CN106811208A - A kind of liquid-crystal compounds, composition and its application - Google Patents
A kind of liquid-crystal compounds, composition and its application Download PDFInfo
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Abstract
The invention discloses a kind of liquid-crystal compounds, composition and its application.The present invention relates to liquid crystal material field, and in particular to a kind of liquid-crystal compounds, the compound has the structure as shown in logical formula (I)：Wherein, R1Represent that there is the alkyl or alkoxy of 1-10 carbon atom, R2Represent-F, with 1-10 the alkyl or alkoxy of carbon atom, ring A represents Isosorbide-5-Nitrae-phenylene that Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-4 hydrogen atom are replaced by fluorine atoms, and n is 0,1 or 2.The liquid-crystal compounds that the present invention is provided has a high negative dielectric anisotropic, relatively low rotary viscosity, using to can effectively reduce driving voltage after liquid-crystal composition, improves the response speed of 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 used 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 the system of tft active matrix, (Twisted Nematic are turned round mainly TN
Bent nematic structure) pattern, IPS (In-Plane Switching, plane conversion), FFS (Fringe
Field Switching, fringe field switching technology) (Vertical Alignment hang down for pattern and VA
Straight orientation) the main display pattern such as pattern.
At present, TFT-LCD product technologies are ripe, successfully solve visual angle, differentiate
The technical barriers such as rate, color saturation and brightness, large scale and small-medium size TFT-LCD show
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 reducing the aspects such as power consumption.
Liquid crystal material effect important to improving the performance of liquid crystal display in itself, especially
Reduce liquid crystal material rotary viscosity and improve the dielectric anisotropy △ ε of liquid crystal material.In order to
The performance for improving material adapts it to new requirement, the synthesis of new structure liquid-crystal compounds and knot
An important process of the research as field of liquid crystals of structure-property relationship.
The content of the invention
The first object of the present invention is to provide a kind of liquid-crystalization of new negative dielectric anisotropic
Compound, the compound has high negative dielectric anisotropic, good liquid crystal intersolubility, phase
The advantages of to low rotary viscosity, these exactly improve required for liquid crystal material, with important
Application value.
Liquid-crystal compounds of the present invention, with following structure：
In formula I, R1Represent that there is the alkyl or alkoxy of 1-10 carbon atom, R2Table
Show-F, with 1-10 the alkyl or alkoxy of carbon atom, ring A represent Isosorbide-5-Nitrae-phenylene,
Isosorbide-5-Nitrae-phenylene that Isosorbide-5-Nitrae-cyclohexylidene or 1-4 hydrogen atom are replaced by fluorine atoms, n is 0,1
Or 2.
Preferably, in formula I, R1Represent that there is the alkyl or alkoxy of 1-5 carbon atom,
R2Represent-F, with 1-5 the alkyl or alkoxy of carbon atom, ring A represent Isosorbide-5-Nitrae-phenylene,
Isosorbide-5-Nitrae-phenylene that Isosorbide-5-Nitrae-cyclohexylidene or 1-4 hydrogen atom are replaced by fluorine atoms, n is 0 or 1.
As preferred technical scheme, in formula I, R1Represent that there is 1-5 carbon atom
Alkyl or alkoxy, R2Represent that there is the alkyl or alkoxy of 1-5 carbon atom, ring A
Represent the 1,4- that 1,4- phenylenes, 1,4- cyclohexylidenes or 1-2 hydrogen atom are replaced by fluorine atoms
Phenylene, n is 0 or 1.
Used as further preferred technical scheme, the liquid-crystal compounds is selected from following compound
It is a kind of：
In I-1~I-6, R1Represent that there is the alkyl or alkoxy of 1-5 carbon atom, R2Table
Show with 1-5 the alkyl or alkoxy of carbon atom.
Used as preferred forms of the 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 synthetic route of methods described is as follows：
Specifically include following steps：
(1)Reacted with organolithium reagent, then reacted with borate, obtained
(2) withIt is raw material, is reacted with organolithium reagent, then
With borate reaction, obtain
(3)By oxidation reaction, obtain
(4) withWithIt is raw material, leads to
Suzuki reactions are crossed, is obtained
(5)Cyclization is carried out under base catalysis, is obtained
ArriveCompounds of formula I；
Wherein, the R in compound involved by each step1、R2, n, ring A and gained liquid-crystalize
R in compound product1、R2, n, ring A represent group it is corresponding.
