CN107286950A - A kind of cyclopenta liquid-crystal compounds, composition and its application - Google Patents
A kind of cyclopenta liquid-crystal compounds, composition and its application Download PDFInfo
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- CN107286950A CN107286950A CN201610204205.0A CN201610204205A CN107286950A CN 107286950 A CN107286950 A CN 107286950A CN 201610204205 A CN201610204205 A CN 201610204205A CN 107286950 A CN107286950 A CN 107286950A
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- 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
- C09K19/063—Non-steroidal liquid crystal compounds containing one non-condensed saturated non-aromatic ring, e.g. cyclohexane ring
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/137—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering
- G02F1/13712—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering the liquid crystal having negative dielectric anisotropy
Abstract
The present invention relates to a kind of new cyclopenta liquid-crystal compounds, the structure of the compound is as shown in formula I；The compound has the advantages that higher negative dielectric anisotropic, good liquid crystal intersolubility, relatively low rotary viscosity, and these exactly improve required for liquid crystal material, with important application value.Liquid-crystal composition invention further provides the preparation method of the liquid-crystal compounds and containing the liquid-crystal compounds.The liquid-crystal compounds and composition containing the liquid-crystal compounds have excellent application effect in field of liquid crystal display especially in liquid crystal display device.
Description
Technical field
The present invention relates to liquid crystal display material field, more particularly to a kind of liquid-crystal compounds, combination
Thing and its application.
Background technology
Liquid crystal material is as environmentally conscious materialses in fields such as presentation of information material, organic optoelectronic materials
In application there is great researching value and fine application prospect.Liquid crystal material is as new
Display material has many advantages, and such as power consumption is extremely low, and driving voltage is low.Simultaneously with other materials phase
Than also with small volume, lightweight, long-life, the big, electromagnetic-radiation-free of display information amount etc.
Advantage, is almost adapted to the requirement of various presentation of information, and especially in TFT-LCD, (film is brilliant
Body Manifold technology) product aspect.
In recent years, the application field of liquid-crystal compounds is more and more wider, is widely used for various types of
Display device, Electrooptical devices, sensor of type etc..Wherein, nematic phase in a display device
Liquid crystal has most broad purposes.Nematic liquid crystal has been widely used for passive TN or STN squares
In battle array display and system with tft active matrix
At present, TFT-LCD product technologies are ripe, successfully solve visual angle, resolution
The technical barriers such as rate, color saturation and brightness, large scale and small-medium size TFT-LCD are shown
Device has gradually occupied the dominant position of flat-panel monitor in respective field.But to Display Technique
Requirement constantly improving always, it is desirable to liquid crystal display realize faster respond, reduce
Driving voltage is with terms of reducing power consumption.
With the development of Display Technique, higher requirement is it is also proposed to liquid crystal material, especially
In quick response, in terms of reducing driving voltage, reduction power consumption.Accordingly, it would be desirable to develop more
Improve the novel liquid crystal compound of performance.
The content of the invention
The first object of the present invention is to provide a kind of new cyclopenta liquid-crystal compounds, the chemical combination
There is thing higher negative dielectric anisotropic, good liquid crystal intersolubility, relatively low rotation to glue
The advantages of spending, these exactly improve required for liquid crystal material, with important application value.
Specifically, cyclopenta liquid-crystal compounds of the present invention, with knot shown in formula I
Structure：
In formula I：R represents alkyl or alkoxy with 1-10 carbon atom；Ring A
Represent the 1,4- that 1,4- phenylenes, 1,4- cyclohexylidenes or 1-4 hydrogen atom are replaced by fluorine atoms
Phenylene；Ring B represents 1,4- phenylenes, 1,4- cyclohexylidenes, 1,4- cyclohexadienylidenes or 1-4
The 1,4- phenylenes that individual hydrogen atom is replaced by fluorine atoms；M is 0,1 or 2, n are 0 or 1,
And be 0 when m, n difference；Wherein, further preferred n=1 and m=0,1 or 2.
