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Coumarin derivates, preparation method thereof and application thereof in white-light organic electroluminescent device

A coumarin derivative, selected technology, applied in the direction of electric solid-state devices, electrical components, luminescent materials, etc.

Inactive Publication Date: 2011-06-22
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The WOLED technology based on the fluorescence / phosphorescence combination mechanism (abbreviated as F / P-WOLED, F for fluorescence and P for phosphorescence) published in the journal Nature in 2006 is considered to be the most ideal and promising way to realize high-efficiency and long-life WOLED. However, this mechanism puts forward new and higher requirements for the main material of the light-emitting layer, and it has also become a "short board" in the entire F / P-WOLED material system
[0007] However, there are very few such host material systems with higher triplet energy levels at present, and the research scope is mainly concentrated on carbazole derivatives. Therefore, in order to improve device performance, it is necessary to find better host materials with higher triplet energy levels. system is very necessary

Method used

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  • Coumarin derivates, preparation method thereof and application thereof in white-light organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Embodiment 1. Synthesis of compound B1, synthetic route:

[0062]

[0063] Synthesis of intermediate M1: Add 7-ethoxy-4-methylcoumarin (2.04g, 10mmol), succinimide (abbreviated as NBS) (2.67g, 15mmol) and benzyl peroxide in a two-neck flask Acyl (referred to as DBP) (20mg) and chloroform (100mL), refluxed for 5 hours. After the reaction was completed, the chloroform layer was concentrated under reduced pressure, and the precipitate was washed with 500 mL of hot water (at a temperature of 50 to 80° C.) (to remove succinimide), filtered, and the resulting crude product was washed with a silica gel column (dichloromethane as a rinse). agent) was isolated and dried in vacuo to obtain intermediate M1 (2.58 g, 9.1 mmol, yield 91%).

[0064] Synthesis of compound B1: under nitrogen protection, add M1 (283mg, 1mmol), 4-triphenylamine borate (289mg, 1mmol), Pd(PPh 3 ) 4(92mg, 0.08mmol), 2M sodium carbonate (3mL), toluene (6mL) and ethanol (2mL), heated to reflux at 115°C f...

Embodiment 2

[0068] The synthesis of embodiment 2. compound B4, synthetic route:

[0069]

[0070] Synthesis of compound B4: under nitrogen protection, intermediate M1 (623mg, 2.2mmol) of Example 1, 1,4-benzenediboronic acid (166mg, 1mmol), Pd(PPh 3 ) 4 (92mg, 0.08mmol), 2M sodium carbonate (3mL), toluene (6mL) and ethanol (2mL), heated to reflux at 115°C for 24 hours. The reaction solution was extracted with chloroform, the extracted product was washed with water, dried over anhydrous magnesium sulfate, and the chloroform solvent was evaporated under reduced pressure. The obtained crude product was separated by a silica gel column (dichloromethane:methanol volume ratio=100:1), and dried in vacuo to obtain a white compound B4 solid (410mg, 0.85mmol, yield 85%).

[0071] Product MS (m / e): 482, corresponding to: C 30 h 26 o 6 =482, proving that the compound is B4.

[0072] Fluorescence quantum yield Φ f =78% (with the fluorescence quantum yield Φ of coumarin-1 in ethyl acetate f =...

Embodiment 3

[0074] The synthesis of embodiment 3. compound B5, synthetic route:

[0075]

[0076] Synthesis of Compound B5: The method and reaction conditions were the same as those of Compound B4 in Synthesis Example 2, except that 1,4-benzenediboronic acid was replaced by 4,4'-biphenyldiboronic acid, and the final product was a white powder.

[0077] Product MS (m / e): 558, corresponding to: C 36 h 30 o 6 =558, proving that the compound is B5.

[0078] Fluorescence quantum yield Φ f =65% (with the fluorescence quantum yield Φ of coumarin-1 in ethyl acetate f = 99% as standard).

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Abstract

The invention belongs to the technical field of organic electroluminescent display, and particularly relates to coumarin derivates, a preparation method thereof and application thereof in a white-light organic electroluminescent device. The coumarin derivates are in any one structure as disclosed in the specification. The coumarin derivate materials provided by the invention can efficiently emit blue fluorescence, and have high color purity, high fluorescence quantum yield, high electroluminescence efficiency and favorable film-forming performance; and the synthesis and purification method ofthe coumarin derivate materials is simple and suitable for mass production. The coumarin derivate materials provided by the invention have a high triplet-state energy level (higher than 2.4eV), and can simultaneously sensitize green and red phosphorescent doped materials. The coumarin derivate materials provided by the invention can be used as main materials in illuminant materials and / or luminescent layers in the organic electroluminescent device and used for preparing the organic electroluminescent device.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence display, and particularly relates to a coumarin derivative and a preparation method thereof, and the application of the coumarin derivative in a white light organic electroluminescence device. Background technique [0002] Lighting consumes a lot of energy. According to statistics, 20% of the world's annual power generation is used for lighting. Incandescent lamps and fluorescent tubes are the two most commonly used traditional white light sources at present, but their energy utilization efficiency is not high: incandescent lamps convert 90% of energy into heat energy, causing a lot of energy waste, while fluorescent tubes only 70% of the energy is used to emit light. Based on this, the luminous efficiency of incandescent lamps is generally 13lm / W to 20lm / W, while that of fluorescent tubes is 90lm / W. In order to save energy and improve energy utilization efficiency, it is mea...

Claims

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Application Information

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IPC IPC(8): C07D311/18C07D405/10C07D405/14C07D413/14C07D409/14C07F5/02C07F7/08C09K11/06H01L51/50H01L51/54
Inventor 张晓宏王静郑才俊李述汤
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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