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Heterocyclic organic electroluminescent material with chrysene as center structure, and preparation method and application thereof

A central structure, electroluminescence technology, applied in the fields of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of immature blue light-emitting devices, low device life and efficiency, etc., and achieve good film stability, good photoelectricity. performance, the effect of not easy to crystallize

Inactive Publication Date: 2019-06-18
VALIANT CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to realize full-color display, light-emitting devices of red, green, and blue colors are required respectively. Compared with red light devices and green light devices, blue light-emitting devices are not mature enough, and the device life and efficiency are low

Method used

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  • Heterocyclic organic electroluminescent material with chrysene as center structure, and preparation method and application thereof
  • Heterocyclic organic electroluminescent material with chrysene as center structure, and preparation method and application thereof
  • Heterocyclic organic electroluminescent material with chrysene as center structure, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] The preparation of embodiment 1 compound 1

[0051]

[0052] (1) Preparation of Intermediate 1-1: In a 2L three-necked flask, add 6,12-dibromochryl (77.2g, 0.20mol), 2-(methoxycarbonyl)phenylboronic acid (75.6g, 0.42mol) , potassium carbonate (82.8g, 0.60mol), tetrakistriphenylphosphine palladium (4.62g, 4.0mmol) and 800g toluene, 250g water, under the protection of nitrogen, react at 100-110°C for 10h, after the reaction, filter, filter cake Purified by column chromatography, and then recrystallized from toluene to obtain intermediate 1-1 with a yield of 87.64%;

[0053] (2) Preparation of Intermediate 1-2: In a 2L three-necked flask, add Intermediate 1-1 (74.5g, 0.15mol), 600g of tetrahydrofuran dehydrated, and stir to cool down to -50~-60°C under nitrogen protection , add methyllithium ether solution (0.90mol) dropwise, keep the temperature at -50~-60°C for 2 hours after the dropwise addition, then raise the temperature to room temperature and stir for 5 hours. ...

Embodiment 2

[0057] The preparation of embodiment 2 compound C02

[0058]

[0059] In a 250ml three-necked flask, under the protection of nitrogen, add compound 1 (6.18g, 0.01mol), 1-naphthylboronic acid (3.78g, 0.022mol), potassium carbonate (2.76g, 0.03mol), tetrakistriphenylphosphine Palladium (116mg, 0.1mmol), 8mL of water and 80mL of toluene were reacted at 80-90°C for 12h. After the reaction, filtered, purified by filter cake column chromatography, and then recrystallized by toluene and petroleum ether to obtain the target product C02, the yield was 82.19 %.

[0060] High resolution mass spectrum, molecular formula C56H40, theoretical value 712.3130, test value 712.3169.

Embodiment 3

[0061] The preparation of embodiment 3 compound C04

[0062] Referring to Example 2, the raw material 1-naphthaleneboronic acid was replaced with 4-biphenylboronic acid in the preparation process to obtain the target product C04 with a yield of 84.57%.

[0063] High resolution mass spectrum, molecular formula C60H44, theoretical value 764.3443, test value 764.3508.

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Abstract

The invention discloses a heterocyclic organic electroluminescent material with chrysene as a center structure, and a preparation method and an application thereof. The heterocyclic organic electroluminescent material with chrysene as the center structure is not prone to crystallize and aggregate, has an appropriate molecular weight, a good film stability and suitable HOMO and LUMO energy levels,and can be used in the field of organic electroluminescence as a luminescent layer for OLEDs. When the material is used as the luminescent layer material for OLEDs, the produced OLEDs have good photoelectric properties.

Description

technical field [0001] The invention belongs to the field of organic electroluminescence, and in particular relates to a heterocyclic organic electroluminescence material with a quinone-centered structure, a preparation method and an application. Background technique [0002] Organic electroluminescent diodes (OLEDs) were produced in the 1980s. They have many advantages such as self-illumination, wide viewing angle, fast response speed, and flexible display, which make them the most favorable competitors for the next generation of flat panel display technology. , has received great attention from people, and after more than 20 years of development, the technology has gradually matured. [0003] At present, organic electroluminescence technology is mainly applied in two fields, namely full-color display and white light illumination. Products based on OLED display technology have been gradually industrialized. For example, this technology has been widely used in products such...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07C13/62C07C13/72C07D307/91C07D333/76C07D213/06C07D251/24C07C211/54C07D209/86C07D209/80C07D235/18C07D239/74H01L51/50H01L51/54
Inventor 高自良张学衡王元勋沈朝祥周银波张书民
Owner VALIANT CO LTD
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