CN113845921A - Liquid crystal composition containing dibenzo derivative and liquid crystal display device thereof - Google Patents

Liquid crystal composition containing dibenzo derivative and liquid crystal display device thereof Download PDF

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CN113845921A
CN113845921A CN202010596439.0A CN202010596439A CN113845921A CN 113845921 A CN113845921 A CN 113845921A CN 202010596439 A CN202010596439 A CN 202010596439A CN 113845921 A CN113845921 A CN 113845921A
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liquid crystal
ring
independently
carbon atoms
crystal composition
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姚利芳
贺笛
丁文全
徐海彬
徐爽
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Jiangsu Hecheng Display Technology Co Ltd
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    • 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
    • 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

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Abstract

The invention discloses a liquid crystal composition containing a dibenzo derivative and a liquid crystal display device thereof. The liquid crystal composition comprises at least one compound of a general formula I and at least one compound of a general formula II. Compared with the prior art, the liquid crystal compound maintains the dielectric constant epsilon perpendicular to the molecular axis on the premise of keeping the optical anisotropy delta n, the clearing point Cp and the dielectric anisotropy delta epsilon at stable levels (even better)⊥Higher vertical dielectric to dielectric ratio epsilon⊥Both/delta epsilon are improved very obviously, so that the penetration rate is improved obviously; in addition, the liquid crystal composition of the invention also has lower rotational viscosity gamma 1 and larger average elastic constant KaveTherefore, the method has the technical effects of quick response and high contrast. The liquid crystal composition can meet the requirements of liquid crystal display devices on quick response, low power consumption and good display effect.

Description

Liquid crystal composition containing dibenzo derivative and liquid crystal display device thereof
Technical Field
The invention relates to the field of liquid crystal display, in particular to a liquid crystal composition containing a dibenzo derivative and a liquid crystal display device thereof.
Background
Liquid Crystal Displays (LCDs) have been rapidly developed due to their small size, light weight, low power consumption and excellent Display quality, and are widely used particularly in portable electronic information products. As the size of a liquid crystal screen for a portable computer, an office application, a video application increases, in order to enable the liquid crystal display to be used for a large screen display and eventually replace a Cathode Ray Tube (CRT), there are still some problems to be solved, such as improvement of viewing angle characteristics, improvement of response speed, increase of contrast, improvement of transmittance, and the like. The narrow viewing angle of the LCD means that the contrast ratio is significantly reduced when viewed from a direction perpendicular to the normal of the liquid crystal cell, and the phenomenon of gray scale and color inversion occurs when the viewing angle is large, which seriously affects the display quality of the LCD, so that the viewing angle problem becomes a great obstacle to the replacement of the CRT technique by the LCD.
The viewing angle problem of the LCD is determined by the operating principle of the liquid crystal. The liquid crystal molecules themselves are rod-shaped, and different molecular alignment modes correspond to different optical anisotropies. The smaller the included angle between incident light and liquid crystal molecules is, the smaller the birefringence is; conversely, the greater the birefringence. The included angles between the light rays entering the liquid crystal box at different angles from the normal direction of the display screen and the director of the liquid crystal molecules are different, so that the effective optical path difference delta n and d is different at different viewing angles. However, the optical path difference of the liquid crystal cell is designed according to the normal direction perpendicular to the liquid crystal cell, and for the light rays with oblique incidence, the minimum transmittance increases with the increase of the included angle, the contrast ratio decreases, and when the included angle is large enough, the contrast ratio even reverses.
At present, many methods for solving the viewing angle problem have been proposed such as: an Optically Compensated Bend (OCB) mode, an in-plane switching (IPS) mode, a Fringe Field Switching (FFS) mode, and a multi-domain vertical alignment (MVA) mode. They all have their own advantages and disadvantages: the MVA mode has high contrast and fast response characteristics, but it requires one biaxial compensation film and two elliptical polarizers, and thus is high in cost; the OCB mode is difficult to maintain stable control with ac voltage, the transmittance of R, G, B three monochromatic lights is different, and in the absence of field, the molecules in the liquid crystal cell are aligned in the direction parallel to the substrate, and in order to achieve bend alignment, a voltage is applied to the cell for several seconds for presetting, and then the alignment can be maintained at a lower voltage, which is inconvenient to use; the IPS mode requires only a linear polarizer and does not require a compensation film, but its response speed is too slow to display a fast moving picture. Since the IPS mode and the FFS mode are simple to manufacture and have a wide viewing angle, they are the most attractive approaches capable of improving viewing angle characteristics and realizing large-area display.
In the early 70 s of the last century, experimental studies have been conducted on the basic electro-optical characteristics of the IPS mode of nematic liquid crystals, both uniformly aligned and twisted, characterized in that a pair of electrodes is made on the same substrate, while the other substrate has no electrode, and the alignment of the liquid crystal molecules is controlled by a transverse electric field applied between the pair of electrodes, and thus this mode can also be called lateral field mode. In the IPS mode, nematic liquid crystal molecules are uniformly arranged in parallel between two substrates, and two polarizing plates are orthogonally arranged. In the IPS mode, when no electric field is applied, incident light is blocked by two orthogonal polarizing plates to be in a dark state, and when an electric field is applied, liquid crystal molecules rotate to cause retardation, so that light leaks from the two orthogonal polarizing plates.
The IPS mode and the FFS mode may use a positive liquid crystal or a negative liquid crystal, and since a driving voltage required for a transmittance of 100% decreases with an increase in absolute value of Δ ∈, the driving voltage required for a transmittance of 100% is lower than that of the negative liquid crystal and a response speed is faster, but the negative liquid crystal has a better transmittance than that of the positive liquid crystal, mainly due to different arrangements of liquid crystal molecules in a liquid crystal cell in the positive and negative IPS modes or FFS modes and different arrangements and rotations of the liquid crystal molecules at power-on. Since the positive liquid crystal molecules are affected by the fringe vertical electric field and the effective Δ n × d is decreased, the transmittance of the positive liquid crystal molecules is lower than that of the negative liquid crystal molecules under the applied electric field condition.
Transmittance equation Transmitance (Transmittance, T). alpha.. DELTA.. epsilon. epsilon./epsilon. according to the Transmittance equation of IPS mode and FFS mode⊥(the term "oc" means an "inverse ratio" relationship), in order to increase the transmittance of positive liquid crystal, it is possible to attempt to decrease Δ ∈ of the liquid crystal medium, but generally, the adjustment range of the driving voltage of the same product is limited. In addition, the liquid crystal molecules will tilt in the Z-axis direction under the action of the vertical component of the fringe electric field, so that the optical anisotropy delta n will change, according to the formula
Figure BDA0002557423960000021
(where χ is the angle between the optic axis of the liquid crystal layer and the optic axis of the polarizer, Δ n is the optical anisotropy, d is the cell gap, λ is the wavelength), it can be considered that the effective Δ n × d affects T, and if the transmittance of the positive liquid crystal is to be improved, the Δ n × d can be increased, but the retardation design of each product is fixed.
