Water-soluble small molecule pyridinium photoelectric material and preparation method and application thereof

A molecular pyridinium salt, photoelectric material technology, applied in photovoltaic power generation, chemical instruments and methods, circuits, etc., can solve the uncertainty of polymer molecular weight, purity and structure, it is difficult to ensure the performance stability of different batches of materials, high Cost of vacuum evaporation process and other issues, to avoid the uncertainty of purity and molecular weight, good carrier injection/extraction characteristics, and low electron injection/extraction energy barriers.

Inactive Publication Date: 2013-07-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the research of this kind of pyridine-based materials, most of them are evaporation-type small molecules. Although they have achieved excellent performance in the application of OLEDs, the complicated device manufacturing process and high-cost vacuum evaporation process make them There are many difficulties in large-scale industrial production; of course, a class of polymer materials containing pyridine groups has also begun to be used in polymer solar cells, but the molecular weight, purity and structure of the polymer itself are uncertain, and it is difficult to guarantee different batches of polymer materials. Performance stability of secondary materials

Method used

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  • Water-soluble small molecule pyridinium photoelectric material and preparation method and application thereof
  • Water-soluble small molecule pyridinium photoelectric material and preparation method and application thereof
  • Water-soluble small molecule pyridinium photoelectric material and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0042] The preparation method of the water-soluble small molecule pyridinium salt photoelectric material of the present embodiment comprises the following steps:

[0043] Step 1: the synthesis of p-bromomethylbenzonitrile, as follows:

[0044]

[0045] Under nitrogen protection, add p-tolunitrile (5.05g, 43mmol) and 50ml of carbon tetrachloride to a 150ml reaction vessel and stir, then add N-bromosuccinimide (7.69g, 43mmol) in Stir at room temperature for 10 minutes. Finally, the catalyst benzoyl peroxide (0.63g.2.0mmol) was added and heated to 80°C for 5 hours in the dark. After the temperature dropped to 60°C, the resulting filtrate was filtered under reduced pressure to obtain a light yellow solid. Recrystallized from a mixed solvent of absolute ethanol: ethyl acetate = 3:1 to obtain 4.67 g of white crystals, with a yield of 55.2%. The nuclear magnetic resonance result of the intermediate product that step one obtains is as follows: 1 H NMR (300MHz, CDCl 3 ), (ppm):...

Embodiment 2

[0056] The preparation method of the water-soluble small molecule pyridinium salt photoelectric material of the present embodiment comprises the following steps:

[0057] Under the protection of nitrogen, add pyridine and acetonitrile into the reaction vessel, heat and stir at 65°C, then add the chloromethylated aromatic heterocyclic compound, wherein the molar ratio of the chloromethylated aromatic heterocyclic compound to pyridine is 1:16, reacted at 70°C for 11 hours, cooled to room temperature, and removed the solvent under reduced pressure. After the crude product was dissolved in methanol, it was precipitated and filtered in ethyl acetate several times. The water-soluble small molecule pyridinium salt material is obtained by vacuum drying.

[0058] The chloromethylated aromatic heterocyclic compound has the following structure:

[0059]

[0060] The water-soluble small molecule pyridinium salt optoelectronic material prepared in this example has the following structu...

Embodiment 3

[0069] The preparation method of the water-soluble small molecule pyridinium salt photoelectric material of the present embodiment comprises the following steps:

[0070] Under the protection of nitrogen, add pyridine and acetonitrile into the reaction vessel, heat to 60°C and stir, then add bromomethylated aromatic heterocyclic compound, wherein the molar ratio of bromomethylated aromatic heterocyclic compound to pyridine is 1:16, reacted at 90°C for 10 hours, cooled to room temperature, and removed the solvent under reduced pressure. After the crude product was dissolved in methanol, it was precipitated and filtered in ethyl acetate several times. The water-soluble small molecule pyridinium salt material is obtained by vacuum drying.

[0071] The bromomethylated aromatic heterocyclic compound has the following structure:

[0072]

[0073] The water-soluble small molecule pyridinium salt photoelectric material prepared in this embodiment has the following chemical structu...

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Abstract

The invention discloses a preparation method of a water-soluble small molecule pyridinium photoelectric material. The method comprises the following steps of: adding pyridine and acetonitrile into a reaction container, heating and stirring the materials, adding a bromomethyl or chloromethylated aromatic heterocyclic compound to the reaction container, cooling the materials to room temperature after the reaction is finished, and removing the solvent under a pressure reduced condition, thus obtaining a coarse product; dissolving the coarse product through methanol, precipitating and filtering the dissolved product for multiple times, and performing vacuum drying on the product to obtain the final product; or dissolving the coarse product through methanol, adding a sodium salt solution containing an anion group to the product, stirring the solution and the product for two days, removing the solvent under a pressure reduced condition, washing and drying the mixture for multiple times, and performing vacuum drying on the dried mixture to obtain the final product. The water-soluble small molecule pyridinium photoelectric material is determinate in structure and molecular weight and is easily purified, avoids the problem that the batch of a polymer interface material is instable, and has the advantages of high water solubility, film-forming property, film morphology stability, high eletrophilicity, deep lowest unoccupied molecular orbital (LUMO) energy level and low electron injection / extracting energy barrier.

Description

technical field [0001] The invention relates to a water-soluble pyridinium salt photoelectric material based on small organic molecules, in particular to a water-soluble small molecule pyridinium salt photoelectric material and a preparation method thereof. Background technique [0002] In the research of organic optoelectronic devices, the application of electron injection / extraction interface materials plays an important role in the improvement of device efficiency, lifetime and stability, and the research in this area is becoming more and more in-depth and extensive. In terms of electron injection / transport materials, due to the good thermal stability, high triplet energy level and excellent electron mobility of materials containing pyridine groups, they can make electrons and A better balance of holes improves the efficiency of the device; at the same time, a class of polymer interface materials based on pyridine groups, with their good film-forming properties, solution ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07F5/02C07D213/06C07D213/127H01L51/54H01L51/46
CPCY02E10/549
Inventor 苏仕健周虎曹镛
Owner SOUTH CHINA UNIV OF TECH
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