CN102249866A - Liquid crystal composition and negative liquid crystal compound with novel structure - Google Patents
Liquid crystal composition and negative liquid crystal compound with novel structure Download PDFInfo
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 32
- 150000001875 compounds Chemical class 0.000 title claims abstract description 23
- 239000000203 mixture Substances 0.000 title claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- -1 2-cyclopropylidene Chemical group 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 239000000178 monomer Substances 0.000 abstract description 5
- 230000008018 melting Effects 0.000 abstract description 2
- 238000002844 melting Methods 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- VJCWGXGMXAVKJU-UHFFFAOYSA-N cyclohexyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1CCCCC1 VJCWGXGMXAVKJU-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GADSJKKDLMALGL-UHFFFAOYSA-N 2-propylbenzoic acid Chemical compound CCCC1=CC=CC=C1C(O)=O GADSJKKDLMALGL-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
- KWRGXZYCXWHKJF-UHFFFAOYSA-N Bc(c(F)c1F)ccc1OC(C1CCC(CCC)CC1)(F)F Chemical compound Bc(c(F)c1F)ccc1OC(C1CCC(CCC)CC1)(F)F KWRGXZYCXWHKJF-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- QCNUKEGGHOLBES-UHFFFAOYSA-N CCCC(CC1)CCC1C(O)=O Chemical compound CCCC(CC1)CCC1C(O)=O QCNUKEGGHOLBES-UHFFFAOYSA-N 0.000 description 1
- XKVIHEAGOHOQTG-UHFFFAOYSA-N CCCC(CC1)CCC1C(Oc(c(F)c1F)ccc1OC(C1CCC(CCC)CC1)(F)F)(F)F Chemical compound CCCC(CC1)CCC1C(Oc(c(F)c1F)ccc1OC(C1CCC(CCC)CC1)(F)F)(F)F XKVIHEAGOHOQTG-UHFFFAOYSA-N 0.000 description 1
- AKWVDCQCLVTVNT-UHFFFAOYSA-N CCCC(CC1)CCC1C(Oc(ccc(C)c1F)c1F)(F)F Chemical compound CCCC(CC1)CCC1C(Oc(ccc(C)c1F)c1F)(F)F AKWVDCQCLVTVNT-UHFFFAOYSA-N 0.000 description 1
- RKUOYIUVPQMBAN-UHFFFAOYSA-N CCCC(CC1)CCC1C(Oc(ccc(O)c1F)c1F)(F)F Chemical compound CCCC(CC1)CCC1C(Oc(ccc(O)c1F)c1F)(F)F RKUOYIUVPQMBAN-UHFFFAOYSA-N 0.000 description 1
- UAGPGGGTQGNVKY-UHFFFAOYSA-N CCCC(CC1)CCC1C1=SCCCS1 Chemical compound CCCC(CC1)CCC1C1=SCCCS1 UAGPGGGTQGNVKY-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention provides a negative liquid crystal monomer of a compound with a general formula I. The negative liquid crystal monomer has an extremely low melting point, a high clear point and low negative dielectric anisotropy. The invention also provides one or more liquid crystal mixtures of negative liquid crystal monomers and an electro-optic display element containing a liquid crystal composition.
Description
Technical field
The present invention relates to a kind of liquid crystalline cpd and liquid-crystal composition, relate in particular to a kind of liquid crystalline cpd and liquid crystal compound with lower fusing point, higher clearing point, fabulous low temperature mutual solubility.
Background technology
Liquid crystal material is a kind of mesomorphic phase material between solid phase and liquid phase, and its phase can roughly be divided into nematic phase, smectic phase and cholesteric phase.In display element, nematic being most widely used.Liquid crystalline cpd is because of the characteristic of its inherent optical anisotropy (Δ n) and dielectric anisotropy (Δ ε), be widely used at present the making of device liquid crystal display device such as robot calculator, meter device, automobile dashboard, electronic memo, mobile telephone, computer, televisor, its range of application is also in expansion year by year.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 dielectricity types such as (FLC).
