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
- Publication number
- 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
- Authority
- CN
- China
- Prior art keywords
- och
- independently
- group
- compound
- liquid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 76
- 150000001875 compounds Chemical class 0.000 title claims abstract description 57
- 239000000203 mixture Substances 0.000 title claims abstract description 38
- 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 2
- 239000007788 liquid Substances 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 150000001721 carbon Chemical group 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
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 8
- 101150065749 Churc1 gene Proteins 0.000 claims description 8
- 102100038239 Protein Churchill Human genes 0.000 claims description 8
- -1 fluoro-1,4-phenylene Chemical group 0.000 claims description 6
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 5
- 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 description 3
- 125000005734 2-chloro-3-fluoro-1,4-phenylene group Chemical group [H]C1=C([H])C([*:1])=C(Cl)C(F)=C1[*:2] 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 8
- 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
- 239000000126 substance Substances 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 229910000104 sodium hydride Inorganic materials 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000010792 warming Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229960000935 dehydrated alcohol Drugs 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 238000005406 washing Methods 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
- 210000002858 crystal cell Anatomy 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 238000010189 synthetic method Methods 0.000 description 5
- XLEILMCZKMFZTO-UHFFFAOYSA-N 2,3-difluorooxirane Chemical class FC1OC1F XLEILMCZKMFZTO-UHFFFAOYSA-N 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000010992 reflux Methods 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
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229960004756 ethanol Drugs 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000000605 extraction Methods 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
- 150000003839 salts Chemical class 0.000 description 3
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004990 Smectic liquid crystal Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000003810 ethyl acetate extraction Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-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
- 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
- 239000007818 Grignard reagent Substances 0.000 description 1
- 239000004991 Lytropic liquid crystal Substances 0.000 description 1
- 238000006411 Negishi coupling reaction Methods 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- 230000018199 S phase Effects 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
- OPPWASLOVKWHCT-UHFFFAOYSA-N boric acid;phenol Chemical compound OB(O)O.OC1=CC=CC=C1 OPPWASLOVKWHCT-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical compound FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol group Chemical group [C@@H]1(CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)[C@H](C)CCCC(C)C HVYWMOMLDIMFJA-DPAQBDIFSA-N 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000008447 perception Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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 composition that the present invention relates to a kind of liquid crystalline cpd and comprise described liquid crystalline cpd more particularly, the present invention relates to a kind of novel liquid crystalline cpd that contains the difluoroethylene ethers and the liquid-crystal composition that comprises described liquid crystalline cpd.
Background technology
On the physics material is divided into three-state, i.e. solid-state, liquid state and gaseous state.At occurring in nature, that most of material variation with temperature only presents is solid-state, liquid state and three kinds of states of gaseous state, liquid crystal (Liquid Crystal) is a kind of new state of matter that is different from common solid-state, liquid state and gaseous state, it is the state of matter that can have liquid and crystal characteristic in certain temperature range concurrently, also be called mesomorphic phase or intermediary's phase, therefore be called again the 4th attitude of material.
The kind of liquid crystal is a lot, and the liquid crystal with synthetic that naturally exists reaches thousands of kinds, but they are organic compound basically.Come inducing classification by the condition that mesomorphic phase forms, liquid crystal can be divided into thermotropic liquid crystal, lytropic liquid crystals, induction liquid crystal and stream and cause liquid crystal.
At present, all be thermotropic liquid crystal basically for the liquid crystal material that shows.Thermotropic liquid crystal is because of the difference of molecular arrangement order state, can be divided into smectic phase (Smectic) liquid crystal (claim not only layered liquid crystal), nematic phase (Nematic) liquid crystal (but also claiming nematic liquid crystal), cholesteryl phase (Cholestevic) liquid crystal (being also referred to as the spirrillum liquid crystal).The physical properties of these phases is known.Be used for the molecular characterization of the compound of field of electro-optics, a rigid backbone is normally arranged, it comprises 1 of for example connection, 4-phenylene or 1,4-cyclohexylidene or heterocyclic system, its each other as far as possible away from the position on by so-called mesomorphic group, replace such as alkyl, alkoxyl group or cyano group.
Be used for the liquid crystal media in electrooptics field by the compositions of mixtures of these compounds, and wherein also use the compound that does not have the conversion from crystal to the mesomorphic phase change.Classify by the liquid-crystal display mode, liquid crystal compound can be divided into dynamic scattering mode (DS type), guest-host type (GH type), twisted nematic (TN type), super-twist nematic (STN type), film transistor type (TFT type) and strong dielectric type (FLC type) etc.Liquid crystal material has been widely used in the making of the liquid crystal display device such as robot calculator, meter device, instrument panel for motor vehicle, electronic memo, mobile telephone, computer, televisor at present.
Up to now, all this used liquid crystal materials have synthesized multiple compounds, visual its display mode or type of drive and uses thereof and be suitable for.Can also strengthen year by year the demand that improves the liquid crystal display device performance on the other hand, for satisfying this demand, need the continual exploitation novel liquid crystal compound.
Summary of the invention
The purpose of this invention is to provide a kind of novel liquid crystalline cpd that contains the difluoroethylene ethers.
Another object of the present invention provides a kind of synthetic method of synthetic described liquid crystalline cpd.
Another purpose of the present invention provides a kind of composition that comprises described liquid crystalline cpd.
A further object of the present invention provides the application of a kind of described liquid-crystal composition in liquid crystal cell, can be used for containing the liquid crystal cell of liquid crystal media, such as the liquid crystal cell of the display formats such as TN, STN, TFT, VA, ECB, OCB, LCP, PDLC, BiNem, LC LENS, FFS and IPS.
