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Organic compound, organic electroluminescent material and application thereof

An organic compound and selected technology, applied in the field of organic electroluminescent materials and organic compounds, can solve the problems of reduced electron transport performance, reduced exciton formation efficiency, low glass transition temperature, etc. The effect of hole blocking ability, improving luminous efficiency and performance stability, and excellent film stability

Active Publication Date: 2020-06-05
WUHAN TIANMA MICRO ELECTRONICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, many electron transport materials used in the market include batho-phenanthroline (BPhen), bathocuproine (BCP) and TmPyPB, etc., which generally meet the market demand of organic electroluminescent panels, but they The glass transition temperature is low, generally less than 85°C. When the device is running, the Joule heat generated will lead to molecular degradation and molecular structure changes, resulting in low panel efficiency and poor thermal stability.
At the same time, the above-mentioned electron transport materials are easy to crystallize after being used for a long time. Once the electron transport materials crystallize, the charge transition mechanism between molecules will be different from the normal operation of the amorphous film mechanism, resulting in a decrease in the performance of electron transport, making the entire The mobility of electrons and holes in the device is unbalanced, the efficiency of exciton formation is greatly reduced, and the formation of excitons will be concentrated at the interface between the electron transport layer and the light-emitting layer, resulting in a serious decrease in device efficiency and lifetime

Method used

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  • Organic compound, organic electroluminescent material and application thereof
  • Organic compound, organic electroluminescent material and application thereof
  • Organic compound, organic electroluminescent material and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102] This embodiment provides an organic compound with the following structure:

[0103]

[0104] The preparation method of this organic compound M1 comprises the following steps:

[0105]

[0106] Under a nitrogen atmosphere, add 100mL of 1,4-dioxane solvent into a 250mL reaction flask, and then add K 2 CO 3 (9mmol), 7-methyl-8-bromoquinoline (3mmol), 7-methyl-8-boronic acid quinoline (3mmol), and palladium catalyst Pd (PPh 3 ) 4 (0.15 mmol), heated to 100°C, and reacted overnight. After the reaction is completed, cool to room temperature, add dichloromethane DCM and H 2 O was extracted, and the collected organic phase was washed with anhydrous Na 2 SO 4 Dry, collect the filtrate by suction filtration, spin off the solvent and perform column chromatography purification to obtain intermediate 1-1;

[0107] Test the structure of intermediate 1-1: m / z obtained by liquid chromatography-mass spectrometry (LC-MS): C 20 h 16 N 2 , the calculated value is 284.35, an...

Embodiment 2

[0119] This embodiment provides an organic compound with the following structure:

[0120]

[0121] The preparation method of this organic compound M301 comprises the following steps:

[0122] (1) The synthetic method of intermediate 1-3 is the same as in Example 1;

[0123]

[0124] Under nitrogen atmosphere, intermediate 1-3 (1 mmol) and zinc powder (5 mmol) were added to 30 mL of acetic acid, the reaction mixture was heated to 130° C., and refluxed for 5 h; the mixture solution gradually became transparent. After the reaction is finished, filter the mixture while it is hot to remove excess zinc; the filtrate is cooled, and as the acetic acid is cooled to room temperature, a solid is precipitated, the crude solid is filtered, and recrystallized with methanol, suction filtered and the filter cake is vacuum-dried to obtain Intermediate 2-1.

[0125] Tested the structure of Intermediate 2-1: LC-MS gave m / z: C 20 h 11 BrN 2 , the calculated value is 359.22, and the me...

Embodiment 3

[0131] This embodiment provides an organic compound with the following structure:

[0132]

[0133] The preparation method of this organic compound M302 comprises the following steps:

[0134] (1) The synthetic method of intermediate 2-1 is the same as in Example 2;

[0135]

[0136] Under a nitrogen atmosphere, add 100mL of 1,4-dioxane solvent into a 250mL reaction flask, and then add K 2 CO 3 (2mmol), intermediate 2-1 (1mmol), 4'-boronic acid-[3,2'; 6',3"]tripyridine (1.2mmol) and Pd(PPh 3 ) 4 (0.05 mmol), heated to 100°C, and reacted overnight. After the reaction is completed, cool to room temperature, add DCM, H 2 O was extracted, and the collected organic phase was washed with anhydrous Na 2 SO 4 After drying, the filtrate was collected by suction filtration, the solvent was spun off and purified by column chromatography to obtain the target product M302.

[0137] Tested the structure of M302: LC-MS got m / z: C 35 h 21 N 5 , the calculated value is 511.57,...

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Abstract

The invention provides an organic compound, an organic electroluminescent material and application thereof. The organic compound has a structure as shown informula I, aza-dibenzophenanthrene is used as a central skeleton structure; through the special design of substitution sites andsubstituent groups, the organic compound is provided with lower HOMO energy level andproper LUMO energy level; the organic compound has relatively high triplet state energy level ET and relatively high electron mobility, so that the electron transport capacity and the hole blocking capacity of the organic compoundas an electroluminescent material are remarkably improved, and meanwhile, the organic compound also has excellent thermal stability and film stability and is suitable for high-performance OLED devices. The organic compound and the organic electroluminescent material provided by the invention are used for an electron transport layer or a hole blocking layer of an OLED device, the luminous efficiency and the performance stability of the device can be effectively improved, and the service life of the device is prolonged.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials, and in particular relates to an organic compound, an organic electroluminescent material and applications thereof. Background technique [0002] Compared with traditional inorganic electroluminescent devices, organic electroluminescent devices (OLEDs) have the advantages of fast response, high luminous efficiency, self-illumination, wide viewing angle, ultra-thin, good temperature adaptability, simple production process and low energy consumption. , has been gradually applied in flexible display, flat panel display, solid-state lighting and vehicle display, and has great potential to replace the mainstream liquid crystal display, becoming a star technology in the display field. At the same time, people's performance requirements for display devices are constantly driving organic photoelectric materials and OLED devices to develop towards higher performance. [0003] ...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07D519/00C07F9/6561C07D221/18C07D401/14C07D403/14C07F9/576C07D409/14C07D405/14C09K11/06H01L51/50H01L51/54
CPCC07D471/04C07D519/00C07F9/65616C07D221/18C07D401/14C07D403/14C07F9/5765C07D409/14C07D405/14C09K11/06C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1044C09K2211/1059C09K2211/1088C09K2211/1092H10K85/615H10K85/624H10K85/626H10K85/654H10K85/6574H10K85/6576H10K85/6572H10K50/16H10K50/18H10K50/11
Inventor 冉佺高威牛晶华张磊代文朋
Owner WUHAN TIANMA MICRO ELECTRONICS CO LTD
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