EP2044168A1 - Oligomères de complexes métalliques d'isonitrile comme émetteur triple pour des applications oled - Google Patents

Oligomères de complexes métalliques d'isonitrile comme émetteur triple pour des applications oled

Info

Publication number
EP2044168A1
EP2044168A1 EP07765025A EP07765025A EP2044168A1 EP 2044168 A1 EP2044168 A1 EP 2044168A1 EP 07765025 A EP07765025 A EP 07765025A EP 07765025 A EP07765025 A EP 07765025A EP 2044168 A1 EP2044168 A1 EP 2044168A1
Authority
EP
European Patent Office
Prior art keywords
dicyanobis
platinum
isocyanide
light
emitting device
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Withdrawn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
EP07765025A
Other languages
German (de)
English (en)
Inventor
Hartmut Yersin
Uwe Monkowius
Tobias Fischer
Walter Finkenzeller
Rafal Czerwieniec
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.)
Merck Patent GmbH
Original Assignee
NovaLED 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 NovaLED GmbH filed Critical NovaLED GmbH
Publication of EP2044168A1 publication Critical patent/EP2044168A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/006—Palladium compounds
    • C07F15/0066—Palladium compounds without a metal-carbon linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0086—Platinum compounds
    • C07F15/0093—Platinum compounds without a metal-carbon linkage
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • 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
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • 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
    • 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]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • triplet emitters can be significantly greater than for purely organic materials. Because of this property, the further development of organometallic materials is of major importance. Triplet emitters are described, for example, in WO 2004/017043 A2 (Thompson), WO 2004/016711 A1 (Thompson), WO 03/095587 (Tsuboyama), US 2003/0205707 (Chi-Ming Che), US Pat
  • a light emitting device comprising (i) an anode, (ii) a cathode and (iii) an emitter layer disposed between and in direct or indirect contact with the anode and the cathode comprising at least one complex of the formula (I)
  • the application can be carried out by a colloidal suspension in a polymer. Oligomer strands can be reduced prior to introduction into the polymer under ultrasonic processing and introduced into the polymer after filtration through nanofilter.
  • the emitter layer preferably has a layer thickness of 10 to 80 nm, in particular from 20 to 60 nm.
  • the group R SO 2 R 1 , wherein R 1 again represents a hydrocarbon group which may contain one or more heteroatoms.
  • R ' is alkyl, aryl, heteroaryl, which may optionally contain one or more functional groups as indicated above.
  • Complexes according to the invention and in particular complexes with M Pt, in which R in each case represents an aliphatic radical, are preferred.
  • R is in particular a saturated hydrocarbon radical, in particular having 1 to 30 C atoms, preferably having 2 to 20 C atoms, which may optionally contain heteroatoms.
  • the complex of formula according to the invention contained in the emitter layer (I) (NC) n M (CNR) n, a complex of formula (II)
  • R 1 represents a radical having a polymerizable group.
  • the polymer containing (NC) n M (CNR 1 ) m moieties may be first prepared and then applied, for example, as a solution by spin coating or inkjet printing. But it is also possible to apply the monomer and to polymerize on site.
  • the complexes are present in a sufficiently high concentration to allow MM interaction.
  • Examples of such polymerizable functions containing the group R 1 are for example olefin groups, in particular vinyl groups, expoxides or cyclic ethers for polymerization reactions, cyanates or alcohols for polyaddition reactions, carboxylates and amines or alcohols for polycondensation reactions and aryl halides and organoboronic acid or halide and olefin coupling reactions.
  • olefin groups in particular vinyl groups, expoxides or cyclic ethers for polymerization reactions, cyanates or alcohols for polyaddition reactions, carboxylates and amines or alcohols for polycondensation reactions and aryl halides and organoboronic acid or halide and olefin coupling reactions.
  • a further variation can be achieved by forming columnar structures of different complexes of formula (I). All ligands and the central atom can be varied independently of each other. In the emitter layer, therefore, e.g. a first complex of formula (I) having a first central atom M and a second complex of formula (I) having a second central atom other than the first central atom.
  • the invention further relates to the use of a compound of the formula (I) as defined herein as an emitter of a light-emitting device, in particular in an organic light-emitting device.
  • R alkyl, aryl, heteroaryl, -SO 2 R ', and functionalized derivatives, and polydentate derivatives (eg, CNCH 2 CH 2 CH 2 NC).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne des dispositifs émettant de la lumière et en particulier des dispositifs émettant de la lumière organique (OLED). L'invention concerne en particulier l'utilisation de complexes métalliques d'isonitrile luminescents comme émetteur oligomère dans des dispositifs de ce type.
EP07765025A 2006-07-04 2007-07-03 Oligomères de complexes métalliques d'isonitrile comme émetteur triple pour des applications oled Withdrawn EP2044168A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200610030860 DE102006030860A1 (de) 2006-07-04 2006-07-04 Oligomere von Isonitril-Metallkomplexen als Triplett-Emitter für OLED-Anwendungen
PCT/EP2007/005882 WO2008003464A1 (fr) 2006-07-04 2007-07-03 Oligomères de complexes métalliques d'isonitrile comme émetteur triple pour des applications oled

