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Organic dyes containing trithienopyrrole-thiophene and their applications in dye-sensitized solar cells

An organic dye, thiophene pyrrole technology, applied in organic dyes, organic chemistry, azo dyes, etc., can solve the problem of narrow spectral absorption range, and achieve the effect of improving photovoltaic performance, improving efficiency, and optimizing dye energy level

Active Publication Date: 2019-01-18
深圳泓越信息科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, organic dyes have a narrow spectral absorption range, and it is difficult to fully absorb and utilize solar energy in the visible region, which has become a bottleneck that limits the further improvement of their photoelectric conversion efficiency.

Method used

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  • Organic dyes containing trithienopyrrole-thiophene and their applications in dye-sensitized solar cells
  • Organic dyes containing trithienopyrrole-thiophene and their applications in dye-sensitized solar cells
  • Organic dyes containing trithienopyrrole-thiophene and their applications in dye-sensitized solar cells

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: the preparation of organic dye 16

[0043] The synthetic route is as follows:

[0044]

[0045] The raw material 1 used in this example was prepared according to the literature Q.Yu, W.Fu, J.Wan, X.Wu, M.Shi, H.Chen.ACSAppl.Mater.Interfaces2014, 6, 5798-5809; raw material 10, 4-hexyloxyaniline and 3-bromo-2-thiophene zinc bromide According to literature Z.Wang, M.Liang, Y.Tan, L.Ouyang, Z.Sun, S.Xue.J.Mater.Chem.A ,2015,3,4865–4874 prepared from 4-hexyl-5-bromo-2-thiophene carboxaldehyde according to literature H.Lee, H.Jo, D.Kim, S.Biswas, G.D.Sharma, J.Ko.Dyes Pigments, 2016, 129, 209-219. Synthesis, other reagents can be obtained commercially.

[0046] Synthesis of Intermediate 2:

[0047] Into a 100mL single-necked round-bottom flask, add 3.75g of raw material 1 and 20mL of N-N dimethyldimethylformamide, then add 2.13g of N-bromosuccinimide to the system in batches, and keep the Light reaction for 8 hours; quenched with water, extracted with eth...

Embodiment 2

[0066] Embodiment 2: the synthesis of organic dye 17

[0067] The synthetic route is as follows:

[0068]

[0069] The raw material 7 and the intermediate 10 can be synthesized with reference to the preparation method of Example 1, and other reagents can be purchased commercially.

[0070] Synthesis of intermediate 13:

[0071] Under the protection of argon, in a 100mL three-necked round-bottomed flask, 0.784g of intermediate 12, 0.296g of 3-hexyl-2-bromothiophene, 0.011g of tetrakis(triphenylphosphine)palladium and 15mL of toluene were added successively, and the reaction system was heated After reacting at 110°C for 12 hours, cool to room temperature, concentrate by rotary evaporation, and purify the crude product by column chromatography (eluent: petroleum ether / dichloromethane=25 / 1~10 / 1) to obtain 0.476g of intermediate 13, pale yellow Viscous liquid, 72% yield. 1 H NMR (400MHz, CDCl 3 ): δ7.52(d, J=8.8Hz, 2H), 7.15(d, J=5.2Hz, 1H), 7.08-7.06(m, 3H), 6.92(d, J=5.4Hz...

Embodiment 3

[0081] Application of the dye 12 prepared in Example 1 in the preparation of dye-sensitized solar cells. Its specific use method is the same as the use method disclosed in the invention patent application with the application number 201510015966.7 and the invention title "A Carbazole-type Photosensitizing Dyestuff and Its Preparation Method and Application". Test light source: AM 1.5 (solar simulator-Oriel 91160-1000, 300W), data acquisition using Keithley 2400 digital source meter. see test results image 3 , the open circuit voltage of the battery (V oc ) is 852mV, short-circuit current density (J sc ) is 14.8mA cm -2 , the fill factor (FF) is 0.66, and the photoelectric conversion efficiency is 8.37%.

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Abstract

The invention discloses a trithienopyrrole-thiophene-containing organic dye, and an application thereof in dye-sensitized solar cells, and belongs to the technical field of solar cells. The organic dye has D-pi-A type structural characteristics, and is obtained through adopting triphenylamine as an electron donor, cyanoacrylic acid as an electron acceptor and a trithienopyrrole-thiophene unit as a conjugated bridge; and long alkyl chains are introduced to two ends of the lateral side of the trithienopyrrole-thiophene conjugated bridge to inhibit dye aggregation and alleviate the battery interface electron compounding. The dye-sensitized solar cells using the organic dye have a photoelectric conversion efficiency of 8.37% .

Description

technical field [0001] The invention belongs to the technical field of organic dyes, and in particular relates to an organic dye containing trithienopyrrole-thiophene, a preparation method thereof and an application in dye-sensitized solar cells. Background technique [0002] As a new generation of photovoltaic technology, dye-sensitized solar cells have (O’Regan, B.; M.Nature1991,353,737.) has the characteristics of high utilization efficiency, simple process and low cost. Among them, photosensitizing dyes are the core components in dye-sensitized solar cells, which undertake the heavy responsibility of light harvesting and play a decisive role in the efficiency of cells. Compared with ruthenium-based and zinc porphyrin dyes, organic dyes have the characteristics of simple synthesis, readily available raw materials, low preparation cost, and more flexible molecular structure modification, and have become a research hotspot in the field of dye-sensitized solar cells. Howe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/22C09B57/00H01G9/20H01G9/042
CPCY02E10/542
Inventor 王志辉鲁玉婷陈然石慧钱国庆丁师杰陈静
Owner 深圳泓越信息科技有限公司
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