CN110407803A - A kind of benzothiophene kind can poly- property compound and its application - Google Patents
A kind of benzothiophene kind can poly- property compound and its application Download PDFInfo
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- CN110407803A CN110407803A CN201810391054.3A CN201810391054A CN110407803A CN 110407803 A CN110407803 A CN 110407803A CN 201810391054 A CN201810391054 A CN 201810391054A CN 110407803 A CN110407803 A CN 110407803A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
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Abstract
The invention belongs to liquid crystal material technical fields, and in particular to a kind of benzothiophene kind can poly- property compound and its application, the compound has structure shown in general formula I.Compound of the present invention is compared to the prior art, more preferable with good dissolubility, orientation effect, and faster, polymerization is more complete for rate of polymerization, and residual is lower, shows bad problem to largely improve.Liquid-crystal composition containing the compound has lower viscosity, quick response may be implemented, there is moderate dielectric anisotropy △ ￡ simultaneously, liquid crystal display element or liquid crystal display comprising the liquid-crystal composition have the performances such as wider nematic temperature range, suitable or higher birefringence anisotropy △ n, higher resistivity, good anti-ultraviolet property, high charge retention rate and low-steam pressure.
Description
Technical field
The invention belongs to liquid crystal material technical field, being related to a kind of benzothiophene kind can poly- property compound and its application.
Background technique
In recent years, liquid crystal display device is widely used in various electronic equipments, such as smart phone, tablet computer, automobile
Navigator, television set etc..Representative liquid crystal display mode has twisted-nematic (TN) type, super twisted nematic (STN) type, face inscribe
Change (IPS) type, fringing field switching (FFS) type and vertical orientation (VA) type.Wherein, when VA mode is due to having quickly decline
Between, the image of high contrast, wide viewing angle and high quality, and receive more and more attention.
However, liquid crystal media used in the display element of the active array addressing mode of VA mode etc., there is not for itself
Foot, if image retention level will be significantly worse than the display element of positive dielectric anisotropy, the response time is slow, and driving voltage is relatively high
Deng.To solve the above-mentioned problems, there are some novel VA display technologies, such as MVA technology, PVA technology, PSVA technology.Its
In, PSVA technology had both realized the similar wide view angle display pattern of MVA/PVA, also simplified CF technique, and realizing reduces CF
While cost, aperture opening ratio is improved, higher brightness can also be obtained, and then obtain higher contrast.Further, since whole
The liquid crystal in face has pre-tilt angle, does not have domino delay phenomenon, can also obtain under the driving voltage maintained like faster
Response time, image retention level will not be affected.
The prior art has been found that the application aspect of LC mixture and RMs in PSA display still has the shortcomings that.It is first
It first, is not up to the present that each desired solvable RM is suitable for PSA display: simultaneously, if it is desired to by means of UV
Light is polymerize (this may be advantageous for certain applications) without adding photoinitiator, then selection becomes smaller: in addition,
LC mixture (hereinafter also referred to as " LC body mixture ") combines " material system " to be formed with selected polymerizable components and answers
With minimum rotary viscosity and best photoelectric properties, for increasing " voltage retention " (VHR) to reach effect.In PSVA
Aspect is very important using the high VHR after the irradiation of (UV) light, otherwise will lead to final display and the problems such as image retention occur.
Up to the present, due to there is no inclination angle to occur or occur deficiency after polymerizable unit is too short for UV sensibility wavelength or illumination
The poor problem of homogeneity after illumination of inclination angle or polymerizable components.Not all LC mixture with polymerizable group
The combination being grouped as is adapted to PSVA display.
Therefore, the synthesis and structure-performance relation of the new structural polymerizable compound with excellent properties are ground
Study carefully an important process as field of liquid crystals.
Summary of the invention
The first object of the present invention be to provide a kind of benzothiophene kind can poly- property compound, polymerizable liquid crystal of the present invention
Compound is compared to the prior art, more preferable with good dissolubility, orientation effect, and faster, polymerization is more complete for rate of polymerization,
Residual is lower, shows bad problem to largely improve.
Liquid-crystal composition containing the compound has lower viscosity, quick response may be implemented, while having moderate
Dielectric anisotropy △ ￡, liquid crystal display element or liquid crystal display comprising the liquid-crystal composition have wider nematic phase
Temperature range, suitable or higher birefringence anisotropy △ n, higher resistivity, good anti-ultraviolet property, height
The performances such as charge conservation rate and low-steam pressure.