Adopt thin film transistor (TFT) display format of liquid crystal molecule arranged vertical (VA) to have wide visual angle, response speed is fast, contrast gradient is bigger advantage, in the large scale liquid crystal TV, be used widely in recent years.Traditional distortion-nematic-mode (TN) uses dielectric anisotropy to be (Δ ε=ε just
//-ε
⊥, Δ ε＞0) liquid crystal material, on the molecular long axis direction, have polar group, make long axis direction specific inductivity (ε
//) greater than perpendicular electric constant (ε
⊥); And the liquid crystal material that the VA pattern requires to be adopted has negative dielectric anisotropic (Δ ε＜0).Purpose of the present invention is exactly that the liquid crystal material that is applicable to that the VA pattern requires will be provided.
Summary of the invention
One aspect of the present invention provides the compound of general formula I,
Wherein:
A
1, A
2And A
3Expression independently of one another do not replace or by one to four F atom replace 1,4-cyclohexylidene, 1,4-phenylidene or 1, the inferior cyclic group dialkylene of 4-, and one of them or two CH
2Group also can be independently of one another by heteroatoms-O-or-S-replaces in the mode that heteroatoms does not directly link to each other each other; 1, the 4-phenylene can be replaced by one or two fluorine or chlorine atom and one of them or two CH
2Group can be replaced by N;
R
1And R
2Expression does not independently of one another replace or by the mono-substituted at least alkyl with 1 to 12 carbon atom of halogen, and wherein one or more non-conterminous CH
2Group also can be separately independently of each other by-O-,-S-or-CO-replaces; Under every kind of situation, adjacent CH
2Group also can by-CH=CH-,-CF=CF-,-COO-,-C ≡ C-or 1, the 2-cyclopropylidene replaces, perhaps three adjacent CH
2Group can be by 1, and the inferior cyclobutyl of 3-replaces, wherein, 1,2-cyclopropylidene and 1, the inferior cyclobutyl of 3-also can be replaced by two F atoms independently of one another;
B
1, B
2And B
3Represent independently of one another singly-bound ,-CH
2CH
2-,-CH
2O-,-OCH
2-,-CH
2CF
2-,-CF
2CH
2-,-CH
2CHF-,-CHFCH
2-,-CF
2O-,-COO-,-OOC-,-CH=CH-,-CF=CF-or-C ≡ C-;
Q
1And Q
2Expression-O-CF independently of one another
2-or-CF
2-O-;
L, m, x and y represent 0 or 1 separately independently of each other, and during m=0, l+x+y≤2; During m=1, l+x+y 〉=0.
In preferred embodiments, described Q
1Be-CF
2O-, described Q
2Be-OCF
2-; Perhaps, described Q
1Be-OCF
2-, described Q
2Be-CF
2O-.
In preferred embodiments, described R
1And R
2Expression independently of one another has the unsubstituted straight chained alkyl of 1-5 carbon atom.
Preferably, the compound of general formula I is selected from the compound to formula I19 as shown in the formula I1:
Preferably, R
1And R
2Expression independently of one another contains the unsubstituted straight chained alkyl of 1 to 5 carbon atom.
Particularly preferred compound is I1, I2, I3, I4, I5, I6 and I12, especially I1, I2, I5 and I6.
Thus, the invention provides a kind of negative liquid crystal monomer, this liquid crystal monomer has utmost point low melting point, higher clearing point, low negative dielectric anisotropic.
Another aspect of the present invention is to contain a kind of or the monomeric liquid crystal compound of several above-mentioned negative liquid crystals, and the electrooptical display cells that comprises described liquid-crystal composition.
