Dihydro acridine derivatives, application thereof and organic electroluminescent device applying same

A technology of dihydroacridine derivatives, which is applied in the field of dihydroacridine derivatives, can solve the problems of luminescence quenching and high cost, and achieve the effects of reducing the turn-on voltage and high current efficiency

Active Publication Date: 2012-04-04
KUNSHAN VISIONOX DISPLAY TECH +2
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem solved by the present invention is to overcome the problems of luminescence quenching and high cost of noble metal phosphorescent materials organic electroluminescent devices at high concentrations, and provide a new class of dihydroacridine derivatives substituted by diphenylphosphine oxide, This type of compound can be used in the field of organic electroluminescent lighting and display technology. Using this type of compound as the host material of doped light-emitting devices can reduce the cost of phosphorescent organic electroluminescent devices and avoid high-concentration quenching of luminescence

Method used

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  • Dihydro acridine derivatives, application thereof and organic electroluminescent device applying same
  • Dihydro acridine derivatives, application thereof and organic electroluminescent device applying same
  • Dihydro acridine derivatives, application thereof and organic electroluminescent device applying same

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preparation example Construction

[0037] The preparation method of the dihydroacridine derivative substituted by diphenylphosphine oxide of the present invention will be described in detail below. The preparation method includes the following steps.

[0038] In the first step, palladium dibenzylideneacetone (Pd(dba) 2 ), tri-tert-butylphosphine (P(t-Bu) 3 ), in the presence of sodium tert-butoxide (NaO(t-Bu)), aniline or diphenylamine or their derivatives, and o-dibromobenzene or 1-bromo-2-iodobenzene or their derivatives, according to the reaction The substitution reaction is carried out at a molar ratio of 1:1.2 or 1:2.2 to obtain triarylamine (intermediate A).

[0039] In the second step, under the system of anhydrous tetrahydrofuran (THF) as the solvent, under the temperature condition of -78°C, add n-butyllithium (n-BuLi) to the intermediate A according to the reaction molar ratio of 1:1.2 or 1 : 2.2 is reacted to obtain the corresponding lithium salt. A THF solution of 4,4'-dibromobenzophenone was ad...

Embodiment 1

[0053] The synthesis of embodiment 1 compound (1)

[0054]

[0055] (1) Synthesis of intermediate (1-A)

[0056] Under nitrogen protection, add 33.8g (0.2mol) diphenylamine, 56.64g (0.24mol) o-dibromobenzene, 0.58g (0.5mol%) Pd (dba) in a 500ml three-neck round bottom flask 2 , 2.0ml (0.5mol%) P(t-Bu) 3 10% cyclohexane solution and 19.2g (0.2mol) NaO(t-Bu), and then 300ml of anhydrous-treated toluene was added to obtain a reaction solution. The above reaction solution was refluxed in an oil bath at 110°C for 4 hours under magnetic stirring, cooled, and then the reaction solution was washed with an appropriate amount of water for 2-3 times before liquid separation, and the obtained organic phase was washed with anhydrous MgSO 4 After drying, the organic solvent was removed by rotary evaporation to obtain the crude product. The crude product was separated by silica gel (200-300 mesh, Qingdao Ocean Chemical Factory) column chromatography to obtain 44.12 g of white crystals,...

Embodiment 2

[0065] The synthesis of embodiment 2 compound (4)

[0066]

[0067] Using 4,4'-dimethyldiphenylamine instead of diphenylamine, and 1-bromo-2-iodo-5-methylbenzene instead of o-dibromobenzene, compound (4) was obtained through the same steps as in Example 1. Yield 88.6%.

[0068] Compound (4) product MS (m / z): 851; elemental analysis (C 58 h 47 NO 2 P 2 ): theoretical value C: 81.77%, H: 5.56%, N: 1.64%; measured value C: 81.70%, H: 5.52%, N: 1.62%.

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Abstract

The invention provides dihydro acridine derivatives, application thereof and an organic electroluminescent device applying the same. The diphenyl phosphine oxide substituted dihydro acridine derivatives have a structural formula shown in the formula (1) in the specification and are used as phosphorescence main material in an organic electroluminescent device. The an organic electroluminescent device applying the compounds has higher current efficiency, and start voltage is reduced effectively.

Description

technical field [0001] The invention relates to a new class of dihydroacridine derivatives substituted by diphenylphosphine oxide and its application in the technical field of organic electroluminescent lighting and display. Background technique [0002] Organic light-emitting diodes (OLEDs) are current-driven light-emitting devices that use organic materials as active materials. Unlike inorganic materials, organic materials have the advantages of low synthesis cost, adjustable functions, flexibility, and good film-forming properties. Moreover, devices based on organic materials are generally simple in manufacturing process, easy to prepare in large areas, and are environmentally friendly, and thin film preparation methods with lower operating temperatures, such as spin coating, inkjet printing, and dipping, can be used. Therefore, OLEDs have the advantage of low manufacturing cost. features. OLEDs have been widely researched, developed and used in the past 20 years due to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/64C09K11/06H01L51/54
Inventor 邱勇刘飞
Owner KUNSHAN VISIONOX DISPLAY TECH
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