+

WO2013031345A1 - Élément organique à électroluminescence - Google Patents

Élément organique à électroluminescence Download PDF

Info

Publication number
WO2013031345A1
WO2013031345A1 PCT/JP2012/065680 JP2012065680W WO2013031345A1 WO 2013031345 A1 WO2013031345 A1 WO 2013031345A1 JP 2012065680 W JP2012065680 W JP 2012065680W WO 2013031345 A1 WO2013031345 A1 WO 2013031345A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
light emitting
layer
organic
compound
Prior art date
Application number
PCT/JP2012/065680
Other languages
English (en)
Japanese (ja)
Inventor
中山　知是
雄史 小野
隼 古川
Original Assignee
コニカミノルタホールディングス株式会社
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 コニカミノルタホールディングス株式会社 filed Critical コニカミノルタホールディングス株式会社
Priority to JP2013531136A priority Critical patent/JP6107657B2/ja
Publication of WO2013031345A1 publication Critical patent/WO2013031345A1/fr

Links

Images

Classifications

    • 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
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • 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
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • H10K50/13—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light comprising stacked EL layers within one EL unit
    • 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
    • H10K2101/27—Combination of fluorescent and phosphorescent emission
    • 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
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the present invention relates to an organic electroluminescence device, and more particularly to a technique suitable for obtaining white light emission excellent in power efficiency and light emission lifetime.
  • an organic electroluminescence element basically has a layer structure composed of an anode / an organic light emitting layer / a cathode, and a layer such as a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer. Is appropriately provided.
  • a layer such as a hole injection layer, a hole transport layer, an electron transport layer, and an electron injection layer.
  • holes and electrons injected from the anode and the cathode recombine to generate excitons, and light emission occurs via the excitons.
  • an organic EL element using a phosphorescent substance (phosphorescent dopant) in an organic light emitting layer see, for example, Patent Documents 1 and 2), or a plurality of phosphorescent dopants
  • An organic EL element in which an exciton blocking layer made of an electron transporting material is provided between organic light emitting layers has been proposed.
  • an organic EL element for example, a blue light emitting material and a green light emitting material are used.
  • a method for obtaining white light by mixing red light emitting materials in one element is known.
  • red light emitting materials for example, in the case of the phosphorescent element, blue, green, and red light emitting materials are used.
  • the phosphorescent light emitting element can be expected to obtain high efficiency in principle as described above, but on the other hand, the luminance life at the time of driving is not always satisfactory at present. This is mainly because the driving stability of the blue phosphorescent material is not good.
  • Patent Documents 4 to 6 organic EL elements using blue fluorescent materials and green and red phosphorescent materials have been proposed (see, for example, Patent Documents 4 to 6).
  • a special bipolar layer is provided between an organic light emitting layer containing a red or green phosphorescent dopant and an organic light emitting layer containing a blue fluorescent dopant (see Patent Document 5).
  • a non-light emitting interface layer is provided (see Patent Document 6) to improve luminous efficiency and device life.
  • JP 2001-284056 A JP-T-2002-525808 JP-T-2004-522276 JP 2004-227814 A Japanese Patent No. 4969948 Japanese Patent No. 4496949
  • the main object of the present invention is to improve power efficiency and light emission lifetime in an organic EL device that obtains white color using a fluorescent light-emitting material such as blue and a phosphorescent light-emitting material of another color different from that.
  • An object of the present invention is to provide an organic EL element capable of suppressing chronological changes in chromaticity and driving voltage.
  • an organic electroluminescence device comprising an anode, a cathode, and a plurality of light emitting layers, wherein the plurality of light emitting layers are disposed between the anode and the cathode
  • the plurality of light emitting layers have a fluorescent light emitting layer and at least two or more phosphorescent light emitting layers, Of the fluorescent light emitting layer and the phosphorescent light emitting layer, the fluorescent light emitting layer is disposed on the anode side,
  • Each layer of the phosphorescent layer contains a phosphorescent dopant and a host compound,
  • the phosphorescent light emitting layer having the longest emission wavelength has a content higher than that of the main phosphorescent light emitting dopant of the layer, and the lowest excited triplet energy T1 is the main phosphorescent light emitting of the layer.
  • the present invention it is possible to improve the power efficiency and the light emission lifetime, and further suppress the change with time of chromaticity and driving voltage.
  • the fluorescent light emitting layer is disposed on the anode side of the phosphorescent light emitting layer.
  • the fluorescent light emitting layer is preferably a blue fluorescent light emitting layer containing a blue fluorescent light emitting dopant.
  • the light emission in the blue region of the blue fluorescent light-emitting layer means that the light emission maximum wavelength is in the range of 430 nm to 480 nm.
  • the phosphorescent light emitting layer has a layer structure of at least two layers.
  • the phosphorescent light emitting layer is preferably composed of a red phosphorescent light emitting layer containing a red phosphorescent light emitting dopant and a green phosphorescent light emitting layer containing a green phosphorescent light emitting dopant.
  • the blue fluorescent light emitting layer, the red phosphorescent light emitting layer, and the green phosphorescent light emitting layer are preferably laminated in this order from the anode to the cathode.
  • 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 between the light emitting layer and the adjacent layer.
  • the structure of the light emitting layer according to the present invention is not particularly limited as long as it satisfies the requirements defined in the present invention.
  • the total thickness of the light emitting layer is not particularly limited, but it prevents the uniformity of the film to be formed, 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. From the viewpoint, it is preferable to adjust to a range of 5 nm to 200 nm, and more preferably to a range of 20 nm to 150 nm. In the structure defined by the structure of the present invention, the thickness of each light emitting layer is preferably adjusted to a range of 5 nm to 200 nm, and more preferably adjusted to a range of 3 nm to 150 nm. is there.
  • the light emitting layer includes a fluorescent light emitting layer and a phosphorescent light emitting layer.
  • the fluorescent light emitting layer contains a fluorescent light emitting dopant and a host compound.
  • the phosphorescent layer also contains a phosphorescent dopant and a host compound.
  • a light emitting dopant or a host compound described later can be used, for example, a vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodget method), an ink jet method, a spray method, a printing method,
  • the film can be formed by a known thin film forming method such as a slot type coater method.
  • the number of layers constituting the light emitting layer is not particularly limited as long as it satisfies the requirements defined in the present invention, but at least two phosphorescent light emitting layers and blue light emitting in one blue region. And a fluorescent light emitting layer.
  • the phosphorescent or fluorescent light-emitting dopant contained in each light-emitting layer may be contained in the light-emitting layer at a uniform concentration in the film thickness direction, but has a concentration distribution. Also good.
  • the phosphorescent host compound contained in the phosphorescent layer of the organic EL device of the present invention is preferably a compound having a phosphorescence quantum yield of phosphorescence emission at room temperature (25 ° C.) of less than 0.1. Preferably, it is a compound having a phosphorescence quantum yield of less than 0.01. Moreover, in the compound contained in a light emitting layer, it is preferable that the mass ratio in the layer is 20 mass% or more.
  • the host compound may be used alone or in combination of two or more.
