CN118291146A - Liquid crystal composition and liquid crystal display device - Google Patents
Liquid crystal composition and liquid crystal display device Download PDFInfo
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- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
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- 230000003287 optical effect Effects 0.000 abstract description 16
- 238000003860 storage Methods 0.000 abstract description 14
- 238000012360 testing method Methods 0.000 description 16
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 125000003342 alkenyl group Chemical group 0.000 description 11
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- ONCZDRURRATYFI-QTCHDTBASA-N methyl (2z)-2-methoxyimino-2-[2-[[(e)-1-[3-(trifluoromethyl)phenyl]ethylideneamino]oxymethyl]phenyl]acetate Chemical compound CO\N=C(/C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-QTCHDTBASA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—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 provides a liquid crystal composition and a liquid crystal display device, wherein the liquid crystal composition comprises at least one compound shown as a general formula I and at least one compound shown as a general formula II. The liquid crystal composition disclosed by the invention maintains relatively good optical anisotropy and clearing point, has a larger absolute value of dielectric anisotropy, a shorter response time (lower rotational viscosity), a larger K value (K 11 and K 33), a higher contrast ratio and a longer low-temperature storage time, and is suitable for a display element of a VA, NFFS or PSA-VA display mode.
Description
Technical Field
The invention relates to the field of liquid crystal materials, in particular to a liquid crystal composition and a liquid crystal display device.
Background
The liquid crystal display device can be used in various household electrical appliances such as a timepiece and an electronic calculator, a measuring device, an automobile panel, a word processor, a computer, a printer, a television, and the like. Types according to display modes are classified into PC (PHASE CHANGE ), TN (TWIST NEMATIC, twisted nematic), STN (super TWISTED NEMATIC ), ECB (ELECTRICALLY CONTROLLED BIREFRINGENCE, electrically controlled birefringence), OCB (optically compensated bend ), IPS (in-PLANE SWITCHING, in-plane transition), VA (VERTICAL ALIGNMENT ), and the like. The driving method of the element is classified into a PM (passive matrix) type and an AM (active matrix) type. PM is classified into static (static) and multiplex (multiplex) types. AM is classified into TFT (thin film transistor ), MIM (metal insulator metal, metal-insulator-metal) and the like. The TFT types are amorphous silicon (amorphous silicon) and polysilicon (polycrystal silicon). The latter is classified into a high temperature type and a low temperature type according to the manufacturing process. Liquid crystal display elements are classified into a reflective type using natural light, a transmissive type using backlight, and a semi-transmissive type using both natural light and backlight, depending on the types of light sources.
In low information content, passive driving is generally used, but as the information content increases, the display size and the number of display paths increases, and crosstalk and contrast reduction become serious, so Active Matrix (AM) driving is generally used, and Thin Film Transistors (TFTs) are currently used for driving. In an AM-TFT element, TFT switching devices are addressed in a two-dimensional grid, and the pixel electrode is recharged for a finite period of time while on, and then turned off until addressed again in the next cycle. Therefore, between two address periods, a change in voltage across the pixel is undesirable, otherwise the light transmittance of the pixel may change, resulting in instability of the display. The discharge rate of a pixel depends on the electrode capacity and the resistivity of the inter-electrode dielectric material. Therefore, the liquid crystal material is required to have higher resistivity, good chemical and thermal stability and stability to electric field and electromagnetic radiation, and simultaneously is required to have proper optical anisotropy, dielectric anisotropy and low-temperature intersolubility and lower threshold voltage so as to achieve the purposes of reducing driving voltage and reducing power consumption; there is also a demand for lower viscosity to meet the need for quick response, but it is difficult to ensure good properties of liquid crystal compositions, which have been reported in many documents.
The liquid crystal display element contains a liquid crystal composition having a nematic phase, and the liquid crystal composition has appropriate characteristics. By improving the characteristics of the liquid crystal composition, an AM element having good characteristics can be obtained. The correlation between the characteristics of the liquid crystal composition and the characteristics of the AM element is summarized in table 1 below.
TABLE 1 Properties of liquid Crystal composition and AM element
From this, it is found that in order to increase the response speed of the liquid crystal display device, the rotational viscosity of the liquid crystal material needs to be reduced as much as possible. However, the clearing point, optical anisotropy, absolute value of dielectric anisotropy, etc. of the liquid crystal material with low viscosity are generally low.
The threshold voltage of the mixed liquid crystal mainly depends on the delta epsilon of the liquid crystal, and the delta epsilon is large, so that the threshold voltage of the liquid crystal is reduced, and the delta epsilon of the mixed liquid crystal is modulated to a proper value through the mixing of monomer liquid crystals with different polarities, so that the requirement of the working voltage of a display device is met. However, increasing Δεof the liquid crystal may increase the viscosity of the liquid crystal and decrease the stability of the liquid crystal. And delta epsilon is large, the threshold voltage is low, the order degree of liquid crystal molecules is low, and the K ave value reflecting the order degree of the liquid crystal molecules is also reduced, so that the light leakage and the contrast of the liquid crystal material are influenced, and the two are generally difficult to be compatible.