Preferably, in formula I：R represents alkyl or alkoxy with 1-5 carbon atom；
Ring A represents what 1,4- phenylenes, 1,4- cyclohexylidenes or 1-4 hydrogen atom were replaced by fluorine atoms
1,4- phenylenes；Ring B represent 1,4- phenylenes, 1,4- cyclohexylidenes, 1,4- cyclohexadienylidenes or
The 1,4- phenylenes that 1-4 hydrogen atom is replaced by fluorine atoms；M be 0,1 or 2, n be 0 or
1, and be 0 when m, n difference；Wherein, further preferred n=1 and m=0,1 or 2.
In such scheme, as m=2, the group that two ring A are represented can with identical,
Can be different.
It is highly preferred that in formula I, R represents alkyl or alcoxyl with 1-5 carbon atom
Base；Ring A represents that 1,4- phenylenes, 1,4- cyclohexylidenes or 1-2 hydrogen atom are taken by fluorine atom
The 1,4- phenylenes in generation；Ring B represents the sub- cyclohexene of 1,4- phenylenes, 1,4- cyclohexylidenes, 1,4-
The 1,4- phenylenes that base or 1-2 hydrogen atom are replaced by fluorine atoms；M is 0 or 1, n are 0
Or 1, and be 0 when m, n difference；Wherein, further preferred n=1 and m=0 or 1.
As currently preferred technical scheme, the liquid-crystal compounds is selected from following compound
It is a kind of：
In I-1~I-16, R represents alkyl or alkoxy with 1-5 carbon atom.
As the preferred forms of the present invention, the liquid-crystal compounds is selected from following compound
It is a kind of：
The second object of the present invention is to provide the preparation method of the liquid-crystal compounds.
The present invention selects different synthetic routes according to ring B difference.
As the first technical scheme, when ring B is Isosorbide-5-Nitrae-phenylene or 1-4 hydrogen atom quilt
During Isosorbide-5-Nitrae-phenylene of fluorine atom substitution, i.e.,
(П), synthetic route is as follows：
Specifically include following steps：
(1)React, then reacted with borate with organolithium reagent, obtained
(2) withWithFor raw material, lead to
Suzuki reactions are crossed, are obtained
Wherein, in compound involved by each step R, m, ring A, ring B and gained liquid crystal
The group that R, m, ring A, ring B are represented in compound product is corresponding.
Step 1 described in the above method) in,Organolithium reagent and borate
Molar ratio be preferably 1: 1.0~4.0: 1.0~4.0, reaction temperature -50~-100 DEG C；
Wherein, the organolithium reagent be selected from s-butyl lithium, tert-butyl lithium or n-BuLi with
One or more in potassium tert-butoxide, it is different that the borate is selected from trimethylborate, boric acid three
One or more in propyl ester, butyl borate or the isobutyl ester of boric acid three.
The step 2) in,With's
Molar ratio is preferably 1: 0.9~1.2,60~120 DEG C of reaction temperature.
As second of technical scheme, when ring B is Isosorbide-5-Nitrae-cyclohexylidene, i.e.,Synthetic route is as follows：
Specifically include following steps：
(1)With organolithium reagent carry out metallization reaction, then withReaction, is obtained
(2)By with BFEE, three
Ethylsilane is reacted, and is obtained
Wherein, in compound involved by each step R, m, ring A and gained LCD compound
The group that R, m, ring A are represented in thing product is corresponding.
Step 1 described in the above method) in,Organolithium reagent withMolar ratio be preferably 1.0~4.0：1.0~4.0: 1,
Reaction temperature -50~-100 DEG C；
Wherein, the organolithium reagent is in s-butyl lithium, tert-butyl lithium or n-BuLi
One or more.
The step 2) in,Boron trifluoride second
The molar ratio of ether and triethyl silicane is preferably 1: 0.5~3.0：0.5~3.0, reaction temperature
- 20~-100 DEG C of degree.
As the third technical scheme, when ring B is Isosorbide-5-Nitrae-cyclohexadienylidene, i.e.,
Synthetic route is as follows：
Specifically include following steps：
(1)With organolithium reagent carry out metallization reaction, then withReaction, is obtained
(2)It is dehydrated, obtains under acid catalysis
Wherein, in compound involved by each step R, m, ring A and gained LCD compound
The group that R, m, ring A are represented in thing product is corresponding.
