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N-type organic semiconductor material based on boron-nitrogen coordination bond and its preparation method and application

An organic semiconductor and coordination bond technology, applied in the fields of semiconductor/solid-state device manufacturing, semiconductor devices, organic chemistry, etc., can solve the problem of difficulty in reducing the LUMO/HOMO energy level, limited n-type molecular design strategies, and low electron mobility, etc. problem, to achieve the effect of favorable charge transport, favorable mass synthesis, and high electron mobility

Active Publication Date: 2020-09-22
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the LUMO / HOMO energy levels of conjugated molecules are difficult to reduce, and the design strategies for n-type molecules are limited, resulting in significantly fewer types and quantities of n-type organic semiconductors than p-type organic semiconductors.
In addition, the electron mobility of n-type organic semiconductor materials is much lower than the hole mobility of p-type materials

Method used

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  • N-type organic semiconductor material based on boron-nitrogen coordination bond and its preparation method and application
  • N-type organic semiconductor material based on boron-nitrogen coordination bond and its preparation method and application
  • N-type organic semiconductor material based on boron-nitrogen coordination bond and its preparation method and application

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Effect test

Embodiment 1

[0068] An n-type organic semiconductor material based on a boron-nitrogen coordination bond, the structural formula is as follows:

[0069]

[0070] Preparation of the above-mentioned n-type organic semiconductor material based on the boron-nitrogen coordination bond:

[0071] Step 1. Accurately weigh 1,3,6,8-tetrabromopyrene (compound 1) (1.00g, 1.93mmol), sodium periodate (3.93g, 18.4mmol) and ruthenium trichloride hydrate into the sealed tube (40mg), then the system was vacuumed, the system was pumped and ventilated several times with argon gas, 45mL of purified acetonitrile and 10mL of primary water were added, the temperature of the system was raised to 120°C, and the reaction was carried out at high temperature and high pressure for 20h. The reaction system was cooled to room temperature, and the solvent was distilled off under reduced pressure to obtain a solid product, which was ultrasonically washed with water, methanol and chloroform in turn, and filtered with suc...

Embodiment 2

[0084] The structural formula of the n-type organic semiconductor material based on the boron-nitrogen coordination bond is as follows:

[0085]

[0086] The preparation of the above-mentioned n-type organic semiconductor material based on boron-nitrogen coordination bond: add the boranation precursor (16.0mg, 0.012mmol) to the polymerization bottle that has been baked clean, then vacuumize and pass argon to the system. Ventilate several times, add distilled toluene solvent (15mL), and add triethylamine (0.20mL, 1.42mmol) and boron trifluoride ether (0.79mL, 2.84mmol) dropwise under reflux at 120°C for 20min Continue to reflux for 6h after the dropwise addition. The reaction system was cooled to room temperature, concentrated under reduced pressure to remove the solvent, added methanol, ultrasonically settled, filtered the solid crude product obtained, and finally column chromatography (trichloromethane:n-hexane=2:1) ​​to obtain a dark green solid (i.e. based on boron Nitr...

Embodiment 3

[0089] The structural formula of the n-type organic semiconductor material based on the boron-nitrogen coordination bond is as follows:

[0090]

[0091] The preparation of the above-mentioned n-type organic semiconductor material based on boron-nitrogen coordination bonds: add the borylation precursor (11.0mg, 0.007mmol) to the polymerization bottle that has been baked clean, then vacuumize and pass argon to the system. Ventilate several times, add distilled toluene solvent (10mL), and add triethylamine (0.12mL, 0.84mmol) and boron trifluoride diethyl ether (0.46mL, 1.68mmol) dropwise under reflux at 120°C for 20min Continue to reflux for 6h after the dropwise addition. The reaction system was cooled to room temperature, concentrated under reduced pressure to remove the solvent, and the solid was added to methanol, ultrasonically settled, filtered to obtain the solid crude product, and finally column chromatography (dichloromethane:n-hexane=2:1) ​​to obtain a dark green so...

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Abstract

The invention relates to an n-type organic semiconductor material based on a boron-nitrogen coordination bond, a preparation method and application thereof, and belongs to the technical field of n-type organic semiconductor materials. Compared with p-type organic semiconductor materials in the prior art, the technical problems of lagging development of n-type organic semiconductor materials, small number of types and low mobility are solved. The n-type organic semiconductor material of the present invention has a chemical structural formula represented by formula (I), formula (II), formula (III) or formula (IV), wherein n and m are integers between 0 and 20 respectively , X is O or S. The organic semiconductor material has a lower LUMO / HOMO energy level in the range of -3.65eV to -4.58eV, has the ability to transport electrons, and is suitable for preparing high-mobility organic field effect transistor devices as a charge transport layer.

Description

technical field [0001] The invention belongs to the technical field of n-type organic semiconductor materials, and in particular relates to an n-type organic semiconductor material based on a boron-nitrogen coordination bond and its preparation method and application. Background technique [0002] Organic semiconducting materials are the basis of organic electronics and have attracted much attention due to their great application prospects in optoelectronic devices such as organic solar cells (OSCs), organic field-effect transistors (OFETs) and organic light-emitting diodes (OLEDs). The advantages of organic semiconductor materials are easy modification and tailoring of structure, adjustable performance, low cost, flexibility and solution processability of photoelectric functional devices. Therefore, the rapid development of organic semiconductors has promoted the rapid development of organic electronics. [0003] In organic solar cells and organic field effect transistors,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02H01L51/05H01L51/30
CPCC07F5/022H10K85/657H10K10/46
Inventor 刘俊窦传冬闵阳王利祥
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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