WO2008058929A1 - Neuartiges hochleitfähiges organisches ladungsträgertransportmaterial - Google Patents

Neuartiges hochleitfähiges organisches ladungsträgertransportmaterial Download PDF

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Publication number
WO2008058929A1
WO2008058929A1 PCT/EP2007/062210 EP2007062210W WO2008058929A1 WO 2008058929 A1 WO2008058929 A1 WO 2008058929A1 EP 2007062210 W EP2007062210 W EP 2007062210W WO 2008058929 A1 WO2008058929 A1 WO 2008058929A1
Authority
WO
WIPO (PCT)
Prior art keywords
transport material
charge carrier
carrier transport
organic
material 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.)
Ceased
Application number
PCT/EP2007/062210
Other languages
German (de)
English (en)
French (fr)
Inventor
Andreas Kanitz
Jürgen Adler
Ralf Krause
Günter Schmid
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.)
Siemens AG
Siemens Corp
Original Assignee
Siemens AG
Siemens Corp
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 Siemens AG, Siemens Corp filed Critical Siemens AG
Priority to KR20097012297A priority Critical patent/KR101482512B1/ko
Priority to DE502007005097T priority patent/DE502007005097D1/de
Priority to EP07822496A priority patent/EP2092041B9/de
Priority to US12/514,986 priority patent/US8309284B2/en
Priority to JP2009536713A priority patent/JP5193218B2/ja
Priority to AT07822496T priority patent/ATE481463T1/de
Priority to CN2007800422590A priority patent/CN101679850B/zh
Publication of WO2008058929A1 publication Critical patent/WO2008058929A1/de
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as 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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • 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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom

Definitions

  • the invention relates to an organic material, in particular a material which can be used as semiconductor material or conductive material in organic electronics.
  • Organic semiconductor materials are subdivided into hole and electron transport materials. These are required for the production of organic electronic components, such as organic light emitting diodes (OLEDs), organic field effect transistors (OFETs) and / or organic solar cells.
  • OLEDs organic light emitting diodes
  • OFETs organic field effect transistors
  • solar cells organic solar cells
  • the semiconducting properties of the materials are achieved by doping, because the base materials alone are never sufficiently conductive.
  • the object of the present invention is therefore to provide an organic electron transport material in which the bandwidth of the electron injection and also the stability in the electron-transporting, reduced state is improved compared to the known materials.
  • the invention relates to an organic charge carrier transport material with which electrons and holes can be transported equally well, with a measurable current density of greater than or equal to 0.5 A / cm 2 being obtained even at 0.25V in a 150 nm thick layer of the undoped material.
  • the invention relates to an organic semiconductive material comprising oligophenylenes of heterocyclic parent compounds of the following structure:
  • Oligophenylens which is organic in the most original sense, thus, containing only carbon, nitrogen and hydrogen, shows a purely organic materials (ie, only C, H and N containing structures) unusual property with an unprecedented many orders of magnitude conductivity in the electrons and holes are transported equally.
  • the layer is transparent, particularly preferably transparent in the entire visible spectral range.
  • the current density achieved here with the undoped material corresponds to a current density that has hitherto only been achieved by so-called doped systems.
  • this BPyPyP material can be used directly instead of an n-doped electron transport matrix to improve the injection of electrons from the cathode in an organic electronic device.
  • the BPyPyP material is deposited by covering vapor deposition with n-doping materials or N-type dopants as a still higher conductive layer. Since the BPyPyP material is an excellent electron transport, it can be used in all organic electronic devices and assemblies in this capacity.
  • the material can also be used in OLED arrangements as ambipolar matrix alone and in any blends for any emitter materials.
  • Substrates are generated which have anodic and / or cathodic function.
  • the excellent current transport seems to come about through a self-organizing ordering of the molecules by the vapor deposition process.
  • FIG. 1 shows the current-voltage characteristic, which shows how the conductivity of the material is in the positive and negative voltage field.
  • Figure 2 shows in the UV / VIS spectrum, the transparency of the material
  • FIG. 3 shows a photoluminescence spectrum of the compound.
  • a typical structure of an organic electronic device includes a substrate, a lower electrode, the semiconducting organic layer, and an upper anode. With a corresponding structure, the measured data contained in the figures were obtained.
  • the substrate was glass
  • the bottom electrode was indium tin oxide (ITO)
  • the semiconducting organic layer was 150 nm thick Layer of BPyPyP with top of a second electrode made of a 100 nm thick aluminum layer.
  • the invention relates to an organic semiconducting material, in particular a material which can be used as semiconductor material or conductive material in organic electronics.
  • a component of the material comprises the oligophenylene of heterocyclic parent compounds of the following structure:

