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Fluorenone derivative, and preparation and application thereof

A technology of derivatives and fluorenones, 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, etc.

Inactive 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

[0050]

[0051] In a 100mL three-necked flask, put 2-bromofluorenone (2.59g, 10mmol), [2,2'-binaphthyl]-6-ylboronic acid (2.98g, 10mmol), cesium carbonate (13.82g, 30mmol), Add 40mL tetrahydrofuran and 20mL water, under nitrogen 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, filtered, concentrated, and separated by column chromatography to obtain 3.63g of the target compound with a yield of 84%.

[0052] Mass spectrometer MALDI-TOF-MS (m / z) = 432.5216, theoretical molecular weight: 432.5220; Anal.Calcd forC 33 h 20 (%): C 91.64, H 4.66, Found: C 91.65, H 4.65.

Embodiment 2

[0054]

[0055] Replace [2,2'-binaphthyl]-6-ylboronic acid (2.98g, 10mmol) with (10-phenylanthracene-9-yl)boronic acid (2.98g, 10mmol), and other basic The same method was used to prepare the target compound in the above formula (the molar ratio of the reactants and the reaction conditions were the same), and 3.46 g of the target compound could be obtained with a yield of 80%. Mass spectrometer MALDI-TOF-MS (m / z) = 432.5218, theoretical molecular weight: 432.5220; Anal.Calcd for C 33 h 20 (%): C 91.64, H 4.66, Found: C 91.64, H 4.65.

Embodiment 3

[0057]

[0058] Replace [2,2'-binaphthyl]-6-ylboronic acid (2.98g, 10mmol) with fluoranthene-3-ylboronic acid (2.46g, 10mmol), and prepare the others in the same manner as in Example 1 The target compound in the formula (the molar ratio of reactants and the same reaction conditions) can obtain 2.93 g of the target compound with a yield of 77%. Mass spectrometer MALDI-TOF-MS (m / z) = 380.4460, theoretical molecular weight: 380.4460; Anal.Calcd for C 29 h 16 (%): C 91.56, H 4.24, Found: C 91.54, H 4.25.

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Abstract

The invention discloses a fluorenone derivative, and preparation and application thereof. The fluorenone derivative takes a fluorenone structure containing electron deficiency carbonyl groups as a core, and an aromatic fused ring compound with the electron deficiency characteristic is further bridged to form a compound with high hole transfer. The fluorenone derivative serving as a hole transfer material and a luminous layer main body material of an OLED device has the advantages of remarkably improved performance of the device in starting voltage, luminous intensity, external quantum efficiency, current efficiency, power efficiency, chromaticity, half-life and the like, and enhanced working stability of the device.

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 characteristics of self-illumination. It uses a 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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IPC IPC(8): C07C49/675C07D209/86C07D333/76C07D307/91C07D241/46C07D265/38C07D279/22C09K11/06H01L51/50H01L51/54C07C45/68
CPCC07C45/68C07C2603/94C07C2603/42C07C2603/40C07C2603/24C07C2603/18C07C2603/26C07C2603/50C09K2211/1011C09K2211/1007C09K2211/1029C09K2211/1033C09K2211/1092C09K2211/1088C09K2211/1044C09K2211/1037H10K85/622H10K85/624H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K50/15H10K50/11
Inventor 穆广园庄少卿任春婷徐鹏
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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