Step 1 described in the above method) in,Organolithium reagent,Molar ratio be preferably 1.0~4.0：1.0~4.0: 1,
Reaction temperature -50~-100 DEG C；
Wherein, the organolithium reagent is in s-butyl lithium, tert-butyl lithium or n-BuLi
One or more.
The step 2) in,With feeding intake for acid
Mol ratio is preferably 1: 0.1~0.2,50~120 DEG C of reaction temperature；
Wherein, the acid is selected from hydrochloric acid, sulfuric acid, formic acid, acetic acid, p-methyl benzenesulfonic acid, sulphur
One or more in potassium hydrogen phthalate, preferably p-methyl benzenesulfonic acid.
It should be further stated that, above-mentioned three kinds prepare scheme and are directed to comprising ring B, i.e.
N=1 liquid-crystal compounds；When in the liquid-crystal compounds be not present ring B, i.e. during n=0,
The structure of liquid-crystal compounds is as follows：
As n=0, m=1, compound is
As n=0, m=2, compound is
Above-mentioned A2、A1Ring A is represented, the two group represented can be with identical, can also not
Together.
For compound shown in logical formula (V), (VI)：As wherein A1For the sub- benzene of 1,4-
During Isosorbide-5-Nitrae-phenylene that base or 1-4 hydrogen atom are replaced by fluorine atoms, in the first above-mentioned preparation
On the basis of technical scheme, without changing substantive operations, corresponding raw material is only simply adjusted,
Logical formula (V) can be prepared, compound shown in (VI)；As wherein A1For the sub- rings of 1,4-
During hexyl, on the basis of above-mentioned second of technology of preparing scheme, without changing substantive behaviour
Make, only simply adjust corresponding raw material, you can prepare logical formula (V), (VI) shownization
Compound.
Method of the present invention, can be related to after conventional post processing, the routine when necessary
Processing is specific such as：Extracted with dichloromethane, ethyl acetate or toluene, point liquid is washed, and is done
Dry, vacuum rotary evaporator evaporates, products therefrom vacuum distillation or recrystallization and/or chromatogram
Partition method is purified, you can.
It can be stablized using above-mentioned preparation method, be efficiently obtained liquid-crystalization of the present invention
Compound.
The third object of the present invention is composition of the protection containing the liquid-crystal compounds.It is described
The mass percent of liquid-crystal compounds in the composition is 1~60%, preferably 3~50%, is entered
One step is preferably 5~25%.
The fourth object of the present invention is the protection liquid-crystal compounds and liquid-crystalized containing described
The composition of compound, in the application of field of liquid crystal display, is preferably in liquid crystal display device
Using.Described liquid crystal display device include but is not limited to TN, ADS, VA, PSVA,
FFS or IPS liquid crystal displays.The liquid-crystal compounds is used or has liquid-crystalized containing described
The composition of compound has high negative dielectric anisotropic, and rotary viscosity is low, so that effectively
Driving voltage is reduced, the response speed of liquid crystal display device is improved, while having optics each
The features such as anisotropy numerical value is moderate, electric charge conservation rate is high.
Embodiment
Following examples are used to illustrate the present invention, but are not limited to the scope of the present invention.
The raw material unless otherwise instructed, can be obtained from open commercial sources.
According to the common detection methods of this area, liquid-crystal compounds is obtained by linear fit
Various performance parameters, wherein, the concrete meaning of each performance parameter is as follows：
Δ n represents optical anisotropy (25 DEG C)；Δ ε represent dielectric anisotropy (25 DEG C,
1000Hz)；γ 1 represents rotary viscosity (mPa.s, 25 DEG C).