WO2022175219A1 discloses a liquid-crystalline compound of the formula I) The liquid crystal compound is a continuous ring composed of a five-membered ring and a six-membered ring. When only adjacent five-membered rings exist in the compound, the structure has large curvature, large bond angle tension between C-C bonds and large intermolecular acting force, and when the structure is acted by an electric field, the response speed to the electric field is high, but carbon atoms of the adjacent pentagons of the structure are extremely active, the whole carbon cage is extremely unstable and cannot exist in air stably, and the structure of the compound is stable by introducing a six-membered ring structure between the adjacent five-membered rings, and the compound can be kept to have larger bond angle tension between C-C bonds and larger intermolecular acting force, so that the compound is focused.
However, it has been found through experiments that when the response speed of a liquid crystal display element containing the liquid crystal compound is high, the driving voltage is also increased, so that the electric power consumption is increased, the normal driving of the liquid crystal display element is seriously affected, and the low-temperature storage time of the liquid crystal display element containing the liquid crystal compound is shorter, and the pursuit of longer low-temperature storage time cannot be satisfied.
It is known that the properties of the liquid crystal material are affected by each other, and that improvement of a certain property index may change other properties, and that creative labor is often required for preparing the liquid crystal material with proper properties. Therefore, how to develop a liquid crystal material, which has proper optical anisotropy and clear point, and simultaneously has smaller rotational viscosity, shorter response time, higher contrast, larger absolute value of dielectric anisotropy and longer low-temperature storage time, is the research focus in the field.
Disclosure of Invention
The invention aims to: in view of the drawbacks of the prior art, an object of the present invention is to provide a liquid crystal composition having suitable optical anisotropy, clear point, low rotational viscosity, short response time, high contrast, high absolute value of dielectric anisotropy, and long low-temperature storage time. The invention also aims to provide a liquid crystal display device comprising the liquid crystal composition.
The technical scheme of the invention is as follows:
in order to achieve the above object, 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:
Wherein R 1、R2 each independently represents a straight chain halogenated or non-halogenated alkyl group containing 1 to 12 (e.g., may be 2,3, 4, 5, 6, 7, 8, 9, 10, 11) carbon atoms, a branched chain halogenated or non-halogenated alkyl group containing 3 to 12 (e.g., may be 3, 4, 5, 6, 7, 8, 9, 10, 11) carbon atoms, wherein one or more than two non-adjacent-CH 2 -groups of the straight-chain halogenated or non-halogenated alkyl groups containing 1 to 12 carbon atoms and the branched-chain halogenated or non-halogenated alkyl groups containing 3 to 12 carbon atoms can be independently substituted with-CH=CH-, -C≡C-, -O-, -S-, -CO-O-, respectively, Or-O-CO-substitution;
R 3、R4 each independently represents-H, straight-chain halogenated or non-halogenated alkyl groups containing 1 to 12 (e.g., may be 2, 3, 4, 5, 6, 7, 8, 9, 10, 11) carbon atoms, branched-chain halogenated or non-halogenated alkyl groups containing 3 to 12 (e.g., may be 3, 4, 5, 6, 7, 8, 9, 10, 11) carbon atoms, a cyclic alkyl group containing 3 to 12 (e.g., may be 3, 4, 5, 6, 7, 8, 9, 10, 11), Wherein one or not adjacent two or more-CH 2 -of the straight-chain halogenated or non-halogenated alkyl group having 1 to 12 carbon atoms and branched-chain halogenated or non-halogenated alkyl group having 3 to 12 carbon atoms may be each independently replaced by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-;
Each L 1、L2、L3、L4 independently represents-H or halogen, wherein L 1、L2 both represent halogen and/or L 3、L4 both represent halogen.
In some embodiments of the present invention, preferably, R 1、R2、R3、R4 each independently represents a straight chain alkyl group containing 1 to 10 carbon atoms, a branched chain alkyl group containing 3 to 10 carbon atoms, a straight chain alkoxy group containing 1 to 9 carbon atoms, a branched chain alkoxy group containing 3 to 9 carbon atoms, a straight chain alkenyl group containing 2 to 10 carbon atoms, or a branched chain alkenyl group containing 3 to 10 carbon atoms.
In some embodiments of the invention, the compounds of formula i comprise from 0.1% to 20% (including all values therebetween) by weight of the liquid crystal composition, for example, from 0.1%, 0.5%, 1%, 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20% or a range of values between any two thereof, preferably from 1 to 20%, further preferably from 2 to 20%.
