CN106811208B - 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 applications.The present invention relates to liquid crystal material fields, and in particular to a kind of liquid-crystal compounds, the compound have the structure as shown in logical formula (I): where R1Indicate the alkyl or alkoxy with 1-10 carbon atom, R2Expression-F, alkyl or alkoxy with 1-10 carbon atom, ring A indicate Isosorbide-5-Nitrae-phenylene that Isosorbide-5-Nitrae-phenylene, 1 or 4 cyclohexylidene or 1-4 hydrogen atom are replaced by fluorine atoms, n 0,1 or 2.Liquid-crystal compounds provided by the invention has high negative dielectric anisotropic, and relatively low rotary viscosity can effectively reduce driving voltage after being applied to liquid-crystal composition, improve the response speed of display device.
Description
Technical field
The present invention relates to liquid crystal display material field, in particular to a kind of liquid-crystal compounds, composition and its application.
Background technique
Liquid crystal material has pole as application of the environmentally conscious materials in the fields such as information display material, organic optoelectronic material
Big researching value and fine application prospect.There are many advantages as novel display material for liquid crystal material, if power consumption is extremely low, drive
Dynamic voltage is low.Simultaneously compared with other materials, also there is small in size, light-weight, long-life, display to contain much information, without electromagnetism spoke
The advantages that penetrating almost is adapted to the requirement that various information are shown, especially in TFT-LCD (thin-film transistor technologies) product side
Face.
In the system of tft active matrix, mainly there are TN (Twisted Nematic, twisted-nematic structure) mode, IPS
(In-Plane Switching, plane conversion), FFS (Fringe Field Switching, fringe field switching technique) mode
With the main display pattern such as VA (Vertical Alignment, vertically oriented) mode.
Currently, TFT-LCD product technology is mature, visual angle, resolution ratio, color saturation and brightness etc. are successfully solved
Technical problem, large scale and small-medium size TFT-LCD display have gradually occupied the mainstream of flat-panel monitor in respective field
Status.But the requirement to display technology is always in the continuous improvement, it is desirable that liquid crystal display realizes faster response, reduces
Driving voltage is to reduce power consumption etc..
Liquid crystal material itself plays an important role to the performance for improving liquid crystal display, especially the rotation of reduction liquid crystal material
Turn viscosity and improves the dielectric anisotropy △ ε of liquid crystal material.New requirement is adapted it in order to improve the performance of material, it is novel
The synthesis of structure liquid-crystal compounds and the research of structure-performance relation become an important process of field of liquid crystals.
Summary of the invention
The first object of the present invention is to provide a kind of liquid-crystal compounds of novel negative dielectric anisotropic, compound tool
There are high negative dielectric anisotropic, good liquid crystal intersolubility, relatively low rotary viscosity, these exactly improve liquid
Required for brilliant material, there is important application value.
Liquid-crystal compounds of the present invention, has the following structure:
In general formula I, R1Indicate the alkyl or alkoxy with 1-10 carbon atom, R2Expression-F, have 1-10 carbon former
The alkyl or alkoxy of son, ring A indicate 1 that Isosorbide-5-Nitrae-phenylene, 1 or 4 cyclohexylidene or 1-4 hydrogen atom are replaced by fluorine atoms,
4- phenylene, n 0,1 or 2.
Preferably, in general formula I, R1Indicate the alkyl or alkoxy with 1-5 carbon atom, R2Expression-F, there is 1-5
The alkyl or alkoxy of a carbon atom, ring A indicate that Isosorbide-5-Nitrae-phenylene, 1 or 4 cyclohexylidene or 1-4 hydrogen atom are taken by fluorine atom
Isosorbide-5-Nitrae-the phenylene in generation, n are 0 or 1.
Technical solution more preferably, in general formula I, R1Indicate the alkyl or alkoxy with 1-5 carbon atom, R2
Indicate that the alkyl or alkoxy with 1-5 carbon atom, ring A indicate Isosorbide-5-Nitrae-phenylene, 1 or 4 cyclohexylidene or 1-2 hydrogen atom
Isosorbide-5-Nitrae-the phenylene being replaced by fluorine atoms, n are 0 or 1.
