CN104610978B - Liquid crystal compounds and liquid crystal medium containing same - Google Patents
Liquid crystal compounds and liquid crystal medium containing same Download PDFInfo
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- CN104610978B CN104610978B CN201510066236.XA CN201510066236A CN104610978B CN 104610978 B CN104610978 B CN 104610978B CN 201510066236 A CN201510066236 A CN 201510066236A CN 104610978 B CN104610978 B CN 104610978B
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Abstract
The invention relates to novel negative dielectric liquid crystal compounds with structural formulas (I) as shown in the specification, wherein A and R1 have the meanings given in claims. The invention further relates to a liquid crystal medium comprising at least one of the compounds with the structural formulas (I) and an electro-optical display containing the liquid crystal medium. The compounds have appropriate negative dielectricity, large K values and low rotational viscosity and are suitable for high-gradient and quick-response VA liquid crystals.
Description
Technical field
The invention belongs to liquid-crystal compoundss and its application are and in particular to a kind of liquid-crystal compoundss and comprise this chemical combination
The liquid crystal media of thing, this kind of liquid crystal media is applied to passive or active driven liquid crystal Display Technique.
Background technology
At present, what the range of application of liquid-crystal compoundss was expanded is increasingly wider, and it can be applicable to polytype display, electricity
In optical device, sensor etc..Species for the liquid-crystal compoundss of above-mentioned display field is various, and wherein nematic liquid crystal is applied
For extensive.Nematic liquid crystal have been applied in passive tn, stn matrix display and there is tft active matrix system in.
For thin-film transistor technologies (tft-lcd) application, although market is very huge in recent years, technology
Gradually ripe, but the requirement to Display Technique for the people also improves continuous, is especially realizing quick response, is reducing and drive electricity
Pressure is to reduce the aspects such as power consumption.Liquid crystal material as one of important photoelectron material of liquid crystal display, to improving liquid crystal display
The important effect of the performance of device.
Tft-lcd has been widely used for industrial circle and household consumption field at present, almost instead of tradition completely
Crt monitor market.According to the difference of liquid crystal display mode, liquid crystal display cells can be divided into twisted nematic (tn) mould
The various modes such as formula, super-twist nematic (stn) pattern, coplanar (ips) pattern, vertical orientation (va) pattern.
Current liquid crystal display cells mostly are twisted nematic (tn) pattern, but it exists, and contrast is low, angle of visibility is narrow
Shortcoming, and the display of vertical orientation (va) pattern, with its wide angle of visibility, high-contrast and without advantages such as friction matchings, has obtained
Apply to extensive, and become the common display pattern of large scale tv tft-lcd, in addition, the contrast that va pattern shows is to liquid
The wavelength dependence degree of brilliant birefringence, the thickness of liquid crystal layer and incident illumination is less, therefore, va pattern become now great before
The lcd technology of scape.
For the liquid crystal material used by the display mode of va pattern etc. it is desirable to low voltage drive, quick response, wide temperature
Scope and good low-temperature stability.In other words, also require us to develop negative dielectric anisotropic absolute value is big, low-viscosity,
Big k33 value and the compound of high clearing point.
Content of the invention
The technical problem to be solved in the invention is to provide a kind of new negative dielectric anisotropic liquid crystal compound and bag
Liquid crystal media containing this compound, this liquid-crystal compounds has a big k value, suitable negative dielectric anisotropic, relatively low rotation
Viscosity；The liquid crystal media comprising this compound have low rotary viscosity, faster response time and suitable negative dielectric respectively to
The opposite sex, and high steepness.
Exactly because this advantage of compound shown in formula provided by the present invention and be used to do the liquid of va pattern display mode
Crystalline medium.
Chemical combination shown in formula provided by the present invention due to the introducing of two ethylene linkages and end group cyclopenta or cyclobutyl, greatly
Improve its k value, especially k33, rotary viscosity is relatively low simultaneously.It is highly suitable for va display pattern, especially high way va
Display, and the va-tft pattern of quick response, va-ips pattern.
For reaching above-mentioned technique effect, the technical solution used in the present invention is:
The invention provides liquid-crystal compoundss shown in formula
Wherein, a represents cyclobutyl or cyclopenta；r1Represent the straight-chain alkenyl that carbon number is 1-10.