In some embodiments of the invention, preferably, the compound of formula ii comprises 0.1% to 40% (including all values therebetween) by weight of the liquid crystal composition, for example 0.1%, 0.5%, 1%, 3%, 5%, 7%, 8%, 10%, 12%, 14%, 17%, 19%, 20%, 22%, 25%, 27%, 30%, 32%, 34%, 37%, 39%, 40% or a range of values between any two thereof, preferably 0.5% to 40%, further preferably 2% to 35%.
In some embodiments of the invention, preferably, the compound of formula i is selected from the group consisting of:
In some embodiments of the present invention, the liquid crystal composition of the present invention is preferably selected from the group consisting of the compound of formula I-8, the compound of formula I-9, the compound of formula I-10 and the compound of formula I-1 in order to have a low rotational viscosity and a fast response time while maintaining optical anisotropy and a clear spot.
In some embodiments of the present invention, preferably, the compound of formula ii is selected from the group consisting of:
in some embodiments of the present invention, the liquid crystal composition of the present invention preferably contains at least one (e.g., may be two) compounds of formula II, preferably, the compound of formula II is selected from the group consisting of the compound of formula II-1, the compound of formula II-3, and the compound of formula II-5, in order to have a larger absolute value of dielectric anisotropy, a longer low temperature storage time and a faster response speed (lower rotational viscosity), a higher contrast ratio, and a larger K value (K 11、K33), with maintaining optical anisotropy and clearing point suitable.
In some embodiments of the present invention, the liquid crystal composition of the present invention preferably contains at least one (e.g., two) compound of formula i, and at least two compounds of formula ii, in order to have a high absolute value of dielectric anisotropy and contrast, with maintaining optical anisotropy, clearing point being appropriate.
In some embodiments of the invention, preferably, the liquid crystal composition further comprises at least one compound of formula iii:
Wherein R 5 represents-H, straight-chain halogenated or unhalogenated alkyl having 1 to 12 carbon atoms, branched-chain halogenated or unhalogenated alkyl having 3 to 12 carbon atoms, wherein one or two or more of the straight-chain halogenated or unhalogenated alkyl having 1 to 12 carbon atoms and branched-chain halogenated or unhalogenated alkyl having 3 to 12 carbon atoms-CH 2 -may each independently be represented by-CH=CH-, -C≡C-, -O-, -S-, -CO-O-, Or-O-CO-substitution;
each L 5、L6 independently represents-H or halogen;
Ring(s) And ringEach independently representsWherein,
The-CH 2 -of which may be replaced by-O-,One or both of the single bonds in the rings may be replaced by a double bond,Wherein-H may be independently substituted with-CN, -F or-Cl, and-ch=may be substituted with-n=in one or more rings;
Z 1、Z2 each independently represents a single bond 、-CO-O-、-O-CO-、-CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-、-(CH2)4-、-CF2O-、-OCF2- or-CF 2CF2 -;
n 1 represents 1 or 2, when n 1 =2, a ring Z 1, which may be the same or different, may be the same or different;
X 1 represents halogen, halogenoalkyl or halogenoalkoxy having 1 to 5 carbon atoms, halogenoalkenyl or halogenoalkenyloxy having 2 to 5 carbon atoms.
In some embodiments of the invention, preferably, L 5 and L 6 each independently represent-H, -F.
In some embodiments of the invention, preferably X 1 represents-F, -Cl, -CF 3、-OCF3, and further preferably X 1 represents-F or-Cl.
In some embodiments of the invention, the compound of formula iii is selected from the group consisting of:
In some embodiments of the invention, preferably, R 5 represents a straight chain alkyl group containing 1 to 10 carbon atoms, a branched chain alkyl group containing 3 to 10 carbon atoms, a straight chain alkoxy group containing 1 to 9 carbon atoms, a branched chain alkoxy group containing 3 to 9 carbon atoms, a straight chain alkenyl group containing 2 to 10 carbon atoms, or a branched chain alkenyl group containing 3 to 10 carbon atoms.
In some embodiments of the invention, preferably, the compound of formula III comprises 0% to 30% (including all values therebetween) by weight of the liquid crystal composition, for example 0%, 0.5%,1%, 3%, 5%, 7%, 8%, 10%, 12%, 14%, 17%, 19%, 20%, 22%, 25%, 27%, 30% or a range of values between any two thereof, preferably 0% to 20%.
In some embodiments of the present invention, the liquid crystal composition of the present invention preferably contains at least one compound of formula III-1 in order to have a higher contrast ratio, a smaller rotational viscosity, a shorter response time and a longer low temperature storage time while maintaining a suitable clearing point, a suitable optical anisotropy.
