CN107312549A - Liquid-crystal compounds and its application containing dimethyl benzene and difluoromethylenedioconnecting linking group - Google Patents
Liquid-crystal compounds and its application containing dimethyl benzene and difluoromethylenedioconnecting linking group Download PDFInfo
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- CN107312549A CN107312549A CN201710432270.3A CN201710432270A CN107312549A CN 107312549 A CN107312549 A CN 107312549A CN 201710432270 A CN201710432270 A CN 201710432270A CN 107312549 A CN107312549 A CN 107312549A
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- 0 *NC(CC1)CCC1C(CC1)CCC1I1=C*1 Chemical compound *NC(CC1)CCC1C(CC1)CCC1I1=C*1 0.000 description 12
- JHLKSIOJYMGSMB-UHFFFAOYSA-N Fc1cc(F)cc(Br)c1 Chemical compound Fc1cc(F)cc(Br)c1 JHLKSIOJYMGSMB-UHFFFAOYSA-N 0.000 description 2
- KUQQNEKJWXTPNC-UHFFFAOYSA-N C=CCc(cc(cc1F)[Br]=C)c1C1=[Si-]CCCS1 Chemical compound C=CCc(cc(cc1F)[Br]=C)c1C1=[Si-]CCCS1 KUQQNEKJWXTPNC-UHFFFAOYSA-N 0.000 description 1
- PIDHFURANSYYKI-UHFFFAOYSA-N CS1=C(c(c(F)cc(Br)c2)c2F)SCCC1 Chemical compound CS1=C(c(c(F)cc(Br)c2)c2F)SCCC1 PIDHFURANSYYKI-UHFFFAOYSA-N 0.000 description 1
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- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
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- C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
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- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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Abstract
The invention discloses a kind of liquid-crystal compounds containing dimethyl benzene and difluoromethylenedioconnecting linking group and its application.The compound is shown in formula I.In the compound of formula I molecular structure that the present invention is provided, contain dimethyl benzene and difluoromethylenedioconnecting (CF2O) the liquid-crystal compounds of linking group, not only with larger dielectric anisotropy, it is often more important that while having the response speed being exceedingly fast and higher clearing point, for allotment liquid crystal compound, the performance has great importance.
Description
The application is that the Application No. 201510555389.0 submitted for 2nd in September in 2015 is entitled " containing diformazan
The division Shen of China's application of liquid-crystal compounds of base benzene and difluoromethylenedioconnecting linking group and preparation method and application "
Please.
Technical field
The present invention relates to the preparation of liquid-crystal compounds and application field, and in particular to one kind is sub- containing dimethyl benzene and difluoro
The liquid-crystal compounds of methoxyl group linking group and its application.
Background technology
At present, what the application of liquid-crystal compounds was expanded is increasingly wider, and it can be applied to polytype display, electricity
In optical device, sensor etc..Species for the liquid-crystal compounds of above-mentioned display field is various, and wherein nematic liquid crystal is using most
To be extensive.Nematic liquid crystal is had been applied in passive TN, STN matrix display and system with tft active matrix.
For thin-film transistor technologies (TFT-LCD) application field, although market is very huge in recent years, technology
It is gradually ripe, but requirement of the people to Display Technique also constantly improving, and is especially realizing quick response, reduction driving electricity
Pressure is with terms of reducing power consumption.Liquid crystal material is as one of important photoelectron material of liquid crystal display, to improving liquid crystal display
The performance of device plays an important role.
As liquid crystal material it is necessary to have good chemically and thermally stability and to electric field and the stabilization of electromagnetic radiation
Property.And as thin-film transistor technologies (TFT-LCD) liquid crystal material, do not need only to have as outside upward stability, should also have
Wider nematic temperature range, suitable birefringence anisotropy, very high resistivity, good uviolresistance
The performances such as energy, high electric charge conservation rate and low-steam pressure.
For dynamic menu show apply, such as LCD TV, in order to realize that high-quality show, eliminate display picture ghost with
Hangover, it is desirable to which liquid crystal has response speed quickly, therefore it is required that liquid crystal has relatively low rotary viscosity γ 1；In addition, in order to drop
Low equipment energy consumption, it is desirable to which the driving voltage of liquid crystal is as low as possible, so improving the dielectric anisotropy △ ε of liquid crystal to mixed liquid crystal
It is significant.
