CN109628107A - One kind having high optically anisotropic liquid-crystal compounds and its application - Google Patents
One kind having high optically anisotropic liquid-crystal compounds and its application Download PDFInfo
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- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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Abstract
The present invention provides one kind to have high optically anisotropic liquid-crystal compounds, liquid-crystal composition and its application including it.The liquid-crystal compounds has general formula I, and general formula I is
Description
Technical field
The present invention relates to liquid crystal material fields, and in particular to a kind of liquid-crystal compounds, comprising its liquid-crystal composition and its
Using.
Background technique
In the 1960s, RCA Corp.'s discovery electro photoluminescence for the first time can change the light transmission mode of liquid crystal, and then application should
After property has issued LCD technology, liquid crystal just gradually causes the great attention of people, and rapidly develops to every field.
1966, after E.I.Du Pont Company is using aromatic polyamides synthesis of liquid crystal Kevlar fiber, liquid crystal material started process of industrialization.
After decades of rapid development, liquid crystal material is by its special performance is widely used to display technology, optical storage is set
The various fields such as standby and solar battery, research range are even more to spread the various fields such as chemistry, biology and information science, become and work as
By one of favor, indispensable new material in modern society.
With making rapid progress for science and technology, requirement of the people to liquid crystal material performance also will be higher and higher.It is expected that from now on
The development of liquid crystal material mainly has the following aspects: (1) explore the new process for preparing existing liquid crystal material, reduce by-product with
The generation of harmful substance reduces production cost；(2) property modification is carried out to available liquid crystal material, as reduced to environment temperature
It is required that improving the diversity rich in color etc. of display liquid crystal material；(3) new function type liquid crystal material is prepared, more necks are met
The high standard requirement in domain, such as display New Liquid Crystal material, the novel photoelectric liquid crystal storage material of information engineering field, life
Novel medicinal liquid crystal material of object engineering field etc..
Liquid crystal display can be divided into passive matrix (also known as passive-matrix or simple matrix) and active matrix (based on also known as
Dynamic matrix) two kinds of driving methods.Wherein, active matrix liquid crystal display is to change the row of liquid-crystal compounds by applying voltage
Column mode, so that the light emitting intensity for changing backlight sending forms image, due to high-resolution, high contrast,
The thin and light feature in low-power, face increasingly has been favored by people.Active matrix liquid crystal display is according to active device
Two types can be divided into: MOS (metal-oxide semiconductor (MOS)) or other diodes on the silicon chip as substrate；Making
For the thin film transistor (TFT) (Thin Film Transistor-TFT) on the glass plate of substrate, wherein development is most rapid at present
It is Thin Film Transistor-LCD (TFT-LCD), shows in mobile phone, computer, LCD TV and camera etc. and obtained in equipment
Good application has been arrived, the main product in current liquid crystal market is become.
With the extensive use of liquid crystal display, the requirement to its performance is also in the continuous improvement, it is desirable that wider array of work
Temperature, faster response speed and higher contrast, and require power consumption lower and lower simultaneously, reducing power consumption means liquid crystal
Show that device will have lower driving voltage and higher light transmittance.The raising of these performances all be unable to do without the improvement of liquid crystal material.
Summary of the invention
The object of the present invention is to provide one kind to have high optically anisotropic liquid-crystal compounds, to improve in the prior art
The characteristics such as optical anisotropy, liquid crystal phase temperature range and the coefficient of elasticity of liquid crystal material, to improve the response of liquid crystal material
Speed increases the use temperature range of liquid crystal material.
It is a further object of the present invention to provide the liquid-crystal compositions comprising above-mentioned liquid-crystal compounds.
The application of liquid-crystal composition it is yet another object of the invention to provide above-mentioned liquid-crystal compounds and comprising it.
Technical solution: to achieve the goals above, according to an aspect of the invention, there is provided a kind of liquid-crystal compounds,
The liquid-crystal compounds has general formula I, the general formula I are as follows:
Wherein,
Y and Y ' is each independently selected from the alkenyl or C2~C7 of H, C1~C7 alkyl, the alkoxy of C1~C7, C2~C7
Alkene alkoxy, wherein H can be replaced by cyclopenta or F, CH2It can be replaced by cyclopenta, O or F, and two adjacent CH2It cannot
Replaced simultaneously by O；Alternatively, the Y and Y ' are each independently selected from cyclopenta, oxygen cyclopentaOxygen methylcyclopentylOxygen ethylcyclopentylOr for the alkyl of C1~C7, the alkoxy of C1~C7, C2~C7 alkenyl
Or cyclopenta, oxygen cyclopenta, oxygen methylcyclopentyl, oxygen ethylcyclopentyl that the alkene alkoxy of C2~C7 replaces；Alternatively, the Y
And Y ' is each independently selected from cyclopentenyl, oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base, or is C1
Cyclopentenyl, the oxygen ring penta of the alkene alkoxy substitution of the alkyl of~C7, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Alkenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base；
A and b is each independently selected from 0,1 or 2, and a and b are not 0 simultaneously；
When a is 1,It is selected from Any one of group of composition；
It include two in general formula when a is 2I.e.Occur in general formula twice, at each occurrenceIt is each independently selected from Any one of group of composition；
When b is 1,It is selected from Any one of group of composition；
It include two in general formula when b is 2I.e.Occur in general formula twice, at each occurrenceIt is each independently selected from Any one of group of composition.
AndIn at least 1 be selected from Any one of group of composition.
According to another aspect of the present invention, a kind of liquid crystal compound is provided, which includes at least one
The liquid-crystal compounds stated.
According to another aspect of the invention, the above-mentioned liquid-crystal compounds of one kind is provided in liquid crystal display material or liquid crystal
Show the application in equipment.
According to another aspect of the invention, the above-mentioned liquid crystal compound of one kind is provided in liquid crystal display material or liquid crystal
Show the application in equipment.
The utility model has the advantages that liquid-crystal compounds of the invention can be effectively improved the optical anisotropy of liquid crystal material, nematic
Phase temperature range and coefficient of elasticity, to improve the response speed and use temperature range of liquid crystal material.
Specific embodiment
It should be noted that in the absence of conflict, the features in the embodiments and the embodiments of the present application can phase
Mutually combination.Below in conjunction with embodiment, the present invention will be described in detail.
In an exemplary embodiment of the invention, a kind of liquid-crystal compounds is provided, which has logical
Formulas I, the general formula I are as follows:
Wherein,
Y and Y ' is each independently selected from the alkenyl or C2~C7 of H, C1~C7 alkyl, the alkoxy of C1~C7, C2~C7
Alkene alkoxy, wherein H can be replaced by cyclopenta or F, CH2It can be replaced by cyclopenta, O or F, and two adjacent CH2It cannot
Replaced simultaneously by O；Alternatively, the Y and Y ' are each independently selected from cyclopenta, oxygen cyclopentaOxygen methylcyclopentylOxygen ethylcyclopentylOr for the alkyl of C1~C7, the alkoxy of C1~C7, C2~C7 alkenyl
Or cyclopenta, oxygen cyclopenta, oxygen methylcyclopentyl, oxygen ethylcyclopentyl that the alkene alkoxy of C2~C7 replaces；Alternatively, the Y
And Y ' is each independently selected from cyclopentenyl, oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base, or is C1
Cyclopentenyl, the oxygen ring penta of the alkene alkoxy substitution of the alkyl of~C7, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Alkenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base；
A and b is each independently selected from 0,1 or 2, and a and b are not 0 simultaneously；
When a is 1,It is selected from Any one of group of composition；
It include two in general formula when a is 2I.e.Occur in general formula twice, at each occurrenceIt is each independently selected from Any one of group of composition；
When b is 1,It is selected from Any one of group of composition；
It include two in general formula when b is 2I.e.Occur in general formula twice, at each occurrenceIt is each independently selected from Any one of group of composition.
Liquid-crystal compounds with general formula I be under pure material state it is white, not according to F atom number and position
It together, can be for low pole or nonpolar liquid-crystal compounds, or the LCD compound with negative polarity or positive polarity
Object can need to choose the structure of different performance according to display.
