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Preparation method of chiral thermally activated delayed fluorescent materials

一种热激活延迟、荧光材料的技术，应用在发光材料、有机化学方法、化学仪器和方法等方向，能够解决圆偏振延迟荧光器件效率低、合成及纯化工艺复杂、合成制备步骤多等问题，达到产率高、制备步骤少、热稳定性好的效果

Active Publication Date: 2021-10-22
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] 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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  • Preparation method of chiral thermally activated delayed fluorescent materials
  • Preparation method of chiral thermally activated delayed fluorescent materials
  • Preparation method of chiral thermally activated delayed fluorescent materials

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Experimental program
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Effect test

Embodiment 1

[0071] The reaction formula is as follows:

[0072]

[0073] The reaction is as follows:

[0074] 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.

[0075] 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 wa...

Embodiment 2

[0083] The reaction formula is as follows:

[0084]

[0085] The reaction is as follows:

[0086] 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%.

[0087] 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 10...

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Abstract

The invention relates to a preparation method of a chiral thermally activated delayed fluorescent material. The preparation method comprises the following steps: reacting 10, 10'-(11, 12-difluorodibenzo[a, c]phenazine-3, 6-diyl)bis(10H-phenoxazine) and 5, 5', 6, 6 ', 7, 7', 8, 8'-octahydrobinaphthol taken as raw materials to prepare the chiral thermally activated delayed fluorescent material R1 and S1; or reacting 10, 10'-(((6, 7-difluoroquinoxaline-2, 3-diyl)bis(4, 1-phenylene))bis(10H-phenoxazine) and 5, 5', 6, 6 ', 7, 7', 8, 8'-octahydrobinaphthol used as raw materials to prepare the chiral thermally activated delayed fluorescent materials R2 and S2. The compounds prepared by the invention have the characteristics of rigid large-plane distortion structure and 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 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 large-scale synthesis and preparation can be realized.

Description

[0001] The present invention is a divisional application of an invention application titled chiral thermally activated delayed fluorescent material and its preparation method, application number CN2020109374617, and application date of September 8, 2020, and belongs to the preparation method technology department. technical field [0002] The invention relates to the field of organic electroluminescence materials, in particular to a preparation method of a chiral heat-activated delayed fluorescent material that can be industrialized and has good performance. Background technique [0003] 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 ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/056C09K11/06H01L51/54H01L51/50
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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