CN102838584B - Liquid crystal monomer bicyclohexyl-containing epoxyethane compound and synthetic method thereof - Google Patents
Liquid crystal monomer bicyclohexyl-containing epoxyethane compound and synthetic method thereof Download PDFInfo
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- CN102838584B CN102838584B CN201210337052.9A CN201210337052A CN102838584B CN 102838584 B CN102838584 B CN 102838584B CN 201210337052 A CN201210337052 A CN 201210337052A CN 102838584 B CN102838584 B CN 102838584B
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Abstract
The invention discloses a liquid crystal monomer bicyclohexyl-containing epoxyethane compound and a synthetic method thereof. The liquid crystal monomer bicyclohexyl-containing epoxyethane compound has a structure shown in the description, wherein R is one of fluorine, chlorine, H, C1-C5 linear chain alkyl and C1-C5 linear chain alkoxy; R' is one of fluorine, chlorine, H, C1-C5 linear chain alkyl, C1-C5 linear chain alkoxy, and cyan; and such compound can be independently or mixed to be used for liquid crystal display in various forms. The liquid crystal monomer bicyclohexyl-containing epoxyethane compound and the synthetic method provided by the invention have the characteristics that the liquid crystal display is achieved, the demands on 3D (three-dimensional) display technology are met, the rotating viscosity of a liquid crystal material is reduced, and the dielectric anisotropy coefficient of the liquid crystal material is improved.
Description
Technical field
The present invention relates to technical field of fine, especially relate to a kind of Liquid crystal monomer bicyclohexyl-containepoxyethane epoxyethane compound and synthetic method thereof, this kind may be used for liquid-crystal display containing two hexanaphthene oxane compounds.
Background technology
Lcd technology has been widely used in daily life, the synthesis of its core material-liquid crystal monomer is the emphasis that chemist pays close attention to always, at present along with the renewal of lcd technology, 3D technique of display is more and more by people are paid close attention to, the mainstream technology type of 3D display, contain spectacle 3D technology and bore hole formula 3D technology, wherein spectacle 3D technology comprises aberration formula 3D technology, polarization type 3D technology and active-shutter 3D technology; Bore hole formula 3D technology comprises disparity barrier formula 3D technology, lens pillar formula 3D technology, points to light-source type 3D technology etc.There is different difference due to its principle shown and mode in above-mentioned various types of 3D technique of display, can mainly polarization type, active-shutter, disparity barrier formula, the lens pillar formula of 3D display be realized with liquid crystal panel and point to light-source type at present, for panel producer, no matter preparation application is any 3D display mode, the time of response of reducing liquid crystal and the important goal making liquid crystal panel have refreshing frequency Ye Shi producer faster constantly to pursue.And reduce liquid crystal material rotation viscosity, to increase the dielectric anisotropy coefficient of liquid crystal material be the key reducing the liquid crystal response time.But this is relevant to the structural performance of liquid crystal material own, current any single liquid crystal material all can not independently meet, display needs can only be met by monomer mixture, therefore develop low rotation viscosity, the liquid crystal material of high dielectric anisotropy coefficient is the field that monomer developer constantly explores, the compound new in this field is also constantly developed.
Summary of the invention
The object of the invention is to the performance improving existing bis cyclohexane liquid crystal, Yin Ru oxane structure in liquid crystal molecule skeleton, both the feature that bis cyclohexane liquid crystal viscosity is low can have been retained, again can the long feature of wide, the pitch of Fa Hui oxane class liquid-crystal phase-transition temperature, and then provide a kind of for liquid-crystal display, the needs meeting 3D technique of display, the rotation viscosity reducing liquid crystal material, the Liquid crystal monomer bicyclohexyl-containepoxyethane epoxyethane compound improving the dielectric anisotropy coefficient of liquid crystal material and synthetic method thereof.
The object of the present invention is achieved like this, a kind of Liquid crystal monomer bicyclohexyl-containepoxyethane epoxyethane compound, is characterized in that this compound structure is as follows:
In formula, R is one of fluorine, chlorine, the straight chained alkyl of H, C1-C5, the unbranched alkoxy of C1-C5, R ' is fluorine, chlorine, the straight chained alkyl of H, C1-C5, one of the unbranched alkoxy, cyano group of C1-C5, and this compounds separately or can be mixed for the liquid-crystal display of various display format.
