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Organic dye taking alkoxy substituted fluorene unit-containing triarylated amine as donor and application thereof in dye-sensitized solar cell

An organic dye, alkoxy-containing technology, applied in the direction of organic dyes, methine/polymethine-based dyes, photovoltaic power generation, etc., can solve the problem of high cost, and achieve the effect of improving open circuit voltage, easy purification, and reducing molecular aggregation.

Active Publication Date: 2013-11-27
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to solve the problem of high cost of existing organic dyes due to the use of precious metals, and to provide a kind of organic dyes with triarylamines containing alkoxy-substituted fluorene units as donors and in dye-sensitized solar Application in battery

Method used

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  • Organic dye taking alkoxy substituted fluorene unit-containing triarylated amine as donor and application thereof in dye-sensitized solar cell
  • Organic dye taking alkoxy substituted fluorene unit-containing triarylated amine as donor and application thereof in dye-sensitized solar cell
  • Organic dye taking alkoxy substituted fluorene unit-containing triarylated amine as donor and application thereof in dye-sensitized solar cell

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Preparation of organic dye (I) with triarylamine containing alkoxy-substituted fluorene unit as donor

[0022] The synthetic route is as follows:

[0023]

[0024] Synthesis of Intermediate 2:

[0025] Add 0.600 g of compound 1, 0.480 g of 4-hexyloxy-N-phenylaniline into the reaction flask, dissolve in 10 ml of toluene, add 0.014 g of tris(dibenzylideneacetone) dipalladium, 0.017 g of gram of 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (Xantphos) and 0.290 gram of sodium tert-butoxide, reflux reaction under argon atmosphere for 12 hours, stop the reaction, cool to room temperature, wash with acetic acid Extract with ethyl ester and water, separate the organic phase, dry with anhydrous sodium sulfate, filter, concentrate the filtrate, and use dichloromethane / petroleum ether (volume ratio 1 / 10) as a developing solvent for column chromatography to obtain 0.835 g of intermediate 2 , yield 95%;

[0026] Synthesis of intermediate 3:

[0027] Add 0.590 gram...

Embodiment 2

[0037] Example 2: Preparation of organic dye (II) with triarylamine containing alkoxy-substituted fluorene unit as donor

[0038] The synthetic route is as follows:

[0039]

[0040] Synthesis of Intermediate 2:

[0041] Add 3.000 grams of compound 1, 0.27 milliliters of aniline in the reaction flask, dissolve in 40 milliliters of toluene, add 0.046 grams of tris(dibenzylideneacetone) dipalladium, 0.052 grams of Xantphos and 0.870 grams of sodium tert-butoxide successively under the protection of argon, Reflux reaction under argon atmosphere for 10 hours, stop the reaction, cool to room temperature, extract with ethyl acetate and water, separate the organic phase, dry the organic phase with anhydrous sodium sulfate, filter, concentrate the filtrate, and wash with ethyl acetate / petroleum ether (Volume ratio 1 / 50) was used as a developing solvent for column chromatography to obtain 2.360 g of intermediate 2 with a yield of 95%;

[0042] Synthesis of Intermediate 3:

[0043...

Embodiment 3

[0053] Example 3: Preparation of organic dye (Ⅲ) with triarylamine containing alkoxy-substituted fluorene unit as donor

[0054] The synthetic route is as follows:

[0055]

[0056] Synthesis of Intermediate 2:

[0057] Add 1.400 grams of compound 1, 0.170 milliliters of benzamide to the reaction flask, dissolve in 40 milliliters of toluene, add 0.042 grams of tris(dibenzylideneacetone) dipalladium, 0.049 grams of Xantphos and 0.670 grams of tert-butanol successively under the protection of argon Sodium, reflux reaction under argon atmosphere for 10 hours, stop the reaction, cool to room temperature, extract with ethyl acetate and water, separate the organic phase, distill off the solvent, add 10 ml of ethanol and 10 ml of 2 moles per liter of sodium hydroxide Aqueous solution, heated to 80 degrees Celsius for 10 hours, cooled to room temperature, extracted with ethyl acetate and water, separated the organic phase, dried the organic phase with anhydrous sodium sulfate, fil...

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Abstract

The invention provides an organic dye taking alkoxy substituted fluorene unit-containing triarylated amine as a donor and the application of the organic dye in a dye-sensitized solar cell, belonging to the field of the organic dye. The organic dye takes alkoxy substituted fluorene as the unit of a triarylated amine donor, so that the electron pushing capability of the dye donor part can be improved due to the alkoxy substituted fluorene-containing structure unit, the gathering of small molecules can be reduced due to the use of the fluorene unit, the electron recombination in the cell can be reduced, the open-circuit voltage of the cell can be effectively improved, and the gathering of the molecule can be reduced and the dissolubility of the dye can be improved due to the introduction of alkyl chain, so that a device can be conveniently optimized. The organic dye provided by the invention is simple in synthetic route, and easy to purify; and according to the dye-sensitized solar cell prepared by the organic dye provided by the invention, the open-circuit voltage reaches to 948 millivolts, the short-circuit photocurrent reaches to 14.36 milliamperes in every square centimeter, and the power conversion efficiency reaches 9.9%.

Description

technical field [0001] The invention relates to the technical field of organic dyes, in particular to an organic dye using triarylamine containing alkoxy-substituted fluorene units as a donor and its application in dye-sensitized solar cells. Background technique [0002] As a clean energy source, solar energy will be more widely developed and utilized under the current crisis situation of traditional energy sources. In the field of solar cells today, silicon-based solar cells dominate, but their manufacturing costs are relatively high, and they cannot yet replace traditional energy sources on a large scale. Dye-sensitized solar cells, as a cheap excitonic solar cell based on organic photoelectric functional materials, have received extensive attention and research at home and abroad. In 1991, Professor Grötzel of the Swiss Federal Institute of Technology reported the breakthrough work of dye-sensitized nanocrystalline solar cells (Nature 1991, 353, 737), which started the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B23/04H01G9/20
CPCY02E10/542
Inventor 王鹏范晔张敏许名飞姚朝阳
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES