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
  • H10K2101/00—Properties of the organic materials covered by group H10K85/00
  • H10K2101/90—Multiple hosts in the emissive layer
• • 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
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. 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
  • H10K85/60—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
• • 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
• • 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

• organic EL devices include an organic EL element consisting of extremely thin layers (e.g. ⁇ 1.0 ⁇ m ) between the anode and the cathode.
• the organic EL element encompasses the layers between the anode and cathode electrodes.
• the invention provides an OLED device comprising a light- emitting layer containing a light emitting bis(azinyl)methene boron complex compound comprising a complex system of at least five fused rings and bearing, on at least one ring carbon or nitrogen, a substituent sufficient to provide a wavelength of maximum emission of less than 520nm as measured at a concentration of ⁇ 10 " M in ethyl acetate solvent.
• the invention also provides a lighting device containing the OLED, the complex compound, and a method of emitting thelight employing the device.
• the invention provides an OLED device that exhibits improved luminance efficiency and a desirable hue.
• 1, 2, 3, 4, 1', 2', 3', and 4' are conveniently all carbon atoms.
• the device may desirably contain at least one or both of ring A or A' that contains substituents joined to form a fused ring.
• the present invention can be employed in most OLED device configurations and light emitting devices including the OLED devices described herein. These include very simple structures comprising a single anode and cathode to more complex devices, such as passive matrix displays comprised of orthogonal arrays of anodes and cathodes to form pixels, and active-matrix displays where each pixel is controlled independently, for example, with a thin film transistor (TFT).
• TFT thin film transistor
• the substrate 101 can either be light fransmissive or opaque, depending on the intended direction of light emission.
• the light fransmissive property is desirable for viewing the EL emission through the substrate.
• Transparent glass or organic material are commonly employed in such cases.
• the fransmissive characteristic of the bottom support is immaterial, and therefore can be light fransmissive, light absorbing or light reflective.
• Substrates for use in this case include, but are not limited to, glass, plastic, semiconductor materials, ceramics, and circuit board materials. Of course it is necessary to provide in these device configurations a light-transparent top electrode.
• Typical substituents include alkyl groups, alkoxy groups, aryl groups, aryloxy groups, and halogen such as fluoride, chloride, and bromide.
• the various alkyl and alkylene groups typically contain from about 1 to 6 carbon atoms.
• the cycloalkyl moieties can contain from 3 to about 10 carbon atoms, but typically contain five, six, or seven ring carbon atoms— e.g., cyclopentyl, cyclohexyl, and cycloheptyl ring structures.
• the aryl and arylene groups are usually phenyl and phenylene moieties.
• the hole-transporting layer can be formed of a single or a mixture of aromatic tertiary amine compounds.
• R represent hydrogen or one or more substituents selected from the following groups: Group 1 : hydrogen, alkyl and alkoxy groups typically having from 1 to 24 carbon atoms; Group 2: a ring group, typically having from 6 to 20 carbon atoms; Group 3: the atoms necessary to complete a carbocyclic fused ring group such as naphthyl, anthracenyl, pyrenyl, and perylenyl groups, typically having from 6 to 30 carbon atoms; Group 4: the atoms necessary to complete a heterocyclic fused ring group such as furyl, thienyl, pyridyl, and quinolinyl groups, typically having from 5 to 24 carbon atoms; Group 5: an alkoxylamino, alkylamino, and arylamino group typically having from 1 to 24 carbon atoms; and Group 6: fluorine, chlorine, bromine and cyano radicals.
• Group 1 hydrogen, alkyl and alkoxy groups typically having from 1 to 24 carbon
• cathode materials include, but are not limited to, those disclosed in US 5,059,861, US 5,059,862, and US 6,140,763.
• the cathode When light emission is viewed through the cathode, the cathode must be transparent or nearly transparent. For such applications, metals must be thin or one must use transparent conductive oxides, or a combination of these materials.
• Optically transparent cathodes have been described in more detail in US 5,776,623.
• Cathode materials can be deposited by evaporation, sputtering, or chemical vapor deposition. When needed, patterning can be achieved through many well known methods including, but not limited to, through-mask deposition, integral shadow masking as described in US 5,276,380 and EP 0 732 868, laser ablation, and selective chemical vapor deposition.
• ⁇ N cvanomethinelquinolinato- Nlboron (Inv-1): A mixture of bis(2-quinolinyl)acetonitrile, diisopropylethylamine, BF 3 -etherate, and acetonitrile were placed in a sealed pressure bottle and heated in a 120 °C oil bath for 8 h. Once cooled to ambient temperature the solid was collected and washed with cold acetonitrile to provide product in 77% yield. Results of 1H ⁇ MR spectroscopic analysis is consistent with the product. Other materials of the invention were prepared in an analogous fashion.
• Example 4 EL Device Fabrication with mixed host - Inventive Example An EL device (Sample 11) satisfying the requirements of the invention was constructed in the following manner: 1.
• HTL Hole-Transporting layer

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

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• 2004
  • 2004-01-30 US US10/768,327 patent/US7329466B2/en not_active Expired - Lifetime
  • 2004-12-31 TW TW093141796A patent/TW200538531A/zh unknown
• 2005
  • 2005-01-18 JP JP2006551408A patent/JP5209208B2/ja not_active Expired - Lifetime
  • 2005-01-18 WO PCT/US2005/002344 patent/WO2005076385A1/en not_active Ceased
  • 2005-01-18 KR KR1020117029518A patent/KR101200863B1/ko not_active Expired - Lifetime
• 2006
  • 2006-07-28 KR KR1020067015410A patent/KR101212582B1/ko not_active Expired - Lifetime

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