Liquid-crystal compounds of the present invention, has the following structure:
Wherein, the P1、P2、P3Acrylate-based, methacrylate, fluoro acrylic ester are indicated independently of one another
Base, chloropropene perester radical, ethyleneoxy, oxetanyl or epoxy group；
The Z1、Z2、Z3Singly-bound ,-O- ,-S- ,-CO- ,-CO-O- ,-O-CO- ,-O-CO-O- ,-CH are indicated independently of one another
=N- ,-N=CH- ,-N=N-, C1-C12Alkylidene or C2-C12Alkenyl, wherein the C1-C12Alkylidene or C2-C12
Alkenyl in one or more hydrogen atoms can be replaced independently of one another by F, Cl or CN, and it is one or more non-conterminous
- CH2Group can independently of one another by-O- ,-S- ,-NH- ,-CO-, COO- ,-OCO- ,-OCOO- ,-SCO- ,-COS- or-
C=C- is replaced in a manner of not being connected directly mutually；
The ring A and ring B indicates 1,4- cyclohexylidene or 1,4- phenylene independently of one another；
The L1, L2, L3Expression-F ,-Cl ,-CN ,-NO independently of one another2、-CH3、-C2H5、-C(CH3)3、-CH(CH3)2、-
CH2CH(CH3)C2H5、-OCH3、-OC2H5、-COCH3、-COC2H5、-COOCH3、-COOC2H5、-CF3、-OCF3、-OCHF2Or-
OC2F5；
r1、r2、r30,1,2 or 3 are indicated independently of one another；
M indicates 0 or 1.
In general formula I, about P1、P2、P3: preferably, P1、P2、P3Methacrylate, propylene are indicated independently of one another
Perester radical, fluoropropenes acid ester group or chloropropene perester radical；
It is highly preferred that P1、P2、P3Methacrylate or acrylate-based is indicated independently of one another.
About Z1、Z2、Z3:
Preferably, Z1、Z2、Z3Singly-bound ,-O- ,-S- ,-CO-O- ,-O-CO-, C are indicated independently of one another1-C6Alkylidene or
C2-C6Alkenyl, wherein the C1-C6Alkylidene or C2-C6Alkenyl in one or more hydrogen atoms can each other solely
On the spot replaced by F, and one or more non-conterminous-CH2Group can be independently of one another by-O- with not mutual direct phase
Mode even replaces；
It is highly preferred that Z1、Z2、Z3Singly-bound ,-O-, C are indicated independently of one another1-C6Alkylidene or alkoxy.
About L1、L2:
Preferably, the L1, L2, L3Expression-F ,-Cl ,-CH independently of one another3、-C2H5、-OCH3、-OC2H5、-CF3Or
OCF3；
It is highly preferred that L1、L2Expression-F ,-Cl ,-CH3、-OCH3、-C2H5、-OC2H5。
About L3:
Preferably, L3Expression-F ,-Cl ,-CH3、-C2H5、-OCH3、-OC2H5、-CF3Or OCF3One of；
It is highly preferred that L3Indicate F or Cl.
About r1、r2、r3:
Preferably, r1、r2、r30,1 or 2 are indicated independently of one another；It is further preferred that r3Indicate 0 or 1.
In compound of the present invention, it is preferable that in general formula I, P1、P2、P3Methacrylic acid is indicated independently of one another
Ester group, acrylate-based, fluoropropenes acid ester group or chloropropene perester radical；
The Z1、Z2、Z3Singly-bound ,-O- ,-S- ,-CO-O- ,-O-CO-, C are indicated independently of one another1-C6Alkylidene or C2-
C6Alkenyl, wherein the C1-C6Alkylidene or C2-C6Alkenyl in one or more hydrogen atoms can be independently of one another
Replaced by F, and one or more non-conterminous-CH2What group can be connected directly mutually by-O- independently of one another
Mode replaces；
The ring A and ring B indicates 1,4- cyclohexylidene or 1,4- phenylene independently of one another；
The L1, L2, L3Expression-F ,-Cl ,-CH independently of one another3、-C2H5、-OCH3、-OC2H5、-CF3Or OCF3；
r1、r2、r30,1 or 2 are indicated independently of one another；
M indicates 0 or 1.
