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Fluorene ring group-containing non-condensed ring organic small molecular material and preparation method and application thereof

A small molecule and organic technology, applied in the field of organic photovoltaic materials, can solve the problems of unstable shape, limited sustainable development, weak light absorption, etc., and achieve the effect of improving solubility, reducing synthesis difficulty, and good film formation

Active Publication Date: 2021-04-06
WUHAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, their shortcomings, such as weak light absorption and morphological instability, limit the sustainable development of this field, and organic nonfullerene acceptors offer the possibility to overcome these shortcomings of fullerene acceptors.

Method used

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  • Fluorene ring group-containing non-condensed ring organic small molecular material and preparation method and application thereof
  • Fluorene ring group-containing non-condensed ring organic small molecular material and preparation method and application thereof
  • Fluorene ring group-containing non-condensed ring organic small molecular material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] The structural formula of the non-condensed ring organic small molecule material Flu-H of this embodiment is as follows:

[0069] wherein R1 is H.

[0070] The preparation steps are as follows:

[0071] Step 1): the preparation of compound 1, the equation is as follows:

[0072]

[0073] Under nitrogen atmosphere, 2,7-bis(4,4,5,5-tetramethyl-1,3-dioxo-2-boryl)-9,9-dioctylfluorene (0.5g, 0.78mmol) and 5-bromothiophene-2-carbaldehyde (0.45g, 2.35mmol) were dissolved in 35mL phase transfer agent tetrahydrofuran, potassium carbonate aqueous solution (1M, 7mL) and tetrakistriphenylphosphine palladium (0.04g, 0.04mmol ) was added to the mixture, and reacted at 80°C for 16h. After the reaction was completed, add water to quench, add dichloromethane to extract the aqueous layer, dry over anhydrous sodium sulfate, remove the solvent by distillation under reduced pressure, and further purify by column chromatography. The eluent is petroleum ether and dichloromethane (3:1,...

Embodiment 2

[0078] The structural formula of the non-condensed ring organic small molecule material Flu-F of this embodiment is as follows:

[0079] where R1 is F.

[0080] The preparation steps are as follows:

[0081] Step 1): same as embodiment 1 step 1)

[0082] Step 2): The difference from step 2) of Example 1 is that 5,6-difluoro-3-(dicyanomethylene) indoketone (0.9g, 4.1mmol) is used to carry out knoevenagel reaction with compound 1, Finally, Flu-F (530 mg, 72%) was obtained as a black solid substance.

Embodiment 3

[0084] The structural formula of the non-condensed ring organic small molecule material BTT6IC-H of this embodiment is as follows:

[0085] wherein R2 is H.

[0086] The preparation steps are as follows:

[0087] Step 1): the preparation of compound 2, the equation is as follows:

[0088]

[0089] Under nitrogen atmosphere, 3-hexylthiophene (9.12g, 54mmol) was dissolved in 250mL of anhydrous tetrahydrofuran, and n-butyllithium (23.85mL, 2.5M in hexane, 59.5mmol) was added dropwise at -78°C. React at -78°C for 1 h, then add tributyltin chloride (19.37 g, 59.5 mmol), slowly rise to room temperature, and react at room temperature for 12 h. After the reaction, the reaction system was quenched by adding distilled water, and the aqueous layer was extracted with petroleum ether. The extracted organic layer was dried with anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure to obtain compound 2 without further purification (24.1g, 97% )....

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Abstract

The invention relates to a fluorene ring group-containing non-condensed ring organic small molecular material and a preparation method and an application thereof. 2, 7-di(4, 4, 5, 5-tetramethyl-1, 3-dioxo-2-borane)-9, 9-dioctyl fluorene is used as a central core unit, and a thiophene unit is introduced to enhance [pi] conjugation of a molecular main chain, on this basis, benzothiadiazole is introduced to increase the electron deficiency capacity of the obtained molecule, thiophene units are connected to the two sides to expand conjugation and finally reduce the energy band gap of the molecule, side chains on thiophene can improve the solubility of the molecule, and fluorine-containing cyanoindanone units are connected to the two ends to form effective charge transfer in the whole molecule.

Description

technical field [0001] The invention belongs to the field of organic photovoltaic materials, and in particular relates to the design and synthesis of non-condensed ring organic small molecule acceptor materials and the preparation of devices. Background technique [0002] Organic photovoltaic (OPV) solar cells have some unique advantages, such as the potential to be fabricated at low cost, as well as the fact that they can be translucent, highly transparent under visible light, flexible and lightweight. These properties are attractive for building integrated solar power and portable devices. The active layer in OPV cells usually consists of a mixture of electron donors (low ionization energy materials) and electron acceptors (high electron affinity materials), which have a bulk heterojunction structure that helps ensure efficient light absorption, charge separation , transport electrons and holes to their corresponding electrodes. Over the past two decades, fullerene deriv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14C07D333/24H01L51/46
CPCC07D417/14C07D333/24H10K85/615H10K85/626H10K85/6576H10K85/657Y02E10/549
Inventor 刘丹庄园蔡金龙汪亮
Owner WUHAN UNIV OF TECH
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