WO2012172025A1 - Élément émetteur de rayonnement et procédé de fabrication d'un élément émetteur de rayonnement - Google Patents

Élément émetteur de rayonnement et procédé de fabrication d'un élément émetteur de rayonnement Download PDF

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Publication number
WO2012172025A1
WO2012172025A1 PCT/EP2012/061374 EP2012061374W WO2012172025A1 WO 2012172025 A1 WO2012172025 A1 WO 2012172025A1 EP 2012061374 W EP2012061374 W EP 2012061374W WO 2012172025 A1 WO2012172025 A1 WO 2012172025A1
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WIPO (PCT)
Prior art keywords
radiation
rare earth
earth metal
emitting
derivatives
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PCT/EP2012/061374
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German (de)
English (en)
Inventor
Günter Schmid
Wiebke Sarfert
David Hartmann
Sabine Szyszkowski
Sebastian Meier
Bernhard HÄUPLER
Original Assignee
Osram Ag
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Publication of WO2012172025A1 publication Critical patent/WO2012172025A1/fr

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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
    • 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
    • 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
    • H10K50/135—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising mobile ions
    • 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
    • H10K85/351—Metal complexes comprising lanthanides or actinides, e.g. comprising europium
    • 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
    • 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

Definitions

  • Organic electroluminescent devices contain at least one organic layer between two electrodes. For example, between the electrodes
  • Hole injection layer a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a hole transport layer, a
  • OLEDs are electrons injected from the cathode in the LUMO (lowest unoccupied molecular orbital) in the organic layer when a voltage is applied, and migrate from there towards the anode. Accordingly, holes injected from the anode migrate through the HOMO (highest occupied molecular orbital) of the organic layer to the cathode. When holes and electrons meet in the organic layer, they can become an excited state, the so-called Excitons, form and emit light at their decay. To decouple the light, at least one of the electrodes is transparent. If small molecules are used in OLED structures, the organic layer stack contains, in addition to the actual emission layer, several functional layers, such as, for example, electron transport layers, hole transport layers, electron block layers,
  • Perforated block layers and optionally further emitting layers are optionally further emitting layers.
  • the ionic component is a component present in the organic layer in addition to the phosphorescent rare earth metal complex, and / or at least one rare earth metal complex itself constitutes an ionic component in the organic layer.
  • Rare earth metal complex comprises, which has a sufficiently high quantum efficiency. Since rare earth metals are inexpensive, even rare earth metal complexes can be inexpensive to be provided. Thus, these emitters provide a cost effective alternative to previously known emitters in radiation emitting devices used in their
  • Radiation-emitting organic layer containing an ionic component is.
  • an ionic component is understood as meaning an anionic or a cationic component.
  • the ionic component may be in the form of a salt, for example.
  • an ionic or neutral rare earth metal complex can be combined with a matrix material comprising an ionic component.
  • Energy transfer to the rare earth metal complex provide and / or radiation having a lower wavelength
  • the rare earth metal complex can emit as the rare earth metal complex. Even when combining the rare earth metal complex with another emitting component, the emitted light of the wavelength emitted by the rare earth metal complex is largely perceptible to an external observer, since usually excited states are present in the lower energy
  • longer wavelength emitting components are formed, for example, when the emitting components are present with a distance of less than 10 nm in the organic layer.
  • the matrix material may be selected from a group comprising ionic liquids, polymers, hole transporting small molecules, electron transporting small molecules, ionic transition metal complexes, and combinations thereof.
  • Triplet-triplet annihilation can occur when the emitters, the rare-earth phosphorescent complex molecules, are present at a short distance in the organic layer.
  • the ionic liquid is used for dilution, so that the excited states formed are no longer mutually exclusive
  • polymers can be used as matrix material in the
  • the polymers may be from a group
  • polyethylene oxides polyethylene glycols