Shown in described formula, liquid-crystal compoundss preferred formula a is to liquid-crystal compoundss shown in formula l
Present invention also offers a kind of liquid crystal media, described liquid crystal media comprises LCD compound shown in one or more formula
Thing.
Liquid crystal media provided by the present invention preferably comprises one or more formula a to liquid-crystal compoundss shown in formula l.
Liquid crystal media provided by the present invention can also comprise compound shown in one or more formula
Wherein, r2、r3Represent that the alkyl for 1-10 for the carbon number or carbon number are the alkenyl of 2-10 independently of one another；
Wherein other, described r2、r3In contain-ch2- group in arbitrary-ch2- by-ch2o-、-och2- ,-c=c- replace
Or unsubstituted, described r2、r3In arbitrary-h replaced or unsubstituted by-f；
It is expressed as follows independently of one another
Group:
The each independent expression 0 or 1 of m, n, o；
z1、z2、z3Each independent expression singly-bound ,-c2h4- ,-ch=ch-,-coo-、-ooc-、-ch2o-、-
och2-、-cf2o-、-ocf2-, wherein other ,-c2h4-, arbitrarily-h can be replaced or unsubstituted by-f in-ch=ch-.
As a component of liquid crystal media provided by the present invention, compound shown in described formula is preferably describedAt least one expression When represented compound.
Liquid crystal media provided by the present invention preferably comprises compound shown in one or more following a to o:
Described formula a to formula o,
Various middle r2、r3May be the same or different, represent that the alkyl for 1-10 for the carbon number or carbon number are independently of one another
The alkenyl of 2-10；Wherein other, described r2、r3In contain-ch2- group in arbitrary-ch2- by-ch2o-、-
och2- ,-c=c- replace or unsubstituted, described r2、r3In arbitrary-h replaced or unsubstituted by-f；
Arbitrary group in expression following groups independently of one another:
Further, liquid crystal media provided by the present invention in compound shown in included one or more formula or
The compound shown in one or more formula can also be comprised on the basis of not contained shown compound
Wherein, r4、r5Represent that the alkyl for 1-10 for the carbon number or carbon number are the alkenyl of 2-10, wherein other,
Described r4、r5In contain-ch2- group in arbitrary-ch2- by-ch2o-、-och2- ,-c=c- replace or unsubstituted, institute
State r2、r3In arbitrary-h replaced or unsubstituted by-f；
It is expressed as follows independently of one another
Group:
P, each independent expression 0 or 1 of q, r；
z4、z5、z6Each independent expression singly-bound ,-c2h4- ,-ch=ch-,-coo-、-ooc-、-ch2o-、-
och2-、-cf2o-、-ocf2-, described-c2h4-, arbitrarily-h is replaced or unsubstituted by-f in-ch=ch-.
The liquid crystal media comprising the compound shown in one or more formula preferably comprises one or more formula a to formula
Compound shown in p
Described formula a to formula p, r2、r3、r4、r5Represent independently of one another following 1. -3. any in shown group
A kind of:
1. the unbranched alkoxy for 1-7 for the straight chained alkyl or carbon number for 1-7 for the carbon number；
2. contain-ch in described 1. shown group2- one or more of group-ch2- by-o- ,-coo- ,-ooc-
Or-ch=ch- replaces formed group；
3. one or more-h quilt-f ,-cl ,-ch=ch in described 1. shown group2Or-ch=ch-ch3Replace and formed
Group.
New negative dielectric anisotropic liquid crystal compound provided by the present invention and the liquid crystal media comprising this compound,
This liquid-crystal compounds has a big k value, suitable negative dielectric anisotropic, relatively low rotary viscosity；Comprise the liquid of this compound
Crystalline medium has low rotary viscosity, faster response time and suitable negative dielectric anisotropic, and high steepness.