In view of the above, the conventional means for increasing the transmittance of the liquid crystal material in the positive IPS mode or FFS mode can be considered from the following two points: (1) by increasing epsilon while keeping constant the dielectric anisotropy Delta epsilon of the liquid crystal composition⊥The transmittance can be effectively improved; (2) the elastic constant K of the liquid crystal composition is increased, so that the liquid crystal molecules have better order degree and less light leakage, and the transmittance is improved. The prior art is mainly enhanced by adding a negative monomer to the positive liquid crystal component. However, the addition of a negative monomer results in a slow response speed and poor reliability. In the presently disclosed patent,. epsilon.⊥Not large enough, in ε⊥When the value is larger, the response is slow, and the K value is not large enough. In view of some of the disadvantages of the prior high liquid crystal compositions, the present invention provides a liquid crystal composition doped with a negative monomer, the liquid crystal composition having ∈⊥Large K value and high transmittance.
Patent application CN110499162A discloses a liquid crystal composition with high transmittance and positive dielectric anisotropy, which improves the transmittance and response time of the whole liquid crystal composition by adding a negative compound of the following structure to the positive liquid crystal component:
Figure BDA0002557423960000022
wherein R is1Represents cyclopropyl, cyclobutyl or cyclopentyl; z represents a single bond, -CH2-、-O-、-CH2CH2-or-CH2O-；R2Represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 7 carbon atoms or an alkoxy group having 1 to 7 carbon atoms; x represents an oxygen atom or a sulfur atom.
However, the liquid crystal compounds have limited improvement in transmittance and viscosity, and particularly have a transmittance of 10% or less. Therefore, based on the prior art, it is desired to develop a liquid crystal composition with higher transmittance, higher contrast and faster response speed, so as to satisfy the requirements of higher visual effect and lower power consumption of liquid crystal displays.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a high clearing point, large optical anisotropy, large dielectric anisotropy, lower rotational viscosity and higher dielectric constant epsilon vertical to a molecular axis⊥Higher vertical dielectric to dielectric ratio epsilon⊥A/delta epsilon and a higher average elastic constant KaveThe liquid crystal composition of (1).
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides a liquid crystal composition comprising at least one compound of formula I, and at least one compound of formula II:
Figure BDA0002557423960000031
and
Figure BDA0002557423960000032
wherein the content of the first and second substances,
r represents-H, halogen, -CN, or straight or branched alkyl containing 1-12 carbon atoms,
Figure BDA0002557423960000033
Figure BDA0002557423960000034
In which a linear or branched alkyl group having 1 to 12 carbon atoms,
Figure BDA0002557423960000035
One or more-CH's not adjacent to each other2-each may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -S-, -CO-O-, or-O-CO-, one or at least two-H may each be independently substituted by-F or-Cl;
Rxrepresents-H, straight chain or branched chain alkyl containing 1-12 carbon atoms, one or more than two non-adjacent-CH in the straight chain or branched chain alkyl containing 1-12 carbon atoms2-each independently can be replaced by-CH ═ CH-, -C ≡ C-, -O-, -S-, -CO-O-, or-O-CO-, one or at least two-H each independently can be substituted by-F or-Cl, and said R isxAnd ring
Figure BDA0002557423960000036
To any carbon atom of;
R1represents a linear or branched alkyl group having 1 to 12 carbon atoms,
Figure BDA0002557423960000037
1 or non-adjacent 2 or more-CH in the linear or branched alkyl containing 1 to 12 carbon atoms2-said linear or branched alkyl radical containing from 1 to 12 carbon atoms which may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-or-O-CO-, respectively,
Figure BDA0002557423960000038
Each of one or at least two of-H may be independently substituted with-F or-Cl;
RYrepresents halogen, haloalkyl or haloalkoxy having 1 to 5 carbon atoms, haloalkenyl or haloalkenyloxy having 2 to 5 carbon atoms;
ring (C)
Figure BDA0002557423960000039
To represent
Figure BDA00025574239600000310
And one or at least two of the ring single bonds in the aforementioned groups may be replaced by a double bond;
ring (C)
Figure BDA00025574239600000311
Ring (C)
Figure BDA00025574239600000312
And ring
Figure BDA00025574239600000313
Each independently represent
Figure BDA00025574239600000314
Figure BDA00025574239600000315
Wherein
Figure BDA00025574239600000316
Of one or at least two-CH2-may be replaced by-O-, one or at most two of the ring single bonds may be replaced by double bonds, wherein
Figure BDA00025574239600000317
May be substituted by-F or-Cl, and one or at least two rings-CH-may be replaced by-N ═ c; the term "one or at least two" in "one or at least two rings may be replaced by-N-means the number of-CH-s in the present inventionThe same meaning is implied by the same expression;
Z1is represented by- (CH)2)aO-or- (CH)2)aS-, wherein a represents an integer of 0 to 7, e.g., 1, 3, 5, etc.;
Z2represents-O-, -S-, -CO-O-, -O-CO-, -CF2O-、-OCF2-、-CH2O-、-CH2S-、-OCH2-、-SCH2-、-CH2-、-CH2CH2-、-(CH2)4-、-CH＝CH-CH2O-、-C2F4-、-CH2CF2-、-CF2CH2-, -CF ═ CF-, -CH ═ CF-, -CF ═ CH-, -CH ═ CH-, -C ≡ C-, or a single bond;
Z3、Z4and Z5Each independently represents a single bond, -CH2CH2-、-CF2CF2-、-CF2O-、-OCF2-、-CO-O-、-O-CO-、-O-CO-O-、-CH＝CH-、-CF＝CF-、-CH2O-or-OCH2-；
L1、L2、L3And L4Each independently represents-F, -Cl, -CF3or-CHF2；
L5And L6Each independently represents-H or a straight chain alkyl group containing 1 to 3 carbon atoms;
x represents-CO-, -S-or-O-;
n represents 0, 1 or 2, wherein when n represents 2, a ring
Figure BDA0002557423960000041
Same or different, Z2The same or different; and is
n1 and n2 each independently represent 0, 1 or 2, and 0. ltoreq. n1+ n 2. ltoreq.3, and when n 1. ltoreq.2, the ring
Figure BDA0002557423960000042
Same or different, Z3Identical or different, when n2 is 2, the ring
Figure BDA0002557423960000043
Same or different, Z4The same or different. When n1 is 2, there are two of the compounds
Figure BDA0002557423960000044
Two of these
Figure BDA0002557423960000045
May have the same structure or different structures, and may illustratively be one of
Figure BDA0002557423960000046
The other is
Figure BDA0002557423960000047
The invention has the same meaning when it relates to expressions of "the same or different";
in the present invention, "… … may be independently replaced" means that they may or may not be replaced, i.e., replaced or not replaced, and they are within the protection scope of the present invention, and "… … may be independently replaced" similarly, and the positions of "replacement" and "replacement" may be arbitrary.