Step 1 described in the above method) in,Organolithium reagent and borate
Molar ratio is 1: 1.0~1.8: 1.0~2.0, reaction temperature -50~-100 DEG C；
Wherein, the organolithium reagent is selected from n-BuLi, s-butyl lithium, tert-butyl lithium or just
One or more in butyl lithium and potassium tert-butoxide, the borate is selected from trimethylborate, boron
One or more in sour three isopropyl esters, butyl borate or the isobutyl ester of boric acid three.
The step 2) in,Organolithium reagent and borate
Molar ratio is 1: 1.0~2.0: 1.0~2.0, reaction temperature -50~-100 DEG C；
Wherein, organolithium reagent be selected from diisopropylamine lithium or 2,2,6,6- tetramethyl piperidine lithiums,
It is different that the borate is selected from trimethylborate, triisopropyl borate ester, butyl borate or boric acid three
Butyl ester.
The step 3) in,With the molar ratio of oxidant
It is 1: 1.0~4.0,40~80 DEG C of reaction temperature；
Above-mentioned oxidant may be selected from hydrogen peroxide or metachloroperbenzoic acid, preferably hydrogen peroxide.
The step 4) in,With's
Molar ratio is 1: 0.9~1.2,60~120 DEG C of reaction temperature；
The step 5) in,With feeding intake mole for alkali
Than being 1: 1.0~4.0,80~150 DEG C of reaction temperature.
" alkali " may be selected from NaOH, potassium hydroxide, sodium carbonate, potassium carbonate or tertiary fourth
One or more in potassium alcoholate, preferably potassium tert-butoxide and/or potassium carbonate.
Method of the present invention, can be related to conventional post processing when necessary, locate after the routine
Reason is specific such as：Extracted with dichloromethane, ethyl acetate or toluene, point liquid, washing is dried,
Vacuum rotary evaporator evaporation, products therefrom vacuum distillation or recrystallization and/or chromatographic isolation
Method is purified, you can.
Can be stablized using above-mentioned preparation method, be efficiently obtained LCD compound of the present invention
Thing.
The third object of the present invention is composition of the protection containing the liquid-crystal compounds.The liquid
Crystallization compound mass percent in the composition is 1~60%, preferably 3~50%, enters one
Step is preferably 5~25%.
The fourth object of the present invention is the protection liquid-crystal compounds and contains the liquid-crystalization
The composition of compound field of liquid crystal display application, preferably in liquid crystal display device should
With.Described liquid crystal display device include but is not limited to TN, ADS, VA, PSVA,
FFS or IPS liquid crystal displays.Use the liquid-crystal compounds or contain the liquid-crystalization
The composition of compound has high negative dielectric anisotropic, and rotary viscosity is low, so as to effectively drop
Low driving voltage, improves the response speed of liquid crystal display device, while having optics each to different
Property is the features such as numerical value is moderate, electric charge conservation rate is high.
Specific 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, each of liquid-crystal compounds is obtained by linear fit
Item performance parameter, wherein, the concrete meaning of each performance parameter is as follows：
△ n represent optical anisotropy (25 DEG C)；△ 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：
Embodiment 2
The structural formula of liquid-crystal compounds is：
Embodiment 3
The structural formula of liquid-crystal compounds is：
Embodiment 4
The structural formula of liquid-crystal compounds is：
Embodiment 5
The structural formula of liquid-crystal compounds is：
Embodiment 6
The structural formula of liquid-crystal compounds is：
Embodiment 7
The structural formula of liquid-crystal compounds is：
Embodiment 8
The structural formula of liquid-crystal compounds is：
Embodiment 9
The structural formula of liquid-crystal compounds is：
Embodiment 10
The structural formula of liquid-crystal compounds is：
Embodiment 11
The structural formula of liquid-crystal compounds is：
Embodiment 12
The structural formula of liquid-crystal compounds is：
Embodiment 13
The structural formula of liquid-crystal compounds is：
Embodiment 14
The structural formula of liquid-crystal compounds is：
Embodiment 15
The preparation method of liquid-crystal compounds BYLC-01 described in embodiment 1 is present embodiments provided,
Its reaction mechanism mechanism of reaction is as follows：
Comprise the following steps that：
(1) synthesis of compound BYLC-01-1：