In some embodiments of the invention, preferably, the liquid crystal composition further comprises at least one compound of formula N:
Wherein,
R N1 and R N2 each independently represent a straight-chain alkyl group containing 1 to 12 (e.g., may be2, 3,4, 5, 6, 7, 8, 9, 10, 11) carbon atoms, a branched-chain alkyl group containing 3 to 12 (e.g., may be 3,4, 5, 6, 7, 8, 9, 10, 11) carbon atoms, a cyclic alkyl group containing a cyclic alkyl group,Wherein one or not adjacent two or more of the linear alkyl group having 1 to 12 carbon atoms and the branched alkyl group having 3 to 12 carbon atoms, -CH 2 -, may be independently replaced with-ch=ch-, -c≡c-, -O-, -CO-O-or-O-CO-, respectively;
Ring(s) And ringEach independently representsWherein the method comprises the steps ofIn which one or more-CH 2 -may be replaced by-O-and one or both single bonds in the ring may be replaced by double bondsIn which-H may be substituted by-F, -Cl or-CN, and-ch=may be substituted by-n=in one or more rings;
Z N1 and Z N2 each independently represent a single bond 、-CO-O-、-O-CO-、-CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-、-CF2CF2-、-(CH2)4-、-CF2O- or-OCF 2 -;
L N1 and L N2 independently represent-H, alkyl having 1 to 3 carbon atoms or halogen; and
N N1 represents 0,1, 2 or 3, n N2 represents 0 or 1, and 0.ltoreq.n N1+nN2.ltoreq.3, when n N1 =2 or 3, the ringZ N1, which may be the same or different, may be the same or different;
The compounds of formula N do not include compounds of formula II.
In some embodiments of the invention, preferably, R N1 and R N2 each independently represent a straight chain alkyl group containing 1 to 10 carbon atoms, a branched chain alkyl group containing 3 to 10 carbon atoms, a straight chain alkoxy group containing 1 to 9 carbon atoms, a branched chain alkoxy group containing 3 to 10 carbon atoms.
In some embodiments of the invention, the compound of formula N comprises 0.1% to 60% (including all values therebetween) by weight of the liquid crystal composition, e.g., 0.1%, 0.5%, 1%, 2%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 30%, 34%, 38%, 40%, 45%, 50%, 55%, 60% or a range of values between any two thereof; preferably, the compound of formula N comprises 5-60% by weight of the liquid crystal composition.
In some embodiments of the invention, preferably, the compound of formula N is selected from the group consisting of:
In some embodiments of the present invention, in order for the composition of the present invention to have a smaller rotational viscosity, a shorter response time, a larger absolute value of dielectric anisotropy, and a higher contrast ratio and longer low temperature storage time while maintaining a proper clearing point, a proper optical anisotropy value, it is preferable that the compound of formula N is selected from the group consisting of the compound of formula N-2, the compound of formula N-9, the compound of formula N-12, the compound of formula N-19, and the compound of formula N-21.
In some embodiments of the invention, preferably, the liquid crystal composition further comprises at least one compound of formula M:
Wherein,
R M1 and R M2 each independently represent a straight-chain alkyl group containing 1 to 12 (e.g., may be2, 3,4, 5, 6, 7, 8, 9, 10, 11) carbon atoms, a branched-chain alkyl group containing 3 to 12 (e.g., may be 3,4, 5, 6, 7, 8, 9, 10, 11) carbon atoms, a cyclic alkyl group containing a cyclic alkyl group,Wherein one or not adjacent two or more-CH 2 -of the straight-chain or branched alkyl group having 1 to 12 carbon atoms and the branched alkyl group having 3 to 12 carbon atoms may be independently replaced with-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-, respectively;
Ring(s) Ring(s)And ringEach independently represents Wherein the method comprises the steps ofOne or more of-CH 2 -may be replaced by-O-and one or both of the single bonds in the ring may be replaced by a double bond,At most one-H of (c) may be substituted by halogen;
z M1 and Z M2 each independently represent a single bond, -CO-O-, -O-CO-, -CH 2O-、-OCH2-、-C≡C-、-CH＝CH-、-CH2CH2 -, or- (CH 2)4 -; and
N M represents 0,1 or 2, wherein when n M =2, the ringZ M2, which may be the same or different, may be the same or different.
In some embodiments of the invention, the compound of formula M comprises 0.1% to 60% (including all values therebetween) by weight of the liquid crystal composition, e.g., 0.1%, 1%, 4%, 6%, 8%, 10%, 12%, 14%, 16%, 18%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60% or a range of values between any two thereof; preferably, the compound of formula M comprises 10-60% by weight of the liquid crystal composition.
In some embodiments of the invention, preferably, R M1 and R M2 each independently represent a straight chain alkyl group containing 1 to 10 carbon atoms, a branched chain alkyl group containing 3 to 10 carbon atoms, a straight chain alkoxy group containing 1 to 9 carbon atoms, a branched chain alkoxy group containing 3 to 10 carbon atoms, a straight chain alkenyl group containing 2 to 10 carbon atoms, or a branched chain alkenyl group containing 3 to 10 carbon atoms.
