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A kind of gear type trimerized perylene diimide compound and its preparation method and application

A technology of trimerized perylenediimide and bromoperyleneimide is applied in the field of gear-type trimerized perylenediimide compound and its preparation, so as to improve the photoelectric conversion efficiency, the design idea is reasonable and effective, and the molecular structure is simple. Effect

Active Publication Date: 2019-02-22
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The first object of the present invention is to provide a gear-type trimeric perylene diimide compound to solve the molecular aggregation caused by the strong force between molecules of traditional perylene imide molecules in the solid state, effectively Improved device efficiency

Method used

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  • A kind of gear type trimerized perylene diimide compound and its preparation method and application
  • A kind of gear type trimerized perylene diimide compound and its preparation method and application
  • A kind of gear type trimerized perylene diimide compound and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1, the preparation of target product 1

[0048] (1) Preparation of Intermediate 1

[0049] In a sealed glass tube, add monobromoperyleneimide (compound of formula a1) (546mg, 0.702mmol), 1,3,5-benzenetriborate (compound of formula b) (100mg, 0.219mmol), tetrahydrofuran 8ml and 4ml of 2M aqueous sodium carbonate solution. The mixture was sparged with argon for 30 min. Tetrakis(triphenylphosphine)palladium (35 mg, 0.026 mmol) was then added under argon. The mixture was heated to reflux for 48h, then cooled to room temperature, 25ml of water was added, extracted with dichloromethane (2×25ml), dried over anhydrous magnesium sulfate, filtered with suction, and the solvent was removed. The crude product was purified by chromatographic column to obtain an orange solid (367mg , 80%), namely intermediate 1. The reaction equation is as follows:

[0050]

[0051] The structural confirmation data of intermediate 1 are as follows: 1 H NMR (400MHz, CDCl 3 )δ=8.67...

Embodiment 2

[0056] Embodiment 2, the preparation of target product 2

[0057] The structural formula of the target product 2 that the present embodiment makes is as follows:

[0058]

[0059] The preparation method is as follows:

[0060] 1) Using tetrahydrofuran and aqueous sodium carbonate as solvents and tetrakis(triphenylphosphine)palladium as a catalyst, heat and reflux monobromoperyleneimide (compound of formula a2) and 1,3,5-benzenetriboronate for 45 hours, intermediate 2 is obtained; wherein, the molar ratio of the monobromoperyleneimide (compound of formula a2) and 1,3,5-benzenetriboronate is 3:1;

[0061]

[0062] 2) Intermediate 2, I 2 The mixture with toluene was irradiated under a mercury lamp for 10h and then extracted with a saturated aqueous solution of sodium sulfite, then washed, dried, filtered, and purified by a chromatographic column to obtain the target product 2; wherein, intermediate 2 and I 2 The mass ratio of intermediate 2 and toluene is 1:1; the mass v...

Embodiment 3

[0063] Embodiment 3, the preparation of target product 3

[0064] The structural formula of the target product 3 that present embodiment makes is as follows:

[0065]

[0066] The preparation method is as follows:

[0067] 1) Using tetrahydrofuran and aqueous sodium carbonate as solvents and tetrakis(triphenylphosphine) palladium as a catalyst, heat monobromoperylene imide (compound of formula a3) and 1,3,5-benzenetriboronate under reflux for 50 hours, intermediate 3 is obtained; wherein, the molar ratio of the monobromoperyleneimide (compound of formula a3) and 1,3,5-benzenetriboronate is 3.5:1;

[0068]

[0069] 2) Intermediate 3, I 2 The mixture with toluene was irradiated under a mercury lamp for 15h and then extracted with a saturated aqueous solution of sodium sulfite, then washed, dried, filtered, and purified by a chromatographic column to obtain the target product 3; wherein, intermediate 3 and I 2 The mass ratio of intermediate 3 to toluene is 3:1; the mass ...

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Abstract

The invention relates to the field of organic photovoltaic materials, in particular to a gear-type trimerized perylene diimide compound and its preparation method and application. The structural formula of the gear type trimerized perylene diimide compound is shown in formula (I): wherein, R 1 Any group selected from the following: C 2‑60 Alkyl, substituted alkyl, alkoxy, substituted alkoxy, aryl, substituted aryl, alkylaryl, substituted alkylaryl, alkylhetero Aryl, substituted alkylheteroaryl, alkylheterocyclyl or substituted alkylheterocyclyl; R 1 same or different. The gear-type trimer perylene diimide compound of the invention obviously improves the photoelectric conversion efficiency, has reasonable and effective design ideas, simple molecular structure, and short synthesis steps, and is an organic solar cell material with important application prospects.

Description

technical field [0001] The invention relates to the field of organic photovoltaic materials, in particular to a gear-type trimerized perylene diimide compound and a preparation method and application thereof. 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 successful electron acceptors. However, due to the disadvantages of fullerene...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/22H01L51/44H01L51/46
CPCC07D471/22H10K85/6572H10K30/80Y02E10/549
Inventor 王朝晖孟东李燕姜玮
Owner INST OF CHEM CHINESE ACAD OF SCI
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