  • the phosphorescent host compound used in the present invention is not particularly limited in terms of structure, but is typically a carbazole derivative, triarylamine derivative, aromatic borane derivative, nitrogen-containing heterocyclic compound, thiophene derivative, furan derivative.
  • a compound having a basic skeleton such as an oligoarylene compound, or a carboline derivative or a diazacarbazole derivative (herein, a diazacarbazole derivative is at least one carbon atom of a hydrocarbon ring constituting a carboline ring of a carboline derivative) Represents the one substituted with a nitrogen atom).
  • a compound represented by the following general formula (a) is preferable.
  • X represents NR ′, O, S, CR′R ′′ or SiR′R ′′, R ′ and R ′′ each represent a hydrogen atom or a substituent.
  • Ar represents an aromatic ring.
  • N represents an integer of 0 to 8.
  • the substituents represented by R ′ and R ′′ may be alkyl groups (for example, methyl group, ethyl group, propyl group, isopropyl group, tert-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, 1-propenyl group, 2 -Butenyl group, 1,3-butadienyl group, 2-pentenyl group, isopropenyl group, etc.
  • alkynyl group for example, ethynyl group, propargyl group, etc.
  • aromatic hydrocarbon group aromatic carbocyclic group, aryl group, etc.
  • phenyl group, p-chlorophenyl group mesityl group, tolyl group, xylyl group, naphthyl group, Tolyl group, azulenyl group, acenaphthen
  • substituents may be further substituted with the above substituents.
  • a plurality of these substituents may be bonded to each other to form a ring.
  • X is preferably NR ′ or O, and R ′ is particularly preferably an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • examples of the aromatic ring represented by Ar include an aromatic hydrocarbon ring and an aromatic heterocyclic ring. Further, the aromatic ring may be a single ring or a condensed ring, and may be unsubstituted or may have a substituent as described later.
  • examples of the aromatic hydrocarbon ring represented by Ar include a benzene ring, biphenyl ring, naphthalene ring, azulene ring, anthracene ring, phenanthrene ring, pyrene ring, chrysene ring, naphthacene ring, triphenylene ring, o-terphenyl ring, m-terphenyl ring, p-terphenyl ring, acenaphthene ring, coronene ring, fluorene ring, fluoranthrene ring, naphthacene ring, pentacene ring, perylene ring, pentaphen ring, picene ring, pyrene ring, Examples include a pyranthrene ring and anthraanthrene ring. These rings may further have a substituent.
  • examples of the aromatic heterocycle represented by Ar include a furan ring, a dibenzofuran ring, a thiophene ring, an oxazole ring, a pyrrole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, and a triazine ring.
  • the aromatic ring represented by Ar is preferably a carbazole ring, a carboline ring, a dibenzofuran ring, or a benzene ring, and particularly preferably used is a carbazole ring, A carboline ring or a benzene ring.
  • a benzene ring having a substituent is preferable, and a benzene ring having a carbazolyl group is particularly preferable.
  • the aromatic ring represented by Ar is preferably a condensed ring having three or more rings, as shown below, and is an aromatic hydrocarbon in which three or more rings are condensed.
  • the condensed ring include naphthacene ring, anthracene ring, tetracene ring, pentacene ring, hexacene ring, phenanthrene ring, pyrene ring, benzopyrene ring, benzoazulene ring, chrysene ring, benzochrysene ring, acenaphthene ring, acenaphthylene ring, Triphenylene ring, coronene ring, benzocoronene ring, hexabenzocoronene ring, fluorene ring, benzofluorene ring, fluoranthene ring, perylene ring, naphthoperylene ring, pent
  • aromatic heterocycle condensed with three or more rings include an acridine ring, a benzoquinoline ring, a carbazole ring, a carboline ring, a phenazine ring, a phenanthridine ring, a phenanthroline ring, a carboline ring, a cyclazine ring, Kindin ring, tepenidine ring, quinindrin ring, triphenodithiazine ring, triphenodioxazine ring, phenanthrazine ring, anthrazine ring, perimidine ring, diazacarbazole ring (any one of the carbon atoms constituting the carboline ring is a nitrogen atom Phenanthroline ring, dibenzofuran ring, dibenzothiophene ring, naphthofuran ring, naphthothiophene ring, benzodifuran ring, benzod
  • the substituents that the aromatic ring represented by Ar may have are the same as the substituents represented by R ′ and R ′′.
  • n represents an integer of 0 to 8, preferably 0 to 2, and particularly preferably 1 or 2 when X is O or S.
  • luminescent host compound represented by the general formula (a) are shown below, but are not limited thereto.
  • the phosphorescent host compound used in the present invention may be a 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 (evaporation polymerizable light emitting host). But it is good.
  • a compound having a hole transporting ability and an electron transporting ability, which prevents the emission of longer wavelengths and has a high Tg (glass transition temperature) is preferable.
  • the host compound in the case of having a plurality of light emitting layers, may be different for each light emitting layer, but the same compound is preferable because excellent driving life characteristics are obtained.
  • the phosphorescent host compound has a lowest excited triplet energy (T1) larger than 2.2 eV because higher luminous efficiency can be obtained.
  • the lowest excited triplet energy as used in the present invention refers to the peak energy of the emission band corresponding to the transition between the lowest vibrational bands of the phosphorescence emission spectrum observed at a liquid nitrogen temperature after dissolving the host compound in a solvent.
  • a compound having a glass transition point of 90 ° C. or higher is preferable, and a compound having a glass transition temperature of 130 ° C. or higher is preferable because excellent driving life characteristics can be obtained.
  • the glass transition point (Tg) is a value determined by a method based on JIS-K-7121 using DSC (Differential Scanning Colorimetry).
  • the host material is responsible for carrier transport
  • a material having carrier transport capability is preferable.
  • Carrier mobility is used as a physical property representing carrier transport ability, but the carrier mobility of an organic material generally depends on the electric field strength. Since a material having a high electric field strength dependency easily breaks the balance of hole and electron injection / transport, it is preferable to use a material having a low electric field strength dependency of mobility for the intermediate layer material and the host material.
  • the phosphorescent host compound can also be used appropriately as a host compound for a fluorescent light-emitting dopant.
  • Fluorescent light emitting dopant also called fluorescent dopant, fluorescent light emitter, etc.
  • dopants can also be used in the present invention.
  • International Publication No. 00/70655 pamphlet JP-A Nos. 2002-280178, 2001-181616, 2002-280179, 2001 -181617, 2002-280180, 2001-247859, 2002-299060, 2001-313178, 2002-302671, 2001-345183, 2002 No. 324679, WO 02/15645, JP 2002-332291, 2002-50484, 2002-332292, 2002-83684, JP 2002-540572, JP 002-117978, 2002-338588, 2002-170684, 2002-352960, WO01 / 93642, JP2002-50483, 2002-1000047 No. 2002-173684, No.
  • the phosphorescent dopant according to the present invention is a compound in which light emission from an excited triplet is observed, specifically, a compound that emits phosphorescence at room temperature (25 ° C.).
  • the phosphorescence quantum yield is defined as a compound of 0.01 or more at 25 ° C., but the preferred phosphorescence quantum yield is 0.1 or more.
  • the phosphorescence quantum yield can be measured, for example, 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 phosphorescent emitter according to the present invention has the phosphorescence quantum yield (0.01 or more) in any solvent. It only has to be achieved.
  • the phosphorescent dopant There are two types of light emission principle of the phosphorescent dopant.
  • One type is that a carrier (electron, hole) is combined on the host compound to which the carrier is transported, and an excited state of the host compound is generated, and this excitation energy is transferred to the phosphorescent dopant. It is an energy transfer type that obtains light emission from.
  • the other type is a carrier trap type in which the phosphorescent light emitting dopant becomes a carrier trap, carrier recombination occurs on the phosphorescent light emitting dopant, and light emission from the phosphorescent light emitting dopant is obtained.
  • the excited state energy of the phosphorescent dopant is preferably lower than the excited state energy of the host compound in order to obtain high light emission efficiency.
  • the phosphorescent light emitting dopant can be appropriately selected from known materials used in the light emitting layer of the organic EL device.
