Red fluorescent dye possessing star project type structure and its synthesis method and use

A red fluorescence, star-emitting technology, applied in the field of fluorescent dye synthesis, can solve the problems of inability to effectively prevent concentration quenching effect, complex synthesis, increase cost, etc., to reduce concentration self-quenching phenomenon, easy to obtain raw materials , the effect of long excited state lifetime

A red fluorescence, star-emitting technology, applied in the field of fluorescent dye synthesis, can solve the problems of inability to effectively prevent concentration quenching effect, complex synthesis, increase cost, etc., to reduce concentration self-quenching phenomenon, easy to obtain raw materials , the effect of long excited state lifetime

CN1219018CInactive Publication Date: 2005-09-14TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Red fluorescent dye possessing star project type structure and its synthesis method and use
  • Red fluorescent dye possessing star project type structure and its synthesis method and use
  • Red fluorescent dye possessing star project type structure and its synthesis method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1: N, N, N-tri-4-[2-[(4-dicyanomethenyl)-8-methyl-5,6,7,8-tetrahydro-4H-1-benzo Pyran]vinyl]aniline

[0042]

[0043] In a round bottom flask, add 0.90g (4mmol) 4-dicyanomethenyl-2,8-dimethyl-5,6,7,8-tetrahydro-4H-1-benzopyran, 0.33g ( 1mmol) N,N,N-tris-(4-formyl)aniline, 15ml acetonitrile, 0.40ml 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 0.67 g of the product with a yield of 70%.

[0044] NMR 1 H NMR (CDCl 3 )δ(ppm): 1.38(d, 9H, J=6.7Hz), 1.55-2.10(m, 12H), 2.80-3.10(m, 9H), 6.60(d, 3H), 6.75(s, 3H), 7.15(d, 6H), 7.30(d, 3H), 7.46(d, 6H);

[0045] Elemental analysis Calculated value (C 63 h 51 N 7 o 3 ): C, 79.31; H, 5.39; N, 10.28;

[0046] Found: C, 79.18; H, 5.52; N, 10.11

[0047] Mass spectrometry (MS + ): 953 (M + )

Embodiment 2

[0048] Example 2: N,N,N-tris-4-[2-[(4-dicyanomethenyl)-6-isopropyl-4H-pyran]vinyl]aniline

[0049]

[0050] Add 0.70g (3.5mmol) 4-dicyanomethenyl-2-methyl-6-isopropyl-4H-pyran, 0.33g (1mmol) N,N,N-tri-( 4-formyl)aniline, 15ml of acetonitrile, 0.40ml of catalyst (the preparation method is: 5ml of hexahydropyridine dissolved in 15ml of acetic acid), heated to reflux for 12 hours. The solvent was distilled off, cooled, and the solid was rinsed with acetonitrile for several times and dried to obtain 0.59 g of the product with a yield of 65%.

[0051] NMR 1 H NMR (CDCl 3 )δ (ppm): 1.42 (d, 18H), 2.8 (m, 3H), 6.59 (d, 3H), 6.72 (s, 3H), 6.81 (s, 3H), 7.15 (d, 6H), 7.32 ( d,3H), 7.51(d,6H)

[0052] Elemental analysis Calculated value (C 57 h 45 N 7 o 2 ): C, 78.15; H, 5.18; N, 11.19

[0053] Found: C, 78.32; H, 5.05; N, 11.41

[0054] Mass spectrometry (MS + ): 875 (M + )

Embodiment 3

[0055] Example 3: N,N,N-tris-4-[2-[(4-dicyanomethenyl)-6-isopropyl-4H-pyran]vinyl]aniline

[0056]

[0057] Add 0.70g (3.5mmol) 4-dicyanomethenyl-2-methyl-6-isopropyl-4H-pyran, 0.33g (1mmol) N,N,N-tri-( 4-formyl) aniline, 15ml acetonitrile, 0.40ml hexahydropyridine, heated to reflux for 12 hours. The solvent was removed by distillation, cooled, and the solid was rinsed with acetonitrile for several times, and dried to obtain 0.66 g of the product with a yield of 75%.

[0058] NMR 1 H NMR (CDCl 3 )δ (ppm): 1.40 (d, 18H), 2.8 (m, 3H), 6.60 (d, 3H), 6.72 (s, 3H), 6.81 (s, 3H), 7.15 (d, 6H), 7.32 ( d,3H), 7.51(d,6H)

[0059] Elemental analysis Calculated value (C 57 h 45 N 7 o 2 ): C, 78.15; H, 5.18; N, 11.19

[0060] Found: C, 78.21; H, 5.15; N, 11.38

[0061] Mass spectrometry (MS + ): 875 (M + )

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Abstract

A red fluorescent dye with star structure is preparde through proportionally adding trianilinoaldehyde and catalyst to the solution of substituted 4-dicyanomethenyl-20methyl-4H-pyran, thermal reflux, distilling for removing solvent, leaching the solid by solvent and drying. It can be used for organic optical conductor, organic non-linear optical material, and luminescent material.

Description

technical field [0001] The invention belongs to the field of synthesis of fluorescent dyes, in particular to red light-emitting fluorescent dyes with a star-ray structure, 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 used the vacuum deposition coating method for the first time in "Applied Physics Letters" 1987, Volume 51, pages 913-915, using diamine derivatives as hole transport layers, and 8-hydroxyquinoline aluminum as The light-emitting layer achieves 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 small size, light weight, small driving voltage, fast response, wide viewing angle, and the ability to realize r...

Claims

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Application Information

Patent Timeline
14 Sep 2005
Publication
CN1219018C
IPC
C09K9/02
Inventors
张宝文; 马昌期