[go: up one dir, main page]

WO2000006665A1 - Dispositifs electroluminescents organiques - Google Patents

Dispositifs electroluminescents organiques Download PDF

Info

Publication number
WO2000006665A1
WO2000006665A1 PCT/US1999/016834 US9916834W WO0006665A1 WO 2000006665 A1 WO2000006665 A1 WO 2000006665A1 US 9916834 W US9916834 W US 9916834W WO 0006665 A1 WO0006665 A1 WO 0006665A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrocarbyl
organic film
film
polymer
occurrence
Prior art date
Application number
PCT/US1999/016834
Other languages
English (en)
Inventor
Mark T. Bernius
Edmund P. Woo
Lisa L. Wujkowski
Michael Inbasekaran
Original Assignee
The Dow Chemical Company
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 The Dow Chemical Company filed Critical The Dow Chemical Company
Publication of WO2000006665A1 publication Critical patent/WO2000006665A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers

Definitions

  • This invention relates to organic-containing electroluminescent devices and, more particularly, to such devices which contain an organic electroluminescent layer and an organic hole-transport layer.
  • An organic electroluminescent device typically consists of an organic film sandwiched between an anode and a cathode, such that when a positive bias is applied to the device, holes are injected into the organic film from the anode and electrons are injected into the organic film from the cathode. The combination of a hole and an electron may give rise to an exciton which may undergo radiative decay to the ground state by releasing a photon.
  • the anode is commonly a mixed oxide of tin and indium for its conductivity and transparency.
  • the mixed oxide (ITO) is deposited on a transparent substrate such as glass or plastic so that the light emitted by the organic film may be observed.
  • the organic film may be the composite of several individual layers each designed for a distinct function.
  • the individual layers of the organic film may be all polymeric in nature or combinations of films of polymers and films of small molecules deposited by thermal evaporation.
  • the cathode is commonly a metallic film deposited on the surface of the organic film by either evaporation or sputtering.
  • this invention is an electroluminescent device comprising a light-emitting organic film, arranged between an anode material and a cathode material such that under an applied voltage, the device is forward biased and holes are injected from the anode material into the organic film adjacent to the anode material and electrons are injected from the cathode material into the organic film adjacent to the cathode material, resulting in light emission from the light-emitting organic film; wherein the device additionally comprises a solution-processed film of a blend of an acid-functional non-conductive polymer and a conductive polymer positioned between the anode material and the light-emitting organic film, wherein the weight ratio of non-conducting polymer to conducting polymer is at least 0.75:1.
  • solution-processed film refers to a film prepared by depositing a water- or organic solvent-based solution of soluble material onto a first substrate, and then removing enough of the water or solvent to form a film of the material which is sufficiently stable to permit it to serve as a substrate for the deposition of additional film-forming liquid materials.
  • Suitable conductive polymers for use in preparing the device of the invention are polymers having an average molecular weight of greater than 1000 Daltons and which can be processed using solution processing techniques into a film having a thickness of less than 10,000 nm. Such polymers also have an electrical conductivity of at least 10 "6 Siemens/cm (S/cm), preferably at least 10 "4 S/cm, and most preferably at least 10 '2 S/cm. Examples of such include polyanilines, polythiophenes, and polypyrroles. Such polymers are typically "doped” to form an electronically-conductive complex of the protonated polymer which is more processible, conductive, or stable than the corresponding polymer in its un-doped form.
  • a preferred method for preparing a water-soluble doped polymer is a template synthesis method as described, for example, in U.S. Patent 5,489,400 and in WO 97/03127.