In order to realize object of the present invention, above-mentioned Liquid crystal monomer bicyclohexyl-containepoxyethane epoxyethane compound adopts following synthetic route:
Ⅰ Ⅱ Ⅲ
With to alkyl bicyclic hexyl formaldehyde and the structure 2-as shown in II of structure as shown in I to alkyl phenyl propylene glycol for raw material, wherein R, R in chemical compounds I, II ' is identical with containing R, R in two hexanaphthene oxane compounds III ', tosic acid is adopted to make catalyzer, take organic solvent as reaction medium, at temperature 35-200 DEG C, reaction 2-12h, obtain corresponding containing two hexanaphthene oxane compounds III, after having reacted, through washing, extraction, recrystallization, its purified ω III > 99%, overall yield of reaction is greater than 70%.
In order to realize object of the present invention further, can be use the quality of catalyzer tosic acid to be the 1%-20% of the quality of starting compound I.
In order to realize object of the present invention further, the one that can be described organic solvent be in toluene, dimethylbenzene, normal heptane, normal hexane.
In order to realize object of the present invention further, can be temperature of reaction be 60-110 DEG C, reaction times 3-8h.
The present invention, when designing compound structure, have selected bis cyclohexane with oxane is as the main body framework of compound, can reduce liquid crystal molecule viscosity, reduce threshold voltage, improve transformation temperature, object makes it can use as liquid crystal monomer, and the synthetic route of this compounds is simple.
Embodiment
Below in conjunction with embodiment, the present invention is described in further detail.
Embodiment 1, a kind of Liquid crystal monomer bicyclohexyl-containepoxyethane epoxyethane compound, is characterized in that this compound structure is as follows:
In formula, R is one of fluorine, chlorine, the straight chained alkyl of H, C1-C5, the unbranched alkoxy of C1-C5, R ' is fluorine, chlorine, the straight chained alkyl of H, C1-C5, one of the unbranched alkoxy, cyano group of C1-C5, this compounds separately or can be mixed for the liquid-crystal display of various display format, is adopt following synthetic route:
Ⅰ Ⅱ Ⅲ
With to alkyl bicyclic hexyl formaldehyde and the structure 2-as shown in II of structure as shown in I to alkyl phenyl propylene glycol for raw material, wherein chemical compounds I, R in II, R ' and the R contained in two hexanaphthene oxane compounds III, R ' is identical, tosic acid is adopted to make catalyzer, take organic solvent as reaction medium, at temperature 35-200 DEG C, reaction 2-12h, obtain corresponding containing two hexanaphthene oxane compounds III, after having reacted, through washing, extraction, recrystallization, its purified ω III > 99%, overall yield of reaction is greater than 70%, the quality of use catalyzer tosic acid is the 1%-20% of the quality of starting compound I, organic solvent is toluene, dimethylbenzene, normal heptane, one in normal hexane, optimal reaction temperature is 60-110 DEG C, reaction times 3-8h,
The present embodiment containing two hexanaphthene oxane compounds be 5-to ethylphenyl-2-(to propyl group bis cyclohexane base)-1,3-diox, represent with III a;
To mechanical stirring is housed, reflux condensing tube, add successively in 250mL tri-mouthfuls of reaction flasks of feed hopper n-propyl dicyclohexyl formaldehyde 24g, 2-is to ethylphenyl propylene glycol 20g, catalyzer tosic acid 3g, toluene 110mL, start stirring heating, 108-110 DEG C of back flow reaction 3-8h, sampling analysis, according to gas phase analysis result determination reaction terminating, cooling, then in reaction solution, water 50mL is added, separatory, aqueous phase toluene 20mL extracts, merge organic phase, be washed to neutrality, with the dry 8h of anhydrous magnesium sulfate 5g, filter, use toluene 10mL drip washing filter cake twice again, sampling analysis determines thick product quality ω III a:76%, after distillation desolventizes, purifying, obtain product III a28.6g, ω III a:99.5%, yield: 70%, product mass spectral results: ES-MS m/z:398 [M]+.
Embodiment 2, a kind of Liquid crystal monomer bicyclohexyl-containepoxyethane epoxyethane compound and synthetic method thereof, the present embodiment containing two hexanaphthene oxane compounds be 5-to ethylphenyl-2-(to propyl group bis cyclohexane base)-1,3-diox, represent with III b;
Add n-pentyl dicyclohexyl formaldehyde 29g successively in 250mL tri-mouthfuls of reaction flasks that mechanical stirring, reflux condensing tube, feed hopper be housed, 2-to ethylphenyl propylene glycol 22g, catalyzer tosic acid 4g, toluene 110mL, start stirring heating, 108-110 DEG C of back flow reaction 3-8h, other conditions with embodiment 1, purifying, obtain product III b33g, ω III b:99.5%, yield: 70.5%, product mass spectral results: ES-MS m/z:426 [M]+.