In the context of the present invention, the short straight lines on one or both sides of the radical structure represent access bonds and do not represent methyl groups, e.g.
Figure BDA0002557423960000048
A short straight line on the right side,
Figure BDA0002557423960000049
Short straight lines on both sides.
In the present invention, the number of carbons of the linear or branched alkyl group having 1 to 12 carbon atoms includes, but is not limited to, 2, 4, 6, 8, 10, etc.
Compared with the technical scheme of improving the transmittance of a positive liquid crystal composition by using a conventional negative liquid crystal compound in the prior art, the liquid crystal composition containing the compound of the general formula I and the compound of the general formula II is improved in transmittanceIt is more obvious that, in addition, the rotational viscosity and K of the liquid crystal compositionaveThe values also improved significantly.
Furthermore, in the compounds of the general formula I according to the invention, the ring
Figure BDA00025574239600000410
Is the structure of an oxa-or thia-five membered ring, the opposite ring
Figure BDA0002557423960000051
As far as the prior art is concerned with five-membered carbocycles, the compounds of the general formula I according to the invention have a relatively large dielectric constant ε perpendicular to the molecular axis⊥Is more beneficial to improving the ratio epsilon of the vertical dielectric to the dielectric of the liquid crystal composition on the premise of maintaining the dielectric anisotropy unchanged⊥The/delta epsilon, thereby realizing the effect of improving the penetration rate of the liquid crystal composition; in addition, the compounds of the general formula I according to the invention have a low rotational viscosity γ 1 and a large average elastic constant KaveThe liquid crystal display device containing the liquid crystal composition has smaller light leakage in a dark state, higher contrast and high response speed.
In some embodiments of the invention, n represents 0.
In the solution according to the invention, the ring is preferably
Figure BDA0002557423960000052
To represent
Figure BDA0002557423960000053
And one or at least two of the ring single bonds in the aforementioned groups may be replaced by a double bond.
In some embodiments of the invention, L1And L2Both represent-F.
In some embodiments of the invention, X represents-O-or-S-.
In some embodiments of the invention, the liquid crystal composition comprises at least one compound of formula I wherein X represents-O-; further preferably, the liquid crystal composition contains at least one compound of the general formula I in which X represents-O-, and at least one compound of the general formula I in which X represents-S-.
In some embodiments of the invention, a represents an integer from 0 to 3, further preferably a represents an integer from 1 to 3, still further preferably a represents 1.
In some embodiments of the invention, R represents a straight chain alkyl or alkoxy group containing from 1 to 12 carbon atoms.
In some embodiments of the invention, Rxrepresents-H or a straight chain alkyl group having 1 to 6 carbon atoms.
In some embodiments of the present invention, the compound of formula I accounts for 0.1-40% of the total weight of the liquid crystal composition, such as 1%, 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, etc., and further preferably, the compound of formula I accounts for 1-30% of the total weight of the liquid crystal composition.
In some embodiments of the invention, the compound of formula II is selected from any one or a combination of at least two of the following compounds:
Figure BDA0002557423960000054
Figure BDA0002557423960000061
wherein the content of the first and second substances,
Z3、Z4and Z4' each independently represents a single bond, -CH2CH2-、-CO-O-、-O-CO-、-CH2O-or-OCH2-；
L3、L4、L7、L8、L10And L11Each independently represents-H, -F;
L5or L9Each independently represents-H or-CH3；
Rarepresents-CH2-or-O-;
a and b each independently represent 0 or 1; and is
RYrepresents-F, -CF3、-OCF3or-CH2CH2CH＝CF2。
In some embodiments of the invention, the compound of formula II comprises 1-30% of the total weight of the liquid crystal composition, e.g., 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, etc.; further, the compound of the general formula II accounts for 1-25% of the total weight of the liquid crystal composition; still further, the compound of the general formula II accounts for 5-20% of the total weight of the liquid crystal composition. The above percentages refer to the mass percentages of the total mass of all compounds of formula II in the composition, and the following references to the same expression are intended to have the same meaning.
In some embodiments of the invention, the liquid crystal composition comprises at least two compounds of formula II; further preferably, the liquid crystal composition contains at least three compounds of formula II; still further preferably, the liquid crystal composition contains at least four compounds of formula II.
In some embodiments of the present invention, the compound of formula II is selected from any one or a combination of at least two of the compounds of formula II-1 and formula II-7.
The alkenyl group in the present invention is preferably a group represented by any one of the formulae (V1) to (V9), and particularly preferably formula (V1), formula (V2), formula (V8), or formula (V9). The groups represented by formulae (V1) to (V9) are shown below:
Figure BDA0002557423960000071
wherein denotes the carbon atom in the ring structure to which it is bonded.
The alkenyloxy group in the present invention is preferably a group represented by any one of formulae (OV1) to (OV9), and particularly preferably formula (OV1), formula (OV2), formula (OV8) or (OV 9). The groups represented by formulae (OV1) to (OV9) are shown below:
Figure BDA0002557423960000072
wherein denotes the carbon atom in the ring structure to which it is bonded.
In some embodiments of the invention, the liquid crystal composition further comprises one or at least two compounds of formula M
Figure BDA0002557423960000073
Wherein the content of the first and second substances,
RM1and RM2Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
Figure BDA0002557423960000074
Figure BDA0002557423960000075
Wherein one or two or more non-adjacent-CH groups in the linear or branched alkyl group having 1 to 12 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-;
ring (C)
Figure BDA0002557423960000076
Ring (C)
Figure BDA0002557423960000077
And ring
Figure BDA0002557423960000078
Each independently represent
Figure BDA00025574239600000710
Figure BDA00025574239600000711
Wherein
Figure BDA00025574239600000712
Of one or at least two-CH2-may be replaced by-O-, wherein
Figure BDA00025574239600000713
At most one-H in (a) may be substituted by halogen;
ZM1and ZM2Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-、-(CH2)4-、-CF2O-、-OCF2-or-CF2CF2-; and is
nM1Represents 0, 1, 2 or 3, wherein when n isM1When 2 or 3, ring
Figure BDA00025574239600000714
Same or different, ZM2The same or different.
In some embodiments of the invention, RM1And RM2Each independently represents a linear alkyl group having 1 to 10 carbon atoms, a linear alkoxy group having 1 to 9 carbon atoms, or a linear alkenyl group having 2 to 10 carbon atoms; further preferably, RM1And RM2Each independently represents a linear alkyl group having 1 to 8 carbon atoms, a linear alkoxy group having 1 to 7 carbon atoms, or a linear alkenyl group having 2 to 8 carbon atoms; even further preferably, RM1And RM2Each independently represents a linear alkyl group having 1 to 5 carbon atoms, a linear alkoxy group having 1 to 4 carbon atoms, or a linear alkenyl group having 2 to 5 carbon atoms.