Embodiment 1
The structural formula of liquid-crystal compounds is：
Prepare compound BYLC-01 synthetic line is as follows：
Comprise the following steps that：
(1) compound BYLC-01-1 synthesis：
Under nitrogen protection, the fluoro- 7- propoxyl group naphthalenes of 24.0g 1,2,8- tri- are added into reaction bulb,
150ml tetrahydrofurans, the n-hexane that 0.12mol n-BuLis are added dropwise in temperature control -70~-80 DEG C is molten
Liquid, drop finishes insulation reaction 1 hour, and 15.6g trimethylborates are added dropwise in temperature control -70~-80 DEG C,
Then rise again naturally to -30 DEG C.Add 2M aqueous hydrochloric acid solutions 300ml to be acidified, carry out
Conventional post processing, petroleum ether is recrystallized to give light yellow solid (compound BYLC-01-1)
25.8g, HPLC：99.2%, yield 91%；
(2) compound BYLC-01 synthesis：
Under nitrogen protection, 24.0g compounds BYLC-01-1,19.0g are added into reaction bulb
Compound 4- cyclopenta bromobenzenes, 150ml DMFs, 50ml deionized waters,
11.6g Anhydrous potassium carbonates, 0.4g tetra-triphenylphosphine palladiums, heating reflux reaction 3 hours.Carry out
Conventional post processing, through chromatogram purification, n-hexane elution, ethyl alcohol recrystallization obtains white solid
(compound BYLC-01) 27.6g, GC：99.7%, yield：85.2%.
Gained white solid BYLC-01 is analyzed using GC-MS, the m/z of product
For 384.1 (M+).
1H-NMR(300MHz,CDCl3):0.87-1.95 (m, 13H), 2.55-2.95 (m, 1H),
3.53-4.15(m,2H),6.95-7.73(m,7H)。
Embodiment 2
Technical scheme according to embodiment 1, it is only necessary to simply replace corresponding raw material, do not change
Any substantive operations, can synthesize following liquid-crystal compounds.
Embodiment 3
The structural formula of liquid-crystal compounds is：
Prepare compound BYLC-03 synthetic line is as follows：
Comprise the following steps that：
(1) compound BYLC-03-1 synthesis：
Nitrogen protection under, into reaction bulb add the fluoro- 7- propoxyl group naphthalenes of 50.4g 1,2,8- tri- and
The hexane solution of 0.23mol butyl lithiums is added dropwise in 320ml tetrahydrofurans, temperature control -75~-85 DEG C,
Drop finishes insulation reaction 1 hour, temperature control -75~-85 DEG C be added dropwise 33.2g cyclopentyl cyclohexyls ketone and
The solution of 60ml tetrahydrofurans composition, then rises again to -30 DEG C naturally.Add 200ml water quenchings
Go out reaction, carry out conventional post processing, obtain light yellow liquid (compound BYLC-03-1)
78.3g, HPLC：93.7%, yield 96.5%；
(2) compound BYLC-03 synthesis：
Under nitrogen protection, 70g compounds BYLC-03-1 and 170ml are added into reaction bulb
40.0g triethyl silicanes are added dropwise in dichloromethane, temperature control -70~-80 DEG C, and drop finishes insulation reaction 0.5
Hour, temperature control -70~-80 DEG C be added dropwise 49.0g BFEEs, then rise again naturally to
-20℃.Add 200ml water quenchings to go out reaction, carry out conventional post processing, obtain white solid and (change
Compound BYLC-03) 52.4g, GC：99.7%, yield 78%；
Gained white solid BYLC-03 is analyzed using GC-MS, the m/z of product
For 390.1 (M+).
1H-NMR(300MHz,CDCl3):0.85-1.93 (m, 23H), 2.55-2.87 (m, 1H),
3.74-4.10(m,2H),6.95-7.55(m,3H)。
Embodiment 4
Technical scheme according to embodiment 3, it is only necessary to simply replace corresponding raw material, do not change
Any substantive operations, can synthesize following liquid-crystal compounds.
Embodiment 5
The structural formula of liquid-crystal compounds is：
Prepare compound BYLC-05 synthetic line is as follows：
Comprise the following steps that：
(1) compound BYLC-05-1 synthesis：
Nitrogen protection under, into reaction bulb add the fluoro- 7- propoxyl group naphthalenes of 25.2g 1,2,8- tri- and
The hexane solution of 0.12mol butyl lithiums is added dropwise in 250ml tetrahydrofurans, temperature control -75~-85 DEG C,
Drop finishes insulation reaction 1 hour, and 24.8g cyclopenta dicyclohexyl ketone is added dropwise in temperature control -75~-85 DEG C
The solution constituted with 60ml tetrahydrofurans, then rises again to -30 DEG C naturally.Add 200ml
Water quenching is gone out reaction, is carried out conventional post processing, is obtained light yellow liquid (compound BYLC-05-1)
46.7g, HPLC：96.8%, yield 95.7%；
(2) compound BYLC-05 synthesis：
45g BYLC-05-1,0.5g p-methyl benzenesulfonic acid, 0.2g 2,6- bis- are added into reaction bulb
Butylated Hydroxytoluene and 300ml toluene, reflux water-dividing react 4 hours.Locate after routine
Reason, obtains white solid (compound BYLC-05) 32.5g, GC：99.7%, yield 75%；
Gained white solid BYLC-05 is analyzed using GC-MS, the m/z of product
For 470.2 (M+).
