A kind of anthracene derivative and its preparation method and application

An anthracene derivative and reaction technology, applied in the field of anthracene derivatives and their preparation, can solve the problems of insufficient carrier injection and transport, and the need to improve the fluorescence quantum efficiency of solid-state thin film aggregated state, so as to be beneficial to factory production. preparation, beneficial to popularization and application, and the effect of improving fluorescence quantum efficiency

Active Publication Date: 2020-10-09
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention provides an anthracene derivative in order to overcome the disadvantages of insufficient balance of carrier injection and transport described in the prior art and the need to improve the quantum efficiency of solid-state thin film aggregated fluorescence. In the provided anthracene derivative, carrier injection and The transmission is more balanced, and the solid-state film aggregation state has high fluorescence quantum efficiency, and can also perform efficient blue light emission in organic solvents

Method used

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  • A kind of anthracene derivative and its preparation method and application
  • A kind of anthracene derivative and its preparation method and application
  • A kind of anthracene derivative and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0066] Example 1 Preparation of 4-(10-(9,9'-spirobis[fluorene]-2-yl)anthracen-9-yl)benzonitrile

[0067] Step 1: Preparation of 4-(10-bromoanthracen-9-yl)benzonitrile:

[0068] Add 9,10-dibromoanthracene (1.67g, 5mmol), 4-cyanophenylboronic acid (0.74g, 5mmol), and tetrakistriphenylphosphine palladium (0.115g, 0.1mmol) into a 250mL two-necked flask in sequence, and The flask was evacuated under vacuum and replaced three times under dry nitrogen, then 40 mL of toluene was added and 10 mL of saturated K 2 CO 3 aqueous solution. The reaction was heated to reflux at 90° C. and stirred for 12 hours. Extract with saturated brine and dichloromethane. Distilled under reduced pressure to obtain a yellow solid, using silica gel powder as a stationary phase and petroleum ether / dichloromethane as an eluent, 0.89 g of a white powder was obtained by column chromatography (yield 50%).

[0069] The reaction equation is as follows:

[0070]

[0071] Step 2: Preparation of 2-boryl-9,9'...

Embodiment 2

[0082] Example 2 Preparation of 4-(10-(9,9-diphenyl-9H-fluoren-2-yl)anthracen-9-yl)benzonitrile

[0083] Step 1 of the present embodiment is the same as embodiment 1, and step 2 and step 3 are as follows:

[0084] Step 2: Preparation of 2-boryl-9,9-diphenyl-9H-fluorene

[0085] 2-Bromo-9,9-diphenyl-9H-fluorene (1.18g, 3mmol), biboronic acid pinacol ester (1.02g, 4mmol), catalyst [1,1'-bis(diphenylphosphine) Ferrocene] palladium dichloride dichloromethane complex (0.073, 0.09mmol), potassium acetate (0.882g, 9mmol) were successively added to a 100mL two-necked flask, and the flask was evacuated under vacuum and replaced three times in dry nitrogen , then 1,4-dioxane (20 mL) was added. After stirring the reaction at 85°C for 8 hours, it was extracted with saturated brine and dichloromethane. Distilled under reduced pressure to obtain a black solid, using silica gel powder as a stationary phase and petroleum ether / dichloromethane as an eluent, 1.02 g of a white oil was obtaine...

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PUM

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Abstract

The invention discloses an anthracene derivative and its preparation method and application. The anthracene derivative has a chemical structure shown in formula (I) or formula (II); the anthracene derivative provided by the invention utilizes the highly efficient fluorescence quantum efficiency of anthracene As a bridge, with the help of the electron-withdrawing and electron-donating properties of the cyano group and the electron-donating properties of the fluorene group, the carrier injection and transport are more balanced, which is conducive to improving the performance of the device; at the same time, the fluorene group with a large steric hindrance twisted structure improves the aggregation state of the solid film High fluorescence quantum efficiency, and efficient blue light emission in organic solvents. The invention also provides a preparation method of the anthracene derivative, and its application in the preparation of blue light-emitting materials, light-emitting devices or smart materials.

Description

technical field [0001] The present invention relates to the technical field of organic luminescent materials, more specifically, to an anthracene derivative and its preparation method and application. Background technique [0002] Organic light-emitting diodes (OLEDs) have huge applications in flat panel displays, smartphones, and solid-state lighting due to their light weight, good flexibility, wide operating temperature range, short response time, high brightness and contrast, and wide viewing angles. potential. Among them, OLED devices are of decisive significance to display technologies such as full-color display and solid-state lighting. So far, although there have been many reports on anthracene-based light-emitting materials based on small-molecule organic electroluminescent devices, due to the large planar nature of anthracene molecules, it will form π-π stacking in the aggregated state, resulting in its fluorescence being quenched. off, thereby reducing the effici...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/50C07C253/30C09K11/06H01L51/54
CPCC07C255/50C09K11/06C07C2603/24C07C2603/94C07C2603/18C09K2211/1007C09K2211/1011H10K85/624H10K85/615H10K85/626
Inventor 籍少敏邢龙江贺佳邱志鹏霍延平杨庆旦
Owner GUANGDONG UNIV OF TECH
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