CN108384558A - A kind of negative type liquid crystal compound, the liquid crystal compound comprising the liquid-crystal compounds and its application - Google Patents
A kind of negative type liquid crystal compound, the liquid crystal compound comprising the liquid-crystal compounds and its application Download PDFInfo
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- CN108384558A CN108384558A CN201810229159.9A CN201810229159A CN108384558A CN 108384558 A CN108384558 A CN 108384558A CN 201810229159 A CN201810229159 A CN 201810229159A CN 108384558 A CN108384558 A CN 108384558A
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- DYSJQUQJVBYIOT-UHFFFAOYSA-N Cc(ccc(C)c1F)c1F Chemical compound Cc(ccc(C)c1F)c1F DYSJQUQJVBYIOT-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
Abstract
The present invention provides a kind of liquid-crystal compounds, which has general formulaWherein R1For H, carbon atom number indicate 1~7 alkyl or alkoxy, carbon atom number be 2~7 alkenyl or alkene alkoxy；R2For H, carbon atom number be 1~7 alkyl, carbon atom number be 1~7 alkoxy, carbon atom number be 2~7 alkenyl, carbon atom number be 2~7 alkene alkoxy, H or CH in abovementioned alkyl, alkoxy, alkenyl and alkene alkoxy2Can be replaced by cyclopenta or cyclopenta, or for be 1~7 by carbon atom number alkyl, carbon atom number be 1~7 alkoxy, carbon atom number be 2~7 alkenyl or carbon atom number be 2~7 the cyclopenta that replaces of alkene alkoxy；A is 0,1 or 2；B is selected from 0 or 1；G is selected from singly-bound ,-COO-,-CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2—、
Description
Technical field
The present invention relates to liquid crystal material fields, and in particular to a kind of liquid-crystal compounds, the liquid crystal comprising the liquid-crystal compounds
Mixture and its application.
Background technology
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 fibers, liquid crystal material started process of industrialization.
By the rapid development of decades, 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 cell, research range are even more to become and work as throughout various fields such as chemistry, biology and information sciences
Favor, indispensable one of new material are received 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 prepare have liquid crystal material new process, 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 type of drive.Wherein, active matrix liquid crystal display is to change the row of liquid-crystal compounds by applying voltage
Row mode forms image to change the light emitting intensity that backlight is sent out, due to high-resolution, high contrast,
Low-power, face is thin and light feature 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)) on the silicon chip as substrate or other diodes；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), has shown 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 continuous development of TFT-LCD, wide viewing angle pattern is
As the target pursued in industry, the wide viewing angle technology of mainstream mainly has VA vertical orientations technology, IPS in-plane switching technologies at present
And the technologies such as FFS fringe field switching technologies, this kind of technology require higher light transmittance and smaller colour cast.Negative type liquid crystal
Close object colour cast and by vertical electric field influenced aspect performance it is more outstanding, compared with eurymeric material, show higher light and penetrate
Rate, thus by extensive use.
With the extensive use of liquid crystal display, the requirement to its performance is also constantly improving.Liquid crystal display height figure
Wider array of operating temperature, faster response speed and higher contrast are required in terms of image quality amount, and requires power consumption lower and lower,
This means that liquid crystal display will have lower driving voltage and higher light transmittance.The raising of these performances all be unable to do without liquid crystal
The improvement of material.
Invention content
The object of the present invention is to provide a kind of liquid-crystal compounds of negative permittivity, to improve liquid crystal material in the prior art
Optical anisotropy, rotary viscosity, dielectric constant and coefficient of elasticity characteristic, to improve the response speed of liquid crystal material, drop
Low driving voltage.
It is a further object of the present invention to provide the liquid crystal compounds for including above-mentioned liquid-crystal compounds.
It is yet another object of the invention to provide the applications of above-mentioned liquid-crystal compounds and liquid crystal compound.
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, and general formula I is：
Wherein,
R1For H, C1~C7 alkyl, C1~C7 alkoxies, C2~C7 alkenyls or C2~C7 alkene alkoxies；
R2For H, C1~C7 alkyl, C1~C7 alkoxies, C2~C7 alkenyls, C2~C7 alkene alkoxy, abovementioned alkyl, alcoxyl
H or CH in base, alkenyl and alkene alkoxy2Can be replaced by cyclopenta, be either cyclopenta or for by C1~C7 alkyl, C1~
The cyclopenta of C7 alkoxies, C2~C7 alkenyls or the substitution of C2~C7 alkene alkoxies；
A is 0,1 or 2；B is selected from 0 or 1；
G is selected from singly-bound ,-COO-,-CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2—、Or any one of-CH=CH-；
It is selected from It is one or more in the group of composition；
It is selected fromIn the group of composition
It is one or more.
