CN102898288A - Difluorovinyl-ether-containing liquid crystal compound and composition and liquid crystal displayer thereof - Google Patents
Difluorovinyl-ether-containing liquid crystal compound and composition and liquid crystal displayer thereof Download PDFInfo
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- CN102898288A CN102898288A CN2012103885347A CN201210388534A CN102898288A CN 102898288 A CN102898288 A CN 102898288A CN 2012103885347 A CN2012103885347 A CN 2012103885347A CN 201210388534 A CN201210388534 A CN 201210388534A CN 102898288 A CN102898288 A CN 102898288A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 92
- 150000001875 compounds Chemical class 0.000 title claims abstract description 72
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- MNCPYCODYCPASZ-UHFFFAOYSA-N 2-(2,2-difluoroethenoxy)-1,1-difluoroethene Chemical compound FC(F)=COC=C(F)F MNCPYCODYCPASZ-UHFFFAOYSA-N 0.000 title abstract description 6
- -1 2, 3-difluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene, 2-chloro-3-fluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, indan-2, 5-diyl Chemical group 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 238000006467 substitution reaction Methods 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 5
- 238000001308 synthesis method Methods 0.000 abstract description 4
- 239000004983 Polymer Dispersed Liquid Crystal Substances 0.000 abstract description 3
- 230000003287 optical effect Effects 0.000 abstract description 3
- 230000000704 physical effect Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- 239000003208 petroleum Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- JLGADZLAECENGR-UHFFFAOYSA-N 1,1-dibromo-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Br)Br JLGADZLAECENGR-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 2
- 230000003098 cholesteric effect Effects 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
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- 238000009987 spinning Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- COIQUVGFTILYGA-UHFFFAOYSA-N (4-hydroxyphenyl)boronic acid Chemical compound OB(O)C1=CC=C(O)C=C1 COIQUVGFTILYGA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- AOIYTIDHFMNVOO-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydro-1h-indene Chemical compound C1CCC=C2CCCC21 AOIYTIDHFMNVOO-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- XRMZKCQCINEBEI-UHFFFAOYSA-N 4-bromo-2-fluoro-1-iodobenzene Chemical compound FC1=CC(Br)=CC=C1I XRMZKCQCINEBEI-UHFFFAOYSA-N 0.000 description 1
- MRQYTJXVULSNIS-UHFFFAOYSA-N 4-bromo-3-fluorophenol Chemical compound OC1=CC=C(Br)C(F)=C1 MRQYTJXVULSNIS-UHFFFAOYSA-N 0.000 description 1
- PKIYFPSPIFCDDB-UHFFFAOYSA-N 4-ethoxy-2,3-difluorophenol Chemical compound CCOC1=CC=C(O)C(F)=C1F PKIYFPSPIFCDDB-UHFFFAOYSA-N 0.000 description 1
- DXYQMEXICHRFCN-XQRVVYSFSA-N C/C=C(/C(C)=C)\F Chemical compound C/C=C(/C(C)=C)\F DXYQMEXICHRFCN-XQRVVYSFSA-N 0.000 description 1
- DVDDAPSLJMAFMX-UHFFFAOYSA-N CC(C1)COc2c1ccc(C)c2F Chemical compound CC(C1)COc2c1ccc(C)c2F DVDDAPSLJMAFMX-UHFFFAOYSA-N 0.000 description 1
- RPMUDXVQHUECRE-UHFFFAOYSA-N CC1COC(C)OC1 Chemical compound CC1COC(C)OC1 RPMUDXVQHUECRE-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N Cc1ccc(C)cc1 Chemical compound Cc1ccc(C)cc1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- JTAUTNBVFDTYTI-UHFFFAOYSA-N Cc1cccc(C)c1F Chemical compound Cc1cccc(C)c1F JTAUTNBVFDTYTI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 238000006411 Negishi coupling reaction Methods 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005701 difluoromethyleneoxy group Chemical group FC(F)([*:1])O[*:2] 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- IRSJDVYTJUCXRV-UHFFFAOYSA-N ethyl 2-bromo-2,2-difluoroacetate Chemical compound CCOC(=O)C(F)(F)Br IRSJDVYTJUCXRV-UHFFFAOYSA-N 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000002535 lyotropic effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention provides difluorovinyl-ether-containing liquid crystal compounds of a general formula (I) and a synthesis method, a composition and use thereof in liquid crystal elements. The novel liquid crystal compound provided by the invention has excellent chemical and physical properties, and lower optical anisotropy and higher dielectric anisotropy than other liquid crystal materials. The liquid crystal composition can be used in liquid crystal elements with the liquid crystal medium, such as TN, STN, TFT, VA, ECB, OCB, LCP, PDLC, BiNem, LC LENS, FFS and IPS liquid crystal elements.
Description
Technical Field
The present invention relates to a liquid crystal compound and a composition comprising the same, and more particularly, to a novel difluorovinylether-containing liquid crystal compound and a liquid crystal composition comprising the same.