  • the phosphorescent dopant according to the present invention is preferably a complex compound containing a group 8-10 metal in the periodic table of elements, more preferably an iridium compound, an osmium compound, or a platinum compound (platinum complex system). Compound) and rare earth complexes, and most preferred is an iridium compound.
  • the phosphorescence emission layer has a layer configuration of at least two layers. Among these phosphorescent light emitting layers, the phosphorescent light emitting layer having the longest emission wavelength contains a special phosphorescent metal complex in addition to the main phosphorescent light emitting dopant of the layer. Yes.
  • the phosphorescent light-emitting layer mainly has the characteristics (i) and (ii).
  • the content of the special phosphorescent metal complex is larger than the content of the phosphorescent dopant that is the main light emission.
  • the lowest excited triplet energy (T1) of the special phosphorescent metal complex is larger than T1 of the phosphorescent dopant that mainly emits light and smaller than T1 of the host compound.
  • T1 of each compound of a phosphorescence emission dopant and a host compound can be measured by a general method in this field.
  • any measuring apparatus of each device company may be used.
  • excitation light is emitted at a low temperature using a spectrofluorometer (F-4500 or F-7000 type spectrofluorometer, Hitachi High-Tech). It is possible to calculate the energy level of the lowest excited triplet state by emitting phosphorescence and measuring the absorption and emission spectra.
  • Injection layer electron injection layer, hole injection layer
  • the injection layer can be provided as necessary, and may exist 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.
  • An injection layer is a layer provided between an electrode and an organic layer in order to lower drive voltage and improve light emission luminance.
  • Organic EL element and its forefront of industrialization June 30, 1998, NTS Corporation) Issue
  • Chapter 2 “ Electrode Materials ”(pages 123 to 166), which is described in detail, and has a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).
  • anode buffer layer hole injection layer
  • copper phthalocyanine Phthalocyanine buffer layer typified by (1)
  • oxide buffer layer typified by vanadium oxide
  • amorphous carbon buffer layer polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene, and the like. It is also preferable to use materials described in JP-T-2003-519432.
  • 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 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 used.
  • ⁇ 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. 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 as needed.
  • the hole blocking layer provided in the organic EL device of the present invention is preferably provided adjacent to the light emitting layer.
  • 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, and transports electrons while transporting holes. 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 transport layer according to the present invention is preferably 3 nm to 100 nm, and more preferably 5 nm to 30 nm.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, 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 further 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
  • 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-4-297076 JP-A-2000-196140, JP-A-2001-102175, J. Pat. Appl. Phys. , 95, 5773 (2004), JP-A-11-251067, J. MoI. Huang et. al. It is also possible to use a hole transport material that has so-called p-type semiconducting properties, as described in the literature (Applied Physics Letters 80 (2002), p. 139), JP 2003-519432 A. it can. In the present invention, it is preferable to use these materials because a light-emitting element with higher efficiency can be obtained.
  • the above hole transport material is used, for example, vacuum deposition method, spin coating method, casting method, LB method (Langmuir-Blodget method), ink jet method, spray method, printing method, slot type coater method, etc.
  • the film can be formed by a known thin film forming method.
  • the film thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 nm to 200 nm.
  • the hole transport layer may have a single layer structure composed of one or more of the above materials.
  • 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
  • an electron transport layer adjacent to the light emitting layer on the cathode side is injected from the cathode.
  • any material selected from conventionally known compounds can be selected and used. For example, 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 derivatives exemplified as the material of the light emitting layer can also be used as an electron transport material, and like the hole injection layer and the hole transport layer, inorganic such as n-type-Si and n-type-SiC can be used.
  • a semiconductor can also be used as an electron transport material.
  • the above-mentioned electron transport material is a known material such as a vacuum deposition method, a spin coating method, a casting method, an LB method (Langmuir-Blodget method), an ink jet method, a spray method, a printing method, or a slot type coater method.
  • the film can be formed by a thin film forming 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 material that has n-type semiconductor properties doped with impurities.
  • 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 material that has such n-type semiconductor properties because an element with lower power consumption can be produced.
  • a compound having a phenylpyridine skeleton is contained, and at least one of an electron donating metal (metal atom), metal ion, or metal complex is doped.
  • the compound having a phenylpyridine skeleton is preferably represented by the general formula (1).
  • the electron-donating metal, metal ion, or metal complex is preferably doped with respect to the electron transport layer and not with the exciton blocking layer (hole blocking layer).
  • “Ar1” represents an m-valent aryl group
  • “R” and “R ′” each represents a hydrogen atom or a substituent.
  • “N” represents an integer of 1 to 6.
  • R and R ′ represent a substituent
  • specific examples of these substituents include an alkyl group (for example, a methyl group, an ethyl group, an isopropyl group, a hydroxyethyl group, a methoxymethyl group, a trimethyl group).
  • substituents include a halogen atom, hydroxyl group, nitro group, cyano group, carboxyl group, sulfo group, alkyl group, aryl group, alkoxy group, aryloxy group, alkylthio group.
  • R and R ′ include a hydrogen atom, an alkyl group, and an aryl group, and a hydrogen atom is more preferable.
  • the benzene ring and the pyridine ring may be bonded at any position, but preferably bonded to the benzene ring at the 2-position of the pyridine, and the benzene ring side is bonded to Ar1. It is preferably bonded to the pyridine ring at the ortho position.
  • a structure in which a benzene ring and a pyridine ring are condensed via R and R ′ may be employed.
  • the aryl group represented by Ar1 is an aromatic hydrocarbon group such as phenyl group, naphthyl group, triphenylene group, biphenyl group, terphenyl group, pyridyl group, pyrimidyl group, triazinyl group, thienyl group, Examples include an aromatic heterocyclic group such as a furyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a quinolyl group, an isoquinolyl group, an azacarbazolyl group, and the aryl group represented by Ar1 may have a substituent.
  • n represents an integer of 1 to 6, and is bonded to the phenylpyridine structure through n bonds from the aryl group.
  • n is preferably 2 or 3, and as specific Ar1 structures, the following structures or combinations thereof are preferably used.
  • Ar2 represents an aryl group and is bonded to the benzene ring of the general formula (1) at the position of “*”.
  • the support substrate (hereinafter also referred to as a substrate, substrate, substrate, support, etc.) applied to the organic EL element of the present invention is not particularly limited in the type of glass, plastic, etc., and may be transparent. It 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, polysulfones, Cycloolefin resins such as polyether imide, polyether ketone imide, polyamide, fluororesin, nylon, polymethyl methacrylate, acrylic or polyarylate, Arton (trade name, manufactured by JSR) or
  • An inorganic or organic film or a hybrid film of both may be formed on the surface of the resin film, and the water vapor permeability measured by a method according to JIS K 7129-1992 is 0.01 g / (m 2 ⁇ 24 h ⁇ atm) or less, and the oxygen permeability measured by a method according to JIS K 7126-1992 is preferably 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less. It is preferable that the film has a water vapor permeability of 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less, and the water vapor permeability and oxygen permeability are both 10 ⁇ 5 g / (m 2 ⁇ 24h) or less is more preferable.