Liquid-crystal compounds with general formula I is conjugated system compound since the rigid radical of main chain is biphenyl structural, because
This optical anisotropy Δ n value with higher.In general, when light enters anisotropic material, vibration will be generally divided into
Dynamic direction is mutually perpendicular to, two waves of spread speed not etc., they have two refracted lights respectively, constitute it is so-called birefringent,
Material is respectively obtained to directional light with to the refractive index of vertical light using polarizing film, and taking its difference is optical anisotropy Δ n
Value.And refractive index is higher, light, with respect to optically thinner medium, is more easy to happen total reflection by opposite optically denser medium directive.And refractive index and
The arrangement of charge is closely related, and charge placement is closer, then refractive index is bigger, and compounds of formula I is conjugated system compound,
Its charge placement is close, thus has biggish refractive index.Wherein optical anisotropy Δ n value is according to pre-set light
(d Δ n) is adjusted path difference, and intima-media thickness d is determined by optical anisotropy △ n, especially in higher d △ n
Under value, if having high value for optical anisotropy △ n, d value can be selected as smaller value, thus the response time
With being more preferably worth.
Although in addition the introducing of F atom can increase the dielectric constant of liquid-crystal compounds, the clear of liquid-crystal compounds can be made
Bright spot temperature is declined, and then influences the use temperature width of liquid crystal material, and the introducing of methyl can not only increase liquid crystal
The clearing point temperature of compound can also be acted on due to the steric hindrance between F atom, destroy the symmetry of liquid-crystal compounds, from
And the fusing point of liquid-crystal compounds is reduced, have the function that increase liquid-crystal compounds liquid crystal width.
In addition the addition of alkyl can also improve the coefficient of elasticity of liquid-crystal compounds, so as to improve light in whole system
Penetrance and contrast, be beneficial to energy conservation, and image displaying quality can be improved, can preferably meet liquid crystal display
Performance requirement.According further to response time formula ON state:OFF state:Response time and elasticity
Coefficient k is inversely proportional, therefore coefficient of elasticity k is bigger, and the response time is shorter, then response speed is faster.
Another outstanding feature of the liquid-crystal compounds of general formula I is when combining with other type liquid-crystal compounds, can both to protect
The advantage for staying its optical anisotropy value high, and its deficiency in terms of viscosity and Low-Temperature Reliability can be improved, so as to
Obtain the liquid crystal material of lower driving voltage, broader operating temperature and faster response speed.Especially with low viscosity liquid crystal
When compound combination, suitable optical characteristics and liquid crystal width can be obtained with small amount addition.Therefore, the liquid-crystalization of general formula I
The liquid crystal compound overall viscosity that conjunction object is combined with other type liquid-crystal compounds is lower, and time formula is opened according to response
State:OFF state:Response time and viscosity γ1It is directly proportional, therefore γ1It is smaller, the response time
Shorter, then response speed is faster.
In addition, it should be clear to a person skilled in the art that, abovementioned alkyl not only includes that straight chained alkyl also includes propping up accordingly
Alkyl group.
In order to obtain more particularly suitable liquid crystal width, higher dielectric anisotropy value, lesser rotary viscosity and be suitable for
Coefficient of elasticity, be more advantageous to improve liquid crystal material response speed, reduce threshold voltage, improve liquid crystal material intersolubility and
Reliability, in a preferred embodiment of the present application, the liquid-crystal compounds of above-mentioned general formula I are the liquid crystal with Formulas I 1 to I87
Compound.The above-mentioned compound formula with general formula I1 to I87 is as follows:
Wherein, R1、R1' be each independently selected from H, C1~C7 alkyl, the alkoxy of C1~C7, C2~C7 alkenyl or
The alkene alkoxy of C2~C7, wherein H can be replaced by cyclopenta or F, CH2It can be replaced by cyclopenta, O or F, and two adjacent CH2
It cannot be replaced simultaneously by O；Alternatively, the R1、R1' it is each independently selected from cyclopenta, oxygen cyclopentaOxygen methyl ring
AmylOxygen ethylcyclopentylIt or is the alkyl of C1~C7, the alkoxy of C1~C7, C2~C7
Cyclopenta, the oxygen cyclopenta, oxygen methylcyclopentyl, oxygen ethylcyclopentyl of the alkene alkoxy of alkenyl or C2~C7 substitution；Alternatively, institute
State R1、R1' it is each independently selected from cyclopentenyl, oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base, Huo Zhewei
Cyclopentenyl, the oxygen ring of the alkene alkoxy substitution of the alkyl of C1~C7, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Pentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base.
Due to the liquid-crystal compounds optical anisotropy value with higher with general formula I of the invention, wide temperature model
The nematic phase enclosed, higher coefficient of elasticity k the liquid-crystal compounds with general formula I combine shape with other type liquid-crystal compounds
When at liquid crystal compound, which can be adjusted in wider range, to meet more liquid crystal materials
Performance requirement.Also, have when the liquid-crystal compounds with general formula I of the invention is mixed with other type liquid-crystal compounds preferable
Intersolubility, for other liquid-crystal compounds etc. type less-restrictive, be applicable to various liquid corresponding with purpose
Brilliant mixture is particularly conducive to improve the bulk properties of liquid crystal compound.In addition, the liquid crystal compound has good UV, light
And thermal stability.
Liquid-crystal composition of the invention can be prepared conventionally.Usually under high temperature by the desired amount of component with
Relatively low amount is dissolved in the component for constituting principal component；The solution of each component organic solvent be can also be mixed into, such as acetone, chloroform are mixed into
Or in methanol, solvent is removed again after being sufficiently mixed, such as solvent is removed by distillation.
The type for the existing liquid-crystal compounds for including in liquid-crystal composition of the invention is not restricted, can be according to purpose
The liquid-crystal compounds of selection any kind constitutes liquid crystal compound together with liquid-crystal compounds of the invention, can also add as needed
Enter other additives of technical field.For example, it is living to add polymerizable compound, optically-active that mass content is 0~20%
Property component and/or stabilizer.
Above-mentioned polymerizable compound general formula is as follows:
Wherein,
-T1With-T2It each independently representsOr epoxy group；
-W1And-W2Singly-bound or carbon atom number are each independently represented as 1~8 alkyl；
-X1And-X2Each independently represent singly-bound ,-O- ,-CO- ,-COO- or-OCO-；
-Z1It is selected from singly-bound ,-O- ,-CO- ,-COO- ,-OCO- ,-CH2O-、-OCH2-、-C2H4-、-CF2O-、-OCF2-、-C
≡ C- ,-CH=CH-, One or both of group of composition；
I is 0,1 or 2；
When i is 1 ,-Z1Indicate singly-bound ,-O- ,-CO- ,-COO- ,-OCO- ,-CH2O-、-OCH2-、-C2H4-、-
CF2O-、-OCF2,-C ≡ C- ,-CH=CH-,
When i is 2 ,-Z1Occur in general formula twice ,-Z1Each independently represent when occurring every time singly-bound ,-O- ,-
CO-、-COO-、-OCO-、-CH2O-、-OCH2-、-C2H4-、-CF2O-、-OCF2,-C ≡ C- ,-CH=CH-,
It indicatesWherein-the CH on cyclohexyl2It can be replaced by O, or indicateWherein benzene
On ring=CH- can replace by N, the H on phenyl ring can be replaced by F, or indicate
When i is 1,It indicatesWherein-the CH on cyclohexyl2It can be replaced by O, or indicateWherein on phenyl ring=CH- can replace by N, the H on phenyl ring can be replaced by F, or indicate
It include two in general formula when i is 2I.e.Occur in general formula twice,?
It is each independently when occurring every timeWherein-the CH on cyclohexyl2It can be replaced by O, or beWherein
On phenyl ring=CH- can replace by N, the H on phenyl ring can be replaced by F, or be
Above-mentioned optically active component is preferred are as follows:
Wherein, R10For H, the halogenation with 1 to 7 carbon atoms or unsubstituted alkyl, alkoxy or alkenyl, wherein H can
Replaced by cyclopenta or F, CH2It can be replaced by cyclopenta, O or F, and two adjacent CH2It cannot be replaced simultaneously by O；The alkane
Base, the alkoxy and the alkenyl are alkyl, alkoxy and the alkenyl of linear chain or branched chain.
