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Fluorenone derivative, and preparation and application thereof

A derivative, fluorenone technology, applied in the field of fluorenone derivatives and their preparation and application, can solve the problems of incomplete removal of long-wave emission, oxygen quenching and the like

Active Publication Date: 2019-04-05
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although the stabilization strategy can improve the luminous efficiency, it can only inhibit the generation of excigroups caused by interchain interactions to a certain extent, and does not completely remove the long-wave emission. Spiro compounds still show obvious Oxygen quenching, therefore, the spectral stability of fluorene derivative materials needs to be further improved

Method used

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  • Fluorenone derivative, and preparation and application thereof
  • Fluorenone derivative, and preparation and application thereof
  • Fluorenone derivative, and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058]

[0059] (1) In a 250mL three-necked flask, put 3-biphenylboronic acid (9.90g, 50mmol), 4-bromopyridine-2-boronic acid (10.09g, 50mmol), potassium carbonate (13.82g, 100mmol), and add 100 mL Toluene, under nitrogen atmosphere, add Pd(PPh 3 ) 4 (0.17g, 0.15mmol), warming up to 85°C and reacting for 6-24h, the liquid phase monitors the completion of the reaction, cooling to room temperature, washing with water, filtering, separating the filtrate, extracting and concentrating the organic layer to obtain the crude intermediate (4-( [1,1'-biphenyl-3-yl)pyridin-2-yl)boronic acid 13.20g, yield 96%;

[0060] (2) In a 100mL three-necked flask, drop 2-bromofluorenone (2.59g, 10mmol), intermediate (4.13g, 15mmol), cesium carbonate (13.82g, 30mmol), add 40mL tetrahydrofuran and 20mL water, and Atmosphere, add PdCl 2 (dppf)-CH 2 Cl 2 (0.16g, 0.2mmol), heated to 65°C and reacted for 6-24h, the liquid phase monitored the completion of the reaction, cooled to room temperature, ...

Embodiment 6

[0071]

[0072] Prepare the target compound in the above formula according to the same method as Example 1 (compared with Example 1, the reactants of each corresponding step can be different, but the reactant molar ratio and reaction conditions are the same), the final product 3.81 g, yield 83%. Mass spectrometer MALDI-TOF-MS (m / z) = 459.5487, theoretical molecular weight: 459.5480; Anal.Calcd forC 34 h 21 N(%): C 88.86, H 4.61, N 3.05, Fnd: C 86.85, H 4.60, N 3.05

[0073]

[0074] Prepare the target compound in the above formula according to the same method as in Example 1 (compared with Example 1, the reactants of each corresponding step can be different, but the reactant molar ratio and reaction conditions are the same), the final product 3.51 g, yield 81%. Mass spectrometer MALDI-TOF-MS (m / z) = 433.5105, theoretical molecular weight: 433.5100; Anal.Calcd forC 32 h 19 N(%): C 88.66, H 4.42, N 3.23, Found: C 88.65, H 4.43, N 3.23.

[0075]

[0076] Prepare th...

Embodiment 11

[0082]

[0083] Prepare the target compound in the above formula according to the same method as Example 1 (compared with Example 1, the reactants of each corresponding step can be different, but the reactant molar ratio and reaction conditions are the same), the final product 4.53 g, yield 79%. Mass spectrometer MALDI-TOF-MS (m / z) = 573.6954, theoretical molecular weight: 573.6950; Anal.Calcd forC 43 h 27 N(%): C 90.03, H 4.74, N 2.44, Found: C 90.02, H 4.75, N 2.44.

[0084]

[0085] Prepare the target compound in the above formula according to the same method as Example 1 (compared with Example 1, the reactants of each corresponding step can be different, but the reactant molar ratio and reaction conditions are the same), the final product 3.99 g, yield 82%. Mass spectrometer MALDI-TOF-MS (m / z) = 486.5735, theoretical molecular weight: 486.5740; Anal.Calcd forC 35 h 22 N 2 (%): C 86.40, H 4.56, N 5.76, Found: C 86.42, H 4.55, N 5.76.

[0086]

[0087] Prepar...

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PUM

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Abstract

The invention discloses a fluorenone derivative, and preparation and application thereof. The fluorenone derivative has the advantages that the fluorenone derivative takes fluorenone as a core, and acompound with new characteristics is formed through bridging between a heterocyclic ring and a receptor gene to serve as a luminous layer main body material and an electron transfer material of an OLED device, so that the performance of the device in starting voltage, luminous intensity, external quantum efficiency, chromaticity, half-life and the like can be remarkably improved, and the working stability of the device can be enhanced.

Description

technical field [0001] The invention belongs to the field of photoelectric material application technology, and in particular relates to a fluorenone derivative and its preparation and application. Background technique [0002] OLED stands for Organic Light Emitting Diode, also known as Organic Laser Display (OLED). OLED has the characteristic of self-illumination. It adopts very thin organic material coating and glass substrate. When the current passes through, the organic material will emit light, and the OLED display screen has a large viewing angle and can significantly save power. Therefore, OLED is regarded as One of the most promising products of the 21st century. [0003] As a compound with a rigid planar biphenyl structure, fluorene has attracted extensive attention in the field of optoelectronic material application technology due to its wide energy gap, high luminous efficiency, and easy structural modification. One of the disadvantages of fluorene materials is ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/50C07D405/04C07D409/04C07D401/04C07D213/74C07D401/10C07D239/26C07D403/04C07D403/10C07D239/42C07D241/12C07D241/20C07D251/22C07D405/14C07D251/24C07D409/14C07D401/14C07D403/14C07D235/18C07D263/57C07D277/66C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D213/50C07D213/74C07D235/18C07D239/26C07D239/42C07D241/12C07D241/20C07D251/22C07D251/24C07D263/57C07D277/66C07D401/04C07D401/10C07D401/14C07D403/04C07D403/10C07D403/14C07D405/04C07D405/14C07D409/04C07D409/14C09K2211/1029C09K2211/1011C09K2211/1044C09K2211/1037C09K2211/1033C09K2211/1007C09K2211/1092C09K2211/1059C09K2211/1088H10K85/622H10K85/624H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/15H10K50/11
Inventor 穆广园庄少卿任春婷徐鹏
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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