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Conjugated polymer containing pyridine on main chain, preparation process and use thereof

A technology of conjugated polymer and pyridine, which is applied to the conjugated polymer containing pyridine on the main chain and the fields of its preparation and use, can solve the problem that polypyridine cannot transport holes well, pollute the environment, and the luminescence performance of polymers, single The problem of low efficiency of layer light-emitting devices, etc., achieves the effects of low cost, changing the light-emitting wavelength, and easy industrial production.

Inactive Publication Date: 2003-10-22
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These pyridine polymers are limited to pyridine homopolymers and polypyridine acetylene. These polymers can only be dissolved in acidic solutions such as formic acid or hydrochloric acid, and cannot be dissolved in common organic solvents. Acidic solvents not only pollute the environment but also have an impact on the luminescent properties of the polymer. , causing a red shift in the emission wavelength
The efficiency of single-layer light-emitting devices made of this polymer is very low [A.P.Monkman et al., SPIE, 1997, 3145, 208-18]
The reason is that polypyridine cannot transport holes very well

Method used

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  • Conjugated polymer containing pyridine on main chain, preparation process and use thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0013] Example 1: A 100 ml three-necked reaction flask is equipped with a water condenser, a constant pressure dropping funnel, and an argon gas introduction tube. The argon gas is led out from the top of the condenser tube, and connected to the atmosphere through a drying tower filled with calcium chloride or sodium hydroxide. A stirring magnet is placed in the bottle, and the reaction bottle is placed on the magnetic stirrer. Before the reaction, pass argon gas for five minutes. Under the protection of argon flow, add 0.38 g (4 mmol) of pyridine N-oxide and 20 ml of chloroform to dissolve the pyridine oxide, then add 3.9 g (24 mmol) of anhydrous ferric trichloride, and keep Add 0.5 g (2 mmol) of N-hexylcarbazole into the pressure dropping funnel and dissolve in 15 ml of chloroform, slowly add N-hexylcarbazole dropwise into the three-necked flask, stir with magnetic force, and react at 28°C for 40 hours. Then the reaction solution was poured into 100ml ethanol, stirred for t...

Embodiment 2

[0014] Embodiment 2: The device used is the same as in Example 1. Add 0.67 g (7 mmol) of pyridine N-oxide and 25 ml of chloroform into the three-necked flask, and after dissolving, add 6.8 g (42 mmol) of anhydrous ferric chloride. Add 0.86 g (3.5 mmol) of triphenylamine and 15 ml of chloroform into the constant pressure dropping funnel. Slowly add triphenylamine dropwise, react at 40°C for 36 hours, pour into 120ml of ethanol, stir for 2 hours, and filter with suction to obtain a conjugated polymer of yellow precipitated pyridine oxide and triphenylamine, which is extracted with ethanol after drying. After drying (50° C.), the weight was 0.72 g, and the yield was 47.1%. Reduction: Dissolve 0.31g of the obtained product in 20ml of frozen chloroform, add 0.4ml of phosphorus trichloride, control the temperature at 75°C, react for one hour and then cool, then add 20ml of water and stir, neutralize with sodium hydroxide until alkaline, Collect the organic phase in the reaction bo...

Embodiment 3

[0015] Example 3: A 100 ml three-necked reaction flask is equipped with a water condenser and an argon inlet tube. The argon gas is led out from the top of the condenser tube, and connected to the atmosphere through a drying tower filled with calcium chloride. A stirring magnet is placed in the bottle, and the reaction bottle is placed on the magnetic stirrer. Before the reaction, pass argon for five minutes. Under the protection of argon flow, add 0.57 g (6 mmol) of pyridine N-oxide and 0.51 g (3 mmol) of fluorene from another opening of the three-neck flask (stopped with a ground stopper before this), 30ml of chloroform was dissolved, then 5.85g (36mmol) of anhydrous ferric trichloride was added, reacted in an ice-salt bath for 48 hours, poured into 100ml of ethanol, stirred for 2 hours, and suction filtered to obtain yellow solid pyridine oxide and The conjugated polymer of fluorene was dried in the air, extracted with ethanol, dried (50° C.), weighed: 0.68 g, and the yiel...

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Abstract

The present invention relates to a conjugated polymer whose main chain contains pyridine. Said invention provides its structure formula and its preparation method. It uses pyridine oxide and correspondent aromatic heterocycle or aromatic carbocydic ring and its derivative as raw material, uses halohydrocarbon or nitrobenzene as solvent, makes them produce reaction in the presence of Lewis acid at-10 deg.C-40 deg.C to obtain the polymer whose main chain contains pyridine oxide, then uses phosphorus trichloride or titanium trichloride to make reduction reaction so as to obtain the required polymer whose main chain contains pyridine. Said invented conjugated polymer can be used as luminou s material of electroluminescence device and electric charge transmission material.

Description

technical field [0001] The invention relates to a conjugated polymer containing pyridine in the main chain, a preparation method and application thereof. Background technique [0002] Pyridine is an electron-deficient aromatic ring, and polypyridine is both a light-emitting material and an efficient electron-transport material, and it is stable to oxygen. Polypyridine is successfully used in organic light-emitting devices and improves the performance of the devices [S. Daily, et al., J. Phys.: Condens. Matter, 10, 5171 (1998)]. Patent WO9629,747 reported that Wang Yunzhang et al. made a bipolar electroluminescent device with polypyridine. These pyridine polymers are limited to pyridine homopolymers and polypyridine acetylene. These polymers can only be dissolved in acidic solutions such as formic acid or hydrochloric acid, but cannot be dissolved in common organic solvents. Acidic solvents not only pollute the environment but also have an impact on the luminescent propertie...

Claims

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Application Information

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IPC IPC(8): C08F126/06
Inventor 詹才茂郑金云
Owner WUHAN UNIV
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