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Five-membered heterocyclic derivative-bridged perylene diimide dipolymer and its preparation method and use in organic photovoltaic device

A perylene diimide dimer and dimer technology, which is applied in the field of asymmetric perylene diimide dimers, can solve the problems of poor solubility and film-forming properties, and limit the application of photovoltaic materials.

Active Publication Date: 2014-09-17
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its solubility and film-forming properties are poor, which limits its application in the field of photovoltaic materials.

Method used

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  • Five-membered heterocyclic derivative-bridged perylene diimide dipolymer and its preparation method and use in organic photovoltaic device
  • Five-membered heterocyclic derivative-bridged perylene diimide dipolymer and its preparation method and use in organic photovoltaic device
  • Five-membered heterocyclic derivative-bridged perylene diimide dipolymer and its preparation method and use in organic photovoltaic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104] Example 1. Preparation of unsymmetrically substituted 1-bromo-7 alkoxy perylene diimide (compound 4a)

[0105]

[0106] Dissolve 3,4,9,10-perylene diacid anhydride (3.82g, 10mmol, compound 1) in 100mL of pyridine, add 2-ethylhexylamine (6.46g, 50mmol), and heat at 120°C , stirred for 24 hours. After the reaction was completed, the reaction solution was poured into an aqueous solution of 1 mol / L hydrochloric acid (1 L), the precipitate was collected by filtration, and dried under heating at 60° C. to obtain product 2. The product was dissolved in 100 mL of dichloromethane without any treatment, and 20 mL of elemental bromine was added dropwise under heating and reflux conditions. After the addition was complete, heating and reflux was continued overnight. The product 3 was obtained by column with H60 silica gel.

[0107] The product 3 (773 mg, 1.0 mmol, compound 3) was dissolved in 10 mL of DMF, and methoxyethanol (384.5 mg, 5.0 mmol) and K 2 CO 3 (691.1mg, 5.0mmo...

Embodiment 2

[0111] Example 2. Preparation of asymmetrically substituted perylene diimide dimer (compound 5)

[0112]

[0113] The product 3 (773.0 mg, 1.0 mmol) was dissolved in 15 mL of DMF, n-butanol (370.6 mg, 5 mmol) and K 2 CO 3 (691.1mg, 5mmol), stirred and reacted for 1 hour under heating at 80°C. After the reaction was completed, the reaction solution was poured into 50 mL of water, the precipitate was collected by filtration, the calcium precipitate was dissolved in a mixed solvent of 50 mL of dichloromethane and 50 mL of water, the dichloromethane layer was collected by liquid separation, and the dichloromethane was distilled off under reduced pressure to obtain purple A black solid was passed through a column with H60 silica gel to obtain the product 4b.

[0114] The characterization data of this product are as follows:

[0115] 1 H-NMR (400MHz, CDCl 3 )δppm:9.47(d,J=8.00Hz,1H),9.34(d,J=8.00Hz,1H),8.79(s,1H),8.58(d,J=8.00Hz,1H),8.50(d, J=8.00Hz,1H),8.39(s,1H),4.46(m,2H...

Embodiment 3

[0119] Example 3. Preparation of asymmetrically substituted perylene diimide dimer (compound 6a)

[0120]

[0121] The product 4a (844.6 mg, 1.1 mmol) was dissolved in 15 mL of toluene, and commercially available thiophene-2,5-di-tributyltin (332.1 mg, 0.5 mmol) and tetrakis(triphenylphosphine) palladium (34.7 mg , 0.03mmol), under the heating condition of 120°C, the reaction was stirred for 36 hours. The toluene in the reaction system was distilled off under reduced pressure to obtain a red-black solid, which was dissolved in a mixed solvent of 50 mL of dichloromethane and 50 mL of water, and the dichloromethane layer was collected by liquid separation, and dichloromethane was distilled off under reduced pressure to obtain a red-black solid. A black solid was passed through a column with H60 silica gel to obtain the product 6a.

[0122] The structural characterization data of this product are as follows:

[0123] 1 H-NMR (400MHz, CDCl 3 )δppm:9.53(d,J=8.00Hz,1.40H),9.4...

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Abstract

The invention provides a 1,1'-dialkoxy-substituted asymmetrical perylene diimide dipolymer having a novel structure, and the perylene diimide dipolymer is an electron acceptor-type organic micromolecule having solution processibility. The invention also provides a method for synthesis of the asymmetrical substituted perylene diimide dipolymer. The asymmetrical substituted perylene diimide dipolymer as a receptor and P3HT isoelectronic donor-type polymer are combined to form an organic solar cell so that high photoelectric conversion efficiency is obtained. The asymmetrical substituted perylene diimide dipolymer provides a novel direction for photovoltaic field research.

Description

technical field [0001] The invention belongs to the field of organic photovoltaic materials, and relates to a 1,1'-dialkoxy substituted asymmetric perylene diimide dimer, its preparation method and its application in the field of organic photovoltaic materials. Background technique [0002] Solar energy is a green and environmentally friendly renewable energy, and its transformation and application is one of the important strategic ways to solve the energy crisis. Compared with the high photoelectric conversion efficiency (20-30%) of silicon-based and inorganic semiconductor photovoltaic materials, the conversion efficiency of polymer photovoltaic materials is still low, only about 6-8%. [0003] Traditional polymer photovoltaic materials use poly(3-hexyl-thiophene) (referred to as P3HT, formula a) as the electron donor material, fullerene derivatives ([6,6]-phenyl-C61-butyric acid methyl ester, referred to as PC61BM or PC60BM and [6,6]-phenyl-C71-butyric acid methyl ester,...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07D471/06H01L51/46H01L51/48C07D495/14C07D495/04
CPCY02E10/549C07D471/06C07D519/00H10K85/649H10K85/655H10K85/6576H10K85/6572
Inventor 姚建年詹传郎陆振欢张昕
Owner INST OF CHEM CHINESE ACAD OF SCI
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