As further preferred technical solution, the liquid-crystal compounds is selected from one kind of following compound:
In I-1~I-6, R1Indicate the alkyl or alkoxy with 1-5 carbon atom, R2Indicate that there is 1-5 carbon atom
Alkyl or alkoxy.
As preferred forms of the invention, the liquid-crystal compounds is selected from one kind of following compound:
The second object of the present invention is to provide the preparation method of the liquid-crystal compounds.
The synthetic route of the method is as follows:
Specifically includes the following steps:
(1)It reacts with organolithium reagent, then is reacted with borate, obtained
(2) withIt for raw material, reacts with organolithium reagent, then is reacted with borate,
It obtains
(3)By oxidation reaction, obtain
(4) withWithIt is anti-by Suzuki for raw material
It answers, obtains
(5)Cyclization is carried out under base catalysis, is obtainedCompounds of formula I；
Wherein, the R in compound involved by each step1、R2, n, R in ring A and gained liquid-crystal compounds product1、R2, n, ring
The group that A is represented is corresponding.
In step 1) described in the above method,The molar ratio of organolithium reagent and borate 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 n-BuLi and potassium tert-butoxide
One or more of, the borate is selected from trimethylborate, three isobutyl ester of triisopropyl borate ester, butyl borate or boric acid
One or more of.
In the step 2),The molar ratio of organolithium reagent and borate
It is 1: 1.0~2.0: 1.0~2.0, reaction temperature -50~-100 DEG C；
Wherein, organolithium reagent is selected from diisopropylamine lithium or 2,2,6,6- tetramethyl piperidine lithiums, and the borate is selected from
Trimethylborate, three isobutyl ester of triisopropyl borate ester, butyl borate or boric acid.
In the step 3),With the molar ratio of oxidant be 1: 1.0~
4.0,40~80 DEG C of reaction temperature；
Above-mentioned oxidant can be selected from hydrogen peroxide or metachloroperbenzoic acid, preferably hydrogen peroxide.
In the step 4),WithFeed intake mole
Than being 1: 0.9~1.2,60~120 DEG C of reaction temperature；
In the step 5),Molar ratio with alkali is 1: 1.0
~4.0,80~150 DEG C of reaction temperature.
" alkali " can be selected from one of sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate or potassium tert-butoxide or several
Kind, preferably potassium tert-butoxide and/or potassium carbonate.
Method of the present invention can be related to conventional post-processing if necessary, and the conventional post-processing is specific such as: using dichloro
Methane, ethyl acetate or toluene extraction, liquid separation are washed, dry, vacuum rotary evaporator evaporation, products therefrom vacuum distillation
Or recrystallization and/or chromatography purify.
It can be stablized using above-mentioned preparation method, be efficiently obtained liquid-crystal compounds of the present invention.
The third object of the present invention is the composition that protection contains the liquid-crystal compounds.The liquid-crystal compounds is combining
Mass percent in object is 1~60%, preferably 3~50%, further preferably 5~25%.
The fourth 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 high negative dielectric anisotropic, and rotary viscosity is low, so that driving voltage be effectively reduced, improves liquid crystal
The response speed of display device, while having the characteristics that optical anisotropy numerical value is moderate, charge conservation rate is high.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..
The raw material unless otherwise instructed, can be obtained from public commercial source.
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).