Under nitrogen protection, to addition 51.6g 2, the fluoro- 6- tolyl ethyl ethers of 3- bis-, 40.3g in reaction bulb
Potassium tert-butoxide and 400ml tetrahydrofurans, temperature control -70~-80 DEG C are added dropwise 0.36mol n-BuLis
Hexane solution, drop finishes insulation reaction 1 hour, and temperature control -70~-80 DEG C are added dropwise 41.6g boric acid three
Methyl esters, then rises again to -30 DEG C naturally.2M aqueous hydrochloric acid solutions 300ml is added to be acidified,
Conventional post processing is carried out, petroleum ether is recrystallized to give light yellow solid (compound BYLC-01-1)
58.9g, HPLC：98.4%, yield 91%；
(2) synthesis of compound BYLC-01-2：
Under nitrogen protection, to the addition fluoro- 4- ethyoxyls bromobenzenes of 51.6g 3- and 350ml in reaction bulb
Tetrahydrofuran, the tetrahydrofuran that temperature control -60~-70 DEG C are added dropwise 0.45mol diisopropylamine lithiums is molten
Liquid, drop finishes insulation reaction 1 hour, and temperature control -70~-80 DEG C are added dropwise 52.0g trimethylborates, so
Rise again naturally afterwards to -30 DEG C.Add 2M aqueous hydrochloric acid solutions 400ml to be acidified, carry out often
Rule post processing, obtains light yellow liquid (compound BYLC-01-2) 78.6g, HPLC：90.9%,
Yield 100%；
(3) synthesis of compound BYLC-01-3：
To 78.6g compound BYLC-01-2 and 100ml tetrahydrofurans are added in reaction bulb, return
Dropwise addition 0.6mol hydrogen peroxide is flowed down, drop finishes back flow reaction 1 hour.Conventional post processing is carried out,
Obtain brown liquid (compound BYLC-01-3) 66.2g, HPLC：91.3%, yield
94%；
(4) synthesis of compound BYLC-01-4：
Under nitrogen protection, to addition 21.6g compounds BYLC-01-1,23.5g in reaction bulb
Compound BYLC-01-3,100ml DMF, 30ml deionized waters, 27.6g
Anhydrous potassium carbonate, 0.2g tetra-triphenylphosphine palladiums, heating reflux reaction 3 hours.After carrying out routine
Treatment, through chromatogram purification, obtains light yellow liquid (compound BYLC-01-4) 28.3g, GC：
94.1%, yield：87%.
(5) synthesis of compound BYLC-01：
Under nitrogen protection, to addition 16.3g compounds BYLC-01-4,100ml in reaction bulb
DMF, 11.2g potassium tert-butoxides, 130-140 DEG C of temperature control reacts 3 hours,
TLC tracking reactions are complete.Conventional post processing is carried out, through chromatogram purification, n-hexane wash-out, second
Alcohol is recrystallized to give white solid (compound BYLC-01) 11.6g, GC：99.9%, receive
Rate：76%.
Gained white crystal BYLC-01 is analyzed using GC-MS, the m/z of product
It is 306.1 (M+).
1H-NMR(300MHz,CDCl3):1.3-2.7 (m, 9H), 4.1-4.3 (m, 4H), 6.9-7.3
(m,3H)。
The various performance parameters of liquid-crystal compounds：△ε：-16.2；γ1：13.3；△n：0.112.
From the foregoing, products therefrom is BYLC-01 structures of the present invention.
Embodiment 16
The preparation method of liquid-crystal compounds BYLC-07 described in embodiment 7 is present embodiments provided,
Its reaction mechanism mechanism of reaction is as follows：
Comprise the following steps that：
(1) synthesis of compound BYLC-07-2：
Under nitrogen protection, to addition 44.7g compounds BYLC-07-1 and 350ml in reaction bulb
Tetrahydrofuran, the tetrahydrofuran that temperature control -60~-70 DEG C are added dropwise 0.23mol diisopropylamine lithiums is molten
Liquid, drop finishes insulation reaction 1 hour, and temperature control -70~-80 DEG C are added dropwise 31.2g trimethylborates, so
Rise again naturally afterwards to -30 DEG C.Add 2M aqueous hydrochloric acid solutions 150ml to be acidified, carry out often
Rule post processing, obtains light yellow solid (compound BYLC-07-2) 45.1g, HPLC：96.9%,
Yield 88%；
(2) synthesis of compound BYLC-07-3：
To 45.1g compound BYLC-07-2 and 100ml tetrahydrofurans are added in reaction bulb, return
Dropwise addition 0.3mol hydrogen peroxide is flowed down, drop finishes back flow reaction 1 hour.Conventional post processing is carried out,
Obtain yellow solid (compound BYLC-07-3) 38.1g, GC：97.7%, yield 92%；
(3) synthesis of compound BYLC-07-4：
Under nitrogen protection, to addition 21.6g compounds BYLC-01-1,31.5g in reaction bulb
Compound BYLC-07-3,200ml DMF, 60ml deionized waters, 27.6g
Anhydrous potassium carbonate, 0.3g tetra-triphenylphosphine palladiums, heating reflux reaction 3 hours.After carrying out routine
Treatment, through chromatogram purification, obtains light yellow solid (compound BYLC-07-4) 33.3g, GC：
95.2%, yield：82%.
