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Pyrene fused ring molecule based on bridged tripolyindole structure and electroluminescent device

A tripolybenzdole and pyrene technology, applied in the field of organic optoelectronics, can solve the problems of poor color purity, unfavorable high-end display applications, etc., and achieve the effects of good solubility, inhibition of non-radiative transition, and reduction of fluorescence quenching

Pending Publication Date: 2022-06-03
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the emission spectrum of most blue fluorescent materials is too broad and the color purity is poor, which is not conducive to high-end display applications.

Method used

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  • Pyrene fused ring molecule based on bridged tripolyindole structure and electroluminescent device
  • Pyrene fused ring molecule based on bridged tripolyindole structure and electroluminescent device
  • Pyrene fused ring molecule based on bridged tripolyindole structure and electroluminescent device

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preparation example Construction

[0042] The present invention has no special limitation on the preparation method of the electroluminescent device, which can be carried out according to the following methods: forming an anode on the substrate; forming one or more organic thin film layers on the anode, including a layer of a light-emitting layer; forming a cathode on the organic thin film layer;

[0043] The light-emitting layer includes one or more pyrene-based fused ring molecules represented by formula (I) and / or formula (II) based on a bridged tripolybenzazole structure.

[0044] The present invention can correspond to the structures and materials of the electroluminescent device in the above preparation method, and the corresponding preferred principles, and the corresponding materials and structures of the aforementioned electroluminescent device, and the corresponding preferred principles, which will not be repeated here. One more elaboration.

[0045] In the present invention, an anode is first formed...

Embodiment 1

[0049]

[0050]1.1 Under argon atmosphere, weigh m-1 (3.45g, 10mmol), cuprous iodide, (190mg, 1mmol), copper powder (2.5g, 40mmol) and potassium carbonate (5.5g, in a 100mL two-necked flask). 40mmol), add 50mL of o-dichlorobenzene (o-DCB), 8ml of methyl o-iodobenzoate (50mmol), warm up to 220 ° C, stir under argon protection for 50 hours, then cool to room temperature, add dichloromethane and After extraction with water, the organic phase was separated, dried by adding anhydrous sodium sulfate, the solvent was removed from the organic phase obtained by filtration, and the product m-2 (800 mg, yield: 13%) was obtained by column separation.

[0051] Elemental Analysis Structure (C 40 H 27 N 3 O 4 ): theoretical C, 78.29; H, 4.43; N, 6.85; tested C, 78.30; H, 4.40; N, 6.80. Matrix-assisted laser desorption-time-of-flight mass spectrometry (MALDI-TOF-MS) theoretical value 613.20; experimental value 613.2 (M + ).

[0052] 1.2 Under an argon atmosphere, m-2 (1.2 g, 2 mmol) ...

Embodiment 2

[0059]

[0060] 2.1 Under argon atmosphere, in a 100mL two-necked flask, weigh m-1 (3.45g, 10mmol), 4-tert-butyl-2-bromoiodobenzene (16.9g, 50mmol), cuprous iodide, (190mg, 1mmol), copper powder (2.5g, 40mmol) and potassium carbonate (5.5g, 40mmol), add 50mL o-dichlorobenzene (o-DCB), warm up to 220°C, stir for 50 hours under argon protection, and then cool to At room temperature, dichloromethane and water were added for extraction, the organic phase was separated, dried by adding anhydrous sodium sulfate, the solvent was removed from the organic phase obtained by filtration, and the product m-6 (900 mg, yield: 12%) was obtained by column separation.

[0061] Elemental Analysis Structure (C 44 H 37 Br 2 N 3 ): theoretical C, 68.85; H, 4.86; N, 5.47; tested C, 68.41; H, 4.80; N, 5.60. Matrix-assisted laser desorption-time-of-flight mass spectrometry (MALDI-TOF-MS) theoretical value 765.14; experimental value 765.1 (M + ).

[0062] 2.2 Under an argon atmosphere, m-6 (76...

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Abstract

The invention provides a pyrene fused ring molecule bridged with a tripolyindole structure. The pyrene fused ring molecule is shown as a formula (I) or a formula (II). Compared with the prior art, the molecule provided by the invention combines the bridged tripolyindole and pyrene, on one hand, the bridged tripolyindole and pyrene have rigid conjugate planes, and non-radiative transition of the molecule caused by rotation or vibration can be inhibited; on the other hand, large intramolecular steric hindrance between the bridged tripolyindole and pyrene is easy to form a distorted molecular structure, and fluorescence quenching caused by intermolecular aggregation is reduced, so that blue fluorescence emission with high fluorescence quantum yield is obtained; in addition, the molecules also have better solubility and are suitable for vacuum evaporation, solution processing and ink-jet printing, so that organic electroluminescent devices prepared based on the molecules can realize efficient and stable blue light emission, and the molecules have development potential and broad prospects in the field of organic electronic display.

Description

technical field [0001] The invention belongs to the technical field of organic optoelectronics, and in particular relates to a pyrene type fused ring molecule and an electroluminescent device based on a bridged tripolybenzazole structure. Background technique [0002] In 1987, Dr. Deng Qingyun of Kodak Company of the United States developed an organic light-emitting diode (OLED) device with a sandwich device structure, and the luminous brightness can reach 1000cd m under the driving of 10V DC voltage. -2 , opening the application in the field of organic electroluminescence. Compared with traditional display technologies, OLEDs have the advantages of self-luminescence, high contrast, low energy consumption, light weight, fast response speed, and the ability to prepare flexible large-area devices. application prospects. [0003] OLED light-emitting devices are usually composed of electrode material film layers and organic functional layers sandwiched between two electrode fi...

Claims

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Application Information

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IPC IPC(8): C07D519/00C07F7/10C07F9/6584C07D471/22C07D498/22C07D513/22C07D517/22C09K11/06H01L51/50H01L51/54
CPCC07D519/00C07F7/0816C07F9/6584C07F7/0812C07D471/22C07D498/22C07D513/22C07D517/22C09K11/06C09K2211/1059C09K2211/1011C09K2211/107C09K2211/1007C09K2211/1062C09K2211/1066H10K85/622H10K85/6572H10K85/657H10K85/40H10K50/11Y02E10/549
Inventor 王利祥童辉吴晓甫刘洋
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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