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Organic electroluminescent element

一种电致发光器件、致发光的技术，应用在电固体器件、电气元件、发光材料等方向，能够解决驱动电压降低发光效率、结果不充分等问题，达到低驱动电压、良好效率、长寿命的效果

Active Publication Date: 2017-08-29
HODOGOYA CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the heat resistance and luminous efficiency etc. of devices using these compounds for the hole injection layer or the hole transport layer are improved, the results are still not sufficient, and further reduction in driving voltage and further improvement in luminous efficiency are required

Method used

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  • Organic electroluminescent element
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  • Organic electroluminescent element

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0382]

[0383] Synthesis of 4,4"'-bis{(biphenyl-4-yl)-phenylamino}-(1,1':4',1":4",1"'-quaterphenyl);

[0384] Into a nitrogen purged reaction vessel was added

[0385]

[0386] And nitrogen gas was passed therethrough for 1 hour. Then, 1.1 g of tetrakis(triphenylphosphine)palladium was added, followed by heating, and stirring was performed at 72° C. for 10 hours. A total of 60 mL of methanol was added after cooling to room temperature. The precipitated solid was collected by filtration and washed with 100 mL of a mixed solution of methanol / water (5 / 1, v / v). Next, 100 mL of 1,2-dichlorobenzene was added and dissolved under heating. Insolubles were removed by filtration, followed by gradual cooling and addition of 200 mL of methanol. The precipitated crude product was collected by filtration. The crude product was washed with 100 mL of methanol at reflux. As a result, 11.8g (yield 81%) of 4,4"'-bis{(biphenyl-4-yl)-phenylamino}-(1,1':4',1":4",1" was obtained '-quater...

Synthetic example 2

[0395]

[0396] 4,4""-bis{(biphenyl-4-yl)-phenylamino}-(1,1':4',1":4",1"':4"',1""-kink phenyl) synthesis;

[0397] Into a nitrogen purged reaction vessel was added

[0398]

[0399] And nitrogen gas was passed therethrough for 1 hour. Then, 1.0 g of tetrakis(triphenylphosphine)palladium was added, followed by heating, and stirring was performed at 72° C. for 18 hours. After cooling to room temperature, a total of 60 mL of methanol was added. The precipitated solid was collected by filtration and washed with 100 mL of a mixed solution of methanol / water (5 / 1, v / v). Next, 100 mL of 1,2-dichlorobenzene was added and dissolved under heating. Insolubles were removed by filtration, followed by gradual cooling and addition of 200 mL of methanol. The precipitated crude product was collected by filtration. The crude product was washed with 100 mL of methanol at reflux. As a result, 9.8 g (yield 66%) of 4,4""-bis{(biphenyl-4-yl)-phenylamino}-(1,1':4',1":4",1 "':4"',1""-kinke...

Synthetic example 3

[0408]

[0409] Synthesis of 4,4"'-bis{(biphenyl-4-yl)-phenylamino}-(1,1':3',1":3",1"'-quaterphenyl);

[0410] The reaction was performed on the same conditions as in Synthesis Example 1 except that 3,3'-dibromobiphenyl was used instead of 4,4'-diiodobiphenyl.

[0411] As a result, 16.2 g (yield 91%) of 4,4"'-bis{(biphenyl-4-yl)-phenylamino}-(1,1':3',1":3",1 "'-quaterphenyl) (compound 1-11) light yellow powder.

[0412]

[0413] The structure of the resulting pale yellow powder was identified using NMR. exist 1 H-NMR (CDCl 3 ), the following 44 hydrogen signals were detected.

[0414] δ(ppm)=7.87(2H)

[0415] 7.48-7.66(18H)

[0416] 7.39-7.48(4H)

[0417] 7.29-7.39(6H)

[0418] 7.18-7.26(12H)

[0419] 7.08(2H)

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Abstract

The present invention provides an organic EL element which sequentially comprises at least a positive electrode, a hole injection layer, a first hole transport layer, a second 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 second hole transport layer contains an arylamine compound having a specific structure and the electron transport layer contains a pyrimidine derivative having a specific structure. This organic EL element has high efficiency, low driving voltage and a longer service life.

Description

technical field [0001] The present invention relates to organic electroluminescent devices, and more particularly, to organic electroluminescent devices (hereinafter, simply referred to as "organic EL devices") using specific arylamine compounds and specific pyrimidine derivatives. Background technique [0002] The organic EL device is a light emitting device, and is brighter, more visible, and capable of displaying more clearly than a liquid crystal device. Therefore, active research has been conducted on organic EL devices. [0003] In 1987, C.W.Tang et al. of Eastman Kodak Company developed a laminated structure device that shared various light-emitting functions among different materials, thus endowing organic EL devices with practical applicability. The developed organic EL device is constituted by laminating layers of phosphors capable of transporting electrons and layers of organic substances capable of transporting holes. As a result of injecting positive and negat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50C07B59/00C07C211/55C07C211/58C07D307/91C07D401/10C09K11/06
CPCC07B59/00C07C211/58C09K11/06C07C211/61C07C2603/18C07B2200/05C07C211/54C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1018C09K2211/1029H10K85/622H10K85/615H10K85/631H10K85/636H10K85/633H10K85/654H10K85/6574H10K50/156H10K50/16H10K50/15H10K50/12H10K85/30H10K85/6572H10K50/11H10K2101/10C07D307/91C07B59/001
Inventor 林秀一神田大三富樫和法
Owner HODOGOYA CHEMICAL CO LTD
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