the light emitting layer of the organic electroluminescence device of the present invention contains a light emitting host and at least one light emitting dopant, and the concentration of the light emitting dopant in the light emitting layer is continuously changed from the anode side to the cathode side.
  • the atmospheric temperature in contact with the back side of the coating film may be lowered by 10 ° C. or more from the atmospheric temperature in contact with the front side of the coating film and dried.
  • a method of controlling the atmospheric temperature of the front and back of the coating film a method of separately controlling the temperature of the drying air sent to the front side and the drying air sent to the back side using an isolated drying box for each of the coated samples, coating
  • a method of controlling the drying air temperature on the front side and the back side is preferable in order to avoid damage to the coating film due to contact.
  • the solvent of the luminescent layer solution has a boiling point of the solvent with the higher luminescent dopant solubility for the mixed solvent of two liquids having different boiling point and luminescent dopant solubility.
  • the dopant solubility is higher than the boiling point of the lower solvent.
  • the light-emitting host has a mass ratio of 20% or more in a compound contained in a light-emitting layer, and a phosphorescence quantum yield of phosphorescence emission is 0 at room temperature (25 ° C.). Less than 1 compound.
  • the phosphorescence quantum yield is preferably less than 0.01.
  • the mass ratio in the layer is 20% or more among the compounds contained in a light emitting layer.
  • a compound having a molecular weight of 700 or more represented by the general formula (2) as a luminescent host.
  • the light emitting host according to the present invention has a molecular weight of 700 or more, preferably a molecular weight of 800 or more and 3,000 or less, 800 or more and 2,000 or less, 800 or more and 1,500 or less, and most preferably a molecular weight of 1,000 or more and 1,500 or less. .
  • Y 1 and Y 2 represent O, S or NR 0 , and R 0 , R 11 to R 18 and R 21 to R 28 represent a hydrogen atom or a substituent. However, at least one of R 11 to R 18 and R 0 is used for connection with X 1, and at least one of R 21 to R 28 and R 0 is used for connection with X 1 .
  • X 1 represents a divalent linking group represented by the following general formula (3) or (4).
  • n1 represents an integer of 1 or more, and when n1 is 2 or more, X 1 may be the same or different.
  • Y 3 represents O, S or NR 30
  • R 30 to R 38 and R 41 to R 46 represent a hydrogen atom or a substituent.
  • at least two of each of R 30 to R 38 and R 41 to R 46 are used for connection, and when R 41 and R 44 are used for connection, at least R 42 , R 43 , R 45 , R 46 are used.
  • R 0 , R 11 to R 18 and R 21 to R 28 , and R 30 to R 38 and R 41 to R 46 have the same meaning as the substituent represented by R 1 in the general formula (1). is there.
  • the light emitting host a known light emitting host may be used alone, or a plurality of kinds may be used in combination.
  • the movement of charges can be adjusted, and the organic EL element can be made highly efficient.
  • 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, and a low molecular compound having a polymerizable group such as a vinyl group or an epoxy group (deposition polymerization property). Light emitting host).
  • a compound that has a hole transporting ability and an electron transporting ability, prevents the emission of longer wavelengths, and has a high Tg (glass transition temperature) is preferable.
  • Luminescent dopant The light emitting dopant according to the present invention will be described.
  • a fluorescent dopant or a phosphorescent dopant can be used. From the viewpoint of obtaining an organic EL element with higher luminous efficiency, it is used for the light-emitting layer and the light-emitting unit of the organic EL element of the present invention.
  • the light emitting dopant it is preferable to contain a phosphorescent dopant at the same time as containing the above light emitting host.
  • the phosphorescent dopant according to the present invention is a compound in which light emission from an excited triplet is observed.
  • the phosphorescent dopant is a compound that emits phosphorescence at room temperature (25 ° C.) and has a phosphorescence quantum yield of 25. It is a compound of 0.01 or more at ° C., and a preferable phosphorescence quantum yield is 0.1 or more.
  • the phosphorescent quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of the Fourth Edition Experimental Chemistry Course 7. Although the phosphorescence quantum yield in a solution can be measured using various solvents, the phosphorescence dopant according to the present invention achieves the phosphorescence quantum yield (0.01 or more) in any solvent. That's fine.
  • phosphorescent dopants There are two types of emission of phosphorescent dopants in principle. One is the recombination of carriers on the light-emitting host on which carriers are transported to generate the excited state of the light-emitting host, and this energy is transferred to the phosphorescent dopant. Energy transfer type to obtain light emission from the phosphorescent dopant, another is that the phosphorescent dopant becomes a carrier trap, carrier recombination occurs on the phosphorescent dopant, and light emission from the phosphorescent dopant is obtained It is a carrier trap type. In any case, it is a condition that the excited state energy of the phosphorescent dopant is lower than the excited state energy of the light emitting host.
  • the phosphorescent dopant can be appropriately selected from known materials used for the light emitting layer of the organic EL element.
  • a phosphorescent dopant represented by the general formula (1) it is preferable to use a phosphorescent dopant represented by the general formula (1) as a light emitting dopant.
  • examples of the substituent represented by R 1 include an alkyl group (for example, methyl group, ethyl group, propyl group, isopropyl group, t- Butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (eg, vinyl group, allyl group) Etc.), alkynyl groups (for example, ethynyl group, propargyl group, etc.), aromatic hydrocarbon ring groups (aromatic carbocyclic group, aryl group, etc.), for example, phenyl group, p-chlorophenyl group, mesity
  • Z represents a nonmetallic atom group necessary for forming a 5- to 7-membered ring.
  • the 5- to 7-membered ring formed by Z include a benzene ring, naphthalene ring, pyridine ring, pyrimidine ring, pyrrole ring, thiophene ring, pyrazole ring, imidazole ring, oxazole ring and thiazole ring. Of these, a benzene ring is preferred.
  • B 1 to B 5 each represent a carbon atom, a nitrogen atom, an oxygen atom or a sulfur atom, and at least one represents a nitrogen atom.
  • the aromatic nitrogen-containing heterocycle formed by these five atoms is preferably a monocycle. Examples include pyrrole ring, pyrazole ring, imidazole ring, triazole ring, tetrazole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, oxadiazole ring, and thiadiazole ring.
  • a pyrazole ring and an imidazole ring are preferable, and an imidazole ring is more preferable.
  • These rings may be further substituted with the above substituents.
  • Preferred as the substituent are an alkyl group and an aryl group, and more preferably an aryl group.
  • L 1 represents an atomic group that forms a bidentate ligand together with X 1 and X 2 .
  • Specific examples of the bidentate ligand represented by X 1 -L 1 -X 2 include, for example, substituted or unsubstituted phenylpyridine, phenylpyrazole, phenylimidazole, phenyltriazole, phenyltetrazole, pyrazabol, picolinic acid And acetylacetone. These groups may be further substituted with the above substituents.
  • M1 represents an integer of 1, 2 or 3
  • m2 represents an integer of 0, 1 or 2
  • m1 + m2 is 2 or 3.
  • m2 is 0 is preferable.
  • a transition metal element of Group 8 to Group 10 (also referred to simply as a transition metal) in the periodic table of elements is used.
  • iridium and platinum are preferable, and iridium is more preferable.
  • the light-emitting dopant represented by the general formula (1) according to the present invention may or may not have a polymerizable group or a reactive group.
  • fluorescent dopant As fluorescent dopants, coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylene dyes, stilbene dyes , Polythiophene dyes, or rare earth complex phosphors.
  • Injection layer electron injection layer, hole injection layer >> The injection layer is provided as necessary, and there are an electron injection layer and a hole injection layer, and as described above, it exists between the anode and the light emitting layer or the hole transport layer and between the cathode and the light emitting layer or the electron transport layer. May be.
  • An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance.
  • Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) 2), Chapter 2, “Electrode Materials” (pages 123 to 166) in detail, and includes a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).
  • anode buffer layer hole injection layer
  • copper phthalocyanine is used.
  • examples thereof include a phthalocyanine buffer layer represented by an oxide, 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 described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc.
  • Metal buffer layer typified by lithium, 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 buffer layer (injection layer) is preferably a very thin film, and the film thickness is preferably in the range of 0.1 nm to 5 ⁇ m, although it depends on the material.
  • ⁇ 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. For example, it is described in JP-A Nos. 11-204258 and 11-204359, and “Organic EL elements and the forefront of industrialization (published by NTT Corporation on November 30, 1998)” on page 237. There is a hole blocking (hole blocking) layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes can be improved by blocking. Moreover, the structure of the electron carrying layer mentioned later can be used as a hole-blocking layer concerning this invention as needed.
  • 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 contains the carbazole derivative mentioned as the light emitting host.
  • the light emitting layer having the shortest wavelength of light emission is preferably 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 light emitting host of the shortest wave emitting layer.
  • the ionization potential is defined by the energy required to emit electrons at the HOMO (highest occupied molecular orbital) level of the compound to the vacuum level, and can be obtained by, for example, the following method.
  • Gaussian 98 (Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.), a molecular orbital calculation software manufactured by Gaussian, USA, is used as a keyword.
  • the ionization potential can be obtained as a value obtained by rounding off the second decimal place of a value (eV unit converted value) calculated by performing structural optimization using B3LYP / 6-31G *. This calculation value is effective because the correlation between the calculation value obtained by this method and the experimental value is high.
  • the ionization potential can also be obtained by a method of directly measuring by photoelectron spectroscopy.
  • 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 has an extremely small ability to transport electrons. By blocking, the recombination probability of electrons and holes can be improved. Moreover, 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 to 100 nm, more preferably 5 to 30 nm.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and in a broad sense, 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 either hole injection or transport or electron barrier properties, and may be either organic or inorganic.
  • triazole derivatives oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline 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.
  • the above-mentioned materials can be used as the hole transport material, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl; N, N′-diphenyl-N, N′— Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminoph
  • No. 5,061,569 Having a condensed aromatic ring of, for example, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPD), JP-A-4-308 4,4 ′, 4 ′′ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine in which three triphenylamine units described in Japanese Patent No. 88 are linked in a starburst type ( MTDATA) and the like.
  • NPD 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • JP-A-4-308 4,4 ′, 4 ′′ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine in which three triphenylamine units described in Japanese Patent No. 88 are linked in a starburst type ( MTDATA) and the
  • 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 injection material and the hole transport material.
  • JP-A-11-251067, J. Org. Huang et. al. A so-called p-type hole transport material described in a book (Applied Physics Letters 80 (2002), p. 139) can also be used.
  • these materials are preferably used because a light-emitting element with higher efficiency can be obtained.