The present invention have selected bis cyclohexane with oxane is as molecular skeleton, design containing two hexanaphthene oxane class liquid crystalline cpd III, and with to alkyl bicyclic hexyl formaldehyde structure as shown in I, with 2-, raw material is depicted as II to alkyl phenyl propylene glycol structure, wherein chemical compounds I, R in II, R ' and the R contained in two hexanaphthene oxane compounds III, R ' is identical, tosic acid is adopted to make catalyzer, take organic solvent as reaction medium, at 35-200 DEG C, reaction 2-12h, obtain corresponding containing two hexanaphthene oxane compounds III, structure is wherein confirmed, determining the mass ratio adopting tosic acid to make catalyzer and starting compound I is 1%-20%, preferably 1%-10%, take organic solvent as reaction medium, organic solvent is toluene preferably, dimethylbenzene, normal heptane, normal hexane equal solvent, at 35-200 DEG C of reaction 2-12h.Temperature of reaction system is 60-110 DEG C preferably, system reaction times preferably 3-8h, and obtain corresponding containing two hexanaphthene oxane compounds III, through washing, extraction, recrystallization, its purified content is greater than 99%, and overall yield of reaction is greater than 70%.
Instrument and reagent
Beijing Analytical Instrument Factory SY25000 type high pressure liquid chromatograph (methyl alcohol is moving phase, and C218 is stationary phase, flow velocity 1mL/min); Japan Shimadzu LC-10ATvp type high pressure liquid chromatograph (methyl alcohol: acetonitrile=2:1, flow velocity 1mL/min); Japan Shimadzu GC-14C, GC-17A gas chromatograph (DB-1 type pillar); 1102 type gas chromatographs (Shanghai analytical instrument factory); Hewlett-Packard Corporation of U.S. HP5989B type mass spectrograph; Hewlett-Packard HP 5989B type mass spectrograph.
Tosic acid, analytical pure (Solution on Chemical Reagents in Shanghai purchasing station); Toluene, analytical pure (Shanghai reagent one factory); Anhydrous magnesium sulfate, analytical pure (four-way chemical plant, Tianjin); To n-propyl dicyclohexyl formaldehyde, to ethylphenyl propylene glycol, open source literature preparation is pressed to n-pentyl dicyclohexyl formaldehyde and 2-.
The present invention is not only confined to instrument and the reagent of above-mentioned employing.
Claims (1)
1. a Liquid crystal monomer bicyclohexyl-containepoxyethane epoxyethane compound, this compound structure is as follows:
It is characterized in that this compound be 5-to ethylphenyl-2-(to propyl group dicyclohexyl)-1,3-diox or 5-to ethylphenyl-2-(to n-pentyl dicyclohexyl)-1,3-diox, this compound has liquid crystal characteristic, may be used for liquid-crystal display.
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| CN201210337052.9A CN102838584B (en) | 2012-09-13 | 2012-09-13 | Liquid crystal monomer bicyclohexyl-containing epoxyethane compound and synthetic method thereof |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5209868A (en) * | 1989-04-08 | 1993-05-11 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Trifluoromethylcyclohexane derivatives |
| EP1362839A2 (en) * | 1998-06-02 | 2003-11-19 | Chisso Corporation | Liquid crystal composition having a delta-epsilon- of not less than zero and liquid crystal display device |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5209868A (en) * | 1989-04-08 | 1993-05-11 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Trifluoromethylcyclohexane derivatives |
| EP1362839A2 (en) * | 1998-06-02 | 2003-11-19 | Chisso Corporation | Liquid crystal composition having a delta-epsilon- of not less than zero and liquid crystal display device |
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Denomination of invention: The invention relates to a liquid crystal monomer containing bicyclohexane oxane compound and a synthetic method thereof Effective date of registration: 20211209 Granted publication date: 20141231 Pledgee: Yantai Bank Co.,Ltd. Haiyang sub branch Pledgor: SHANDONG SHENGHUA ELECTRONIC NEW MATERIAL CO.,LTD. Registration number: Y2021980014417 |
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