  • Such a method generally includes the steps of complexing the monomers used to prepare the conductive polymer with the long-chain dopant, and then adding an oxidant to the complex and polymerizing the complexed monomers to form the conductive polymer.
  • Suitable non-conductive polymers for use in the invention are polymers having an average molecular weight of greater than 1 ,000 Daltons, which can be processed using solution processing techniques into a film having a thickness of less than 10,000 nm.
  • Such polymers have an electrical conductivity of less than 10 "10 S/cm and a pKa of less than 5, more preferably less than 3, and most preferably of less than 1.
  • Examples of such include polymers having pendant groups selected from sulfonic acid, sulfinic acid, carboxylic acid, phosphoric acid, phosphonic acid, phosphinic acid, and -N+(R) 2 H where R is selected from hydrogen, C ⁇ C ⁇ hydrocarbyl, hydroxy, alkoxy, and aryloxy.
  • acid polymers include poly(styrenesulfonic acid) (PSS), poly(2-acrylamido-2-methyl-1 -propanesulfonic acid) (AMP), polyacrylic acid, polymethacrylic acid; all are available commercially.
  • Other acid polymers useful in the invention are sulfonated polyphenylenes such as those disclosed by Rulkens et al. in Ber. Bunsenges. Phys. Chem. Vol. 100, pp. 707-714, 1996 and by Rau and Rehahn in Polymer Communications, Vol. 34, pp. 2889-2893, 1993, and polyphenylenes bearing carboxylic acid functional groups such as the one reported by Chaturvedi et al. in Macromolecules, Vol. 26, pp. 2606-2611 , 1993 and blends thereof.
  • the (a) non-conductive polymer and (b) conductive polymers are preferably utilized in an amount sufficient to provide a weight ratio of (a):(b) of at least 0.75:1 , more preferably at least 1 :1 , and most preferably at least 1.5:1. If the conductive polymer is doped with a non-conductive polymeric acid, for the purposes of determining the weight ratios of non-conductive:conductive polymer, the non- conductive polymer amounts referred to above refer to polymers which are present in an excess amount, relative to the stoichiometric amount needed to dope the conductive polymer.
  • the devices of the invention may be prepared by any suitable method, but are preferably prepared by depositing relatively thin films of organic and inorganic materials onto a transparent substrate, starting with an anode material, optionally followed by one or more films of any additional organic or inorganic hole-transport materials, followed by one or more films of at least one electroluminescent polymer, optionally followed by any additional layers of organic or inorganic and electron- transport material(s) (in addition to the cathode material), which are then followed by depositing a layer of a cathode material.
  • the layers of material may be prepared by any method suitable for the preparation of a thin film thereof, such as, for example, sputtering, spin-coating, or vapor deposition. Further, the particular technique employed to deposit a thin layer of organic material may require the use of a suitable organic solvent.
  • anode material refers to a semi-transparent or transparent conducting film with a work function between 4.5 eV and 5.5 eV.
  • suitable anode materials include oxides and mixed oxides of indium and tin, and gold, but is preferably a mixed oxide of tin and indium ("ITO").
  • the metal o oxide is deposited on a transparent substrate such as glass or a solvent-resistant transparent plastic material such as a polyester sheet, so that the light emitted by the EL organic film may be observed.
  • the organic film(s) within the device may be a multi-layer composite of several individual layers, each of which are designed for a distinct function, or may be one or more layers of a single material.
  • any organic film next to the anode material needs to have the functionality of transporting holes.
  • any layer next to the cathode material needs to have the functionality of transporting electrons.
  • a layer of an electroluminescent organic material is also required.
  • a single organic material can perform the combined functions of hole and electron transport and light emission.
  • the term "Electroluminescent organic film” as used herein refers to an organic film which, upon the injection of electrons and holes into it from opposite sides of the film, produce excitons which can relax to the ground state by emitting photons, preferably corresponding to wavelengths in the visible range.
