Oxadiazole phosphinic imide/iridium complex, and preparation method and application thereof

An oxadiazole phosphinic imide iridium complex technology is applied in the field of organic electroluminescence display, which can solve the problems of long luminous life, hinder the application of OLED, poor carrier transport performance, etc., and achieves improved luminous efficiency, The effect of improving the efficiency roll-off phenomenon and improving the carrier transport performance

Inactive Publication Date: 2017-01-04
SHANGQIU NORMAL UNIVERSITY
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Problems solved by technology

However, for phosphorescent OLED devices, there is often an efficiency roll-off phenomenon caused by triplet-triplet annihilation (TTA) and triplet-polaron quenching (TPQ), that is, with the increase in luminous brightness and current density The device efficiency drops sharply with the increase of
The main reasons are: on the one hand, for phosphorescent dyes, the luminescence lifetime is long (microseconds to milliseconds), and the excited state cannot quickly return to the ground state, resulting in luminescence quenching and a decrease in the luminous efficiency of the device; on the other hand , the carrier transport performance of the complex luminescent dye is poor, and the electron and hole carriers transported by the electron transport layer and the hole transport layer cannot be effectively transported, so that the carriers and excitons gather, so that the concentration is too high Larger makes the device efficiency drop sharply
These problems have seriously hindered the application of OLEDs in full-color flat panel displays and solid-state white lighting.

Method used

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  • Oxadiazole phosphinic imide/iridium complex, and preparation method and application thereof
  • Oxadiazole phosphinic imide/iridium complex, and preparation method and application thereof
  • Oxadiazole phosphinic imide/iridium complex, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Synthesis of complex 1:

[0033] Under anhydrous and oxygen-free conditions, bis-[7,8-benzoquinoline]iridium dichloride (0.50 g, 0.43 mmol) and 2-(N-diphenylphosphinyl)-amino- The potassium salt of 5-phenyl-[1,3,4]-oxadiazole (0.43 g, 1.08 mmol) was dissolved in 15 ml of ethylene glycol monoethyl ether, reacted at 120°C for 12 hours, filtered, and recrystallized. Finally, it was purified by column chromatography to obtain the complex bis[7,8-benzoquinoline]-{2-(N-diphenylphosphoryl)-amino-5-phenyl-[1,3,4] -Oxadiazole} iridium (1).

[0034] Synthesis of complex 2:

[0035] Under anhydrous and oxygen-free conditions, bis-[2-phenylquinoline] iridium dichloride (0.50 g, 0.39 mmol) and 2-(N-diphenylphosphinyl)-amino-5- The potassium salt of phenyl-[1,3,4]-oxadiazole (0.39 g, 0.98 mmol) was dissolved in 15 ml of ethylene glycol monoethyl ether, reacted at 130 ° C for 12 hours, filtered, recrystallized, and finally passed Purified by column chromatography to obtain the com...

Embodiment 2

[0055] UV absorption spectra, emission spectra and other characterizations of complexes 1, 2 and 3:

[0056] Complexes 1, 2 and 3 were dissolved in acetonitrile (10 -5 M), oxygen removal, respectively measure its absorption and emission spectra (containing low temperature and thin film emission spectra) on Agilent Cary 60 and Hitachi F-7000 spectrometer:

[0057] The peak positions of the absorption and emission spectra of the complex are:

[0058] Bis[7,8-benzoquinoline]-{2-(N-diphenylphosphinyl)-amino-5-phenyl-[1,3,4]-oxadiazole}iridium(1) :

[0059] lambda abs,max , nm 255, 299, 441 (see attached Figure 4 )

[0060] lambda em,max , nm 539 (acetonitrile solution), 518 (low temperature), 534 (film) (see attached Figure 4 )

[0061] Bis[2-phenylquinoline]-{2-(N-diphenylphosphinyl)-amino-5-phenyl-[1,3,4]-oxadiazole}iridium (2):

[0062] lambda abs,max , nm 270, 337, 453 (see attached Figure 5 )

[0063] lambda em,max , nm 592 (acetonitrile solution), 575 (low te...

Embodiment 3

[0071] Preparation of organic electroluminescent devices OLEDs with complexes 1, 2 and 3 as luminescent centers:

[0072] Device preparation equipment: MB-MO-SE1 vacuum thermal evaporation coating equipment from Mbraun, Germany; testing equipment: Keithley Source 2400, Photo Research PR650 spectrometer.

[0073] The structure of the device is:

[0074] D1: ITO / HIO2(25nm) / NPB(5nm) / TCTA(10nm) / mCP:Complex 1(20nm) / TPBI(40nm) / Liq(1nm) / Al(100nm)D1

[0075]D2: ITO / HIO2(25nm) / NPB(5nm) / TCTA(10nm) / mCP:Complex 2(20nm) / TPBI(40nm) / Liq(1nm) / Al(100nm)D2

[0076] D3: ITO / HIO2(25nm) / NPB(5nm) / TCTA(10nm) / mCP:Complex 3(20nm) / TPBI(40nm) / Liq(1nm) / Al(100nm)D3

[0077] The current efficiency (cd / A) of the device is obtained from the I-V and L-V characteristics of the device:

[0078] n c = L / I (1)

[0079] The power efficiency of the device can be calculated by the following formula:

[0080] n p =π×S×L / (I×V) (2)

[0081] Wherein, L is the luminous brightness, I is the current density, S is t...

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Abstract

The invention discloses oxadiazole phosphinic imide / iridium complex, prepared from bis[7,8-benzoquinoline]-{2-(N-diphenylphosphino)-amino-6-phenyl-[1,3,4]-oxadiazole}iridium, bis[2-phenylquinoline]-{2-(N-diphenylphosphino)-amino-5-phenyl-[1,3,4]-oxadiazole}iridium, and bis[1-phenylisoquinoline]-{2-(N-diphenylphosphino)-amino-5-phenyl-[1,3,4]-oxadiazole}iridium. A ligand herein contains two electron transport groups (namely oxadiazole and phosphinoxy), it is possible to improve carrier transport performance of a dye of such complex, and therefore, light-emitting efficiency of an electroluminescent device with the complex is improved and efficiency roll-off thereof is improved.

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 Light-Emitting Diodes (hereinafter referred to as OLEDs) are widely used in various fields due to their ultra-thin, fast response, self-illumination, full curing, good temperature characteristics, and flexible display. [0003] In 1963, Pope et al. (J.Chem.Phys.1963,38:2042-2043) studied blue electroluminescent devices based on anthracene single crystal wafers (10-20 μm). Due to the restriction of electrode materials (silver colloid and sodium chloride solution), the luminous starting voltage of the device is as high as 400V, and the efficiency and brightness are low. However, the discovery opens up a new field of light-emitting technology. Over the next two decades, OLED research progressed slowly. Until 1987, C.W....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342
Inventor 张付力李素芝翟滨臧运波曹广秀
Owner SHANGQIU NORMAL UNIVERSITY
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