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Fluorenyl phenylquinoline iridium complex with saturated red luminescence

A technology of fluorenylbenzoquinoline iridium and red light emission, which is applied in the direction of light-emitting materials, indium organic compounds, platinum group organic compounds, etc., and can solve problems such as inconvenient operation and complicated process

Active Publication Date: 2020-10-27
BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] In the light-emitting devices reported in the above two literatures, both the hole transport and light-emitting layers are dry-processed by vacuum evaporation, and the process is complicated and inconvenient to operate.

Method used

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  • Fluorenyl phenylquinoline iridium complex with saturated red luminescence
  • Fluorenyl phenylquinoline iridium complex with saturated red luminescence
  • Fluorenyl phenylquinoline iridium complex with saturated red luminescence

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 2

[0083] Example 1 Bis[2-(4-(N-9,9-diethylfluorene-N-3,5-xylanilino)phenyl)-4-phenylquinoline-C 2 ,N]iridium (2-pyridone) ((FPAPPQ) 2 Synthesis of Ir(acac)(7a)):

[0084] (1) Under argon protection, add 3,5-xylaniline (2.95g, 24.37mmol), 2-bromo-9,9-diethylfluorene (5.91g, 19.6mmol) into a 250ml single-necked round bottom flask ), Na-O-t-Bu (2.638g, 27.45mmol) and toluene, put into a magnet, stir and dissolve, fill a 50ml single-necked round bottom flask with argon (Ar) for 3 times, then add Pd(AcO) 2 (0.044g, 0.195mmol), X-phos (0.28g, 0.587mmol), toluene, after being dissolved, quickly added to the above reaction solution, filled with argon (Ar) twice, sealed with liquid paraffin, magnetically stirred, heated Temperature 110°C, 20h reaction, ethyl acetate extraction, drying, concentration, silica gel column separation, 2-(3,5-xylanilino)-9,9-diethylfluorene (fpa) white solid, yield 85.3%;

[0085] (2) Take a 250ml round bottom flask, put it into a magnet, weigh 1.974g (5.4...

Embodiment 2

[0091] Example 2: Bis[2-(4-(N-9,9-diethylfluorene-N-3,5-xylanilino)phenyl)-4-phenylquinoline-C 2 ,N]iridium (2-pyridine acid) ((FPAPPQ) 2 Synthesis of Ir(pic)(7b))

[0092] Steps (1)-(3) are the same as in Example 1;

[0093] (4) Take 0.44g intermediate [Ir(ppq) 2 Cl] 2 , 0.067g of sodium carbonate and pyridine acid (0.051g) were dissolved in ethylene glycol monomethyl ether (14ml), and refluxed for 20 hours under argon protection. After cooling, the mixture was separated through a silica gel column to obtain an orange-yellow solid (FPAPPQ) 2 Ir(pic)(7b)), yield 71.8%.

[0094] Product Confirmation:

[0095] 1 H NMR (400MHz, CDCl 3 )–δ(ppm):0.34–0.38(t,12H),1.90–2.01(m,8H),2.26(s,12H),6.73–7.07(m,12H),7.25–7.31(m,8H), 7.42–7.61(m,20H),7.73(d,2H),7.75-8.42(m,4H),8.56(d,2H),8.36–8.38(d,1H),9.11(s,1H);

[0096] Elemental analysis (molecular formula C 98 h 82 IrN 5 o 2 ): theoretical value: C, 75.75; H, 5.32; N, 4.51, tested value: C, 75.39; H, 5.28; N, 4.42.

Embodiment 3 2

[0097] Example 3 Bis[2-(4-(2-diethylfluorenyl)phenyl)-4-phenylquinoline-C 2 ,N]iridium(pentanedione)((FPPQ) 2 Synthesis of Ir(acac)(5a)):

[0098] (1) Dissolve 2-bromo-9,9'-diethylfluorene (30mmol, 9.0g) in 200ml tetrahydrofuran in a round-bottomed flask, and cool to -78°C under the protection of argon; add n-butyl dropwise Lithium base (1.6M, 45mmol, 28.1ml) was reacted for 1 hour, trimethyl borate (45mmol, 8.83g) was added once; the reaction was raised to room temperature for 30 minutes, and then reacted for 1 hour; treated with dilute acid and extracted with ethyl acetate , dried, concentrated, and separated by silica gel column chromatography to obtain a white solid 9,9'-diethylfluorene-2-boronic acid with a yield of 52.3w%;

[0099] (2) Under the protection of argon, 2-(4-bromophenyl)-4-phenylquinoline (2.484g, 6.90mmol), 9,9'-diethylfluorene-2-boronic acid (2.02g, 7.58mmol), dissolved in 36ml of anhydrous toluene and 24ml of absolute ethanol, adding 2M Na 2 CO 3(3....

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Abstract

The invention relates to a fluorenyl phenylquinoline iridium complex with saturated red luminescence, and belongs to the technical field of luminescent materials. A general formula structure of the complex is shown as the specification, wherein the structure of Y is as shown in the specification; according to the fluorenyl phenylquinoline iridium complex with saturated red luminescence can keep the two important characteristics of high light emitting efficiency and saturated red light coordinates (0.67, 0.33) of a 2-phenylquinoline iridium complex, the conjugation degree of molecules can alsobe expanded, strong contact and internal rotation among the molecules are effectively inhibited, non-radiative relaxation is reduced, thermal stability and film-forming property are improved, the holetransport capacity of the compound and energy transfer from a host to an object are enhanced, and the red light efficiency of the material and the device is effectively improved.

Description

technical field [0001] The invention relates to a luminescent material for a white organic electroluminescence device, in particular to a fluorenylbenzoquinoline iridium complex emitting saturated red light, and belongs to the technical field of luminescent materials. Background technique [0002] White organic electroluminescent devices (WOLEDs) have potential applications in many aspects such as backlight display, full-color display, and solid-state luminescence. When phosphorescent materials are used in white organic electroluminescent devices, their efficiency and full-color active matrix display have been significantly improved. [0003] White organic electroluminescent devices are most commonly composed of three primary colors of red-green-blue, but in order to simplify the device, orange (or orange-red)-blue two colors form two independent layers in a certain proportion, which can be adjusted by adjusting the doping concentration, luminescence The thickness of the la...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54H01L51/50
CPCC07F15/0033C09K11/06C09K2211/185C09K2211/1029H10K85/342H10K50/11Y02B20/00
Inventor 张文官
Owner BEIJING INSTITUTE OF GRAPHIC COMMUNICATION
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