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Organic compound using diphenyleneimine as core as well as preparation method and application thereof

A technology of organic compounds and compounds, applied in organic chemistry, semiconductor/solid-state device manufacturing, electrical components, etc., can solve different problems and achieve high glass transition temperature, structural optimization, good film formation and thermal stability.

Inactive Publication Date: 2019-10-01
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, for the collocation of OLED devices with different structures, the photoelectric functional materials used have strong selectivity, and the performance of the same material in devices with different structures may be completely different.

Method used

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  • Organic compound using diphenyleneimine as core as well as preparation method and application thereof
  • Organic compound using diphenyleneimine as core as well as preparation method and application thereof
  • Organic compound using diphenyleneimine as core as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: the synthesis of intermediate X1:

[0068]

[0069] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material O1, 0.012mol raw material P1, 150ml toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(Ph) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , obtain target product intermediate X1; HPLC purity 99.67%, yield 77.4%; Elemental analysis structure (molecular formula C 21 h 19 N): Theoretical value C, 88.38;; H, 6.71; N, 4.91 Test value: C, 88.39; H, 6.7; N, 4.92. ESI-MS (m / z) (M+): The theoretical value is 285.39, and the measured value is 285.41.

Embodiment 2

[0070] Embodiment 2: the synthesis of intermediate Y1:

[0071]

[0072] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of intermediate X, 0.012mol of raw material N1, 150ml of toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(Ph) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampling plate, showed no bromide remaining, the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , to obtain the target product intermediate Z;

[0073] Under nitrogen atmosphere, weigh 0.02mol intermediate Z, 0.012mol bis(pinacolate) diboron, 0.0002mol Pd(dppf)Cl 2 1. Dissolve 0.05mol potassium acetate in toluene, react at 100-120°C for 12-24 hours, take a sample point plate, react completely, cool naturally, filter, and spin evaporate the filtrate to obtain a crude product, pass through a neutral silic...

Embodiment 3

[0078] Embodiment 3: the synthesis of compound 1:

[0079]

[0080] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material 1, 0.012mol intermediate X1, 150ml toluene and stir to mix, then add 5×10 -5 molPd 2 (dba) 3 , 5×10 -5 mol P(t-Bu) 3 , 0.03mol sodium tert-butoxide, heated to 105°C, refluxed for 24 hours, sampled on the plate, showed no bromide remaining, and the reaction was complete; naturally cooled to room temperature, filtered, the filtrate was rotary evaporated to no fraction, passed through a neutral silica gel column , the target product was obtained, the HPLC purity was 99.86%, and the yield was 78.3%. Elemental analysis structure (molecular formula C 45 h 32 N 2 ): theoretical value: C, 89.97; H, 5.37; N, 4.66; test value C, 89.98; H, 5.37; N, 4.65. HPLC-MS: The molecular weight of the material is 600.76, and the measured molecular weight is 600.73.

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Abstract

The invention relates to an organic compound using diphenyleneimine as a core as well as a preparation method and application thereof. Through Pi conjugation effect in the compound provided by the invention, the compound has high hollow hole transmission capability; the initial voltage of a device can be reduced through high hollow hole transmission speed; the efficiency of an organic electroluminescence device can be improved. In addition, an unsymmetrical triarylated amine structure can reduce the crystallinity of molecules; the plane performance of the molecules can be reduced; the movementof the molecules on the plane can be prevented, so that the thermal stability of the molecules can be improved. Meanwhile, through a structure of the compound provided by the invention, the distribution of electrons and hollow holes in the luminous layer is more balanced; at the proper HOMO energy stage, the hollow hole injection and transmission performance is improved; at the proper LUMO energystage, the electron blocking effect is achieved, and the compounding efficiency of excitons in a luminous layer is improved; when the compound is used as a luminous function layer material of the OLED luminous device, the diphenyleneimine is matched with the branch chain in the scope of the invention, and the exciton utilization rate and the radiation efficiency can be effectively improved.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound with azafluorene as the core, a preparation method and an application thereof. 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. As a current device, when a voltage is applied to the electrodes at both ends of the OLED light-emitting device, and the positive...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/20C07D405/12C07D401/12C07D413/12C07D405/14C07D221/06C07D213/38C07D471/04H01L51/50H01L51/54
CPCC07D221/20C07D405/12C07D401/12C07D413/12C07D405/14C07D221/06C07D213/38C07D471/04H10K85/636H10K85/631H10K85/615H10K85/654H10K85/6574H10K85/6572H10K85/657H10K50/00
Inventor 吴秀芹李崇张兆超张小庆唐丹丹
Owner JIANGSU SUNERA TECH CO LTD
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