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2-(2'-hydroxylphenyl)-benzothiazole derivative luminescent materials

A technology of hydroxyphenyl and benzothiazole, which is applied in the field of organic electroluminescent materials, can solve the problems of high driving voltage, difficult growth of single crystal, stagnation, etc., and achieve the effect of high reaction yield and simple synthesis method

Inactive Publication Date: 2011-05-11
吉林吉大瑞博光电科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the development of organic electroluminescence has been stagnant due to the difficulty in growing single crystals, high driving voltage, and almost no practical use of the technology used.

Method used

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  • 2-(2'-hydroxylphenyl)-benzothiazole derivative luminescent materials
  • 2-(2'-hydroxylphenyl)-benzothiazole derivative luminescent materials
  • 2-(2'-hydroxylphenyl)-benzothiazole derivative luminescent materials

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis of 2-(4'-dimethylamino-2'-methoxybenzene)-benzothiazole (P-1)

[0026]P-aminosalicylic acid (6g, 39.21mmol) and o-aminothiophenol (6mL, 55.68mmol) were mixed, and polyphosphoric acid (200mL) was used as solvent and dehydrating agent. Under nitrogen protection, heat in an oil bath with mechanical stirring at 150-160°C for 4 hours. After the reaction was cooled, it was poured into ice water to produce a large amount of yellow solid, which was filtered by suction. Add the solid to sodium bicarbonate aqueous solution to remove the remaining phosphoric acid, filter the off-white solid with column chromatography (silica gel, dichloromethane) to obtain the milky white pure product 2-(4'-amino-2'-hydroxyphenyl)-benzene And thiazole (P) 6.2g, yield 65.33%.

[0027] 2-(4'-amino-2'-hydroxybenzene)-benzothiazole (P) (1.33g, 5.496mmol), NaH (790mg, 32.917mmol), CH 3 I (2.05 mL, 32.915 mmol), THF (100 mL, dry) were added into a three-neck flask, and the reacti...

Embodiment 2

[0028] Example 2: Synthesis of 2-(4'-dimethylamino-2'-hydroxybenzene)-benzothiazole (P-2)

[0029] Mix P-1 (1.109g) and pyridine hydrochloride (anhydrous) thoroughly, and heat in an oil bath at 170-185°C for 2 hours under the protection of nitrogen. Add NaHCO after the reaction cools 3 The aqueous solution was freed from bubbles, extracted with dichloromethane, and evaporated to dryness under reduced pressure. The resulting solid was separated by column chromatography (silica gel, the volume ratio of dichloromethane / petroleum ether was 1:1) to obtain the product P-2 (744.9 mg, yield 71%) as light yellow powder. By-products are amino monosubstituents. The molecular ion mass determined by liquid mass analysis is: 271.1; theoretical element content (%) C 15 h 14 N 2 OS: C, 66.64; H, 10.36; N, 5.22, measured element content (%): C, 66.75; H, 10.34; N, 5.131. The above analysis results indicated that the obtained product was the expected product.

Embodiment 3

[0030] Example 3: Synthesis of 2-(4'-dianilino-2'-methoxybenzene)-benzothiazole (P-3)

[0031] (1) The basic molecule P (4g, 16.529mmol), phthalic anhydride (2.69g, 18.176mmol), triethylamine (4mL), xylene (200mL) were added to a three-necked flask, and the reaction mixture was decomposed under nitrogen protection. Heat to reflux for 9 hours. After stopping the reaction, the reaction mixture was suction filtered, washed with water several times, and then dried to obtain 5.99 g of milky white flocculent solid (PDoOH). The product PDoOH, dried potassium carbonate (3.33g, 24.130mmol), and 300mL acetonitrile (analytical grade untreated) were added into a one-necked bottle, and heated to reflux for 3 hours under nitrogen protection. After cooling, add CH 3 I (1.5mL, 24.1mmol), continue to heat under slow reflux for 10 hours. After the reaction, cool and filter with CH 2 Cl 2 Wash the filter cake, evaporate the filtrate to dryness under reduced pressure to obtain PDoMe as a mil...

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Abstract

The invention belongs to the field of organic electroluminescent materials and particularly relates to 2-(2'-hydroxylphenyl)-benzothiazole derivative luminescent materials containing meta and para substituent amino groups. In the invention, 12 organic micromolecules are obtained through modifying the amino groups and regulating electrondonating groups of molecules, wherein solid fluorescence containing hydroxyl group (-OH) substituent crosses the whole visible light region. The materials provided by the invention have the advantages of simple synthesis method and higher reaction yield of all steps. The compounds provided by the invention can be used as a luminescent layer of an electroluminescent device and can be applied to the fields of lighting sources, signal lamps, letter digital displays, sign cards, photoelectric couplers, flat-panel displays, and the like.

Description

technical field [0001] The invention belongs to the field of organic electroluminescent materials, in particular to 2-(2'-hydroxyphenyl)-benzothiazole derivative luminescent materials containing meta- and para-substituted amino groups and their application in the preparation of electroluminescent devices . Background technique [0002] The phenomenon of organic electroluminescence was first reported in the early 1960s. PoPe and others observed the blue light emitted by anthracene when a high voltage of 400 volts was applied to both sides of anthracene single crystal (see M.Pope, H.Kallmann and P . Magnante, J. Chem. Phys., 1963, 38, 2042). However, due to the difficulty in growing single crystals, the high driving voltage, and almost no practical use of the technology used, the development of organic electroluminescence has been stagnant. [0003] Until 1987, C.W.Tang et al. of Kokak Company in the United States used ultra-thin film technology to use diamine derivatives wi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66C07D417/10C09K11/06H01L51/54
Inventor 王悦
Owner 吉林吉大瑞博光电科技有限公司
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