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 derivati

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

Example Embodiment

[0049] Example 1

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

[0051] Add 1,12-dichloro-perylene imide (1g, 1.3mmol) with the structure shown in formula (II) and 60ml of concentrated sulfuric acid with a mass concentration of 98% into a 100ml two-necked flask. After mixing well, add liquid bromine (18.66g, 0.116mol), the reaction was stirred at room temperature for two days. After the reaction, it was poured into 1000ml of saturated sodium sulfite aqueous solution, and the precipitate was collected by suction filtration, washed with saturated sodium sulfite aqueous solution and water, dried, purified by silica gel column, dichloride Using methane / petroleum ether as a developing agent, the intermediate compound formula (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), ...

Example Embodiment

[0062] Example 2

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

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

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

[0066] Add the compound of formula (IV-A) (250mg, 0.16mmol), palladium acetate (80mg, 0.36mmol), tris(cyclohexyl) phosphorus (70mg, 0.25mmol) and potassium tert-butoxide (200mg, 1.79) into a 50ml two-necked flask. mmol), then add aniline (110mg, 1.18mmol) and toluene (10ml), under the protection of argon, 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 with numerous sodium sulfates, purified by silica gel column, dichloromethane / petroleum ether as a developing agent, to obtain the compound of formula (I-B) (153 mg) as a red solid 6 with a yi...

Example Embodiment

[0070] Example 3

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

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

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

[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 under argon protection for 12h, after cooling to room temperature, poured into water, pumped The precipitate was collected by filtration, washed with water, dried, and purified by a silica gel column using dichloromethane / petroleum ether as a developing solvent to obtain the compound of formula (I-C) (121 mg) 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); 1...

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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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