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Organic compound based on pyridine and benzimidazole and application of organic compound

An organic compound, 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.

Inactive Publication Date: 2017-07-21
VALIANT 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 of organic compound
  • Organic compound based on pyridine and benzimidazole and application of organic compound
  • Organic compound based on pyridine and benzimidazole and application of organic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Embodiment 1: the synthesis of intermediate I

[0067] Taking the synthesis of intermediate A1 as an example

[0068]

[0069] In a 250mL three-necked flask, blow nitrogen gas, add 0.04mol raw material 2,3-dibromo-5,6-dichloropyrazine, 100ml THF, 0.1mol phenylboronic acid, 0.0008mol tetrakis(triphenylphosphine) palladium, Stir, then add 0.12mol of K 2 CO 3 Aqueous solution (2M), heated to 80°C, refluxed for 5 hours, sampled and plated, 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 intermediate A1 with a HPLC purity of 99.7% and a yield of 87.2%.

[0070] Elemental analysis structure (molecular formula C 16 h 10 Cl 2 N 2 ): theoretical value C, 63.81; H, 3.35; Cl, ​​23.54; N, 9.30; test value: C, 63.79; H, 3.34; Cl, ​​23.55; N, 9.32. ESI-MS(m / z)(M + ): The theoretical value is 300.02,...

Embodiment 2

[0079] Embodiment 2: the synthesis of intermediate II

[0080] Take the synthesis of intermediate B1 as an example

[0081]

[0082] In a 250mL three-necked flask, nitrogen gas was introduced, and 0.02mol of intermediate A6, 100ml of THF, 0.03mol of (4-(9-H-carbazol-9-yl)phenyl)boronic acid, and 0.0004mol of tetrakis(triphenyl) Phosphine) palladium, stir, then add the K of 0.06mol 2 CO 3 Aqueous solution (2M), heated to 80°C, refluxed for 5 hours, sampled and plated, 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 intermediate B1 with a HPLC purity of 99.4% and a yield of 75.3%.

[0083] Elemental analysis structure (molecular formula C 34 h 22 ClN 3 ): theoretical value C, 80.38; H, 4.36; Cl, ​​6.98; N, 8.27; test value: C, 80.41; H, 4.35; Cl, ​​6.99; N, 8.25. ESI-MS(m / z)(M + ): The theoretic...

Embodiment 3

[0088] Embodiment 3: intermediate Synthesis

[0089] When R 1 When expressed as a structure of general formula (5),

[0090]

[0091] (1) In a 250mL three-necked flask, feed nitrogen gas, add 0.02mol raw material 2-bromo-benzimidazole, 0.03molAr 5 -I, 0.04mol sodium hydride, 0.004mol cuprous iodide and 0.01mol o-phenanthroline were dissolved in 100ml 1,3-dimethyl-2-imidazolidinone, stirred for 20-30h, after the reaction, add water And extract with dichloromethane, dry the organic layer with anhydrous sodium sulfate, use the mixture of petroleum ether and ethyl acetate as eluent rinse, the volume ratio of petroleum ether and ethyl acetate in the eluent is 1:100, column layer analysis and purification to obtain intermediate M;

[0092]

[0093] (2) Under a nitrogen atmosphere, weigh the intermediate M and dissolve it in tetrahydrofuran, and then dissolve the Br-Ar 1 -B(OH) 2 And tetrakis (triphenylphosphine) palladium is added, the mixture is stirred, and then satur...

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Abstract

The invention relates to an organic compound taking pyridine and benzimidazole as a core and an application of the organic compound on an OLED (organic light emitting diode) device. The compound has relatively high glass state temperature and molecular heat stability, low absorption and high refractive index in the field of visible light, and can effectively improve light extraction efficiency of the OLED device after the compound is applied to a CPL (circular-polarizing filter) layer of the OLED device. The compound further has an HOMO (highest occupied molecular orbital) energy level and high electron mobility, and can serve as a hole obstruction / electronic transmission layer material of the OLED device and effectively prevent a hole or energy from being transmitted to one side of an electronic layer from a light emitting layer, so that the combination efficiency of the hole and an electron on the light emitting layer is improved; and the light emitting efficiency and a service life of the OLED device are improved and prolonged.

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): C07D403/14C07D401/14C07D403/10C07D405/14C07D471/04H01L51/54
CPCC07D401/14C07D403/10C07D403/14C07D405/14C07D471/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044H10K85/631H10K85/636H10K85/626H10K85/654H10K85/6574H10K85/6572H10K50/00
Inventor 张兆超李崇唐丹丹金伟新王淼
Owner VALIANT CO LTD
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