Organic metal iridium complex and application thereof

A technology of iridium complexes and organometallics, applied in indium organic compounds, platinum group organic compounds, organic chemistry, etc., can solve problems such as poor carrier transport ability, affecting product quality and commercial competitiveness, high cost, etc., to achieve The effect of maintaining the stability of the film layer, good industrialization prospects, and avoiding aggregation

Inactive Publication Date: 2019-07-05
JIANGSU SUNERA TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the serious triplet-triplet annihilation and poor carrier transport ability of the currently reported phosphorescent complexes, the complexes often need to be in a very low and narrow doping concentration range to achieve high High-performance electroluminescence, which requires relatively harsh device preparation conditions, resulting in higher costs in industrial production and affecting product quality and commercial competitiveness

Method used

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  • Organic metal iridium complex and application thereof
  • Organic metal iridium complex and application thereof
  • Organic metal iridium complex and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Example 1 Synthesis of Intermediate M1

[0061]

[0062] In a 250mL three-necked flask, nitrogen gas was introduced, 0.04mol of raw material A1, 150ml of THF, 0.05mol of raw material B1, 0.0004mol of tetrakis(triphenylphosphine) palladium were added, stirred, and then 0.06mol of K 2 CO 3 Aqueous solution (2M), heated to 80°C, refluxed for 10 hours, sampled and plated, the reaction was complete. Cool naturally, extract with 200ml of dichloromethane, separate layers, dry the extract with anhydrous sodium sulfate, filter, rotate the filtrate, and purify through a silica gel column to obtain intermediate M1 with a HPLC purity of 99.5% and a yield of 75.4%.

[0063] According to mass spectrometry, its molecular weight is 226.30 (C13H10N2S). The elemental analysis results are: C, 69.04; H, 4.43; N, 12.40; Theoretical values ​​are: C, 69.00; H, 4.45; N, 12.38.

[0064] The intermediate Mn was prepared by the synthesis method of the intermediate M1, and the specific struc...

Embodiment 2

[0067] The synthesis of embodiment 2 intermediate N1

[0068]

[0069] In a 250ml three-necked flask, add 0.01mol A1, 0.025mol C1, 0.03mol sodium tert-butoxide, 1×10 -4 mol Pd 2 (dba) 3 , 1×10 -4 mol of tri-tert-butylphosphine, 150ml of toluene, heated to reflux for 24 hours, sampling plate, reaction complete, natural cooling, filtration, filtrate rotary evaporation, silica gel column to obtain the target product with a purity of 99.2% and a yield of 55.8%.

[0070] According to mass spectrometry, its molecular weight is 209.30 (C13H11N3). The elemental analysis results are: C, 74.64; H, 5.33; N, 20.10; theoretical values: C, 74.62; H, 5.30; N, 20.08.

[0071] Intermediate Nn was prepared by the synthesis method of intermediate N1, and the specific structure is shown in Table 1.

[0072] Table 1

[0073]

[0074]

Embodiment 3

[0075] Example 3 Synthesis of Compound 1

[0076]

[0077] In a 150mL three-necked flask, add 0.02mol of compound N1, 3g (0.01mol) of IrCl 3 (Iridium trichloride), 60ml of ethylene glycol ether, 30mL of distilled water, nitrogen protection, heated to 120 ° C, reflux for 24 hours, then stop the reaction, naturally cooled to room temperature. Add 80 mL of 1 mol / L dilute hydrochloric acid, stir evenly, filter, rinse the filter cake 3 times with distilled water, then rinse 2 times with absolute ethanol, and vacuum dry to obtain dark green intermediate B1 with a yield of 65.5%.

[0078] In a 150mL three-necked flask, add 0.005mol B1, 0.01mol C1, 0.015mol sodium carbonate (Na 2 CO 3 ), 100mL of ethylene glycol ether, nitrogen protection, heated to 110 ° C, reflux reaction for 20 hours, then stop the reaction, naturally cooled to room temperature. Filtration, the filter cake was rinsed 3 times with distilled water, then rinsed 2 times with absolute ethanol, then dissolved with ...

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Abstract

The invention discloses an organic metal iridium complex and application thereof. Application of the complex to making of OLED devices can acquire good device performance. When the metal iridium complex is used as a luminescent layer doping material of OLED devices, the current efficiency, power efficiency and external quantum efficiency of the devices are all greatly improved. The metal iridium complex provided by the invention has good application effect in OLED devices, and has good industrialization prospects.

Description

technical field [0001] The invention relates to the technical field of semiconductors, in particular to a complex and its application as a doping material in a light-emitting layer in an organic light-emitting diode. Background technique [0002] Organic electroluminescent (OLED: Organic Light Emission Diodes) device technology can be used to manufacture new display products and also can be used to make new lighting products, which is expected to replace the existing liquid crystal display and fluorescent lighting, and has a wide application prospect. [0003] Currently, OLED display technology has been applied in smart phones, tablet computers and other fields, and will further expand to large-size applications such as TVs. However, compared with the actual product application requirements, the luminous efficiency and service life of OLED devices need to be further improved. [0004] The OLED light-emitting device is like a sandwich structure, including electrode material ...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC07F15/0033C09K11/06C09K2211/185H10K85/342H10K50/11H10K2102/00H10K2102/301
Inventor 徐凯李崇张兆超叶中华张小庆
Owner JIANGSU SUNERA TECH CO LTD
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