In some embodiments of the invention, RM1And RM2Each independently represents a straight-chain alkenyl group having 2 to 8 carbon atoms; further preferably, RM1And RM2Each independently represents a straight-chain alkenyl group having 2 to 5 carbon atoms.
In some embodiments of the invention, RM1And RM2One of them is a linear alkenyl group having 2 to 5 carbon atoms, and the other is a linear alkyl group having 1 to 5 carbon atoms.
In some embodiments of the invention, RM1And RM2Each independently represents a linear alkyl group having 1 to 8 carbon atoms, or a linear alkoxy group having 1 to 7 carbon atoms; further preferably, RM1And RM2Each independently represents a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms.
In some embodiments of the invention, RM1And RM2Either one of which is a linear alkyl group having 1 to 5 carbon atoms and the other is a linear alkyl group having 1 to 5 carbon atoms or a linear alkoxy group having 1 to 4 carbon atoms; further preferably, RM1And RM2Both of which are each independently a linear alkyl group having 1 to 5 carbon atoms.
In some embodiments of the invention, the compound of formula M is selected from any one or a combination of at least two of the following compounds:
Figure BDA0002557423960000081
Figure BDA0002557423960000091
Figure BDA0002557423960000101
the lower limit of the content of the compound of formula M is 10%, 20%, 25%, 30%, 40% or 50% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the content of the compound of formula M is 70%, 65%, 60%, 55%, 45%, 35% or 25% with respect to the total weight of the liquid crystal composition of the present invention.
For adjusting the clearing point of the liquid crystal composition,Viscosity, low-temperature storage stability and the like, so that the obtained liquid crystal display device has excellent transmittance and color expression and better application value, and the component composition of the liquid crystal composition needs to be adjusted; in particular, relative to the total weight of the liquid crystal composition of the present invention, wherein the ring
Figure BDA0002557423960000102
To represent
Figure BDA0002557423960000103
The content of the compound of the general formula (M) is 10 to 50%, for example, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, etc.; preferably, wherein the ring
Figure BDA0002557423960000104
To represent
Figure BDA0002557423960000105
The content of the compound of the general formula M is 20 to 45%.
The content of the compound of formula M is preferably higher in the lower limit and higher in the upper limit when the viscosity of the liquid crystal composition of the present invention needs to be kept low and the response time is short; further, when it is necessary to keep the clearing point of the liquid crystal composition of the present invention high and the temperature stability good, it is preferable that the lower limit value is high and the upper limit value is high; when the absolute value of the dielectric anisotropy is increased in order to keep the driving voltage low, it is preferable that the lower limit value is lowered and the upper limit value is lowered.
In the case where reliability is important, R is preferableM1And RM2Each independently is alkyl; in the case where importance is attached to reduction in volatility of the compound, R is preferablyM1And RM2Each independently is an alkoxy group; when importance is attached to the reduction in viscosity, R is preferably usedM1And RM2At least one of which is alkenyl.
In some embodiments of the invention, to further reduce the liquid crystal populationThe viscosity of the composition, the liquid crystal composition preferably comprises one or at least two of RM1And/or RM2Compounds of the formula M1 being n-propyl
Figure BDA0002557423960000106
In some embodiments of the invention, the liquid crystal composition further comprises one or at least two compounds of formula N:
Figure BDA0002557423960000107
wherein the content of the first and second substances,
RN1and RN2Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
Figure BDA0002557423960000111
Figure BDA0002557423960000112
In which one or more than two non-adjacent-CH groups in the linear or branched alkyl group containing 1-12 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-;
ring (C)
Figure BDA0002557423960000113
And ring
Figure BDA0002557423960000114
Each independently represent
Figure BDA0002557423960000115
Wherein
Figure BDA0002557423960000116
Of one or at least two-CH2-may be replaced by-O-, one or at most two of the ring single bonds may be replaced by double bonds, wherein
Figure BDA0002557423960000117
May be substituted by-F or-Cl, and one or at least two rings-CH-may be replaced by-N ═ c;
ZN1and ZN2Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-、-(CH2)4-、-CF2O-、-OCF2-or-CF2CF2-；
LN1And LN2Each independently represents-H or methyl; and is
nN1Represents 0, 1, 2 or 3, nN2Represents 0 or 1, and 0. ltoreq. nN1+nN2Is less than or equal to 3, wherein when n isN1When 2 or 3, ring
Figure BDA0002557423960000118
Same or different, ZN1The same or different.
In some embodiments of the invention, RN1And RN2Each independently represents a linear or branched alkyl or alkoxy group having 1 to 8 carbon atoms, or a linear or branched alkenyl or alkenyloxy group having 2 to 8 carbon atoms, and further preferably RN1And RN2Each independently a linear or branched alkyl or alkoxy group containing 1 to 5 carbon atoms, or a linear or branched alkenyl or alkenyloxy group containing 2 to 5 carbon atoms.
In some embodiments of the invention, RN1Further preferred is a linear or branched alkyl group having 1 to 5 carbon atoms or a linear or branched alkenyl group having 2 to 5 carbon atoms, RN1Still more preferably a linear or branched alkyl group having 2 to 5 carbon atoms or an alkenyl group having 2 to 3 carbon atoms; rN2Further preferred is a straight-chain or branched alkoxy group having 1 to 4 carbon atoms.
In some embodiments of the invention, the ring
Figure BDA0002557423960000119
And ring
Figure BDA00025574239600001110
Each independently represent
Figure BDA00025574239600001111
In some embodiments of the invention, the compound of formula N is selected from any one or a combination of at least two of the following compounds:
Figure BDA0002557423960000121
Figure BDA0002557423960000131
Figure BDA0002557423960000141
the lower limit of the content of the compound of formula N is 10%, 13%, 15%, 18%, 20%, 23%, 25%, 28%, 30%, 33%, 35%, 38%, or 40% with respect to the total weight of the liquid crystal composition of the present invention; the upper limit of the content of the compound of formula N is 75%, 72%, 70%, 68%, 65%, 63%, 60%, 55%, 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15%, or 10% with respect to the total weight of the liquid crystal composition of the present invention.
With respect to the content of the compound of the general formula N, when it is necessary to keep the response time of the liquid crystal display device of the present invention short, the lower limit value and the upper limit value thereof are preferably low; further, when the liquid crystal display device of the present invention needs to maintain a wider operating temperature range, it is preferable that the lower limit value and the upper limit value are lower; when the absolute value of the dielectric anisotropy is increased in order to keep the driving voltage of the liquid crystal composition low, it is preferable that the lower limit value is increased and the upper limit value is increased.