Above stabilizer preferably has one of compound shown in general formula VI1~VI5 or a variety of:
In 1~VI5 of Formula IV, R9For H, the alkyl with 1~7 carbon atom, the alkoxy with 1~7 carbon atom or
Alkenyl with 2~7 carbon atoms, wherein H can be replaced by cyclopenta or F, CH2It can be replaced by cyclopenta, O or F, and adjacent
Two CH2It cannot be replaced simultaneously by O；The alkyl, the alkoxy and the alkenyl are alkyl, the alcoxyl of linear chain or branched chain
Base and alkenyl；
It is selected from Any one of group of composition.
In a preferred embodiment of the present application, above-mentioned liquid-crystal composition further include at least one polar compound and/
Or at least one non-polar compound.The polar compound is positive polar compound and/or negative polarity compound, the anode
Property compound be selected from one of compound shown in 1~X105 of Formula X or a variety of, the negative polarity compound be selected from Formula II 1~
One of compound shown in II98 is a variety of, and the non-polar compound is in compound shown in 1~III36 of formula III
It is one or more.
Wherein, the positive polarity compound with X1 to X105 is respectively as follows:
The Formula X 1 is into X105, R7For H, carbon atom number be 1~7 alkyl, carbon atom number be 1~7 alkoxy, carbon
The alkene alkoxy that the alkenyl or carbon atom number that atomicity is 2~7 are 2~7, wherein H can be replaced by cyclopenta or F, CH2It can be by ring
Amyl, O or F replace, and two adjacent CH2It cannot be replaced simultaneously by O；It or is cyclopenta, oxygen cyclopenta
Oxygen methylcyclopentylOxygen ethylcyclopentylOr for the alkyl of C1~C7, C1~C7 alkoxy,
Cyclopenta, the oxygen cyclopenta, oxygen methylcyclopentyl, oxygen ethyl ring penta that the alkenyl of C2~C7 or the alkene alkoxy of C2~C7 replace
Base；Perhaps cyclopentenyl, oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base or the alkane for C1~C7 are selected from
Cyclopentenyl, the oxygen cyclopentenyl, oxygen of the alkene alkoxy substitution of base, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Methyl cyclopentene base, oxygen ethylcyclopentene base；R8For H, F, CN, NCS, Cl, OCF3, alkyl, alcoxyl with 1 to 7 carbon atoms
Base, alkenyl or alkene alkoxy, wherein H or CH2It can be replaced by cyclopenta or F；R8It can also be cyclopenta, oxygen cyclopenta
Oxygen methylcyclopentylOr oxygen ethylcyclopentylIt or is the alkyl of C1~C7, the alcoxyl of C1~C7
Cyclopenta, the oxygen cyclopenta, oxygen methylcyclopentyl, oxygen ethyl ring of the alkene alkoxy substitution of base, the alkenyl of C2~C7 or C2~C7
Amyl；Perhaps selected from cyclopentenyl, oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base or be C1~C7's
Alkyl, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7 alkene alkoxy replace cyclopentenyl, oxygen cyclopentenyl,
Oxygen methyl cyclopentene base, oxygen ethylcyclopentene base；It is described to have 1 to 7 carbon atom alkyls preferred are as follows:-CH3、-C2H5、-C3H7、-
C4H9、-C5H11、-C6H13Or-C7H15；The alkenyl for having 1 to 7 carbon atoms is preferred are as follows:-CH=CH2,-CH=CHCH3、-
CH=CHC2H5,-CH=CHC3H7、-C2H4CH=CH2、-C2H4CH=CHCH3、-C3H6CH=CH2Or-C3H6CH=CHCH3；Institute
It is preferred to state the alkoxy with 1 to 7 carbon atoms are as follows:-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13Or-
OC7H15；The alkene alkoxy for having 1 to 7 carbon atoms is preferred are as follows:-OCH=CH2、-OCH2CH=CH2、-OCH2CH=
CHCH3Or-OCH2CH=CHC2H5；X9、X10And V1It is each independently selected from H, methyl or F.
Above-mentioned positive polarity liquid-crystal compounds X1~X105 has positive dielectric anisotropy, can group with above-mentioned liquid-crystal composition
Positive dielectric liquid crystal mixture is synthesized, the liquid crystal compound with negative dielectric can also be combined into, can be used for the dielectric of regulation system
The parameters such as constant, refraction coefficient, rotary viscosity, coefficient of elasticity and clearing point temperature.It is added in positive dielectric liquid crystal mixture suitable
The negative dielectric liquid crystal compound of amount, can be by introducing the negative higher vertical dielectric constant ε of dielectric liquid crystal compound⊥, Lai Gaishan
The light transmittance of positive dielectric liquid crystal mixture, and then be beneficial to energy conservation.And on the basis of above-mentioned composition be added structural difference compared with
Big positive dielectric liquid crystal compound, advantageously reduces fusing point, improves the Low-Temperature Reliability of liquid crystal compound, to reduce liquid crystal Jie
Matter uses lower limit temperature, widens the operating temperature range of liquid crystal media.
Wherein, the negative polarity compound with II1~II98 is respectively as follows:
In 1~II98 of Formula II, R3And R4It is each independently H, the alkyl that carbon atom number is 1~7, carbon atom number are 1~7
Alkoxy, carbon atom number be 2~7 alkenyl or carbon atom number be 2~7 alkene alkoxy, wherein H can be taken by cyclopenta or F
Generation, CH2It can be replaced by cyclopenta, O or F, and two adjacent CH2It cannot be replaced simultaneously by O；It or is cyclopenta, oxygen ring penta
BaseOxygen methylcyclopentylOxygen ethylcyclopentylOr alkyl for C1~C7, C1~
Cyclopenta that the alkene alkoxy of the alkoxy of C7, the alkenyl of C2~C7 or C2~C7 replaces, oxygen cyclopenta, oxygen methylcyclopentyl,
Oxygen ethylcyclopentyl；Or it is selected from cyclopentenyl, oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base, Huo Zhewei
Cyclopentenyl, the oxygen ring of the alkene alkoxy substitution of the alkyl of C1~C7, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Pentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base；The alkyl that the carbon atom number is 1~7 is-CH3、-C2H5、-
C3H7、-C4H9、-C5H11、-C6H13Or-C7H15；The alkenyl that the carbon atom number is 2~7 is preferably-CH=CH2,-CH=
CHCH3,-CH=CHC2H5,-CH=CHC3H7、-C2H4CH=CH2、-C2H4CH=CHCH3、-C3H6CH=CH2Or-C3H6CH=
CHCH3；The alkoxy that the carbon atom number is 1~7 is preferably-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13
Or-OC7H15；The alkene alkoxy that the carbon atom number is 2~7 is preferably-OCH2CH=CH2、-OCH2CH=CHCH3Or-OCH2CH
=CHC2H5。
Above-mentioned polarity liquid-crystal compounds II1~II98 has negative dielectric anisotropic, negative permittivity liquid-crystal compounds
Feature is that have biggish dipole effect on perpendicular to molecular long axis direction, thus corresponding dielectric constant is in vertical direction
Component it is relatively large, i.e., vertical dielectric constant ε with higher⊥, liquid crystal molecule tend to along perpendicular to direction of an electric field be distributed,
And negative type liquid crystal material is all to arrange under fringe field on the horizontal level, pre-tilt angle distribution is uniform compared with eurymeric material, thus
Show higher light transmittance and wide viewing angle；In addition the curved of system can be improved in the addition of the liquid-crystal compounds of negative permittivity
Bent coefficient of elasticity k33, so as to improve light in the penetrance of whole system, it is beneficial to energy conservation, and be conducive to improve contrast.Separately
The addition of outer variety classes liquid-crystal compounds also helps the Low-Temperature Reliability for improving liquid crystal media, reduces the use of liquid crystal media
Lower limit temperature widens the operating temperature range of liquid crystal media.