Compound in structural formula I has wide range of application.Depend on substituent selection, these compounds can be used as the base mateiral of main composition liquid crystal media; Yet the compound that also might add general formula I so that for example improve dielectric optical anisotropy of this type, is optimized its threshold voltage in the liquid crystal base mateiral that is selected from the other types compound.
Description of drawings
Fig. 1 is the mass spectrum of the compound of formula I1.
Embodiment
Following embodiment is intended to explain the present invention, but does not limit the present invention in any form.All per-cents are represented weight percent.Following temperature is a centigradetemperature.H represents hour, and min represents minute that Mp represents fusing point, and Cp represents clearing point, V
ThThe expression threshold voltage, Δ n represents specific refractory power, and ε ⊥ represents specific inductivity, and Visc represents kinetic viscosity.
Embodiment 1
Synthesis path 1
According to synthesis path 1 (with reference to Angew.Chem.Int.Ed.2001,40, NO.8,1480-1484), in toluene and (90-120) the sherwood oil volume ratio be with 1 of the trifluoromethayl sulfonic acid of 1.3 times of molar weights and 1.3 times of molar weights in 1: 1 the mixed solvent, the 3-dimercaptopropane joins in commercially available the propyl group hexahydrobenzoic acid, 95 ± 5 ℃ of reacting by heating.Behind the 6h, make system temperature reduce to 20 ℃ under the nitrogen protection, 80 ℃ of water-bath temperature controls, toluene distillation and sherwood oil under vacuum-0.8MPa when product becomes thick liquid or solid, stop distillation, and logical nitrogen is to normal pressure.Adding ether again in reaction vessel was not as the criterion to have product 0.5cm.Again product is changed over to below the cyrogenic equipment temperature control-20 ℃ and preserve more than the 8h.Freezing end back suction strainer gets white or faint yellow solid powder, i.e. intermediate product a1.
Under the nitrogen, in-85 ℃ with 2 of 1.3 times of molar weights, the 3-difluorophenol mixes with the triethylamine of 1.3 times of molar weights, is added drop-wise to the CH of intermediate product a1
2Cl
2In the solution, behind the reaction 1.5h, under-80 ℃, successively the liquid bromine of the compound trihydrofluoride of the triethylamine of 5 times of molar weights and 5 times of molar weights is added drop-wise in the reaction system, behind the reaction 1h, reaction solution is poured in the mixture of ice and water, aqueous sodium hydroxide solution adjust pH with 20% is to 5-8, the dichloromethane extraction water, the combined dichloromethane layer is washed to neutrality, again with extremely clarification of anhydrous sodium sulfate drying, concentrate weak yellow liquid (hereinafter to be referred as conventional processing), column chromatography purification (60-100 order silica gel, eluent are sherwood oil) concentrates except that after desolvating and obtains intermediate a2.
Under the nitrogen, in THF, must n-Butyl Lithium intermediate a2 be carried out lithiumation with-78 ℃ with the commercially available of 1.1 times of molar weights, behind the reaction 2h, under-75 ℃, boric acid three isobutyl esters are joined in this organometallic compound, be warming up to-30 ℃ naturally behind the reaction 1h, use the dilute hydrochloric acid acidifying, the water layer ethyl acetate extraction, merge the oil phase after washing to neutral, use anhydrous sodium sulfate drying again, concentrate do the back with sherwood oil handle intermediate a3.
In methylene dichloride, dioxane and deionized water volume ratio is with 30%H in 3: 2: 1 the mixed solvent
2O
2Join among the intermediate a3,, obtain intermediate a4 through the routine processing in 38-40 ℃ of reaction 8-12 hour.With intermediate a1 and a4 is main raw material, adopts the synthetic method of intermediate a2 to make final product I1.Mp＝60.35-62.55℃，Cp＝155.74-157.58℃。
The mass spectrum of product I1 as shown in Figure 1.
Embodiment 2
Synthesis path 2
According to embodiment 1 described method, be that initial feed finally makes product I5 through several synthesis steps with commercially available propyl group dicyclohexyl formic acid and valeric acid, concrete implementation step such as composite diagram 2 statement.
