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Organic light-emitting materials containing dinitrogen difluoride-boron-oxygen heterocyclic receptor structural unit and application thereof

A luminescent material, a technology of nitrogen difluoride, which is applied in the field of organic luminescent materials, OLED display and lighting, and can solve the problems that blue phosphorescent materials are difficult to meet the requirements of commercial applications, limited metal phosphorescent materials, and limited resources.

Active Publication Date: 2019-07-12
ZHEJIANG HONGWU TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although metal-organic phosphorescent materials have made great progress, red and green metal iridium complex phosphorescent materials have been applied in commercial electronic products, but metals that can meet commercial requirements in terms of quantum efficiency and stability Phosphorescent materials are also extremely limited, especially blue phosphorescent materials have been difficult to meet the requirements of commercial applications; in addition, rare heavy metal materials are extremely expensive and resources are limited, which are serious shortcomings

Method used

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  • Organic light-emitting materials containing dinitrogen difluoride-boron-oxygen heterocyclic receptor structural unit and application thereof
  • Organic light-emitting materials containing dinitrogen difluoride-boron-oxygen heterocyclic receptor structural unit and application thereof
  • Organic light-emitting materials containing dinitrogen difluoride-boron-oxygen heterocyclic receptor structural unit and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] Embodiment 1: The luminescent material NOBF2-1 can be synthesized according to the following route:

[0082]

[0083] Synthesis of Intermediate 1: Add 2,4-dibromopyridine (15.72g, 66.40mmol, 1.0 equivalent), 2-methoxyphenylboronic acid (11.10g ,73.01mmol,1.1eq), Pd(PPh 3 ) 4 (2.30g, 1.99mmol, 3mol%), Na 2 CO 3 (21.11g, 199.20mmol, 3.0 equivalents), nitrogen was pumped three times. Tetrahydrofuran (120 mL) and water (30 mL) were added under nitrogen protection. The mixture was stirred and reacted in an oil bath at 85°C for 48 hours, monitored by thin-layer chromatography until the reaction of the raw materials was completed, and then cooled to room temperature. The reaction mixture was extracted with ethyl acetate (50mL×3), the combined organic phases were washed with anhydrous Na 2 SO 4 dry. After filtration, the solvent was distilled off under reduced pressure, and the crude product was separated and purified by silica gel chromatography. The eluent was petr...

Embodiment 2

[0089] Embodiment 2: The luminescent material NOBF2-2 can be synthesized according to the following route:

[0090]

[0091] Synthesis of intermediate OCH3-2: Add intermediate 2 ((2.49g, 8.41mmol, 1.0 equivalent), 3,6-di-tert-butylcarbazole ( 2.59g, 9.25mmol, 1.1 equiv), Pd 2 (dba) 3 (231.0 mg, 0.25 mmol, 3.0 mol%), sodium tert-butoxide (1.62 g, 16.82 mmol, 2.0 equiv). The nitrogen was replaced three times, and tri-tert-butylphosphine (1.6mL, 0.67mmol, 8.0mol%; 10wt% hexane solution, density: 0.861 g / mL) and o-xylene 30mL were added under the protection of nitrogen, and the temperature of the oil bath was raised to Stir and react at 130°C for 12.0 hours, monitor by thin-layer chromatography until the reaction of the raw materials is complete, and cool to room temperature. The solvent was distilled off under reduced pressure, the sample was loaded by dry method, separated and purified by silica gel column chromatography, and the eluent was petroleum ether / ethyl acetate =...

Embodiment 3

[0095] Embodiment 3: The luminescent material NOBF2-3 can be synthesized according to the following route:

[0096]

[0097] Synthesis of intermediate OCH3-3: Intermediate 2 (592 mg, 2 mmol, 1.0 equivalent), 3,6-diphenylcarbazole (2.4 mmol, 767 mg, 1.2 equivalent), tert-butyl Sodium alkoxide (6mmol, 577mg, 3.0eq) and Pd(OAc) 2 (0.06mmol, 14mg, 3mol%). Then replace nitrogen three times, inject t-Bu 3 P (376μl, 0.16mmol, 8mol%, 10wt% hexane solution, density; 0.861g / mL), xylene (36mL), refluxed in an oil bath at 150°C for 48 hours, and monitored by thin-layer chromatography until the reaction of the raw materials was complete. Add a small amount of water to quench, extract three times with ethyl acetate, combine the organic phases, and use Na 2 SO 4 Dry, filter, and distill off the solvent under reduced pressure. The crude product was separated and purified by silica gel column chromatography, eluent: petroleum ether / ethyl acetate=10:1-3:1, and 1149 mg of a light yellow s...

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Abstract

The invention discloses organic light-emitting materials containing a dinitrogen difluoride-boron-oxygen heterocyclic receptor structural unit that are as shown in the formula (1) or the formula (2) and application thereof. By using the high-eletrophilicity dinitrogen difluoride-boron-oxygen heterocyclic structural unit as the receptor and combining different donors, a thermotropic delayed fluorescent material with high quantum efficiency, easily-adjustable emitting color, good device performance and high device luminance can be formed. The material has a huge application prospect in the fieldof OLED materials.

Description

technical field [0001] The invention belongs to the field of organic light-emitting materials, in particular to a class of organic light-emitting materials containing nitrogen difluoride-boron-oxapolycyclic acceptor structural units, which can be used in the fields of OLED display and lighting. Background technique [0002] An organic light-emitting diode (OLED, Organic Light-Emitting Diode) is also called an organic light-emitting device (Organic Light-Emitting Device) or an organic electroluminescent device (Organic Electroluminescent Device). Organic electroluminescence refers to a luminescence phenomenon in which small organic molecules, metal-organic complex molecules or polymer molecular light-emitting materials directly convert electrical energy into light energy under the action of a forward bias electric field. OLED is self-luminous, without backlight, and energy-saving; it also has the characteristics of fast response, low driving voltage, high luminous efficiency ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06H01L51/54
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1037C09K2211/104C09K2211/1044H10K85/657H10K85/6572H10K85/322
Inventor 李贵杰娄微微邓超
Owner ZHEJIANG HONGWU TECH CO LTD
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