  • the material for forming the barrier film may be any material as long as it has a function of suppressing intrusion of elements that cause deterioration of the element 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.
  • a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used, but an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is also preferable.
  • the opaque support substrate examples include metal plates / films such as aluminum and stainless steel, opaque resin substrates, ceramic substrates, and the like.
  • Examples of the sealing means used for sealing the organic EL element of the present invention include a method of bonding a sealing member, an electrode, and a support substrate with an adhesive.
  • the sealing member may be disposed so as to cover the display area of the organic EL element, and may be a concave plate shape or a flat plate shape. Moreover, transparency and electrical insulation are not particularly limited.
  • 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 organic EL element can be thinned.
  • the polymer film preferably has an oxygen permeability of 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less and a water vapor permeability of 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less. Further, it is more preferable that both the water vapor permeability and the oxygen permeability are 10 ⁇ 5 g / (m 2 ⁇ 24 h) or less.
  • 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.
  • fever and chemical curing types such as an epoxy type, can be mentioned.
  • 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 it like screen printing.
  • the electrode and the organic layer on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and form an inorganic or organic layer in contact with the support substrate to form a sealing film.
  • the material for forming the film may be any material that has a function of suppressing intrusion of elements that cause deterioration of the element such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like is used. it can.
  • vacuum deposition sputtering, reactive sputtering, molecular beam epitaxy, 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 is injected in the gas phase and the liquid phase.
  • a vacuum can also be used.
  • a hygroscopic compound can also be enclosed inside.
  • hygroscopic compound examples include metal oxides (eg, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide), sulfates (eg, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate).
  • metal oxides eg, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide
  • sulfates eg, 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, barium perchlorate
  • Magnesium perchlorate, etc. anhydrous salts are preferably used in sulfates, metal halides and perchloric acids.
  • a protective film or a protective plate may be provided outside the sealing film or the sealing film on the side facing the support substrate with the organic layer interposed therebetween.
  • 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, but the polymer film is light and thin. Is preferably used.
  • 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.
  • an electrode substance include conductive transparent materials such as metals such as Au, CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • conductive transparent materials such as metals such as Au, CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming 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 the pattern accuracy is not required (about 100 ⁇ m or more) ), A pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered. Or when using the substance which can be apply
  • 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, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
  • 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 nm to 200 nm.
  • the emission luminance is advantageously improved.
  • 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 nm to 20 nm. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
  • a desired electrode material for example, a thin film made of a material for an anode is formed on a suitable support substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably 10 nm to 200 nm.
  • a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably 10 nm to 200 nm.
  • the vapor deposition method, the wet process spin coating method, casting method, ink jet method, printing method, LB method (Langmuir-Blodgett method), spray method, printing method,
  • vacuum deposition, spin coating, ink-jet, printing, and slot-type coater methods are particularly preferred from the standpoint that a homogeneous film is easily obtained and pinholes are not easily formed. preferable.
  • the vapor deposition conditions vary depending on the type of compound used, but generally the boat heating temperature is 50 ° C. to 450 ° C., the degree of vacuum is 10 ⁇ 6 Pa to 10 ⁇ 2 Pa, and the vapor deposition rate is 0. It is desirable to select appropriately within the range of 01 nm / second to 50 nm / second, substrate temperature ⁇ 50 ° C. to 300 ° C., film thickness 0.1 nm to 5 ⁇ m, preferably 5 nm to 200 nm.
  • 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 thickness of 1 ⁇ m or less, preferably in the range of 50 nm to 200 nm, and a cathode is provided.
  • a desired organic EL element can be obtained.
  • the organic EL element is preferably manufactured from the hole injection layer to the cathode consistently by a single evacuation, but may be taken out halfway and subjected to different film forming methods. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.
  • a DC voltage is applied to the multicolor display device thus obtained, light emission can be observed by applying a voltage of about 2 V 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.
  • An organic electroluminescence device emits light inside a layer having a refractive index higher than that of air (refractive index of about 1.6 to 2.1), and can extract only about 15% to 20% of light generated in the light emitting layer. It is generally said that there is no. 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 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 direction of the side surface of the device.
  • a technique for improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate to prevent total reflection at the transparent substrate and the air interface (for example, US Pat. No. 4,774,435), A method for improving efficiency by providing light condensing property (for example, Japanese Patent Laid-Open No. 63-134795), a method for forming a reflective surface on the side surface of an element (for example, Japanese Patent Laid-Open No. 1-220394), a substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the substrate and the light emitter (for example, Japanese Patent Laid-Open No.
  • these methods can be used in combination with the organic electroluminescence device of the present invention, but a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, A method of forming a diffraction grating between any layers of the transparent electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used.
  • the light extracted from the transparent electrode has a higher extraction efficiency to the outside as the refractive index of the medium is lower.
  • 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. Furthermore, it is preferable that it is 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 that causes total reflection or in any medium has a feature that the effect of improving the light extraction efficiency is high.
  • 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 or second-order diffraction.
  • the 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 the transparent substrate or transparent electrode). , Trying to extract light 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. In other words, the light extraction efficiency does not increase so much.
  • the refractive index distribution a two-dimensional distribution
  • the light traveling in all directions is diffracted, and the light extraction efficiency is increased.
  • the position where the diffraction grating is introduced may be in any layer or in the medium (in the transparent substrate or transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated. At this time, 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 electroluminescence device of the present invention is processed to provide, for example, a structure on a microlens array on the light extraction side of a support substrate (substrate), or in combination with a so-called condensing sheet, for example, a specific direction, By condensing in the front direction with respect to the element light emitting surface, the luminance in a specific direction can be increased.
  • 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 ⁇ m 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, an LED backlight of a liquid crystal display device that has been put into practical use.
  • a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.
  • BEF brightness enhancement film
  • a substrate may be formed with a ⁇ -shaped stripe having an apex angle of 90 degrees and a pitch of 50 ⁇ m, or the apex angle is rounded and the pitch is changed randomly. Other shapes may also be used.
