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Fluorene derivative and electronic device

A technology of fluorene derivatives and electronic devices, applied in the field of organic optoelectronic materials

Inactive Publication Date: 2020-04-24
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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  • Fluorene derivative and electronic device
  • Fluorene derivative and electronic device
  • Fluorene derivative and electronic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0214] Embodiment 1: the synthesis of compound 19

[0215] (Synthesis of Intermediate 1)

[0216] The synthetic route of intermediate 1 is as follows:

[0217]

[0218] Under nitrogen, add 6.7g (47.8mmol) 2-fluorophenylboronic acid, 8.4g (79.6mmol) anhydrous sodium carbonate, 9.3g (39.8mmol) 2-bromo-6-fluoro Methyl benzoate, 470.8 mg (4.8 mmol) tetrakis(triphenylphosphine) palladium and 100 mL of a mixed solvent (toluene:water:ethanol=5:1:1 (V / V)). The system was gradually heated to reflux and reacted overnight under reflux. After the reaction was completed, the heating was stopped, and the reaction system was cooled to room temperature by itself. The reaction solution was poured into about 200 mL of water, and extracted with dichloromethane. The organic phase was dried with anhydrous sodium sulfate, concentrated under reduced pressure, and further purified by column chromatography (350 mesh silica gel, eluent: petroleum ether: dichloromethane = 15:1 (V / V)) to obtain li...

Embodiment 2

[0236] Embodiment 2: the synthesis of compound 20

[0237] (Synthesis of Intermediate 20A)

[0238] The synthetic route of intermediate 20A is shown below:

[0239]

[0240] 5g (23mmol) of intermediate 2, 14.1g (50.6mmol) of 3,6-di-tert-butylcarbazole and 12.7g (92mmol) of anhydrous potassium carbonate were successively added into a dry and clean 250mL three-necked flask. The system was replaced with nitrogen back and forth three times to remove the air therein. Add 150mL of N-methylpyrrolidone, gradually raise the temperature to 180°C, and react at this temperature overnight. After the reaction was cooled, the inorganic salt was removed by suction filtration, and the filtrate was distilled under reduced pressure to obtain a reddish-brown residue. The crude product was further purified by column chromatography (350 mesh silica gel, eluent: petroleum ether:dichloromethane=4:1 (V / V)) to obtain 16.3 g of orange-red solid with a yield of 96%. MS(EI): m / z: 735.01[M + ]. An...

Embodiment 3

[0249] Embodiment 3: the synthesis of compound 353

[0250] (Synthesis of compound 353)

[0251] The synthetic route of compound 353 is as follows:

[0252]

[0253] Under nitrogen protection, 2.0 g (8.9 mmol) of 2-bromobiphenyl and 150 mL of anhydrous tetrahydrofuran were added to a dry and clean 250 mL three-neck flask, and stirred to dissolve at room temperature. The system was cooled to -78°C, and 3.9 mL (2.5 M, 9.8 mmol) of n-butyllithium was added dropwise at this temperature, and stirring was continued at this temperature for 1.5 h after the addition was complete. Subsequently, 4.1 g (8.1 mmol) of intermediate 19A was added in one batch. After the addition, the cooling bath was removed, and the reaction was warmed to room temperature by itself and continued to stir overnight. After the reaction, it was washed with water, dried, and spin-dried to obtain a white solid.

[0254] The above white solid was transferred to a 250mL one-necked bottle equipped with a reflux...

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PUM

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Abstract

The invention provides a fluorene derivative and an electronic device. A fluorene rigid structure is introduced into the fluorene derivative, so that the obtained fluorene 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 fluorene 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 and brightness, prolong the service life and the like. In addition, the preparation method of the fluorene 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 fluorene derivatives and electronic devices containing the fluorene derivatives. More specifically, the present invention relates to 1,5-disubstituted fluorene derivatives suitable for electronic devices, especially organic electroluminescent devices, organic field effect transistors and organic solar cells, and electronic devices using the fluorene 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, a metal cathode, and an organic layer san...

Claims

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Application Information

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IPC IPC(8): C07D221/20C07D401/14C07D417/14C07D413/14C07D409/14C07D405/14C07C255/51C07C211/61C07D209/86C07D209/88C07D209/94C07D519/00C07D307/91C07D333/76C07D241/36C07D239/26C07D251/24C07D471/10C07D213/06C07F9/53C07F5/02C07D279/22C07D265/38C07D219/02C07D235/20C07D498/10C07D513/10C07F9/6584C07F7/10C07F7/08C07F7/30C09K11/06H01L51/30H01L51/46H01L51/54
CPCC07D221/20C07D401/14C07D417/14C07D413/14C07D409/14C07D405/14C07C255/51C07C211/61C07D209/86C07D209/88C07D209/94C07D519/00C07D307/91C07D333/76C07D241/36C07D239/26C07D251/24C07D471/10C07D213/06C07F9/5325C07F5/027C07F7/0805C07D279/22C07D265/38C07D219/02C07D235/20C07D498/10C07D513/10C07F9/6584C07F7/0816C07F7/30C09K11/06C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092H10K85/649H10K85/622H10K85/636H10K85/633H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K85/40H10K50/18H10K50/15H10K50/16H10K50/17H10K50/11Y02E10/549
Inventor 崔林松刘向阳张业欣陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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