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Organic compound based on binaphthylamine derivative and organic electroluminescent device

A technology of organic compounds and derivatives, applied in the field of organic electroluminescent devices, can solve the problems of wide spectrum, inability to meet the requirements of high color purity in the display field, loss of energy, etc., and achieve the effect of narrow emission spectrum characteristics

Pending Publication Date: 2022-07-15
JIHUA HENGYE (FOSHAN) ELECTRONIC MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, conventional TADF materials are easily affected by the vibration and rotational motion between donor and acceptor, resulting in a wider spectrum, and more energy will be lost in the actual commercial panel preparation.
Although a wider spectrum is beneficial for lighting applications, it cannot meet the requirements of high color purity in the display field

Method used

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  • Organic compound based on binaphthylamine derivative and organic electroluminescent device
  • Organic compound based on binaphthylamine derivative and organic electroluminescent device
  • Organic compound based on binaphthylamine derivative and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Preparation of Example 1 Compound (1-1-1)

[0084] The synthetic route of compound 1-1-1 is as follows:

[0085]

[0086] Under nitrogen atmosphere, [1,1'-binaphthyl]-2,2'-diamine (2.7 g, 9.5 mmol, 1 eq (equiv), iodobenzene (4.2 g, 20.9 mmol, 2.2 eq), tris( Dibenzylideneacetone)dipalladium (Pd 3 (dba) 2 ) (173 mg, 0.19 mmol, 0.02 eq), 1,1'-bis(diphenylphosphino)ferrocene (dppf) (107 mg, 0.19 mmol, 0.02 eq) and sodium tert-butoxide (NaOtBu) (2.6 g, 28.4 mmol, 3 eq) was dispersed in 20 mL of toluene (Toluene). The reaction was carried out at 120°C for 12 hours. After the reaction, the solvent was spun dry, and the crude product was further purified by column chromatography using petroleum ether:dichloromethane (90:10 by volume). The intermediate product P-1 was obtained in a yield of 3.5 g (85% yield).

[0087] Under nitrogen atmosphere, intermediate P-1 (3.1 g, 7.1 mmol, 1 eq), sodium hydride (NaH) (0.33 g, 14.1 mmol, 2 eq) and o-cyanotetrafluorobenzene (1.4 g, ...

Embodiment 2

[0089] Preparation of Example 2 Compound (1-1-4)

[0090] The synthetic route of compound 1-1-4 is shown below:

[0091]

[0092] Under nitrogen atmosphere, 5-bromo-1,3-difluoro-2-iodobenzene (20.0 g, 62.7 mmol, 1 eq), tetra-tert-butylphenol (28.2 g, 188.1 mmol, 3 eq) and sodium hydride (4.5 g, 188.1 mmol, 3 eq) was dispersed in 80 mL of N,N'-dimethylformamide (DMF). The product was stirred at room temperature for 12 hours. After cooling to room temperature, the reactant was poured into ice water, the precipitate was filtered and washed with water, the crude product was extracted with dichloromethane and water, the organic layer was collected, the organic layer was dried over anhydrous magnesium sulfate, the solvent was spin-dried, and the crude product was passed through a column Chromatography was further purified using petroleum ether:dichloromethane (90:10 by volume). Intermediate P-3 was obtained in a yield of 29.0 g (80% yield).

[0093] Under a nitrogen atmospher...

Embodiment 3

[0098] Preparation of Example 3 Compound (1-1-24)

[0099]The synthetic route of compound 1-1-24 is shown below:

[0100]

[0101] Under nitrogen atmosphere, 5,5',6,6',7,7',8,8'-octahydro-[1,1'-binaphthyl]-2,2'-diamine (2.8 g, 9.5mmol, 1eq), iodobenzene (4.2g, 20.9mmol, 2.2eq), tris(dibenzylideneacetone)dipalladium()(173mg, 0.19mmol, 0.02eq), 1,1'-bis(diphenyl) phosphine)ferrocene (dppf) (107 mg, 0.19 mmol, 0.02 eq) and sodium tert-butoxide (2.6 g, 28.4 mmol, 3 eq) were dispersed in 20 mL of toluene (Toluene). The reaction was carried out at 120°C for 12 hours. After the reaction, the solvent was spun dry and the crude product was further purified by column chromatography using petroleum ether:dichloromethane (90:10). The intermediate product P-8 was obtained in a yield of 3.5 g (85% yield).

[0102] Under nitrogen atmosphere, intermediate P-8 (3.1 g, 7.1 mmol, 1 eq), sodium hydride (NaH) (0.33 g, 14.1 mmol, 2 eq) and o-bromotetrafluorobenzene (2.1 g, 7.1 mmol, 1 eq) we...

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Abstract

The invention relates to the technical field of organic electroluminescence, and discloses an organic compound based on a binaphthylamine derivative and an organic electroluminescence device, the structural general formula of the organic compound based on the binaphthylamine derivative is shown in the specification, and the organic compound based on the binaphthylamine derivative has narrow emission spectrum characteristics and high quantum yield. And the photoelectric property requirement of the organic electroluminescent device is met.

Description

technical field [0001] The present application relates to the technical field of organic electroluminescence, and mainly relates to organic compounds and organic electroluminescence devices based on binaphthylamine derivatives. Background technique [0002] Organic Light Emitting Diode (OLED) has the advantages of high efficiency, low turn-on voltage, and wide viewing angle, and has become a new generation of display and lighting technology. With the wide application of OLED in display fields such as smartphones, TVs, and wearables, the three East Asian countries (China, Japan, and South Korea) have invested trillions of RMB in OLED panel production lines in the past decade or so. [0003] Since the research of Forrest et al. of Princeton University in the United States in 1998 found that the organic light-emitting device prepared by the general organic fluorescent dye doping technology can realize the process of electroluminescence under the condition of electricity, so the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D403/14C07D409/14C07D413/14C07D487/04C07D495/04C07D495/14C07D495/22C07D519/00C07F5/02C09K11/06H01L51/54H01L51/50
CPCC07D403/14C07D487/04C07D409/14C07F5/027C07D495/04C07D495/14C07D413/14C07D401/14C07D519/00C07D495/22C09K11/06C09K2211/1085C09K2211/1074C09K2211/1044C09K2211/1059C09K2211/1092C09K2211/1011C09K2211/1096C09K2211/1029C09K2211/1033H10K85/615H10K85/626H10K85/654H10K85/657H10K85/6576H10K85/6572H10K85/6574H10K50/11
Inventor 晏志平宋小贤梁洁毕海王悦
Owner JIHUA HENGYE (FOSHAN) ELECTRONIC MATERIALS CO LTD
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