Novel n-type quinoid-structure small molecule and application thereof in organic photoelectric devices

A small molecule, n-type technology, applied to a new n-type quinoid structure small molecule and its application in organic optoelectronic devices, can solve the problems of insufficient absorption spectrum and low absorption coefficient, etc., to improve the absorption coefficient and electrons. Mobility, photocurrent enhancement, and effects of cell device efficiency

Active Publication Date: 2018-03-13
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The main reason is that the absorption coefficient of the existing receptors is not high and the absorption spectrum is not wide enough.

Method used

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  • Novel n-type quinoid-structure small molecule and application thereof in organic photoelectric devices
  • Novel n-type quinoid-structure small molecule and application thereof in organic photoelectric devices
  • Novel n-type quinoid-structure small molecule and application thereof in organic photoelectric devices

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A representative synthetic route is as follows:

[0037]

[0038]

[0039] (1) Dibromonaphthalimide was synthesized according to the method disclosed in the literature [Journal of Materials Chemistry C, 2015, 3(34):8904-8915.].

[0040] Put 1.8g of dibromonaphthalimide, 210mg of pyromellitidine hydrochloride, and 200mg of potassium acetate in a 100ml two-necked bottle, react at 85°C for 36 hours under nitrogen protection, and add deionized water to quench the reaction. The product was extracted with dichloromethane and purified by column chromatography to obtain 1.2 g of product A with a yield of 75%.

[0041] Take 313mg of the product A obtained in the previous step, add 50mg of orthodiphenol, 33mg of potassium carbonate and react at 85°C for 12 hours under the protection of nitrogen, cool to room temperature, add 1g of lead dioxide to the reaction mixture, and overnight at 85°C. After cooling and filtering, the product was purified by column chromatography to o...

Embodiment 2

[0046] The quinone structure small molecules S1, S2, and S3 synthesized in Example 1 are used as electron acceptors in organic photovoltaic devices (ITO cathode / cathode interface layer / active layer / anode-machine interface layer / anode).

[0047] Pre-cut the ITO conductive glass with a square resistance of 20 ohms / cm2 into 15mm×15mm square pieces. Use acetone, special detergent for micron-sized semiconductors, deionized water, and isopropanol to clean ultrasonically in sequence, blow nitrogen whistle, and place in a constant temperature oven for later use. Spin-coat a layer of PFN-Br with a thickness of 5nm on ITO, and then spin-coat the active layer materials PTB7-Th / S1, PTB7-Th / S2,

[0048] PTB7-Th / S3 with a thickness of 110nm and finally evaporated MoO 3 and Al electrodes. All preparations were carried out in a glove box under a nitrogen atmosphere. The current-voltage curves of the fabricated flip-chip devices are as follows: image 3 The relevant data are listed in Tabl...

Embodiment 3

[0050] The quinone structure small molecules S1, S2, and S3 synthesized in Example 1 are used as electron acceptors in organic photovoltaic devices (ITO anode / anode interface layer / active layer / cathode interface layer / cathode).

[0051] Pre-cut the ITO conductive glass with a square resistance of 20 ohms / cm2 into 15mm×15mm square pieces. Use acetone, special detergent for micron-sized semiconductors, deionized water, and isopropanol to clean ultrasonically in sequence, blow nitrogen whistle, and place in a constant temperature oven for later use. Spin-coat a layer of PEDOT:PSS with a thickness of 20 nm on the ITO, and then spin-coat the active layer materials PTB7-Th / S1, PTB7-Th / S2, and PTB7-Th / S3 with a thickness of 100 nm. Then spin-coat a layer of PFN-Br with a thickness of 5nm, and finally evaporate Al electrodes. All preparations were carried out in a glove box under a nitrogen atmosphere. The current-voltage curves of the prepared positive battery devices are as follow...

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Abstract

The invention relates to a novel n-type quinoid-structure small molecule and application thereof in organic photoelectric devices. The novel n-type quinoid-structure small molecule is composed of three parts, namely naphthalimide, a pyromellitic tetramine group that may form quinoid structure and terminal benzoheterocycle; the novel n-type quinoid-structure small molecule that is a conjugated small molecule has high absorption coefficient and electron migration rate and may serve as an efficient electron receptor in efficient organic photovoltaic devices. The quinoid small molecule is designedherein, absorption coefficient of a polymer can be greatly increased, photoelectric current and battery device efficiency of a battery device are greatly increased; the novel quinoid small molecule may act as the electron receptor to arrive at balance among short circuit current, open circuit voltage and filling factor, an organic photovoltaic device with energy conversion efficiency of higher than 10% can be prepared, and the organic photovoltaic device is far beyond existing naphthalimide batteries in terms of performance.

Description

technical field [0001] The invention relates to the field of organic photoelectric materials, in particular to a novel n-type quinone structure small molecule and its application in organic photoelectric devices. Background technique [0002] With the increasing global demand for energy, the depletion of traditional energy sources such as oil and coal, and the need to protect the earth's ecological environment, more and more scientists around the world are focusing their research on inexhaustible hydrogen, solar energy, etc. Inexhaustible renewable clean energy. [0003] Mature photovoltaic devices based on inorganic materials such as inorganic silicon, gallium arsenide, and indium phosphide have dominated the market. However, due to their high requirements for material purity, high energy consumption and pollution will occur during processing. And its price is very expensive, so its large-scale application is limited in today's pursuit of low cost and environmental protect...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/22C07D495/22H01L51/46
CPCC07D491/22C07D495/22H10K85/657Y02E10/549
Inventor 黄飞唐浩然应磊曹镛
Owner SOUTH CHINA UNIV OF TECH
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