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Phosphorescence manganese coordination complex, method for preparing same and application of phosphorescence manganese coordination complex

A manganese complex and phosphorescence technology, which is applied in chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, luminescent materials, etc., can solve the problem of less manganese complexes, etc., and achieves simple synthesis operation and raw material storage capacity. Large, Inexpensive Effects

Active Publication Date: 2018-08-17
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, the research on manganese complexes is still relatively small, especially in the application of electroluminescent devices.

Method used

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  • Phosphorescence manganese coordination complex, method for preparing same and application of phosphorescence manganese coordination complex
  • Phosphorescence manganese coordination complex, method for preparing same and application of phosphorescence manganese coordination complex
  • Phosphorescence manganese coordination complex, method for preparing same and application of phosphorescence manganese coordination complex

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preparation example Construction

[0030] The preparation method of phosphorescent manganese complex in the present invention comprises the following steps:

[0031] The first step, according to the molar ratio 1: (2 ~ 3): (2 ~ 4): (3 ~ 6) to take 3,6-diiodo-N-toluenesulfonylcarbazole, 3,6-di-tert-butyl Carbazole, copper powder and K 2 CO 3 After mixing, dissolve in the nitrobenzene solution, react for 12 to 24 hours under the condition of nitrogen protection and temperature at 170°C, cool to room temperature, and then remove the solvent (nitrobenzene solution) by distillation under reduced pressure to obtain the mixture. Dichloromethane was added to and the mixture was filtered to obtain a crude product. The crude product was extracted with water and dichloromethane to extract the organic layer, and the organic layer was extracted with anhydrous NaSO 4After drying, filter, concentrate, separate and purify to obtain 3,6-bis(3,6-di-tert-butylcarbazole N-)carbazole-N-tosylcarbazole;

[0032] The second step is...

Embodiment 1

[0039] When n is 1, the preparation method of 3,6-bis(3,6-di-tert-butylcarbazole N-)carbazole-N-tosylcarbazole (compound 4) is as follows:

[0040] Under nitrogen protection conditions, 3,6-diiodo-N-tosylcarbazole (1.00g, 1.7mmol), 3,6-di-tert-butylcarbazole (1.18g, 4.25mmol), copper powder ( 0.25g, 3.9mmol) and K 2 CO 3 (1.17g, 8.5mmol) were mixed and dissolved in nitrobenzene (7mL) solution to obtain a mixed solution, and the mixed solution was heated to 170°C for 12 hours. After the reaction, the mixed solution was cooled to room temperature, and the solvent was distilled off under reduced pressure. Additional dichloromethane was added and the mixture was filtered to give crude product. Water was added to the crude product and the organic layer was extracted with dichloromethane. The organic layer was dried over anhydrous NaSO4, filtered, concentrated, separated and purified to finally obtain the corresponding 3,6-bis(3,6-di-tert-butylcarbazole N- )carbazole-N-tosylcarba...

Embodiment 2

[0060] When n is 4, the preparation method of 3,6-bis(3,6-di-tert-butylcarbazole N-)carbazole-N-tosylcarbazole (compound 4) and compound TCz in this example is the same as Embodiment 1 is the same.

[0061] Compound TCz-(CH 2 ) 6 The preparation method of Br is as follows:

[0062] Under nitrogen protection, the compound TCz (0.7 g, 1.0 mmol) and t-BuOK (0.1 g, 1.0 mmol) were dissolved in dry THF (20 mL), and then 1,3-dibromohexane (23 μL, 1.5mmol), stirred and refluxed at 40°C for 10 hours, cooled to room temperature after the reaction, removed THF under reduced pressure, then added water and extracted the organic layer with dichloromethane, and the organic layer was washed with anhydrous NaSO 4 Dry, filter, concentrate, separate and purify to obtain the corresponding compound TCz-(CH 2 ) 6 Br, compound TCz-(CH 2 ) 6 Br is a white solid with a yield of 60%; compound TCz-(CH 2 ) 6 The structural characterization data of Br has a hydrogen spectrum, which is: 1 H NMR (...

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Abstract

The invention relates to a method for preparing a phosphorescence manganese compound. The method includes carrying out reaction on 3, 6-di-iodine-N-tosyl carbazole, 3-6-di-tert-butyl carbazole, copperpowder and K2CO3 to obtain 3, 6-bis-(3, 6- di-tert-butyl carbazole N-) carbazole-N-tosyl carbazole; carrying out reaction on the 3, 6-bis-(3, 6- di-tert-butyl carbazole N-) carbazole-N-tosyl carbazole and KOH to obtain compounds TCz; carrying out reaction on the compounds TCz, t-BuOK and dibromo alkane to obtain compounds TCz-R'; carrying out reaction on the compounds TCz-R' and PPh3 to obtain compounds L; carrying out reaction on the compounds L and MnBr2.4H2O to obtain the phosphorescence manganese compound. The method has the advantages that synthesis operation is simple, the method is lowin cost, products are high in luminescence quantum efficiency and current carrier efficiency, and luminescence materials and transporting materials which are good in performance can be obtained by the aid of the method.

Description

technical field [0001] The invention relates to a phosphorescent manganese complex based on a tricarbazole functionalized dendritic structure and a preparation method and application thereof, belonging to the technical field of organic photoelectric functional materials. Background technique [0002] Phosphorescent organic light-emitting diodes (PhOLEDs) have attracted extensive attention due to their potential applications in full-color flat panel displays and solid-state lighting. Phosphorescent emitters are considered superior to their phosphors due to their high photoluminescence quantum yield (PLQY) and ability to trap singlet and triplet excitons, thereby achieving 100% internal quantum efficiency. Phosphorescent emitters based on noble metals such as iridium(III), platinum(II), ruthenium(II) and osmium(II) have been extensively studied in the past decades. Significant progress has been made in the research of phosphorescent heavy metal complexes as light-emitting mat...

Claims

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Application Information

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IPC IPC(8): C07F9/6558C09K11/06C09K11/61H01L51/54H01L51/05H01L51/30
CPCC09K11/06C09K11/615C07F9/65583C09K2211/1029C09K2211/1014C09K2211/1007H10K85/6572H10K10/50
Inventor 赵强刘淑娟秦妍妍佘鹏飞李向领黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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