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Triptycene D-A type thermal activation delayed fluorescence material, electronic device and application thereof

A technology of thermally activated delayed and fluorescent materials, applied in luminescent materials, electric solid devices, electrical components, etc., can solve problems including high cost, strong triplet annihilation, low blue emission stability, etc., and achieve good solubility, The effect of good thermal stability and easy regulation of molecular structure

Inactive Publication Date: 2020-11-27
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although phosphorescent materials have been widely used in OLED technology, there are significant problems including high cost, low stability of blue emission, and strong triplet annihilation at high current densities.

Method used

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  • Triptycene D-A type thermal activation delayed fluorescence material, electronic device and application thereof
  • Triptycene D-A type thermal activation delayed fluorescence material, electronic device and application thereof
  • Triptycene D-A type thermal activation delayed fluorescence material, electronic device and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046]The structural formulas of the thermally activated delayed fluorescent materials TTC-DMAC-TRZ (compound 60) and TTC-DMAC-PM (compound 61) in this example are as follows:

[0047]

[0048] The specific synthesis process of the above thermally activated delayed fluorescent material is as follows:

[0049]

[0050] Preparation of Compound 2: Select a 100mL two-necked flask, add 1-aminotriptycene (2.36g, 10mmol), methyl anthranilate (3.62g, 24mmol), palladium acetate (224.5mg, 1mmol) under argon protection , cesium carbonate (13.0 g, 40 mmol), tri-tert-butylphosphonium tetrafluoroborate (754.3 mg, 2.6 mmol) and 30 mL of toluene were reacted at 120° C. for 12 hours. After cooling to room temperature, the inorganic salt was filtered through diatomaceous earth, and separated by silica gel column chromatography to obtain 2.86 g of white solid with a yield of 76%. MS(EI):m / z 430.1[M + ].

[0051]

[0052] Preparation of TTC-DMAC: Compound 2 (1.30 g, 3.4 mmol) was diss...

Embodiment 2

[0058] The preparation of the TTC-PXZ of the present embodiment, reaction formula is as follows:

[0059]

[0060] Preparation of Compound 2: Select a 250mL two-necked flask, add 2-hydroxytriptycene (1.60g, 5.9mmol) and 30mL toluene under the protection of argon, and slowly add N-bromosuccinimide (1.05g, 5.9mmol) , reacted at 0°C for 2 hours. After the reaction, it was separated by silica gel column chromatography to obtain 1.80 g of white solid with a yield of 90%. MS(EI):m / z 348.0[M + ].

[0061] Preparation of compound 3: Select a 100mL two-necked flask, add compound 2 (0.80g, 2.3mmol), o-fluoronitrobenzene (0.39g, 2.7mmol), potassium carbonate (0.63g, 4.6mmol) and 30mL under the protection of argon N,N-Dimethylformamide (DMF), reacted at 100°C for 12 hours. After cooling to room temperature, it was poured into water and filtered to obtain a solid, which was separated by silica gel column chromatography to obtain 0.86 g of a white solid with a yield of 78%. MS(EI):m...

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Abstract

The invention discloses a triptycene D-A type thermal activation delayed fluorescent material, an electronic device and an application thereof. The fluorescent material has one of the following structural general formulas: X1 is selected from non-bonding, single bond, -N (R1)-,-O-,-S-,-S=O-,-SO2-,-C (R1R2)-,-S (R1R2)-,-P (R1)-and-P=O (R1)-; M1 is selected from hydrogen, deuterium, alkenyl, alkynyl, amido, nitro, carbonyl, sulfuryl, halogen, cyano, alkyl, alkoxy, substituted C6-C60 aromatic ring groups, unsubstituted C7-C60 aromatic ring groups and C3-C60 aromatic heterocyclic groups; Y1 is selected from hydrogen, deuterium, alkenyl, alkynyl, amido, nitro, carbonyl, sulfuryl, halogen, cyano, alkyl, alkoxy, substituted C6-C60 aromatic ring groups, unsubstituted C7-C60 aromatic ring groups and C3-C60 aromatic heterocyclic groups.

Description

technical field [0001] The invention relates to the technical field of organic electroluminescent materials, in particular to a triptycene-based D-A type thermally activated delayed fluorescent material, electronic devices and applications. Background technique [0002] In recent years, organic light-emitting diodes (OLEDs) have developed into an emerging substitute for materials such as traditional lighting and displays. It has developed rapidly in the field of light-emitting materials due to its excellent properties such as bendability, low power consumption, and bright colors. [0003] Luminescent materials are the core of organic light-emitting diode technology. The energy utilization efficiency (IQE) of the first generation of traditional fluorescent materials is only 25%. The research has now reached 100% IQE. Although phosphorescent materials have been widely used in OLED technology, there are significant problems including high cost, low stability of blue emission, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/80C07D221/22C07D265/34C07D279/36C07D401/04C07D401/10C07D403/10C07D405/04C07D409/04C07D413/04C07D413/10C07D417/04C07D417/10C07F5/02C07F7/10C09K11/06H01L51/54H01L51/50
CPCC07D265/34C07D413/04C07D413/10C07F5/027C07D279/36C07D417/04C07F7/0816C07D417/10C07D221/22C07D409/04C07D405/04C07D401/10C07D401/04C07D209/80C07D403/10C09K11/06C09K2211/1011C09K2211/1033C09K2211/1014C09K2211/1007C09K2211/1059C09K2211/1092C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1037C09K2211/1096C09K2211/104H10K85/615H10K85/654H10K85/6576H10K85/6574H10K85/6572H10K85/657H10K85/40H10K50/11
Inventor 占群邹洋杨楚罗
Owner SHENZHEN UNIV
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