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Benzo-biheterocycle compound, display panel and display device

A heterocyclic compound and display panel technology, applied in organic chemistry, chemical instruments and methods, organic semiconductor devices, etc., can solve problems such as insufficient light extraction effect, insufficient refractive index, and large refractive index difference, etc., to achieve improved Light extraction effect, high refractive index, small refractive index change effect

Active Publication Date: 2019-01-18
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, in the case of applying Alq3 to a blue light-emitting device, there is a problem that the color purity decreases
[0008] The existing problems of CPL materials include: (1) the refractive index is not high enough, and the light extraction effect is not good enough; (2) the difference of the refractive index measured in the respective wavelength regions of blue light, green light and red light is relatively large
Therefore, all light in a light-emitting device that emits blue, green, and red light cannot simultaneously achieve high light extraction efficiency

Method used

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  • Benzo-biheterocycle compound, display panel and display device
  • Benzo-biheterocycle compound, display panel and display device
  • Benzo-biheterocycle compound, display panel and display device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0095] Synthesis of Compound P1

[0096]

[0097] Weigh S1 (10.0mmol) into a 100mL two-necked flask, add 30mL of toluene degassed with nitrogen to dissolve S1, one port of the two-necked flask is connected to a constant pressure dropping funnel, and replace the gas in the reaction system with nitrogen . Weigh NBS (N-bromosuccinimide) (10.5mmol), add 20mL of toluene to dissolve it, and add the toluene solution of NBS to S1 After stirring for 2 h, the temperature of the reaction system was slowly raised to room temperature and stirred 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 The organic phase is dried. The dried organic phase was filtered, and the solvent was distilled off under reduced pressure with a rotary evaporator to obtain a crude product. The crude product was purified by gradient elution...

Embodiment 2

[0129] Synthesis of Compound P2

[0130]

[0131] Put S2 (10mmol), S12 (10.5mmol), tris(dibenzylideneacetone) dipalladium (0) (0.05mmol), sodium tert-butoxide (14mmol), tert-butylphosphine (0.2mmol) into a 50mL three-necked 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 under reflux for 3 hours under nitrogen flow, and then left to cool to room temperature. Water was added to the cooled reaction solution, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was removed by distillation, and purified using column chromatography to obtain intermediate S13 (7.8 mmol, 78%).

[0132] MALDI-TOF MS: C 24 h 18 N 2 , calculated m / z: 334.2; tested: 334.3.

[0133] Elemental Analysis Calculated: C, 86.20; H, 5.43; N, 8.38; Tested: C, 86.22; H, 5.41; N, 8.37.

[0134]

[0135] Put ...

Embodiment 3

[0143] Synthesis of compound P3

[0144]

[0145] Put S8 (10mmol), S13 (21.5mmol), tris(dibenzylideneacetone) dipalladium (0) (0.05mmol), sodium tert-butoxide (14mmol), tert-butylphosphine (0.2mmol) into a 50mL three-necked 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 under reflux for 3 hours under nitrogen flow, and then left to cool to room temperature. Water was added to the cooled reaction solution, extracted with dichloromethane, and washed with saturated brine. After drying the organic layer with anhydrous sodium sulfate, the solvent was removed by distillation, and purified using column chromatography to obtain intermediate S15 (7.6 mmol, 76%).

[0146] MALDI-TOF MS: C 76 h 78 N 4 S 2 Si2 , calculated m / z: 1166.5; tested: 1166.6.

[0147] Elemental Analysis Calculated: C, 78.17; H, 6.73; N, 4.80; S, 5.49; Si, 4.81; Tested: C, 78.19;

[0148]

...

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PUM

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Abstract

The invention provides a benzo-biheterocycle compound with a structure shown as formula (I), wherein Y1 and Y2 respectively are oxygen or sulfur atoms; Ar1 and Ar2 respectively are single-bond, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted acenaphthyleneand substituted or unsubstituted heteroaromatic ring; m and n respectively are 0 or 1; D1 and D2 respectively are aryl and heteroaryl; Ar3 and Ar4 respectively are aryl and heteroaryl; R1 is hydrogenatom, phenyl and naphthyl. According to the invention, benzene ring of benzo-biheterocycle is modified; the introduction of thiophene or furan unit is capable of effectively promoting refractive index; thiophene or furan unit is not located on a main conjugated chain and is impossible to effectively expand conjugation or cause red shift of compound absorption spectrum, so that the absorption of the compound in visible region is lower; when the benzo-biheterocycle compound provided by the invention is used as a material of a cathode cap layer, light emitting of OLED (Organic Light Emitting Diode) is not interfered and the OLED can maintain higher color purity.

Description

technical field [0001] The present invention relates to the technical field of organic electroluminescent materials, in particular to a benzobiheterocyclic compound, a display panel and a display device comprising the benzobiheterocyclic compound. Background technique [0002] According to the direction in which the organic light emitting layer emits light, the OLED display can be classified into a bottom emission OLED display and a top emission OLED display. 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 below the organic light emitting layer. If the OLED display is an active matrix OLED display, the thin film transistors formed therein partially do not transmit light, resulting in a reduced light emitting area. In a top-emitting OLED display, a transparent electrode is formed above the organic light-emitting layer, and a reflective electrode ...

Claims

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Application Information

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IPC IPC(8): C07D493/04C07D495/04C07D519/00H01L51/52
CPCC07D493/04C07D495/04C07D519/00H10K85/636H10K85/626H10K85/633H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K59/873H10K59/879C09K11/06H10K50/15H10K50/11C09K2211/1018H10K50/844H10K50/16H10K50/17H10K50/18H10K50/156H10K50/171H10K2102/351
Inventor 高威张磊朱晴牛晶华安平黄高军
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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