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Conjugated small organic molecule interface modification material, preparation method thereof, and organic solar cell formed by the material

An organic solar cell and interface modification technology, which is applied in the preparation of organic compounds, organic chemistry, carboxylate preparation, etc., to achieve the effects of reducing electron transport barriers, increasing extraction rates, and improving performance

Active Publication Date: 2019-06-07
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The conjugated organic small molecule interface modification material is used to modify the surface of metal oxides by self-assembly

Method used

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  • Conjugated small organic molecule interface modification material, preparation method thereof, and organic solar cell formed by the material
  • Conjugated small organic molecule interface modification material, preparation method thereof, and organic solar cell formed by the material
  • Conjugated small organic molecule interface modification material, preparation method thereof, and organic solar cell formed by the material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Add 1 molar equivalent of 1,3-indanedione, 1.2 molar equivalent of p-aldehyde benzoic acid and 0.1 molar equivalent of β-alanine into the dry reaction bottle. Then according to the feeding amount, add 10ml of mixed solvent of ethanol and 1,2-dichloroethane for every 2mmol of 1,3-indanedione, wherein the volume ratio of ethanol to 1,2-dichloroethane is 1:1. Then react at 80°C under reflux for 8h. During the reaction, a yellow solid was precipitated, and after the reaction was completed, the precipitated solid was obtained by suction filtration. The solid was washed three times with a mixed solvent of ethanol and 1,2-dichloroethane to obtain SAM1. The NMR spectrum of SAM1 is as follows Figure 4 shown. 1 H NMR (DMSO-d6, 500MHz): δ13.28(s, 1H), 8.48(d, J=10Hz, 2H), 8.02(d, J=10Hz, 2H), 7.94-8.00(m, 4H), 7.86(s,1H).

Embodiment 2

[0035]Add 1 molar equivalent of rhodanine, 2 molar equivalents of p-aldehyde benzoic acid and 1 molar equivalent of β-alanine into the dry reaction bottle. Then according to the feeding amount, add 10ml of mixed solvent of ethanol and 1,2-dichloroethane for every 2mmol of rhodanine, wherein the volume ratio of ethanol and 1,2-dichloroethane is 1:1. Then react at 80°C under reflux for 8h. During the reaction, a yellow solid was precipitated, and after the reaction was completed, the precipitated solid was obtained by suction filtration. The solid was washed three times with a mixed solvent of ethanol and 1,2-dichloroethane to obtain SAM2. The NMR spectrum of SAM2 is as follows Figure 5 shown. 1 H NMR (DMSO-d 6 ,500MHz):δ8.05(d,J=10Hz,2H),7.85(s,1H),7.73(d,2H),4.06-4.10(m,4H),1.19(t,J=7.5Hz,3H ).

Embodiment 3

[0037] Add 1 molar equivalent of dicyanorhadanine, 1.6 molar equivalent of p-aldehyde benzoic acid and 0.6 molar equivalent of β-alanine in a dry reaction flask, wherein the volume ratio of ethanol to 1,2-dichloroethane is 1:1, wherein the volume ratio of ethanol to 1,2-dichloroethane is 1:1. Then according to the feeding amount, add 10ml of mixed solvent of ethanol and 1,2-dichloroethane for every 2mmol of dicyanorhadenine. Then react at 80°C under reflux for 8h. During the reaction, a yellow solid was precipitated, and after the reaction was completed, the precipitated solid was obtained by suction filtration. The solid was washed three times with a mixed solvent of ethanol and 1,2-dichloroethane to obtain SAM3. The NMR spectrum of SAM3 is as follows Figure 6 shown. 1 H NMR (DMSO-d 6 , 500MHz): δ8.09-8.11 (m, 3H), 7.78 (d, J = 10Hz, 2H), 4.13-4.17 (m, 2H), 1.28-1.31 (t, J = 7.5Hz, 3H).

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Abstract

The invention discloses a conjugated organic small molecule interface modification material, a preparation method and an organic solar cell formed by the conjugated organic small molecule interface modification material. The organic small-molecular interface modification materials SAM1, SAM2 and SAM3 are obtained through one-step condensation synthesis of p-aldehyde benzoic acid and 1,3-indanedione, rhodanine and dicyanorhodanine. According to the organic small molecule interface modification material, zinc oxide can be subjected to surface modification through physical adsorption and chemicalreaction; not only can the defect state density of hydroxyl dangling bonds on the surface of zinc oxide be reduced, but also the energy level arrangement can be optimized to reduce the electron transport barrier at the interface, thereby improving the interface charge extraction of the solar cell device and reducing the interface carrier recombination. The modification efficiency and the device efficiency of the inversion type organic solar cell prepared from the material are obviously improved. After the SAM1 is modified, the device efficiency of the PBDB-T / ITIC system is improved to 10.82%from 10.13%, and the device efficiency of the PBDB-T-SF / IT-4F system is improved to 13.25% from 12.18%.

Description

technical field [0001] The invention belongs to the field of energy materials, in particular to a conjugated organic small molecule interface modification material, a preparation method and an organic solar cell composed of the same. Background technique [0002] The efficient conversion of sunlight into electrical energy through solar cells has always been a focus of attention and research in academia and industry. Inorganic solar cells dominated by silicon-based solar cells are currently the most mature varieties of solar cells, with relatively high photoelectric conversion efficiency, but high energy consumption and pollution in the manufacturing process have brought high production costs, and at the same time Pollution to the surrounding environment. [0003] Solution-processable solar cells can achieve clean, efficient, and large-scale mass production through roll-to-roll technology, which is one of the future development directions of solar cells. Research on the pho...

Claims

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Application Information

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IPC IPC(8): C07D277/34C07D277/36C07C65/38C07C51/373H01L51/46
CPCY02E10/549
Inventor 李昌治刘浩燃王树旭
Owner ZHEJIANG UNIV
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