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An organic electroluminescent material with oxygen fluorene structure, its preparation method and its application

An electroluminescence, electromechanical 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, and achieve high thermal stability and optoelectronic performance. Agglomeration, good film-forming effect

Active Publication Date: 2018-05-18
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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  • An organic electroluminescent material with oxygen fluorene structure, its preparation method and its application
  • An organic electroluminescent material with oxygen fluorene structure, its preparation method and its application
  • An organic electroluminescent material with oxygen fluorene structure, its preparation method and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The preparation of embodiment 1 intermediate 1

[0044] Preparation of Intermediate 1-1: In a 500mL three-necked flask, add methyl 5-bromo-2-iodoformate (34.1g, 0.10mol), dibenzofuran-4-boronic acid (23.3g, 0.11mmol), carbonic acid Potassium (27.6g, 0.20mol), 82.8g water, Pd(PPh 3 ) 4 (578mg, 0.5mmol), toluene (150mL), absolute ethanol (50mL), N 2Protection, heating to reflux, heat preservation reaction, 4 hours, stopping the reaction, cooling to 25°C, separating liquids, collecting the organic phase, washing with water until neutral, and removing the solvent from the organic phase under reduced pressure to obtain the crude product of intermediate 1-1, which is not Refined, directly into the next reaction.

[0045] Preparation of Intermediate 1-2: In a 500mL three-neck flask, add Intermediate 1-1 (38.1g, 0.10mol), sodium hydroxide (12.0g, 0.30mol), absolute ethanol (200mL), N 2 Protect, heat up to reflux, keep warm for 3 hours, cool down to 25°C, add 10% dilute hydr...

Embodiment 2

[0050] The preparation of embodiment 2 compound C02

[0051]

[0052] In a 250mL three-necked flask, add intermediate 1 (6.14g, 10mmol), 1-naphthaleneboronic acid (3.78g, 22mmol), potassium carbonate (4.15g, 30mmol), Pd(PPh 3 ) 4 (58mg, 0.05mmol), mixed xylenes (80mL), N 2 Protect, raise the temperature to reflux, keep the reaction for 8 hours, stop the reaction, lower the temperature to 25°C, add 50mL deionized water, stir for 5min, separate the liquid, collect the organic phase, remove the solvent, and obtain the crude product of CO2, which is purified by silica gel column chromatography , to obtain the target compound C01, with an HPLC purity of 99.83% and a yield of 82.65%. High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 55 h 32 O, theoretical value 708.2453, test value 708.2456. Elemental analysis (C 55 h 32 O), theoretical value C: 93.19, H: 4.55, O: 2.26, measured value C: 93.17, H: 4.56, O: 2.27.

Embodiment 3

[0053] The preparation of embodiment 3 compound C04

[0054] Carry out with reference to Example 2, the raw materials are intermediate 1 and 4-biphenylboronic acid, to obtain the C04 compound, the HPLC purity is 99.95%, and the yield is 78.52%. High resolution mass spectrometry, ESI source, positive ion mode, molecular formula C 59 h 36 O, theoretical value 760.2766, test value 760.2761. Elemental analysis (C 59 h 36 O), theoretical value C: 93.13, H: 4.77, O: 2.10, measured value C: 93.11, H: 4.76, O: 2.13.

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Abstract

The invention discloses an organic electroluminescent material with an oxyfluorene structure, its preparation method and its application. The organic electroluminescent material has a molecular structure represented by the following formula: the novel organic fluorene with an oxyfluorene structure The spiro-ring small molecule organic electroluminescent material has the characteristics of intermolecular crystallization, aggregation and good film-forming properties. It has suitable HOMO and LUMO energy levels and can be used as a light-emitting layer in organic electroluminescent devices. , so that this type of organic electroluminescent device has high thermal stability and photoelectric performance.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an organic electroluminescent material with an oxyfluorene structure, a preparation method and an application thereof. 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 electroluminescent technology is mainly used in two fields, namely full-color display and white lighting. Commodities based on OLED display technology have gradually realized industrialization, for example, in products such as smart phones and curved TVs. , this technique has...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D307/77C07D405/14C07D307/91C07D405/04H01L51/54
CPCC09K11/06C07D307/77C07D307/91C07D405/04C07D405/14C09K2211/1029C09K2211/1088H10K85/622H10K85/626H10K85/615H10K85/6574H10K85/6572H10K50/11
Inventor 高自良张成新石宇李庆胡葆华孟凡民
Owner VALIANT CO LTD