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Organic electroluminescent device

An electroluminescent device and luminescent technology, applied in the direction of electric solid-state devices, electrical components, luminescent materials, etc., can solve the problems of insufficient current efficiency, low driving voltage, and insufficient

Inactive Publication Date: 2018-04-17
HODOGAYA KAGAKU IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] However, devices using these compounds in the hole injection layer, hole transport layer, or electron blocking layer have improved heat resistance, luminous efficiency, etc., but still cannot be said to be sufficient. Can't say enough, there is also a problem in the aspect of non-crystallinity

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0196]

[0197] Under a nitrogen atmosphere, 3.0 g of 2,8-dibromodibenzofuran, 8.4 g of (4'-diphenylamino-biphenyl-4-yl)-phenylamine, 2.7 g of sodium tert-butoxide, and toluene 60ml was added to the reaction vessel, followed by adding tert-butylphosphine 0.2g, Pd 2 (dba) 3 0.2 g and heated, stirring at reflux for 10 hours. 30 ml of toluene was added, and the filtrate obtained by filtration was concentrated. After the concentrate was purified by column chromatography (carrier: silica gel, eluent: toluene / cyclohexane), N,N'-bis(4 '-diphenylamino-biphenyl-4-yl)-N,N'-diphenyl-dibenzofuran-2,8-diamine (compound 2) light yellow powder 7.6g (yield: 83.5%).

[0198]

[0199] For the obtained pale yellow powder, NMR was used for structural identification. Will 1 H-NMR measurement results are shown in figure 1 .

[0200] pass 1 H-NMR (THF-d 8 ) detected the following 52 hydrogen signals. δ(ppm)=7.78(2H), 7.53(2H), 7.45(8H), 7.27(2H), 7.24-7.19(12H), 7.07(20H), 6.98(4H),...

Embodiment 2

[0202]

[0203] Under a nitrogen atmosphere, 5.0 g of 4,6-diiododibenzofuran, 11.8 g of (4'-diphenylamino-biphenyl-4-yl)-phenylamine, 4.9 g of potassium carbonate, hydrogen sulfite 0.4 g of sodium, 0.3 g of 3,5-di-tert-butylsalicylic acid, 10 ml of xylene, 5 ml of dodecylbenzene, and 0.1 g of copper powder were added to the reaction vessel, heated, and stirred at 210° C. for 12 hours. 60 ml of toluene was added, and the filtrate obtained by filtration was concentrated. After the concentrate was purified by column chromatography (carrier: silica gel, eluent: toluene / cyclohexane), N,N'-bis(4 '-Diphenylamino-biphenyl-4-yl)-N,N'-diphenyl-dibenzofuran-4,6-diamine (compound 33) white powder 9.3g (yield: 78.9 %).

[0204]

[0205] For the obtained pale yellow powder, NMR was used for structural identification. Will 1 H-NMR measurement results are shown in figure 2 .

[0206] pass 1 H-NMR (THF-d 8 ) detected the following 52 hydrogen signals. δ(ppm)=7.82(2H), 7.33(8H), ...

Embodiment 3

[0208]

[0209] Under a nitrogen atmosphere, 5.0 g of 2,8-dibromodibenzothiophene, 13.3 g of (4'-diphenylamino-biphenyl-4-yl)-phenylamine, 4.2 g of sodium tert-butoxide, and toluene 100ml was added to the reaction vessel, followed by adding 0.3g of tert-butylphosphine, Pd 2 (dba) 3 0.3 g and heated, stirring at reflux for 5.5 hours. After adding 50 ml of water and cooling to room temperature, the precipitated solid was obtained by filtration. The obtained solid was recrystallized from dichlorobenzene, thereby obtaining N,N'-bis(4'-diphenylamino-biphenyl-4-yl)-N,N'-diphenyl-dibenzo 11.3 g of light yellow powder of thiophene-2,8-diamine (compound 56) (yield: 76.9%).

[0210]

[0211] For the obtained white powder, NMR was used for structural identification. Will 1 H-NMR measurement results are shown in image 3 .

[0212] pass 1 H-NMR (THF-d 8 ) detected the following 52 hydrogen signals. δ(ppm)=7.94(2H), 7.81(2H), 7.46(4H), 7.45(4H), 7.25-7.19(14H), 7.08-7.05(20H...

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Abstract

An object of the present invention is to provide an organic electroluminescent device having high efficiency, low driving voltage, and a long lifetime by combining various materials which are excellent in hole and electron injection / transport performances, an electron blocking ability, stability as a thin film and durability for an organic electroluminescent device of high efficiency and high durability, in such a manner that the materials can effectively exhibit characteristics thereof. The organic electroluminescent device includes at least an anode, a hole transport layer, a light emittinglayer, an electron transport layer and a cathode in this order. The hole transport layer includes an arylamine compound of the following general formula (1).

Description

technical field [0001] The present invention relates to an organic electroluminescent device which is a self-luminescent device suitable for various display devices, and specifically relates to an organic electroluminescent device using a specific arylamine compound (and a specific compound having an anthracycline structure) device (hereinafter also referred to as an organic EL device). Background technique [0002] Since the organic EL device is a self-luminous device, it is brighter than a liquid crystal device, has excellent visibility, and can display clearly, so its research is becoming more and more active. [0003] In 1987, C.W.Tang et al. of Eastman Kodak Company developed a laminated structure device in which each material shared various roles, thus making organic EL devices using organic materials practical. They layered a phosphor capable of transporting electrons and an organic substance capable of transporting holes, injected two types of charges into the phosp...

Claims

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Application Information

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IPC IPC(8): H01L51/50C09K11/06
CPCC09K11/06H10K50/10
Inventor 加濑幸喜长冈诚骏河和行
Owner HODOGAYA KAGAKU IND
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