Thermal activated delayed fluorescence material based on arylboronic derivative and organic electroluminescence device

A technology based on derivatives and aryl groups, applied in the field of thermally activated delayed fluorescent materials and organic electroluminescent devices, can solve the problems of weak rigidity, high non-radiative transition rate, and low luminous efficiency

Active Publication Date: 2018-12-07
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the weak rigidity of this type of molecules, the high non-radiative transition rate leads to low luminous efficiency.
At the same time, most of the existing phosphorescent materials and TADF materials have a significant concentration quenching effect, resulting in most of the existing high-efficiency OLED devices being doped devices
However, the selection of the host material and the co-deposition preparation of the light-emitting layer are relatively complicated in the preparation of doped devices.

Method used

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  • Thermal activated delayed fluorescence material based on arylboronic derivative and organic electroluminescence device
  • Thermal activated delayed fluorescence material based on arylboronic derivative and organic electroluminescence device
  • Thermal activated delayed fluorescence material based on arylboronic derivative and organic electroluminescence device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Synthetic method of structural compound shown in formula I-1:

[0074]

[0075] 2-Bromo-3-fluorotoluene (1.89g, 10mmol), carbazole (1.67g, 10mmol) and cesium carbonate (6.52g, 20mmol) were added to 15mL dimethylformamide (DMF), and the mixture was stirred at 150°C After 12 hours, it was poured into 200ml of water, and the precipitate was collected by filtration. After column purification, a total of 3.1 g of white solid 9-(2-bromo-3-methylphenyl)carbazole was obtained, with a yield of 92%.

[0076] 9-(2-bromo-3-methylphenyl)carbazole (5mmol, 1.68g) was dissolved in 15mL of dry cyclopentyl methyl ether, and n-BuLi hexane solution (2.5 M, 2mL, 5mmol), and continued to stir at this temperature for 30 minutes, then added dropwise a solution (5mL) of bis(trimethylphenyl)boron fluoride (1.34g, 5mmol) in cyclopentyl methyl ether, dropwise Upon completion the mixture was warmed to room temperature and stirred overnight. After completion of the reaction, add saturated aque...

Embodiment 2

[0080] Synthesis method of the structural compound shown in formula I-2: the reactant carbazole is replaced by 3,6-di-tert-butyl carbazole, and through the same synthesis method as in Example 1, the structural compound shown in formula I-2 is obtained, and the total product rate of 61%.

[0081] The molecular weight obtained by mass spectrometry: 617.42

[0082] The relative molecular mass percentages of each element (C / H / N) obtained by elemental analysis: C, 87.63; H, 8.45; N, 2.22.

Embodiment 3

[0084] Synthesis method of the structural compound shown in formula I-3: the reactant carbazole is replaced by 9,10-dihydro-9,9-dimethylacridine, and the compound of formula I-3 is obtained through the same synthesis method as in Example 1 The structure compound is shown, and the total yield is 57%.

[0085] The molecular weight obtained by mass spectrometry: 547.34

[0086] The relative molecular mass percentages of each element (C / H / N) obtained by elemental analysis: C, 87.78; H, 7.75; N, 2.50.

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Abstract

The invention relates to a thermal activated delayed fluorescence material based on an arylboronic derivative and an organic electroluminescence device. The thermal activated delayed fluorescence material based on the arylboronic derivative has a structure shown as formula A. The invention also relates to the organic electroluminescence device which comprises a light-emitting layer, wherein the activated delayed fluorescence material is served as a luminescent dye in the light-emitting layer. A singlet state-triplet state energy gap of the thermal activated delayed fluorescence material is tiny; under room temperature, triplet excitons can be up-converted to triplet exciton luminescence through thermal activation; the thermal activated delayed fluorescence material is simply compounded andhas high luminescence efficiency, small concentration quenching effect and excellent dissolving property; the organic electroluminescence device based on the material can acquire higher efficiency and higher stability.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials and devices, in particular to a thermally activated delayed fluorescent material and organic electroluminescent devices based on aryl boron derivatives. Background technique [0002] Organic light emitting diode (OLED) technology has attracted much attention due to its great application potential in the fields of display and lighting. Among them, the development of luminescent materials is the core of OLED technology and the focus of industry competition. According to spin statistics, the ratio of singlet excitons to triplet excitons generated by the recombination of holes and electrons in the light-emitting material is 1:3. It is generally believed that traditional fluorescent materials can only use singlet excitons to emit light, and the highest theoretical internal quantum efficiency of the device is 25%. Phosphorescent materials based on platinum heavy metal complexes have...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06C09B57/00H01L51/50H01L51/54
CPCC09K11/06C07F5/027C09B57/00C09K2211/1007C09K2211/1014C09K2211/1029H10K85/6572H10K50/11
Inventor 卢灿忠陈旭林贾吉慧
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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