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An organic dye, its preparation method and a sensitized solar cell containing the organic dye

A technology of organic dyes and solar cells, applied in the field of dye-sensitized solar cells and sensitized solar cells, can solve the problems of dye-sensitized solar cells that cannot be industrialized on a large scale, and the photothermal stability of devices is not good, and achieve industrial production Bright prospects, low cost, and good photothermal stability

Active Publication Date: 2017-11-17
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
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Problems solved by technology

[0003] The invention aims to solve the technical problem that dye-sensitized solar cells cannot be industrialized on a large scale due to poor photothermal stability of devices prepared by existing materials, and provides a twisted electronic skeleton combined with a non-electronically active side modification group Organic dye with better three-dimensional structure, preparation method thereof, and sensitized solar cell comprising the organic dye

Method used

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  • An organic dye, its preparation method and a sensitized solar cell containing the organic dye
  • An organic dye, its preparation method and a sensitized solar cell containing the organic dye
  • An organic dye, its preparation method and a sensitized solar cell containing the organic dye

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preparation example Construction

[0039] The preparation method of organic dye provided by the invention comprises the following steps:

[0040] Step 1, have the compound of formula (1) structural formula in Pd(OAc) 2 , PCy 3 ·HBF 4 , PivOH and K 2 CO 3 Under the action, the compound with the structural formula of the formula (3) is obtained through the coupling reaction of the compound of the structural formula of the formula (2) through the activation of the C-H bond;

[0041]

[0042] Step 2-1, have the compound of formula (3) structural formula in Pd(OAc) 2 , PCy 3 ·HBF 4 , PivOH and K 2 CO 3 Under the action, the dye precursor butyl ester compound is obtained through the C-H bond activation and the compound having the formula (4) for coupling reaction;

[0043]

[0044]Or step 2-2, the compound with formula (3) structural formula carries out bromination with NBS reagent, and the bromination product obtained is in Pd(PPh 3 ) 2 Cl 2 , triphenylphosphine, cuprous iodide, and diisopropylamin...

Embodiment 1

[0053]

[0054] Compound 2 was synthesized according to references (M. Zhang, Y. Wang, M. Xu, W. Ma, R. Li, P. Wang, Energy Environ. Sci., 2013, 6, 2944). In the present invention, the sources of other raw material compounds, solvents, and catalysts in the process of preparing organic dyes are not particularly limited, and can be commercially available or prepared according to methods known in the art.

[0055] Synthesis of compound shown in formula (II):

[0056] In a three-neck round bottom flask, 2.70 g of compound 1 was dissolved in 40 ml of toluene, and 1.62 g of compound 2, 45 mg of Pd(OAc) were added to the reaction system under the protection of argon. 2 , 151 mg PCy 3 ·HBF 4 , 104 mg PivOH and 705 mg K 2 CO 3 , heated to reflux, and reacted overnight with stirring.

[0057] After the reaction was finished, the reaction system was cooled to room temperature, 40 ml of water was added, the resulting mixed solution was extracted three times with chloroform, the or...

Embodiment 2

[0063]

[0064] Compound 3 was synthesized according to literature (Z. Yao, H. Wu, Y. Li, J. Wang, J. Zhang, M. Zhang, Y. Guo and P. Wang, Energy Environ. Sci., 2015, 8, 3192). In the present invention, the sources of other raw material compounds, solvents, and catalysts in the process of preparing organic dyes are not particularly limited, and can be commercially available or prepared according to methods known in the art.

[0065] Synthesis of target product III:

[0066] In a three-neck round bottom flask, 2.70 g of compound 1 was dissolved in 40 ml of toluene, and 1.72 g of compound 3, 45 mg of Pd(OAc) were added to the reaction system under the protection of argon. 2 , 151 mg PCy 3 ·HBF 4 , 104 mg PivOH and 705 mg K 2 CO 3 , heated to reflux, and reacted overnight with stirring.

[0067] After the reaction was finished, the reaction system was cooled to room temperature, 40 ml of water was added, the resulting mixed solution was extracted three times with chlorofo...

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Abstract

The invention relates to an organic dye, a preparation method thereof and a sensitized solar cell containing the organic dye, belonging to the technical field of dye-sensitized solar cells. The organic dye has the following structure, wherein R1, R2 are independently selected from any one of H, C1~C18 alkyl, and C1~C18 alkoxy; R3, R4 are independently selected from H, C1~C18 alkyl, C1 Any one of ~C18 alkylphenyl, C1~C18 alkoxyphenyl; R5, R6 are independently selected from H, F, C1~C18 alkyl, C1~C18 alkylphenyl, C1~C18 alkoxy Any one of phenyl groups; x, y are 0 or 1. The dye of the present invention has a twisted electron skeleton, and at the same time combines side modifying groups to make it have a better three-dimensional structure. The sensitized solar cell prepared by the dye has higher voltage and can be used as a co-sensitizer in combination with other high-efficiency dyes to prepare a device with excellent performance and good photothermal stability. The preparation method of the organic dye has rich sources of raw materials, low cost, good photothermal stability of the prepared device, and bright prospect of industrial production.

Description

technical field [0001] The invention relates to the technical field of dye-sensitized solar cells, in particular to an organic dye with a better three-dimensional structure, a preparation method thereof, and a sensitized solar cell containing the organic dye. Background technique [0002] With the sharp increase in energy demand, solar energy as a renewable and clean energy has received widespread attention all over the world. Since 1991, Since the research team reported dye-sensitized solar cells, the photoelectric conversion efficiency of dye-sensitized solar cells has increased rapidly. At present, some metal ruthenium complexes and zinc porphyrin dyes have achieved a photoelectric conversion efficiency of about 13%. The photoelectric conversion efficiency of devices prepared with pure organic dyes has reached 13%. However, the photothermal stability of the devices prepared by the above materials is not satisfactory. Therefore, photothermal stability has become the c...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B57/00C07D417/14H01G9/20
CPCY02E10/542
Inventor 王鹏薛中原杨林陈淑刘娇
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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