  • polyethylenediamines polyethylenediamines
  • polyacrylates such as polymethyl methacrylate (PMMA) or polyacrylic acid or salts thereof
  • Polystyrenes such as poly-p-hydroxy-styrene, polyvinyl alcohols, polyesters, polyurethanes, polyvinylcabazoles, polytriarylamines, Polythiophene and Polyvinylidenphenylene includes.
  • Polymers as matrix materials can improve the semiconductive properties. Alternatively or additionally, as a matrix material
  • Compounds in the organic layer may be present, for example, to improve the electron and hole conductor capabilities.
  • the following compounds can be used by way of example as hole-transporting small molecules:
  • ionic transition metal complexes can also be used as matrix material in the organic layer.
  • examples of such complexes are bis [2- (4, 6-difluorophenyl) pyridinato-N, C2] iridium (III) [1,1'-dimethyl-3,3'-methylenediimidazoline-2,2'-diylidene] hexafluorophosphate (Ir (ppy) 2 (pbpy) PFg or (bis [2- (4,6-difluorophenyl) pyridinato-N,] iridium (III) [1, 1 '-dimethyl-
  • Rare earth metal complex to be selected from a group, the anionic rare earth metal complexes of the general formula
  • the coordination number of rare earth metals is generally 8, the denticity of the ligands may therefore be selected between 1 and 8, preferably between 1 and 3. Accordingly, depending on the denticity, different numbers of ligands may be coordinated to the rare earth metal atom.
  • n is preferably equal to 1
  • cationic rare earth metal complexes is preferably 3.
  • the notation [cat] + n is one
  • Cation mixtures containing a cation Katj_, a cation Katj, and a cation Kat ⁇ with the respective charges + o, + p and + q contain, wherein the sum of the charges o, p and q equal to n.
  • the countercations in the general formula I can be selected from a group comprising metal cations,
  • alkali metal or alkaline earth metal cations and complex derivatives such as 18-crown-6-potassium, substituted and unsubstituted ammonium compounds, for example
  • Fluoride chloride, bromide, iodide, sulfate, phosphate, carbonate, trifluoromethanesulfonate,
  • Trifluoroacetate, tosylate, bis (trifluoromethylsulfone) imide Trifluoroacetate, tosylate, bis (trifluoromethylsulfone) imide
  • Tetrafluoroborate, hexafluoroantimonate, Tetrapyrazolatoborat and complex anions such as Fe (CNG) 3 ⁇ , Fe (CN) g ⁇ ⁇ , Cr (C 2 04) 3_, Cu (CN) 4 3_ and Ni (CN) 4 comprises 2_.
  • the ligands L ⁇ j , L ⁇ , Ly and L ⁇ may independently of one another be selected from a group comprising the 2,2'-bipyridine derivatives, phenanthroline derivatives, 2, 2 ', 2''- terpyridyl derivatives, imidazoles, benzimidazoles, oxazoles,
  • Hydrazides oxo compounds of N-heterocycles, crown ethers, pyridine derivatives with azo compounds, alcohols, phenols,
  • Acetylacetates are selected.
  • the ligands may be substituted or
  • unsubstituted 2, 2 'bipyridine derivatives include, as well as
  • Phenanthroline derivatives Also derivatives with higher
  • Teeth such as 2, 2 ', 2' '-Terpyridylderivate
  • nitrogen derivatives such as imidazoles, benzimidazoles, oxazoles, triazines,
  • Phthalocyanines amine acids such as pyridine carboxylic acids or EDTA, and 2, 6-bis (2'-quinolyl) pyridine.
  • the ligands may, for example, selected from complex pyridine ligands with azo compounds such as 2, 6-pyridinediyl bis [a- (ethylidene hydrazone benzyl alcohol)], or oximes, nitroso compounds, amides, hydrazides, oxo compounds of N-heterocycles such as lactams or succinimides and cryptands be.
  • azo compounds such as 2, 6-pyridinediyl bis [a- (ethylidene hydrazone benzyl alcohol)]
  • oximes nitroso compounds
  • amides amides
  • hydrazides oxo compounds of N-heterocycles
  • lactams or succinimides cryptands be.
  • Further examples of ligands are alcohols, phenols,
  • ketones for example salicylaldehyde
  • Sulfur derivatives can also be selected as ligands.
  • ligands Exemplary here are sulfoxides, sulfonamides, thiols,
  • Thiocarboxylates dithiocarbamic acids, thioureas, sulfur-containing heterocycles such as 1, 4-oxathiane or dithiane, and called Bistrimethylsilylamide.
  • phosphorus derivatives such as phosphines, phosphine oxides, phosphoric acids and their esters, phosphorous acid and its esters, amides of phosphinic acid and amides of phosphonic acid.
  • amides of sulfur and arsenic acids are also possiblee.
  • Suitable ligands may also be selected from inorganic derivatives such as hydroxo, nitrato, azido, halo, phosphato, sulfito, sulfato,
  • An example of an anionic ligand is bis (trifluoromethylsulfone) amide.
  • the ligands can be combined in almost any manner.
  • the choice of ligands can be made according to their respective charge, depending on what is to be achieved for a total charge of the rare earth metal complex.
  • Ligands acetylacetonates with different substituents for example, F, Cl, Br, I, aromatics, substituted and unsubstituted benzoates or higher homologs