One aspect of the present invention provides a kind of novel liquid crystal compound, and described compound has the structure shown in the logical formula I:
Wherein,
R
1And R
2Identical or not identical, be selected from independently of one another by-H ,-F ,-Cl ,-CN ,-NCS ,-SCN ,-OCN ,-NCO,
The halo of 1-20 carbon atom or not halo or the not thiazolinyl of the straight or branched of halo or the group that alkene oxygen base forms of the alkyl of the straight or branched of halo or alkoxyl group and 2-20 carbon atom, wherein, at described R
1With described R
2In at least one-CH
2-can by-O-,-S-,-SiH
2-,-CH=CH-,-C ≡ C-,-CF=CF-,-CH=CF-,
-CO-O-or-O-CO-substitutes, its prerequisite is that heteroatoms directly is not connected to each other;
Ring A
1, A
2, A
3, A
4, A
5And A
6Identical or different, be selected from independently of one another by
The ring texture of the group that forms;
Wherein,
Described ring texture can also meet following a), b), c) and d) at least one:
A) the one or more hydrogen atoms in the described ring texture can by-D ,-F ,-Cl ,-CN ,-CF
3,-OCF
3,-CH
2F ,-OCH
2F ,-CF
2H ,-OCF
2H ,-OCH
3Or-CH
3Substitute;
B) one or more-CH in the described ring texture
2-quilt-O-,-SiH
2-,-S-or-CO-substitutes, its prerequisite is that heteroatoms directly is not connected to each other;
C) in described ring texture, in the aromatic ring structure one or more-CH-can substitute by N;
D) one or more in the described ring texture
Can by
Substitute;
Z
1, Z
3, Z
4And Z
5Identical or different, be selected from independently of one another by carbon-carbon single bond ,-CO-O-,-CF
2O-,-CH
2O-,-OCH
2-,-CH
2CH
2-,-CF
2CH
2-,-CF=CF-,-CH=CH-,-CH=CF-,-C
2F
4-,-(CH
2)
4-,-(CF
2)
4-,-OCF
2CF
2O-,-CF
2CF
2CF
2O-,-CH
2CH
2CF
2O-,-OCH
2CF
2O-,-CH
2CF
2OCH
2-,-CH=CHCF
2O-,-CF
2OCH=CH-,-CF
2OCF=CH-,-CF
2OCH=CF-,-CF=CFCF
2O-,-CF
2OCF=CF-,-CH=CHCH
2CH
2-,-CH
2CH=CHCH
2-,-C
2H
4OCH
2-,-OCH
2CH
2CH
2-,-CF=CF=CF=CF-,-C ≡ C-CF=CF-,-C ≡ C-CF=CF-C ≡ C-,-C ≡ C-,-CF=CF-C ≡ C-CF=CF-and-C ≡ C-CF
2The group that O-forms;
A be 0 or 1, b, c and d identical or different, be 0,1 or 2 independently of one another.
In some preferred embodiments, R
1And R
2Identical or different, be selected from independently of one another by H ,-F ,-Cl ,-CN ,-NCS,
The halo of the halo of 1-10 carbon atom or the alkyl of unsubstituted straight or branched or alkoxyl group and 2-10 carbon atom or the group that forms of the thiazolinyl of the straight or branched of halo or alkene oxygen base not, wherein, at described R
1With described R
2In at least one-CH
2-can by-O-,-CH=CH-,-C ≡ C-,-CF=CF-,-CH=CF-,
Or-CO-O-is alternative, and its prerequisite is that heteroatoms directly is not connected to each other.
In some preferred embodiments, ring A
1, A
2, A
3, A
4, A
5And A
6Identical or different, be selected from independently of one another by
The group that forms.
In some preferred embodiments, ring A
1, A
2, A
3, A
4, A
5And A
6Be independently from each other separately by
The ring texture of the group that forms.
In some preferred embodiments, Z
1, Z
3, Z
4And Z
5Identical or different, be selected from independently of one another by-CO-O-,-CF
2O-,-CH
2O-,-OCH
2-,-CH
2CH
2-,-CF=CF-,-CH=CH-,-(CH
2)
4-,-C
2F
4-,-(CF
2)
4-,-OCF
2CF
2O-,-CF=CFCF
2O-,-group that C ≡ C-and carbon-carbon single bond form.
In some preferred embodiments, Z
1, Z
3, Z
4And Z
5Be independently from each other separately by-CO-O-,-CF
2O-,-CH
2O-,-CH
2CH
2-,-CF=CF-,-CH=CH-,-C
2F
4-,-(CH
2)
4-,-(CF
2)
4-,-OCF
2CF
2O-,-CF=CFCF
2O-,-group that C ≡ C-and carbon-carbon single bond form.
In some preferred embodiments, Z
1, Z
3, Z
4And Z
5Be independently from each other separately by-CF
2O-,-CH
2O-,-CH
2CH
2-,-CF=CF-,-CH=CH-,-CF=CFCF
2O-,-group that C ≡ C-and carbon-carbon single bond form.
In some preferred embodiments, a is 0 or 1; B+c+d≤3.
In some preferred embodiments, the compound of logical formula I is particularly preferably one or more in the group that following compound forms:
Wherein,
R
1And R
2Identical or different, be selected from independently of one another by H ,-F ,-Cl ,-halo or the alkyl of unsubstituted straight or branched or the group that alkoxyl group forms of CN and 1-7 carbon atom, wherein, at described R
1With described R
2In at least one-CH
2-can by-O-,-CH=CH-,-C ≡ C-,-CF=CF-,-CH=CF-,
Or-CO-O-is alternative, and its prerequisite is that heteroatoms directly is not connected to each other.
