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Organic compound taking carbazole as core as well as preparation method and application thereof

An organic compound and compound technology, applied in the fields of organic chemistry, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve different problems, achieve high glass transition temperature, improve optoelectronic properties, and good thermal stability.

Pending Publication Date: 2020-06-05
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 carbazole as core as well as preparation method and application thereof
  • Organic compound taking carbazole as core as well as preparation method and application thereof
  • Organic compound taking carbazole as core as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Embodiment 1: the synthesis of intermediate E:

[0067]

[0068] (1) Under nitrogen atmosphere, weigh raw material A and raw material B and dissolve in toluene, then add Pd (PPh 3 ) 4 and sodium carbonate, stir the mixture, heat the mixed solution of the above reaction to 95-110°C, and heat to reflux for 10-24h. After the reaction, cool to room temperature, and filter the reaction solution. Column, obtain intermediate C;

[0069] Wherein, the molar ratio of the raw material A to the raw material B is 1:(1.0~1.5), and the Pd(PPh 3 ) 4 The mol ratio with raw material A is (0.005~0.01): 1, and the mol ratio of described sodium carbonate and raw material A is (1.5~3.0): 1;

[0070] (2) Under nitrogen atmosphere, weigh intermediate C and raw material D and dissolve in toluene, then add Pd (PPh 3 ) 4 and sodium carbonate, stir the mixture, heat the mixed solution of the above reaction to 95-110°C, and heat to reflux for 10-24h. After the reaction, cool to room temper...

Embodiment 2

[0081] Example 2: Synthesis of Intermediate F:

[0082]

[0083] Using raw materials 1 and 2 as raw materials, ethylene glycol dimethyl ether as a solvent, and adding PdCl to the reaction system under a nitrogen atmosphere 2 (PPh 3 ) 2 and 2-2.5M potassium carbonate aqueous solution, deoxygenated for 30 minutes, reacted at 60°C for 5-8 hours, cooled naturally to room temperature, and filtered the reaction solution, and the filtrate was subjected to vacuum rotary evaporation, and passed through a neutral silica gel column to obtain the intermediate product M ; The consumption of the ethylene glycol dimethyl ether is 50-80ml per gram of raw material 1; the molar ratio of the raw material 1 to the raw material 2 is 1:0.8-1; the PdCl 2 (PPh 3 ) 2 The molar ratio with the raw material 1 is 0.005~0.01:1; the molar ratio of the potassium carbonate and the raw material 1 is 2~2.5:1;

[0084]

[0085] Use raw material 3 and intermediate M as raw materials, ethylene glycol di...

Embodiment 3

[0097] Embodiment 3: the synthesis of compound 1:

[0098]

[0099] In a 250ml three-neck flask, under the protection of nitrogen, add 0.01mol intermediate E1, 0.012mol intermediate F1, 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, reflux reaction for 24 hours, sampling point plate, showed no iodide 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 99.43%, and the yield was 73.9%. Elemental analysis structure (molecular formula C 48 h 31 NO): Theoretical: C, 90.40; H, 4.90; N, 2.20; 0, 2.51; Tested: C, 90.42; H, 4.91; N, 2.18; HPLC-MS: The molecular weight of the material is 637.78, and the measured molecular weight is 637.89.

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Abstract

The invention relates to an organic compound taking carbazole as a core as well as a preparation method and application thereof, and belongs to the technical field of semiconductors, and the compoundhas a structure as shown in a general formula (1). The invention also discloses the preparation method and the application of the compound. The compound provided by the invention has relatively stronghole transport capability, and the hole injection and transport performance is improved under a proper HOMO energy level; under a proper LUMO energy level, the electron blocking effect is achieved, and the recombination efficiency of excitons in the light-emitting layer is improved; when the compound is used as a light-emitting functional layer material of an OLED light-emitting device, the exciton utilization rate and the radiation efficiency can be effectively improved by matching with the 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 carbazole 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 a...

Claims

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Application Information

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IPC IPC(8): C07D405/10C07D209/86C07D471/04C07D401/10C09K11/06H01L51/54
CPCC07D405/10C07D209/86C07D471/04C07D401/10C09K11/06C09K2211/1088C09K2211/1029C09K2211/1007C09K2211/1011H10K85/624H10K85/654H10K85/653
Inventor 李崇王芳徐浩杰谢丹丹
Owner JIANGSU SUNERA TECH CO LTD
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