It is further preferred that in general formula I, P1、P2、P3Methacrylate or acrylate are indicated independently of one another
Base；
The Z1、Z2、Z3Singly-bound ,-O-, C are indicated independently of one another1-C6Alkylidene or alkoxy；
The ring A and ring B indicates 1,4- cyclohexylidene or 1,4- phenylene independently of one another；
L1、L2Expression-F ,-Cl ,-CH3、-OCH3、-C2H5、-OC2H5；
L3Indicate F or Cl；
r1、r2、r30,1 or 2 are indicated independently of one another.
M indicates 0 or 1；
As present invention technical solution still more preferably, in the compound:
Work as m=0, when ring A is 1 or 4 cyclohexylidene, L1、L2、L3Expression-F or-Cl independently of one another；
Or, work as m=1, ring A is 1 or 4 cyclohexylidene, and when ring B is Isosorbide-5-Nitrae-phenylene, r3Indicate 0；
Or, work as m=1, and when ring A and ring B are 1 or 4 cyclohexylidene, r1=r2=0；
Or, working as r1And/or r2When indicating 2, r3Indicate 0；
Or, working as L2Expression-CH3、-OCH3、-C2H5、-OC2H5One of, and r2When not being 0, r3Indicate 0；
Or, when ring A is Isosorbide-5-Nitrae-phenylene, r1+r2+r3≤4。
As most preferred technique scheme of the invention, the compound is selected from one kind of following compound:
As preferred forms of the invention, the compound is selected from one of following compound:
Second purpose of hair invention is the composition that protection contains the liquid-crystal compounds.Preferably, the compound exists
Mass percent in composition is 0.01~10%, more preferably 0.01~5%, further preferably 0.1~3%.
The third object of the present invention is that the protection liquid-crystal compounds and the composition containing the liquid-crystal compounds exist
The application of field of liquid crystal display, the application preferably in liquid crystal display device.The liquid crystal display device includes but not
It is limited to TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.It has used the liquid-crystal compounds or has contained the LCD compound
The composition of object has wider nematic temperature range, suitable or higher birefringence anisotropy △ n, higher electricity
The performances such as resistance rate, good anti-ultraviolet property, high charge retention rate and low-steam pressure.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention., all other without departing from the present invention
The lower equivalent change or modification completed of revealed spirit, should be included in the scope of the said claims.
Each liquid-crystal compounds used by below in an example unless otherwise instructed, can pass through well known method
Carry out synthesize or obtained from public commercial source, these synthetic technologys be it is conventional, acquired each liquid-crystal compounds accords with after tested
Close standard for electronic compounds.
According to the common detection methods of this field, the various performance parameters of liquid-crystal compounds are obtained by linear fit,
In, the concrete meaning of each performance parameter is as follows:
△ n represents optical anisotropy (25 DEG C)；△ ε represents dielectric anisotropy (25 DEG C, 1000Hz)；γ 1 represents rotation
Turn viscosity (mPa.s, 25 DEG C)；Cp represents clearing point.
Embodiment 1
The structural formula of liquid-crystal compounds are as follows:
The synthetic line of prepare compound BYLC-01 is as follows:
Specific step is as follows:
(1) synthesis of compound BYLC-01-1:
45.0g Y-1,34.2g 3,5- dihydroxybiphenyl boric acid, 16.0g Anhydrous potassium carbonate, 200ml are added in reaction flask
Toluene, 150ml ethyl alcohol, 150ml water, tetra- triphenylphosphine of 0.3g close palladium, and heating reflux reaction 8h carries out conventional post-processing, obtains
Off-white powder (compound BYLC-01-1) 56.5g, HPLC:99.5%, yield 85.2%；
(2) synthesis of compound BYLC-01-2:
Addition 56.5g compound BYLC-01-1,8.0g NaOH, 200ml deionized water in reaction flask, 200ml ethyl alcohol, 65
DEG C~70 DEG C of reaction 2h.After being acidified with hydrochloric acid, conventional post-processing is carried out, white solid (compound BYLC-01-2) is obtained,
53.4g, HPLC:99.6%, yield 92.6%
(3) synthesis of compound BYLC-01:
Under nitrogen protection, 53.4g compound BYLC-01-2,35.5g triethylamine and 300mL dichloro are added into reaction flask
Methane is cooled to -10 DEG C, and 36.8g methacrylic chloride is added dropwise in -10 DEG C of temperature control~0 DEG C, is warmed to room temperature reaction 6h and falls reaction solution
Enter in water, neutralized with bicarbonate uranium aqueous solution, carry out conventional post-processing, through chromatogram purification, n-hexane elution, ethyl alcohol recrystallization is obtained
To white solid (compound BYLC-01) 69.2g, LC:99.5%, yield: 80.5%.