Background
Physically, substances are classified into three states, namely solid, liquid and gaseous. In nature, most materials exhibit only three states of solid, Liquid and gas depending on temperature, and Liquid Crystal (Liquid Crystal) is a new state of matter different from the ordinary solid, Liquid and gas states, and is a state of matter having both Liquid and Crystal properties in a certain temperature range, also called a Liquid Crystal phase or an intermediate phase, and is also called a fourth state of matter.
Liquid crystals are in many kinds, and naturally occurring and artificially synthesized liquid crystals are in many thousands, but they are basically organic compounds. Liquid crystals are classified into thermotropic liquid crystals, lyotropic liquid crystals, induced liquid crystals and flow-induced liquid crystals, according to the conditions under which the liquid crystal phase is formed.
At present, liquid crystal materials used for display are basically thermotropic liquid crystals. Thermotropic liquid crystals are classified into Smectic (semiconducting) liquid crystals (also called lamellar liquid crystals), Nematic (Nematic) liquid crystals (also called filamentous liquid crystals), and cholesteric (cholesteric) liquid crystals (also called helical liquid crystals) depending on the molecular arrangement order state. The physical properties of these phases are known. The molecular structural features of compounds used in the field of electro-optics are generally a rigid backbone comprising, for example, linked 1, 4-phenylene or 1, 4-cyclohexylene groups or heterocyclic ring systems, which are substituted at positions as far apart from one another as possible by so-called mesogenic groups, such as alkyl, alkoxy or cyano groups.
Liquid-crystalline media used in the electro-optical field consist of mixtures of these compounds, and compounds which do not have a interconversion from the crystalline phase to the liquid-crystalline phase are also used. Liquid crystal mixtures are classified into a dynamic scattering type (DS type), a guest-host type (GH type), a twisted nematic type (TN type), a super twisted nematic type (STN type), a thin film transistor type (TFT type), a ferroelectric type (FLC type), and the like. Liquid crystal materials have been widely used for producing liquid crystal display elements such as electronic computers, various measuring instruments, instrument panels for automobiles, electronic notebooks, cellular phones, computers, and televisions.
Hitherto, liquid crystal materials used therefor have been synthesized into various compounds, and they are suitable for use in accordance with the display mode or driving mode and the use thereof. On the other hand, the demand for improving the performance of liquid crystal display elements has been increasing year by year, and in order to meet this demand, development of novel liquid crystal compounds has been continued.
Disclosure of Invention
The invention aims to provide a novel liquid crystal compound containing difluorovinylether.
Another object of the present invention is to provide a synthesis method for synthesizing the liquid crystal compound.
It is still another object of the present invention to provide a composition comprising the liquid crystal compound.
It is a further object of the present invention to provide a use of the liquid crystal composition in liquid crystal devices, which can be used for liquid crystal devices having liquid crystal media, such as TN, STN, TFT, VA, ECB, OCB, LCP, PDLC, BiNem, LC LENS, FFS, and IPS display modes.
One aspect of the present invention provides a novel liquid crystal compound having a structure represented by general formula (i):
wherein,
R1and R2Identical or different, each independently selected from the group consisting of-H, -F, -Cl, -CN, -NCS, -SCN, -OCN, -NCO,
A halogenated or non-halogenated linear or branched alkyl or alkoxy group of 1 to 20 carbon atoms and a halogenated or non-halogenated linear or branched alkenyl or alkenyloxy group of 2 to 20 carbon atoms, wherein, in said R1And said R2At least one of-CH2May be substituted by-O-, -S-, -SiH2-、-CH=CH-、-C≡C-、-CF=CF-、-CH=CF-、
-CO-O-or-O-CO-substitution, with the proviso that the heteroatoms are not directly linked to one another;
ring A1、A2、A3、A4、A5And A6Are the same or different and are each independently selected from the group consisting of
A cyclic structure of the group;
wherein,
the cyclic structure may also conform to at least one of the following a), b), c) and d):
a) one or more hydrogen atoms in the cyclic structure may be replaced by-D, -F, -Cl, -CN, -CF3、-OCF3、-CH2F、-OCH2F、-CF2H、-OCF2H、-OCH3or-CH3Replacement;
b) one or more-CH in the cyclic structure2-by-O-, -SiH2-, -S-or-CO-substitution, with the proviso that the heteroatoms are not directly connected to one another;
c) in the cyclic structure, one or more-CH-in the aromatic ring structure may be replaced by N;
d) one or more of the ring structuresCan be covered with
Replacement;
Z1、Z3、Z4and Z5The same or different, each independently selected from the group consisting of carbon-carbon single bond, -CO-O-, -CF2O-、-CH2O-、-OCH2-、-CH2CH2-、-CF2CH2-、-CF=CF-、-CH=CH-、-CH=CF-、-C2F4-、-(CH2)4-、-(CF2)4-、-OCF2CF2O-、-CF2CF2CF2O-、-CH2CH2CF2O-、-OCH2CF2O-、-CH2CF2OCH2-、-CH=CHCF2O-、-CF2OCH=CH-、-CF2OCF=CH-、-CF2OCH=CF-、-CF=CFCF2O-、-CF2OCF=CF-、-CH=CHCH2CH2-、-CH2CH=CHCH2-、-C2H4OCH2-、-OCH2CH2CH2-, -CF = CF = CF-, -C.ident.C-CF = CF-C.ident.C-, -CF = CF-C.ident.C-CF = CF-and-C.ident.C-CF2O-;
a is 0 or 1, b, c and d are the same or different and are each independently 0, 1 or 2.
