WO2005083813A2 - Diode electroluminescente organique comprenant un element de protection contre les uv - Google Patents

Diode electroluminescente organique comprenant un element de protection contre les uv Download PDF

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Publication number
WO2005083813A2
WO2005083813A2 PCT/IB2005/050519 IB2005050519W WO2005083813A2 WO 2005083813 A2 WO2005083813 A2 WO 2005083813A2 IB 2005050519 W IB2005050519 W IB 2005050519W WO 2005083813 A2 WO2005083813 A2 WO 2005083813A2
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WO
WIPO (PCT)
Prior art keywords
emitting diode
organic light
filter
layer
diode according
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PCT/IB2005/050519
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English (en)
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WO2005083813A3 (fr
Inventor
Hans-Helmut Bechtel
Dietrich Bertram
Wolfgang Busselt
Joachim Opitz
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Philips Intellectual Property & Standards Gmbh
Koninklijke Philips Electronics N. V.
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Publication of WO2005083813A2 publication Critical patent/WO2005083813A2/fr
Publication of WO2005083813A3 publication Critical patent/WO2005083813A3/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/844—Encapsulations

Definitions

  • Organic light-emitting diode comprising a UV-protective member
  • the present invention relates to an organic light-emitting diode (OLED), which comprises a front electrode member, a counterelectrode member, an organic electroluminescent member comprising an organic electroluminescent material arranged between the front electrode member and the counterelectrode member, said organic electroluminescent material being degradable upon exposure to UV radiation.
  • the organic light-emitting diode also comprises a UV-protective member.
  • a light-emitting diode is a device which, by making use of the phenomenon of electroluminescence, emits light when the device is suitably connected to a power supply.
  • a light-emitting diode in general is based on the fact that semiconductors can be of two types, p-type or n-type, depending on whether dopants pull electrons out of the crystal, forming holes, or add electrons.
  • a light- emitting diode is formed when p-type and n-type semiconductor materials are joined. When a voltage is applied, causing electrons to flow through the structure, electrons flow into the p-type material and holes flow into the n-type material. An electron-hole combination is unstable; there is too much potential energy to be released. As a result, they combine and release the energy in the form of light. This can be a very efficient way to convert electricity into light.
  • LEDs in accordance with the state of the art usually are inorganic semiconductor diodes, i.e. diodes whose emitter material is an inorganic semiconductor, for example ZnS, silicon, germanium or a III-V semiconductor such as InP, GaAs, GaAlAs, GaP, or GaN with suitable dopants.
  • inorganic semiconductor diodes i.e. diodes whose emitter material is an inorganic semiconductor, for example ZnS, silicon, germanium or a III-V semiconductor such as InP, GaAs, GaAlAs, GaP, or GaN with suitable dopants.
  • organic compounds e.g. long-chain conjugated diene, which have many characteristics in common with inorganic semiconductors. They have energy gaps of about the same magnitude, they are poor conductors without dopants, and they can be doped to conduct by means of electrons(n-type) or holes (p- type) transport.
  • organic light-emitting diodes can be manufactured by spin-coating of organic electroluminescent materials between electrodes on a substrate. This process creates organic light-emitting diodes having an extended two- dimensional luminous surface area on a single substrate. This simple manufacturing process also makes the use of organic light- emitting diodes as sources of light for general illumination attractive—such as for large- area lighting in the workplace and for the home.
  • organic light-emitting diodes One major limitation of organic light-emitting diodes is the susceptibility of the organic electroluminescent material to light degradation.
  • the organic electroluminescent material may degrade or become detached from the electrodes under excessive ultra-violet (UV) radiation exposure in terms of total flux owing to either high doses or lower doses over long periods.
  • UV ultra-violet
  • the decreased luminance of organic light-emitting diodes resulting from the deterioration of the organic electroluminescent material represents a serious problem in the practical use of the light-emitting diodes.
  • An attempt to address this problem has been made in that packing techniques are used to reduce the amount of oxygen molecules in organic light-emitting devices, as it is generally believed that photodegradation of the organic electroluminescent materials is caused by photo-oxidation.
