Organic eurepium compound based on functional o-phenan throline ligand and its electroluminous device

A technology of o-phenanthroline and functionalization, applied in the field of polymer electroluminescent devices, can solve the problems affecting the application of organic europium complexes, low luminous efficiency and luminous brightness, low luminous efficiency and luminous brightness, etc., to achieve improved Luminous efficiency and luminous brightness, improved electrical performance, good effect of monochromaticity

Inactive Publication Date: 2007-04-18
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The current problem is: the luminous efficiency and luminous brightness of polymer electroluminescent devices doped with organic europium complexes are not high, and are far lower than the luminous effic...

Method used

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  • Organic eurepium compound based on functional o-phenan throline ligand and its electroluminous device
  • Organic eurepium compound based on functional o-phenan throline ligand and its electroluminous device
  • Organic eurepium compound based on functional o-phenan throline ligand and its electroluminous device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Synthesis of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl-diphenylamine

[0052]

[0053]Add 8.87g (15.0mmol) of 4-bromotriphenylamine and 100mL of THF that was dried under sodium reflux and redistilled in a 250mL three-necked flask. 30.0mmol) of 2.2M n-butyllithium, after the dropwise addition, react at -78°C for 2h, then quickly add 10.0mL (45.0mmol) of 2-isopropoxy-4,4,5,5- Tetramethyl-1,3,2-dioxaborane, continue to react at -78°C for 3h, then naturally rise to room temperature for 24h, add an appropriate amount of distilled water to terminate the reaction, extract with anhydrous ether, wash with saturated saline , dried overnight over anhydrous magnesium sulfate, spin off the solvent, dry in vacuo, and separate by column chromatography (200-300 mesh silica gel, eluent: V 正己烷 / V 乙酸乙酯 =95 / 5), to obtain 3.8 g of white powder solid, yield 68.2%, melting point (m.p.): 92.0-93.0°C. H NMR spectrum ( 1 H NMR) (400Hz, CDCl 3 )δppm: 7.67(d, J=8.40Hz, 2H), 7.2...

Embodiment 2

[0055] Synthesis of Ligand 3,8-bis[4'-(diphenylamino)-phenyl]-1,10-phenanthroline (DTPA-Phen)

[0056]

[0057] In a 25mL three-neck flask, add 0.2523g (0.75mmol) homemade 3,8-dibromo-1,10-phenanthroline, 0.6138g (1.65mmol) 4-(4,4,5,5- Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl-diphenylamine, 0.78g (2.5mmol) of Ba(OH) 2 8H 2 O, 6mL freshly steamed toluene, 1mL distilled water, nitrogen deoxygenation for 30min, then add 33.8mg (0.03mmol) tetrakis (triphenylphosphine) palladium, under nitrogen protection, heat to reflux for 24h, CHCl 3 Extraction, dried overnight with anhydrous magnesium sulfate, solvent removal, vacuum drying, column chromatography (200-300 mesh silica gel, eluent: V CH2Cl2 / V CH3CN =10 / 1), to obtain 548mg of light yellow solid, yield 49.8%, m.p.: 269.0~272.0°C, 1 H NMR (400Hz, CDCl 3 )δppm: 9.57(d, J=2.3Hz, 2H), 8.44(d, J=2.3Hz, 2H), 7.91(s, 2H), 7.68(d, J=8.6Hz, 4H), 7.34(t, J=7.8Hz, 8H), 7.23~7.04 (m, 16H).

Embodiment 3

[0059] Synthesis of 4-bromo-4',4"-di-tert-butyl-triphenylamine

[0060]

[0061] 11.4g (44mmol) p-tert-butyl iodobenzene, 3.4g (20mmol) p-bromoaniline, 2.0g (20mmol) anhydrous K 2 CO 3 , 0.6g (10mmol) of activated copper powder and 60mL of o-dichlorobenzene were added to a 100mL three-necked flask, heated to 180-190°C under nitrogen protection, and reacted for 21h. Cool to about 100°C, filter while hot, evaporate the solvent under reduced pressure, and separate by column chromatography (200-300 mesh silica gel, eluent: V 正己烷 / V 二氯甲烷 =1 / 10), recrystallized from methanol to obtain 2.6 g of colorless needle crystals, yield 30.5%, m.p.112-114°C. 1 H NMR (400MHz, CDCl 3 ) δppm: 7.29 (m, 2H), 7.24 (m, 2H), 7.00 (d, J=7.72Hz, 4H), 6.93 (d, J=8.2Hz, 4H), 1.31 (s, 18H).

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Abstract

The present invention discloses an organic europium compound based on functional o-phenanthroline ligand and its electroluminescence device. It is characterized by that it uses dibenzoyl methane (DBM) as first ligand and uses the o-phenanthroline neutral ligand having triarylamine functional group with hole transmission performance or having oxdiazole functional group with electronic transmission performance as second ligand; because of action of the functional o-phenanthroline neutral ligand the organic europium compound based on functional o-phenanthroline ligand has obviously-improved electrical performance and dispersion property in polymer material, so that said compound has high luminescent effect and luminance in the polymer electroluminescence device.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to an organic europium complex electroluminescent material based on a functionalized o-phenanthroline ligand containing triarylamine or oxadiazole functional groups, and an electroluminescent material made of the complex Polymer electroluminescent devices. Background technique [0002] Organic europium complexes are considered to be the first choice materials for realizing high-efficiency red electroluminescence due to their advantages such as narrow emission band (half-peak width about 5nm), high color purity, and high fluorescence quantum efficiency (up to 100% in theory). It is one of the hot spots in the research of organic electroluminescent materials. In the past ten years, a lot of research work has been carried out around the electroluminescent materials of europium complexes and their electroluminescent devices, mainly including (1) organic small molecul...

Claims

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Application Information

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IPC IPC(8): C07D471/04C07F5/00H01L51/50H01L51/54C07D213/00C07D271/00C09K11/06
Inventor 朱卫国刘煜罗翠萍胡峥勇朱美香
Owner XIANGTAN UNIV
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