  • a light diffusing 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.
  • the organic EL element of the present invention is used for a multicolor or white display device.
  • a shadow mask is provided only at the time of forming a light emitting layer, and a film can be formed on one surface by vapor deposition, casting, spin coating, ink jet, printing, slot coater, or the like.
  • the method is not limited, but a vapor deposition method, an inkjet method, and a printing method are preferable. In the case of using a vapor deposition method, patterning using a shadow mask is preferable.
  • the alternating current waveform to be applied may be arbitrary.
  • the organic EL device of the present invention may be used as a kind of lamp such as an illumination or exposure light source, a projection device that projects an image, or a display device that directly recognizes a still image or a moving image. (Display) may be used.
  • the driving method when used as a display device for moving image reproduction may be either a simple matrix (passive matrix) method or an active matrix method.
  • patterning may be performed by a metal mask, an inkjet printing method, or the like at the time of film formation, if necessary.
  • patterning only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire element layer may be patterned.
  • the light emitting dopant used in the light emitting layer is not particularly limited.
  • the platinum complex according to the present invention or the wavelength range corresponding to the CF (color filter) characteristics Any one of known light-emitting dopants may be selected and combined, or combined with the light extraction and / or light collecting sheet according to the present invention to be whitened.
  • the white organic EL element of the present invention is taken out from the organic electroluminescence element by combining the CF (color filter) and arranging the element and the driving transistor circuit in accordance with the CF (color filter) pattern.
  • white light as a backlight
  • blue light, green light, and red light are obtained through a blue filter, a green filter, and a red filter, so that a full-color organic electroluminescence display with a low driving voltage and a long life can be obtained.
  • a white light emitting organic EL element using a blue fluorescent light emitting dopant and a longer wave (green and red) phosphorescent light emitting dopant in combination is provided.
  • White light-emitting organic EL devices using a blue fluorescent dopant and a longer-wave phosphorescent dopant in combination have been developed since long life and high color rendering properties can be expected.
  • a three-layer structure having three different colors of B (blue), G (green), and R (red) is preferable.
  • the inventors of the present invention have a preferable stacking order of blue / phosphorescent light (at least two layers) from the anode side, particularly blue / red / green with less energy loss (excitation energy diffusion) to the outside of the light emitting unit (light emitting layer). I found out.
  • the central light emitting layer where the energy tends to concentrate tends to increase the light emission intensity, and it is necessary to reduce the thickness of the light emitting layer compared to the multilayer in order to achieve white balance.
  • the luminance life of an organic EL element tends to be shortened when the light emitting layer is thin.
  • the carrier trap frequency per molecule of the light emitting material is increased and the material is easily deteriorated from radicals. In the case of white, for example, chromaticity is likely to change due to a change in carrier balance during storage over time.
  • the present inventors have incorporated a phosphorescent metal complex having the above-described characteristics into the red light emitting layer located in the center in the above light emitting layer structure, particularly the blue / red / green light emitting layer structure. It has been found that the luminance life can be improved while maintaining high efficiency (see Example 1). The cause of this is not clear, but it is presumed that, for example, the presence of the metal complex could reduce the radical state existence frequency of the red light emitting material. Furthermore, the present inventors can relax the change over time by doping an electron-donating metal in the electron transport layer and suppress fluctuations in chromaticity and driving voltage, and particularly with an electron transport material having a phenylpyridine skeleton. It has been found that the combination exhibits an excellent fluctuation suppressing effect (see Example 2).
  • each blue, red, and green light emitting layer of each organic EL element shown below is selected so as to exhibit white light emission in the range of the correlated color temperature from 4400K to 4000K at a luminance of 1000 cd / m 2 .
  • the compounds used below have the following structures.
  • organic EL element 101 After patterning on a support substrate in which ITO (indium tin oxide) was formed to a thickness of 110 nm on a glass substrate having a thickness of 30 mm ⁇ 30 mm and a thickness of 0.7 mm as an anode, The transparent support substrate with the ITO transparent electrode is ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes. Then, the transparent support substrate is placed on a substrate holder of a commercially available vacuum deposition apparatus. Fixed.
  • ITO indium tin oxide
  • Each of the vapor deposition crucibles in the vacuum vapor deposition apparatus was filled with the constituent material of each layer in an optimum amount for device fabrication.
  • the evaporation crucible used was made of a resistance heating material made of molybdenum or tungsten. After reducing the vacuum to 1 ⁇ 10 ⁇ 4 Pa, the deposition crucible containing the compound M-1 was heated by energization, and deposited on a transparent support substrate at a deposition rate of 0.1 nm / second. An injection layer was provided. Next, ⁇ -NPD was deposited in the same manner to provide a 70 nm hole transport layer.
  • Compound GD-1 and Compound H-1 are co-evaporated at a deposition rate of 0.1 nm / second so that the concentration of Compound GD-1 is 9% by volume to form a green phosphorescent light emitting layer having a thickness of 15 nm. did.
  • compounds GD-1, RD-1 and compound H-1 were co-deposited at a deposition rate of 0.1 nm / second so that the concentration of compound GD-1 was 9% by volume and RD-1 was 2% by volume.
  • a red phosphorescent light emitting layer having a thickness of 7 nm was formed. In the red phosphorescent light emitting layer, main light emission is caused by the compound RD-1.
  • the compound RD-1 corresponds to a main phosphorescent light emitting dopant
  • the compound GD-1 corresponds to a special phosphorescent metal complex.
  • the content of compound GD-1 is higher than the content of compound RD-1.
  • the value of T1 of compound GD-1 is larger than the value of T1 of compound RD-1, and smaller than the value of T1 of compound H-1.
  • Compound BD-1 and Compound H-2 were co-deposited at a deposition rate of 0.1 nm / second so that the concentration of Compound BD-1 was 7%, and a blue fluorescent light-emitting layer having a thickness of 35 nm was formed. .
  • compound HB-1 was deposited to a thickness of 10 nm at a deposition rate of 0.1 nm / second to form an exciton blocking layer, and then compound E-1 was deposited to a thickness of 25 nm at a deposition rate of 0.1 nm / second.
  • an electron transport layer was formed.
  • KF was formed to a thickness of 2 nm
  • aluminum was deposited with a thickness of 110 nm to form a cathode.
  • FIG. 1 shows a schematic diagram of an organic EL element.
  • the organic EL element 101 is covered with a glass cover 102.
  • the sealing operation with the glass cover 102 was performed in a glove box (in an atmosphere of high-purity nitrogen gas having a purity of 99.999% or more) in a nitrogen atmosphere without bringing the organic EL element 101 into contact with the atmosphere.
  • FIG. 2 shows a cross-sectional view of the organic EL element.
  • an organic EL layer 106 and a cathode 105 are laminated and formed on a glass substrate 107 with a transparent electrode.
  • the glass cover 102 is filled with nitrogen gas 108 and a water catching agent 109 is provided.
  • Compound GD-1 and Compound H-1 are co-deposited at a deposition rate of 0.1 nm / second so that the concentration of Compound GD-1 is 9% by volume, thereby forming a green phosphorescent light emitting layer having a thickness of 25 nm. did.
  • compound HB-1 was deposited to a thickness of 10 nm at a deposition rate of 0.1 nm / second to form an exciton blocking layer, and then compound E-1 was deposited to a thickness of 25 nm at a deposition rate of 0.1 nm / second.
  • an electron transport layer was formed.
  • KF was formed to a thickness of 2 nm
  • aluminum was deposited with a thickness of 110 nm to form a cathode.