Specific embodiment
In following embodiments, involved number is weight percentage, temperature unit be DEG C, other symbols concrete
Meaning and test condition are as follows:
S-n represents the crystalline state of liquid crystal to nematic fusing point (DEG C)；
C.p. the clearing point (DEG C) of liquid crystal, test instrunment: the micro- heat analysis of mettler-toledo-fp system are represented
Instrument；
γ 1 be rotary viscosity (mpa s), test condition is: 25 DEG C, instec:alct-ir1,18 microns of vertical cassette；
k11For distorting elastic constant, k33For splay elastic constant, test condition is: 25 DEG C, instec:alct-ir1,18
Micron vertical cassette；
△ ε represents dielectric anisotropy, △ ε=ε∥-ε⊥, wherein, ε∥It is the dielectric constant parallel to molecular axis, ε⊥It is vertical
Straight in the dielectric constant of molecular axis, test condition: 25 DEG C, instec:alct-ir1,18 microns of vertical cassette；
δ n represents optical anisotropy, △ n=no-ne, wherein, noFor the refractive index of ordinary light, neFor extraordinary ray
Refractive index, test condition: 589nm, 25 ± 0.2 DEG C；
The compound of structural formula can be prepared as follows:
Reaction process:
Ring a has the meaning representated by claim 1, and r represents the straight chained alkyl of c1-c5
Specific embodiment be given below:
" conventional post processing " refers to, if necessary to add water, mixture dichloromethane, ether, methyl tertiary butyl ether(MTBE) or
Toluene extracts, and split-phase is dried organic faciess and evaporation, and then product is by vacuum distillation or crystallization and/or chromatography purification.
Embodiment 1:
Ring a represents cyclopenta, and r1 represents vinyl.
Step 1.1
2l there-necked flask adds 0.9mol chloromethyl ether triphenyl microcosmic salt, 1l oxolane, and stirred under nitrogen atmosphere is cooled to 0
DEG C, it is dividedly in some parts 1mol potassium tert-butoxide, 0-10 DEG C of temperature control, reactant liquor becomes bronzing.Add potassium tert-butoxide, stirring reaction 2 hours,
The 100ml tetrahydrofuran solution of Deca 0.8mol Ketocyclopentane, below 10 DEG C of temperature control, drips off stirring reaction 3 hours, hydrolysis, point liquid,
500ml methylbenzene extraction aqueous solution twice, merges, is washed to neutrality.Solvent evaporated, air-distillation, obtain product0.67mol, gc:95% yield 83.8%.
Step 1.2
1l there-necked flask adds 0.67mol500ml oxolane cools to 0 DEG C, Deca 200ml
Concentrated hydrochloric acid adds 100ml aqueous solution, reacts 4 hours, carry out conventional post processing, obtain target product 0.56mol below 10 DEG C of temperature control,
Gc:98%, yield: 83.6%.
Step 1.3
1l there-necked flask adds 0.56mol300ml oxolane, the boron hydrogen of lower Deca 0.73mol of stirring
Change potassium 200ml aqueous solution, heat release simultaneously releases a large amount of hydrogen, completion of dropping, room temperature reaction 1 hour is heated to reflux 2 hours, carries out
Conventional post processing, obtains target product 0.56mol, gc:96%, yield: 100%
Step 1.4
2l there-necked flask adds 0.56mol cyclopentyl carbinol, 0.6mol iodine, 0.6mol imidazoles, 500ml toluene, room temperature (25-
30 DEG C) stirring 6h, reaction finishes, and carries out conventional post processing, obtains product 0.42mol cyclopentyl-methyl iodine, yield 75%, gc:
96%.
Step 1.5
2l there-necked flask adds 0.42mol2,3- difluorophenol, the sodium hydroxide of 0.48mol, 400mlthf, and stirring and dissolving is complete
Quan Hou, Deca 0.42mol200ml tetrahydrofuran solution, drip off room temperature reaction 1 hour, back flow reaction 1 is little
When, conventional post processing, obtain product 0.4mol, gc:98%, yield 95%.
Step 1.6
2l there-necked flask adds 0.4molIt is cooled to -70 under the dry oxolane of 400ml, stirring
DEG C, Deca 0.44mol n-BuLi, t -70 DEG C of keeping temperature, after completion of dropping, -70 low temperature stirring 1h, Deca 0.4mol200ml tetrahydrofuran solution, exothermic heat of reaction, -70 DEG C of temperature control -- 75 DEG C of Deca, drip off within about 1 hour, add temperature control
Reaction 3 hours, reaction finishes, and Deca 500ml hydrolyzes, point liquid, and 200ml methylbenzene extraction aqueous phase merges organic faciess, in being washed to
Property, obtain about 1l toluene solution, standby.