Embodiment 1
The structural formula of liquid-crystal compounds are as follows:
Embodiment 2
The structural formula of liquid-crystal compounds are as follows:
Embodiment 3
The structural formula of liquid-crystal compounds are as follows:
Embodiment 4
The structural formula of liquid-crystal compounds are as follows:
Embodiment 5
The structural formula of liquid-crystal compounds are as follows:
Embodiment 6
The structural formula of liquid-crystal compounds are as follows:
Embodiment 7
The structural formula of liquid-crystal compounds are as follows:
Embodiment 8
The structural formula of liquid-crystal compounds are as follows:
Embodiment 9
The structural formula of liquid-crystal compounds are as follows:
Embodiment 10
The structural formula of liquid-crystal compounds are as follows:
Embodiment 11
The structural formula of liquid-crystal compounds are as follows:
Embodiment 12
The structural formula of liquid-crystal compounds are as follows:
Embodiment 13
The structural formula of liquid-crystal compounds are as follows:
Embodiment 14
The structural formula of liquid-crystal compounds are as follows:
Embodiment 15
The preparation method of liquid-crystal compounds BYLC-01 described in embodiment 1 is present embodiments provided, the reaction mechanism mechanism of reaction is as follows:
Specific step is as follows:
(1) synthesis of compound BYLC-01-1:
Under nitrogen protection, into reaction flask be added 51.6g 2, the fluoro- 6- tolyl ethyl ether of 3- bis-, 40.3g potassium tert-butoxide and
The hexane solution of 0.36mol n-BuLi is added dropwise in 400ml tetrahydrofuran, temperature control -70~-80 DEG C, and it is small to drip complete insulation reaction 1
When, 41.6g trimethylborate is added dropwise in temperature control -70~-80 DEG C, then rises again naturally to -30 DEG C.2M aqueous hydrochloric acid solution is added
300ml is acidified, and conventional post-processing is carried out, and 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, the fluoro- 4- ethyoxyl bromobenzene of 51.6g 3- and 350ml tetrahydrofuran, temperature control-are added into reaction flask
The tetrahydrofuran solution of 60~-70 DEG C of dropwise addition 0.45mol diisopropylamine lithiums, drips and finishes insulation reaction 1 hour, temperature control -70~-80
DEG C be added dropwise 52.0g trimethylborate, then rise again naturally to -30 DEG C.2M aqueous hydrochloric acid solution 400ml is added to be acidified, carries out
Conventional post-processing, obtains light yellow liquid (compound BYLC-01-2) 78.6g, HPLC:90.9%, yield 100%；
(3) synthesis of compound BYLC-01-3:
78.6g compound BYLC-01-2 and 100ml tetrahydrofuran are added into reaction flask, the lower dropwise addition 0.6mol that flows back is bis-
Oxygen water drips and finishes back flow reaction 1 hour.Conventional post-processing is carried out, brown liquid (compound BYLC-01-3) 66.2g is obtained,
HPLC:91.3%, yield 94%；
(4) synthesis of compound BYLC-01-4:
Under nitrogen protection, 21.6g compound BYLC-01-1,23.5g compound BYLC-01-3 are added into reaction flask,
100ml n,N-Dimethylformamide, 30ml deionized water, 27.6g Anhydrous potassium carbonate, 0.2g tetra-triphenylphosphine palladium are heated to reflux
Reaction 3 hours.It carries out conventional post-processing and obtains light yellow liquid (compound BYLC-01-4) 28.3g, GC through chromatogram purification:
94.1%, yield: 87%.
(5) synthesis of compound BYLC-01:
Under nitrogen protection, 16.3g compound BYLC-01-4,100ml n,N-Dimethylformamide are added into reaction flask,
11.2g potassium tert-butoxide, 130-140 DEG C of temperature control is reacted 3 hours, and TLC tracks fully reacting.Conventional post-processing is carried out, through chromatographically pure
Change, n-hexane elution, ethyl alcohol recrystallization obtains white solid (compound BYLC-01) 11.6g, GC:99.9%, yield: 76%.
Gained white crystal BYLC-01 is analyzed using GC-MS, the m/z of product 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；γ 1:13.3；△ n:0.112.
It can be seen from the above, products therefrom is BYLC-01 structure of the present invention.
