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Organic electroluminescent material with dibenzofuran structure and preparation method and application thereof

A luminescent and electromechanical technology, applied in luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of immature blue light-emitting devices, low device life and low efficiency, and achieve high thermal stability and photoelectric performance. Aggregation, not easy to crystallize

Active Publication Date: 2017-03-29
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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  • Organic electroluminescent material with dibenzofuran structure and preparation method and application thereof
  • Organic electroluminescent material with dibenzofuran structure and preparation method and application thereof
  • Organic electroluminescent material with dibenzofuran structure and preparation method and application thereof

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, cool down 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 a dibenzofuran structure and a preparation method and application thereof. The organic electroluminescent material has the following molecular structure (the structure is shown in the description). The novel spiro-type micromolecular organic electroluminescent material with the dibenzofuran structure has the advantages that molecules are not prone to be crystallized or aggregated, and the good film forming property is achieved, has the suitable HOMO and LUMO energy levels and can be applied in organic electroluminescent devices by serving as a luminescent layer, and therefore the organic electroluminescent devices achieve the high thermal stability and photoelectric property.

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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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
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