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Substituted tricarbonyl chloride 2, 2', 4, 2'-terpyridyl rhenium (I) coordination compound, preparation method and application thereof

A technology for chlorinating tricarbonyl and terpyridine, which is applied in the field of organic electroluminescence devices, can solve the problems of annihilation, unachieved carrier transport performance, long excited state lifetime, etc., and achieves stable properties, high yield, and improved performance. Effect

Inactive Publication Date: 2014-12-03
NANJING UNIV OF INFORMATION SCI & TECH
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AI Technical Summary

Problems solved by technology

However, the rhenium complexes reported in the literature have longer excited state lifetimes, and are prone to triplet-triplet and triplet-polaron annihilation, and the carrier transport performance of the material has not reached that of organic electroluminescent devices OLEDs. Require

Method used

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  • Substituted tricarbonyl chloride 2, 2', 4, 2'-terpyridyl rhenium (I) coordination compound, preparation method and application thereof
  • Substituted tricarbonyl chloride 2, 2', 4, 2'-terpyridyl rhenium (I) coordination compound, preparation method and application thereof
  • Substituted tricarbonyl chloride 2, 2', 4, 2'-terpyridyl rhenium (I) coordination compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Ligand Preparation and Structure Verification

[0028] The ligands are: 4-carbazole-2,2',4,2'-terpyridine (L1), 4-dianilino-2,2',4,2'-terpyridine (L2), 4- Bis(4-tert-butyl)anilino-2,2',4,2'-terpyridine (L3), 4-(N-phenyl-1-naphthalene)amino-2,2',4,2' -Terpyridine (L4), 4-(N-phenyl-2-naphthalene)amino-2,2',4,2'-terpyridine (L5).

[0029] 1. The preparation method of the ligand: in a reaction kettle, carbazole, diphenylamine, two (4-tert-butyl) aniline, (N phenyl-1-naphthalene) amine or (N phenyl-2-naphthalene) amine ( 3.0 mmol) with 4-Cl-2,2',4,2'-tripyridine (0.22 g, 0.82 mmol), potassium tert-butoxide (0.22 g, 2.0 mmol) and 1,3-dimethyl-3, 4,5,6-tetrahydro-2(1H)-pyrimidinedione (DMPU) (0.1 mL) mixed, under pure nitrogen atmosphere, at 205 o C reacted for 10-15 hours; after the reaction, the reaction mixture was cooled to 20 o C-25 oC , to extract the ligand 4-carbazole-2,2',4,2'-terpyridine (code L1, to obtain 0.12 g, yield: 39%) or diphenylamine-2,2',...

Embodiment 2

[0064] Example 2: Preparation and structural verification of complexes

[0065]The complexes are tricarbonyl chloride (4-carbazole-2,2',4,2'-terpyridine) rhenium (I) (code named as Re1), tricarbonyl chloride (4-diphenylamino-2 ,2',4,2'-terpyridine) rhenium (I) (code named Re2), tricarbonyl chloride (4-bis(4-tert-butyl)anilino-2,2',4,2 '-terpyridine) rhenium (I) (code named Re3), tricarbonyl chloride (4-(N-phenyl-1-naphthalene) amino-2,2',4,2'-terpyridine) Rhenium (I) (code name is Re4), tricarbonyl chloride (4-(N-phenyl-2-naphthalene) amino-2,2',4,2'-terpyridine) rhenium (I) (code name Set to Re5).

[0066] 1. Preparation of complexes

[0067] Each ligand is mixed with rhenium pentacarbonyl chloride (i.e. (Re(CO) 5 Cl) were mixed according to equimolar ratio (0.10 mmol), heated to 110 in anhydrous toluene (30 mL) o C reflux reaction for 6 hours, after the reaction finished, the solvent in the reaction mixture was distilled off, and the obtained yellow solid was purified ...

Embodiment 3

[0101] Example 3 Fluorescent Characterization of Complexes

[0102] Complexes include: tricarbonyl chloride (4-carbazole-2,2',4,2'-terpyridine) rhenium (I) Re1), tricarbonyl chloride (4-dianilino-2,2' ,4,2'-terpyridine) rhenium(I) (Re2), tricarbonyl chloride (4-di(4-tert-butyl)anilino-2,2',4,2'-terpyridine) Rhenium(I)(Re3), tricarbonyl chloride (4-(Nphenyl-1-naphthalene)amino-2,2',4,2'-terpyridine) rhenium(I)(Re4) and chlorine Tricarbonyl (4-(N-phenyl-2-naphthalene)amino-2,2',4,2'-terpyridine) rhenium(I)(Re5).

[0103] Using dichloromethane as a solvent, the above-mentioned complexes of rhenium were made into concentrations of 10 -3 M's solution. At room temperature, the following data of each complex were determined separately:

[0104] Chlorotricarbonyl (4-carbazole-2,2',4,2'-terpyridine) rhenium(I)(Re1)

[0105] l abs , nm 224, 277, 295, 397 (see figure 1 )

[0106] l ex , max , nm 459, 578 (see figure 2 )

[0107] l em , max , nm 551 (see image 3 )

[010...

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Abstract

The invention provides a substituted tricarbonyl 2, 2', 4, 2'- terpyridyl rhenium (I) coordination compound, a preparation method and functions thereof. The preparation method for the rhenium (I) coordination compound includes steps of preparing a ligand and preparing the coordination compound. The rhenium (I) coordination compound has the advantages that triplet state annihilation is reduced, charge carrier transmission performance is improved, and an organic light-emitting device made of the provided rhenium (I) coordination compound can be simplified in structure and improved in performance. The rhenium (I) coordination compound is simple in synthesizing, quite high in yield, easy to purify and stable in property in the air.

Description

technical field [0001] The present invention relates to complexes of rhenium, and also relates to organic electroluminescent devices. Background technique [0002] Organic Light-emitting Diodes (OLEDs for short), also known as light-emitting diodes, are devices that convert electrical energy into light energy (Organic Electroluminescence, EL or OEL for short) in the device. Compared with other flat-panel display technologies such as inorganic electroluminescent display, liquid crystal display, and plasma display, organic electroluminescent display has the characteristics of low energy consumption, low cost, wide viewing angle, high brightness, large area, and wide luminous range. more and more noticeable. [0003] In 1987, C. W. Tang et al. of Kodak Corporation of the United States [see: Tang, C. W.; Vanslyke, S. A. Appl. Phys. Lett. 1987, 51, 913] used ultra-thin-film technology to prepare an electroluminescent (EL) device with low-voltage start-up, high-efficiency and h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F13/00H01L51/54C09K11/06
Inventor 周永慧陈敏东李俊郭彦孔庆刚
Owner NANJING UNIV OF INFORMATION SCI & TECH
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