Embodiment 16
The preparation method of liquid-crystal compounds BYLC-07 described in embodiment 7 is present embodiments provided, the reaction mechanism mechanism of reaction is as follows:
Specific step is as follows:
(1) synthesis of compound BYLC-07-2:
Under nitrogen protection, 44.7g compound BYLC-07-1 and 350ml tetrahydrofuran, temperature control -60 are added into reaction flask
The tetrahydrofuran solution of~-70 DEG C of dropwise addition 0.23mol diisopropylamine lithiums, drips and finishes insulation reaction 1 hour, temperature control -70~-80 DEG C
31.2g trimethylborate is added dropwise, then rises again naturally to -30 DEG C.2M aqueous hydrochloric acid solution 150ml is added to be acidified, carries out normal
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:
45.1g compound BYLC-07-2 and 100ml tetrahydrofuran are added into reaction flask, the lower dropwise addition 0.3mol that flows back is bis-
Oxygen water drips and finishes back flow reaction 1 hour.Conventional post-processing is carried out, yellow solid (compound BYLC-07-3) 38.1g, GC is obtained:
97.7%, yield 92%；
(3) synthesis of compound BYLC-07-4:
Under nitrogen protection, 21.6g compound BYLC-01-1,31.5g compound BYLC-07-3 are added into reaction flask,
200ml n,N-Dimethylformamide, 60ml deionized water, 27.6g Anhydrous potassium carbonate, 0.3g tetra-triphenylphosphine palladium are heated to reflux
Reaction 3 hours.It carries out conventional post-processing and obtains light yellow solid (compound BYLC-07-4) 33.3g, GC through chromatogram purification:
95.2%, yield: 82%.
(4) synthesis of compound BYLC-07:
Under nitrogen protection, 20.3g compound BYLC-07-4,100ml n,N-Dimethylformamide are added into reaction flask,
11.2g potassium tert-butoxide, 130-140 DEG C of temperature control is reacted 3 hours, and TLC tracks fully reacting.Conventional post-processing is carried out, through chromatographically pure
To change, n-hexane elution, ethyl 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 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；γ 1:118；△ n:0.151.
It can be seen from the above, products therefrom is BYLC-07 structure of the present invention.
Embodiment 17
The preparation method of liquid-crystal compounds BYLC-10 described in embodiment 10 is present embodiments provided, the reaction mechanism mechanism of reaction is as follows:
Specific step is as follows:
(1) synthesis of compound BYLC-10-2:
Under nitrogen protection, 43.8g compound BYLC-10-1 and 350ml tetrahydrofuran, temperature control -60 are added into reaction flask
The tetrahydrofuran solution of~-70 DEG C of dropwise addition 0.23mol diisopropylamine lithiums, drips and finishes insulation reaction 1 hour, temperature control -70~-80 DEG C
31.2g trimethylborate is added dropwise, then rises again naturally to -30 DEG C.2M aqueous hydrochloric acid solution 150ml is added to be acidified, carries out normal
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:
41.8g compound BYLC-10-2 and 100ml tetrahydrofuran are added into reaction flask, the lower dropwise addition 0.3mol that flows back is bis-
Oxygen water drips and finishes back flow reaction 1 hour.Conventional post-processing is carried out, yellow solid (compound BYLC-10-3) 34.5g, GC is obtained:
98.3%, yield 90%；
(3) synthesis of compound BYLC-10-4:
Under nitrogen protection, 17.3g compound BYLC-01-1,24.6g compound BYLC-10-3 are added into reaction flask,
160ml n,N-Dimethylformamide, 40ml deionized water, 22.1g Anhydrous potassium carbonate, 0.2g tetra-triphenylphosphine palladium are heated to reflux
Reaction 3 hours.It carries out conventional post-processing and obtains light yellow solid (compound BYLC-10-4) 26.8g, GC through chromatogram purification:
97.8%, yield: 84%.
(4) synthesis of compound BYLC-10:
Under nitrogen protection, 24.0g compound BYLC-10-4,120ml n,N-Dimethylformamide are added into reaction flask,
13.4g potassium tert-butoxide, 130-140 DEG C of temperature control is reacted 3 hours, and TLC tracks fully reacting.Conventional post-processing is carried out, through chromatographically pure
Change, n-hexane elution, ethyl 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 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；γ 1:110；△ n:0.221.
It can be seen from the above, products therefrom is BYLC-10 structure of the present invention.
The preparation of 2~embodiment of embodiment 6,8~embodiment of embodiment 9,11~embodiment of embodiment, 14 liquid-crystal compounds
Method is similar to embodiment 1, embodiment 7, the preparation method of embodiment 10, it is only necessary to which the corresponding raw material of simple replacement does not change
Any substantive operations, those skilled in the art can grasp completely, and details are not described herein.
