Polythiophene compound, intermedium thereof and preparation method and application of same two to solar battery

A technology of polythiophenes and compounds, applied in the direction of organic chemistry, etc., to achieve the effects of correct structure, easy film formation, and improved carrier mobility

Inactive Publication Date: 2011-06-15
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But the traditional material poly(3-hexylthiophene) only has about 46% (Soci, C., Hwang, I.-W., Moses, D., Zhu, Z., Waller, D. to the absorption of sunlight). , Guadiana, R., Brabec, C.J., Heeger, A.J., Adv.Funct.Mater.2007, 17, 632.), most of the light in the infrared region is still not effectively absorbed

Method used

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  • Polythiophene compound, intermedium thereof and preparation method and application of same two to solar battery
  • Polythiophene compound, intermedium thereof and preparation method and application of same two to solar battery
  • Polythiophene compound, intermedium thereof and preparation method and application of same two to solar battery

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preparation example Construction

[0057] The reaction equation of the method for preparing polythiophenes provided by the invention is as follows:

[0058]

[0059]

[0060] (i) THF, t-BuOK, n-C 6 h 13 Br, room temperature, 12-18h; (ii) ClCH 2 CH 2 Cl, POCl 3 , DMF, reflux, 24-36h; (iii) CHCl 3 , HOAc, NBS, room temperature, 6-12h; (iv) NBS, BPO, CCl 4 , reflux, 4-6h; (v)P(OC 2 h 5 ) 3 , reflux, 1h; (vi)THF, n-BuLi, -78℃, (n-Bu) 3 SnCl, -78°C-room temperature, 24h; (vii) diethyl ether, C 6 h 13 Br, Mg, Ni(dppf)Cl 2 , reflux, 48h;

Embodiment 1

[0062] Embodiment 1, prepare the intermediate of polythiophene compound

[0063] The method for preparing the intermediate of polythiophene compounds provided by the invention comprises the following steps:

[0064] 1) Under the protection of nitrogen, dissolve 0.1 mol of carbazole in 100 mL of tetrahydrofuran, and add 0.2 mol of t-BuOK; under the protection of nitrogen, 0.2 mol of n-C 6 h 13 Br was dissolved in 100mL tetrahydrofuran in another bottle, and then the solution was transferred to a tetrahydrofuran solution containing carbazole, reacted at room temperature for 12 hours, extracted, dried, and recrystallized in methanol to obtain N-hexylcarbazole with a yield of 85%. about;

[0065] Add 0.5mol N-hexylcarbazole prepared above to 1.5mol POCl 3 and 0.525mol of DMF, refluxed for 24 hours, cooled, extracted, dried, and separated by column chromatography to obtain 3-formaldehyde-N-hexylcarbazole (as shown in formula IV), with a yield of about 90%.

[0066] 2) Dissolve ...

Embodiment 2

[0070] Embodiment 2, preparation polythiophene compound

[0071] The method for preparing the polythiophene compounds shown in the general structural formula of formula III provided by the present invention comprises the following steps:

[0072] 1) Under the protection of nitrogen, dissolve 0.2mol of 2,5-dibromothiophene in 150mL of tetrahydrofuran, freeze to -78°C, add 0.5mol of butyllithium, and react at -78°C for 2 hours, then add 0.5mol of 3-Butyltin chloride, slowly warming up to room temperature, reacting for 24 hours, extracting, washing, and vacuum distillation to obtain 2,5-bis(tributyltin-based)thiophene with a yield of about 95%;

[0073] 2) The above-mentioned 2,5-bis(tributyltin-based)thiophene and the intermediate of the polythiophene compound prepared in Example 1 were dissolved in 20ml of toluene in an equimolar ratio (the amount was 1 mmol), and 1% (the Consumption is the catalyst Pd (PPh 3 ) 4 , refluxed for 24-48 hours, cooled, settled in methanol, filte...

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Abstract

The invention discloses polythiophene compound, intermedium thereof and a preparation method and application of the same two to a solar battery. The intermedium of the polythiophene compound has the structural formula I, and the polythiophene compound has the structural formula II, wherein m is more than or equal to 10 and is less than or equal to 100, and n is more than or equal to 0 and is lessthan or equal to 100. The novel polythiophene compound is obtained in such a way that a lateral group is connected to an electron-donating group, thereby the conjugate length of a main chain of polythiophene is increased, the carrier mobility and the sun light absorbance of polymer are improved. The polymer with different compounding ratios can be obtained by adjusting the proportion of an electron-donating lateral group to a 3-hexylthiophene as required. The polythiophene compound has correct structure, simple preparation method, easy operation and high yield. Containing the electron-donating lateral group with nitrogen (N), the polythiophene compound is easy to form into a film and is improved in the crystallinity in the film and can be widely used for preparing the solar battery.

Description

technical field [0001] The present invention relates to a kind of polythiophene compound and its intermediate and their preparation method and application, especially a kind of polythiophene compound with side group containing electron-donating group and its intermediate and their preparation method and application in solar cell in the application. Background technique [0002] Since Stang announced the first organic solar cell in the mid-1980s (C.W.Tang, Appl. Phys. Lett. 1986, 48, 183-184.), organic solar cells are easy to manufacture because of their low density and low price. And the high stability has attracted the attention of many research groups and companies all over the world (Thompson, B.C.; Frechet, J.M.J.Angew.Chem.Int.Ed.2008, 47, 58; Mayer, A.C.; Scully, S.R.; Hardin, B.E.; Rowell, M.W.; McGehee, M.D. Materials today, 2007, 10, 28; Li, G.; Shrotriya, V.; Yao, Y.; Huang, J.; Yang, Y.J. Mater. Chem., 2007, 17, 3126) Among them, with polythiophene polymer as th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/06
Inventor 薄志山李韦伟韩洋陈于蓝
Owner INST OF CHEM CHINESE ACAD OF SCI
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