In some embodiments of the present invention, the liquid crystal composition further comprises at least one compound of formula A-1 and/or at least one compound of formula A-2:
Figure BDA0002557423960000142
wherein the content of the first and second substances,
RA1and RA2Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
Figure BDA0002557423960000143
Figure BDA0002557423960000144
In which one or more than two non-adjacent-CH groups in the linear or branched alkyl group containing 1-12 carbon atoms2-linear or branched alkyl containing 1 to 12 carbon atoms which may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-or-O-CO-, respectively,
Figure BDA0002557423960000145
Each of one or at least two of-H may be independently substituted with-F or-Cl;
ring (C)
Figure BDA0002557423960000151
Ring (C)
Figure BDA0002557423960000152
Ring (C)
Figure BDA0002557423960000153
And ring
Figure BDA0002557423960000154
Each independently represent
Figure BDA0002557423960000155
Wherein
Figure BDA0002557423960000156
Figure BDA0002557423960000157
At most one-CH in2-may be replaced by-O-and one or at least two ring single bonds may be replaced by double bonds, wherein
Figure BDA0002557423960000158
Wherein one or at least two of-H may be independently substituted by-F, -Cl, -CN, -CH3or-OCH3Substituted, and one or at least two rings-CH-may be replaced by-N ═ N;
ring (C)
Figure BDA0002557423960000159
And ring
Figure BDA00025574239600001510
Contains at most one-F;
ZA11、ZA21and ZA22Each independently represents a single bond, -CH2CH2-、-CF2CF2-、-CO-O-、-O-CO-、-O-CO-O-、-CH＝CH-、-CF＝CF-、-CH2O-or-OCH2-；
LA11、LA12、LA13、LA21And LA22Each independently represents-H, an alkyl group containing 1 to 3 carbon atoms or halogen;
XA1and XA2Each independently represents halogen, straight or branched haloalkyl or haloalkoxy having 1 to 5 carbon atoms, or straight or branched haloalkenyl or haloalkenyloxy having 2 to 5 carbon atoms;
nA11represents 0, 1, 2 or 3, wherein when n isA11When 2 or 3, ring
Figure BDA00025574239600001511
The same or different，ZA11The same or different;
nA12represents 1 or 2, wherein when nA12When 2, ring
Figure BDA00025574239600001512
The same or different; and is
nA2Represents 1, 2 or 3, wherein when n isA2When 2 or 3, ring
Figure BDA00025574239600001513
Same or different, ZA21The same or different.
In some embodiments of the invention, the compound of formula A-1 is selected from any one or a combination of at least two of the following compounds:
Figure BDA00025574239600001514
Figure BDA0002557423960000161
Figure BDA0002557423960000171
Figure BDA0002557423960000172
and
Figure BDA0002557423960000173
wherein the content of the first and second substances,
RA1represents a straight-chain or branched alkyl group having 1 to 8 carbon atoms,
Figure BDA0002557423960000174
In which one of the linear or branched alkyl groups containing 1 to 8 carbon atomsOr more than two non-adjacent-CH2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-, respectively, and one or at least two-H groups among linear or branched alkyl groups containing 1 to 8 carbon atoms may be independently substituted by-F or-Cl, respectively;
LA11、LA12、LA14、LA15and LA16Each independently represents-H or-F;
LA13represents-H or-CH3(ii) a And is
XA1represents-F, -CF3or-OCF3。
The lower limit of the weight percentage of the compound of formula a-1 with respect to the total weight of the liquid crystal composition of the present invention is 0%, 0.5%, 1%, 1.5%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 12%, 14%, 15%, 16%, 18%, 20%, 25%, or 30%; the upper limit value of the weight percentage of the compound of formula a-1 with respect to the total weight of the liquid crystal composition of the present invention is 50%, 45%, 40%, 38%, 36%, 34%, 32%, 30%, 28%, 26%, 24%, 20%, or 18%.
In some embodiments of the invention, the weight percentage of the compound of formula a-1 to the liquid crystal composition is 0% to 50%, e.g., 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, etc.; preferably, the compound of the general formula A-1 accounts for 1 to 40 percent of the weight of the liquid crystal composition; further preferably, the compound of the general formula A-1 accounts for 3-30% of the liquid crystal composition by weight.
In some embodiments of the invention, the compound of formula A-2 is selected from the group consisting of any one or a combination of at least two of the following compounds:
Figure BDA0002557423960000181
Figure BDA0002557423960000191
Figure BDA0002557423960000192
and
Figure BDA0002557423960000193
wherein the content of the first and second substances,
RA2represents a linear or branched alkyl group having 1 to 8 carbon atoms, wherein one or two or more-CH groups which are not adjacent to each other are present in the linear or branched alkyl group having 1 to 8 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-, respectively, and one or at least two-H groups present in these groups may be independently substituted by-F or-Cl, respectively;
LA21、LA22、LA23、LA24and LA25Each independently represents-H, F or-Cl; and is
XA2represents-F, -CF3、-OCF3or-CH2CH2CH＝CF2。
The lower limit of the weight percentage of the compound of formula a-2 with respect to the total weight of the liquid crystal composition of the present invention is 0%, 0.5%, 1%, 2%, 4%, 5%, 6%, 8%, 10%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 20%, 25%, 30%, 35%, 40%, 45%, or 50%; the upper limit value of the weight percentage of the compound of formula a-2 with respect to the total weight of the liquid crystal composition of the present invention is 50%, 45%, 40%, 35%, 30%, 28%, 27%, 26%, 25%, 24%, 23%, 22%, 21%, or 20%.
In some embodiments of the invention, the weight percentage of the compound of formula a-2 to the liquid crystal composition is 0% to 50%, e.g., 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 44%, 46%, 48%, etc.; preferably, the compound of the general formula A-2 accounts for 1 to 50 percent of the weight of the liquid crystal composition; further preferably, the compound of the general formula A-2 accounts for 2-40% of the liquid crystal composition by weight.
In some embodiments of the present invention, one or at least two other additives known to those skilled in the art and described in the literature may be added to the liquid crystal composition.
Further, additives such as an antioxidant and a light stabilizer used in the liquid crystal composition of the present invention are preferably as follows:
Figure BDA0002557423960000201
Figure BDA0002557423960000211
Figure BDA0002557423960000221
wherein n represents a positive integer of 1 to 12.
Preferably, the stabilizer is selected from the stabilizers shown below.
Figure BDA0002557423960000231
In some embodiments of the invention, the stabilizer comprises 0-5% by weight of the total liquid crystal composition; preferably, the stabilizer is 0-1% of the total weight of the liquid crystal composition; more preferably, the stabilizer is present in an amount of 0.01 to 0.1% by weight based on the total weight of the liquid crystal composition.
In another aspect, the present invention also provides a liquid crystal display device comprising the liquid crystal composition, wherein the liquid crystal display device is a TN mode, IPS mode or FFS mode liquid crystal display device.