Gained white solid BYLC-01 is analyzed using GC-MS, the m/z of product is 538.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,9H),5.35-6.55(m,6H),6.65-7.95(m,
11H)。
Embodiment 2
The structural formula of liquid-crystal compounds are as follows:
The synthetic line of prepare compound BYLC-02 is as follows:
Specific step is as follows:
The synthesis of compound BYLC-02:
Under nitrogen protection, 42.0g compound BYLC-01-2,31.0g triethylamine and 250mL dichloro are added into reaction flask
Methane is cooled to -10 DEG C, and 27.0g acryloyl chloride is added dropwise in -10 DEG C of temperature control~0 DEG C, is warmed to room temperature reaction 6h for reaction solution and pours into water
In, it is neutralized with bicarbonate uranium aqueous solution, carries out conventional post-processing, through chromatogram purification, n-hexane elution, ethyl alcohol recrystallization obtains white
Color solid (compound BYLC-02) 53.3g, LC:99.7%, yield: 85.6%.
Gained white solid BYLC-02 is analyzed using GC-MS, the m/z of product is 496.1 (M+).
1H-NMR(300MHz,CDCl3):5.15-5.75(m,3H),5.85-6.85(m,8H),7.05-7.95(m,9H)。
Embodiment 3
The structural formula of liquid-crystal compounds are as follows:
WithInstead ofOther reaction conditions are the same as embodiment 1.
Gained white solid BYLC-03 is analyzed using GC-MS, the m/z of product is 574.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,7H),5.35-6.55(m,6H),6.65-7.95(m,
11H)。
Embodiment 4
The structural formula of liquid-crystal compounds are as follows:
WithInstead ofOther reaction conditions are the same as embodiment 1.
Gained white solid BYLC-04 is analyzed using GC-MS, the m/z of product is 556.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,8H),5.35-6.55(m,6H),6.65-7.95(m,
11H)。
Embodiment 5
The structural formula of liquid-crystal compounds are as follows:
WithInstead ofOther conditions are the same as embodiment 1.
Gained white solid BYLC-05 is analyzed using GC-MS, the m/z of product is 556.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,8H),5.35-6.55(m,6H),6.65-7.95(m,
11H)。
Embodiment 6
The structural formula of liquid-crystal compounds are as follows:
WithInstead ofOther reaction conditions are the same as embodiment 1.
Gained white solid BYLC-06 is analyzed using GC-MS, the m/z of product is 538.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,7H),5.35-6.55(m,8H),6.65-7.95(m,
11H)。
Embodiment 7
The structural formula of liquid-crystal compounds are as follows:
WithInstead ofOther conditions are the same as embodiment 1.
Gained white solid BYLC-07 is analyzed using GC-MS, the m/z of product is 552.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,8H),5.35-6.55(m,8H),6.65-7.95(m,
11H)。
Embodiment 8
The structural formula of liquid-crystal compounds are as follows:
Gained white solid BYLC-08 is analyzed using GC-MS, the m/z of product is 598.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,9H),5.35-6.85(m,14H),7.05-7.95(m,
7H)。
Embodiment 9
The structural formula of liquid-crystal compounds are as follows:
WithInstead ofOther reaction conditions are the same as embodiment 1.
Gained white solid BYLC-09 is analyzed using GC-MS, the m/z of product is 462.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,9H),5.35-6.85(m,8H),7.05-7.95(m,5H)。
Embodiment 10
The structural formula of liquid-crystal compounds are as follows:
Gained white solid BYLC-10 is analyzed using GC-MS, the m/z of product is 554.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,9H),2.35-4.15(m,3H),5.35-6.85(m,6H),
7.05-7.95(m,7H)。
Embodiment 11
The structural formula of liquid-crystal compounds are as follows:
Gained white solid BYLC-11 is analyzed using GC-MS, the m/z of product is 552.1 (M+).