  • organic film as used herein means a film of an organic polymer, or a film of one or more organic molecules deposited by thermal evaporation or by solution processing. It is preferred that the total thickness of each organic film be less than 5000 nanometers (nm). It is more preferred that the thickness of the combined layers of organic film(s) be less than 5000 nm, and most preferably less than 3000 nm.
  • the ITO-coated glass which preferably serves as the anode and the substrate for depositing the organic film(s) thereon is preferably cleaned with detergent, organic solvents or UV-ozone treated prior to deposition of the organic film(s).
  • hole-transporting organic film refers to a layer of a film of a compound or polymer which, when disposed between two electrodes to which a field is applied and holes are injected from the anode, permits adequate transport of holes into the EL organic film.
  • electron-transporting organic film refers to a layer of a film of a compound or polymer which, when disposed between two electrodes to which a field is applied and electrons are injected from the cathode, permits adequate transport of electrons into the electroluminescent organic film.
  • a separate hole-transport organic film and/or electron-transport film is used to prepare the electroluminescent device, such films may also have some degree of electroluminescence, but their electroluminescence efficiency will be less than that of the electroluminescent film.
  • the film of a blend of conductive and non-conductive polymers preferably serves as a hole-transport layer in the device of the invention.
  • additional layers of other organic materials which have a hole-transport function may also be utilized as additional layers in the device.
  • Hole-transporting polymers typically are comprised of triarylamine moieties. In cases where a separate organic layer selected for its hole-transport properties is utilized, the polymeric arylamines described in W097/33193; U.S. Patent Application Serial No.
  • this hole-transport layer(s) to erosion by the solution of the organic films which may be subsequently applied to the composite structure is obviously critical to the successful fabrication of multi-layer devices. Resistance to erosion may be increased by, for example, choosing a high molecular weight or crosslinkable hole-transport polymer, or by selecting a hole-transport polymer which is insoluble in the particular solvent used to deposit the electroluminescent polymer.
  • the thickness of this hole-transport layer is preferably 500 nm or less, preferably 300 nm or less, most preferably 150 nm or less.
  • layers of hole-transporting polymer films are arranged so that the layer closest to the anode has the lower oxidation potential, with the adjacent layers having progressively higher oxidation potentials.
  • electroluminescent devices having relatively high light output per unit voltage may be prepared.
  • a separate electron-transporting organic layer it may be applied either by thermal evaporation of low molecular weight materials or by solution coating of a polymer with a solvent that would not cause significant damage to the underlying electroluminescent organic film.
  • low molecular weight materials include the metal complexes of 8-hydroxyquinoline (as described in Burrows et al., Applied Physics Letters. Vol. 64, pp. 2718-2720 (1994)), metallic complexes of 10-hydroxybenzo(h)quinoline (as described in Hammed et al., Chemistry Letters, pp.
  • Polymeric electron-transporting materials useful in making electron- transporting organic films are exemplified by 1 ,3,4-oxadiazole-containing polymers (as described in Li et al., Journal of Chemical Society, pp. 221 1 -2212 (1995), and in Yang and Pei, Journal of Applied Physics. Vol. 77, pp. 4807-4809 (1995)), 1 ,3,4- triazole-containing polymers (as described in Strukelj et al., Science, Vol. 267, pp. 1969-1972 (1995)), quinoxaline-containing polymers (as described in Yamamoto et al., Japan Journal of Applied Physics, Vol. 33, pp.
  • the thickness of this layer may be 500 nm or less, preferably 300 nm or less, most preferably 150 nm or less.
  • the electroluminescent organic film is a film containing at least one fluorene based polymer.
  • the flourene based polymer comprises monomeric units of the formula:
  • R 1 is independently in each occurrence H, C, .20 hydrocarbyl or
  • C 1 20 hydrocarbyl containing one or more S, N, O, P or Si atoms, C 416 hydrocarbyl carbonyloxy, C 4 16 aryl(trialkylsiloxy) or both R 1 may form with the 9-carbon on the fluorene ring a C 520 cycloaliphatic structure or a C 420 cycloaliphatic structure containing one or more heteroatoms of S, N or O; R 2 is independently in each occurrence C 1 20 hydrocarbyl, C 1 20 hydrocarbyloxy,
  • the fluorene monomeric unit preferably occurs at least 10 times and no more than 10,000 times in the polymer.
  • R 1 is preferably in each occurrence n-octyl.
  • the preferred polymer may be a homopolymer of fluorene or may be a copolymer of the fluorene monomeric unit with an additional monomeric unit such as
  • R is a hydrocarbyl having 1 -20 carbon atoms, e.g., methyl, ethyl, isopropyl, n-hexyl, n-octyl, phenyl, benzyl, and naphthyl, optionally further substituted by substituents containing heteroatoms such as oxygen, nitrogen, and sulfur.
  • R 3 is independently in each occurrence carboxyl, 0,-0 ⁇ alkyl, C ⁇ -C ⁇ alkoxy or a group of the formula -CO 2 R 4 wherein R" is a C ⁇ C ⁇ alkyl; and b is independently in each occurrence an integer from 0 to 3.
  • the monomeric units are preferably alternating.
  • Blends of the polymers are especially preferred, such as a blend of a homopolymer of the monomer of formula 1 with from 0.1 to 50 percent by weight of an alternating copolymer of monomers of formula 1 with the comonomers listed above.
  • a preferred example of such copolymers has the formula:
  • R 1 is as defined for formula 1 and n is an integer greater than 10 and less than 10,000.
  • the BT polymer is preferably used in an amount, based on the weight of the polymers in the blend, of at least 1 percent, more preferably at least about 3 percent; but preferably no greater than 20 percent, more preferably no greater than 10 percent, and most preferably no greater than 5 percent.
  • cathode material refers to a conducting metal film with a work function between 2.5 eV and 4.5 eV.
  • the cathode material comprises calcium.
  • the cathode of calcium may be deposited by any suitable technique, such as thermal evaporation or by sputtering.
  • the thickness of the cathode is preferably from 1 nm to 10,000 nm.
  • the film of calcium may be coated with another film of a metal having a higher work function, such as aluminum or silver, to improve stability.
  • the thickness of the additional layer is preferably at least 100 nm, more preferably at least 250 nm, most preferably at least 500 nm; but preferably no greater than 10,000 nm, more preferably no greater than 5,000 nm, and most preferably no greater than 1 ,000 nm.
  • calcium preferably comprises at least 20 percent of the thickness of such film, more preferably at least 50 percent, and most preferably 100 percent.
  • the devices of this invention preferably emit light having a brightness of at least 100 Cd/m 2 when subjected to an applied voltage of no more than 50 volts, preferably no more than 10 volts, and most preferably no more than 5 volts.
  • Electroluminescent devices are prepared by depositing a water-based blend as described in Table 1 onto indium-tin-oxide-coated glass and allowing the film to dry.
  • the conducting polymer is doped poly(3,4-ethyienedioxythiophene, purchased as 1.3 weight percent aqueous dispersion of poly(3,4-ethylenedioxythiophene) and poly(styrenesulfonic acid) in a weight ratio of 1 :16 or mole ratio of 1 :1.2 (as Baytron P TM from Bayer).
  • the excess acid polymers used are poly(styrenesulfonic acid) (PSS) obtained from Scientific Polymer Products, Inc.
  • An electroluminescent film of a polymer blend (5 weight percent of BT and 95 weight percent of F8; having a thickness of about 150 nm, is then prepared on top of the film containing poly(3,4-ethylenedioxythiophene).
  • Cathodes are then deposited on the electroluminescent layer using a vapor deposition technique from calcium (approximately 150 nm) with a silver overcoat (approximately 160 nm) using a vapor deposition technique.
  • Each device is characterized by the voltage and current required to reach brightness of 200 Cd/m 2 and 4000 Cd/m .
  • Device efficiency is expressed as Cd/A and lumens/watt (Lu/W).
  • the values presented in Table 1 are average values of 8-10 devices.