Another object of the present invention provides a kind of method for preparing above-claimed cpd, comprises the steps:
The compound of general formula (III-2) and sodium hydride form sodium salt, again with the tetrafluorodibromoethane reaction, obtain the compound of general formula (III-1); The compound process Lithium Aluminium Hydride reduction of general formula (III-1) obtains the compound of logical formula III.
The compound of logical formula III and sodium hydride form sodium salt, and the compound with general formula (IV) reacts again, obtains the compound of logical formula I.
The compound of general formula (III-2) and logical formula III mainly is by commercially available intermediate or the synthetic method known altogether is synthetic obtains, and the synthetic method of wherein knowing altogether comprises that esterification, witting reaction, carbon-carbon cross coupling reaction (Suzuki coupling, Negishi coupling, Heck coupling, Sonogashira coupling and transition metal-catalyzed Grignard reagent cross-coupling reaction etc.) and reduction reaction etc. obtain.
The process of principal reaction is as follows:
1) in the anhydrous dimethyl formamide solvent; under the argon shield; the compound that adds general formula (III-2); add sodium hydride in batches; be warming up to 60 ℃ of reactions 1 hour; after being cooled to room temperature, drip the dimethyl formamide solution of ethyl bromide difluoride, room temperature reaction obtained the compound of general formula (III-1) in 12 hours again.
2) compound dissolution of general formula (III-1) adds zinc powder under the nitrogen protection in anhydrous acetonitrile, and the 10 ~ 12h that refluxes obtains the compound of logical formula III.
3) compound dissolution of logical formula IV is in the anhydrous dimethyl formamide solvent, N
2Add sodium hydride under the lower protection, be warming up to 60 ℃ of reaction 1h, add the compound of general formula (III-1), 60 ℃ are reacted 1h, obtain the compound of logical formula V.
Another purpose of the present invention provides a kind of liquid-crystal composition, comprises the described liquid crystalline cpd of one or more logical formula I.
In some embodiments, described liquid-crystal composition comprises a kind of to five kinds of described liquid crystalline cpds of logical formula I, is preferably described liquid-crystal composition and comprises two kinds to the four kinds described liquid crystalline cpds of logical formula I.
Can be usually known mesomorphic compound according to the other blending ingredients of liquid-crystal composition of the present invention, can mixedly form the compound of mesomorphic phase with its pure state or with other components.Some this type of compound for example is being mentioned among D E1804894 and the CN1158602A.Preferably, in some embodiments, described liquid-crystal composition also comprises the liquid crystalline cpd of at least a logical formula II:
Wherein,
R
3And R
4Identical or different, be selected from independently of one another by-H ,-F ,-Cl ,-CN ,-NCS ,-SCN ,-OCN ,-NCO ,-OCH=CF
2With the halo of 1-20 carbon atom or the group that forms of the alkyl of the straight or branched of halo or alkoxyl group not, wherein, at described R
3With described R
4In at least one-CH
2-can by-O-,-S-,-SiH
2-,-CH=CH-,-C ≡ C-,-CF=CF-,-CH=CF-,
-CO-O-or-O-CO-substitutes, its prerequisite is that heteroatoms directly is not connected to each other;
B
1, B
2And B
3And B
4Identical or different, be selected from independently of one another by
2,3-, two fluoro-Isosorbide-5-Nitrae-phenylenes, 3-fluoro-Isosorbide-5-Nitrae-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2-fluoro-Isosorbide-5-Nitrae-phenylene, 2,6-two fluoro-1,4-phenylene, 3,5-two fluoro-Isosorbide-5-Nitrae-phenylenes, indane-2,5-two bases, piperidines-Isosorbide-5-Nitrae-two base, naphthalene-2,6-two bases, perhydronaphthalene-2,6-two bases and 1,2,3,4-naphthane-2, the group that 6-two bases form, described
In one or two non-conterminous-CH
2-can by-O-or-S-substitutes, and is described
Upper one or more H can be replaced by F independently of one another, and is described
In one or two non-conterminous-CH-can be substituted by N, described
In one or two non-conterminous-CH
2-can be substituted by O, described
Upper one or more H can be replaced by F independently of one another;
Y
1, Y
2And Y
3Identical or different, be selected from independently of one another by-OCO-,-CO-O-,-CF
2O-,-CH
2O-,-OCH
2-,-CH
2CH
2-,-CF
2CH
2-,-CF=CF-,-CH=CH-,-CH (CH
3) CH
2-,-CH
2CH (CH
3)-,-(CH
2)
3O-,-O (CH
2)
3-,-COS-,-SCO-,-CH=CF-,-C
2F
4-,-(CH
2)
4-,-C
4F
8-,-OCF
2CF
2O-,-CF
2CF
2CF
2O-,-CH
2CH
2CF
2O-,-CH
2CF
2OCH
2-,-CH=CHCF
2O-,-CF
2OCH=CH-,-CF
2OCF=CH-,-CF
2OCH=CF-,-CF=CFCF
2O-,-CF
2OCF=CF-,-CH=CHCH
2CH
2-,-C
2H
4OCH
2-,-CH
2CH=CHCH
2-,-OCH
2CH
2CH
2-,-CF=CF-CF=CF-,-C ≡ C-CF=CF-,-C ≡ C-CF=CF-C ≡ C-,-CF=CF-C ≡ C-CF=CF-,-C ≡ C-CF
2O-,-group that C ≡ C-and singly-bound form, wherein, at described Y
1And Y
2In any one-CH
2-can be by-SiH
2-substitute;
M, n and p are identical or different, are 0,1 or 2 independently of one another.
