Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Tetra-substituted perylene diimide dimer, preparation method of tetra-substituted perylene diimide dimer and use of tetra-substituted perylene diimide dimer in organic photovoltaic device

A perylene diimide dimer and dimer technology, which is applied in the fields of electric solid-state devices, semiconductor devices, semiconductor/solid-state device manufacturing, etc., can solve the problems of limiting the application of photovoltaic materials, poor solubility and film-forming properties, etc.

Inactive Publication Date: 2014-12-03
INST OF CHEM CHINESE ACAD OF SCI
View PDF4 Cites 27 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Tetra-substituted perylene diimide dimer, preparation method of tetra-substituted perylene diimide dimer and use of tetra-substituted perylene diimide dimer in organic photovoltaic device
  • Tetra-substituted perylene diimide dimer, preparation method of tetra-substituted perylene diimide dimer and use of tetra-substituted perylene diimide dimer in organic photovoltaic device
  • Tetra-substituted perylene diimide dimer, preparation method of tetra-substituted perylene diimide dimer and use of tetra-substituted perylene diimide dimer in organic photovoltaic device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0099] Example 1. Preparation of asymmetrically substituted 1,12-dialkoxy-6-bromo-perylenediimide represented by formula II (compound 3a)

[0100]

[0101] The preparation of compound 1 in this note was synthesized according to the literature (Y.G.Zhen, H.L.Qian, J.F.Xiang, J.Q.Qu, Z.H.Wang, Org.Let,., 2009, 11, 3084-3087).

[0102] Dissolve 1 (136.4 mg, 0.2 mmol) in 10 mL of DMF, add methoxyethanol (76.1 mg, 1.0 mmol) and K 2 CO 3 (140.0mg, 1.0mmol), under the heating condition of 80 ℃, stir reaction for 24 hours. After the reaction was completed, the reaction solution was poured into 50 mL of water, the precipitate was collected by filtration, 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 product 2a (83.9 mg, 0.110 mmol, yield:...

Embodiment 2

[0107] Example 2. Preparation of asymmetrically substituted 1,12-dialkoxy-6-bromo-perylenediimide represented by formula II (compound 3b)

[0108]

[0109] Dissolve 1 (136.4 mg, 0.2 mmol) in 10 mL of DMF, add methoxyethanol (74.1 mg, 1.0 mmol) and K 2 CO 3 (140.0mg, 1.0mmol), under the heating condition of 80 ℃, stir reaction for 24 hours. After the reaction was completed, the reaction solution was poured into 50 mL of water, the precipitate was collected by filtration, 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 product 2b (86.6 mg, 0.114 mmol, yield: 57%).

[0110] Dissolve 2b (75.8 mg, 0.1 mmol) in 20 mL of dichloromethane, add 1 mL of elemental bromine dropwise under heating and reflux, and continue heating to reflux overni...

Embodiment 3

[0114] Example 3, Preparation of asymmetrically substituted perylene diimide dimer (compound 4) shown in formula I

[0115]

[0116] The product 3b (921.6 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, the dichloromethane layer was collected by liquid separation, and the dichloromethane was distilled off under reduced pressure to obtain a red A black solid was passed through a H60 silica gel column to obtain product 4 (727.5 mg, 0.455 mmol, yield: 91%).

[0117] The structural characterization data of this product are as follows:

[0118] 1 H-NMR (400MHz, CDCl 3 )δ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention provides 1, 1', 12, 12'-tetra-alkoxy-substituted perylene diimide dimer having a novel structure. The dimer is an electron acceptor-type organic micromolecule of which the solution can be processed. The invention also provides a novel method for synthesis of the tetra-alkoxy-substituted perylene diimide dimer. The perylene diimide dimer as a receptor and a P3HT electron donor-type polymer are combined so that an organic solar cell is obtained. Through the perylene diimide dimer, high photoelectric conversion efficiency is obtained and a novel direction for photovoltaic field research is provided.

Description

technical field [0001] The invention belongs to the field of organic photovoltaic materials, and relates to a 1,1',12,12'-tetraalkoxy substituted 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C07D519/00C07D471/06H01L51/46H01L51/48
CPCC07D471/06C07D519/00H10K85/649H10K85/655H10K85/6576H10K85/657H10K85/6572Y02E10/549
Inventor 姚建年詹传郎张昕陆振欢
Owner INST OF CHEM CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com