In some preferred embodiments, R1And R2Same or different, eachIndependently selected from the group consisting of H, -F, -Cl, -CN, -NCS,
A halogenated or unsubstituted linear or branched alkyl or alkoxy group of 1 to 10 carbon atoms and a halogenated or non-halogenated linear or branched alkenyl or alkenyloxy group of 2 to 10 carbon atoms, wherein, in said R1And said R2At least one of-CH2May be substituted by-O-, -CH = CH-, -C.ident.C-, -CF = CF-, -CH = CF-,
or-CO-O-substitution, provided that the heteroatoms are not directly linked to one another.
In some preferred embodiments, ring A1、A2、A3、A4、A5And A6Are the same or different and are each independently selected from the group consisting of
Group (d) of (a).
In some preferred embodiments, ring A1、A2、A3、A4、A5And A6Each independently of the other is selected from
A cyclic structure of the group.
In some preferred embodiments, Z1、Z3、Z4And Z5The same or different, each independently selected from the group consisting of-CO-O-, -CF2O-、-CH2O-、-OCH2-、-CH2CH2-、-CF=CF-、-CH=CH-、-(CH2)4-、-C2F4-、-(CF2)4-、-OCF2CF2O-、-CF=CFCF2O-, -C.ident.C-and carbon-carbon single bonds.
In some preferred embodiments, Z1、Z3、Z4And Z5Each independently of the others selected from the group consisting of-CO-O-, -CF2O-、-CH2O-、-CH2CH2-、-CF=CF-、-CH=CH-、-C2F4-、-(CH2)4-、-(CF2)4-、-OCF2CF2O-、-CF=CFCF2O-, -C.ident.C-and carbon-carbon single bonds.
In some preferred embodiments, Z1、Z3、Z4And Z5Each independently of the others from the group consisting of-CF2O-、-CH2O-、-CH2CH2-、-CF=CF-、-CH=CH-、-CF=CFCF2O-, -C.ident.C-and carbon-carbon single bonds.
In some preferred embodiments, a is 0 or 1; b + c + d is less than or equal to 3.
In some preferred embodiments, the compound of formula (i) is particularly preferably one or more of the group consisting of:
wherein,
R1and R2The same or different, each independently selected from the group consisting of H, -F, -Cl, -CN, and a halogenated or unsubstituted, linear or branched alkyl or alkoxy group of 1 to 7 carbon atoms, wherein, in said R1And said R2At least one of-CH2May be substituted by-O-, -CH = CH-, -C.ident.C-, -CF = CF-, -CH = CF-,
or-CO-O-substitution, provided that the heteroatoms are not directly linked to one another.
Another object of the present invention is to provide a process for preparing the above compound, comprising the steps of:
the compound of the general formula (III-2) and sodium hydride form sodium salt, and then react with tetrafluorodibromoethane to obtain a compound of the general formula (III-1); and (3) reducing the compound of the general formula (III-1) by lithium aluminum hydride to obtain the compound of the general formula (III).
The compound of formula (III) and sodium hydride form a sodium salt which is then reacted with a compound of formula (IV) to give a compound of formula (I).
The compounds of the general formula (III-2) and the general formula (III) are mainly synthesized by a commercially available intermediate or a commonly known synthesis method, wherein the commonly known synthesis method comprises esterification reaction, witting reaction, carbon-carbon cross-coupling reaction (Suzuki coupling, Negishi coupling, Heck coupling, Sonogashira coupling, transition metal catalysis Grignard reagent cross-coupling reaction and the like), reduction reaction and the like.
The main reaction process is as follows:
1) adding a compound of a general formula (III-2) into anhydrous dimethylformamide solvent under the protection of argon, adding sodium hydride in batches, heating to 60 ℃, reacting for 1 hour, cooling to room temperature, then dropwise adding a dimethylformamide solution of ethyl difluorobromoacetate, and reacting for 12 hours at room temperature to obtain the compound of the general formula (III-1).
2) Dissolving the compound of the general formula (III-1) in anhydrous acetonitrile, adding zinc powder under the protection of nitrogen, and refluxing for 10-12 h to obtain the compound of the general formula (III).
3) The compound of the general formula (IV) is dissolved in anhydrous dimethylformamide solvent, N2Adding sodium hydride under the protection, heating to 60 ℃, reacting for 1h, adding the compound of the general formula (III-1), and reacting for 1h at 60 ℃ to obtain the compound of the general formula (V).
It is a further object of the present invention to provide a liquid crystal composition comprising one or more liquid crystal compounds of formula (I).
In some embodiments, the liquid crystal composition comprises one to five liquid crystal compounds of formula (I), preferably the liquid crystal composition comprises two to four liquid crystal compounds of formula (I).
