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Yellow-green light cuprous complex with thermally activated delayed fluorescence properties and preparation method thereof

A technology of yellow-green light cuprous and thermal activation delay, which is applied in the field of organic electroluminescence display, and can solve the problems that vacuum evaporation OLED cannot be used, device efficiency is not high, and thermal volatility is poor.

Active Publication Date: 2016-08-10
SHANGQIU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The cuprous complexes that have been published in the literature are mostly ionic compounds with poor thermal volatility, and OLEDs cannot be prepared by vacuum evaporation, and the device efficiency is not high

Method used

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  • Yellow-green light cuprous complex with thermally activated delayed fluorescence properties and preparation method thereof
  • Yellow-green light cuprous complex with thermally activated delayed fluorescence properties and preparation method thereof
  • Yellow-green light cuprous complex with thermally activated delayed fluorescence properties and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Embodiment one: the synthesis of complex Cu1, Cu2 and Cu3 of the present invention:

[0032] 0.5mmol bis[(2-diphenylphosphino)phenyl] ether (POP) and 0.5mmol [Cu(CH 3 EN) 4 ][PF 6 ] was dissolved in 80 mL of dichloromethane, stirred at room temperature for 2 h, and then 0.54 mmol of ligand ECAF was added to the above solution, and stirred at room temperature for 4 h. The solvent was removed under reduced pressure, separated by column chromatography (eluent: dichloromethane: acetone=20:1) to obtain bright yellow solid hexafluorophosphoric acid-bis[(2-diphenylphosphino)phenyl]ether-[ 9,9-bis(9-ethylcarbazol-3-yl)-4,5-diazafluorene]copper(I)(complex Cu1)([Cu(POP)(ECAF)](PF 6 )).

[0033] 0.5mmol bis[(2-diphenylphosphino)phenyl] ether (POP) and 0.5mmol [Cu(CH 3 EN) 4 ][PF 6 ] was dissolved in 80 mL of dichloromethane, stirred at room temperature for 2 h, and then 0.54 mmol of ligand EHCAF was added to the above solution, and stirred at room temperature for 4 h. The ...

Embodiment 2

[0051] Embodiment 2: UV-visible absorption spectrum, emission spectrum and other characterizations of complexes Cu1, Cu2 and Cu3 of the present invention:

[0052] The complexes Cu1, Cu2 and Cu3 were dissolved in dichloromethane (10 -5 M), measure its absorption spectrum on Agilent 8453 UV-visible spectrophotometer, measure its fluorescence emission spectrum under its solid powder and film state on Jobin Yvon FluoroMax-3 fluorescence spectrometer:

[0053] At room temperature, the peak positions of the absorption and emission spectra are:

[0054] Hexafluorophosphoric acid-bis[(2-diphenylphosphino)phenyl]ether-[9,9-bis(9-ethylcarbazol-3-yl)-4,5-diazafluorene]copper ( I) (complex Cu1):

[0055] lambda abs,max , nm 230, 286, 340, 403 (see Figure 4 );

[0056] lambda em,max , nm 550 (powder, room temperature); 568 (powder, 77K); 528 (film, 5% in PMMA) (see Figure 5 )

[0057] Hexafluorophosphoric acid-bis[(2-diphenylphosphino)phenyl]ether-[9,9-bis(9-ethylhexylcarbazol-3...

Embodiment 3

[0064] Example 3: Preparation of organic electroluminescent devices OLEDs with complexes Cu1, Cu2 and Cu3 as light-emitting centers:

[0065] Device preparation equipment: multi-source organic molecular beam deposition system; testing equipment: Keithley Source 4200, Photo Research PR705 spectrometer.

[0066] The structure of the device is:

[0067] D1-2: ITO / PEDOT:PSS / TCTA(15nm) / mCP:10wt%Cu1(30nm) / TmPyPb(50nm) / LiF(0.5nm) / Al(100nm);

[0068] D2-2:ITO / PEDOT:PSS / TCTA(15nm) / mCP:10wt%Cu2(30nm) / TmPyPb(50nm) / LiF(0.5nm) / Al(100nm)

[0069] D3-2:ITO / PEDOT:PSS / TCTA(15nm) / mCP:10wt%Cu3(30nm) / TmPyPb(50nm) / LiF(0.5nm) / Al(100nm)

[0070] The current efficiency (cd / A) of the device is obtained from the I-V and L-V characteristics of the device:

[0071] n c =L / I

[0072] Wherein, L is the luminous brightness, I is the current density, and V is the voltage applied to both ends of the electroluminescent device.

[0073] Take 15Ω / sq ITO glass as the substrate, first clean it with glass cle...

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Abstract

The invention discloses a yellow-green light cuprous complex with thermally activated delayed fluorescence properties. The yellow-green light cuprous complex can be hexafluorophosphate-bis[(2-diphenylphosphino)phenyl]ether-[9, 9-bis(9-ethylcarbazole-3-yl)-4, 5-diazafluoren]copper (I), hexafluorophosphate-bis[(2-diphenylphosphino)phenyl]ether-[9, 9-bis(9-ethylhexylcarbazole-3-yl)-4, 5-diazafluoren]copper (I), hexafluorophosphate-bis[(2-diphenylphosphino)phenyl]ether-[9, 9-bis(9-phenylcarbazole-3-yl)-4, 5-diazafluoren]copper (I), and the structural formulas are shown as the specification, and the compounds adopt an ITO / PEDOT:PSS / TCTA(15nm) / mCP:10wt% Cu(I) complex (30nm) / TmPyPb(50nm) / LiF(0.5nm) / Al(100nm) electroluminescence device structure. The maximum brightness, current efficiency and external quantum efficiency of a complex Cu1 based electroluminescence device (D1-2) are 11010cd / m<-2>, 47.03cd / A and 14.81%, when the voltage is 7V, the emission peak is located at 548nm, and the color coordinates are (CIE, x=0.37, y=0.55), and the light is yellow green. The electroluminescence device of the complex Cu2 and the electroluminescence device of the complex Cu3 have similar properties.

Description

technical field [0001] The invention relates to an organic electroluminescence material and its application in an organic electroluminescence device, belonging to the technical field of organic electroluminescence display. Background technique [0002] Organic Electroluminescence Devices (Organic Electroluminescence Devices or Organic Light-Emitting Diodes, hereinafter referred to as OLEDs) are widely used in various fields due to their ultra-thin, fully cured, self-illuminating, fast response, good temperature characteristics, and flexible displays. Has a wide range of applications. [0003] Research on OLEDs 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 (silver colloid and sodium chloride solution), the luminous starting voltage of the device...

Claims

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Application Information

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IPC IPC(8): C07F1/08C09K11/06H01L51/54
Inventor 张付力翟滨李素芝刘双曹广秀
Owner SHANGQIU NORMAL UNIVERSITY