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Organic compound taking azafluorene as core, preparation method and applications thereof

A technology of organic compounds and azafluorene, which is applied in the field of organic compounds and their preparation, can solve different problems, achieve high glass transition temperature, meet application requirements, and have good film-forming and thermal stability effects

Active Publication Date: 2020-02-25
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 taking azafluorene as core, preparation method and applications thereof
  • Organic compound taking azafluorene as core, preparation method and applications thereof
  • Organic compound taking azafluorene as core, preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Embodiment 1: the synthesis of intermediate B1:

[0076]

[0077]In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material 1-1, 0.012mol raw material 2-1, 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, 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 B1; HPLC purity 99.32%, yield 73.8%; Elemental analysis structure (molecular formula C 27 h 23 N): theoretical value C, 89.71; H, 6.41; N, 3.87; tested value: C, 89.75; H, 6.43; N, 3.89. ESI-MS (m / z) (M+): The theoretical value is 361.49, and the measured value is 361.61.

Embodiment 2

[0078] Embodiment 2: the synthesis of intermediate C1:

[0079]

[0080] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol of intermediate B1, 0.012mol of raw material 3-1, 150ml of 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, 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 X1;

[0081] Under a nitrogen atmosphere, weigh 0.02mol of intermediate X1, 0.012mol of bis(pinacolate) diboron, 0.0002mol of 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 rotate the filtrate to obtain a crude product, pass through a neut...

Embodiment 3

[0087] Embodiment 3: the synthesis of compound 1:

[0088]

[0089] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol raw material A1, 0.012mol intermediate B1, 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, 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 , the target product was obtained, the HPLC purity was 99.73%, and the yield was 76.1%. Elemental analysis structure (molecular formula C 55 h 44 N 2 ): theoretical value: C, 90.13; H, 6.05; N, 3.82; test value C, 90.14; H, 6.04; N, 3.85. HPLC-MS: The molecular weight of the material is 732.97, and the measured molecular weight is 733.07.

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Abstract

The invention discloses an organic compound taking azafluorene as a core, a preparation method and applications thereof. According to the invention, the compound has strong hole transport capability based on the pi conjugation effect in the compound, wherein the high hole transport rate can reduce the initial voltage of a device and improve the efficiency of an organic electroluminescent device; the asymmetric triarylamine structure can reduce the crystallinity of molecules, reduce the planarity of molecules and enhance the rigidity of molecules so as to improve the thermal stability of molecules; and with the application of the organic compound as the light-emitting functional layer material of an OLED light-emitting device, the utilization rate and the radiation efficiency of excitons can be effectively improved by matching azafluorene and branched chains in the range of the invention.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to an organic compound with azafluorene as its core, a preparation method and 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 an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/20C07D401/12C07D405/12C07D405/14C07D471/04H01L51/50H01L51/54
CPCC07D221/20C07D401/12C07D405/12C07D405/14C07D471/04H10K85/615H10K85/626H10K85/654H10K85/6574H10K85/6572H10K50/00H10K50/11H10K50/15
Inventor 李崇王芳徐浩杰
Owner JIANGSU SUNERA TECH CO LTD
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