Substituted tetraphenyl-silicon alkoxyl dibenzothiophene based derivative, and preparation method for derivative

A technology of alkoxy dibenzothiophene and tetraphenyl silicon, which is applied in the field of organic electroluminescent display materials and preparation, can solve the problems of no contribution to electroluminescence, achieve good thermal stability, improve charge transport performance, Reduces the effects of agglomeration and interactions

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

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Problems solved by technology

So in most organic molecules, phosphorescence from radiative transitions of triplet excitons contributes little to electroluminescence

Method used

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  • Substituted tetraphenyl-silicon alkoxyl dibenzothiophene based derivative, and preparation method for derivative
  • Substituted tetraphenyl-silicon alkoxyl dibenzothiophene based derivative, and preparation method for derivative
  • Substituted tetraphenyl-silicon alkoxyl dibenzothiophene based derivative, and preparation method for derivative

Examples

Experimental program
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Embodiment 1

[0030] Example 1, a tetraphenyl silicon-substituted alkoxydibenzothiophene derivative, the structure of which is shown in Formula I:

[0031]

[0032] where R 1 =R 2 =CH 3 、C 2 h 5 、C 3 h 7 Any one of them, in this example R 1 =R 2 =CH 3 , with the following structure:

[0033]

[0034] The preparation route is as follows:

[0035] .

[0036] The preparation of intermediate II: under the protection of argon, add 74.2g of bis(4-bromophenyl)-phenylsilane and 50ml of tetrahydrofuran to the three-necked flask successively, cool to -78°C, add 225mL of n-butyllithium dropwise, After the dropwise addition was completed, stir at -78°C for 1 hour, then slowly add 124.28 g of tributyl borate dropwise, after the dropwise addition, keep warm for 1 hour, then automatically heat up and react overnight. Add 400ml of water, 400ml of concentrated hydrochloric acid, and 550ml of petroleum ether into the reaction flask, and stir for 2h. The organic layer was washed twice wit...

Embodiment 2

[0044] Example 2, a tetraphenyl silicon-substituted alkoxydibenzothiophene derivative, the structure of which is shown in Formula I:

[0045]

[0046] where R 1 =R 2 =CH 3 、C 2 h 5 、C 3 h 7 Any one of them, in this example R 1 =R 2 =C 2 h 5 , the structural formula is as follows:

[0047]

[0048] The preparation route is as follows:

[0049] .

[0050] The preparation of intermediate II: under the protection of argon, add 163.2g of bis(4-bromophenyl)-phenylsilane and 110ml of tetrahydrofuran to the three-necked flask successively, cool to -78°C, add 495mL of n-butyllithium dropwise, After the dropwise addition is completed, stir at -78°C for 1 hour, then slowly add 313.0 g of tributyl borate dropwise, after the dropwise addition is completed and keep warm for 1 hour, the temperature rises automatically, and the reaction lasts overnight. Add 880ml of water, 880ml of concentrated hydrochloric acid, and 1000ml of petroleum ether into the reaction flask, and ...

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Abstract

The invention discloses a substituted tetraphenyl-silicon alkoxyl dibenzothiophene based derivative. The derivative has a structure represented by a formula shown in the description. The derivative disclosed by the invention is a hole-transporting material in an OLED apparatus. By using tetraphenyl-silicon as a main body, dibenzothienyl groups with hole-transporting ability are connected to para-positions of tetraphenyl-silicon. In order to better adjust the HOMO energy level, alkoxy goups with electron donating ability are introduced onto the dibenzothienyl groups, so that the HOMO energy level of the material is improved, the glass transition temperature of the material is improved, and the material has a relatively high energy level in a triplet state and has excellent hole-transporting ability. The material disclosed by the invention is simple in preparation process and provides an excellent material for OLED display and illumination.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent display materials and preparation methods, and more specifically relates to derivatives of tetraphenylsilicon and alkoxydibenzothiophene and their preparation. Background technique [0002] Due to its ability to utilize triplet and singlet excitons, the internal quantum efficiency of phosphorescent organic light-emitting diodes (OLEDs) can theoretically reach 100%, which has attracted close attention from scholars and experts in the industry. [0003] Organic electroluminescent materials are divided into two categories: organic electroluminescent materials and organic electrophosphorescent materials. Fluorescence and phosphorescence are both processes of radiation transitions, and the final state of the transition is the ground state. The difference between the two lies in the transition of the former The initial state is an excited singlet state, while the latter is an excited ...

Claims

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Application Information

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IPC IPC(8): C07F7/08H01L51/54
CPCC07F7/0812H10K85/40
Inventor 史永文王作鹏郭艳云王金荣谢英张琼张文清
Owner 山东盛华新材料科技股份有限公司
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