Described liquid crystalline cpd is selected from the group that is comprised of following compound:
In some embodiments, described liquid-crystal composition comprises that accounting for described liquid-crystal composition gross weight 5-50% leads to the described compound of formula I; Account for the logical described compound of formula II of described liquid-crystal composition gross weight 50-95%, preferably account for the logical described compound of formula I of described liquid-crystal composition gross weight 10-30%; Account for the logical described compound of formula II of described liquid-crystal composition gross weight 70-90%.
Another purpose of the present invention provides a kind of liquid-crystal display, and described liquid-crystal display comprises the liquid-crystal composition that contains liquid crystalline cpd of the present invention.
A further object of the present invention provides a kind of novel liquid crystalline cpd that contains the difluoroethylene ethers, it is suitable as the composition of liquid crystal media, can be applicable to contain the liquid crystal cell of liquid crystal media, such as the liquid crystal cell of the display formats such as TN, STN, TFT, VA, ECB, OCB, LCP, PDLC, BiNem, LC LENS, FFS and IPS.
The novel liquid crystalline cpd that contains six hydrogen indenes classes provided by the invention has good chemistry and physical properties, has lower viscosity than other liquid crystal material, larger optical anisotropy and larger dielectric anisotropy.
Embodiment
Below with reference to specific embodiments the present invention is described.Need to prove, the following examples are example of the present invention, only are used for illustrating the present invention, and are not used for limiting the present invention.In the situation that do not depart from purport of the present invention or scope, can carry out the present invention and conceive interior other combination and various improvement.
For ease of expressing, below among each embodiment, the unit structure of liquid crystalline cpd is with the listed coded representation of table 1:
The unit structure code of table 1 liquid crystalline cpd
Take the compound of following structural formula as example:
This structural formula is such as by code listed in Table 1 expression, and then can be expressed as: 3PUQUF, the Q in the code represent difluoro methylene oxygen base; C in the code represents cyclohexyl; U in the code represents 2,5-, two fluoro phenylenes.
Embodiment 1
The synthetic route of the compound H CLC-12 of preparation is as follows,
Its concrete technology step is as follows:
1) HCLC-12-2's is synthetic
The 500mL there-necked flask adds 21.8g the third ring phenol, 200mL dimethyl formamide (DMF); dissolving adds 8g60% sodium hydride (NaH) under the nitrogen protection, be warming up to 60 ℃ of reaction 1h; be cooled to 30 ℃, drip tetrafluorodibromoethane 31.2g, add room temperature reaction 12h.Add ethyl acetate 200ml, water 200ml, layering, water layer is used the 200ml ethyl acetate extraction again, merges organic layer, wash 2 times, the salt solution washed twice, the dry crude product 38.5g that concentrates to get, the thick post of crossing of sherwood oil obtains 34g.GC:98.8%, yield 85.6%.
2) HCLC-12-1's is synthetic
Add 20gHCLC-12-2,6g zinc powder and 100ml acetonitrile in the 250ml reaction flask, refluxed under nitrogen 11h is cooled to room temperature, and suction filtration is spin-dried for to get crude product.After crude product added petroleum ether dissolution, sherwood oil stripped post, was spin-dried for to get product 13.4g.Yield 89%, GC:86.3%.
3) HCLC-12's is synthetic
Add 1.9g60% sodium hydride NaH, 3.2g2 in the 250ml reaction flask, 3-two fluoro-4-thanatol and 100mlDMF, N
2Under be warming up to 60 ℃ the reaction 1h, add 6g HCLC-12-1,60 ℃ of reaction 6h add water 300ml, ethyl acetate 200ml extraction, washing, the salt water washing, drying, concentrated, sherwood oil ether column chromatography gets the 8.4g colorless oil, obtain water white transparency oily thing 1.97g, GC:99.7%, yield 25% with 10ml ethanol for four times at-30 ℃ of lower recrystallizations again.
1H?NMR(300MHz,CDCl
3)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)。
Embodiment 2
The synthetic route of the compound H CLC-12K of preparation is as follows,
[4,4-, two fluoro-(3,4,5-trifluoromethoxy phenoxy base) methyl]-3,5-difluorobenzene boric acid can be with prior art perception method synthetic (but its synthetic method reference European Journal of Organic Chemistry, 2008, V20p3479 – 3487) altogether.
Its concrete technology step is as follows:
1) HCLC-12K-4's is synthetic
The 250mL there-necked flask adds 15g n-propyl phenol and 150mL DMF, and dissolving adds 4.4g sodium hydride (NaH) under the nitrogen protection, is warming up to 60 ℃ of reaction 1h, is cooled to 30 ℃, drips tetrafluorodibromoethane 36g, adds room temperature reaction 12h.Add ethyl acetate 200ml, water 200ml, layering, water layer is used the 200ml ethyl acetate extraction again, merges organic layer, wash 2 times, the salt solution washed twice, the dry crude product 30g that concentrates to get, the thick post of crossing of sherwood oil obtains 22.5g.GC:96.5%, yield 64.8%.
2) HCLC-12K-3's is synthetic
Add 22.5g HCLC-12K-4,10g zinc powder and 150ml acetonitrile in the 250ml reaction flask, refluxed under nitrogen 11h is cooled to room temperature, and suction filtration is spin-dried for to get crude product.Crude product is crossed post after adding petroleum ether dissolution, is spin-dried for to get product 9.6g.Yield 62.3%, GC:85.8%.
3) HCLC-12K-2's is synthetic
Add 20g para hydroxybenzene boric acid, 43.5g3-fluoro-4-iodine tribromophenyl, 30.5g anhydrous sodium carbonate, 144mL deionized water, 160mL toluene and 80mL dehydrated alcohol in the single port bottle of 1L dried and clean, after the usefulness argon replaces is emptying, add 0.5g Pd[P (Ph)
3]
4Reflux 6h under the argon shield; separatory after the reaction solution cooling, the 20g anhydrous sodium sulfate drying, organic phase is steamed to the greatest extent toluene; cross silicagel column; with sherwood oil and the eluent ethyl acetate of 3:1, chromatographic solution steams to the greatest extent solvent with Rotary Evaporators, obtains the 42g light yellow solid; crude product is used 100mL dehydrated alcohol and 100ml toluene recrystallization again; obtain the 31.5g white solid, GC content 99.6%, yield 82%.