  • the photostability of organic material can also be enhanced by the incorporation of a plurality of particles which may, for example, have a diameter of 0.03 microns to 2.5 microns.
  • the organic material may be a light-absorbing material and may be photoluminescent or electroluminescent.
  • Compositions in accordance with the invention of WO2003035795 incorporating an electroluminescent material of enhanced photostability may be used in an organic light- emitting diode.
  • the interaction of the particles with the organic material which provides the photostabilization is difficult to predict and has to be carefully tested and controlled with regard to particle quantity and total particle surface area.
  • OLED light sources for general lighting purposes do not need to be on the same par as perhaps OLED light sources for a computer display, where human attention will be most acutely focused.
  • an organic light-emitting diode comprising a front electrode member, a counterelectrode member, an organic electroluminescent member comprising an organic electroluminescent material arranged between the front electrode member and the counterelectrode member, and a UV-protective filter member.
  • the invention is based on the recognition that it is the ultra-violet part of the ambient light that together with oxygen and moisture inside the organic electroluminescent member causes photo-oxidation of the organic electroluminescent material of the organic light-emitting diode.
  • the UV-protective filter member comprises a long-pass filter to absorb UV-radiation, whose wavelength is below a cut-off wavelength ⁇ k , and to transmit electromagnetic radiation whose wavelength is above said cut-off wavelength ⁇ k .
  • the UV- protective filter member comprises a UV-absorbing filter material.
  • UV-absorbing filter material that is selected from the group comprising Ti ⁇ 2, ZnO, CdO; Zn ⁇ _ x Cd x O, wherein 0 ⁇ x ⁇ 1, AI2O3 and Si ⁇ 2-
  • UV-absorbing filter material that is selected from the group comprising Ti ⁇ 2, ZnO, CdO; Zn ⁇ _ x Cd x O, wherein 0 ⁇ x ⁇ 1, AI2O3 and Si ⁇ 2-
  • UV-protective filter member comprises a UV-reflective filter material.
  • the UV-reflective filter material is an interference filter material.
  • Use may be made of an interference filter material that is a dielectric filter layer stack comprising layers alternately having a high and a low refractive index.
  • the layers having a high refractive index may comprise one or more of the materials selected from titanium oxide T1O2, zirconium oxide Zr ⁇ 2, hafnium oxide Hf ⁇ 2, tantalum oxide Ta2 ⁇ 5 and niobium oxide Nb2 ⁇ 5 and the layers having a low refractive index may comprise one or more of the materials selected from magnesium fluoride MgF2 and silicon oxide Si ⁇ 2-
  • an interference filter material that is a metal-dielectric filter layer stack comprising alternately a metal layer and a layer of dielectric material.
  • a metal-dielectric interference filter is particularly preferred because only few additional layers are required to construct such an interference filter.
  • An organic light-emitting diode in accordance with the invention comprises a front electrode member, a counterelectrode member, an organic electroluminescent member comprising an organic electroluminescent material arranged between the front electrode member and the counterelectrode member, and a UV-protective filter member.
  • Such an organic light-emitting diode typically comprises an arrangement of superposed and partly juxtaposed individual layers. To form such an arrangement of layers use may be made of all layer structures and materials known to those skilled in the art.
  • the organic light-emitting diodes comprise an electroluminescent layer arranged between a positive electrode as the front electrode and a negative electrode as the counterelectrode, one or both electrodes possibly being transparent and/or segmented.
  • one or more electron-injection layers and/or electron- transport layers may be arranged between the electroluminescent layer and the positive electrode.
  • one or more hole-injection layers and/or hole-transport layers may be arranged between the electroluminescent layer and the negative electrode.
  • This arrangement of layers may be provided on a substrate of glass, quartz, ceramic material, synthetic resin, or a transparent flexible plastic film. Suitable synthetic resins are, for example, polyimides, polyethyleneterephtalate, and polytetrafluoroethylene.
  • the electroluminescent layer is arranged between two electrode layers.
  • the negative electrode supplies electrons which combine with the holes in the organic electroluminescent layer originating from the positive electrode so as to form excitons, emitting photons during the recombination process.