Numerous studies show that liquid crystal molecule is introduced after difluoromethylenedioconnecting (- CF2O-) linking group, can make liquid crystal
Rotary viscosity γ 1 decrease.Additionally, due to the contribution of the dipole moment of difluoromethylenedioconnecting (- CF2O-) bridge, end group fluorine atom
Dipole moment be also improved to some extent so that the dielectric anisotropy △ ε of liquid crystal molecule increased.Merck KGaA and
Japanese Chisso Corporation (CN1717468A, CN101143808A, CN101157862A etc.) has been disclosed for some and taken with difference
The Dai Ji liquid-crystal compounds with difluoromethylenedioconnecting linking group (- CF2O-).But the introducing of (- CF2O-) group can make liquid
Brilliant clearing point is greatly lowered.Need to add the bigger high clearing point compound of viscosity when allocating liquid crystal compound to balance
Clearing point caused by (- CF2O-) group declines, so as to constrain the space of liquid crystal compound response speed lifting.
Liquid crystal as liquid crystal display device Core Feature material, in order to meet the various performance parameters of liquid crystal display device
Requirement, in order to adapt to the technological requirement of liquid crystal display device, it is necessary to which liquid crystal material has extensive multiple performance parameter, and appoints
A kind of what monomeric liquid crystal material is impossible to meet all these requirements, it is therefore desirable to the different monomer liquid crystal of synthesis performance, leads to
Toning matches somebody with somebody the method for mixed liquid crystal to meet the characteristic of LCD device requirement.
The content of the invention
The technical problem to be solved in the invention is to provide one kind and contains dimethyl benzene and difluoromethylenedioconnecting linking group
Liquid-crystal compounds and its application, the clearing point existed to improve existing liquid-crystal compounds with difluoromethylenedioconnecting declines
The problem of, lift the response speed of liquid crystal compound.
In order to solve the above technical problems, the technical solution adopted in the present invention is：
Liquid-crystal compounds containing dimethyl benzene and difluoromethylenedioconnecting linking group, the structural formula of the compound is as led to
Shown in formula I,
Wherein,
It is selected fromAny one in group；
X1、X2、X3Selected from H, F, OCF3In any one；
R1Straight-chain alkenyl that the straight chained alkyl for being 1~6 selected from carbon atom, carbon number are 2~6, carbon number are 3~6
Cycloalkyl in any one；
M is selected from 0 or 1；
N is selected from 1 or 2.
Technical solution of the present invention further improvement is that：Compound shown in the formula I is specially the institute of formula I -1 to I -4
The compound shown,
Technical solution of the present invention further improvement is that：Compound shown in the formula I is specially the -1-1 of formula I to I -4-
Compound shown in 2,
The liquid-crystal composition of liquid-crystal compounds composition containing dimethyl benzene and difluoromethylenedioconnecting linking group, the liquid
Crystal composite include as shown in formula I compound group into component A, as shown in formula II one or two kinds of compound groups into group
Point B, as shown in general formula III three to ten kinds of compound groups into component C, the component A, component B, component C mass ratio for 1~
40：5~40：5~80,
Wherein,
R1、R2It is any one in the straight-chain alkenyl that the straight chained alkyl for being 1~6 selected from carbon number, carbon number are 2~6
Kind；
R3It is any one in 1~6 straight chained alkyl selected from H, F, carbon number；
Any one in Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylene and fluoro Isosorbide-5-Nitrae-phenylene；
P is 2 or 3；
(F) H or F is represented.
Technical solution of the present invention further improvement is that：Compound shown in the formula II is specially formula II -1 to formula
Compound shown in II -9,
Technical solution of the present invention further improvement is that：Compound shown in the general formula III is specially formula III -1 to formula
Compound shown in III -10,
Technical solution of the present invention further improvement is that：Component A, component B, component C matter in the liquid-crystal composition
Amount is than being 10~35：15~35：25~75.
Technical solution of the present invention further improvement is that：Also comprising the weight for accounting for liquid-crystal composition in the liquid-crystal composition
Amount percentage composition is not more than 0.05% additive, and the additive is at least one in antioxidant, anti ultraviolet agent, chiral agent
Kind.
By adopting the above-described technical solution, the technological progress that the present invention is obtained is：
The liquid-crystal compounds containing dimethyl benzene and difluoromethylenedioconnecting linking group of the present invention, with wider application model
Enclose.It may be used as the basic material of liquid crystal compound, it is also possible to other kinds of compound can be added to as added material
Among the liquid crystal basic material constituted, such as dielectric anisotropy △ ε, rotary viscosity γ to improve liquid crystal compound1, threshold
Threshold voltage Vth, the parameter such as contrast, optical anisotropy △ n, clearing point Cp under low temperature.
The present invention's contains dimethyl benzene and difluoromethylenedioconnecting linker it can be seen from embodiment 1-8 monomer parameters
The advantage that the liquid-crystal compounds of group is protruded is to be conducive to adjusting the liquid crystal mixing of wide operating temperature with high clearing point Cp
Thing.