  • substituents for example, F, Cl, Br, I, aromatics, substituted and unsubstituted benzoates or higher homologs
  • Other possible ligands are, for example
  • Monodentate ligands can, for example, Cl ⁇ , Br ", I and CN ⁇ be.
  • anionic ligands in the anionic complexes are replaced by neutral ligands, cationic rare earth metal complexes according to the general formula II are obtained.
  • at least one of the ligands is uncharged.
  • substituted or unsubstituted 2, 2 'bipyridines or bridged phenantroline derivatives can be used. Also mono- or polydentate phosphine ligands are conceivable.
  • neutral rare earth metal complex according to the general formula III, it is possible in particular to use three singly negatively charged, bidentate ligands and one bidentate neutral ligand.
  • An example of such a complex is tris (benzoylacetonato) mono (phenanthroline) europium (III).
  • ligands can be found, for example, in the Gmelin Handbook of Inorganic Chemistry, Sc, Y, La-Lu Rare Earth Elements, parts D1 to D5.
  • Radiation-emitting device can be transparent
  • Electrode a cathode and the second electrode to be an anode or vice versa may contain indium tin oxide (ITO).
  • ITO indium tin oxide
  • Other materials include aluminum zinc oxide (AZO) or doped Tin oxides.
  • electrode materials may also be selected from gold, silver and aluminum.
  • Electrode material can furthermore also be used PEDOT: PSS (poly-3,4-ethylenedioxythiophene doped with polystyrene sulfonate) or polyaniline, which additionally provide planarization and uniform current distribution in the respective electrode.
  • PEDOT poly-3,4-ethylenedioxythiophene doped with polystyrene sulfonate
  • polyaniline which additionally provide planarization and uniform current distribution in the respective electrode.
  • the radiation-emitting component may be an organic light-emitting electrochemical cell.
  • an electric field is applied in a light-emitting electrochemical cell, the mobile ions in the organic layer redistribute under the electric field. As a result, a high electric field is generated at the electrodes, which makes both contacts ohmic and thus the
  • Rare earth metal complexes in organic light-emitting electrochemical cells brings cost advantages due to the favorable emitter material with it. It will continue a process for producing a
  • the organic solution contains an ionic component and comprises a solvent and at least one phosphorescent rare earth metal complex.
  • the organic solution contains an ionic component and comprises a solvent and a phosphorescent rare earth metal complex
  • the ionic component in the solution is the phosphorescent rare earth metal complex and / or other components, such as matrix materials, are present in the solution which have ionic components.
  • the solvent for producing the organic solution may be selected from a group called PGMEA
  • organic solvents which are not explicitly mentioned here are also usable.
  • the application of the organic solution may be carried out by a method selected from a group consisting of
  • Printing techniques include flexographic printing, gravure printing, inkjet printing and screen printing.
  • the organic solution can be applied by a wet chemical method, which allows the use of rare earth metal complexes
  • the organic solution can be dried before process step C). Thus, the solvent is removed, so that the organic layer, the at least one
  • Such a layer may, for example, have a thickness of 50 to 200 nm.
  • Rare earth metal complex as a radiation-emitting material in a radiation-emitting device specified, wherein the radiation-emitting device is an ionic
  • the radiation-emitting component may be an organic light-emitting component
  • Figure lb shows the schematic side view of another embodiment of an organic light-emitting electrochemical cell
  • Figure 2 shows the schematic side view of a
  • FIGS. 3a to 3c show results of comparative measurements on an organic light emitting diode
  • FIGS. 4a to 4d show characteristic measured values of an organic light-emitting electrochemical cell.
  • Figure la shows the schematic side view of a
  • the encapsulation 50 can encapsulate the entire component, even at the lateral edges, which is not shown here for reasons of clarity.
  • the substrate 10 may comprise glass, for example.
  • the first electrode 20 may be transparent, for example, so that the device is a bottom emitter.
  • Materials of the first electrode 20 may be, for example, ITO, AZO or doped tin oxide.
  • the second electrode 40 may include materials such as Au, AI and Ag included. If both electrodes 20, 40 are to be made transparent, the second electrode 40 may also contain, for example, ITO, AZO or doped tin oxide. Also, only the second electrode 40 may be formed transparent, which is a top emitter in the device.
  • Matrix materials can be an ionic or neutral
