Condensed ring quinoxaline imide non-fullerene acceptor material and preparation method and application thereof

A quinoxaline imide-based, non-fullerene acceptor technology is applied in the field of condensed ring quinoxaline imide-based non-fullerene acceptor materials and the field of preparation thereof, and can solve the problem of shallow HOMO energy level, low energy consumption Few types of bulk material matching, low open circuit voltage, etc.

Active Publication Date: 2021-03-26
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

Method used

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  • Condensed ring quinoxaline imide non-fullerene acceptor material and preparation method and application thereof
  • Condensed ring quinoxaline imide non-fullerene acceptor material and preparation method and application thereof
  • Condensed ring quinoxaline imide non-fullerene acceptor material and preparation method and application thereof

Examples

Experimental program
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Effect test

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 non-fullerene acceptor material and a preparation method and application thereof. The condensed ring quinoxaline imide non-fullerene acceptormaterial comprises a condensed ring quinoxaline imide central core and electron deficiency end groups, the condensed ring quinoxaline imide central core is of a nitrogen bridge trapezoidal condensedring structure, and the electron withdrawing end groups are connected to the two ends of the central core. The acceptor material has good solubility and is easy to process into a film. An organic/polymer solar cell and an organic photodetector device which are prepared by taking the condensed ring quinoxaline imide non-fullerene acceptor material as an active layer show excellent performance, theenergy conversion efficiency of an organic photovoltaic cell is over 12 percent, and the dark current density of an organic photodetector is lower than 1mA/cm < 2 >; the non-fullerene acceptor material has a wide market prospect 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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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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