1H-NMR(300MHz,CDCl3):0.85-2.10 (m, 31H), 3.79-4.10 (m, 2H),
5.53-6.12(m,1H),6.63-7.75(m,3H)。
Embodiment 6
Technical scheme according to embodiment 5, it is only necessary to simply replace corresponding raw material, do not change
Any substantive operations, can synthesize following liquid-crystal compounds.
Experimental example 1
By the compound BYLC-01 and the liquid-crystal compounds of comparative example 1 obtained by embodiment 1
Performance parameter data carry out contrast arrangement, and testing result is as shown in table 1：
Table 1：The performance test results of liquid-crystal compounds
By the testing result of table 1, it is apparent that the liquid-crystal compounds that provides of the present invention with
The negative dielectric anisotropic compound phase ratio of traditional similar chemical structure, bears with higher
Dielectric anisotropy, rotary viscosity γ 1 are moderate, good low temperature intersolubility and higher limpid
Point performance, these exactly improve required for liquid crystal material, can effectively improve liquid crystal combination
The dielectric anisotropy Δ ε of thing, reduces driving voltage, the faster liquid crystal group of the speed that meets with a response
Compound.
Experimental example 2
By the compound obtained by embodiment 2 and the liquid-crystal compounds performance parameter of comparative example 2
Data carry out contrast arrangement, and testing result is as shown in table 2：
Table 2：The performance test results of liquid-crystal compounds
By the testing result of table 2, it is apparent that the liquid-crystal compounds that provides of the present invention with
The negative dielectric anisotropic compound phase ratio of traditional similar chemical structure, bears with higher
Dielectric anisotropy, rotary viscosity γ 1 are moderate, good low temperature intersolubility and higher limpid
Point performance, these exactly improve required for liquid crystal material, can effectively improve liquid crystal combination
The dielectric anisotropy Δ ε of thing, reduces driving voltage, the faster liquid crystal group of the speed that meets with a response
Compound.
Experimental example 3
By the compound obtained by embodiment 4 and the liquid-crystal compounds performance parameter of comparative example 3
Data carry out contrast arrangement, and testing result is as shown in table 3：
Table 3：The performance test results of liquid-crystal compounds
By the testing result of table 3, it is apparent that the liquid-crystal compounds that provides of the present invention with
The negative dielectric anisotropic compound phase ratio of traditional similar chemical structure, bears with higher
Dielectric anisotropy, rotary viscosity γ 1 are moderate, good low temperature intersolubility and higher limpid
Point performance, these exactly improve required for liquid crystal material, can effectively improve liquid crystal combination
The dielectric anisotropy Δ ε of thing, reduces driving voltage, the faster liquid crystal group of the speed that meets with a response
Compound.
In addition, herein described compound to be particularly applicable in the liquid-crystal composition of conventional system
In after find, it can improve the dielectric anisotropy Δ ε of liquid-crystal composition, at the same keep compared with
Low rotary viscosity γ 1 and appropriate refractive anisotrop Δ n, gained liquid-crystal composition has
Significant quick response feature and low voltage drive feature.
Although above having made in detail to the present invention with a general description of the specific embodiments
Most description, but on the basis of the present invention, it can be made some modifications or improvements, this is to this
It is obvious for art personnel.Therefore, on the basis without departing from spirit of the present invention
Upper these modifications or improvements, belong to the scope of protection of present invention.
