EP1716724A1 - Organische elektronische vorrichtungen - Google Patents
Organische elektronische vorrichtungenInfo
- Publication number
- EP1716724A1 EP1716724A1 EP05707510A EP05707510A EP1716724A1 EP 1716724 A1 EP1716724 A1 EP 1716724A1 EP 05707510 A EP05707510 A EP 05707510A EP 05707510 A EP05707510 A EP 05707510A EP 1716724 A1 EP1716724 A1 EP 1716724A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- organic
- electronic device
- organic electronic
- compound
- 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- Withdrawn
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
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
-
- 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]
- H10K50/14—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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- Ci to C 22 alkoxy group is particularly preferably understood to mean methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
- An organic electronic device is preferred, characterized in that the compound of the formula (1) is amorphous and the glass transition temperature T g of the compound is greater than 80 ° C, particularly preferably greater than 100 ° C, in particular greater than 130 ° C.
- radicals R 1 and R 2 contain no condensed aromatic ring systems with three or more condensed benzene units, that is to say for example no anthracene, pyrene, phenanthrene, perylene, etc. A maximum of two condensed benzene units are therefore preferred. However, this does not exclude that these residues can contain condensed heteroaromatic ring systems with three or more condensed rings, for example phenanthroline, acridine, etc.
- the compound of the formula (1) contains more than one carbonyl group.
- the arrangement of the carbonyl groups in the molecule can be linear or branched, or they can also be arranged dendritic. Preference is given to compounds which have a denditic structure. 1,3,5-Trisubstituted benzenes are also preferred.
- the radical R 1 then represents a bridging group between two or more carbonyl functions.
- an organic electroluminescent device characterized in that the emitter or emitters in the emission layer with suitable excitation in the visible spectral range with one or more maxima between 380 nm and 750 nm fluoresce. It may also be preferred if the emitters have several different emission maxima, so that white emission results overall.
- an organic electronic device characterized in that one or more layers are coated with a sublimation process.
- the materials are evaporated in vacuum sublimation systems at a pressure of less than 10 "5 mbar, preferably less than 10 " 6 mbar, particularly preferably less than 10 "7 mbar.
- An organic electronic device is also preferred, characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) process or with the aid of a carrier gas sublimation.
- the materials are applied at a pressure between 10 "5 mbar and 1 bar.
- the compounds according to formula (1) have a higher charge carrier mobility than electron transport materials according to the prior art, such as. B. AIQ 3 .
- thicker electron transport layers can be used. As already described above, this is important for avoiding short circuits and is furthermore particularly necessary for the combination of fluorescent and phosphorescent OLEDs in a display, since the thicker layer thicknesses of the phosphorescent OLEDs must be compensated for by a thicker electron transport layer of the fluorescent OLEDs.
- the starting materials (solvent, zinc, zinc cyanide, tetrakis (triphenylphosphine) palladium (0), phenylmagnesium bromide solution, EDTA, 1-bromonaphthalene, 4-methyl-1-naphthalene boronic acid, n-BuLi solution 2.5 molar in ⁇ -hexane, N, N-dimethyl-carbamic acid chloride, 2,7-dibromofluorenone) were obtained from ALDRICH and ABCR. 1,3,5-tris (4-bromophenyl) benzene was prepared according to M.
- the precipitated solid was filtered off with suction, washed with 100 ml of water and ethanol each time and dried.
- the solid was placed in a Soxhlett extractor and extracted with chloroform through a glass fiber extraction thimble (pore size 0.1 ⁇ m).
- the chloroform was concentrated to a volume of 100 ml and 500 ml of ethanol were added.
- the resulting precipitate was filtered off and washed with ethanol.
- Tm 329 ° C
- T g 139 ° C.
- the yield of the electron transport material E3 was 36.9 g (59 mmol), corresponding to 78.7 % of theory, with a purity of> 99.9% (according to HPLC).