Further mixing components of the liquid-crystalline composition according to the invention may be generally known mesogenic compounds, i.e. compounds which form liquid-crystalline phases, either neat or mixed with other components. Some such compounds are mentioned for example in D E1804894 and CN 1158602A. Preferably, in some embodiments, the liquid crystal composition further comprises at least one liquid crystal compound of formula (ii):
wherein,
R3and R4The same or different, each independently selected from the group consisting of-H, -F, -Cl, -CN, -NCS, -SCN, -OCN, -NCO, -OCH = CF2And a halogenated or non-halogenated linear or branched alkyl or alkoxy group of 1 to 20 carbon atoms, wherein in said R3And said R4At least one of-CH2May be substituted by-O-, -S-, -SiH2-、-CH=CH-、-C≡C-、-CF=CF-、-CH=CF-、
-CO-O-or-O-CO-substitution, with the proviso that the heteroatoms are not directly linked to one another;
B1、B2and B3And B4Are the same or different and are each independently selected from the group consisting of
2, 3-difluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene, 2-chloro-3-fluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, indan-2, 5-diyl, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl, and 1,2,3, 4-tetrahydronaphthalene-2, 6-diylOne or two non-adjacent-CH2-may be replaced by-O-or-S-, saidOne or more of H may each independently be substituted by F, said
One or two non-adjacent-CH-s may be replaced by N, said
One or two non-adjacent-CH2May be replaced by O, said
Each of the one or more H may be independently substituted with F;
Y1、Y2and Y3The same or different, each independently selected from the group consisting of-OCO-, -CO-O-, -CF2O-、-CH2O-、-OCH2-、-CH2CH2-、-CF2CH2-、-CF=CF-、-CH=CH-、-CH(CH3)CH2-、-CH2CH(CH3)-、-(CH2)3O-、-O(CH2)3-、-COS-、-SCO-、-CH=CF-、-C2F4-、-(CH2)4-、-C4F8-、-OCF2CF2O-、-CF2CF2CF2O-、-CH2CH2CF2O-、-CH2CF2OCH2-、-CH=CHCF2O-、-CF2OCH=CH-、-CF2OCF=CH-、-CF2OCH=CF-、-CF=CFCF2O-、-CF2OCF=CF-、-CH=CHCH2CH2-、-C2H4OCH2-、-CH2CH=CHCH2-、-OCH2CH2CH2-、-CF=CF-CF=CF-、-C≡C-CF=CF-、-C≡C-CF=CF-C≡C-、-CF=CF-C≡C-CF=CF-、-C≡C-CF2O-, -C ≡ C-and a single bond, wherein in the Y1And Y2Any one of-CH2May be-SiH2-substitution;
m, n and p are the same or different and are each independently 0, 1 or 2.
The liquid crystal compound is selected from the group consisting of:
in some embodiments, the liquid crystal composition comprises 5 to 50% by weight of the total weight of the liquid crystal composition of a compound of formula (I); 50-95% of the compound of formula (II) by total weight of the liquid crystal composition, preferably 10-30% of the compound of formula (I) by total weight of the liquid crystal composition; 70-90% of the compound of the general formula (II) based on the total weight of the liquid crystal composition.
It is still another object of the present invention to provide a liquid crystal display comprising a liquid crystal composition comprising the liquid crystal compound of the present invention.
It is still another object of the present invention to provide a novel difluorovinylether-containing liquid crystal compound which is suitable as a composition of a liquid crystal medium and applicable to liquid crystal devices containing a liquid crystal medium, such as TN, STN, TFT, VA, ECB, OCB, LCP, PDLC, BiNem, LC LENS, FFS, and IPS display mode liquid crystal devices.
The novel hexahydroindene-containing liquid crystal compound provided by the invention has good chemical and physical properties, and has lower viscosity, larger optical anisotropy and larger dielectric anisotropy compared with other liquid crystal materials.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
For convenience of expression, in the following examples, the group structures of the liquid crystal compounds are represented by the codes listed in Table 1:
TABLE 1 radical structural code of liquid crystal compounds
Compounds of the following formula are exemplified:
the structural formula is represented by the code listed in Table 1, and can be expressed as: 3PUQUF, Q in the code represents difluoromethyleneoxy; c in the code represents cyclohexane; u in the code represents 2, 5-difluorophenylene.
Example 1
The synthetic route of the compound HCLC-12 prepared is shown below,
the specific process steps are as follows:
1) synthesis of HCLC-12-2
Adding 21.8g of propiophenol and 200mL of Dimethylformamide (DMF) into a 500mL three-neck flask, dissolving, adding 8g of 60% sodium hydride (NaH) under the protection of nitrogen, heating to 60 ℃, reacting for 1h, cooling to 30 ℃, dropwise adding 31.2g of tetrafluorodibromoethane, and reacting for 12h at room temperature. Adding ethyl acetate 200ml and water 200ml, layering, extracting water layer with ethyl acetate 200ml, combining organic layers, washing with water for 2 times, washing with brine twice, drying and concentrating to obtain crude product 38.5g, and crude petroleum ether passing through column to obtain 34 g. GC: 98.8% and yield 85.6%.
