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A kind of phosphorus-containing bicyclic compound and its preparation method and application

A ring compound and compound technology, which is applied in the field of phosphorus-containing bicyclic compounds and their preparation, can solve problems such as low transmission efficiency, unstable device performance, and short lifespan, and achieve improved luminous efficiency, increased glass transition temperature, and less crystallization Effect

Active Publication Date: 2021-09-24
NINGBO LUMILAN NEW MATERIAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Therefore, the technical problem to be solved by the present invention is to overcome defects such as low transmission efficiency, unstable device performance, and short lifespan of electron transport materials in the prior art, thereby providing a phosphorus-containing bicyclic compound and its preparation method and application

Method used

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  • A kind of phosphorus-containing bicyclic compound and its preparation method and application
  • A kind of phosphorus-containing bicyclic compound and its preparation method and application
  • A kind of phosphorus-containing bicyclic compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] This embodiment provides a phosphorus-containing bicyclic compound, which has the structure shown in the following formula C-1:

[0044]

[0045]The synthetic route of the compound shown in formula C-1 is as follows:

[0046]

[0047] The preparation method of the compound shown in formula C-1 specifically comprises the following steps:

[0048] (1) Preparation of intermediate (F-1)

[0049] Under the protection of nitrogen, put diisopropylamine (72.8g, 0.72mol, 1.06eq) and anhydrous tetrahydrofuran 1500mL into a 5L dry and clean four-neck round bottom flask, cool to -70°C, add n-butyllithium solution (272mL , 2.5M, 0.68mol, 1.0eq), stirred and cooled to -70°C, slowly added D-1 (130g, 0.68mol, 1.0eq), added dropwise and maintained the reaction for 1h, slowly added iodine-tetrahydrofuran solution (172g iodine / 300ml THF, 0.68mol, 1.0eq), the reaction was maintained for 1h after the addition was completed, and then the temperature was slowly raised to room tempera...

Embodiment 2

[0058] This embodiment provides a phosphorus-containing bicyclic compound, which has the structure shown in the following formula C-2:

[0059]

[0060] The synthetic route of the compound shown in formula C-2 is as follows:

[0061]

[0062] The preparation method of the compound shown in formula C-2 specifically comprises the following steps:

[0063] (1) Preparation of intermediate (F-2)

[0064] Under the protection of nitrogen, put diisopropylamine (72.8g, 0.72mol, 1.06eq) and anhydrous tetrahydrofuran 1500mL into a 5L dry and clean four-neck round bottom flask, cool to -70°C, add n-butyllithium solution (272mL , 2.5M, 0.68mol, 1.0eq), stirred and cooled to -70°C, slowly added D-2 (139g, 0.68mol, 1.0eq) dropwise, maintained the reaction for 1h after adding, slowly added iodine-tetrahydrofuran solution (172g iodine / 300ml THF, 0.68mol, 1.0eq), the reaction was maintained for 1h after the addition was completed, and then the temperature was slowly raised to room tem...

Embodiment 3

[0073] This embodiment provides a phosphorus-containing bicyclic compound, which has the structure shown in the following formula C-3:

[0074]

[0075] The synthetic route of the compound shown in formula C-3 is as follows:

[0076]

[0077] The preparation method of the compound shown in formula C-3 specifically comprises the following steps:

[0078] (1) Preparation of intermediate (D-3)

[0079]Under nitrogen protection, compound (M-3) (270g, 1.0mol, 1.0eq), compound (N-3) (122g, 1.0mol, 1.0eq) and toluene 2500mL were added to a 5L four-neck round bottom flask, and then added Sodium carbonate (212g, 2.0mol, 2.0eq) and purified water (360g, 20mol, 20eq), nitrogen purging 30mins, add tetrakis (triphenylphosphine) palladium (11.5g, 0.01mol, 0.01eq) again, be warming up to The reaction was carried out at 110°C for 15 hours, and the reaction was monitored by HPLC to be complete. Add diatomaceous earth to filter, and the organic phase is washed with 2000 mL of saturated...

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Abstract

The invention belongs to the technical field of electroluminescent materials, and in particular relates to a phosphorus-containing bicyclic compound and its preparation method and application. The phosphorus-containing bicyclic compound provided by the present invention has a structure as shown in formula (I) or formula (II). This type of compound is centered on a bibenzodiphosphoryl seven-membered ring, and an appropriate substituent is introduced into the side chain, Form a large electron-deficient conjugated system, and the formed closed-loop structure has excellent electron transport properties; the compound provided by the invention has suitable HOMO energy level and LUMO energy level, which can reduce the need to overcome the electron injection from the cathode to the light-emitting layer. The potential barrier increases the effective injection of electrons, which is beneficial to reduce the working voltage of the device and improve the luminous efficiency of the device; at the same time, the molecular weight of the material is between 550 and 920, and the molecule has a large rigid structure, which makes the thermal stability better. , which can be adapted to the evaporation process of small molecule organic electroluminescent devices.

Description

technical field [0001] The invention belongs to the technical field of electroluminescent materials, and in particular relates to a phosphorus-containing bicyclic compound and its preparation method and application. Background technique [0002] Organic light-emitting diodes (organic light-emitting diodes, OLEDs) is an emerging flat-panel display, compared with traditional displays, it has fast response, low energy consumption, self-illumination, wide color gamut, ultra-thin, foldable and With the advantages of flexibility and the ability to make large-size panels, it is the most ideal and promising new display technology in the future. [0003] OLED is a carrier double-injection light-emitting device. The light-emitting mechanism is: driven by an external electric field, electrons and holes are injected into the organic light-emitting layer from the cathode and anode respectively, and recombine in the organic light-emitting layer to generate excitons. The radiative transit...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6568C09K11/06H01L51/50H01L51/54
CPCC07F9/65685C09K11/06C09K2211/1096C09K2211/1007C09K2211/1011H10K85/615H10K85/6574H10K85/657H10K50/16
Inventor 张玉祥张庆云丁欢达陈志宽
Owner NINGBO LUMILAN NEW MATERIAL CO LTD
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