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Liquid crystal compound containing 4-(biphenylethynyl)-1,8 naphthalimide, preparation method and application thereof

A technology of naphthalimide and biphenylacetylene, which is applied in the field of display materials, can solve the problems of not being able to meet the various photoelectric characteristics of liquid crystal displays, and achieve the effects of novel structure, good order parameters, and easy-to-obtain raw materials

Inactive Publication Date: 2019-02-12
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Pure liquid crystal materials can no longer meet the various optoelectronic characteristics of liquid crystal displays.

Method used

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  • Liquid crystal compound containing 4-(biphenylethynyl)-1,8 naphthalimide, preparation method and application thereof
  • Liquid crystal compound containing 4-(biphenylethynyl)-1,8 naphthalimide, preparation method and application thereof
  • Liquid crystal compound containing 4-(biphenylethynyl)-1,8 naphthalimide, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of liquid crystal dye Z1

[0031] (1) Synthesis of 2-methyl-4-(4'-ethylbiphenyl) 3-butyne-2-methanol (compound 1)

[0032]

[0033] 302 mg (1 mmol) 4'-bromo-4-ethylbiphenyl and 100 μL (1 mmol) 2-methyl-3-butyn-2-ol and 7 mg ditriphenylphosphine palladium dichloride, 15 mg triphenyl Phosphine and 8 mg CuI were added as catalysts into a 50 mL double-necked round bottom flask, and 15 mL of dry triethylamine was used as an acid-binding agent and solvent. Stir under nitrogen protection and heat to reflux to complete the reaction. Triethylamine was removed under reduced pressure, the crude product was subjected to silica gel chromatography (eluent: dichloromethane), and the solvent was removed under reduced pressure to obtain 281.7 mg of white solid 2-methyl-4-(4'-ethylbiphenyl) 3 - Butyne-2-methanol, yield 92%. Melting point: 48.4-49.7°C.

[0034] 1 H-NMR (400MHz, CDCl3): δ=7.54(s, 4H), 7.50(d, J=8.0Hz, 2H), 7.25(d, J=3.2Hz, 2H), 3.12(s, 1H), 2.68 -2.61(m,...

Embodiment 2

[0048] Synthesis of liquid crystal dye Z2

[0049] In addition to replacing n-butylamine with 3-dimethylaminopropylamine in step (3), replace it with 4-bromo-N-(3-dimethylamino-n-propyl)-1,8-naphthalimide in step (4). Except for 4-bromo-N-n-butyl-1,8-naphthoimide, other operating steps were the same as in Example 1 to obtain bright yellow solid Z2 with a yield of 60%.

[0050] 1 H NMR (500MHz, CDCl 3 )δ8.77(dd, J=8.4,1.1Hz,1H),8.65(dd,J=7.3,1.1Hz,1H),8.56(d,J=7.6Hz,1H),7.97(d,J=7.6 Hz,1H),7.85(dd,J=8.3,7.3Hz,1H),7.76–7.71(m,2H),7.70–7.64(m,2H),7.57(d,J=8.2Hz,2H),7.32 (d, J=8.3Hz, 2H), 4.28(t, J=7.3Hz, 2H), 2.77–2.65(m, 4H), 2.46(s, 6H), 2.08(dt, J=14.2, 7.2Hz, 2H), 1.29(t, J=7.6Hz, 3H).

[0051] 13 C NMR (126MHz, CDCl 3 )δ163.87(d,J=34.5Hz),144.30(s),142.20(s),137.33(s),132.57(s),132.35(s),131.69(s),131.57(s),130.49( s), 130.49(s), 128.51(s), 128.05(s), 127.91(s), 127.44(s), 127.07(s), 126.99(s), 122.74(s), 121.73(s), 120.63( s), 99.48(s), 86.82(s), 56.73(s), 53.43(s)...

Embodiment 3

[0054] Synthesis of liquid crystal dye Z3

[0055] In addition to replacing 4'-bromo-4-ethylbiphenyl with 4'-bromo-4-n-pentylbiphenyl in step (1), 2-methyl-4-(4'- n-pentylbiphenyl) 3-butyne-2-methanol is replaced with 2-methyl-4-(4'-ethylbiphenyl) 3-butyne-2-methanol, and other operating steps are the same as in Example 1, to obtain Yellow solid Z3, 70% yield.

[0056] 1 H NMR (500MHz, CDCl 3 )δ8.76(dd, J=8.3,0.9Hz,1H),8.67–8.63(m,1H),8.57(d,J=7.6Hz,1H),7.97(d,J=7.6Hz,1H), 7.85(dd,J=8.2,7.4Hz,1H),7.76–7.71(m,2H),7.69–7.64(m,2H),7.56(d,J=8.2Hz,2H),7.29(d,J= 8.2Hz, 2H), 4.19(dd, J=8.5, 6.7Hz, 2H), 2.71–2.62(m, 2H), 1.74(ddd, J=15.3, 11.0, 7.6Hz, 2H), 1.66(dd, J =15.1,7.5Hz,2H),1.46(dq,J=14.9,7.4Hz,2H),1.40–1.33(m,4H),1.01–0.97(m,3H),0.94–0.88(m,3H).

[0057] 13 C NMR (126MHz, CDCl 3 )δ163.86(d,J=33.7Hz),143.00(s),142.15(s),137.30(s),132.33(s),131.54(s),130.66(s),130.34(s),129.04( s), 128.05(s), 127.62(s), 127.39(s), 127.05(s), 126.89(s), 123.02–122.82(m), 122.07(s), 120...

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Abstract

The invention discloses a liquid crystal compound containing 4-(biphenyl acetenyl)-1,8 naphthalimide, a preparing method and application. Solubility of molecules in mixed liquid crystal is improved by the compound, the linear structure of the molecules is enhanced, and the dichroism of the liquid crystal compound is improved; a push-drawing electron system is formed through high-delocalization electrons on a benzene ring and electron-withdrawing capacity of bisamide bonds. The maximum emission wavelength of the liquid crystal compound in dichloromethane is 502 nm, the liquid crystal compound emits glaucous fluorescence, the fluorescence quantum yield is 0.88, high dichroic ratio and order parameters are represented in liquid crystal, and the liquid crystal compound serving as guest liquid crystal dye can be used for manufacturing a liquid crystal display product particularly a guest-host type liquid crystal displayer. The liquid crystal compound has a typical nematic phase within the temperature range of 160-250 DEG C, and birefringence of a liquid crystal body can be improved by adding the liquid crystal compound into smectic phase liquid crystal, or nematic phase liquid crystal or cholesteric phase liquid crystal.

Description

technical field [0001] The invention relates to a liquid crystal compound containing 4-(biphenylethynyl)-1,8-naphthalimide and an application thereof, belonging to the field of display materials. Background technique [0002] The rapid development of informatization has promoted the development of liquid crystal panel technology and industry. The high-power and large-volume cathode ray tube technology has been replaced by flat panel display, which has brought revolutionary changes to people's lives. [0003] The "guest-host" display is a new display mode emerging in recent years. The "guest-host" (GH) mode is a working mode that shows color changes, and was proposed by G. Heilmeier et al. almost simultaneously with the DS mode. Some dichroic dyes are doped in the main material of the nematic liquid crystal. The dye changes the absorption spectrum due to the molecular direction and has light absorption anisotropy. The two constitute a pair of "guest-host" materials, and an e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/14C09K19/34C09K19/56C09K11/06C09B57/08
CPCC09B57/08C09K11/06C09K19/3447C09K19/56C09K2211/1029
Inventor 李晓莲王召芬
Owner DALIAN UNIV OF TECH
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