  • the positive electrode is made of a non- stoichiometric or doped tin oxide, for example ITO, or of a metal with a high work function, for example gold or silver.
  • ITO non- stoichiometric or doped tin oxide
  • metal with a high work function for example gold or silver.
  • These electrode materials can be readily used to form transparent layers.
  • ITO can suitably be used for this purpose as it is highly electroconductive and transparent.
  • use may be made of a layer of a conductive polyaniline or poly-3,4-ethylenedioxythiophene, whether or not in combination with an ITO layer as the transparent positive electrode.
  • the negative electrode which injects electrons into the organic electroluminescent layer, should have a low work function.
  • the organic light-emitting diode includes an organic electroluminescent member comprising an organic electroluminescent material in which luminescence is generated by application of an electric field (electroluminescence).
  • electroluminescence A light emission in returning to a base state from a singlet excitation state (fluorescence) and a light emission in returning to a base state from a triplet excitation state (phosphorescence) exist as the luminescence in the organic electroluminescent material.
  • Organic electroluminescent materials used for organic light-emitting diodes include: (a) Organic molecules such as Alq3 (8-hydroxyquinolene aluminum) or paraphenylenevinylene. These are often blended with a charge-transporting matrix to increase electrical conduction. Many such molecular compounds exist, but their common feature is an electronic excited state that, when decaying, emits a photon in the visible wavelength range. (b) Organic conjugated polymers such as PPV (poly(phenylene vinylene)) and polyfluorenes. The conjugated polymer may be a cross-linked polymer, star polymer, dendrimer, or a linear chain polymer.
  • Organo-metallics these are complexes of organic ligand groups and metal ions, e.g. lanthanide atoms or iridium. These can be both photoluminesent and electroluminescent and the excitation is transported via an organic ligand to the lanthanide. The lanthanide excited state decays emitting a photon, but in a very narrow spectral bandwidth. The pure color is beneficial to color displays. Also the lifetime of the excited state is much longer, which may make laser action easier to achieve.
  • the diode in accordance with the invention comprises a UV-protective filter member, which is embodied so as to be a long-pass edge filter for UV-radiation with a cut-off wavelength ⁇ k ⁇ f 380 to 440 nm, preferably 380 nm.
  • Said long-pass filter has a low transmission in the range below the cut-off wavelength of 500 nm (stop band) and a high transmission in the range above the cut- off wavelength (passband).
  • the UV-protective filters are selected and employed to provide a transmittance at a wavelength of 380 nm T(380)of not more than 20% and at 350 nm T(350) of less than T(380), at 300nm T(300) less than T(350), a transmittance at a wavelength of 400 nm T(400) of not less than 30%, and at 420 nm T(420) of not less than 55%.
  • the use of a UV-protective long-pass filters provides a steeply rising transmittance curve at wavelengths between 380 to 440 nm.
  • UV-protective filter members Various arrangements with absorption and interference UV-protective filter members are proposed to impede the degradation of the organic electroluminescent materials of the light-emitting diode.
  • a UV-filter material that absorbs throughout the ultra violet spectral range is arranged in front of the diode.
  • the application of a UV-protective filter member on front and back of the light-emitting diode is recommended for transparent organic light-emitting diodes (TOLEDS).
  • UV-absorbing materials of the state of the art are organic polymeric compounds ("UV-absorber"), such as aromatic polyester, polycarbonate, polystyrene, and poly methacry late.
  • UV-absorber organic polymeric compounds
  • aromatic polyester polycarbonate
  • polystyrene polystyrene
  • poly methacry late organic polymeric compounds
  • these have various problems associated therewith, especially with regard to providing a desired sharp cut-off at approximately 380 to 440 nm while also providing complete protection throughout the UV range. They may also suffer from thermal instability.
  • a thin film layer comprising an UV-absorbing inorganic pigment is preferred as their UV-absorbing material.
  • Such UV-absorbing filter members of the invention may contain as their UV-absorbing material particles of an inorganic compound selected from titanium dioxide, zinc oxide, cadmium oxide, mixed crystals of zinc oxide and cadmium oxide, aluminum oxide, silicon dioxide, zirconium oxide, calcium silicate, aluminum silicate, magnesium silicate, and calcium phosphate.
