CN109207158A - A kind of liquid-crystal compounds of the negative dielectric anisotropic containing alkenes and its application - Google Patents
A kind of liquid-crystal compounds of the negative dielectric anisotropic containing alkenes and its application Download PDFInfo
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- CN109207158A CN109207158A CN201710515586.9A CN201710515586A CN109207158A CN 109207158 A CN109207158 A CN 109207158A CN 201710515586 A CN201710515586 A CN 201710515586A CN 109207158 A CN109207158 A CN 109207158A
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- phenylene
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 92
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 86
- 150000001336 alkenes Chemical class 0.000 title description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims abstract 6
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- 239000000463 material Substances 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- -1 boronate ester Chemical class 0.000 claims description 6
- 125000001979 organolithium group Chemical group 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 claims description 3
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 claims description 3
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- 238000006264 debenzylation reaction Methods 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 2
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims description 2
- RGOVYLWUIBMPGK-UHFFFAOYSA-N nonivamide Chemical compound CCCCCCCCC(=O)NCC1=CC=C(O)C(OC)=C1 RGOVYLWUIBMPGK-UHFFFAOYSA-N 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 2
- 239000012286 potassium permanganate Substances 0.000 claims description 2
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 claims description 2
- 238000006751 Mitsunobu reaction Methods 0.000 claims 2
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 claims 2
- 239000007868 Raney catalyst Substances 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 238000006069 Suzuki reaction reaction Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 claims 1
- LHJSLDBKUGXPMI-UHFFFAOYSA-N tris(2-methylpropyl) borate Chemical compound CC(C)COB(OCC(C)C)OCC(C)C LHJSLDBKUGXPMI-UHFFFAOYSA-N 0.000 claims 1
- 230000004044 response Effects 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 4
- 230000003287 optical effect Effects 0.000 abstract description 3
- 230000014759 maintenance of location Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000012805 post-processing Methods 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 3
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- BRZYZVXYQQVYNT-UHFFFAOYSA-N 1-cyclohexylprop-2-en-1-ol Chemical compound C=CC(O)C1CCCCC1 BRZYZVXYQQVYNT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- NBHAHMHUMMWFPJ-UHFFFAOYSA-N 1-bromo-2-phenylmethoxybenzene Chemical compound BrC1=CC=CC=C1OCC1=CC=CC=C1 NBHAHMHUMMWFPJ-UHFFFAOYSA-N 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/13712—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering the liquid crystal having negative dielectric anisotropy
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
本发明涉及液晶领域，具体涉及一种含烯类负介电各向异性的液晶化合物及其制备方法与应用，所述液晶化合物具有通式(I)所示的结构，其中，R表示具有2‑10个碳原子的直链烯基，环A表示1,4‑亚苯基、1,4‑亚环己基或1‑4个氢原子被氟原子取代的1,4‑亚苯基；环B表示1,4‑亚苯基、1,4‑亚环己基、1,4‑亚环己烯基或1‑4个氢原子被氟原子取代的1,4‑亚苯基；m为1或2，n为0或1。本发明所述液晶化合物或含有所述液晶化合物的组合物具有较高的负介电各向异性，旋转粘度低，从而有效降低驱动电压，提高了液晶显示装置的响应速度，同时具有光学各向异性数值适中、电荷保持率高等特点，具有广阔的应用前景。 The present invention relates to the field of liquid crystals, in particular to a liquid crystal compound containing olefinic negative dielectric anisotropy, a preparation method and application thereof, wherein the liquid crystal compound has a structure represented by the general formula (I), wherein R represents a - Straight-chain alkenyl of 10 carbon atoms, ring A represents 1,4-phenylene, 1,4-cyclohexylene or 1,4-phenylene in which 1-4 hydrogen atoms are substituted by fluorine atoms; ring B represents 1,4-phenylene, 1,4-cyclohexylene, 1,4-cyclohexenylene or 1,4-phenylene in which 1-4 hydrogen atoms are substituted by fluorine atoms; m is 1 or 2, and n is 0 or 1. The liquid crystal compound or the composition containing the liquid crystal compound of the present invention has high negative dielectric anisotropy and low rotational viscosity, thereby effectively reducing the driving voltage, improving the response speed of the liquid crystal display device, and having optical anisotropy. It has the characteristics of moderate anisotropy value and high charge retention rate, and has broad application prospects.