The response speed t of liquid-crystal composition and the thickness d of liquid crystal cell, the rotary viscosity γ 1 of liquid crystal meet t ∝ γ 1d2's
Relation, thus it is shorter with its response time of relatively low rotary viscosity γ 1 liquid crystal.And the compound of formula I molecule that the present invention is provided
In structure, contain dimethyl benzene and difluoromethylenedioconnecting (- CF2O-) the liquid-crystal compounds of linking group, not only with larger
Dielectric anisotropy △ ε, it is often more important that while having faster response speed t, relatively low rotary viscosity γ 1 and well low
Warm nature energy, for allotment liquid crystal compound, the performance has great importance.
This patent liquid-crystal composition is provided simultaneously with each to different with big dielectric it can be seen from composition embodiment 9-11
Property △ ε, high clearing point, high refractive index, low driving voltage (big dielectric anisotropy △ ε) can be realized simultaneously, wide
Temperature use environment (high clearing point), low liquid crystal cell are thick (high refractive index), applied to liquid crystal panel, can more power saving and
Quick response.
Compound shown in pure formula I is colourless, and is shown higher to light, heat, chemical stability.Especially
It is that the response that compound shown in Formulas I is shown under big dielectric anisotropy △ ε and good cryogenic property such as low temperature is fast
Degree and contrast, and also have the advantages that to suppress to form smectic phase, this shows the liquid crystal compound for having used compound shown in formula I
With preferable low-temperature storage stability.
The liquid-crystal compounds containing dimethyl benzene and difluoromethylenedioconnecting linking group that the present invention is provided and its composition
Application of the liquid-crystal composition in liquid crystal display device material or electro-optical display part material is prepared, and comprising containing diformazan
The liquid crystal display device material or electrooptics of the liquid-crystal compounds or liquid-crystal composition of base benzene and difluoromethylenedioconnecting linking group
Display device material, falls within protection scope of the present invention.
Embodiment
The present invention is described in further details with reference to embodiment：
The invention discloses the liquid-crystal compounds containing dimethyl benzene and difluoromethylenedioconnecting linking group, the compound
Structural formula as shown in formula I,
Wherein,
It is selected fromIt is any one in group
Kind；
X1、X2、X3Selected from H, F, Cl, CF3、CHF2、OCF3And OCHF2In any one；
R1Straight-chain alkenyl that the straight chained alkyl for being 1~6 selected from carbon atom, carbon number are 2~6, carbon number are 3~6
Cycloalkyl in any one；
M is selected from 0 or 1；
N is selected from 1 or 2.
Specifically, compound shown in formula I is specially the compound shown in formula I -1 to I -4,
The preparation for also disclosing the liquid-crystal compounds containing dimethyl benzene and difluoromethylenedioconnecting linking group of the present invention
Method,
The synthetic route of compound is shown in formula I,
The present invention further discloses the composition of the liquid-crystal compounds containing dimethyl benzene and difluoromethylenedioconnecting linking group
Liquid-crystal composition, liquid-crystal composition include as shown in formula I compound group into component A, it is a kind of as shown in formula II or two
Kind of compound group into component B, as shown in general formula III three to ten kinds of compound groups into component C, the component A, component B, group
The mass ratio for dividing C is 1~40：5~40：5~80,
Wherein,
R1、R2It is any one in the straight-chain alkenyl that the straight chained alkyl for being 1~6 selected from carbon number, carbon number are 2~6
Kind；
R3It is any one in 1~6 straight chained alkyl selected from H, F, carbon number；
Any one or a few in Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylene and fluoro Isosorbide-5-Nitrae-phenylene；
P is 2 or 3；
(F) H or F is represented.
Preferably, the component A, component B, component C mass ratio are 10~35：15~35：25~75.More preferably institute
It is 5~10 to state component A, component B, component C mass ratio：25：75, the component A, component B, component C mass ratio are specific
For 5：25：75 or 10：25：75.
With reference to specific embodiment, the present invention is further elaborated, but the present invention is not limited to following examples.Institute
It is conventional method unless otherwise instructed to state method.The raw material can be obtained from open commercial sources unless otherwise instructed.
The specific meaning and test condition of symbol in embodiment are as follows：
Cp：Unit DEG C, represents the clearing point of liquid crystal.
S-N：Unit DEG C, represents the crystalline state of liquid crystal to nematic fusing point.
△n：Optical anisotropy, △ n=no-ne, wherein, no is the refractive index of ordinary light, and ne is the folding of extraordinary ray
Rate is penetrated, test condition is, 589nm, 25 ± 0.5 DEG C.