2) Synthesis of HCLC-12-1
20g of HCLC-12-2, 6g of zinc powder and 100ml of acetonitrile are added into a 250ml reaction bottle, reflux is carried out for 11h under nitrogen, the temperature is reduced to room temperature, and the crude product is obtained after suction filtration and spin drying. After the crude product is dissolved by adding petroleum ether, the petroleum ether is eluted and passes through a column, and the product is dried by spinning to obtain 13.4 g. Yield 89%, GC: 86.3 percent.
3) Synthesis of HCLC-12
A250 ml reaction flask was charged with 1.9g of 60% sodium hydride NaH, 3.2g of 2, 3-difluoro-4-ethoxyphenol and 100ml of DMF, N2Heating to 60 ℃ to react for 1h, adding 6g of HCLC-12-1, reacting at 60 ℃ for 6h, adding 300ml of water and 200ml of ethyl acetate to extract, washing with water, washing with brine, drying, concentrating, performing petroleum ether column chromatography to obtain 8.4g of colorless oily substance, and recrystallizing with 10ml of ethanol at-30 ℃ for four times to obtain 1.97g of colorless transparent oily substance, wherein GC: 99.7% and a yield of 25%.
1H NMR(300MHz,CDCl3)δ7.50-7.21(m,2H),6.94-6.76(m,2H),6.55-6.60(m,2H),4.09(q,J=11.8Hz,2H),2.69-2.73(m,1H),1.89-1.09(m,16H),0.93-0.82(m,3H)。
Example 2
The synthetic route of the compound HCLC-12K prepared is shown as follows,
[4, 4-difluoro- (3,4, 5-trifluorophenoxy) methyl ] -3, 5-difluorophenylboronic acid can be synthesized by a method known in the art (see European Journal of Organic Chemistry, 2008, V20p 3479-3487).
The specific process steps are as follows:
1) synthesis of HCLC-12K-4
Adding 15g of p-propylphenol and 150mL of DMF into a 250mL three-neck flask, dissolving, adding 4.4g of sodium hydride (NaH) under the protection of nitrogen, heating to 60 ℃, reacting for 1h, cooling to 30 ℃, dropwise adding 36g of tetrafluorodibromoethane, and reacting for 12h at room temperature. Adding 200ml ethyl acetate and 200ml water, separating layers, extracting water layer with 200ml ethyl acetate, combining organic layers, washing with water for 2 times, washing with brine for two times, drying and concentrating to obtain crude product 30g, and passing petroleum ether crude product through column to obtain 22.5 g. GC: 96.5% and yield 64.8%.
2) Synthesis of HCLC-12K-3
22.5g of HCLC-12K-4, 10g of zinc powder and 150ml of acetonitrile are added into a 250ml reaction bottle, reflux is carried out for 11h under nitrogen, the temperature is reduced to room temperature, suction filtration and spin drying are carried out, and a crude product is obtained. The crude product is dissolved by adding petroleum ether, and then the solution is passed through a column and is dried by spinning to obtain 9.6g of a product. Yield 62.3%, GC: 85.8 percent.
3) Synthesis of HCLC-12K-2
A1L dry clean single neck flask was charged with 20g of p-hydroxyphenylboronic acid, 43.5g of 3-fluoro-4-iodobromobenzene, 30.5g of anhydrous sodium carbonate, 144mL of deionized water, 160mL of toluene and 80mL of anhydrous ethanol, purged with argon, and then 0.5g of Pd [ P (Ph)3]4. Heating and refluxing for 6h under the protection of argon, cooling the reaction liquid, separating the liquid, drying 20g of anhydrous sodium sulfate, evaporating the toluene of the organic phase, passing through a silica gel column, eluting with 3:1 petroleum ether and ethyl acetate, evaporating the solvent of the chromatographic liquid by using a rotary evaporator to obtain 42g of light yellow solid, and recrystallizing the crude product by using 100mL of anhydrous ethanol and 100mL of toluene to obtain 31.5g of white solid, wherein the GC content is 99.6%, and the yield is 82%.
4) Synthesis of HCLC-12K-1
A250 mL dry clean single-neck bottle was charged with 6g of HCLC-12K-2, 8g of [4, 4-difluoro- (3,4, 5-trifluorophenoxy) methyl]-3, 5-difluorophenylboronic acid, 4.8g of anhydrous sodium carbonate, 25mL of deionized water, 100mL of toluene, and 25mL of anhydrous ethanol, purged with argon, and then 0.5g of Pd [ P (Ph)3]4. Heating and refluxing for 12h under the protection of argon, cooling the reaction liquid, separating the liquid, evaporating the organic phase to remove toluene, passing through a silica gel column, eluting with 3:1 petroleum ether and ethyl acetate, evaporating the solvent from the chromatographic solution by using a rotary evaporator to obtain 11g of light yellow solid, and recrystallizing the crude product by using 20mL of toluene and 10mL of anhydrous ethanol to obtain 9.5g of white solid, wherein the GC content is 99.7%, and the yield is 85%.
