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Derivative of tetraphenyl silicane and dibenzothiophene and method for preparing derivative

A technology of dibenzothiophene and tetraphenylsilicon is applied in the field of organic electroluminescence display, which can solve the problem of rare hole transport materials, improve electron injection/transport capability, and reduce intermolecular agglomeration and interaction. , the effect of good thermal stability

Active Publication Date: 2016-03-23
山东盛华新材料科技股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a variety of newly developed hole-transport materials have been applied to electroluminescent devices, there are still few hole-transport materials that can combine high electron mobility and high stability.

Method used

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  • Derivative of tetraphenyl silicane and dibenzothiophene and method for preparing derivative
  • Derivative of tetraphenyl silicane and dibenzothiophene and method for preparing derivative
  • Derivative of tetraphenyl silicane and dibenzothiophene and method for preparing derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1, a derivative of tetraphenylsilicon and dibenzothiophene, the derivative has the following structure:

[0027] , the derivative has hole transport properties and can be used for OLED display; in this embodiment, R is methyl, and the structure of the derivative is as follows:

[0028]

[0029] Above-mentioned derivative adopts following steps to prepare:

[0030]

[0031] Wherein the preparation of compound I:

[0032]

[0033] Under the protection of argon, add 14.87g of 1,4-dibromobiphenyl and 210mL of tetrahydrofuran to the three-necked flask successively, cool to -78°C, add 26.25mL of n-butyllithium dropwise, and stir at -78°C for 1 After 1 hour, slowly add 7.59 g of dichlorodiphenylsilane dropwise. After the dropwise addition, the temperature is automatically raised after 1 hour of heat preservation reaction, and the reaction is carried out overnight. Add water to quench the reaction, distill off the solvent, add dichloromethane and water to d...

Embodiment 2

[0057] Example 2, a derivative of tetraphenylsilicon and dibenzothiophene. In this example, R is ethyl, and the structure of the derivative is as follows:

[0058]

[0059] The preparation method of above-mentioned derivative is as follows:

[0060]

[0061] Derivative VII-2 refers to the preparation process of Example 1, except that methyl iodide in the fourth step is changed to ethyl bromide. Derivative VII-2: 1 HNMR (400MHz, CDCl 3 )δ=8.69(dd,J=4.5,1.6Hz,2H,Ar-H),8.24–8.10(m,2H,Ar-H),7.89–7.73(m,7H,Ar-H),7.74–7.62 (m,6H,Ar-H),7.62–7.40(m,12H,Ar-H),3.98(m,4H,OCH 2 -H), 1.33(m,6H,Me-H); LC-MS (ESI): 683[M-H] - , element analysis measured value (calculated value) / %: C79.03 (79.01), H5.45 (5.47), N2.05 (2.03), O4.68 (4.70), S4.69 (4.70), Si4.11 (4.10).

[0062] Melting point: 291°C, glass transition temperature: 118°C, decomposition temperature: 435°C

[0063] Absorption spectrum: λmax=282nm

[0064] Fluorescence spectrum: λmax=378nm

[0065] Hole Mobility: 4.0×1...

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Abstract

The invention discloses a derivative of tetraphenyl silicane and dibenzothiophene. The derivative has a shown structure. A method for preparing the derivative of the tetraphenyl silicane and the dibenzothiophene includes dissolving pyridyl-4-boric acid and dibenzothiophene and tetraphenyl silicane phenylbromostannyl with alkoxy in organic solvents of toluene and ethanol or THF (tetrahydrofuran) and water according to a proportion of 1 mol:1.0-3.3 mol; enabling the pyridyl-4-boric acid, the dibenzothiophene and tetraphenyl silicane phenylbromostannyl with the alkoxy and the organic solvents to react with one anot her under the condition of temperatures of 50-100 DEG C under the catalytic effects of polymer carrier loading Pd catalysts and PSQ type silicon-based co-catalysts for 5-10 h to obtain the derivative of the tetraphenyl silicane and the dibenzothiophene. The derivative and the method have the advantages of excellent thermal stability, high quantum efficiency and triplet-state energy level, simplicity in preparation and the like.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence display, and in particular relates to a derivative of tetraphenyl silicon and dibenzothiophene, a preparation method and application thereof. Background technique [0002] Organic light-emitting diode (OLED) is a display technology with high quantum efficiency, high luminous efficiency, high brightness and low driving voltage, which was first developed by Deng Qingyun and others of Kodak Company in 1987 by using a multilayer film structure. OLED has become a hotspot in the research of light-emitting devices. Compared with traditional light-emitting and display technologies, OLED has the advantages of low driving voltage, small size, light weight, rich material types, etc., and it is easy to realize large-area preparation, wet preparation and preparation of flexible devices. However, organic electroluminescent devices still have many problems, such as short lifetime and low lum...

Claims

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Application Information

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IPC IPC(8): C07F7/10H01L51/54
CPCC07F7/0812H10K85/40
Inventor 郭艳云王作鹏史永文王金荣谢英李佩珊宋禹东
Owner 山东盛华新材料科技股份有限公司
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