Compared with the prior art, the invention has the following beneficial effects:
compared with the prior art, the liquid crystal compound containing the compound of the general formula I and the liquid crystal compound of the general formula II maintains the dielectric constant epsilon vertical to the molecular axis on the premise of keeping the optical anisotropy delta n, the clearing point Cp and the dielectric anisotropy delta epsilon at stable levels (even better)⊥Higher vertical dielectric to dielectric ratio epsilon⊥Both/delta epsilon are improved very obviously, so that the penetration rate is improved obviously; in addition, the liquid crystal composition of the invention also has lower rotational viscosity gamma 1 and larger average elastic constant KaveTherefore, the method has the technical effects of quick response and high contrast. The liquid crystal composition can meet the requirements of liquid crystal display devices on quick response, low power consumption and good display effect, and has higher application value in TN mode, IPS mode and FFS mode liquid crystal displays.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
In the present invention, unless otherwise specified, all the ratios mentioned in the present invention are weight ratios and all the temperatures are given in degrees Celsius.
For convenience of expression, in each of the following examples and comparative examples, the group structure of the liquid crystal compound is represented by the code listed in Table 1:
TABLE 1 radical structural code of liquid crystal compounds
Figure BDA0002557423960000232
Figure BDA0002557423960000241
Figure BDA0002557423960000251
Compounds of the following formula are exemplified:
Figure BDA0002557423960000252
the structural formula is represented by the code listed in Table 1, and can be expressed as: nCCGF, wherein n in the code represents the number of C atoms of the left alkyl group, for example, n is 3, namely, the alkyl group is-C3H7(ii) a C in the code represents 1, 4-cyclohexylene, G represents 2-fluoro-1, 4-phenylene and F represents a fluoro substituent.
The abbreviated symbols of the test items in the following examples and comparative examples are as follows:
cp clearing Point (nematic phase-isotropic phase transition temperature, ° C)
Delta epsilon dielectric anisotropy (1KHz, 25 ℃ C.)
ε⊥Dielectric constant perpendicular to molecular axis (1KHz, 25 ℃ C.)
ε⊥Ratio of/delta epsilon vertical dielectric to dielectric
Δ n optical anisotropy (illumination wavelength 589nm, 25 ℃ C.)
Gamma.1 rotational viscosity (mPa. multidot.s, 25 ℃ C.)
KaveAverage elastic constant
T penetration (DMS-505, cell thickness 3.5 μm,%)
Wherein the content of the first and second substances,
cp: obtained by testing by a melting point measuring method;
Δε：Δε＝ε∥-ε⊥wherein, epsilon∥Is a dielectric constant parallel to the molecular axis,. epsilon⊥For the dielectric constant perpendicular to the molecular axis, test conditions: a TN90 type test box with the box thickness of 7 μm and the temperature of 25 ℃;
Δ n: testing with Abbe refractometer under sodium lamp (589nm) at 25 deg.C;
γ1: testing by using an LCM-2 type liquid crystal physical property evaluation system; and (3) testing conditions are as follows: 25 ℃, 240V and the thickness of the test box is 20 mu m;
Figure BDA0002557423960000253
K11、K22、K33the liquid crystal display device is obtained by using an LCR instrument and an antiparallel friction box to test a C-V curve of liquid crystal and calculating the following test conditions: a 7-micron antiparallel friction box, wherein V is 0.1-20V;
test conditions of the transmittance: V-T curve of light modulation device is tested by DMS 505 photoelectric comprehensive tester, T in V-T curvemaxThe value is the penetration rate of the liquid crystal material, the light modulation device is a positive IPS type test box, the thickness of the box is 3.5 mu m, and V is 0-20V.
The components used in the following examples can be synthesized by a known method or obtained commercially. These synthesis techniques are conventional and the resulting liquid crystal compositions are tested for compliance with electronic compound standards.
Liquid crystal compositions were prepared according to the formulation of each liquid crystal composition specified in the following examples. The liquid crystal composition is prepared by a conventional method in the art, such as mixing in a prescribed ratio by heating, ultrasonic wave, suspension, etc.
Comparative example 1
The composition of the components of comparative example 1 is shown in table 2:
TABLE 2 compositions and Performance parameters of the liquid Crystal compositions
Figure BDA0002557423960000254
Figure BDA0002557423960000261
Comparative example 2
The composition of the components of comparative example 2 is shown in table 3:
TABLE 3 composition and Performance parameters of the liquid Crystal compositions
Figure BDA0002557423960000262
Example 1
The composition of the components of example 1 is shown in table 4:
TABLE 4 composition and Performance parameters of the liquid Crystal compositions
Figure BDA0002557423960000263
Figure BDA0002557423960000271
Example 2
The composition of the components of example 2 is shown in table 5:
TABLE 5 composition and Performance parameters of the liquid Crystal compositions
Figure BDA0002557423960000272
Example 3
The composition of the components of example 3 is shown in table 6:
TABLE 6 composition and Performance parameters of the liquid Crystal compositions
Figure BDA0002557423960000273
Figure BDA0002557423960000281
Example 4
The composition of the components of example 4 is shown in table 7:
TABLE 7 composition and Performance parameters of the liquid Crystal compositions
Figure BDA0002557423960000282
Example 5
The composition of the components of example 5 is shown in table 8:
TABLE 8 composition and Performance parameters of the liquid Crystal compositions
Figure BDA0002557423960000283
Figure BDA0002557423960000291
Example 6
The composition of the components of example 6 is shown in table 9:
TABLE 9 composition and Performance parameters of the liquid Crystal compositions
Figure BDA0002557423960000292
Example 7
The composition of the components of example 7 is shown in table 10:
TABLE 10 compositions and Performance parameters of the liquid Crystal compositions
Figure BDA0002557423960000293
Figure BDA0002557423960000301
As can be seen from comparison of comparative example 1 with examples 1-7, the liquid crystal composition comprising the compound of formula I and the liquid crystal compound of formula II of the present invention maintains the optical anisotropy Δ N, clearing point Cp, and dielectric anisotropy Δ ε at stable levels (even at stable levels) as compared to the prior art solutions using conventional negative liquid crystal compounds (e.g., compounds of formula N2 and formula N14) to improve the transmittance of positive liquid crystal compositionsAnd more preferably) a dielectric constant ε perpendicular to the molecular axis⊥Higher vertical dielectric to dielectric ratio epsilon⊥Both/delta epsilon are improved very obviously, so that the penetration rate is improved obviously; in addition, the liquid crystal composition of the invention also has lower rotational viscosity gamma 1 and larger average elastic constant KaveTherefore, the method has the technical effects of quick response and high contrast.
As can be seen from comparison of comparative example 2 with example 2, the dielectric constant ε perpendicular to the molecular axis of the liquid crystal composition can be obtained by replacing a prior art dibenzo-based compound having a five-membered carbocyclic ring with the compound of formula I having an oxa-or thia-five-membered ring according to the present invention⊥The ratio of vertical dielectric to dielectric epsilon⊥The/delta epsilon is obviously improved, the effect of obviously improving the penetration rate of the liquid crystal composition is realized, the average elastic constant Kave and the rotational viscosity gamma 1 are improved, and the technical effects of quick response and high contrast are realized.