(4) synthesis of compound BYLC-07：
Under nitrogen protection, to addition 20.3g compounds BYLC-07-4,100ml in reaction bulb
DMF, 11.2g potassium tert-butoxides, 130-140 DEG C of temperature control reacts 3 hours,
TLC tracking reactions are complete.Conventional post processing is carried out, through chromatogram purification, n-hexane wash-out, second
Alcohol+re-crystallizing in ethyl acetate obtains white solid (compound BYLC-07) 14.2g, GC：
99.9%, yield：74%.
Gained white crystal BYLC-07 is analyzed using GC-MS, the m/z of product
It is 386.2 (M+).
1H-NMR(300MHz,CDCl3):0.96-2.7 (m, 23H), 4.0-4.3 (m, 2H), 6.9-7.3
(m,3H)。
The various performance parameters of liquid-crystal compounds：△ε：-16.6；γ1：118；△n：0.151.
From the foregoing, products therefrom is BYLC-07 structures of the present invention.
Embodiment 17
The preparation method of liquid-crystal compounds BYLC-10 described in embodiment 10 is present embodiments provided,
Its reaction mechanism mechanism of reaction is as follows：
Comprise the following steps that：
(1) synthesis of compound BYLC-10-2：
Under nitrogen protection, to addition 43.8g compounds BYLC-10-1 and 350ml in reaction bulb
Tetrahydrofuran, the tetrahydrofuran that temperature control -60~-70 DEG C are added dropwise 0.23mol diisopropylamine lithiums is molten
Liquid, drop finishes insulation reaction 1 hour, and temperature control -70~-80 DEG C are added dropwise 31.2g trimethylborates, so
Rise again naturally afterwards to -30 DEG C.Add 2M aqueous hydrochloric acid solutions 150ml to be acidified, carry out often
Rule post processing, obtains light yellow solid (compound BYLC-10-2) 41.8g, HPLC：98.2%,
Yield 83%；
(2) synthesis of compound BYLC-10-3：
To 41.8g compound BYLC-10-2 and 100ml tetrahydrofurans are added in reaction bulb, return
Dropwise addition 0.3mol hydrogen peroxide is flowed down, drop finishes back flow reaction 1 hour.Conventional post processing is carried out,
Obtain yellow solid (compound BYLC-10-3) 34.5g, GC：98.3%, yield 90%；
(3) synthesis of compound BYLC-10-4：
Under nitrogen protection, to addition 17.3g compounds BYLC-01-1,24.6g in reaction bulb
Compound BYLC-10-3,160ml DMF, 40ml deionized waters, 22.1g
Anhydrous potassium carbonate, 0.2g tetra-triphenylphosphine palladiums, heating reflux reaction 3 hours.After carrying out routine
Treatment, through chromatogram purification, obtains light yellow solid (compound BYLC-10-4) 26.8g, GC：
97.8%, yield：84%.
(4) synthesis of compound BYLC-10：
Under nitrogen protection, to addition 24.0g compounds BYLC-10-4,120ml in reaction bulb
DMF, 13.4g potassium tert-butoxides, 130-140 DEG C of temperature control reacts 3 hours,
TLC tracking reactions are complete.Conventional post processing is carried out, through chromatogram purification, n-hexane wash-out, second
Alcohol+re crystallization from toluene obtains white solid (compound BYLC-10) 17.3g, GC：99.9%,
Yield：76%.
