EP1652410A1 - Utilisation d'une couche formee d'aromates hydrophobes, polycycliques lineaires ou bidimensionnels, comme couche d'arret ou de blindage, et composants electriques dotes d'une couche de ce type et de polymeres organiques - Google Patents

Utilisation d'une couche formee d'aromates hydrophobes, polycycliques lineaires ou bidimensionnels, comme couche d'arret ou de blindage, et composants electriques dotes d'une couche de ce type et de polymeres organiques

Info

Publication number
EP1652410A1
EP1652410A1 EP04762620A EP04762620A EP1652410A1 EP 1652410 A1 EP1652410 A1 EP 1652410A1 EP 04762620 A EP04762620 A EP 04762620A EP 04762620 A EP04762620 A EP 04762620A EP 1652410 A1 EP1652410 A1 EP 1652410A1
Authority
EP
European Patent Office
Prior art keywords
layer
metal
groups
hil
injecting
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Withdrawn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
EP04762620A
Other languages
German (de)
English (en)
Inventor
Thomas Dobbertin
Wolfgang Kowalsky
Hans-Hermann Johannes
Eike Becker
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.)
Technische Universitaet Braunschweig
Original Assignee
Technische Universitaet Braunschweig
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
Priority claimed from DE10339629A external-priority patent/DE10339629B4/de
Application filed by Technische Universitaet Braunschweig filed Critical Technische Universitaet Braunschweig
Publication of EP1652410A1 publication Critical patent/EP1652410A1/fr
Withdrawn legal-status Critical Current

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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • 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
    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • C09K2211/187—Metal complexes of the iron group metals, i.e. Fe, Co or Ni
    • 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
    • C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/301—Details of OLEDs
    • H10K2102/302—Details of OLEDs of OLED structures
    • H10K2102/3023—Direction of light emission
    • H10K2102/3031—Two-side emission, e.g. transparent OLEDs [TOLED]
    • 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
    • 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
    • H10K50/171—Electron injection 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
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/844—Encapsulations
    • 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
    • H10K85/311—Phthalocyanine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]

