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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- liquid crystal
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- epoxyethane
- bicyclohexyl
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 40
- -1 epoxyethane compound Chemical class 0.000 title claims abstract description 23
- 239000000178 monomer Substances 0.000 title claims abstract description 16
- 238000010189 synthetic method Methods 0.000 title abstract description 7
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 9
- 125000000217 alkyl group Chemical group 0.000 abstract description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 abstract description 6
- 239000000460 chlorine Substances 0.000 abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 abstract description 6
- 239000011737 fluorine Substances 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 16
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- OMZUSEQVUVSWND-UHFFFAOYSA-N 3-phenylpentane-2,3-diol Chemical compound CCC(O)(C(C)O)C1=CC=CC=C1 OMZUSEQVUVSWND-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical group C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- LLOCCQQYPYWUCK-UHFFFAOYSA-N cyclohexyl-(1-pentylcyclohexyl)methanone Chemical compound C1CCCCC1C(=O)C1(CCCCC)CCCCC1 LLOCCQQYPYWUCK-UHFFFAOYSA-N 0.000 description 2
- LQKJINMGJGSJDD-UHFFFAOYSA-N cyclohexyl-(1-propylcyclohexyl)methanone Chemical compound C(CC)C1(CCCCC1)C(=O)C1CCCCC1 LQKJINMGJGSJDD-UHFFFAOYSA-N 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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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| Application Number | Priority Date | Filing Date | Title |
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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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| Publication Number | Publication Date |
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| CN102838584A CN102838584A (en) | 2012-12-26 |
| CN102838584B true CN102838584B (en) | 2014-12-31 |
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| CN107573948B (en) * | 2017-09-11 | 2020-08-04 | 陕西莱特光电材料股份有限公司 | Cyclohexane liquid crystal monomer compound and preparation method thereof |
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 |
-
2012
- 2012-09-13 CN CN201210337052.9A patent/CN102838584B/en active Active
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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| CN102838584A (en) | 2012-12-26 |
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