EP1730797A2 - Diode electroluminescente organique et ses utilisations - Google Patents

Diode electroluminescente organique et ses utilisations

Info

Publication number
EP1730797A2
EP1730797A2 EP05747924A EP05747924A EP1730797A2 EP 1730797 A2 EP1730797 A2 EP 1730797A2 EP 05747924 A EP05747924 A EP 05747924A EP 05747924 A EP05747924 A EP 05747924A EP 1730797 A2 EP1730797 A2 EP 1730797A2
Authority
EP
European Patent Office
Prior art keywords
organic light
emitting diode
units
organic
diode according
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP05747924A
Other languages
German (de)
English (en)
Inventor
Karsten Heuser
Arvid Hunze
Andreas Kanitz
Wolfgang Rogler
Debora Henseler
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ams Osram International GmbH
Original Assignee
Osram Opto Semiconductors GmbH
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 Osram Opto Semiconductors GmbH filed Critical Osram Opto Semiconductors GmbH
Publication of EP1730797A2 publication Critical patent/EP1730797A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • 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
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H10K50/165—Electron transporting layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/30—Doping active layers, e.g. electron transporting layers
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/114—Poly-phenylenevinylene; Derivatives thereof

Definitions

  • the invention relates to an organic light-emitting diode (OLED) with improved service life and improved transport of negative charge carriers.
  • OLED organic light-emitting diode
  • OLEDs based on semiconducting material with, for example, a backbone of polyarylene vinylene or polyparaphenylene (in particular polyfluorene and / or polyspirofluorene) are known in which, in addition to these constituents, proportions of other chromophores and / or triarylamine derivatives are also polymerized or in the form brought in by blends.
  • the chromophores generally produce strong long-wave, that is to say essentially green or red, emission bands in the resulting electroluminescence spectra.
  • the triarylamin units typically have a minor influence on the emission spectrum of the organic light-emitting diodes and serve primarily to transport positive charges via the conjugated polymer chain and / or the oxidation stability of the organic semiconducting material.
  • Polymer OLEDs represent the reduction stability of the semiconducting, organic material. end because in an organic semiconducting material the charge transport is effected via individual oxidations and reductions, a subunit involved in charge transport typically having to be oxidized or reduced many billions of times during the operating life of the component. An irreversible chemical degradation during such a process leads to a deterioration in the charge transport properties and at the same time a decrease in the luminance.
  • the object of the present invention is therefore to create an organic light-emitting diode with an increased redox stability of the semiconducting organic material, so that it has an extended operating life.
  • the invention relates to an organic light emitting diode or light display with an organic semiconducting material of an active layer, into which at least partially triaryl-substituted Lewis acid units are polymerized and / or admixed in the form of blends as a polymer component.
  • the invention also relates to the use of the organic light-emitting diode for lighting purposes and / or for monochrome, multicolor or full-color organic light-emitting displays based on color filters or structured, RGB-pixelated emitter layers, and for passive matrix displays.
  • An organic light-emitting diode comprises at least one substrate, a transparent lower electrode layer, at least one active layer and an upper electrode layer.
  • the organic light-emitting diode is advantageously encapsulated against undesirable environmental influences.
  • polymerized in and / or admixed in the form of blends as a polymer component means that the triaryl-substituted Lewis acid units are either in a copolymer with other units such as polya- rylene vinylene or polyp raphenylene (especially polyfluorene and / or poly-spiro-fluorene) units are copolymerized or there is a blend in which the triaryl-substituted Lewis acid units are mixed as a polymer with at least one other polymeric organic semiconducting material (blended) has been.
  • the two alternatives can also be present together at the same time, so that on the one hand there is a blend of several polymers, including a polymer comprising triaryl-substituted Lewis acid units, and on the other hand there is a copolymer with a repeating unit comprising a triaryl-substituted Lewis acid ,
  • the triarylic acid units improve the transport of negative charge carriers and increase the stability of the polymer with respect to electrochemical reduction, which inevitably occurs when the negative charge carriers are transported.
  • Lewis acid is an electron pair acceptor, i.e. a molecule or ion with an incomplete electron configuration that can hold a pair of electrons, ie a negative charge.
  • Triaryl-leic acid units are particularly suitable for use as electron-transporting components of a copolymeric organic semiconducting material, because this component can not only take up a negative charge, but also stabilize it through the aryl radicals.
  • Suitable Lewis acids are, for example, those which have a boron or an aluminum atom as the central atom, the aluminum Lewis acids in question also having a complex backbond to the aromatic system for reasons of stability.