  • the hole transport layer can be 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. it can.
  • the thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 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 examples thereof include JP-A-4-297076, JP-A-2000-196140, JP-A-2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), and the like.
  • a hole transport layer having such a high p property because a device with lower power consumption can be produced.
  • 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 used for an electron transport layer adjacent to the light emitting layer on the cathode side is injected from the cathode.
  • Any material may be used as long as it has a function of transferring electrons to the light-emitting layer, and any material can be selected from conventionally known compounds. Examples include nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like.
  • 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-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), and the like, and the central metals of these metal complexes are In, Mg, Metal complexes replaced with Cu, Ca, Sn, Ga or Pb can also be used as the electron transport material.
  • metal-free or metal phthalocyanine or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material.
  • the distyrylpyrazine derivative exemplified as the material for the light emitting layer can also be used as an electron transport material, and an inorganic semiconductor such as n-type-Si, n-type-SiC, etc. as in the case of the hole injection layer and the hole transport layer. Can also be used as an electron transporting material.
  • the electron transport layer can be 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.
  • the thickness of the electron transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 to 200 nm.
  • 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 may be used.
  • examples thereof include JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, JP-A-2001-102175, J. Pat. Appl. Phys. 95, 5773 (2004), and the like.
  • an electron transport layer having such a high n property because an element with lower power consumption can be produced.
  • an organic compound having a reactive group may be used.
  • reactive organic compound There is no restriction
  • Reactive organic compounds can be reacted on a substrate to form a network polymer with organic molecules.
  • production of a network polymer can suppress element deterioration by Tg (glass transition point) adjustment of a structure layer. It is also possible to change the emission wavelength of the organic EL element, suppress deterioration of the specific wavelength, etc. by adjusting the reaction accompanied by the cleavage or generation of the conjugated system of the molecule using the active radical in use. is there.
  • the lower layer is not dissolved in the upper layer coating solution, and upper layer coating can be made possible by resinating the lower layer and degrading solvent solubility.
  • 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 substances include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) that can form a transparent conductive film may be used.
  • these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when pattern accuracy is not so high (about 100 ⁇ m or more)
  • a pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.
  • wet film-forming methods such as a printing system and a coating system, can also be used.
  • the transmittance is greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the material, it is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.
  • cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture
  • a magnesium / aluminum 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.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
  • the light emission luminance is improved, which is convenient.
  • a transparent or semi-transparent cathode can be produced by producing the conductive transparent material mentioned in the description of the anode on the cathode after producing the metal with a film thickness of 1 to 20 nm. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
  • 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. May be opaque. When extracting light from the support substrate side, the support substrate is preferably transparent. Examples of the transparent support substrate preferably used include glass, quartz, and a 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, cellulose diacetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate (CAP), Cellulose esters such as cellulose acetate phthalate (TAC) and cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfone , Polyetherimide, polyether ketone imide, polyamide, fluorine resin, nylon, polymethyl methacrylate, acrylic or polyarylates, and cycloolefin resins such as ARTON (manufactured by J
  • An inorganic or organic film or a hybrid film of both may be formed on the surface of the resin film, and it is preferably a barrier film having a water vapor permeability of 0.01 g / m 2 / day ⁇ atm or less. Furthermore, a high barrier film having an oxygen permeability of 10 ⁇ 3 g / m 2 / day or less and a water vapor permeability of 10 ⁇ 5 g / m 2 / day or less is preferable.
  • the material for forming the barrier film may be any material that has a function of suppressing the intrusion of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like can be used.
  • the method for forming the barrier film is not particularly limited.
  • the vacuum deposition method, sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma weight A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, and the like can be used, but an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is particularly preferable.
  • the opaque support substrate examples include metal plates such as aluminum and stainless steel, films, opaque resin substrates, ceramic substrates, and the like.
  • the external extraction quantum 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 (%) the number of photons emitted to the outside of the organic EL element / the number of electrons sent to the organic EL element ⁇ 100.
  • 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.
  • the ⁇ max of light emission of the organic EL element is preferably 480 nm or less.
  • a sealing means used for this invention the method of adhere
  • a sealing member it should just be arrange
  • Specific examples include a glass plate, a polymer plate / film, and a metal plate / film.
  • the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium 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, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.
  • a polymer film and a metal film can be preferably used because the element can be thinned.
  • the polymer film oxygen permeability measured by the method based on JIS K 7126-1987 is 1 ⁇ 10 -3 ml / m 2 / 24h or less, as measured by the method based on JIS K 7129-1992, water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)%) is preferably that of 1 ⁇ 10 -3 g / (m 2 / 24h) or less.
  • sealing member For processing the sealing member into a concave shape, sandblasting, chemical etching, or the like is used.
  • the adhesive include photocuring and thermosetting adhesives having reactive vinyl groups of acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. be able to.
  • hot-melt type polyamide, polyester, and polyolefin can be mentioned.
  • a cationic curing type ultraviolet curing epoxy resin adhesive can be mentioned.
  • an organic EL element may deteriorate by heat processing, what can be adhesively cured from room temperature to 80 ° C. is preferable.
  • a desiccant may be dispersed in the adhesive.
  • coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print like screen printing.
  • the electrode and the organic layer are coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer is formed in contact with the support substrate to form a sealing film.
  • the material for forming the film may be a material having 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.
  • vacuum deposition method sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma
  • a polymerization method a plasma CVD method, a laser CVD 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 fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase.
  • a vacuum can also be used.
  • a hygroscopic compound can also be enclosed inside.
  • hygroscopic compound examples include metal oxides (for example, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide) and sulfates (for example, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt 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, cobalt sulfate.
  • metal halides eg calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide etc.
  • perchloric acids eg perchloric acid Barium, magnesium perchlorate, and the like
  • 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 on the side facing the support substrate with the organic layer interposed therebetween or on the sealing film.
  • the mechanical strength is not necessarily high, and thus it is preferable to provide such a protective film and a protective plate.
  • the same glass plate, polymer plate / film, metal plate / film, etc. used for the sealing can be used. It is preferable to use a film.
  • the organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1) and can extract only about 15% to 20% of the light generated in the light emitting layer. It is generally said. This is because light incident on the interface (interface between the transparent substrate and air) at an angle ⁇ greater than the critical angle causes total reflection and cannot be taken out of the device, or between the transparent electrode or light emitting layer and the transparent substrate. This is because the light is totally reflected between the light and the light is guided through the transparent electrode or the light emitting layer, and as a result, the light escapes in the side surface direction of the element.
  • a method of improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate and preventing total reflection at the transparent substrate and the air interface (US Pat. No. 4,774,435), A method for improving efficiency by giving light condensing property to a substrate (Japanese Patent Laid-Open No. 63-314795), a method of forming a reflective surface on the side surface of an element (Japanese Patent Laid-Open No. 1-220394), and light emission from the substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the bodies (Japanese Patent Laid-Open No.
  • these methods can be used in combination with the organic EL device of the present invention.
  • a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, transparent A method of forming a diffraction grating between any layers of the 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 aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 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 that has 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 in any layer or medium (in a transparent substrate or transparent electrode), and the light is removed. I want to take it out.
  • the diffraction grating to be introduced has a two-dimensional periodic refractive index. This is because light emitted from the light-emitting layer is randomly generated in all directions, so in a general one-dimensional diffraction grating having a periodic refractive index distribution only in a certain direction, only light traveling in a specific direction is diffracted. Therefore, the light extraction efficiency does not increase so much. However, by making the refractive index distribution a two-dimensional distribution, light traveling in all directions is diffracted, and light extraction efficiency is increased.
  • the position where the diffraction grating is introduced may be in any of the layers or in the medium (in the transparent substrate or the 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 1/2 to 3 times the wavelength of light in the medium.
  • the arrangement of the diffraction grating 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 is processed on the light extraction side of the substrate so as to provide, for example, a microlens array structure, or combined with a so-called condensing sheet, for example, with respect to a specific direction, for example, the device light emitting surface.
  • a specific direction for example, the device light emitting surface.
  • quadrangular pyramids having a side of 30 ⁇ m and an apex angle of 90 degrees are arranged two-dimensionally on the light extraction side of the substrate.
  • One side is preferably 10 to 100 ⁇ m. If it becomes smaller than this, the effect of diffraction will generate
  • the condensing sheet it is possible to use, for example, a sheet that has been put to practical use in an LED backlight of a liquid crystal display device.
  • a sheet for example, Sumitomo 3M brightness enhancement film (BEF) can be used.
  • BEF Sumitomo 3M brightness enhancement film
  • the base material may be formed by forming a ⁇ -shaped stripe having a vertex angle of 90 degrees and a pitch of 50 ⁇ m, or the vertex angle is rounded and the pitch is changed randomly. Other shapes may be used.
  • a light diffusion plate / film may be used in combination with the light collecting sheet.
  • 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 film thickness of 1 ⁇ m or less, preferably 10 to 200 nm, thereby producing an anode.