Above-mentioned nonpolarity liquid-crystal compounds is selected from one of compound shown in 1~III36 of formula III or a variety of, wherein formula
III1~III36 is as follows:
In the 1~III36 of formula III, R5、R6It is each independently selected from H, F, the alkyl that carbon atom number is 1~7, carbon atom
The alkoxy for 1~7, the alkenyl that carbon atom number is 2~7 or the alkene alkoxy that carbon atom number is 2~7 are counted, wherein H can be by ring penta
Base or F replace, CH2It can be replaced by cyclopenta, O or F, and two adjacent CH2It cannot be replaced simultaneously by O；It or is ring penta
Base, oxygen cyclopentaOxygen methylcyclopentylOxygen ethylcyclopentylIt or is C1~C7's
Cyclopenta, the oxygen cyclopenta, oxygen first of the alkene alkoxy substitution of alkyl, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Cyclopentyl, oxygen ethylcyclopentyl；Or it is selected from cyclopentenyl, oxygen cyclopentenylOxygen methyl cyclopentene baseOxygen ethylcyclopentene baseIt or is the alkyl of C1~C7, the alkoxy of C1~C7, C2~C7
Alkenyl or C2~C7 alkene alkoxy replace cyclopentenyl, oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene
Base；The alkyl that the carbon atom number is 1~7 is-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13Or-C7H15；The carbon is former
The alkenyl that subnumber is 2~7 is preferably-CH=CH2,-CH=CHCH3,-CH=CHC2H5,-CH=CHC3H7、-C2H4CH=CH2、-
C2H4CH=CHCH3、-C3H6CH=CH2Or-C3H6CH=CHCH3；The carbon atom number be 1~7 alkoxy preferably-
OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13Or-OC7H15；The alkene alkoxy that the carbon atom number is 2~7 is excellent
It is selected as-OCH=CH2、-OCH2CH=CH2、-OCH2CH=CHCH3Or-OCH2CH=CHC2H5。
Above-mentioned nonpolarity liquid-crystal compounds III1 to III9 has lower rotary viscosity γ1, the response time and rotation
Viscosity γ1It is directly proportional, illustrate rotary viscosity γ1Value is lower, and the response time is lower, then response speed is faster, can will have above-mentioned non-
The liquid crystal compound of polarity liquid-crystal compounds III1 to III9 is used to manufacture the liquid crystal media of quick response.Above-mentioned nonpolarity liquid crystal
Compound III10 to III20 clearing point temperature with higher, is mainly used for the T of regulation systemNIValue, to have above-mentioned non-
The liquid crystal compound of polarity liquid-crystal compounds III10 to III20 is conducive to improve the SC service ceiling temperature of liquid crystal media, widens liquid
The operating temperature range of crystalline medium.Above-mentioned nonpolarity liquid-crystal compounds III21 to III27 has terphenyl structure, and III28 is extremely
III33 has alkynyl benzene structure, is big conjugated system compound, is conducive to the optical anisotropy △ n value of increase system, leads to
The value of ordinary light path difference d △ n be it is prespecified, then △ n value is higher, and d value is lower, and response speed is inversely proportional with d value, thus
The response speed of liquid crystal compound with above-mentioned nonpolarity liquid-crystal compounds III21 to III33, which has, to be more preferably worth.It is above-mentioned
Nonpolar liquid-crystal compounds III34 to III36 has biggish coefficient of elasticity, and the response time is inversely proportional with coefficient of elasticity, explanation
Elasticity values are higher, and the response time is lower, then response speed is faster, therefore have above-mentioned nonpolar liquid-crystal compounds III34
Liquid crystal compound to III36 has ideal response speed.
The outstanding feature of liquid-crystal compounds shown in formula of I of the present invention is when combining with Low-Viscosity Liquid-Crystal Compound, with
Small amount addition can be obtained suitable photoelectric characteristic, therefore can reduce the overall viscosity of liquid crystal compound, increase response speed
Degree.It is preferred that a kind of low viscosity nonpolarity liquid-crystal compounds that structural formula is III 1 to III 9 is at least added in liquid crystal compound,
To obtain the liquid crystal compound of low viscosity, response speed is improved.A kind of structural formula is at least added in particularly preferred liquid crystal compound
Response speed is improved for the low viscosity nonpolarity liquid-crystal compounds of III3 to obtain the liquid crystal compound of low viscosity.III3 is into one
Step is preferably R5For propyl, R6For the compound of vinyl.The liquid crystal compound can be applied to eurymeric display pattern, can also
To be applied to minus display pattern, or both combination, be particularly applicable to twisted-nematic (TN), vertically oriented display (VA),
In the vertical arrangement (PSVA) or fringe field switching (FFS) type of polymer stabilizing etc. liquid crystal display mode.
The content of liquid-crystal compounds in above-mentioned liquid crystal compound can be adjusted according to the performance requirement of liquid crystal material.
In order to obtain more particularly suitable liquid crystal width, higher dielectric anisotropy value, lesser rotary viscosity and suitable elasticity system
Number is more advantageous to the response speed for improving liquid crystal material, reduces threshold voltage, improves the intersolubility of liquid crystal material, in the present invention
In a kind of preferred embodiment, the weight content of the liquid-crystal compounds in above-mentioned liquid crystal compound with general formula I is 0.1~
75%, preferably 0.1~50%, further preferred 0.1~30%.Remaining ingredient can be added in above-mentioned introduction according to the present invention
Add.The mass fraction of the polarity liquid-crystal compounds is preferably 0~80%, and the mass fraction of the nonpolarity liquid-crystal compounds is excellent
It is selected as 0~80%.In short, the sum of degree of each ingredient is 100%.
In a kind of typical embodiment of the application, liquid-crystal compounds shown in a kind of above-mentioned general formula I is provided in liquid
Application in crystal display device.In the application in another typical embodiment, provide a kind of comprising liquid shown in general formula I
Application of the liquid crystal compound of brilliant compound in liquid crystal display.Liquid-crystal compounds of the invention is applied and is preparing liquid crystal
In display material or liquid crystal display, the performance of liquid crystal display material or liquid crystal display can significantly improve.
Below with reference to embodiment and comparative example, beneficial effects of the present invention are further illustrated.
The following example is to be used to explain the present invention rather than limit it.Percentage involved in embodiment is quality percentage
Than, temperature with degree Celsius indicating.Surveyed physico-chemical parameter is expressed as follows: TNIIndicate clearing point；△ n indicates optical anisotropy (△ n
=ne-no, 589nm, 25 DEG C of temperature of measurement)；△ ε indicates dielectric anisotropy (△ ε=ε∥-ε⊥, measure 25 DEG C of temperature)；k11Table
Show Splay elastic constant (25 DEG C of temperature of measurement)；k33Indicate elasticity of flexure coefficient (25 DEG C of temperature of measurement)；γ1Indicate rotary viscosity
(25 DEG C of temperature of measurement), and use dsc measurement TNI；△ n is measured using abbe refractometer；△ ε, k are measured using CV11、k33With
γ1。
In the various embodiments of the invention, liquid crystal molecule main chain is named: cyclohexylIt is indicated with letter C；Phenyl ringIt is indicated with alphabetical P；Cyclohexenyl groupIt is indicated with A；Positive dielectric difluorobenzeneIt is indicated with Y；OxinaneIt is indicated with J；Methoxyl group bridge-CH2O- is indicated with B；Difluoro-methoxy bridge-CF2O- is indicated with Q；Alkynyl-C ≡ C- is with G table
Show；Single fluorobenzeneIt is indicated with alphabetical H1；Negative dielectric difluorobenzeneIt is indicated with W；Difluorodiphenyl and furansIt is indicated with alphabetical X1；Methyl list fluorobenzeneIt is indicated with alphabetical K1.
The correspondence code of specific unit structure is as shown in table 1.
