Fluorene derivative and electronic device

A technology of fluorene derivatives and electronic devices, which is applied in the field of organic optoelectronic materials and achieves the effects of simple preparation method, broad industrialization prospect and lower driving voltage.

Active Publication Date: 2019-05-17
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

[0170] Embodiment 1: the synthesis of compound 10

[0171] (Synthesis of Intermediate 1)

[0172] The synthetic route of intermediate 1 is as follows:

[0173]

[0174] In a 250mL three-necked flask equipped with a thermometer, dropping funnel and mechanical stirring, add 10.0g (36.21mmol) of 2-amino-5,4'-dibromo-benzophenone and 80mL of water, and slowly drop Add 5.0g (50mmol) 98% concentrated sulfuric acid, stir for 30 minutes, cool to 0°C, add dropwise a solution of 1.5g (21mmol) sodium nitrite dissolved in 5mL water, after the dropwise addition is complete, keep this temperature for 30 minutes, slowly Raise the temperature to 60°C. After the bubbles are completely released, cool to room temperature and filter to obtain a light yellow crystalline solid. The solid was separated by column chromatography (350 mesh silica gel, the eluent was petroleum ether:dichloromethane=20:1 (V / V)), the solvent was evaporated, and after drying, 7.50 g of light yellow crystals were obtai...

Embodiment 2

[0184] Embodiment 2: the synthesis of compound 5

[0185] The synthetic route of compound 5 is as follows:

[0186]

[0187] In a 250mL three-necked flask equipped with a reflux condenser, add 10g (28.4mmol) intermediate 2A, 18.69g (85.21mmol) 1-naphthylaminobenzene, 318mg (1.42mmol) palladium acetate, 824mg (2.84mmol) ) tri-tert-butylphosphine tetrafluoroborate, 27.3g (284mmol) sodium tert-butoxide and 100ml anhydrous toluene, heated to reflux, and reacted overnight. Filter after the reaction, spin the filtrate to dryness, and separate by column chromatography (350 mesh silica gel, eluent is petroleum ether: dichloromethane = 4:1 (V / V)), evaporate the solvent, and dry to obtain white Crystallization 15.0g, yield 84%. MS(EI):m / z 628.82[(M+1) + ]. Anal.calcd for C 47 h 36 N 2 (%): C 89.77; H 5.77; N 4.46; found: C 89.50; H 5.98; N 4.52.

Embodiment 3

[0188] Embodiment 3: the synthesis of compound 17

[0189] The synthetic route of compound 17 is as follows:

[0190]

[0191] In a 250mL three-neck flask equipped with a reflux condenser, under nitrogen protection, add 10g (28.4mmol) of intermediate 2A, 29.0g (59.65mmol) of N-(4-(9-phenylcarbazol-3-yl)benzene base) biphenyl-4-amine, 318mg (1.42mmol) palladium acetate, 824mg (2.84mmol) tri-tert-butylphosphine tetrafluoroborate, 5.46g (56.8mmol) sodium tert-butoxide and 100ml anhydrous toluene, heated to reflux , reacted overnight. Filter after the reaction, spin the filtrate to dryness, and separate by column chromatography (350 mesh silica gel, eluent is petroleum ether: dichloromethane = 4:1 (V / V)), evaporate the solvent, and dry to obtain white Crystallization 29.0g, yield 87%. MS(EI):m / z 1163.48[(M+1) + ]. Anal.calcd for C 87 h 62 N 4 (%): C 89.81; H 5.37; N 4.82; found: C89.60; H 5.48; N 4.92.

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Abstract

The invention relates to a fluorene derivative and an electronic device. By introducing a fluorene rigid structure, the obtained fluorene derivative has excellent film forming property and thermal stability, and can be used for preparing organic electroluminescent devices, organic field effect transistors and organic solar cells; in addition, the fluorene derivative can be used as a constituent material of a hole injection layer, a hole transport layer, a luminescent layer, an electron blocking layer, a hole blocking layer or an electron transport layer, a driving voltage can be reduced, efficiency and brightness can be improved, and the service life is prolonged; and in addition, the preparation method of the fluorene derivative is simple, raw materials are easily available, and industrial development requirements 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 2,6-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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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07D519/00C07D209/86C07C211/54C07D251/24C07D403/10C07D221/20C07D401/04C07D401/14C07F9/576C07F7/08C07D471/06C07F9/6561C07D498/06C07D513/06C07F5/02C07F9/6584C07D471/10C07D498/10C07D513/10C07D241/38C07D333/76C07D307/91C09K11/06H01L51/50H01L51/54
CPCC07C211/61C07D519/00C07D209/86C07C211/54C07D251/24C07D403/10C07D221/20C07D401/04C07D401/14C07F9/5765C07F7/0814C07D471/06C07F9/65616C07D498/06C07D513/06C07F5/02C07F9/6584C07D471/10C07D498/10C07D513/10C07D241/38C07D333/76C07D307/91C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092C07C2603/18H10K85/624H10K85/626H10K85/633H10K85/615H10K85/631H10K85/654H10K85/6576H10K85/6574H10K85/657H10K85/40H10K85/6572H10K50/15H10K50/16H10K50/17H10K50/18H10K50/11C07F7/08C07F9/576C07F9/6561Y02E10/549H10K50/00
Inventor 崔林松张业欣林久栋陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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