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A [3+2+1] coordination configuration iridium metal complex and its preparation method and organic electroluminescent device

A complex and metal technology, applied in the [3+2+1] coordination configuration iridium metal complex and its preparation and the field of organic electroluminescence devices, can solve the problems of difficult adjustment and reduced quantum efficiency, etc.

Active Publication Date: 2021-03-19
深圳普瑞材料技术有限公司
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0006] However, the phosphorescent metal complexes in the light-emitting layer in the prior art have the following technical difficulties: 1. The color peak of the blue light-emitting material of the metal iridium (III) complex is mainly concentrated in sky blue (the main wavelength peak is located at about ~460nm), which is difficult to adjust From ultraviolet to deep blue (the main wavelength peak is between 380nm–450nm); 2. After the emission peak of the metal iridium (III) complex is adjusted to red by the ligand, the quantum efficiency is greatly reduced

Method used

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  • A [3+2+1] coordination configuration iridium metal complex and its preparation method and organic electroluminescent device
  • A [3+2+1] coordination configuration iridium metal complex and its preparation method and organic electroluminescent device
  • A [3+2+1] coordination configuration iridium metal complex and its preparation method and organic electroluminescent device

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102] Synthesis of iridium complexes (L A1 )Ir(L B1 )(L C1 ) - Synthesis of Example Ir1a:

[0103]

[0104] Add [H to a 25 mL Schlenk tube with a magnet under nitrogen protection 3 L A1 ]Br 2 (0.7g, 1.45mmol), iridium metal precursor ([Ir(cod)Cl] 2 , 0.48g, 0.73mmol) and acetonitrile (20mL). Nitrogen was introduced by needle and the solution was degassed for 5 minutes, after which triethylamine (2 mL) was added and heated to 90° C., and the reaction was quenched after 4 hours. After removing the organic solvent under low pressure, add HL under the protection of nitrogen B1 (0.276g, 1.45mmol) and propionic acid (10mL). The mixture was heated to 150°C and stirred overnight. After stopping the reaction, it was cooled to room temperature and then filtered. The luminescent substance was extracted with dichloromethane (150 mL×3) until a small amount of black solid residue remained. The dichloromethane solution was concentrated to about 5 mL, diethyl ether (20 mL to 50...

Embodiment 2

[0106] Synthesis of iridium complexes (L A1 )Ir(L B1 )(L C2 ) - Synthesis of Example Ir1b:

[0107]

[0108] Add (L A1 )Ir(L B1 )(L C1 ) (0.18g, 0.23mmol), silver cyanide (45mg, 0.34mmol) and N,N-dimethylformamide (10mL). The reaction solution was heated to 90° C., and the reaction was stopped after half an hour. N,N-Dimethylformamide was removed under reduced pressure to give a luminescent solid. Silica gel column chromatography was used for separation, and the mobile phase was dichloromethane to dichloromethane / acetonitrile (volume ratio: 10:1) to obtain the target product (0.1 g, 0.14 mmol), yield: 60%. 1 HNMR (500 MHz, deuterated chloroform): δ = 10.27 (d, J = 5.4Hz, 1H), 8.39 (d, J = 9.8Hz, 1H), 7.89 (t, J = 7.9Hz, 1H), 7.47 (d,J=2.0Hz,2H),7.31–7.27(m,1H),7.24–7.20(m,1H),7.13(d,J=7.8Hz,2H),6.76(d,J=2.0Hz, 2H), 6.25 (ddd, J=13.1, 8.9, 2.4Hz, 1H), 5.48 (dd, J=8.6, 2.4Hz, 1H), 3.26 (ddd, J=13.5, 10.0, 6.0Hz, 2H), 3.17 (ddd,J=13.4,10.0,5.8Hz,2H),1.46–1.38(m,2H),1...

Embodiment 3

[0110] Synthesis of iridium complexes (L A1 )Ir(L B1 )(L C3 ) - Synthesis of Example Ir1c:

[0111]

[0112] Add (L A1 )Ir(L B1 )(L C1 ) (0.55, 0.70 mmol), silver cyanate (0.13, 0.87 mmol) and N,N-dimethylformamide (10 mL). The reaction solution was heated to 90° C., and the reaction was stopped after half an hour. N,N-Dimethylformamide was removed under reduced pressure to give a luminescent solid. Silica gel column chromatography was used for separation, and the mobile phase was dichloromethane to dichloromethane / acetonitrile (volume ratio: 10:1) to obtain the target product (0.42 g, 0.56 mmol), yield: 80%. 1 HNMR (400 MHz, deuterated chloroform): δ = 9.93–9.86 (m, 1H), 8.43–8.36 (m, 1H), 7.93–7.86 (m, 1H), 7.48 (d, J = 2.0Hz, 2H ),7.40(ddd,J=7.2,5.6,1.3Hz,1H),7.24(dd,J=8.6,6.8Hz,1H),7.18–7.13(m,2H),6.75(d,J=2.1Hz, 2H), 6.22(ddd, J=13.1, 9.0, 2.5Hz, 1H), 5.48(dd, J=9.4, 2.5Hz, 1H), 3.30–3.12(m, 4H), 1.41–1.30(m, 2H) , 1.19–1.06(m,2H), 0.94–0.84(m,2H), 0.84–0.69(...

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Abstract

The invention belongs to the technical field of organic photoelectric materials. The invention discloses an iridium metal complex in a [3+2+1] coordination configuration, a preparation method and application thereof, and has a structure shown in formula (I). The iridium metal complex realizes the emission wavelength from deep ultraviolet to infrared by synergistically adjusting bidentate ligands, and utilizing the strong-field ligand action of tridentate ligands and monodentate ligands, with higher quantum efficiency and adjustable Phosphorescence lifetime. The iridium metal complex is applied to prepare the guest material of the light-emitting layer in the organic electroluminescent device. The invention also discloses an organic electroluminescent device. At least one functional layer contains the above-mentioned iridium metal complex, and the above-mentioned complex is used as the guest material of the light-emitting layer to prepare an OLED device with high blue light luminous efficiency.

Description

Technical field: [0001] The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. More particularly, it relates to a phosphorescent light-emitting material comprising a metal iridium (III) complex formed in a [3+2+1] type coordination mode and the use of the series of complexes for preparing organic electroluminescent devices and compound synthesis formula. Background technique: [0002] Organic light emitting diodes (OLEDs, Organic Light Emitting Diodes) were first disclosed by Deng Qingyun et al. in (U.S. Patent 4,356,429) and in (Appl.Phys.Lett.1987,51,913). Due to the characteristics of wide viewing angle, ultra-thin, self-illumination, low voltage and high efficiency, and flexible display, OLEDs are the development trend of the next generation of display and lighting, and have become one of the most promising display technologies. [0003] Fluorescent OLEDs only use singlets to emit light, and its interna...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54H01L51/50
CPCC07F15/0033C09K11/06C09K2211/185C09K2211/1044C09K2211/1029C09K2211/1092C09K2211/1037H10K85/342H10K50/11
Inventor 杨琛吴远
Owner 深圳普瑞材料技术有限公司
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