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Dithienopyridine zinc coordination compound luminescence material and preparation method thereof

A technology of phenopyridine zinc and luminescent materials, which is applied in the direction of luminescent materials, zinc organic compounds, chemical instruments and methods, etc., can solve the problems of insufficient simplification of the production process, short device life, and low product share, and achieve structural stability, High atom economy and wide-ranging effects

Inactive Publication Date: 2015-12-23
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, devices made of organic materials have entered the market in small batches, but due to many problems such as low yield, short device life, and insufficient simplification of the production process, the market share of the products is not high, and sales are low. expensive

Method used

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  • Dithienopyridine zinc coordination compound luminescence material and preparation method thereof
  • Dithienopyridine zinc coordination compound luminescence material and preparation method thereof
  • Dithienopyridine zinc coordination compound luminescence material and preparation method thereof

Examples

Experimental program
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Effect test

example example 1

[0031] Example 1 The preparation process of bisthiophene pyridine zinc complex luminescent material I

[0032] Add 3,4-diaminothieno[2,3-b]thiophene-2,5-dinitrile (1mmol) and acetone (4mL) to a 12mL polytetrafluoroethylene liner in a hydrothermal reactor, and stir until evenly dispersed, add ZnCl 2 (5mmol), the polytetrafluoroethylene liner was reacted at 140°C for 3.0h. After the reaction, directly filter and wash with water. The crude product was recrystallized with ethanol and water to obtain pale yellow crystals (I), and the single crystal structure of complex I was as follows: figure 2 a, the yield is about 60% (mother liquor recovery), m.p.>300°C. The reaction formula of 3,4-diaminothieno[2,3-b]thiophene-2,5-dinitrile and acetone is:

[0033]

[0034] The spectral data of product (I) is 1 HNMR (DMSO-d 6 ,400MHz)δ:7.55(s,4H,NH 2 ),6.58(s,2H,ArH),2.72(s,6H,CH 3 ). 13 CNMR (DMSO-d 6 ,100MHz) δ: 155.7, 151.9, 146.7, 146.0, 129.7, 119.0, 104.1, 22.8.

example example 2

[0035] Example 2 The preparation process of bisthiophene pyridine zinc complex luminescent material II

[0036] Add 3,4-diaminothieno[2,3-b]thiophene-2,5-dicarbonitrile (1mmol) and cyclohexanone (4mL) into a 25ml one-necked flask, stir until uniformly dispersed, add ZnCl 2 (5 mmol), and then rapidly heated to reflux at 150° C., and reacted with magnetic stirring for 4 h. After the reaction, directly filter and wash with water to obtain a solid mixture. The crude product was recrystallized from a mixture of DMF and water to obtain white crystals (II), and the single crystal structure of complex I was as follows: figure 2 a, the yield is about 74% (mother liquor recovery), m.p.>300°C. Measure its thermal weight, such as image 3 shown. The reaction formula of 3,4-diaminothieno[2,3-b]thiophene-2,5-dicarbonitrile and cyclohexanone is:

[0037]

[0038] The spectral data of product (II) is: 1 HNMR (DMSO-d 6 ,400MHz)δ:7.25(s,4H,NH 2 ),3.27(s,4H,CH 2 ),2.57(s,4H,CH 2 ), 1...

example example 3

[0039] Fluorescence test of example 3 bisthiophene pyridine zinc complexes

[0040] The bisthiophene pyridine zinc complex prepared in Example 2 was dissolved in DMSO and prepared as 1*10 -2 mol / L stock solution. Take 3uL from the stock solution and add it to 3mL water to prepare 1*10 -5 mol / L ethanol solution, the fluorescence emission performance test was carried out on a Hitachi F-7000 fluorescence spectrometer.

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Abstract

The present invention discloses a dithienopyridine zinc coordination compound and a preparation method thereof. The dithienopyridine zinc coordination compound is formed by complexing a ligand dithienopyridine and zinc chloride, wherein the molecular structure general formula is defined in the specification, the skeletal structure of ligand is a binding body of thiophthene and pyridine, contains two nitrogen atoms capable of simultaneously performing chelating coordination, and provides good coordination ability on transition metals, and the ligand has a rigid plane-like structure and the conjugating system is large so as to achieve the good fluorescence property. According to the present invention, 3,4-diaminothieno[2,3-b]thiophene-2,5-dinitrile is adopted as the raw material, the 3,4-diaminothieno[2,3-b]thiophene-2,5-dinitrile and ketone are subjected to a Friedlander reaction under the induction of zinc chloride, a series of the dithienopyridine zinc coordination compounds are synthesized through the one-pot method, and the ligand and the ZnCl2 can be subjected to in situ coordination to form the stable coordination compound without separation, such that the operation process is simple, the atom economy is high, the reaction conditions are mild, and the yield is high; and the coordination compound material can be used as the luminescence material, and can be used as the luminescence layer material in the luminescence device.

Description

(1) Technical field [0001] The invention relates to a complex and a preparation method thereof, in particular to a bisthienopyridine zinc complex luminescent material with yellow luminescence performance and a preparation method thereof, belonging to the technical field of metal complex solid luminescent materials. (2) Background technology [0002] Organic light-emitting materials can be divided into organic small molecule compound materials and high molecular polymer materials according to the molecular structure of the compound. Small organic molecular compound materials have attracted more and more attention because of their strong chemical modification, wide selection range, easy purification, high fluorescence quantum efficiency, and the ability to generate various colors of light. Metal complexes are between organic and inorganic substances. They have the advantages of good stability of inorganic substances and high fluorescence quantum efficiency of organic substance...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F3/06
Inventor 李加荣杨俊娟邱发东史大昕张奇
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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