4) HCLC-12K-1's is synthetic
Add 6g HCLC-12K-2,8g[4 in the single port bottle of 250mL dried and clean, 4-two fluoro-(3,4,5-trifluoromethoxy phenoxy base) methyl]-3,5-difluorobenzene boric acid, 4.8g anhydrous sodium carbonate, 25mL deionized water, 100mL toluene and 25mL dehydrated alcohol, after emptying with argon replaces, add 0.5g Pd[P (Ph)
3]
4Reflux 12h under the argon shield; separatory after the reaction solution cooling; organic phase is steamed to the greatest extent toluene, crosses silicagel column, with sherwood oil and the eluent ethyl acetate of 3:1; chromatographic solution steams to the greatest extent solvent with Rotary Evaporators; obtain the 11g light yellow solid, crude product is used 20mL toluene and 10mL dehydrated alcohol recrystallization again, obtains the 9.5g white solid; GC content 99.7%, yield 85%.
5) HCLC-12K's is synthetic
Add 0.7g60%NaH, 5g HCLC-12K-1,50ml DMF in the 100ml reaction flask, N
2Under be warming up to 60 ℃ of reaction 1h, add 3.0gHCLC-12K-3,60 ℃ of reaction 1h, add water 100ml, ethyl acetate 200ml extraction, washing, salt water washing, drying, concentrated, cross silicagel column, sherwood oil and eluent ethyl acetate with 5:1, chromatographic solution steams most solvent with Rotary Evaporators and gets the 6.4g colorless oil, use 15ml toluene, and the 20ml ethyl alcohol recrystallization obtains white solid 2.9g four times again, GC:99.6%, yield 42%.
1H?NMR(300MHz,CDCl
3)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)。
Embodiment 3
The synthetic route of the compound H CLC-12M of preparation is as follows,
Its concrete technology step is as follows:
1) HCLC-12M-1's is synthetic
Add 4g p bromophenol, 7.8g[4 in the single port bottle of 250mL dried and clean, 4-two fluoro-(3,4,5-trifluoromethoxy phenoxy base) methyl]-3,5-difluorobenzene boric acid, 4.8g anhydrous sodium carbonate, 25mL deionized water, 100mL toluene and 25mL dehydrated alcohol, after emptying with argon replaces, add 0.5g Pd[P (Ph)
3]
4Reflux 12h under the argon shield; separatory after the reaction solution cooling; organic phase is steamed to the greatest extent toluene, crosses silicagel column, with sherwood oil and the eluent ethyl acetate of 3:1; chromatographic solution steams to the greatest extent solvent with Rotary Evaporators; obtain the 9.2g light yellow solid, crude product is used 20mL dehydrated alcohol recrystallization twice again, obtains the 8.1g white solid; GC content 99.6%, yield 87%.
2) HCLC-12M's is synthetic
Add 0.7g60%NaH, 5g HCLC-12M-1 and 50ml DMF in the 100ml reaction flask, N
2Under be warming up to 60 ℃ of reaction 1h, add 2.6g HCLC-12K-3,60 ℃ of reaction 1h, add water 100ml, ethyl acetate 200ml extraction, washing, salt water washing, dry, concentrated, cross silicagel column, with sherwood oil and the eluent ethyl acetate of 5:1, chromatographic solution steams to the greatest extent with Rotary Evaporators, and solvent gets the 6.9g colorless oil, obtain white solid 2.9g four times with 20ml sherwood oil and 20ml ethyl alcohol recrystallization again, GC:99.6%., yield 39%.
1H?NMR(300MHz,CDCl
3)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)。
Embodiment 4
The synthetic route of the compound H CLC-12N of preparation is as follows,
According to the method for synthetic HCLC-12M-1, replace p bromophenol synthetic with 3-fluoro-4-bromophenol when synthetic HCLC-12N-1, the synthetic method according to compound H CLC-12M can obtain white solid HCLC-12N again.