5) Synthesis of HCLC-12K
0.7 is added into a 100ml reaction bottleg60%NaH、5g HCLC-12K-1、50ml DMF，N2Heating to 60 ℃ for reaction for 1h, adding 3.0g of HCLC-12K-3, reacting at 60 ℃ for 1h, adding 100ml of water and 200ml of ethyl acetate for extraction, washing with water, washing with brine, drying, concentrating, passing through a silica gel column, eluting with 5:1 petroleum ether and ethyl acetate, evaporating the solvent of the chromatographic solution by using a rotary evaporator to obtain 6.4g of colorless oily matter, recrystallizing with 15ml of toluene and 20ml of ethanol for four times to obtain 2.9g of white solid, and performing GC: 99.6% and a yield of 42%.
1H NMR(300MHz,CDCl3)δ7.94(dd,J=15.0,10.1Hz,1H),7.71(dd,J=16.0,3.0Hz,1H),7.62–7.53(m,2H),7.36–7.28(m,,2H),7.08–6.97(m,3H),6.95–6.76(m,6H),2.61(t,J=15.5Hz,2H),1.74–1.55(m,2H),0.94(t,J=13.2Hz,3H)。
Example 3
The synthetic route of the compound HCLC-12M prepared is shown below,
the specific process steps are as follows:
1) synthesis of HCLC-12M-1
A250 mL dry clean single-neck bottle was charged with 4g of p-bromophenol, 7.8g of [4, 4-difluoro- (3,4, 5-trifluorophenoxy) methyl]-3, 5-difluorophenylboronic acid, 4.8g of anhydrous sodium carbonate, 25mL of deionized water, 100mL of toluene, and 25mL of anhydrous ethanol, purged with argon, and then 0.5g of Pd [ P (Ph)3]4. Heating and refluxing for 12h under the protection of argon, cooling the reaction liquid, separating the liquid, evaporating the organic phase to remove toluene, passing through a silica gel column, eluting with 3:1 petroleum ether and ethyl acetate, evaporating the solvent from the chromatographic solution by using a rotary evaporator to obtain 9.2g of light yellow solid, and recrystallizing the crude product twice by using 20mL of absolute ethyl alcohol to obtain 8.1g of white solid, wherein the GC content is 99.6%, and the yield is 87%.
2) Synthesis of HCLC-12M
A100 ml reaction flask was charged with 0.7g60% NaH, 5g HCLC-12M-1 and 50ml DMF, N2Heating to 60 ℃ for reaction for 1h, adding 2.6g of HCLC-12K-3, reacting at 60 ℃ for 1h, adding 100ml of water and 200ml of ethyl acetate for extraction, washing with water, washing with brine, drying, concentrating, passing through a silica gel column, eluting with 5:1 petroleum ether and ethyl acetate, evaporating the solvent of the chromatographic solution by using a rotary evaporator to obtain 6.9g of colorless oily matter, and recrystallizing with 20ml of petroleum ether and 20ml of ethanol for four times to obtain 2.9g of white solid, and performing GC: 99.6%, yield 39%.
1H NMR(300MHz,CDCl3)δ7.62–7.53(m,2H),7.29–7.35(m,2H),7.06–6.97(m,2H),6.93–6.76(m,6H),2.61(t,J=15.6Hz,2H),1.74–1.55(m,2H),0.94(t,J=13.2Hz,3H)。
Example 4
The synthetic route of the prepared compound HCLC-12N is shown as follows,
when synthesizing HCLC-12N-1, according to the method for synthesizing HCLC-12M-1, 3-fluoro-4-bromophenol is used to replace p-bromophenol for synthesis, and then according to the method for synthesizing compound HCLC-12M, white solid HCLC-12N can be obtained.
1H NMR(300MHz,CDCl3)δ7.62-7.57(m,1H),7.27-7.09(m,5H),6.95-6.83(m,4H),6.53-6.62(m,1H),2.62(t,J=15.6Hz,2H),1.68-1.55(m,2H),0.93(t,J=13.2Hz,3H)。
Example 5 below is the results of a performance test of a liquid crystal composition of the invention:
the abbreviated codes of the test items in the following examples are as follows:
cp (. degree. C.): clearing points (nematic-isotropic phase transition temperature)
Eta: flow viscosity (mm)2·s-120 ℃ unless otherwise stated)
Δ n: optical anisotropy (589 nm, 20 ℃ C.)
Δ ε: dielectric anisotropy (1 KHz, 25 ℃ C.)