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Photovoltaic Devices (AREA)
  • Led Devices (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Light Receiving Elements (AREA)
  • Liquid Deposition Of Substances Of Which Semiconductor Devices Are Composed (AREA)
PCT/EP2007/062210 2006-11-14 2007-11-12 Neuartiges hochleitfähiges organisches ladungsträgertransportmaterial Ceased WO2008058929A1 (de)

Priority Applications (7)

Application Number Priority Date Filing Date Title
KR20097012297A KR101482512B1 (ko) 2006-11-14 2007-11-12 신규한 고 전도성 유기 전하 캐리어 수송 물질
DE502007005097T DE502007005097D1 (de) 2006-11-14 2007-11-12 Neuartiges hochleitfähiges organisches ladungsträgertransportmaterial
EP07822496A EP2092041B9 (de) 2006-11-14 2007-11-12 Neuartiges hochleitfähiges organisches ladungsträgertransportmaterial
US12/514,986 US8309284B2 (en) 2006-11-14 2007-11-12 Highly conductive organic charge carrier transport material
JP2009536713A JP5193218B2 (ja) 2006-11-14 2007-11-12 新規の高導電性の有機電荷キャリア輸送材料
AT07822496T ATE481463T1 (de) 2006-11-14 2007-11-12 Neuartiges hochleitfähiges organisches ladungsträgertransportmaterial
CN2007800422590A CN101679850B (zh) 2006-11-14 2007-11-12 新型高导电性有机载流子输送材料

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006053644.4 2006-11-14
DE102006053644A DE102006053644A1 (de) 2006-11-14 2006-11-14 Neuartiges hochleitfähiges organisches Ladungsträgertransportmaterial

Publications (1)

Publication Number Publication Date
WO2008058929A1 true WO2008058929A1 (de) 2008-05-22

Family

ID=39034834

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/062210 Ceased WO2008058929A1 (de) 2006-11-14 2007-11-12 Neuartiges hochleitfähiges organisches ladungsträgertransportmaterial

Country Status (8)

Country Link
US (1) US8309284B2 (https=)
EP (1) EP2092041B9 (https=)
JP (1) JP5193218B2 (https=)
KR (1) KR101482512B1 (https=)
CN (1) CN101679850B (https=)
AT (1) ATE481463T1 (https=)
DE (2) DE102006053644A1 (https=)
WO (1) WO2008058929A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009047880A1 (de) 2009-09-30 2011-03-31 Osram Opto Semiconductors Gmbh Organische elektronische Vorrichtung und Verfahren zu dessen Herstellung

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2395571B1 (en) 2010-06-10 2013-12-04 Novaled AG Organic electronic device comprising an organic semiconducting material
DE102012205945A1 (de) 2012-04-12 2013-10-17 Siemens Aktiengesellschaft Organische Superdonoren mit mindestens zwei gekoppelten Carben-Gruppen und deren Verwendung als n-Dotierstoffe
DE102012217574A1 (de) 2012-09-27 2014-03-27 Siemens Aktiengesellschaft Phosphoroxo-Salze als n-Dotierstoffe für die organische Elektronik
DE102012217587A1 (de) 2012-09-27 2014-03-27 Siemens Aktiengesellschaft Salze des Cyclopentadiens als n-Dotierstoffe für die organische Elektronik
DE102015210388A1 (de) 2015-06-05 2016-12-08 Siemens Aktiengesellschaft Organische Heterozyklische Alkalimetallsalze als n-Dotierstoffe in der Organischen Elektronik
DE102016208298A1 (de) 2016-05-13 2017-11-16 Siemens Aktiengesellschaft Organische elektronenleitende Schicht mit n-Dotierstoff

