Conjugated organic molecule and preparation method and application thereof

An organic molecule and conjugation technology, applied in the field of solar cells, can solve the problems of complex preparation process of organic solar cells, hindering the commercial application of organic solar cells, and increasing production costs, achieving broad commercial application prospects, low production costs, and high-tech The effect of simple process

Active Publication Date: 2022-05-27
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, high-efficiency organic solar cells prepared by blending small-molecule donor materials and non-fullerene acceptor materials Y6 almost all require thermal annealing, solvent annealing, and the use of additives to optimize the morphology of organic thin films. , otherwise most of its photovoltaic efficiencies are lower than 6%, which will lead to more complicated preparation process of organic solar cells and higher production costs, hindering the commercial application of organic solar cells

Method used

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  • Conjugated organic molecule and preparation method and application thereof
  • Conjugated organic molecule and preparation method and application thereof
  • Conjugated organic molecule and preparation method and application thereof

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preparation example Construction

[0058] The present invention also provides the preparation method of the above-mentioned conjugated organic molecule, comprising:

[0059] S11, dissolving the first precursor and the second precursor in the first solvent, and reacting to obtain the third precursor;

[0060] S12, dissolving the third precursor and the precursor containing the electron withdrawing unit in the second solvent, and reacting to obtain a conjugated organic molecule.

[0061] In step S11, the first precursor includes at least a compound represented by the following formula (8),

[0062]

[0063] where R 9 , R 10 , R 11 Independently selected from at least one of straight-chain alkyl groups having 1-10 carbon atoms and branched-chain alkyl groups having 2-10 carbon atoms;

[0064] The first precursor is preferably a compound represented by the following formula (8-1),

[0065]

[0066] The function of the first precursor is to provide terphenyl dithiophene as the central unit of the conjugat...

Embodiment 1

[0112] The conjugated organic molecule 3BDT-4 was prepared by the following procedure:

[0113]

[0114] In the three-necked flask, add compound 8-1 (1.03 g, 0.50 mmol), compound 9-1 (0.41 g, 1.05 mmol), and 70 mL of anhydrous toluene, feed N 2 Deoxygenation was carried out for 30 min, then tetrakistriphenylphosphonium palladium (60 mg) was added, and the reaction was refluxed for about 24 h. After the reaction was completed, it was concentrated to dryness under reduced pressure, and subjected to column chromatography (eluent: petroleum ether (PE): chloroform (CHCl) 3 )=3:1) separation and purification to obtain a dark purple solid compound 10-10.60 g with a yield of 51%. HNMR test data: H NMR (400MHz, CDCl 3 ,ppm)δ:9.75(s,2H,-CHO),7.58(d,2H,J=2.8Hz,ArH),7.42-7.38(m,6H,ArH),7.27-7.25(m,6H,ArH) ,7.05(d,2H,J=3.2Hz,ArH),6.92(d,6H,J=2.8Hz,ArH),6.82(s,2H,ArH),2.95(d,12H,J=6.4Hz,- CH 2 -),2.63(t,4H,J=7.2Hz,-CH 2 -),1.84-1.76(m,6H,-CH-),1.62-1.29(m,72H,-CH-) 2 -),1.06-0.88(m,...

Embodiment 2

[0117] The conjugated organic molecule 3BDT-5 was prepared by the following scheme:

[0118]

[0119] The preparation method of compound 10-1 is the same as that in Example 1. Next, in a three-necked flask, add compound 10-1 (0.30 g, 0.128 mmol), compound 13-1 (0.25 g, 1.28 mmol) and 60 mL of chloroform, and 0.1 mL of piperidine, and react at 60 ° C for 24 h under nitrogen protection . After the reaction, it was poured into 200 mL of methanol for sedimentation, and the obtained solid was separated and purified by column chromatography (eluent: PE:CHCl). 3 = 1:2), the crude product is obtained. Using methanol:chloroform (volume ratio 1:2) as a mixed solvent, recrystallization was performed twice, and finally a dark red solid 3BDT-50.28g was obtained with a yield of 82%. The HNMR test data are as follows: HNMR (400MHz, CDCl 3 ,ppm)δ:8.03(s,2H,ArH),7.59(s,2H,ArH),7.36-7.25(m,12H,ArH),7.03(s,2H,ArH),6.93-6.91(m,6H ,ArH),6.82(s,2H,ArH),4.12(br,4H,-OCH 2 -),2.97(d,12H,J=6.0...

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Abstract

The invention relates to a conjugated organic molecule as well as a preparation method and application thereof. The structural formula of the organic conjugated molecule is shown in the following formula (1), Ar1 represents an electron withdrawing unit, Ar2 represents a side chain substitution unit, and R1 and R2 are independently selected from at least one of hydrogen atoms, alkyl with the carbon atom number being 2-20 and alkoxy with the carbon atom number being 2-20. The organic conjugated molecule has high visible light absorptivity, can form good complementation with the absorption of a low-band-gap acceptor material, and is beneficial to obtaining high short-circuit current. When the conjugated organic molecule and a non-fullerene receptor are blended to prepare an active layer of an organic solar cell, high photovoltaic efficiency can be obtained without any thin film morphology optimization means.

Description

technical field [0001] The invention relates to the field of solar cells, in particular to a conjugated organic molecule and a preparation method and application thereof. Background technique [0002] Organic solar cells are a new generation of green energy technology with broad development prospects. Among many organic solar cells, organic solar cells with fullerenes as acceptor materials are a common type. However, the disadvantages of high preparation cost, difficult purification, and almost no absorption in the visible and near-infrared regions restrict the development of such organic solar cells. Therefore, non-fullerenes are currently used as acceptor materials, and Y6 is a material with better photovoltaic performance among non-fullerene acceptors. However, the high-efficiency organic solar cells prepared by blending the currently reported small molecule donor materials with the non-fullerene acceptor material Y6 almost all require additional means of optimizing the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/42H01L51/46H01L51/50H01L51/54H01L51/05H01L51/30
CPCC07D519/00H10K85/655H10K85/6576H10K10/00H10K30/00H10K50/00Y02E10/549
Inventor 葛子义杨道宾郁魁保徐俊
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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