  • Rare earth metal complex with an ionic matrix material an ionic rare earth metal complex with a neutral matrix material or an ionic or neutral
  • a hole transport layer 25 is arranged between the first electrode 20 and the organic layer 30.
  • Hole transport layer 25 may, for example, the first
  • the OLED according to FIG. 2 has a hole injection layer 31 on the first electrode 20.
  • This can, for example, a 100 nm thick PEDO: PSS layer (PEDOT: PSS: poly-3, 4-ethylenedioxythiophen, with
  • the emission layer 32 for example a 30 nm thick layer comprising a matrix material and a
  • Emission layer 32 is a hole block layer 33 is arranged, which can be 20 nm thick example, and 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP) may contain.
  • the active area of an OLEEC device is about 4 mm 2 .
  • Anode 20 further layers are deposited by spin coating techniques or vapor deposition.
  • the cathode 40 consisting of a 150 to 200 nm thick Al layer is vapor-deposited and encapsulated with a glass cap 50 to interact with the organic layers
  • the voltage U is set to a constant value in each case and the current and luminance D, L are sampled in steps of 1 s.
  • the OLED current-voltage characteristic is measured, for example, by means of a Keithley SMU 236, a source measuring unit, ie a power supply with built-in current-voltage measurement.
  • the luminance L is measured here by means of color-calibrated photodiodes (type 6514, Keithley Instruments).
  • EL spectra are detected by means of a spectral camera (PR650) in the visible wavelength range between 380 nm and 780 nm.
  • FIGS. 3a to 3c show the results of FIG
  • the rare earth metal complex (hereinafter also Eu complex) sodium tetrakis (dibenzoylmethane) europium (III)
  • All layers except for the hole injection layer 31 are applied by vapor deposition.
  • the hole injection layer 31 is applied by spin coating.
  • FIG. 3a shows the result of the LIV measurement on the OLED described above, in which the current density D is measured as a function of the voltage U.
  • FIG. 3b correspondingly shows the luminance L as a function of the voltage U measured for the OLED described above.
  • Figures 3a and 3b show characteristic graphs of the OLED.
  • FIG. 3 a shows how the current changes as the voltage increases.
  • the y-axis is logarithmic, so the increase of the current with the voltage is expotential, which corresponds to a diode characteristic.
  • the current flowing through the component generates excitons which decay with the release of light. How this light output changes with the voltage and therefore the current is shown in FIG. 3b. From this can be, for example, the
  • Figure 3c shows the electroluminescence spectrum measured for the OLED described above. It is the relative
  • the OLED lights red.
  • the electroluminescence in the OLED device can be attributed to the matrix having three functions
  • Electroluminescence of rare earth metal complexes can be shown in OLEEC devices.
  • the OLEEC component is composed of:
  • PEDOT hole transport layer 25 PSS having a thickness of 100 nm
  • the ionic liquid (IL) is imidazolium BMIM-PF 6 im
  • Rare earth metal complex is selected 0: 100, 90:10, 70:30 and 50:50 vol%. Both the PEDOT: PSS layer 25 and the radiation-emitting organic layer 30 are applied by spin-coating. Matrix material and emitter are dissolved in anisole. The solids concentration in solution is 4% by weight for all subsequent mixtures.
  • Composition K [Eu (NTA) 4 ] Na + IL
  • Composition L S-TAD: [Eu (NTA) 4 ] Na (70:30) + IL
  • Composition P Ir-749-PF 6 : [Eu (NTA) 4 ] Na (50:50) + IL.
  • compositions 0 and P Compositions 0 and P and compared to the
  • Composition S in which no emitter, but only IL and the matrix material Ir-749-PF6 is present in the organic layer 30, is shown.
  • the normalized intensity I n is plotted as a function of ⁇ .
  • composition O is similar to the EL spectrum of that of a "pure" Ir-749-PF6 device (Composition S) . This OLEEC will be light blue in operation
  • composition P increases the tunneling probability for the excitation energy from the matrix material (high energy host) to the Eu emitter (low energy guest) with subsequent radiative recombination of the triplet excitons.
  • Such OLEECs turn red during operation.
  • FIG. 4c and 4d show typical OLEEC characteristics for compositions 0 at 6V and 9V, and P at 15V.
  • FIG. 4c shows the current density D as a function of the time t in [min]
  • FIG. 4d shows the luminance L in
  • Solubilities of some exemplary Eu complexes in various solvents are also shown in Table 1 below. It can be seen that the solubility depends not only on the solvent but also on the choice
  • Solubility is, the easier the complexes can be deposited, that is, the easier the manufacturing process for producing an OLEEC.
  • the product is analyzed analytically by elemental analysis

