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Preparation method and application of two-dimensional aza-indacene-based organic solar cell donor materials

A technology of solar cells and donors, applied in luminescent materials, organic chemistry, electric solid devices, etc., can solve problems such as insufficient supply of raw materials, achieve broad commercial application prospects, increase planarity, and easily obtain raw materials

Inactive Publication Date: 2015-12-30
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the highest photoelectric conversion efficiency of solar cell donor materials is about 10%, and the supply of raw materials is insufficient, so it still has certain limitations in large-scale commercial production.

Method used

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  • Preparation method and application of two-dimensional aza-indacene-based organic solar cell donor materials
  • Preparation method and application of two-dimensional aza-indacene-based organic solar cell donor materials
  • Preparation method and application of two-dimensional aza-indacene-based organic solar cell donor materials

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 2,7-Ditriisopropylchlorosilane-1,3,b-6,8,b'-Dithiazoleindacene-4,9-dione (Azaindacene) (2g, 3.3mmol) Under the protection of nitrogen, the carbon dichloride solution was added dropwise in the dichloromethane solution of carbon tetrabromide (4.4g, 13.2mmol) and triphenylphosphine (6.9g, 26.3mmol), reacted for 20min, and the solution changed from yellow to After a period of reaction, a red solid appeared after a purple-black reaction, and the TLC plate was used to detect the reaction. After the reaction was free of raw materials. Quenched with water, dichloro extracted, anhydrous Na 2 SO 4 To dry, spin dry. Then, a silica gel column was used for column separation (PE:DCM=4:1) to obtain 2.78 g of a bright red solid with a yield of 92%. 1 HNMR (400MHz, CDCl3), δ (TMS, ppm): δ8.47 (s, 2H), 1.44 (dq, J = 14.4, 7.4Hz, 6H), 1.20 (d, J = 7.4Hz, 36H).HRMS :m / z915.9218(M+ ,calcd916.0034).

[0037] The structure of NIDT4Br is shown below:

[0038]

Embodiment 2

[0040] NIDT4Br (1.39g, 1.5mmol), 5-hexylthiophene-2-tributyltin (4.12g, 9.0mmol), Pd (PPh 3 ) 4 (0.11g, 0.1mmol), dissolved in 100ml of toluene solution, passed through nitrogen for half an hour, reacted under nitrogen protection for 24 hours, and the reaction temperature was 120°C. After the reaction, the solution was cooled to room temperature, poured into water, extracted with dichloromethane, washed the organic layer with water, dried over anhydrous magnesium sulfate, filtered, and evaporated by rotary evaporation. The product was passed through the column with a mixture of n-hexane and dichloromethane (volume ratio of the mixture = 3-4:1) as the eluent. The yield of purple viscous NIDT4ThC6TIPS (1.76g) was 93%.

[0041] 1 HNMR (400MHz, CDCl 3 ), δ(TMS, ppm): δ7.62(d, J=3.7Hz, 2H), 7.08(d, J=3.5Hz, 2H), 6.85(d, J=3.5Hz, 2H), 6.70(d ,J=3.7Hz,2H),6.67(s,2H),δ2.93(t,J=7.6Hz,4H),2.83(t,J=7.7Hz,4H),1.36(m,38H),1.12 (d,J=7.4Hz,36H),0.99–0.83(m,12H).HRMS:m / z1268.6062(M + ,...

Embodiment 3

[0044] NIDT4ThC6TIPS (1.76g, 1.39mmol) was dissolved in tetrahydrofuran (THF), and 5.5ml of tetrabutylammonium fluoride (1M / THF) was added dropwise to the system in a nitrogen atmosphere. React for 1 hour under ice-water bath. The system was poured into water, extracted with dichloromethane, the organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered, and rotovapped. The product was passed through the column with a mixture of n-hexane and dichloromethane (volume ratio of the mixture = 2:1). A dark red solid NIDT4ThC6 (1.3 g) was obtained with a yield of 99%. 1 HNMR (400MHz, CDCl 3 ),δ(TMS,ppm):δ8.52(s,2H),7.57(d,J=3.7Hz,2H),7.08(t,J=6.6Hz,2H),6.88(d,J=3.5Hz ,2H),6.85(d,J=3.7Hz,2H),6.51(s,2H),2.93(t,J=7.6Hz,4H),2.83(t,J=7.7Hz,4H),1.79(dt ,J=15.3,7.6Hz,6H),1.70(dt,J=15.4,7.6Hz,6H),1.52–0.80(m,32H).HRMS:m / z956.3394(M + ,calcd956.8754).

[0045]

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Abstract

The invention discloses a preparation method and application of a series of two-dimensional aza-indacene-based organic solar cell donor materials. The method disclosed by the invention is used for preparing high-yield solar cell materials taking two-dimensional conjugated aza-indacene as a core through simple and efficient Still reaction. Through testing, the two-dimensional aza-indacene-based organic solar cell donor materials have favorable optical properties; when the materials are mixed with PC71BM in a proportion of 1:2, the photoelectric conversion efficiency is as high as 7%; and reaction conditions are simple, raw materials are easy to obtain, the yield is relatively high, and generated compounds are stable and simple to store.

Description

[0001] The invention relates to the technical fields of organic synthesis chemistry and functional material chemistry, in particular to a preparation method and application of a photoluminescence material. Background technique [0002] Organic solar cells (polymer and small molecule solar cells, dye-sensitized solar cells) are new types of solar cells developed in the 1990s. Compared with inorganic solar cells, organic solar cells have the characteristics of low melting point, high compression coefficient, low cost, ultra-thin, and light weight. Organic materials can use relatively cheap processing techniques, including direct printing, spin coating, inkjet, etc. Printing, screen printing and other solution-based methods. These methods are not only easier to implement than inorganic semiconductors when applied to large-area circuits, but also provide the possibility of flexible electronic devices, making people full of expectations for cheap, large-area, and printable flexible...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04C09K11/06H01L51/46
CPCC09K11/06C07D513/04C09K2211/1092H10K85/657H10K30/00Y02E10/549
Inventor 王金亮宋晓欣常峥峰
Owner BEIJING INSTITUTE OF TECHNOLOGYGY