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A class of benzothrone liquid crystal dyes containing a 3-position substituent, its preparation method and application

A technology of benzranthrone and a substituent is applied in the field of display materials, which can solve the problems that various characteristics of liquid crystal materials cannot be satisfied, and achieve the effects of novel structure, improved linear structure, and improved photoelectric performance.

Inactive Publication Date: 2018-01-09
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Pure liquid crystal materials can no longer meet the various characteristics of liquid crystal materials, such as light, electricity, heat, etc.

Method used

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  • A class of benzothrone liquid crystal dyes containing a 3-position substituent, its preparation method and application
  • A class of benzothrone liquid crystal dyes containing a 3-position substituent, its preparation method and application
  • A class of benzothrone liquid crystal dyes containing a 3-position substituent, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of Liquid Crystal Dye F1

[0029] (1) Synthesis of 2-methyl-4-(4'-ethylbiphenyl) 3-butyne-2-methanol (compound 1)

[0030]

[0031] 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 a white solid with a yield of 92%. Melting point: 48.4-49.7°C.

[0032] 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,2H),1.69-1.60(m,2H),1.38-1.31(m,4H),0.90(t...

Embodiment 2

[0044] Synthesis of liquid crystal dye F2

[0045] The synthetic method is the same as F1, and the 4'-bromo-4-ethylbiphenyl in step (1) is changed into 4'-bromo-4-n-pentylbiphenyl. The developer in step (3) was DCM:PE=2:1, and 406.3 mg of the final product was obtained as a yellow solid with a yield of 85%.

[0046] 1 H NMR (500MHz, CDCl3) δ8.84(dd, J=19.2, 7.7Hz, 2H), 8.51(d, J=7.9Hz, 1H), 8.43(d, J=7.8Hz, 1H), 8.33(d ,J=8.1Hz,1H),7.96–7.84(m,2H),7.75(dd,J=15.9,8.1Hz,3H),7.66(d,J=8.3Hz,2H),7.57(t,J= 8.3Hz, 3H), 7.29(d, J=8.1Hz, 2H), 2.70–2.63(m, 2H), 1.72–1.62(m, 2H), 1.42–1.32(m, 4H), 0.95–0.88(m ,3H).

[0047] 13 C NMR (126MHz, CDCl3) δ153.46(s), 144.11(s), 141.40–141.13(m), 137.51(s), 137.03(s), 136.10(s), 132.44(s), 132.26(s) ,131.43(s),130.23(s),129.71(s),129.61(d,J=5.4Hz),129.43(d,J=4.1Hz),128.76(s),128.47(s),128.13(s) ,128.13(s),126.96(s),125.10(s),123.67(s),122.52(s),122.30(d,J=5.7Hz),97.13(s),87.39(s),58.41(s) , 29.71(s), 28.56(s), 18.46(s), 15.56(s).

[004...

Embodiment 3

[0050] Synthesis of Liquid Crystal Dye F3

[0051] The synthetic method is the same as step (3) in F1, the difference is that the 4'-ethynyl-4-ethylbiphenyl in the step (3) is changed into p-n-butoxyphenylacetylene. The developer was DCM:PE=1:2, and 313.6 mg of the orange-yellow final product was obtained with a yield of 78%.

[0052] 1 H NMR (500MHz, CDCl3) δ8.82(dd, J=15.1, 7.7Hz, 2H), 8.50(d, J=7.9Hz, 1H), 8.41(d, J=7.7Hz, 1H), 8.33(d ,J=8.1Hz,1H),7.88(dd,J=16.2,8.0Hz,2H),7.75(t,J=7.6Hz,1H),7.64–7.52(m,3H),6.94(d,J= 8.7Hz, 2H), 4.02(t, J=6.5Hz, 2H), 1.84–1.76(m, 2H), 1.57–1.48(m, 2H), 1.00(t, J=7.4Hz, 3H).

[0053] 13 C NMR (126MHz, CDCl3) δ183.61(s), 159.79(s), 135.75(s), 133.47(s), 133.35(s), 133.26(s), 132.71(s), 130.30(s), 130.12 (s), 128.41(s), 128.16(s), 126.99(s), 126.56(s), 123.86(s), 123.52(s), 123.15(s), 114.70(d, J=9.7Hz), 97.48 (s), 85.90(s), 67.87(s), 31.26(s), 19.25(s), 13.86(s).

[0054] Melting point: 150.1-151.2°C. TOF MS EI+(m / z): Calculated value:...

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Abstract

The invention discloses a 3-substituent benzanthrone liquid crystal dye, as well as a preparation method and application thereof. According to the preparation method, different acetenyl groups are introduced to the 3-bit of 3-bromobenzanthracen serving as a parent to improve the solubility of a molecule in a liquid crystal and reinforce the linear structure of the molecule, so that the dichroism of a liquid crystal compound can be improved; and highly delocalized electron and parent on a benzene ring are utilized to form a large conjugated system. The synthesized benzanthrone fluorescent bidirectional liquid crystal dye has a maximum absorption wavelength concentrated in a visible region and a transmission wavelength concentrated at about 500nm, and has the advantages of novel structure, easily available raw materials and simple synthesis method; and the dye has a better dichroic ratio and orderly parameters in the liquid crystal, can be used for manufacturing liquid crystal display products, and especially has high dichroism in guest-host liquid crystal displays.

Description

technical field [0001] The invention relates to a novel benzothrone liquid crystal dye compound containing 3 different substitutions and an application thereof, which belongs to the field of display materials. Background technique [0002] The rapid development of informatization has driven the development of liquid crystal panel technology and industry. The traditional cathode ray tube (CRT) 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 nematic liquid crystal host material to form a pair of "guest-host" materials, and an electric field is applied to it, and the orientation of the liquid crystal molecules changes. The "guest-host" (GH) mode is t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09B3/06C09K19/32C09K19/44G02F1/137
CPCC09B3/06C09K19/32C09K19/44G02F1/13725
Inventor 李晓莲王召芬
Owner DALIAN UNIV OF TECH
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