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A-d-a conjugated molecule based on dithienoindacene and its preparation method and application

A technology of conjugated molecule and dithiophene, which is applied in the field of A-D-A conjugated molecule based on dithiophene and indacene and its preparation and application, to achieve good thermal stability, good light absorption and excellent thermal stability Effect

Active Publication Date: 2017-04-05
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there is no literature or patent report based on the application of Inda province's A-D-A conjugated small molecules in organic solar cells

Method used

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  • A-d-a conjugated molecule based on dithienoindacene and its preparation method and application
  • A-d-a conjugated molecule based on dithienoindacene and its preparation method and application
  • A-d-a conjugated molecule based on dithienoindacene and its preparation method and application

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Experimental program
Comparison scheme
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 (0.1gmL -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 present invention relates to a class of A-D-A conjugated molecules based on a dithieno-indazene unit as a core, an oligomerized five-membered aromatic heterocycle as a bridging unit, and an electron-drawing unit at the end and a preparation method thereof, and the class Applications of molecules as active layer electron donor or electron acceptor materials in organic solar cells. The A-D-A conjugated molecule based on dithienoindacene of the present invention can be processed by solution method, has suitable energy level, strong sunlight capture ability and thermal stability, and is an electron donor or Ideal materials for electron acceptors. It has the following general structure:

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.,2013,46,2645...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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