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An orange-red photothermally activated delayed fluorescent material and an organic electroluminescent device

An electroluminescent device, thermal activation delay technology, applied in the direction of luminescent materials, electric solid devices, organic chemistry, etc., can solve the problems of expensive raw materials, many synthesis and preparation steps, and difficult synthesis and preparation, and achieve simple synthesis and purification process, Few synthesis preparation steps, good luminescence stability

Inactive Publication Date: 2021-04-27
SUZHOU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of the above-mentioned analysis, the object of the present invention is to: (1) provide a kind of novel 3,6,11-three (9,9-dimethylacridin-10 (9H)-yl) dibenzo[a,c ] The synthetic preparation method of the orange-red photothermally activated delayed fluorescence material of phenazine; And [a,c] phenazine's orange-red photothermally activated delayed fluorescent material OLED, to achieve the goal of its electroluminescence wavelength peak exceeding 600nm, and its EQE exceeding 22%, to solve the orange-red / red emission peak greater than 600nm Difficult synthesis and preparation of optical TADF light-emitting materials, few types of materials, and low PLQY of orange-red / red thermally activated delayed fluorescent devices; at the same time, it solves the problems of many steps in the synthesis and preparation of existing orange-red / red TADF materials, expensive raw materials, synthesis and purification processes Complicated, low yield, difficult to mass-produce

Method used

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  • An orange-red photothermally activated delayed fluorescent material and an organic electroluminescent device
  • An orange-red photothermally activated delayed fluorescent material and an organic electroluminescent device
  • An orange-red photothermally activated delayed fluorescent material and an organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The reaction formula is as follows:

[0039]

[0040] The specific reaction is as follows:

[0041] 1. Add 0.40g (2.14mmol) 4-bromobenzene-1,2-diamine and 0.65g (1.78mmol) 3,6-dibromo-9,10-phenanthrenequinone into a 150mL three-necked flask, then add 100mL without Use water and ethanol as a solvent, stir under the protection of nitrogen, heat to 100°C, condense and reflux for 2 hours, a large amount of solid precipitates, filter and recrystallize to obtain light yellow solid 3,6,11-tribromodibenzo[a,c] Phenazine, its productive rate is 95%;

[0042] 2. Add 0.55g (1.06mmol) 3,6,11-tribromodibenzo[a,c]phenazine and 0.78g (3.72mmol) 9,9-dimethyl-9,10 to a 150mL three-necked flask - Acridine, 50ml toluene, 0.41g (4.24mmol) sodium tert-butylate, 0.048g (0.053mmol) tris(dibenzylideneacetone) dipalladium(0), 0.015g (0.053mmol) tetrafluoroboric acid Tri-tert-butylphosphine was heated to 110°C under nitrogen protection, and stirred and refluxed for 24h. After the reaction...

Embodiment 2

[0053] 3,6,11-tris(9,9-dimethylacridin-10(9H)-yl) dibenzo[a,c]phenazine (3DMAC-BP) prepared in Example 1 as the light-emitting layer Preparation and performance evaluation of organic electroluminescent devices.

[0054] Concrete preparation steps are as follows:

[0055] 1. The pretreatment of glass anode: choose the glass substrate that has 3 * 3mm indium tin oxide (ITO) film pattern as transparent electrode; After described glass substrate is washed with ethanol, process with UV-ozone again, obtain pretreatment Processed glass substrates.

[0056] 2. Vacuum evaporation: vacuum evaporation of each layer is carried out on the pretreated glass substrate by a vacuum evaporation method. First, put the processed glass substrate into the vacuum evaporation chamber, the vacuum degree is ≤2×10 -4 Pa, MoO 3 The deposition rate is The deposition rate of TADF luminescent material is about The deposition rate of the host material is about LiF layer deposition rate is Al depos...

Embodiment 3

[0062] 3,6,11-tris(9,9-dimethylacridin-10(9H)-yl) dibenzo[a,c]phenazine (3DMAC-BP) prepared in Example 1 as the light-emitting layer Preparation and performance evaluation of organic electroluminescent devices.

[0063] Concrete preparation steps:

[0064] Except for the doping concentration, the method for preparing an organic electroluminescent device is the same as in Example 2; The weight percentage of [a,c]phenazine in the light-emitting layer is 15%wt.

[0065] Performance evaluation:

[0066]The open-circuit voltage of the organic electroluminescence device made is 3.3V, and luminous wavelength is 600nm, and external quantum efficiency is 19.6%, and current efficiency is 37.9cd / A, and power efficiency is 35.0m / W, and CIE color coordinate value is (0.565 ,0.432).

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Abstract

The invention discloses an orange-red photothermally activated delayed fluorescent material, which is 3,6,11-tris(9,9-dimethylacridin-10(9H)-yl)dibenzo[a,c]phenazine (3DMAC‑BP). The fluorescent material has a rigid large plane twisted structure and a significant internal charge transfer (ICT) effect, has orange-red photothermally activated delayed fluorescence properties (TADF), high fluorescence quantum yield (PLQY) and excellent thermal stability, and its 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 are possible. The organic electroluminescent device based on this material can emit orange-red fluorescence (λ=606nm), the external quantum efficiency EQE of the device is as high as 22%, and has the advantages of low driving voltage and good luminescence stability. , night vision and biological imaging and other fields have good application prospects.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an orange-red photothermal activation delayed fluorescent material and an organic electroluminescent device that can be industrialized, have high fluorescence quantum yield and good luminous performance. 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. The first-generation light-emitting device OLED based on conventional fluorescent materials shows an internal quantum efficiency (IQE) of up to 25%, and an external quantum efficiency (EQE) of 5-7.5%, which is because the emitting material can only obtain singlet exciton emission. Sincerely. The second-generation phosphorescent materials containing noble metal atoms can effectively utilize singlet and triplet excitons to emit light through spin-orbit coupling, and its IQE can r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/14C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07D401/14C09K2211/1044H10K85/636H10K85/633H10K85/615H10K85/654H10K50/12
Inventor 赵鑫谢凤鸣李昊泽吴平
Owner SUZHOU UNIV OF SCI & TECH
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