Publications (1)

Publication Number Publication Date
EP2044168A1 true EP2044168A1 (fr) 2009-04-08

Family

ID=38475962

Family Applications (1)

Application Number Title Priority Date Filing Date
EP07765025A Withdrawn EP2044168A1 (fr) 2006-07-04 2007-07-03 Oligomères de complexes métalliques d'isonitrile comme émetteur triple pour des applications oled

Country Status (6)

Country Link
US (1) US9130178B2 (fr)
EP (1) EP2044168A1 (fr)
JP (1) JP6013698B2 (fr)
DE (1) DE102006030860A1 (fr)
TW (1) TW200838975A (fr)
WO (1) WO2008003464A1 (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102008013691A1 (de) * 2008-03-11 2009-09-17 Merck Patent Gmbh Verwendung von Zusammensetzungen neutraler Übergangsmetallkomplexe in opto-elektronischen Bauelementen
DE102008036247A1 (de) * 2008-08-04 2010-02-11 Merck Patent Gmbh Elektronische Vorrichtungen enthaltend Metallkomplexe
DE102008053121A1 (de) * 2008-10-24 2010-04-29 Merck Patent Gmbh Doppelkomplex-Salze als Emitter in OLED-Vorrichtungen
DE102008053107B4 (de) 2008-10-24 2022-05-12 Cynora Gmbh Verwendung von unterschiedlich geladenen Metallkomplexen als Absorber in organischen Solarzellen sowie organische Solarzelle diese umfassend
DE102010005463A1 (de) * 2010-01-20 2011-07-21 cynora GmbH, 76344 Blau-Licht-Emitter mit Singulett-Harvesting-Effekt zur Verwendung in OLEDs und anderen organisch-elektronischen Vorrichtungen
DE102010027319A1 (de) 2010-07-16 2012-01-19 Merck Patent Gmbh Metallkomplexe
DE102011017572A1 (de) * 2011-04-27 2012-10-31 Siemens Aktiengesellschaft Bauteil mit orientiertem organischem Halbleiter
CN102336775B (zh) * 2011-07-15 2013-11-06 华中师范大学 双异氰桥链双金化合物的制造方法与应用
KR101701584B1 (ko) * 2012-04-23 2017-02-01 코니카 미놀타 가부시키가이샤 유기 일렉트로루미네센스 소자
KR102599157B1 (ko) 2015-08-14 2023-11-06 메르크 파텐트 게엠베하 유기 전계발광 소자용 페녹사진 유도체
DE102016105205A1 (de) * 2016-03-21 2017-09-21 Osram Oled Gmbh Optoelektronisches Bauelement und Verfahren zum Betreiben eines optoelektronischen Bauelements
CN111212493A (zh) * 2018-11-21 2020-05-29 台达电子工业股份有限公司 照明装置