  • the non-light-emitting surface was covered with a glass case, and an “organic EL element 102” was produced.
  • the compound RD-1 corresponds to a main phosphorescent light emitting dopant
  • the compound GD-1 corresponds to a special phosphorescent metal complex.
  • the content of compound GD-1 is higher than the content of compound RD-1.
  • the value of T1 of compound GD-1 is larger than the value of T1 of compound RD-1, and smaller than the value of T1 of compound H-1.
  • Compound GD-1 and Compound H-1 are co-evaporated at a deposition rate of 0.1 nm / second so that the concentration of Compound GD-1 is 9% by volume, thereby forming a green phosphorescent light emitting layer having a thickness of 30 nm. did.
  • compound HB-1 was deposited to a film thickness of 10 nm at a deposition rate of 0.1 nm / second to form an exciton blocking layer (hole blocking layer), and then compound E-1 was deposited to a film thickness of 25 nm at a deposition rate of 0
  • the electron transport layer was formed by vapor deposition at a rate of 1 nm / second.
  • KF was formed to a thickness of 2 nm
  • aluminum was deposited with a thickness of 110 nm to form a cathode.
  • the non-light-emitting surface was covered with a glass case to produce an "organic EL element 103".
  • Organic EL element 104 It carried out similarly to the organic EL element 102, and provided even the blue fluorescence light emitting layer.
  • Compound GD-1 and Compound H-1 are co-evaporated at a deposition rate of 0.1 nm / second so that Compound GD-1 has a concentration of 9% by volume to form a green phosphorescent light emitting layer having a thickness of 18 nm. did.
  • compounds GD-1, RD-1 and H-1 were co-polymerized at a deposition rate of 0.1 nm / second so that the concentration of compound GD-1 was 9% by volume and the concentration of compound RD-1 was 2% by volume.
  • red phosphorescent light emitting layer having a thickness of 8 nm.
  • main light emission is caused by the compound RD-1.
  • the compound RD-1 corresponds to a main phosphorescent light emitting dopant
  • the compound GD-1 corresponds to a special phosphorescent metal complex.
  • the content of compound GD-1 is higher than the content of compound RD-1.
  • the value of T1 of compound GD-1 is larger than the value of T1 of compound RD-1, and smaller than the value of T1 of compound H-1.
  • compound HB-1 was deposited to a thickness of 10 nm at a deposition rate of 0.1 nm / second to form an exciton blocking layer, and then compound E-1 was deposited to a thickness of 25 nm at a deposition rate of 0.1 nm / second.
  • an electron transport layer was formed.
  • KF was formed to a thickness of 2 nm
  • aluminum was deposited with a thickness of 110 nm to form a cathode.
  • the non-light-emitting surface was covered with a glass case, and an “organic EL element 104” was produced.
  • the compound RD-1 corresponds to a main phosphorescent light emitting dopant
  • the compound AD-1 corresponds to a special phosphorescent metal complex.
  • the content of compound AD-1 is higher than the content of compound RD-1.
  • the value of T1 of compound AD-1 is larger than the value of T1 of compound RD-1, and smaller than the value of T1 of compound H-1.
  • Compound GD-1 and Compound H-1 are co-evaporated at a deposition rate of 0.1 nm / second so that the concentration of Compound GD-1 is 9% by volume, thereby forming a green phosphorescent light emitting layer having a thickness of 30 nm. did.
  • compound HB-1 was deposited to a thickness of 10 nm at a deposition rate of 0.1 nm / second to form an exciton blocking layer, and then compound E-1 was deposited to a thickness of 25 nm at a deposition rate of 0.1 nm / second.
  • an electron transport layer was formed.
  • KF was formed to a thickness of 2 nm
  • aluminum was deposited with a thickness of 110 nm to form a cathode.
  • the non-light emitting surface was covered with a glass case, and an “organic EL element 105” was produced.
  • the organic EL elements 103 to 105 of the present invention have improved power efficiency and light emission lifetime compared to the comparative organic EL elements 101 to 102, and also have good storage stability. It was excellent.
  • the organic EL elements 103 and 105 in which a blue fluorescent light emitting layer, a red phosphorescent light emitting layer, and a green phosphorescent light emitting layer are laminated in this order from the anode side to the cathode side show better performance.
  • the phosphorescent phosphor layer is formed on the anode side and has a higher content in the red phosphorescent emitting layer than the phosphorescent dopant (compound RD-1), which is the main light emission, and the lowest excited triplet energy is the main phosphorescence.
  • Compound RD-1 the phosphorescent dopant
  • Compound H-1 the host compound
  • Organic EL element 201 The hole blocking layer was provided in the same manner as the organic EL element 103. Next, compounds E-1 and KF were co-evaporated at a deposition rate of 0.1 nm / second so that the concentration of KF was 17% by volume to form an electron transport layer having a thickness of 20 nm. Subsequently, aluminum 110nm was vapor-deposited and the cathode was formed. Thereafter, in the same manner as in the case of the organic EL element 103, the non-light-emitting surface was covered with a glass case, and an "organic EL element 201" was produced.
  • organic EL element 204 It carried out similarly to the organic EL element 103, and provided to the hole-blocking layer. Next, the compound E-1 and the 8-hydroxyquinoline lithium complex were co-evaporated at a deposition rate of 0.1 nm / second so that the concentration of the 8-hydroxyquinoline lithium complex was 30% by volume, and an electron transport layer having a thickness of 20 nm was formed. Formed. Subsequently, aluminum 110nm was vapor-deposited and the cathode was formed. Thereafter, in the same manner as in the case of the organic EL element 103, the non-light-emitting surface was covered with a glass case, and an “organic EL element 204” was produced.
  • Organic EL Element 205 The hole blocking layer was provided in the same manner as the organic EL element 103. Next, Compound E-2 was deposited to a thickness of 20 nm at a deposition rate of 0.1 nm / second to form an electron transport layer. Further, after KF was formed to a thickness of 2 nm, aluminum was deposited with a thickness of 110 nm to form a cathode. Next, in the same manner as in the case of the organic EL element 103, the non-light-emitting surface was covered with a glass case, and an "organic EL element 205" was produced.
  • Organic EL Element 207 The hole blocking layer was provided in the same manner as the organic EL element 103. Next, Compound E-3 was deposited to a film thickness of 20 nm at a deposition rate of 0.1 nm / second to form an electron transport layer. Further, after KF was formed to a thickness of 2 nm, aluminum was deposited with a thickness of 110 nm to form a cathode. Next, in the same manner as in the case of the organic EL element 103, the non-light-emitting surface was covered with a glass case, and an “organic EL element 207” was produced.
  • Organic EL Element 208 The hole blocking layer was provided in the same manner as the organic EL element 103. Next, compounds E-3 and KF were co-evaporated at a deposition rate of 0.1 nm / second so that the concentration of KF was 20% by volume to form an electron transport layer having a thickness of 20 nm. Subsequently, aluminum 110nm was vapor-deposited and the cathode was formed. Next, in the same manner as in the case of the organic EL element 103, the non-light emitting surface was covered with a glass case, and an “organic EL element 208” was produced.
  • an electron transport layer containing electron transport materials E-1, E-2, E-3 having a phenylpyridine skeleton and doped with an alkali metal compound or an alkali metal organic complex The organic EL elements 201 to 204, 206, 208 having the organic EL elements 103, 205, 207 not doped with the metal compound, and the electron transport materials E-4, E having no phenylpyridine skeleton in the molecule. It can be seen that the organic EL elements 209 to 212 containing -5 have favorable performance with little change in chromaticity and increase in voltage during storage.
  • the organic EL element doped with K has good performance.
  • the metal compound is almost doped with chromaticity and voltage during storage. It can be seen that there is no effect of suppressing fluctuation.
  • Organic EL element 301 It carried out similarly to the organic EL element 103, and provided to the electron carrying layer. Next, after forming LiF to a thickness of 1.5 nm, aluminum was deposited to have a thickness of 110 nm to form a cathode. Next, in the same manner as in the case of the organic EL element 103, the non-light-emitting surface was covered with a glass case to produce an "organic EL element 301".
  • the present invention can be particularly suitably used for obtaining white light emission excellent in power efficiency and light emission lifetime.

