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Organic dye with five-element heterocycle and derivative thereof as conjugate unit, and dye sensitization solar cell prepared thereby

A technology of organic dyes and derivatives, applied in the field of dye-sensitized solar cells, can solve problems such as limiting practical applications

Active Publication Date: 2012-07-04
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Sensitizing materials are a key material for improving battery efficiency. At present, the dye sensitizers with the best performance are organometallic sensitizers containing noble metals, such as polypyridine ruthenium complexes (J.Am.Chem.Soc.2008, 130 , 10720-10728), however, its practical application is limited due to its high price and limited resources of precious metals

Method used

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  • Organic dye with five-element heterocycle and derivative thereof as conjugate unit, and dye sensitization solar cell prepared thereby
  • Organic dye with five-element heterocycle and derivative thereof as conjugate unit, and dye sensitization solar cell prepared thereby
  • Organic dye with five-element heterocycle and derivative thereof as conjugate unit, and dye sensitization solar cell prepared thereby

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Embodiment 1: the synthetic route of dyestuff I is as follows:

[0071]

[0072] The specific synthesis method is:

[0073] Dissolve 5.24 g of compound a-1, 5.5 g of 2-selenophenetributyltin, and 0.7 g of bistriphenylphosphine palladium dichloride in 50 mL of THF, reflux the reaction under argon for 12 h, remove the solvent, and perform column chromatography on the residue Compound b-1 was obtained. React 0.57g of compound b-1, 0.2mL of phosphorus oxychloride, DMF and 10mL of chloroform at room temperature for 5h, dilute with chloroform, wash with saturated sodium bicarbonate solution and saturated brine successively, remove the solvent, and obtain the compound by column chromatography c-1. Dissolve 0.5 g of compound c-1, 0.21 g of cyanoacetic acid and 0.6 mL of piperidine in 10 mL of chloroform, reflux for 4 h under argon, remove the solvent, and obtain dye I by column chromatography.

[0074] NMR data of dye I: 1 H NMR (400MHz, DMSO-d 6 )δ: 0.88(t, 6H), 1.30(m...

Embodiment 2

[0076] Using 2,2'-diselenol-5-tributyltin instead of 2-selenophene tributyltin as the starting material, dye II was prepared according to the same experimental process as in Example 1.

[0077] NMR data of dye II: 1 H NMR (400MHz, DMSO-d 6 )δ: 0.88(t, 6H), 1.31(m, 8H), 1.40(m, 4H), 1.68(m, 4H), 3.94(t, 4H), 6.72(d, 2H), 6.91(d, 4H ), 7.04(d, 4H), 7.45(d, 2H), 7.48(d, 1H), 7.49(d, 1H), 7.66(d, 1H), 8.07(d, 1H), 8.40(s, 1H) .

Embodiment 3

[0079] Using 2-tributyltin furan instead of 2-tributyltin selenophene as the starting material, dye III was prepared according to the same experimental process as in Example 1.

[0080] NMR data of dye III: 1 H NMR (400MHz, DMSO-d 6 )δ: 0.88(t, 6H), 1.31(m, 8H), 1.42(m, 4H), 1.70(m, 4H), 3.94(t, 4H), 6.75(d, 2H), 6.92(d, 4H ), 7.08 (d, 4H), 7.11 (d, 1H), 7.51 (d, 1H), 7.70 (d, 2H), 7.982 (s, 1H), 13.48 (s, 1H).

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Abstract

The invention provides an organic dye which uses five-membered heterocyclic ring, derivatives thereof and a dye-sensitized solar cell prepared by the organic dye. The dye uses the five-membered heterocyclic ring or the derivatives thereof as a Pi unit, uses substituted triarylamine as an electron donor, uses cyanoacetic acid structure as an electron acceptor, and belongs to molecule of D-Pi-A structure. The dye molecule belongs to pure organic compounds, the structure of the materials is simple and is easy to be obtained; expensive materials of metal of Ru and purifying agent of polydextrose do not need to use, the compound yield is higher, so the total yield is between 40 percent and 70 percent; besides, the performance of spectral absorption and molar extinction coefficient and the like of the dye are excellent; and the peak value of the spectral absorption is over 550nm at the most, the molar extinction coefficient is over 48000M<-1>cm<-1>, the peak value and the coefficient are more than the Ru dye, therefore, the dye has wider absorption range to the sunlight. The dye-sensitized solar cell prepared by the organic dye has the maximum of quantum conversion efficiency of 97 percent and the highest photoelectric conversion efficiency of more than 8.0 percent.

Description

technical field [0001] The invention relates to an organic dye with a five-membered heterocyclic ring and its derivatives as a conjugated unit and a dye-sensitized solar cell prepared therefrom. Background technique [0002] With the increasing scarcity of fossil energy, how to develop alternative energy has attracted more and more attention. As a renewable clean energy, solar energy is an ideal energy for human long-term survival. In 1991, the Swiss Federal Institute of Technology The team reported the breakthrough work of high-efficiency dye-sensitized nanocrystalline solar cells (Nature 1991, 353, 737), which brought hope for human beings to provide low-cost, high-efficiency, and long-lived green renewable energy. Sensitizing materials are a key material for improving battery efficiency. At present, the dye sensitizers with the best performance are organometallic sensitizers containing noble metals, such as polypyridine ruthenium complexes (J.Am.Chem.Soc.2008, 130 , 1...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/04H01G9/20H01G9/022
CPCY02E10/542H01L51/0067H01L51/0061H01L51/0065H01G9/2059H01G9/2031H01L51/0068C09B23/0058C09B57/008Y02E10/549H10K85/653H10K85/655H10K85/636H10K85/654
Inventor 张广良许名飞李仁志吕学举孟哈日巴拉王鹏
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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