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9-(1-fluoro-9H-fluoren-9-yl)anthracene and preparation method thereof

A compound and zinc powder technology, applied in the field of blue luminescent materials and their preparation, to achieve the effects of stable structure, easy storage and high luminous efficiency

Inactive Publication Date: 2011-08-31
SHANGHAI UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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The synthesis method of this compound has not been reported yet

Method used

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  • 9-(1-fluoro-9H-fluoren-9-yl)anthracene and preparation method thereof

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Effect test

Embodiment 1

[0028] Embodiment 1: Preparation of 9-(1-fluoro-9H-fluorene-9-yl)anthracene adopts the following steps: 1. add 9-bromo-1-fluoro-9H in a 50 ml round-bottomed flask equipped with a reflux condenser - 0.53 g of fluorene, 0.356 g of anthracene, 0.13 g of zinc powder, and 15 ml of carbon disulfide. ②The reactant was stirred and reacted under reflux for 24 hours, and then the reaction was stopped. ③ After the reaction is completed, cool to room temperature, remove the zinc powder by suction filtration, and concentrate the filtrate. ③ The obtained concentrate was separated by silica gel chromatography, using petroleum ether as a developer, and then recrystallized from petroleum ether / ethyl acetate to obtain 0.45 g of white crystals, with a yield of 62%.

Embodiment 2

[0029] Embodiment 2: Preparation of 9-(1-fluoro-9H-fluorene-9-yl) anthracene adopts the following steps: 1. add 9-bromo-1-fluoro-9H in a 250 ml round-bottomed flask equipped with a reflux condenser - fluorene 4.78g, anthracene 3.2g, zinc powder 1.17g, carbon disulfide 100ml. ②The reactant was stirred and reacted under reflux for 24 hours, and then the reaction was stopped. ③ After the reaction is completed, cool to room temperature, remove the zinc powder by suction filtration, and concentrate the filtrate. ③ The obtained concentrated solution was separated by silica gel chromatography, using petroleum ether as a developer, and then recrystallized from petroleum ether / ethyl acetate to obtain 4.15 g of white crystals, with a yield of 64%.

Embodiment 3

[0030] Example Three: The following steps are used to prepare 9-(1-fluoro-9H-fluorene-9-yl)anthracene: 1. add 9-bromo-1-fluoro-9H to a 2-liter round-bottomed flask equipped with a reflux condenser - fluorene 43.1g, anthracene 28.8g, zinc powder 10.53g, carbon disulfide 1200ml. ②The reactant was stirred and reacted under reflux for 24 hours, and then the reaction was stopped. ③After the reaction is completed, cool to room temperature, remove the zinc powder by suction filtration, and concentrate the filtrate. ③ The obtained concentrated solution was separated by silica gel chromatography, using petroleum ether as a developer, and then recrystallized from petroleum ether / ethyl acetate to obtain 34.9 g of yellow-green crystals, with a yield of 60%.

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Abstract

The invention relates to 9-(1-fluoro-9H-fluoren-9-yl)anthracene and a preparation method thereof. The structural formula of the compound is shown in the specification of the invention. In the preparation method, anthracene is connected with the site 9 of fluorene creatively; and fluorene atom is introduced to the site 1 of a fluorene ring to investigate the influence of the fluorene atom on the three-dismetional structure and performance of the whole compound. Experiments show that the compound has high fluorescence quantum efficiency and thermal stability, stable structure, high luminous efficiency and good color purity and is easy to store; the fluorescent emission wavelength of the compound is 438nm in solution, which is in the blue luminous range; and the fluorescent efficiency is 71% in solution. The method uses common raw materials easily obtained, is very simple to operate and convenient in synthesis; and the total yield is 60%-65% and the method is suitable for mass production.

Description

technical field [0001] The invention relates to a blue luminescent material and a preparation method thereof, in particular to 9-(1-fluoro-9H-fluoren-9-yl)anthracene and a preparation method thereof. Background technique [0002] With the advancement of science and technology and the development of the times, people need a new generation of flat-panel displays with better performance and better meet the needs of future life, especially the future trend is to transmit a large amount of information and images on light and flexible bodies, and flat-panel displays are no longer In line with these requirements, organic light-emitting diodes (OLEDs) have become a very popular emerging flat-panel display industry at home and abroad this year, mainly because OLED displays have self-illumination, wide viewing angles (over 170°), and fast response times (1us order of magnitude) ), high luminous efficiency, low working voltage (3-10V), thin panel thickness (less than 2mm), large-size a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/22C07C17/266C09K11/06
Inventor 王静万文赵伟明蒋海珍郝健
Owner SHANGHAI UNIV