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Organic compound containing pyridine and application thereof in OLED device

An electroluminescent device and organic compound technology, applied to organic electroluminescent devices, in the field of organic compounds containing azabenzene, can solve the problems affecting the angular distribution of OLED radiation spectrum and complex manufacturing process, etc.

Inactive Publication Date: 2019-07-02
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, and the process of using a surface covering layer is simple, and the luminous efficiency is increased by more than 30%, which is particularly concerned by people.

Method used

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  • Organic compound containing pyridine and application thereof in OLED device
  • Organic compound containing pyridine and application thereof in OLED device
  • Organic compound containing pyridine and application thereof in OLED device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] intermediate Synthesis

[0067] (1) with R 1 , R 2 or R 3 When expressed as a structure of general formula (2) as an example,

[0068]

[0069] 1) In the three-necked flask, feed nitrogen, add raw materials B, I-Ar 4 , sodium hydride, cuprous iodide and o-phenanthroline were dissolved in 1,3-dimethyl-2-imidazolidinone, and stirred for 30 hours. After the reaction, water was added and extracted with dichloromethane. The organic layer was washed with anhydrous Dry over sodium sulfate, rinse with a mixture of petroleum ether and ethyl acetate as eluent, and purify by column chromatography to obtain intermediate M;

[0070]

[0071] 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 were added, the mixture was stirred, and saturated potassium carbonate aqueous solution was added, and the mixed solution of the above-mentioned reactants was ...

Embodiment 2

[0103] Embodiment 2: the synthesis of compound 1:

[0104]

[0105] In a 250mL three-necked flask, nitrogen was introduced, 0.01mol of intermediate A1, 150ml of DMF, 0.03mol of intermediate B2, 0.0002mol of palladium acetate were added, stirred, and then 0.02mol. L -1 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 intermediate 1 with a HPLC purity of 99.2% and a yield of 53.6%.

[0106] Elemental analysis structure (molecular formula C 16 h 9 Cl 2 N 6 ): theoretical value C, 56.16; H, 2.65; N, 20.47; Cl, ​​20.72; found value: C, 56.22; H, 2.69; N, 20.49; ESI-MS(m / z)(M + ): The theoretical value is 341.02, and the measured value is 341.05.

[0107] In a 250mL three-necked flask, nitrogen was in...

Embodiment 3

[0109] Embodiment 3: the synthesis of compound 6:

[0110]

[0111] The preparation method of compound 6 is the same as that of Example 2, except that intermediate B2 is replaced by intermediate B1. Elemental analysis structure (molecular formula C 38 h 23 N 9 ): theoretical value C, 75.36; H, 3.83; N, 20.81; test value: C, 75.39; H, 3.85; N, 20.85. ESI-MS(m / z)(M + ): The theoretical value is 605.21, and the measured value is 605.29.

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Abstract

The invention relates to an organic compound containing pyridine and an application thereof in an OLED device. The structure of the compound of the invention is as shown in the general formula (1): the compound has higher glass transition temperature and molecular thermal stability; in the visible light field, the absorption is low and the refractive index is high. After the organic compound is applied to the CPL layer of the OLED device, the light extraction efficiency of the OLED device can be effectively improved. The compounds of the present invention also have deep HOMO levels and high electron mobility, The organic compound can be used as a hole blocking / electron transport layer material of the OLED device, holes or energy can be effectively blocked from being transferred from the light emitting layer to the electron layer side, thereby improving the recombination efficiency of holes and electrons in the light emitting layer, and further improving the light emitting efficiency and service life of the OLED device.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound containing azabenzene and its application in an organic electroluminescent device. 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 an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/14C07D401/14C07D413/14H01L51/50H01L51/54
CPCC07D403/14C07D401/14C07D413/14H10K85/654H10K85/6572H10K85/657H10K50/14H10K50/16
Inventor 王芳张兆超李崇张小庆
Owner JIANGSU SUNERA TECH CO LTD
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