1H?NMR(300MHz,CDCl
3)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)。
Following embodiment 5 is the performance test results of liquid-crystal composition of the present invention:
In following examples test event to write a Chinese character in simplified form code name as follows:
Cp(℃): clearing point (to row-isotropic phase transition temperature)
η: kinetic viscosity (mm
2S
-1, 20 ℃, except as otherwise noted)
Δ n: optical anisotropy (589nm, 20 ℃)
Δ ε: dielectric anisotropy (1KHz, 25 ℃)
Embodiment 5
Table 2 is the relevant parameter that HCLC-12K and HCLC-12M are configured to liquid-crystal composition and obtain:
Claims (15)
1. the compound of a kind as logical formula I:
Wherein,
R
1And R
2Identical or not identical, be selected from independently of one another by-H ,-F ,-Cl ,-CN ,-NCS ,-SCN ,-OCN ,-NCO,
The halo of 1-20 carbon atom or not halo or the not thiazolinyl of the straight or branched of halo or the group that alkene oxygen base forms of the alkyl of the straight or branched of halo or alkoxyl group and 2-20 carbon atom, wherein, at described R
1With described R
2In at least one-CH
2-can by-O-,-S-,-SiH
2-,-CH=CH-,-C ≡ C-,-CF=CF-,-CH=CF-,
-CO-O-or-O-CO-substitutes, its prerequisite is that heteroatoms directly is not connected to each other;
Ring A
1, A
2, A
3, A
4, A
5And A
6Identical or different, be selected from independently of one another by
The ring texture of the group that forms;
Selectively, described ring texture also meet following a), b), c) and d) at least one:
A) one or more hydrogen atom in the described ring texture can by-D ,-F ,-Cl ,-CN ,-CF
3,-OCF
3,-CH
2F ,-OCH
2F ,-CF
2H ,-OCF
2H ,-OCH
3Or-CH
3Substitute;
B) one or more-CH in the described ring texture
2-quilt-O-,-SiH
2-,-S-or-CO-substitutes, its prerequisite is that heteroatoms directly is not connected to each other;
C) in described ring texture, in the aromatic ring structure one or more-CH-can substitute by N;
D) one or more in the described ring texture
Can by
Substitute;
Z
1, Z
3, Z
4And Z
5Identical or different, be selected from independently of one another by carbon-carbon single bond ,-CO-O-,-CF
2O-,-CH
2O-,-OCH
2-,-CH
2CH
2-,-CF
2CH
2-,-CF=CF-,-CH=CH-,-CH=CF-,-C
2F
4-,-(CH
2)
4-,-(CF
2)
4-,-OCF
2CF
2O-,-CF
2CF
2CF
2O-,-CH
2CH
2CF
2O-,-OCH
2CF
2O-,-CH
2CF
2OCH
2-,-CH=CHCF
2O-,-CF
2OCH=CH-,-CF
2OCF=CH-,-CF
2OCH=CF-,-CF=CFCF
2O-,-CF
2OCF=CF-,-CH=CHCH
2CH
2-,-CH
2CH=CHCH
2-,-C
2H
4OCH
2-,-OCH
2CH
2CH
2-,-CF=CF=CF=CF-,-C ≡ C-CF=CF-,-C ≡ C-CF=CF-C ≡ C-,-C ≡ C-,-CF=CF-C ≡ C-CF=CF-and-C ≡ C-CF
2The group that O-forms;
A be 0 or 1, b, c and d identical or different, be 0,1 or 2 independently of one another.
2. compound according to claim 1 is characterized in that, R
1And R
2Identical or different, be selected from independently of one another by H ,-F ,-Cl ,-CN ,-NCS,
The halo of the halo of 1-10 carbon atom or the alkyl of unsubstituted straight or branched or alkoxyl group and 2-10 carbon atom or the group that forms of the thiazolinyl of the straight or branched of halo or alkene oxygen base not, wherein, at described R
1With described R
2In at least one-CH
2-can by-O-,-CH=CH-,-C ≡ C-,-CF=CF-,-CH=CF-,
Or-CO-O-is alternative, and its prerequisite is that heteroatoms directly is not connected to each other.
3. compound according to claim 1 is characterized in that, ring A
1, A
2, A
3, A
4, A
5And A
6Identical or different, be selected from independently of one another by
The group that forms.
4. compound according to claim 3 is characterized in that, ring A
1, A
2, A
3, A
4, A
5And A
6Be independently from each other separately by
The ring texture of the group that forms.
5. compound according to claim 1 is characterized in that, Z
1, Z
3, Z
4And Z
5Identical or different, be selected from independently of one another by-CO-O-,-CF
2O-,-CH
2O-,-OCH
2-,-CH
2CH
2-,-CF=CF-,-CH=CH-,-(CH
2)
4-,-C
2F
4-,-(CF
2)
4-,-OCF
2CF
2O-,-CF=CFCF
2O-,-group that C ≡ C-and carbon-carbon single bond form.
6. compound according to claim 5 is characterized in that, Z
1, Z
3, Z
4And Z
5Be independently from each other separately by-CO-O-,-CF
2O-,-CH
2O-,-CH
2CH
2-,-CF=CF-,-CH=CH-,-C
2F
4-,-(CH
2)
4-,-(CF
2)
4-,-OCF
2CF
2O-,-CF=CFCF
2O-,-group that C ≡ C-and carbon-carbon single bond form.
7. compound according to claim 6 is characterized in that, Z
1, Z
3, Z
4And Z
5Be independently from each other separately by-CF
2O-,-CH
2O-,-CH
2CH
2-,-CF=CF-,-CH=CH-,-CF=CFCF
2O-,-group that C ≡ C-and carbon-carbon single bond form.
8. compound according to claim 1 is characterized in that, a is 0 or 1; B+c+d≤3.
9. described compound is characterized in that according to claim 1-8, and described compound is selected from the group that is comprised of following compound:
Wherein,
R
1And R
2Identical or different, be selected from independently of one another by H ,-F ,-Cl ,-halo or the alkyl of unsubstituted straight or branched or the group that alkoxyl group forms of CN and 1-7 carbon atom, wherein, at described R
1With described R
2In at least one-CH
2-can by-O-,-CH=CH-,-C ≡ C-,-CF=CF-,-CH=CF-,
Or-CO-O-is alternative, and its prerequisite is that heteroatoms directly is not connected to each other.
10. the liquid-crystal composition that comprises one of according to claim 1 at least a-9 described compounds.
11. liquid-crystal composition according to claim 10, it is characterized in that, described liquid-crystal composition comprises a kind of to five kinds of described liquid crystalline cpds one of according to claim 1-10, preferably, described liquid crystal compound comprises two kinds to four kinds one of according to claim 1-10 described liquid crystalline cpds.