Landscapes

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

Abstract

La présente invention concerne un dispositif électroluminescent (LE) contenant un film organique photoémetteur, disposé entre un matériau anodique et un matériau cathodique, de façon qu'à l'application d'une tension, le dispositif subisse une polarisation postéro-antérieure. En outre, des trous sont injectés depuis le matériau anodique dans le film organique au voisinage du matériau anodique, et des électrons sont injectés depuis le matériau cathodique dans le film organique au voisinage du matériau cathodique. Il en résulte l'émission de lumière de la part du film photoémetteur. Le dispositif comporte également un film traité en solution et fait d'un mélange d'un polymère à fonction acide et non conducteur, et d'un polymère conducteur disposé entre le matériau anodique et le film organique photoémetteur, pour un rapport massique entre polymère non conducteur et polymère conducteur d'au moins 0,75:1.
PCT/US1999/016834 1998-07-28 1999-07-23 Dispositifs electroluminescents organiques WO2000006665A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US12327198A 1998-07-28 1998-07-28
US09/123,271 1998-07-28

Publications (1)

Publication Number Publication Date
WO2000006665A1 true WO2000006665A1 (fr) 2000-02-10

Family

ID=22407686

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/016834 WO2000006665A1 (fr) 1998-07-28 1999-07-23 Dispositifs electroluminescents organiques

Country Status (1)

Country Link
WO (1) WO2000006665A1 (fr)

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001099207A3 (fr) * 2000-06-20 2002-04-18 Uniax Corp Structures multicouches en tant qu'electrodes stables d'injection de trous a utiliser dans des dispositifs electroniques organiques a haute efficacite
WO2001099208A3 (fr) * 2000-06-20 2002-05-02 Uniax Corp Traitement thermique d'une couche electroactive organique traitee par une solution dans un dispositif electronique organique
WO2001099192A3 (fr) * 2000-06-20 2003-01-16 Uniax Corp Polymeres conducteurs haute resistance, utilises dans des dispositifs electroniques organiques pixelises a haut rendement
US6680578B2 (en) 2001-09-19 2004-01-20 Osram Opto Semiconductors, Gmbh Organic light emitting diode light source
WO2004019346A1 (fr) * 2002-08-23 2004-03-04 Agfa-Gevaert Configuration de couche comprenant un element de blocage d'electrons
US6977390B2 (en) 2002-08-23 2005-12-20 Agfa Gevaert Layer configuration comprising an electron-blocking element
US7056600B2 (en) * 2002-08-23 2006-06-06 Agfa Gevaert Layer configuration comprising an electron-blocking element
US7112368B2 (en) 2001-11-06 2006-09-26 E. I. Du Pont De Nemours And Company Poly(dioxythiophene)/poly(acrylamidoalkyslufonic acid) complexes
US7307276B2 (en) 2002-08-23 2007-12-11 Agfa-Gevaert Layer configuration comprising an electron-blocking element
WO2008026649A1 (fr) 2006-08-30 2008-03-06 Sumitomo Chemical Company, Limited Élément à électroluminescence organique
WO2008032843A1 (fr) 2006-09-14 2008-03-20 Sumitomo Chemical Company, Limited Dispositif électroluminescent organique
DE112006002668T5 (de) 2005-10-07 2008-08-14 Sumitomo Chemical Company, Ltd. Copolymer und polymere lichtemittierende Vorrichtung unter Verwendung desselben
DE112006002998T5 (de) 2005-11-18 2008-09-18 Sumitomo Chemical Co., Ltd. Polymerverbindung und Polymer enthaltende Licht ermittierende Vorrichtung, die diese verwendet
DE112006003090T5 (de) 2005-11-11 2008-09-25 Sumitomo Chemical Co. Ltd. Konjugierte Polymerverbindung und polymere lichtemittierende Vorrichtung unter deren Verwendung
DE112006002147T5 (de) 2005-08-12 2008-10-23 Sumitomo Chemical Co., Ltd. Polymerverbindung und polymere lichtemittierende Vorrichtung diese verwendend
DE112006003570T5 (de) 2005-12-28 2008-11-06 Sumitomo Chemical Co., Ltd. Blockcopolymer
WO2008136492A1 (fr) 2007-04-27 2008-11-13 Sumitomo Chemical Company, Limited Polymère de pyrène et élément luminescent fabriqué avec ce polymère
WO2008149829A1 (fr) 2007-05-30 2008-12-11 Sumitomo Chemical Company, Limited Dispositif électroluminescent organique et dispositif d'affichage utilisant ce dispositif
WO2009008543A1 (fr) 2007-07-12 2009-01-15 Sumitomo Chemical Company, Limited Procédé de fabrication d'un composant électroluminescent organique
WO2009069820A1 (fr) 2007-11-29 2009-06-04 Sumitomo Chemical Company, Limited Dispositif électroluminescent organique et son procédé de fabrication
WO2009084590A1 (fr) 2007-12-28 2009-07-09 Sumitomo Chemical Company, Limited Dispositif électroluminescent à polymère, son procédé de fabrication et dispositif d'affichage électroluminescent à polymère
EP2107076A1 (fr) 2002-03-15 2009-10-07 Sumitomo Chemical Company, Limited Polymères conjuguées contenant unités de dibenzothiophene ou de dibenzofuran et utilisation en PLEDs
WO2010041559A1 (fr) 2008-10-06 2010-04-15 住友化学株式会社 Composé polymère contenant une structure hétérocyclique contenant de l'azote et composition, solution, film mince et élément électroluminescent polymère contenant chacun celui-ci
WO2010087510A1 (fr) 2009-01-29 2010-08-05 住友化学株式会社 Composé de masse moléculaire élevée et élément émettant de la lumière l'utilisant
WO2010100232A2 (fr) 2009-03-05 2010-09-10 Basf Se Formulation de dérivés d'astaxanthine et leur utilisation iii
WO2010100229A1 (fr) 2009-03-05 2010-09-10 Basf Se Compositions pulvérulentes de dérivés d'astaxanthine ii
WO2011049241A1 (fr) 2009-10-22 2011-04-28 住友化学株式会社 Élément électroluminescent organique
EP2325225A1 (fr) 2002-10-30 2011-05-25 Sumitomo Chemical Company, Limited Composés de copolymère d'aryle et dispositif électroluminescents à polymère fabriqués à partir de ceux-ci
WO2011093428A1 (fr) 2010-01-28 2011-08-04 住友化学株式会社 Composé polymère et dispositif électroluminescent l'utilisant
US8039041B2 (en) 1996-07-29 2011-10-18 Cambridge Display Technology, Ltd. Electroluminescent devices with electrode protection
CN103232473A (zh) * 2013-04-22 2013-08-07 南京邮电大学 一种芴基有机框架材料及其制备和应用方法
WO2013178975A1 (fr) * 2012-05-28 2013-12-05 Cambridge Display Technology Limited Dispositif électroluminescent organique à anode métallique et couche d'injection de trous polymère