According to another aspect of the present invention, a kind of liquid crystal compound with negative dielectric anisotropic, the liquid crystal are provided
Compound includes at least one above-mentioned liquid-crystal compounds.
According to another aspect of the invention, a kind of above-mentioned liquid-crystal compounds is provided in liquid crystal display material or liquid crystal
Show the application in equipment.
According to another aspect of the invention, a kind of above-mentioned liquid crystal compound is provided in liquid crystal display material or liquid crystal
Show the application in equipment.
Advantageous effect：The liquid-crystal compounds of the present invention can be effectively improved the optical anisotropy of liquid crystal material, to
The response speed of liquid crystal material is improved, driving voltage is reduced.
Specific implementation mode
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 a kind of typical embodiment of the present invention, a kind of liquid-crystal compounds is provided, which has logical
Formulas I, general formula I are
In general formula I
R1For H, carbon atom number indicate 1~7 alkyl or alkoxy, carbon atom number be 2~7 alkenyl or alkene alkoxy；
R2For H, carbon atom number be 1~7 alkyl, carbon atom number be 1~7 alkoxy, carbon atom number be 2~7 alkene
Base, the alkene alkoxy that carbon atom number is 2~7, H or CH in abovementioned alkyl, alkoxy, alkenyl and alkene alkoxy2It can be by cyclopenta
Substitution or cyclopenta, or for be 1~7 by carbon atom number alkyl, carbon atom number be 1~7 alkoxy, carbon atom number 2
The cyclopenta that the alkene alkoxy that~7 alkenyl or carbon atom number is 2~7 replaces；
A is 0,1 or 2；B is selected from 0 or 1；
G is selected from singly-bound ,-COO-,-CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2—、Or any one of-CH=CH-；
It is selected from It is one or more in the group of composition；
It is selected fromIn the group of composition
It is one or more.
The liquid-crystal compounds of negative permittivity with general formula I is white under pure material state, has higher light
Learn anisotropy Δ n values, wider nematic temperature range.Wherein optical anisotropy Δ n values are according to pre-set
(d Δs n) is adjusted optical path difference, and intima-media thickness d is determined by optical anisotropy △ n, especially in higher d △
Under n values, if having high value for optical anisotropy △ n, d values can be selected as smaller value, when to respond
Between have more preferably be worth.In addition the addition of cyclopenta can further improve driving voltage, improve response speed and widen liquid crystal
Phase range.
The characteristics of liquid-crystal compounds of negative permittivity is that on molecular long axis direction there is larger dipole to make
With, thus corresponding dielectric constant is relatively large in vertically-oriented component, that is, has higher vertical dielectric constant ε⊥, because
This dielectric anisotropy △ ε=ε//-ε⊥Show as negative value.Due to higher vertical dielectric constant ε⊥, liquid crystal molecule tendency
It is distributed in along perpendicular to direction of an electric field, thus shows lower pre-tilt angle, and negative type liquid crystal material is all under fringe field
It arranging on the horizontal level, pre-tilt angle distribution is uniform compared with eurymeric material, thus shows higher light transmittance and wide viewing angle,
VA, PSVA and FFS type liquid crystal material particularly useful for making high-penetration rate wide viewing angle；In addition the LCD compound of negative permittivity
The addition of object can improve the elasticity of flexure COEFFICIENT K of system33, so as to improve penetrance and comparison of the light in whole system
Degree, is conducive to energy saving, and can improve image displaying quality, preferably to meet the performance requirement of liquid crystal display.
Another outstanding feature of the liquid-crystal compounds of the negative permittivity of general formula I is combined with other type liquid-crystal compounds
When, suitable optical characteristics and dielectric constant can be obtained with small amount addition.Therefore, the liquid crystal of the negative permittivity of general formula I
The liquid crystal compound overall viscosity that compound is combined with other type liquid-crystal compounds is relatively low, and viscosity reduction can effectively drop
The response time of low liquid crystal material increases response speed.
In addition, it should be clear to a person skilled in the art that, abovementioned alkyl includes not only that straight chained alkyl also includes corresponding branch
Alkyl group.
In order to obtain more particularly suitable liquid crystal width, higher dielectric anisotropy value, smaller rotary viscosity and suitable
Coefficient of elasticity K, be more advantageous to improve liquid crystal material response speed, reduce threshold voltage, improve the intersolubility of liquid crystal material,
In a kind of preferred embodiment of the application, the liquid-crystal compounds of the negative permittivity of above-mentioned general formula I is with Formulas I 1 to I46's
Negative polarity liquid-crystal compounds.