Claims (10)
1. a kind of cyclopenta liquid-crystal compounds, it is characterised in that with the structure shown in formula I：
In the formula I：R represents alkyl or alkoxy with 1-10 carbon atom；
Ring A represents that 1,4- phenylenes, 1,4- cyclohexylidenes or 1-4 hydrogen atom are taken by fluorine atom
The 1,4- phenylenes in generation；
Ring B represents 1,4- phenylenes, 1,4- cyclohexylidenes, 1,4- cyclohexadienylidenes or 1-4 hydrogen
The 1,4- phenylenes that atom is replaced by fluorine atoms；
M is 0,1 or 2, n are 0 or 1, and is 0 when m, n difference.
2. cyclopenta liquid-crystal compounds according to claim 1, it is characterised in that institute
State in formula I：R represents alkyl or alkoxy with 1-5 carbon atom；Ring A represents 1,4-
The 1,4- phenylenes that phenylene, 1,4- cyclohexylidenes or 1-4 hydrogen atom are replaced by fluorine atoms；
Ring B represents 1,4- phenylenes, 1,4- cyclohexylidenes, 1,4- cyclohexadienylidenes or 1-4 hydrogen atom
The 1,4- phenylenes being replaced by fluorine atoms；M is 0,1 or 2, n are 0 or 1, and m, n
It is asynchronously 0；
Preferably, in the formula I：R represents alkyl or alcoxyl with 1-5 carbon atom
Base；Ring A represents that 1,4- phenylenes, 1,4- cyclohexylidenes or 1-2 hydrogen atom are taken by fluorine atom
The 1,4- phenylenes in generation；Ring B represents the sub- cyclohexene of 1,4- phenylenes, 1,4- cyclohexylidenes, 1,4-
The 1,4- phenylenes that base or 1-2 hydrogen atom are replaced by fluorine atoms；M is 0 or 1, n are 0
Or 1, and be 0 when m, n difference.
3. cyclopenta liquid-crystal compounds according to claim 1 or 2, it is characterised in that
In the formula I, n=1.
4. cyclopenta liquid-crystal compounds according to claim 1, it is characterised in that choosing
Self-drifting I-1~compound shown in I-16：
In the I-1~I-16, R represents alkyl or alkoxy with 1-5 carbon atom.
5. cyclopenta liquid-crystal compounds according to claim 1, it is characterised in that choosing
One kind from following compound：
6. the preparation method of cyclopenta liquid-crystal compounds described in Claims 1 to 5 any one,
Characterized in that, when ring B is that Isosorbide-5-Nitrae-phenylene or 1-4 hydrogen atom are replaced by fluorine atoms
During Isosorbide-5-Nitrae-phenylene, synthetic route is as follows：
Specifically include following steps：
(1)React, then reacted with borate with organolithium reagent, obtained
Arrive
(2) withWithFor raw material,
Reacted, obtained by Suzuki
7. the preparation method of cyclopenta liquid-crystal compounds described in Claims 1 to 5 any one,
Characterized in that, when ring B is Isosorbide-5-Nitrae-cyclohexylidene, synthetic route is as follows：
Specifically include following steps：
(1)With organolithium reagent carry out metallization reaction, then withReaction, is obtained
(2)By with BFEE, three
Ethylsilane is reacted, and is obtained
8. the preparation method of cyclopenta liquid-crystal compounds described in Claims 1 to 5 any one,
Characterized in that, when ring B is Isosorbide-5-Nitrae-cyclohexadienylidene, synthetic route is as follows：
Specifically include following steps：
(1)With organolithium reagent carry out metallization reaction, then with
Reaction, is obtained
(2)It is dehydrated, obtains under acid catalysis
9. include the liquid crystal group of cyclopenta liquid-crystal compounds described in Claims 1 to 5 any one
Compound.
10. cyclopenta liquid-crystal compounds or claim 9 described in Claims 1 to 5 any one
The liquid-crystal composition, in the application of field of liquid crystal display, is preferably in liquid crystal display device
Using.
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| CN111592889A (en) * | 2019-02-20 | 2020-08-28 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound and preparation method and application thereof |
| CN113214083A (en) * | 2021-04-06 | 2021-08-06 | 北京八亿时空液晶科技股份有限公司 | Self-alignment polymerizable compound and application thereof |
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