Description
Technical field
The invention belongs to liquid-crystal compounds and its application field, be related to a kind of novel negative dielectric anisotropic compound and its
Preparation method and application.
Background technique
Liquid crystal display device development in recent years is more and more rapider, also develops different type, such as vehicle-mounted small-sized liquid crystal display
Device, portable liquid crystal device, ultrathin liquid crystal display device etc., this field exploitation is making progress, with TV
For, its main feature is that it is light-weight, take up space small, conveniently moving, there are also subnotebook PC, palm PC, mobile phones etc..
Liquid crystal material has pole as application of the environmentally conscious materials in the fields such as information display material, organic optoelectronic material
Big researching value and fine application prospect successfully solve visual angle, divide currently, TFT-LCD product technology is mature
The technical problems such as resolution, color saturation and brightness, large scale and small-medium size TFT-LCD display respective field gradually
Occupy the dominant position of flat-panel monitor.But the requirement to display technology is always in the continuous improvement, it is desirable that liquid crystal display
Realize faster response, reduce driving voltage to reduce power consumption etc., also require liquid crystal material have low voltage drive,
Quick response, wide temperature range and good low-temperature stability.
Liquid crystal material itself plays an important role to the performance for improving liquid crystal display, especially the rotation of reduction liquid crystal material
Turn viscosity and improves the dielectric anisotropy △ ε of liquid crystal material.New requirement is adapted it in order to improve the performance of material, it is novel
The synthesis of structure liquid-crystal compounds and the research of structure-performance relation become an important process of field of liquid crystals.
Summary of the invention
The first object of the present invention is to provide a kind of liquid-crystal compounds of negative dielectric anisotropic containing alkenes, compound tool
There is higher negative dielectric anisotropic, there is good low temperature intersolubility, can reduce liquid-crystal composition rotary viscosity to be promoted
The advantages that response time, required for these exactly improve liquid crystal material, has important application value.
Liquid-crystal compounds of the present invention, has the following structure:
Wherein, R indicate have 2-10 carbon atom straight-chain alkenyl, ring A expression Isosorbide-5-Nitrae-phenylene, 1 or 4 cyclohexylidene or
The 1,4- phenylene that 1-4 hydrogen atom is replaced by fluorine atoms；Ring B indicates 1,4- phenylene, 1,4- cyclohexylidene, the Asia 1,4- hexamethylene
The 1,4- phenylene that alkenyl or 1-4 hydrogen atom are replaced by fluorine atoms；
M is 1 or 2, and n is 0 or 1.
Preferably, in general formula I, R indicates that the straight-chain alkenyl with 2-5 carbon atom, ring A indicate Isosorbide-5-Nitrae-phenylene, 1,
The 1,4- phenylene that 4- cyclohexylidene or 1-4 hydrogen atom are replaced by fluorine atoms；Ring B indicates that 1,4- phenylene or 1-4 hydrogen are former
The 1,4- phenylene that son is replaced by fluorine atoms；
M is 1 or 2, and n is 0 or 1.
Technical solution more preferably, in general formula I, R indicate that the straight-chain alkenyl with 2-5 carbon atom, ring A indicate
1,4- cyclohexylidene；Ring B indicates the 1,4- phenylene that 1,4- phenylene or 1-2 hydrogen atom are replaced by fluorine atoms；
M is 1 or, 2, n be 0 or 1.
As further preferred technical solution, the liquid-crystal compounds is selected from one kind of following compound:
R indicates the straight-chain alkenyl with 2-5 carbon atom in I-1~I-4.
As preferred forms of the invention, the liquid-crystal compounds is selected from one kind of following compound:
The second object of the present invention is to provide the preparation method of above-mentioned liquid-crystal compounds.
According to the difference of n value, the present invention provides two different synthetic routes:
As a kind of technical solution, when n is 0, i.e., the described liquid-crystal compounds are as follows:
When, synthetic route is as follows:
Specifically includes the following steps:
(1)It reacts with organolithium reagent, then is reacted with borate, obtained
(2)It is synthesized by oxidation reaction
(3)WithProlong reaction by light, obtains
Wherein, R, m, the ring A in compound involved by each step are represented with R, m, ring A in gained liquid-crystal compounds product
Group is corresponding (ibid).
