Conjugated polymer based on condensed ring thiophene and diazosulfide as well as preparation method and application thereof

A technology of benzothiadiazole and conjugated polymers, which is applied in the field of conjugated polymers based on fused ring thiophene and benzothiadiazoles and their preparation and application, and can solve the problems of large gaps, no absorption, and hole migration Low efficiency and other problems, to achieve the effect of good processability and good thermal stability

Active Publication Date: 2010-03-17
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

In 2007, the American scientist Alan Heeger's research team used a new device manufacturing process to increase the efficiency of organic solar cells to 6.5% (J.Y.Kim, K.Lee, N.E.Coates, D.Moses, T.-Q.Nguyen, M. Dante, A.J.Heeger, "Efficient tandem polymer solar cells fabricated by al

Method used

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  • Conjugated polymer based on condensed ring thiophene and diazosulfide as well as preparation method and application thereof
  • Conjugated polymer based on condensed ring thiophene and diazosulfide as well as preparation method and application thereof
  • Conjugated polymer based on condensed ring thiophene and diazosulfide as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The synthetic route of polymer P1 is as follows figure 1 shown.

[0050] (1) 2,6-bis(3-dodecylthiophene)-trithiophene

[0051] Add 2-bromo-3-dodecylthiophene (1.25mmol, 664mg) and 2,6-bis(tributyltin)trithiophene (0.41mmol, 320mg) into a 50ml three-necked flask, and deoxygenate with nitrogen for 30 minutes , inject 10ml of dry toluene under the condition of isolated air, and add the catalyst Pd(PPh 3 ) 4 (Tetrakistriphenylphosphopalladium) (26 μmol, 30 mg), heated to 110° C., and reacted overnight with stirring. Cool to room temperature, add potassium fluoride aqueous solution 10ml (8g KF) and stir for 2.5 hours to precipitate and remove organic tin impurities. The reaction solution was extracted with chloroform, and the organic phase was collected and washed twice, dried over anhydrous magnesium sulfate, and purified by column chromatography (silica gel column, petroleum ether rinse) to obtain an orange solid (228mg, 79 %). 1 H NMR (400MHz, CDCl 3 ): δ7.29(s, 2H...

Embodiment 2

[0057] The synthetic route of polymer P2 is as follows Figure 6 shown.

[0058] (1) 2,6-Dibromo-3,5-Didecyltrithiophene

[0059] Add 3,5-didecyltrithiophene (0.42 g, 0.88 mmol), 10 ml of chloroform, and 10 ml of glacial acetic acid into a 100 ml single-necked bottle. The one-mouth bottle was wrapped with tin foil and cooled to 0°C. NBS (N-bromosuccinimide) (410mg, 2.30mmol) was dissolved in 3ml of dimethylformamide (DMF), then added dropwise to the one-necked bottle, stirred, and reacted for 1 hour to rise to Stir at room temperature for 4 hours. The yellow mixture was added to 200ml (2M) iced NaOH solution and stirred for 10 minutes. The organic phase was then extracted with 200ml×2 of dichloromethane, collected and dried over anhydrous magnesium sulfate. After filtration and spin-drying, it was washed with petroleum ether and separated through a silica gel column, and the solvent was removed to obtain a pale yellow solid (385 mg, 69%). 1 HNMR (400MHz, CDCl 3 ): δ2.73...

Embodiment 3

[0063] The synthetic route of polymer P3 is as follows Figure 11 shown.

[0064] Poly{[4,4-bis(decyl)dithienocyclopentadiene]-alternate-(2,1,3-benzothiadiazole)} (P3)

[0065] Add 2,7-dibromo-4,4-didecyldithienocyclopentadiene (2,7-dibromo-4,4-didecyldithiophene to a 25 ml three-neck round bottom flask Pentacyclopentadiene was synthesized according to the following literature: M.Zhang, H.N.Tsao, W.Pisula, C.Yang, A.K.Mishra, K.Müllen, "Field-effecttransistors based on a benzothiadiazole-cyclopentadithiophene copolymer", J.Am. Chem.Soc., 2007,129,3472) (123mg, 0.2mmol) and double borate substituted benzothiadiazole (78mg, 0.2mmol), then add toluene (2ml) and potassium carbonate aqueous solution (2ml, 550mg , 4 mmol), and deoxygenated by nitrogen for 30 minutes. Under the protection of nitrogen, the catalyst Pd(PPh 3 ) 4 (10 μmol, 12 mg), heated to 100°C. The reaction was stirred at 100°C for 3 days. Cool to room temperature, extract the organic phase with 100ml×2 chloro...

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Abstract

The invention relates to a conjugated polymer based on condensed ring thiophene and diazosulfide, a preparation method and an application of the conjugated polymer as an active layer material in organic optoelectronic devices, such as polymer solar energy cells, organic field effect transistors and organic light emitting diodes. The conjugated polymer based on condensed ring thiophene and diazosulfide has an excellent sunlight capture ability and a hole transmission ability, and the conjugated polymer solution has good processability, thermostability, charge transmission performance and lightadsorption and is an ideal organic semiconducting material in the organic electronic devices, such as solar energy cells, field effect transistors and light emitting diodes. A general formula of the conjugated polymer is shown as above.

Description

technical field [0001] The present invention relates to a class of conjugated polymers based on fused ring thiophene and benzothiadiazole and a preparation method thereof, and the conjugated polymers are used as active layer materials in organic optoelectronic devices such as polymer solar cells, organic field effect transistors and Applications in Organic Light Emitting Diodes. Background technique [0002] Currently used solar cells mainly rely on panels made of inorganic materials such as silicon or rare metal alloys to achieve photoelectric conversion. Although inorganic solar cells have the advantages of high efficiency and long life, the inorganic semiconductor materials are expensive and the preparation process is complicated. The cost is too high, etc. However, these factors always limit its large-scale application. In order for solar photovoltaic power generation to be popularized on a large scale, it is necessary to find cheaper solar cell materials. The organic ...

Claims

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Application Information

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IPC IPC(8): C08G61/12C09K11/06H01L51/00H01L51/46H01L51/30H01L51/54
CPCY02E10/50Y02E10/549
Inventor 占肖卫张仕明刘瑶
Owner INST OF CHEM CHINESE ACAD OF SCI
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