  • the light emitting layer of the organic EL device of the present invention is formed by a wet process as described above.
  • a method for forming an organic layer other than the light emitting layer there are a vapor deposition method, a wet process (spin coating method, die coating method, casting method, ink jet method, spray method, printing method), etc., but a homogeneous film is easily obtained.
  • film formation by a coating method such as a spin coating method, a die coating method, an ink jet method, a spray method, a printing method, or the like is preferable for part or all of the organic layer in view of the difficulty of generating pinholes.
  • 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, halogenated hydrocarbons such as dichlorobenzene, toluene, xylene, and mesitylene.
  • Aromatic hydrocarbons such as 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 by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 50 to 200 nm, and a cathode is provided.
  • a desired organic EL element can be obtained.
  • a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 to 40 V with the positive polarity of the anode and the negative polarity of the cathode.
  • An alternating voltage may be applied.
  • the alternating current waveform to be applied may be arbitrary.
  • Example 1 Production of organic EL element >> [Production of Organic EL Element 111] After patterning a substrate (NH technoglass NA45) formed by depositing 100 nm of ITO (indium tin oxide) on a 100 mm ⁇ 100 mm ⁇ 1.1 mm glass substrate as an anode, a substrate provided with this ITO transparent electrode was formed. Ultrasonic cleaning with isopropyl alcohol, drying with dry nitrogen gas, and UV ozone cleaning were performed for 5 minutes.
  • ITO indium tin oxide
  • This substrate was transferred to a nitrogen atmosphere, and a solution obtained by dissolving 60 mg of Exemplified Compound 4-1 in 10 ml of toluene on the first hole transport layer was formed into a film (film thickness) by spin coating under conditions of 1000 rpm and 30 seconds. About 40 nm) and irradiated with ultraviolet light for 30 seconds, followed by heat drying at 120 ° C. for 30 minutes to form a second hole transport layer.
  • the light emitting layer composition 1 having the following composition was discharged and injected using an inkjet head (manufactured by Epson; MJ800C) so that the wet film thickness was 4 ⁇ m.
  • This substrate was fixed to a substrate holder of a drying box provided with upper and lower partition walls and provided with an independent drying air temperature controller at the upper and lower portions of the partition wall, and heating controlled to 120 ° C. on the upper surface of the substrate (light emitting layer coating surface). Dry nitrogen was circulated, and heated dry nitrogen circulated at 80 ° C. on the back side of the substrate. In this state, the light emitting layer was dried by performing a drying process for 10 minutes. It was confirmed that the temperature of dry nitrogen circulated on both sides of the substrate was controlled within ⁇ 1 ° C. from the start to the end of drying.
  • the organic EL element 111 was formed in the same manner except that the temperature of nitrogen to be circulated to the substrate upper surface side and the substrate rear surface side in the drying step after the discharge injection of the light emitting layer composition 1 was changed as shown in Table 1. EL elements 112 to 114 were produced.
  • Organic EL Elements 121-123, 131-133, 141-142 are produced in the production of the organic EL element 111, the material constituting the light emitting layer composition 1 is changed as shown in Table 1, and nitrogen circulated between the substrate upper surface side and the substrate back surface side in the drying step after the discharge injection of the light emitting layer composition.
  • Organic EL elements 121 to 123, 131 to 133, and 141 to 142 were fabricated in the same manner except that the temperature was changed as shown in Table 1.
  • the concentration distribution of the light-emitting dopant contained in the light-emitting layer of the obtained organic EL element is detected by analyzing the Ir distribution in the film thickness direction by TOF-SIMS (time-of-flight secondary ion mass spectrometry). Can do.
  • Table 1 shows the concentration distribution from the anode side to the cathode side in the light emitting layers of the organic EL devices 111 to 114, 121 to 123, 131 to 133, and 141 to 142.
  • the external extraction quantum efficiency of the organic EL elements 121 to 123 is a relative value with the measured value of the organic EL element 123 (comparative) as 100, and the external extraction efficiency of the organic EL elements 131 to 133 is a measurement of the organic EL element 133 (comparative).
  • the relative value with the value of 100, the external extraction quantum efficiency of the organic EL elements 141 to 143 is the relative value with the measured value of the organic EL element 143 (comparison) as 100, and the external extraction efficiency of the organic EL elements 151 to 153 is the organic EL
  • the relative value when the measured value of the element 153 (comparison) is 100 and the external extraction efficiency of the organic EL elements 161 to 162 are expressed as relative values when the measured value of the organic EL element 162 (comparative) is 100. .
  • the produced organic EL element was continuously driven by applying a current that would give a front luminance of 1000 cd / m 2 .
  • the time required for the front luminance to reach the initial half value (500 cd / m 2 ) is obtained, and the light emission lifetimes of the organic EL elements 111 to 116 are relative values with the measured value of the organic EL element 116 (comparative) as 100. expressed.
  • the light emission lifetimes of the organic EL elements 121 to 123 are relative values with the measured value of the organic EL element 123 (comparative) as 100, and the light emission lifetimes of the organic EL elements 131 to 133 are the measured value of the organic EL element 133 (comparative) as 100.
  • the relative lifetimes of the organic EL elements 141 to 143 are relative values with the measured value of the organic EL element 143 (comparison) as 100, and the emission lifetimes of the organic EL elements 151 to 153 are those of the organic EL element 153 (comparative).
  • the relative value when the measured value is 100, and the light emission lifetimes of the organic EL elements 161 to 162 are expressed as relative values when the measured value of the organic EL element 162 (comparative) is 100.
  • the organic EL device of the present invention can continuously change the concentration of the light-emitting dopant in the light-emitting layer even in the manufacturing method using the wet process. As a result, the external extraction quantum efficiency and the light emission lifetime are improved. It can be seen that it has improved.
  • Example 2 Production of organic EL element >> [Production of Organic EL Element 211] After patterning a substrate (NH technoglass NA45) formed by depositing 100 nm of ITO (indium tin oxide) on a 100 mm ⁇ 100 mm ⁇ 1.1 mm glass substrate as an anode, a substrate provided with this ITO transparent electrode was formed. Ultrasonic cleaning with isopropyl alcohol, drying with dry nitrogen gas, and UV ozone cleaning were performed for 5 minutes.
  • ITO indium tin oxide
  • polystyrene sulfonate PEDOT / PSS, Bayer, Baytron P Al 4083
  • PEDOT / PSS polystyrene sulfonate
  • the film was dried at 200 ° C. for 1 hour to provide a first hole transport layer having a thickness of 30 nm.
  • This substrate was transferred to a nitrogen atmosphere, and a solution obtained by dissolving 60 mg of Exemplified Compound 4-1 in 10 ml of toluene on the first hole transport layer was formed into a film (film thickness) by spin coating under conditions of 1000 rpm and 30 seconds. About 40 nm) and irradiated with ultraviolet light for 30 seconds, followed by heat drying at 120 ° C. for 30 minutes to form a second hole transport layer.
  • the light emitting layer composition 1 having the following composition was discharged and injected using an inkjet head (manufactured by Epson; MJ800C) so that the wet film thickness was 4 ⁇ m.
  • the substrate was subjected to a drying treatment for 10 minutes in a 120 ° C. drying box to form the light emitting layer 1.
  • Light emitting layer composition 1 (2) -16 1.0 part by mass (1) -79 0.18 part by mass Toluene 100 parts by mass
  • a light emitting layer composition 2 having the following composition was wet filmed using an inkjet head (manufactured by Epson; MJ800C). The discharge was injected so that the thickness was 2 ⁇ m. This substrate was subjected to a drying treatment for 10 minutes in a drying box at 120 ° C. to form a 20 nm light emitting layer 2.
  • (Light emitting layer composition 2) (2) -16 1.0 part by mass (1) -79 0.02 part by mass Toluene 100 parts by mass This substrate was fixed to the substrate holder of the vacuum evaporation apparatus, while 200 mg of ET-A was added to a molybdenum resistance heating boat. Then, 100 mg of CsF was put into another resistance heating boat made of molybdenum, and attached to a vacuum deposition apparatus. The vacuum chamber was depressurized to 4 ⁇ 10 ⁇ 4 Pa, and then heated by energizing the heating boat containing ET-A and CsF, and the light emitting layer was deposited at a deposition rate of 0.2 nm / second and 0.03 nm / second, respectively. An electron transport layer having a film thickness of 40 nm was further provided. Subsequently, 110 nm of aluminum was deposited to form a cathode, and an organic EL element 211 was produced.
  • the light emitting dopant / light emitting host ratio of the solution coated on the most anode side among the two or more kinds of light emitting layer solutions having different light emitting dopant concentrations of claim 7 and claim 8 is 100. This corresponds to an emission dopant / emission host ratio of 5 to 0% by mass of the solution coated on the cathode side, and in this case, the emission dopant / emission host ratio of the solution applied on the anode side is 18%.
  • the light emitting dopant / light emitting host ratio of the solution applied on the most cathode side is 2% by mass.
  • organic EL elements 212 to 218 were produced in the same manner except that the compositions and film thicknesses of the light emitting layer compositions 1 and 2 were changed as shown in Table 2.
  • the organic EL elements 212 and 213 are also equivalent to claims 7 and 8, respectively, and the emission dopant / emission host ratio of the solution coated on the most anode side is 20% by mass, 40% by mass, and most on the cathode side, respectively.
  • the ratio of the luminescent dopant / luminescent host of the solution applied to is 0% by mass and 0% by mass, respectively.
  • the organic EL element 214 is claimed in claim 7, but the light emitting dopant / light emitting host ratio of the solution coated on the most anode side is 14% by mass, and the light emitting dopant / light emitting host ratio of the solution coated on the most cathode side is mass. Since it is 6%, it does not correspond to Claim 8.
  • the solubility of the luminescent dopant ((1) -79) in chlorobenzene is higher than that of toluene, and the boiling point of chlorobenzene is higher. That is, it corresponds to claim 9.
  • the organic EL element 218 has a higher solubility in the luminescent dopant ((1) -79) in chlorobenzene than p-xylene, and conversely, the boiling point of p-xylene is equal to or higher than that of chlorobenzene. Does not correspond to 9.
  • the organic EL device of the present invention can continuously change the concentration of the light-emitting dopant in the light-emitting layer even in the manufacturing method using the wet process, and as a result, the external extraction quantum efficiency and the light emission lifetime are improved. It can be seen that it has improved.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention a trait à un procédé de fabrication d'un dispositif électroluminescent organique présentant une efficacité lumineuse élevée et une longue durée de vie, dans lequel un dispositif électroluminescent organique peut être produit de façon stable à l'aide d'un procédé d'attaque à l'acide. De façon spécifique, la présente invention a trait à un procédé de fabrication d'un dispositif électroluminescent organique qui comprend au moins, sur un substrat, une anode, une cathode et une couche électroluminescente intercalée entre l'anode et la cathode et contenant un hôte luminescent et un dopant luminescent. Ce procédé de fabrication d'un dispositif électroluminescent organique est caractérisé en ce que la couche électroluminescente est formée au moyen d'un procédé d'attaque à l'acide et en ce que la concentration du dopant luminescent contenu dans la couche électroluminescente est modifiée en continu du côté de l'anode vers le côté de la cathode.
PCT/JP2008/072756 2007-12-28 2008-12-15 Dispositif électroluminescent organique et procédé de fabrication de dispositif électroluminescent organique WO2009084413A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2009547981A JPWO2009084413A1 (ja) 2007-12-28 2008-12-15 有機エレクトロルミネッセンス素子、及び有機エレクトロルミネッセンス素子の製造方法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007339104 2007-12-28
JP2007-339104 2007-12-28

