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Conjugated polymers and their use in optoelectronic devices

A polymer, optoelectronic technology, applied in the direction of electric solid devices, photovoltaic power generation, electrical components, etc., can solve problems such as poor air stability

Active Publication Date: 2016-06-29
RAYNERGY TEK INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is well known that P3HT has poor air stability

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0215] Example 1 - Synthetic monomer

example 1

[0216] Example 1A: Preparation of 4,7-dibromo-5,6-difluorobenzo[1,2,5]thiadiazole

[0217] Step 1: 5,6-Difluorobenzo[1,2,5]thiadiazole

[0218]

[0219] At room temperature, the SOCl 2(4.04 mL, 0.055 mol) was added dropwise to 4,5-difluorobenzene-1,2-diamine (2.0 g, 0.014 mol) and triethylamine (7.8 mL, 0.056 mol) in dichloromethane (80 mL) in the solution. The resulting reaction mixture was heated to reflux overnight. The reaction mixture was then allowed to cool to room temperature and carefully quenched with water. The resulting mixture was extracted with dichloromethane, washed with Na 2 SO 4 Drying and concentration on a rotary evaporator afforded a white solid as crude compound. The crude product was purified by flash column chromatography (silica gel, hexanes) to give 5,6-difluorobenzo[1,2,5]thiadiazole (1.4 g, 58% yield) as a white crystalline solid ). 1 HNMR (CDCl 3 500MHz): δ: 7.76 (t, 2H, J=8.5Hz). 13 CNMR (CDCl 3 , 500MHz): δ154.94, 154.78, 152.86, ...

example 1

[0223] example 1B: Preparation of 4,7-bis-(5-bromo-thiophen-2-yl)-5, 6- Difluoro-benzo[1,2,5]thiadiazole

[0224] Step 1: 5,6-Difluoro-4,7-di-thiophen-2-yl-benzo[l,2,5]thiadiazole

[0225]

[0226] 4,7-dibromo-5,6-difluoro-benzo[1,2,5]thiadiazole (0.29g, lmmol), tributyl-thiophen-2-yl-stannane (0. 86g, 2.3mmo1) and Pd(PPh 3 ) 4 (20mg) into a 50mL Schlenk flask. The system was evacuated and backfilled with argon for three cycles, followed by the addition of 20 mL of anhydrous toluene. The mixture was heated at 105°C for 4 days. After the reaction cooled down, the solvent was removed by rotary evaporation. The product was further purified by silica gel column with toluene / hexane (v / v, 1 / 2) as eluent and recrystallized from hexane / isopropanol mixture. After drying in vacuo, the final product was obtained as red needles (0.276 g, 93.0% yield). 1 HNMR (CDCl 3 , 500MHz): δ8.33(d×d, 2H, J=4.0Hz×1.0Hz), δ7.66(d×d, 2H, J=5.5Hz×1.0Hz), 67.30( d×d, 2H, J=5.5Hz×4.0Hz).

...

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PUM

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Abstract

Certain polymeric compounds and their use as organic semiconductors in organic and hybrid optical, optoelectronic and / or electronic devices such as photovoltaic cells, light emitting diodes, light emitting transistors and field effect transistors are disclosed herein. The disclosed compounds can provide improved device performance, for example when used in photovoltaic cells or transistors as measured by power conversion efficiency, fill factor, open circuit voltage, field effect mobility, on / off current ratio, and / or air stability . The disclosed compounds may have good solubility in common solvents, enabling device fabrication via solution methods.

Description

Background technique [0001] A new generation of optoelectronic devices, such as organic photovoltaics (OPVs) and organic light-emitting transistors (OLETs), are fabricated using organic semiconductors as their active components. To be commercially meaningful, these organic semiconductor-based devices should be processable in a cost-effective manner. [0002] Bulk heterojunction (BHJ) solar cells are generally regarded as the most promising OPV structures because they can be fabricated using roll-to-roll and mass production. BHJ solar cells include a photoactive layer disposed between an anode and a cathode, wherein the photoactive layer is composed of a blend film including a "donor" material and an "acceptor" material. Current state-of-the-art BHJ solar cells use fullerene-based compounds as acceptor materials. Typical fullerenes include C60 or C70 "bucky ball" compounds that are functionalized with solubilizing side chains such as [6,6]-phenyl-C 61 - Butyric acid methyl e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): H01L51/00H10K99/00
CPCY02E10/549C08G61/123C08G2261/124C08G2261/1412C08G2261/1424C08G2261/146C08G2261/3223C08G2261/3243C08G2261/3246C08G2261/344C08G2261/364C08G2261/414C08G2261/512C08G2261/794C08G2261/91C08G2261/92C08G2261/95H10K85/113H10K85/151H10K85/40H10K30/30H10K50/14H10K50/11C08G75/06C08G61/00H10K85/111
Inventor 朱正国潘华龙M·椎斯H·乌斯塔吕少峰A·菲奇提
Owner RAYNERGY TEK INC
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