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0690052A2 (de) * 1994-07-01 1996-01-03 Hoechst Aktiengesellschaft Verwendung von Pyrimidingruppen enthaltenden konjugierten Verbindungen als Elektrolumineszenzmaterialien

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6025973A (ja) * 1983-07-20 1985-02-08 Chisso Corp ピリミジン類
EP1063554B1 (en) 1994-12-28 2004-03-03 Seiko Epson Corporation Polarization luminaire and projector using it
CN1064046C (zh) * 1997-11-12 2001-04-04 南开大学戈德防伪技术公司 螺环类光致变色化合物及其制备方法
GB0225244D0 (en) * 2002-10-30 2002-12-11 Ciba Sc Holding Ag Electroluminescent device
KR100573137B1 (ko) * 2004-04-02 2006-04-24 삼성에스디아이 주식회사 플루오렌계 화합물 및 이를 이용한 유기 전계 발광 소자

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0690052A2 (de) * 1994-07-01 1996-01-03 Hoechst Aktiengesellschaft Verwendung von Pyrimidingruppen enthaltenden konjugierten Verbindungen als Elektrolumineszenzmaterialien

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
R. GOMPPER ET. AL.: "Synthesis of Oligo(diazaphenyls). Tailor-Made Fluorescent Heteroaromatics and Pathways to Nanostructures", SYNTHESIS, vol. 6, 1997, Thieme, pages 696 - 708, XP002469293 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102009047880A1 (de) 2009-09-30 2011-03-31 Osram Opto Semiconductors Gmbh Organische elektronische Vorrichtung und Verfahren zu dessen Herstellung
WO2011039323A2 (de) 2009-09-30 2011-04-07 Osram Opto Semiconductors Gmbh Organische elektronische vorrichtung und verfahren zu dessen herstellung
WO2011039323A3 (de) * 2009-09-30 2011-06-23 Osram Opto Semiconductors Gmbh Organische elektronische vorrichtung und verfahren zu dessen herstellung
CN102576823A (zh) * 2009-09-30 2012-07-11 欧司朗光电半导体有限公司 有机电子装置和其制造方法
JP2013506984A (ja) * 2009-09-30 2013-02-28 オスラム オプト セミコンダクターズ ゲゼルシャフト ミット ベシュレンクテル ハフツング 有機電子装置およびその製造方法
CN102576823B (zh) * 2009-09-30 2015-05-20 欧司朗光电半导体有限公司 有机电子装置和其制造方法
US9520570B2 (en) 2009-09-30 2016-12-13 Osram Oled Gmbh Organic electronic device and method for the production thereof
KR101770437B1 (ko) 2009-09-30 2017-09-05 오스람 오엘이디 게엠베하 유기 전자 장치 및 그 제조 방법

Also Published As

Publication number Publication date
CN101679850A (zh) 2010-03-24
EP2092041B9 (de) 2011-11-09
DE102006053644A1 (de) 2008-06-12
JP2010509781A (ja) 2010-03-25
EP2092041A1 (de) 2009-08-26
KR101482512B1 (ko) 2015-01-13
CN101679850B (zh) 2013-05-29
ATE481463T1 (de) 2010-10-15
DE502007005097D1 (de) 2010-10-28
US8309284B2 (en) 2012-11-13
EP2092041B1 (de) 2010-09-15
US20100112471A1 (en) 2010-05-06
KR20090106472A (ko) 2009-10-09
JP5193218B2 (ja) 2013-05-08

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