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Fluorine atom substituted benzo heterocycle based conjugated molecule material as well as preparation method and application thereof

A technology of conjugated molecules and fluorine atoms, which is applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve the problems of organic solar cell energy conversion rate attenuation, high price, weak absorption, etc., and achieve the improvement of carrier Transport characteristics, good planarity and rigidity, and the effect of promoting charge transfer

Inactive Publication Date: 2018-06-29
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the shortcomings of fullerene derivatives are mainly reflected in: (1) the mass content of the photoactive layer is generally more than 50%, but the absorption is very weak in the wavelength range of 500-900nm, which is not conducive to further improving the performance of organic solar cells. short-circuit current density; (2) easy to spontaneously form microscopic crystal regions, which is not conducive to the long-term stability of the microscopic morphology of the photoactive layer, resulting in rapid decay of the energy conversion rate of organic solar cells; (3) very high synthesis and modification costs, and Expensive price is not conducive to further reducing the production cost of organic solar cells

Method used

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  • Fluorine atom substituted benzo heterocycle based conjugated molecule material as well as preparation method and application thereof
  • Fluorine atom substituted benzo heterocycle based conjugated molecule material as well as preparation method and application thereof
  • Fluorine atom substituted benzo heterocycle based conjugated molecule material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Synthesis of Conjugated Molecular Materials (IffBR) Based on Indadodithiophene, 5,6-Fluorobenzo[d][1,2,5]thiadiazole and Rhodamine

[0061] The synthetic route is as follows:

[0062]

[0063] Preparation of 4-Bromo-5,6-difluoro-7-methylbenzene[c][1,2,5]thiadiazole (Compound 1)

[0064] Under argon atmosphere, in a 100 mL two-necked round bottom flask, dissolve 4-bromo-5,6-difluorobenzene[c][1,2,5]thiadiazole (1.0 g, 4.0 mmol) in 50 mL of tetrahydrofuran , lithium diisopropylamide (12 mL, 2.0 Min THF) was added dropwise and stirred at -78 °C for 1 h. Iodomethane (1.2 g, 8.0 mmol) was then added to the reaction mixture, the reaction apparatus was returned to room temperature, and the reaction was stirred for 8 hours. After the reaction was completed, the reaction was quenched with water, poured into water, extracted with dichloromethane, dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The crude product was further p...

Embodiment 2

[0075] Synthesis of Conjugated Molecular Materials (IFBR-p for short) based on indahenodithiophene, 5-fluorobenzo[d][1,2,5]thiadiazole and rhodamine

[0076] The synthetic route is as follows:

[0077]

[0078] Preparation of 5-Fluoro-3-methylbenzene-1,2-diamine (Compound 6)

[0079] Under an argon atmosphere, in a 250 mL two-necked round-bottomed flask equipped with a reflux condenser, add 5-fluoro-3-methyl-2-nitroaniline (5.0 g, 29.4 mmol) and dissolve it in 50 mL of ethanol , while adding Fe powder (8.2 g, 147 mmol), then the reaction device was placed in an oil bath, and the temperature was raised to 80 °C. Then HCl (31 mL, 12M) diluted with 30 mL of ethanol was added slowly. The reaction was refluxed for 8 hours and the temperature was lowered to room temperature. The reaction solution was poured into cold NaOH aqueous solution, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 3...

Embodiment 3

[0095] Synthesis of Conjugated Molecular Materials (IFBR-d) Based on Indabodithiophene, 5-Fluorobenzo[d][1,2,5]thiadiazole and Rhodamine

[0096] The synthetic route is as follows:

[0097]

[0098] Preparation of 2-bromo-4-fluoro-6-nitroaniline (compound 12)

[0099] Under an argon atmosphere, in a 250 mL two-necked round-bottomed flask equipped with a condensing device, 4-fluoro-2-nitroaniline (5 g, 32 mmol) was dissolved in 35 mL of acetic acid, and the liquid Br was added dropwise. 2 (10.24 g, 64 mmol) was added to the reaction apparatus. The reaction apparatus was then placed in an oil bath, heated to 60°C and held for 8 hours. After the reaction was complete, the reaction mixture was then poured into NaHSO 3 In aqueous solution, 7 g of yellow solid were obtained. The product did not require further purification. Yield 93%.

[0100] Preparation of 3-bromo-5-fluorobenzene-1,2-diamine (compound 13)

[0101] Under an argon atmosphere, in a 250 mL two-necked round-b...

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Abstract

The invention discloses a fluorine atom substituted benzo heterocycle based conjugated molecule material as well as a preparation method and application thereof. The conjugated molecule material is ofan acceptor-donor-acceptor type structure, wherein an acceptor unit is constructed by using a fluorine atom substituted benzo heterocycle structure and an electron-absorbing dye unit jointly. The conjugated molecule material has the characteristics of easiness in regulation and control of absorption spectrum and molecular energy level, high light absorption, high electron mobility and the like and has a huge application prospect in the fields of organic photovoltaics and organic field-effect transistors.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronic materials, and particularly relates to the preparation of a class of conjugated molecules based on fluorine atom-substituted benzoheterocycles and their application in the technical field of organic optoelectronics. Background technique [0002] Compared with traditional silicon-based solar cells, organic solar cells (Organic Photovoltaics) have the advantages of low cost, large area, flexibility, lightness, and solution processing, and have become a new focus of scientists' research. Over the past 20 years, researchers have synthesized a large number of organic electron-donating materials and blended them with fullerene derivatives (PCBM) as a photoactive layer to prepare solar cell devices. At present, the laboratory efficiency of single-layer organic solar cells has reached 10.3. % [Nat. Commun., 5(2014) 5293], and the energy conversion rate of tandem organic solar cells also rea...

Claims

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Application Information

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IPC IPC(8): C07D495/04H01L51/46
CPCC07D495/04H10K85/656H10K85/6576H10K30/00Y02E10/549
Inventor 应磊钟文楷黄飞曹镛
Owner SOUTH CHINA UNIV OF TECH
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