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A-D-A conjugated molecule, preparation method, application in organic solar cell, and organic solar cell

An A-D-A, conjugated molecule technology, applied in organic chemistry, chemical instruments and methods, circuits, etc., can solve problems such as difficulty in adjusting absorption and energy level, no absorption of visible light, difficult purification, etc., and achieves large molar extinction coefficient and high photoelectricity. Conversion efficiency, effect of broad absorption spectrum

Active Publication Date: 2019-11-08
UZHOU QIANXUN NEW ENERGY TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, fullerene derivatives also have problems such as non-absorption of visible light, difficulty in adjusting absorption and energy levels, difficulty in purification and high cost, so it is difficult to apply them in practice.

Method used

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  • A-D-A conjugated molecule, preparation method, application in organic solar cell, and organic solar cell
  • A-D-A conjugated molecule, preparation method, application in organic solar cell, and organic solar cell
  • A-D-A conjugated molecule, preparation method, application in organic solar cell, and organic solar cell

Examples

Experimental program
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Effect test

preparation example Construction

[0077] The present invention also provides a method for preparing A-D-A conjugated molecules, including the following steps:

[0078] 2,5-Dibromopyrazine and compound A are cross-coupling to obtain compound B, wherein the structural formula of compound A is The structural formula of compound B is Ar is a thiophene group, a thiophene derivative group, a dithiophene group, a dithiophene derivative group, a trithiophene group, a trithiophene derivative group, a benzodithiophene group, a benzodithiophene group Thiophene derivative group, pyrrolodithiophene group, pyrrolodithiophene derivative group, pentadithiophene group, or pentadithiophene group;

[0079] Compound B and boron tribromide undergo a condensation ring-closure reaction to obtain compound C, where the structural formula of compound C is

[0080] Compound C and dialkylaryl zinc are substituted to obtain compound D, wherein the structural formula of compound D is R 1 For 4-alkylphenyl, 4-alkoxyphenyl, 4-alkylthiophenyl, 4...

preparation Embodiment 1

[0094] The steps of preparing the A-D-A conjugated molecule of Example 1 include:

[0095] (1) 2,5-Dibromopyrazine and compound A undergo crossover (Stille) coupling reaction to obtain compound B:

[0096]

[0097] Weigh 1.0g (4.2mmol) of 2,5-dibromopyrazine and 4.1mg (10.5mmol) of compound A, put them into a 250mL round-bottomed flask, pump twice and add bis-tetratriphenylphosphine palladium Pd( PPh 3 ) 4 After repeatedly exhausting the gas in the reaction vessel and injecting inert gas to remove the air in the reaction vessel, adding 20 mL of toluene, stirring and reacting at a temperature of 110°C for 12 hours, and then cooling to room temperature; the resulting reaction liquid was rotary evaporated The solvent was removed, and the solid product obtained was separated by silica gel (200-300 mesh) column chromatography. The eluent was petroleum ether / dichloromethane (the volume ratio of the two was 3:1) to obtain a red solid ( 1.7g), which is compound B.

[0098] (2) Compound B i...

Embodiment 2

[0111] The difference between the preparation steps of the A-D-A conjugated molecule in Example 2 and the preparation step of the A-D-A conjugated molecule in Example 1 is that the end-capping group EG that reacts with compound E is different:

[0112]

[0113] Compound E (0.25g, 0.2mmol) and EG2 (0.194g, 1mmol) were sequentially added to a 50mL two-necked flask, pumped three times, and then passed N 2 Add chloroform (20 mL) in the case of, and stir for 5 min to completely dissolve the two compounds. Then pyridine (0.6 mL) was added and the solution slowly turned green. The mixture was refluxed at 65°C for 20 hours, and most of the solvent was evaporated. The crude product was washed with methanol to remove excess EG2, and was further purified by column chromatography using n-hexane: dichloromethane (2:1) as the eluent to obtain the ADA conjugated molecule of Example 2 as a dark blue solid .

[0114] The chemical structure of the ADA conjugated molecule in Example 2 was character...

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Abstract

The invention provides an A-D-A conjugated molecule and a preparation method thereof, an organic solar cell and application of the A-D-A conjugated molecule in the organic solar cell. The A-D-A conjugated molecule has the general structure shown in the specification, wherein R1 is 4-alkylphenyl, 4-alkoxyphenyl, 4-alkylthiophenyl, 4-alkylthienyl, 4-alkoxythienyl, 4-alkylthiothienyl, 4-alkylthiothienyl, 4-alkylselenophenyl or 4-alkylthioselenophenyl; ar is thiophene group, thiophene derivative group, bithiophene group, bithiophene derivative group, dithienothiophene group, dithienothiophene derivative group, benzobithiophene group, benzobithiophene derivative group, pyrrolo bithiophene group, pyrrolo bithiophene derivative group, pentane bithiophene group, or pentane bithiophene derivative group; and EG is a capping group. The A-D-A conjugated molecule has stronger light absorption capability, better charge transmission performance and appropriate electron energy level.

Description

Technical field [0001] The present invention relates to the technical field of organic solar cells, in particular to an A-D-A conjugated molecule, a preparation method of A-D-A conjugated molecule, organic solar cell, and application of A-D-A conjugated molecule in organic solar cell, and organic solar cell. Background technique [0002] Organic solar cells are solar cells that use organic matter as the light-absorbing active layer material. Compared with inorganic solar cells, organic solar cells have the advantages of low cost, light weight, flexible devices and solution processing, etc., so they have gradually gained academic And industry. [0003] The active layer of an organic solar cell often uses a bulk heterojunction structure to promote the separation of electrons. This structure is divided into two components, namely, an electron donor and an electron acceptor. In previous studies, fullerene derivatives were often used as electron acceptors because of their high electron...

Claims

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Application Information

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IPC IPC(8): C07F5/02H01L51/42H01L51/46
CPCC07F5/02H10K85/626H10K85/657H10K30/30Y02E10/549
Inventor 刘焘杨涛
Owner UZHOU QIANXUN NEW ENERGY TECH CO LTD
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