  • an inorganic compound selected from titanium dioxide, zinc oxide, cadmium oxide, mixed crystals of zinc oxide and cadmium oxide, aluminum oxide, silicon dioxide, zirconium oxide, calcium silicate, aluminum silicate, magnesium silicate, and calcium phosphate.
  • titanium dioxide, zinc oxide, cadmium oxide, and mixed crystals of zinc oxide and cadmium oxide Especially preferred is titanium dioxide. Its action substantially resides in the reflection, scattering and absorption of damaging UV radiation and is substantially dependent on the primary particle size. Particle size should be less than 200 nm.
  • Such a long-pass UV-absorbing filter member contains an UV-absorbing inorganic pigment uniformly distributed or dissolved in a carrier, or applied onto a carrier.
  • Suitable carriers are glass as well as optically transparent synthetic resins, such as polyester, polyacrylates, polymethylmethacrylates, polyolefins, polycarbonates, polystyrenes, and the like.
  • Polyethyleneterephtalates and polybutyleneterephtalates are polyesters that are particularly suitable.
  • the long-pass UV-absorbing filter member may be embodied so as to be a self- supporting foil or a thin-film coating. Said long-pass UV-protective filter may be arranged in any location in the organic light-emitting diode in front of the electroluminescent layer.
  • a self-supporting foil has a thickness in a range from 50 ⁇ m to 1000 ⁇ m, and a thin-film coating has a thickness in a range from 1 ⁇ m to 100 ⁇ m.
  • the support may also be a clear lacquer, for example an acrylic resin clear lacquer or a urethane clear lacquer, or it may be a synthetic resin coating.
  • the clear lacquer or synthetic resin coating serving as a long-pass UV-protective filter may be applied to one of the layers of the organic light-emitting diode in front of the electroluminescent layer.
  • the UV-protective member comprises a UV- reflective filter.
  • the simplest embodiment of a UV-reflective filter comprises a UV- reflective material.
  • the UV reflecting materials when properly located on the organic light- emitting diode, will redirect the unconverted UV radiation back to the ambience, preventing the UV radiation from reaching the organic light-emitting diode.
  • the preferred UV-reflecting materials are alumina-containing compounds. Alumina compounds will reflect UV light.
  • the UV-reflecting material may contain alpha alumina, gamma alumina, and mixtures thereof. The preferred material contains between about 5 and 80% by weight of gamma alumina and between about 20 and 95% by weight of alpha alumina.
  • the use of a UV-reflecting material such as alumina-containing compounds also leads to soft, diffuse light output similar to that of fluorescent lamps.
  • Stacks of layers that act as interference filters should be used for obtaining a higher performance of UV protection.
  • the structure of the interference filter There are various possibilities for the structure of the interference filter.
  • a so-called "all-dielectric" multilayer filter comprising a minimum number of 2 layers alternately having a high and a low refractive index.
  • Such a filter typically comprises 10 to 40 layers, the layers alternately consisting of a material having a low refractive index and a material having a high refractive index.
  • magnesium fluoride (MgF2) or silicon oxide (Si ⁇ 2) is chosen for the layers with low refractive index, which materials are suitable for all cutoff wavelengths.
  • a UV-reflective multilayer interference filter comprises alternating layers of high and low refractive index materials, for example Ti ⁇ 2 as the high index layer and Si ⁇ 2 as the low index layer.
  • a typical filter would have 22 layers in the pattern design, beginning at the inner surface of the diode panel 0.125H, 0.25L, 0.25H, (0.25L, 0.25H)*8, 0.25L, 0.25H, 0. 25L, where H is Ti ⁇ 2, L is Si ⁇ 2 and the numerical coefficients indicate optical thickness, n x d, where n is the refractive index and d is the physical thickness of the layer.
  • Such a filter would be substantially transmissive in the visible region of the spectrum, i.e., above 400 nm, and substantially reflective in the UV region, below 400 nm. Actual filters may show a small amount of absorption.
