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Oxadiazole-containing imide blue-ray iridium complex as well as preparation method thereof and application thereof

A technology of oxadiazole imide and iridium complex, which is applied in the direction of indium organic compounds, platinum group organic compounds, chemical instruments and methods, etc., can solve the problems of device efficiency roll-off, limit the application of OLEDs, and unsatisfactory performance. Achieve the effects of improving efficiency roll-off, improving carrier transport performance, and improving luminous efficiency

Inactive Publication Date: 2017-09-08
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In contrast, the performance of blue phosphorescent OLEDs is very unsatisfactory, mainly in the following aspects: the efficiency roll-off of the device is very obvious at higher current densities, which greatly limits the application of OLEDs in the fields of high-brightness display and solid-state lighting. It is one of the important issues to be solved urgently in this field

Method used

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  • Oxadiazole-containing imide blue-ray iridium complex as well as preparation method thereof and application thereof
  • Oxadiazole-containing imide blue-ray iridium complex as well as preparation method thereof and application thereof
  • Oxadiazole-containing imide blue-ray iridium complex as well as preparation method thereof and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment one: the synthesis of complex 1:

[0034] Under anhydrous and oxygen-free conditions, bis-[2-(2,4-difluorophenyl)pyridine]iridium dichloride (1.07 g, 0.88 mmol) and 2-(N-benzoyl)- The potassium salt of amino-5-phenyl-[1,3,4]-oxadiazole (0.65 g, 2.16 mmol) was dissolved in 20 ml of ethylene glycol monoethyl ether, reacted at 130°C for 12 hours, filtered, and finally Purified by column chromatography to obtain the complex bis[2-(2,4-difluorophenyl)pyridine]-{2-(N-benzoyl)-amino-5-phenyl-[1,3,4 ]-oxadiazole} iridium (1). The yield is 33%:

[0035] 1 H NMR (400MHz, CDCl 3 ,δ):8.55(d,J=4.0Hz,1H),8.32–8.25(m,3H),8.08(d,J=4.0Hz,2H),7.82(d,J=8.0Hz,2H),7.76 (d,J=4.0Hz,2H),7.45–7.39(m,4H),7.33(t,J=8.0Hz,,2H),7.12–7.06(m,2H),6.48–6.40(m,2H) ,5.79–5.74(m,2H).

[0036] MS(ESI-MS)[m / z]:m / z 837.75(M+H) + .

[0037] Elemental analysis results: Calculated values: C(%): 53.11, H(%): 2.65, N(%): 8.37.

[0038] Measured values: C (%): 53.16, H (%): 2.68, N (%): 8.33. ...

Embodiment 2

[0040] Under anhydrous and oxygen-free conditions, bis-[2-(2,4-difluorophenyl)-4-methylpyridine] iridium dichloride (1.08 g, 0.88 mmol) and 2-(N- Diphenylphosphinyl)-amino-5-phenyl-[1,3,4]-oxadiazole potassium salt (0.86 g, 2.16 mmol) was dissolved in 15 ml of ethylene glycol monoethyl ether at 130 ℃ for 12 hours, filtered, and finally purified by column chromatography to obtain the complex bis[2-(2,4-difluorophenyl)-4-methylpyridine]-{2-(N-diphenylphosphine Acyl)-amino-5-phenyl-[1,3,4]-oxadiazole} iridium (2).

[0041] The yield is 38%:

[0042] 1 H NMR (400MHz, CDCl 3 ,δ):8.99(d,J=4.0Hz,1H),8.02–7.92(m,3H),7.76–7.72(m,2H),7.63(s,2H),7.39–7.32(m,9H), 7.09(d,J=4.0Hz,2H),6.97(d,J=4.0Hz,1H),6.43–6.33(m,2H),6.28(d,J=4.0Hz,1H),5.76(d,J =8.0Hz, 1H), 5.61(d, J=8.0Hz, 1H), 2.54(s, 3H), 2.38(s, 3H).

[0043] MS(ESI-MS)[m / z]:m / z 961.75(M+H) + .

[0044] Elemental analysis results: Calculated values: C(%): 55.00, H(%): 3.25, N(%): 7.29.

[0045] Measured values: C (%): 54.98, H...

Embodiment 3

[0047] Under anhydrous and oxygen-free conditions, bis-[2′,6′-difluoro-2,3′-bipyridine] iridium dichloride (1.07 g, 0.88 mmol) and 2-(N-diphenyl Phosphinyl)-amino-5-phenyl-[1,3,4]-oxadiazole potassium salt (0.86 g, 2.16 mmol) was dissolved in 15 ml of ethylene glycol monoethyl ether and reacted at 130°C 12 hours, filtered, and finally purified by column chromatography to obtain the complex bis[2′,6′-difluoro-2,3′-bipyridine]-{2-(N-diphenylphosphoryl)-amino -5-Phenyl-[1,3,4]-oxadiazole}iridium (3). The yield is 44%:

[0048] 1 H NMR (400MHz, DMSO-d 6 ,δ):9.03(d,J=4.0Hz,1H),8.34(d,J=4.0Hz,1H),8.24(d,J=8.0Hz,1H),8.11(d,J=8.0Hz,2H ),7.84(dd,J=8.0Hz and 4.0Hz,1H),7.76–7.71(m,2H),7.55–7.46(m,9H),7.35(t,J=4.0Hz,1H),7.28–7.18 (m, 4H), 6.94 (dd, J = 8.0Hz and 4.0Hz, 1H), 5.72 (s, 1H), 5.52 (s, 1H).

[0049] MS(ESI-MS)[m / z]:m / z 935.46(M+H) + .

[0050] Elemental analysis results: Calculated values: C(%): 51.39, H(%): 2.70, N(%): 10.49.

[0051] Measured values: C (%): 51.44, H ...

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Abstract

The invention discloses oxadiazole-containing imide blue-ray iridium complex as well as a preparation method thereof and application thereof. A structural formula of the complex is one of the following: the structural formulas are shown in the description. The complex contains two electron transport groups (namely oxadiazole and Phosphine oxygen group), and can improve carrier transmission performance of blue-ray complex dye, so that luminous efficiency of an electroluminescent device is improved, and an efficiency roll-off phenomenon is improved.

Description

technical field [0001] The invention relates to an organic electroluminescent material and its application in an organic electroluminescent device, in particular to a blue light iridium complex containing oxadiazole imide, its preparation method and application. 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/12
Inventor 陈旻彧司长峰赵艺凌志天杨佳丽陈果魏斌
Owner SHANGHAI UNIV
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