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Organic dye centered on phenanthrene and carbazole, preparation method thereof and organic dye sensitized solar cell

An organic dye, phenanthrocarbazole technology, applied in the field of organic dye-sensitized solar cells, can solve the problems of specific efficiency gap, limit the application of noble metal dyes, and limited reserves of precious metals, and achieve low cost, environmental friendliness, and avoid the use of heavy metals Effect

Active Publication Date: 2014-11-19
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the practical application of noble metal dyes is limited due to the limited reserves of noble metals.
However, the highest efficiency of pure organic dye-sensitized cells without noble metals is only 8.8%, and there is still a large gap in the specific efficiency of ruthenium-based dyes.

Method used

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  • Organic dye centered on phenanthrene and carbazole, preparation method thereof and organic dye sensitized solar cell
  • Organic dye centered on phenanthrene and carbazole, preparation method thereof and organic dye sensitized solar cell
  • Organic dye centered on phenanthrene and carbazole, preparation method thereof and organic dye sensitized solar cell

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preparation example Construction

[0054] The present invention also provides a method for preparing an organic dye with phenanthrocarbazole as the core, comprising:

[0055] The compound shown in formula (IV) is reacted with N,N-dimethylformamide and phosphorus oxychloride, and then with the triphenylamine borate derivative shown in formula (Ⅴ), in palladium acetate, Sphos and potassium phosphate Under the effect of reacting, finally react with cyanoacrylic acid under the effect of ammonium acetate, obtain the organic dye shown in formula (1);

[0056]

[0057] in,

[0058] R 1 from C 1 ~C 18 alkyl;

[0059] R 2 , R 3 Independently selected from H, C 1 ~C 18 Alkyl or C 1 ~C 18 Any of the alkoxy groups;

[0060] y is 0;

[0061] x is halogen.

[0062] First, the compound shown in formula (IV) is reacted with N,N-dimethylformamide and phosphorus oxychloride, and the reaction scheme is as follows:

[0063]

[0064] Specifically, first mix the compound represented by formula (IV) with 1,2-dichl...

Embodiment 1

[0105] The preparation of the organic dye of formula (II) structure, synthetic route is as follows:

[0106]

[0107] Compound 1 was synthesized according to references (W. Jiang, H. Qian, Y. Li, Z. Wang, J. Org. Chem. 2008, 73, 7369.).

[0108] In a dry Schlenk reaction flask, dissolve 2.00g of compound 1 in 20mL of 1,2-dichloroethane, cool the reaction system to 0°C on ice, and add 0.31mL of N,N-dimethylformamide to the reaction system And 0.40mL of phosphorus oxychloride, heated up to 40 ℃ and reacted overnight.

[0109] After the reaction, cool the reaction system to room temperature, add 20 mL of water and stir for 2 hours, extract three times with chloroform, combine the organic phases, dry the organic phases with anhydrous sodium sulfate, filter to remove the desiccant, concentrate the filtrate, and use ethyl acetate / petroleum ether (Volume ratio 1 / 20) was used as a developing solvent for column chromatography to obtain 1.76 g of intermediate 2 with a yield of 84%. ...

Embodiment 2

[0134] Preparation of organic dye Ⅲ

[0135] The reaction scheme is as follows:

[0136]

[0137] Synthesis of intermediate 5:

[0138] Compound 4 was synthesized according to literature (R. Li, J. Liu, N. Cai, M. Zhang and P. Wang, J. Phys. Chem. B, 2010, 114, 4461.).

[0139] In a dry Schlenk reaction flask, 500mg of compound 4 and 218mg of triisopropylsilylacetylene were dissolved in 20ml of toluene, and 67mg of Pd(PPh 3 ) 2 Cl 2 , 18mg cuprous iodide and 2mL triethylamine. The reaction system was heated to reflux overnight.

[0140] After the reaction was complete, the temperature of the system was lowered to room temperature. After adding 30 mL of distilled water, extracted three times with chloroform, combined the organic phases, dried the organic phases with anhydrous sodium sulfate, filtered to remove the desiccant, concentrated the filtrate, and used ethyl acetate / petroleum ether (volume ratio 1 / 50) was used as a developing agent for column chromatography to ...

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Abstract

The invention provides an organic dye whose structure is as shown in formula (1). The invention is centered on phenanthrene and carbazole, and replaced triphenylamine donors and cyano acrylic acid receptors are used to regulate the energy level structure of dye molecules, so that various effective donor receptor organic dyes are designed and formed. An organic dye sensitized solar cell prepared from the dye molecules has a power conversion efficiency of over 10 percent which is far higher than other organic dye sensitized solar cells centered on phenanthrene and carbazole. The organic dye provided by the invention is prepared without the use of heavy metals, and has the advantages of abundant source of raw materials, lower cost and environmentally friendly industrial production.

Description

technical field [0001] The invention relates to the technical field of organic dyes, in particular to an organic dye with phenanthrocarbazole as the core, a preparation method thereof, and an organic dye-sensitized solar cell. Background technique [0002] With the increase of energy demand, the search for clean and sustainable energy has gradually become a global research hotspot. Among them, solar energy is a renewable clean energy, and its development and utilization is one of the important topics in the field of energy research. [0003] At present, silicon-based solar cells have achieved high photoelectric conversion efficiency and are widely used in various fields of national production including aerospace. Among them, crystalline silicon solar cells are the most widely used technology, accounting for more than 80% of solar cells. However, it has disadvantages such as high manufacturing cost, harsh process conditions, high energy consumption and serious pollution in t...

Claims

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Application Information

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IPC IPC(8): C09B57/00H01G9/20H01G9/042
CPCY02E10/542Y02P70/50
Inventor 王鹏姚朝阳张敏李仁志马文涛
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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