A-D-A conjugated molecule on the basis of dithiophene indacene, and preparation method and application thereof

A technology of A-D-A and conjugated molecules, applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., to achieve excellent thermal stability, good light absorption, and high charge transport performance

Active Publication Date: 2015-04-29
INST OF CHEM CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • A-D-A conjugated molecule on the basis of dithiophene indacene, and preparation method and application thereof
  • A-D-A conjugated molecule on the basis of dithiophene indacene, and preparation method and application thereof
  • A-D-A conjugated molecule on the basis of dithiophene indacene, and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0083] The synthetic route of A-D-A conjugated molecule 1 based on dithienoindacene is as follows:

[0084]

[0085] Take 246mg (0.20mmol) of compound a and 159.5mg (0.50mmol) of compound b in a 50mL three-necked flask, add 25mL of freshly distilled anhydrous toluene; under stirring, pass argon for 15 minutes to remove the air in the three-necked flask, then Under the protection of Pd(PPh 3 ) 4 (40mg, 0.034mmol), heated to 110°C, refluxed for 24 hours; after cooling to room temperature, add 10mL (0.1g mL -1 ) KF aqueous solution, stirred overnight at room temperature to remove tin impurities; add 100mL water, CHCl 3 (2 × 100mL) extraction; organic phase with anhydrous MgSO 4 Carry out drying; After filtering and spinning to remove the solvent, use petroleum ether / dichloromethane mixed solvent (volume ratio 1:2) as eluent, silica gel (200~300 mesh) column chromatography separation and purification, obtain black solid (248mg , 89.7%), which is the A-D-A conjugated molecul...

Embodiment 2

[0088] The synthetic route of A-D-A conjugated molecule 2 based on dithienoindacene is as follows:

[0089]

[0090] Take 492mg (0.40mmol) of compound a, 302mg (1.0mmol) of compound c in a 50mL three-necked flask, add 30mL of freshly distilled anhydrous toluene; under stirring, pass argon for 15 minutes to remove the air in the three-necked flask, and then Under protection, adding Pd(PPh 3 ) 4 (40mg, 0.034mmol), heated to 110°C, refluxed for 24 hours; after cooling to room temperature, add 10mL (0.1g mL -1 ) KF aqueous solution, stirred overnight at room temperature to remove tin impurities; add 100mL water to the reactant, CH 2 Cl 2 (2 × 100mL) extraction; organic phase with anhydrous MgSO 4 Carry out drying; After filtering and spinning to remove the solvent, use petroleum ether / dichloromethane mixed solvent (volume ratio 1:4) as eluent, silica gel (200~300 mesh) column chromatography separation and purification to obtain a black solid (181mg , 33.5%), which is the A...

Embodiment 3

[0093] That is, the synthetic route of A-D-A conjugated molecule 3 based on dithienoindacene is as follows:

[0094]

[0095] Take 221.8mg (0.18mmol) of compound a and 165mg (0.45mmol) of compound d in a 50mL three-necked flask, add 20mL of freshly distilled anhydrous toluene; under stirring, pass argon for 15 minutes to remove the air in the three-necked flask, then Under the protection of Pd(PPh 3 ) 4 (40mg, 0.034mmol), heated to 110°C, refluxed for 24 hours; after cooling to room temperature, add 40mL (0.1g mL -1 ) KF aqueous solution, stirred overnight at room temperature to remove tin impurities; add 100mL water, CHCl 3 (2 × 100mL) extraction; organic phase with anhydrous MgSO 4 Carry out drying; After filtering and spinning to remove the solvent, use petroleum ether / dichloromethane mixed solvent (volume ratio 1:4) as eluent, silica gel (200~300 mesh) column chromatography separation and purification to obtain a black solid (230mg , 86.4%), which is the A-D-A conju...

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Abstract

The invention relates to an A-D-A conjugated molecule with dithiophene indacene as a core, and oligomerizing pentatomic aromatic heterocyclic rings as a bridging unit and electron withdrawing unit at the end, a preparation method thereof and an application of the molecule, as an active-layer electron donor or electron receptor material, in an organic solar battery. The A-D-A conjugated molecule can be processed by a solution method, has proper energy level, strong sunlight trapping capability and thermal stability, is an ideal material of the electron donor or the electron receptor in the organic solar battery, and has the following general-formula structure shown in the specification.

Description

technical field [0001] The present invention relates to an A-D-A conjugated molecule based on a dithienyl-indase unit as a core, an oligomerized five-membered aromatic heterocycle as a bridging unit, and an electron-withdrawing unit at the end, and a preparation method thereof, and the electron donor of this type of molecule as an active layer Applications of Bulk or Electron Acceptor Materials in Organic Solar Cells (OPVs). Background technique [0002] Due to the advantages of low cost, light weight, bendability, solution processability and large area preparation, organic solar cells have received extensive attention in academia. In recent years, polymer and small molecule solar cells have developed rapidly and achieved remarkable results (X.Zhan, D.Zhu, Conjugated polymers for high-efficiency organic photovoltaics, Polym.Chem., 2010, 1,409; Y.Chen, X .Wan, G.Long, High performance photovoltaic applications using solution-processed small molecules, Acc.Chem.Res., 2013, 46...

Claims

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Application Information

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IPC IPC(8): C07D495/04C07D519/00H01L51/46
CPCC07D495/04C07D519/00H10K85/649H10K85/653H10K85/655H10K85/656H10K85/615H10K85/6576H10K85/6572H10K85/657Y02E10/549
Inventor 占肖卫白会涛林禹泽
Owner INST OF CHEM CHINESE ACAD OF SCI
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