△ε：Dielectric anisotropy, △ ε=ε∥-ε⊥, wherein, ε∥For the dielectric constant parallel to molecular axis, ε⊥To be vertical
In the dielectric constant of molecular axis, test condition is 25 ± 0.5 DEG C；1KHz；HP4284A；5.2 microns of left-handed boxes of TN.
γ1：Rotary viscosity, unit mPas, test condition is 25 ± 0.5 DEG C.
VHR：Voltage retention (%), test condition is 20 ± 2 DEG C, voltage is that ± 5V, pulse width be 10ms, voltage guarantor
Hold time 16.7ms.Test equipment is TOYO Model6254 liquid crystal property comprehensive testers.
Contrast is the ratio between liquid crystal display on state of and dark-state, and its assay method is as follows：Liquid crystal is poured into liquid crystal cell, patch is inclined
Mating plate, normal white mode determines driving voltage according to the threshold voltage of liquid crystal, then by the liquid crystal cell extraction wire posted, constant
Backlight under tested, be not added with voltage tester on state of light intensity to liquid crystal cell, making alive test dark-state light intensity, on state of and dark-state
The ratio between light intensity is contrast.
Contrast under normal temperature low temperature contrast rate of change (%)=(contrast under contrast-low temperature under normal temperature)/normal temperature ×
100 (%), normal temperature is 25 DEG C, and low temperature is -20 DEG C.
Cp represents clearing point, and the clearing point can directly be determined and obtained, can be according to such as the compound that can not directly determine
Lower method calculates its fitting data：
Due in the modulated process of mixed liquid crystal, mixed by selecting a variety of and appropriate monomer liquid crystals to allocate, can be with
Form the fusing point of eutectic mixture, effectively reduction liquid crystal；While the monomer liquid crystal by adding high clearing point, it is possible to increase mixed
The clearing point of liquid crystal is closed, so that modulating nematic temperature range meets desired mixed liquid crystal, mixed liquid crystal and monomer liquid crystal
Clearing point and concentration meet following relational expression：
Tc=∑s XiTi
Wherein, Tc represents the clearing point of mixed liquid crystal, XiRepresent concentration of the monomer liquid crystal in mixed liquid crystal, TiRepresent single
The brilliant clearing point of body fluid.
Embodiment 1~8 is the preparation embodiment of liquid-crystal compounds.The general process that reaction is monitored by TLC of course of reaction,
The post processing that reaction terminates is usually washing, extractions, merges and is dried after organic phase, is evaporated off solvent under decompression, and recrystallize, post
Chromatography, those skilled in the art can realize the present invention as described herein below.
Embodiment 1
Liquid crystal compound shown in the -2-14 of formula I, structural formula is as follows,
Synthetic route is,
The following steps a~step f totally six steps are specifically included,
A) in an inert atmosphere, by 242.4g (2.4mol) raw materialIt is dissolved in 1L tetrahydrofurans, is cooled to -30
960ml n-BuLis are added dropwise to after DEG C, rear insulated and stirred are dripped 30 minutes, it is standby.In an inert atmosphere, by 386g (2mol)It is dissolved in 1.5L tetrahydrofurans and is cooled to after -80 DEG C, keeps constant temperature to be added dropwise to the lithium diisopropylamine prepared
Solution, drips rear insulated and stirred 30 minutes, maintains the temperature at and carbon dioxide is passed through in reaction system, reacts 1 hour, stops logical
Carbon dioxide, heats up naturally, in the mixed liquor for reaction solution being poured into 1L water and 0.5L concentrated hydrochloric acids, separates organic layer, extracts, water
Wash, steam neat solvent, obtained product re crystallization from toluene obtains 308g white crystalsYield 64%.
B) by 200g (0.83mol) product obtained by step a)It is dissolved in 1.5L toluene, adds 108g
(1mol) 1,3- dimercaptopropanes, are warming up to 60 DEG C under stirring, 150g (1mol) trifluoromethanesulfonic acids (CF is added dropwise3SO3H), risen after adding
Temperature is to flowing back, and point water, back flow reaction 12 hours, cooling is evaporated toluene, adds 1L methyl tertiary butyl ether(MTBE)s and washes, suction strainer obtains 220g
ProductYield 58%.