Table 1
Each compound branch is converted to chemical formula according to following table 2, and left side branch indicates that right side branch is with R2 table with R1
Show.Wherein, group CnH2n+1And CmH2m+1It is the straight chained alkyl for being respectively provided with n and m carbon atom, CpIndicate cyclopentaCnH2n+1CpIndicate the cyclopenta with n carbon atom straight chain alkyl.Main chain is preceding when name, and branch is in rear, main chain
It is separated between branch with "-", such asIt is indicated with PK1P-32；
It is indicated with PK1W-CpO2；It is indicated with WW-2OO2；With CCBW-
3O2 is indicated；It is indicated with PW-3O2；It is indicated with X1-2OO2；It is indicated with X1-CpOO2；It is indicated with W-CpOO4；It is indicated with PH1P-2Cp；It is indicated with PWP-3Cp3；It is indicated with PGW-3O2；It is indicated with X1-2OH.
Table 2
| Code | R1 | R2 |
| nm | CnH2n+1 | CmH2m+1 |
| nH | CnH2n+1 | H |
| nOH | OCnH2n+1 | H |
| nOm | CnH2n+1 | OCmH2m+1 |
| nOOm | OCnH2n+1 | OCmH2m+1 |
| nCp | CnH2n+1 | Cp |
| nmCp | CnH2n+1 | CmH2m+1Cp |
| nF | CnH2n+1 | F |
| nOTF | CnH2n+1 | OCF3 |
| Cpm | Cp | CmH2m+1 |
| CpH | Cp | H |
| CpOH | OCp | H |
| CpOm | Cp | OCmH2m+1 |
| CpOOm | OCp | OCmH2m+1 |
| CpF | Cp | F |
| nCpm | CnH2n+1Cp | CmH2m+1 |
| nCpH | CnH2n+1Cp | H |
| nCpOm | CnH2n+1Cp | OCmH2m+1 |
| nCpOOm | OCnH2n+1Cp | OCmH2m+1 |
| nCpF | CnH2n+1Cp | F |
In addition, liquid-crystal compoundsIt is indicated with 3HHV；Liquid-crystal compoundsWith
4HHV is indicated；It is indicated with 5HHV；It is indicated with VHHP1；It is indicated with CC31D1；It is indicated with PH1P-F3；It is indicated with WW-2OO5V1；It is indicated with V2PP1.
Embodiment 1
The synthetic method of PK1P-32 is as follows:
(1) the fluoro- 3- methyl-1 of the bromo- 4'- ethyl -2- of 4-, the preparation of 1'- biphenyl
Thermometer, mechanical stirring and constant pressure funnel are installed in 2000ml four-hole bottle, lead to nitrogen, to reaction system
The middle deionized water that the fluoro- 4- iodotoluene of the bromo- 3- of 75g (0.525mol) 1-, 138g (1mol) Anhydrous potassium carbonate and 150ml is added,
4.5g tetrakis triphenylphosphine palladium is added to instead by 8g tetrabutylammonium bromide, 200ml toluene, 50ml ethyl alcohol, stirring heating at 45 DEG C
It answers in system, finishes, continue heating and be stirred to react to micro- reflux, pre-configured 75g 4- ethylo benzene is added dropwise into system
The ethanol solution of boric acid keeps micro- reflux, and drop finishes, and sampling analysis after back flow reaction 4h is warming up at 70~80 DEG C, wait react
Bi Hou, into system plus toluene/ethyl acetate dilutes, and is subsequently poured into deionized water, stratification separates upper organic phase, so
Ethyl acetate extracts lower layer's water phase afterwards, neutrality is washed to after lower layer's ethyl acetate phase is merged with organic phase, then with anhydrous sulphur
Sour magnesium is dry, and takes off dry solvent, then uses alcohol crystal, obtains the bromo- 4'- ethyl -2- of 4- of 99.5% or more 132g G/C content
Fluoro- 3- methyl-1,1'- biphenyl.
(2) preparation of PK1P-32
Thermometer, mechanical stirring and constant pressure funnel are installed in 2000ml four-hole bottle, lead to nitrogen, to reaction system
The fluoro- 3- methyl-1 of the bromo- 4'- ethyl -2- of middle addition 132g (0.45mol) 4-, 1'- biphenyl, 118.3g (0.857mol) anhydrous carbon
The deionized water of sour potassium and 130ml, 6.9g tetrabutylammonium bromide, 200ml toluene, 50ml ethyl alcohol, stirring heating will at 45 DEG C
3.96g tetrakis triphenylphosphine palladium is added in reaction system, is finished, and is continued heating and is stirred to react to micro- reflux, drips into system
The ethanol solution for adding pre-configured 70.3g 4- propyl phenyl boric acid keeps micro- reflux, and drop finishes, and is warming up to 70~80 DEG C next time
Sampling analysis after stream reaction 4h, to after completion of the reaction, toluene/ethyl acetate dilution be added into system, is subsequently poured into deionized water,
Stratification separates upper organic phase, and then ethyl acetate extracts lower layer's water phase, and lower layer's ethyl acetate phase is merged with organic phase
After be washed to neutrality, it is then dry with anhydrous magnesium sulfate, and take off dry solvent, then use alcohol crystal, obtain 128g G/C content
99.5% or more PK1P-32.
The liquid crystal compound of embodiment 1 forms and measurement parameter is shown in Table 3.
Table 3
Note: the liquid-crystal compounds of serial number 1 is the liquid-crystal compounds with general formula I, the liquid-crystal compounds of serial number 2~9
For the liquid-crystal compounds with negative permittivity, serial number 10~12 is nonpolar liquid-crystal compounds.
Embodiment 2
The liquid crystal compound of embodiment 2 forms and measurement parameter is shown in Table 4.
Table 4
Note: the liquid-crystal compounds of serial number 1 is the liquid-crystal compounds with general formula I, the liquid-crystal compounds of serial number 2~7
For the liquid-crystal compounds with negative permittivity, the liquid-crystal compounds of serial number 8~13 is nonpolar liquid-crystal compounds.
Embodiment 3
The liquid crystal compound of embodiment 3 forms and measurement parameter is shown in Table 5.
Table 5
Note: the liquid-crystal compounds of serial number 1~2 is the liquid-crystal compounds with general formula I, the LCD compound of serial number 3~8
Object is the liquid-crystal compounds with negative permittivity, and the liquid-crystal compounds of serial number 9~12 is nonpolar liquid-crystal compounds.
Embodiment 4
The synthetic method of PK1P-Cp2 is as follows:
(1) the fluoro- 3- methyl-1 of the bromo- 4'- ethyl -2- of 4-, the preparation of 1'- biphenyl
Thermometer, mechanical stirring and constant pressure funnel are installed in 2000ml four-hole bottle, lead to nitrogen, to reaction system
The middle deionized water that the fluoro- 4- iodotoluene of the bromo- 3- of 75g (0.525mol) 1-, 138g (1mol) Anhydrous potassium carbonate and 150ml is added,
4.5g tetrakis triphenylphosphine palladium is added to instead by 8g tetrabutylammonium bromide, 200ml toluene, 50ml ethyl alcohol, stirring heating at 45 DEG C
It answers in system, finishes, continue heating and be stirred to react to micro- reflux, pre-configured 75g 4- ethylo benzene is added dropwise into system
The ethanol solution of boric acid keeps micro- reflux, and drop finishes, and sampling analysis after back flow reaction 4h is warming up at 70~80 DEG C, wait react
Bi Hou, into system plus toluene/ethyl acetate dilutes, and is subsequently poured into deionized water, stratification separates upper organic phase, so
Ethyl acetate extracts lower layer's water phase afterwards, neutrality is washed to after lower layer's ethyl acetate phase is merged with organic phase, then with anhydrous sulphur
Sour magnesium is dry, and takes off dry solvent, then uses alcohol crystal, obtains the bromo- 4'- ethyl -2- of 4- of 99.5% or more 132g G/C content
Fluoro- 3- methyl-1,1'- biphenyl.