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997032452A1 (fr) * 1996-02-29 1997-09-04 Uniax Corporation Longue duree de vie pour diodes electroluminescentes polymeres
WO1997033323A1 (fr) * 1996-03-04 1997-09-12 Uniax Corporation Polyfluorenes constituant des materiaux pour la photoluminescence et l'electroluminescence
EP0813212A2 (fr) * 1996-06-10 1997-12-17 Nippon Shokubai Co., Ltd. Polyaniline électriquement conductrice et soluble dans l'eau et méthode de fabrication de celle-ci et agent antistatique utilisant un polymère électriquement conducteur soluble dans l'eau
WO1998005187A1 (fr) * 1996-07-29 1998-02-05 Cambridge Display Technology Limited Dispositifs electroluminescents avec protection d'electrode
US5777070A (en) * 1997-10-23 1998-07-07 The Dow Chemical Company Process for preparing conjugated polymers
EP0949850A1 (fr) * 1998-04-02 1999-10-13 Cambridge Display Technology Limited Supports flexibles pour dispositif organique

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997032452A1 (fr) * 1996-02-29 1997-09-04 Uniax Corporation Longue duree de vie pour diodes electroluminescentes polymeres
WO1997033323A1 (fr) * 1996-03-04 1997-09-12 Uniax Corporation Polyfluorenes constituant des materiaux pour la photoluminescence et l'electroluminescence
EP0813212A2 (fr) * 1996-06-10 1997-12-17 Nippon Shokubai Co., Ltd. Polyaniline électriquement conductrice et soluble dans l'eau et méthode de fabrication de celle-ci et agent antistatique utilisant un polymère électriquement conducteur soluble dans l'eau
WO1998005187A1 (fr) * 1996-07-29 1998-02-05 Cambridge Display Technology Limited Dispositifs electroluminescents avec protection d'electrode
US5777070A (en) * 1997-10-23 1998-07-07 The Dow Chemical Company Process for preparing conjugated polymers
EP0949850A1 (fr) * 1998-04-02 1999-10-13 Cambridge Display Technology Limited Supports flexibles pour dispositif organique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CARTER S A ET AL: "Polymeric anodes for improved polymer light-emitting diode performance", APPLIED PHYSICS LETTERS, vol. 70, no. 16, 21 April 1997 (1997-04-21), pages 2067 - 2069 2069, XP002110222, ISSN: 0003-6951 *

