Cyano anthraquinone derivatives, preparation method and organic electroluminescent devices thereof

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

Active Publication Date: 2014-04-02
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

Experimental program
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preparation example Construction

[0021] Another object of the present invention is to provide a preparation method of cyanoanthraquinone derivatives, which includes 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 The aromatic boric acid or structural formula is The aromatic borate is soluble in organic solvents; among them, 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 anthraquinone to aromatic boric acid or aromatic boric acid ester is 1:2-1:4;

[0023] Step S2, adding lye and catalyst to step S1, stirring and mixing, and synthesizing reaction at 60-130°C for 10 to 48 hours to obtain the cyanoanthraquinone derivative of the following general formula (I):

[0024]

[0025] The reaction formula is as follows:

[0026]

[0027] The further optimization scheme of the above preparation method is that the crude product of the cyanoanthraquinone derivative o...

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 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), pyreneboric acid (5.76g, 23.4mmol) and tetra Triphenylphosphine palladium (104 mg, 0.09 mmol) was dissolved in 80 ml of ethylene glycol dimethyl ether, then sodium carbonate solution (2.0 mol / L, 90 mL) was added and mixed; the mixture was stirred vigorously at 90° C. for 12 hours. Cooled to room temperature, extracted three times with dichloromethane, combined the organic phases, washed with 1mol / L sodium hydroxide solution, dried over anhydrous magnesium sulfate and spin-dried. The crude product was petroleum ether: ethyl acetate (10:1) as The eluent is separated by silica gel chromatography to obtain a white solid, namely 2,6-dipyrene-9,10-diene-11,11,12,12-te...

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 target molecule is as follows:

[0050] Under the protection of nitrogen, 2,6-dibromo-9,10-diene-11,11,12,12-tetracyanoanthraquinone (4.15g, 9mmol), 9-phenyl-10-anthraboronic acid (5.76 g, 23.4mmol) and bistriphenylphosphonium 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 stirred vigorously at 90°C for 18h. Cooled to room temperature, extracted three times with dichloromethane, combined the organic phases, washed with 1mol / L sodium hydroxide solution, dried over anhydrous magnesium sulfate and spin-dried. The crude product was petroleum ether: ethyl acetate (10:1) as The eluent is separated by silica gel chromatography to obtain a white solid, namely 2,6-bis[10'-(9'-phen...

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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 present invention relates to the technical field of organic photoelectric materials, in particular to a class of cyanoanthraquinone derivatives which are organic semiconductor materials. The present invention also relates to a preparation method of the cyanoanthraquinone derivative; the present invention further relates to an organic electroluminescence device using the cyanoanthraquinone derivative as a light-emitting layer. Background technique [0002] Since C.W.Tang et al. first reported on organic light-emitting diodes (OLED), both small molecule and polymer light-emitting diodes have made great progress. Its potential applications are full-color flat panel displays and solid-state white light illumination. Among the three primary colors, both red and green diodes are close to the requirements of practical applications. However, due to the wider band gap and lower highest occupied orbital (HOMO) energy level of blue light materials, there is a lar...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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