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A-D-A type organic small molecule and preparation and application thereof

An A-D-A, small molecule technology, used in organic chemistry, semiconductor/solid-state device manufacturing, photovoltaic power generation, etc., can solve problems such as low solar cell efficiency, achieve high yield, and avoid the formation of unilateral by-products.

Inactive Publication Date: 2018-12-28
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the all-small-molecule solar cells in which the donor / acceptor are small-molecule materials are relatively inefficient

Method used

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  • A-D-A type organic small molecule and preparation and application thereof
  • A-D-A type organic small molecule and preparation and application thereof
  • A-D-A type organic small molecule and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Preparation of compound shown in formula (Ⅲ):

[0028] Under the protection of argon, add the compound (2.24g, 10.0mmol) represented by the formula (I) and 20mL of redistilled chloroform into a 100mL double-necked bottle, and add the compound represented by the formula (II) in batches under ice bath after the dissolution is complete. Compound (3.18g, 10.5mmol), stirred at room temperature (25-30°C) for 12h in the dark, poured the reaction solution into water (100mL) and extracted with dichloromethane (50mL×3), and the organic phase was washed with anhydrous MgSO 4 After drying, the filtrate was filtered to remove the solvent by a rotary evaporator to obtain a crude product. The crude product was passed through a silica gel chromatography column (the effective length of silica gel is 10 cm) with petroleum ether as the eluent, and the effluent fraction was collected to obtain the compound represented by formula (III) (2.83 g, 9.3 mmol, 93.5%). 1 H NMR (500MHz, CDCl ...

Embodiment 2

[0039]

[0040] (1) Preparation of compound shown in formula (IX):

[0041] Under the protection of argon, add the compound represented by formula (VII) (i.e., silacyclopentadithiophene with trimethyltin on both sides) (300mg, 0.403mmol) into a 100mL double-necked bottle pretreated in anhydrous and anaerobic conditions, The compound shown in formula (Ⅷ) (i.e. 2-isooctyl substituted thiophene bromaldehyde) (488.9mg, 1.612mmol) and ultra-dry toluene (30mL), after dissolution was complete, tetrakistriphenylphosphine palladium (186.0mg, 0.161 mmol), heated to 110°C and stirred at reflux for 24h. Cool to room temperature (25-30°C, the same below), pour the cooled reaction solution into water (100mL) and extract with dichloromethane (100mL×2), wash the organic phase twice with anhydrous MgSO 4 After drying, the filtrate was filtered to remove the solvent by a rotary evaporator to obtain a crude product. The crude product is passed through a silica gel chromatography column (the...

Embodiment 3

[0046] Embodiment 3 ultraviolet-visible absorption spectrum

[0047] Compound DINTTDTS in embodiment 2 is made into 10 respectively -5 mol / L and 10 -2 mol / L chloroform solution, respectively measure the UV absorption of the solution and the film, where the film is coated on a quartz plate with a spin coater at 1200rpm, the scanning range is 300-800nm, and the measuring instrument is Jasco V-570 UV / VIS / NIR Spectrophotometer and compared with compound DINDTS. The UV-Vis absorption curves of compounds DINDTS and DINTTDTS in chloroform are as follows figure 2 As shown in a, the maximum absorption peaks are 590nm and 561nm respectively, and the absorption coefficients are 6.49×10 4 m -1 cm -1 and 5.42×10 4 m -1 cm -1 . Compared with the compound DINDTS, the maximum absorption peak of the compound DINTTDTS with a longer effective conjugation degree has a blue shift. The LUMO energy level is mainly determined by the electron-withdrawing ability of the electron-deficient u...

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Abstract

The invention discloses an A-D-A type organic small molecule and the preparation and an application thereof. Dithiophene-pyrrole is utilized as a core, and thiophthene (TT) or monothiophene is used asnovel A-D-A type small molecule DINTTDTS and DINDTS of different Pi-bridges. The DINTTDTS and the DINDTS are used as donors to prepare all-small molecule solar cells that can be subjected to solutiontreatment. A DINDTS-based device has the energy conversion efficiency of 4.52%, the current density (Jsc) of 19.96 mAcm^2 and the fill factor (FF) of 57.5%. However, a DINTTDTS-based device has the energy conversion efficiency of 2.79%, the Jsc of 8.98 mA cm^2 and the FF of 39.5%.

Description

technical field [0001] The invention relates to a synthesis method of an A-D-A type organic photovoltaic small molecule and a research on the photovoltaic performance of an all-small molecule organic solar device based on a solution-processable small molecule donor material. Background technique [0002] Fullerenes and their derivatives are often used as acceptor materials in organic solar cells, but fullerenes and their derivatives have weak spectral absorption in the visible-near infrared, high cost, difficult storage, and difficult optical and electrical properties. Defects such as coordination greatly limit the application and further improvement of the efficiency of organic solar cells based on fullerene acceptor materials. Therefore, non-fullerene acceptor materials with higher absorption coefficient, adjustable energy level and relatively low cost are more and more favored by researchers. In recent years, through the design and improvement of non-fullerene acceptor m...

Claims

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Application Information

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IPC IPC(8): C07D519/00H01L51/42H01L51/46
CPCC07D519/00H10K85/626H10K85/615H10K85/6576H10K30/00Y02E10/549
Inventor 邱化玉张倩陈显杰尹守春林志靖王兆龙徐欣
Owner HANGZHOU NORMAL UNIVERSITY
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