Publications (1)

Publication Number Publication Date
WO2009084413A1 true WO2009084413A1 (fr) 2009-07-09

Family

ID=40824134

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/072756 WO2009084413A1 (fr) 2007-12-28 2008-12-15 Dispositif électroluminescent organique et procédé de fabrication de dispositif électroluminescent organique

Country Status (2)

Country Link
JP (1) JPWO2009084413A1 (fr)
WO (1) WO2009084413A1 (fr)

Cited By (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011051404A1 (fr) 2009-10-28 2011-05-05 Basf Se Complexes hétéroleptiques à base de carbène et leur utilisation dans l'électronique organique
WO2011073149A1 (fr) 2009-12-14 2011-06-23 Basf Se Complexes métalliques contenant des ligands diazabenzimidazole-carbéniques et leur utilisation dans des oled
WO2011132550A1 (fr) * 2010-04-20 2011-10-27 コニカミノルタホールディングス株式会社 Élément électroluminescent organique, dispositif d'affichage, et dispositif d'éclairage
WO2012039241A1 (fr) * 2010-09-24 2012-03-29 コニカミノルタホールディングス株式会社 Élément électroluminescent organique et procédé de fabrication d'un élément électroluminescent organique
JP2012084415A (ja) * 2010-10-13 2012-04-26 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子の製造方法および有機エレクトロルミネッセンス素子
WO2012077714A1 (fr) * 2010-12-09 2012-06-14 コニカミノルタホールディングス株式会社 Élément électroluminescent organique et dispositif d'éclairage
WO2013008835A1 (fr) * 2011-07-12 2013-01-17 株式会社日立製作所 Matériau pour formation de couche luminescente organique, liquide de revêtement pour formation d'élément luminescent organique, élément luminescent organique, dispositif de source lumineuse, et procédés de fabrication associés
WO2013046264A1 (fr) * 2011-09-28 2013-04-04 パナソニック株式会社 Encre destinée à un élément électroluminescent organique et procédé de production de ladite encre
WO2013046265A1 (fr) * 2011-09-28 2013-04-04 パナソニック株式会社 Procédé de production d'un élément électroluminescent organique, élément électroluminescent organique, écran organique, dispositif électroluminescent organique, procédé de formation de couche fonctionnelle, matériau fonctionnel, écran et dispositif électroluminescent
WO2013168534A1 (fr) * 2012-05-09 2013-11-14 コニカミノルタ株式会社 Élément à électroluminescence organique, procédé de production d'un élément à électroluminescence organique, dispositif d'affichage et dispositif d'éclairage
WO2014012972A1 (fr) 2012-07-19 2014-01-23 Basf Se Complexes métalliques binucléaires comprenant des ligands carbènes et leur utilisation dans des diodes électroluminescentes organiques (oled)
US8691401B2 (en) 2010-04-16 2014-04-08 Basf Se Bridged benzimidazole-carbene complexes and use thereof in OLEDS
WO2014147134A1 (fr) 2013-03-20 2014-09-25 Basf Se Complexes de carbène d'azabenzimidazole formant des amplificateurs d'efficacité dans des oled
JP2014526144A (ja) * 2011-07-05 2014-10-02 プレックストロニクス インコーポレーティッド 垂直に相分離している有機半導体材料層
WO2014177518A1 (fr) 2013-04-29 2014-11-06 Basf Se Complexes de métal de transition avec des ligands carbène et leur utilisation dans des delo
WO2015000955A1 (fr) 2013-07-02 2015-01-08 Basf Se Complexes de métal et de carbène de type diazabenzimidazole monosubstitué destinés à être utilisés dans des diodes électroluminescentes organiques
US9142792B2 (en) 2010-06-18 2015-09-22 Basf Se Organic electronic devices comprising a layer comprising at least one metal organic compound and at least one metal oxide
WO2016016791A1 (fr) 2014-07-28 2016-02-04 Idemitsu Kosan Co., Ltd (Ikc) Benzimidazolo[1,2-a] benzimidazoles 2,9-fonctionnalisé utilisés comme hôtes pour diodes électroluminescentes organiques (oled)
EP2982676A1 (fr) 2014-08-07 2016-02-10 Idemitsu Kosan Co., Ltd. Benzimidazo [2,1-B] benzoxazoles pour applications électroniques
EP2993215A1 (fr) 2014-09-04 2016-03-09 Idemitsu Kosan Co., Ltd. Azabenzimidazo[2,1-a]benzimidazoles pour applications électroniques
US9315724B2 (en) 2011-06-14 2016-04-19 Basf Se Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs
EP3015469A1 (fr) 2014-10-30 2016-05-04 Idemitsu Kosan Co., Ltd. 5-((benz)imidazol-2-yl)benzimidazo[1,2-a]benzimidazoles pour des applications électroniques
WO2016079169A1 (fr) 2014-11-18 2016-05-26 Basf Se Complexes de pt-carbène ou de pd-carbène destinés à être utilisés dans des diodes électroluminescentes organiques
WO2016079667A1 (fr) 2014-11-17 2016-05-26 Idemitsu Kosan Co., Ltd. Dérivés d'indole pour des applications électroniques
US9373802B2 (en) 2011-02-07 2016-06-21 Idemitsu Kosan Co., Ltd. Biscarbazole derivatives and organic electroluminescence device employing the same
EP3034507A1 (fr) 2014-12-15 2016-06-22 Idemitsu Kosan Co., Ltd Dibenzothiophènes et dibenzofurannes 1-functionalisés pour diodes électroluminescentes organiques (OLED)
EP3034506A1 (fr) 2014-12-15 2016-06-22 Idemitsu Kosan Co., Ltd Dérivés de carbazole 4-fonctionnalisés pour applications électroniques
EP3053918A1 (fr) 2015-02-06 2016-08-10 Idemitsu Kosan Co., Ltd Benzimidazoles substitués par un 2-carbazole pour des applications électroniques
EP3054498A1 (fr) 2015-02-06 2016-08-10 Idemitsu Kosan Co., Ltd. Bisimidazodiazocines
EP3061759A1 (fr) 2015-02-24 2016-08-31 Idemitsu Kosan Co., Ltd Dibenzofuranes à substituant nitrile
US9450193B2 (en) 2009-11-03 2016-09-20 Samsung Sdi Co., Ltd. Compound for organic photoelectric device and organic photoelectric device including the same
EP3070144A1 (fr) 2015-03-17 2016-09-21 Idemitsu Kosan Co., Ltd. Composés cycliques à sept chaînons
EP3072943A1 (fr) 2015-03-26 2016-09-28 Idemitsu Kosan Co., Ltd. Benzonitriles de dibenzofurane/carbazole-substitué
EP3075737A1 (fr) 2015-03-31 2016-10-05 Idemitsu Kosan Co., Ltd Benzimidazolo [1,2-a] benzimidazole portant des groupes heteroarylnitril aryl- ou pour diodes électroluminescentes organiques
US9478755B2 (en) 2009-11-03 2016-10-25 Cheil Industries, Inc. Compound for organic photoelectric device and organic photoelectric device including the same
WO2016193243A1 (fr) 2015-06-03 2016-12-08 Udc Ireland Limited Dispositifs oled très efficaces à temps de déclin très courts
EP3150606A1 (fr) 2015-10-01 2017-04-05 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazoles avec des groupements benzofurane ou benzothiophène pour des diodes émittant de la lumière
EP3150604A1 (fr) 2015-10-01 2017-04-05 Idemitsu Kosan Co., Ltd. Groupes benzimidazolo [1,2-a] benzimidazoles portant des benzimidazolo [1,2-a] benzimidazolyles, groupes carbazolyles, groupes benzofuranes ou benzothiophènes pour diodes électroluminescentes organiques
WO2017056055A1 (fr) 2015-10-01 2017-04-06 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole portant des groupes triazine pour diodes électroluminescentes organiques
WO2017056053A1 (fr) 2015-10-01 2017-04-06 Idemitsu Kosan Co., Ltd. Groupes benzimidazolo[1,2-a]benzimidazolyle, groupes carbazolyle, groupes benzofuranne ou groupes benzothiophène portant un composé benzimidazolo[1,2-a] benzimidazole pour diodes électroluminescentes organiques
WO2017078182A1 (fr) 2015-11-04 2017-05-11 Idemitsu Kosan Co., Ltd. Hétéroaryles fusionnés à un benzimidazole
WO2017093958A1 (fr) 2015-12-04 2017-06-08 Idemitsu Kosan Co., Ltd. Dérivés benzimidazolo[1,2-a]benzimidazole pour des diodes électroluminescentes organiques
WO2017109722A1 (fr) 2015-12-21 2017-06-29 Idemitsu Kosan Co., Ltd. Composés hétérocycliques azotés et dispositifs électroluminescents organiques contenant ceux-ci
WO2017178864A1 (fr) 2016-04-12 2017-10-19 Idemitsu Kosan Co., Ltd. Composés cycliques à sept anneaux
EP3239161A1 (fr) 2013-07-31 2017-11-01 UDC Ireland Limited Complexes de carbène-métal diazabenzimidazole luminescent
US9862739B2 (en) 2014-03-31 2018-01-09 Udc Ireland Limited Metal complexes, comprising carbene ligands having an O-substituted non-cyclometalated aryl group and their use in organic light emitting diodes
EP3415521A1 (fr) 2011-06-14 2018-12-19 UDC Ireland Limited Complexes de métal comprenant des ligands de carbène d'azabenzimidazole et leur utilisation dans des oled
US10347851B2 (en) 2013-12-20 2019-07-09 Udc Ireland Limited Highly efficient OLED devices with very short decay times

