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Organic small molecule semiconductor materials, their synthesis methods and applications

A small molecule and semiconductor technology, applied in the field of linear oligothiophene organic small molecule semiconductor materials, can solve the problems of high price, slow development of electronic materials, complex synthesis and purification process, etc., and achieve easy preparation, simple synthesis and purification process, low cost effect

Active Publication Date: 2018-12-25
SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the development of electron-accepting materials is relatively slow, and the most commonly used in organic photovoltaic devices are fullerene derivatives
The absorption of fullerene derivatives in the visible light range is very weak, and its synthesis and purification process is relatively complicated, which makes its price very high, which increases the cost of organic photovoltaic devices

Method used

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  • Organic small molecule semiconductor materials, their synthesis methods and applications
  • Organic small molecule semiconductor materials, their synthesis methods and applications
  • Organic small molecule semiconductor materials, their synthesis methods and applications

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preparation example Construction

[0039] Another aspect of the present invention provides a method for synthesizing an organic small-molecule semiconductor material, comprising: providing a first compound comprising a diaromatic pentadiene-like π-conjugated unit and a second compound comprising an aromatic group, The organic small molecule semiconductor material is obtained through transition metal catalyzed condensation reaction.

[0040] Wherein, the first compound may have the following structural formula:

[0041]

[0042] Wherein, the second compound may have the following structural formula:

[0043]

[0044] Among them, X 1 、X 2 independently selected from O, S or Se, X 3 Selected from O, S, Se, NR 2 , C(R 2 ) 2 or Si(R 2 ) 2 , X 4 、X 5 independently selected from halogen atoms, Sn(R 4 ) 3 , BO(R 5 ) 2 Or a 5-7 membered ring substituted or unsubstituted boron ester containing -O-B-O-, and only one of X4 and X5 is a halogen atom, R 1It is selected from a straight chain or branched ch...

Embodiment 1

[0062] Embodiment 1 refers to figure 1 , the synthesis and preparation process of the organic small molecule semiconductor material can be:

[0063] Add raw material A (2.51g, 7.77mmol) into a 100ml single-necked round bottom flask, add pinacol diboronate (3.9g) and [1,1'-bis(diphenylphosphino)ferrocene] under nitrogen atmosphere Palladium dichloride (570mg), potassium acetate (2.28g), ethylene glycol dimethyl ether (55ml). Stir the reaction at 70° C. for 10-15 hours, wash with water after the reaction, separate the liquids, and combine the organic phases. The organic phase was dried over anhydrous sodium sulfate, and the organic solution was removed by rotary evaporation. The crude product was recrystallized from methanol to obtain the final product B (2.11 g), with a yield of 75%.

[0064] The characterization data for this product B are as follows: 1 H NMR (400MHz, CDCl 3 )δ=7.76(s,1H),7.66(s,1H),2.90–2.78(m,2H),1.56(dd,J=14.7,7.1Hz,2H),1.34(s,13H),1.32–1.27 (m, 6H), ...

Embodiment 2

[0065] Embodiment 2 refers to figure 2 , the synthesis and preparation process of the organic small molecule semiconductor material can be:

[0066] Add raw material B (50mg, 135μmol), raw material C (30mg, 54μmol) into a 25ml single-necked round bottom flask, tris(dibenzylideneacetone) dipalladium (7mg, 6.75μmol), tri-tert-butylphosphine tetrafluoroborate (3.9 mg, 13.5μmol) was added to the reactor under nitrogen protection, and fully degassed tetrahydrofuran (3ml) was added to the reactor, stirred to dissolve the raw material and catalyst, sodium carbonate solution (0.81ml, 1mol / L) was dropped into the reaction solution, and stirred After about 2 hours, after the reaction was completed, it was washed with water, separated, and the organic phases were combined. The organic phase was dried over anhydrous sodium sulfate, the organic solution was removed by rotary evaporation, and purified by thin-plate chromatography to obtain the final product D (47.9 mg) with a yield of 74%...

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Abstract

Disclosed are an organic small molecular semiconductor material, and a synthetic method therefor. The semiconductor material comprises a diaromatic ring pentalene π-conjugate unit and an aromatic group, and has the following structural formula (I), wherein X1 and X2 are independently selected from O, S or Se; X3 is selected from O, S, Se, NR2, C(R2)2 or Si(R2)2; R2 is selected from a linear or branched alkyl group comprising 1-20 carbon atoms, and a linear or branched modified alkaryl or heterocyclic aryl comprising 7-20 carbon atoms; R1 is selected from a hydrogen atom, a linear or branched alkyl group comprising 1-20 carbon atoms, and a linear or branched modified alkaryl or heterocyclic aryl comprising 7-20 carbon atoms; and A is an electron-withdrawing unit. The semiconductor material can be synthesised by a transition metal catalysed condensation reaction. The semiconductor material of the present invention has a small spectrum band gap, a long spectrum absorption wavelength, a relatively low highest occupied molecular orbital and lowest unoccupied molecular orbital energy level, and can be used as a photoelectric material, especially as a receptor material in an organic photovoltaic device, and it also has advantages such as a simple preparation process, a low cost, etc.

Description

technical field [0001] The invention particularly relates to a linear oligothiophene organic small molecule semiconductor material, its preparation method and application, such as application in photosensitive devices. Background technique [0002] Organic semiconductor materials have the advantages of light weight, low production cost, and easy large-scale production, making the design and synthesis of organic semiconductor materials an important technology in the field of organic electronics. The flexibility of organic semiconductor materials greatly reduces their production and transportation costs. Lay the foundation for personalized electronics. [0003] Organic semiconductor materials can be divided into electron-donating materials and electron-accepting materials according to their use in organic electronics. Among them, electron-donating materials have developed very rapidly in recent years, and many high-performance organic electron-donor semiconductor materials ha...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04C07D495/14C07F7/10C08G61/12C08L65/00H01L51/46
CPCC07D495/04C07D495/14C07F7/10C08G61/12C08L65/00
Inventor 武建昌马玉超王立磊马昌期
Owner SUZHOU INST OF NANO TECH & NANO BIONICS CHINESE ACEDEMY OF SCI
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