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Fluorine-containing dibenzothiophene sulfone single liquid crystal and preparation method and applications thereof

A thiophene sulfone and monomer technology is applied in the field of fluorine-containing dibenzothiophene sulfone monomer liquid crystal and its preparation, which can solve the problems of insufficient dielectric constant and high threshold voltage of fluorine-containing liquid crystal materials, and achieve large anisotropy and The effect of permittivity, improved clearing point, wide nematic temperature range

Active Publication Date: 2013-05-08
烟台海川化学制品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005]The fluorine-containing liquid crystal material developed in the early stage has a high threshold voltage because the dielectric constant is not large enough

Method used

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  • Fluorine-containing dibenzothiophene sulfone single liquid crystal and preparation method and applications thereof
  • Fluorine-containing dibenzothiophene sulfone single liquid crystal and preparation method and applications thereof
  • Fluorine-containing dibenzothiophene sulfone single liquid crystal and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 13

[0032] Synthesis of Example 13,7-bis(2,3-difluoro-4-pentyl-phenyl)-dibenzothiophene sulfone

[0033] In a 500ml three-necked round-bottom flask protected by nitrogen, add 5.6g (0.015mol) 3,7-dibromo-dibenzothiophene sulfone, 7.5g (0.033nol) 2,3-difluoro-4-pentyl- Phenylboronic acid, 10.4g (0.075mol) potassium carbonate, 112g tetrahydrofuran, 31.2g water, 0.087g (0.000075mol) tetrakis(triphenylphosphine)palladium, heated and refluxed for 2 hours to obtain a light yellow solution, cooled, added 200g toluene and stirred After 0.5 hours, separate layers, wash the organic phase with water, dry over anhydrous sodium sulfate, remove the desiccant, remove the solvent under reduced pressure with a rotary evaporator to obtain 9 g of light yellow solid, and recrystallize the product with toluene to obtain 7.9 g of white crystal, Y: 90.8 %. The purity tested by gas chromatography is 99.9%, and the phase transition point is tested by differential scanning calorimeter (DSC) and microscope:...

Embodiment 23

[0034] Synthesis of Example 23,7-bis(2-fluoro-4-propyl-phenyl)-dibenzothiophene sulfone

[0035] In a 500ml three-necked round-bottom flask protected by nitrogen, add 5.6g (0.015mol) 3,7-dibromo-dibenzothiophene sulfone, 6.3g (0.030nol) 2-fluoro-4-propyl-phenylboronic acid, 1.2g (0.030mol) sodium hydroxide, 16.8g toluene, 25.6g water, 0.000336g (0.0000015mol) tetrakis (triphenylphosphine) palladium, heated and refluxed for 1 hour to obtain a light yellow solution, cooled, added 200g toluene and stirred for 0.5 Hours, separate layers, wash the organic phase with water, dry over anhydrous sodium sulfate, remove the desiccant, remove the solvent under reduced pressure with a rotary evaporator to obtain 8g of light yellow solid, and recrystallize the product with toluene to obtain 6.1g of white crystal, Y: 90.5% . The purity tested by gas chromatography is 99.7%, and the phase transition point is tested by differential scanning calorimeter (DSC) and microscope: crystal phase (Cr)...

Embodiment 33

[0036] Example 33, Synthesis of 7-bis(2-fluoro-4-butyl-phenyl)-dibenzothiophene sulfone

[0037] In a 500ml three-necked round-bottomed flask protected by nitrogen, add 5.6g (0.015mol) 3,7-dibromo-dibenzothiophene sulfone, 10.26g (0.045nol) 2,3-difluoro-4-pentyl- Phenylboronic acid, 12g (0.12mol) potassium bicarbonate, 56g petroleum ether, 45g water, 0.05895g (0.00015mol) dichlorodiphenylphosphine palladium, heated and refluxed for 5 hours to obtain a light yellow solution, cooled, added 300g toluene and stirred for 1.5 Hours, separate layers, wash the organic phase with water, dry over anhydrous sodium sulfate, remove the desiccant, and remove the solvent under reduced pressure with a rotary evaporator to obtain 12g of a light yellow solid. The product is recrystallized with toluene to obtain 10.8g of white crystals, Y: 90.9% . The purity tested by gas chromatography is 99.7%, and the phase transition point is tested by differential scanning calorimeter (DSC) and microscope:...

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Abstract

The invention relates to the field of liquid crystals, and in particular relates to fluorine-containing dibenzothiophene sulfone single liquid crystal applied in a liquid crystal composition and a liquid crystal display, and a preparation method thereof. The fluorine-containing dibenzothiophene sulfone single liquid crystal has the structure formula shown in the specification, wherein in the formula, X is H or F, Y is H or F, W is linear-chain alkyl or linear-chain alkoxyl of C1-C10; and at least one substituent group of X and Y is F. According to the fluorine-containing dibenzothiophene sulfone single liquid crystal and the preparation method and applications thereof, not only is the synthesis method simple, but also the fluorine-containing dibenzothiophene sulfone single liquid crystal contains the two polar groups of fluorine and dibenzothiophene sulfone, so that the polarity of molecules can be enhanced, and the product has wider nematic phase temperature range, as well as larger anisotropicity and higher resistivity; and the fluorine-containing dibenzothiophene sulfone single liquid crystal can be liquid crystal components to improve the property of the liquid crystal material, and can also be used for producing the liquid crystal display.

Description

technical field [0001] The invention relates to the field of liquid crystals, in particular to a fluorine-containing dibenzothiophene sulfone monomer liquid crystal used in liquid crystal compositions and liquid crystal displays and a preparation method thereof. Background technique [0002] Dibenzothiophene sulfone group is an aromatic polar group, and many compounds containing this group have great applications in many fields, such as dibenzothiophene compounds disclosed in patent CN101955491 where R 1 , R 2 It represents H or F, and it is used as a new induction layer material, which is suitable for inducing the weak epitaxial growth of non-planar metal phthalocyanine, and has a good application prospect in the semiconductor field. Patent JP6228555 discloses X-C≡C-Y-C≡C-Z, wherein when Y represents dibenzothiophene sulfone, it exhibits good luminous efficiency and fluorescence intensity. We introduced this group into liquid crystal molecules, and found that the liquid...

Claims

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Application Information

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IPC IPC(8): C09K19/34C07D333/76G02F1/13
Inventor 钟尚宾贾公明姜雪松黄永彤乔松乔广杰王晔
Owner 烟台海川化学制品有限公司
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