Gained white crystal BYLC-10 is analyzed using GC-MS, the m/z of product
It is 380.1 (M+).
1H-NMR(300MHz,CDCl3):0.95-2.8 (m, 13H), 3.9-4.2 (m, 2H), 6.9-7.5
(m,7H)。
The various performance parameters of liquid-crystal compounds：△ε：-17.2；γ1：110；△n：0.221.
From the foregoing, products therefrom is BYLC-10 structures of the present invention.
2~embodiment of embodiment 6,8~embodiment of embodiment 9,11~embodiment of embodiment 14
The preparation method of liquid-crystal compounds and embodiment 1, embodiment 7, the preparation method of embodiment 10
It is similar, it is only necessary to simply to replace corresponding raw material, any substantive operations, this area are not changed
Technical staff can grasp completely, will not be repeated here.
Comparative example 1
This comparative example provides a kind of traditional negative dielectric anisotropic compound, its concrete structure
Formula is as follows：
The various performance parameters of liquid-crystal compounds：△ε：-7.2；γ1：13.6；△n：0.113.
Comparative example 2
This comparative example provides another traditional negative dielectric anisotropic compound, its specific knot
Structure formula is as follows：
The various performance parameters of liquid-crystal compounds：△ε：-5.6；γ1：120；△n：0.156.
Experimental example 1
By compound BYLC-01 and the liquid-crystal compounds of comparative example 1 obtained by embodiment 15
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
The BYLC-01 of embodiment 15 is similar with the chemical constitution of comparative example 1, by the detection of table 1
Result is, it is apparent that the liquid-crystal compounds and traditional similar chemical structure of present invention offer
Negative dielectric anisotropic compound phase ratio, with high negative dielectric anisotropic △ ε, rotation
Turn viscosity γ 1 relatively small, these exactly improve required for liquid crystal material, can effectively carry
The dielectric anisotropy △ ε of liquid-crystal composition high, reduce driving voltage, meet with a response speed more
Fast liquid-crystal composition.
Experimental example 2
By embodiment 16, embodiment 17 obtained respectively compound BYLC-07, BYLC-10
Contrast arrangement, testing result such as table are carried out with the liquid-crystal compounds performance parameter data of comparative example 2
Shown in 2：
Table 2：The performance test results of liquid-crystal compounds
BYLC-07, the BYLC-10 of embodiment 17 and the chemistry of comparative example 2 of embodiment 16
Structure is similar, by the testing result of table 2, it is apparent that the LCD compound of present invention offer
The negative dielectric anisotropic compound phase ratio of thing and traditional similar chemical structure, with high
△ ε, rotary viscosity γ 1 are relatively small for negative dielectric anisotropic, and these exactly improve liquid crystal material
Required, the dielectric anisotropy △ ε of liquid-crystal composition can be effectively improved, reduce and drive
Voltage, the faster liquid-crystal composition of the speed that meets with a response.
Additionally, herein described compound is particularly applicable in the liquid-crystal composition of conventional system
After find, its dielectric anisotropy △ ε that can significantly improve liquid-crystal composition, at the same keep
Relatively low rotary viscosity γ 1 and appropriate refractive anisotrop △ n, gained liquid-crystal composition tool
There are 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 liquid-crystal compounds, it is characterised in that：The compound has such as logical formula (I)
Shown structure：
Wherein, R1Represent that there is the alkyl or alkoxy of 1-10 carbon atom, R2Expression-F,
With 1-10 the alkyl or alkoxy of carbon atom, ring A represents Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-Asia ring
Isosorbide-5-Nitrae-phenylene that hexyl or 1-4 hydrogen atom are replaced by fluorine atoms, n is 0,1 or 2.
2. compound according to claim 1, it is characterised in that：The R1Represent tool
There are 1-5 the alkyl or alkoxy of carbon atom, R2Represent-F, with the 1-5 alkane of carbon atom
Base or alkoxy, ring A represent Isosorbide-5-Nitrae-phenylene, Isosorbide-5-Nitrae-cyclohexylidene or 1-4 hydrogen atom quilt
Isosorbide-5-Nitrae-the phenylene of fluorine atom substitution, n is 0 or 1.
3. compound according to claim 2, it is characterised in that：R1Represent that there is 1-5
The alkyl or alkoxy of individual carbon atom, R2Represent that there is the alkyl or alkoxy of 1-5 carbon atom,
Ring A represents what 1,4- phenylenes, 1,4- cyclohexylidenes or 1-2 hydrogen atom were replaced by fluorine atoms
Isosorbide-5-Nitrae-phenylene, n is 0 or 1.
