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• • 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
• • 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
  • C07F15/0033—Iridium compounds
• • 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
• • 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

Definitions

• the present invention relates to an iridium complex compound, and more specifically to an iridium complex compound having phosphorescence, an organic electroluminescent device obtained by using the same and uses thereof.
• a vacuum vapor deposition method of low molecular weight organic compounds and a coating method of polymer compound solutions are usually used for forming a luminescent layer in an organic EL device.
• the coating method is advantageous in terms of low production cost of the device and easy production of large-area device, and techniques for producing devices by the coating method are desired to be improved in the future.
• conventional iridium complex compounds usually have inferior solubility, and crystallization is brought about in a certain case by aggregation and association in forming a film by coating. Further, there has been a problem that if a film in which crystals are aggregated or associated is used for a luminescent layer of an organic EL device, not only emission is uneven but also a life of the device is shortened. [0005]
• R 5 to R 8 are each independently a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 40 carbon atoms, an amino group which may be substituted with an alkyl group having 1 to 30 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, a silyl group which may be substituted with an alkyl group having 1 to 30 carbon atoms or a specific electron-withdrawing group; at least one of R 5 to R 8 is the specific electron- withdrawing group; (with the proviso that R 1 to R 8 are not combined with each other to form rings) ; and the specific electron-withdrawing group is selected from the group consisting of a halogen atom, an alkyl group having 1 to 10 carbon atoms which is substituted with fluorine, an alkoxy group having 1 to 10 carbon atoms which is substituted with fluorine, a cyano group, an aldehy
• R 14 is a hydrocarbon group having 1 to 10
• R 1 to R 4 are groups having 2 or more carbon atoms.
• R 1 to R 4 is a group having 2
• the iridium complex compound according to the present invention has excellent solubility, and the organic EL device prepared by using the complex compound has a high luminous efficiency and is extended in life.
• Luminescent layer 4 Cathode BEST MODE FOR CARRYING OUT THE INVENTION
• two or more of R 1 to R 4 may be groups having 2 or more carbon atoms.
• the iridium complex compound tends to be excellent in solubility when at least one of R 1 to R 4 is a hydrocarbon group having a branched structure or when two or more of R 1 to R 4 are groups having 2 or more carbon atoms.
• R 9 to R 11 are each
• R 2 and R 3 are preferably the groups having 2 or more carbon atoms.
• R 4 is the group having 2 or more carbon atoms
• the peak emission wavelength tends to be shifted to a longer wavelength side as compared with a complex compound which is not substituted, and the value of the compound as a blue light emitting material is a little inferior.
• R 1 is the group having 2 or more carbon atoms
• the improvement of solubility is somewhat small due to a steric structural factor.
• the iridium complex compound represented by Formula (3) described above has a tertiary butyl group and therefore is excellent in solubility. Since the tertiary butyl group is a bulky group, the tertiary butyl group sterically isolates an excited state of the reactive iridium complex compound of the present invention from other molecules contained in the luminescent layer and therefore is advantageous for extending the life of the organic EL device. [0064]
• the iridium complex compound of the present invention may be a mixture of a facial complex and a meridional complex.
• the facial complex preferably accounts for not less than 50%, more preferably not less than 95%, particularly preferably 100% of the iridium complex compound.
• the facial complex is preferred since it has a higher quantum efficiency of emission as compared with that of the meridional complex.
• the hole-transporting polymerizable compound and the electron-transporting polymerizable compound are not particularly limited as long as they have a polymerizable functional group, and publicly known charge-transporting compounds can be used.
• Preferred examples of the hole-transporting polymerizable compounds include compounds represented by the following Formulas (El) to (E6) .
• the compounds represented by the following Formulas (El) to (E3) are more preferred from the viewpoint of charge mobility in the non-conjugated polymer compound.
• Preferred examples of the electron-transporting polymerizable compounds include compounds represented by the following Formulas (E7) to (E15) .
• the compounds represented by the following Formulas (E7) and (E12) to (E14) are more preferred from the viewpoint of charge mobility in the non-conjugated polymer compound.
• the charge-transporting non-conjugated polymer compound described above may be produced by any of radical polymerization, cationic polymerization, anionic polymerization and addition polymerization.
• the radical polymerization is preferred.
