Quinoline triazole rare-earth compound as well as preparation method and application thereof

A technology of rare earth complexes and quinoline triazoles, which is applied in the fields of chemical instruments and methods, semiconductor/solid-state device manufacturing, electrical components, etc., and can solve the problems of poor stability and light stability of rare earth complexes

Inactive Publication Date: 2018-06-22
GUANGDONG RES INSTITITUTE OF PETROCHEM & FINE CHEM ENG +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The stability of these mixed-ligand rare earth complexes, especially the photostability, is generally poor

Method used

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  • Quinoline triazole rare-earth compound as well as preparation method and application thereof
  • Quinoline triazole rare-earth compound as well as preparation method and application thereof
  • Quinoline triazole rare-earth compound as well as preparation method and application thereof

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Experimental program
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preparation example Construction

[0042] The preparation method of the quinolinetriazole rare earth complex comprises the following steps:

[0043] 1) Oxidation of quinoline to nitrogen oxides

[0044] 2) Nitrogen oxide N Substituting O with cyano groups gives 2-cyano-N-quinolines

[0045] 3O) 2N-cyanoquinoline Hydrazine reacts with carboxylic acid or carboxylic acid derivative N to give ligand compound

[0046]

[0047] 4) reacting the ligand compound with the rare earth metal salt to obtain the quinolinetriazole rare earth complex with the structure shown in formula (1).

[0048] The synthetic route diagram of this quinoline triazole rare earth complex preparation method is shown in the appendix figure 1 .

[0049] Preferably, in step 1) of the preparation method, specifically adding an oxidizing agent to perform an oxidation reaction; the oxidizing agent used in the oxidation reaction is at least one of m-chloroperoxybenzoic acid and hydrogen peroxide; the molar ratio of the oxidizing agent to...

Embodiment 1

[0071] Synthesis of tris[5-(quinolin-2-yl)-1,2,4-1H-triazole]europium(III)(compound 5)

[0072] The first step: the preparation of N-oxo-quinoline (compound 2)

[0073]

[0074] First, quinoline (compound 1, 129g) and acetic acid (600mL) were added into a 2L three-necked flask, stirred evenly, and the mass fraction of adding 30% H 2 o 2 (100mL), heated to 70-75°C, stirred for 3 hours, cooled to room temperature, added mass fraction of 30% H 2 o 2 (100mL), continue heating to 60-110°C, and react for 3 hours. After cooling to room temperature, the acetic acid was concentrated under reduced pressure to obtain a red viscous oil, which was diluted with water (1000 mL), and the pH was adjusted to 8-9 with solid sodium carbonate. The resulting solution was extracted with dichloromethane (1000 mL+500 mL×3), and the organic phases were combined and dried with anhydrous sulfuric acid. After filtration, the filtrate was concentrated under pressure to obtain an orange-red oil, whi...

Embodiment 2

[0089] Preparation of tris[5-(quinolin-2-yl)-1,2,4-1H-triazole]samarium(III)(compound 6)

[0090]

[0091] Compound 4 (5.9g) and samarium trichloride hexahydrate (3.7g) obtained in Example 1 were dissolved in 50mL of 2-ethoxyethanol:water (V:V)=1:3 mixed solvent , dubbed solutions C and D. Add 1.2g of sodium hydroxide to solution C, and stir for half an hour. Then, the D solution was added dropwise into the reaction bottle of the C solution, and the reaction was stirred at room temperature for 8 hours. After the reaction was completed, the solvent was evaporated to dryness under reduced pressure, and the solid was vacuum-dried at 50° C. for 3 hours to obtain 6.5 g of gray-yellow powder.

[0092] MS: [M+1] 735.9, SmC 33 h 21 N 12 M.W.=735, M+H peak 735.9 and M+Na peak 758.1 were detected.

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Abstract

The invention discloses a quinoline triazole rare-earth compound as well as a preparation method and application thereof. The quinoline triazole rare-earth compound has a structural formula shown as aformula (I) in the description. In the formula (I), the R1 is selected from hydrogen, alkyl, halogenated alkyl or aryl; the Ln is selected from any one kind of materials from yttrium, lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium and lutecium. Meanwhile, the invention also discloses the preparation method of the quinoline triazole rare-earth compound, and also discloses the application of the quinoline triazole rare-earth compound. Through the preparation of a series of organic ligands simultaneously havingquinoline structures and triazole structures, the rare-earth compound is further prepared; the novel rare-earth compound combining the characteristics of two kinds of structures of quinoline and triazole inherits the characteristics of the two structures in aspects of luminescence property and stability; the goal of improving the performance of the rare-earth organic luminous material is achieved.

Description

technical field [0001] The invention relates to a quinolinetriazole rare earth complex, a preparation method and application thereof. Background technique [0002] OLED (Organic Light-Emitting Diode) technology is a next-generation display and lighting technology recognized by global R&D and commercial organizations. Compared with existing technologies, OLED is lightweight, ultra-thin, bendable, and has vivid and saturated colors. , high contrast and energy saving and other major advantages. [0003] The earliest report of organic electroluminescence should be traced back to 1963. Pope et al. prepared organic electroluminescent devices with anthracene single crystals. However, it was not until 1987 that C W Tang et al. successfully used aniline-TPD as the hole transport layer and aluminum and 8-hydroxyquinoline complex (Alq3) as the light-emitting layer to develop an organic light-emitting diode. Working voltage is less than 10V, brightness up to 1000cd / m 2 , such brightn...

Claims

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Application Information

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IPC IPC(8): C07D401/04C09K11/06H01L51/54
CPCC09K11/06C07D401/04C09K2211/182H10K85/351H10K50/11
Inventor 史华红麦裕良梁东陈捷陈少渠
Owner GUANGDONG RES INSTITITUTE OF PETROCHEM & FINE CHEM ENG
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