The above-mentioned compound formula with general formula I1 to I46 is as follows：
Wherein,
R1' be H, carbon atom number indicate 1~7 alkyl or alkoxy, carbon atom number be 2~7 alkenyl or alkene alkoxy；
R2' it is H, the alkene that the alkoxy that the alkyl that carbon atom number is 1~7, carbon atom number are 1~7, carbon atom number are 2~7
Base, the alkene alkoxy that carbon atom number is 2~7, H or CH in abovementioned alkyl, alkoxy, alkenyl and alkene alkoxy2It can be by cyclopenta
Substitution or cyclopenta, or for be 1~7 by carbon atom number alkyl, carbon atom number be 1~7 alkoxy, carbon atom number 2
The cyclopenta that the alkene alkoxy that~7 alkenyl or carbon atom number is 2~7 replaces；
Since the liquid-crystal compounds of the negative permittivity with general formula I of the invention is with higher optical anisotropy
Value combines with other type liquid-crystal compounds the liquid-crystal compounds with general formula I to form the liquid crystal with negative permittivity and mix
When closing object, it should can be adjusted in wider range with the liquid crystal compound characteristic of negative permittivity, to meet more liquid
The performance requirement of brilliant material；Also, the liquid-crystal compounds of the negative permittivity with general formula I of the present invention and other type liquid crystal
There is preferable intersolubility when compound mixes, for other liquid-crystal compounds etc. type less-restrictive, it is applicable
In various liquid crystal compounds corresponding with purpose, it is particularly conducive to improve the bulk properties of liquid crystal compound；In addition, the liquid crystal is mixed
Closing object has good UV, light and thermal stability.
The liquid crystal compound with negative permittivity of the present invention can be prepared conventionally.Usually under high temperature
The desired amount of component is dissolved in the component for being constituted principal component with relatively low amount；The solution of each component can also be mixed into organic solvent,
Such as be mixed into acetone, chloroform or 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 the liquid crystal compound with negative permittivity of the present invention is not
It is restricted, the liquid-crystal compounds of any kind can be selected to constitute liquid crystal mixing together with the liquid-crystal compounds of the present invention according to purpose
Other additives of technical field can be also added in object as needed.For example, can add mass content be 0~20% can
Polymerizable compound and/or stabilizer.
Above-mentioned polymerizable compound general formula is as follows：
Wherein
—T1With-T2It each independently representsOr epoxy group；
—Y1- and-Y2- 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-；
M is 0,1 or 2；
When m is 1 ,-Z1- indicate singly-bound ,-O-,-CO-,-COO-,-OCO-,-CH2O—、—
OCH2—、—C2H4—、—CF2O—、—OCF2—、- CH=CH-,
When m is 2 ,-Z1- occur in general formula twice ,-Z1- each independently represent when occurring every time singly-bound ,-
O—、—CO—、—COO—、—OCO—、—CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2—、- CH=CH-,
It indicatesWherein on cyclohexyl-CH2- 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
When m is 1,It indicatesWherein on cyclohexyl-CH2- 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
When m is 2, general formula includes twoI.e.Occur in general formula twice,
It is each independently when occurring every timeWherein on cyclohexyl-CH2- can be replaced by O, or beIts
On middle phenyl ring=CH-can replace by N, the H on phenyl ring can be replaced by F, or be
Aforementioned stable agent is preferably with one or more in compound shown in general formula IV1~IV5.
In 1~IV5 of formula IV,
R7For halogenation or unsubstituted alkyl, alkoxy or alkenyl with 1~7 carbon atom, abovementioned alkyl, alkoxy
Or alkyl, alkoxy or the alkenyl that alkenyl is linear chain or branched chain；
For
Any one of group of composition.
In a kind of preferred embodiment of the application, above-mentioned liquid crystal compound further include at least one polar compound and/
Or at least one non-polar compound.Polar compound is preferably negative polarity compound, and negative polarity compound is preferably selected from formula
One or more in II1~II92 compounds represented, 1~II92 of Formula II is respectively：
Wherein, R3And R4Each independently represent H, the alkyl with 1 to 7 carbon atoms, the alkane with 1 to 7 carbon atoms
Oxygroup, the alkenyl with 2 to 7 carbon atoms or the alkene alkoxy with 2 to 7 carbon atoms, abovementioned alkyl, alkoxy, alkenyl
With H or CH in alkene alkoxy2It can be replaced by cyclopenta；R3And R4It is alternatively cyclopenta or alkyl, alkane for 1 to 7 carbon atoms
Oxygroup or the cyclopenta of alkenyl substitution；It is with 1 to 7 carbon atom alkyls：-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-
C6H13Or-C7H15；Alkenyl with 1 to 7 carbon atoms is preferably-CH=CH2,-CH=CHCH3,-CH=CHC2H5,-CH=
CHC3H7、-C2H4CH=CH2、-C2H4CH=CHCH3、-C3H6CH=CH2Or-C3H6CH=CHCH3；With 1 to 7 carbon atoms
Alkoxy is preferably-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13Or-OC7H15；With 1 to 7 carbon atoms
Alkene alkoxy is preferably-OCH2CH=CH2、-OCH2CH=CHCH3Or-OCH2CH=CHC2H5。
Above-mentioned polarity liquid-crystal compounds II1~II92 has negative dielectric anisotropic, and with general formula I compounds represented
It is combined into negative dielectric liquid crystal mixture, can be used for the dielectric constant, refraction coefficient, rotary viscosity γ of regulation system1, elasticity system
The parameters such as number and clearing point temperature are advantageously reduced with being collocated with conducive to the Low-Temperature Reliability of liquid crystal compound is improved for general formula I
Liquid crystal media uses lower limit temperature, widens the operating temperature range of liquid crystal media.