• the layers may be formed by mixing materials having different functions, for example, a luminescent material, a hole-transporting material, an electron- transporting material and the like.
• the organic layer including the iridium complex compound and the non- conjugated polymer compound may further contain other hole- transporting material and/or electron-transporting material for the purpose of supplementing the charge-transporting property.
• Such transporting materials may be low molecular weight compounds or polymer compounds.
• the electron- transporting materials may be used singly or in a mixture of two or more kinds, and different electron-transporting materials may be used as a laminate.
• the thickness of the electron-transporting layer depends on conductivity of the electron-transporting layer and is variable. Preferably, the thickness is 1 nm to 5 ⁇ m, more preferably 5 nm to 1 ⁇ m, and particularly preferably 10 nm to 500 nm.
• a hole-blocking layer may be provided adjacent to the luminescent layer on the cathode side for the purposes of inhibiting the holes from passing through the luminescent layer and of allowing the holes and electrons to recombine efficiently in the luminescent layer.
• the hole-blocking layer may be produced using publicly known materials such as triazole derivatives, oxadiazole derivatives and phenanthroline derivatives.
• the organic EL device according to the present invention is suitably used for display devices in computers, televisions, mobile terminals, portable phones, car navigation systems, viewfinders of video cameras and the like, and for backlights, light sources of electrophotography, light sources of illumination, light sources of recording, light sources of exposure, light sources of reading, indicators, advertising displays, interiors, optical communications and the like.
• the compound weighed 367 mg, and the yield was 85%. The compound was used directly for the subsequent step without identification .
• the respective fractions were recrystallized from a mixed solvent of methanol and dichloromethane. Consequently, the mer complex was obtained in the form of a yellow crystal and the fac complex was obtained in the form of a yellow fine crystal.
• the mer complex weighed 127 mg, and the yield thereof was 34%.
• the fac complex weighed 125 mg, and the yield thereof was 34%.
• the identification was made by 1 H- NMR and CHN elemental analysis.
• the organic layer obtained was dried over magnesium sulfate and then filtered, and the solvent was removed by evaporation.
• the residue was purified by medium pressure silica gel column chromatography (eluent: chloroform), and the solvent was removed by evaporation.
• the residue was dried under reduced pressure to give 2- (2, 4-difluorophenyl) -5-ethyl-4- propylpyridine in the form of a colorless liquid.
• the product weighed 1.40 g, and the yield was 41%.
• Example 5 Solubility test The facial and meridional iridium complex compounds (A) synthesized in Example 1 and the facial iridium complex compounds (B) to (D) synthesized in Examples 2 to 4 were tested for solubility. The results are shown in Table 1. The test was carried out by mixing the iridium complex compound with chloroform or toluene so that a prescribed concentration was obtained, and visually determining if the iridium complex compound was completely dissolved or partially undissolved after the mixture had been stirred at room temperature for one hour.
• An organic EL device was produced with use of a substrate (manufactured by Nippo Electric Co., Ltd.) provided with ITO (indium tin oxide) which was composed of a 25 mm square glass substrate and in which two stripe ITO electrodes having a width of 4 mm were formed as anodes on one surface.
• the substrate with the ITO electrodes (anodes) was spin coated with poly (3,4- ethylenedioxythiophene) -polystyrenesulfonic acid (trade name "Baytron P", manufactured by Bayer AG) at 3500 rpm for a coating time of 40 seconds. The coating was dried at 60 0 C for 2 hours under reduced pressure in a vacuum drying machine to form an anode buffer layer.
• the anode buffer layer thus obtained had a thickness of about 50 nm.
• the organic EL device was allowed to emit light by application of a voltage by means of programmable direct- current voltage/current source TR6143 manufactured by ADVANTEST CORPORATION.
• the emission luminance thereof was measured by means of luminance meter BM-8 manufactured by TOPCON CORPORATION.
• Table 2 shows luminescent color, emission uniformity, external quantum efficiency at 100 cd/m 2 and luminance half-life in operating at a constant current relative to the initial luminance of 100 cd/m 2 (the values of the external quantum efficiency and the luminance half-life are averages of the four organic EL devices formed on one substrate) .
• the luminance half-life in Table 2 is a relative value based on the measured value (100) of a device 7 described later.
• Devices 2 to 6 were prepared by the same method as producing the device 1, except that the facial complex compound (A) was changed to the luminescent materials shown in Table 2. The luminescent characteristics of these devices were evaluated in the same manner as in the device 1. The results are shown in Table 2.

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• 2007
  • 2007-11-05 US US12/445,536 patent/US20090315454A1/en not_active Abandoned
  • 2007-11-05 KR KR1020097011660A patent/KR101073232B1/ko active Active
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