In step 1) described in the above method,The molar ratio of organolithium reagent and borate is 1
: 0.9~1.8: 0.9~3.0.
Wherein, one or more of the organolithium reagent selected from n-BuLi, s-butyl lithium or tert-butyl lithium, and/
Or, the borate is selected from one of trimethylborate, three isobutyl ester of triisopropyl borate ester, butyl borate or boric acid or several
Kind.
Preferably, reaction temperature can be at -50~-100 DEG C；
In the step 2),Molar ratio with oxidising agent is 1: 0.5~3.0.
Wherein, the oxidising agent is selected from the one or more of potassium permanganate, hydrogen peroxide or potassium bichromate.
Preferably, reaction temperature can be at 20~120 DEG C；
In the step 3),With diisopropyl azodiformate
Molar ratio is 1.0:0.9~1.5:1.0~3.0；
Preferably, reaction temperature can be at -30~50 DEG C；
Work as n=1, i.e., the described liquid-crystal compounds are as follows:When,
Synthetic route is as follows:
Specifically includes the following steps:
(1)WithIt is reacted, is obtained by suzuki
(2)By adding hydrogen debenzylation, obtain
(3)WithProlong reaction by light, obtains
Wherein, R, m in R, m in compound involved by each step, ring A, ring B and gained liquid-crystal compounds product, ring A,
The group that ring B is represented is corresponding (ibid).
In step 1) described in the above method,WithFeed intake mole
Than for 1.0:0.9~1.5；
Preferably, reaction temperature can be at 50~150 DEG C；
In the step 2),The mass ratio that feeds intake with catalyst is 1:0.03
~0.15；
Wherein, the catalyst is selected from one or more of Pd/C, Raney's nickel, Pt/C, preferably Pd/C.
Preferably, reaction temperature can be at 10~70 DEG C；
In the step 3),It is different with azoformic acid two
Propyl ester molar ratio is 1.0:0.9~1.5:1.0~3.0；
Preferably, reaction temperature can be at -30~50 DEG C；
It is above-mentionedAnd
Reagent etc. all uses/be related to can be by method known per se in public commercial source or document
Synthesis obtains.
Method of the present invention can be related to conventional post-processing if necessary, and the conventional post-processing is specific such as: using dichloro
Methane, ethyl acetate or toluene extraction, liquid separation are washed, dry, vacuum rotary evaporator evaporation, products therefrom vacuum distillation
Or recrystallization and/or chromatography purify.
It can be stablized using above-mentioned preparation method, be efficiently obtained liquid-crystal compounds of the present invention.
The third object of the present invention is the composition that protection contains the liquid-crystal compounds.The liquid-crystal compounds is combining
Mass percent in object is 1~60%, preferably 3~50%, further preferably 5~25%.
The fourth object of the present invention is that the protection liquid-crystal compounds and the composition containing the liquid-crystal compounds exist
The application of field of liquid crystal display, the application preferably in liquid crystal display device.The liquid crystal display device includes but not
It is limited to TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.It has used the liquid-crystal compounds or has contained the LCD compound
The composition of object negative dielectric anisotropic with higher, rotary viscosity is low, so that driving voltage be effectively reduced, improves liquid crystal
The response speed of display device, while having the characteristics that optical anisotropy numerical value is moderate, charge conservation rate is high.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..
The raw material unless otherwise instructed, can be obtained from public commercial source.
According to the common detection methods of this field, the various performance parameters of liquid-crystal compounds are obtained by linear fit,
In, the concrete meaning of each performance parameter is as follows:
△ n represents optical anisotropy (25 DEG C)；△ ε represents dielectric anisotropy (25 DEG C, 1000Hz)；γ 1 represents rotation
Turn viscosity (mPa.s, 25 DEG C)；Cp represents clearing point.