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1174083A (ja) * 1997-09-01 1999-03-16 Seiko Epson Corp 電界発光素子およびその製造方法
JP2003229272A (ja) * 2002-01-31 2003-08-15 Toyota Industries Corp 有機ｅｌ素子
JP2004006102A (ja) * 2002-05-31 2004-01-08 Canon Inc エレクトロルミネッセンス素子
JP2005038672A (ja) * 2003-07-18 2005-02-10 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、照明装置及び表示装置
JP2006066294A (ja) * 2004-08-27 2006-03-09 Hitachi Displays Ltd 電子装置の製造方法およびこの製造に用いる非晶質薄膜形成用インク組成物
JP2007042314A (ja) * 2005-08-01 2007-02-15 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP2007221132A (ja) * 2006-02-13 2007-08-30 Samsung Sdi Co Ltd 有機発光素子
JP2007250716A (ja) * 2006-03-15 2007-09-27 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020025918A (ko) * 2002-02-15 2002-04-04 박병주 습식 공정으로 제작된 유기 반도체 디바이스 및 유기전계발광 소자
JP2004273423A (ja) * 2002-09-27 2004-09-30 Katsuo Orihara ポリマーデバイス、及びその製造方法
DE202005012650U1 (de) * 2005-08-11 2005-11-24 Lichtenhagen, Stefan Kabelbinder
US8920942B2 (en) * 2006-03-23 2014-12-30 Konica Minolta Holdings, Inc. Organic electroluminescent element, display device and illuminating device

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1174083A (ja) * 1997-09-01 1999-03-16 Seiko Epson Corp 電界発光素子およびその製造方法
JP2003229272A (ja) * 2002-01-31 2003-08-15 Toyota Industries Corp 有機ｅｌ素子
JP2004006102A (ja) * 2002-05-31 2004-01-08 Canon Inc エレクトロルミネッセンス素子
JP2005038672A (ja) * 2003-07-18 2005-02-10 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、照明装置及び表示装置
JP2006066294A (ja) * 2004-08-27 2006-03-09 Hitachi Displays Ltd 電子装置の製造方法およびこの製造に用いる非晶質薄膜形成用インク組成物
JP2007042314A (ja) * 2005-08-01 2007-02-15 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP2007221132A (ja) * 2006-02-13 2007-08-30 Samsung Sdi Co Ltd 有機発光素子
JP2007250716A (ja) * 2006-03-15 2007-09-27 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置

