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Electroluminescent metallo-supramolecules with terpyridine-based groups

A supramolecular and metal technology, applied in luminescent materials, 2/12 group organic compounds without C-metal bonds, circuits, etc.

Inactive Publication Date: 2009-07-22
VERSITECH LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, only UV-vis, GPC and NMR studies are reported

Method used

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  • Electroluminescent metallo-supramolecules with terpyridine-based groups
  • Electroluminescent metallo-supramolecules with terpyridine-based groups
  • Electroluminescent metallo-supramolecules with terpyridine-based groups

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Synthesis of model compound 5a - heating zinc acetate dihydrate (1 mmol) and 4'-phenyl-2,2':6' in 10 ml of N-methylpyrrolidone (NMP) under nitrogen atmosphere at 100 °C , 2"-terpyridine (1mmol) for 3 hours. After filtration, an excess of potassium hexafluorophosphate (KPF 6 ). The precipitate was washed with methanol, and the solid was washed with ethanol and CH 3 The CN mixture was recrystallized. Yield: 86%. FABMS: m / e 685; C 42 h 30 N 6 Calculated m / e 684.1 for Zn.

[0057] 1 H NMR (DMSO, δ, ppm): 9.38 (1H, s), 9.12 (4H, d, J=8.0Hz), 8.41 (4H, d, J=7.1Hz), 8.27 (4H, t, J=7.5 Hz), 7.94(4H, d, J=4.2Hz), 7.5(6H, m), 7.48(4H, t, J=6.1Hz). 13 C NMR (DMSO, δ, ppm): 155.1, 149.4, 147.7, 141.2, 135.7, 131.1, 129.8, 129.4, 128.1, 127.6, 123.5, 121.1.

Embodiment 2

[0059] Synthesis of model compound 5b - Yield: 80%. FABMS: m / e 885; C 54 h 54 N 6 o 2 Calculated m / e 884.4 for Zn.

[0060] 1 H NMR (CDCl 3 , δ, ppm): 9.33 (4H, s), 9.14 (4H, d, J=8.0Hz), 8.44 (4H, d, J=8.5Hz), 8.27 (4H, t, J=7.6Hz), 7.93 (4H, d, J = 4.7Hz), 7.48 (4H, dd, J = 12.6 Hz, J = 5.6Hz), 7.29 (4H, d, J = 8.7Hz), 4.17 (4H, t, J = 6.6Hz ), 1.81(8H, m), 1.48(4H, m), 0.92(6H, t, J=6.8Hz). 13 C NMR (CDCl 3 , δ, ppm): 161.9, 155.1, 149.8, 148.3, 141.7, 130.3, 128.1, 127.7, 123.9, 120.4, 115.8, 68.4, 31.5, 29.1, 25.7, 22.6, 14.4.

Embodiment 3

[0062] Synthesis of Monomer 6a - To a suspension of 100 ml DMSO in KOH (2.5 mmol) was added 4'-(4-hydroxyphenyl)-2,2':6',2"-terpyridine (2.05 mmol). Stir at 90° C. for 1 hour, add 1,8-dibromooctane (1.0 mmol) and KI (catalytic amount). The resulting mixture is stirred for 24 hours. The suspension is cooled to room temperature and poured into 500 ml of water. The precipitate is filtered. The resulting The solid was recrystallized from a mixture of ethanol and acetone. Yield: 72%. FABMS: m / e761;C 50 h 44 N 6 o 2 Calculated m / e 760.9.

[0063] 1 H NMR (CDCl 3 , δ, ppm): 8.71 (8H, m), 8.66 (6H, d, J=8.0Hz), 7.86 (8H, m), 7.34 (4H, dt, J=4.8Hz, J=1.0Hz), 7.02 (4H, d, J=8.8Hz), 4.04(4H, t, J=6.5Hz), 1.83(4H, m), 1.50(8H, m). 13 C NMR (CDCl 3 , δ, ppm): 156.4, 155.8, 149.8, 149.1, 136.8, 130.5, 128.5, 123.7, 121.3, 118.2, 118.1, 114.9, 68.1, 29.3, 29.2, 26.3.

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Abstract

Highly fluorescent metal-supramolecules based on terpyridyl monomers and transition metals were obtained. These robust supramolecules offer high quantum yields from violet to blue, green or yellow emission. Owing to desirable properties such as high brightness, high purity, low cost, and high thermal stability, these supramolecules appear to be promising emitters for polymeric light-emitting diodes (PLEDs). The molecular structure of the supramolecule is represented by formula I: (I) wherein M represents IB, IIB, VIIA, VIIIA group or lanthanide metal; R is each independently selected from hydrogen, halogen, alkyl, substituted Alkyl, aryl, substituted aryl or well-known donor and acceptor groups; X is independently in each occurrence and is a nitrogen or carbon atom; R' is selected from alkoxy, aryloxy, hetero Aryloxy, alkyl, aryl, heteroaryl, alkyl ketone, aryl ketone, heteroaryl ketone, alkyl ester, aryl ester, heteroaryl ester, alkyl amide, aryl amide, heteroaryl amide, alkylthio, arylthio, fluoroalkyl, fluoroaryl, amine, imide, carboxylate, sulfonyl, alkyleneoxy, polyalkyleneoxy, or combinations thereof . n is an integer from 1 to 100,000; Z is a counterion selected from the group consisting of acetate, acetylacetonate, cyclohexanebutyrate, ethylhexanoate, halide, hexafluorophosphate, hexafluoroacetylacetonate, nitrate, Perchlorate, phosphate, sulfate, tetrafluoroborate or fluoromethanesulfonate; y is an integer from 0-4.

Description

field of invention [0001] The present invention relates to highly fluorescent metallo-supramolecules that exhibit strong and distinct color emissions through modification of the supramolecular groups, offering new perspectives for the design of efficient electroluminescent light-emitting polymers and devices. Background technique [0002] Products featuring organic and polymeric light-emitting devices (OLEDs and PLEDs), first entered the market in 1999 and 2002. Due to the many advantages of LCD technology, such as simple structure, thin-layer thickness, light-weight, wide viewing angle, low operating voltage, and possibility of producing large-area displays, it is very popular with more than 100 manufacturers Committed to the development of OLED and PLED. [0003] The device has been fabricated with organic materials including small molecules and polymers. Small molecule developers include Eastman Kodak Corporation, Inemitsu Kosan Co., Ltd., Sony Chemical Corporation, and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G79/00C07D213/22C07D271/06C07F3/00C09K11/06H01L51/00H01L51/30H01L51/50
CPCC09K2211/1475H01L51/0037C09K2211/188C07F3/003C07D213/22C09K2211/1466H01L51/0035H01L51/0077C08G83/008H01L51/0043H01L51/0039Y10S428/917H01L51/0038H01L51/5012C07D271/06C09K11/06H10K85/111H10K85/1135H10K85/115H10K85/114H10K85/151H10K85/30H10K50/11
Inventor 支志明余思捷
Owner VERSITECH LTD
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