Novel Organic Dye And Preparation Method Thereof

A technology of organic dyes and dyes, applied in the directions of organic dyes, anthracene dyes, azo dyes, etc., can solve the problems of low conversion efficiency, low driving stability, etc., and achieve the effect of improving efficiency and high molar absorption coefficient

Inactive Publication Date: 2012-11-28
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 known organic dyes show low conversion efficiency and low drive stability compared with ruthenium metal complex dyes, so currently Aiming at changing the types of such electron donors and acceptors or the length of the π-bond, new dyes that have a significantly higher molar absorptivity than conventional organic dyes and exhibit high photoelectric conversion efficiency are being developed. the dye effort

Method used

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  • Novel Organic Dye And Preparation Method Thereof
  • Novel Organic Dye And Preparation Method Thereof
  • Novel Organic Dye And Preparation Method Thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0410] Embodiment 1: the synthesis of chemical formula 8

[0411] 1) Synthesis of intermediate (8a)

[0412] 2,7-dibromo-9-phenylacridine (2,7-dibromo-9-phenylacridine), 3',4-dihexyl-2,2'-dithiophen-5-ylboronic acid (3', 4-dihexyl-2, 2′-bithiophen-5-ylboronic acid), Pd(PPh 3 ) 4 and 2M of K 2 CO 3 The aqueous solution was 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 (10a) having the following chemical structural formula.

[0413] [Intermediate 8a]

[0414]

[0415] 2) Synthesis of intermediate (8b)

[0416] The intermediate (8a) produced above was added to an absolute ethanol solution, and n-BuLi was further added under argon. After 3 hours, DMF was added to the resulting reaction product at 0° C. under argon gas, followed by washing with 5% KOH. The resulting reaction solution was dried over magne...

Embodiment 2

[0424] Embodiment 2: the synthesis of compound formula 10

[0425] 1) Synthesis of intermediate (10a)

[0426] Instead of 3',4-dihexyl-2,2'-dithiophen-5-ylboronic acid use 7-(5-(5,5-dimethyl-1,3-di Alkyl-2-yl)thieno[3,2-b]thiophen-2-yl)-2,3-dihydrothiophene[3,4-b][1,4]di In-5-ylboronic acid was carried out in the same manner as in Example 1 above except that, to obtain an intermediate (10a) of the following chemical structural formula.

[0427] [Intermediate 10a]

[0428]

[0429] 2) Synthesis of intermediate (10b)

[0430] In 2) of Example 1 above, the intermediate (10a) produced above was dissolved in tetrahydrofuran (THF), and trifluoroacetic acid and water were added dropwise to the resulting solution, followed by stirring for 4 hours under a nitrogen atmosphere.

[0431] After completion of the stirring, the resulting reaction solution was extracted with dichloromethane and water, and the organic layer was evaporated, and purified by column chromatography to obta...

Embodiment 3

[0439] Embodiment 3: the synthesis of chemical formula 18

[0440] 1) Synthesis of intermediate (18a)

[0441] Tetraethyl(9-phenylacridine-2,7-diyl)bis(methylene)diphosphate and 7-(5-(5,5-dimethyl-1,3-di Alkyl-2-yl)thieno[3,2-b]thiophen-2-yl)-2,3-dihydrothieno[3,4-b][1,4]di In-5-carbaldehyde was subjected to Wittig reaction in THF solvent in the presence of potassium tert-butoxide to obtain intermediate (18a) of the following chemical structural formula.

[0442] [Intermediate 18a]

[0443]

[0444] 2) Synthesis of intermediate (18b)

[0445] The intermediate (18b) having the following chemical structural formula was obtained in the same manner as in Example 1 except that the intermediate (18a) produced above was used instead of the intermediate (8a) in Example 1.

[0446] [Intermediate 18b]

[0447]

[0448] 3) Synthesis of compound formula 18

[0449] In the above-mentioned Example 1, except that the intermediate (18b) produced above was used instead of the int...

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Abstract

The present invention relates to a novel organic dye for a dye-sensitized photoelectric conversion device, and a preparation method thereof. The organic dye according to the present invention is used as a dye-sensitized photoelectric conversion device in a dye-sensitized solar cell (DSSC) and provides improved molar absorptivity, Jsc (short circuit photocurrent density) and photoelectric conversion efficiency when compared with known dyes, thereby being capable of remarkably improving the efficiency of the solar cell.

Description

technical field [0001] The invention relates to a novel organic dye for dye-sensitized photoelectric conversion elements used in a dye-sensitized solar cell (dye-sensitized solar cell, DSSC) and a manufacturing method thereof. Background technique [0002] Since Michael Gratzel's research group at the Swiss National Institute of Technology Lausanne (EPFL) developed a dye-sensitized nanoparticle titanium oxide solar cell in 1991, a lot of research has been done on this field. Dye-sensitized solar cells are expected to be able to replace conventional amorphous silicon-based solar cells because they have higher efficiency and significantly lower manufacturing costs than conventional silicon-based solar cells. Unlike silicon-based solar cells, dye-sensitized solar cells are photoelectrochemical solar cells that use dyes that generate electron-hole pairs by absorbing visible light and transition metal oxides that transfer the generated electrons. . [0003] Conventionally, ruth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B1/00C09B15/00C09B29/039H01L31/042
CPCY02E10/542C09B15/00C09B21/00C09B23/00C09B57/008H01G9/2031H01G9/2059Y02E10/549Y02P70/50H10K85/6576H10K85/657
Inventor 裵镐基安贤哲李钟灿
Owner DONGJIN SEMICHEM CO LTD
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