(2) preparation of PK1P-Cp2
Thermometer, mechanical stirring and constant pressure funnel are installed in 2000ml four-hole bottle, lead to nitrogen, to reaction system
The fluoro- 3- methyl-1 of the bromo- 4'- ethyl -2- of middle addition 132g (0.45mol) 4-, 1'- biphenyl, 118.3g (0.857mol) anhydrous carbon
The deionized water of sour potassium and 130ml, 6.9g tetrabutylammonium bromide, 200ml toluene, 50ml ethyl alcohol, stirring heating will at 45 DEG C
3.96g tetrakis triphenylphosphine palladium is added in reaction system, is finished, and is continued heating and is stirred to react to micro- reflux, drips into system
The ethanol solution for adding pre-configured 81.4g 4- cyclopenta phenyl boric acid, keeps micro- reflux, and drop finishes, is warming up at 70~80 DEG C
Sampling analysis after back flow reaction 4h, to after completion of the reaction, toluene/ethyl acetate dilution be added into system, is subsequently poured into deionization
Water, stratification separate upper organic phase, and then ethyl acetate extracts lower layer's water phase, by lower layer's ethyl acetate phase and organic phase
Neutrality is washed to after merging, it is then dry with anhydrous magnesium sulfate, and dry solvent is taken off, alcohol crystal is then used, 138g GC is obtained and contains
The PK1P-Cp2 of 99.5% or more amount.
The liquid crystal compound of embodiment 4 forms and measurement parameter is shown in Table 6.
Table 6
Note: the liquid-crystal compounds of serial number 1 is the liquid-crystal compounds with general formula I, the liquid-crystal compounds of serial number 2~9
For the liquid-crystal compounds with negative permittivity, the liquid-crystal compounds of serial number 10~11 is nonpolar liquid-crystal compounds.
Embodiment 5
The synthetic method of PK1P-3Cp is as follows:
(1) the fluoro- 3- methyl-1 of the bromo- 4'- cyclopenta -2- of 4-, the preparation of 1'- biphenyl
Thermometer, mechanical stirring and constant pressure funnel are installed in 2000ml four-hole bottle, lead to nitrogen, to reaction system
The middle deionized water that the fluoro- 4- iodotoluene of the bromo- 3- of 75g (0.525mol) 1-, 138g (1mol) Anhydrous potassium carbonate and 150ml is added,
4.5g tetrakis triphenylphosphine palladium is added to instead by 8g tetrabutylammonium bromide, 200ml toluene, 50ml ethyl alcohol, stirring heating at 45 DEG C
It answers in system, finishes, continue heating and be stirred to react to micro- reflux, pre-configured 95g 4- cyclopenta is added dropwise into system
The ethanol solution of phenyl boric acid keeps micro- reflux, and drop finishes, and sampling analysis after back flow reaction 4h is warming up at 70~80 DEG C, wait react
After, into system plus toluene/ethyl acetate dilutes, and is subsequently poured into deionized water, and stratification separates upper organic phase,
Then ethyl acetate extracts lower layer's water phase, neutrality is washed to after lower layer's ethyl acetate phase is merged with organic phase, then with anhydrous
Magnesium sulfate is dry, and takes off dry solvent, then uses alcohol crystal, obtains the bromo- 4'- ring penta of 4- of 99.5% or more 150g G/C content
The fluoro- 3- methyl-1 of base -2-, 1'- biphenyl.
(2) preparation of fluoro- 3'- methyl -4'- 4 ' the 1 "-terphenyl of propyl -1,1 ' of 4- cyclopenta -2'-
Thermometer, mechanical stirring and constant pressure funnel are installed in 2000ml four-hole bottle, lead to nitrogen, to reaction system
The fluoro- 3- methyl-1 of the bromo- 4'- cyclopenta -2- of middle addition 150g (0.45mol) 4-, 1'- biphenyl, 118.3g (0.857mol) are anhydrous
The deionized water of potassium carbonate and 130ml, 6.9g tetrabutylammonium bromide, 200ml toluene, 50ml ethyl alcohol, stirring heating, at 45 DEG C
3.96g tetrakis triphenylphosphine palladium is added in reaction system, is finished, continues heating and is stirred to react to micro- reflux, into system
The ethanol solution of pre-configured 70.3g 4- propyl phenyl boric acid is added dropwise, keeps micro- reflux, drop finishes, is warming up at 70~80 DEG C
Sampling analysis after back flow reaction 4h, to after completion of the reaction, toluene/ethyl acetate dilution be added into system, is subsequently poured into deionization
Water, stratification separate upper organic phase, and then ethyl acetate extracts lower layer's water phase, by lower layer's ethyl acetate phase and organic phase
Neutrality is washed to after merging, it is then dry with anhydrous magnesium sulfate, and dry solvent is taken off, alcohol crystal is then used, 159.6g GC is obtained
The PK1P-3Cp of 99.5% or more content.
The liquid crystal compound of embodiment 5 forms and measurement parameter is shown in Table 7.
Table 7
Note: the liquid-crystal compounds of serial number 1~2 is the liquid-crystal compounds with general formula I, the liquid-crystalization of serial number 3~10
Conjunction object is the liquid-crystal compounds with negative permittivity, and the liquid-crystal compounds of serial number 11~13 is nonpolar liquid-crystal compounds.
Embodiment 6
The liquid crystal compound of embodiment 6 forms and measurement parameter is shown in Table 8.
Table 8
Note: the liquid-crystal compounds of serial number 1 is the liquid-crystal compounds with general formula I, the liquid-crystal compounds of serial number 2~5
For the liquid-crystal compounds with positive dielectric constant, the liquid-crystal compounds of serial number 6~10 is nonpolar liquid-crystal compounds.
Embodiment 7
The liquid crystal compound of embodiment 7 forms and measurement parameter is shown in Table 9.
Table 9
Note: the liquid-crystal compounds of serial number 1 is the liquid-crystal compounds with general formula I, the liquid-crystal compounds of serial number 2~7
For the liquid-crystal compounds with positive dielectric constant, the liquid-crystal compounds of serial number 8~10 is nonpolar liquid-crystal compounds.
Embodiment 8
The liquid crystal compound of embodiment 8 forms and measurement parameter is shown in Table 10.
Table 10
Note: the liquid-crystal compounds of serial number 1 is the liquid-crystal compounds with general formula I, the liquid-crystal compounds of serial number 2~6
For the liquid-crystal compounds with positive dielectric constant, the liquid-crystal compounds of serial number 7~11 is nonpolar liquid-crystal compounds.
Embodiment 9
The liquid crystal compound of embodiment 9 forms and measurement parameter is shown in Table 11.
Table 11
Note: the liquid-crystal compounds of serial number 1 is the liquid-crystal compounds with general formula I, the liquid-crystal compounds of serial number 2~6
For the liquid-crystal compounds with positive dielectric constant, the liquid-crystal compounds of serial number 7~10 is nonpolar liquid-crystal compounds.
Embodiment 10
The liquid crystal compound of embodiment 10 forms and measurement parameter is shown in Table 12.
Table 12
Note: the liquid-crystal compounds of serial number 1 is the liquid-crystal compounds with general formula I, the liquid-crystal compounds of serial number 2~4
For the liquid-crystal compounds with negative permittivity, the liquid-crystal compounds of serial number 5~8 is the LCD compound with positive dielectric constant
Object, the liquid-crystal compounds of serial number 9~13 are nonpolar liquid-crystal compounds.
Embodiment 11
The liquid crystal compound of embodiment 11 forms and measurement parameter is shown in Table 13.
Table 13
Note: the liquid-crystal compounds of serial number 1~2 is the liquid-crystal compounds with general formula I, the LCD compound of serial number 3~6
Object is the liquid-crystal compounds with positive dielectric constant, and the liquid-crystal compounds of serial number 7~10 is nonpolar liquid-crystal compounds.
Embodiment 12
The liquid crystal compound of embodiment 12 forms and measurement parameter is shown in Table 14.
Table 14
Note: the liquid-crystal compounds of serial number 1~2 is the liquid-crystal compounds with general formula I, the LCD compound of serial number 3~8
Object is the liquid-crystal compounds with positive dielectric constant, and the liquid-crystal compounds of serial number 9~11 is nonpolar liquid-crystal compounds.
Comparative example 1
The liquid crystal compound of comparative example 1 forms and measurement parameter is shown in Table 15.
Table 15
Comparative example 2
The liquid crystal compound of comparative example 2 forms and measurement parameter is shown in Table 16.