Definitions

  • the optically active layer is expediently composed of several layers, at least one layer specifically for hole formation (hole injection layer, HIL) or for hole conduction (hole transport layer, HTL) and another layer are trained in particular for electron release layer (EIL), for electron transport layer (ETL) or for light emission (emission layer, EML).
  • the known structure of such OLEDs provides a glass substrate on which a transparent anode made of a transparent conductive oxide
  • TCO indium tin oxide
  • HIL indium tin oxide
  • EML EML
  • ETL ETL
  • EIL metallic cathode
  • OLEDs of the known type are either made only from layers of different small molecules (SM-OLED, small molecule OLED) or from different polymers (PM- OLED), the small molecules are successively applied as thin layers on the substrate by vacuum sublimation, whereas polymers are processed from a solution (water or organic solvent), polymer layers offer particular advantages as HIL and HTL, since they show good hole transport properties
  • SM-OLED small molecule OLED
  • PM- OLED polymers
  • HIL and HTL since they show good hole transport properties
  • Molecules which are suitable as HILs are, for example, anthracene, tetracene and pentacene (cf. EP 0 278 758 B1).
  • the layers of the OLEDs are highly susceptible to moisture, so that after the application of the second electrode, the OLEDs are encapsulated in such a way that only connections of the electrodes are accessible.
  • Small molecules are therefore organic molecules that do not form chains or networks through polymerization.
  • the present invention is therefore based on the object of eliminating or at least reducing the restrictions on the structure of electrical components made of organic substances due to moisture sensitivity and diffusion phenomena.
  • This object is surprisingly achieved by using a layer of hydrophobic, linear or two-dimensional polycyclic aromatics with three to twelve ring structures, including metal-containing or metal-free phthalocyanines, which are residual groups - H and / or -F, alkyl groups, aryl groups and / or fluorinated hydrocarbons have, as a barrier layer in or as an encapsulation of electrical components constructed with organic layers.
  • the present invention is based on the knowledge that the layers mentioned, in particular and preferably made of pentacene, can not only be a functional layer in the construction of organic electrical components, but also unexpectedly has barrier properties which make it possible to counteract the corresponding layer as a barrier layer Use moisture to protect the underlying layers and the metallic cathode.
  • the layer used according to the invention is preferably made of a material from the group consisting of anthracene, phenanthrene, tetracene, chrysene, pentacene, hexacene, perylene, triphenylene, corones, m-naphthodianthracene, m-anthracenoditetracene, m-tetracenodipentacene, pyrene, benzopyrene, ovals, violanthrene and Derivatives of the aforementioned substances with residual groups -H and / or -F, alkyl groups, aryl groups and / or fluorinated hydrocarbons is formed.
  • each R is an -H and / or -F and / or an alkyl group and / or an aryl group and / or a can be fluorinated hydrocarbon. In all cases it is preferred if the number of ring structures of the aromatic is between 5 and 10, preferably between 4 and 10, preferably between 5 and 8.
  • organic electrical components can be constructed in which the layer both fulfills an electrical function and is constructed as a barrier layer or as an in-situ encapsulation.
  • an organic light-emitting diode with a substrate, a first electrode applied to the substrate, at least one electron-injecting and transporting zone, at least one hole-injecting and transporting zone and a second electrode is characterized in that the hole-injecting and transporting zone is a layer of linear or two-dimensionally linked polycyclic aromatics with 3 to 12 ring structures, including metal-containing or metal-free phthalocyanines which have -H and / or -F, alkyl groups, aryl groups and / or fluorinated hydrocarbons as residual groups, this layer being designed as an encapsulation layer.
  • the layer structure is designed so that the layer covers all moisture-sensitive layers that have been built up beforehand.
  • the invention further enables an organic light-emitting diode with a substrate, a cathode applied to the substrate, at least one electron-injecting and transporting zone, at least a hole-injecting and transporting zone and a translucent anode, the electron-injecting and transporting zone being built up with small molecules and attached to it a layer of linearly or two-dimensionally linked polycyclic aromatics with 3 to 12 ring structures, including metal-containing or metal-free phthalocyanines, which act as residual groups -H and / or -F, alkyl groups, aryl groups and / or fluorinated hydrocarbons connected to the anode.
  • the present invention therefore also enables an organic light-emitting diode (OLED) constructed in a hybrid structure, in which the radiation is “upward”, that is to say away from the substrate side.
  • OLED organic light-emitting diode
  • the invention enables an optimized structure of an upward-radiating OLED because the said layer acts as an effective barrier layer which prevents the diffusion of water into the layers below it.
  • an aqueous polymer film for example made of PDOT: PSS, can preferably be applied to the said layer as an additional hole-injecting layer towards the anode to reduce the required operating voltage of the OLED.
  • Examples of substances from which the layer serving as a barrier layer or encapsulation according to the invention can be formed are: anthracene
  • R H and / or F and / or alkyl, aryl, and / or fluorinated r ⁇ ⁇ ⁇ ci iw Döci oiunc;
  • FIG. 1 shows a schematic structure of an “upward” emitting OLED with an HIL layer as the encapsulation layer, all layers being constructed as SM layers.
  • Figure 2 shows a schematic structure of an OLED with a hybrid structure of SM layers and a polymer layer.
  • the OLEDs shown in FIGS. 1 and 2 emit upwards. They consist of a substrate 1 on which a metal layer as cathode 2 is applied.
  • a suitable metal layer is magnesium or an alloy of LiF / Al.
  • An electron-injecting layer EIL adjoins the cathode 2 and provides free electrons in a known manner. These recombine with holes from the other layers explained in more detail below in an emission layer EML, in which electroluminescence is produced by the recombination, that is to say light is emitted.
  • HTLs There may be several hole-conducting layers HTLs above the emission layer EML. These are covered by a jicant layer HIL 1, which can be formed from pentacene in the illustrated embodiment. This layer is used as an encapsulation layer in that it is formed in the real construction in such a way that it covers the other layers below.
  • the HIL 1 is followed by a transparent anode 3, which preferably consists of indium tin oxide.
  • the layers EIL, EML, HTL and HIL 1 are formed in a known manner as thin layers and emit light when a sufficient voltage relative to the cathode 2 is applied to the anode 3.
  • the upward emission is illustrated in Figure 1 by an arrow.
  • HIL 1 layer as an encapsulation layer eliminates the need to subsequently (ex-situ) encapsulate the OLED.
  • the OLED according to the invention according to FIG. 1 is therefore encapsulated in situ, so that subsequent encapsulation can be carried out in a much simpler manner due to the reduced requirements with regard to its permeability to water vapor.
  • the structure of the OLED shown in FIG. 2 is basically the same, the layers EIL, EML, HTL and HIL 1 all consisting of small molecules (as SM layers).
  • a layer HIL 2 is also applied, which is designed as a polymer layer, for example PDOT.
  • This polymer layer HIL 2 is applied wet, but does not damage the underlying moisture-sensitive layers HTL, EML and EIL because of the barrier layer effect of HIL 1.
  • the layer HIL 2 enables the working voltage between the anode 3 and the cathode 2 to be reduced or increases the efficiency of the emission, which also takes place upward in the exemplary embodiment according to FIG. 2.
  • the layer HIL 1 can also be formed as an encapsulation layer in this exemplary embodiment, that is to say cover the layers HTL, EML and EIL underneath.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un composant électrique formé de couches organiques dont une couche d'arrêt ou de blindage composée d'un aromate hydrophobe, polycyclique linéaire ou bidimensionnel, avec 3 à 12 structures cycliques, y compris des phtalocyanines avec ou sans métal, comportant comme groupes résiduels des groupes H et/ou F, des groupes alkyle, des groupes aryle et/ou des hydrocarbures fluorés. Il est ainsi possible d'obtenir des structures hybrides comprenant des couches SM et des couches polymères, un blindage ultérieur du composant étant en outre superflu.
EP04762620A 2003-08-05 2004-08-04 Utilisation d'une couche formee d'aromates hydrophobes, polycycliques lineaires ou bidimensionnels, comme couche d'arret ou de blindage, et composants electriques dotes d'une couche de ce type et de polymeres organiques Withdrawn EP1652410A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10336531 2003-08-05
DE10339629A DE10339629B4 (de) 2003-08-05 2003-08-28 Verwendung einer Schicht aus hydrophoben, linear oder zweidimensional polyzyklischen Aromaten als Sperrschicht oder Kapselung und mit einer derartigen Schicht aufgebaute elektrische Bauelemente mit organischen Polymeren
PCT/DE2004/001775 WO2005015959A1 (fr) 2003-08-05 2004-08-04 Utilisation d'une couche formee d'aromates hydrophobes, polycycliques lineaires ou bidimensionnels, comme couche d'arret ou de blindage, et composants electriques dotes d'une couche de ce type et de polymeres organiques

