Polycyclic organoboron derivative and electronic device

An electronic device and organoboron technology, applied in the fields of polycyclic organoboron derivatives and electronic devices, achieves the effects of simple preparation method, broad industrialization prospect and high thermal stability

Active Publication Date: 2020-03-24
SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Overall, the future direction of organic electroluminescent devices is to develop high-efficiency, long-life, low-cost white light devices and full-color display devices, but the industrialization process of this technology still faces many key problems

Method used

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  • Polycyclic organoboron derivative and electronic device
  • Polycyclic organoboron derivative and electronic device
  • Polycyclic organoboron derivative and electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0156] Embodiment 1: the synthesis of compound 1

[0157] (Synthesis of Intermediate 1-1)

[0158]

[0159] Under a nitrogen atmosphere, add 2,6-difluoroiodobenzene (10g, 41.67mmol), dibenzofuran-1-ol (16.9g, 91.67mmol), and potassium carbonate to a three-necked flask equipped with a reflux condenser. (23g, 166.68mmol) and 200mL N-methylpyrrolidone (NMP), and heated to reflux for 6h. After the reaction, the system was cooled to room temperature. A large amount of water was added to form a white precipitate, which was collected by suction filtration. The precipitate was washed successively with water and methanol (50% (V / V)). Finally, the obtained filter cake was dissolved in an appropriate amount of dichloromethane, and further purified by column chromatography (mobile phase: petroleum ether:dichloromethane=3:1 (V / V)) to obtain 20 g of white solid with a yield of 83%. MS (EI): m / z: 568.28 [M + ]. Anal.calcd for C 30 h 17 IO 4 (%): C 63.40, H 3.01; found: C 63.38, H...

Embodiment 2

[0164] Embodiment 2: the synthesis of compound 26

[0165] (Synthesis of Intermediate 1-2)

[0166] The synthetic route of intermediate 1-2 is shown below:

[0167]

[0168] Under nitrogen atmosphere, compound 1 (1.9 g, 4.2 mmol) was dissolved in 200 mL of chloroform and cooled to 0°C. To the above system, 10 mL of a chloroform solution of N-bromosuccinimide (NBS) (822 mg, 4.6 mmol) was added dropwise. After the dropwise addition was completed, the cooling bath was removed, the system rose to room temperature by itself, and the reaction was continued overnight at room temperature. After the reaction was completed, the reaction solution was poured into water, extracted with dichloromethane, and the organic phase was washed with water, 1N sodium hydroxide solution, and water successively. After the organic phase was dried, the solvent was removed under reduced pressure, and the resulting crude product was recrystallized from absolute ethanol to obtain 2.0 g of a light yell...

Embodiment 3

[0173] Embodiment 3: the synthesis of compound 133

[0174] (Synthesis of Intermediate 133-1)

[0175] The synthetic route of intermediate 133-1 is shown below:

[0176]

[0177] Under a nitrogen atmosphere, add 2,6-difluoroiodobenzene (10g, 41.67mmol), dibenzofuran-4-ol (16.9g, 91.67mmol), and potassium carbonate to a three-necked flask equipped with a reflux condenser. (23g, 166.68mmol) and 200mL N-methylpyrrolidone (NMP), and heated to reflux for 6h. After the reaction, the system was cooled to room temperature. A large amount of water was added to form a white precipitate, which was collected by suction filtration. The precipitate was washed successively with water and methanol (50% (V / V)). Finally, the obtained filter cake was dissolved in an appropriate amount of dichloromethane, and further purified by column chromatography (mobile phase: petroleum ether:dichloromethane=3:1 (V / V)) to obtain 22 g of a white solid with a yield of 93%. MS(EI): m / z: 568.32[M + ]. ...

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Abstract

The invention relates to a polycyclic organoboron derivative and an electronic device. According to the polycyclic organoboron derivative disclosed by the invention, a cyclic rigid structure is introduced, so that the obtained organoboron derivative is excellent in film-forming property and thermal stability, and can be used for preparing an organic light-emitting device, an organic field effect transistor and an organic solar cell. In addition, the polycyclic organoboron derivative can be used as a constituent material of a hole injection layer, a hole transport layer, a light emitting layer,an electron blocking layer, a hole blocking layer or an electron transport layer, and can reduce the driving voltage, improve the efficiency, improve the brightness, prolong the service life and thelike. In addition, the preparation method of the polycyclic organic boron derivative is simple, raw materials are easy to obtain, and the industrial development requirement can be met.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and relates to polycyclic organic boron derivatives and electronic devices containing the polycyclic organic boron derivatives. More specifically, the present invention relates to polycyclic organoboron derivatives suitable for electronic devices, especially organic electroluminescent devices, organic field effect transistors and organic solar cells, and electronic devices using the polycyclic organoboron derivatives. Background technique [0002] Organic electroluminescent devices have a series of advantages such as self-luminescence, low-voltage drive, full curing, wide viewing angle, simple composition and process, etc. Compared with liquid crystal displays, organic electroluminescent devices do not need a backlight. Therefore, organic electroluminescent devices have broad application prospects. [0003] An organic electroluminescent device generally includes an anode,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C07F9/6561C09K11/06H01L51/00H10K99/00
CPCC07F5/02C07F9/6561C09K11/06C09K2211/1092C09K2211/1096C09K2211/1088C09K2211/1033C09K2211/1037C09K2211/1029C09K2211/1011C09K2211/1014C09K2211/1044C09K2211/1059H10K85/623H10K85/622H10K85/636H10K85/633H10K85/654H10K85/657H10K85/6576H10K85/6574H10K85/6572Y02E10/549Y02P70/50
Inventor 崔林松刘向阳张业欣陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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