  • Tri-aryl Lewis acids with boron as the central atom are particularly suitable because a boranate anion is stable to reduction.
  • no irreversible secondary reactions are to be expected here. This concept is supported, for example, by cyclic voltammetry Measurements on trimesitylborane confirmed that show a completely reversible reduction of the triarylborane unit.
  • triaryl-Lewis acid units as a stable electron transport unit can be used for negative charges analogously to the already known use of triarylamine derivatives as a stable hole transport unit for positive charges.
  • the negative or positive charge carriers on the Lewis acid central or nitrogen atoms are stabilized, charge transport to the next stabilizing subunit is nevertheless possible via the conjugation of the carbon skeleton.
  • the triarylated Lewis acid units are advantageously borane units.
  • the aryl substituents can be the same or different.
  • Aryl substituents are understood to mean (homo) aromatic or heteroaromatic compounds. As a rule, at least two of the three aryl substituents will be part of the main polymer chain, so that the polymer main chain of at least one polymeric component of the organic semiconducting material has a component -Ar-B (Ar) -Ar-.
  • the organic semiconducting material comprises at least one active layer of the OLED 50% of the repeating units of arylene vinylene and / or para-phenylene derivative units and between 1 and 50% of the repeating units, preferably 1 to 30% and particularly preferably 1 to 20% triaryl substituted Lewis acid units. It is particularly preferred if the para-phenylene derivative units used are fluorene derivative units and / or poly-spirofluorene units. According to a further embodiment, the organic semiconducting material at least one active layer of the OLED also comprises between 1 and 49% of repeating units of triarylamine de-civat units, in particular from 1 to
  • the triarylated Lewis acid units show a blue emission in the organic semiconducting material or they have no noticeable influence on the emission spectrum (shift less than 30 nm).
  • the triarylided Lewis acid units are electron donated, so that a chromophore center is formed and the emission is shifted into the long-wave range.
  • triarylamine and borane units are combined in an organic semiconducting material trial of at least one active layer in such a way that efficiency and service life are optimized for specific driver conditions, e.g. for passive matrix updates at a given multiplex rate, pulse frequency and / or brightness.
  • the proportion of negative charge carriers in the total current and thus the efficiency of the organic light-emitting diode and the position of the recombination zone within the layer can be optimized by using triarylborane electron transporter units.
  • the triaryllic acid (for example the tri-arylborane) units do not significantly influence the electroluminescence of the semiconducting copolymer, so that despite these additional electron-transporting components the emission of the Polyarylene vinylene or poly-para-phenylene backbone and the emission of any chromophore components present dominate the spectrum.
  • the triaryl ligand on the Lewis acid central atom can also be electron donor-substituted, which means that this unit can then be changed into a chromophore center with long-wavelength shifted emission. Then OLEDs with such a structure emit in a broadband changed emission.
  • the organic light emitting diode or light display can be used for monochrome, multicolor or full color organic electroluminescent displays with active or passive matrix control.
  • it can be used for full-color organic electroluminescent displays on the basis of white emitters and color filters or on the basis of structured RGB-pixelated emitter layers.
  • the OLED according to the invention can be used in such a way that the content of the Lewis acid units is matched to the pulsed driver conditions in a passive matrix display.
  • the invention for the first time provides an organic light-emitting diode with a triaryl-Lewis acid component as an electron-transporting unit in an organic semiconducting material of an active layer, in which the problem of the insufficient reduction stability of conjugated carbon-hydrogen polymers is overcome.
  • the perarylated Lewis acid units ensure that the entire organic semiconducting material than the active layer and thus an extended life of the LED during operation.
  • an improved efficiency and / or a control of the position of the emission zone within the active layer made of organic semiconducting material is possible through targeted variation of the proportion of, for example, tri-arylborane units as triaryl-Lewis acid units.
  • the invention relates to an organic light-emitting diode (OLED) with improved service life and improved transport of negative charge carriers.
  • OLED organic light-emitting diode
  • the organic light-emitting diode based on an organic semiconducting material in which the transport of negative charge carriers and the stability with regard to reduction are determined by triarylated Lewis acid units, in particular by perarylated borane units.
  • triarylated Lewis acid units in particular by perarylated borane units.
  • the invention relates to organic light-emitting diodes in which the position of the emission zone in the emitter layer and the color of the emission can be influenced in a targeted manner by triarylated Lewis acids such as perarylated borane units.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Manufacturing & Machinery (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)