Embodiment 1
The structural formula of liquid-crystal compounds are as follows:
The synthetic line of prepare compound BYLC-01 is as follows:
Specific step is as follows:
(1) synthesis of compound BYLC-01-1:
35.2g 1- (2- fluoroethane oxygroup) -2,3- difluorobenzene, 300ml tetrahydrofuran, temperature control -70 are added in reaction flask
The hexane solution of~-80 DEG C of dropwise addition 0.24mol n-BuLis drips and finishes insulation reaction 1 hour, and temperature control -70~-80 DEG C are added dropwise
Then 31.8g trimethylborate is risen again naturally to -30 DEG C.2M aqueous hydrochloric acid solution 200ml is added to be acidified, after carrying out routine
Processing, petroleum ether are recrystallized to give light yellow solid (compound BYLC-01-1) 40.9g, HPLC:99.4%, yield 93.0%；
(2) synthesis of compound BYLC-01-2:
40.0g compound BYLC-01-1,200ml tetrahydrofuran are added in reaction flask, 50ml water is heated with stirring to 60 DEG C
~70 DEG C, 60 DEG C~70 DEG C of temperature control are added dropwise the solution that 30.0g hydrogen peroxide (30%)+30ml water forms, then 60~70 DEG C of temperature control
4h is reacted, conventional post-processing is carried out, obtains light yellow solid (compound BYLC-01-2): 30.0g, GC:99.5%, yield:
85.8%；
(3) synthesis of compound BYLC-01:
Under nitrogen protection, 30.0g compound BYLC-01-2,21.8g vinyl cyclohexyl methanol are added into reaction flask,
49.0g triphenylphosphine, 200ml tetrahydrofuran, 0 DEG C~10 DEG C dropwise addition 47.2g diisopropyl azodiformates of temperature control are then natural
It returns and warms to room temperature, react 6 hours.Conventional post-processing is carried out, through chromatogram purification, n-hexane elution, ethyl alcohol recrystallization obtains white
Solid (compound BYLC-01) 41.0g, GC:99.6%, yield: 83.6%.
Gained white solid BYLC-01 is analyzed using GC-MS, the m/z of product is 314.1 (M+).
1H-NMR(300MHz,CDCl3): 1.35-2.20 (m, 10H), 3.63-4.25 (m, 4H), 4.35-5.45 (m, 4H),
5.65-6.10(m,1H),6.25-6.75(m,2H)。
Embodiment 2
The structural formula of liquid-crystal compounds are as follows:
The synthetic line of prepare compound BYLC-02 is as follows:
Specific step is as follows:
The synthesis of compound BYLC-02:
Under nitrogen protection, 25.0g compound BYLC-01-2,27.5g vinyl dicyclohexyl first are added into reaction flask
Alcohol, 44.3g triphenylphosphine, 150ml tetrahydrofuran, 0 DEG C~10 DEG C dropwise addition 42.0g diisopropyl azodiformates of temperature control, then
Naturally it returns and warms to room temperature, react 6 hours.Conventional post-processing is carried out, through chromatogram purification, n-hexane elution, ethyl alcohol recrystallization is obtained
White solid (compound BYLC-02) 43.5g, GC:99.8%, yield: 84.5%.
Gained white solid BYLC-02 is analyzed using GC-MS, the m/z of product is 396.1 (M+).
1H-NMR(300MHz,CDCl3): 1.35-2.20 (m, 20H), 3.63-4.25 (m, 4H), 4.35-5.45 (m, 4H),
5.65-6.10(m,1H),6.25-6.75(m,2H)。
Embodiment 3
According to embodiment 1, the technical solution of embodiment 2, it is only necessary to which the corresponding raw material of simple replacement does not change any essence
Property operation, following liquid-crystal compounds can be synthesized.
Embodiment 4
The structural formula of liquid-crystal compounds are as follows:
The synthetic line of prepare compound BYLC-04 is as follows:
Specific step is as follows:
(1) synthesis of compound BYLC-04-1:
Under nitrogen protection, the addition 25.0g BYLC-01-1 into reaction flask, 30.2g benzyloxy bromobenzene, 80ml toluene,
40ml deionized water, 20ml ethyl alcohol, 20.0g natrium carbonicum calcinatum, tetra- triphenylphosphine of 0.4g conjunction palladium, heating reflux reaction 3 hours.Into
The conventional post-processing of row, through chromatogram purification, n-hexane elution, ethyl alcohol recrystallization obtains white solid (compound BYLC-04-1)
33.5g, GC:99.6%, yield: 82.5%.
