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Luminescent material based on fluorene arylamine compounds, preparation method of luminescent material and organic electroluminescent device

A technology of luminescent materials and compounds, applied in luminescent materials, electrical solid devices, silicon organic compounds, etc., can solve the problems of destroying hole-electron charge balance, quantum efficiency and service life deterioration, and quantum efficiency reduction.

Pending Publication Date: 2021-02-19
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, OLEDs using these materials have problems in deteriorating quantum efficiency and lifetime
This is because when the OLED is driven at high current, thermal stress occurs between the anode and the hole injection layer, and said thermal stress significantly reduces the lifetime of the device
In addition, since the organic material used in the hole transport region has very high hole mobility, the hole-electron charge balance may be disrupted and the quantum efficiency (cd / A) may decrease

Method used

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  • Luminescent material based on fluorene arylamine compounds, preparation method of luminescent material and organic electroluminescent device
  • Luminescent material based on fluorene arylamine compounds, preparation method of luminescent material and organic electroluminescent device
  • Luminescent material based on fluorene arylamine compounds, preparation method of luminescent material and organic electroluminescent device

Examples

Experimental program
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Effect test

Embodiment 1

[0084] This material example provides a luminescent material based on fluorene aromatic amine compounds, and its synthesis route is as follows:

[0085]

[0086] Its preparation method is as follows:

[0087] (1) Add reactant B-4 (110mmol) into a three-necked flask, add 500mL of anhydrous tetrahydrofuran, replace with nitrogen three times, then cool the reaction system to -78°C, and add (2.5M) n-BuLi (110mmoL) dropwise , stirred at -78°C for 2h. Reactant A-4 (100mol) was dissolved in tetrahydrofuran and added dropwise to the reaction system. After the dropwise addition was completed, the temperature was raised to room temperature and stirred for 10 h. Distilled water was added to terminate the reaction, the organic phase was collected by liquid separation, and dried by adding anhydrous magnesium sulfate. The remaining water was removed, anhydrous magnesium sulfate was removed by filtration, and the organic phase was removed by a rotary evaporator to obtain a solid organic...

Embodiment 2

[0097] This material example provides a luminescent material based on fluorene aromatic amine compounds, and its synthesis route is as follows:

[0098]

[0099] Its preparation method is as follows:

[0100] (1) Add reactant B-50 (110mmol) into a three-necked flask, add 500mL of anhydrous tetrahydrofuran, replace with nitrogen three times, then cool the reaction system to -78°C, and add (2.5M) n-BuLi (110mmoL) dropwise , stirred at -78°C for 2h. The reactant A-50 (100mol) was dissolved in tetrahydrofuran and added dropwise to the reaction system. After the dropwise addition was completed, the temperature was raised to room temperature and stirred for 10 h. Distilled water was added to terminate the reaction, the organic phase was collected by liquid separation, and dried by adding anhydrous magnesium sulfate. The remaining water was removed, anhydrous magnesium sulfate was removed by filtration, and the organic phase was removed by a rotary evaporator to obtain a solid o...

Embodiment 3

[0110] This material example provides a luminescent material based on fluorene aromatic amine compounds, and its synthesis route is as follows:

[0111]

[0112] Its preparation method is as follows:

[0113] (1) Add reactant B-75 (110mmol) into a three-necked flask, add 500mL of anhydrous tetrahydrofuran, replace with nitrogen three times, then cool the reaction system to -78°C, and add (2.5M) n-BuLi (110mmoL) dropwise , stirred at -78°C for 2h. The reactant A-75 (100mol) was dissolved in tetrahydrofuran and added dropwise to the reaction system. After the dropwise addition was completed, the temperature was raised to room temperature and stirred for 10 h. Distilled water was added to terminate the reaction, the organic phase was collected by liquid separation, and dried by adding anhydrous magnesium sulfate. The remaining water was removed, anhydrous magnesium sulfate was removed by filtration, and the organic phase was removed by a rotary evaporator to obtain a solid o...

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Abstract

The invention discloses a luminescent material based on fluorene arylamine compounds, a preparation method of the luminescent material and an organic electroluminescent device, and belongs to the technical field of chemical and luminescent materials. The structural general formula of the luminescent material is shown in the description, wherein X is selected from chemical bonds, O, S, Si(R5R6), C(R7R8) or NR9; any two of a, b, c and d are 1, and the rest are 0; R1 to R4 are independently selected from hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3-membered to 30-membered heteroaryl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryloxy, and C3-C30 aliphatic ring or C6-C30 aromatic ring connected with an adjacent substituent to form a monocyclic or polycyclic aromatic ring. The organic electroluminescent device containing the luminescent material is relatively low in drivingvoltage, relatively long in service life and relatively high in efficiency.

Description

technical field [0001] The invention relates to the technical field of chemistry and luminescent materials, in particular to a luminescent material based on a fluorene aromatic amine compound, a preparation method thereof, and an organic electroluminescent device. Background technique [0002] After entering the 21st century, people need a new generation of flat panel displays that can better meet the needs of future life and better performance to meet "4C" (ie communications, automotive electronics, computers, consumer electronics equipment) and "4G" (ie the fourth generation The advent of the mobile communication era. Organic Light Emitting Diode (OLED), as a new generation of display technology, has unparalleled advantages over LCD flat panel displays. An organic electrical element utilizing the organic light emitting phenomenon generally has a structure including an anode, a cathode and an organic layer therebetween. In order to improve the efficiency and stability of ...

Claims

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Application Information

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IPC IPC(8): C07C211/55C07C211/58C07C211/61C07C217/84C07D209/86C07D307/91C07D311/82C07D311/90C07D335/20C07D401/04C07D405/12C07D405/14C07D407/12C07D409/12C07F7/08C09K11/06H01L51/54H01L51/50
CPCC07D311/90C07D405/14C07D409/12C07D407/12C07D405/12C07D311/82C07C211/58C07C211/61C07C211/55C07C217/84C07D307/91C07D209/86C07D335/20C07F7/0816C07D401/04C09K11/06C07C2603/18C07C2603/24C09K2211/1096C09K2211/1088C09K2211/1092C09K2211/1029C09K2211/1007C09K2211/1011C09K2211/1014H10K85/636H10K85/626H10K85/633H10K85/615H10K85/631H10K85/6576H10K85/6574H10K85/6572H10K85/40H10K50/11
Inventor 汪康王进政孙向南王士凯陈振生韩文坤马晓宇
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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