As can also be seen from a comparison of example 5 with example 6, in the solution according to the invention, the ring
Figure BDA0002557423960000302
The compound with the middle heteroatom in the ortho position is more favorable for improving the vertical dielectric constant to dielectric constant ratio epsilon of the liquid crystal composition relative to the compound with the heteroatom in the meta position⊥/. DELTA.. epsilon. and elastic constant KaveAnd further is more beneficial to improving the transmittance and the contrast of the liquid crystal composition.
The above embodiments are merely illustrative of the technical concept and features of the present invention, and the present invention is not limited thereto, and equivalent changes and modifications made according to the spirit of the present invention should be covered thereby.

Claims (10)

1. A liquid crystal composition comprising at least one compound of formula I, and at least one compound of formula II:
Figure FDA0002557423950000011
wherein the content of the first and second substances,
r represents-H, halogen, -CN, or straight or branched alkyl containing 1-12 carbon atoms,
Figure FDA0002557423950000012
Figure FDA0002557423950000013
In which a linear or branched alkyl group having 1 to 12 carbon atoms,
Figure FDA0002557423950000014
Figure FDA0002557423950000015
One or more-CH's not adjacent to each other2-each may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -S-, -CO-O-, or-O-CO-, one or at least two-H may each be independently substituted by-F or-Cl;
Rxrepresents-H, straight chain or branched chain alkyl containing 1-12 carbon atoms, one or more than two non-adjacent-CH in the straight chain or branched chain alkyl containing 1-12 carbon atoms2-each independently can be replaced by-CH ═ CH-, -C ≡ C-, -O-, -S-, -CO-O-, or-O-CO-, one or at least two-H each independently can be substituted by-F or-Cl, and said R isxAnd ring
Figure FDA0002557423950000016
To any carbon atom of;
R1represents a linear or branched alkyl group having 1 to 12 carbon atoms,
Figure FDA0002557423950000017
The straight chain or branched chain alkyl containing 1 to 12 carbon atoms1 or non-adjacent 2 or more-CH2-said linear or branched alkyl radical containing from 1 to 12 carbon atoms which may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-or-O-CO-, respectively,
Figure FDA0002557423950000021
Each of one or at least two of-H may be independently substituted with-F or-Cl;
RYrepresents halogen, haloalkyl or haloalkoxy having 1 to 5 carbon atoms, haloalkenyl or haloalkenyloxy having 2 to 5 carbon atoms;
ring (C)
Figure FDA0002557423950000022
To represent
Figure FDA0002557423950000023
And one or at least two of the ring single bonds in the aforementioned groups may be replaced by a double bond;
ring (C)
Figure FDA0002557423950000024
Ring (C)
Figure FDA0002557423950000025
And ring
Figure FDA0002557423950000026
Each independently represent
Figure FDA0002557423950000027
Figure FDA0002557423950000028
Wherein
Figure FDA0002557423950000029
Of one or at least two-CH2-may be replaced by-O-, one or at most two ring single bonds may be replaced byDouble bond substitution, wherein
Figure FDA00025574239500000210
May be substituted by-F or-Cl, and one or at least two rings-CH-may be replaced by-N ═ c;
Z1is represented by- (CH)2)aO-or- (CH)2)aS-, wherein a represents an integer of 0 to 7;
Z2represents-O-, -S-, -CO-O-, -O-CO-, -CF2O-、-OCF2-、-CH2O-、-CH2S-、-OCH2-、-SCH2-、-CH2-、-CH2CH2-、-(CH2)4-、-CH＝CH-CH2O-、-C2F4-、-CH2CF2-、-CF2CH2-, -CF ═ CF-, -CH ═ CF-, -CF ═ CH-, -CH ═ CH-, -C ≡ C-, or a single bond;
Z3、Z4and Z5Each independently represents a single bond, -CH2CH2-、-CF2CF2-、-CF2O-、-OCF2-、-CO-O-、-O-CO-、-O-CO-O-、-CH＝CH-、-CF＝CF-、-CH2O-or-OCH2-；
L1、L2、L3And L4Each independently represents-F, -Cl, -CF3or-CHF2；
L5And L6Each independently represents-H or a straight chain alkyl group containing 1 to 3 carbon atoms;
x represents-CO-, -S-or-O-;
n represents 0, 1 or 2, wherein when n represents 2, a ring
Figure FDA00025574239500000211
Same or different, Z2The same or different; and is
n1 and n2 each independently represent 0, 1 or 2, and 0. ltoreq. n1+ n 2. ltoreq.3, and when n 1. ltoreq.2, the ring
Figure FDA0002557423950000031
Same or different, Z3Identical or different, when n2 is 2, the ring
Figure FDA0002557423950000032
Same or different, Z4The same or different.
2. The liquid crystal composition according to claim 1, wherein n represents 0;
preferably, the ring
Figure FDA0002557423950000033
To represent
Figure FDA0002557423950000034
And one or at least two of the ring single bonds in the aforementioned groups may be replaced by a double bond.
3. Liquid crystal composition according to claim 1 or 2, wherein L is1And L2All represent-F, and X represents-O-or-S-.
4. The liquid crystal composition according to any one of claims 1 to 3, wherein the liquid crystal composition comprises at least one compound of formula I wherein X represents-O-; further preferably, the liquid crystal composition contains at least one compound of the general formula I in which X represents-O-, and at least one compound of the general formula I in which X represents-S-.
5. The liquid crystal composition according to any one of claims 1 to 4, wherein the compound of formula I is present in an amount of 0.1 to 40% by weight, and more preferably in an amount of 1 to 30% by weight, based on the total weight of the liquid crystal composition.
6. The liquid crystal composition of any one of claims 1 to 5, wherein the compound of formula II is selected from any one or a combination of at least two of the following compounds:
Figure FDA0002557423950000035
Figure FDA0002557423950000041
Figure FDA0002557423950000042
and
Figure FDA0002557423950000043
wherein the content of the first and second substances,
Z3、Z4and Z4' each independently represents a single bond, -CH2CH2-、-CO-O-、-O-CO-、-CH2O-or-OCH2-；
L3、L4、L7、L8、L10And L11Each independently represents-H, -F;
L5or L9Each independently represents-H or-CH3；
Rarepresents-CH2-or-O-;
a and b each independently represent 0 or 1; and is
RYrepresents-F, -CF3、-OCF3or-CH2CH2CH＝CF2；
Preferably, the compound of the general formula II accounts for 1-30% of the total weight of the liquid crystal composition; further, the compound of the general formula II accounts for 1-25% of the total weight of the liquid crystal composition; still further, the compound of the general formula II accounts for 5-20% of the total weight of the liquid crystal composition.
