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Compound, light extraction material, organic photo-electric device and electronic device

A compound and light extraction technology, applied in organic chemistry, circuits, electrical components, etc., can solve the problems of insufficient light extraction effect, insufficient high refractive index, and large difference in refractive index, etc., to improve luminous performance, High color purity, enhanced π-π stacking effect

Inactive Publication Date: 2019-09-20
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] (1) The refractive index is not high enough, and the light extraction effect is not good enough;
[0011] (2) The difference in refractive index measured in the respective wavelength regions of blue, green, and red is large, so high light extraction efficiency cannot be obtained simultaneously for all the light in each of the blue, green, and red light-emitting devices

Method used

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  • Compound, light extraction material, organic photo-electric device and electronic device
  • Compound, light extraction material, organic photo-electric device and electronic device
  • Compound, light extraction material, organic photo-electric device and electronic device

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0124] Compound M1 was prepared by the following method:

[0125]

[0126] Weigh S1 (10mmol) into a 100mL two-necked flask, add 30mL nitrogen degassed toluene to dissolve S1, one of the ports is connected to a constant pressure dropping funnel, and nitrogen replaces the gas in the reaction system. Weigh NBS (10.5mmol), add 20mL of toluene to dissolve it, and add the toluene solution of NBS to the toluene solution of S1 drop by drop through the dropping funnel under the condition of 0°C and protected from light. After stirring for 2h, slowly Warm to room temperature and stir overnight. After the reaction was completed, 50 mL of deionized water was added to quench the reaction, extracted with dichloromethane (100 mL × 3), and the organic phase was collected and washed with anhydrous Na 2 SO 4 Dry processing. After filtration, the solvent was distilled off under reduced pressure with a rotary evaporator to obtain a crude product. The crude product was purified by gradient ...

preparation example 2

[0137] Compound M27 was prepared by the following method:

[0138]

[0139] Put S2 (6.5mmol), S6 (6.8mmol), tris(dibenzylideneacetone) dipalladium (0) (0.05mmol), sodium tert-butoxide (14mmol), tert-butylphosphine (0.2mmol) into 50mL three ports In the flask, while stirring, degassing and nitrogen replacement were rapidly repeated 3 times, and 20 mL of toluene was added through a syringe. The mixture was heated to reflux for 3 hours under nitrogen flow. After the reaction, water was added to the reaction solution left to cool to room temperature, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain intermediate S7 (8.6 mmol, 86%).

[0140] MALDI-TOF MS: C 28 h 20 N 2 , calculated m / z: 384.2; tested: 384.5.

[0141]

[0142] Add S8 (6.2mmol), S7 (13.2mmol), tris(dibenzylideneacetone)dipalladium (0) (0.03mmol), sodium...

preparation example 3

[0146] Compound M53 was prepared by the following method:

[0147]

[0148] Add S9 (5.2mmol), S10 (5.5mmol), tris(dibenzylideneacetone)dipalladium (0) (0.05mmol), sodium tert-butoxide (10.0mmol), tert-butylphosphine (0.2mmol) into 50mL In the three-necked flask, while stirring, degassing and nitrogen replacement were repeated 3 times rapidly, and 20 mL of toluene was added through a syringe. The mixture was heated to reflux for 3 hours under nitrogen flow. After the reaction, water was added to the reaction solution left to cool to room temperature, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and purified by column chromatography to obtain intermediate S11 (3.5 mmol, 67%).

[0149] MALDI-TOF MS: C 36 h 24 FNS, m / z calculated: 521.2; found: 521.5.

[0150]

[0151] Put S11 (7.8mmol), S12 (8.3mmol), tris(dibenzylideneacetone)dipalladium (0) (0.08mmol), sodi...

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Abstract

The invention relates to a compound, a light extraction material, an organic photo-electric device and an electronic device. The compound has a structure represented by a formula (I), the index of refraction can be effectively increased by a dibenzothiophene or dibenzofuran parent nucleus, and substituents are all substituted on the same benzene ring, so that a dibenzothiophene or dibenzofuran unit is not located on a main conjugated chain, conjugation cannot be effectively extended, the bathochromic shift of an absorption spectrum of the compound cannot be caused, and thus, the visible region absorption of the compound is relatively low; and the compound is used as the light extraction material and is matched with a specific electron-donating group, so that the compound has relatively high light extraction efficiency, and the stability of long-time work of devices is high. In addition, the compound can also be used as organic thin layer materials such as a hole transport layer, an optical auxiliary layer and an electron barrier layer, so that the improvement on luminescence performance of the devices is facilitated.

Description

technical field [0001] The invention relates to the field of organic electroluminescence, in particular to a compound, a light extraction material, an organic photoelectric device and electronic equipment. Background technique [0002] Organic light emitting diode (OLED) displays can be classified into bottom emission OLED displays and top emission OLED displays according to the direction in which light is emitted from the organic light emitting layer. In a bottom emission OLED display, light is emitted toward a substrate, a reflective electrode is formed on an organic light emitting layer, and a transparent electrode is formed under the organic light emitting layer. Here, if the OLED display is an active matrix OLED display, the thin film transistor formed therein partially does not transmit light, so the light emitting area is reduced. On the other hand, in a top-emitting OLED display, a transparent electrode is formed on the organic light-emitting layer, and a reflective...

Claims

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Application Information

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IPC IPC(8): C07D409/14C07D417/14C07D333/76C07D405/14C07D307/91C07D409/12H01L51/50H01L51/54
CPCC07D409/14C07D417/14C07D333/76C07D405/14C07D307/91C07D409/12H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/657H10K85/6572H10K50/00
Inventor 高威刘营张磊代文朋卢艳牛晶华刘忆
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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