Table 16
Wherein, with liquid-crystal compounds in comparative example 1Instead of 2 formula of I of embodiment
CompoundWith liquid-crystal compounds in comparative example 2Instead of
The compound of 9 formula of I of embodiment
From above-described embodiment it can be found that the addition of general formula I is particularly conducive to raising system photoelectricity anisotropy value, and
System nematic temperature range, regulation system dielectric constant values can be improved and improve system coefficient of elasticity, so as to improve using
Temperature range, response speed, and improve light in the penetrance of whole system, it is beneficial to energy conservation, and be conducive to improve contrast.When
It is available to have suitable optical anisotropy, dielectric respectively to different when general formula I is mixed with other variety classes liquid-crystal compounds
Property, high clearing point compared with low viscosity and the liquid crystal compound of higher elasticity coefficient, especially III3 are more preferably R5It is third
Base, R6For vinyl compound when, the liquid crystal compound of low viscosity can be obtained, can be used for manufacturing quick response liquid crystal be situated between
Matter.Above-mentioned measurement parameter is related with the composition physico-chemical property of all liquid-crystal compounds of liquid crystal media, liquid crystal mixing of the invention
Object is mainly used for the liquid crystal parameter of regulation system.
By the comparison of embodiment 2 and comparative example 1 it can be found that when including that there is general formula I in negative dielectric liquid crystal mixture
Liquid-crystal compounds when, it is available have relatively high optical anisotropy, higher clearing point and higher elasticity of flexure coefficient
k33Liquid crystal compound, these are for obtaining wider array of operating temperatures, faster response speed, higher contrast and light transmission
Rate, lower power consumption are helpful.
The comparison of embodiment 9 and comparative example 2 is it can be found that when including the liquid with general formula I in positive dielectric liquid crystal mixture
It is available that there is relatively high optical anisotropy, higher clearing point, higher dielectric constant Δ ε and exhibition when brilliant compound
Bent coefficient of elasticity k11Liquid crystal compound, these are for obtaining wider array of operating temperatures, faster response speed, higher comparison
Degree and light transmittance, lower power consumption are helpful.
In summary, the addition of the liquid-crystal compounds with general formula I is particularly conducive to increase optical anisotropy value, and
Adjustable system viscosity, regulation system dielectric constant values and raising system coefficient of elasticity, can also improve liquid crystal and use temperature
Width, thus be conducive to manufacture quick response, it is wider using temperature, low energy consumption, high contrast liquid crystal display device.
Though the not exhaustive claimed all liquid-crystal compounds of the present invention and liquid crystal compound, those skilled in the art
It predictably, can be in a similar manner only in conjunction with the profession trial of itself on the basis of published above-described embodiment
Other similar liquid crystal materials are obtained without making the creative labor.Herein since length is limited, representative reality is only enumerated
Apply mode.
The foregoing is only a preferred embodiment of the present invention, is not intended to restrict the invention, for the skill of this field
For art personnel, the invention may be variously modified and varied.All within the spirits and principles of the present invention, made any to repair
Change, equivalent replacement, improvement etc., should all be included in the protection scope of the present invention.
Claims (10)
1. one kind has high optically anisotropic biphenyl liquid crystal compound object, which is characterized in that the liquid-crystal compounds has logical
Formulas I, the general formula I are as follows:
Wherein,
Y and Y ' is each independently selected from the alkene of H, C1~C7 alkyl, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Alkoxy, wherein H can be replaced by cyclopenta or F, CH2It can be replaced by cyclopenta, O or F, and two adjacent CH2It cannot be simultaneously
Replaced by O；Alternatively, the Y and Y ' are each independently selected from cyclopenta, oxygen cyclopentaOxygen methylcyclopentylOxygen ethylcyclopentylOr for the alkyl of C1~C7, the alkoxy of C1~C7, C2~C7 alkenyl
Or cyclopenta, oxygen cyclopenta, oxygen methylcyclopentyl, oxygen ethylcyclopentyl that the alkene alkoxy of C2~C7 replaces；Alternatively, the Y
And Y ' is each independently selected from cyclopentenyl, oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base, or is C1
Cyclopentenyl, the oxygen ring penta of the alkene alkoxy substitution of the alkyl of~C7, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Alkenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base；
A and b is each independently selected from 0,1 or 2, and a and b are not 0 simultaneously；
When a is 1,It is selected from Any one of group of composition；
It include two in general formula when a is 2I.e.Occur in general formula twice, at each occurrenceIt is each independently selected from
Any in the group of composition
Kind；
When b is 1,It is selected from Any one of group of composition；
It include two in general formula when b is 2I.e.Occur in general formula twice, at each occurrenceIt is each independently selected from Any one of group of composition,
AndIn at least 1 be selected from Any one of group of composition.
2. liquid-crystal compounds according to claim 1, which is characterized in that the general formula I is
Wherein, R1、R1' be each independently selected from H, C1~C7 alkyl, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~
The alkene alkoxy of C7, wherein H can be replaced by cyclopenta or F, CH2It can be replaced by cyclopenta, O or F, and two adjacent CH2It can not
To be replaced simultaneously by O；Alternatively, the R1、R1' it is each independently selected from cyclopenta, oxygen cyclopentaOxygen methyl ring penta
BaseOxygen ethylcyclopentylOr for the alkyl of C1~C7, the alkoxy of C1~C7, C2~C7 alkene
Cyclopenta, the oxygen cyclopenta, oxygen methylcyclopentyl, oxygen ethylcyclopentyl of the alkene alkoxy of base or C2~C7 substitution；Alternatively, described
R1、R1' it is each independently selected from cyclopentenyl, oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base, or be C1
Cyclopentenyl, the oxygen ring penta of the alkene alkoxy substitution of the alkyl of~C7, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Alkenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base.
3. a kind of liquid crystal compound, which is characterized in that the liquid crystal compound includes at least one liquid of any of claims 1 or 2
Brilliant compound.
4. liquid crystal compound according to claim 3, which is characterized in that include that there is general formula I in the liquid crystal compound
Liquid-crystal compounds weight content be 0.1~75%, preferably 0.1~50%, further preferably 0.1~30%.