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • Inorganic Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne un élément émetteur de rayonnement qui comporte une première électrode (20), une couche organique émettrice de rayonnement (30) sur la première électrode (20) et une deuxième électrode (40) sur la couche organique émettrice de rayonnement (30), la couche organique (30) contenant un composant ionique et au moins un complexe métallique de terre rare phosphorescent. L'invention concerne également un procédé de fabrication d'un élément émetteur de rayonnement ainsi que l'utilisation d'un complexe métallique de terre rare phosphorescent dans un élément émetteur de rayonnement.
PCT/EP2012/061374 2011-06-14 2012-06-14 Élément émetteur de rayonnement et procédé de fabrication d'un élément émetteur de rayonnement WO2012172025A1 (fr)

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DE102011104169A DE102011104169A1 (de) 2011-06-14 2011-06-14 Strahlungsemittierendes Bauelement und Verfahren zur Herstellung eines strahlungsemittierenden Bauelements

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8784690B2 (en) 2010-08-20 2014-07-22 Rhodia Operations Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels and foams

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017194435A1 (fr) * 2016-05-11 2017-11-16 Merck Patent Gmbh Compositions pour cellules électrochimiques

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000044851A2 (fr) * 1999-02-01 2000-08-03 South Bank University Enterprises Ltd Materiaux electroluminescents
US20060054886A1 (en) * 2004-09-03 2006-03-16 The Regents Of The University Of California Methods and devices utilizing soluble conjugated polymers
US20070082227A1 (en) * 2005-09-29 2007-04-12 Tsuyoshi Kobayashi Light-emitting device
US20070215879A1 (en) * 2006-03-20 2007-09-20 General Electric Company Opto-electronic devices exhibiting enhanced efficiency
US20070281386A1 (en) * 2006-05-31 2007-12-06 Byoung-Choo Park Organic semiconductor device and method for manufacturing the same

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4428450A1 (de) * 1994-08-11 1996-02-15 Philips Patentverwaltung Organisches, elektrolumineszentes Bauteil
CN1441826A (zh) * 2000-06-12 2003-09-10 美商·麦克斯登股份有限公司 聚合物基质电致发光材料及装置
TWI289156B (en) * 2001-08-09 2007-11-01 Ritek Corp Phosphorescent material
DE102008033929A1 (de) * 2008-07-18 2010-01-21 Siemens Aktiengesellschaft Phosphoreszente Metallkomplexverbindung, Verfahren zur Herstellung dazu und strahlungsemittierendes Bauelement

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000044851A2 (fr) * 1999-02-01 2000-08-03 South Bank University Enterprises Ltd Materiaux electroluminescents
US20060054886A1 (en) * 2004-09-03 2006-03-16 The Regents Of The University Of California Methods and devices utilizing soluble conjugated polymers
US20070082227A1 (en) * 2005-09-29 2007-04-12 Tsuyoshi Kobayashi Light-emitting device
US20070215879A1 (en) * 2006-03-20 2007-09-20 General Electric Company Opto-electronic devices exhibiting enhanced efficiency
US20070281386A1 (en) * 2006-05-31 2007-12-06 Byoung-Choo Park Organic semiconductor device and method for manufacturing the same

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
LIS S ET AL: "Photoluminescence and electrochemiluminescence studies of chosen rare earths systems", JOURNAL OF RARE EARTHS, INTERNATIONAL ACADEMIC PUBLISHERS, BEIJING, CN, vol. 26, no. 2, 1 April 2008 (2008-04-01), pages 192 - 197, XP022934022, ISSN: 1002-0721, [retrieved on 20080401], DOI: 10.1016/S1002-0721(08)60063-0 *
WANG Z ET AL: "Energy transfer from a polymer host to a europium complex in light-emitting diodes", JOURNAL OF LUMINESCENCE, ELSEVIER BV NORTH-HOLLAND, NL, vol. 111, no. 3, 1 February 2005 (2005-02-01), pages 199 - 203, XP027659738, ISSN: 0022-2313, [retrieved on 20050201] *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8784690B2 (en) 2010-08-20 2014-07-22 Rhodia Operations Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels and foams
US9552903B2 (en) 2010-08-20 2017-01-24 Rhodia Operations Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels and foams

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