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Organic semiconductor material containing carbazole, preparation method thereof, and organic electroluminescent device

An organic semiconductor and carbazole technology, which is applied in the field of organic electroluminescent devices, can solve the problems of lack of blue light materials and affect the life development of white light devices, etc., and achieve simple process, good hole transport ability and luminous efficiency, and simple preparation method Effect

Inactive Publication Date: 2014-05-07
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is a lack of thermally stable blue light materials, which affects the life and development of white light devices

Method used

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  • Organic semiconductor material containing carbazole, preparation method thereof, and organic electroluminescent device
  • Organic semiconductor material containing carbazole, preparation method thereof, and organic electroluminescent device
  • Organic semiconductor material containing carbazole, preparation method thereof, and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] A carbazole-containing organic semiconductor material, namely 2-(4-(9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole (named CzPPI), which is the compound P1 shown in the following structural formula:

[0042]

[0043] The preparation method of the above-mentioned carbazole-containing organic semiconductor material compound P1 comprises the following steps:

[0044] (1) Provide compound A (2-(4-bromophenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole) and compound B1 (carbazole) represented by the following structural formula respectively,

[0045]

[0046] (2) Under nitrogen protection, add 2-(4-bromophenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole 3mmol, carbazole 3.0mmol, toluene 25mL, and add Pd( OAc) 2 0.09mmol, t-BuONa 5.4mmol, (t-Bu) 3 PHBF 4 0.27mmol, reflux and stir at 110°C for coupling reaction for 20h. After the reaction, cool down, pour the reaction solution into a saturated ammonium chloride aqueous solution, extract three times...

Embodiment 2

[0050] A carbazole-containing organic semiconductor material, namely 2-(4-(3,6-methyl-9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthrene[9,10 -d] imidazole (named MCzPPI), which is the compound P2 shown in the following structural formula:

[0051]

[0052] The preparation method of the above-mentioned carbazole-containing organic semiconductor material compound P2 comprises the following steps:

[0053] (1) Compound A (2-(4-bromophenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole) and compound B2 (3,6-dimethyl base carbazole),

[0054]

[0055] (2) Under nitrogen protection, add 2-(4-bromophenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole 3mmol, 3,6-dimethylcarbazole 3.5mmol, di Add 0.03mmol of CuI to 25mL of toluene under stirring, add 0.09mmol of o-phenanthroline and CuI for co-catalysis, 18.0mmol of KOH, and reflux and stir the coupling reaction at 130°C for 40h. After the reaction, cool down, pour the reaction solution into dilute hydrochloric acid solution, extract ...

Embodiment 3

[0058] A carbazole-containing organic semiconductor material, namely 2-(4-(3,6-ethyl-9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthrene[9,10 -d] imidazole (named ECzPPI), which is the compound P3 shown in the following structural formula:

[0059]

[0060] The preparation method of the above-mentioned carbazole-containing organic semiconductor material (i.e. compound P3) comprises the following steps:

[0061] (1) Compound A (2-(4-bromophenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole) and compound B3 (3,6-diethyl base carbazole),

[0062]

[0063] (2) Add 4.0mmol of 2-(4-bromophenyl)-1-phenyl-1H-phenanthrene[9,10-d]imidazole and 6.0mmol of 3,6-diethylcarbazole sequentially under argon protection , o-dichlorobenzene 25mL, add Cu powder 6mmol under stirring, add 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) 1.0mmol as a phase transfer catalyst, K 2 CO 3 27.0 mmol was refluxed and stirred at 185° C. for 48 h for the coupling reaction. After the reaction, pass thr...

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Abstract

The invention provides an organic semiconductor material containing carbazole, a preparation method thereof, and an organic electroluminescent device. The organic semiconductor material containing carbazole is represented in the description as a compound P, wherein in the structure formula, the R represents an H atom or a C1-C4 alkyl group. The compound P is prepared through a Suzuki coupling reaction. The organic semiconductor material containing carbazole contains 1,2-diphenyl-1H-phenanthro[9,10-d]imidazole groups and carbazole groups, these groups all have a very good hole transport property and high thermostability, and thus the service life of luminescent device is prolonged.

Description

technical field [0001] The invention relates to the field of photoelectric materials, in particular to a carbazole-containing organic semiconductor material, a preparation method thereof, and an organic electroluminescent device. Background technique [0002] With the development of the information age, high-efficiency, energy-saving, lightweight organic electroluminescent flat panel displays (OLEDs) 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, lightness, thinness, good contrast, low energy consumption, and flexible devices have put forward higher requirements for organic semiconductor materials. [0003] In 1987, Tang and Van Slyke of Eastman Kodak Company in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C09K11/06H01L51/54
CPCC09K11/06C07D403/10C09K2211/1044H10K85/6572
Inventor 周明杰王平梁禄生张娟娟
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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