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Thermally activated delayed fluorescence material with phenanthroimidazole structure, preparation method of material and application of material

A technology of thermally induced delayed fluorescence and phenanthroimidazole, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve problems such as efficiency roll-off

Active Publication Date: 2019-10-08
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, for all TADF devices, at high current densities, singlet-triplet annihilation (STA), triplet-triplet annihilation (TTA), triplet-polaron annihilation (TPQ), and excited states The non-radiative attenuation caused by molecular vibration relaxation will cause the efficiency roll-off to be very serious. Therefore, the further development of TADF materials and the solution to the problem of its efficiency roll-off are current research hotspots in the field of OLEDs.

Method used

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  • Thermally activated delayed fluorescence material with phenanthroimidazole structure, preparation method of material and application of material
  • Thermally activated delayed fluorescence material with phenanthroimidazole structure, preparation method of material and application of material
  • Thermally activated delayed fluorescence material with phenanthroimidazole structure, preparation method of material and application of material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Embodiment 1: The present invention is that the above compound 1 (PPZPPI) can be synthesized by the following method.

[0086]

[0087] (1) Dissolve phenanthrenequinone (31.23g, 150mmol), aniline (16.76g, 180mmol), 4-bromobenzaldehyde (33.30g, 180mmol), ammonium acetate (23.12g, 300mmol) in a 500ml three-necked flask in 300mL Add acetic acid to the reactor, under nitrogen atmosphere, heat up to 115°C and react for 12 hours, the liquid phase monitors the completion of the reaction, cool to room temperature, wash with water twice, filter, and recrystallize twice with ethyl acetate to obtain 78.35g intermediate Body a, yield 85%;

[0088] (2) Dissolve phenazine (36.04g, 200mmol) in 200mL ethanol and add it to a 1000mL reactor, blow nitrogen into it, heat up to 85°C, dissolve sodium dithionite (174.10g, 1000mmol) in 400mL pure water The liquid funnel was slowly added dropwise to the reactor. After the dropwise addition, stirred for 30 minutes, cooled to room temperature...

Embodiment 2

[0090] Example 2: The above compound 2 (PPZTPI) of the present invention can be synthesized by the following method.

[0091]

[0092] (1) In a 500ml three-necked flask, phenanthrenequinone (31.23g, 150mmol), 4-tert-butylaniline (26.86g, 180mmol), 4-bromobenzaldehyde (33.30g, 180mmol), ammonium acetate (23.12g, 300mmol ) was dissolved in 300mL of acetic acid and added to the reactor, under a nitrogen atmosphere, the temperature was raised to 115°C for 10 hours, and the reaction was completed by liquid phase monitoring, cooled to room temperature, washed twice with water, filtered, and recrystallized twice from ethyl acetate, namely 67.48g of intermediate a can be obtained with a yield of 89%.

[0093] (2) The synthesis method of intermediate b 5,10-dihydrophenazine is the same as in Example 1.

[0094] (3) In a 500mL three-necked flask, add 5,10-dihydrophenazine (18.22g, 100mmol), bromobenzene (15.70g, 100mmol), potassium carbonate (41.46g, 300mmol), crown ether (2.64g, 10...

Embodiment 3

[0095] Example 3: The above compound 7 of the present invention can be synthesized by the following method.

[0096]

[0097] (1) In a 500ml three-necked flask, phenanthrenequinone (31.23g, 150mmol), 4-(9H-carbazol-9-yl)aniline (46.49g, 180mmol), 4-bromobenzaldehyde (33.30g, 180mmol), Ammonium acetate (23.12g, 300mmol) was dissolved in 300mL of acetic acid and added to the reactor. Under a nitrogen atmosphere, the temperature was raised to 115°C for 12 hours. The reaction was completed by liquid phase monitoring, cooled to room temperature, washed twice with water, filtered, and ethyl acetate The ester was recrystallized twice to obtain 78.35 g of intermediate a with a yield of 85%.

[0098] (2) The synthesis method of intermediate b 5,10-dihydrophenazine is the same as in Example 1.

[0099] (3) In a 500mL three-necked flask, add 5,10-dihydrophenazine (18.22g, 100mmol), bromobenzene (15.70g, 100mmol), potassium carbonate (41.46g, 300mmol), crown ether (2.64g, 10mmol ), 200...

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Abstract

The invention belongs to the field of photoelectric material applied technologies, and particularly relates to a thermally activated delayed fluorescence material with a phenanthroimidazole structure,an application of the material and an electroluminescence device. The phenanthroimidazole structure rich in electrons and holes and a phenazine structure are connected through an aromatic group to form the material, and the delayed fluorescence material simultaneously meets a larger radiation transition constant kr and a smaller single-triplet-state energy gap delta EST. Dense donor-receptor group combinations effectively avoid energy consumption of triplet-state charge reaction caused by electron and hole carrier density imbalance of a device, so that the problem of roll off of the device isimproved. The phenanthroimidazole structure and the phenazine structure are designed, orbital overlap is effectively increased, molecular rigidity is increased, non-radiation transition is restrained, luminous efficiency of the device is effectively improved, and the material is an excellent luminous layer object material, emergent layer material and luminous layer subject material.

Description

technical field [0001] The invention belongs to the field of photoelectric material application technology, and in particular relates to a thermally induced delayed fluorescent material with a phenanthroimidazole structure and a preparation method and application thereof. Background technique [0002] Organic electroluminescent device (OLED) is a new display technology with ultra-thin, high brightness, wide viewing angle, self-illumination, low power consumption, low cost, bendable and low temperature conditions (the liquid crystal in TFT-LCD is in It will solidify under such conditions) and can work normally. It is praised by the industry as the ideal and most promising next-generation display technology after LCD. [0003] Organic light-emitting materials are the key factors affecting organic electroluminescent devices. In order to improve the performance of light-emitting diodes and the yield rate of OLED panels, various light-emitting material systems based on fluorescen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/10C07D401/14C07D403/10C07D403/14C07D413/10C07D413/14C07D417/10C07D417/14C09K11/06H01L51/54
CPCC07D403/10C07D403/14C07D413/10C07D413/14C07D417/10C07D417/14C07D401/10C07D401/14C09K11/06C09K2211/1044H10K85/631H10K85/657H10K85/6572
Inventor 穆广园庄少卿任春婷
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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