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Difluorobithiophene-based donor-acceptor polymers for electronic and photonic applications

A conjugated polymer, D-A technology, applied in the field of new organic compounds, D-A conjugated polymers, can solve the problems of PSC performance deterioration and achieve the effects of life and efficiency improvement, good application prospects, and excellent solubility

Active Publication Date: 2017-08-18
THE HONG KONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, fluorination of the donor moiety of D-A conjugated polymers has rarely been reported to improve the performance of PSC devices.
In previous failure cases, it was believed that the perfluorinated polymer backbone (both donor and acceptor blocks contain fluorine) would degrade the performance of PSCs, resulting in extremely strong self-assembly properties and fluorine-phobic effects of polymers.

Method used

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  • Difluorobithiophene-based donor-acceptor polymers for electronic and photonic applications
  • Difluorobithiophene-based donor-acceptor polymers for electronic and photonic applications
  • Difluorobithiophene-based donor-acceptor polymers for electronic and photonic applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0129] Example 1 - Synthesis of monomers

[0130]

[0131] step 1: Preparation of 4,7-bis(4-(2-octyldodecyl)-2-thienyl)-2,1,3-benzothiadiazole (S3)

[0132] 3-(2-Octyldodecyl)thiophene (5.00 g, 13.7 mmol) was dissolved in 50 mL THF to obtain a solution, and the solution was cooled to -78° C. under nitrogen protection. Lithium diisopropylamide (2M, 8.3 mL, 16.6 mmol) was slowly added dropwise thereto, and the mixture was stirred at -78°C for 1 hour, then returned to 0°C and stirred for another 1 hour. The mixture was then cooled to -78°C and tri-n-butyltin chloride (6.50 g, 20 mmol) was added in one portion. The reaction mixture was brought to room temperature and stirred overnight. After adding KF aqueous solution, the organic phase was washed three times with water, and then washed with Na 2 SO 4 dry. The solvent was removed by rotary evaporation to obtain a yellow oily crude product, which was used directly without further purification. 2-(tri-n-butylstannyl)-4-...

Embodiment 2

[0138] Example 2 - Synthesis of polymers

[0139]

[0140] ffT2-TBTT can be synthesized by microwave reaction or conventional reaction. in N 2 In a protected glove box, monomer S4 (96.5mg, 0.095mmol), (3,3'-difluoro-[2,2'-dithiophene]-5,5'-diyl)bis(trimethyl stannane) (50.2mg, 0.095mmol), Pd 2 (dba) 3 (1.1mg, 0.002mmol) and P(o-tol) 3 (2.4 mg, 0.008 mmol) was added 1.6 mL of chlorobenzene. The reaction mixture was then sealed and heated at 145°C for 2 days (or microwaved at 160°C for 30 minutes). The mixture was cooled to room temperature, and 10 mL of toluene was added, followed by precipitation with methanol. The crude product was collected by filtration and extracted by Soxhlet (CH 2 Cl 2 , CHCl 3 and chlorobenzene) and repeated precipitation to purify. The solvent was removed by rotary evaporation, and the residue was dissolved in chlorobenzene and precipitated with methanol. The solid was collected by filtration and dried in vacuo to afford the polymer (89...

Embodiment 3

[0144] Example 3 - Characterization of polymers

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PUM

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Abstract

An organic compound, a donor-acceptor conjugated polymer, a formulation and a thin film, wherein a solution of the donor-acceptor conjugated polymer exhibits a peak optical absorption spectrum red shift of at least 100 nm when the donor-acceptor conjugated polymer solution is cooled from 140 DEG C to room temperature.

Description

[0001] related application [0002] This patent application claims priority to US Provisional Patent Application No. 62 / 122,479, filed October 22, 2014, by the inventors of the present application, which is incorporated herein by reference in its entirety. technical field [0003] This patent mainly involves: new organic compounds, D-A conjugated polymers; their preparation methods and intermediate products used in the preparation process; preparations containing such polymers as semiconductors in organic electronic (OE) devices, especially organic photovoltaic ( OPV) devices and organic field-effect transistor (OFET) devices; and OE devices and OPV devices made from these formulations. Background technique [0004] In recent years, there has been increasing interest in the application of organic semiconducting materials, including conjugated polymers, in various electronic fields. [0005] Organic photovoltaic materials (OPV) is a part that cannot be ignored in the field o...

Claims

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Application Information

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IPC IPC(8): C07D409/00C08G61/12H01L51/42C08L81/00
CPCC08G61/122C08G61/123C08G61/124C08G61/126C08G2261/124C08G2261/1412C08G2261/146C08G2261/18C08G2261/3223C08G2261/3241C08G2261/334C08G2261/344C08G2261/364C08G2261/414C08G2261/91Y02E10/549C08K3/045C07D333/28C07F7/2208H01B1/127C07D417/14H10K85/113H10K85/215H10K30/50C08L65/00H10K30/30C08G2261/3246C08G2261/41C08G2261/92
Inventor 颜河李正珂
Owner THE HONG KONG UNIV OF SCI & TECH
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