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Novel organic dye and method for preparing same

A technology of organic dyes and dyes, applied in the directions of organic dyes, acridine dyes, azo dyes, etc., can solve the problems of low conversion efficiency and low driving stability, and achieve the effect of improving efficiency and reducing the cost of dye synthesis

Inactive Publication Date: 2012-09-26
DONGJIN SEMICHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, most of the organic dyes known so far show low conversion efficiency and low driving stability compared with ruthenium metal complex dyes, so it is thought that by changing the types of such electron donors and acceptors or π -bond length, thereby developing new dyes with improved molar absorptivity than existing organic dye compounds, exhibiting high photoelectric conversion efficiencies

Method used

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  • Novel organic dye and method for preparing same
  • Novel organic dye and method for preparing same
  • Novel organic dye and method for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0301] 1-1) Synthesis of intermediate (la)

[0302] 2,7-dibromo-9-phenylacridine and (E)-(5-oxothiophen-2(5H)-ylidene)methylboronic acid, tetrakis(triphenylphosphine)palladium and 2M K 2 CO 3 Aqueous, mixed in dimethylformamide (DMF) and refluxed for 12 hours. The resulting reaction solution was cooled, water (30 ml) and brine were added, and the organic layer was separated and purified to obtain an intermediate having the following chemical formula.

[0303] [intermediate la]

[0304]

[0305] 1-2) Synthesis of Compound 1

[0306] The intermediate (la) and cyanoacetic acid produced in the above Example 1-1) were mixed and the produced mixture was vacuum-dried, mixed with acetocyanide and piperidine, and refluxed for 6 hours. After cooling the resulting reaction solution, the organic layer was removed under vacuum. The resulting solid matter was purified by silica gel chromatography to obtain the following Compound 1. As a result of performing FD-MS (Field desorption ...

Embodiment 2

[0310] Except in Example 1 above, instead of (E)-(5-oxothiophen-2(5H)-ylidene)methylboronic acid, (E)-(5-oxothieno[3,2-b ]thiophene-2(5H)-ylidene)methylboronic acid, the same method as in Example 1 was sequentially carried out to obtain the following compound 2. As a result of performing FD-MS on the above compounds, it was confirmed that for C 39 h 19 N 3 o 4 S 4 =722, m / z (measured value)=721.

[0311] [Compound 2]

[0312]

Embodiment 3

[0314] Except in Example 1 above, instead of (E)-(5-oxothiophene-2(5H)-ylidene)methylboronic acid, (E)-(7-oxo-2,3-dihydrothiophene And [3,4-b][1,4] two Except for eng-5(7H-ylidene)methylboronic acid, the same method as in Example 1 was sequentially carried out to obtain the following compound 3. As a result of performing FD-MS on the above compounds, it was confirmed that for C 39 h 23 N 8 o 3 S 2 =726, m / z (measured value)=725.

[0315] [Compound 3]

[0316]

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PUM

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Abstract

The present invention relates to novel organic dye and method for preparing the same. A dye compound of the present invention comprises: a specific aliphatic compound as an electron donor; and a thiopheneic or dehydrothiopheneic unit in an intermediate connecting part (spacer). The dye compound of the present invention is used in a dye-sensitized solar cell (DSSC) to improve a molar extinction coefficient, Jsc (short circuit photocurrent density) and photoelectric conversion efficiency as compared with those of conventional dyes, and thus significantly improves the efficiency of the solar cell. The dye compound of the present invention can be refined without using expensive columns, thereby remarkably reducing costs for dye synthesis.

Description

technical field [0001] The present invention relates to a dye used in a dye-sensitized solar cell (DSSC) and a manufacturing method thereof. Background technique [0002] Since the development of dye-sensing nanoparticle titanium oxide solar cells in 1991 by Michael Gratzel's research group at the Swiss Federal Institute of Technology in Lausanne (EPFL), much research has been carried out in this area. Compared with the existing silicon-based solar cells, dye-sensing solar cells have high efficiency and significantly lower manufacturing cost, and have the possibility of replacing the existing amorphous silicon solar cells. Unlike silicon solar cells, dye-sensing solar cells can be Photoelectrochemical solar cells that absorb visible light to form electron-hole (hole) pairs and transition metal oxides that transfer the generated electrons are the main constituent materials. [0003] As dyes for dye-sensing solar cells, ruthenium metal complexes exhibiting high photoelectric ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B15/00C09B3/10C09B29/036C09B29/40
CPCY02E10/542Y02E10/549
Inventor 安贤哲李钟灿
Owner DONGJIN SEMICHEM CO LTD
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