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Organic semiconductor material containing dibenzothiophene sulfone, preparation method of organic semiconductor material and organic electroluminescent device

An organic semiconductor, benzothiophene sulfone technology, applied in the field of organic electroluminescent materials, can solve the problems of less electroluminescent blue light, high mobility, lack of high thermal stability, etc., achieve easy control, improved electron transport performance, excellent thermal stability The effect of stability

Active Publication Date: 2013-09-11
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 efficient and stable electroluminescent blue light and white light devices, and blue light materials with high mobility and high thermal stability are still relatively lacking.

Method used

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  • Organic semiconductor material containing dibenzothiophene sulfone, preparation method of organic semiconductor material and organic electroluminescent device
  • Organic semiconductor material containing dibenzothiophene sulfone, preparation method of organic semiconductor material and organic electroluminescent device
  • Organic semiconductor material containing dibenzothiophene sulfone, preparation method of organic semiconductor material and organic electroluminescent device

Examples

Experimental program
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Effect test

Embodiment 1

[0028] This embodiment discloses a dibenzothiophene sulfone-containing organic semiconductor material with the following structure, namely 2,7-bis(3-(carbazol-9-yl)phenyl)dibenzothiophene sulfone (DCzFSO):

[0029]

[0030] Step 1, the preparation of 2,7-dibromodibenzothiophene sulfone:

[0031]

[0032] Dissolve 4 mmol of dibenzothiophene sulfone in 30 ml of concentrated H 2 SO 4 In, add 8.2mmol NBS at room temperature, stir. After 24 hours, the reaction solution was poured into water, filtered with suction, washed with water and methanol. The remaining solid was recrystallized from chlorobenzene to give 2,7-dibromodibenzothiophene sulfone as a colorless needle solid. Yield: 49%. MS: m / z 374 (M + ).

[0033] Step 2, the preparation of 2,7-bis(3-(carbazol-9-yl)phenyl)dibenzothiophene sulfone (DCzFSO):

[0034]

[0035] Add 3 mmol of 2,7-dibromodibenzothiophene sulfone, 6.3 mmol of 3-(carbazol-9-yl)phenylboronic acid, and 0.27 mmol of tetrakistriphenylphosphine ...

Embodiment 2

[0037] This embodiment discloses a dibenzothiophene sulfone-containing organic semiconductor material with the following structure, that is, 2,7-bis(3-(3,6-di-tert-butylcarbazol-9-yl)phenyl)dibenzothiophene sulfone (Dt-BuCzFSO):

[0038]

[0039] Step 1: same as step 1 of embodiment 1;

[0040] Step 2: Preparation of 2,7-bis(3-(3,6-di-tert-butylcarbazol-9-yl)phenyl)dibenzothiophene sulfone (Dt-BuCzFSO):

[0041]

[0042] 2,7-dibromodibenzothiophene sulfone sulfone 3mmol, 3-(3,6-di-tert-butylcarbazol-9-yl)phenylboronic acid 9.0mmol, tris(dibenzylideneacetone)dipalladium 0.03mmol Add it into the reaction bottle, vacuumize and circulate nitrogen for 3 times, make the reaction system in anaerobic state, under the protection of nitrogen, add 50mL of toluene solution, 2mol / L K 2 CO 3 45ml of aqueous solution, the mixture was heated to 115°C and refluxed for Suzuki coupling reaction for 30h. After the reaction, the reaction solution was poured into saturated ammonium chlori...

Embodiment 3

[0044] This embodiment discloses a dibenzothiophene sulfone-containing organic semiconductor material with the following structure, that is, 2,7-bis(3-(3,6-di-n-hexylcarbazol-9-yl)phenyl)dibenzothiophene sulfone ( DHCzFSO):

[0045]

[0046] Step 1: same as step 1 of embodiment 1;

[0047] Step 2: Preparation of 2,7-bis(3-(3,6-di-n-hexylcarbazol-9-yl)phenyl)dibenzothiophene sulfone (DHCzFSO):

[0048]

[0049] 2,7-dibromodibenzothiophene sulfone sulfone 3mmol, 3-(3,6-di-n-hexylcarbazol-9-yl)phenyl borate 6.4mmol, bis(triphenylphosphine)palladium dichloride 0.003mmol was added to the reaction flask, and after evacuation and nitrogen circulation for 3 times, the reaction system was in an anaerobic state. Under the protection of nitrogen, 55mL of ethylene glycol dimethyl ether solution and 2mol / L Li 2 CO 3 45ml of aqueous solution, the mixture was heated to 100°C and refluxed for Suzuki coupling reaction for 20h. After the reaction, the reaction solution was poured into s...

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Abstract

The invention belongs to the field of organic electroluminescent materials and discloses an organic semiconductor material containing dibenzothiophene sulfone, a preparation method of the organic semiconductor material and an organic electroluminescent device. The organic semiconductor material has a general formula shown in a drawing, wherein R is a hydrogen atom or C1-C8 alkyl. The organic semiconductor material containing dibenzothiophene sulfone, disclosed by the invention, has excellent thermal stability and has good solubility and film forming property, and shown by spectrum tests, the maximum light emission wavelength of the material is located in a blue light range; meanwhile, due to the existence of carbazole and dibenzothiophene sulfone in the structure of the material, the material has bipolar transmission performance.

Description

technical field [0001] The invention relates to an organic electroluminescence material, in particular to an organic semiconductor material containing dibenzothiophene sulfone and a preparation method thereof. The invention also relates to an organic electroluminescent device using the dibenzothiophene sulfone-containing organic semiconductor material as a light-emitting layer. 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 con...

Claims

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Application Information

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IPC IPC(8): C07D409/14C09K11/06H01L51/54
Inventor 周明杰王平梁禄生钟铁涛
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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