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Organic dye-stuff with multi-heterocycle derivant as conjugation unit and dye sensitized solar battery produced with the same

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: 2009-05-13
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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-stuff with multi-heterocycle derivant as conjugation unit and dye sensitized solar battery produced with the same
  • Organic dye-stuff with multi-heterocycle derivant as conjugation unit and dye sensitized solar battery produced with the same
  • Organic dye-stuff with multi-heterocycle derivant as conjugation unit and dye sensitized solar battery produced with the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] The synthetic route of dye I is as follows:

[0071]

[0072] The specific synthesis method is:

[0073] Compound c10g, compound d10.3g, Pd(PPh 3 ) 4 2.2 g, 250 mL of toluene were refluxed for 12 hours under the protection of argon, the solvent was removed, and the compound e was obtained by column chromatography. Dissolve compound e2.4g in 30mL DMF, protect with argon, cool to 0°C, add dropwise the solution of NBS in DMF, continue to complete the reaction after the addition, extract with chloroform, wash with water, dry over magnesium sulfate, remove the solvent and perform column chromatography Compound f. Take compound f1.3g, compound g0.72g, Pd(PPh 3 ) 4 0.23g, K 2 CO 3(2M) solution 6.9mL and THF 70mL were refluxed for 12h under the protection of argon, the solvent was removed, and the compound h was obtained by column chromatography. Compound h0.7g, POCl 3 0.2mL, 0.75mL of DMF and 10mL of dichloroethane were refluxed for 6h under the protection of argon...

Embodiment 2

[0076] The synthetic route of dye II is as follows:

[0077]

[0078] The specific synthesis method is:

[0079] Take compound f 1.3g, compound j 1.05g, Pd(PPh 3 ) 4 0.23g, K 2 CO 3 (2M) solution 6.9mL and THF 70mL were refluxed for 12h under the protection of argon, the solvent was removed, and compound k was obtained by column chromatography. Compound k 0.4g, POCl 3 0.1mL, DMF 0.4mL and dichloroethane 10mL were refluxed for 6h under the protection of argon, diluted with chloroform, washed with water, saturated sodium carbonate solution and saturated brine successively, dried over magnesium sulfate, and concentrated column chromatography to obtain compound 1. 0.2 g of compound 1, 0.1 g of cyanoacetic acid, 0.1 mL of piperidine, and 5 mL of chloroform were refluxed overnight under the protection of argon, the solvent was removed, and the dye II was obtained by column chromatography.

[0080] NMR data of dye II: 1 H NMR (400MHz, DMSO, δ H ): 0.88(t, 6H), 1.32(m, 8H)...

Embodiment 3

[0081] Example 3: Dye-sensitized solar cells prepared by organic dyes I

[0082] TiO with a particle size of 20nm 2 Colloid coating on fluorine-doped SnO 2 On conductive glass, nano-TiO is formed 2 The crystal film was baked at 400 °C for 12 hours to obtain TiO with a thickness of 7 μm 2 crystal film; the obtained TiO 2 Using the same method on the layer film, the particle size is 400nmTiO 2 , fired TiO with a thickness of 5 μm 2 Light scattering film; obtained TiO 2 Nanostructured bilayer membrane electrodes. Specific preparation of TiO 2 Nanocrystalline and TiO 2 For the method of nanostructured double-layer membrane electrode, see the article (Wang P. et al., Enhance the Performance of Dye-Sensitized SolarCells by Co-grafting Amphiphilic Sensitizer and Hexadecylmalonic Acidon TiO 2 Nanocrystals, J. Phys. Chem. B., 107, 2003, 14336).

[0083] Prepared TiO 2 The nanostructured double-layer membrane electrode was immersed in a chlorobenzene solution containing 300 μ...

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Abstract

The invention belongs to the technical field of solar cell and relates to an organic dye using a multi-heterocyclic derivant as a conjugate unit and a dye-sensitized solar cell made from the dye. The dye uses a plurality of heterocyclic derivants as a pi unit and belongs to a molecule with a D-pi-A structure. The dye has wide absorption spectrum and high photoelectric conversion efficiency and has application prospect in the solar cell through substituting for a noble metal dye. The dye molecule belongs to a pure organic compound; compared with the prior ruthenium dye, the organic dye does not need to use expensive metal ruthenium as a raw material and glucan as a purifying agent; additionally, the synthesis yield is high (the total yield is more than 40 percent); therefore, the organic dye has the advantages of low cost and simple production; in addition, the absorption spectrum of the dye exceeds 550 nm and the molar extinction coefficient exceeds 45000 M-1cm-1, which are far larger than the absorption spectrum and the molar extinction coefficient of the ruthenium dye; therefore, the organic has wider absorption range to solar ray. The dye-sensitized solar cell prepared from the dye has high quanta conversion efficiency (IPCE); the maximum of the quanta conversion efficiency exceeds 95 percent (nm); and the photoelectric conversion efficiency is more than 8.0 percent and exceeds that of other most pure organic dye-sensitized solar cells.

Description

technical field [0001] The invention relates to organic dyes with polyheterocyclic derivatives as conjugated units and dye-sensitized solar cells 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 , 10720-10728), however, its pra...

Claims

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Application Information

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IPC IPC(8): C09B57/00H01G9/042H01G9/20
CPCY02E10/542H01L51/0073H01L51/0061H01G9/2059H01G9/2031H01L51/0068Y02E10/549C09B23/005C09B23/0058C09B23/105C09B57/008H10K85/636H10K85/655H10K85/6574
Inventor 张广良许名飞高飞飞王鹏
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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