  • a typical method of forming such a filter is by vapor deposition, although other techniques are also possible.
  • a simpler way to realize a broadband long pass all-dielectric UV-filter is a three- or five-layer coating consisting of an indium-tin oxide layer also used as transparent electrode, and alternating layers of Ti ⁇ 2 and SiO2.lt fulfils the requirement of high reflectivity and has low absorption in the visible range. All layers can be deposited by reactive dc magnetron sputtering at room temperature, which is a potential advantage over evaporation. Filter designs containing more layers are less favorable with respect to production cost and throughput time.
  • the UV-protective interference filter may be in the form of a "metal-dielectric" filter, which comprises alternately a metal layer and a dielectric layer, and which has to include only few layers, e.g. 3 to 5 layers. It was found to be particularly desirable to use silver for the metal and titanium dioxide or magnesium fluoride for the dielectric in a multi-layer system.
  • the metal layer of the front electrode member and counterelectrode member of the organic light-emitting diode may be part of the metal-dielectric filter layer stack. The transmittance to light of the metal layer of the front electrode member and/or counterelectrode member decreases with an increasing thickness of the metal layer.
  • the dielectric filter layer within the metal-dielectric interference filter can be selected such that its index of refraction, and thus the intensity of reflection with a suitable matching of the layer thickness, results in interference phenomena within the visible spectral range.
  • the thickness of the layers is so selected that in the ideal case reflection on the electrode layer and at the dielectric layer are compensated. This increases the transmittance to light within the visible spectral range of the metal- dielectric filter system.
  • FIG. 1 shows an organic light-emitting diode with a long-pass UV- absorbing filter.
  • Said organic light-emitting diode comprises a glass substrate 1, an anode 2 of ITO with contact terminals 3, an electroluminescent layer stack 4 comprising a layer of PEDOT (40nm), a layer of NPD of 30nm thickness, a layer of Firpic of 20nm thickness, a layer of BCP (3nm), a layer of Btp2 Ir(acac) of 2nm thickness, and a layer of BCP of 30 nm thickness, a cathode of Al/LiF 5, a passivation layer of polyimide 6, and a long-pass UV-absorbing filter 7.
  • Long-pass UV-absorbing filter 7 is formed by a layer comprising colloidal ZnO, the layer thickness being 2 ⁇ m.
  • Said organic light-emitting diode comprises a glass substrate 1, an anode 2 of ITO with contact terminals 3, an electroluminescent layer stack 4 comprising a layer of PEDOT (40nm), a layer of NPD of 30nm thickness, a layer of Firpic of 20nm thickness, a layer of BCP (3nm), a layer of Btp2 Ir(acac) of 2nm thickness, and a layer of BCP of 30 nm thickness, a cathode of Al/LiF 5, a passivation layer of polyimide 6, a first long-pass UV-absorbing filter 7, and a second long pass UV-absorbing filter 7'.
  • Long-pass UV-absorbing filters 7,7' are formed by layers comprising Ti ⁇ 2 pigment with a particle size of 10 to 15 nm, the layer thickness being 2 ⁇ m.
  • Example 3 shows an organic light-emitting diode with a long-pass UV- reflective all-dielectric interference filter 8.
  • Said organic light-emitting diode comprises a glass substrate 1, an anode 2 of ITO with contact terminals 3, an electroluminescent layer stack 4 comprising a layer of PEDOT (40nm), a layer of NPD of 30nm thickness, a layer of Firpic of 20nm thickness, a layer of BCP (3nm), a layer of Btp2 Ir(acac) of 2nm thickness, and a layer of BCP of 30 nm thickness, a cathode of Al/LiF 5, a passivation layer of polyimide 6, and a UV-reflective interference filter 8.
  • UV-reflective all-dielectric interference filter 8 is former by a first layer consisting of Ti ⁇ 2, layer thickness 129.38 nm, a first layer of Si ⁇ 2, layer thickness 10.5 nm, a second layer consisting of Ti ⁇ 2, layer thickness 102.46 nm, and a second layer of Si ⁇ 2, layer thickness 64.37 nm.
