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Anthraquinone derivative material and preparation method and application thereof

An anthraquinone derivative and compound technology, applied in the field of anthraquinone derivative materials and their preparation, can solve the problems of inability to form high-quality thin films, pinholes, poor thermal stability, etc., and achieve excellent structural stability and excellent thermal stability. performance, good thermal stability

Active Publication Date: 2012-11-28
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, 9,10-dinaphthylanthracene has poor thermal stability and cannot form high-quality films, and the films deposited by evaporation are prone to crystallization, resulting in rough surfaces, grain boundaries, and pinholes, which eventually lead to the use of this 9,10 - Failure of organic electroluminescent devices by dinaphthylanthracene

Method used

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  • Anthraquinone derivative material and preparation method and application thereof
  • Anthraquinone derivative material and preparation method and application thereof
  • Anthraquinone derivative material and preparation method and application thereof

Examples

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preparation example Construction

[0041] A preparation method of the above-mentioned anthraquinone derivative material P, comprising the following steps:

[0042] Step S1, providing compound A represented by the following structural formula, and boronic acid or boronic acid ester corresponding to Ar.

[0043] A is: Wherein X is Cl or Br, preferably Br.

[0044] The boric acid corresponding to Ar is:

[0045]

[0046] The boronate corresponding to Ar is:

[0047]

[0048] Among them, -Ar is:

[0049]

[0050] Step S2, dissolving the boric acid or boric acid ester corresponding to compound A and Ar in an organic solvent at a molar ratio of 1:2 to 1:4, then adding a catalyst, and reacting at 70°C to 130°C for 10 hours to 48 hours to obtain Anthraquinone derivative material represented by the following structural formula:

[0051]

[0052] The overall reaction equation is as follows:

[0053]

[0054] The reaction temperature is preferably 80°C to 100°C.

[0055] The molar ratio of compound ...

Embodiment 1

[0061] The present embodiment prepares 2,6-dipyrene-9, and the reaction process of 10-anthraquinone is as follows:

[0062]

[0063] Above-mentioned 2,6-dipyrene-9, the preparation of 10-anthraquinone is as follows:

[0064] Under nitrogen protection, 2,6-dibromo-9,10-anthraquinone (3.29g, 9mmol), pyreneboronic acid (5.76g, 23.4mmol) and tetrakistriphenylphosphine palladium (Pd(PPh 3 ) 4) (208mg, 0.18mmol) was dissolved in 80ml of benzene, and then sodium carbonate solution (2.0mol / L, 90mL) was added. The mixture was vigorously stirred and reacted at 110°C for 10 h, then cooled to room temperature, extracted three times with dichloromethane, the organic phases were combined, washed with 1 mol / L sodium hydroxide solution, dried with anhydrous magnesium sulfate and then spin-dried, and the crude product was obtained by petroleum ether The volume ratio of ethyl acetate to 10:1 was used as eluent and separated by silica gel chromatography to obtain a white solid with a yield ...

Embodiment 2

[0071] The present embodiment prepares 2,6-two (10'-(9'-phenyl)anthracene)-9, the reaction process of 10-anthraquinone is as follows:

[0072]

[0073] The preparation of above-mentioned 2,6-two (10'-(9'-phenyl)anthracene)-9,10-anthraquinone is as follows:

[0074] Under nitrogen protection, 2,6-dibromo-9,10-anthraquinone (3.29g, 9mmol), 9-phenyl-10-anthraceneboronic acid (5.76g, 23.4mmol) and bistriphenylphosphine dichloride Palladium chloride (315.9 mg, 0.45 mmol) was dissolved in 80 ml of ethylene glycol dimethyl ether, and then potassium hydroxide solution (2.0 mol / L, 90 mL) was added. The mixture was vigorously stirred and reacted at 70°C for 36 hours, then cooled to room temperature, extracted three times with dichloromethane, combined organic phases, washed with 1mol / L sodium hydroxide solution, dried over anhydrous magnesium sulfate and then spin-dried, and the crude product was obtained by petroleum ether The volume ratio of ethyl acetate to 10:1 was used as the e...

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Abstract

The invention discloses an anthraquinone derivative material, which has the following structural formula: wherein -Ar is FORMULA. The anthraquinone derivative material has excellent thermal stability and conjugate structure, and emits blue light. The invention also provides a preparation method for the anthraquinone derivative material and application of the material in organic electroluminescent devices.

Description

【Technical field】 [0001] The invention relates to the field of optoelectronics, in particular to an anthraquinone derivative material and its preparation method and application. 【Background technique】 [0002] In recent years, organic light-emitting diodes (OLEDs) have made great progress. Among the three primary colors, red and green light diodes are already close to the requirements of practical applications, but the blue light material has a wider band gap and a lower highest occupied orbital (HOMO) energy level, so there is a larger carrier injection energy. At the same time, blue light materials have high emission energy, are unstable, and are prone to energy transfer, resulting in impure emission colors, so the development is relatively slow. [0003] Anthracene derivatives have become a research hotspot due to their ultra-high fluorescence quantum yield and excellent electroluminescent and electrochemical properties, and are widely used in the construction of high-ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/16C07C46/00C07C225/34C07C221/00C07D209/86C09K11/06H01L51/54
Inventor 周明杰王平张振华梁禄生
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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