Above-mentioned nonpolarity liquid-crystal compounds is one or more in compound shown in 1~III30 of formula III；Wherein, formula
III1~III30 is as follows：
In 1~III30 of formula III, R5、R6For the alkyl with 1 to 7 carbon atoms, the alcoxyl with 1 to 7 carbon atoms
Base, the alkenyl with 2 to 7 carbon atoms or the alkene alkoxy with 2 to 7 carbon atoms, abovementioned alkyl, alkoxy, alkenyl and
H or CH in alkene alkoxy2It can be replaced by cyclopenta；R5、R6It is alternatively cyclopenta or alkyl, alcoxyl for 1 to 7 carbon atoms
Base or the cyclopenta of alkenyl substitution；It is above-mentioned to have the alkyl of 1 to 7 carbon atoms for-CH3、-C2H5、-C3H7、-C4H9、-C5H11、-
C6H13Or-C7H15；The above-mentioned alkenyl preferably-CH=CH with 2 to 7 carbon atoms2,-CH=CHCH3,-CH=CHC2H5、-
CH=CHC3H7、-C2H4CH=CH2、-C2H4CH=CHCH3、-C3H6CH=CH2Or-C3H6CH=CHCH3；It is above-mentioned that there are 1 to 7
The alkoxy of carbon atom is preferably-OCH3、-OC2H5、-OC3H7、-OC4H9、-OC5H11、-OC6H13Or-OC7H15；It is above-mentioned to have 2
Alkene alkoxy to 7 carbon atoms is preferably-OCH2CH=CH2、-OCH2CH=CHCH3Or-OCH2CH=CHC2H5.This field
Technical staff is noted that abovementioned alkyl, alkoxy, alkenyl, alkene alkoxy either straight chained alkyl, straight chain alcoxyl
Base, straight-chain alkenyl, straight chain alkene alkoxy can also be alkyl, alkoxy, alkenyl and alkene alkoxy with branch.
Above-mentioned nonpolarity liquid-crystal compounds III1 to III20 has lower rotary viscosity γ1, the response time with 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 III20 is used to manufacture the liquid crystal media of quick response.Above-mentioned non-polar liquid
Brilliant compound III21 to III28 has terphenyl structure, is conducive to the optical anisotropy △ n values of increase system, usual light path
The value of poor d △ n is prespecified, then △ n values are higher, and d values are lower, and response speed is inversely proportional with d values, to upper
State the liquid crystal compound of nonpolar liquid-crystal compounds III21 to III28 response speed have more preferably be worth.Above-mentioned nonpolarity
Liquid-crystal compounds III29 to III30 has higher clearing point temperature, is mainly used for the T of regulation systemNIValue, to upper
The liquid crystal compound for stating nonpolar liquid-crystal compounds III29 to III30 is conducive to improve the SC service ceiling temperature of liquid crystal media, opens up
The operating temperature range of wide liquid crystal media.
The outstanding feature of liquid-crystal compounds shown in formula of I of the present invention is when being combined with Low-Viscosity Liquid-Crystal Compound, with
Small amount addition can be obtained suitable optical characteristics, 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 20 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
For the low viscosity nonpolarity liquid-crystal compounds of III5.The liquid crystal compound is preferably applied to vertical orientation and shows (VA), polymer
In stable vertical arrangement (PSVA) or fringe field switching (FFS) type 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, smaller rotary viscosity and suitable elasticity system
Number K, 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, in above-mentioned liquid crystal compound the weight content of the liquid-crystal compounds with general formula I be 0.1~
75%, preferably 1~50%, further preferred 1~30%.Remaining ingredient can be added according to the above-mentioned introduction of the present invention.
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.The liquid-crystal compounds of the present 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, the advantageous effect that further illustrates the present invention.
