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Thiophene-based fused aromatic systems

A technology of alkyl aryl and alkyl, applied in the field of preparation of photoactive layer

Active Publication Date: 2020-07-14
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, how to minimize the voltage loss (less than 0.7 V) in such low-bandgap small-molecule acceptors is an ongoing challenge.

Method used

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  • Thiophene-based fused aromatic systems
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  • Thiophene-based fused aromatic systems

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0245] The synthesis of embodiment 1-TTDTT-CHO

[0246]

[0247] At -78°C, to a solution of thiophene[3,2-b]thiophene (3.00 g, 21.40 mmol) in THF was added dropwise a 2.0 M solution of n-butyllithium in hexane (11.20 mL , 22.47mmol). The reaction mixture was stirred at -78 °C for 1 h, then TIPSCl (4.54 g, 23.53 mmol) was added. The mixture was returned to room temperature and stirred overnight. The reaction was quenched with water and extracted three times with ethyl acetate. The combined organic phases were washed with water and brine successively, and then the solution was washed with Na 2 SO 4 Dry and concentrate under reduced pressure. The crude product was purified by flash column chromatography (eluent: n-hexane) to give a white solid product (4.24 g, 67%).

[0248]

[0249] At -78°C, to compound 1 (4.24g, 14.28mmol) in THF solution, under N 2 A 2.0M solution of n-butyllithium in hexane (7.80 mL, 15.71 mmol) was added dropwise under protection. The reaction...

Embodiment 2-IX

[0258] The synthesis of embodiment 2-IXIC

[0259]

[0260] in N 2 , to TTTDT-CHO (60 mg, 0.053 mmol) and 1,1-dicyanomethylene-3-indanone (102 mg, 0.53 mmol) in anhydrous CHCl 3 To a solution in (10 mL) was added pyridine (0.1 mL). The mixture was refluxed for 16 h, then cooled to room temperature, and the mixture was poured into CH 3 OH (100mL) and filtered, the residue remaining in the filter paper was passed through CHCl 3 dissolve. After removal of the solvent, the residue was purified using silica gel column chromatography using petroleum ether / CH 2 Cl 2 (1:1, v / v) as eluent, a dark green solid (50 mg, 64%) was obtained. 1 H NMR (400MHz, CDCl 3 , ppm): δ=8.837(s, 2H), 8.664-8.644(m, 2H), 8.107(s, 2H), 7.912-7.891(m, 2H), 7.762-7.703(m, 4H), 7.212-7.155 (m, 16H), 2.581(t, 8H, J=7.8Hz), 1.604-1.526(m, 8H), 1.342-1.247(m, 24H), 0.862(t, 12H, J=6.8Hz); 13 CNMR (100MHz, CDCl 3 ,ppm):δ=188.502,160.525,152.739,149.361,148.531,147.357,143.165,142.844,140.264,139.752,...

Embodiment 3-IX

[0261] The synthesis of embodiment 3-IXIC-2F

[0262]

[0263] in N 2 , to TTDTT-CHO (54 mg, 0.047 mmol), 2-(5-fluoro-3-oxo-2,3-dihydro-1H-indan-1-alkylene)malononitrile and 2-( 6-Fluoro-3-oxo-2,3-dihydro-1H-indenyl-1-alkylene)malononitrile (100 mg, 0.47 mmol) in anhydrous CHCl 3 (10 mL) was added pyridine (0.1 mL). The mixture was refluxed for 16 h, then cooled to room temperature, and the mixture was poured into CH 3 OH (100mL) and filtered, the residue remaining in the filter paper was passed through CHCl 3 dissolve. After removing the solvent, use petroleum ether / CH 2 Cl 2 The residue was purified using column chromatography on silica gel (1:1, v / v) as eluent to give a dark green solid (41 mg, 57%).

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Abstract

The invention relates to thiophene-based small molecule acceptors, their methods of preparation, and formulations thereof useful for preparing photoactive layers in organic solar cells (OSCs).

Description

[0001] Cross References to Related Applications [0002] This application claims priority and benefit to U.S. Provisional Patent Application No. 62 / 709,172, filed January 10, 2018, the disclosure of which is incorporated herein by reference in its entirety technical field [0003] The present invention generally relates to organic semiconductors, processes for their preparation and their formulations for the preparation of photoactive layers in organic solar cells. Background technique [0004] Organic solar cells are considered to be a promising, low-cost, and environmentally friendly solar technology because they can be produced with less-costly printing methods, often without the need for any toxic materials. [0005] A typical organic solar cell device consists of a pair of materials that act as electron donor and electron acceptor. The most commonly used class of electron acceptors is the fullerene class of electron acceptors. Conventional fullerene-based organic sol...

Claims

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Application Information

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IPC IPC(8): H01L51/00C07D495/22H01L51/42
CPCC07D495/22Y02E10/549Y02P70/50H10K85/113H10K85/151H10K85/621H10K85/6576H10K30/30H10K30/57
Inventor 颜河陈于中
Owner THE HONG KONG UNIV OF SCI & TECH
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