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

AI Technical Summary

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

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

Examples

Experimental program
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Example Embodiment

[0140]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, compound and synthetic steps

[0143]The target compound is as follows:

[0144]

[0145]

Example Embodiment

[0146]Example 1: 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 dried reactor. Ciparateing to 10 to 15 ° C, compound 1 (4 mmol) was dissolved in anhydrous tetrahydrofuran (30 mL), slowly added to the reaction kettle (holding temperature at 15 ° C), after the dropping was added, stirred for 45min, then cool down 0 ~ 5 ° C; pentachloropropane (1 mmol) was dissolved in anhydrous tetrahydrofuran (11 mL), slowly added to the reaction elbow, after the dropwise addition, naturally heated to room temperature, reaction 44 h. After the TLC and MS monitoring reaction, water (30 ml) was slowly added to the reaction kettle, and after the reaction liquid acidified with concentrated hydrochloric acid, ethyl acetate (30 mL) was added, stirred after 30min, and then deposited, and ethyl acetate with acetate. Extraction, combined organic phase, washed with saturated brine...

Example Embodiment

[0151]Example 2: Synthesis of Compound PD-2

[0152]

[0153]Compound PD-2 synthesis

[0154]Under nitrogen protection, anhydrous tetrahydrofuran (230 mL) and lithium hydride (0.88 g) were added to the dried reaction kettle. Covered to 10 to 15 ° C, the compound 2 (4 mmol) was dissolved in anhydrous tetrahydrofuran (30 mL), slowly added to the reaction kettle (holding temperature below 15 ° C), after the dropping was added, stirred for 45min, then cool down 0 ~ 5 ° C; pentachloropropane (1 mmol) was dissolved in anhydrous tetrahydrofuran (11 mL), slowly added to the reaction elbow, after the dropwise addition, naturally heated to room temperature, reaction 44 h. After the TLC and MS monitoring reaction, water (30 ml) was slowly added to the reaction kettle, and after the reaction liquid acidified with concentrated hydrochloric acid, ethyl acetate (30 mL) was added, stirred after 30min, and then deposited, and ethyl acetate with acetate. Extraction, combined organic phase, washed with saturat...

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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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