Organic compound based on pyridine and benzimidazole and application thereof in organic light emitting diodes (OLED)

An organic compound and benzimidazole technology, applied in the field of organic compounds and its application in OLED, can solve the problems affecting the angular distribution of OLED radiation spectrum and complex manufacturing process, etc.

Active Publication Date: 2017-12-01
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The first two structures will affect the angular distribution of the radiation spectrum of the OLED. The third structure is complicated to manufacture, but the process of using the surface covering layer is simple, and the luminous efficiency can be increased by more than 30%, which is particularly concerned by people.

Method used

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  • Organic compound based on pyridine and benzimidazole and application thereof in organic light emitting diodes (OLED)
  • Organic compound based on pyridine and benzimidazole and application thereof in organic light emitting diodes (OLED)
  • Organic compound based on pyridine and benzimidazole and application thereof in organic light emitting diodes (OLED)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: the synthesis of intermediate I

[0068] When azabenzene and Ar 1 When connected by C-C bond,

[0069]

[0070] Under nitrogen atmosphere, weigh Ar 1 The bromide was dissolved in tetrahydrofuran (THF), and then bis(pinacolyl)diboron, (1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium(II) and potassium acetate were added, The mixture is stirred, and the mixed solution of the above reactants is heated to reflux at a reaction temperature of 70-90° C. for 5-10 hours; after the reaction is completed, water is added to cool, and the mixture is filtered and dried in a vacuum oven. The obtained residue was separated and purified by silica gel column to obtain Ar 1 pinacol borate;

[0071]

[0072] Under a nitrogen atmosphere, weigh raw material A and dissolve it in N,N-dimethylformamide (DMF), and then and palladium acetate, stir the mixture, then add potassium phosphate aqueous solution, heat the mixed solution of the above reactants to reflux at...

Embodiment 2

[0095] Embodiment 2: intermediate Synthesis

[0096] When R 1 or R 2 When expressed as a structure of general formula (6),

[0097]

[0098] (1) In a 250mL three-necked flask, feed nitrogen, add 0.02mol raw material 2-bromo-benzimidazole, 0.03mol I-Ar 4 , 0.04mol sodium hydride, 0.004mol cuprous iodide and 0.01mol o-phenanthroline were dissolved in 100ml 1,3-dimethyl-2-imidazolidinone, stirred and reacted for 20-30h, after the reaction, add water and use two Extract with methyl chloride, dry the organic layer with anhydrous sodium sulfate, rinse with a mixture of petroleum ether and ethyl acetate as eluent, the volume ratio of petroleum ether and ethyl acetate in the eluent is 1:100, and purify by column chromatography , to obtain intermediate M;

[0099]

[0100] (2) Under a nitrogen atmosphere, weigh the intermediate M and dissolve it in tetrahydrofuran, and then dissolve the Br-Ar 2 -B(OH) 2 And tetrakis (triphenylphosphine) palladium is added, the mixture is ...

Embodiment 3

[0132] Embodiment 3: the synthesis of compound 3:

[0133]

[0134] In a 250mL three-neck flask, blow nitrogen, add 0.01mol intermediate A1, 150ml DMF, 0.03mol intermediate B1, 0.0002mol palladium acetate, stir, and then add 0.02mol K 3 PO 4 The aqueous solution was heated to 150°C, refluxed for 24 hours, sampled and plated, and the reaction was complete. Cool naturally, extract with 200ml of dichloromethane, separate layers, dry the extract with anhydrous sodium sulfate, filter, rotate the filtrate, and purify through a silica gel column to obtain the target product with a HPLC purity of 99.4% and a yield of 64.7%.

[0135] Elemental analysis structure (molecular formula C 55 h 37 N 5 ): theoretical value C, 86.02; H, 4.86; N, 9.12; test value: C, 86.05; H, 4.85; N, 9.10. ESI-MS(m / z)(M + ): The theoretical value is 767.30, and the measured value is 767.58.

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Abstract

The invention relates to an organic compound taking pyridine and benzimidazole as a core and application thereof in organic light emitting diode (OLED) devices. The compound disclosed by the invention has higher glass transition temperature and molecular heat stability; the compound has low absorption and high refractive index in the field of visible light; after being applied to CPL layers of the OLED devices, the compound can effectively improve light extraction efficiency of the OLED devices. The compound disclosed by the invention further has a deep HOMO energy level and high electronic mobility, can serve as a cavity blocking/electron transfer layer material of the OLED devices and can effectively prevent cavities or energy from being transmitted to one side of an electronic layer from a luminescent layer; thus, composition efficiency of the cavities and the electrons in the luminescent layer is improved, and further luminous efficiency and service life of the OLED devices are improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound with azabenzene and benzimidazole as the core and its application in OLEDs. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. The OLED light-emitting device is like a sandwich structure, including electrode material film layers and organic functional materials sandwiched between different electrode film layers. Various functional materials are superimposed on each other according to the application to form an OLED light-emitting device. OLED light-emitting devices are current devices. When a voltage is applied to the electrodes at both ends, and the positive and negat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/14C07D471/04C07D405/14C07D401/10C07D519/00C07D401/04C07D403/14C07D403/10C09K11/06H01L51/50H01L51/52H01L51/54
CPCC09K11/06C07D401/04C07D401/10C07D401/14C07D403/10C07D403/14C07D405/14C07D471/04C07D519/00C09K2211/1044C09K2211/1007C09K2211/1022C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1088H10K85/636H10K85/631H10K85/654H10K85/6574H10K85/657H10K85/6572H10K50/16H10K50/18H10K50/85
Inventor 张兆超李崇
Owner JIANGSU SUNERA TECH CO LTD
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