4. compound according to claim 1, it is characterised in that：The LCD compound
Thing is selected from one kind of following compound：
Wherein, R1Represent that there is the alkyl or alkoxy of 1-5 carbon atom, R2Expression has
1-5 the alkyl or alkoxy of carbon atom.
5. compound according to claim 4, it is characterised in that：The LCD compound
Thing is selected from one kind of following compound：
6. the preparation method of compound described in any one of claim 1-5, it is characterised in that：
The reaction mechanism mechanism of reaction is as follows：
Specifically include following steps：
(1)Reacted with organolithium reagent, then reacted with borate, obtained
(2) withIt is raw material, is reacted with organolithium reagent, then
With borate reaction, obtain
(3)By oxidation reaction, obtain
(4) withWithIt is raw material, leads to
Suzuki reactions are crossed, is obtained
(5)Cyclization is carried out under base catalysis, is obtained
ArriveCompounds of formula I；
Wherein, the R in compound involved by each step1、R2, n, ring A is with claim 1-5
Any one.
7. method according to claim 6, it is characterised in that：The step 1) in,The molar ratio of organolithium reagent and borate for 1: 1.0~1.8: 1.0~
2.0, reaction temperature -50~-100 DEG C；It is preferred that the organolithium reagent is selected from n-BuLi, secondary
One or more in butyl lithium, tert-butyl lithium or n-BuLi and potassium tert-butoxide, the boric acid
Ester is selected from trimethylborate, triisopropyl borate ester, butyl borate or the isobutyl ester of boric acid three
One or more；
Step 2) in,The throwing of organolithium reagent and borate
Material mol ratio is 1: 1.0~2.0: 1.0~2.0, reaction temperature -50~-100 DEG C；It is preferred that described
Organolithium reagent is selected from diisopropylamine lithium or 2,2,6,6- tetramethyl piperidine lithiums, the borate
Selected from trimethylborate, triisopropyl borate ester, butyl borate or the isobutyl ester of boric acid three；
Step 3) in,Molar ratio with oxidant is
1: 1.0~4.0,40~80 DEG C of reaction temperature；It is preferred that the oxidant be selected from hydrogen peroxide or
Chloroperoxybenzoic acid；
Step 4) in,WithFeed intake
Mol ratio is 1: 0.9~1.2,60~120 DEG C of reaction temperature；
Step 5) in,Molar ratio with alkali is
1: 1.0~4.0,80~150 DEG C of reaction temperature；It is preferred that the alkali is selected from NaOH, hydrogen-oxygen
Change one or more in potassium, sodium carbonate, potassium carbonate or potassium tert-butoxide.
8. a kind of liquid-crystal composition containing liquid-crystal compounds described in claim any one of 1-5,
Characterized in that, liquid-crystal compounds mass percent in the composition is 1~60%, it is excellent
Elect 3~50%, more preferably 5~25% as.
9. compound described in any one of claim 1-5 or composition described in claim 8 are in liquid
Application in crystal device.
10. application according to claim 9, it is characterised in that：Described liquid crystal display
Device is TN, ADS, VA, PSVA, FFS or IPS liquid crystal display.
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| CN109207159A (en) * | 2017-06-30 | 2019-01-15 | 北京八亿时空液晶科技股份有限公司 | A kind of liquid-crystal compounds of negative dielectric anisotropic and the preparation method and application thereof |
| CN109206302A (en) * | 2017-07-06 | 2019-01-15 | Dic株式会社 | The manufacturing method of phenylphenol derivative and the dibenzofuran derivative using it |
| CN111484853A (en) * | 2019-01-29 | 2020-08-04 | 北京八亿时空液晶科技股份有限公司 | Novel liquid crystal compound and preparation method and application thereof |
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| CN113698942A (en) * | 2020-05-22 | 2021-11-26 | 江苏和成显示科技有限公司 | Liquid crystal compound with negative dielectric anisotropy, liquid crystal composition and display device thereof |
| CN113698942B (en) * | 2020-05-22 | 2024-02-27 | 江苏和成显示科技有限公司 | Liquid crystal compound with negative dielectric anisotropy, liquid crystal composition thereof and display device |
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