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A-A type conjugated polymer based on isoindigo-blue and preparation method and application thereof

A conjugated polymer, A-A technology, applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc., can solve problems such as high cost, difficult preparation and purification, and low light absorption coefficient

Active Publication Date: 2016-07-06
UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, fullerene acceptor materials also have some disadvantages, such as their low absorption coefficient in visible light, difficulty in preparation and purification, high cost, and limited open-circuit voltage of devices due to the difficulty in adjusting the energy level structure, etc. Further improvements in the efficiency of organic solar cells

Method used

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  • A-A type conjugated polymer based on isoindigo-blue and preparation method and application thereof
  • A-A type conjugated polymer based on isoindigo-blue and preparation method and application thereof
  • A-A type conjugated polymer based on isoindigo-blue and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] This embodiment provides an A-A type conjugated polymer based on isoindigo, and the general structural formula is shown in formula (I);

[0046] Formula (I)

[0047] Wherein, R is a C1-C32 alkane group, a C2-C32 alkene group, a C2-C32 alkynyl group, an etheroxy group, an alkyl chain amine or a mercapto group; n is an integer greater than or equal to 4 and less than or equal to 100;

[0048] Ar is an aromatic compound fragment, specifically:

[0049]

[0050] Therefore, the chemical formula of the A-A type conjugated polymer of this embodiment is specifically shown in formula (II), formula (III) or formula (IV);

[0051] formula (II);

[0052] formula (III);

[0053] Formula (IV).

[0054] The conjugated polymer of formula (II) is designated as PIIG-NDI(OD), the conjugated polymer of formula (III) is designated as PIIG-PDI(OD), and the conjugated polymer of formula (IV) is designated as PIIG-PDI (EH). exist figure 1 The UV-Vis absorption spectra of PIIG...

Embodiment 2

[0056] This example provides a method for preparing the A-A type conjugated polymer PIIG-NDI(OD) represented by the above formula (II).

[0057] 6,6'-(N,N'-2-octyldodecyl)-Pinacoldiboronisoindigo and N,N'-bis were catalyzed by tris(dibenzylideneacetone)dipalladium and tris(o-methylphenyl)phosphorus (2-octyldodecyl)-2,6-dibromonaphthalene-1,4,5,8-bis(dicarboximide) was reacted in an organic solvent at 90°C-100°C for 70 hours-72 hours to obtain the conjugate of the above formula (II) polymer.

[0058] In this method, 6,6'-(N,N'-2-octyldodecyl)-Pinacoldiboronisoindigo and N,N'-bis(2-octyldodecyl)-2,6-dibromonaphthalene-1,4,5,8-bis( dicarboximide) in a molar ratio of 1:0.99-1.05, preferably 1:1. The dosage of tris(dibenzylideneacetone)dipalladium is 1%-2% of the molar dosage of 6,6'-(N,N'-2-octyldodecyl)-Pinacoldiboronisoindigo, and the dosage of tris(o-methylphenyl)phosphorus It is 5%-6% of the molar amount of 6,6'-(N,N'-2-octyldodecyl)-Pinacoldiboronisoindigo. The organic so...

Embodiment 3

[0062] The third embodiment provides a specific method for the A-A type conjugated polymer PIIG-NDI(OD) represented by the above formula (II).

[0063]

[0064] First of all, in the above formula, the place marked 1 is compound 1, and the place marked 2 is compound 2.

[0065] Under nitrogen protection, into a 25ml Schlenk tube, add 109.7mg (0.102mmol) of compound 1, 100.5mg (0.102mmol) of compound 2, 108.5mg (0.5mmol) of potassium phosphate, 50mg of tetrabutylammonium chloride , 1.4 mg (1.5 mol%) of Pd 2 (dba) 3 , 1.9 mg (6 mol%) of P-(o-Tol) 3 , 7ml of toluene, 1.5ml of water. The reaction was stirred at 90°C for 3 days.

[0066] It was then capped with pinacol phenylboronic acid and bromobenzene.

[0067] Then the product PIIG-NDI (OD) 116.3 mg was obtained from chloroform by Soxhlet extraction with a yield of 69%.

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Abstract

The embodiment of the invention relates to an A-A type conjugated polymer based on isoindigo-blue and a preparation method and application thereof.The structural general formula of the A-A type conjugated polymer based on isoindigo-blue is shown in the description, wherein Ar is an aromatic compound fragment, and R is alkane of C1-C32, alkenyl of C2-C32 and alkyne or ether oxygen or alkyl chain amines or sulfydryl of C2-C32; n is an integer larger than or equal to 4 and smaller than or equal to 100.According to the A-A type conjugated polymer based on isoindigo-blue, the solubility is good, the light absorbance is strong, the absorption range is wide, the sunshine utilization rate is high, the LUMO energy level is low, the A-A type conjugated polymer can replace fullerene and derivatives thereof as an acceptor material for preparing a full-polymer organic light detector and an organic solar cell.

Description

technical field [0001] The present invention relates to a conjugated polymer, in particular to an A-A type conjugated polymer based on isoindigo and its preparation method and application. Background technique [0002] As a new type of functional materials, organic conjugated polymers have attracted extensive attention of scientists in recent years. At present, organic optoelectronic devices have realized part of the functions of inorganic semiconductor optoelectronic devices, such as electroluminescent diodes, organic solar cells, organic field effect transistors, and organic information storage. [0003] Conjugated polymers can also be used as active layer materials for photodetectors. Currently, polymers / fullerenes are mainly used as active layer materials. For the photodetector based on polymer / fullerene, Liang Yongye's group successfully reduced the dark current to 2.6×10 by optimizing the molecular structure. -10 A cm -2 at-0.2V without much influence on its transmi...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCC08G61/124C08G2261/124C08G2261/141C08G2261/91C08G2261/64C08G2261/228C08G2261/324C08G2261/18C08G2261/411H10K85/111Y02E10/549
Inventor 黄辉王小芬吕磊
Owner UNIVERSITY OF CHINESE ACADEMY OF SCIENCES
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