Naphthalimide fluorescent dichroic dye containing aromatic ester group and application thereof

A technology of naphthalene imide and aromatic ester, applied in the field of display materials, can solve problems such as restricting application development, and achieve the effects of novel structure, easy availability of raw materials and simple synthesis method

Inactive Publication Date: 2011-01-12
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the fluorescent dichroic liquid crystal dyes reported in the literature are positive dichroic dyes, which greatly limits their application and development.

Method used

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  • Naphthalimide fluorescent dichroic dye containing aromatic ester group and application thereof
  • Naphthalimide fluorescent dichroic dye containing aromatic ester group and application thereof
  • Naphthalimide fluorescent dichroic dye containing aromatic ester group and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis of 4-(p-hexyloxybenzoate)-N-n-propyl-1,8-naphthalimide (N1)

[0026] (1) In a 100mL two-necked flask, add 2.77g 4-bromo-1,8-naphthalene anhydride (10mmol), 40mL DMF, 0.97g NaN 3 (15 mmol), heated to 60° C. for 5 hours, followed by TLC plate to the end of the reaction. Let stand, cool, and slowly pour into 400mL of ice water, a large amount of yellow solid is precipitated, filtered, washed, and dried to obtain 2.27g of yellow solid, yield: 95%.

[0027]

[0028]

[0029] (2) In a 75mL autoclave, add 2g of 4-azido-1,8-naphthalene anhydride (8.4mmol), 0.36g of 10% palladium carbon catalyst, 35mL of DMF, evacuate several times, fill with 1.5MPa hydrogen, and React at 60°C for 4 hours, cool, filter, and wash with hot DMF solution. After the filtrate is cooled to room temperature, pour it into 200mL ice water, a large amount of yellow solid precipitates, filter, wash, and dry to obtain 1.6g of solid, melting point:> 300°C, Yield: 90%.

[0030]

[0031]...

Embodiment 2

[0040] Synthesis of 4-(p-hexyloxybenzoate)-N-n-butyl-1,8-naphthalimide (N2)

[0041] Except that n-butylamine was used instead of n-propylamine, other synthesis and purification methods were the same as in Example 1 to obtain the target product N2 with a yield of 44% and a melting point of 146.5-147.4°C.

[0042] 1 H-NMR (400MHz, CDCl 3 ), δH (ppm): 8.67 (d, J=8.0Hz, 2H), 8.33 (d, J=8.4Hz, 1H), 8.28 (d, J=8.8Hz, 2H), 7.77 (dd, J1=J2 =8.0Hz, 1H), 7.68 (d, J=8.0Hz, 1H), 7.07 (d, J=8.8Hz, 2H), 4.20 (t, J1=J2=7.6Hz, 2H), 4.09 (t, J1 =J2=6.4Hz, 2H), 1.85 (m, 2H), 1.73 (m, 2H), 1.43 (m, 8H), 0.99 (t, J1=J2=7.2Hz, 3H), 0.93 (t, J1= J2=6.8Hz, 3H).

[0043] API-ES MS (m / z): 474.3 ([M+H] + ), 496.3 ([M+Na] + ).

Embodiment 3

[0045] Synthesis of 4-(p-hexyloxybenzoate)-N-n-hexyl-1,8-naphthalimide (N3)

[0046] Except that n-hexylamine was used instead of n-propylamine, other synthesis and purification methods were the same as in Example 1 to obtain the target product N3 with a yield of 46% and a melting point of 137.4-138.1°C.

[0047] 1 H-NMR (400MHz, CDCl 3 ), δH (ppm): 8.65 (d, J=8.0Hz, 2H), 8.31 (d, J=8.0Hz, 1H), 8.26 (d, J=8.8Hz, 2H), 7.76 (dd, J1=7.2 Hz, J2=8.0Hz, 1H), 7.66 (d, J=8.0Hz, 1H), 7.05 (d, J=8.8Hz, 2H), 4.18 (t, J1=J2=8.0Hz, 2H), 4.09 ( t, J1=J2=6.4Hz, 2H), 1.84 (m, 2H), 1.73 (m, 2H), 1.43 (m, 12H), 0.93 (t, J1=J2=7.2Hz, 3H), 0.88 (t , J1=J2=6.8Hz, 3H).

[0048] API-ES MS(m / z): 502.2([M+H] + ), 524.2 ([M+Na] + ).

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Abstract

The invention relates to a naphthalimide fluorescent dichroic dye containing an aromatic ester group and an application thereof, belonging to the field of display materials. In the naphthalimide fluorescent dichroic dye containing an aromatic ester group, naphthalimide is used as the parent body, and an ester group is introduced to 4-site to be directly connected with the parent body so as to achieve negative fluorescent dichroism. The dye has the advantages of novel structure, easy acquisition of raw materials and simple synthesis method. Tests show that this series of dye emits vivid blue fluorescence, the maximum emission wavelength is 405nm, the fluorescence quantum yield is 0.44-0.70, better dichroism can be indicated in liquid crystal MLC6237-01 epsilon, the absorption order parameter is -0.20- -0.23, the dichroic ratio is 2.0-2.3, the fluorescent order parameter is -0.37- -0.38, and the fluorescent dichroic ratio is 5.2-5.7.

Description

technical field [0001] The invention relates to a class of aromatic ester group-containing naphthalimide fluorescent dichroic dyes and applications thereof, belonging to the field of display materials. Background technique [0002] The reason why the "guest-host" liquid crystal display can become a kind of display with application prospects is that it not only displays information with bright colors, high brightness, good contrast, and wide viewing angle, but also only needs to use a polarizer or even a single polarizer when assembling. No polarizer is used, which greatly improves the light utilization efficiency of the backlight source. Especially in recent years, the development of fluorescent dichroic liquid crystal dyes, which are applied to "guest-host" display, can combine the bright color light and high brightness of emissive display with the characteristics of liquid crystal display, and can become a kind of energy consumption Lower portable electronics displays. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/08C09K11/06C09K19/52G02F1/1333
Inventor 李晓莲王兵
Owner DALIAN UNIV OF TECH
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