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Organic element for electroluminescent devices

a light-emitting diode and electroluminescent technology, applied in the direction of group 3/13 element organic compounds, discharge tube luminescnet screens, natural mineral layered products, etc., can solve the problems of low quantum efficiency of electroluminescence of unsubstituted or alkyl substituted pyrromethene-bf2 complexes, and the inability to obtain luminance efficient green oleds conveniently, etc., to achieve desirable hue and improve luminance efficiency

Inactive Publication Date: 2006-09-21
GLOBAL OLED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0010] The invention provides an OLED device that exhibits improved luminance efficiency and a desirable hue.

Problems solved by technology

While organic electroluminescent (EL) devices have been known for over two decades, their performance limitations have represented a barrier to many desirable applications.
However, the green-emitting unsubstituted or alkyl substituted pyrromethene-BF2 complexes exhibit relatively low quantum efficiencies of electroluminescence.
In simple terms, luminance efficient green OLEDs do not appear to be conveniently obtained with pyrromethene BF2 complexes used as dopants.

Method used

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  • Organic element for electroluminescent devices
  • Organic element for electroluminescent devices
  • Organic element for electroluminescent devices

Examples

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examples

Maximum Emission and Luminance Efficiency

[0153] Emission spectra were obtained for a series of the above inventive examples and the following comparative examples.

Example# RingsStructureComp-13Comp-24Comp-35

[0154] The emission spectra and quantum yields were obtained at room temperature in ethyl acetate solution at concentrations of 10−5 to 10−6M and expressed as quanta per unit time per unit wavelength interval against wavelength. A fluorescence procedure is well known to those skilled in the art [see, for example, C. A. Parker and W. T. Rees, Analyst, 85, 587 (1960)]. The maximum of emission spectra is defined as the wavelength corresponding to the highest point of such spectrum. The results are shown in the following table.

TABLE 1SOLUTION (ETOAC) DATAExampleTypeE max (soln.)Quantum Yield.Comp-1Comparative492 nm0.15Comp-2Comparative498 nm0.63Comp-3Comparative520 nm0.96Inv-1Inventive490 nm0.72Inv-2Inventive500 nm0.67Inv-3Inventive506 nm0.77Inv-4Inventive476 nm0.86Inv-5Inventi...

example 2

EL Device Fabrication—Inventive Example

[0159] An EL device (Sample 1) satisfying the requirements of the invention was constructed in the following manner: [0160] 1. A glass substrate coated with an 85 nm layer of indium-tin oxide (ITO) as the anode was sequentially ultrasonicated in a commercial detergent, rinsed in deionized water, degreased in toluene vapor and exposed to oxygen plasma for about 1 min. [0161] 2. Over the ITO was deposited a 1 nm fluorocarbon (CFx) hole-injecting layer (HIL) by plasma-assisted deposition of CHF3. [0162] 3. A hole-transporting layer (HTL)of N,N′-di-1-naphthyl-N,N′-diphenyl-4,4′-diaminobiphenyl (NPB) having a thickness of 75 nm was then evaporated from a tantalum boat. [0163] 4. A 25 nm light-emitting layer (LEL) of 2-tert-butyl-9,10-di-(2-naphthyl)anthracene (TBADN) and Inv-1 (0.7% wt %) were then deposited onto the hole-transporting layer. These materials were also evaporated from tantalum boats. [0164] 5. A 35 nm electron-transporting layer (ETL...

example 3

EL Device Fabrication—Inventive Example

[0170] An EL device (Sample 6) satisfying the requirements of the invention was constructed in the following manner: [0171] 1. A glass substrate coated with an 85 nm layer of indium-tin oxide (ITO) as the anode was sequentially ultrasonicated in a commercial detergent, rinsed in deionized water, degreased in toluene vapor and exposed to oxygen plasma for about 1 min. [0172] 2. Over the ITO was deposited a 1 nm fluorocarbon (CFx) HIL by plasma-assisted deposition of CHF3. [0173] 3. A HTL of N,N′-di-1-naphthalenyl-N,N′-diphenyl-4,4′-diaminobiphenyl (NPB) having a thickness of 75 nm was then evaporated from a tantalum boat. [0174] 4. A 37.5 nm LEL of tris(8quinolinolato)aluminum (III) (AlQ3) and Inv-1 (0.7 wt %) were then deposited onto the hole-transporting layer. These materials were also evaporated from tantalum boats. [0175] 5. A 37.5 nm ETL of tris(8quinolinolato)aluminum (III) (AlQ3) was then deposited onto the light-emitting layer. This ma...

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Abstract

Disclosed is 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 520 nm as measured at a concentration of <10−3M in ethyl acetate solvent.

Description

FIELD OF THE INVENTION [0001] This invention relates to organic light emitting diode (OLED) electroluminescent (EL) device comprising a light-emitting layer containing a boron dopant compound containing a bis(azinyl)methene boron group. BACKGROUND OF THE INVENTION [0002] While organic electroluminescent (EL) devices have been known for over two decades, their performance limitations have represented a barrier to many desirable applications. In simplest form, an organic EL device is comprised of an anode for hole injection, a cathode for electron injection, and an organic medium sandwiched between these electrodes to support charge recombination that yields emission of light. These devices are also commonly referred to as organic light-emitting diodes, or OLEDs. Representative of earlier organic EL devices are Gurnee et al. U.S. Pat. No. 3,172,862, issued Mar. 9, 1965; Gurnee U.S. Pat. No. 3,173,050, issued Mar. 9, 1965; Dresner, “Double Injection Electroluminescence in Anthracene”, ...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): H05B33/14C07F5/02C09K11/06H01L51/30H01L51/50
CPCH01L51/0052H01L51/0059H01L51/0062Y10S428/917H01L51/5012H01L2251/5384H01L51/0079H10K85/649H10K85/321H10K85/631H10K85/615H10K50/11H10K2101/90C09K11/06
Inventor VARGAS, J. RAMONKONDAKOV, DENIS Y.
Owner GLOBAL OLED TECH
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