Publications (1)

Publication Number Publication Date
EP1652410A1 true EP1652410A1 (fr) 2006-05-03

Family

ID=34137315

Family Applications (1)

Application Number Title Priority Date Filing Date
EP04762620A Withdrawn EP1652410A1 (fr) 2003-08-05 2004-08-04 Utilisation d'une couche formee d'aromates hydrophobes, polycycliques lineaires ou bidimensionnels, comme couche d'arret ou de blindage, et composants electriques dotes d'une couche de ce type et de polymeres organiques

Country Status (5)

Country Link
US (1) US20070166547A1 (fr)
EP (1) EP1652410A1 (fr)
JP (1) JP2007501510A (fr)
KR (1) KR20060113884A (fr)
WO (1) WO2005015959A1 (fr)

Cited By (1)

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US20140035314A1 (en) * 2012-08-01 2014-02-06 Henniges Automotive Sealing Systems North America, Inc. Dual end cap for a seal assembly

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WO2010011927A1 (fr) 2008-07-25 2010-01-28 Noventis, Inc. Compositions et procédés pour la prévention et le traitement de maladies cardiovasculaires
US8241749B2 (en) * 2008-09-11 2012-08-14 Fujifilm Corporation Barrier laminate, gas barrier film, and device using the same
US8277697B2 (en) * 2008-10-29 2012-10-02 Global Oled Technology Llc Color filter element with improved colorant dispersion
KR101311942B1 (ko) 2009-12-31 2013-09-26 제일모직주식회사 레지스트 하층막용 방향족 고리 함유 화합물 및 이를 포함하는 레지스트 하층막용　조성물
KR101253529B1 (ko) * 2010-06-29 2013-04-11 차혁진 봉지막 및 이를 포함하는 유기전자소자
BR112013001594A2 (pt) 2010-07-22 2016-05-17 Reven Pharmaceuticals Inc métodos de tratamento ou melhoria de doenças e para melhorar o desempenho compreendendo o uso de uma solução dipolo magnético estabilizada
KR20160119614A (ko) 2015-04-06 2016-10-14 주식회사 나노솔루션 유기발광표시장치용 봉지재 및 이를 사용한 유기발광표시장치의 제조방법

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Publication number Priority date Publication date Assignee Title
US20140035314A1 (en) * 2012-08-01 2014-02-06 Henniges Automotive Sealing Systems North America, Inc. Dual end cap for a seal assembly
US9038318B2 (en) * 2012-08-01 2015-05-26 Henniges Automotive Sealing Systems North America, Inc. Dual end cap for a seal assembly

Also Published As

Publication number Publication date
WO2005015959A1 (fr) 2005-02-17
KR20060113884A (ko) 2006-11-03
JP2007501510A (ja) 2007-01-25
US20070166547A1 (en) 2007-07-19

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