CN113845919A - 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 PDFInfo
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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 M. Compared with the prior art, the liquid crystal composition containing the compound of the general formula I has higher dielectric constant epsilon vertical to the molecular axis on the premise of maintaining basically equivalent clearing point, optical anisotropy and dielectric anisotropy through the structural optimization of the compound of the general formula I⊥Higher ratio of perpendicular dielectric to dielectric absolute value epsilon⊥/| Δ ε | and higher average elastic constants KaveThereby allowing a liquid crystal comprising the liquid crystal composition to be displayedThe display device has higher penetration rate and higher contrast. The liquid crystal composition can meet the requirements of liquid crystal display devices on low power consumption and good display effect, and has higher application value in IPS mode, FFS mode and VA mode liquid crystal displays.
Description
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. Liquid crystal displays are classified into types of PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), FFS (fringe field switching), VA (vertical alignment), and PSA (polymer stable alignment), etc., according to the type of display mode.
Among these modes, the IPS mode, FFS mode, and VA mode are known to improve the disadvantage of narrow viewing angle in the operation modes such as TN mode and STN mode. Liquid crystal displays of these display modes mainly use a liquid crystal composition having negative dielectric anisotropy. In order to further improve the characteristics of the liquid crystal display, the composition preferably has the following physical properties (1) to (8):
(1) high stability to heat, light, and the like;
(2) high definition bright spots;
(3) the lower limit temperature of the liquid crystal phase is low;
(4) low viscosity;
(5) appropriate optical anisotropy;
(6) a large negative value of dielectric anisotropy;
(7) a suitable elastic constant;
(8) the liquid crystal compound has good compatibility.
The physical properties of the liquid crystal composition have an important influence on the display effect of the liquid crystal display. For example, the liquid crystal composition with high stability to heat, light and the like can increase the voltage holding ratio of the liquid crystal display, thereby prolonging the service life of the liquid crystal display; the liquid crystal composition with high clearing point and low liquid crystal phase lower limit temperature can expand the usable temperature range of the liquid crystal display; the liquid crystal composition with low viscosity can shorten the response time of the liquid crystal display; the liquid crystal composition with appropriate optical anisotropy can improve the contrast of the liquid crystal display, and when the liquid crystal display gradually moves to be thinner, the liquid crystal composition with larger optical anisotropy is more appropriate; the liquid crystal composition having a large negative dielectric anisotropy can reduce the threshold voltage of a liquid crystal display element, thereby reducing power consumption; the liquid crystal composition with large elastic constant can shorten the response time of the liquid crystal display, and the liquid crystal composition with small elastic constant can reduce the threshold voltage of the liquid crystal display; the good compatibility of the liquid crystal compounds is beneficial to the adjustment of the physical properties of the liquid crystal composition by mixing the liquid crystal compounds with different physical properties.
In addition, it is also one of the targets of the industry to improve the contrast of the liquid crystal display. Studies have shown that the most significant factor affecting the contrast of a liquid crystal display element is the light leakage of the liquid crystal material, while the major factor affecting the light leakage is the light Scattering (LC Scattering) of the liquid crystal material, which is associated with the average elastic constant KaveThe relationship of (A) is as follows:
wherein d represents the cell gap, neDenotes the extraordinary refractive index, noIndicating the ordinary refractive index. According to the relation, LC Scattering and KaveIn inverse proportion, in increasing KaveIn the case of (2), light leakage of the liquid crystal material can be reduced.
Further, the Contrast (CR) and the luminance (L) are related as follows:
CR＝L255/L0×100％，
wherein L is255Is at on-state brightness, L0Is off state brightness. It can be seen that what significantly affects CR should be L0A change in (c). In the off state, L0The smaller the LC Scattering, L, is, regardless of the dielectric of the liquid crystal molecules, and of the liquid crystal material itself0The smaller the CR, the more significant the CR will be.
In addition, the current liquid crystal display device has a problem of high power consumption because only about 5% of the backlight can penetrate through the display device and be captured by human eyes, and most of the light is wasted. If a liquid crystal with high light penetration rate can be developed, the backlight intensity can be reduced, so that the purpose of saving energy consumption is achieved, and the service life of the equipment is prolonged.
