Electroluminescent device based on chiral thermal activation delayed fluorescence material and preparation method thereof

An electroluminescent device, thermal activation delay technology, applied in the direction of luminescent materials, electro-solid devices, chemical instruments and methods, etc. problem, to achieve the effect of high yield, few preparation steps and good thermal stability

Active Publication Date: 2020-12-04
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The invention discloses an electroluminescent device based on a chiral thermally activated delayed fluorescent material and a preparation method thereof. The chemical name of the chiral thermally activated delayed fluorescent material is R / S-18,21-bis(10H-phenoxazine -10-yl)-3,4,5,6,7,8,9,10-octahydrodibenzo[a,c]dinaphtho[2',1':5,6; 1'', 2'': 7,8][1,4]dioxin[2,3-i]phenazine or R / S-16,17-bis(4-(10H-phenoxazin-10-yl)benzene base)-3,4,5,6,7,8,9,10-octahydrobina[2',1':5,6; 1'',2'':7,8][1, 4] Dioxane[2,3-g]quinoxaline, which is used to solve the problems of difficult synthesis and preparation of chiral delayed fluorescent light-emitting materials, few types of materials, and low efficiency of circularly polarized delayed fluorescent devices; Red light TADF materials have many preparation steps, expensive raw materials, complex synthesis and purification processes, low yield, and difficulty in mass production; especially, the CP- OLED, achieving its EQE exceeding 20%, and the asymmetry factor g greater than 10 -3 The goal

Method used

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  • Electroluminescent device based on chiral thermal activation delayed fluorescence material and preparation method thereof
  • Electroluminescent device based on chiral thermal activation delayed fluorescence material and preparation method thereof
  • Electroluminescent device based on chiral thermal activation delayed fluorescence material and preparation method thereof

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Effect test

Embodiment 1

[0051] The reaction formula is as follows:

[0052]

[0053] The reaction is as follows:

[0054] Add 0.45 g (3.12 mmol) of 4,5-difluorobenzene-1,2-diamine and 1.12 g (3.06 mmol) of 3,6-dibromo-9,10-phenanthrenequinone into a 150 mL three-necked flask, and then add 100 mL of absolute ethanol as a solvent, stirred under the protection of nitrogen, reacted at 80 °C for 2 hours, then filtered the reaction solution, and recrystallized the filter cake with absolute ethanol to obtain a light yellow solid 3,6-dibromo-11,12-di Fluorodibenzo[a,c]phenazine in 95% yield.

[0055] 0.50 g (1.05 mmol) 3,6-dibromo-11,12-difluorodibenzo[a,c]phenazine, 0.40 g (2.18 mmol) 10H-phenoxazine, 0.41 g (4.27 mmol) sodium tert-butoxide, 0.016 g (0.055 mmol) tri-tert-butylphosphine tetrafluoroborate, 0.05 g (0.055 mmol) tris(dibenzylideneacetone) dipalladium (0), then add 50 mL toluene As a solvent, the reaction was heated at 100 °C under the protection of nitrogen; after the reaction was complete...

Embodiment 2

[0063] The reaction formula is as follows:

[0064]

[0065] The reaction is as follows:

[0066] 0.45 g (3.12 mmol) 4,5-difluorobenzene-1,2-diamine and 1.12 g (3.04 mmol) 1,2-bis(4-bromophenyl)ethane-1 were added to a 150 mL three-neck flask, 2-diketone, then add 100 mL of absolute ethanol as a solvent, stir under the protection of nitrogen, react at 80 °C for 2 hours, then filter the reaction solution, and recrystallize the filter cake with absolute ethanol to obtain a light yellow solid 2,3- Bis(4-bromophenyl)-6,7-difluoroquinoxaline, yield 95%.

[0067]1.00 g (2.10 mmol) 2,3-bis(4-bromophenyl)-6,7-difluoroquinoxaline, 0.80 g (4.36 mmol) 10H-phenoxazine, 1.00 g (10.4 mmol) sodium tert-butoxide, 0.032 g (0.11 mmol) tri-tert-butylphosphine tetrafluoroborate, 0.10 g (0.11 mmol) tris(dibenzylideneacetone) dipalladium (0), and then add 50 mL toluene for Solvent, heat reaction at 100 ℃ under the protection of nitrogen; after the reaction is completed, extract with 100 mL of...

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Abstract

The invention relates to an electroluminescent device based on a chiral thermal activation delayed fluorescent material. The electroluminescent device comprises a chiral thermal activation delayed fluorescent material doped light-emitting layer, wherein a hole injection layer, a hole transport layer, a barrier layer, a light-emitting layer, an electron transport layer, an electron injection layerand a cathode are sequentially evaporated on an anode in vacuum, so that the electroluminescent device based on the chiral thermal activation delayed fluorescence material is obtained. The circular polarization electroluminescent device based on the chiral thermal activation delayed fluorescence material can emit yellow or orange red fluorescence (lambda=548 or 600 nm), the external quantum efficiency EQE of the device reaches 28.3% and 20.3%, the asymmetric factors are 6.0*10<-4> and 2.4*10<-3>, and the electroluminescent device has the advantages of being low in driving voltage, good in light emitting stability and the like.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an electroluminescent device based on a chiral thermally activated delayed fluorescent material that can be industrialized and has good performance and a preparation method thereof. Background technique [0002] Electroluminescence (English electroluminescent), also known as electric field luminescence, or EL for short, is to generate an electric field by applying a voltage to two electrodes, and the electrons excited by the electric field hit the luminescent center, causing electrons to transition, change, A physical phenomenon in which recombination results in luminescence. It is generally believed that under the action of a strong electric field, the energy of the electrons increases correspondingly until it far exceeds the energy of the electrons in the thermal equilibrium state and becomes a superheated electron. The superheated electrons can ionize the cr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): H01L51/50H01L51/54H01L51/56C07D493/04C09K11/06
CPCC07D493/04C09K11/06C09K2211/1048C09K2211/1033H10K71/164H10K85/657H10K50/11H10K71/00
Inventor 李艳青谢凤鸣唐建新周经雄曾馨逸
Owner SUZHOU UNIV
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