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Phosphoryl and/or sulfo-phosphoryl-modified N-phenyl carbazole compound, preparation method of the phosphoryl and/or sulfo-phosphoryl-modified N-phenyl carbazole compound, and organic electroluminescent device

A thiophosphoryl and phenylcarbazole technology, applied in the field of N-phenylcarbazole compounds and organic electroluminescence devices, can solve the problems of affecting the luminous efficiency of the luminescent center, and achieve enhanced electron injection/transport performance, The effect of simplified structure and high device performance

Active Publication Date: 2013-03-20
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

But the quaternary ammonium salt polar group will affect the luminescence efficiency of the luminescent center

Method used

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  • Phosphoryl and/or sulfo-phosphoryl-modified N-phenyl carbazole compound, preparation method of the phosphoryl and/or sulfo-phosphoryl-modified N-phenyl carbazole compound, and organic electroluminescent device
  • Phosphoryl and/or sulfo-phosphoryl-modified N-phenyl carbazole compound, preparation method of the phosphoryl and/or sulfo-phosphoryl-modified N-phenyl carbazole compound, and organic electroluminescent device
  • Phosphoryl and/or sulfo-phosphoryl-modified N-phenyl carbazole compound, preparation method of the phosphoryl and/or sulfo-phosphoryl-modified N-phenyl carbazole compound, and organic electroluminescent device

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preparation example Construction

[0068] The invention discloses a preparation method of phosphoryl and / or thiophosphoryl modified N-phenylcarbazole compounds, which comprises the following steps:

[0069]The compound is reacted by Suzuki-Miyaura through two intermediates of formula (II) and formula (III) to obtain phosphoryl and / or thiophosphoryl modified N-phenyl as shown in formula (I) Carbazole compounds;

[0070]

[0071]

[0072] Among them, the central core, X, Y, R in formula (II) and formula (III) 1 , R 2 , R 3 , R 4 , R 5 , n and the central core are defined the same as in formula (I);

[0073] Z is a reactive group, including trifluoromethylsulfonate, Cl, Br or I.

[0074] The phosphoryl and / or thiophosphoryl-modified N-phenylcarbazole compounds represented by formula (I) do not include compounds represented by the following formula (1):

[0075]

[0076] In the present invention, a compound having a structure of formula (II) and a compound represented by formula (III) are used as ra...

Embodiment 1

[0131] Example 1 Synthesis of compounds with (II-1) structure

[0132] The synthetic route of the (II-1) compound is as follows:

[0133]

[0134] The synthesis of 9-(4-bromophenyl)-9H-carbazole refers to the method described in Journal of Materials Chemistry 2004, 14, 895-900.

[0135] Take a 100mL three-neck round bottom flask, bake the flask three times, add 0.99g (3.1mmol) of 9-(4-bromophenyl)-9H-carbazole, 0.87g (3.4mmol) of pinacol bisboronate, 71mg (87 μmol) of PdCl 2 (dppf), 0.90g (9.2mmol) of potassium acetate, pumped argon three times, then added 18mL dimethyl sulfoxide (DMSO), pumped again, placed in an oil bath, heated to 80°C, and stirred for 8h. After the reaction finished, the product after the reaction was all poured into a large amount of distilled water, extracted with diethyl ether, dried and spin-dried, and obtained by V 石油醚 :V 二氯甲烷 =5:1 is the eluent, 200-300 mesh silica gel is the stationary phase, and the column is separated to obtain 9-(4-(4,4,5,...

Embodiment 2

[0142] Take a 100mL two-necked round bottom flask, add 1.29g (2.01mmol) of the compound having the formula (II-1) prepared in Example 1, 1.04g (2.38mmol) of 9-(4-bromophenyl)-3 , 6-di-tert-butyl-9H-carbazole, 49.0mg (42.4μmol) of Pd(PPh 3 ) 4 . The argon was replaced three times, and then 4 mL of potassium carbonate aqueous solution and 12 mL of tetrahydrofuran were added. Stir in an oil bath and heat to reflux overnight. After the reaction, the solvent was distilled off under normal pressure, dichloromethane was added to dissolve the product, washed with saturated NaCl water, and washed twice with distilled water, the oil phase was obtained by liquid separation, and dried over anhydrous sodium sulfate. Using 200-300 mesh silica gel as the stationary phase and ethyl acetate as the mobile phase, 0.82 g of white solid was separated, which was the compound with the structure of formula (I-1), and the yield was 47.0%. The result of its nuclear magnetic resonance analysis is: ...

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Abstract

The invention relates to a phosphoryl and / or sulfo-phosphoryl-modified N-phenyl carbazole compound, its preparation method and use, and an organic electroluminescent device. Through introduction of a phosphoryl and / or sulfo-phosphoryl-modified N-phenyl carbazole unit, the phosphoryl and / or sulfo-phosphoryl-modified N-phenyl carbazole compound effectively improves an electron injection / transmission capacity of an organic electronic device in use of a high-work function cathode, realizes performance optimization of an organic electronic device and especially realizes performance optimization of the organic electroluminescent device.

Description

technical field [0001] The invention relates to the field of organic electroluminescence, in particular to phosphoryl and / or thiophosphoryl modified N-phenylcarbazole compounds, a preparation method thereof and an organic electroluminescence device. Background technique [0002] Organic electroluminescent devices are a lighting / display technology emerging in the past three decades, starting from the work of C.W.Tang et al. in 1987 (Appl.Phys.Lett.1987,51,913). They introduced the concept of diodes into organic light-emitting devices, and by introducing a thin organic layer between the cathode and anode, they realized the light emission of organic light-emitting devices at low driving voltage for the first time. In the subsequent development, organic electroluminescent devices exhibited many advantages such as ultra-thin, self-illumination, wide viewing angle, fast response, low cost, flexibility, etc. The most potential third-generation display technology after that. [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6558C07F9/572C09K11/06H01L51/54
Inventor 王利祥丁军桥陈博孟彬
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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