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N-type organic semiconductor material as well as preparation method and application thereof

An organic semiconductor, n-type technology, applied in the field of n-type organic semiconductor materials and their preparation, can solve problems such as poor light absorption ability, difficulty in regulating physical and chemical properties due to fixed structure, and limited practical application prospects of fullerene acceptor materials.

Active Publication Date: 2019-03-26
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the intrinsic properties of fullerene materials themselves determine their limitations
For example, it is difficult to control its physical and chemical properties due to fixed structure, poor ability to absorb light and poor photothermal stability, etc.
These limit the practical application prospects of fullerene acceptor materials

Method used

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  • N-type organic semiconductor material as well as preparation method and application thereof
  • N-type organic semiconductor material as well as preparation method and application thereof
  • N-type organic semiconductor material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0165] This embodiment prepares the brominated monomer (compound 4) of the n-type organic semiconductor material having the structure shown in formula II through the following steps:

[0166] Step (1): Synthesis of Compound 2

[0167]

[0168] Compound 1 (1.03 g, 2.0 mmol) was dissolved in 20 mL of chloroform. Then add 320 mg of liquid bromine and 10 mg of ferric chloride. The reaction was carried out in the dark at room temperature overnight. After the reaction is complete, add sodium sulfite aqueous solution, stir vigorously for 30 minutes, extract, dry, and spin out the solvent to obtain the initial product, which is further purified by silica gel chromatography to obtain a white solid product 2 with a mass of 450 mg (yield 38%), nuclear magnetic resonance Hydrogen spectrum such as Figure 1A As shown, the carbon NMR spectrum is as Figure 1B shown.

[0169] 1 H NMR (400MHz, CDCl 3 )δ:7.74-7.73(d,1H),7.70(s,1H),7.28-7.27(d,1H),4.23-4.22(d,2H),1.90(s,1H),1.36-1.25(m...

Embodiment 2

[0179] This embodiment prepares the brominated monomer (compound 6) of the n-type organic semiconductor material having the structure shown in formula III through the following steps:

[0180] Synthesis of compound 6

[0181]

[0182] Compound 5 (130 mg, 0.129 mmol) was dissolved in 20 mL of chloroform. Add 44 mg of liquid bromine and 2 mg of ferric chloride. The reaction mixture was reacted for 12 hours in the dark. After the reaction was complete, an aqueous solution of sodium sulfite was added and stirred for 30 minutes. Extraction, drying and further purification by silica gel chromatography column to obtain yellow solid product 6, the quality is 130mg, the yield is 87%, and the hydrogen nuclear magnetic resonance spectrum is as follows: Figure 4A As shown, the carbon NMR spectrum is as Figure 4B shown.

[0183] 1 H NMR (400MHz, CDCl 3 )δ:7.80(s,2H),4.32-4.30(d,4H),1.96(s,2H),1.40-1.25(m,64H),0.90-0.86(m,12H). 13 C NMR (100MHz, CDCl 3 )δ:160.69,160.05,139.94,...

Embodiment 3

[0185] This embodiment prepares the brominated monomer (compound 8) of the n-type organic semiconductor material having the structure shown in formula IV through the following steps:

[0186]

[0187] Compound 7 (149 mg, 0.1 mmol) was dissolved in 20 mL of chloroform. Add 35 mg of liquid bromine and 2 mg of ferric chloride. The reaction mixture was reacted for 12 hours in the dark. After the reaction was complete, an aqueous solution of sodium sulfite was added and stirred for 30 minutes. Extraction, drying and further purification by silica gel chromatography until the yellow solid product 8, 153 mg, yield 92%, H NMR spectrum as Figure 5 shown.

[0188] 1 H NMR (400MHz, CDCl 3 )δ:7.53(s,2H),4.37-4.35(d,2H),4.31-4.29(d,4H),2.12(s,1),2.0(s,2H),1.40-1.27(m,96H) ,0.89-0.86(m,18H).

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Abstract

The invention provides an n-type organic semiconductor material as well as a preparation method and application thereof. The n-type organic semiconductor material has structures represented by formulae I-VII (shown in the description). The n-type organic semiconductor material prepared by virtue of the preparation method has very high electronic transmission performance, excellent dissolubility, high skeleton planarity, good crystallinity and adjustable and controllable photoelectric property, can be taken as an acceptor material for a solar cell, can be taken as an electronic transmission material in an n-type field effect transistor and has huge utilization potentiality and values in the organic semiconductor materials.

Description

technical field [0001] The invention belongs to the field of semiconductors, and relates to an n-type organic semiconductor material and its preparation method and application. Background technique [0002] At present, polymer semiconductors with π-conjugated structures have attracted great attention both in the field of basic scientific research and in the field of practical application in industry. It has great application potential in various electronic components, such as organic thin film transistors and polymer solar cells. [0003] In recent years, a large number of hole transport materials have been used in field effect transistor devices, and their performance has been improved to a level comparable to that of inorganic materials. In terms of solar energy, p-type materials are widely used in the research of donor materials. However, the development of n-type organic semiconductor materials lags behind that of p-type materials, and usually exhibits poor electrical ...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/30H01L51/46
CPCC08G61/121C08G61/126C08G2261/124C08G2261/1412C08G2261/3246C08G2261/37C08G2261/354C08G2261/91H10K85/151H10K85/113Y02E10/549
Inventor 郭旭岗王英锋闫政龙郭晗凌少华
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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