2l there-necked flask adds upper ground beetle benzole soln, p-methyl benzenesulfonic acid 5g, ethylene glycol 200ml, heated and stirred, steams solvent,
Steam to 110 DEG C, change reflux water-dividing, after anhydrous separate again after, cooling, add 500ml water, a stirring point liquid, wash organic faciess, in
After property, anhydrous sodium sulfate drying, column chromatography once, solution for standby, gc:99%, yield: 100%
Step 1.7
2l there-necked flask adds step product, 200ml dehydrated alcohol, 5%pd/c, installs sealed stirring device, nitrogen
Emptying 5 times, hydrogen exchange 5 times, stirring hydrogenation 5 hours, no longer inhale hydrogen, reaction finishes, and suction strainer removes pd/c, column chromatography, is evaporated
Solvent obtains product gc:99%, yield 95%
Step 1.8
1l there-necked flask adds step product, 280ml 85% formic acid, 200ml toluene on 0.4mol, and 40-50 DEG C of stirring is anti-
Answer 6h, reaction finishes.Carry out conventional post processing, obtain target product 0.32mol (trans), gc:99%, yield: 80%.
Step 1.9
2l there-necked flask adds 0.6mol chloromethyl ether triphenyl microcosmic salt, 600ml oxolane, and stirred under nitrogen atmosphere is cooled to
0 DEG C, it is dividedly in some parts 0.7mol potassium tert-butoxide, 0-10 DEG C of temperature control, reactant liquor becomes bronzing.Add potassium tert-butoxide, stirring reaction 2 is little
When, Deca 0.4mol400ml tetrahydrofuran solution, below 10 DEG C of temperature control, drip off stirring
Reaction 3 hours, conventional post processing, obtain product 0.32mol, gc:99%, yield 80%
Step 1.10
2l there-necked flask adds step product on 0.32mol, and 1000ml oxolane cools to 0 DEG C, and Deca 200ml concentrated hydrochloric acid adds
100ml aqueous solution, reacts 4 hours below 10 DEG C of temperature control, carries out conventional post processing, obtain target product 0.28mol, gc:98%,
Yield: 87.5%
Step 1.12
2l there-necked flask adds 1mol chloromethyl ether triphenyl microcosmic salt, 1l oxolane, and stirred under nitrogen atmosphere is cooled to 0 DEG C,
It is dividedly in some parts 1.1mol potassium tert-butoxide, 0-10 DEG C of temperature control, reactant liquor becomes bronzing.Add potassium tert-butoxide, stirring reaction 2 hours,
Deca 0.9mol200ml tetrahydrofuran solution, below 10 DEG C of temperature control, drip off stirring reaction 3
Hour, hydrolysis, point liquid, 500ml methylbenzene extraction aqueous solution twice, merges, is washed to neutrality.Solvent evaporated, air-distillation, obtain mesh
Mark product 0.83mol, gc:95% yield 92%.
Step 1.13
2l there-necked flask adds step product, 400ml thf on 0.83mol, and ice salt bath is cooled to 0 DEG C, and Deca 100ml is dense
Hydrochloric acid and the mixed solution of 100ml water, 5 DEG C of keeping temperature t, the 4h of low temperature stirring afterwards, reaction finishes, and adds 400ml dichloromethane
Alkane and 400ml water, point liquid, carry out conventional post processing, obtain product to Formyl-cyclohexyl methyl formate (trans 75%), standby
2l there-necked flask adds 400ml absolute methanol, 0.42mol potassium hydroxide, is cooled to 5 DEG C, Deca pair after stirring and dissolving
Formyl-cyclohexyl methyl formate, 10 DEG C of keeping temperature t, after completion of dropping, low temperature stirs 4h, and reaction finishes, after carrying out routine
Process, obtain trans to Formyl-cyclohexyl methyl formate 0.80mol, yield: 96.4%, gc:93.2%.
Step 1.14
1l there-necked flask adds 0.12mol bromomethane triphenylphosphine salt, 500mlthf, under nitrogen protection, is cooled to 0 DEG C, point
Criticize and add 0.12mol potassium tert-butoxide, keep 5 DEG C of t, finish low temperature stirring 1h, Deca 0.1mol is to Formyl-cyclohexyl formic acid first
Ester, keeps 5 DEG C of t, the 1h of low temperature stirring afterwards, 6h is stirred at room temperature, reaction finishes, carries out conventional post processing, obtain target product
(trans) 0.06mol, yield: 60%, gc:97.5%.