- HIL Hole injection layer
- PEDOT poly (3,4-ethylenedioxy-2,5-thiophene) hole transport layer
- HTM hole transport layer 20 nm NaphDATA (evaporated; obtained from SynTec; 4,4 ', 4 "tris (N-1-naphthyl-N-phenylamino) triphenylamine hole transport layer (HTM) 20 nm S-TAD (evaporated; produced according to WO 99/12888; 2,2 ', 7,7'-tetrakis (diphenylamino) -spiro- 9,9'-bifluorene) emission layer (EML) Spiro-DPVBi (manufactured according to WO 02/10093, 2,2', 7,7'-tetrakis (2,2'-diphenylvinyl) -spiro-9,
- OLEDs which have not yet been optimized, have been characterized as standard; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A), the power efficiency (measured in Im / W) depending on the brightness, calculated from current-voltage-brightness characteristics (IUL characteristics), and the service life were determined.
- the lifetime is defined as the time after which the initial brightness of the OLED has halved at a constant current density of 10 mA / cm 2 .
- the layer thickness was optimized separately for each material for the electron transport layer. For a better comparison, however, the thicker AIQ 3 layer thicknesses are also listed, which are directly comparable with the layer thicknesses of E1 and E2.
- the composition of the ETL including the layer thicknesses being listed in each case.
- the ETLs contain the compounds E1 as electron transport material to E4.
- OLEDs which contain AIQ 3 as the electron conductor according to the prior art serve as comparative examples.
- All OLEDs show blue emission, which comes from the fluorescence emitter S-DPVBi. Higher photometric efficiencies are obtained in devices in which the AIQ 3 electron conductor has been replaced by the electron conductors E1 to E4 according to the invention. Since the voltages required to achieve a certain brightness are also low here, very good power efficiency is obtained.
- the service life increases from approx. 650 h to over 1100 h. In particular, with the same layer thickness of the ETL, the efficiencies, the power efficiencies, the service life and the color are better with the electron transport materials according to the invention than with the standard electron conductor AIQ 3 .
- OLEDs manufactured according to the new design principle, have a higher efficiency at lower voltages and a longer service life, as can easily be seen in Table 1.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102004008304A DE102004008304A1 (de) | 2004-02-20 | 2004-02-20 | Organische elektronische Vorrichtungen |
PCT/EP2005/001709 WO2005084081A1 (de) | 2004-02-20 | 2005-02-18 | Organische elektronische vorrichtungen |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1716724A1 true EP1716724A1 (de) | 2006-11-02 |
Family
ID=34832853
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05715402A Withdrawn EP1716725A1 (de) | 2004-02-20 | 2005-02-18 | Organische elektronische vorrichtungen |
EP05707510A Withdrawn EP1716724A1 (de) | 2004-02-20 | 2005-02-18 | Organische elektronische vorrichtungen |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP05715402A Withdrawn EP1716725A1 (de) | 2004-02-20 | 2005-02-18 | Organische elektronische vorrichtungen |
Country Status (7)
Country | Link |
---|---|
US (2) | US7838126B2 (de) |
EP (2) | EP1716725A1 (de) |
JP (2) | JP5253739B2 (de) |
KR (2) | KR20060127138A (de) |
CN (2) | CN1922929A (de) |
DE (1) | DE102004008304A1 (de) |
WO (2) | WO2005084082A1 (de) |
Families Citing this family (254)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102004008304A1 (de) * | 2004-02-20 | 2005-09-08 | Covion Organic Semiconductors Gmbh | Organische elektronische Vorrichtungen |
EP1871856A1 (de) * | 2005-04-12 | 2008-01-02 | Merck Patent GmbH | Organische elektrolumineszenzvorrichtungen |
US8334058B2 (en) * | 2005-04-14 | 2012-12-18 | Merck Patent Gmbh | Compounds for organic electronic devices |
DE102005040411A1 (de) | 2005-08-26 | 2007-03-01 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102005043163A1 (de) | 2005-09-12 | 2007-03-15 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
US8206839B2 (en) * | 2005-10-04 | 2012-06-26 | Fujifilm Corporation | Organic electroluminescent element |
