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Naphthoyl imine luminescence material to luminesce with red fluorescence

A technology of naphthalimide and luminescent materials, which is applied in the direction of luminescent materials, chemical instruments and methods, etc., can solve the problems of fluorescence quenching, and achieve the effect of avoiding the reduction of fluorescence efficiency

Inactive Publication Date: 2001-12-05
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although in the production of red-emitting diodes, the energy transfer principle is used to transfer the energy of small molecules or conjugated polymers that emit short-wave fluorescence (blue light) to the guest luminescent body, which can improve the performance of red-emitting diodes. However, the phenomenon of fluorescence quenching due to the increase of concentration cannot be avoided.

Method used

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  • Naphthoyl imine luminescence material to luminesce with red fluorescence
  • Naphthoyl imine luminescence material to luminesce with red fluorescence

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Synthesis of N-n-butyl-4-(p-methoxybenzaldehyde hydrahydrazino)-1,8-naphthalimide (compound NA1)

[0023] In a 100ml round bottom flask, add 1g of N-butyl-4-hydrazino-1,8-naphthalimide (3.5mmol), 0.49g of p-methoxybenzaldehyde (3.6mmol) and 60ml of absolute ethanol , heated to reflux for 2.5 hours, stood to cool and precipitated a red solid, filtered, and the crude product was recrystallized with absolute ethanol to obtain 1.2 g of red powder with a yield of 87%. m.p.215-216°C. MS-EI: 401(M+). 1 H-NMR (in DMSO-d 6 )δ(ppm):8.79(d,J=8.37Hz,1H),8.48(d,J=7.22Hz,1H),8:42(s,1H),8.37(d,J=8.53Hz,1H) ,7.78(m,3H),7.70(d,J=4.58Hz,1H),7.05(d,J=8.75Hz,2H),4.03(t,NCH 2 -,2H),1.60(m,-CH 2 -,2H),1.35(m,-CH 2 -,2H),0.93(t,-CH 3 ,3H).

Embodiment 2

[0025] Synthesis of N-n-butyl-4-(9-anthracene formaldehyde hydrahydrazino)-1,8-naphthalimide (compound NA2)

[0026] Replace the p-methoxybenzaldehyde in embodiment 1 with 9-anthracene formaldehyde, thick product recrystallizes with the mixed solvent of dehydrated alcohol / acetone (1: 1v: v), other is identical with embodiment 1, and the result is as follows:

[0027] Red needle-like crystals, yield: 83%. m.p.: 238~240℃. MS-EI: 471(M+) 1 H-NMR (in DMSO-d 6 )δ(ppm):9.72(s,1H),8.89(d,J=8.42Hz,1H),8.84(d,J=8.42Hz,2H),8.70(s,1H),8.54(d,J= 7.18Hz, 1H), 8.44(d, J=8.46Hz, 1H), 8.20(d, J=8.47Hz, 2H), 7.89(t, J=7.70Hz, J=8.00Hz, 1H), 7.73(m ,3H),7.62(t,J=7.57Hz,J=7.36Hz,2H),4.05(t,NCH 2 -,2H),1.62(m,-CH 2 -,2H),1.36(m,-CH 2 -,2H),0.93(t,-CH 3 ,3H).

Embodiment 3

[0029] Synthesis of Compound N-n-Butyl-4-(Benzaldehyde Hydrahydrazino)-1,8-Naphthimide (Compound NAR)

[0030] Replace the p-methoxybenzaldehyde in embodiment 1 with benzaldehyde, and thick product recrystallizes with dehydrated alcohol, and other is identical with embodiment 1, and the result is as follows:

[0031] Yellow powder, yield 85%. m.p.: 204-206°C. MS-EI: 371(M+). 1 H-NMR (inDMSO-d 6 )δ(ppm):8.79(d,J=8.36Hz,1H),8.48(d,J=6.72Hz,1H),8.46(s,2H),8.38(d,J=8.49Hz,1H),7.81 (m,3H),7.75(d,J=8.13Hz,1H),7.50~7.42(m,3H),4.03(t,NCH 2 -,2H),1.60(m,-CH 2 -,2H),1.35(m,-CH 2 -,2H),0.93(t,-CH 3 ,3H).

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Abstract

The present invention discloses a kind of luminescent material capable of giving out red fluorescence in pure solid film. This material contains 1.8-naphthoylimine function group, and the increment of conjugate delocalization extent in whole molecular or increment of para-substitutent electron donating property makes the maximum fluorescence emission wavelength red of this compound move to above 618nm under the condition of pure solid film state, and can make the said luminescent material give out bright red fluorescence, and prevent the fluorescence efficiency reduction due to concentration quenching. This said invention also provides the structural formula of said material.

Description

technical field [0001] The invention relates to a naphthalimide compound, in particular to a class of red fluorescent naphthalimide compounds. Background technique [0002] The full-color display of red-green-blue ternary colors is one of the most attractive goals in the field of organic electroluminescent materials. In order to achieve this goal, chemists from all over the world have made unremitting exploration and efforts. Since the maximum luminous efficiency comes from self-emitting color materials, it is of great significance to develop photoluminescent materials that can emit red, green, and blue light respectively for the development of electroluminescent devices. [0003] There are many types of luminescent materials that can emit green and blue light, and they have high luminous efficiency in practical applications, while the types of luminescent materials that emit red light are rare, such as: 4-(dinitrile methylene base)-2-methyl-6-(p-dime...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06
Inventor 田禾陈孔常甘家安王巧纯
Owner EAST CHINA UNIV OF SCI & TECH