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Nitrogen-containing heterocyclic ring substituted cyclopropane compound and application thereof

A technology of cyclopropane and nitrogen heterocycle, applied in the field of electroluminescent materials, can solve the problems of lifespan decline, insufficient stability of organic light-emitting diodes, and pollution of devices, etc.

Pending Publication Date: 2021-04-09
GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, these current doping compounds have many defects when they are used for doping, such as unstable operation in the fabrication process of OLEDs, insufficient stability when driving OLEDs, and reduced lifetime, or when using vacuum evaporation. When plating is used to manufacture OLEDs, the above compounds will diffuse in the device and contaminate the device

Method used

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  • Nitrogen-containing heterocyclic ring substituted cyclopropane compound and application thereof
  • Nitrogen-containing heterocyclic ring substituted cyclopropane compound and application thereof
  • Nitrogen-containing heterocyclic ring substituted cyclopropane compound and application thereof

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specific Embodiment

[0141] The synthesis method of the compound according to the present invention is exemplified, but the present invention is not limited to the following examples.

[0142] 1. Compounds and synthetic steps

[0143] The target compound is as follows:

[0144]

[0145]

Embodiment 1

[0146] Embodiment 1: the synthesis of compound PD-1

[0147]

[0148] Synthesis of Compound PD-1

[0149] Under nitrogen protection, anhydrous tetrahydrofuran (230 mL) and lithium hydride (0.88 g) were added to the dry reaction kettle. Cool down to 10-15°C, dissolve compound 1 (4mmol) in anhydrous tetrahydrofuran (30mL), and slowly add it dropwise into the reaction kettle (keep the temperature below 15°C). After the dropwise addition, stir for 45min, then cool down to 0-5°C; Dissolve pentachlorocyclopropane (1mmol) in anhydrous tetrahydrofuran (11mL), slowly add dropwise to the reaction kettle, after the dropwise addition, naturally warm up to room temperature, and react for 44h. After the reaction was monitored by TLC and MS, water (30mL) was slowly added to the reaction kettle. After the reaction solution was acidified with concentrated hydrochloric acid, ethyl acetate (30mL) was added and stirred for 30min. Extract, combine the organic phases, wash with saturated brine...

Embodiment 2

[0151] Embodiment 2: the synthesis of compound PD-2

[0152]

[0153] Synthesis of compound PD-2

[0154] Under the protection of nitrogen, anhydrous tetrahydrofuran (230 mL) and lithium hydride (0.88 g) were added into the dry reaction kettle. Cool down to 10-15°C, dissolve compound 2 (4mmol) in anhydrous tetrahydrofuran (30mL), and slowly add it dropwise into the reaction kettle (keep the temperature below 15°C). After the dropwise addition, stir for 45min, then cool down to 0-5°C; Dissolve pentachlorocyclopropane (1mmol) in anhydrous tetrahydrofuran (11mL), slowly add dropwise to the reaction kettle, after the dropwise addition, naturally warm up to room temperature, and react for 44h. After the reaction was monitored by TLC and MS, water (30mL) was slowly added to the reaction kettle. After the reaction solution was acidified with concentrated hydrochloric acid, ethyl acetate (30mL) was added and stirred for 30min. Extract, combine the organic phases, wash with satura...

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Abstract

The invention relates to a nitrogen-containing heterocyclic ring substituted cyclopropane compound and application thereof. The compound has a structure shown as a formula (1), shows excellent hole transport property and stability, can be used as a hole injection layer material in an organic electroluminescent element, and can also be used as a doping agent to be doped in a hole injection layer or a hole transport layer, so that the compound can be driven by low voltage, the electroluminescent efficiency can be improved, and the service life of a device can be prolonged.

Description

[0001] This application claims the priority of the Chinese patent application submitted to the China Patent Office on October 8, 2019, the application number is 201910948284X, and the title of the invention is "a nitrogen-containing heterocyclic substituted cyclopropane compound and its application", the entire content of which Incorporated in this application by reference. technical field [0002] The invention relates to the field of electroluminescent materials, in particular to a cyclopropane compound substituted by a nitrogen-containing heterocyclic ring and its application in organic electronic devices. Background technique [0003] Organic light-emitting diodes (OLEDs) have great potential for applications in optoelectronic devices such as flat panel displays and lighting due to the synthetic versatility, relatively low fabrication cost, and excellent optical and electrical properties of organic semiconductor materials. [0004] The organic electroluminescence phenome...

Claims

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Application Information

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IPC IPC(8): C07D251/20C07D239/30C07D239/28C07D241/16C07D213/85C07D213/84C07D217/02C07D241/42C07D239/74C09K11/06H01L51/50H01L51/54
CPCC07D251/20C07D239/30C07D239/28C07D241/16C07D213/85C07D213/84C07D217/02C07D241/42C07D239/74C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1059H10K85/654H10K85/6572H10K50/15H10K50/17
Inventor 温华文杨曦刘爱香宋晶尧李们在李先杰王煦张月
Owner GUANGZHOU CHINARAY OPTOELECTRONICS MATERIALS
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