Landscapes

  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un élément organique électroluminescent (101) pourvu d'une électrode positive, d'une électrode négative, et d'une pluralité de couches émettrices de lumière, ladite pluralité de couches émettrices de lumière se trouvant entre l'électrode positive et l'électrode négative. Dans l'élément organique électroluminescent (101), la pluralité de couches émettrices de lumière comportent une couche émettrice de lumière fluorescente et deux couches émettrices de lumière phosphorescente ou plus. Parmi la couche émettrice de lumière fluorescente et les couches émettrices de lumière phosphorescente, la couche émettrice de lumière fluorescente se trouve du côté de l'électrode positive, et chaque couche émettrice de lumière phosphorescente contient un dopant émetteur de lumière phosphorescente et un composé hôte; et parmi les couches émettrices de lumière phosphorescente, la couche émettrice de lumière phosphorescente ayant la longueur d'onde d'émission la plus longue contient un complexe métallique émetteur de lumière phosphorescente dont la teneur est supérieure à celle du dopant principal émetteur de lumière phosphorescente de ladite couche, et l'énergie du triplet le moins excité (T1) du complexe métallique étant supérieure à la T1 du principal dopant émetteur de lumière phosphorescente de ladite couche et inférieure à la T1 du composé hôte.
PCT/JP2012/065680 2011-09-02 2012-06-20 Élément organique à électroluminescence WO2013031345A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2013531136A JP6107657B2 (ja) 2011-09-02 2012-06-20 有機エレクトロルミネッセンス素子

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2011-191237 2011-09-02
JP2011191237 2011-09-02

Publications (1)

Publication Number Publication Date
WO2013031345A1 true WO2013031345A1 (fr) 2013-03-07

Family

ID=47755857

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/065680 WO2013031345A1 (fr) 2011-09-02 2012-06-20 Élément organique à électroluminescence

Country Status (2)

Country Link
JP (1) JP6107657B2 (fr)
WO (1) WO2013031345A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2014209604A (ja) * 2013-03-26 2014-11-06 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器、および照明装置
WO2015022988A1 (fr) * 2013-08-16 2015-02-19 コニカミノルタ株式会社 Élément électroluminescent organique, dispositif électroluminescent, dispositif d'éclairage, dispositif d'affichage et dispositif électronique
JP2016072250A (ja) * 2014-09-30 2016-05-09 株式会社半導体エネルギー研究所 発光装置、電子機器、及び照明装置
WO2017038381A1 (fr) * 2015-09-03 2017-03-09 株式会社カネカ Dispositif d'émission électroluminescent organique
EP2329544B1 (fr) * 2008-09-04 2017-05-17 Universal Display Corporation Dispositifs organiques émettant une lumière phosphorescente blanche
KR20190068103A (ko) * 2017-12-08 2019-06-18 엘지디스플레이 주식회사 내열 특성이 우수한 유기 화합물, 이를 포함하는 유기발광다이오드 및 유기발광장치
CN111081888A (zh) * 2018-10-22 2020-04-28 乐金显示有限公司 有机发光二极管和具有该发光二极管的有机发光装置
CN112969695A (zh) * 2018-11-30 2021-06-15 株式会社Lg化学 化合物及包含其的有机发光器件
CN113363400A (zh) * 2021-06-02 2021-09-07 南京昀光科技有限公司 有机发光器件及其制作方法以及显示面板
KR20210138157A (ko) * 2013-08-26 2021-11-18 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 표시 장치, 조명 장치, 및 전자 기기

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63299092A (ja) * 1987-05-29 1988-12-06 Ricoh Co Ltd 薄膜エレクトロルミネッセントパネル
JP2004047329A (ja) * 2002-07-12 2004-02-12 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子及び表示装置
JP2004214179A (ja) * 2002-12-17 2004-07-29 Fuji Photo Film Co Ltd 有機電界発光素子
JP2005123168A (ja) * 2003-09-24 2005-05-12 Fuji Photo Film Co Ltd 有機電界発光素子
JP2005267990A (ja) * 2004-03-18 2005-09-29 Hitachi Ltd 有機発光表示装置
JP2006156942A (ja) * 2004-11-27 2006-06-15 Samsung Sdi Co Ltd 有機電界発光素子
JP2006270053A (ja) * 2005-02-28 2006-10-05 Fuji Photo Film Co Ltd 有機電界発光素子
JP2006278137A (ja) * 2005-03-29 2006-10-12 Konica Minolta Holdings Inc 面発光体
JP2008091860A (ja) * 2006-09-06 2008-04-17 Fujifilm Corp 有機電界発光素子および表示装置
JP2010530466A (ja) * 2007-06-19 2010-09-09 ゼネラル・エレクトリック・カンパニイ 有機電子デバイス用のカルバゾリルポリマー
JP2010205427A (ja) * 2009-02-27 2010-09-16 Dainippon Printing Co Ltd 有機エレクトロルミネッセンス素子

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006159642A (ja) * 2004-12-07 2006-06-22 Fuji Photo Film Co Ltd 発熱素子の抵抗値測定方法及び装置
JP2007250239A (ja) * 2006-03-14 2007-09-27 Konica Minolta Holdings Inc 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ディスプレイ
US7579773B2 (en) * 2006-06-05 2009-08-25 The Trustees Of Princeton University Organic light-emitting device with a phosphor-sensitized fluorescent emission layer
CN103329621A (zh) * 2011-01-20 2013-09-25 出光兴产株式会社 有机电致发光元件