Embodiment 3
Synthesis path 3
According to synthesis path 3, under the nitrogen, under-78 ℃, the n-Butyl Lithium of 1.1 times of molar weights joined in commercially available the 1,2-Difluorobenzene react 2h, in the organometallics that forms, feed excessive CO again
2Until reaction system no longer because of feeding CO
2And heat up, stop to feed CO
2Reaction solution is regulated pH value 1-2 with 10% aqueous hydrochloric acid, water with the toluene extraction after, the oil phase anhydrous sodium sulfate drying, concentrated faint yellow solid gets straight product 2 through the sherwood oil recrystallization, 3-difluoro-benzoic acid, i.e. intermediate b1.Utilize embodiment 1 described method, 2, the 3-difluoro-benzoic acid can make intermediate b2 by two-step reaction.Adopt the synthetic method of intermediate b1 intermediate b2 can be prepared into intermediate b3.And the b3 intermediate can be prepared into intermediate b4 by embodiment 1 described method.With intermediate b4 and 4-propylphenol is main raw material, adopts embodiment 1 described method sintetics I5.
Embodiment 4
Synthesis path 4
According to embodiment 1 described method, be that initial feed finally makes product I6 through several synthesis steps with commercially available propylbenzoic acid and propyl group dicyclohexyl formic acid, concrete implementation step such as synthesis path 4 statement.
Embodiment 5-7
Synthetic with common known method equally:
Embodiment 8
Preparation has the liquid-crystal composition of forming shown in the table 1:
Table 1
Wherein, clearing point is to use the fusing point instrument to test; Threshold voltage is to use liquid crystal device parametric synthesis tester LCT-5016C to test; Specific refractory power and specific refractory power anisotropy use Abbe refractometer under sodium lamp (589nm) light source, 20 ℃ test; The dielectric testing cassete is the TN90 type, the thick 7 μ m of box; Kinetic viscosity Visc uses cone-and-plate viscometer to test;
According to above method, it is as follows to record parameters:
Δ n=0.1223 (probe temperature is 20 ℃);
ε⊥＝10.13；
Cp＝119.2℃；
Vth=2.8v (probe temperature is 20 ℃);
η=57.8 (probe temperature is 20 ℃).
Claims (7)
1. the compound of general formula I,
Wherein:
A
1, A
2And A
3Expression independently of one another do not replace or by one to four F atom replace 1,4-cyclohexylidene, 1,4-phenylidene or 1, the inferior cyclic group dialkylene of 4-, and one of them or two CH
2Group also can be independently of one another by heteroatoms-O-or-S-replaces in the mode that heteroatoms does not directly link to each other each other; 1, the 4-phenylene can be replaced by one or two fluorine or chlorine atom and one of them or two CH
2Group can be replaced by N;
R
1And R
2Expression does not independently of one another replace or by the mono-substituted at least alkyl with 1 to 12 carbon atom of halogen, and wherein one or more non-conterminous CH
2Group also can be separately independently of each other by-O-,-S-or-CO-replaces; Under every kind of situation, adjacent CH
2Group also can by-CH=CH-,-CF=CF-,-COO-,-C ≡ C-or 1, the 2-cyclopropylidene replaces, perhaps three adjacent CH
2Group can be by 1, and the inferior cyclobutyl of 3-replaces, wherein, 1,2-cyclopropylidene and 1, the inferior cyclobutyl of 3-also can be replaced by two F atoms independently of one another;
B
1, B
2And B
3Represent independently of one another singly-bound ,-CH
2CH
2-,-CH
2O-,-OCH
2-,-CH
2CF
2-,-CF
2CH
2-,-CH
2CHF-,-CHFCH
2-,-CF
2O-,-COO-,-OOC-,-CH=CH-,-CF=CF-or-C ≡ C-;
Q
1And Q
2Expression-O-CF independently of one another
2-or-CF
2-O-;
L, m, x and y represent 0 or 1 separately independently of each other, and during m=0, l+x+y≤2; During m=1, l+x+y 〉=0.