1H-NMR(300MHz,CDCl3):1.55-2.15(m,12H),5.35-6.55(m,6H),6.65-7.95(m,
9H)。
Embodiment 12
Technical solution according to above embodiments, it is only necessary to which the corresponding raw material of simple replacement does not change any substantive behaviour
Make, following liquid-crystal compounds can be synthesized.
Embodiment 13
The property of liquid crystal compound BHR87800 is listed in Table 1 below:
1 mixed crystal BHR87800 property summary sheet of table
Wherein, mixture BHR87800 is purchased from Bayi Space liquid crystal Science and Technology Co., Ltd..The embodiment of addition 0.3%
In the liquid-crystal composition BHR87800 of polymerizable compound BYLC-01 to 99.7% provided by 1, uniform dissolution is mixed
Object PM-1.
The liquid-crystal composition of polymerizable compound BYLC-02 to 99.7% provided by the embodiment 2 of addition 0.3%
In BHR87800, uniform dissolution obtains mixture PM-2.
The liquid-crystal composition of polymerizable compound BYLC-06 to 99.7% provided by the embodiment 6 of addition 0.3%
In BHR87800, uniform dissolution obtains mixture PM-3.
The liquid-crystal composition of polymerizable compound BYLC-07 to 99.7% provided by the embodiment 7 of addition 0.3%
In BHR87800, uniform dissolution obtains mixture PM-4.
The physical property of PM-1, PM-2, PM-3, PM-4 and the physical property of said mixture BHR87800 are almost without difference.It uses
PM-1, PM-2, PM-3, PM-4 injection gap are 4.0 μm and had in the testing cassete of vertical orientation by priming by vacuum method.On one side
Application frequency is 60HZ, and driving voltage is the square wave of 16V, irradiates ultraviolet light to testing cassete with high-pressure mercury ultraviolet lamp on one side, adjusts
The exposure intensity for saving box surface is 30mW/cm2, irradiates 600s, the liquid crystal display element of the vertical orientation after being polymerize makes
Pre-tilt angle is measured with LCT-5016E liquid crystal electro-optic parameter tester, testing cassete is then decomposed, is surveyed using high-efficient liquid phase chromatogram HPLC
Determine remaining polymerizable compound in liquid-crystal composition, is as a result summarized in table 2 and table 3.
Comparative example
In the liquid-crystal composition BHR87800 of the polymerizable compound to 99.7% of the CP of addition 0.3%, uniform dissolution is obtained
To mixture PM-5.The physical property of PM-5 and the physical property of said mixture BHR87800 are almost without difference.Use priming by vacuum method
PM-5 injection gap is 4.0 μm and had in the testing cassete of vertical orientation.Applying frequency on one side is 60HZ, and driving voltage is
The square wave of 16V, irradiates ultraviolet light to testing cassete with high-pressure mercury ultraviolet lamp on one side, and the exposure intensity adjusted to box surface is
30mW/cm2, irradiates 600s, and the liquid crystal display element of the vertical orientation after being polymerize is joined using LCT-5016E liquid crystal electro-optic
Number tester measures pre-tilt angle, then decomposes testing cassete, using remaining in high-efficient liquid phase chromatogram HPLC measurement liquid-crystal composition
As a result polymerizable compound is summarized in table 2 and table 3.
Pre-tilt angle summary sheet before and after 2 UV of table
3 polymer residue data summary table of table
From the correlation data of table 2 and table 3 it is found that polymerizable compound relative polymerization liquid-crystal compounds CP of the invention,
The orientation effect being formed by is more preferable, and faster, polymerization is more complete for rate of polymerization, and residual is lower, so that biggish improve display
Bad problem.
Although above having used general explanation, specific embodiment and test, the present invention is made to retouch in detail
It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Range.
