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A derivative of tetraphenyl silicon and dibenzothiophene and its preparation method

A technology of dibenzothiophene and tetraphenylsilicon, which is applied in the field of organic electroluminescent display, can solve the problems of rare hole transport materials, achieve improved electron injection/transport capabilities, good thermal stability, and reduce molecular weight. Effects of agglomeration and interaction between

Active Publication Date: 2018-03-13
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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  • A derivative of tetraphenyl silicon and dibenzothiophene and its preparation method
  • A derivative of tetraphenyl silicon and dibenzothiophene and its preparation method
  • A derivative of tetraphenyl silicon and dibenzothiophene and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1, a derivative of tetraphenylsilicon and dibenzothiophene, the derivative has the following structure:

[0026] , 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:

[0027]

[0028] Above-mentioned derivative adopts following steps to prepare:

[0029]

[0030] Wherein the preparation of compound I:

[0031]

[0032] Under the protection of argon, add 14.87g of 1,4-dibromobiphenyl and 210 mL of tetrahydrofuran to the three-necked flask successively, cool to -78 °C, add 26.25 mL of n-butyllithium dropwise, after the addition is complete, stir at -78 °C After 1 hour, 7.59 g of dichlorodiphenylsilane was slowly added dropwise. After the dropwise addition, the temperature was automatically raised after 1 hour of heat preservation reaction, and the reaction was carried out overnight. Add water to quench the reaction, distill off the solvent, ...

Embodiment 2

[0056] Example 2, a derivative of tetraphenylsilicon and dibenzothiophene. In this example, R is ethyl, and the structure of the derivative is as follows:

[0057]

[0058] The preparation method of above-mentioned derivative is as follows:

[0059]

[0060] 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 H NMR (400 MHz, CDCl 3 ) δ= 8.69 (dd, J = 4.5, 1.6 Hz, 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).

[0061] Melting point: 291°C, glass transition temperature: 118°C, decomposition temperature: 435°C

[0062] Absorption spectrum: λmax=282nm

[0063] Fluorescence spectrum: λmax=37...

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Abstract

The invention discloses a derivative of tetraphenylsilicon and dibenzothiophene. The derivative has the following structure: a mixture of dibenzothiophene tetraphenylsilicon bromide with an alkoxy group and pyridine-4 ‑Boronic acid, with the ratio of 1mol: 1.0~3.3mol, dissolved in the organic solvent of toluene and ethanol or THF and water, under the catalysis of polymer support Pd catalyst and PSQ type silicon-based cocatalyst, at 50~100 Under the condition of ℃, react for 5~10h to get derivatives of tetraphenyl silicon and dibenzothiophene. The invention has the characteristics of excellent thermal stability, high quantum efficiency, relatively high triplet energy level, simple 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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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/10H01L51/54
CPCC07F7/0812H10K85/40
Inventor 郭艳云鲍斌史永文王作鹏
Owner 山东盛华新材料科技股份有限公司