  • FIG. 4 shows an organic light-emitting diode with a metal-dielectric UV- protective filter 9.
  • Said organic light-emitting diode comprises a glass substrate 1, an anode 2 of ITO with contact terminals 3, an electroluminescent layer stack 4 comprising a layer of PEDOT (40nm), a layer of NPD of 30nm thickness, a layer of Firpic of 20nm thickness, a layer of BCP (3nm), a layer of Btp2 Ir(acac) of 2nm thickness, and a layer of BCP of 30 nm thickness, a cathode of Ag 5, a passivation layer of polyimide 6, and a metal-dielectric filter layer comprising Ti ⁇ 2-
  • the metal-dielectric filter is comprised of a layer 9 comprising Ti ⁇ 2 layer thickness 20nm, and a cathode layer 5, the layer thickness of cathode 5 being 20 nm.
  • FIG. 1 diagrammatically shows the structure of an organic light-emitting diode with an UV-absorbing filter on the front electrode member.
  • FIG. 2 diagrammatically shows the structure of an organic light-emitting diode with an UV-absorbing filter on the front electrode member and the counterelectrode member.
  • FIG. 3 diagrammatically shows the structure of an organic light-emitting diode with an UV-reflective interference all-dielectric filter on the front plate.
  • FIG. 4 diagrammatically shows the structure of an organic light-emitting diode with an UV-reflective metal-dielectric filter on the front plate.

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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Illuminated Signs And Luminous Advertising (AREA)
  • Led Device Packages (AREA)

Abstract

L'invention concerne une diode électroluminescente organique comprenant un élément d'électrode frontal, un élément de contre-électrode, un élément électroluminescent organique comprenant un matériau électroluminescent organique disposé entre l'élément d'électrode frontal et l'élément de contre-électrode, ainsi qu'un élément de filtre de protection contre les UV.
PCT/IB2005/050519 2004-02-20 2005-02-10 Diode electroluminescente organique comprenant un element de protection contre les uv WO2005083813A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP04100672.7 2004-02-20
EP04100672 2004-02-20

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WO2005083813A2 true WO2005083813A2 (fr) 2005-09-09
WO2005083813A3 WO2005083813A3 (fr) 2006-05-11

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DE102006059129A1 (de) * 2006-07-31 2008-02-07 Osram Opto Semiconductors Gmbh Strahlungsemittierendes Bauelement
FR2937467A1 (fr) * 2008-10-21 2010-04-23 Saint Gobain Dispositif a diode electroluminescente organique
DE102011079101A1 (de) * 2011-07-13 2013-01-17 Osram Opto Semiconductors Gmbh Organisches optoelektronisches bauteil und verfahren zu dessen herstellung
US8358066B1 (en) 2011-08-10 2013-01-22 General Electric Company Organic light emitting diode package with energy blocking layer
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Cited By (14)

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DE102006059129A1 (de) * 2006-07-31 2008-02-07 Osram Opto Semiconductors Gmbh Strahlungsemittierendes Bauelement
FR2937467A1 (fr) * 2008-10-21 2010-04-23 Saint Gobain Dispositif a diode electroluminescente organique
DE102011079101A1 (de) * 2011-07-13 2013-01-17 Osram Opto Semiconductors Gmbh Organisches optoelektronisches bauteil und verfahren zu dessen herstellung
CN103733371A (zh) * 2011-08-10 2014-04-16 通用电气公司 具有能量阻挡层的有机发光二极管包装
WO2013022557A1 (fr) * 2011-08-10 2013-02-14 General Electric Company Boîtier de diode électroluminescente organique avec couche de blocage d'énergie
US8358066B1 (en) 2011-08-10 2013-01-22 General Electric Company Organic light emitting diode package with energy blocking layer
DE102012206967A1 (de) * 2012-04-26 2013-10-31 Osram Opto Semiconductors Gmbh Optoelektronisches Bauelement und Verfahren zum Herstellen eines optoelektronischen Bauelements
US9478761B2 (en) 2012-04-26 2016-10-25 Osram Oled Gmbh Optoelectronic component having a UV-protecting substrate and method for producing the same
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