Linear (d-π-a-π)2-d type organic small molecule photovoltaic materials containing benzotriazole units and their preparation and application

A technology of benzotriazole and photovoltaic materials, which is applied in the field of organic small molecule photovoltaic materials and its preparation, can solve the problems of low overall efficiency of solar cells, and achieve the effect of improving solubility

Inactive Publication Date: 2018-08-14
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the overall efficiency of bulk heterojunction solar cells based on small molecules as donors is still lower than that of the same type of polymer materials, so it is urgent to design and synthesize new small molecule photovoltaic materials to enrich their research scope

Method used

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  • Linear (d-π-a-π)2-d type organic small molecule photovoltaic materials containing benzotriazole units and their preparation and application
  • Linear (d-π-a-π)2-d type organic small molecule photovoltaic materials containing benzotriazole units and their preparation and application
  • Linear (d-π-a-π)2-d type organic small molecule photovoltaic materials containing benzotriazole units and their preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] This example discloses the linear (D-π-A-π) 2 -The specific synthesis process of D-type organic small molecule donor material F1 includes the following steps:

[0039]Under nitrogen protection, compound M2 (122 mg, 0.1 mmol), N-(4-(4,4,5,5-tetramethyl-[2,1,3]dioxaborolyl)benzene base)-N-phenylaniline ie Q represents D2 when C-C (93 mg, 0.25 mmol), potassium carbonate (552 mg, 4.0 mmol) and tetrakis(triphenylphosphine)palladium (11 mg, 0.01 mmol) were dissolved in toluene (4 mL), deionized water (2 mL) and ethanol (1 mL), and reflux at 110°C for 18-24 hours. After the reaction mixture was cooled to room temperature, it was poured into 20 mL deionized water for separation, and extracted with dichloromethane. The organic phases were combined and dried over anhydrous sodium sulfate. The organic solvent was removed by rotary evaporation, and the crude product was purified by column chromatography using petroleum ether / dichloromethane (v:v, 3:1) as a developing solvent to ...

Embodiment 2

[0046] This example discloses the linear (D-π-A-π) 2 -The specific synthesis process of D-type organic small molecule donor material F2 includes the following steps:

[0047] Under the protection of nitrogen, the compound M2 (122 mg, 0.1 mmol), 4-(N,N-diphenylamino) styrene, that is, D2 when Q represents C=C (68 mg, 0.25 mmol), palladium acetate (2 mg, 0.01 mmol), sodium acetate (205 mg, 2.5 mmol) and TBAB (13 mg, 0.04 mmol) were dissolved in N,N-dimethylformamide (10 mL) solution, and refluxed at 100°C for 36 hours . After the reaction solution was cooled to room temperature, it was poured into 50 mL deionized water and extracted with dichloromethane, and then the organic phase was washed with deionized water. Finally the organic phase was dried over anhydrous sodium sulfate. After rotary evaporation to remove the organic solvent, the crude product was purified by column chromatography using petroleum ether / dichloromethane (v:v, 5:2) as the developing solvent to obtain a r...

Embodiment 3

[0054] This example discloses the linear (D-π-A-π) 2 -The specific synthesis process of D-type organic small molecule donor material F3 includes the following steps:

[0055] Compound M2 (244 mg, 0.2 mmol), 4-(N,N-diphenylamino) phenylacetylene, that is, D2 (134 mg, 0.5 mmol) when Q represents C≡C, bis(triphenylphosphine) di Palladium chloride (4 mg, 0.005 mmol) and cuprous iodide (2 mg, 0.01 mmol) were dissolved in a mixed solution of tetrahydrofuran (20 mL) and triethylamine (15 mL), and reacted under reflux at 70°C for 24 hours. After the reaction solution was cooled to room temperature, it was poured into 50 mL of deionized water and extracted with dichloromethane. The organic phases were combined and dried over anhydrous sodium sulfate. After rotary evaporation to remove the organic solvent, the crude product was purified by column chromatography using petroleum ether / dichloromethane (v:v, 5:2) as the developing solvent to obtain the target product as an orange-red solid...

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Abstract

A linear (D-π-A-π)2-D type organic small molecule photovoltaic material containing a benzotriazole unit and a preparation method and application thereof belong to the technical field of photoelectric materials. The material uses carbazole as the core, benzotriazole-triphenylamine as the side chain, and thiophene and C-C, C=C or C≡C as the connecting bridge; multiple π structural units are introduced into the molecular skeleton , which effectively prolongs the conjugation length, enhances the intramolecular charge transport, thereby improving the charge transport capability of the material and adjusting the energy level structure of the molecule; and by introducing an alkyl chain on the nitrogen atom of benzotriazole and The way of introducing a triphenylamine group with a three-dimensional configuration in the side chain effectively improves the solubility of the material and the film-forming property of the device. This type of compound has a clear structure and molecular weight, good solubility and film-forming properties, and has the potential to be used as a high-efficiency organic small molecule photovoltaic material, and effectively solves the photoelectric conversion efficiency (PCE) of organic small molecule photovoltaic devices containing benzotriazole units Less than 1.0% defects.

Description

technical field [0001] The invention belongs to the field of photoelectric materials, and in particular relates to an organic small molecule photovoltaic material containing a benzotriazole unit, a preparation method thereof and the application of the compound as a bulk heterojunction solar cell donor material. Background technique [0002] In recent years, solar energy has been extensively studied as a green renewable energy source. Compared with inorganic solar cells, organic solar cells have the characteristics of lightness and portability, simple manufacturing process, and good mechanical properties and flexibility of the device. Organic solar cell materials can be broadly classified into polymers and small molecules. Among them, organic small molecule bulk heterojunction solar cell materials have attracted more and more attention because of their advantages such as clear molecular structure, easy purification, low device manufacturing cost and good repeatability. At p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/14H01L51/46
CPCC07D409/14H10K85/655H10K85/631H10K85/654H10K30/00Y02E10/549Y02P70/50
Inventor 汲长艳殷伦祥李艳芹
Owner DALIAN UNIV OF TECH
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