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Chiral thermal activation delayed fluorescence material and preparation method thereof

A technology of thermally activated delay and fluorescent materials, which is applied in the direction of luminescent materials, organic chemical methods, chemical instruments and methods, etc., and can solve the problems of low yield, difficulty in large-scale mass production, and few types of materials.

Active Publication Date: 2020-12-15
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 thermal activation delayed fluorescence material and preparation method thereof
  • Chiral thermal activation delayed fluorescence material and preparation method thereof
  • Chiral thermal activation delayed fluorescence material and preparation method thereof

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Embodiment 1

[0070] The reaction formula is as follows:

[0071]

[0072] The reaction is as follows:

[0073]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.

[0074] 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...

Embodiment 2

[0082] The reaction formula is as follows:

[0083]

[0084] The reaction is as follows:

[0085] 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%.

[0086] 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 o...

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Abstract

The invention relates to a chiral thermal activation delayed fluorescence material and a preparation method thereof. The delayed fluorescence material is R / S-18,21-di(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[2,3i]phenazine, or R / S-16,17-bis(4-(10H-phenoxazine-10-yl)phenyl)3,4,5,6,7,8,9,10-octahydronaphthalo[2',1':5,6; 1',2'':7,8][1,4]dioxane[2,3g] quinoxaline. The compound provided by the invention has the characteristics of a rigid large-plane twisted structure and a remarkable internal charge transfer (ICT) effect, and has the advantages of typical thermal activation delayed fluorescence (TADF) property, circular polarization (CPL) property, high fluorescence quantum yield (PLQY), good thermal stability and the like. The method has the advantages of few synthesis and preparation steps, readily available raw materials, simple synthesis and purification processes and high yield, and can be used for large-scale synthesis andpreparation.

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 Applications(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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