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6H-pyrrolo[3,4-f]benzotriazole-5,7-dione-containing corrugated polymer and applications thereof

A benzotriazole-conjugated polymer technology, applied in photovoltaic power generation, electrical components, climate sustainability, etc., can solve the problems of restricting the development of photoelectric materials and the weak electron-absorbing ability of benzotriazole, and achieve high The effect of energy conversion efficiency

Active Publication Date: 2015-07-01
东莞伏安光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the electron-withdrawing ability of benzotriazole is weak, which seriously restricts the development of optoelectronic materials.

Method used

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  • 6H-pyrrolo[3,4-f]benzotriazole-5,7-dione-containing corrugated polymer and applications thereof
  • 6H-pyrrolo[3,4-f]benzotriazole-5,7-dione-containing corrugated polymer and applications thereof
  • 6H-pyrrolo[3,4-f]benzotriazole-5,7-dione-containing corrugated polymer and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The preparation of 4,7-di(thiophene-2-yl)-5,6-diamino-N-alkyl-isoindole-1,3-dione, the reaction formula is shown in formula I:

[0035]

[0036] 4,7-bis(thiophene-2-yl)-1,2,5-benzothiadiazole-N-alkyl-5,6-dibasic carboxylic acid imide (a) synthetic reference in formula I Literature [Wang LX, Cai DD, Zheng QD, et al. ACS Macro Lett. 2013, 2, 605-608].

[0037] The preparation of 4,7-bis(thiophen-2-yl)-5,6-diamino-N-octyl-isoindole-1,3-dione is illustrated as an example. Add 4,7-bis(thiophen-2-yl)-1,2,5-benzothiadiazole-N-octyl-5,6-dibasic carboxylic acid imide (0.87g, 1.82mmol) and iron powder (1.22g, 21.8mmol), then add 30ml of glacial acetic acid, stir and reflux under nitrogen for 5h, then pour the reaction solution into water, a yellow-green solid precipitates, filter, take the filter residue, and use silica gel chromatography Column separation and purification gave yellow solid 4,7-bis(thiophen-2-yl)-5,6-diamino-N-octyl-isoindole-1,3-dione (0.6g, yield 73%) . ...

Embodiment 2

[0045] 4,8-bis(thiophene-2-yl)-1H-6-R 1 The preparation of base-6H-pyrrolo[3,4-f]benzotriazole-5,7-dione, the reaction formula is shown in formula II:

[0046]

[0047] The preparation of 4,8-bis(thiophen-2-yl)-1H-6-octyl-6H-pyrrolo[3,4-f]benzotriazole-5,7-dione is illustrated as an example. 4,7-bis(thiophen-2-yl)-5,6-diamino-N-octyl-isoindole-1,3-dione (2g, 4.4mmol) was dissolved in 30ml THF and stirred until complete Dissolve, then add 4ml glacial acetic acid. NaNO 2 (1.5 g, 22 mmol) in water was added dropwise into the reaction vessel. After reacting at room temperature for 6 h, the reaction solution was poured into water and extracted with dichloromethane. Dry the organic phase with anhydrous magnesium sulfate, filter, and spin dry the organic phase to obtain a light yellow solid 4,8-di(thiophen-2-yl)-1H-6-octyl-6H-pyrrolo[3,4-f] Benzotriazole-5,7-dione (1.7g, crude yield 86%), the obtained product can be directly carried out to the next reaction without further pu...

Embodiment 3

[0051] 4,8-di(thiophen-2-yl)-6-R 1 Base–2–R 2 The preparation of base-6H-pyrrolo[3,4-f]benzotriazole-5,7-dione, the reaction formula is shown in formula III:

[0052]

[0053]

[0054] Taking the preparation of 4,8-di(thiophen-2-yl)-6-octyl-2-octyl-6H-pyrrolo[3,4-f]benzotriazole-5,7-dione as an example illustrate. Add 4,8-bis(thiophene-2-yl)-1H-6-octyl-6H-pyrrolo[3,4-f]benzotriazole-5,7-dione (1.7 g, 3.66mmol), 1-bromooctane (0.85g, 4.4mmol) and potassium tert-butoxide (0.5g, 4.4mmol), then add 50ml of anhydrous methanol and stir evenly, and reflux under nitrogen for 24h. The reaction solution was poured into water and extracted with dichloromethane. Dry the organic phase with anhydrous magnesium sulfate, filter, spin-dry the organic phase, and then separate and purify with silica gel chromatography to obtain a yellow solid 4,8-di(thiophene-2-yl)-6-octyl-2-octyl- 6H-pyrrolo[3,4-f]benzotriazole-5,7-dione (0.75 g, 35.5% yield).

[0055] 1 H NMR (300MHz, CDCl 3 ): δ...

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Abstract

The invention discloses a 6H-pyrrolo[3,4-f]benzotriazole-5,7-dione-containing corrugated polymer, with the structural formula as shown in the specification. The prepared copolymer has fluorescence, and wide absorption to sunshine, thus being applied to production of active layers of polymer light-emitting diode devices, polymer field-effect transistors and polymer solar cells.

Description

technical field [0001] The invention relates to a new polymer used in the field of optoelectronic materials and devices, in particular to a novel conjugated polymer containing 6H-pyrrolo[3,4-f]benzotriazole-5,7-dione and Its preparation and application. Background technique [0002] In the past ten years, organic solar thin-film batteries have been very popular, and the efficiency of organic thin-film batteries has also hit new highs frequently. At present, the highest efficiency of single-layer devices has exceeded 10%, and the market prospect is very bright. In order to obtain high-efficiency polymer solar cell devices, materials are one of the most important factors. Generally speaking, an ideal material should have broad absorption, high carrier mobility, and suitable energy level. Among many optoelectronic materials, optoelectronic materials containing triazole heterocyclic units (such as benzotriazole) have been widely used in organic electroluminescence, organic sol...

Claims

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Application Information

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IPC IPC(8): C08G61/12C08L65/00H01L51/46
CPCY02E10/549Y02P70/50
Inventor 黄飞兰柳元曹镛
Owner 东莞伏安光电科技有限公司