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2,4,7-Trisubstituted fluorene compounds and their electronic devices

A technology of fluorene compounds and electronic devices, which is applied in the field of organic optoelectronic materials to achieve good film-forming properties, thermal stability, high luminous efficiency, and improved electron transmission efficiency

Active Publication Date: 2021-05-07
SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the operating lifetime of devices, especially for blue-light devices, remains an open question in this field.

Method used

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  • 2,4,7-Trisubstituted fluorene compounds and their electronic devices
  • 2,4,7-Trisubstituted fluorene compounds and their electronic devices
  • 2,4,7-Trisubstituted fluorene compounds and their electronic devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0296] Embodiment 1: the synthesis of compound 2-1

[0297] (Synthesis of Compound M1)

[0298] The synthetic route of compound M1 is as follows:

[0299]

[0300] In a 100 mL two-necked flask, 1.6 g (6.2 mmol) of 4-bromo-fluorenone was dissolved in 50 mL of dichloromethane, and stirred in an ice bath. Add 0.67 mL (12.8 mmol) of liquid bromine dropwise with a constant pressure dropping funnel. After the addition was complete, the system was gradually warmed up to room temperature and reacted for 6 hours. After the reaction was complete, the reaction solution was poured into a saturated sodium bisulfite solution, extracted three times with dichloromethane, the organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by spinning to obtain a crude product. The crude product was separated and purified on a silica gel column with an eluent of petroleum ether:dichloromethane=5:1 (volume ratio) to obtain 2.3 g of M1 with a yield of 90%. MS (EI): m / z 4...

Embodiment 2

[0311] Embodiment 2: the synthesis of compound 2-13

[0312] (Synthesis of compound M3)

[0313] The synthetic route of compound M3 is as follows:

[0314]

[0315] Under nitrogen, add 4.1 g (10 mmol) M1, 4.2 g (40 mmol) anhydrous sodium carbonate, 9.7 g (35 mmol) 2-boronic acid-4,6-diphenyl -1,3,5-triazine, 115.4 mg (0.1 mmol) tetrakis (triphenylphosphine) palladium and 100 mL mixed solvent (toluene: water: ethanol = 5:1:1 (volume ratio)), the system was heated to Reflux and react 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 over anhydrous sodium sulfate, concentrated under reduced pressure, and further purified by column chromatography (350 mesh silica gel, eluent: petroleum ether: dichloromethane = 4:1 (volume ratio)) to obtain a yellow solid ...

Embodiment 3

[0322] Embodiment 3: the synthesis of compound 1-23

[0323] (Synthesis of compound M4)

[0324] The synthetic route of compound M4 is as follows:

[0325]

[0326] Under nitrogen, 2.6 g (10 mmol) methyl o-iodobenzoate, 4.2 g (40 mmol) anhydrous sodium carbonate, 1.9 g (10 mmol) 2,4-di Chlorophenylboronic acid, 115.4 mg (0.1 mmol) tetrakis(triphenylphosphine) palladium and 100 mL mixed solvent (toluene: water: ethanol = 5:1:1 (volume ratio)), the system was heated to reflux and under reflux React overnight. 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 = 2:3 (volume ratio)) to obtain a white liqui...

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Abstract

The present invention provides 2,4,7-trisubstituted fluorene compounds and electronic devices thereof. The 2,4,7-trisubstituted fluorene compound of the present invention has excellent film-forming property and thermal stability by introducing a fluorene-based rigid structure, and can be used for preparing organic electroluminescence devices, organic field effect transistors and organic solar cells. In addition, the 2,4,7-trisubstituted fluorene-based compound of the present invention 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 driving voltage, improve efficiency, brightness and life, etc. The preparation method of the 2,4,7-trisubstituted fluorene compound of the present invention is simple, the raw materials are easily obtained, and the development requirements of industrialization can be met.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, and relates to 2,4,7-trisubstituted fluorene compounds and electronic devices thereof. More specifically, the present invention relates to 2,4,7-trisubstituted fluorene compounds suitable for electronic devices (especially organic electroluminescent devices, organic field effect transistors and organic solar cells), and electronic devices comprising the compounds. 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 sandwiched betwe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/61C07C211/54C07D209/86C07D519/00C07D209/94C07D307/91C07D251/24C07D219/02C07D239/26C07D265/38C07D213/06C07C13/567C07D241/38C07D333/76C07D403/10C07D491/048C07D487/04C07D403/04C07F5/02C07D311/96C07D405/14H01L51/30H01L51/54H01L51/46
CPCC07C211/61C07C211/54C07D209/86C07D519/00C07D209/94C07D307/91C07D251/24C07D219/02C07D239/26C07D265/38C07D213/06C07C13/567C07D241/38C07D333/76C07D403/10C07D491/048C07D487/04C07D403/04C07F5/027C07D311/96C07D405/14C07C2603/18C07C2603/94C07B2200/05H10K85/615H10K85/624H10K85/631H10K85/636H10K85/626H10K85/633H10K85/654H10K85/657H10K85/6572H10K85/6574Y02E10/549
Inventor 朱向东张业欣陈华
Owner SUZHOU JOYSUN ADVANCED MATERIALS CO LTD
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