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Dibenzothiophene sulphone containing organic semiconductor material and preparation method thereof and organic electroluminescent device

A technology of organic semiconductor and thiophene sulfone, applied in the field of organic electroluminescent devices, can solve the problems of high mobility, lack of high thermal stability blue light materials, etc., and achieve the effects of excellent thermal stability, convenient operation and good electron transport performance

Inactive Publication Date: 2013-06-26
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are relatively few high-efficiency and stable electric devices, and blue light materials with high mobility and high thermal stability are still relatively lacking.

Method used

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  • Dibenzothiophene sulphone containing organic semiconductor material and preparation method thereof and organic electroluminescent device
  • Dibenzothiophene sulphone containing organic semiconductor material and preparation method thereof and organic electroluminescent device
  • Dibenzothiophene sulphone containing organic semiconductor material and preparation method thereof and organic electroluminescent device

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preparation example Construction

[0027] The preparation method of the above-mentioned organic semiconductor material containing dibenzothiophene sulfone, the steps are as follows:

[0028] S1, provide the following compounds:

[0029] Compound I: Compound II: or Among them, in the compound formula II, A- is a fluorine atom (-F), a cyano group (-CN) or a nitro group (-NO 2 any of );

[0030] S2. In an inert gas atmosphere (including nitrogen or argon, etc.), dissolve compounds I and II in an organic solvent containing a catalyst and an alkali solution at a molar ratio of 1:2 to 1:3, and heat to reflux at 70 to 110°C Carry out the Suzuki reaction under the condition for 20~48h, the obtained structural formula is The compound, namely ASiF; the reaction formula is as follows:

[0031]

[0032] Wherein, in step S2 of the above-mentioned preparation method, the catalyst is organic palladium (such as tetrakis(triphenylphosphine) palladium (Pd(PPh 3 ) 4 ), tris(dibenzylideneacetone)dipalladium (Pd 2 (...

Embodiment 1

[0043] This embodiment discloses a dibenzothiophene sulfone-containing organic semiconductor material with the following structural formula, namely 2,7-bis(4-((4-cyanophenyl)diphenylsilyl)phenyl)thiophene (DCNSiF)

[0044]

[0045] Preparation of 2,7-bis(4-((4-cyanophenyl)diphenylsilyl)phenyl)thiophene (DCNSiF):

[0046]

[0047]Add 3mmol of 2,7-dibromothiophene, 6.0mmol of 4-((4-cyanophenyl)diphenylsilyl)phenylboronic acid, and 0.003mmol of tetrakis(triphenylphosphine)palladium into the reaction flask, vacuumize, After circulating nitrogen for 3 times, the reaction system was in an oxygen-free state. Under the protection of nitrogen, 50 mL of tetrahydrofuran and 2 mol / L Na 2 CO 3 Aqueous solution 35ml, the mixture was heated to 70 ° C reflux Suzuki reaction 48h.

[0048] After the reaction, the reaction solution was poured into saturated ammonium chloride aqueous solution, extracted three times with dichloromethane, the organic phase was washed with sodium chloride aq...

Embodiment 2

[0052] This embodiment discloses a dibenzothiophene sulfone-containing organic semiconductor material having the following structural formula, that is, 2,7-bis(4-((4-fluorophenyl)diphenylsilyl)phenyl)thiophene (DFSiF)

[0053]

[0054] Preparation of 2,7-bis(4-((4-fluorophenyl)diphenylsilyl)phenyl)thiophene (DFSiF):

[0055]

[0056] Add 3 mmol of 2,7-dibromothiophene, 6.4 mmol of 4-((4-fluorophenyl)diphenylsilyl)phenylboronate, and 0.09 mmol of bis(triphenylphosphine)palladium dichloride to the reaction flask , after evacuating and circulating argon for 3 times, the reaction system was in an oxygen-free state. Under the protection of argon, 50 mL of ethylene glycol dimethyl ether and 2 mol / L of Cs were added. 2 CO 3 Aqueous solution 40ml, the mixture was heated to 90 ℃ reflux Suzuki reaction for 36h.

[0057] After the reaction, the reaction solution was poured into saturated ammonium chloride aqueous solution, extracted three times with dichloromethane, the organic p...

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Abstract

The invention belongs to organic semiconductor materials, and discloses a dibenzothiophene sulphone containing organic semiconductor material and a preparation method thereof and an organic electroluminescent device. The dibenzothiophene sulphone containing organic semiconductor material has the chemical structural formula as shown in the specification, wherein A- is -F, -CN or -NO2. According to the dibenzothiophene sulphone containing organic semiconductor material provided by the invention, performance of the dibenzothiophene sulphone containing organic semiconductor material is characterized by differential thermal analysis. The result shows that the material has excellent thermal stability, and meanwhile, the material has good solubility and film-forming property. Through a spectral test, the maximum light emitting wavelength of the material is in a blue light range with wider energy gap. In addition, the light emitting material has dibenzothiophene sulphone, tetra-aryl silicon radicals in the structure, so that the material has better carrier transport performance.

Description

technical field [0001] The invention relates to the field of organic semiconductor materials, in particular to an organic semiconductor material containing dibenzothiophene sulfone, a preparation method thereof, and an organic electroluminescent device. Background technique [0002] With the development of the information age, organic electroluminescent flat panel displays (OLEDs) with high efficiency, energy saving and light weight and large-area white light illumination have attracted more and more attention. OLED technology has attracted the attention of scientists around the world, and related companies and laboratories are conducting research and development of this technology. As a new type of LED technology, organic electroluminescent devices with the characteristics of active light emission, lightness, thinness, good contrast, low energy consumption, and flexible devices can put forward higher requirements for materials. [0003] In 1987, Tang and VanSlyke of Eastma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C07F7/10C09K11/06H01L51/54
Inventor 周明杰王平梁禄生张振华
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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