(2) synthesis of compound BYLC-04-2:
30.0g compound BYLC-04-1,1.3g palladium carbon, 50ml toluene, 50ml ethyl alcohol, hydrogen displacement are added in reaction flask
Twice, 10~20 DEG C of hydrogenation reaction 6h of temperature control carry out conventional post-processing, obtain light yellow solid (compound BYLC-04-2):
22.4g, GC:99.5%, yield: 96.0%；
(3) synthesis of compound BYLC-04:
Under nitrogen protection, 20.0g compound BYLC-04-2,10.5g vinyl cyclohexyl methanol are added into reaction flask,
25.4g triphenylphosphine, 100ml tetrahydrofuran, 0 DEG C~10 DEG C dropwise addition 22.7.0g diisopropyl azodiformates of temperature control, then certainly
It so returns and warms to room temperature, react 6 hours.Conventional post-processing is carried out, through chromatogram purification, n-hexane elution, ethyl alcohol recrystallization obtains white
Color solid (compound BYLC-04) 24.6g, GC:99.7%, yield: 84.8%.
Gained white solid BYLC-04 is analyzed using GC-MS, the m/z of product is 390.1 (M+).
1H-NMR(300MHz,CDCl3): 1.35-2.20 (m, 10H), 3.63-4.25 (m, 4H), 4.35-5.45 (m, 4H),
5.65-6.10(m,1H),6.35-7.55(m,6H)。
Embodiment 5
Technical solution according to embodiment 4, it is only necessary to the corresponding raw material of simple replacement does not change any substantive operations,
Following liquid-crystal compounds can be synthesized.
Experimental example 1
By compound BYLC-01 obtained by embodiment 1 and comparative example 1 (known common another like liquid-crystal compounds)
Liquid-crystal compounds performance parameter data compare arrangement, testing result is as shown in table 1:
Table 1: the performance test results of liquid-crystal compounds
By the testing result of table 1, it is apparent that liquid-crystal compounds provided by the invention and traditional chemistry similar knot
Structure compound, which is compared, has bigger negative dielectric anisotropic, is more advantageous to the negative dielectric anisotropic for promoting liquid-crystal composition,
It is further reduced polar monomer use, effectively reduces liquid-crystal composition rotary viscosity to promote the response time.
Experimental example 2
By compound BYLC-02 obtained by embodiment 2 and comparative example 2 (known common another like liquid-crystal compounds)
Liquid-crystal compounds performance parameter data compare arrangement, testing result is as shown in table 2:
Table 2: the performance test results of liquid-crystal compounds
By the testing result of table 2, it is apparent that liquid-crystal compounds provided by the invention and traditional chemistry similar knot
Structure compound, which is compared, has bigger negative dielectric anisotropic, is more advantageous to the negative dielectric anisotropic for promoting liquid-crystal composition,
It is further reduced polar monomer use, effectively reduces liquid-crystal composition rotary viscosity to promote the response time.
Experimental example 3
By compound BYLC-03 obtained by embodiment 3 and comparative example 3 (known common another like liquid-crystal compounds)
Liquid-crystal compounds performance parameter data compare arrangement, testing result is as shown in table 3:
Table 3: the performance test results of liquid-crystal compounds
By the testing result of table 3, it is apparent that liquid-crystal compounds provided by the invention and traditional chemistry similar knot
Structure compound, which is compared, has bigger negative dielectric anisotropic, is more advantageous to the negative dielectric anisotropic for promoting liquid-crystal composition,
It is further reduced polar monomer use, effectively reduces liquid-crystal composition rotary viscosity to promote the response time.
In addition, discovery after herein described compound is particularly applicable in the liquid-crystal composition of conventional system, it can be with
The dielectric anisotropy △ ε of liquid-crystal composition is improved, while keeping rotary viscosity γ 1 appropriate and refractive index appropriate respectively to different
Property △ n, gained liquid-crystal composition have the characteristics that significant quick response and low voltage drive feature.
Although above the present invention is described in detail with a general description of the specific embodiments,
On the basis of the present invention, it can be made some modifications or improvements, this will be apparent to those skilled in the art.Cause
This, these modifications or improvements, fall within the scope of the claimed invention without departing from theon the basis of the spirit of the present invention.
Claims (10)
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