C) by 220g (0.48mol) product obtained by step b)It is molten with 1L dichloromethane
Solution, is cooled to -75 DEG C under inert gas shielding, 97g (0.96mol) triethylamines and 88g (0.5mol) is added dropwise
1L dichloromethane solutions, add rear insulation reaction 1 hour, be added dropwise 161g (1.44mol) trihydrofluoride triethylamine, drip off insulation
Reaction 30 minutes, then 160g (1.44mol) Br2 is added dropwise to, -20 DEG C, reaction are warmed naturally to after dripping off insulation reaction 30 minutes
Liquid is poured into the saturated solution of 1L sodium hydrogensulfites, point liquid, is extracted, washing, crosses silicagel column, and concentration obtains 42g productsYield 13%.
D) by 164g (1mol) raw material174g (1mol) m-bromofluorobenzene, 2L toluene, 500ml
It is anti-that ethanol, 1.5L water, 159g (1.5mol) sodium carbonate and the mixing of catalyst 3g tetra-triphenylphosphine palladiums are heated to reflux progress SUZUKI
Answer after 4 hours, reaction solution is poured into 2L water, point liquid is extracted, washing, cross silicagel column, concentration, product ethyl alcohol recrystallization is obtained
ProductYield 90%.
E) 214g (1mol) product obtained step d)It is dissolved in 2L tetrahydrofurans, fills
Nitrogen displacement air, is cooled to -80 DEG C, and 443ml (1.1mol) n-BuLi lithium generation is added dropwise, obtains lithium reagent, is dripped again after adding
Plus the 500ml tetrahydrofuran solutions substitution lithium of 125g (1.2mol) trimethylborate, warm naturally to after 0 DEG C, pour into 2L water,
Plus 200ml concentrated hydrochloric acids, point liquid, extract, washing is evaporated, obtains 168g productsYield
65%.
F) 258g (1mol) product obtained step e)Obtained with step c)
458g (1.1mol) product3L toluene, 500ml ethanol, 1.5L water, 159g
(1.5mol) sodium carbonate and the mixing of catalyst 3g tetra-triphenylphosphine palladiums are heated to reflux after carrying out SUZUKI reactions 4 hours, reaction solution
Pour into 2L water, point liquid is extracted, washing, cross silicagel column, concentration, product re crystallization from toluene obtains 467gYield 85%.
Embodiment 2
Liquid crystal compound shown in the -2-16 of formula I, structural formula is as follows,
Synthetic route is,
The following steps a~step f totally six steps are specifically included,
A) the step a) of reference implementation example 1 is obtained
B) the step b) of reference implementation example 1 is obtained
C) the step c) of reference implementation example 1 is obtained
D) by 176g (1mol) raw material174g (1mol) m-bromofluorobenzene, 2L toluene, 500ml
It is anti-that ethanol, 1.5L water, 159g (1.5mol) sodium carbonate and the mixing of catalyst 3g tetra-triphenylphosphine palladiums are heated to reflux progress SUZUKI
Answer after 4 hours, reaction solution is poured into 2L water, point liquid is extracted, washing, cross silicagel column, concentration, product ethyl alcohol recrystallization is obtained
203g productsYield 90%.
E) 226g (1mol) product obtained step d)It is dissolved in 2L tetrahydrofurans, fills
Nitrogen displacement air, is cooled to -80 DEG C, and 443ml (1.1mol) n-BuLi lithium generation is added dropwise, obtains lithium reagent, is dripped again after adding
Plus the 500ml tetrahydrofuran solutions substitution lithium of 125g (1.2mol) trimethylborate, warm naturally to after 0 DEG C, pour into 2L water,
Plus 200ml concentrated hydrochloric acids, point liquid, extract, washing is evaporated, obtains 175g productsYield
65%.
F) 270g (1mol) product obtained step e)The 458g obtained with step c)
(1.1mol)3L toluene, 500ml ethanol, 1.5L water, 159g (1.5mol) sodium carbonate and catalyst
The mixing of 3g tetra-triphenylphosphine palladiums is heated to reflux after carrying out SUZUKI reactions 4 hours, and reaction solution is poured into 2L water, point liquid, is extracted, and is washed,
Silicagel column is crossed, is concentrated, product re crystallization from toluene obtains 477g productsReceive
Rate 85%.
Embodiment 3
Liquid crystal compound shown in the -2-18 of formula I, structural formula is as follows,
Synthetic route is,
The following steps a~step f totally six steps are specifically included,
A) the step a) of reference implementation example 1 is obtained
B) the step b) of reference implementation example 1 is obtained
C) the step c) of reference implementation example 1 is obtained
D) by 190g (1mol) raw material174g (1mol) m-bromofluorobenzene, 2L toluene, 500ml
It is anti-that ethanol, 1.5L water, 159g (1.5mol) sodium carbonate and the mixing of catalyst 3g tetra-triphenylphosphine palladiums are heated to reflux progress SUZUKI
Answer after 4 hours, reaction solution is poured into 2L water, point liquid is extracted, washing, cross silicagel column, concentration, product ethyl alcohol recrystallization is obtained
216g productsYield 90%.