Cited By (86)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11871654B2 (en) 2009-10-28 2024-01-09 Udc Ireland Limited Heteroleptic carbene complexes and the use thereof in organic electronics
WO2011051404A1 (fr) 2009-10-28 2011-05-05 Basf Se Complexes hétéroleptiques à base de carbène et leur utilisation dans l'électronique organique
US11189806B2 (en) 2009-10-28 2021-11-30 Udc Ireland Limited Heteroleptic carbene complexes and the use thereof in organic electronics
US9450193B2 (en) 2009-11-03 2016-09-20 Samsung Sdi Co., Ltd. Compound for organic photoelectric device and organic photoelectric device including the same
US9478755B2 (en) 2009-11-03 2016-10-25 Cheil Industries, Inc. Compound for organic photoelectric device and organic photoelectric device including the same
US10916716B2 (en) 2009-12-14 2021-02-09 Udc Ireland Limited Metal complexes comprising diazabenzmidazolocarbene ligands and the use thereof in OLEDS
WO2011073149A1 (fr) 2009-12-14 2011-06-23 Basf Se Complexes métalliques contenant des ligands diazabenzimidazole-carbéniques et leur utilisation dans des oled
US11839140B2 (en) 2009-12-14 2023-12-05 Udc Ireland Limited Metal complexes comprising diazabenzmidazolocarbene ligands and the use thereof in OLEDS
US11444254B2 (en) 2009-12-14 2022-09-13 Udc Ireland Limited Metal complexes comprising diazabenzmidazolocarbene ligands and the use thereof in OLEDs
US10090476B2 (en) 2009-12-14 2018-10-02 Udc Ireland Limited Metal complexes comprising diazabenzmidazolocarbene ligands and the use thereof in OLEDs
US9487548B2 (en) 2009-12-14 2016-11-08 Udc Ireland Limited Metal complexes comprising diazabenzimidazolocarbene ligands and the use thereof in OLEDs
US8691401B2 (en) 2010-04-16 2014-04-08 Basf Se Bridged benzimidazole-carbene complexes and use thereof in OLEDS
JPWO2011132550A1 (ja) * 2010-04-20 2013-07-18 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、表示装置及び照明装置
WO2011132550A1 (fr) * 2010-04-20 2011-10-27 コニカミノルタホールディングス株式会社 Élément électroluminescent organique, dispositif d'affichage, et dispositif d'éclairage
US9142792B2 (en) 2010-06-18 2015-09-22 Basf Se Organic electronic devices comprising a layer comprising at least one metal organic compound and at least one metal oxide
WO2012039241A1 (fr) * 2010-09-24 2012-03-29 コニカミノルタホールディングス株式会社 Élément électroluminescent organique et procédé de fabrication d'un élément électroluminescent organique
JP2012084415A (ja) * 2010-10-13 2012-04-26 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子の製造方法および有機エレクトロルミネッセンス素子
JPWO2012077714A1 (ja) * 2010-12-09 2014-05-22 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子及び照明装置
JP5831459B2 (ja) * 2010-12-09 2015-12-09 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子及び照明装置
WO2012077714A1 (fr) * 2010-12-09 2012-06-14 コニカミノルタホールディングス株式会社 Élément électroluminescent organique et dispositif d'éclairage
US9373802B2 (en) 2011-02-07 2016-06-21 Idemitsu Kosan Co., Ltd. Biscarbazole derivatives and organic electroluminescence device employing the same
US10230057B2 (en) 2011-02-07 2019-03-12 Idemitsu Kosan Co., Ltd. Biscarbazole derivatives and organic electroluminescence device employing the same
US9818958B2 (en) 2011-02-07 2017-11-14 Idemitsu Kosan Co., Ltd. Biscarbazole derivatives and organic electroluminescence device employing the same
EP3415521A1 (fr) 2011-06-14 2018-12-19 UDC Ireland Limited Complexes de métal comprenant des ligands de carbène d'azabenzimidazole et leur utilisation dans des oled
US9315724B2 (en) 2011-06-14 2016-04-19 Basf Se Metal complexes comprising azabenzimidazole carbene ligands and the use thereof in OLEDs
JP2014526144A (ja) * 2011-07-05 2014-10-02 プレックストロニクス インコーポレーティッド 垂直に相分離している有機半導体材料層
WO2013008835A1 (fr) * 2011-07-12 2013-01-17 株式会社日立製作所 Matériau pour formation de couche luminescente organique, liquide de revêtement pour formation d'élément luminescent organique, élément luminescent organique, dispositif de source lumineuse, et procédés de fabrication associés
US9954193B2 (en) 2011-07-12 2018-04-24 Hitachi, Ltd. Material for forming organic light-emitting layer, coating liquid for forming organic light-emitting element, organic light-emitting element and light source device, and method for manufacturing same
US8822986B2 (en) 2011-09-28 2014-09-02 Panasonic Corporation Method for manufacturing organic light-emitting element, organic light-emitting element, organic display device, organic light-emitting device, method for forming functional layer, functional member, display device, and light-emitting device
JPWO2013046265A1 (ja) * 2011-09-28 2015-03-26 パナソニック株式会社 有機発光素子の製造方法、有機発光素子、有機表示装置、有機発光装置、機能層の形成方法、機能性部材、表示装置および発光装置
WO2013046264A1 (fr) * 2011-09-28 2013-04-04 パナソニック株式会社 Encre destinée à un élément électroluminescent organique et procédé de production de ladite encre
JPWO2013046264A1 (ja) * 2011-09-28 2015-03-26 パナソニック株式会社 有機発光素子用インク、および当該インクの製造方法
US9023239B2 (en) 2011-09-28 2015-05-05 Joled Inc. Ink for organic light-emitting element and a method for producing the same
WO2013046265A1 (fr) * 2011-09-28 2013-04-04 パナソニック株式会社 Procédé de production d'un élément électroluminescent organique, élément électroluminescent organique, écran organique, dispositif électroluminescent organique, procédé de formation de couche fonctionnelle, matériau fonctionnel, écran et dispositif électroluminescent
KR101900960B1 (ko) 2011-09-28 2018-09-20 가부시키가이샤 제이올레드 유기 발광 소자용 잉크, 및 당해 잉크의 제조 방법
CN103125030A (zh) * 2011-09-28 2013-05-29 松下电器产业株式会社 有机发光元件用墨及其制造方法
CN103141158A (zh) * 2011-09-28 2013-06-05 松下电器产业株式会社 有机发光元件的制造方法、有机发光元件、有机显示装置、有机发光装置、功能层的形成方法、功能性部件、显示装置以及发光装置
CN103141158B (zh) * 2011-09-28 2016-06-22 株式会社日本有机雷特显示器 有机发光元件的制造方法、有机发光元件、有机显示装置、有机发光装置、功能层的形成方法、功能性部件、显示装置以及发光装置
WO2013168534A1 (fr) * 2012-05-09 2013-11-14 コニカミノルタ株式会社 Élément à électroluminescence organique, procédé de production d'un élément à électroluminescence organique, dispositif d'affichage et dispositif d'éclairage
JPWO2013168534A1 (ja) * 2012-05-09 2016-01-07 コニカミノルタ株式会社 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、表示装置および照明装置
US9590196B2 (en) 2012-07-19 2017-03-07 Udc Ireland Limited Dinuclear metal complexes comprising carbene ligands and the use thereof in OLEDs
EP3133079A1 (fr) 2012-07-19 2017-02-22 UDC Ireland Limited Complexes de métal binucléaire comportant des ligands de carbène et leur utilisation dans des oled
WO2014012972A1 (fr) 2012-07-19 2014-01-23 Basf Se Complexes métalliques binucléaires comprenant des ligands carbènes et leur utilisation dans des diodes électroluminescentes organiques (oled)
WO2014147134A1 (fr) 2013-03-20 2014-09-25 Basf Se Complexes de carbène d'azabenzimidazole formant des amplificateurs d'efficacité dans des oled
