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Anthracene derivative and preparation method and application thereof

A technology of anthracene derivatives and compounds, applied in the field of anthracene derivatives and their preparation, can solve the problem of low fluorescence quantum yield, achieve the effects of improving fluorescence quantum yield, inhibiting π-π stacking, and reducing injection barriers

Active Publication Date: 2021-11-09
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The primary purpose of the present invention is to overcome the problem that the above-mentioned existing fluorescence quantum yield is not high, and to provide a kind of anthracene derivative

Method used

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  • Anthracene derivative and preparation method and application thereof
  • Anthracene derivative and preparation method and application thereof
  • Anthracene derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] An anthracene derivative with the molecular structure described in the following formula, named pipdAnCz:

[0063]

[0064] The preparation method of the anthracene derivative comprises the following steps:

[0065] Preparation of S1.9-(4-(10-boryl anthracene-9-yl)phenyl)-9H-carbazole:

[0066] 9-(4-(10-bromoanthracen-9-yl)phenyl)-9H-carbazole (1g, 2mmol), pinacol diboronate (0.76g, 3mmol), potassium acetate (0.4g, 4mmol ), bistriphenylphosphine palladium dichloride (0.07g, 0.1mmol) were successively added in a 100ml two-necked flask, the flask was evacuated under vacuum and replaced three times in dry nitrogen, and then added 1,4-dioxane alkane (30mL), stirred and reacted at 100°C for 24h, extracted with saturated brine and dichloromethane, and distilled under reduced pressure to obtain a black solid, using silica gel powder as the stationary phase, petroleum ether / dichloromethane as the eluent, Obtain 0.77g of white powder (yield 71%) by column chromatography;

...

Embodiment 2

[0074] A kind of anthracene derivative, has the molecular structure described in the following formula, named pipdAnTPA:

[0075]

[0076] The preparation method of the anthracene derivative comprises the following steps:

[0077] Preparation of S1.4-(10-boryl anthracene-9-yl)-N,N-diphenylaniline:

[0078] 4-(10-bromoanthracen-9-yl)-N,N-diphenylaniline (1g, 2mmol), pinacol diboronate (0.76g, 3mmol), potassium acetate (0.4g, 4mmol), Bistriphenylphosphine palladium dichloride (0.07g, 0.1mmol) was successively added in a 100ml two-necked flask, the flask was evacuated under vacuum and replaced three times in dry nitrogen, then added 1,4-dioxane ( 30mL), stirred and reacted at 100°C for 24h, extracted with saturated saline and dichloromethane, and distilled under reduced pressure to obtain a black solid, using silica gel powder as the stationary phase and petroleum ether / dichloromethane as the eluent, passing through the column Chromatography obtained 0.84 g of yellow powder ...

Embodiment 3

[0086] This embodiment provides an anthracene derivative, the preparation method of which is similar to that of Example 1. The molecular structural formula of the anthracene derivative is as follows:

[0087]

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Abstract

The invention discloses an anthracene derivative and a preparation method and application thereof. According to the anthracene derivative, anthracene serves as a bridge, (4-bromophenyl) (3-phenylimidazo [1, 2-a] pyridine-2-yl) ketone serves as a receptor, adjustment of absorption and emission spectrums is achieved by introducing a proper electron donor, a donor-acceptor structure is constructed to regulate LUMO and HOMO energy levels, transmission of balanced carriers is facilitated, and injection barriers of holes and electrons are effectively reduced. The anthracene derivative has a very twisted structure, can inhibit pi-pi accumulation among molecules and improve the fluorescence quantum yield, and can be used for preparing luminescent materials and organic electroluminescent devices.

Description

technical field [0001] The present invention relates to the 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. [0003] The luminescent material is the substance responsible for emitting light in the OLED device, so the properties of the luminescent material, such as luminous efficiency, luminous lifetime, and luminous color, will affect the performance of the OLED device. As a light-emitting material in an OLED, the following conditions should be met: 1) high fluorescence quantum yield, no serious aggregation quenching (ACQ) effect to ensure high device efficiency; 2) high thermal ...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06H01L51/54
CPCC07D471/04C09K11/06C09K2211/1044C09K2211/1011C09K2211/1007C09K2211/1029C09K2211/1014C09K2211/1037C09K2211/1033H10K85/615H10K85/631H10K85/626H10K85/657H10K85/6572Y02E10/549
Inventor 籍少敏王瑞城邢龙江霍延平陈文铖
Owner GUANGDONG UNIV OF TECH
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