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Benzoheterocyclic 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 the problems of high light extraction efficiency, insufficient light extraction effect, and large refractive index difference, etc., to achieve high light extraction Efficiency, avoiding the effect of reducing color purity

Active Publication Date: 2019-02-01
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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  • Benzoheterocyclic compound, display panel and display device
  • Benzoheterocyclic compound, display panel and display device
  • Benzoheterocyclic compound, display panel and display device

Examples

Experimental program
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Effect test

Embodiment 1

[0095] Synthesis of Compound P1

[0096]

[0097] Weigh S1 (10mmol) 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 of ...

Embodiment 2

[0113] Synthesis of Compound P4

[0114]

[0115] Put S2 (10mmol), S8 (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 repeated three times quickly, 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 S9 (7.2 mmol, 72%).

[0116] MALDI-TOF MS: C30 h 22 N 2 S 4 , calculated m / z: 538.1; tested: 538.4.

[0117] Elemental Analysis Calculated: C, 66.88; H, 4.12; N, 5.20; S, 23.81; Tested: C, 66.90; H, 4.15; N, 5.18;

[0118] ...

Embodiment 3

[0127] Synthesis of Compound P5

[0128]

[0129] Under nitrogen protection, weigh compound S5 (25mmol), S12 (25mmol), [Pd 2 (dba) 3 ]·CHCl 3 (0.5mmol) and HP(tBu) 3 ·BF 4 (1.0mmol), was added to a 250mL two-necked flask. Inject 100mL of toluene into the two-necked flask (introduce N in advance 2 15min to remove oxygen), and then add 12mL of K with a concentration of 1M dropwise 2 CO 3 Aqueous solution (into N in advance 2 15min to remove oxygen), and stirred overnight at room temperature. After the reaction was completed, 100 mL of deionized water was added, followed by a few drops of 2M HCl. Extract with dichloromethane, collect the organic phase, and wash with anhydrous Na 2 SO 4 The organic phase is dried. The dried organic phase was filtered, and the solvent was removed by a rotary evaporator to obtain a crude product. The crude product was purified by silica gel column chromatography to obtain solid S13 (18.8 mmol, 75%).

[0130] MALDI-TOF MS: C 14 h ...

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Abstract

The invention provides a benzoheterocyclic compound. The benzoheterocyclic compound has a structure represented by formula (I); and in the formula, R1 is any one of hydrogen atom, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthryl group and a phenanthryl group, Y1 and Y2 are respectively independently selected from a carbon atom, an oxygen atom and a sulfur atom, one of the Y1 and Y2 is the carbon atom, Ar1 is a single-bond or monosubstituted or unsubstituted group of any one of a phenyl group, a naphthyl group, a fluorenyl group, a phenanthryl group, anacenaphthenyl group and an aromatic heterocyclic ring, m is 0 or 1, D1 and D2 are respectively independently selected from an aryl group or a heteroaryl group, and Ar2 and Ar3 are respectively independently selected from an aryl group and a heteroaryl group. The benzoheterocyclic compound can be used as a material for a capping layer (CPL) of an OLED device to obtain a high light extraction efficiency and avoid the problem of reduction of the color purity of the blue light-emitting device.

Description

technical field [0001] The present invention relates to the technical field of organic electroluminescence materials, in particular to a benzo heterocyclic compound, a display panel and a display device containing the benzo heterocyclic 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 i...

Claims

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Application Information

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IPC IPC(8): C07D409/14C07D417/14C07D333/76C07D333/54C07D405/14C09K11/06H01L51/54H01L51/50
CPCC09K11/06C07D333/54C07D333/76C07D405/14C07D409/14C07D417/14C09K2211/1044C09K2211/1037C09K2211/1029C09K2211/1092C09K2211/1088H10K85/636H10K85/615H10K85/6576H10K85/6574H10K85/657H10K50/16H10K59/879H10K85/633H10K85/6572H10K50/15H10K50/11H10K2102/3026H10K50/156
Inventor 高威张磊朱晴牛晶华黄高军
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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