The following example be for explain the present invention and it is unrestricted it.Percentage involved in embodiment is quality percentage
Than, temperature with degree Celsius indicating.Surveyed physico-chemical parameter indicates as follows：TNIIndicate clearing point；△ n indicate optical anisotropy (△ n
=ne-no, 589nm, 25 DEG C of measuring temperature)；ε⊥Indicate vertical dielectric constant (25 DEG C of measuring temperature)；△ ε indicate dielectric respectively to different
Property (△ ε=ε∥-ε⊥, 25 DEG C)；k33Indicate elasticity of flexure coefficient (25 DEG C of measuring temperature)；γ1Indicate rotary viscosity (measuring temperature
25 DEG C), and using dsc measurement TNI；△ n are measured using abbe refractometers；ε is measured using CV⊥、△ε、k33And 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；DifluorobenzeneIt is indicated with PFF；Tetrahydrochysene
PyransIt is indicated with Py；-CH2O- is indicated with B；AlkynylIt is indicated with G.
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, wherein group CnH2n+1And CmH2m+1It is to have respectively
There are the straight chained alkyl of n and m carbon atom, CpIndicate cyclopentaCnH2n+1CpIndicate n carbon atom straight chain alkyl of band
Cyclopenta.Main chain is preceding when name, and branch is rear, such as
It is indicated with PGPFFCpO2；With
PGPFF3CpO2 expressions,It is indicated with CPGPFFCpO2,It is indicated with CAPFF3O2,It is indicated with CBPFF3O2,It is indicated with PPFP2Cp.
Table 2
| Code | R1 | R2 |
| nm | CnH2n+1 | CmH2m+1 |
| nH | CnH2n+1 | H |
| Cpm | Cp | CmH2m+1 |
| CpH | Cp | H |
| nCpm | CnH2n+1Cp | CmH2m+1 |
| CpOm | Cp | OCmH2m+1 |
| nCpOm | CnH2n+1Cp | OCmH2m+1 |
| nCpH | CnH2n+1Cp | H |
| nOm | CnH2n+1 | OCmH2m+1 |
| nCp | CnH2n+1 | Cp |
| nmCp | CnH2n+1 | CmH2m+1Cp |
In addition, liquid-crystal compoundsIt is indicated with 3HHV；With
VHHP1 is indicated；It is indicated with CC31D1.
Embodiment 1
The synthetic method of PGPFFCpO2 is as follows：
1, the preparation of 1- cyclopenta -4- acetylenylbenzenes
Under nitrogen protection, 22.5g (0.1mol) is added into 500ml four-hole bottles to cyclopenta bromobenzene, the drying of 250ml
5.04g (0.105mol) sodium acetylide (18% xylene solution, 95% purity) is slowly added into system, 55 by the DMF crossed
It is reacted at DEG C for 24 hours, solution becomes milky from yellow；Reaction finishes, and is filtered after chloroform dissolving, after organic phase is washed 2 times, revolving
Then concentration uses the too short silica gel of n-hexane, TLC analyses to collect sterling.
2, the preparation of 1- ((4- cyclopentyl phenyls) acetenyl) -4- ethyoxyl -2,3- difluorobenzenes
Under nitrogen protection, 17.03g (0.1mol) 1- cyclopenta -4- acetylenylbenzenes, 23.2g are added into system
2,3-, the bis- fluoro- 4- ethyoxyls bromobenzenes of (0.105mol), the triethylamine of 20.24g (0.2mol), 5% palladium carbon of 0.85g, 0.85g
Triphenylphosphine, the cuprous iodide of 0.85g, the acetonitrile of 100ml is heated to reflux 3h, samples GC, after completion of the reaction, ethyl acetate
After extraction is washed to neutrality, concentrated by rotary evaporation, then it is 99.9% or more that can obtain 9.7g purity with ethyl alcohol recrystallization
PGPFFCpO2。
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.
Embodiment 2
The liquid crystal compound of embodiment 2 forms and measurement parameter is shown in Table 4.
Table 4
Note：Serial number 1 is the liquid-crystal compounds with general formula I.
Embodiment 3
The liquid crystal compound of embodiment 3 forms and measurement parameter is shown in Table 5.
Table 5
Note：Serial number 1 is the liquid-crystal compounds with general formula I.
Embodiment 4
The liquid crystal compound of embodiment 4 forms and measurement parameter is shown in Table 6.
Table 6
Note：Serial number 1 is the liquid-crystal compounds with general formula I.
Embodiment 5
The synthetic method of PGPFF3CpO2 is as follows：
1,1- acetenyls -4- (3- propyl cyclopenta) benzene
Under nitrogen protection, 22.5g (0.1mol) is added into 500ml four-hole bottles to propyl cyclopenta bromobenzene, 250ml's
5.04g (0.105mol) sodium acetylide (18% xylene solution, 95% purity) is slowly added into system by dried DMF
In, it is reacted at 55 DEG C for 24 hours, solution becomes milky from yellow；Reaction finishes, and is filtered after chloroform dissolving, organic phase is washed 2 times
Afterwards, then concentrated by rotary evaporation uses the too short silica gel of n-hexane, TLC analyses to collect sterling.
