Organic dye and preparation method thereof, and sensitized solar cell containing organic dye

A technology of organic dyes and solar cells, which is applied in the field of sensitized solar cells and dye-sensitized solar cells, can solve the problems of poor photothermal stability of devices and the inability of large-scale industrialization of dye-sensitized solar cells, and achieve industrial production Bright prospects, low cost, and good photothermal stability

Active Publication Date: 2016-03-30
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Organic dye and preparation method thereof, and sensitized solar cell containing organic dye
  • Organic dye and preparation method thereof, and sensitized solar cell containing organic dye
  • Organic dye and preparation method thereof, and sensitized solar cell containing 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 and a preparation method thereof, and a sensitized solar cell containing the organic dye, and belongs to the technical field of dye-sensitized solar cell. The organic dye has the following structure described in the description, wherein R1 and R2 are independently selected from any one of H, C1-C18 alkyl and C1-C18 alkoxy, R3 and R4 are independently selected from any one of H, C1-C18 alkyl, C1-C18 alkyl phenyl and C1-C18 alkoxy phenyl, R5 and R6 are independently selected from any one of H, F, C1-C18 alkyl, C1-C18 alkyl phenyl, and C1-C18 alkoxy phenyl, and x and y are 0 or 1. The dye has a twisted electronic skeleton and is combined with a side modifying group to make the dye have a better three-dimensional structure at the same time. The sensitized solar cell prepared by the dye has a higher voltage, and the dye can be used as a co-sensitization agent for being combined with other high-efficiency dyes to prepare a device with excellent performance and good light and thermal stability. The preparation method of the organic dye has the advantages of abundant raw material sources, lower cost, good light and thermal stability of the prepared device, and grander industrialized production prospect.

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 Applications(China)
IPC IPC(8): C09B57/00C07D417/14H01G9/20
CPCY02E10/542C09B57/00C07D417/14H01G9/2059H01G9/2063
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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