Organic electroluminescent element

An electroluminescent device and a luminescent technology, which are applied in the direction of organic semiconductor devices, electric solid devices, electrical components, etc., can solve problems such as insufficiency

Active Publication Date: 2017-12-01
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, it is proposed that in the hole injection layer or the hole transport layer, by further P-doping tribromoaniline hexachloroantimonate, axene derivatives, F4-TCNQ, etc., the materials commonly used in the layer can improve Hole-injecting properties (see Patent Document 6 and Non-Patent Document 5), low driving voltage, heat resistance, luminous efficiency, etc. of devices obtained by using these compounds in the hole-injection layer or hole-transport layer are improved, However, it is still not sufficient, and further lower driving voltage and higher luminous efficiency are required

Method used

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0241]

[0242]Add (biphenyl-4-yl)-aniline 39.5g, 4,4"-diiodo-1,1'; 4',1"-terphenyl 32.4g, copper powder 0.42g, potassium carbonate 27.8 g to the reaction vessel g, 1.69 g of 3,5-di-tert-butylsalicylic acid, 2.09 g of sodium bisulfite, 32 ml of dodecylbenzene, and 50 ml of toluene, and heated to 210°C while distilling off the toluene. After stirring for 30 hours, it cooled, and 50 ml of toluene and 100 ml of methanol were added. The precipitated solid was collected by filtration, washed with 500 ml of a mixed solution of methanol / water (5 / 1, v / v), then 350 ml of 1,2-dichlorobenzene was added and heated, and insoluble matter was removed by filtration. After natural cooling, 400 ml of methanol was added, and the precipitated crude product was collected by filtration, and reflux washing was performed with 500 ml of methanol to obtain 4,4"-bis{(biphenyl-4-yl)-phenylamino}-1 ,1'; 4',1"-terphenyl (compound 1-1) gray powder 45.8g (91% yield).

[0243]

[0244] The structure of...

Embodiment 2

[0248]

[0249] 16.7 g of (biphenyl-4-yl)-4-toluidine, 12.9 g of 4',1"-terphenyl, 0.17 g of copper powder, 11.2 g of potassium carbonate, 0.71 g of 3,5-di-tert-butylsalicylic acid, 0.89 g of sodium bisulfite, 20 ml of dodecylbenzene, and 20 ml of toluene were heated to 210°C while distilling off the toluene, and stirred for 28 hours. After cooling, 150 ml of toluene was added, and insoluble matter was removed by filtration. Add 100ml of methanol, collect the precipitated crude product by filtration, and repeat recrystallization three times with a mixed solvent of toluene / methanol to obtain 4,4"-bis{(biphenyl-4-yl)-4-toluene 12.3 g (yield: 61%) of yellow-white powder of 1-amino}-1,1'; 4',1"-terphenyl (compound 1-10).

[0250]

[0251] For the obtained yellow-white powder, NMR was used to identify the structure.

[0252] use 1 H-NMR (CDCl 3 ) detected the following 44 hydrogen signals.

[0253] δ (ppm) = 7.68-7.62 (4H), 7.61-7.41 (16H), 7.38-7.08 (18H), 2.38 (6H).

Embodiment 3

[0255]

[0256] Add (biphenyl-4-yl)-(phenyl-d 5 )amine 25.3g, 4,4"-diiodo-1,1'; 4',1"-terphenyl 20.3g, copper powder 0.30g, potassium carbonate 17.5g, 3,5-di-tert-butyl salicylic acid 1.05g, 1.31g of sodium bisulfite, 20ml of dodecylbenzene, and 30ml of toluene were heated to 210°C while distilling off the toluene. After stirring for 23 hours, it cooled, and 30 ml of toluene and 60 ml of methanol were added. The precipitated solid was collected by filtration, washed with 180 ml of a mixed solution of methanol / water (1 / 5, v / v), and then washed with 90 ml of methanol. 210 ml of 1, 2- dichlorobenzene was added to the obtained gray powder, it heated, and the insoluble matter was removed by filtration. After natural cooling, 210ml of methanol was added, and the precipitated crude product was collected by filtration, and 210ml of methanol was used for reflux washing to obtain 4,4"-bis{(biphenyl-4-yl)-(phenyl-d 5 )amino}-1,1'; 29.3g (yield: 96%) of gray powder of 4',1"-terphenyl...

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Abstract

To provide an organic electroluminescent element which has low driving voltage, high luminous efficiency and a long service life by combining various materials for organic electroluminescent elements having excellent injection / transport ability for holes and electrons, excellent electron blocking ability, or excellent stability and durability in a thin film state so that the characteristics of respective materials can be effectively exerted as materials for organic electroluminescent elements having high luminous efficiency and high durability. To also provide an organic electroluminescent element wherein low driving voltage is maintained or increase in the driving voltage is effectively suppressed by controlling the doping concentration of an electron acceptor and / or the film thickness of an organic layer that contains an electron acceptor. An organic electroluminescent element which sequentially comprises at least a positive electrode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a negative electrode in this order, and which is characterized in that the hole injection layer contains an aryl amine compound represented by general formula (1) and an electron acceptor. (In the formula, Ar1-Ar4 may be the same as or different from each other, and each represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.)

Description

technical field [0001] The present invention relates to a self-luminescent device suitable for various display devices, that is, an organic electroluminescent device, and in particular, to an organic electroluminescent device using a specific aromatic amine compound doped with an electron acceptor (hereinafter sometimes referred to as an organic electroluminescent device). Organic EL devices). 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 perform clear display, so active research has been conducted. [0003] In 1987, C.W.Tang et al. of Eastman Kodak Co. developed an organic EL device using an organic material by developing a laminated structure device in which various functions are allocated to each material. They laminated a phosphor capable of transporting electrons and an organic material capable of transporting holes, injected two kinds of charges into t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50C07C211/54C07C211/58C07C211/61C07C255/51C07D209/14C07D307/91
CPCC07C255/51C07C211/54C07C211/58C07C211/61C07D209/14C07D307/91H10K71/30H10K85/633H10K85/631H10K85/6574H10K85/6572H10K50/17H10K50/00C09K11/06C09K2211/1011H10K50/12H10K50/14H10K50/11H10K85/30H10K85/60H10K85/636H10K50/15H10K50/16H10K50/81H10K50/82H10K85/622H10K85/626H10K2101/10H10K2102/351C07C2603/42C07C2603/18C07C2603/26
Inventor 林秀一富樫和法望月俊二内藤慧悟
Owner HODOGOYA CHEMICAL CO LTD
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