Step 1.15
1l single port bottle adds 0.12mol potassium borohydride and 200ml methanol, Deca 0.06mol's
100mlthf, is stirred at room temperature 6h, and reaction finishes, and Deca 1:1 concentrated hydrochloric acid, to acid, carry out conventional post processing, obtains 0.1mol mesh
Mark product, yield 83.3%, gc:97.5%.
Step 1.16
500ml there-necked flask adds 0.1mol0.11mol iodine, 0.11mol imidazoles, 100ml first
Benzene, (25-30 DEG C) stirring 6h of room temperature, reaction finishes, and carries out conventional post processing, obtains product 0.075molYield 75%, gc:97%.
Step 1.17
500ml there-necked flask adds 0.075mol0.1mol triphenylphosphine, 100ml toluene, heating
To flowing back, react 4h, filter, toluene rinse filter cake, obtain product 0.07molYield
94.6%
Step 1.18
1l there-necked flask adds 0.1mol200mlthf, under nitrogen protection, is cooled to 0 DEG C,
It is dividedly in some parts 0.12mol potassium tert-butoxide, keeps 5 DEG C of t, finish low temperature stirring 1h, Deca 0.07molKeep 5 DEG C of t, the 1h of low temperature stirring afterwards, 6h is stirred at room temperature, reaction finishes, and enters
Row routine post processing, obtains target product (trans) 0.04mol, yield: 60%, gc:99.5%
The similar compound being prepared for following structural formula:
Embodiment 2
Ring a represents cyclopenta, r1Representative-ch2-ch2- ch=ch2,
Step 2.1
1l there-necked flask add 0.1mol chloromethyl ether triphenylphosphine salt, 100ml oxolane, stirring be cooled to 5 DEG C, in batches plus
Enter 0.12mol potassium tert-butoxide, 0-10 DEG C of stirring 1h of temperature control, Deca 0.09mol50ml tetrahydrochysene furan
Mutter solution, 0-10 DEG C of temperature control, drip off reaction 3 hours, carry out conventional post processing, obtain product 0.072molYield 80%, gc:97%.
Step 2.2
500ml there-necked flask adds step product, 100ml thf on 0.072mol, and ice salt bath is cooled to 0 DEG C, Deca
50ml concentrated hydrochloric acid and the mixed solution of 50ml water, 5 DEG C of keeping temperature t, the 4h of low temperature stirring afterwards, reaction finishes, and adds 100ml
Dichloromethane and 100ml water, point liquid, carry out conventional post processing, obtain product0.070mol, receives
Rate: 97%, gc:95.2%.
Step 2.3
500ml there-necked flask adds 0.1mol chloromethyl ether triphenylphosphine salt, 100ml oxolane, and stirring is cooled to 5 DEG C, point
Criticize and add 0.10mol potassium tert-butoxide, 0-10 DEG C of stirring 1h of temperature control, Deca 0.07mol50ml tetra-
Hydrogen tetrahydrofuran solution, 0-10 DEG C of temperature control, drip off reaction 3 hours, carry out conventional post processing, obtain product 0.06molYield 85%, gc:96%.
Step 2.4
Can be obtained trans with reference to step 2.20.052mol, yield 86.7%, gc:94%
Step 2.5
3- cyclobutenyl methyl cyclohexanecarboxylaand 0.04mol, yield 77%, gc:97% can be obtained with reference to step 1.14
Step 2.6
Can be obtained with reference to step 1.150.1mol, yield 83.3%, gc:97.5%.
Step 2.7
Can prepare with reference to step 1.16Yield 80%, gc:96%
Step 2.8
Can be obtained with reference to step 1.17Yield 85%
Step 2.9
Can be obtained with reference to step 1.18Yield 65%, gc:99.5%
The similar following compounds that synthesized:
Part of compounds parameter
Can be seen that compared with analog structure common compound from compound data and comparative example data, the present invention is carried
For compound there is bigger refractive index, higher clearing point, suitable dielectric (△ ε)；Contribute phase DANGSHEN in the composition
During number, rotary viscosity (γ1) relatively small；There is bigger k33, especially k33/k11Larger, in high steepness va liquid crystal, va-
There is good using value in tft, va-ips liquid crystal.Liquid crystal media embodiment:
Example 3 below～9 weigh in proportion respectively formula, liquid-crystal compoundss, be prepared into liquid crystal media.