12. liquid-crystal composition according to claim 10 is characterized in that, described liquid-crystal composition also comprises the liquid crystalline cpd of at least a general formula II:
Wherein,
R
3And R
4Identical or different, be selected from independently of one another by-H ,-F ,-Cl ,-CN ,-NCS ,-SCN ,-OCN ,-NCO ,-OCH=CF
2, a 1-20 carbon atom halo or not halo or the not thiazolinyl of the straight or branched of halo or the group that alkene oxygen base forms of the alkyl of the straight or branched of halo or alkoxyl group and 2-20 carbon atom, wherein, at described R
3With described R
4In at least one-CH
2-can by-O-,-S-,-SiH
2-,-CH=CH-,-C ≡ C-,-CF=CF-,-CH=CF-,
-CO-O-or-O-CO-substitutes, its prerequisite is that heteroatoms directly is not connected to each other;
B
1, B
2And B
3And B
4Identical or different, be selected from independently of one another by
2,3-, two fluoro-Isosorbide-5-Nitrae-phenylenes, 3-fluoro-Isosorbide-5-Nitrae-phenylene, 2-chloro-3-fluoro-1,4-phenylene, 2-fluoro-Isosorbide-5-Nitrae-phenylene, 2,6-two fluoro-1,4-phenylene, 3,5-two fluoro-Isosorbide-5-Nitrae-phenylenes, indane-2,5-two bases, piperidines-Isosorbide-5-Nitrae-two base, naphthalene-2,6-two bases, perhydronaphthalene-2,6-two bases and 1,2,3,4-naphthane-2, the group that 6-two bases form, wherein said
In one or two non-conterminous-CH
2-can by-O-or-S-substitutes, and is described
Upper one or more H can be replaced by F independently of one another, and is described
In one or two non-conterminous-CH-can be substituted by N, described
In one or two non-conterminous-CH
2-can be substituted by O, described
Upper one or more H can be replaced by F independently of one another;
Y
1, Y
2And Y
3Identical or different, be selected from independently of one another by-OCO-,-CO-O-,-CF
2O-,-CH
2O-,-OCH
2-,-CH
2CH
2-,-CF
2CH
2-,-CF=CF-,-CH=CH-,-CH (CH
3) CH
2-,-CH
2CH (CH
3)-,-(CH
2)
3O-,-O (CH
2)
3-,-COS-,-SCO-,-CH=CF-,-C
2F
4-,-(CH
2)
4-,-C
4F
8-,-OCF
2CF
2O-,-CF
2CF
2CF
2O-,-CH
2CH
2CF
2O-,-CH
2CF
2OCH
2-,-CH=CHCF
2O-,-CF
2OCH=CH-,-CF
2OCF=CH-,-CF
2OCH=CF-,-CF=CFCF
2O-,-CF
2OCF=CF-,-CH=CHCH
2CH
2-,-C
2H
4OCH
2-,-CH
2CH=CHCH
2-,-OCH
2CH
2CH
2-,-CF=CF-CF=CF-,-C ≡ C-CF=CF-,-C ≡ C-CF=CF-C ≡ C-,-CF=CF-C ≡ C-CF=CF-,-C ≡ C-CF
2O-,-group that C ≡ C-and singly-bound form, wherein, at described Y
1And Y
2In any one-CH
2-can be by-SiH
2-substitute;
M, n and p are identical or different, are 0,1 or 2 independently of one another.
13. liquid-crystal composition according to claim 12 is characterized in that, the liquid crystalline cpd of described logical formula II is selected from the group that is comprised of following compound:
14. described liquid-crystal composition is characterized in that according to claim 10-13, described liquid-crystal composition comprises and accounts for the described compound of described liquid-crystal composition gross weight 5-50% formula I; Account for the described compound of described liquid-crystal composition gross weight 50-95% general formula II, preferably, described liquid-crystal composition comprises that accounting for described liquid-crystal composition gross weight 10-30% leads to the described compound of formula I; Account for the logical described compound of formula II of described liquid-crystal composition gross weight 70-90%.
15. a liquid-crystal display, described liquid-crystal display comprise according to claim 10 one of-14 described liquid-crystal compositions.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210388534.7A CN102898288B (en) | 2012-10-13 | 2012-10-13 | Difluorovinyl-ether-containing liquid crystal compound and composition and liquid crystal displayer thereof |
| TW102136572A TWI499661B (en) | 2012-10-13 | 2013-10-09 | A liquid crystal compound having difluoro-vinyl diether-based structure, a liquid crystal composition comprising said compound and applicaton thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210388534.7A CN102898288B (en) | 2012-10-13 | 2012-10-13 | Difluorovinyl-ether-containing liquid crystal compound and composition and liquid crystal displayer thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102898288A true CN102898288A (en) | 2013-01-30 |
| CN102898288B CN102898288B (en) | 2014-08-13 |
Family
ID=47570813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210388534.7A Active CN102898288B (en) | 2012-10-13 | 2012-10-13 | Difluorovinyl-ether-containing liquid crystal compound and composition and liquid crystal displayer thereof |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN102898288B (en) |
| TW (1) | TWI499661B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103361074A (en) * | 2013-07-01 | 2013-10-23 | 江苏和成新材料有限公司 | Liquid-crystal compound containing polyfluorinated unsaturated indene ring as well as composite and application thereof |
| 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104402683B (en) * | 2014-11-21 | 2017-02-01 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound and liquid crystal mixture containing same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010050324A1 (en) * | 2008-10-27 | 2010-05-06 | チッソ株式会社 | Liquid crystal composition and liquid crystal display element |
-
2012
- 2012-10-13 CN CN201210388534.7A patent/CN102898288B/en active Active
-
2013
- 2013-10-09 TW TW102136572A patent/TWI499661B/en active
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》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103361074A (en) * | 2013-07-01 | 2013-10-23 | 江苏和成新材料有限公司 | Liquid-crystal compound containing polyfluorinated unsaturated indene ring as well as composite and application thereof |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI499661B (en) | 2015-09-11 |
| TW201414812A (en) | 2014-04-16 |
