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Triazole structure unit-based tetradentate cyclometalated platinum (II) and palladium (II) complex phosphorescent materials

A phosphorescent luminescent material, metal platinum technology, applied in luminescent materials, palladium organic compounds, platinum group organic compounds, etc., can solve problems such as spectral blue shift, and achieve the effect of reducing energy, strong molecular rigidity, and high phosphorescent luminescence intensity

Active Publication Date: 2017-09-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, the research on phosphorescent molecules of tetradentate ring metal palladium(II) complexes is still in its infancy, and there are few related reports, but palladium salts are more economical than platinum salts, which can reduce the cost of phosphorescent materials, and more importantly, for The spectrum of phosphorescent molecules of platinum(II) complexes and palladium(II) complexes with the same ligand will have an obvious blue shift, which provides a new way for the development of efficient and stable blue light materials that have not been solved for a long time in the OLED field. It is of great significance for the development of new phosphorescent materials

Method used

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  • Triazole structure unit-based tetradentate cyclometalated platinum (II) and palladium (II) complex phosphorescent materials
  • Triazole structure unit-based tetradentate cyclometalated platinum (II) and palladium (II) complex phosphorescent materials
  • Triazole structure unit-based tetradentate cyclometalated platinum (II) and palladium (II) complex phosphorescent materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: The synthetic route of the phosphorescent material Pt1 of tetracyclic metal platinum complex is as follows:

[0045]

[0046] Synthesis of 3-(3-(1-(1H-1,2,3-triazolyl))phenoxy)-(2-pyridyloxy)benzene Ligand 1: Reaction to a dry 25 mL with a magnetic rotor 1-(3-hydroxyphenyl)-1H-1,2,3-triazole (644.6mg, 4.0mmol, 1.0eq), 3-bromo-(2-pyridyloxy)benzene (1.20g , 4.8mmol, 1.2eq), cuprous iodide (76.2mg, 0.4mmol, 0.1eq), ligand 2-pyridinecarboxylic acid (98.5mg, 0.8mmol, 0.2eq), potassium phosphate (1.78g, 8.4mmol, 2.1 eq). The nitrogen was purged three times, then the solvent dimethyl sulfoxide (5 mL) was added. Then the reaction mixture was stirred at 105°C for 3 days, cooled to room temperature, diluted with a large amount of ethyl acetate, filtered and washed with ethyl acetate. The obtained filtrate was washed 3 times with water and dried over anhydrous sodium sulfate. Filtration, the filtrate was rotary evaporated under reduced pressure to remove the sol...

Embodiment 2

[0049] Embodiment 2: The synthesis route of tetradentate ring metal platinum complex phosphorescent material Pt2 is as follows:

[0050]

[0051] Synthesis of 3-(3-(2-(2H-1,2,3-triazolyl))phenoxy)-(2-pyridyloxy)benzene ligand 2: reaction to a dry 25 mL with a magnetic rotor 2-(3-hydroxyphenyl)-2H-1,2,3-triazole (644.6mg, 4.0mmol, 1.0eq), 3-bromo-(2-pyridyloxy)benzene (1.20g , 4.8mmol, 1.2eq), cuprous iodide (76.2mg, 0.4mmol, 0.1eq), ligand 2-pyridinecarboxylic acid (98.5mg, 0.8mmol, 0.2eq), potassium phosphate (1.78g, 8.4mmol, 2.1 eq). The nitrogen was purged three times, then the solvent dimethyl sulfoxide (5 mL) was added. Then the reaction mixture was stirred at 105°C for 3 days, cooled to room temperature, diluted with a large amount of ethyl acetate, filtered and washed with ethyl acetate. The obtained filtrate was washed 3 times with water and dried over anhydrous sodium sulfate. Filtration, the filtrate was rotary evaporated under reduced pressure to remove the s...

Embodiment 3

[0054] Example 3: The synthesis route of the phosphorescent material Pd1 of tetradentate ring metal platinum complex is as follows:

[0055]

[0056] Add Ligand 1 (486.8mg, 1.5mmol, 1.0eq) obtained in the previous step, Pd(OAc) 2 (364.2mg, 1.6mmol, 1.1eq) and n Bu 4 NBr (48.3 mg, 0.15 mmol, 0.1 eq). The nitrogen was purged three times, then the solvent acetic acid (88 mL) was added. The reaction was then stirred at 110°C for 2 days. The reaction mixture was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography, eluting agent (petroleum ether / dichloromethane=1:1-1:4), and 417.9 mg of white solid was obtained. rate of 64%.

[0057] 1 H NMR (500MHz, DMSO-d 6 ):δ6.94(dd, J=6.0,1.5Hz,1H),7.04(dd,J=8.0,1.0Hz,1H),7.11(dd,J=8.0,0.5Hz,1H),7.23(t, J=8.0Hz, 1H), 7.36(t, J=8.0Hz, 1H), 7.44-7.48(m, 2H), 7.68(dd, J=8.0, 1.0Hz, 1H), 8.17(ddd, J=...

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Abstract

The invention discloses tetradentate cyclometalated platinum (II) and palladium (II) complex phosphorescent materials containing a five-membered heteroaryl ring. The tetradentate cyclometalated platinum (II) or palladium (II) phosphorescent material is shown as formula 1 or formula 2 (shown in the description), wherein M1 or M2 is respectively platinum or palladium, R1, R2, R3, R4, R5, R6, R7 or R8 is respectively hydrogen, deuterium, C1-C6 alkyl, C1-C6 alkoxy, halogen, amino, C6-C20 aryl or C6-C20 heteroaryl, or two carbons neighboring a heteroaryl ring are connected to a cyclosubstituent, n1-n8 represent the number of substituents, n1 or n5 is respectively 1 to 2, and n2, n3, n4, n6, n7 or n8 is respectively 1 to 3. The phosphorescent materials disclosed by the invention can effectively increase the chemical stability and thermostability of molecules, have good luminescent property, and can be used in organic light-emitting devices.

Description

technical field [0001] The invention relates to the field of phosphorescent luminescent materials, in particular to a class of tetracyclic metal platinum (II) and palladium (II) complex phosphorescent materials containing a triazole five-membered heteroaromatic ring. Background technique [0002] OLED is an Organic Light-Emitting Diode (Organic Light-Emitting Diode) or an Organic Light-Emitting Device (Organic Light-Emitting Device), also known as an Organic Electroluminescent Device. Organic electroluminescence refers to a luminescence phenomenon in which small organic molecules, metal-organic complex molecules or polymer molecular light-emitting materials directly convert electrical energy into light energy under the action of a forward bias electric field. [0003] OLED is an autonomous light-emitting device without a backlight. It has the characteristics of fast response, low driving voltage, high luminous efficiency and resolution, high contrast, and wide viewing angle....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/54
CPCC09K11/06C07F15/006C07F15/0086C09K2211/185H10K85/341H10K85/346
Inventor 李贵杰佘远斌赵向东温媛媛
Owner ZHEJIANG UNIV OF TECH
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