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A compound and organic technology, applied in the field of ionic iridium metal complexes, can solve problems such as response time and stability are not very ideal
Active Publication Date: 2012-09-05
TSINGHUA UNIV +1
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[0017] Organic electrochemical cell light-emitting devices generally use a single-layer device structure of anode / luminescent layer / inert metal cathode. For electrochemical cell light-emitting devices based on heavy metal ionic complexes, the color purity of blue light needs to be improved urgently. In addition, this electrochemical cell The response time and stability of the device are not very ideal
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Embodiment 1
[0101] The synthesis of embodiment one compound (1)
[0102] Reaction formula:
[0103]
[0104] process:
[0105] In a 100mL three-neck flask equipped with a magnetic stirrer, a condensing reflux device and an argon protection device, add [Ir(ppy) 2 Cl] 2 (0.1mmol, 0.1072g), 2-(1-pyrazolyl)pyridine (0.20mmol, 0.0326g), ethylene glycol 20ml, heated at 150°C under the protection of argon for 15 hours. Remove from heat and cool to room temperature.
[0106] Under stirring, slowly add NH dissolved in the reaction solution dropwise 4 PF 6 (2mmol, 0.326g) saturated aqueous solution, stirred at room temperature for 1h after the dropwise addition, left to freeze for 2h, filtered with suction, washed the solid with deionized water, a small amount of methanol solvent, and dried in vacuum for 5h to obtain a crude product. The crude product was subjected to column separation (dichloromethane:acetone=20:1) to obtain a yellow solid powder with a yield of 80%.
[0107] Product MS ...
Embodiment 2
[0108] The synthesis of embodiment two compound (2)
[0109] The process is the same as in Example 1, except that the ion salt in the ion exchange reaction is changed to NaBF 4 , a yellow product was obtained.
[0110] Product MS (m / e): 646.6; elemental analysis (CHNO): theoretical value C: 49.19, H: 3.16, N: 9.56; found value C: 49.08, H: 3.10, N: 9.64.
Embodiment 3
[0111] The synthesis of embodiment three compound (3)
[0112] Process is the same as embodiment one, just changes the ionic salt in the ion exchange reaction into NaClO 4 , a yellow product was obtained.
[0113] Product MS (m / e): 646.4; elemental analysis (CHNO): theoretical value C: 48.35, H: 3.11, N: 9.40; found value C: 48.29, H: 3.04, N: 9.35.
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Abstract
The invention relates to an ionic iridium complex which can be used as doping phosphorescence dye of organic light emitting diode or luminescent layer dye of electromechanical cell lighting device. The compound formula of the invention is represented as below, wherein C^N represents a hetero-aromatic ring first ligand coordinated with sp2 hybridized C atom and sp2 hybridized N atom, N^N represents a neutral hetero-aromatic ring second ligand coordinated with lone-pair electrons on two sp2 hybridized N atoms, while the hetero-aromatic ring second ligand with two sp2 hybridized N atoms further comprises electronegative N and O atoms with conjugated with lone-pair electrons, A is a counterbalance anion with a negative charge. The inventive compound has high thermal-stability, high illuminating efficiency, and simple adjustment of illuminating color, simple synthesis process and easy purification.
Description
technical field [0001] The present invention relates to a kind of two sp 2 An ionic iridium metal complex with a neutral heteroaromatic bidentate ligand coordinated by a lone pair of electrons on a hybridized N atom as a second ligand, which can be used as an organic light-emitting diode Doped with phosphorescent dyes or used as light-emitting layer materials in electrochemical cell light-emitting devices. Background technique [0002] Organic electroluminescent devices (hereinafter referred to as organic EL) are widely used in various fields due to their ultra-thin, fully cured, self-luminous, fast response, good temperature characteristics, and flexible display. [0003] Research on organic EL began in the 1960s. In 1963, Pope et al. (J.Chem.Phys.1963, 38:2042~2043) studied the blue electroluminescence of anthracene single crystal (10~20μm), because the anthracene single crystal light-emitting layer was thick and the electrodes used Due to the constraints of materials (...
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