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8039041B2 (en) 1996-07-29 2011-10-18 Cambridge Display Technology, Ltd. Electroluminescent devices with electrode protection
WO2001099208A3 (fr) * 2000-06-20 2002-05-02 Uniax Corp Traitement thermique d'une couche electroactive organique traitee par une solution dans un dispositif electronique organique
WO2001099192A3 (fr) * 2000-06-20 2003-01-16 Uniax Corp Polymeres conducteurs haute resistance, utilises dans des dispositifs electroniques organiques pixelises a haut rendement
US7504655B2 (en) 2000-06-20 2009-03-17 E. I. Du Pont De Nemours & Company Multilayer structures as stable hole-injecting electrodes for use in high efficiency organic electronic devices
WO2001099207A3 (fr) * 2000-06-20 2002-04-18 Uniax Corp Structures multicouches en tant qu'electrodes stables d'injection de trous a utiliser dans des dispositifs electroniques organiques a haute efficacite
US7319440B2 (en) 2001-09-19 2008-01-15 Osram Opto Semiconductors Gmbh Organic light emitting diode light source
US6680578B2 (en) 2001-09-19 2004-01-20 Osram Opto Semiconductors, Gmbh Organic light emitting diode light source
US7112368B2 (en) 2001-11-06 2006-09-26 E. I. Du Pont De Nemours And Company Poly(dioxythiophene)/poly(acrylamidoalkyslufonic acid) complexes
EP2107076A1 (fr) 2002-03-15 2009-10-07 Sumitomo Chemical Company, Limited Polymères conjuguées contenant unités de dibenzothiophene ou de dibenzofuran et utilisation en PLEDs
US7056600B2 (en) * 2002-08-23 2006-06-06 Agfa Gevaert Layer configuration comprising an electron-blocking element
US6977390B2 (en) 2002-08-23 2005-12-20 Agfa Gevaert Layer configuration comprising an electron-blocking element
WO2004019346A1 (fr) * 2002-08-23 2004-03-04 Agfa-Gevaert Configuration de couche comprenant un element de blocage d'electrons
US7307276B2 (en) 2002-08-23 2007-12-11 Agfa-Gevaert Layer configuration comprising an electron-blocking element
EP2325224A1 (fr) 2002-10-30 2011-05-25 Sumitomo Chemical Company, Limited Composés de copolymère d'aryle et dispositif électroluminescents à polymère fabriqués à partir de ceux-ci
EP2325226A1 (fr) 2002-10-30 2011-05-25 Sumitomo Chemical Company, Limited Composés de copolymère d'aryle et dispositif électroluminescents à polymère fabriqués à partir de ceux-ci
EP2325223A1 (fr) 2002-10-30 2011-05-25 Sumitomo Chemical Company, Limited Composés de copolymère d'aryle et dispositif électroluminescents à polymère fabriqués à partir de ceux-ci
EP2325225A1 (fr) 2002-10-30 2011-05-25 Sumitomo Chemical Company, Limited Composés de copolymère d'aryle et dispositif électroluminescents à polymère fabriqués à partir de ceux-ci
DE112006002147T5 (de) 2005-08-12 2008-10-23 Sumitomo Chemical Co., Ltd. Polymerverbindung und polymere lichtemittierende Vorrichtung diese verwendend
DE112006002668T5 (de) 2005-10-07 2008-08-14 Sumitomo Chemical Company, Ltd. Copolymer und polymere lichtemittierende Vorrichtung unter Verwendung desselben
DE112006003090T5 (de) 2005-11-11 2008-09-25 Sumitomo Chemical Co. Ltd. Konjugierte Polymerverbindung und polymere lichtemittierende Vorrichtung unter deren Verwendung
DE112006002998T5 (de) 2005-11-18 2008-09-18 Sumitomo Chemical Co., Ltd. Polymerverbindung und Polymer enthaltende Licht ermittierende Vorrichtung, die diese verwendet
DE112006003570T5 (de) 2005-12-28 2008-11-06 Sumitomo Chemical Co., Ltd. Blockcopolymer
WO2008026649A1 (fr) 2006-08-30 2008-03-06 Sumitomo Chemical Company, Limited Élément à électroluminescence organique
WO2008032843A1 (fr) 2006-09-14 2008-03-20 Sumitomo Chemical Company, Limited Dispositif électroluminescent organique
WO2008136492A1 (fr) 2007-04-27 2008-11-13 Sumitomo Chemical Company, Limited Polymère de pyrène et élément luminescent fabriqué avec ce polymère
WO2008149829A1 (fr) 2007-05-30 2008-12-11 Sumitomo Chemical Company, Limited Dispositif électroluminescent organique et dispositif d'affichage utilisant ce dispositif
WO2009008543A1 (fr) 2007-07-12 2009-01-15 Sumitomo Chemical Company, Limited Procédé de fabrication d'un composant électroluminescent organique
WO2009069820A1 (fr) 2007-11-29 2009-06-04 Sumitomo Chemical Company, Limited Dispositif électroluminescent organique et son procédé de fabrication
WO2009084590A1 (fr) 2007-12-28 2009-07-09 Sumitomo Chemical Company, Limited Dispositif électroluminescent à polymère, son procédé de fabrication et dispositif d'affichage électroluminescent à polymère
WO2010041559A1 (fr) 2008-10-06 2010-04-15 住友化学株式会社 Composé polymère contenant une structure hétérocyclique contenant de l'azote et composition, solution, film mince et élément électroluminescent polymère contenant chacun celui-ci
WO2010087510A1 (fr) 2009-01-29 2010-08-05 住友化学株式会社 Composé de masse moléculaire élevée et élément émettant de la lumière l'utilisant
WO2010100232A2 (fr) 2009-03-05 2010-09-10 Basf Se Formulation de dérivés d'astaxanthine et leur utilisation iii
WO2010100229A1 (fr) 2009-03-05 2010-09-10 Basf Se Compositions pulvérulentes de dérivés d'astaxanthine ii
WO2011049241A1 (fr) 2009-10-22 2011-04-28 住友化学株式会社 Élément électroluminescent organique
WO2011093428A1 (fr) 2010-01-28 2011-08-04 住友化学株式会社 Composé polymère et dispositif électroluminescent l'utilisant
WO2013178975A1 (fr) * 2012-05-28 2013-12-05 Cambridge Display Technology Limited Dispositif électroluminescent organique à anode métallique et couche d'injection de trous polymère
CN103232473A (zh) * 2013-04-22 2013-08-07 南京邮电大学 一种芴基有机框架材料及其制备和应用方法