In some embodiments of the invention, preferably, R M1 and R M2 each independently represent a straight chain alkenyl group containing 2 to 8 carbon atoms; further preferably, R M1 and R M2 each independently represent a straight chain alkenyl group containing 2 to 5 carbon atoms.
In some embodiments of the invention, preferably, one of R M1 and R M2 is a linear alkenyl group containing 2 to 5 carbon atoms, and the other is a linear alkyl group containing 1 to 5 carbon atoms.
In some embodiments of the invention, preferably, R M1 and R M2 each independently represent a linear alkoxy group containing 1 to 8 carbon atoms; further preferably, R M1 and R M2 each independently represent a straight-chain alkoxy group containing 1 to 5 carbon atoms.
In some embodiments of the invention, preferably, one of R M1 and R M2 is a linear alkoxy group containing 1 to 5 carbon atoms, and the other is a linear alkyl group containing 1 to 5 carbon atoms.
In some embodiments of the invention, where reliability is important, it is preferred that both R M1 and R M2 are alkyl; where importance is attached to reducing the volatility of the compound, it is preferable that both R M1 and R M2 are alkoxy groups; in the case where the viscosity reduction is important, at least one of R M1 and R M2 is preferably an alkenyl group.
As used herein, the term "containing 1-r carbon atoms" (where r is an integer greater than 1) may be any integer between 1 and r (inclusive of the end values 1 and r) carbon atoms, for example, containing 2 carbon atoms, containing (r-1) carbon atoms, or containing r carbon atoms. For example, "containing 1-12 carbon atoms" may be containing 1,2, 3,4, 5, 6, 7, 8, 9, 10, 11, or 12 carbon atoms.
As used herein, the term "integer of y 1-y2" may be any integer between the ranges (inclusive of the endpoints y 1 and y 2). For example, an "integer of 0-12" may be 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, or 12.
The alkenyl group in the present invention is preferably selected from the group represented by any one of the formulas (V1) to (V9), and particularly preferably is formula (V1), formula (V2), formula (V8) or (V9). The groups represented by the formulas (V1) to (V9) are as follows:
wherein represents the attachment site in the bonded ring structure.
The alkenyloxy group in the present invention is preferably selected from the group represented by any one of the formulae (OV 1) to (OV 9), and particularly preferably is the formula (OV 1), the formula (OV 2), the formula (OV 8) or the formula (OV 9). The groups represented by the formulas (OV 1) to (OV 9) are as follows:
wherein represents the attachment site in the bonded ring structure.
In some embodiments of the invention, preferably, the compound of formula M is selected from the group consisting of:
In some embodiments of the present invention, the compound of formula M is preferably selected from the group consisting of a compound of formula M-1, a compound of formula M-4, and a compound of formula M-11 in order for the composition of the present invention to have a smaller rotational viscosity, a faster response time, and a higher contrast ratio while maintaining a suitable clearing point and a suitable optical anisotropy.
In some embodiments of the invention, it is preferred to adjust the content of the compound of formula M in order to provide the composition of the invention with a smaller rotational viscosity, a faster response time and a higher contrast and better low temperature storage time while maintaining a suitable clearing point, a suitable optical anisotropy, a suitable absolute value of the dielectric anisotropy.
In some embodiments of the present invention, the liquid crystal composition further comprises at least one additive, and in addition to the above-mentioned compounds, the liquid crystal composition of the present invention may contain a usual nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, dopant, antioxidant, ultraviolet absorber, infrared absorber, polymerizable monomer, light stabilizer, or the like.
Possible dopants preferably added to the liquid crystal composition according to the invention are shown below:
In some embodiments of the invention, the dopant comprises 0% to 5% by weight of the liquid crystal composition; preferably, the dopant comprises 0.01% to 1% by weight of the liquid crystal composition.
The additives such as antioxidants, light stabilizers, and ultraviolet absorbers used in the liquid crystal composition of the present invention are preferably the following:
Wherein n represents a positive integer of 1 to 12.
Preferably, the antioxidant is selected from the compounds shown below:
in some embodiments of the invention, the light stabilizer comprises 0% to 5% by weight of the total weight of the liquid crystal composition; preferably, the light stabilizer comprises 0.01% to 1% by weight of the total weight of the liquid crystal composition.