Patent application CN107973766A discloses a liquid crystal compound containing a fluorene derivative with cycloalkyl group, the structure is shown as follows:
wherein H represents one of cyclopropyl, cyclobutyl, cyclopentyl or 2-tetrahydrofuryl; z represents a single bond, -CH2-、-O-、-CH2CH2-or-CH2One of O < - >; x represents one of 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.
The liquid crystal compound of the dibenzofuran derivative with the cycloalkyl has good intersolubility with other liquid crystal compounds, and the low-temperature stability is correspondingly improved. However, the transmittance of the liquid crystal composition containing the compound is still to be further improved.
Therefore, based on the prior art, it is desired to develop a liquid crystal composition with higher transmittance and higher contrast ratio, so as to satisfy the requirements of higher visual effect and low power consumption of liquid crystal display.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims atTo provide a polymer having a higher dielectric constant ε perpendicular to the molecular axis while maintaining substantially equivalent clearing point, optical anisotropy and dielectric anisotropy⊥Higher ratio of perpendicular dielectric to dielectric absolute value epsilon⊥/| Δ ε | and higher average elastic constants KaveThe liquid crystal composition of (1).
In order to achieve the purpose, the invention adopts the following technical scheme:
in a first aspect, the present invention provides a liquid crystal composition comprising a dibenzo derivative, comprising at least one compound of formula I, at least one compound of formula M:
wherein the content of the first and second substances,
r represents-H, halogen, -CN, or straight or branched alkyl containing 1-12 carbon atoms,
In which a linear or branched alkyl group having 1 to 12 carbon atoms,
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 atoms2Each independently may be-CH-CH-, -C ≡ C-, -O-, -S-, -CO-O-, or-O-CO-substituted, one or at least two-H may each be independently substituted by-F or-Cl, and said R isxAnd ring
To any carbon atom of;
RM1and RM2Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
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)
To represent
The above-mentioned
One or at least two of the ring single bonds may be replaced by a double bond;
ring (C)
To represent
Wherein
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
May be substituted by-F or-Cl, and one or at least two rings-CH-may be replaced by-N ═ c; the expression "one or at least two" in "one or at least two rings may be replaced by-N-means the number of-CH-s replaced by-N-and the present invention relates to the same expression, all having the same meaning;
ring (C)
Ring (C)
And ring
Each independently represent
Wherein
Of one or at least two-CH2-may be replaced by-O-, wherein
At most one-H in (a) may be substituted by halogen;
Z1is represented by- (CH)2)aO-or- (CH)2)aS-, wherein a represents an integer of 0 to 7, e.g., 1, 2, 3, 4, 5, 6, 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;
ZM1and ZM2Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-、-(CH2)4-、-CF2O-、-OCF2-or-CF2CF2-；
L1And L2Each independently represents-F, -Cl, -CF3or-CHF2；
X represents-CO-, -S-or-O-;
n represents 0, 1 or 2, wherein when n represents 2, a ring
Same or different, Z2The same or different; and is
nM1Represents 0, 1, 2 or 3, wherein when n isM1When 2 or 3, ring
Same or different, ZM2The same or different. When n isM1When 2, two of the compounds are present
Two of these
May have the same structure or different structures, and may illustratively be one of
The other is
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.
A short straight line on the right side,
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.
In the compounds of the general formula I according to the invention, the ring
Is the structure of an oxa-or thia-five membered ring, the opposite ring
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 constant to the dielectric absolute value of the liquid crystal composition on the premise of maintaining the dielectric anisotropy unchanged⊥/| 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 also have a relatively large average elastic constant KaveThe liquid crystal display device containing the liquid crystal composition has smaller light leakage in a dark state and higher contrast.
The present inventors have also surprisingly found that, in the compounds of the formula I, Z1Is the structure of alkyleneoxy or alkylenethio, with respect to Z1In the case of the straight-chain alkyl group, the compounds of the formula I are represented as a wholeThe conjugation is stronger, and the ratio epsilon of the vertical dielectric constant to the dielectric absolute value after the synergistic effect of the groups in the molecule⊥/| Δ ε | and the average elastic constant KaveAll have obvious promotion function, and are more favorable for realizing the effects of high penetration rate and high contrast.
In some embodiments of the invention, n represents 0.