Similar Documents

Publication Publication Date Title
WO2000006665A1 (fr) Dispositifs electroluminescents organiques
EP0988337B1 (fr) Polymeres contenant du fluorene et dispositifs electroluminescents obtenus a partir de ceux-ci
US5986400A (en) Electroluminescent device comprising a transparent structured electrode layer made from a conductive polymer
CN101622731B (zh) 在光电器件中的传导聚合物组合物
US7531831B2 (en) Electroluminescent device comprising a cross-linked hole transporting and electron blocking material
JP3724589B2 (ja) エレクトロルミネセンス素子
EP1537612B1 (fr) Procédé de formation d'un dispositif optique
WO1999054943A1 (fr) Dispositifs electroluminescents organiques a stabilite amelioree dans l'air
Elschner et al. Gallium Complexes in Three‐Layer Organic Electroluminescent Devices
WO2001018888A1 (fr) Dispositifs electroniques organiques presentant des couches tampon polymeres auto-dopees conductrices
CN101911334A (zh) 发光器件及其使用的材料
CN101107884A (zh) 电致发光材料和器件
WO2007129015A1 (fr) Polymères et dispositifs opto-électriques
GB2539507A (en) Light emitting composition and device
Rao et al. Solution-processed cesium carbonate doped electron transport layer for multilayered polymer light emitting devices
US11555146B2 (en) Fluorescent infrared emitting composition
JP2004107614A (ja) フェナントロリン構造を有する高分子、該高分子の製造方法、該高分子からなる電子輸送性材料、該電子輸送性材料の製造方法、該電子輸送性材料を含む有機発光素子及び該発光素子の製造方法
TRANSPARENT et al. Staring et 81.
HK1077921B (en) Method of forming an optical device
HK1085053B (en) Electroluminescent device

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA CN JP KR SG

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase