Conjugated polymer containing 7H-pyrrolo [3,4-g] quinoxaline-6,8-diketone and application of conjugated polymer

A conjugated polymer, quinoxaline-technology, applied in the field of new conjugated polymers, can solve the problems of not very strong electron-absorbing ability and difficult to form wide-absorbing polymers, and achieve novel structure and improved electron-absorbing ability , the effect of high mobility

Active Publication Date: 2015-07-01
SOUTH CHINA UNIV OF TECH
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Problems solved by technology

However, the chemical functional group of benzimide also has its limitations, mainly because the electron-withdrawing ability is not very strong, and it is difficult to form a wide-absorbing polymer after copolymerization with other aromatic groups.

Method used

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  • Conjugated polymer containing 7H-pyrrolo [3,4-g] quinoxaline-6,8-diketone and application of conjugated polymer
  • Conjugated polymer containing 7H-pyrrolo [3,4-g] quinoxaline-6,8-diketone and application of conjugated polymer
  • Conjugated polymer containing 7H-pyrrolo [3,4-g] quinoxaline-6,8-diketone and application of conjugated polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 4,7-di(thiophen-2-yl)-5,6-diamino-N-R 1 The preparation of base-isoindole-1,3-diketone, the reaction formula is as shown in formula I:

[0033]

[0034] In formula I, 4,7-bis(thiophen-2-yl)-1,2,5-benzothiadiazole-N-R 1 The synthesis of base-5,6-dicarboxylic acid imide (a) refers to [Wang LX, Cai DD, Zheng QD, et al.ACS Macro Lett.2013,2,605-608].

[0035] 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

[0043] 5,9-di(thiophen-2-yl)-7-R 1 Base–2–R 2 Base–3–R 3 The preparation of base-7H-pyrrolo[3,4-g]quinoxaline-6,8-dione, the reaction formula is shown in formula II:

[0044]

[0045] To prepare 5,9-bis(thiophen-2-yl)-7-octyl-2,3-bis(4-octyloxyphenyl)-7H-pyrrolo[3,4-g]quinoxaline- 6,8-diketone is used as an example to illustrate. Add 4,7-bis(thiophene-2-yl)-5,6-diamino-N-octyl-isoindole-1,3-dione (0.38g, 0.83mmol) and 1 ,2-bis(4-octyloxyphenyl)ethane-1,2-diketone (0.42g, 0.87mmol), then add 45ml glacial acetic acid, stir and reflux under nitrogen overnight, then pour the reaction solution into water , 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 an orange solid 5,9-di(thiophene-2-yl)-7-octyl-2,3-di (4-octyloxyphenyl)-7H-pyrrolo[3,4-g]quinoxaline-6,8-dione (0.63 g, 86% yield).

[0046] 1 H NMR (300MHz, CDCl 3 ):δ=7.68-7...

Embodiment 3

[0059] 5,9-bis(5-bromo-thiophen-2-yl)-7-R 1 Base–2–R 2 Base–3–R 3 The preparation of base-7H-pyrrolo[3,4-g]quinoxaline-6,8-dione, the reaction formula is shown in formula III:

[0060]

[0061] To prepare 5,9-bis(5-bromo-thiophen-2-yl)-7-octyl-2,3-bis(4-octyloxyphenyl)-7H-pyrrolo[3,4-g] Quinoxaline-6,8-dione is used as an example to illustrate. Add 5,9-bis(thiophene-2-yl)-7-octyl-2,3-bis(4-octyloxyphenyl)-7H-pyrrolo[3,4-g]quinone into 100ml two-neck bottle Oxaline-6,8-diketone (0.63g, 0.71mmol), and then add 30ml of chloroform and 10ml of glacial acetic acid and stir well. NBS (N-bromosuccinimide, N-bromosuccinimide) (0.31 g, 1.71 mmol) was added under ice-bath conditions, and the reaction was carried out at room temperature for 24 h. 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 ob...

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Abstract

The invention discloses a conjugated polymer containing 7H-pyrrolo [3,4-g] quinoxaline-6,8-diketone and an application thereof. A structural formula is described in the description. The prepared conjugated polymer containing 7H-pyrrolo [3,4-g] quinoxaline-6,8-diketone has fluorescence and broad sunlight absorption range, so that the conjugated polymer containing 7H-pyrrolo [3,4-g] quinoxaline-6,8-diketone can be applied to production of a polymeric light-emitting diode device and active layers of a polymer field effect transistor and a polymer solar battery. The structural formula is described in the description.

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 7H-pyrrolo[3,4-g]quinoxaline-6,8-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. So this requires us to innovate materials and develop more new conjugated polymer materials. Among many photoelectric materials, photoelectric materials containing quinoxaline groups or imide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C08L65/00H01L51/46
CPCY02E10/549
Inventor 黄飞兰柳元曹镛
Owner SOUTH CHINA UNIV OF TECH
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