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS63299092A (ja) * 1987-05-29 1988-12-06 Ricoh Co Ltd 薄膜エレクトロルミネッセントパネル
JP2004047329A (ja) * 2002-07-12 2004-02-12 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子及び表示装置
JP2004214179A (ja) * 2002-12-17 2004-07-29 Fuji Photo Film Co Ltd 有機電界発光素子
JP2005123168A (ja) * 2003-09-24 2005-05-12 Fuji Photo Film Co Ltd 有機電界発光素子
JP2005267990A (ja) * 2004-03-18 2005-09-29 Hitachi Ltd 有機発光表示装置
JP2006156942A (ja) * 2004-11-27 2006-06-15 Samsung Sdi Co Ltd 有機電界発光素子
JP2006270053A (ja) * 2005-02-28 2006-10-05 Fuji Photo Film Co Ltd 有機電界発光素子
JP2006278137A (ja) * 2005-03-29 2006-10-12 Konica Minolta Holdings Inc 面発光体
JP2008091860A (ja) * 2006-09-06 2008-04-17 Fujifilm Corp 有機電界発光素子および表示装置
JP2010530466A (ja) * 2007-06-19 2010-09-09 ゼネラル・エレクトリック・カンパニイ 有機電子デバイス用のカルバゾリルポリマー
JP2010205427A (ja) * 2009-02-27 2010-09-16 Dainippon Printing Co Ltd 有機エレクトロルミネッセンス素子

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2329544B1 (fr) * 2008-09-04 2017-05-17 Universal Display Corporation Dispositifs organiques émettant une lumière phosphorescente blanche
JP2014209604A (ja) * 2013-03-26 2014-11-06 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器、および照明装置
US10249837B2 (en) 2013-03-26 2019-04-02 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device
WO2015022988A1 (fr) * 2013-08-16 2015-02-19 コニカミノルタ株式会社 Élément électroluminescent organique, dispositif électroluminescent, dispositif d'éclairage, dispositif d'affichage et dispositif électronique
JPWO2015022988A1 (ja) * 2013-08-16 2017-03-02 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、発光装置、照明装置、表示装置及び電子機器
KR20210138157A (ko) * 2013-08-26 2021-11-18 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 표시 장치, 조명 장치, 및 전자 기기
KR20230042543A (ko) * 2013-08-26 2023-03-28 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 표시 장치, 조명 장치, 및 전자 기기
US12171127B2 (en) 2013-08-26 2024-12-17 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, display module, lighting module, light-emitting device, display device, electronic appliance, and lighting device
KR102618863B1 (ko) * 2013-08-26 2023-12-28 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 표시 장치, 조명 장치, 및 전자 기기
US11825718B2 (en) 2013-08-26 2023-11-21 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, display module, lighting module, light-emitting device, display device, electronic appliance, and lighting device
KR102403208B1 (ko) * 2013-08-26 2022-05-30 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 표시 장치, 조명 장치, 및 전자 기기
KR20220075449A (ko) * 2013-08-26 2022-06-08 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 표시 장치, 조명 장치, 및 전자 기기
KR102513242B1 (ko) * 2013-08-26 2023-03-24 가부시키가이샤 한도오따이 에네루기 켄큐쇼 발광 소자, 발광 장치, 표시 장치, 조명 장치, 및 전자 기기
JP2016072250A (ja) * 2014-09-30 2016-05-09 株式会社半導体エネルギー研究所 発光装置、電子機器、及び照明装置
WO2017038381A1 (fr) * 2015-09-03 2017-03-09 株式会社カネカ Dispositif d'émission électroluminescent organique
KR20190068103A (ko) * 2017-12-08 2019-06-18 엘지디스플레이 주식회사 내열 특성이 우수한 유기 화합물, 이를 포함하는 유기발광다이오드 및 유기발광장치
KR102469693B1 (ko) * 2017-12-08 2022-11-21 엘지디스플레이 주식회사 내열 특성이 우수한 유기 화합물, 이를 포함하는 유기발광다이오드 및 유기발광장치
KR102600295B1 (ko) * 2018-10-22 2023-11-08 엘지디스플레이 주식회사 유기발광다이오드 및 유기발광장치
KR20200045292A (ko) * 2018-10-22 2020-05-04 엘지디스플레이 주식회사 유기발광다이오드 및 유기발광장치
US11895915B2 (en) 2018-10-22 2024-02-06 Lg Display Co., Ltd Organic light emitting diode and organic light emitting device having the same
CN111081888A (zh) * 2018-10-22 2020-04-28 乐金显示有限公司 有机发光二极管和具有该发光二极管的有机发光装置
CN112969695A (zh) * 2018-11-30 2021-06-15 株式会社Lg化学 化合物及包含其的有机发光器件
CN112969695B (zh) * 2018-11-30 2024-10-25 株式会社Lg化学 化合物及包含其的有机发光器件
CN113363400A (zh) * 2021-06-02 2021-09-07 南京昀光科技有限公司 有机发光器件及其制作方法以及显示面板

Also Published As

Publication number Publication date
JP6107657B2 (ja) 2017-04-05
JPWO2013031345A1 (ja) 2015-03-23

Similar Documents

Publication Publication Date Title
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
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
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
JP5857754B2 (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
JP5233081B2 (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
JP5163642B2 (ja) 有機エレクトロルミネセンス素子
JP6107657B2 (ja) 有機エレクトロルミネッセンス素子
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
JP2013110262A (ja) 有機ｅｌ素子ならびに有機ｅｌモジュールおよびその製造方法
JP6225915B2 (ja) 有機エレクトロルミネッセンス素子
WO2011052250A1 (fr) Élément électroluminescent organique, matériau pour éléments électroluminescents organiques, dispositif d'affichage et dispositif d'éclairage
JP5353006B2 (ja) 有機エレクトロルミネッセンス素子、液晶表示装置及び照明装置
JP5261745B2 (ja) 有機エレクトロルミネッセンス素子、表示装置、液晶表示装置及び照明装置
JP2011009517A (ja) 有機エレクトロルミネッセンス素子
JP5061423B2 (ja) 有機エレクトロルミネッセンス素子
JP2010219410A (ja) 有機エレクトロルミネッセンス素子、それを用いた表示装置及び照明装置
JP2010219275A (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材料、表示装置及び照明装置
JP2007059310A (ja) 有機エレクトロルミネッセンス素子、照明装置
JP2008235503A (ja) 有機エレクトロルミネッセンス素子及びそれを用いた照明装置
JP2013102006A (ja) 有機ｅｌ素子
JP2013172071A (ja) 有機エレクトロルミネッセンス素子及び照明装置
JP2013089608A (ja) 有機ｅｌ素子
WO2014034341A1 (fr) Élément électroluminescent organique

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: 12828742

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2013531136

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 12828742

Country of ref document: EP

Kind code of ref document: A1

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载