Comparative example 1
This comparative example provides a kind of traditional negative dielectric anisotropic compound, and concrete structure formula is as follows:
The various performance parameters of liquid-crystal compounds: △ ε: -7.2；γ 1:13.6；△ n:0.113.
Comparative example 2
This comparative example provides another traditional negative dielectric anisotropic compound, and concrete structure formula is as follows:
The various performance parameters of liquid-crystal compounds: △ ε: -5.6；γ 1:120；△ n:0.156.
Experimental example 1
The liquid-crystal compounds performance parameter data of compound BYLC-01 obtained by embodiment 15 and comparative example 1 are carried out
Comparison arranges, 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 1 chemical structure of comparative example, by the testing result of table 1, it is apparent that originally
The liquid-crystal compounds provided is invented compared with the negative dielectric anisotropic compound of traditional similar chemical structure, is had high
Negative dielectric anisotropic △ ε, rotary viscosity γ 1 is relatively small, required for these exactly improve liquid crystal material, can effectively mention
The dielectric anisotropy △ ε of high liquid-crystal composition reduces driving voltage, obtains the faster liquid-crystal composition of response speed.
Experimental example 2
By the liquid-crystalization of embodiment 16, the difference of embodiment 17 obtained compound BYLC-07, BYLC-10 and comparative example 2
It closes physical performance supplemental characteristic and compares arrangement, testing result is as shown in table 2:
Table 2: the performance test results of liquid-crystal compounds
BYLC-07, the BYLC-10 of embodiment 17 of embodiment 16 are similar with 2 chemical structure of comparative example, by the detection of table 2
As a result, it is apparent that the negative dielectric anisotropic of liquid-crystal compounds provided by the invention and traditional similar chemical structure
It closes object to compare, there is high negative dielectric anisotropic △ ε, rotary viscosity γ 1 is relatively small, these exactly improve liquid crystal material
It is required, it can effectively improve the dielectric anisotropy △ ε of liquid-crystal composition, reduce driving voltage, obtain response speed more
Fast liquid-crystal composition.
In addition, discovery after herein described compound is particularly applicable in the liquid-crystal composition of conventional system, it can be with
The dielectric anisotropy △ ε of liquid-crystal composition is significantly improved, while keeping lower rotary viscosity γ 1 and refractive index appropriate each
Anisotropy △ n, gained liquid-crystal composition have the characteristics that significant quick response and low voltage drive feature.
Although above the present invention is described in detail with a general description of the specific embodiments,
On the basis of the present invention, it can be made some modifications or improvements, this will be apparent to those skilled in the art.Cause
This, these modifications or improvements, fall within the scope of the claimed invention without departing from theon the basis of the spirit of the present invention.
Claims (16)
1. a kind of liquid-crystal compounds, it is characterised in that: the compound has the structure as shown in logical formula (I):
Wherein, R1Indicate the alkyl or alkoxy with 1-10 carbon atom, R2Indicate the alkyl or alkane with 1-10 carbon atom
Oxygroup, ring A indicate that Isosorbide-5-Nitrae-phenylene that Isosorbide-5-Nitrae-phenylene, 1 or 4 cyclohexylidene or 1-4 hydrogen atom are replaced by fluorine atoms, n are
0,1 or 2.
2. compound according to claim 1, it is characterised in that: the R1Indicate the alkyl or alkane with 1-5 carbon atom
Oxygroup, R2Indicate that the alkyl or alkoxy with 1-5 carbon atom, ring A indicate Isosorbide-5-Nitrae-phenylene, 1 or 4 cyclohexylidene or 1-4
Isosorbide-5-Nitrae-phenylene that a hydrogen atom is replaced by fluorine atoms, n are 0 or 1.
3. compound according to claim 2, it is characterised in that: R1Indicate the alkyl or alcoxyl with 1-5 carbon atom
Base, R2Indicate that the alkyl or alkoxy with 1-5 carbon atom, ring A indicate Isosorbide-5-Nitrae-phenylene, 1 or 4 cyclohexylidene or 1-2
Isosorbide-5-Nitrae-phenylene that hydrogen atom is replaced by fluorine atoms, n are 0 or 1.