WO2014177518A1 (fr) 2013-04-29 2014-11-06 Basf Se Complexes de métal de transition avec des ligands carbène et leur utilisation dans des delo
EP3608329A1 (fr) 2013-07-02 2020-02-12 UDC Ireland Limited Complexes métalliques contenant des ligands diazabenzimidazole-carbéniques monosubstitués destinés à être utilisés dans des diodes électroluminescentes organiques
EP3266789A1 (fr) 2013-07-02 2018-01-10 UDC Ireland Limited Complexes métalliques contenant des ligands diazabenzimidazole-carbéniques monosubstitués destinés à être utilisés dans des diodes électroluminescentes organiques
WO2015000955A1 (fr) 2013-07-02 2015-01-08 Basf Se Complexes de métal et de carbène de type diazabenzimidazole monosubstitué destinés à être utilisés dans des diodes électroluminescentes organiques
EP3239161A1 (fr) 2013-07-31 2017-11-01 UDC Ireland Limited Complexes de carbène-métal diazabenzimidazole luminescent
US10347851B2 (en) 2013-12-20 2019-07-09 Udc Ireland Limited Highly efficient OLED devices with very short decay times
US11765967B2 (en) 2013-12-20 2023-09-19 Udc Ireland Limited Highly efficient OLED devices with very short decay times
US11075346B2 (en) 2013-12-20 2021-07-27 Udc Ireland Limited Highly efficient OLED devices with very short decay times
EP3916822A1 (fr) 2013-12-20 2021-12-01 UDC Ireland Limited Dispositifs oled hautement efficaces avec de très courts temps de détérioration
US10118939B2 (en) 2014-03-31 2018-11-06 Udc Ireland Limited Metal complexes, comprising carbene ligands having an o-substituted non-cyclometalated aryl group and their use in organic light emitting diodes
US9862739B2 (en) 2014-03-31 2018-01-09 Udc Ireland Limited Metal complexes, comprising carbene ligands having an O-substituted non-cyclometalated aryl group and their use in organic light emitting diodes
US10370396B2 (en) 2014-03-31 2019-08-06 Udc Ireland Limited Metal complexes, comprising carbene ligands having an O-substituted non-cyclometallated aryl group and their use in organic light emitting diodes
WO2016016791A1 (fr) 2014-07-28 2016-02-04 Idemitsu Kosan Co., Ltd (Ikc) Benzimidazolo[1,2-a] benzimidazoles 2,9-fonctionnalisé utilisés comme hôtes pour diodes électroluminescentes organiques (oled)
EP2982676A1 (fr) 2014-08-07 2016-02-10 Idemitsu Kosan Co., Ltd. Benzimidazo [2,1-B] benzoxazoles pour applications électroniques
EP2993215A1 (fr) 2014-09-04 2016-03-09 Idemitsu Kosan Co., Ltd. Azabenzimidazo[2,1-a]benzimidazoles pour applications électroniques
EP3015469A1 (fr) 2014-10-30 2016-05-04 Idemitsu Kosan Co., Ltd. 5-((benz)imidazol-2-yl)benzimidazo[1,2-a]benzimidazoles pour des applications électroniques
WO2016067261A1 (fr) 2014-10-30 2016-05-06 Idemitsu Kosan Co., Ltd. 5-((benz)imidazol-2-yl) benzimidazo[1,2-a]benzimidazoles utilisés pour des applications électroniques
WO2016079667A1 (fr) 2014-11-17 2016-05-26 Idemitsu Kosan Co., Ltd. Dérivés d'indole pour des applications électroniques
WO2016079169A1 (fr) 2014-11-18 2016-05-26 Basf Se Complexes de pt-carbène ou de pd-carbène destinés à être utilisés dans des diodes électroluminescentes organiques
WO2016097983A1 (fr) 2014-12-15 2016-06-23 Idemitsu Kosan Co., Ltd. Dibenzothiophènes et dibenzofurannes fonctionnalisés en 1 pour diodes électroluminescentes organiques (oled)
EP3034507A1 (fr) 2014-12-15 2016-06-22 Idemitsu Kosan Co., Ltd Dibenzothiophènes et dibenzofurannes 1-functionalisés pour diodes électroluminescentes organiques (OLED)
EP3034506A1 (fr) 2014-12-15 2016-06-22 Idemitsu Kosan Co., Ltd Dérivés de carbazole 4-fonctionnalisés pour applications électroniques
WO2016125110A1 (fr) 2015-02-06 2016-08-11 Idemitsu Kosan Co., Ltd. Bis-imidazolo-diazocines
EP3053918A1 (fr) 2015-02-06 2016-08-10 Idemitsu Kosan Co., Ltd Benzimidazoles substitués par un 2-carbazole pour des applications électroniques
EP3054498A1 (fr) 2015-02-06 2016-08-10 Idemitsu Kosan Co., Ltd. Bisimidazodiazocines
EP3061759A1 (fr) 2015-02-24 2016-08-31 Idemitsu Kosan Co., Ltd Dibenzofuranes à substituant nitrile
EP3070144A1 (fr) 2015-03-17 2016-09-21 Idemitsu Kosan Co., Ltd. Composés cycliques à sept chaînons
EP3072943A1 (fr) 2015-03-26 2016-09-28 Idemitsu Kosan Co., Ltd. Benzonitriles de dibenzofurane/carbazole-substitué
EP3075737A1 (fr) 2015-03-31 2016-10-05 Idemitsu Kosan Co., Ltd Benzimidazolo [1,2-a] benzimidazole portant des groupes heteroarylnitril aryl- ou pour diodes électroluminescentes organiques
WO2016157113A1 (fr) 2015-03-31 2016-10-06 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole portant des groupes aryl- ou hétéroarylnitrile pour diodes électroluminescentes organiques
WO2016193243A1 (fr) 2015-06-03 2016-12-08 Udc Ireland Limited Dispositifs oled très efficaces à temps de déclin très courts
EP4060757A1 (fr) 2015-06-03 2022-09-21 UDC Ireland Limited Dispositifs delo hautement efficaces avec de très courts temps de déclin
EP3150604A1 (fr) 2015-10-01 2017-04-05 Idemitsu Kosan Co., Ltd. Groupes benzimidazolo [1,2-a] benzimidazoles portant des benzimidazolo [1,2-a] benzimidazolyles, groupes carbazolyles, groupes benzofuranes ou benzothiophènes pour diodes électroluminescentes organiques
EP3150606A1 (fr) 2015-10-01 2017-04-05 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazoles avec des groupements benzofurane ou benzothiophène pour des diodes émittant de la lumière
WO2017056055A1 (fr) 2015-10-01 2017-04-06 Idemitsu Kosan Co., Ltd. Benzimidazolo[1,2-a]benzimidazole portant des groupes triazine pour diodes électroluminescentes organiques
WO2017056053A1 (fr) 2015-10-01 2017-04-06 Idemitsu Kosan Co., Ltd. Groupes benzimidazolo[1,2-a]benzimidazolyle, groupes carbazolyle, groupes benzofuranne ou groupes benzothiophène portant un composé benzimidazolo[1,2-a] benzimidazole pour diodes électroluminescentes organiques
WO2017056052A1 (fr) 2015-10-01 2017-04-06 Idemitsu Kosan Co., Ltd. Groupes benzimidazolo[1,2-a]benzimidazolyle, groupes carbazolyle, groupes benzofuranne ou groupes benzothiophène portant un composé benzimidazolo[1,2-a] benzimidazole pour diodes électroluminescentes organiques
WO2017078182A1 (fr) 2015-11-04 2017-05-11 Idemitsu Kosan Co., Ltd. Hétéroaryles fusionnés à un benzimidazole
WO2017093958A1 (fr) 2015-12-04 2017-06-08 Idemitsu Kosan Co., Ltd. Dérivés benzimidazolo[1,2-a]benzimidazole pour des diodes électroluminescentes organiques
WO2017109722A1 (fr) 2015-12-21 2017-06-29 Idemitsu Kosan Co., Ltd. Composés hétérocycliques azotés et dispositifs électroluminescents organiques contenant ceux-ci
WO2017109727A1 (fr) 2015-12-21 2017-06-29 Idemitsu Kosan Co., Ltd. Phénylquinazolines hétérocondensées et leur utilisation dans des dispositifs électroniques
WO2017178864A1 (fr) 2016-04-12 2017-10-19 Idemitsu Kosan Co., Ltd. Composés cycliques à sept anneaux