The composition of the invention may also comprise a polymerizable compound comprising at least one compound of formula RM:
Wherein P 1 and P 2 each independently represent Or-SH;
r 1 represents an integer of 1 to 3 (e.g., 1,2, or 3);
r 2 and r 3 each independently represent an integer of 0 to 6 (e.g., 0, 1,2, 3, 4, 5, or 6);
r 4 and r 5 each independently represent an integer of 0 to 4 (e.g., 0,1, 2, 3, or 4);
Z represents a single bond, -CH 2CH2-、-COO-、-OCO-、-CH2O-、-OCH2 -, or-CH=CH-COO-;
Z p1 and Z p2, which are identical or different, each independently represent a single bond 、-O-、-S-、-NH-、-NHCOO-、-OCONH-、-CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH2CH2-、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CF＝CH-、-CH＝CF-、-CF＝CF-、-CO-、-COO-、-OCO-、-OCOO-、-CH2-、-OCH2-、-SCH2-、-CH2S-、-CH＝CH-、-C≡C-、-CH＝CH-COO- or-OCO-CH=CH-;
Y 1 and Y 2 each independently represent H, halogen, straight-chain alkyl or alkoxy groups containing 1 to 3 carbon atoms, branched-chain alkyl or alkoxy groups containing 3 carbon atoms.
In some embodiments of the invention, preferably, P 1 and P 2 each independently represent
In some embodiments of the invention, the compound of formula RM is selected from the group consisting of:
When the liquid crystal composition and the polymerizable compound are polymerized, the formed polymerized particles are relatively uniform, larger polymerized particles are not easy to form, and bright spots are not formed in the panel to influence the display effect.
In addition, the liquid crystal composition may further contain a polymerization initiator in order to promote polymerization. Examples of the polymerization initiator include benzoin ethers, benzophenones, acetophenones, benzil ketals, and acylphosphine oxides.
In another aspect, the present invention also provides a liquid crystal display device comprising the above liquid crystal composition.
The liquid crystal composition of the invention can be applied to display elements of VA, NFFS or PSA-VA display modes, and is particularly applicable to display elements of NFFS display modes.
The beneficial effects are that:
The liquid crystal composition disclosed by the invention maintains relatively good optical anisotropy and clearing point, has a larger absolute value of dielectric anisotropy, a shorter response time (lower rotational viscosity), a larger K value (K 11 and K 33), a higher contrast ratio and a longer low-temperature storage time, and is suitable for a display element of a VA, NFFS or PSA-VA display mode.
Detailed Description
The invention will be described below in connection with specific embodiments. 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 of the invention may be made without departing from the spirit or scope of the invention.
In the invention, unless otherwise specified, the proportions are weight ratios, and all temperatures are temperatures of degrees celsius.
For ease of expression, in the following examples, the group structures of the liquid crystal compositions are represented by the codes listed in Table 2:
TABLE 2 group Structure codes for liquid Crystal Compounds
The structural code is illustrated by way of example for a compound of the formula:
The formula can be expressed as nCPPm if it is expressed by the code shown in Table 2, where n represents the number of carbon atoms in the left alkyl group, e.g., n is 3, i.e., the alkyl group is C 3H7 -, and C in the code represents P representsM represents the number of carbon atoms of the right-end alkyl group, for example, m is 2, that is, represents that the alkyl group is-C 2H5.
In the following examples, shorthand designations of performance test items are shown in Table 3.
Table 3 shorthand code for performance test items
| Code number of test item | Meaning of |
| Δn | Optical anisotropy (589 nm,20 ℃ C.) |
| Δε | Dielectric anisotropy (1 KHz,20 ℃ C.) |
| Cp | Clearing point (nematic-isotropic phase transition temperature, DEG C) |
| γ1 | Rotational viscosity (mPa.s, 20 ℃ C.) |
| K11 | Elastic constant of splay |
| K33 | Flexural spring constant |
| t-40℃ | Low temperature storage time (h, at-40 ℃ C.) |
| τ | Response time (ms) |
| CR | Contrast ratio |
Wherein Δn: the sample was measured at 20℃under a sodium light (589 nm) using an Abbe refractometer.
Δ∈=ε ∥-ε⊥, where ε ∥ is the dielectric constant parallel to the molecular axis, ε ⊥ is the dielectric constant perpendicular to the molecular axis, test conditions: 20 ℃ and 1KHz, the test box is of VA type and the thickness of the box is 6 mu m.
Cp: obtained by a melting point tester test.
K 11、K33 is the capacitance-voltage characteristic curve (C-V curve) of the liquid crystal material using an LCR meter and a VA test cell and calculated, test conditions: 6 mu mVA test box, V=0.1-20V, 20 ℃.
T -40℃: the nematic liquid crystal medium was placed in a glass bottle, stored at-40 ℃ and the time recorded when crystal precipitation was observed.
Τ: test using DMS505 tester at 20 ℃ under the following conditions: negative IPS type test cartridge with a cartridge thickness of 3.5 μm at 20℃under V90 drive.
Gamma 1: the liquid crystal physical property evaluation system TOYO6254 is used for testing and obtaining; the test temperature was 20deg.C, the test voltage was 90V, and the test cartridge thickness was 20 μm.