2, the preparation of two fluoro- 4- of 1- ethyoxyls -2,3- ((4- (3- propyl cyclopenta) phenyl) acetenyl) benzene
Under nitrogen protection, 17.03g (0.1mol) 1- acetenyls -4- (3- propyl cyclopenta) benzene is added into system,
2,3-, the bis- fluoro- 4- ethyoxyls bromobenzenes of 23.2g (0.105mol), the triethylamine of 20.24g (0.2mol), 5% palladium carbon of 0.85g,
The triphenylphosphine of 0.85g, the cuprous iodide of 0.85g, the acetonitrile of 100ml are heated to reflux 3h, sample GC, after completion of the reaction, acetic acid
After ethyl ester extraction is washed to neutrality, concentrated by rotary evaporation, then it is 99.9% or more that can obtain 10.3g purity with ethyl alcohol recrystallization
PGPFF3CpO2。
The liquid crystal compound of embodiment 5 forms and measurement parameter is shown in Table 7.
Table 7
Note：Serial number 1 is the liquid-crystal compounds with general formula I.
Embodiment 6
The liquid crystal compound of embodiment 6 forms and measurement parameter is shown in Table 8.
Table 8
Note：Serial number 1 is the liquid-crystal compounds with general formula I.
Embodiment 7
The liquid crystal compound of embodiment 7 forms and measurement parameter is shown in Table 9.
Table 9
Note：Serial number 1 is the liquid-crystal compounds with general formula I.
Embodiment 8
The liquid crystal compound of embodiment 8 forms and measurement parameter is shown in Table 10.
Table 10
Note：Serial number 1 is the liquid-crystal compounds with general formula I.
Embodiment 9
The liquid crystal compound of embodiment 9 forms and measurement parameter is shown in Table 11.
Table 11
Note：Serial number 1 is the liquid-crystal compounds with general formula I.
Embodiment 10
The synthetic method of PPGPFFCpO2 is as follows：
1, the preparation of 4- cyclopenta -4'- acetenyls -1,1'- biphenyl
Under nitrogen protection, bromo- 4'- cyclopenta -1, the 1'- connection of 30.12g (0.1mol) 4- are added into 500ml four-hole bottles
Benzene, the dried DMF of 250ml are slow by 5.04g (0.105mol) sodium acetylide (18% xylene solution, 95% purity)
It is added in system, is reacted at 55 DEG C for 24 hours, solution becomes milky from yellow；Reaction finishes, and is filtered after chloroform dissolving, organic
After mutually washing 2 times, then concentrated by rotary evaporation uses the too short silica gel of n-hexane, TLC analyses to collect sterling.
2, the preparation of 4- cyclopenta -4'- ((4- ethyoxyl -2,3- difluorophenyls) acetenyl) -1,1'- biphenyl
Under nitrogen protection, 24.63g (0.1mol) 4- cyclopenta -4'- acetenyl -1,1'- biphenyl is added into system,
2,3-, the bis- fluoro- 4- ethyoxyls bromobenzenes of 23.2g (0.105mol), the triethylamine of 20.24g (0.2mol), 5% palladium carbon of 0.85g,
The triphenylphosphine of 0.85g, the cuprous iodide of 0.85g, the acetonitrile of 100ml are heated to reflux 3h, sample GC, after completion of the reaction, acetic acid
After ethyl ester extraction is washed to neutrality, concentrated by rotary evaporation, alcohol crystal.It is 99.9% that 12.2g purity, which can be obtained, with ethyl alcohol recrystallization again
Above PPGPFFCpO2.
The liquid crystal compound of embodiment 10 forms and measurement parameter is shown in Table 12.
Table 12
Note：Serial number 1 is the liquid-crystal compounds with general formula I.
Embodiment 11
The liquid crystal compound of embodiment 11 forms and measurement parameter is shown in Table 13.
Table 13
Note：Serial number 1 is the liquid-crystal compounds with general formula I.
Embodiment 12
The liquid crystal compound of embodiment 12 forms and measurement parameter is shown in Table 14.
Table 14
Note：Serial number 1 is the liquid-crystal compounds with general formula I.
Embodiment 13
The liquid crystal compound of embodiment 13 forms and measurement parameter is shown in Table 15.
Table 15
Note：Serial number 1 and 2 is the liquid-crystal compounds with general formula I.
Embodiment 14
The liquid crystal compound of embodiment 14 forms and measurement parameter is shown in Table 16.
Table 16
Note：Serial number 1 and 2 is the liquid-crystal compounds with general formula I.
Embodiment 15
The liquid crystal compound of embodiment 15 forms and measurement parameter is shown in Table 17.