5. liquid crystal compound according to claim 3, which is characterized in that the liquid crystal compound further includes at least one pole
Property liquid-crystal compounds and/or at least one nonpolar liquid-crystal compounds, the polar compound is positive polar compound and/or negative
Polar compound, the positive polarity compound are selected from one of compound shown in 1~X105 of Formula X or a variety of, the negative polarity
Compound is selected from one of compound shown in 1~II98 of Formula II or a variety of, the non-polar compound be selected from formula III 1~
One of compound shown in III36 is a variety of,
Wherein, the positive polarity compound with X1 to X105 is respectively as follows:
The Formula X 1 is into X105, R7For H, carbon atom number be 1~7 alkyl, carbon atom number be 1~7 alkoxy, carbon atom
The alkene alkoxy that the alkenyl or carbon atom number that number is 2~7 are 2~7, wherein H can be replaced by cyclopenta or F, CH2It can be by ring penta
Base, O or F replace, and two adjacent CH2It cannot be replaced simultaneously by O；It or is cyclopenta, oxygen cyclopentaOxygen
MethylcyclopentylOxygen ethylcyclopentylIt or is the alkyl of C1~C7, the alkoxy of C1~C7, C2
Cyclopenta, the oxygen cyclopenta, oxygen methylcyclopentyl, oxygen ethylcyclopentyl that the alkenyl of~C7 or the alkene alkoxy of C2~C7 replace；
Perhaps selected from cyclopentenyl, oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base or for C1~C7 alkyl,
Cyclopentenyl, the oxygen cyclopentenyl, oxygen methyl of the alkene alkoxy substitution of the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Cyclopentenyl, oxygen ethylcyclopentene base；R8For H, F, CN, NCS, Cl, OCF3, alkyl with 1 to 7 carbon atoms, alkoxy,
Alkenyl or alkene alkoxy, wherein H can be replaced by cyclopenta or F, CH2It can be replaced by cyclopenta, O or F, and two adjacent CH2No
It can be replaced simultaneously by O；R8It can also be cyclopenta, oxygen cyclopentaOxygen methylcyclopentylOr oxygen ethyl
CyclopentaOr the alkene alcoxyl for the alkyl of C1~C7, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Cyclopenta, the oxygen cyclopenta, oxygen methylcyclopentyl, oxygen ethylcyclopentyl of base substitution；Or it is selected from cyclopentenyl, oxygen cyclopentene
Base, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base, or for the alkyl of C1~C7, the alkoxy of C1~C7, C2~C7 alkene
Cyclopentenyl, the oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base of the alkene alkoxy of base or C2~C7 substitution；
It is described to have 1 to 7 carbon atom alkyls preferred are as follows:-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-C6H13Or-C7H15；The tool
There is the alkenyl of 1 to 7 carbon atoms preferred are as follows:-CH=CH2,-CH=CHCH3,-CH=CHC2H5,-CH=CHC3H7、-C2H4CH=
CH2、-C2H4CH=CHCH3、-C3H6CH=CH2Or-C3H6CH=CHCH3；The alkoxy for having 1 to 7 carbon atoms is preferred
Are as follows:-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13Or-OC7H15；The alkene alkane that there are 1 to 7 carbon atoms
Oxygroup is preferred are as follows:-OCH=CH2、-OCH2CH=CH2、-OCH2CH=CHCH3Or-OCH2CH=CHC2H5；X9、X10And V1Respectively
Independently selected from H, methyl or F,
The negative polarity compound with II1~II98 is respectively as follows:
In 1~II98 of Formula II, R3And R4It is each independently H, the alkane that the alkyl that carbon atom number is 1~7, carbon atom number are 1~7
The alkene alkoxy that the alkenyl or carbon atom number that oxygroup, carbon atom number are 2~7 are 2~7, wherein H can be replaced by cyclopenta or F,
CH2It can be replaced by cyclopenta, O or F, and two adjacent CH2It cannot be replaced simultaneously by O；It or is cyclopenta, oxygen cyclopentaOxygen methylcyclopentylOxygen ethylcyclopentylOr alkyl, C1~C7 for C1~C7
Alkoxy, C2~C7 alkenyl or C2~C7 alkene alkoxy replace cyclopenta, oxygen cyclopenta, oxygen methylcyclopentyl, oxygen
Ethylcyclopentyl；Perhaps selected from cyclopentenyl, oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base or be C1
Cyclopentenyl, the oxygen ring penta of the alkene alkoxy substitution of the alkyl of~C7, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Alkenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base；The alkyl that the carbon atom number is 1~7 is-CH3、-C2H5、-C3H7、-
C4H9、-C5H11、-C6H13Or-C7H15；The alkenyl that the carbon atom number is 2~7 is preferably-CH=CH2,-CH=CHCH3、-CH
=CHC2H5,-CH=CHC3H7、-C2H4CH=CH2、-C2H4CH=CHCH3、-C3H6CH=CH2Or-C3H6CH=CHCH3；It is described
The alkoxy that carbon atom number is 1~7 is preferably-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13Or-OC7H15；Institute
Stating the alkene alkoxy that carbon atom number is 2~7 is preferably-OCH2CH=CH2、-OCH2CH=CHCH3Or-OCH2CH=CHC2H5；
The non-polar compound with III1~III36 is respectively as follows:
In the 1~III36 of formula III, R5、R6It is each independently selected from H, F, the alkyl that carbon atom number is 1~7, carbon atom number are
The alkene alkoxy that the alkenyl or carbon atom number that 1~7 alkoxy, carbon atom number are 2~7 are 2~7, or be H or CH2By ring
Alkoxy that alkyl that the carbon atom number that amyl, cyclopentenyl or F replace is 1~7, carbon atom number are 1~7, carbon atom number 2
The alkene alkoxy that~7 alkenyl or carbon atom number is 2~7, wherein H can be replaced by cyclopenta or F, CH2It can be by cyclopenta, O or F
Replace, and two adjacent CH2It cannot be replaced simultaneously by O；It or is cyclopenta, oxygen cyclopentaOxygen methyl ring penta
BaseOxygen ethylcyclopentylOr for the alkyl of C1~C7, the alkoxy of C1~C7, C2~C7 alkene
Cyclopenta, the oxygen cyclopenta, oxygen methylcyclopentyl, oxygen ethylcyclopentyl of the alkene alkoxy of base or C2~C7 substitution；Or it is selected from
Cyclopentenyl, oxygen cyclopentenylOxygen methyl cyclopentene baseOxygen ethylcyclopentene base
Or the cyclopentene of the alkene alkoxy substitution for the alkyl of C1~C7, the alkoxy of C1~C7, the alkenyl of C2~C7 or C2~C7
Base, oxygen cyclopentenyl, oxygen methyl cyclopentene base, oxygen ethylcyclopentene base；The alkyl that the carbon atom number is 1~7 is-CH3、-
C2H5、-C3H7、-C4H9、-C5H11、-C6H13Or-C7H15；The alkenyl that the carbon atom number is 2~7 is preferably-CH=CH2、-CH
=CHCH3,-CH=CHC2H5,-CH=CHC3H7、-C2H4CH=CH2、-C2H4CH=CHCH3、-C3H6CH=CH2Or-C3H6CH
=CHCH3；The alkoxy that the carbon atom number is 1~7 is preferably-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13
Or-OC7H15；The alkene alkoxy that the carbon atom number is 2~7 is preferably-OCH=CH2、-OCH2CH=CH2、-OCH2CH=
CHCH3Or-OCH2CH=CHC2H5,
Preferably, at least one polarity liquid-crystal compounds and/or at least one nonpolarity are included in the liquid crystal compound
The mass fraction of liquid-crystal compounds is 0~80%.
6. liquid crystal compound according to claim 5, which is characterized in that the non-polar compound is shown in formula III 3
Compound.
7. the liquid crystal compound according to any one of claim 3~6, which is characterized in that in the liquid crystal compound
The polymerizable compound for being also 0~20% comprising mass fraction, the polymerizable compound general formula are as follows:
Wherein
—T1With-T2It each independently representsOr epoxy group；
—W1- and-W2- singly-bound or carbon atom number are each independently represented as 1~8 alkyl；
—X1- and-X2- each independently represent singly-bound ,-O-,-CO-,-COO-or-OCO-；
—Z1- it is selected from singly-bound ,-O-,-CO-,-COO-,-OCO-,-CH2O—、—OCH2—、—C2H4—、—
CF2O—、—OCF2- ,-C ≡ C- ,-CH=CH-, One or both of group of composition；
I is 0,1 or 2；
Each independently represent when occurring every time on unsubstituted or cyclohexylidene-CH2- by O
ReplaceOn unsubstituted or sub- phenyl ring=CH-replaced by NWhat the H on ring was replaced by F
8. the liquid crystal compound according to any one of claim 3~6, which is characterized in that in the liquid crystal compound
The stabilizer for being also 0~20% comprising mass fraction, it is preferable that the stabilizer is with chemical combination shown in general formula VI1~VI5
One of object is a variety of:
Wherein, R9For the alkyl with 1~7 carbon atom, the alkoxy with 1~7 carbon atom or there are 2~7 carbon atoms
Alkenyl, wherein H can be replaced by cyclopenta or F, CH2It can be replaced by cyclopenta, O or F, and two adjacent CH2It cannot be simultaneously
Replaced by O；The alkyl, the alkoxy and the alkenyl are alkyl, alkoxy and the alkenyl of linear chain or branched chain；
It is selected from Any one of group of composition.
9. application of the liquid-crystal compounds of any of claims 1 or 2 in liquid crystal display material or liquid crystal display.
10. the answering in liquid crystal display material or liquid crystal display of liquid crystal compound described in any one of claim 3 to 8
With.
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| CN110760311A (en) * | 2019-10-31 | 2020-02-07 | 武汉轻工大学 | Lateral methyl poly-biphenyl liquid crystal compound, liquid crystal composition and application thereof |
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| WO2022142821A1 (en) * | 2020-12-28 | 2022-07-07 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal compound, preparation method therefor, and application thereof |
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