Spirofluorenexanthene type electron transport material and preparation method and application thereof

An electron transport material, the technology of spirofluorene xanthene, which is applied in the direction of circuits, electrical components, electric solid devices, etc., can solve the problems of poor transmission performance, and achieve the effects of low cost, easy solution processing, and high rigidity

Inactive Publication Date: 2019-05-24
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to solve the above-mentioned problems existing in the prior art, and to propose a spirofluorene xanthene-type electron transport material with excellent criss-cross prope

Method used

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  • Spirofluorenexanthene type electron transport material and preparation method and application thereof
  • Spirofluorenexanthene type electron transport material and preparation method and application thereof
  • Spirofluorenexanthene type electron transport material and preparation method and application thereof

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preparation example Construction

[0059] The present invention also discloses a preparation method of a spirofluorene xanthene-type electron transport material, which specifically includes the following steps:

[0060] S1: The 2-bromospirofluorene xanthene derivative in the general formula I (1) is obtained by palladium-catalyzed Suzuki coupling reaction to obtain 2-(1,3,5-s-triazine)-spirofluorene xanthene derivative thing;

[0061] S2: The 2,7-dibromospirofluorene xanthene derivative in the general formula I (1) is obtained by palladium-catalyzed Suzuki coupling reaction to obtain 2,7-bis(1,3,5-s-triazine)- Spirofluorene xanthene derivatives;

[0062] Its reaction scheme general formula I is:

[0063]

[0064] Among them: L is one of the following structures

[0065]

[0066] Among them, R in the structural formula 3 and R 4 Independently of hydrogen, C1-C12 alkyl, C1-C12 alkoxy, C6-C60 aryl or C3-C60 heteroaryl;

[0067] Ar 1 and Ar 2 Independent of one of the following structural formulas:

...

Embodiment 1

[0078] Following formula is the chemical reaction formula of embodiment 1:

[0079]

[0080] Prepare B from A:

[0081] Assemble the two-neck flask, magnet, and condenser tube, leaving only the sample injection port in the sealed system, while bubbling the refined 1,4-dioxane to remove the air inside. Raw material compound A (1.00g, 2.44mmol), pinacol diboronate (0.92g, 3.62mmol), potassium acetate (0.72g, 7.32mmol), 1,1'-bisdiphenylphosphinoferrocene Palladium chloride (0.36g, 0.48mmol) was added into the flask, the system was sealed, and the reaction flask was wrapped with tinfoil. Vacuum blow nitrogen 2-3 times, inject 5 mL of 1,4-dioxane into the reaction flask. 100 ℃ oil bath stirring and heating reaction for 24h, after the reaction was completed, the organic layer was extracted with dichloromethane, the organic phase was combined, dried with anhydrous sodium sulfate, concentrated by rotary evaporation to remove the solvent, separated and purified by column chromatog...

Embodiment 2

[0085] Following formula is the chemical reaction formula of embodiment 2:

[0086]

[0087] Prepare E from D:

[0088] Assemble the two-neck flask, magnet, and condenser tube, leaving only the sample injection port in the sealed system, while bubbling the refined 1,4-dioxane to remove the air inside. The raw material compound D (1.00g, 2.05mmol), biboronic acid pinacol ester (0.78g, 3.07mmol), potassium acetate (0.60g, 6.11mmol), 1,1'-bisdiphenylphosphinoferrocene Palladium chloride (0.30 g, 0.41 mmol) was added into the flask, the system was sealed, and the reaction bottle was wrapped with tinfoil. Vacuum blow nitrogen 2-3 times, inject 5 mL of 1,4-dioxane into the reaction flask. Stir and heat the reaction in an oil bath at 90°C for 24 hours. After the reaction, extract the organic layer with dichloromethane, combine the organic phases, dry with anhydrous sodium sulfate, concentrate by rotary evaporation to remove the solvent, and separate and purify by column chromato...

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Abstract

The invention discloses a spirofluorenexanthene type electron transport material and a preparation method and application thereof. Active sites on a skeleton of fluorene and xanthene can be introducedinto photoelectric active groups, and are easy to modify without changing a cross structure, so that electron-transport is facilitated. The spirofluorenexanthene type electron transport material hasgood thermal, electrochemical and spectral stability by means of the cross structure, and the optical property and the electrical property can be achieved by changing the photoactive active groups. Therefore, the spirofluorenexanthene type electron transport material has good application prospects in the field of organic photoelectricity.

Description

technical field [0001] The invention relates to a spirofluorene xanthene-type electron transport material and its preparation method and application, which can be used in technical fields such as organic electrical storage, organic electro / photoluminescence, photovoltaic cells, organic nonlinear optics, and organic lasers. Background technique [0002] During the past three decades, organic light emitting diodes (OLEDs) have attracted enormous attention for lighting applications and for use in flat panel displays (Applied Physics Letters, 1986, 48, 183). In 1987, the first generation of fluorescent materials successfully achieved light emission. According to quantum spin statistics, the lowest excited singlet state (S 1 ) is emitted in traditional fluorescent materials (the lowest excited singlet state (S 1 ) to ground state (S 0 ))), the maximum internal quantum efficiency is only 25%, which determines that the maximum external quantum efficiency is only 5%. In the emiss...

Claims

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Application Information

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IPC IPC(8): C07D405/04C07D405/14H01L51/50H01L51/54
Inventor 解令海曹洪涛李波洪朝燊万俊黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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