| CN102898288B (en) | 2014-08-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101143808B (en) | Fluorine phenyl compounds for liquid crystalline mixtures | |
| CN101180294B (en) | Pyran/dioxan derivatives and use thereof in liquid crystal media | |
| KR101868658B1 (en) | Ortho ester derivative, liquid crystal composition, and liquid crystal display element | |
| CN102690167B (en) | Liquid crystal compound containing saturated indene rings and composition thereof | |
| KR101258384B1 (en) | Tetrahydropyran compounds, liquid crystal compositions, and liquid crystal displays containing the compositions | |
| CN103467253B (en) | Cycloheptane derivative and preparation method thereof and application | |
| CN102898288B (en) | Difluorovinyl-ether-containing liquid crystal compound and composition and liquid crystal displayer thereof | |
| KR20110021805A (en) | Liquid crystalline tetracyclic compound having fluorine atom, liquid crystal composition and liquid crystal display element | |
| CN102898272B (en) | Containing six hydrogen indenes class novel liquid crystals and composition thereof and application in a liquid crystal display | |
| CN103772335B (en) | A kind of liquid crystalline cpd and liquid-crystal composition thereof containing five fluorine propylene and pyranoid ring | |
| TWI588243B (en) | Compounds having a fluorinated naphthalene structure and liquid crystal | |
| CN102898287B (en) | Novel two fluoro second two ethers liquid crystal and compositions thereof | |
| CN103058836B (en) | Liquid crystal compound containing indan and difluoro methylenedioxy bridge, as well as preparation method and application thereof | |
| CN102898414B (en) | Novel dioxa saturation naphthalene nucleus liquid crystal compound, composition of liquid crystal compound and application of liquid crystal compound | |
| KR100794480B1 (en) | Liquid crystalline compound having difluoropropyleneoxy group as bonding group, liquid crystal composition and liquid crystal display element | |
| JP5077621B2 (en) | Difluorobenzene derivative and liquid crystal composition using the same | |
| CN102898413B (en) | Novel liquid crystal compound with dioxa saturated indene ring and composition thereof | |
| CN102899049A (en) | Novel double-halogenated vinyl ether liquid crystal compound and composition of novel double-halogenated vinyl ether liquid crystal compound and liquid crystal display | |
| JPH10298127A (en) | Fluoroalkyl ether compound, liquid crystal composition, and liquid crystal element | |
| CN102898273B (en) | Containing six hydrogen pentalene class novel liquid crystal compounds and composition thereof and application | |
| CN102992971B (en) | Poly-fluoroethane ether liquid crystal compound and composition thereof | |
| CN102807551B (en) | Liquid crystal compound containing dioxa saturated azulenes and composition thereof | |
| CN102964324B (en) | Containing the liquid crystalline cpd of 4-tetrahydropyrans structure and composition thereof and application | |
| KR102077868B1 (en) | Liquid crystal compound, liquid crystal composition and liquid crystal display device | |
| CN104513139A (en) | Liquid crystal compound with terminal position containing difluoroethylene group and difluoromethyleneoxyl group |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C53 | Correction of patent of invention or patent application | ||
| CB03 | Change of inventor or designer information |
Inventor after: Ruan Qunqi Inventor after: Huang Wanyu Inventor after: Shi Zhibing Inventor after: Tan Yudong Inventor after: Fang Yuanfei Inventor after: Chu Zhulong Inventor after: Huang Wei Inventor after: Ding Wenquan Inventor after: Ding Yan Inventor after: Wang Junzhi Inventor before: Ruan Qunqi Inventor before: Shi Zhibing Inventor before: Tan Yudong Inventor before: Fang Yuanfei Inventor before: Chu Zhulong Inventor before: Huang Wei Inventor before: Ding Wenquan Inventor before: Ding Yan |
|
| COR | Change of bibliographic data |
Free format text: CORRECT: INVENTOR; FROM: RUAN QUNQI SHI ZHIBING TAN YUDONG FANG YUANFEI CHUZHULONG HUANG WEI DING WENQUAN DING YAN TO: RUAN QUNQI SHI ZHIBING TAN YUDONG FANG YUANFEI CHUZHULONG HUANG WEI DING WENQUAN DING YAN WANG JUNZHI HUANG WANYU |
|
| ASS | Succession or assignment of patent right |
Owner name: DAXING MATERIALS CORP. Effective date: 20140516 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20140516 Address after: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Applicant after: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Applicant after: Daxin Materials Corp. Address before: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Applicant before: Jiangsu Hecheng Display Technology Co.,Ltd. |
|
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CP03 | Change of name, title or address | ||
| CP03 | Change of name, title or address |
Address after: East side of Yangtze River bridge, Yangzhong, Yangzhong, Jiangsu Co-patentee after: Daxin Materials Corp. Patentee after: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Address before: 212212 Yangtze River bridge, Jiangsu, Yangzhong, Yangzhong on the eastern side of the road Co-patentee before: Daxin Materials Corp. Patentee before: Jiangsu Hecheng Display Technology Co.,Ltd. |
|
| CP02 | Change in the address of a patent holder |
Address after: Building 2, Sino Japan Cooperation Innovation Park, No. 16, Zidan Road, Qinhuai District, Nanjing, Jiangsu Patentee after: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Patentee after: Daxin Materials Corp. Address before: 212212 east side of Yangzhong Yangtze River Bridge, Yangzhong City, Jiangsu Province Patentee before: JIANGSU HECHENG DISPLAY TECHNOLOGY Co.,Ltd. Patentee before: Daxin Materials Corp. |
|
| CP02 | Change in the address of a patent holder |