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A fused ring quinoxaline imide-based non-fullerene acceptor material and its preparation method and application

A quinoxaline imide-based, non-fullerene acceptor technology, which is applied in the field of fused ring quinoxaline imide-based non-fullerene acceptor materials and its preparation, and can solve the lack of matching types of donor materials , shallow HOMO energy level, low open circuit voltage, etc., to achieve the effect of improving carrier mobility, increasing interaction, and enhancing π-π interaction

Active Publication Date: 2022-03-29
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In view of the problems of poor stability, shallow HOMO energy level, low open circuit voltage and few types of matching with donor materials in existing organic / polymer solar cells, the purpose of the present invention is to provide a Fused ring quinoxaline imide-based non-fullerene acceptor material and its preparation method and application

Method used

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  • A fused ring quinoxaline imide-based non-fullerene acceptor material and its preparation method and application
  • A fused ring quinoxaline imide-based non-fullerene acceptor material and its preparation method and application
  • A fused ring quinoxaline imide-based non-fullerene acceptor material and its preparation method and application

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specific Embodiment 1

[0094] A fused ring quinoxaline imide-based non-fullerene acceptor material whose chemical structure is Z1, its synthetic route is as follows:

[0095]

[0096] (1) Synthesis of an intermediate whose chemical structure is b: under nitrogen protection, add 12,13-bis(2-ethylhexyl)-3,9-dodecane-12,13-dihydro- [1,2,5]thiadiazolo[3,4-e]thiophene[2",3":4',5']thiophene[2',3':4,5]pyrrole[3,2- g] Thiophene[2',3':4,5]thiophene[3,2-b]indole (a) (0.001mol), iron powder (0.01mol), 0.07L acetic acid solvent. After refluxing for 10 hours, cool to room temperature. Using dichloromethane for extraction, the organic phase was dried with magnesium sulfate, and the solvent was spin-dried to obtain a crude product. The crude product was directly used in the next step without purification.

[0097] MALDI-TOF-MS: m / z=943.57 (M + ).

[0098] (2) Synthesis of an intermediate with the chemical structural formula d: under nitrogen protection, compound b (0.001 mol), diethyl dioxosuccinate (0.01 mo...

specific Embodiment 2

[0123] A kind of condensed ring quinoxaline imide based non-fullerene acceptor material whose chemical structure is Z2, its synthetic route is as follows:

[0124]

[0125] The experimental procedure of the fused ring quinoxaline imide-based non-fullerene acceptor material Z2 is basically the same as that of Example 1, and compound h is prepared according to the experimental procedure of Example 1; compound h and 5,6-dichloro-3- (Dicyanomethylene) indoketone (2ClINCN) reacted to obtain fused ring quinoxaline imide-based non-fullerene acceptor material Z2.

[0126] Synthesis of fused ring quinoxaline imide-based non-fullerene acceptor material with chemical structural formula Z2: under nitrogen protection, compound h (0.001mol), 5,6-dichloro-3-( Dicyanomethylene) indoketone (2ClINCN) (0.003 mol), pyridine (0.001 mol) and 0.04 L of chloroform solvent. After refluxing for 12 hours, cool to room temperature. Extract with dichloromethane, dry the organic phase with anhydrous m...

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Abstract

The invention discloses a condensed ring quinoxaline imide-based non-fullerene acceptor material as well as a preparation method and application thereof. The fused-ring quinoxalineimide-based non-fullerene acceptor material includes a fused-ring quinoxalineimide-based central core and an electron-deficient end group, and the fused-ring quinoxalineimide-based central core is a nitrogen bridge Ladder fused ring structure, with electron-withdrawing end groups connected to both ends of the central core. This type of receptor material has good solubility and is easy to process into a film. The organic / polymer solar cell and organic photodetector device prepared by the fused ring quinoxaline imide-based non-fullerene acceptor material of the present invention as the active layer all exhibit excellent performance, and the energy conversion efficiency of the organic photovoltaic cell Above 12%, the dark current density of organic photodetectors is below 1mA / cm 2 , which fully demonstrates that this kind of non-fullerene acceptor material has broad market prospects in organic photovoltaics, logic complementary circuits, organic photodetectors, organic field effect transistors, and organic light-emitting diodes.

Description

technical field [0001] The invention belongs to the technical field of organic semiconductor materials, and in particular relates to a fused-ring quinoxaline imide-based non-fullerene acceptor material and a preparation method and application thereof. Background technique [0002] In recent years, non-fullerene acceptor materials have been greatly developed, and the efficiency of single-layer heterojunction organic / polymer solar cells has reached more than 16% (Sci China Chem, 2019, 62:746–752 ), it is very likely to be applied in a large area in the future, and form a complementary advantage with silicon-based batteries. However, this kind of acceptor materials has problems such as poor stability, shallow highest occupied molecular orbital (HOMO) energy level, low open circuit voltage, and few types of matching with donor materials. Therefore, exploring new design strategies and seeking new receptor building blocks is still one of the effective ways to solve these problems...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/22H01L51/05H01L51/30H01L51/42H01L51/46H01L51/50H01L51/54
CPCC07D495/22H10K85/615H10K85/654H10K10/46H10K30/00H10K50/00Y02E10/549
Inventor 应磊朱春光黄飞曹镛
Owner SOUTH CHINA UNIV OF TECH
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