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Organic compound based on azabenzene and application thereof in OLED

A technology for organic compounds and azepines, which is applied to organic compounds and their application on OLEDs, can solve the problems of affecting the angular distribution of OLED radiation spectrum, complicated manufacturing processes, etc.

Active Publication Date: 2019-09-13
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 azabenzene and application thereof in OLED
  • Organic compound based on azabenzene and application thereof in OLED
  • Organic compound based on azabenzene and application thereof in OLED

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0089] Embodiment 1: the synthesis of intermediate II

[0090] When Ar 1 and Ar 4 When linked with azabenzene by C-C bond,

[0091]

[0092] Under nitrogen atmosphere, weigh raw material A and dissolve it in DMF, then add and palladium acetate, stir the mixture, then add aqueous potassium phosphate solution, heat the mixed solution of the above reactants to reflux at 120-150°C for 5-15 hours; after the reaction is completed, add water after cooling, filter the mixture and store in a vacuum oven After drying, the obtained residue was purified by silica gel column to obtain compound intermediate I;

[0093] The raw material A and The molar ratio of palladium acetate and raw material A is 1:1.0~3, the mol ratio of palladium acetate and raw material A is 0.001~0.04:1, the molar ratio of potassium phosphate and raw material A is 1.0~4.0:1, and the consumption ratio of raw material A and DMF is 1g: 10-30ml;

[0094]

[0095] Under nitrogen atmosphere, weigh intermediat...

Embodiment 2

[0120] Embodiment 2: the synthesis of compound 1:

[0121]

[0122] 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%.

[0123] Elemental analysis structure (molecular formula C 37 h 23 N 3 o 2 ): theoretical value C, 82.05; H, 4.28; N, 7.76; 0, 5.91; test value: C, 82.06; ESI-MS(m / z)(M + ): The theoretical value is 541.18, and the measured value is 541.26.

Embodiment 3

[0124] Embodiment 3: the synthesis of compound 10:

[0125]

[0126] In a 250mL three-necked flask, nitrogen was introduced, 0.01mol of intermediate A2, 150ml of DMF, 0.03mol of intermediate B1, 0.0002mol of palladium acetate were added, stirred, and then 0.02mol of 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 99.1% and a yield of 67.2%.

[0127] Elemental analysis structure (molecular formula C 41 h 25 N 3 o 2 ): theoretical value C, 83.23; H, 4.26; N, 7.10; O, 5.41; test value: C, 83.26; H, 4.29; N, 7.15; ESI-MS(m / z)(M + ): The theoretical value is 591.19, and the measured value is 591.26.

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Abstract

The invention relates to an organic compound based on azabenzene and an application thereof in an OLED device. The compound has relatively high glass transition temperature and molecular thermal stability; the compound has low absorption and high refractive index in the visible light field, and light extraction efficiency of the OLED device can be effectively improved after the compound is appliedin a CPL layer of the OLED device; and the compound also has deep HOMO energy level and high electron mobility, and can be used as a hole blocking / electron transport layer material of the OLED device, transmission of holes or energy from a luminescent layer to the side of an electron layer can be effectively blocked, and thus composite efficiency of holes and electrons in the luminescent layer isimproved, and luminescent efficiency and service life of the OLED device are improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound containing an azobenzene structure 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 negative charges...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10C07D413/14C07D417/10C07D417/14C07D471/04C07D519/00H01L51/54H01L51/52
CPCC07D413/14C07D471/04C07D413/10C07D519/00C07D417/14C07D417/10H10K85/636H10K85/633H10K85/631H10K85/615H10K85/654H10K85/6574H10K85/6572H10K85/657H10K50/858
Inventor 李崇王芳张兆超张小庆
Owner JIANGSU SUNERA TECH CO LTD
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