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Chiral thermally activated delayed fluorescent material and preparation method thereof

A technology of thermally activated delayed and fluorescent materials, which is applied in the direction of luminescent materials, organic chemical methods, chemical instruments and methods, etc., can solve the problems of low efficiency of circularly polarized delayed fluorescent devices, complex synthesis and purification processes, and many synthesis and preparation steps. Achieve high yield, less preparation steps, and good thermal stability

Active Publication Date: 2021-08-27
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The invention discloses 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-phenoxazin-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)phenyl)-3,4 ,5,6,7,8,9,10-octahydrobinaphtho[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 luminescent materials, few types of materials, and low efficiency of circularly polarized delayed fluorescent devices; at the same time, it solves the synthesis and preparation of existing orange-red / red-light TADF materials There are many steps, expensive raw materials, complicated synthesis and purification processes, low yield, and difficulty in mass production; especially, the CP-OLED prepared by the chiral thermally activated delayed fluorescent material doped light-emitting layer achieves an EQE exceeding 20%, the asymmetry factor g is greater than 10 -3 The goal

Method used

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  • Chiral thermally activated delayed fluorescent material and preparation method thereof
  • Chiral thermally activated delayed fluorescent material and preparation method thereof
  • Chiral thermally activated delayed fluorescent material and preparation method thereof

Examples

Experimental program
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Embodiment 1

[0070] The reaction formula is as follows:

[0071] The reaction is as follows:

[0072]Add 0.45 g (3.12 mmol) 4,5-difluorobenzene-1,2-diamine and 1.12 g (3.06 mmol) 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.

[0073] 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 completed, it was extract...

Embodiment 2

[0081] The reaction formula is as follows:

[0082] The reaction is as follows:

[0083] 0.45 g (3.12 mmol) of 4,5-difluorobenzene-1,2-diamine and 1.12 g (3.04 mmol) of 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%.

[0084] 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 di...

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Abstract

The invention relates to a chiral thermally activated delayed fluorescent material and a preparation method thereof, which 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)phenyl)‑3,4,5,6,7,8,9, 10‑octahydrobinaphtho[2′,1′:5,6;1″,2″:7,8][1,4]dioxane[2,3‑g]quinoxaline. The compound provided by the present invention has the characteristics of rigid large plane twisted structure and significant internal charge transfer (ICT) effect, and has typical thermally activated delayed fluorescence properties (TADF), circular polarization (CPL) properties, and high fluorescence quantum yield ( PLQY) and good thermal stability. In addition, the synthesis and preparation steps are few, the raw materials are easy to obtain, the synthesis and purification process is simple, the yield is high, and the method can be synthesized and prepared on a large scale.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a chiral thermally activated delayed fluorescent material with industrialization and good performance and an electroluminescent device thereof. Background technique [0002] Organic light-emitting diodes (OLEDs) have attracted widespread attention due to their huge applications in light sources and flexible flat-panel displays. OLEDs, the first-generation light-emitting devices based on conventional fluorescent materials, show an internal quantum efficiency (IQE) as high as 25% and an external quantum efficiency (EQE) of 5–7.5%, because the emitting material can only obtain singlet excitons. The second-generation phosphorescent materials containing noble metal atoms can effectively utilize singlet and triplet excitons through spin-orbit coupling, and their IQE can reach 100%; however, considering that iridium (Ir) and platinum (Pt) are scarce and Expensive, th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/06C09K11/06H01L51/54H01L51/50
CPCC09K11/06C09K2211/1048C09K2211/1033C07B2200/07C07D491/056H10K85/657H10K50/12H10K50/11
Inventor 唐建新谢凤鸣李艳青周经雄曾馨逸
Owner SUZHOU UNIV
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