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Cyano anthraquinone derivatives, preparation method and organic electroluminescent devices thereof

A cyano-anthraquinone and tetracyano-anthraquinone technology, applied in the field of organic optoelectronic materials, can solve the problems of inability to form high-quality thin films, device failure, rough surface, etc., and achieve good morphology stability and high singlet energy. The effect of grade and simple preparation process

Active Publication Date: 2012-11-21
OCEANS KING LIGHTING SCI&TECH CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it does not form high-quality films, and films deposited by evaporation are prone to crystallization, resulting in rough surfaces, grain boundaries, and pinholes, which eventually lead to device failure

Method used

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  • Cyano anthraquinone derivatives, preparation method and organic electroluminescent devices thereof
  • Cyano anthraquinone derivatives, preparation method and organic electroluminescent devices thereof
  • Cyano anthraquinone derivatives, preparation method and organic electroluminescent devices thereof

Examples

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preparation example Construction

[0021] Another object of the present invention is to provide a preparation method of cyanoanthraquinone derivatives, comprising the following steps:

[0022] Step S1, the structural formula is The 2,6-dihalo-9,10-diene-11,11,12,12-tetracyanoanthraquinone with the structural formula is The aromatic boronic acid or structural formula is The aromatic borate is dissolved in an organic solvent; where Ar is an aromatic group; X is Cl or Br; 2,6-dihalo-9,10-diene-11,11,12,12-tetracyano The molar ratio of base anthraquinone to aromatic boric acid or aromatic borate is 1:2-1:4;

[0023] Step S2, add lye and catalyst to step S1, stir and mix, and synthesize and react at 60-130°C for 10-48 hours to obtain the cyanoanthraquinone derivative of the following general formula (I):

[0024]

[0025] The reaction formula is as follows:

[0026]

[0027] Further optimization of the above preparation method, that is, the crude product of the cyanoanthraquinone derivative obtained in ...

Embodiment 1

[0041] This example discloses 2,6-dipyrene-9,10-diene-11,11,12,12-tetracyanoanthraquinone with the following structural formula.

[0042]

[0043] The preparation of the above-mentioned target molecule is as follows:

[0044] Under the protection of nitrogen, 2,6-dibromo-9,10-diene-11,11,12,12-tetracyanoanthraquinone (4.15g, 9mmol), pyreneboronic acid (5.76g, 23.4mmol) and four Triphenylphosphine palladium (104mg, 0.09mmol) was dissolved in 80ml of ethylene glycol dimethyl ether, then sodium carbonate solution (2.0mol / L, 90mL) was added and mixed; the mixture was vigorously stirred at 90°C for 12h. Cool to room temperature, extract three times with dichloromethane, combine the organic phases, wash with 1mol / L sodium hydroxide solution, spin dry after drying over anhydrous magnesium sulfate, use petroleum ether:ethyl acetate (10:1) as the crude product The eluent was separated by silica gel chromatography to obtain a white solid, namely 2,6-dipyrene-9,10-diene-11,11,12,12-t...

Embodiment 2

[0047] This example discloses 2,6-bis[10'-(9'-phenyl)anthracene]-9,10-diene-11,11,12,12-tetracyanoanthraquinone with the following structural formula.

[0048]

[0049] The preparation of the above-mentioned target molecule is as follows:

[0050] Under nitrogen protection, 2,6-dibromo-9,10-diene-11,11,12,12-tetracyanoanthraquinone (4.15g, 9mmol), 9-phenyl-10-anthraceneboronic acid (5.76 g, 23.4mmol) and bistriphenylphosphine palladium dichloride (315.9mg, 0.45mmol) were dissolved in 80ml of tetrahydrofuran, and then sodium carbonate solution (2.0mol / L, 90mL) was added. The mixture was vigorously stirred at 90°C for 18h. Cool to room temperature, extract three times with dichloromethane, combine the organic phases, wash with 1mol / L sodium hydroxide solution, spin dry after drying over anhydrous magnesium sulfate, use petroleum ether:ethyl acetate (10:1) as the crude product The eluent was separated by silica gel chromatography to obtain a white solid, namely 2,6-bis[10'-(...

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Abstract

The present invention belongs to the technical field of organic photoelectric materials, and discloses a class of cyano anthraquinone derivatives, a preparation method and an application thereof. The cyano anthraquinone derivatives have the following general formula (I), wherein Ar is an aromatic group. The cyano anthraquinone derivatives of the present invention have characteristics of simple preparation process, good morphology stability, good film forming property, and high singlet state energy level, and are suitable host materials. In addition, electroluminescent devices prepared by adopting the cyano anthraquinone derivatives as a light emitting layer have high luminous efficiency.

Description

technical field [0001] The invention relates to the technical field of organic photoelectric materials, in particular to a class of cyanoanthraquinone derivatives used as organic semiconductor materials. The present invention also relates to a preparation method of the cyanoanthraquinone derivative; the present invention further relates to an organic electroluminescent device using the cyanoanthraquinone derivative as a light-emitting layer. Background technique [0002] Since the organic light-emitting diodes (OLEDs) were first reported by C.W. Tang et al., both small-molecule and polymer-based LEDs, great progress has been made. Its potential applications are full-color flat-panel displays and solid-state white lighting. Among the three primary colors, red and green light diodes are close to the requirements of practical applications, but blue light materials have larger carrier injection due to their wider band gap and lower highest occupied orbital (HOMO) energy level. ...

Claims

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Application Information

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IPC IPC(8): C07C255/31C07C253/30C07D209/86C09K11/06H01L51/00H01L51/54
Inventor 周明杰王平张振华张娟娟
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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