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Copolymer containing cyclopentadiene bithiophene-benzo-2 (benzothiadiazole) and preparation method and application thereof

A technology of benzothiadiazole and copolymers, which is applied in semiconductor/solid-state device manufacturing, organic chemistry, electric solid-state devices, etc., can solve the problems of low energy conversion efficiency of organic solar cells, lower photon absorption rate, wide energy bandgap, etc. question

Inactive Publication Date: 2014-05-07
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-benzo-2 (benzothiadiazole) and preparation method and application thereof
  • Copolymer containing cyclopentadiene bithiophene-benzo-2 (benzothiadiazole) and preparation method and application thereof
  • Copolymer containing cyclopentadiene bithiophene-benzo-2 (benzothiadiazole) and preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0042] One embodiment contains the preparation method of benzothiophene-benzobis(benzothiadiazole) copolymer, 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 for C 1 ~C 20 the alkyl group, R 3 , R 4 for H or 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:

[...

Embodiment 1

[0088] This example discloses poly{5,6-bis(3,7-dimethyl)octylbenzo[c]thiophene-6,7-bis(3,7-dimethyl)octyl- Benzo[2,1-e:3,4-e]bis(benzothiadiazole)} (containing benzothiophene-benzobis(benzothiadiazole) copolymer P1):

[0089]

[0090] The preparation process of the above-mentioned benzothiophene-benzobis(benzothiadiazole) copolymer P1 is as follows:

[0091] 1.1. Preparation of compound 5-nitro-2,1,3 benzothiadiazole

[0092]

[0093] 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%;

[0094] 1.2. Preparation of compound 4,7-dibr...

Embodiment 2

[0117]This embodiment discloses poly{benzo[c]thiophene-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3,4-e]di (benzothiadiazole)} (containing benzothiophene-benzobis(benzothiadiazole) copolymer P2):

[0118]

[0119] The preparation process of the above-mentioned benzothiophene-benzobis(benzothiadiazole) copolymer P2 is as follows:

[0120] 2.1, 4,9-dibromo-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole) Prepare with embodiment 1.

[0121] 2.2. Preparation of 1,3-bis(tributyltin)benzo[c]thiophene

[0122]

[0123] Under the protection of nitrogen, add 1,3-dibromobenzo[c]thiophene (2.92g, 0.01mol) into the three-necked flask, add 80ml of tetrahydrofuran solvent, and then slowly inject it with a syringe at -78°C. Butyllithium (8.4mL, 2.5M, 0.02mol), continue to stir the reaction for 1h, inject tributyltin chloride (5.6mL, 0.02mol) with a syringe under the condition of -78°C, heat up to room temperature and stir for 1 hour React for 6 hours. Saturated aqueo...

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Abstract

A copolymer containing benzothiadiazole thiophene-benzo-2 (benzothiadiazole) has the following structural formula: (shown in the Specification), wherein the R1 and R2 are alkyls from C1 to C20; the R3 and R4 are H or the alkyls from C1 to C20; the n is an integer from 1 to 100. The above benzothiadiazole thiophene-benzo-2 (benzothiadiazole) copolymer has a relatively narrow energy gap. The invention further provides a preparation method of the benzothiadiazole thiophene-benzo-2 (benzothiadiazole) copolymer as well as solar battery devices and organic electroluminescent devices which adopt the benzothiadiazole thiophene-benzo-2 (benzothiadiazole) copolymer.

Description

technical field [0001] The invention relates to a benzothiophene-benzobis(benzothiadiazole) copolymer, a preparation method thereof and a solar cell device using the benzothiophene-benzobis(benzothiadiazole) copolymer 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, which i...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D513/04H01L51/46H01L51/54
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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