Polysubstituted quinoline-coordinated iridium-hybridized compound as well as preparation method and application of compound

A compound and multi-substitution technology, applied in indium organic compounds, platinum group organic compounds, chemical instruments and methods, etc., can solve the problems of high cost, high material labor and material cost, and difficult purification, and achieve high-efficiency mass production. cost, and the effect of improving fluorescence quantum efficiency

Inactive Publication Date: 2017-12-12
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Each step of this route has a lot of competing side reactions, which need to be carefully separated by column chromatography, and the efficiency is very low. The actual yield of the ligand reported in the literature is up to about 10%.
And the reaction also involves the introduction of alkyl suzuki coupling, the conditions are harsh and the cost is high
Combining the above factors, the manpower and material costs of materials prepared by known industrial routes are very high, the purification is extremely difficult, and a large amount of waste residue and waste liquid are produced

Method used

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  • Polysubstituted quinoline-coordinated iridium-hybridized compound as well as preparation method and application of compound
  • Polysubstituted quinoline-coordinated iridium-hybridized compound as well as preparation method and application of compound
  • Polysubstituted quinoline-coordinated iridium-hybridized compound as well as preparation method and application of compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] The preparation of embodiment 1 iridium complex 11

[0065] R a = p-tolyl, R b = methyl, R c = phenyl, R d = methyl, R e = Hydrogen, R f = Methyl

[0066](1) Synthesis of N-(4'-methyl-[1,1'-biphenyl]-4-yl)-3-oxo-2-phenylbutanamide. Add 4'-methyl-[1,1'-biphenyl]-4-amine (1g, 5.5mmol), ethyl 2-phenylacetoacetate (3.1g, 15mmol) and xylene ( 15 mL), reaction system N 2 After bubbling for three minutes, the temperature was slowly raised to 145°C, and stirred at 145°C for 16 hours. TLC (petroleum ether: ethyl acetate = 5:1) showed that the reaction was complete, the reaction solution was cooled to room temperature, the product was precipitated, filtered, and dried in air to obtain pale yellow N-(4'-methyl-[1,1'- Biphenyl]-4-yl)-3-oxo-2-phenylbutanamide (500 mg, 26% yield). 1 H NMR (300MHz, DMSO) δ10.40(s, 1H), 7.66(d, J=8.7Hz, 2H), 7.60(d, J=8.7Hz, 2H), 7.53(d, J=8.1 Hz, 2H ), 7.38–7.31 (m, 5H), 7.24 (d, J=7.8Hz, 2H), 5.00 (s, 1H), 2.33 (s, 3H), 2.19 (s, 3H).

[0...

Embodiment 2

[0077] The preparation of embodiment 2 iridium complex 126

[0078] R a = methyl, R b = p-tolyl, R c = Hydrogen, R d = methyl, R e = Hydrogen, R f = Methyl

[0079] (1) Synthesis of 3-oxo-N,3-di-p-tolylpropionamide. Add p-toluidine (2.7g, 25 mmol), 3-oxo-3-p-tolyl-propionic acid ethyl ester (10.3g, 50mmol) and xylene (20mL) to 100ml sealed tube, reaction system N 2 After bubbling for three minutes, the temperature was slowly raised to 145°C, and stirred at 145°C for 16 hours. TLC (petroleum ether: ethyl acetate = 5:1) showed that the reaction was complete, the reaction solution was cooled to room temperature, the product was precipitated, filtered, and dried in air to obtain white 3-oxo-N, 3-di-p-tolylpropane Amide (3.4 g, 60%). 1 H NMR (300MHz, CDCl 3 )δ9.21(s,1H),7.94(d,J=8.1Hz,2H),7.46(d,J=7.5Hz,2H),7.31(d,J=8.1Hz,2H),7.13(d, J=7.5Hz,2H),4.07(s,1H),4.04(br,1H), 2.44(s,3H),2.32(s,3H).

[0080]

[0081] (2) Synthesis of 6-methyl-4-(p-tolyl)quinolin-2-ol. Add 3-...

Embodiment 3

[0090] The preparation method of embodiment 3 iridium complex 201

[0091] R a = methyl, R b = p-tolyl, R c = Hydrogen, R d = Hydrogen, R e = methyl, R f = Methyl

[0092]

[0093] (1) Synthesis of dimer 201. Add 6-methyl-2,4-bis-p-tolylquinoline (61.6 mg, 0.2 mmol), iridium trichloride trihydrate (14.1 mg, 0.04 mmol), ethylene glycol ether ( 3 mL) and water (1 mL), nitrogen was bubbled for three minutes, and the reaction system was heated to reflux for 12 hours. The reaction solution was cooled to room temperature, solid precipitated, filtered, and dried in air to obtain dimer 201 (25 mg, 76%), which was directly used in the next step.

[0094] (2) Synthesis of iridium complex 201. Add dimer (160.6mg, 0.1mmol), pentane-2,4-dione (40mg, 0.4mmol), sodium carbonate (53mg, 0.5mmol) and ethylene glycol ether (3mL) to a 75ml sealed tube, Nitrogen was bubbled for three minutes, and the reaction system was heated to reflux for 12 hours. The reaction solution was cooled ...

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Abstract

The invention discloses a polysubstituted quinoline-coordinated iridium-hybridized compound, a preparation method thereof and application of the compound in electroluminescent materials. A modified ligand of the compound comprises 3,5-bis-substituted(R<d> R<d>) in 2-subsittued phenyl, 4-substituted(R<e>) and 3,4,5-tri-substituted(R<d> R<e> R<d>)phenyl. The specific synthesis route of the polysubstituted quinoline-coordinated iridium-hybridized compound comprises the steps of generating substituted quinoline by virtue of amine ester exchange reaction, acid-catalysis Skraup cyclocondensation and hydroxyl halogenating reaction, and preparing ligand by virtue of Suzuki coupling reaction. According to the route, the side reactions of alkyl suzuki coupling reaction and competition of multiple reaction sites are avoided, so that the synthesis efficiency can be improved, and the purifying difficulty can be reduced. According to molecular spectral features and compound modification functions, the iridium-hybridized compound can be clearly used as an electroluminescent material for use in organic photoelectric appliances.

Description

technical field [0001] The invention belongs to the technical field of electronic materials, and in particular relates to a polysubstituted quinoline-coordinated iridium heterocomplex compound, a preparation method thereof, and an application of the compound in electroluminescent materials. Background technique [0002] Optoelectronic devices utilizing organic light-emitting materials are becoming increasingly popular for a number of reasons: Organic light-emitting materials are relatively cheap, so organic optoelectronic devices have a potential cost advantage over inorganic devices. Furthermore, the inherent properties of organic materials, such as their flexibility, can make them well suited for some specialized applications, such as processing on flexible substrates. Organic optoelectronic devices include organic light-emitting diodes (OLEDs), organic transistors, organic solar cells, and organic photodetectors. For OLEDs, organic light-emitting materials have performan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/11
Inventor 杭晓春陈志宽王英徐丹丹张宏海
Owner NANJING UNIV OF TECH
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