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, L1And L2All represent-F, and 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 present invention, the compound of formula M comprises 10-70% of the total weight of the liquid crystal composition, such as 15%, 20%, 25%, 3%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, etc.
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:
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:
wherein denotes the carbon atom in the ring structure to which it is bonded.
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:
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.
In order to adjust the performance of the liquid crystal composition in aspects of clearing point, viscosity, low-temperature storage stability and the like, so that the obtained liquid crystal display device has better application value besides excellent transmittance and color expression, 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
To represent
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
To represent
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 the present inventionIn some embodiments of the invention, to further reduce the viscosity of the liquid crystal composition, the liquid crystal composition preferably comprises one or at least two of RM1And/or RM2Compounds of the formula M1 being n-propyl
In some embodiments of the invention, to further increase the K of the liquid crystal compositionaveAnd a liquid crystal display device having a higher transmittance and a higher contrast, particularly preferably a compound of the general formula M having a biphenyl structure, further more preferably any one or at least two combinations of compounds of the general formula M6, the general formula M7, the general formula M16, the general formula M17, the general formula M18, the general formula M19, the general formula M20, the general formula M27, the general formula M28, the general formula M29, the general formula M30, and the general formula M31, further more preferably any one or at least two combinations of compounds of the general formula M6 and the general formula M16, and further more preferably still more preferably R6 and at least two combinations of compounds of the general formula M16M1And RM2Any one or a combination of at least two of the compounds of formula M6 and formula M16, at least one of which is alkenyl.
In some embodiments of the invention, the liquid crystal composition further comprises one or at least two compounds of formula N:
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,
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-, respectively, and one or at least two-H groups present in these groups may be independently substituted by-F or-Cl, respectively;
ring (C)
And ring
Each independently represent
Wherein
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
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
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
And ring
Each independently represent
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:
in some embodiments of the present invention, the compound of formula N is preferably selected from any one of compounds of formula N2, formula N5, formula N14, formula N17, or a combination of at least two thereof.
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 invention, the liquid crystal composition further comprises one or at least two compounds of formula L:
wherein the content of the first and second substances,
RLrepresents a linear or branched alkyl group having 1 to 12 carbon atoms,
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-;
L3and L4Each independently represents-H or-F;
XLrepresents halogen, haloalkyl or haloalkoxy having 1 to 5 carbon atoms, haloalkenyl or haloalkenyloxy having 2 to 5 carbon atoms.
The lower limit of the content of the compound of formula L is 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, or 4% 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 L is 25%, 23%, 20%, 18%, 15% or 10% with respect to the total weight of the liquid crystal composition of the present invention.
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:
wherein n represents a positive integer of 1 to 12, such as 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, etc.
Preferably, the stabilizer is selected from the stabilizers shown below.
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 a second aspect, the present invention also provides a liquid crystal display device comprising the liquid crystal composition, wherein the liquid crystal display device is an IPS mode, FFS mode or VA 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 composition containing the compound of the general formula I has higher dielectric constant epsilon vertical to the molecular axis on the premise of maintaining basically equivalent clearing point, optical anisotropy and dielectric anisotropy through the structural optimization of the compound of the general formula I and the structural optimization of the compound of the general formula I⊥Higher ratio of perpendicular dielectric to dielectric absolute value epsilon⊥/| Δ ε | and higher average elastic constants KaveThereby enabling the liquid crystal display device comprising the liquid crystal composition to have higher transmittance and higher contrast. The liquid crystal composition can meet the requirements of liquid crystal display devices on low power consumption and good display effect, and has higher application value in IPS mode, FFS mode and VA mode liquid crystal displays.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
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 the following examples, the group structures of the liquid crystal compounds are represented by the codes listed in Table 1:
TABLE 1 radical structural code of liquid crystal compounds
Compounds of the following formula are exemplified:
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 codes of the test items in the following 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/| Δ ε | vertical dielectric to dielectric absolute value
Δ n optical anisotropy (illumination wavelength 589nm, 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;
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, and the light modulation device is a negative IPS type test box with the thickness of 3.5 mu m.
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
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
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
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
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
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
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
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
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
As can be seen from comparative example 1 and comparative example 1, Z in the compounds of the formula I1In the case of alkyleneoxy or alkylenethio groups (example 1), the (. epsilon.) for the liquid crystal composition is compared to the linear alkyl group (comparative example 1)⊥、ε⊥/|Δε|、KaveAnd T (%) is obviously improved, so that the penetration rate and the contrast of the liquid crystal display device are further improved.