Also Published As

Publication number Publication date
JPWO2009084413A1 (ja) 2011-05-19

Similar Documents

Publication Publication Date Title
JP5967057B2 (ja) 有機エレクトロルミネッセンス素子とその製造方法、照明装置及び表示装置
JP5181676B2 (ja) 有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP5609641B2 (ja) 有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP5765223B2 (ja) 有機エレクトロルミネッセンス素子の製造方法、並びに有機エレクトロルミネッセンス素子を備えた照明装置及び表示装置
JP5359869B2 (ja) 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、表示装置及び照明装置
JP5018891B2 (ja) 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP5600894B2 (ja) 白色有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP5103781B2 (ja) 化合物、該化合物を含む有機エレクトロルミネッセンス素子、照明装置
WO2009084413A1 (fr) Dispositif électroluminescent organique et procédé de fabrication de dispositif électroluminescent organique
JP5076899B2 (ja) 有機エレクトロルミネッセンス素子、その製造方法、該有機エレクトロルミネッセンス素子を有する表示装置及び照明装置
JP5201054B2 (ja) 有機エレクトロルミネッセンス材料、有機エレクトロルミネッセンス素子、青色燐光発光素子、表示装置及び照明装置
JP5499890B2 (ja) 有機エレクトロルミネッセンス素子、及びその製造方法
WO2010032663A1 (fr) Élément électroluminescent organique, dispositif d'affichage, dispositif d'éclairage et matériau d'élément électroluminescent organique
WO2009104488A1 (fr) Dispositif électroluminescent organique émettant de la lumière blanche
JP2008207520A (ja) 有機薄膜、有機薄膜の製造方法、電子デバイス、有機エレクトロルミネッセンス素子、表示装置及び照明装置
JPWO2008090795A1 (ja) 有機エレクトロルミネッセンス素子、表示装置及び照明装置
JP5423363B2 (ja) 有機エレクトロルミネッセンス素子、表示装置及び照明装置
WO2010119891A1 (fr) Élément électroluminescent organique
WO2011052250A1 (fr) Élément électroluminescent organique, matériau pour éléments électroluminescents organiques, dispositif d'affichage et dispositif d'éclairage
JP2010118591A (ja) 有機エレクトロルミネッセンス素子、表示装置、照明装置及び有機エレクトロルミネッセンス素子材料
JP2011009517A (ja) 有機エレクトロルミネッセンス素子
JP5521753B2 (ja) 有機エレクトロルミネッセンス素子
WO2012039241A1 (fr) Élément électroluminescent organique et procédé de fabrication d'un élément électroluminescent organique
JP5655616B2 (ja) 有機エレクトロルミネッセンス素子及び有機エレクトロルミネッセンス素子の製造方法
JP5835217B2 (ja) 有機エレクトロルミネッセンス素子

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08866750

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2009547981

Country of ref document: JP

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 08866750

Country of ref document: EP

Kind code of ref document: A1