7. The liquid crystal composition of any one of claims 1 to 6, further comprising one or at least two compounds of formula M:
Figure FDA0002557423950000051
wherein the content of the first and second substances,
RM1and RM2Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
Figure FDA0002557423950000052
Figure FDA0002557423950000053
Wherein one or two or more non-adjacent-CH groups in the linear or branched alkyl group having 1 to 12 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-;
ring (C)
Figure FDA0002557423950000054
Ring (C)
Figure FDA0002557423950000055
And ring
Figure FDA0002557423950000056
Each independently represent
Figure FDA0002557423950000057
Figure FDA0002557423950000058
Wherein
Figure FDA0002557423950000059
Of one or at least two-CH2-may be replaced by-O-, wherein
Figure FDA00025574239500000510
At most one-H in (a) may be substituted by halogen;
ZM1and ZM2Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-、-(CH2)4-、-CF2O-、-OCF2-or-CF2CF2-; and is
nM1Represents 0, 1, 2 or 3, wherein when n isM1When 2 or 3, ring
Figure FDA00025574239500000511
Same or different, ZM2The same or different.
8. Liquid crystal composition according to any of claims 1 to 7, characterized in that it further comprises one or at least two compounds of general formula N:
Figure FDA0002557423950000061
wherein the content of the first and second substances,
RN1and RN2Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
Figure FDA0002557423950000062
Figure FDA0002557423950000063
Wherein one or two or more non-adjacent-CH groups in the linear or branched alkyl group having 1 to 12 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-;
ring (C)
Figure FDA0002557423950000064
And ring
Figure FDA0002557423950000065
Each independently represent
Figure FDA0002557423950000066
Wherein
Figure FDA0002557423950000067
Of one or at least two-CH2-may be replaced by-O-, one or at most two of the ring single bonds may be replaced by double bonds, wherein
Figure FDA0002557423950000068
May be substituted by-F or-Cl, and one or at least two rings-CH-may be replaced by-N ═ c;
ZN1and ZN2Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-、-(CH2)4-、-CF2O-、-OCF2-or-CF2CF2-；
LN1And LN2Each independently represents-H or methyl; and is
nN1Represents 0, 1, 2 or 3, nN2Represents 0 or 1, and 0. ltoreq. nN1+nN2Is less than or equal to 3, wherein when n isN1When 2 or 3, ring
Figure FDA0002557423950000069
Same or different, ZN1The same or different.
9. Liquid crystal composition according to any of claims 1 to 8, further comprising at least one compound of formula a-1 and/or at least one compound of formula a-2:
Figure FDA0002557423950000071
wherein the content of the first and second substances,
RA1and RA2Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
Figure FDA0002557423950000072
Figure FDA0002557423950000073
In which one or more than two non-adjacent-CH groups in the linear or branched alkyl group containing 1-12 carbon atoms2-linear or branched alkyl containing 1 to 12 carbon atoms which may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-or-O-CO-, respectively,
Figure FDA0002557423950000074
Figure FDA0002557423950000075
Each of one or at least two of-H may be independently substituted with-F or-Cl;
ring (C)
Figure FDA0002557423950000076
Ring (C)
Figure FDA0002557423950000077
Ring (C)
Figure FDA0002557423950000078
And ring
Figure FDA0002557423950000079
Each independently represent
Figure FDA00025574239500000710
Wherein
Figure FDA00025574239500000711
Figure FDA00025574239500000712
At most one-CH in2-may be replaced by-O-and one or at least two ring single bonds may be replaced by double bonds, wherein
Figure FDA00025574239500000713
Wherein one or at least two of-H may be independently substituted by-F, -Cl, -CN, -CH3or-OCH3Substituted, and one or at least two rings-CH-may be replaced by-N ═ N;
ZA11、ZA21and ZA22Each independently represents a single bond, -CH2CH2-、-CF2CF2-、-CO-O-、-O-CO-、-O-CO-O-、-CH＝CH-、-CF＝CF-、-CH2O-or-OCH2-；
LA11、LA12、LA13、LA21And LA22Each independently represents-H, an alkyl group containing 1 to 3 carbon atoms or halogen;
XA1and XA2Each independently represents halogen, straight or branched haloalkyl or haloalkoxy having 1 to 5 carbon atoms, or straight or branched haloalkenyl or haloalkenyloxy having 2 to 5 carbon atoms;
nA11represents 0, 1, 2 or 3, wherein when n isA11When 2 or 3, ring
Figure FDA0002557423950000081
Same or different, ZA11The same or different;
nA12represents 1 or 2, wherein when nA12When 2, ring
Figure FDA0002557423950000082
The same or different; and is
nA2Represents 1, 2 or 3, wherein when n isA2When 2 or 3, ring
Figure FDA0002557423950000083
Same or different, ZA21The same or different.
10. A liquid crystal display device comprising the liquid crystal composition according to any one of claims 1 to 9, wherein the liquid crystal display device is a TN mode, IPS mode or FFS mode liquid crystal display device.
CN202010596439.0A 2020-06-28 2020-06-28 Liquid crystal composition containing dibenzo derivative and liquid crystal display device thereof Pending CN113845921A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115612501A (en) * 2022-08-04 2023-01-17 Tcl华星光电技术有限公司 Liquid crystal composition, liquid crystal medium and electro-optical display element
CN115678568A (en) * 2021-07-22 2023-02-03 江苏和成显示科技有限公司 Liquid crystal composition and liquid crystal display device comprising same

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107973766A (en) * 2016-10-21 2018-05-01 石家庄诚志永华显示材料有限公司 The liquid-crystal compounds of dibenzofuran derivative containing cycloalkyl and its application
JP2019077792A (en) * 2017-10-25 2019-05-23 Jnc株式会社 Liquid crystal composition and liquid crystal display element
WO2019107394A1 (en) * 2017-11-30 2019-06-06 Jnc株式会社 Compounds having dibenzothiophene ring, liquid crystal composition, and liquid crystal display element
JP2019147859A (en) * 2018-02-26 2019-09-05 Jnc株式会社 Liquid crystal composition and liquid crystal display element
CN110300746A (en) * 2017-02-27 2019-10-01 捷恩智株式会社 Compound, liquid-crystal composition and liquid crystal display element with dibenzofurans ring

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107973766A (en) * 2016-10-21 2018-05-01 石家庄诚志永华显示材料有限公司 The liquid-crystal compounds of dibenzofuran derivative containing cycloalkyl and its application
CN110300746A (en) * 2017-02-27 2019-10-01 捷恩智株式会社 Compound, liquid-crystal composition and liquid crystal display element with dibenzofurans ring
JP2019077792A (en) * 2017-10-25 2019-05-23 Jnc株式会社 Liquid crystal composition and liquid crystal display element
WO2019107394A1 (en) * 2017-11-30 2019-06-06 Jnc株式会社 Compounds having dibenzothiophene ring, liquid crystal composition, and liquid crystal display element
JP2019147859A (en) * 2018-02-26 2019-09-05 Jnc株式会社 Liquid crystal composition and liquid crystal display element

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115678568A (en) * 2021-07-22 2023-02-03 江苏和成显示科技有限公司 Liquid crystal composition and liquid crystal display device comprising same
CN115612501A (en) * 2022-08-04 2023-01-17 Tcl华星光电技术有限公司 Liquid crystal composition, liquid crystal medium and electro-optical display element

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