Example 5
Table 2 shows the liquid crystal compositions of HCLC-12K and HCLC-12M and the corresponding parameters obtained:
Claims (15)
1. A compound of formula (I):
wherein,
R1and R2Identical or different, each independently selected from the group consisting of-H, -F, -Cl, -CN, -NCS, -SCN, -OCN, -NCO,
A halogenated or non-halogenated linear or branched alkyl or alkoxy group of 1 to 20 carbon atoms and a halogenated or non-halogenated linear or branched alkenyl or alkenyloxy group of 2 to 20 carbon atoms, wherein, in said R1And said R2At least one of-CH2May be substituted by-O-, -S-, -SiH2-、-CH=CH-、-C≡C-、-CF=CF-、-CH=CF-、
-CO-O-or-O-CO-substitution, with the proviso that the heteroatoms are not directly linked to one another;
ring A1、A2、A3、A4、A5And A6Are the same or different and are each independently selected from the group consisting of
A cyclic structure of the group;
optionally, the cyclic structure further conforms to at least one of the following a), b), c) and d):
a) one or more hydrogen atoms in the cyclic structure may be replaced by-D, -F, -Cl, -CN, -CF3、-OCF3、-CH2F、-OCH2F、-CF2H、-OCF2H、-OCH3or-CH3Replacement;
b) one or more-CH in the cyclic structure2-by-O-, -SiH2-, -S-or-CO-substitution, with the proviso that the heteroatoms are not directly connected to one another;
c) in the cyclic structure, one or more-CH-in the aromatic ring structure may be replaced by N;
d) one or more of the ring structures
Can be covered with
Replacement;
Z1、Z3、Z4and Z5The same or different, each independently selected from the group consisting of carbon-carbon single bond, -CO-O-, -CF2O-、-CH2O-、-OCH2-、-CH2CH2-、-CF2CH2-、-CF=CF-、-CH=CH-、-CH=CF-、-C2F4-、-(CH2)4-、-(CF2)4-、-OCF2CF2O-、-CF2CF2CF2O-、-CH2CH2CF2O-、-OCH2CF2O-、-CH2CF2OCH2-、-CH=CHCF2O-、-CF2OCH=CH-、-CF2OCF=CH-、-CF2OCH=CF-、-CF=CFCF2O-、-CF2OCF=CF-、-CH=CHCH2CH2-、-CH2CH=CHCH2-、-C2H4OCH2-、-OCH2CH2CH2-, -CF = CF = CF-, -C.ident.C-CF = CF-C.ident.C-, -CF = CF-C.ident.C-CF = CF-and-C.ident.C-CF2O-;
a is 0 or 1, b, c and d are the same or different and are each independently 0, 1 or 2.
2. A compound of claim 1, wherein R is1And R2The same or different, each independently selected from the group consisting of H, -F, -Cl, -CN, -NCS,
A halogenated or unsubstituted linear or branched alkyl or alkoxy group of 1 to 10 carbon atoms and a halogenated or non-halogenated linear or branched alkenyl or alkenyloxy group of 2 to 10 carbon atoms, wherein, in said R1And stationR is2At least one of-CH2May be substituted by-O-, -CH = CH-, -C.ident.C-, -CF = CF-, -CH = CF-,
or-CO-O-substitution, provided that the heteroatoms are not directly linked to one another.
3. The compound of claim 1, wherein ring a is1、A2、A3、A4、A5And A6Are the same or different and are each independently selected from the group consisting of
Group (d) of (a).
4. The compound of claim 3, wherein ring A is1、A2、A3、A4、A5And A6Each independently of the other is selected from
A cyclic structure of the group.
5. The compound of claim 1, wherein Z is1、Z3、Z4And Z5The same or different, each being independentSelected from-CO-O-, -CF2O-、-CH2O-、-OCH2-、-CH2CH2-、-CF=CF-、-CH=CH-、-(CH2)4-、-C2F4-、-(CF2)4-、-OCF2CF2O-、-CF=CFCF2O-, -C.ident.C-and carbon-carbon single bonds.
6. A compound according to claim 5, wherein Z is1、Z3、Z4And Z5Each independently of the others selected from the group consisting of-CO-O-, -CF2O-、-CH2O-、-CH2CH2-、-CF=CF-、-CH=CH-、-C2F4-、-(CH2)4-、-(CF2)4-、-OCF2CF2O-、-CF=CFCF2O-, -C.ident.C-and carbon-carbon single bonds.
7. The compound of claim 6, wherein Z is1、Z3、Z4And Z5Each independently of the others from the group consisting of-CF2O-、-CH2O-、-CH2CH2-、-CF=CF-、-CH=CH-、-CF=CFCF2O-, -C.ident.C-and carbon-carbon single bonds.
8. The compound of claim 1, wherein a is 0 or 1; b + c + d is less than or equal to 3.
9. The compound of claims 1-8, wherein the compound is selected from the group consisting of:
wherein,
R1and R2The same or different, each independently selected from the group consisting of H, -F, -Cl, -CN, and a halogenated or unsubstituted, linear or branched alkyl or alkoxy group of 1 to 7 carbon atoms, wherein, in said R1And said R2At least one of-CH2May be substituted by-O-, -CH = CH-, -C.ident.C-, -CF = CF-, -CH = CF-,
or-CO-O-substitution, provided that the heteroatoms are not directly linked to one another.
10. Liquid crystal composition comprising at least one compound according to one of claims 1 to 9.
11. Liquid crystal composition according to claim 10, characterized in that it comprises one to five liquid crystal compounds according to one of claims 1 to 10, preferably the liquid crystal mixture comprises two to four liquid crystal compounds according to one of claims 1 to 10.