E) 240g (1mol) product obtained step d)It is dissolved in 2L tetrahydrofurans, fills
Nitrogen displacement air, is cooled to -80 DEG C, and 443ml (1.1mol) n-BuLi lithium generation is added dropwise, obtains lithium reagent, is dripped again after adding
Plus the 500ml tetrahydrofuran solutions substitution lithium of 125g (1.2mol) trimethylborate, warm naturally to after 0 DEG C, pour into 2L water,
Plus 200ml concentrated hydrochloric acids, point liquid, extract, washing is evaporated, obtains 184g productsYield
65%.
F) 184g (1mol) product obtained step e)Obtained with step c)
458g (1.1mol)3L toluene, 500ml ethanol, 1.5L water, 159g (1.5mol)
Sodium carbonate and the mixing of catalyst 3g tetra-triphenylphosphine palladiums are heated to reflux after carrying out SUZUKI reactions 4 hours, and reaction solution pours into 2L water
In, point liquid is extracted, washing, crosses silicagel column, and concentration, product re crystallization from toluene obtains 489g productsYield 85%.
Embodiment 4
Liquid crystal compound shown in the -2-15 of formula I, structural formula is as follows,
Synthetic route is,
The following steps a~step f totally six steps are specifically included,
A) the step a) of reference implementation example 1 is obtained
B) the step b) of reference implementation example 1 is obtained
C) the step c) of reference implementation example 1 is obtained
D) by 176g (1mol) raw material174g (1mol) m-bromofluorobenzene, 2L toluene,
500ml ethanol, 1.5L water, 159g (1.5mol) sodium carbonate and catalyst 3g tetra-triphenylphosphine palladiums, which are mixed, to be heated to reflux carrying out
After SUZUKI reacts 4 hours, reaction solution is poured into 2L water, point liquid, is extracted, washing, crosses silicagel column, concentration, product ethanol weight
Crystallization, obtains 203g productsYield 90%.
E) 226g (1mol) product obtained step d)It is dissolved in 2L tetrahydrofurans,
Inflated with nitrogen displaced air, is cooled to -80 DEG C, and 443ml (1.1mol) n-BuLi lithium generation is added dropwise, lithium reagent is obtained, after adding again
The 500ml tetrahydrofuran solutions substitution lithium of 125g (1.2mol) trimethylborate is added dropwise, warms naturally to after 0 DEG C, pours into 2L water
In, plus 200ml concentrated hydrochloric acids, point liquid, extract, washing is evaporated, obtains product175g,
Yield 65%.
F) 270g (1mol) product obtained step e)Obtained with step c)
458g (1.1mol)3L toluene, 500ml ethanol, 1.5L water, 159g (1.5mol)
Sodium carbonate and the mixing of catalyst 3g tetra-triphenylphosphine palladiums are heated to reflux after carrying out SUZUKI reactions 4 hours, and reaction solution pours into 2L water
In, point liquid is extracted, washing, crosses silicagel column, and concentration, product re crystallization from toluene obtains 477g productsYield 85%.
Embodiment 5
Liquid crystal compound shown in the -2-1-1 of formula I, structural formula is as follows,
Synthetic route is,
The following steps a~step f totally six steps are specifically included,
A) the step a) of reference implementation example 1 is obtained
B) the step b) of reference implementation example 1 is obtained
C) the step c) of reference implementation example 1 is obtained
D) by 170g (1mol) raw material174g (1mol) m-bromofluorobenzene, 2L toluene, 500ml
It is anti-that ethanol, 1.5L water, 159g (1.5mol) sodium carbonate and the mixing of catalyst 3g tetra-triphenylphosphine palladiums are heated to reflux progress SUZUKI
Answer after 4 hours, reaction solution is poured into 2L water, point liquid is extracted, washing, cross silicagel column, concentration, product ethyl alcohol recrystallization is obtained
198g productsYield 90%.
E) 220g (1mol) product obtained step d)It is dissolved in 2L tetrahydrofurans, fills
Nitrogen displacement air, is cooled to -80 DEG C, and 443ml (1.1mol) n-BuLi lithium generation is added dropwise, obtains lithium reagent, is dripped again after adding
Plus the 500ml tetrahydrofuran solutions substitution lithium of 125g (1.2mol) trimethylborate, warm naturally to after 0 DEG C, pour into 2L water,
Plus 200ml concentrated hydrochloric acids, point liquid, extract, washing is evaporated, obtains 171g productsYield
65%.
