Red fluorescence dyestuff and its synthesizing method and usage

A technology of red fluorescence and synthesis method, which is applied in the field of fluorescent dyes with red light emission and its synthesis, can solve the problems of reducing reaction yield, increasing cost, raw material consumption, etc., and achieves high yield, long excited state life, and reaction The effect of fewer steps

Inactive Publication Date: 2003-07-23
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] Due to the generation of dicondensed by-products, the consumption of raw materials in the production process reduces the yield of the reaction; at the same time, because the dicondensed products can quench the fluorescence of monocondensed compounds, dyes are required to have high performance in the field of electroluminescence. Purity, which requires us to separate and remove the dicondensation by-product from the monocondensation compound, but in fact, once this by-product is formed, 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 fluorescence dyestuff and its synthesizing method and usage
  • Red fluorescence dyestuff and its synthesizing method and usage
  • Red fluorescence dyestuff and its synthesizing method and usage

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: N, N-bis-[4-[2-(4-dicyanomethenyl)-8-methyl-5,6,7,8-tetrahydro-4H-1-benzopyran ]vinyl]phenylaniline

[0048] Add 0.56g (2.5mmol) 4-dicyanomethenyl-2,8-dimethyl-5,6,7,8-tetrahydro-4H-1-benzopyran to a round bottom flask, 0.30g (1 mmol) N, N-bis-(4-formylphenyl) aniline, 15 ml acetonitrile, 0.40 ml hexahydropyridine, heated to reflux for 24 hours. The solvent was removed by distillation, cooled, and the solid was rinsed with acetonitrile for several times, and dried to obtain 0.52 g of the product with a yield of 72%.

[0049] NMR 1 H NMR (CDCl 3 )δ (ppm): 1.37 (d, 6H), 1.5-2.1 (m, 8H), 2.89 (m, 6H), 6.52 (d, 2H), 6.70 (s, 2H), 7.00-7.40 (m, 15H )

[0050] Elemental analysis calculated value (C 38 h 39 N 5 o 2 ): C, 80.31; H, 5.48; N, 9.76

[0051] Found: C, 80.13; H, 5.85; N, 9.44

[0052] Mass spectrometry (MS + ): 717 (M + )

Embodiment 2

[0053] Example 2: N, N-bis-[4-[2-(4-dicyanomethenyl)-8-methyl-5,6,7,8-tetrahydro-4H-1-benzopyran ]vinyl]phenyl-4-methylaniline

[0054] Add 0.56g (2.5mmol) 4-dicyanomethenyl-2,8-dimethyl-5,6,7,8-tetrahydro-4H-1-benzopyran to a round bottom flask, 0.32g (1mmol) N, N-bis-(4-formylphenyl)-4-methylaniline, 15ml acetonitrile, 0.40ml catalyst (its preparation method is: 5ml hexahydropyridine is dissolved in 15ml acetic acid), heated to reflux for 24 Hour. The solvent was removed by distillation, cooled, and the solid was rinsed with acetonitrile for several times, and dried to obtain 0.48 g of the product with a yield of 65%.

[0055] NMR 1 H NMR (CDCl 3 )δ (ppm): 1.38 (d, 6H), 1.5-2.1 (m, 8H), 2.64 (s, 3H), 2.87 (m, 6H), 6.52 (d, 2H), 6.70 (s, 2H), 6.80-7.40(m, 14H)

[0056] Elemental analysis calculated value (C 49 h 41 N 5 o 2 ): C, 80.41; H, 5.65; N, 9.57

[0057] Found: C, 80.32; H, 5.85; N, 9.41

[0058] Mass spectrometry (MS + ): 731 (M + )

Embodiment 3

[0059] Example 3: N, N-bis-[4-[2-(4-dicyanomethenyl)-8-methyl-5,6,7,8-tetrahydro-4H-1-benzopyran ]vinyl]phenyl-4-methoxyaniline

[0060] In a round bottom flask, add 0.68g (3mmol) 4-dicyanomethenyl-2,8-dimethyl-5,6,7,8-tetrahydro-4H-1-benzopyran, 0.33g ( 1mmol) N, N-bis-(4-formylphenyl)-4-methoxyaniline, 15ml acetonitrile, 0.40ml catalyst (its preparation method is: 5ml hexahydropyridine is dissolved in 15ml acetic acid), heated to reflux for 24 Hour. The solvent was removed by distillation, cooled, and the solid was rinsed with acetonitrile for several times, and dried to obtain 0.53 g of the product with a yield of 71%.

[0061] NMR 1 H NMR (CDCl 3 )δ (ppm): 1.38 (d, 6H), 1.5-2.1 (m, 8H), 2.87 (m, 6H), 4.41 (s, 3H), 6.52 (d, 2H), 6.70 (s, 2H), 6.80-7.40(m, 14H)

[0062] Elemental analysis calculated value (C 49 h 41 N 5 o 3 ): C, 78.69; H, 5.53; N, 9.36

[0063] Found: C, 78.13; H, 5.85; N, 9.24

[0064] Mass spectrometry (MS + ): 747 (M + )

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Abstract

A red fluorescence dye used for organic optical conductor, non-linear organic optical material, or electroluminescent device is prepared through adding, arylamine bialdehyde and catalyst in the solution of substituted 4-diacyno methylenyl-2-methyl-4H-pyran, heating, reflux, distilling to remove solvent, leaching solid with solvent, and drying.

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 as the light-emitting layer, achieved a brightness of 1000 cd / 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 small size, light weight, small driving voltage, fast response, wide viewing angle, and the ability to realize red, green, and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/04C07D309/34C09K11/06
Inventor 张宝文马昌期王雪松曹怡
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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