The various liquid crystal monomers being used all can be synthesized by known method, or by being either commercially available.
Prepare the equipment used by liquid crystal media and instrument be:
(1) precise electronic balance (degree of accuracy 0.1mg)
(2) rustless steel beaker: for weighing liquid crystal
(3) spoon: for adding monomer
(4) magnetic rotor: for stirring
(5) temperature control magnetic stirrer
The preparation method of liquid crystal media comprises the following steps:
(1) monomer used is put neatly in order；
(2) rustless steel beaker is placed on balance, is contained monomer in rustless steel beaker with little spoon；
(3) press required weight successively and add monomer liquid crystal；
(4) the rustless steel beaker adding honest material is placed on heating and melting on magnetic agitation instrument；
(5) after the most thawing of mixture in rustless steel beaker, toward in rustless steel beaker, add a magnetic rotor, will
Liquid crystal compound stirs, and obtains final product liquid crystal media after being cooled to room temperature.
The liquid crystal media of gained is filled between liquid crystal display two substrates and carries out performance test.The monomer of particular compound
Structure, consumption (weight percentage), the performance parameter test result of the liquid crystal media of gained are all listed in table.
The component proportion of liquid-crystal composition of table 1 comparative example and its performance parameter
The component proportion of liquid crystal media of table 2 embodiment 3 and its performance parameter
The component proportion of liquid crystal media of table 3 embodiment 4 and its performance parameter
The component proportion of liquid crystal media of table 4 embodiment 5 and its performance parameter
The component proportion of liquid crystal media of table 5 embodiment 6 and its performance parameter
The component proportion of liquid crystal media of table 6 embodiment 7 and its performance parameter
The component proportion of liquid crystal media of table 7 embodiment 8 and its performance parameter
The component proportion of liquid crystal media of table 8 embodiment 9 and its performance parameter
The performance parameter of the liquid-crystal composition shown in embodiment 2～9, the liquid-crystal composition of the present invention has comparison
The bigger k value of ratio, suitable optical anisotropy, relatively low rotary viscosity, good low-temperature stability, is highly suitable for having
Source or passive matrix display element, such as ecb, ffs or ips, the Active Matrix Display of mva effect and vehicle-mounted black and white va show
Show.
Although the present invention only lists the particular compound of above-mentioned 7 embodiments and its proportioning consumption, and (weight percent contains
Amount), and carried out performance test, but the liquid-crystal composition of the present invention can be on the basis of above-described embodiment, using this
Bright involved formula,, representative liquid-crystal compoundss and formula, preferred liquid-crystal compoundss carry out
Expand further and change, by suitably being adjusted to its proportioning consumption, all can reach the purpose of the present invention.
Claims (9)
1. liquid-crystal compoundss shown in formula
Wherein, a represents cyclobutyl or cyclopenta；r1Represent the straight-chain alkenyl that carbon number is 1-10.
2. formula a is to liquid-crystal compoundss shown in formula l
3. liquid crystal media is it is characterised in that described liquid crystal media comprises to liquid-crystalize shown in one or more claim 1 Chinese style
Compound.
4. liquid crystal media is it is characterised in that described liquid crystal media comprises shown in one or more claim 2 Chinese style a to l
Liquid-crystal compoundss.
5. liquid crystal media according to claim 3 is it is characterised in that described liquid crystal media also comprises one or more formula
Shown compound
Wherein, r2、r3Represent that the alkyl for 1-10 for the carbon number or carbon number are the alkenyl of 2-10 independently of one another；Wherein
Other, described r2、r3In contain-ch2- group in arbitrary-ch2- by-ch2o-、-och2- ,-c=c- replace or not
Replace, described r2、r3In arbitrary-h replaced or unsubstituted by-f；
It is expressed as follows group independently of one another:
The each independent expression 0 or 1 of m, n, o；
z1、z2、z3Each independent expression singly-bound ,-c2h4- ,-ch=ch-,-coo-、-ooc-、-ch2o-、-
och2-、-cf2o-、-ocf2-, wherein other ,-c2h4-, arbitrarily-h can be replaced or unsubstituted by-f in-ch=ch-.
