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Organic thermally-induced delayed fluorescence material based on pyrazine receptor as well as preparation method and application of organic thermally-induced delayed fluorescence material

A thermally induced delayed fluorescence, organic technology, applied in the direction of luminescent materials, organic chemistry, chemical instruments and methods, etc., can solve the problems of reducing radiation attenuation rate, reducing oscillation intensity, etc., to achieve improved emission efficiency, good thermal stability, and suppression Effects of nonradiative transitions

Active Publication Date: 2021-06-15
UNIV OF ELECTRONICS SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Connecting the electron donor (D) unit to the electron acceptor (A) unit via a highly twisted bridge to break their conjugation can effectively reduce ΔEst, but the weakened D–A connection also reduces the oscillation strength (fs) and Reduce radiation decay rate

Method used

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  • Organic thermally-induced delayed fluorescence material based on pyrazine receptor as well as preparation method and application of organic thermally-induced delayed fluorescence material
  • Organic thermally-induced delayed fluorescence material based on pyrazine receptor as well as preparation method and application of organic thermally-induced delayed fluorescence material
  • Organic thermally-induced delayed fluorescence material based on pyrazine receptor as well as preparation method and application of organic thermally-induced delayed fluorescence material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] This example proposes an organic thermally induced delayed fluorescence material based on a pyrazine acceptor, the molecular structure of which is DPXZ-BPDF as follows:

[0070]

[0071] The synthetic route is as follows:

[0072]

[0073] Specifically include the following steps:

[0074] Step 1: Add 3,6-dibromophenanthrenequinone (366mg, 1mmol), phenoxazine (420mg, 2.3mmol), and palladium acetate (8.42mg, 0.04mmol) to a 100mL two-necked round-bottom flask with a magnet in sequence , sodium tert-butoxide (217mg, 2.25mmol) and tri-tert-butylphosphine tetrafluoroborate (29mg, 0.1mmol), the nitrogen was replaced three times, and under the protection of nitrogen, 30mL of toluene was extracted with a 50mL syringe and added to the round bottom flask , rotate the reaction at an oil bath temperature of 110°C; use thin-layer chromatography (TCL) to spot plate detection, wait until 3,6-dibromophenanthrenequinone has completely reacted (reaction 20h), and use a Buchner fun...

Embodiment 2

[0086] This example proposes an organic thermally induced delayed fluorescence material based on a pyrazine acceptor, and the molecular structure is TPXZ-BPF as shown below:

[0087]

[0088] The synthetic route is as follows:

[0089]

[0090] Specifically include the following steps:

[0091] Step 1: Add phenoxazine (183mg, 1.1mmol) and sodium hydride (36mg, 1.5mmol) successively to the first 100mL two-necked round-bottomed flask with a magnet, replace the nitrogen three times, under the protection of nitrogen, Use a 50mL syringe to extract 20mL of ultra-dry N,N-dimethylformamide into a round bottom flask under the condition of an ice bath. After the reaction solution in the round bottom flask turns dark green, remove the ice bath and raise the temperature to 70 °C to obtain a mixed solution D;

[0092] Step 2: Add the pyrazine acceptor-based organic thermally induced delayed fluorescent material (DPXZ-BPDF) (678mg, 1mmol) obtained in Example 1 to the second 100mL ro...

Embodiment 3

[0102] This example proposes an organic thermally induced delayed fluorescence material based on a pyrazine acceptor, the molecular structure of which is DPXZ-BPDPA as shown below:

[0103]

[0104] The synthetic route is as follows:

[0105]

[0106] Specifically include the following steps:

[0107] Step 1: Add intermediate A (570mg, 1mmol) and 4-bromo-o-phenylenediamine (190mg, 1.1mmol) successively to a 100mL two-necked round-bottomed flask with a magnet, and replace the nitrogen three times. , use a 50mL syringe to extract 30mL of acetic acid and add it to a round bottom flask, and rotate the reaction at an oil bath temperature of 110°C; use a TCL spot plate to detect, wait until the intermediate A is completely reacted (reaction 8h), use a separatory funnel to separate the reaction system Extract the medium acetic acid (with dichloromethane and water), then wash the funnel with 200mL of dichloromethane, add 200-300 mesh thick silica gel to the filtrate and distill...

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Abstract

The invention provides an organic thermally-induced delayed fluorescence material based on a pyrazine receptor as well as a preparation method and application of the organic thermally-induced delayed fluorescence material, and belongs to the technical field of organic light-emitting diodes. Four organic thermally-induced delayed fluorescence materials are synthesized by taking a pyrazine receptor as a core, and corresponding organic light-emitting devices containing the pyrazine receptor-based organic thermally-induced delayed fluorescence materials are provided according to different organic thermally-induced delayed fluorescence materials. The organic thermally-induced delayed fluorescent material has small [delta]Est and large f and shows good TADF characteristics, and the pyrazine structural unit has certain rigidity, can well inhibit non-radiative transition and improve orange / red light emission efficiency, has wide application prospects and is expected to be widely applied to the fields of panel display, solid-state illumination and the like.

Description

technical field [0001] The invention belongs to the technical field of organic light-emitting diodes, and in particular relates to an organic heat-induced delayed fluorescent material based on a pyrazine acceptor, a preparation method and an application. Background technique [0002] Organic light-emitting diodes (OLEDs) are also called organic light-emitting devices (Organic Light-Emitting Device) or organic electroluminescent devices (Organic Electroluminescent Device). Organic electroluminescence refers to a light-emitting phenomenon in which small organic molecules, metal-organic complex molecules or polymer molecular light-emitting materials directly convert electrical energy into light energy under the action of a forward bias electric field. OLED can not only emit light independently, without backlight and energy saving, but also has the characteristics of fast response, low driving voltage, high luminous efficiency, high resolution, wide viewing angle and high contra...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/14C09K11/06H01L51/50H01L51/54
CPCC07D413/14C09K11/06C09K2211/1033C09K2211/1044C09K2211/1014C09K2211/1007H10K85/636H10K85/633H10K85/657H10K85/6572H10K50/11Y02E10/549
Inventor 郑才俊蒲春鹏银培峰
Owner UNIV OF ELECTRONICS SCI & TECH OF CHINA
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