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A kind of fluorine boron fluorescent organic small molecule dimer and its preparation method and application in organic photovoltaic devices

An organic and carbon atom technology, applied in the field of organic photovoltaics, fluorine-boron-fluorescent small molecule dimer and its preparation field, can solve the problems of restricting light absorption performance and weak absorption, etc.

Active Publication Date: 2019-04-09
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

The corresponding product exhibits two strong and broad absorption peaks covering the near-infrared region (650-800nm) and the near-ultraviolet region (350-480nm). light absorption properties

Method used

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  • A kind of fluorine boron fluorescent organic small molecule dimer and its preparation method and application in organic photovoltaic devices
  • A kind of fluorine boron fluorescent organic small molecule dimer and its preparation method and application in organic photovoltaic devices
  • A kind of fluorine boron fluorescent organic small molecule dimer and its preparation method and application in organic photovoltaic devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Example 1: Preparation of compound 3a

[0076]

[0077] 110 mL of freshly distilled dichloromethane was added to a 500 mL round-bottomed flask, followed by N 2 to remove oxygen from the system. Then compound 1a (267.1 mg, 1 mmol) and compound 2a (209.3 mg, 2.2 mmol) were added to the flask, followed by 50 μL of trifluoroacetic acid, and the color of the reaction system quickly changed from pale yellow to reddish brown. After stirring continued for 1 hour, DDQ (249.7 mg, 1.1 mmol) was added rapidly to the reaction. After the oxidation reaction was carried out for 2 hours, DIEA 3 mmol was added dropwise to the flask, and the reaction was continued for 50-60 minutes to neutralize the acid produced in the reaction system, and then the BF was stirred vigorously. 3 ·OEt 2 4.5 mmol was slowly added to the system and stirring was continued for 80 minutes. The above reaction processes were all carried out in the dark and under the protection of nitrogen. After the reacti...

Embodiment 2

[0078] Example 2: Preparation of compound 5a

[0079]

[0080] Compound 3a (485.2 mg, 1 mmol), compound 4a (612.5 mg, 2.2 mmol), and 300 mg of 4A molecular sieves were added to the reaction flask, followed by injection of 12 mL of toluene solution, and nitrogen gas was continuously injected for 30 minutes to ensure the inert atmosphere of the reaction system, and then Anhydrous acetic acid (0.8 mL) and piperidine (1 mL) were rapidly injected into the system. The reaction was then sealed and heated in a 100°C oil bath for 10 hours. After the reaction was completed, the reaction system was cooled to room temperature, and the solution was poured into 50 mL of water to remove water-soluble impurities. Extraction was then carried out with 100 mL of dichloromethane solution. After liquid separation, the dichloromethane layer was collected, and after rotary evaporation under reduced pressure, a black-green solid was obtained, which was passed through a silica gel column to obtai...

Embodiment 3

[0081] Example 3: Preparation of compound 7a

[0082]

[0083] Inject 10 mL of ultra-dry tetrahydrofuran into the reaction flask, then add compound 6a (637.0 mg, 1 mmol), bisborate (635.0 mg, 2.5 mmol), and after evacuating the gas through the double-row pipe for 3 times, seal the reaction flask and place it side by side In a low temperature reactor at -30°C, 1.5 mL of LDA solution in tetrahydrofuran (commercially available, concentration 2 mol / L) was added dropwise to the system, and the reaction system was gradually raised to room temperature after 1 hour. After the reaction was completed, 50 mL of water was added to the system to quench the reaction and 80 mL of chloroform was used for extraction. The obtained organic phase was concentrated to 25 mL by reduced pressure distillation, the obtained concentrated solution was poured into 150 mL of cold acetone, and the pink solid was obtained by suction filtration, which was compound 7a. . 1 H NMR (400MHz, CDCl 3 ):δ9.12(s,...

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Abstract

The invention relates to a compound of general formula I, a preparation method thereof and an application thereof in the field of organic photovoltaics. The invention also relates to an organic solar cell containing a compound of general formula I and a method for preparing the same. The compound of general formula I is a BODIPY small molecule dimer structure bridged by position 8, which has a wide spectrum coverage (300-800nm) in the visible light region, and can more effectively and fully utilize sunlight. Moreover, the crystalline bridging unit in the compound of formula I can facilitate the orderly accumulation of molecules in the mixed state with the acceptor material, and significantly increase the current of the solar cell device, thereby improving the efficiency of the material.

Description

technical field [0001] The invention belongs to the field of organic photovoltaic materials, and relates to a fluorine-boron-fluorescent small-molecule dimer bridged at the 8th position, a preparation method thereof, and an application thereof in the field of organic photovoltaics. Background technique [0002] Solar energy has the advantages of clean, renewable and huge reserves. Effective use of solar energy is a way to solve the problems of energy crisis and environmental pollution in the 21st century. Using solar cells to convert solar energy into electrical energy is a research hotspot in recent years. [0003] Compared with silicon-based and inorganic semiconductor photovoltaic materials, solution-processable organic polymers and small-molecule photovoltaic materials have the advantages of low cost and suitable for large-area flexible processing. Donor materials in the active layer of batteries can be divided into polymers and small molecules. Compared with polymer m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/42H01L51/46H01L51/48
CPCC09K11/06C07F5/022C09K2211/1092H10K85/6576H10K85/6572H10K30/00Y02E10/549Y02P70/50
Inventor 姚建年詹传郎刘文旭
Owner INST OF CHEM CHINESE ACAD OF SCI
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