6. liquid crystal media according to claim 5 is it is characterised in that describedIn at least one be selected from
7. liquid crystal media according to claim 5 it is characterised in that described liquid crystal media comprise one or more following
Compound shown in a to o:
Described formula a to formula o,
Various middle r2、r3May be the same or different, represent that the alkyl for 1-10 for the carbon number or carbon number are 2-10 independently of one another
Alkenyl；Wherein other, described r2、r3In contain-ch2- group in arbitrary-ch2- by-ch2o-、-och2-、-c
=c- replaces or unsubstituted, described r2、r3In arbitrary-h replaced or unsubstituted by-f；
Arbitrary group in expression following groups independently of one another:
8. according to described liquid crystal media arbitrary in claim 3 to 7 it is characterised in that described liquid crystal media comprises one kind or many
Compound shown in the formula of kind
Wherein, r4、r5Represent that the alkyl for 1-10 for the carbon number or carbon number are the alkenyl of 2-10, wherein other, described
r4、r5In contain-ch2- group in arbitrary-ch2- by-ch2o-、-och2- ,-c=c- replace or unsubstituted, described r4、
r5In arbitrary-h replaced or unsubstituted by-f；
It is expressed as follows group independently of one another:
P, each independent expression 0 or 1 of q, r；
z4、z5、z6Each independent expression singly-bound ,-c2h4- ,-ch=ch-,-coo-、-ooc-、-ch2o-、-
och2-、-cf2o-、-ocf2-, described-c2h4-, arbitrarily-h is replaced or unsubstituted by-f in-ch=ch-.
9. according to claim 8 liquid crystal media it is characterised in that described liquid crystal media comprises one or more formula a extremely
Compound shown in formula p
Described formula a to formula p, r4、r5Represent independently of one another following 1. -3. any one in shown group:
1. the unbranched alkoxy for 1-7 for the straight chained alkyl or carbon number for 1-7 for the carbon number；
2. contain-ch in described 1. shown group2- one or more of group-ch2- by-o- ,-coo- ,-ooc- or-ch
=ch- replaces formed group；
3. one or more-h quilt-f ,-cl ,-ch=ch in described 1. shown group2Or-ch=ch-ch3Replace formed base
Group.
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| CN109722256B (en) * | 2017-10-27 | 2021-08-10 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition and application thereof |
| CN114369466B (en) * | 2021-11-11 | 2024-04-05 | 烟台显华科技集团股份有限公司 | Negative dielectric anisotropy liquid crystal composition with high gradient and application thereof |
| CN115612503B (en) * | 2022-08-29 | 2024-09-27 | 重庆汉朗精工科技有限公司 | Quick response negative liquid crystal composition and liquid crystal display |
| CN116286023A (en) * | 2022-09-08 | 2023-06-23 | 重庆汉朗精工科技有限公司 | Negative liquid crystal composition and application thereof in liquid crystal display device |
| CN116286024B (en) * | 2022-09-08 | 2024-09-27 | 重庆汉朗精工科技有限公司 | Negative liquid crystal composition and application thereof |
| CN116814277B (en) * | 2023-08-29 | 2023-12-26 | 烟台显华科技集团股份有限公司 | High-gradient high-brightness negative dielectric anisotropy liquid crystal composition and application thereof |
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| DE19814550A1 (en) * | 1998-04-01 | 1999-10-07 | Merck Patent Gmbh | Vinylene and ethyl compounds |
| JP5279975B2 (en) * | 2000-12-19 | 2013-09-04 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | Negative DC anisotropic alkenyl compound and liquid crystalline medium |
| JP4923380B2 (en) * | 2003-12-22 | 2012-04-25 | Ｊｎｃ株式会社 | Low refractive index anisotropic compounds, compositions and polymers or polymer compositions thereof |
| JP2007002132A (en) * | 2005-06-24 | 2007-01-11 | Chisso Corp | Liquid crystal composition and liquid crystal display element |
| CN101928199B (en) * | 2010-08-04 | 2013-02-13 | 烟台万润精细化工股份有限公司 | Divinyl liquid crystal compound and preparation method thereof |
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