CR: the transmittance of the liquid crystal cells, tr 255 and Tr 0, were measured at 255 gray scale voltages and 0 gray scale voltages, respectively, using a DMS 505 tester, obtained from Tr 255/Tr0, under the following test conditions: negative IPS type test kit with a thickness of 3.5 μm at 20 ℃.
The components used in the liquid crystal compositions of the following examples were synthesized by a known method or obtained commercially, and the components of the obtained liquid crystal compositions were tested to meet the electronic compound standards.
The liquid crystal compositions in the following examples were prepared in accordance with the proportions of the respective components (the formulas of the components belonging to the brackets at the ends of the components in the examples) and were mixed by a conventional preparation method such as heating, ultrasonic wave, suspension and the like to obtain liquid crystal compositions.
Liquid crystal compositions as given in the following examples were prepared and studied. The results of performance testing of the compositions of the respective liquid crystal compositions and the filling between the two substrates of the liquid crystal display are shown below.
Comparative example 1: in this comparative example, the liquid crystal composition includes components in mass percent as shown in the following table, and the performance test results thereof are shown in the following table:
example 1: in this example, the liquid crystal composition includes components in the mass percentages shown in the following table, and the performance test results are shown in the following table:
As can be seen from the comparison between the comparative example 1 and the example 1, when the compound of the general formula I and the compound of the general formula II are used in combination, the absolute value of the dielectric anisotropy can be significantly improved, and the rotational viscosity of the liquid crystal composition can be reduced, so that the liquid crystal composition has a faster response speed on the premise that the clearing point and the optical anisotropy of the liquid crystal composition are maintained at a stable level; in addition, the low-temperature storage time of the liquid crystal composition can be improved, and the K 11、K33 value of the liquid crystal composition can be improved, so that the liquid crystal composition has higher contrast ratio, and the liquid crystal composition has better display quality.
Example 2: in this example, the liquid crystal composition includes components in the mass percentages shown in the following table, and the performance test results are shown in the following table:
example 3: in this example, the liquid crystal composition includes components in the mass percentages shown in the following table, and the performance test results are shown in the following table:
example 4: in this example, the liquid crystal composition includes components in the mass percentages shown in the following table, and the performance test results are shown in the following table:
Example 5: in this example, the liquid crystal composition includes components in the mass percentages shown in the following table, and the performance test results are shown in the following table:
example 6: in this example, the liquid crystal composition includes components in the mass percentages shown in the following table, and the performance test results are shown in the following table:
As can be seen from examples 1-6 above, the liquid crystal composition of the present invention can achieve a larger absolute value of dielectric anisotropy, a shorter response time (lower rotational viscosity), a higher contrast ratio, a longer low-temperature storage time, and still have a larger K value (K 11 and K 33) in the system of different levels of Deltan, cp.
In summary, the liquid crystal composition of the invention maintains relatively good optical anisotropy and clearing point, and has a larger absolute value of dielectric anisotropy, a shorter response time (lower rotational viscosity), a larger K value (K 11 and K 33), a higher contrast ratio and a longer low-temperature storage time, and is suitable for a display element of VA, NFFS or PSA-VA display modes.
The above embodiments are only for illustrating the technical concept and features of the present invention, and are intended to enable those skilled in the art to understand the present invention and to implement it, but not limit the scope of the present invention, and all equivalent changes or modifications made according to the spirit of the present invention should be included in the scope of the present invention.
Claims (10)
1. A liquid crystal composition, characterized in that it comprises at least one compound of formula i and at least one compound of formula ii:
Wherein R 1、R2 each independently represents a straight-chain halogenated or non-halogenated alkyl group having 1 to 12 carbon atoms, a branched-chain halogenated or non-halogenated alkyl group having 3 to 12 carbon atoms, wherein one or two or more non-adjacent-CH 2 -groups of the straight-chain halogenated or non-halogenated alkyl group having 1 to 12 carbon atoms and the branched-chain halogenated or non-halogenated alkyl group having 3 to 12 carbon atoms may be independently represented by-CH=CH-, -C≡C-, -O-, -S-, -CO-O-, respectively, Or-O-CO-substitution;
R 3、R4 each independently represents-H, straight-chain halogenated or non-halogenated alkyl having 1 to 12 carbon atoms, branched halogenated or non-halogenated alkyl having 3 to 12 carbon atoms, Wherein one or not adjacent two or more-CH 2 -of the straight-chain halogenated or non-halogenated alkyl group having 1 to 12 carbon atoms and branched-chain halogenated or non-halogenated alkyl group having 3 to 12 carbon atoms may be each independently replaced by-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-;
Each L 1、L2、L3、L4 independently represents-H or halogen, wherein L 1、L2 both represent halogen and/or L 3、L4 both represent halogen.
