Phosphorescent iridium complex and electroluminescence device thereof

A technology of phosphorescent iridium complexes and complexes, which is applied in electric solid devices, electrical components, semiconductor devices, etc., can solve problems such as insufficient thermal stability, unsatisfactory energy level structure, triplet-triplet quenching, etc. Achieve the effect of reducing self-quenching, improving electrical properties, and reducing direct effects

Inactive Publication Date: 2011-08-03
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] When applied to electroluminescent devices, phosphorescent materials such as iridium complexes often have insufficient thermal stability, lum

Method used

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  • Phosphorescent iridium complex and electroluminescence device thereof
  • Phosphorescent iridium complex and electroluminescence device thereof
  • Phosphorescent iridium complex and electroluminescence device thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1. Synthesis of 3-methyl-6-di2',4'-(fluorophenyl)pyridazine [3-methyl-6-(2,4-difluoro-phenyl)pyridazine, referred to as MDFPPya]. Take 250mg of 3-methyl-6-chloropyridazine, 463mg of 2,4-difluorophenylboronic acid and 67mg of tetraphenylphosphopalladium in a two-necked flask, add 12ml of toluene, 2ml of ethanol and 2.1ml of 2M K 2 CO 3 solution. At a temperature of 100°C, reflux for 24h. Stand to cool, quench with dichloromethane, and then use anhydrous magnesium sulfate to remove water. The solvent was evaporated under reduced pressure, and the ligand MDFPPya (79%) was obtained by silica gel chromatography.

Embodiment 2

[0033] Example 2, three (3-methyl-6-two (2 ', 4'-fluorophenyl) pyridazine) iridium [tris [3- (2, 4-difluoro-phenyl) -6-methylpyridazinato-N 1 , C 2 ]iridium, abbreviated as Ir(MDFPPya) 3 ]Synthesis. Take the ligand 3-methyl-6-bis(2',4'-fluorophenyl)pyridazine (MDFPPya) 163mg and 100mg IrCl 3 ·H 2 O In a two-necked flask, add 6ml of 2-ethoxyethanol and 2ml of deionized water. At a temperature of 110°C, reflux for 12h. Let stand to cool, add 5ml deionized water, and filter. After vacuum drying at 60°C for 4 hours, 151mg (75%) of chlorine-bridged dimer was obtained. Then dimer, 62mg MDFPPya and 104mg K 2 CO 3 Add to the two-necked bottle, add 5ml glycerin. At a temperature of 185°C, react for 12h. Standing for cooling, quenching with dichloromethane and distilling under reduced pressure to remove solvent, silica gel chromatography to obtain the final product Ir(MDFPPya) 3 135mg (71%). Ir(MDFPPya) 3 The NMR spectrum is: 1 HNMR (TMS is internal standard, solvent CDCl ...

Embodiment 3

[0034] Example 3, three-(3,6-bis(4'-fluorophenyl) pyridazine) iridium [tris[3,6-bis(4-fluorophenyl)pyri-dazinato-N 1 , C 2 ]iridium, referred to as Ir(BFPPya) 3 ]Synthesis. in N 2 Under protection, 378.0mg 3,6-bis(4'-fluorophenyl)pyridazine (BFPPya) and 172.4mg tris(acetylacetonato)iridium(III)[Ir(acac) 3 ] into 5ml glycerin. Raise the temperature to 50°C, and pump air for 4 hours with a vacuum pump. Then the temperature was raised to 190°C and refluxed for 12h. After a large amount of yellow solids were precipitated, stop the reaction, cool to room temperature, extract with dichloromethane, distill off the solvent under reduced pressure, filter, wash with a small amount of methanol, and dry in vacuo to obtain 232 mg of orange-yellow solid powder (crude yield 67.6%) ). Then it was separated by silica gel column chromatography using dichloromethane as the eluent to obtain an orange-yellow solid powder. Ir(BFPPya) 3 The NMR spectrum is: 1 HNMR (TMS is internal standard...

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Abstract

The invention discloses a phosphorescent iridium complex with high luminescent quantum efficiency and thermal stability and an electroluminescence device of the complex. In the phosphorescent iridium complex, the ligands are characterized by 3-or 6-phenyl pyridazine, a central metal ion is Ir (III), and the metal ion and three ligands form a neutral complex with the same cyclic metal ligands. In the ligand in the invention, the atom adjacent to coordination N atom is also N atom, thereby avoiding the interference of H atom on the adjacent C atom on complexing of N and metal when pyridine is taken as ligand so that the binding between the ligands and the metal ion is firmer and metal ligand charge transfer (MLCT) process is facilitated. Thus, the iridium complex has high luminescent quantum efficiency and thermal stability. Simultaneously, the energy gap of the iridium complex can be regulated through changing other functional groups on the ligand, so as to regulate the emission wavelength of a material. The iridium complex has an application potential in the aspects of organic electroluminescent display based on red-blue-green three primary colors, backlight in liquid crystal display, organic solid illumination and the like.

Description

technical field [0001] The invention belongs to the application field of organic phosphorescent materials and organic electroluminescence, including iridium complex materials with high-efficiency triplet light emission and their electroluminescence, which are expected to be obtained in the fields of organic electroluminescence displays, liquid crystal backlight sources, and organic solid luminescence application. Background technique [0002] Organic light-emitting diode (OLED) is a device that uses organic materials to emit light under electrical injection. It has all-solid-state, self-luminous, high brightness, wide viewing angle (up to 170 degrees or more), and fast response speed (about tens of nanoseconds). , thin thickness, can use flexible substrate, low voltage DC drive (3 ~ 10V), low power consumption, wide operating temperature range and other advantages. Moreover, devices based on organic materials have a simple manufacturing process, are easy to prepare in large...

Claims

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Application Information

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IPC IPC(8): C07F15/00H01L51/50H01L51/54
Inventor 密保秀高志强黄维廖章金
Owner NANJING UNIV OF POSTS & TELECOMM
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