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Quinoxaline compound, polymer, organic electronic device and display panel

A technology of organic electronic devices and quinoxalines, which is applied in the field of organic optoelectronic materials, can solve problems such as interfacial miscibility and interfacial erosion, and achieve good thermal stability, compact stacking, and low-cost effects

Active Publication Date: 2021-08-13
GUANGDONG JUHUA PRINTING DISPLAY TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Based on this, it is necessary to provide a quinoxaline compound, a quinoxaline polymer, an organic electronic device and a display panel for the problems of interfacial miscibility and interfacial erosion when a multilayer organic light-emitting diode is prepared by a solution processing method.

Method used

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  • Quinoxaline compound, polymer, organic electronic device and display panel
  • Quinoxaline compound, polymer, organic electronic device and display panel
  • Quinoxaline compound, polymer, organic electronic device and display panel

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preparation example Construction

[0105] The preparation method of precursors A and P can be prepared according to the following preparation method provided herein, but is not limited to the preparation method provided by the present invention.

[0106] Preparation process of precursor A:

[0107]

[0108] Where X 1 , X 2 Can be BR, H, C 6 Hide 13 Any combination of the groups.

[0109] Specifically, raw metal (5 mmol), diamine (5 mmol) is added to the flask, and then 80 ml of acetic acid is added as a solvent. After 8 hours of heating, the reaction is completed, then cool to the room temperature and pour the reaction liquid into 200 ml of ethanol, Then filtration was performed, and the filter residue was cleaned multiple times. Then, the crude product was separated from the silica gel column, and the eluent was used as n-hexane / dichloromethane, and the solvent collection product was spurly evaporated. The last room temperature was vacuum drying 12h, weighed, and the yield was about 80%.

[0110] Preparation p...

Embodiment 1

[0118] Example 1 Preparation of Compound M1

[0119]

[0120] 3 mmol intermediate A1, 15 mmol boronic acid vinyl derivative P3, 0.8 mmol tricyclic hexylphosphine Pcy3 and 0.4 mmol catalyst tris (dibenzyl acetone) di palladium Pd were added to a 500 ml of two bottles. 2 (DBA) 3 For evacuation of nitrogen, it is repeated three times, so that the pressure tube is in a nitrogen atmosphere; adding 150 ml of 1,4-dioxane solvent and 2.4 mol / L Na 2 CO 3 The solution is 150 ml. At 100 ° C, in a nitrogen atmosphere, the mixed liquid refluxed overnight. After completion of the reaction, the reaction solution was filtered, then extracted, followed by separating the reaction liquid to the silica gel column, using n-hexane / ethyl acetate as a washing off agent, spurly removed the solvent collection product, last room temperature vacuum dry 12h The M1 is obtained, the weight is about 82%. The product M1 nuclear magnetic data is as follows:

[0121] 1 HNMR (300 MHz, DMSO), (TMS, PPM): 9.27 (...

Embodiment 2

[0122] Example 2 Preparation method of Compound M4

[0123]

[0124] A 3 mmol intermediate B1, 12 mmol boric acid vinyl derivative P2, 0.6 mmol tricyclic hexylphosphine Pcy3 and 0.3 mmol catalyst tris (dibenzyl acetone) di palladium Pd were added to a 500 ml of two bottles. 2 (DBA) 3 For vacuum changing nitrogen operation, repeated three times, in the pressure tube in a nitrogen atmosphere; add 100 ml of 1,4-dioxane solvent and 2.4 mol / L Na 2 CO 3 The solution was 110 ml. At 100 ° C, in a nitrogen atmosphere, the mixed liquid refluxed overnight. After completion of the reaction, the reaction solution was filtered, then extracted, followed by separating the reaction liquid to the silica gel column, using n-hexane / ethyl acetate as a washing off agent, spurly removed the solvent collection product, last room temperature vacuum dry 12h The M4 is obtained, the yield is about 79%. The product M4 nuclear magnetic data is as follows:

[0125] 1 HNMR (300MHz, DMSO), (TMS, PPM): 9.27 ...

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Abstract

The invention relates to a quinoxaline compound. The structure of the compound is shown as a general formula (M), in the general formula (M), R1, R2, R3 and R4 are independently selected from any one of hydrogen atoms, alkyl groups or an aryl group shown in the specification, Ar is selected from groups containing aromatic rings or heteroaromatic rings, and at least two of R1, R2, R3 and R4 are independently selected from the aryl group shown in the specification. The invention also relates to a quinoxaline polymer, an organic electronic device and a display panel.

Description

Technical field [0001] The present invention relates to the field of organic photoelectric materials, and more particularly to a quinoxaline compound, quinoxaline polymer, an organic electronic device, and a display panel. Background technique [0002] OLED (Organic Light-Emitting Diode, an organic light-emitting diode) device is a small molecule organic electroluminescent device such as a light-emitting material such as an organic dye and pigment, in order to achieve high performance luminescent devices. Outside of the material, a multi-layer device structure is often used, that is, in addition to the light-emitting layer, there is an electron transport layer / hole injection layer or an electron transport layer / electron injection layer. [0003] Conventional OLED devices are obtained by obtaining multi-layer high-efficiency organic electroluminescent devices by means of small molecule vacuum vapor deposition, but due to the vacuum vapor deposition method having excessive pric...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/38C07D401/14C08G61/12C08F12/34H01L51/54H01L51/50
CPCC07D241/38C07D401/14C08G61/122C08F12/34C08G2261/135C08G2261/143C08G2261/324C08G2261/419C08G2261/514C08G2261/592C08G2261/95H10K85/111H10K85/141H10K85/654H10K50/12H10K85/6572H10K50/16Y02E10/549
Inventor 郑江波周兴邦
Owner GUANGDONG JUHUA PRINTING DISPLAY TECH CO LTD