12. The liquid crystal composition of claim 10, further comprising at least one liquid crystal compound of formula ii:
wherein,
R3and R4The same or different, each independently selected from the group consisting of-H, -F, -Cl, -CN, -NCS, -SCN, -OCN, -NCO, -OCH = CF2A halogenated or non-halogenated linear or branched alkyl or alkoxy group of 1 to 20 carbon atoms and a halogenated or non-halogenated linear or branched alkenyl or alkenyloxy group of 2 to 20 carbon atoms, wherein in said R3And said R4At least one of-CH2May be substituted by-O-, -S-, -SiH2-、-CH=CH-、-C≡C-、-CF=CF-、-CH=CF-、
-CO-O-or-O-CO-substitution, with the proviso that the heteroatoms are not directly linked to one another;
B1、B2and B3And B4Are the same or different and are each independently selected from the group consisting of
2, 3-difluoro-1, 4-phenylene, 3-fluoro-1, 4-phenylene, 2-chloro-3-fluoro-1, 4-phenylene, 2, 6-difluoro-1, 4-phenylene, 3, 5-difluoro-1, 4-phenylene, indan-2, 5-diyl, piperidine-1, 4-diyl, naphthalene-2, 6-diyl, decahydronaphthalene-2, 6-diyl, and 1,2,3, 4-tetrahydronaphthalene-2, 6-diyl, wherein said
One or two non-adjacent-CH2-may be replaced by-O-or-S-, said
One or more of H may each independently be substituted by F, said
One or two non-adjacent-CH-s may be replaced by N, said
One or two non-adjacent-CH2May be replaced by O, saidEach of the one or more H may be independently substituted with F;
Y1、Y2and Y3The same or different, each independently selected from the group consisting of-OCO-, -CO-O-, -CF2O-、-CH2O-、-OCH2-、-CH2CH2-、-CF2CH2-、-CF=CF-、-CH=CH-、-CH(CH3)CH2-、-CH2CH(CH3)-、-(CH2)3O-、-O(CH2)3-、-COS-、-SCO-、-CH=CF-、-C2F4-、-(CH2)4-、-C4F8-、-OCF2CF2O-、-CF2CF2CF2O-、-CH2CH2CF2O-、-CH2CF2OCH2-、-CH=CHCF2O-、-CF2OCH=CH-、-CF2OCF=CH-、-CF2OCH=CF-、-CF=CFCF2O-、-CF2OCF=CF-、-CH=CHCH2CH2-、-C2H4OCH2-、-CH2CH=CHCH2-、-OCH2CH2CH2-、-CF=CF-CF=CF-、-C≡C-CF=CF-、-C≡C-CF=CF-C≡C-、-CF=CF-C≡C-CF=CF-、-C≡C-CF2O-, -C ≡ C-and a single bond, wherein in the Y1And Y2Any one of-CH2May be-SiH2-substitution;
m, n and p are the same or different and are each independently 0, 1 or 2.
13. The liquid crystal composition of claim 12, wherein the liquid crystal compound of formula (ii) is selected from the group consisting of:
14. the liquid crystal composition of claims 10-13, wherein the liquid crystal composition comprises 5-50% by weight of the total weight of the liquid crystal composition of the compound of formula i; 50-95% of the compound of formula II based on the total weight of the liquid crystal composition, preferably, the liquid crystal composition comprises 10-30% of the compound of formula (I) based on the total weight of the liquid crystal composition; 70-90% of the compound of the general formula (II) based on the total weight of the liquid crystal composition.
15. A liquid crystal display comprising the liquid crystal composition according to any one of claims 10 to 14.
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| CN109061976A (en) * | 2017-06-13 | 2018-12-21 | 江苏和成显示科技有限公司 | A kind of liquid crystal display device and its application |
| CN109085725A (en) * | 2017-06-13 | 2018-12-25 | 江苏和成显示科技有限公司 | A kind of liquid crystal display device and its application |
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Non-Patent Citations (2)
| Title |
|---|
| ALEXEI I.MUSHTA ET AL.: "Synthesis and some chemical properties of 1-aryloxy-2-chloro-1,2-difluoroethenes", 《JOURNAL OF FLUORINE CHEMISTRY》 * |
| JUSTIN D.MOODY ET AL.: "Synthesis of internal fluorinated alkenes via facile aryloxylation of substituted phenols with aryl trifluorovinyl ethers", 《ORGANIC & BIOMOLECULAR CHEMISTRY》 * |
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| CN103361074B (en) * | 2013-07-01 | 2015-08-26 | 江苏和成新材料有限公司 | Comprise polyfluoro for the liquid crystalline cpd of unsaturated indenes ring and composition thereof and application |
| CN109061976A (en) * | 2017-06-13 | 2018-12-21 | 江苏和成显示科技有限公司 | A kind of liquid crystal display device and its application |
| CN109085725A (en) * | 2017-06-13 | 2018-12-25 | 江苏和成显示科技有限公司 | A kind of liquid crystal display device and its application |
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