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6830828B2 (en) * 1998-09-14 2004-12-14 The Trustees Of Princeton University Organometallic complexes as phosphorescent emitters in organic LEDs
US6137118A (en) * 1999-01-05 2000-10-24 Regents Of The University Of Minnesota Vapochromic photodiode
US6160267A (en) * 1999-01-05 2000-12-12 Regents Of The University Of Minnesota Vapochromic led
SE0001151D0 (sv) * 2000-03-31 2000-03-31 Amarin Dev Ab Method for producing a controlled-release composition
JP2001296819A (ja) * 2000-04-17 2001-10-26 Nec Corp 有機薄膜ｅｌデバイス及びその製造方法
US6984591B1 (en) * 2000-04-20 2006-01-10 International Business Machines Corporation Precursor source mixtures
JP4215145B2 (ja) 2001-02-21 2009-01-28 富士フイルム株式会社 発光素子用材料及び発光素子
US7026480B2 (en) * 2001-03-08 2006-04-11 The University Of Hong Kong Organometallic light-emitting material
SG92833A1 (en) * 2001-03-27 2002-11-19 Sumitomo Chemical Co Polymeric light emitting substance and polymer light emitting device using the same
US7250226B2 (en) * 2001-08-31 2007-07-31 Nippon Hoso Kyokai Phosphorescent compound, a phosphorescent composition and an organic light-emitting device
KR100543837B1 (ko) * 2001-09-04 2006-01-23 캐논 가부시끼가이샤 고분자 화합물 및 유기 발광 소자
US6653654B1 (en) * 2002-05-01 2003-11-25 The University Of Hong Kong Electroluminescent materials
JP2003332074A (ja) 2002-05-09 2003-11-21 Canon Inc 金属配位化合物を用いた発光素子
CN100340630C (zh) 2002-08-16 2007-10-03 南加利福尼亚大学 有机发光材料和器件
WO2004017043A2 (fr) 2002-08-16 2004-02-26 The University Of Southern California Matériaux électroluminescents organiques comprenant un ligand anionique
JP4531342B2 (ja) * 2003-03-17 2010-08-25 株式会社半導体エネルギー研究所 白色有機発光素子および発光装置
CA2435997C (fr) * 2003-07-24 2012-01-31 Evl Inc. Un engrais comportant un ferment comprenant une bacterie active et une methode pour le produire
DE10338550A1 (de) * 2003-08-19 2005-03-31 Basf Ag Übergangsmetallkomplexe mit Carbenliganden als Emitter für organische Licht-emittierende Dioden (OLEDs)
DE10350606A1 (de) * 2003-10-30 2005-06-09 Covion Organic Semiconductors Gmbh Verfahren zur Herstellung heteroleptischer, ortho-metallierter Organometall-Verbindungen
DE10358665A1 (de) * 2003-12-12 2005-07-07 Basf Ag Verwendung von Platin(II)-Komplexen als lumineszierende Materialien in organischen Licht-emittierenden Dioden (OLEDs)
JP2005276581A (ja) * 2004-03-24 2005-10-06 Aitesu:Kk 平面発光装置
DE102004018145A1 (de) * 2004-04-08 2005-10-27 Basf Ag Verwendung von Metallocenkomplexen von Metallen der 4. Nebengruppe des Periodensystems als Triplettemitter in organischen Leuchtdioden (OLEDs)
EP1703572A1 (fr) * 2005-01-25 2006-09-20 SONY DEUTSCHLAND GmbH Redresseurs moleculaires

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
None *
See also references of WO2008003464A1 *

Also Published As

Publication number Publication date
US9130178B2 (en) 2015-09-08
TW200838975A (en) 2008-10-01
JP2009542023A (ja) 2009-11-26
DE102006030860A1 (de) 2008-01-10
WO2008003464A1 (fr) 2008-01-10
US20100141120A1 (en) 2010-06-10
JP6013698B2 (ja) 2016-10-25

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