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Novel heterocycle perylene imide dimer compound as well as preparation method and application thereof

A dimer perylene imide, perylene imide technology, applied in organic chemistry, semiconductor/solid-state device manufacturing, photovoltaic power generation, etc., can solve the problems of few derivative products and low yield of perylene diimide derivatives

Inactive Publication Date: 2015-11-11
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the invention, a 1,6,7,12-tetrasubstituted-perylene diimide derivative, a preparation method thereof, and a solar cell using a perylene diimide derivative as an acceptor material and a preparation method thereof, To solve the problem of low yield of perylene diimide derivatives and few derivative products

Method used

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  • Novel heterocycle perylene imide dimer compound as well as preparation method and application thereof
  • Novel heterocycle perylene imide dimer compound as well as preparation method and application thereof
  • Novel heterocycle perylene imide dimer compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] (1) Preparation of intermediate compound formula (Ⅲ-A):

[0051] Add 1,12-dichloro-peryleneimide (1g, 1.3mmol) and 60ml mass concentration of 98% concentrated sulfuric acid with a structure shown in formula (II) in a 100ml two-necked bottle, after mixing evenly, add liquid bromine (18.66g, 0.116mol), stirred and reacted at room temperature for two days, poured into 1000ml saturated aqueous sodium sulfite solution after the reaction was completed, collected the precipitate by suction filtration, washed successively with saturated aqueous sodium sulfite solution and water, dried, purified by silica gel column, dichloro Using methane / petroleum ether as a developer, the intermediate compound (III-A) (991 mg) was obtained as an orange-red solid powder with a yield of 90.1%.

[0052]

[0053] (2) Preparation of intermediate compound formula (IV-A):

[0054] In a 100ml two-necked flask, add the compound of formula (Ⅲ-A) (423mg, 0.50mmol), copper powder (<100nmparticlesize,...

Embodiment 2

[0063] (1) Preparation of intermediate compound formula (Ⅲ-A): the method is the same as in Example 1;

[0064] (2) Preparation of intermediate compound formula (IV-A): the method is the same as in Example 1;

[0065] (3) Preparation of formula (I-B) compound

[0066] Add formula (IV-A) compound (250mg, 0.16mmol), palladium acetate (80mg, 0.36mmol), three (cyclohexyl) phosphorus (70mg, 0.25mmol) and potassium tert-butoxide (200mg, 1.79mmol) in 50ml two-necked bottle mmol), then add aniline (110mg, 1.18mmol) and toluene (10ml), under argon protection, reflux for 5h, cool to room temperature, remove the solvent under reduced pressure, wash the crude product with HCl, extract with dichloromethane, and separate the organic phase , washed with brine, dried over countless sodium sulfates, purified on a silica gel column, and dichloromethane / petroleum ether was used as a developing solvent to obtain the compound (153 mg) of formula (I-B) as a red solid 6 with a yield of 60%.

[006...

Embodiment 3

[0071] (1) Preparation of intermediate compound formula (Ⅲ-A): the method is the same as in Example 1;

[0072] (2) Preparation of intermediate compound formula (IV-A): the method is the same as in Example 1;

[0073] (3) Preparation of formula (I-C) compound:

[0074] Sodium selenide (99mg, 0.79mmol) was added to the DMF solution of the compound of formula (IV-A) (400mg, 0.26mmol), reacted at 120°C for 12h under the protection of argon, cooled to room temperature, poured into water, pumped The precipitate was collected by filtration, washed with water, dried, and purified on a silica gel column using dichloromethane / petroleum ether as a developing solvent to obtain compound (121 mg) of formula (I-C) as a red solid 7 with a yield of 30%.

[0075]

[0076] Characterization data of the compound of formula (I-C): 1 HNMR (400MHz, CDCl 3 )δ=9.62(d,2H),9.46(d,2H),8.73(d,2H),8.28(d,2H),8.16(t,2H),5.22(m,4H),2.29(m,8H ),1.88(m,8H),1.27(d,48H),0.81(m,24H); 13 CNMR (100MHz, CDCl...

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PUM

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Abstract

The invention provides a novel heterocycle perylene imide dimer compound with the structure shown in a formula (I) and a preparation method thereof as well as an application of the perylene imide dimer as an electron acceptor in an organic photovoltaic material. The compound shown in the formula (I) has the advantages that the problem that molecules aggregate owing to a very large acting force among the molecules when the traditional perylene imide molecules are in a solid state is solved, and heteroatoms are introduced at four positions, namely 6, 7, 6' and 7', of perylene diimide dimer in a single bond chain, so that close packing among the molecules can be effectively prevented, the crystallinity of a material is inhibited, the amorphous form performance is improved, the open-circuit voltage and light absorption efficiency are improved, and the photoelectric conversion efficiency is high.

Description

technical field [0001] The invention belongs to the field of organic photovoltaic materials, and in particular relates to a novel heterocyclic dimerized peryleneimide compound and a preparation method thereof, and a solar cell using the dimerized peryleneimide as an acceptor material. Background technique [0002] Solar energy is the safest, greenest and most ideal renewable clean energy for human beings. Organic photovoltaic cells use organic photovoltaic materials to prepare devices to achieve photoelectric conversion, and can be made into flexible large-area devices through solution processing technology, which has the advantages of light weight, low cost, and portability. Organic photovoltaic cells are an international cutting-edge interdisciplinary research field and have broad application prospects. [0003] Organic photovoltaic materials can be divided into electron donors and electron acceptors, and fullerene derivatives are currently the most widely used and most s...

Claims

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Application Information

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IPC IPC(8): C07D519/00H01L51/46
CPCC07D519/00H10K85/657H10K85/6572Y02E10/549
Inventor 王朝晖孟东李燕姜玮
Owner INST OF CHEM CHINESE ACAD OF SCI
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