Closed-loop triphenylamine derivative copolymer and preparing method and application thereof

A kind of copolymer and triphenylamine technology, applied in the field of polymer photovoltaics, can solve the problems of unfavorable charge separation, the energy conversion efficiency of solar cells cannot be improved, and achieve lower energy bandgap, excellent photovoltaic performance, and increased spectral absorption range. Effect

Inactive Publication Date: 2015-04-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Polymer-based solar cells mainly involve electron donor materials and electron acceptor materials. Initially, the battery devices made are solar cells with a double-layer structure; however, batteries with such structures are not conducive to charge separation, so solar cells The energy conversion efficiency of the battery is not improved

Method used

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  • Closed-loop triphenylamine derivative copolymer and preparing method and application thereof
  • Closed-loop triphenylamine derivative copolymer and preparing method and application thereof
  • Closed-loop triphenylamine derivative copolymer and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of Methyl 2-iodobenzoate

[0033]

[0034] Methyl anthranilate (30.2g, 200mmol) and concentrated hydrochloric acid (36%, 35ml) were successively added to 100ml of distilled water, and stirred for 15min under an ice bath. Slowly add an aqueous solution of sodium nitrite (27.6g, 400mmol), stir in an ice bath for 1 hour, then slowly add an aqueous solution of potassium iodide (90g, 600mmol), control the reaction temperature at 5-8°C, and react overnight in the dark. The reaction solution was extracted with 200ml of dichloromethane, the extract was washed 3 times with saturated sodium chloride solution, and the extract was dried with magnesium sulfate. Dichloromethane was distilled off under reduced pressure, and the initial product was chromatographed on a silica gel / petroleum ether column to obtain 42 g of a colorless liquid with a yield of 80.5%.

Embodiment 2

[0036] Synthesis of 2,2',2"-trimethylcarboxymethyl triphenylamine

[0037]

[0038] Methyl o-iodobenzoate (42g, 161mmol), methyl anthranilate (8.2g, 54mmol), potassium carbonate (18g, 13mmol), copper powder (0.75g, 11.4mmol), cuprous iodide (1.05 g, 5.45 mmol) was added into 300 ml of phenyl ether, nitrogen gas was passed for 5 min, and the reaction was heated and stirred at 190° C. for 48 hours. After cooling, filter with suction, and distill the filtrate to remove the solvent under reduced pressure to obtain a crude product, which is recrystallized from ethanol to obtain 16.97 g of yellow crystals with a yield of 75%.

Embodiment 3

[0040] Synthesis of 2,2',2"-tris(bis(4-methylphenyl)hydroxymethyl)triphenylamine

[0041]

[0042]Dissolve p-bromotoluene (9.6 g, 56 mmol) in anhydrous tetrahydrofuran, and stir at -78°C for 15 minutes under nitrogen protection. Add n-butyllithium (22.5ml, 2.5M, 56.25mmol) dropwise to the p-bromotoluene solution, and stir at -78°C for 1 hour. Add 2,2',2"-trimethylcarboxymethyl triphenylamine (2.1g, 5mmol) in tetrahydrofuran solution dropwise, slowly rise to room temperature, and react overnight. Quench with an appropriate amount of saturated ammonium chloride aqueous solution, and distill under pressure to remove tetrahydrofuran The resulting yellow solid was added to 50ml of ethanol, heated to boiling, and stirred for 0.5 hours. After cooling, it was suction filtered, and the solid was washed once with water, ethanol, and petroleum ether, and dried to obtain 3.9 g of a yellow-green solid with a yield of 89%.

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Abstract

The invention discloses a closed-loop triphenylamine derivative copolymer and a preparing method and application of the closed-loop triphenylamine derivative copolymer. The preparing method includes the steps that a closed-loop triphenylamine unit containing di-pinacol boric-acid-ester groups and a copolymerization unit containing di-bromine groups are reacted for 12-48 hours with a palladium compound serving as a catalyst, organic alkali or inorganic alkali serving as an alkali source and methylbenzene serving as a solvent under protection of inert gas at the temperature of 25-130 DEG C, and finally the closed-loop triphenylamine derivative copolymer is obtained, wherein the molar content of a palladium compound accounts for 0.1-10% of the content of a closed-loop triphenylamine derivative, and the molar concentration of a reactant monomer is between 0.1 mole per liter and 1 mole per liter. By copolymerizing various narrow-band-gap units provided with a donor-acceptor-donor (D-A-D) structure and the closed-loop triphenylamine derivative, narrow-band-gap conjugated polymers with high heat stability and high wide-spectrum absorbing performance are obtained. The closed-loop triphenylamine derivative copolymer prepared through the method serves as a donor material to be applied to polymer solar cells.

Description

technical field [0001] The invention belongs to the technical field of polymer photovoltaics, and in particular relates to a closed-loop triphenylamine derivative copolymer and its preparation method and application. Background technique [0002] Since 1986, C.W.Tang (Appl.Phys.Lett.48,183,1986) prepared a double-layer organic solar cell for the first time, and its energy conversion efficiency reached 1%, and the fill factor FF=65%; subsequently, organic solar cells Batteries, as a new type of solar cells, have attracted great attention. However, on the basis of organic solar cells, scientists have developed polymer-based solar cells. Polymer solar cell materials, due to their low production cost, large-area manufacturing and flexible solar cells that can be bent, have quickly received widespread attention from all over the world, and a lot of research has been invested. Polymer-based solar cells mainly involve electron donor materials and electron acceptor materials. Init...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 张斌彭沣杨伟曹镛
Owner SOUTH CHINA UNIV OF TECH
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