F) 264g (1mol) product obtained step e)Obtained with step c)
458g (1.1mol) product3L toluene, 500ml ethanol, 1.5L water, 159g
(1.5mol) sodium carbonate and the mixing of catalyst 3g tetra-triphenylphosphine palladiums are heated to reflux after carrying out SUZUKI reactions 4 hours, reaction solution
Pour into 2L water, point liquid is extracted, washing, cross silicagel column, concentration, product re crystallization from toluene obtains 472g productsYield 85%.
Embodiment 6
Liquid crystal compound shown in the -2-5-1 of formula I, structural formula is as follows,
Synthetic route is,
The following steps a~step f totally six steps are specifically included,
A) the step a) of reference implementation example 1 is obtained
B) the step b) of reference implementation example 1 is obtained
C) by step 2) gained 220g (0.48mol) productIt is molten with 1L dichloromethane
Solution, is cooled to -75 DEG C under inert gas shielding, 97g (0.96mol) triethylamines and 121g (0.5mol) is added dropwise1L dichloromethane solutions, add rear insulation reaction 1 hour, be added dropwise 161g (1.44mol) trihydrofluoride
Triethylamine, drips off insulation reaction 30 minutes, then is added dropwise to 160g (1.44mol) Br2, risen naturally after dripping off insulation reaction 30 minutes
Temperature is to -20 DEG C, and reaction solution is poured into the saturated solution of 1L sodium hydrogensulfites, point liquid, extracts, washing, crosses silicagel column, and concentration is obtained
To product (6-a) 44g, yield 19%.
D) the step d) of reference implementation example 1 is obtained
E) the step e) of reference implementation example 1 is obtained
F) 258g (1mol) product obtained step e)Obtained with step c)
530g (1.1mol) product (6-a), 3L toluene, 500ml ethanol, 1.5L water, 159g (1.5mol) sodium carbonate and the triphenyls of catalyst 3g tetra-
The mixing of phosphine palladium is heated to reflux after carrying out SUZUKI reactions 4 hours, and reaction solution is poured into 2L water, point liquid, is extracted, and is washed, and crosses silicagel column,
Concentration, product re crystallization from toluene obtains 524g products
Yield 85%.
Embodiment 7
Liquid crystal compound shown in the -2-7-1 of formula I, structural formula is as follows,
Synthetic route is,
The following steps a~step f totally six steps are specifically included,
A) the step a) of reference implementation example 1 is obtained
B) the step b) of reference implementation example 1 is obtained
C) by 220g (0.48mol) product obtained by step b)It is molten with 1L dichloromethane
Solution, is cooled to -75 DEG C under inert gas shielding, 97g (0.96mol) triethylamines and 113g (0.5mol) is added dropwise1L dichloromethane solutions, add rear insulation reaction 1 hour, be added dropwise 161g (1.44mol) trihydrofluoride
Triethylamine, drips off insulation reaction 30 minutes, then is added dropwise to 160g (1.44mol) Br2, risen naturally after dripping off insulation reaction 30 minutes
Temperature is to -20 DEG C, and reaction solution is poured into the saturated solution of 1L sodium hydrogensulfites, point liquid, extracts, washing, crosses silicagel column, and concentration is obtained
To 38g productsYield 17%.
D) the step d) of reference implementation example 1 is obtained
E) the step e) of reference implementation example 1 is obtained
F) 258g (1mol) obtained step e)The 512g obtained with step c)
(1.1mol) product3L toluene, 500ml ethanol, 1.5L water, 159g (1.5mol) sodium carbonate and catalysis
The mixing of agent 3g tetra-triphenylphosphine palladiums is heated to reflux after carrying out SUZUKI reactions 4 hours, and reaction solution is poured into 2L water, point liquid, is extracted, and is washed,
Silicagel column is crossed, is concentrated, product re crystallization from toluene obtains 510g products
Yield 85%.
Embodiment 8
Liquid crystal compound shown in the -1-2-1 of formula I, structural formula is as follows,
Synthetic route is,
The following steps a~step f totally six steps are specifically included,
A) the step a) of reference implementation example 1 is obtained
B) the step b) of reference implementation example 1 is obtained
C) the step c) of reference implementation example 1 is obtained
F) 458g (1.0mol) product obtained step c)180g(1.1mol)3L toluene, 500ml ethanol, 1.5L water, 159g (1.5mol) sodium carbonate and the triphens of catalyst 3g tetra-
The mixing of base phosphine palladium is heated to reflux after carrying out SUZUKI reactions 4 hours, and reaction solution is poured into 2L water, point liquid, is extracted, and is washed, and crosses silicon
Glue post, concentration, product re crystallization from toluene obtains 387g productsReceive
Rate 85%.