2. The liquid crystal composition according to claim 1, wherein the compound of formula i is selected from the group consisting of:
3. The liquid crystal composition according to claim 1 or 2, characterized in that the compound of formula ii is selected from the group consisting of:
4. the liquid crystal composition according to claim 1, characterized in that it further comprises at least one compound of formula iii:
Wherein R 5 represents-H, straight-chain halogenated or unhalogenated alkyl having 1 to 12 carbon atoms, branched-chain halogenated or unhalogenated alkyl having 3 to 12 carbon atoms, wherein one or two or more of the straight-chain halogenated or unhalogenated alkyl having 1 to 12 carbon atoms and branched-chain halogenated or unhalogenated alkyl having 3 to 12 carbon atoms-CH 2 -may each independently be represented by-CH=CH-, -C≡C-, -O-, -S-, -CO-O-, Or-O-CO-substitution;
each L 5、L6 independently represents-H or halogen;
Ring(s) And ringEach independently representsWherein,The-CH 2 -of which may be replaced by-O-,One or both of the single bonds in the rings may be replaced by a double bond,Wherein-H may be independently substituted with-CN, -F or-Cl, and-ch=may be substituted with-n=in one or more rings;
Z 1、Z2 each independently represents a single bond 、-CO-O-、-O-CO-、-CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-、-(CH2)4-、-CF2O-、-OCF2- or-CF 2CF2 -;
n 1 represents 1 or 2, when n 1 =2, a ring Z 1, which may be the same or different, may be the same or different;
X 1 represents halogen, halogenoalkyl or halogenoalkoxy having 1 to 5 carbon atoms, halogenoalkenyl or halogenoalkenyloxy having 2 to 5 carbon atoms.
5. The liquid crystal composition of claim 4, further comprising at least one compound of formula N:
Wherein,
R N1 and R N2 each independently represent a linear alkyl group having 1 to 12 carbon atoms branched alkyl groups having 3 to 12 carbon atoms,Wherein one or not adjacent two or more of the linear alkyl group having 1 to 12 carbon atoms and the branched alkyl group having 3 to 12 carbon atoms, -CH 2 -, may be independently replaced with-ch=ch-, -c≡c-, -O-, -CO-O-or-O-CO-, respectively;
Ring(s) And ringEach independently representsWherein the method comprises the steps ofIn which one or more-CH 2 -may be replaced by-O-and one or both single bonds in the ring may be replaced by double bondsIn which-H may be substituted by-F, -Cl or-CN, and-ch=may be substituted by-n=in one or more rings;
Z N1 and Z N2 each independently represent a single bond 、-CO-O-、-O-CO-、-CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-、-CF2CF2-、-(CH2)4-、-CF2O- or-OCF 2 -;
L N1 and L N2 independently represent-H, alkyl having 1 to 3 carbon atoms or halogen; and
N N1 represents 0,1, 2 or 3, n N2 represents 0 or 1, and 0.ltoreq.n N1+nN2.ltoreq.3, when n N1 =2 or 3, the ringZ N1, which may be the same or different, may be the same or different;
The compounds of formula N do not include compounds of formula II.
6. The liquid crystal composition according to claim 5, wherein the compound of formula N is selected from the group consisting of:
7. the liquid crystal composition according to claim 5, further comprising at least one compound of formula M:
Wherein,
R M1 and R M2 each independently represent a linear alkyl group having 1 to 12 carbon atoms branched alkyl groups having 3 to 12 carbon atoms,Wherein one or not adjacent two or more-CH 2 -of the straight-chain or branched alkyl group having 1 to 12 carbon atoms and the branched alkyl group having 3 to 12 carbon atoms may be independently replaced with-ch=ch-, -c≡c-, -O-, -CO-O-, or-O-CO-, respectively;
Ring(s) Ring(s)And ringEach independently represents Wherein the method comprises the steps ofOne or more of-CH 2 -may be replaced by-O-and one or both of the single bonds in the ring may be replaced by a double bond,At most one-H of (c) may be substituted by halogen;
z M1 and Z M2 each independently represent a single bond, -CO-O-, -O-CO-, -CH 2O-、-OCH2-、-C≡C-、-CH＝CH-、-CH2CH2 -, or- (CH 2)4 -; and
N M represents 0,1 or 2, wherein when n M =2, the ringZ M2, which may be the same or different, may be the same or different.
8. The liquid crystal composition according to claim 7, wherein the compound of formula M is selected from the group consisting of:
9. The liquid crystal composition according to claim 7, wherein the compound of formula i is 0.1 to 20% by weight of the liquid crystal composition, the compound of formula ii is 0.1 to 40% by weight of the liquid crystal composition, the compound of formula iii is 0 to 30% by weight of the liquid crystal composition, the compound of formula N is 0.1 to 60% by weight of the liquid crystal composition, and the compound of formula M is 0.1 to 60% by weight of the liquid crystal composition.
10. A liquid crystal display device comprising the liquid crystal composition according to any one of claims 1 to 9.
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