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A conjugated polymer containing acenaphtho[1,2-b]quinoxaline diimide and its preparation method and application

A quinoxaline diimide and conjugated polymer technology, applied in the field of conjugated polymers, can solve problems such as limitations, and achieve the effects of good thermal stability, novel structure and strong solar photon absorption ability

Active Publication Date: 2020-03-31
INST OF CHEM ENG GUANGDONG ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the current development of polymer receptor materials is still insufficient, limited to perylene diimide, naphthalene diimide and B-N compound materials

Method used

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  • A conjugated polymer containing acenaphtho[1,2-b]quinoxaline diimide and its preparation method and application
  • A conjugated polymer containing acenaphtho[1,2-b]quinoxaline diimide and its preparation method and application
  • A conjugated polymer containing acenaphtho[1,2-b]quinoxaline diimide and its preparation method and application

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preparation example Construction

[0025] The preparation method of the above-mentioned conjugated polymer containing acenaphtho[1,2-b]quinoxaline diimide comprises the following steps:

[0026] 1) With 4,7-bis(thiophen-2-yl)-1,2,5-benzothiadiazole-N-R 1 Base-5,6-dibasic carboxylic acid imide as the parent, adding iron powder for reduction to obtain 4,7-bis(thiophen-2-yl)-5,6-diamino-N-R 1 Base-isoindole-1,3-dione, and then with 2-R 2 -6,7-dihydro-1H-indeno(6,7,1-def)isoquinoline-1,3,6,7(2H)-tetraketone undergoes dehydration condensation reaction to obtain N-R 1 -N'-R 2 -7,10-bis(thiophen-2-yl)-1H-pyrido[3',4',5',5,6]acenaphtho[1,2-b]quinoxaline-8,9-di Carboxylic acid imide-1,3(2H)-dione, and then brominated by N-bromosuccinimide to obtain monomer N-R 1 -N'-R 2 -7,10-bis(5-bromo-thiophen-2-yl)-1H-pyrido[3',4',5',5,6]acenaphtho[1,2-b]quinoxaline-8 ,9-dicarboxylic acid imide-1,3(2H)-dione;

[0027] 2) Metal-catalyzed coupling reaction: react the monomer containing the Ar structure with the monomer prepared...

Embodiment 1

[0030] 4,7-bis(thiophen-2-yl)-5,6-diamino-N-R 1 The preparation of base-isoindole-1,3-diketone, reaction formula is as shown in formula I:

[0031]

[0032] 4,7-bis(thiophen-2-yl)-1,2,5-benzothiadiazole-N-R in formula I 1 The synthesis of base-5,6-dicarboxylic acid imide (a) refers to literature [Wang LX, Cai DD, Zheng QD, et al.ACS Macro Lett.2013,2,605-608].

[0033] Take the preparation of 4,7-di(thiophen-2-yl)-5,6-diamino-N-(2-decyltetradecyl)-isoindole-1,3-dione as an example to illustrate: Add 4,7-bis(thiophen-2-yl)-1,2,5-benzothiadiazole-N-(2-decyltetradecyl)-5,6-binary Carboxylic acid imide (1.41g, 2mmol) and iron powder (1.34g, 24mmol), then add 30mL of glacial acetic acid, stir and reflux for 5h under nitrogen, then pour the reaction solution into water, a yellow-green solid precipitates, filters, and takes The filter residue was separated and purified by silica gel chromatography to obtain a yellow solid, that is, 4,7-bis(thiophen-2-yl)-5,6-diamino-N-(2-decylt...

Embodiment 2

[0035] N-R 1 -N'-R 2 -7,10-bis(thiophen-2-yl)-1H-pyrido[3',4',5',5,6]acenaphtho[1,2-b]quinoxaline-8,9-di The preparation of carboxylic acid imide-1,3(2H)-diketone, the reaction formula is as shown in formula II:

[0036]

[0037] 2-R in Formula II 2 -6,7-Dihydro-1H-indeno[6,7,1-def]isoquinoline-1,3,6,7(2H)-tetraketone (c) Synthetic Reference [Herrera H, Echegaray PD, Urdanpilleta M, et al. Chem Commun. 2013, 49, 713].

[0038] To prepare N,N-bis(2-decyltetradecyl)-7,10-bis(thiophen-2-yl)-1H-pyrido[3',4',5',5,6]acenaphthene Take [1,2-b]quinoxaline-8,9-dicarboxylic acid imide-1,3(2H)-dione as an example to illustrate: add 4,7-di (Thien-2-yl)-5,6-diamino-N-(2-decyltetradecyl)-isoindole-1,3-dione (0.54g, 0.8mmol) and 2-(2 -decyltetradecyl)-6,7-dihydro-1H-indeno[6,7,1-def]isoquinoline-1,3,6,7(2H)-tetraone (0.47g, 0.8mmol), then add 45mL glacial acetic acid, stir and reflux overnight under nitrogen, then pour the reaction solution into water, extract with dichloromethane, dr...

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Abstract

The present invention disclosed a consecutive polymer and its preparation methods and applications of the co -pyramidis amine in the [1,2‑b] 喹 喹 啉 本, which contains [1,2‑b] 喹 啉 啉 本 duvin duetin duplex.The structural general formula of the co -pyramid polymeter of the alumine is: where R 1 R 2 Independent from cH, C 1 ~ C 24 Alkyl or C 1 ~ C 24 The alkoxyl, AR is an aromatic group, N is a natural number of 1 to 100,000, 0 <x <1, 0 <y <1, x+y = 1.The preparation method is as follows: 1) Single N‑r 1 ‑N′‑R 2 (7,10‑ II (5, bromine 噻 噻 ‑ 2‑ ‑ ‑ ‑ ‑1H‑pim pyridine and [3 ', 4', 5,6] 苊 and [1,2‑b] 喹 啉 啉 ‑ 8, 9酸DD. The preparation of dibitone in ‑1,3 (2H) of olsine; 2) Metal catalytic coupling reaction.The consensus of the present invention also [1,2‑b] The co -pyramid polymer structure of the pyrine dilate is novel, good thermal stability, strong sunshine absorption, and appropriate electronic energy level. It is suitable for organic solar cellsThe electronic receptor or electron supply material, and it is soluble in organic solvents such as chloroform, tetrahydrofu, and chloropene benzene, and can be processed by solution.

Description

technical field [0001] The invention relates to a conjugated polymer containing acenaphtho[1,2-b]quinoxaline diimide, a preparation method and application thereof. Background technique [0002] Organic solar cells have attracted extensive attention due to their advantages of low cost, light weight, translucency, and solution processing into large-area flexible thin-film devices. In recent years, with the continuous optimization of active layer materials, device structures and preparation process conditions, organic solar cells have developed rapidly and achieved remarkable results. At present, the photoelectric conversion efficiency of solar cells prepared by blending polymer donors or small molecule donors with fullerene acceptors has exceeded 11%, and the market prospect is bright. Materials are one of the most important determinants for obtaining high-efficiency organic solar cell devices. [0003] At present, the development of donor materials is rapid, while the devel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/12C08G61/126C08G2261/91C08G2261/414C08G2261/64C08G2261/592C08G2261/18C08G2261/3241C08G2261/3223C08G2261/122C08G2261/146C08G2261/1412H10K85/113Y02E10/549
Inventor 兰柳元麦裕良文武李岱远张磊高敏廖兵
Owner INST OF CHEM ENG GUANGDONG ACAD OF SCI