Table 17
Note：Serial number 1 and 2 is the liquid-crystal compounds with general formula I.
Embodiment 16
The liquid crystal compound of embodiment 16 forms and measurement parameter is shown in Table 18.
Table 18
Note：Serial number 1,2 and 3 is the liquid-crystal compounds with general formula I.
Comparative example 1
The liquid crystal compound of comparative example 1 forms and measurement parameter is shown in Table 19.
Table 19
Comparative example 2
The liquid crystal compound of comparative example 2 forms and measurement parameter is shown in Table 20.
Table 20
Wherein, with liquid-crystal compounds in comparative example 1Instead of embodiment 1
InAnd with liquid-crystal compounds in comparative example 2Instead of in embodiment 12
From above-described embodiment it can be found that with general formula I liquid-crystal compounds be particularly conducive to increase system optics respectively to
Opposite sex value, and the elasticity of flexure COEFFICIENT K that system viscosity can be reduced, improve system33And vertical dielectric constant ε⊥, to improve
Response speed, improve light whole system penetrance, be conducive to it is energy saving, and be conducive to improve contrast.When the liquid of general formula I
When brilliant compound is mixed with other variety classes liquid-crystal compounds, can obtain with high light anisotropy, high clearing point,
Compared with low viscosity and the liquid crystal compound of higher elasticity coefficient, especially (such as with the nonpolar liquid-crystal compounds with general formula III 5
Code is the nonpolar liquid-crystal compounds of 3HHV) mixing when, the liquid crystal compound of low viscosity can be obtained, can be used for manufacturing quick
The liquid crystal media of response.Above-mentioned measurement parameter is related with the composition physico-chemical property of all liquid-crystal compounds of liquid crystal media, this hair
Bright liquid crystal compound is mainly used for the liquid crystal parameter of regulation system.
By being apparent that the comparison of when embodiment 12 and comparative example 2 for embodiment 1 and comparative example 1, work as liquid
When in brilliant mixture comprising the liquid-crystal compounds with general formula I, there is relatively high optical anisotropy value, it is relatively low
Rotary viscosity, is particularly conducive to the liquid crystal media of manufacture quick response, and is conducive to the suitable clearing point T of regulation systemNI, it is curved
Bent coefficient of elasticity K33, vertical dielectric constant ε⊥And dielectric anisotropy Δ ε values, these are for obtaining wider array of operating temperature, more
Fast response speed, higher contrast and light transmittance, lower power consumption are helpful.
Though the claimed all liquid crystal compounds of the non-limit of the present invention, those skilled in the art will envision that
It is on the basis of published above-described embodiment, only in conjunction with the profession of itself to attempt that it can be obtained with similar reaction route
His similar compound is without making the creative labor.Herein since length is limited, representative embodiment is only enumerated.
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, any made by repair
Change, equivalent replacement, improvement etc., should all be included in the protection scope of the present invention.
Claims (10)
1. a kind of liquid-crystal compounds, which is characterized in that the liquid-crystal compounds have general formula I, the general formula I be：
Wherein,
R1For H, carbon atom number indicate 1~7 alkyl or alkoxy, carbon atom number be 2~7 alkenyl or alkene alkoxy；
R2For H, carbon atom number be 1~7 alkyl, carbon atom number be 1~7 alkoxy, carbon atom number be 2~7 alkenyl, carbon
The alkene alkoxy that atomicity is 2~7, H or CH in abovementioned alkyl, alkoxy, alkenyl and alkene alkoxy2It can be replaced by cyclopenta,
Or cyclopenta, or for be 1~7 by carbon atom number alkyl, carbon atom number be 1~7 alkoxy, carbon atom number be 2~7
The cyclopenta that the alkene alkoxy that alkenyl or carbon atom number are 2~7 replaces；
A is 0,1 or 2；B is selected from 0 or 1；
G is selected from singly-bound ,-COO-,-CH2O—、—OCH2—、—C2H4—、—CF2O—、—OCF2- ,-C ≡ C- or-CH
Any one of=CH-；
It is selected from It is one or more in the group of composition；
It is selected fromOne in the group of composition
Kind is a variety of.
2. liquid-crystal compounds according to claim 1, which is characterized in that the general formula I is any one in general formula I1~I46
Kind：
Wherein,
R1' be H, carbon atom number indicate 1~7 alkyl or alkoxy, carbon atom number be 2~7 alkenyl or alkene alkoxy；
R2' it is H, the alkenyl that the alkoxy that the alkyl that carbon atom number is 1~7, carbon atom number are 1~7, carbon atom number are 2~7, carbon
The alkene alkoxy that atomicity is 2~7, H or CH in abovementioned alkyl, alkoxy, alkenyl and alkene alkoxy2It can be replaced by cyclopenta,
Or cyclopenta, or for be 1~7 by carbon atom number alkyl, carbon atom number be 1~7 alkoxy, carbon atom number be 2~7
The cyclopenta that the alkene alkoxy that alkenyl or carbon atom number are 2~7 replaces.
