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Imide conjugated small molecule based on multi-component aromatic ring, and preparation method thereof, and applications in organic photoelectric devices

An aromatic ring and imide technology, applied in the field of organic optoelectronic materials, can solve the problems of narrow energy level regulation range, weak absorption in the visible light region, poor morphology stability, etc., to achieve absorption and utilization, improve molar absorption coefficient, excellent The effect of device efficiency

Active Publication Date: 2020-02-21
SOUTH CHINA UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the shortcomings of fullerene derivatives such as weak light absorption in the visible light region, narrow energy level regulation range, photochemical instability, and poor shape stability make scientists have to look for acceptor materials to replace them (Acc.Chem.Res.2012 ,45,723-733)

Method used

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  • Imide conjugated small molecule based on multi-component aromatic ring, and preparation method thereof, and applications in organic photoelectric devices
  • Imide conjugated small molecule based on multi-component aromatic ring, and preparation method thereof, and applications in organic photoelectric devices
  • Imide conjugated small molecule based on multi-component aromatic ring, and preparation method thereof, and applications in organic photoelectric devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: compound 1 and compound 2 obtain compound 3 through stille coupling reaction:

[0049]

[0050] Synthesis of compound 3: Add compound 1 (4.51g, 6.02mmol), compound 2 (1.55g, 2.01mmol) and tetrakistriphenylphosphine palladium (115.92mg, 0.1mmol) in a 100ml round bottom flask, and nitrogen gas for 15 minutes , then inject 30ml toluene therein, heat to reflux reaction, react after 15 hours, take a sample, TLC detects, stop heating. The belt was cooled to room temperature, extracted with dichloromethane, concentrated, and purified by silica gel (200-300 mesh) column chromatography, the eluent was petroleum ether / dichloromethane (2:1), and black solid compound 3 (2.15g , 70%). 1 H NMR (500MHz, CDCl3) δ8.67(s, 2H), 8.19(q, J=8.2Hz, 4H), 7.30(s, 2H), 7.23(d, J=5.4Hz, 2H), 7.02(d ,J=5.4Hz,2H),4.14(ddd,J=24.2,15.3,7.5Hz,8H),2.03(s,2H),1.94(dt,J=12.9,6.5Hz,2H),1.46–1.12( m,80H),0.98–0.78(m,28H). 13 C NMR(126MHz,CDCl3)δ163.66,163.53,146.01,145.56,140.31,135.72...

Embodiment 2

[0051] Embodiment 2: compound 3 is prepared compound 4 by Vilsmeier-Haack reaction:

[0052]

[0053] Synthesis of Compound 4: Add Compound 3 (1.00g, 0.65mmol) in a 100ml round bottom flask, nitrogen gas for 15 minutes, then inject anhydrous N,N-dimethylformamide (20ml) into it, and finally Phosphorus oxychloride was added dropwise, and heated to reflux for reaction. After 16 hours of reaction, samples were taken, detected by TLC, and the heating was stopped. After the reaction solution was cooled to room temperature, ice water was added to quench the reaction, and saturated K 2 CO 3 The pH of the aqueous solution is adjusted to be neutral. It was extracted with dichloromethane, concentrated, purified by silica gel (200-300 mesh) column chromatography, and the eluent was petroleum ether / dichloromethane (1:1) to obtain compound 4 (978 mg, 95%) as a green solid. 1 HNMR (500MHz, CDCl 3 )δ9.93(s, 2H), 8.65(s, 2H), 8.23(d, J=8.2Hz, 2H), 8.15(d, J=8.1Hz, 2H), 7.68(s, 2H), 7.3...

Embodiment 3

[0054] Embodiment 3: compound 4 obtains compound 5 through oxidative ring-closing reaction:

[0055]

[0056] The synthesis of compound 5: add compound 4 (400mg, 0.25mmol) in 100ml round-bottomed flask, iodine simple substance one grain, nitrogen gas 15 minutes, inject chlorobenzene (30ml) thereinto then, heat to reflux reaction, and reaction exposes Under the irradiation of ultraviolet light (Guanghao ZF-A, 365nm), after reacting for 32 hours, samples were taken, detected by TLC, and the heating was stopped. After the reaction solution was cooled to room temperature, ice water was added to quench the reaction, extracted with dichloromethane, concentrated, and purified by silica gel (200-300 mesh) column chromatography, and the eluent was petroleum ether / dichloromethane (1:1 ) to obtain compound 5 (315 mg, 80%) as a green solid. 1 H NMR (500MHz, CDCl 3 )δ9.98(s,2H),9.90(t,J=11.1Hz,2H),9.52–9.42(m,2H),7.62(s,2H),5.47–4.43(m,8H),2.19(d ,J=0.7Hz,2H),1.77–0.13(m,106H). 13 C...

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Abstract

The invention relates to an imide conjugated small molecule based on a multi-component aromatic ring, and a preparation method thereof, and applications in organic photoelectric devices, wherein fusedring perylene diimide is taken as a central core, an electron withdrawing unit is taken as a terminal group, the fused ring perylene diimide is formed by perylene diimide and a conjugated aromatic ring unit through an oxidation ring closing reaction, and the electron withdrawing terminal groups are linked to two terminals of the central core. According to the invention, the small molecule has wide spectral absorption and high molar absorption coefficient, can be used as an electron acceptor in an organic photovoltaic device, and can obtain high-efficiency organic solar cell devices.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a class of imide conjugated small molecules based on multiple aromatic rings, its preparation method and its application in organic photoelectric devices. Background technique [0002] Energy shortage and environmental pollution are major problems facing my country's sustainable economic development. The development of new green energy technology is one of the important ways to solve the above problems, and solar power generation (photovoltaic power generation) is a leader among many green and renewable energy sources, which plays an important role in reducing pollution and carbon dioxide emissions and realizing the development of a low-carbon economy. significance. Organic / polymer solar cells have attracted widespread attention of researchers because of their outstanding advantages such as low cost, large-area devices that can be prepared by solution processing, a...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07D495/22H01L51/46
CPCC07D519/00C07D495/22H10K85/626H10K85/657H10K85/6572H10K85/6576H10K30/00Y02E10/549
Inventor 张杰李力黄飞
Owner SOUTH CHINA UNIV OF TECH
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