4. compound according to claim 1, it is characterised in that: the liquid-crystal compounds is selected from the one of following compound
Kind:
Wherein, R1Indicate the alkyl or alkoxy with 1-5 carbon atom, R2Indicate the alkyl or alcoxyl with 1-5 carbon atom
Base.
5. compound according to claim 4, it is characterised in that: the liquid-crystal compounds is selected from the one of following compound
Kind:
6. the preparation method of any one of the claim 1-5 compound, it is characterised in that: the reaction mechanism mechanism of reaction is as follows:
Specifically includes the following steps:
(1)It reacts with organolithium reagent, then is reacted with borate, obtained
(2) withIt for raw material, reacts with organolithium reagent, then is reacted with borate, obtained
(3)By oxidation reaction, obtain
(4) withWithIt for raw material, is reacted, is obtained by Suzuki
It arrives
(5)Cyclization is carried out under base catalysis, is obtainedCompounds of formula I；
Wherein, the R in compound involved by each step1、R2, n, ring A is the same as any one of claim 1-5.
7. according to the method described in claim 6, it is characterized by: in the step 1),Organolithium reagent
Molar ratio with borate is 1: 1.0~1.8: 1.0~2.0, reaction temperature -50~-100 DEG C；In step 2),The molar ratio of organolithium reagent and borate is 1: 1.0~2.0: 1.0~2.0,
Reaction temperature -50~-100 DEG C；
In step 3),Molar ratio with oxidant is 1: 1.0~4.0, reaction temperature
40~80 DEG C of degree；In step 4),WithMolar ratio
It is 1: 0.9~1.2,60~120 DEG C of reaction temperature；
In step 5),Molar ratio with alkali is 1: 1.0~4.0, instead
Answer 80~150 DEG C of temperature.
8. according to the method described in claim 7, it is characterized by: the organolithium reagent is selected from positive fourth in the step 1)
Base lithium, s-butyl lithium, tert-butyl lithium or one or more of n-BuLi and potassium tert-butoxide, the borate are selected from boric acid three
One or more of methyl esters, three isobutyl ester of triisopropyl borate ester, butyl borate or boric acid.
9. according to the method described in claim 7, it is characterized by: it is different that the organolithium reagent is selected from two in the step 2)
Propylamino lithium or 2,2,6,6- tetramethyl piperidine lithiums, the borate are selected from trimethylborate, triisopropyl borate ester, three fourth of boric acid
Three isobutyl ester of ester or boric acid.
10. according to the method described in claim 7, it is characterized by: in the step 3), the oxidant be selected from hydrogen peroxide or
Metachloroperbenzoic acid.
11. according to the method described in claim 7, it is characterized by: the alkali is selected from sodium hydroxide, hydrogen in the step 5)
One or more of potassium oxide, sodium carbonate, potassium carbonate or potassium tert-butoxide.
12. a kind of liquid-crystal composition containing any one of the claim 1-5 liquid-crystal compounds, which is characterized in that the liquid
The mass percent of brilliant compound in the composition is 1~60%.
13. liquid-crystal composition according to claim 12, it is characterised in that: the matter of the liquid-crystal compounds in the composition
Measuring percentage is 3~50%.
14. liquid-crystal composition according to claim 13, it is characterised in that: the matter of the liquid-crystal compounds in the composition
Measuring percentage is 5~25%.
15. any one of any one of the claim 1-5 compound or claim 12-14 composition is filled in liquid crystal display
Application in setting.
16. application according to claim 15, it is characterised in that: the liquid crystal display device be TN, ADS, VA,
PSVA, FFS or IPS liquid crystal display.
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| CN109082281B (en) * | 2017-06-14 | 2021-09-07 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound with negative dielectric anisotropy as well as preparation method and application thereof |
| 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 |
| JP2019014675A (en) * | 2017-07-06 | 2019-01-31 | Dic株式会社 | Phenyl phenol derivative and method for producing dibenzofuran derivative using the same |
| CN111484853B (en) * | 2019-01-29 | 2021-08-10 | 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 |
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