3. a kind of liquid crystal compound with negative permittivity, which is characterized in that the liquid crystal compound includes at least one right
It is required that the liquid-crystal compounds described in 1 or 2.
4. the liquid crystal compound according to claim 3 with negative permittivity, which is characterized in that the liquid crystal compound
The weight content for including the liquid-crystal compounds with general formula I is 0.1~75%, preferably 0.1~50%, further preferably
0.1~30%.
5. the liquid crystal compound according to claim 3 with negative permittivity, which is characterized in that the liquid crystal compound
Further include at least one polarity liquid-crystal compounds and/or at least one nonpolar liquid-crystal compounds；
Preferably, the polar compound is negative polarity liquid-crystal compounds, and the negative polarity compound is selected from 1~II92 of Formula II
One or more in compound represented, the non-polar compound is in formula III 1~III30 compounds represented
It is one or more；
Formula II 1~II92 difference is as follows：
In 1~II92 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, or be H or CH2Replaced by cyclopenta
Carbon atom number be 1~7 alkyl, carbon atom number be 1~7 alkoxy, carbon atom number be 2~7 alkenyl or carbon atom number
For 2~7 alkene alkoxy, be either cyclopenta or for be 1~7 by carbon atom number alkyl, carbon atom number be 1~7 alkane
The cyclopenta that the alkenyl that oxygroup or carbon atom number are 2~7 replaces；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；
1~the III30 of formula III is respectively：
In the 1~III30 of formula III, R5、R6It is 1~7 to be each independently alkyl, carbon atom number that carbon atom number is 1~7
The alkene alkoxy that the alkenyl or carbon atom number that alkoxy, carbon atom number are 2~7 are 2~7, or be H or CH2It is taken by cyclopenta
The alkenyl or carbon atom that alkoxy that alkyl that the carbon atom number in generation is 1~7, carbon atom number are 1~7, carbon atom number are 2~7
Number for 2~7 alkene alkoxy, be either cyclopenta or for be 1~7 by carbon atom number alkyl, carbon atom number be 1~7
The cyclopenta that the alkenyl that alkoxy or carbon atom number are 2~7 replaces；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；
Preferably, the non-polar compound is 5 compound represented of formula III.
6. the liquid crystal compound according to claim 5 with negative permittivity, which is characterized in that the liquid crystal compound
In the mass fraction comprising at least one polarity liquid-crystal compounds and/or at least one nonpolar liquid-crystal compounds be 0~
80%.
7. the liquid crystal compound with negative permittivity according to any one of claim 3~6, which is characterized in that
Also include the polymerizable compound that mass fraction is 0~20% in the liquid crystal compound, the polymerizable compound general formula is such as
Under：
Wherein
—T1With-T2It each independently representsOr epoxy group；
—Y1- and-Y2- 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- selected from singly-bound ,-O-,-CO-,-COO-,-OCO-,-CH2O—、—OCH2—、—C2H4—、—
CF2O—、—OCF2- ,-C ≡ C- ,-CH=CH-,One or both of group of composition；
M is 0,1 or 2；
Each independently represent when occurring every time on unsubstituted or cyclohexylidene-CH2-is by O
SubstitutionOn unsubstituted or sub- phenyl ring=CH-replaced by NWhat the H on ring was replaced by F
8. the liquid crystal compound with negative permittivity according to any one of claim 3~6, which is characterized in that
Also include the stabilizer that mass fraction is 0~20% in the liquid crystal compound, it is preferable that the stabilizer is with general formula
It is one or more in IV1~IV5 compounds represented：
Wherein,
R7For the alkyl with 1~7 carbon atom, the alkoxy with 1~7 carbon atom, the alkene with 2~7 carbon atoms
Base, the halogenated alkyl with 1~7 carbon atom, the halogenated alkoxy with 1~7 carbon atom or with 2~7 carbon atoms
Halogenation alkenyl；The alkyl, the alkoxy and the alkenyl are alkyl, alkoxy and the alkenyl of linear chain or branched chain；
For Any one of group of composition.
9. application of the liquid-crystal compounds as claimed in claim 1 or 2 in liquid crystal display material or liquid crystal display, preferably
Application in minus display pattern, the minus display pattern are preferably VA, PSVA or FFS display pattern.
10. liquid crystal compound the answering in liquid crystal display material or liquid crystal display described in any one of claim 3 to 8
With the preferably application in minus display pattern, the minus display pattern is preferably VA, PSVA or FFS display pattern.
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