JP5080774B2 (ja) * | 2005-10-04 | 2012-11-21 | 富士フイルム株式会社 | 有機電界発光素子 |
DE102005058557A1 (de) * | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung |
WO2007065550A1 (de) * | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Neue materialien für organische elektrolumineszenzvorrichtungen |
DE102005058543A1 (de) | 2005-12-08 | 2007-06-14 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtungen |
DE102006013802A1 (de) | 2006-03-24 | 2007-09-27 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
JP4273132B2 (ja) * | 2006-04-03 | 2009-06-03 | セイコーエプソン株式会社 | 有機発光素子の製造方法 |
DE102006031990A1 (de) | 2006-07-11 | 2008-01-17 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
WO2008142921A1 (ja) * | 2007-05-24 | 2008-11-27 | Nitto Denko Corporation | 光学フィルム、画像表示装置、ジエチニルフルオレン及びそのポリマー |
JP5133034B2 (ja) * | 2007-05-24 | 2013-01-30 | 日東電工株式会社 | 光学フィルム、画像表示装置、ジエチニルフルオレン及びそのポリマー |
DE102007024850A1 (de) | 2007-05-29 | 2008-12-04 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
US20090191427A1 (en) * | 2008-01-30 | 2009-07-30 | Liang-Sheng Liao | Phosphorescent oled having double hole-blocking layers |
DE102008018670A1 (de) | 2008-04-14 | 2009-10-15 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008035413A1 (de) | 2008-07-29 | 2010-02-04 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtungen |
DE102008054141A1 (de) | 2008-10-31 | 2010-05-06 | Merck Patent Gmbh | Neue Materialien für organische Elektrolumineszenzvorrichtungen |
DE102008063490B4 (de) | 2008-12-17 | 2023-06-15 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung und Verfahren zum Einstellen des Farbortes einer weiß emittierenden Elektrolumineszenzvorrichtung |
DE102009005289B4 (de) | 2009-01-20 | 2023-06-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen, Verfahren zu deren Herstellung und elektronische Vorrichtungen, enthaltend diese |
DE102009005290A1 (de) | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Verbindungen für elektronische Vorrichtungen |
DE102009005288A1 (de) | 2009-01-20 | 2010-07-22 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009005746A1 (de) | 2009-01-23 | 2010-07-29 | Merck Patent Gmbh | Materialien für organische Elektrolumineszenzvorrichtungen |
DE102009009277B4 (de) | 2009-02-17 | 2023-12-07 | Merck Patent Gmbh | Organische elektronische Vorrichtung, Verfahren zu deren Herstellung und Verwendung von Verbindungen |
DE102009012346B4 (de) | 2009-03-09 | 2024-02-15 | Merck Patent Gmbh | Organische Elektrolumineszenzvorrichtung und Verfahren zu deren Herstellung |
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- 2005-02-18 EP EP05715402A patent/EP1716725A1/de not_active Withdrawn
- 2005-02-18 WO PCT/EP2005/001710 patent/WO2005084082A1/de not_active Application Discontinuation
- 2005-02-18 US US10/589,847 patent/US7838126B2/en not_active Expired - Fee Related
- 2005-02-18 KR KR1020067016642A patent/KR20060127138A/ko not_active Application Discontinuation
- 2005-02-18 US US10/590,037 patent/US7776455B2/en active Active
- 2005-02-18 JP JP2006553551A patent/JP5253739B2/ja not_active Expired - Fee Related
- 2005-02-18 CN CNB2005800054975A patent/CN100482023C/zh active Active
- 2005-02-18 WO PCT/EP2005/001709 patent/WO2005084081A1/de not_active Application Discontinuation
- 2005-02-18 EP EP05707510A patent/EP1716724A1/de not_active Withdrawn
- 2005-02-18 JP JP2006553552A patent/JP2007527116A/ja active Pending
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2006
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CN100482023C (zh) | 2009-04-22 |
KR20060127138A (ko) | 2006-12-11 |
EP1716725A1 (de) | 2006-11-02 |
US7776455B2 (en) | 2010-08-17 |
JP5253739B2 (ja) | 2013-07-31 |
KR20060133584A (ko) | 2006-12-26 |
WO2005084081A1 (de) | 2005-09-09 |
WO2005084082A1 (de) | 2005-09-09 |
US20070164273A1 (en) | 2007-07-19 |
JP2007526634A (ja) | 2007-09-13 |
CN1922929A (zh) | 2007-02-28 |
JP2007527116A (ja) | 2007-09-20 |
KR101175959B1 (ko) | 2012-08-22 |
DE102004008304A1 (de) | 2005-09-08 |
US7838126B2 (en) | 2010-11-23 |
US20070170419A1 (en) | 2007-07-26 |
CN1922930A (zh) | 2007-02-28 |
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