Novel organic dye and method for preparing same

A technology of organic dyes and dyes, applied in the directions of organic dyes, sulfur dyes, azo dyes, etc., can solve the problems of low conversion efficiency, low driving stability, etc., and achieve high efficiency, high molar absorption coefficient, and lower dye synthesis costs. Effect

Inactive Publication Date: 2011-05-25
DONGJIN SEMICHEM CO LTD
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  • Abstract
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Problems solved by technology

[0007] However, most of the currently known organic dyes exhibit low conversion efficiency and low drive stability compared to ruthenium metal complex dyes, so research aimed at changing such electron donors and acceptors is currently underway. Efforts to develop new dyes that have a higher molar absorptivity than existing organic dye compounds and exhibit high photoelectric conversion efficiency by species or π-bond length

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

[0202] Synthesis of the compound of embodiment 1 chemical formula 1a

[0203] (1-1) (2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)trimethylstannane (0.40g, 1.34mmol), chemical formula 2a After the compound (0.75g, 1.12mmol), Pd(PPh3)4 (0.065g, 0.056mmol) was dissolved in THF (40ml), it was refluxed under nitrogen atmosphere for 8 hours. Next, after extracting the organic layer with dichloromethane and water, distillation, and column chromatography (eluent-MC:Hx=1:4), the compound of chemical formula 4a was synthesized.

[0204] 1 H NMR (CDCl3): [ppm] = 0.96 (m, 6H), 1.29 (m, 4H), 1.96 (m, 4H), 2.55 (m, 8H), 2.62 (m, 4H), 4.68 (s, 2H ), 4.71(s, 2H), 6.71(m, 2H), 6.96(s, 1H), 7.08(s, 1H), 7.18(m, 4H), 7.38(m, 2H), 7.45(m, 6H) , 7.55(d, 3JHH=8.8Hz, 2H).

[0205] (1-2) After the compound of chemical formula 4a (0.87g, 1.2mmol) was dissolved in DMF (20ml), POCl3 (0.13ml 1.44mmol) was slowly added dropwise at 0°C, and stirred at 80°C for 4 hours. After the stirring was completed, t...

Embodiment 2

[0209] Synthesis of the compound of embodiment 2 chemical formula 1b

[0210] (2-1) (2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)trimethylstannane (0.40g, 1.34mmol), chemical formula 2b After the compound (1g, 1.12mmol) and Pd(PPh3)4 (0.065g, 0.056mmol) were dissolved in THF (40ml), it was refluxed under nitrogen atmosphere for 8 hours. Next, after extracting the organic layer with dichloromethane and water, distillation, and column chromatography (eluent-MC:Hx=1:4), the compound of chemical formula 4b was synthesized.

[0211] 1 H NMR (CDCl3): [ppm] = 0.96 (m, 6H), 1.29 (m, 4H), 1.44 (s, 12H), 1.96 (m, 4H), 2.55 (m, 8H), 2.62 (m, 4H ), 4.68(s, 2H), 4.71(s, 2H), 6.91(s, 1H), 6.96(s, 1H), 7.08(s, 1H), 7.18(m, 6H), 7.38(m, 6H) , 7.55(m, 4H), 7.82(d, 3JHH=8.8Hz, 2H).

[0212] (2-2) After the compound of chemical formula 4a (1.14g, 1.2mmol) was dissolved in DMF (20ml), POCl3 (0.13ml1.44mmol) was slowly added dropwise at 0°C, and stirred at 80°C for 4 hours. After the stirring wa...

Embodiment 3

[0216] Synthesis of the compound of embodiment 3 chemical formula 1e

[0217] (3-1) (2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)trimethylstannane (0.40g, 1.34mmol), 5- Bromo-2-(4-(2,2-diphenylethenyl) phenyl)-3-hexylthiophene (compound of chemical formula 2e) (0.67g, 1.34mmol), Pd(PPh3) 4 (0.065g, 0.056 mmol) was dissolved in THF (40ml), and refluxed under nitrogen atmosphere for 8 hours. Next, after extracting the organic layer with dichloromethane and water, distillation, and column chromatography (eluent-MC:Hx=1:4), the compound of chemical formula 4e was synthesized.

[0218] 1 H NMR (CDCl3): [ppm] = 0.88 (m, 3H), 1.29 (m, 2H), 1.86 (m, 2H), 2.55 (m, 4H), 2.62 (m, 2H), 4.68 (s, 2H ), 4.71(s, 2H), 6.71(s, 1H), 6.96(s, 1H), 7.08(s, 1H), 7.18(m, 4H), 7.38(m, 2H), 7.45(m, 6H) , 7.55(d, 3JHH=8.8Hz, 2H).

[0219] (3-2) After the compound of chemical formula 4e (1.14g, 1.2mmol) was dissolved in DMF (20ml), POCl3 (0.13ml 1.44mmol) was slowly added dropwise at 0°C, and stirred a...

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Abstract

The present invention relates to a novel organic dye and to a method for preparing same. A dye compound of the present invention is used in a DSSC (dye-sensitized solar cell) to achieve dramatically improved molar absorptivity, short-circuit photocurrent density (Jsc), and photoelectric conversion efficiency as compared to conventional dyes, and enables refining even without using an expensive column, thus significantly reducing the costs of the synthesis of dyes.

Description

technical field [0001] The invention relates to a novel dye for dye-sensitized solar cells (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 have higher efficiency and significantly lower manufacturing costs than existing silicon-based solar cells, so they have the possibility of being able to replace existing amorphous silicon-based solar cells, and are different from silicon-based solar cells A dye-sensitized solar cell is a photoelectrochemical solar cell mainly composed of dye molecules capable of generating electron-hole (hole) pairs by absorbing visible light and transition metal oxides that transfer the generated electrons. [0003] Ruthenium metal complexes exhibiting hig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B49/00C09B49/12
CPCY02E10/542H01G9/2059H01L51/0072C09B57/00C09B23/105H01L51/006C09B23/148H01L51/0068C09B57/008H01L51/0037Y02E10/549C09B23/0008Y02P70/50H10K85/1135H10K85/655H10K85/633H10K85/6572C09B49/00C09B49/12
Inventor 李钟灿白宗协杨会泽
Owner DONGJIN SEMICHEM CO LTD
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