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Red to near-infrared phosphorescent iridium complex light-emitting material and application thereof to electroluminescent device

A technology for phosphorescent iridium complexes and luminescent materials, which is applied in the field of red to near-infrared phosphorescent iridium complex luminescent materials, and can solve problems such as high prices, difficult industrial production, and difficulties in large-scale industrial production

Active Publication Date: 2016-08-03
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, platinum complexes have a long phosphorescence lifetime, serious efficiency roll-off with the increase of voltage, and high prices, which make it difficult for large-scale industrial production. At present, red to near-infrared phosphorescence that can meet industrial needs There are still few optical materials, and the currently reported red phosphorescent materials used in organic electroluminescent devices all have serious triplet-triplet quenching and poor carrier transport properties at high concentrations. This makes phosphorescent materials usually doped in the host material with a very low doping concentration and within a narrow doping range as a light-emitting layer to achieve high-performance electroluminescence. In addition, some devices can achieve high-performance electroluminescence by designing complex device structures. To confine carriers and excitons to achieve high performance, all of which require relatively harsh device preparation technology, it is difficult to achieve large-scale industrial production in the future

Method used

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  • Red to near-infrared phosphorescent iridium complex light-emitting material and application thereof to electroluminescent device
  • Red to near-infrared phosphorescent iridium complex light-emitting material and application thereof to electroluminescent device
  • Red to near-infrared phosphorescent iridium complex light-emitting material and application thereof to electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the synthesis of compound 1-phenylisoquinoline (PIQ):

[0041]

[0042] Add phenylboronic acid (16mmol), 1-chloroisoquinoline (12mmol), tetrakis(triphenylphosphine)palladium (0.06mmol), 2mol / L sodium carbonate solution (60ml), tetrahydrofuran (60mL) into a two-necked flask , N 2 Under protection, heat and reflux in an oil bath at 123°C for 12 hours. Stop the reaction, pour the reaction mixture into distilled water, extract and separate the liquids with dichloromethane, collect the organic phase, and then separate it by column chromatography (silica gel, dichloromethane) The target product was obtained as white powder.

[0043] The synthesis method of other 1-phenylisoquinoline derivatives containing various substituent groups involved in the present invention is the same, and can be synthesized from phenylboronic acid substituted by corresponding substituents according to the above reaction conditions.

Embodiment 2

[0044] Embodiment 2: Chlorine bridged intermediate [Ir(piq) 2 (μ-Cl)] 2 Synthesis:

[0045]

[0046] 1-phenylisoquinoline (12mmol), iridium trichloride trihydrate (5mmol), ethylene glycol ether (15ml), purified water (5ml) were added in the two-necked flask, N 2 Under protection, it was heated to reflux in an oil bath at 150°C for 12h. Stop the reaction, add 150 mL of distilled water to precipitate a precipitate, filter the reaction mixture, wash the filter cake with absolute ethanol, and dry to obtain the red powdery target product.

[0047] The synthesis method of other iridium chloride bridged intermediate derivatives containing various substituent groups involved in the present invention is the same, and can be synthesized from corresponding 1-phenylisoquinoline derivatives according to the above reaction conditions.

Embodiment 3

[0048] Embodiment 3: the synthesis of compound 1:

[0049]

[0050] Add 41mg (0.4mmol) of diisopropylamine and 10mL of n-hexane into a 50mL three-necked flask, under nitrogen protection and at -78°C, add 0.15mL of 2.6M / L n-butyllithium dropwise, react for one hour under stirring, and add dropwise N , N′-diisopropylcarbodiimide 50mg (0.4mmol), after the dropwise addition, gradually rise to room temperature, continue to react for one hour under stirring, slowly add 0.2mmol of [Ir( piq) 2 (μ-Cl)] 2 in n-hexane solution. After the dropwise addition was completed, the temperature was slowly raised to 80° C., and the reaction was carried out for 8 hours. The reaction was stopped, the mixture was cooled to room temperature, the solvent was spin-dried under reduced pressure, and the obtained solid product was washed three times with ether, 20 mL each time. Vacuum sublimation obtained red powdery compound 1 (281.2 mg, yield 85%), and the molecular ion mass determined by mass spe...

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Abstract

The invention discloses a red to near-infrared phosphorescent iridium complex light-emitting material and application thereof to an electroluminescent device, belongs to the technical field of organic electroluminescence, and particularly relates to a dark red to near-infrared phosphorescent iridium complex light-emitting material with a 1-phenyl quinoline derivative as a first ligand and an amidino-guanidyl derivative as an auxiliary ligand. The general formula of a compound of the material is shown as follows. The red to near-infrared phosphorescent iridium complex light-emitting material is doped in a main material as a phosphorescent object to form a light-emitting layer of the organic electroluminescent device. The compound has the advantages that the preparation process is simple, and the manufactured electroluminescent device is high in efficiency and long in service life. The device can be used in the application fields of panel display, illumination, light sources and the like. The formula is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to a red-to-near-infrared phosphorescent iridium complex luminescent material in which the first ligand is a 1-phenylisoquinoline derivative and the auxiliary ligand is an amidinoguanidine derivative and its application in organic electroluminescent devices. Background technique [0002] Pope et al first reported the phenomenon of organic electroluminescence in the early 1960s. They observed the blue light emitted by anthracene when a high voltage of 400 volts was applied to both sides of anthracene single crystal. However, because single crystals are difficult to grow and the driving voltage of the device is very high (400-2000V), the technology they use has almost no practical application. Until 1987, C.W.Tang et al. of Kodak Corporation of the United States used ultra-thin film technology to use aromatic amines with better hole transport effects as...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/6572H10K85/342H10K50/11
Inventor 王悦刘宇叶开其
Owner JILIN UNIV
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