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Vertical benzodithiophene-based donor-acceptor polymers for electronic and photonic applications

A conjugated polymer and acceptor technology, applied in the field of OE devices and OPV devices, can solve problems such as poor performance, and achieve the effects of wide optical band gap, high charge mobility, and strong temperature-dependent aggregation characteristics

Active Publication Date: 2019-12-03
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, such thiophene-vBDT-thienyl donor polymers may exhibit poor performance

Method used

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  • Vertical benzodithiophene-based donor-acceptor polymers for electronic and photonic applications
  • Vertical benzodithiophene-based donor-acceptor polymers for electronic and photonic applications
  • Vertical benzodithiophene-based donor-acceptor polymers for electronic and photonic applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0218] Example 1: Synthesis of PvBDTTAZ

[0219]

[0220] step 1: 4,8-bis(4-(2-decyltetradecyl)thiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene (S1)。

[0221] To a solution of 3-(2-decyltetradecyl)thiophene (4.2 g, 10 mmol) in THF (40 mL) was added dropwise a solution of butyllithium (5 mL, 2.0 M in hexane) at 0°C. The solution was then stirred at 0 °C for 1 hour, after which benzo[1,2-b:4,5-b']dithiophene-4,8-dione (550 mg, 2.5 mmol) was added in one portion. The resulting yellow solution was stirred at 50 °C for 2 h before adding SnCl in 10% HCl solution (40 mL) 2 2H 2 O (11 g, 50 mmol) and the solution was stirred for another 2 hours. Hexane was added to the mixture, then, washed 3 times with water and dried over sodium sulfate. The resulting yellow oil was purified by flash chromatography to give the pure product (1.8 g, 70%) as a yellow oil.

[0222] 1 H NMR: (400MHz, CDCl 3 )7.65(d, J=5.6Hz, 2H), 7.45(s, 2H), 7.29(d, J=1.2Hz, 2H), 7.08(d, J=0.8Hz, 2H), 2.66(d,...

Embodiment 2

[0238] Example 2: Synthesis of PvBDTTAZ-Th

[0239]

[0240] ((2,6-bis(5-methylthiophen-2-yl)benzo[1,2-b:4,5-b']dithiophene-4,8-diyl)bis(3-(2 - decane Tetradecyl)thiophene-5,2-diyl))bis(trimethylsilane)(S5)

[0241] in N 2 S4 (860mg, 0.647mmol), tributyl (5-methylthiophen-2-yl) stannane (600.9mg, 1.55mmol), Pd 2 (dba) 3 (11mg, 0.02mmol) and P(o-tol) 3 (24 mg, 0.08 mmol) in 10 mL THF was refluxed overnight. The reaction mixture was then cooled to room temperature and the solvent was evaporated. The residue was purified by flash column chromatography (eluent: n-hexane) to obtain the product (573.8 mg, 65%) as a yellow liquid.

[0242]

[0243] 4,8-bis(5-bromo-4-(2-decyltetradecyl)thiophen-2-yl)-2,6-bis(5-methylthiophen-2-yl)benzo [1,2-b:4,5-b']dithiophene (S6)

[0244] N-Bromosuccinimide (263.5 mg, 1.48 mmol) was added to a mixture of S5 (1.01 g, 0.74 mmol) and silica gel (20 mg) in 20 mL of chloroform at 0°C. The reaction mixture was allowed to warm to roo...

Embodiment 3

[0247] Embodiment 3: the synthesis of PvBDTWBT

[0248]

[0249] The PvBDTWBT-Th polymer can be synthesized by microwave reaction or conventional reaction. In use N 2 To monomer S6 (19.7mg, 0.014mmol), S7 (9.5mg, 0.014mmol), Pd in ​​the protected glove box 2 (dba) 3 (1.1mg, 0.002mmol) and P(o-tol) 3 (2.4 mg, 0.008 mmol) was added 0.2 mL of chlorobenzene. The reaction mixture was then sealed and heated at 140°C for 2 days (or 140°C for 2 hours for microwave reactions). The mixture was cooled to room temperature and 10 mL of toluene was added before precipitation with methanol. The solid was collected by filtration and added to the extraction thimble and sequentially washed with CH 2 Cl 2 、CHCl 3 and toluene wash. Finally the polymer was collected from toluene. The toluene solution was then concentrated by evaporation and precipitated into methanol. The solid was collected by filtration and dried in vacuo to afford the polymer as a red solid.

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Abstract

Provided herein are donor-acceptor conjugated vertical benzodithiophene-based polymers, methods for their preparation and intermediates used therein, the use of formulations containing such polymers in the preparation of semiconductors in organic electronic devices, e.g., in organic photovoltaic and organic field-effect transistor devices, and to OE and OPV devices made from these formulations.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Application 62 / 602,474, filed April 25, 2017, the contents of which are hereby incorporated by reference in their entirety for all purposes. technical field [0003] The present disclosure relates to donor-acceptor conjugated polymers, methods for their preparation and intermediates used therein, compositions containing these polymers for the preparation of organic electronic (OE) devices, such as organic photovoltaic (OPV) devices and organic Use of semiconductors in field effect transistor (OFET) devices and OE and OPV devices made from these formulations. Background technique [0004] In recent years, there has been increasing interest in using organic semiconductors including conjugated polymers for various electronic application devices. [0005] A particular area of ​​focus is the development of organic photovoltaics (OPVs). Organic semiconductors (OSCs) can be...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/00H01L51/46H10K99/00
CPCC08G61/126C08G2261/124C08G2261/1412C08G2261/146C08G2261/148C08G2261/149C08G2261/3223C08G2261/3241C08G2261/3243C08G2261/3246C08G2261/364C08G2261/414C08G2261/92C08K3/045H10K85/211C08L65/00
Inventor 颜河陈尚尚
Owner THE HONG KONG UNIV OF SCI & TECH
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