The performance parameter for the liquid-crystal compounds that embodiment 1~8 is prepared is as shown in the table.
Embodiment 9
According to the mass ratio of following ingredients, liquid-crystal composition M1 is prepared.
According to the mass ratio 25 between component B and component C:75, component is constituted with liquid-crystal compounds shown in 25 parts of formulas II
B, with compound group shown in the general formula III of following mass fractions into component C, prepares liquid-crystal composition M1.
Embodiment 10
According to the mass ratio of following ingredients, liquid-crystal composition a is prepared.
Embodiment 11
According to the mass ratio of following ingredients, liquid-crystal composition b is prepared
The performance test results of liquid-crystal composition in embodiment 9~11 are as shown in the table.
| Liquid-crystal composition | Δn | Δε | Cp | γ1 |
| M1 | 0.100 | 10.6 | 95 | 130 |
| a | 0.102 | 11.1 | 100 | 125 |
| b | 0.101 | 11.0 | 101 | 123 |
It is added to by compound shown in formula I it can be seen from embodiment 9~11 in liquid-crystal composition, with increasing liquid crystal
Contrast changes less feature under composition dielectric anisotropy Δ ε, reduction mixture rotary viscosity γ 1, low temperature.
Claims (8)
1. the liquid-crystal compounds containing dimethyl benzene and difluoromethylenedioconnecting linking group, it is characterised in that：The compound
Structural formula as shown in formula I,
Wherein,
It is selected fromAny one in group；
X1、X2、X3Selected from H, F, OCF3In any one；
R1The cycloalkanes that straight-chain alkenyl that the straight chained alkyl for being 1~6 selected from carbon atom, carbon number are 2~6, carbon number are 3~6
Any one in base；
M is selected from 0 or 1；
N is selected from 1 or 2.
2. the liquid-crystal compounds according to claim 1 containing dimethyl benzene and difluoromethylenedioconnecting linking group, it is special
Levy and be：Compound shown in the formula I is specially the compound shown in formula I -1 to I -4,
3. the liquid-crystal compounds according to claim 1 containing dimethyl benzene and difluoromethylenedioconnecting linking group, it is special
Levy and be：
Compound shown in the formula I is specially the compound shown in the -1-1 of formula I to I -4-2,
4. the liquid-crystal composition of the liquid-crystal compounds composition containing dimethyl benzene and difluoromethylenedioconnecting linking group, its feature exists
In：The liquid-crystal composition include as shown in formula I compound group into component A, one or two kinds of chemical combination as shown in formula II
Thing composition component B, as shown in general formula III three to ten kinds of compound groups into component C, the component A, component B, component C matter
Amount is than being 1~40：5~40：5~80,
Wherein,
R1、R2Any one in the straight-chain alkenyl that the straight chained alkyl for being 1~6 selected from carbon number, carbon number are 2~6；
R3It is any one in 1~6 straight chained alkyl selected from H, F, carbon number；
Any one in Isosorbide-5-Nitrae-cyclohexylidene, Isosorbide-5-Nitrae-phenylene and fluoro Isosorbide-5-Nitrae-phenylene；
P is 2 or 3；
(F) H or F is represented.
5. the liquid-crystal compounds composition according to claim 4 containing dimethyl benzene and difluoromethylenedioconnecting linking group
Liquid-crystal composition, it is characterised in that：Compound shown in the formula II is specially the compound shown in formula II -1 to formula II -9,
6. the liquid-crystal compounds composition according to claim 4 containing dimethyl benzene and difluoromethylenedioconnecting linking group
Liquid-crystal composition, it is characterised in that：
Compound shown in the general formula III is specially the compound shown in formula III -1 to formula III -10,
7. the liquid-crystal compounds composition according to claim 4 containing dimethyl benzene and difluoromethylenedioconnecting linking group
Liquid-crystal composition, it is characterised in that：Component A, component B, component C mass ratio are 10~35 in the liquid-crystal composition：15~
35：25~75.
8. the liquid-crystal compounds composition according to claim 7 containing dimethyl benzene and difluoromethylenedioconnecting linking group
Liquid-crystal composition, it is characterised in that：Also it is not more than in the liquid-crystal composition comprising the weight percentage for accounting for liquid-crystal composition
0.05% additive, the additive is at least one of antioxidant, anti ultraviolet agent, chiral agent.
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| CN113897202A (en) * | 2021-11-17 | 2022-01-07 | 浙江工业大学 | Difluoromethyleneoxy liquid crystal compound and synthesis method thereof |
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