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A thermally induced delayed fluorescent material and its preparation method and application

A technology of thermally induced delayed fluorescence and reactants, which is applied in the fields of luminescent materials, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problems of poor performance and efficiency roll-off of TADF devices, so as to avoid non-radiative transitions and expand distance, improving the effect of device efficiency roll-off

Active Publication Date: 2021-02-09
WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported high-efficiency deep blue thermally induced delayed fluorescent materials and device maximum efficiencies are basically at extremely low current densities (2 ), the performance of deep blue TADF devices is far inferior to other light colors
In addition, all TADF devices, at high current densities, singlet-triplet annihilation (STA), triplet-triplet annihilation (TTA), triplet-polaron annihilation (TPQ), and excited states The non-radiative attenuation caused by molecular vibration relaxation will make the efficiency roll-off very serious, and the roll-off performance is more obvious for deep blue TADF devices. Therefore, the further design and synthesis of TADF materials can improve device efficiency from the perspective of regulating excitonic transitions. Roll-off is a hot spot in the field of OLED research

Method used

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  • A thermally induced delayed fluorescent material and its preparation method and application
  • A thermally induced delayed fluorescent material and its preparation method and application
  • A thermally induced delayed fluorescent material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Embodiment 1: the present invention is that above-mentioned compound 1 can be synthesized by the following method:

[0061]

[0062] (1) In a 1L reaction flask, add 2-chloro-10H-phenothiazine (46.74g, 200mmol), bromobenzene (31.40g, 200mmol), 1,2-cyclohexanediamine (2.28g, 20mmol), Cuprous iodide (0.76g, 4mmol), sodium tert-butoxide (38.44g, 400mmol), 500g 1,4-dioxane, under the protection of nitrogen, heated up to 95°C, reacted for 10h, liquid phase monitoring completed the reaction, Cool down to stop the reaction. Filter the reaction solution with a silica gel funnel, wash the filtrate with water, separate layers, concentrate, and beat once with 1:10 petroleum ether and ethyl acetate to obtain 48.95 g of intermediate b with a yield of 79%;

[0063] (2) In a 1L reaction flask, add intermediate b (37.18g, 120mmol), dichloromethane (250mL), hydrogen peroxide (H 2 o 2 ) (25mL), acetic acid (AcOH) (125mL), the temperature was raised to 70°C, and the reaction was carr...

Embodiment 2

[0066] Embodiment 2: The present invention is that the above-mentioned compound 10 can be synthesized by the following method.

[0067]

[0068] (1) In a 1L reaction flask, add 2-chloro-10H-phenothiazine (46.74g, 200mmol), 1-bromodibenzofuran (49.42g, 200mmol), 1,2-cyclohexanediamine (2.28 g, 20mmol), cuprous iodide (0.76g, 4mmol), sodium tert-butoxide (38.44g, 400mmol), 500g 1,4-dioxane, under the protection of nitrogen, the temperature was raised to 95°C, and the reaction was carried out for 10h. The phase monitoring reaction is completed, and the temperature is lowered to stop the reaction. Filter the reaction solution with a silica gel funnel, wash the filtrate with water, separate layers, concentrate, and beat once with 1:10 petroleum ether and ethyl acetate to obtain 59.98 g of intermediate b with a yield of 75%;

[0069] (2) In a 1L reaction flask, add intermediate b (47.98g, 120mmol), dichloromethane (400mL), hydrogen peroxide (H 2 o 2 ) (40mL), acetic acid (AcOH...

Embodiment 3

[0072] Example 3: The present invention is that the above-mentioned compound 21 can be synthesized by the following method.

[0073]

[0074] (1) In a 1L reaction flask, add 2-chloro-10H-phenothiazine (46.74g, 200mmol), 9-(4-bromophenyl)-9H-carbazole (64.44g, 200mmol), 1,2 -cyclohexanediamine (2.28g, 20mmol), cuprous iodide (0.76g, 4mmol), sodium tert-butoxide (38.44g, 400mmol), 500g 1,4-dioxane, under nitrogen protection, the temperature was raised to 95°C, react for 10h, monitor the completion of the reaction by liquid phase monitoring, and stop the reaction by lowering the temperature. Filter the reaction solution with a silica gel funnel, wash the filtrate with water, separate layers, concentrate, and beat once with 1:10 petroleum ether and ethyl acetate to obtain 73.15 g of intermediate b with a yield of 77%;

[0075] (2) In a 1L reaction flask, add intermediate b (57.00g, 120mmol), dichloromethane (500mL), hydrogen peroxide (H 2 o 2 ) (50 mL), acetic acid (AcOH) (2...

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Abstract

The invention belongs to the field of photoelectric material application technology, and in particular relates to a thermally induced delayed fluorescent material and its preparation method and application. The present invention constitutes a thermally induced delayed fluorescent material by introducing a "benzene bridge" between the donor and acceptor fragments or on the donor / acceptor fragments, expanding its π conjugation degree, expanding the distance for separating electrons, and material delocalization effect The design avoids triplet-charge reaction energy loss, and improves device efficiency roll-off from the perspective of regulating excitonic transition. When used as a light-emitting layer guest material or a light-extracting layer material in a device, the N substitution on the donor-acceptor segment will cause a blue shift in the light-emitting wavelength, weaken the electron-absorbing ability of diphenylsulfone, and help widen the energy gap to achieve deep blue light, and The triplet energy level lower than that of the host material can effectively inhibit the triplet energy backflow from the guest to the host, thereby confining the triplet excitons in the light-emitting layer and improving the light extraction efficiency. It is an ideal light-emitting layer guest material and light extraction. layer material.

Description

technical field [0001] The invention belongs to the field of photoelectric material application technology, and in particular relates to a thermally induced delayed fluorescent material and its preparation method and application. Background technique [0002] OLED stands for Organic Light-Emitting Diode (Organic Light-Emitting Diode), also known as Organic Electroluminescence Display (OELD). OLED has the characteristics of self-illumination. It uses a very thin organic material coating and glass substrate. When the current passes through, the organic material will emit light, and the OLED display screen has a large viewing angle and can significantly save power. Therefore, OLED is regarded as One of the most promising products of the 21st century. [0003] Although organic electroluminescent materials and devices can achieve an internal quantum efficiency close to 100%, the commonly used transition metal iridium and platinum complexes are too expensive and have limited rese...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/10C07D417/14C07D279/34C09K11/06H01L51/54
CPCC07D417/10C07D417/14C07D279/34C09K11/06C09K2211/1044C09K2211/1092C09K2211/1088C09K2211/1037H10K85/615H10K85/631H10K85/6576H10K85/6574H10K85/657H10K85/6572
Inventor 穆广园庄少卿任春婷
Owner WUHAN SUNSHINE OPTOELECTRONICS TECH CO LTD
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