Abstract

L'invention concerne une diode électroluminescente organique (OLED) à durée de vie améliorée et à transport amélioré du porteur de charge négatif. La diode électroluminescente organique est à base d'un matériau semi-conducteur organique dans lequel le transport du porteur de charge négatif et la stabilité de réduction sont déterminés par des motifs acide de Lewiss triarylés, en particulier par des motifs borane perarylés. Ceci permet d'obtenir une durée de vie améliorée de la couche d'émission, ce qui augmente la durée de vie du composant et évite le réglage ultérieur de la luminosité au cours du fonctionnement. En outre, l'invention concerne les diodes électroluminescentes organiques précitées dans lesquelles la position de la zone d'émission dans la couche émettrice, et la couleur de l'émission peuvent être modifiées de manière appropriée par des acides de Lewiss triarylés, tels que des motifs borane perarylés.
EP05747924A 2004-03-31 2005-03-23 Diode electroluminescente organique et ses utilisations Withdrawn EP1730797A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004015845A DE102004015845B4 (de) 2004-03-31 2004-03-31 Organische Leuchtdiode, sowie Verwendungen davon
PCT/EP2005/051349 WO2005096402A2 (fr) 2004-03-31 2005-03-23 Diode electroluminescente organique et ses utilisations

Publications (1)

Publication Number Publication Date
EP1730797A2 true EP1730797A2 (fr) 2006-12-13

Family

ID=34965766

Family Applications (1)

Application Number Title Priority Date Filing Date
EP05747924A Withdrawn EP1730797A2 (fr) 2004-03-31 2005-03-23 Diode electroluminescente organique et ses utilisations

Country Status (7)

Country Link
US (1) US8580392B2 (fr)
EP (1) EP1730797A2 (fr)
JP (1) JP2007531993A (fr)
KR (1) KR101282049B1 (fr)
CN (1) CN1938877B (fr)
DE (1) DE102004015845B4 (fr)
WO (1) WO2005096402A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004036496A1 (de) 2004-07-28 2006-03-23 Siemens Ag Organische Leuchtdiode mit erhöhter Radikalanionenstabilität, sowie Verwendungen davon
US20070215864A1 (en) 2006-03-17 2007-09-20 Luebben Silvia D Use of pi-conjugated organoboron polymers in thin-film organic polymer electronic devices

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001284052A (ja) * 2000-04-04 2001-10-12 Matsushita Electric Ind Co Ltd 有機発光素子

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4055363B2 (ja) * 1999-01-08 2008-03-05 チッソ株式会社 ボラン誘導体および有機電界発光素子
JP4023204B2 (ja) * 2001-05-02 2007-12-19 淳二 城戸 有機電界発光素子
US6597012B2 (en) * 2001-05-02 2003-07-22 Junji Kido Organic electroluminescent device
GB0111549D0 (en) * 2001-05-11 2001-07-04 Cambridge Display Tech Ltd Polymers, their preparation and uses
GB0125622D0 (en) * 2001-10-25 2001-12-19 Cambridge Display Tech Ltd Method of polymerisation
JP4196747B2 (ja) 2002-06-26 2008-12-17 住友化学株式会社 高分子化合物およびそれを用いた高分子発光素子
WO2004003053A1 (fr) * 2002-06-26 2004-01-08 Sumitomo Chemical Company, Limited Polymere et element luminescent polymere comprenant ce polymere
US7951874B2 (en) * 2003-05-08 2011-05-31 Osram Opto Semiconductors Gmbh Non-conjugated polymeric perarylated boranes, use thereof as organically semiconductor transmitters and/or transport materials, methods for producing same and uses thereof
DE102004001865A1 (de) * 2003-05-08 2004-12-16 Siemens Ag Nicht konjugierte polymere perarylierte Borane, deren Verwendung als organisch halbleitende Emitter und/oder Transportmaterialien, Verfahren zu deren Herstellung und Anwendungen davon
JP2005093428A (ja) * 2003-08-14 2005-04-07 Mitsubishi Chemicals Corp 有機電界発光素子用組成物及び有機電界発光素子
JP2005093427A (ja) 2003-08-14 2005-04-07 Mitsubishi Chemicals Corp 有機電界発光素子用組成物及び有機電界発光素子の製造方法
US20060182993A1 (en) * 2004-08-10 2006-08-17 Mitsubishi Chemical Corporation Compositions for organic electroluminescent device and organic electroluminescent device

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001284052A (ja) * 2000-04-04 2001-10-12 Matsushita Electric Ind Co Ltd 有機発光素子

Also Published As

Publication number Publication date
WO2005096402A2 (fr) 2005-10-13
US20090289544A1 (en) 2009-11-26
JP2007531993A (ja) 2007-11-08
WO2005096402A3 (fr) 2005-11-24
CN1938877B (zh) 2012-11-14
KR101282049B1 (ko) 2013-07-04
CN1938877A (zh) 2007-03-28
US8580392B2 (en) 2013-11-12
DE102004015845A1 (de) 2005-11-03
KR20060135050A (ko) 2006-12-28
DE102004015845B4 (de) 2012-12-20

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