As can be seen from the comparison of example 1 and comparative example 2, the compound of formula I containing an oxa-or thia-five membered ring (example 1) of the present invention was applied to a liquid crystal composition having ε⊥、ε⊥/|Δε|、KaveAnd T (%) is obviously improved, so that the penetration rate and the contrast of the liquid crystal display device are further improved.
Therefore, the liquid crystal composition containing the compound of the general formula I has higher dielectric constant epsilon vertical to the molecular axis on the premise of maintaining basically equivalent clearing point, optical anisotropy and dielectric anisotropy through the structural optimization of the compound of the general formula I⊥Higher ratio of perpendicular dielectric to dielectric absolute value epsilon⊥/| Δ ε | and higher average elastic constants KaveThereby enabling the liquid crystal display device comprising the liquid crystal composition to have higher transmittance and higher contrast. Further, it is understood from comparative example 1 and example 7 that when the compound of the general formula M containing a biphenyl structure is applied to a liquid crystal composition, K isaveThe T (%) is improved more obviously, thereby further improving the penetration rate and the contrast of the liquid crystal display device.
The liquid crystal composition can meet the requirements of liquid crystal display devices on low power consumption and good display effect, and has higher application value in IPS mode, FFS mode and VA mode liquid crystal displays.
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 a dibenzo derivative, comprising at least one compound of formula I, and at least one compound of formula M:
wherein the content of the first and second substances,
r represents-H, halogen, -CN, or straight or branched alkyl containing 1-12 carbon atoms,
In which a linear or branched alkyl group having 1 to 12 carbon atoms,
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
To any carbon atom of;
RM1and RM2Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
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)
To represent
The above-mentioned
One or at least two of the ring single bonds may be replaced by a double bond;
ring (C)
To represent
Wherein
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
May be substituted by-F or-Cl, and one or at least two rings-CH-may be replaced by-N ═ c;
ring (C)
Ring (C)
And ring
Each independently represent
Wherein
Of one or at least two-CH2-may be replaced by-O-, wherein
At most one-H in (a) may be substituted by halogen;
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;
ZM1and ZM2Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-、-(CH2)4-、-CF2O-、-OCF2-or-CF2CF2-；
L1And L2Each independently represents-F, -Cl, -CF3or-CHF2；
X represents-CO-, -S-or-O-;
n represents 0, 1 or 2, wherein when n represents 2, a ring
Same or different, Z2The same or different; and is
nM1Represents 0, 1, 2 or 3, wherein when n isM1When 2 or 3, ring
Same or different, ZM2The same or different.
2. The liquid crystal composition according to claim 1, wherein n represents 0.
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. Liquid crystal composition according to any one of claims 1 to 5, characterized in that the compound of formula M represents from 10 to 70% of the total weight of the liquid crystal composition.
7. The liquid crystal composition of any one of claims 1 to 6, wherein the compound of formula M is selected from any one or a combination of at least two of the following compounds:
preferably, one or at least two of R are contained in the liquid crystal compositionM1And/or RM2A compound of formula M1 which is n-propyl;
preferably, the liquid crystal composition contains a compound of a general formula M with a biphenyl structure; further preferably, the compounds contain compounds represented by the general formula M6, the general formula M7, the general formula M16, the general formula M17, the general formula M18, the general formula M19, the general formula M20, the general formula M27, the general formula M28, the general formula M29, the general formula M30 and the general formula M31Any one or at least two combinations of compounds, more preferably any one or at least two combinations of compounds represented by the general formulae M6 and M16, and still more preferably RM1And RM2Any one or a combination of at least two of the compounds of formula M6 and formula M16, at least one of which is alkenyl.
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:
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,
Wherein one or two or more non-adjacent-CH groups in the linear or branched alkyl group having 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,
Each of one or at least two of-H may be independently substituted with-F or-Cl;
ring (C)
And ring
Each independently represent
Wherein
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
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
Same or different, ZN1The same or different.
9. The liquid crystal composition according to any one of claims 1 to 8, further comprising one or at least two additives.
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 an IPS-mode, FFS-mode, or VA-mode liquid crystal display device.
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