Indacenodithiophene-based non-fullerene organic solar energy electron acceptor material

A technology for solar cells and acceptor materials is applied in the field of acceptor materials for organic solar cells based on thiophene non-fullerenes, and achieves the effects of lowering the energy level, reducing the energy gap, and having strong light absorption capability.

Active Publication Date: 2019-09-03
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional classic small molecule organic solar cell acceptor material - fullerene, has been proved that many of its shortcomings cannot be avoided and improved, such as energy level and ultraviolet absorption problems

Method used

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  • Indacenodithiophene-based non-fullerene organic solar energy electron acceptor material
  • Indacenodithiophene-based non-fullerene organic solar energy electron acceptor material
  • Indacenodithiophene-based non-fullerene organic solar energy electron acceptor material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation of non-fullerene organic solar cell acceptor material with the following structural formula

[0026]

[0027] Accurately weigh 0.488g (0.4mmol) of 4,4,9,9-tetrahexadecyl-4,9-dihydro-S-indacene[1,2-b:5,6-b' ] Dithiophene-2,7-dialdehyde, 0.388g (2.0mmol) 3-(dicyanomethylene) indoketone, 0.006g (0.07mmol) β-alanine, put into 250mL two round bottoms In the flask, keep the condition protected from light, and carry out vacuum operation. After vacuuming, blow nitrogen into the flask, repeat the above operation at least 3 times, measure 50mL of 1,2-dichloroethane and 25mL of methanol with a graduated cylinder, inject them into the flask through a syringe, and keep stirring during this process. The temperature of the oil bath was raised to 80°C, the reaction was refluxed for 12 hours, the heating was turned off, and the stirring was continued until the temperature of the reaction system returned to room temperature. Next, the product was extracted with dichlorom...

Embodiment 2

[0029] Preparation of non-fullerene organic solar cell acceptor material with the following structural formula

[0030]

[0031] In this embodiment, the 3-(dicyanomethylene) indoketone used in Example 1 is replaced with 5,6-difluoro-3-(dicyanomethylene) indoketone in the amount of the same substance, The other steps were the same as in Example 1, and the dark blue-black powder acceptor material IDT-IC2F was obtained with a yield of 67.3%, and the structural characterization data were: 1 H NMR (400MHz, CDCl 3 )δ(ppm):8.97(s,2H),8.64-8.47(m,2H),7.72(s,2H),7.71-7.63(m,2H),7.60(s,2H),2.06(t,J =13.6Hz,4H),1.98-1.86(m,4H),1.14(dd,J=24.9,15.7Hz,104H),0.92-0.73(m,20H); MS(ESI)m / z:1645.10[M +H]+.

Embodiment 3

[0033] Preparation of non-fullerene organic solar cell acceptor material with the following structural formula

[0034]

[0035] In this example, the 3-(dicyanomethylene) indoketone used in Example 1 is replaced with thienindanone in the same amount of substances, and the other steps are the same as in Example 1 to obtain dark blue black powder receptor Material IDT-ICTh, the yield is 75.4%, and the structural characterization data are: 1 H NMR (400MHz, CDCl 3 )δ(ppm):8.90(s,2H),8.39(s,2H),7.95(s,2H),7.68(s,2H),7.58(s,2H),2.05(t,J=13.1Hz, 4H), 1.93(t, J=12.4Hz, 4H), 1.11(d, J=17.5Hz, 104H), 0.90-0.73(m, 20H); MS(ESI) m / z: 1585.27[M+H] +.

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Abstract

The invention discloses an indacenodithiophene-based non-fullerene organic solar energy electron acceptor material, which is based on indacenodithiophene as a center, and uses different electron-withdrawing units as terminal groups, wherein the indacenodithiophene unit has a rigid plane structure, and can enhance the intramolecular pi-pi stacking, optimize the crystallization property and the electrochemical property of the molecule and improve the carrier mobility, the long alkyl side chain can enhance the solubility of the molecule and change the morphology of the active layer, and the terminal group strong electron-withdrawing unit can easily dissociate and transport the excitons so as to further reduce the energy level and reduce the energy gap. According to the present invention, theacceptor material has good film forming property, has good absorption in a visible light near infrared range, has characteristics of moderate energy level and a certain thermal stability, and can be matched with polymer donor materials and greatly improve the energy conversion efficiency of organic solar cells.

Description

technical field [0001] The invention belongs to the technical field of solar cell materials, and in particular relates to a non-fullerene organic solar cell acceptor material based on indaproteothiophene. Background technique [0002] In the past ten years, organic solar cells have been developing strongly. Due to their many advantages, including simple preparation, low cost, light weight, and large-scale production, organic solar cells have attracted the attention of researchers. The traditional classic small molecule organic solar cell acceptor material - fullerene, has been proved that many of its shortcomings cannot be avoided and improved, such as the problems of energy level and ultraviolet absorption. In recent years, scientists have focused on non-fullerene small molecule acceptor materials. In recent years, fused-ring electron acceptors have attracted much attention. Their own structure has a large rigid conjugation plane, which can significantly increase the π-π s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04H01L51/42H01L51/46
CPCC07D495/04H10K85/6576H10K30/00H10K85/6572Y02E10/549
Inventor 王强林浩张倩
Owner SHAANXI NORMAL UNIV
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