Claims (10)
1. a kind of benzothiophene kind can poly- property compound, which is characterized in that have structure shown in general formula I:
Wherein, the P1、P2、P3Acrylate-based, methacrylate, fluoropropenes acid ester group, chlorine are indicated independently of one another
For acrylate-based, ethyleneoxy, oxetanyl or epoxy group；
The Z1、Z2、Z3Singly-bound ,-O- ,-S- ,-CO- ,-CO-O- ,-O-CO- ,-O-CO-O- ,-CH=are indicated independently of one another
N- ,-N=CH- ,-N=N-, C1-C12Alkylidene or C2-C12Alkenyl, wherein the C1-C12Alkylidene or C2-C12's
One or more hydrogen atoms in alkenyl can be replaced by F, Cl or CN independently of one another, and it is one or more it is non-conterminous-
CH2Group can be independently of one another by-O- ,-S- ,-NH- ,-CO-, COO- ,-OCO- ,-OCOO- ,-SCO- ,-COS- or-C=
C- is replaced in a manner of not being connected directly mutually；
The ring A and ring B indicates 1,4- cyclohexylidene or 1,4- phenylene independently of one another；
The L1, L2, L3Expression-F ,-Cl ,-CN ,-NO independently of one another2、-CH3、-C2H5、-C(CH3)3、-CH(CH3)2、-
CH2CH(CH3)C2H5、-OCH3、-OC2H5、-COCH3、-COC2H5、-COOCH3、-COOC2H5、-CF3、-OCF3、-OCHF2Or-
OC2F5；
The r1、r2、r30,1,2 or 3 are indicated independently of one another；
The m indicates 0 or 1.
2. compound according to claim 1, which is characterized in that P1、P2、P3Methacrylate is indicated independently of one another
Base, acrylate-based, fluoropropenes acid ester group or chloropropene perester radical；
Preferably, P1、P2、P3Methacrylate or acrylate-based is indicated independently of one another.
3. compound according to claim 1 or 2, which is characterized in that Z1、Z2、Z3Independently of one another indicate singly-bound ,-O- ,-
S-、-CO-O-、-O-CO-、C1-C6Alkylidene or C2-C6Alkenyl, wherein the C1-C6Alkylidene or C2-C6Alkene
One or more hydrogen atoms in base can be replaced by F independently of one another, and one or more non-conterminous-CH2Group can be with
It is replaced in a manner of not being connected directly mutually by-O- independently of one another；
Preferably, Z1、Z2、Z3Singly-bound ,-O-, C are indicated independently of one another1-C6Alkylidene or alkoxy.
4. compound according to claim 1-3, which is characterized in that the L1, L2Independently of one another expression-F ,-
Cl、-CH3、-C2H5、-OCH3、-OC2H5、-CF3Or OCF3；
Preferably, L1、L2Expression-F ,-Cl ,-CH independently of one another3、-OCH3、-C2H5Or-OC2H5。
5. compound according to claim 1-4, which is characterized in that the L3Expression-F ,-Cl ,-CH3、-
C2H5、-OCH3、-OC2H5、-CF3Or OCF3One of；
Preferably, L3Indicate F or Cl.
6. compound according to claim 1-5, which is characterized in that the r1、r2、r3It indicates independently of one another
0,1 or 2；
Preferably, the r3Indicate 0 or 1.
7. compound according to claim 1-6, which is characterized in that in general formula I:
Work as m=0, when ring A is 1 or 4 cyclohexylidene, L1、L2、L3Expression-F or-Cl independently of one another；
Or, work as m=1, ring A is 1 or 4 cyclohexylidene, and when ring B is Isosorbide-5-Nitrae-phenylene, r3Indicate 0；
Or, work as m=1, and when ring A and ring B are 1 or 4 cyclohexylidene, r1=r2=0；
Or, working as r1And/or r2When indicating 2, r3Indicate 0；
Or, working as L2Expression-CH3、-OCH3、-C2H5、-OC2H5One of, and r2When not being 0, r3Indicate 0；
Or, when ring A is Isosorbide-5-Nitrae-phenylene, r1+r2+r3≤4。
8. compound according to claim 1-7, which is characterized in that one kind selected from following compound:
Preferably, selected from one of following compound:
9. a kind of liquid-crystal composition, which is characterized in that contain the described in any item compounds of claim 1-8；
Preferably, the mass percent of the compound in the composition be 0.01~10%, more preferably 0.01~
5%, further preferably 0.1~3%.
10. the described in any item compounds of claim 1-8 and/or composition as claimed in claim 9 are in field of liquid crystal display
Application, the application preferably in liquid crystal display device；The more preferably described liquid crystal display device include TN, ADS, VA,
PSVA, FFS or IPS liquid crystal display.
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