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N-type organic semiconductor material based on boron and nitrogen coordinate bond as well as preparation method and application of n-type organic semiconductor material

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

Active Publication Date: 2019-10-15
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 and nitrogen coordinate bond as well as preparation method and application of n-type organic semiconductor material
  • N-type organic semiconductor material based on boron and nitrogen coordinate bond as well as preparation method and application of n-type organic semiconductor material
  • N-type organic semiconductor material based on boron and nitrogen coordinate bond as well as preparation method and application of n-type organic semiconductor material

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Experimental program
Comparison scheme
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 and nitrogen coordinate bond as well as a preparation method and application of the n-type organic semiconductor material, belongs to the technical field of n-type organic semiconductor materials, and solves the technical problems of lagged development, fewer types and quantities and low migration rate of the n-typeorganic semiconductor material compared with a p-type organic semiconductor material in the prior art. The chemical structural formula of the n-type organic semiconductor material is shown as a formula (I), a formula (II), a formula (III) or a formula (IV) as shown in the specification, wherein n and m respectively express integers between 0 to 20, and X is O or S. The organic semiconductor material has relatively low LUMO / HOMO energy level and electronic transmission capability within the range of -3.65 eV and -4.58 eV, and is suitable for being used for preparing an organic field effect transistor device with high migration rate as a charge transmission 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 Applications(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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