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Red fluorescent dye and its systhesis method and use

A technology of red fluorescence and synthesis method, which is applied in the field of fluorescent dyes with red light emission and its synthesis, which can solve the problems of reducing reaction yield, raw material consumption, and increasing cost, and achieve high yield, few reaction steps, and good red color Effects of Chromaticity Properties

Inactive Publication Date: 2008-08-06
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0023] Due to the generation of dicondensation by-products, the consumption of raw materials in the production process reduces the yield of the reaction; at the same time, because the dicondensation products can quench the fluorescence of the target compound, it is required that the organic electroluminescent fluorescent dye has a high Purity, so the dicondensation by-product must be separated from the target product; in fact, once this by-product is generated, it is difficult to remove it from the target product (C.H.Chen, C.W.Tang, J.Shi, K.P.Klubek, Macromol. Symp., 1997, 125, 49)
This will greatly increase the cost of production

Method used

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  • Red fluorescent dye and its systhesis method and use
  • Red fluorescent dye and its systhesis method and use
  • Red fluorescent dye and its systhesis method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Example 1: 4-Dicyanomethenyl-8-methyl-2-(4-dimethylaminostyryl)-5,6,7,8-tetrahydro-4H-1-benzopyran

[0085] (1). Synthesis of 1-(4-morpholine)-6-methyl-cyclohexene

[0086]

[0087] Add 11.2g (0.1mol) of 2-methylcyclohexanone, 14g (0.12mol) of morpholine, 200ml of toluene, and 1g (0.006mol) of p-toluenesulfonic acid into a round bottom flask, and heat to reflux to separate water for 5 hours. The solvent was distilled off, and 14.5 g of the product 1-(4-morpholine)-6-methyl-cyclohexene was collected by vacuum distillation at 100-102° C. / 6 mmHg, with a yield of 78%.

[0088] (2). Synthesis of 2,8-dimethyl-5,6,7,8-tetrahydro-4H-1-benzopyran-4-one

[0089]

[0090] Add 18.1g (0.1mol) 1-(4-morpholine)-6-methyl-cyclohexene, 28.5g (0.2mol) 2,2,6-trimethyl-1,3- Dioxin-4-one was heated to reflux at 150°C for 8 hours. Cool, add 500ml chloroform, wash three times with 100ml 5%-10% sodium hydroxide aqueous solution, then wash three times with 100ml water, dry with anhydrou...

Embodiment 2

[0103] Example 2: 4-Dicyanomethenyl-8-methyl-2-(4-dimethylaminostyryl)-5,6,7,8-tetrahydro-4H-1-benzopyran

[0104] (1). The synthetic method of 1-(4-morpholine)-6-methyl-cyclohexene is the same as step (1) in Example 1

[0105] (2). Synthesis of 4-dicyanomethenyl-2,8-dimethyl-5,6,7,8-tetrahydro-4H-1-benzopyran

[0106]

[0107] Add 18.1g (0.1mol) 1-(4-morpholine)-6-methyl-cyclohexene, 28.5g (0.2mol) 2,2,6-trimethyl-1,3- Dioxin-4-one was heated to reflux at 150°C for 8 hours. Cool, add 500ml chloroform, wash three times with 150ml 5%-10% aqueous sodium hydroxide solution, then wash three times with 100ml water, dry with anhydrous sodium sulfate, distill off chloroform, then add 13.2g (0.2mol) malononitrile, 150ml Ethanol, 15ml catalyst (5ml hexahydropyridine + 15ml acetic acid), heated to reflux for 2 hours. The solvent was distilled off under reduced pressure, cooled, the solid was washed with water, and dried. The solid was recrystallized with chloroform / n-hexane to obt...

Embodiment 3

[0116] Example 3: 4-Dicyanomethenyl-8-methyl-2-(juloridine-9-vinyl)-5,6,7,8-tetrahydro-4H-1-benzopyran

[0117] (1). The synthetic method of 1-(4-morpholine)-6-methyl-cyclohexene is the same as step (1) in Example 2

[0118](2).4-dicyanomethenyl-2,8-dimethyl-5,6,7,8-tetrahydro-4H-1-benzopyran synthetic method and steps in Example 2 ( 2) the same, wherein the catalyst is changed to 15ml hexahydropyridine

[0119] (3).4-Dicyanomethenyl-8-methyl-2-(juloridine-9-vinyl)-5,6,7,8-tetrahydro-4H-1-benzopyran

[0120]

[0121] In a round bottom flask, add 0.23g (1mmol) 4-dicyanomethenyl-2,8-dimethyl-5,6,7,8-tetrahydro-4H-1-benzopyran, 0.22g ( 1.1mmol) of 9-formyl juloridine, 15ml of acetonitrile, 0.10ml of hexahydropyridine, and heated to reflux for 20 hours. Acetonitrile was distilled off, cooled, the solid was rinsed with acetonitrile several times, and dried to obtain 0.29 g of the product, with a yield of 71%.

[0122] NMR 1 H NMR (CDCl 3 )δ(ppm): 1.38(d, 3H), 1.5-1.9(m, 8H...

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Abstract

A red fluorescent dye able to emit red light is prepared through reaction between substituted naphthenone solution, alkaline emine compound and catalyst to obtain enamine compound, thermal reflux reaction on 2,2,6-trimethyl-1,3-dioxin-4-one at 110-160 deg.c for 3-10 hr to obtain 2-methyl-4H-pyran-4-one, reaction on malonomitrile and catalyst to obtain substituted 4-diacynomethylene-2-methyl-4H-pyran, adding arylaminal and catalyst, thermal reflux for 5-30 hr, distilling to remove solvent, leaching the solid, and drying. It can be used as luminescent material in optical and photoelectric devices.

Description

technical field [0001] The invention belongs to the field of synthesis of fluorescent dyes, in particular to fluorescent dyes with red light emission and their synthesis method and application. Background technique [0002] With the rapid development of information technology, people have higher requirements for high-density and high-definition display technology. In 1987, C.W.Tang and S.A.Van Slyke (C.W.Tang and S.A.Van Slyke, Appl.Phys.Lett., 1987, 51, 913-915) used the vacuum deposition coating method for the first time, using diamine derivatives as hole transport layers , 8-hydroxyquinoline aluminum (Alq 3 ) as a light-emitting layer, and achieved a brightness of 1000cd / m at a driving voltage of 10V 2 Green light emission, and the efficiency of the device is 1.5lm / W, and the lifetime is more than 100 hours. Since then, due to its advantages of small size, light weight, low driving voltage, fast response, wide viewing angle, and the ability to realize red, green, and b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06
Inventor 张宝文马昌期梁志王雪松曹怡
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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