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Copolymer containing cyclopentadiene bithiophene-benzobis(benzothiadiazole), preparation method and applications thereof

A benzothiadiazole and copolymer technology, which is applied in the fields of semiconductor/solid-state device manufacturing, organic chemistry, electric solid-state devices, etc., can solve the problem of low energy conversion efficiency, wide energy band gap, and reduced photon absorption rate of organic solar cells. question

Inactive Publication Date: 2014-07-23
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing polymers containing benzothiadiazole units have a wide bandgap (the energy level difference between the HOMO energy level and the LUMO energy level), which reduces the absorption rate of photons in the solar spectrum, making it possible to use Organic solar cells with polymers containing bithiazole units have low energy conversion efficiencies

Method used

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  • Copolymer containing cyclopentadiene bithiophene-benzobis(benzothiadiazole), preparation method and applications thereof
  • Copolymer containing cyclopentadiene bithiophene-benzobis(benzothiadiazole), preparation method and applications thereof
  • Copolymer containing cyclopentadiene bithiophene-benzobis(benzothiadiazole), preparation method and applications thereof

Examples

Experimental program
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preparation example Construction

[0042]One embodiment contains 3,6-carbazole-benzo two (benzothiadiazole) copolymer preparation method, such as figure 1 shown, including the following steps:

[0043] Step S100, providing compound A and compound B.

[0044] A is: B is: Among them, R 1 , R 2 , R 3 for C 1 ~C 20 of alkyl.

[0045] Wherein the preparation of compound A comprises the following steps:

[0046] Step S111, adding 2-amino-5-nitroaniline to thionyl chloride (SOCl 2 ), add pyridine dropwise while stirring (the structural formula is Molecular formula is C 5 h 5 N,), wherein the solid-to-liquid ratio of 2-amino-5-nitroaniline to pyridine is 3mol:40ml, and then heated to 80°C~90°C for reflux reaction for 24 hours, then remove excess thionyl chloride, add after cooling Precipitate with deionized water, collect the solid, wash it and dry it in vacuum to obtain 5-nitro-2,1,3 benzothiadiazole.

[0047] The reaction formula of this step is:

[0048]

[0049] Step S112, mixing 5-nitro-2,1,3-...

Embodiment 1

[0100] This example discloses poly{9-octyl-3,6-carbazole-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3, 4-e] bis(benzothiadiazole)} (containing 3,6-carbazole-benzobis(benzothiadiazole) copolymer P1):

[0101]

[0102] The preparation process of the above-mentioned 3,6-carbazole-benzobis(benzothiadiazole) copolymer P1 is as follows:

[0103] 1.1. Preparation of compound 5-nitro-2,1,3 benzothiadiazole

[0104]

[0105] Add 2-amino-5-nitroaniline (22.95g, 0.15mol) and 100ml of thionyl chloride into a three-necked flask, stir and slowly add 2ml of pyridine dropwise, heat and reflux at 80~90°C for 24h, stop the reaction , heated to 80°C and rotary evaporated excess SOCl 2 Finally, the reaction product was cooled to room temperature, poured into a large amount of water, stirred, filtered, washed with water, and then vacuum-dried to obtain 21.7 g of the product 5-nitro-2,1,3-benzothiadiazole with a yield of 80%.

[0106] 1.2. Preparation of compound 4,7-dibromo-5-nitro-2,1,3 benz...

Embodiment 2

[0127] This example discloses poly{9-methyl-3,6-carbazole-6-(3,7-dimethyl)octyl-7-n-eicosyl-benzo[2, 1-e:3,4-e]bis(benzothiadiazole)} (containing 3,6-carbazole-benzobis(benzothiadiazole) copolymer P2):

[0128]

[0129] The above-mentioned preparation process containing 3,6-carbazole-benzobis(benzothiadiazole) copolymer P2 is as follows:

[0130] 2.1. The preparation of 4,4'-dibromo-6,6'-diiodo-linked 2,1,3 benzothiadiazole is the same as in Example 1.

[0131] 2.2. Preparation of 4,9-dibromo-6-(3,7-dimethyl)octyl-7-eicosylbenzo[2,1-e:3,4-e]bis(benzothio oxadiazole)

[0132]

[0133] Add 4,4'-dibromo-6,6'-diiodo-bi-2,1,3 benzothiadiazole (3.4g, 5mmol) into the three-necked flask, add 2,6-dimethyl-9- Triacyne (4.47g, 10mmol), 25ml DMF, stirred with nitrogen for 20min, added Bu 3 N (0.907g, 10mmol) and Pd(OAc) 2 (115 mg, 0.5 mmol), heated to 130 ° C, heated for 4 h, cooled, washed with water, extracted with dichloromethane to obtain an organic layer, dried over anhydrou...

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Abstract

The invention provides a copolymer containing 3,6-carbazole-benzobis(benzothiadiazole), a preparation method and applications thereof. The copolymer containing 3,6-carbazole-benzobis(benzothiadiazole) is represented by a formula which is represented in the description; wherein in the formula, the R1, R2 and R3 individually represent a C1-C20 alkyl group, and n is an integer in a range of 1 to 100. The energy gap of the copolymer containing 3,6-carbazole-benzobis(benzothiadiazole) is narrow.

Description

technical field [0001] The invention relates to a 3,6-carbazole-benzobis(benzothiadiazole) copolymer, its preparation method and the use of the 3,6-carbazole-benzobis(benzothiadiazole) copolymer Copolymer solar cell devices and organic electroluminescent devices. Background technique [0002] The energy issue is a major issue of great concern to all countries in the world. Solar energy is the most ideal alternative energy source for humans in the future, and solar cells that convert solar energy into electrical energy are also research hotspots. Conjugated polymer thin film solar cells emerging in recent years have outstanding advantages such as low cost, light weight, simple manufacturing process, and can be prepared into flexible devices. In addition, organic materials are diverse and highly designable, promising to improve the performance of solar cells through material design and optimization. [0003] The benzothiadiazole unit has excellent reduction reversibility, w...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D513/04C07D519/00H01L51/46H01L51/54
CPCY02E10/549
Inventor 周明杰管榕黎乃元黄佳乐李满园
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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