2. compound according to claim 1 is characterized in that, described Q
1Be-CF
2O-, described Q
2Be-OCF
2-.
3. compound according to claim 1 is characterized in that, described Q
1Be-OCF
2-, described Q
2Be-CF
2O-.
4. compound according to claim 1, described compound has one of following general formula:
5. compound according to claim 4 is characterized in that, described R
1And R
2Expression independently of one another has the unsubstituted straight chained alkyl of 1-5 carbon atom.
6. a liquid-crystal composition is characterized in that, described liquid-crystal composition comprises at least a as the described compound of one of claim 1 to 5.
7. an electrooptical display cells is characterized in that, described electrooptical display cells comprises liquid-crystal composition as claimed in claim 6.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103254907A (en) * | 2013-04-23 | 2013-08-21 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition with negative dielectric anisotropy |
| CN103725292A (en) * | 2012-10-15 | 2014-04-16 | 达兴材料股份有限公司 | Negative dielectric anisotropy liquid crystal compound and liquid crystal composition comprising same |
| CN104245757A (en) * | 2012-04-24 | 2014-12-24 | 捷恩智株式会社 | Compound having four polymerizable groups, liquid crystal composition, and liquid crystal display element |
| CN104531166A (en) * | 2014-12-12 | 2015-04-22 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound containing cyclopropyl and liquid crystal mixture |
| CN106675576A (en) * | 2015-11-06 | 2017-05-17 | 江苏和成显示科技股份有限公司 | Dielectric negative liquid crystal compound and preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| CN101162333A (en) * | 2006-10-12 | 2008-04-16 | 默克专利股份有限公司 | Liquid-crystal display |
| US20090109392A1 (en) * | 2007-10-24 | 2009-04-30 | Chung-Ching Hsieh | Liquid crystal mixture for psa process and liquid crystal display device |
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| CN104245757A (en) * | 2012-04-24 | 2014-12-24 | 捷恩智株式会社 | Compound having four polymerizable groups, liquid crystal composition, and liquid crystal display element |
| US9617477B2 (en) | 2012-04-24 | 2017-04-11 | Jnc Corporation | Compound having four polymerizable groups, liquid crystal composition and liquid crystal display device |
| CN103725292A (en) * | 2012-10-15 | 2014-04-16 | 达兴材料股份有限公司 | Negative dielectric anisotropy liquid crystal compound and liquid crystal composition comprising same |
| CN103725292B (en) * | 2012-10-15 | 2016-01-20 | 达兴材料股份有限公司 | Negative dielectric anisotropy liquid crystal compound and liquid crystal composition comprising same |
| CN103254907A (en) * | 2013-04-23 | 2013-08-21 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition with negative dielectric anisotropy |
| CN103254907B (en) * | 2013-04-23 | 2016-01-20 | 石家庄诚志永华显示材料有限公司 | Negative dielectric anisotropy liquid crystal composition |
| CN104531166A (en) * | 2014-12-12 | 2015-04-22 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound containing cyclopropyl and liquid crystal mixture |
| CN104531166B (en) * | 2014-12-12 | 2016-09-07 | 石家庄诚志永华显示材料有限公司 | Liquid-crystal compounds containing cyclopropyl and liquid crystal compound |
| CN106675576A (en) * | 2015-11-06 | 2017-05-17 | 江苏和成显示科技股份有限公司 | Dielectric negative liquid crystal compound and preparation method and application thereof |
| CN106675576B (en) * | 2015-11-06 | 2018-09-04 | 江苏和成显示科技有限公司 | A kind of dielectric negative liquid crystal compound and the preparation method and application thereof |
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