CN111117655B - Liquid crystal composition and display device thereof - Google Patents
Liquid crystal composition and display device thereof Download PDFInfo
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- CN111117655B CN111117655B CN201811272254.3A CN201811272254A CN111117655B CN 111117655 B CN111117655 B CN 111117655B CN 201811272254 A CN201811272254 A CN 201811272254A CN 111117655 B CN111117655 B CN 111117655B
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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
Abstract
The invention discloses a liquid crystal composition, which comprises the following components in part by weight: one or more compounds of formula (I); one or more compounds of formula II; one or more compounds of formula M; one or more compounds of formula A-1; and one or more compounds of formula A-2. The invention also discloses a display device containing the liquid crystal composition. The liquid crystal composition provided by the invention has higher clearing point, larger dielectric anisotropy, lower driving voltage, better low-temperature intersolubility, larger transmittance and larger K while maintaining optical anisotropy of proper sizeaveThe liquid crystal display device containing the liquid crystal composition has small light scattering and high contrast, and is particularly suitable for liquid crystal display elements driven by active matrix thin film transistors (AM-TFTs).
Description
Technical Field
The invention relates to the field of liquid crystal materials, in particular to a liquid crystal composition and a display device thereof.
Background
Liquid crystal display elements are used in various household appliances such as watches and calculators, measuring instruments, automobile panels, word processors, computers, printers, televisions, and the like. The display mode is classified into PC (phase change), TN (twisted nematic), STN (super twisted nematic), ECB (electrically controlled birefringence), OCB (optically compensated bend), IPS (in-plane switching), VA (vertical alignment), and the like, according to the type of the display mode. 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 a TFT (thin film transistor), an MIM (metal insulator metal), and the like. The types of TFTs are amorphous silicon (amorphous silicon) and polycrystalline silicon (polysilicon). The latter is classified into a high temperature type and a low temperature type according to a manufacturing process. Liquid crystal display elements are classified into a reflection type using natural light, a transmission type using backlight, and a semi-transmission type using both light sources of natural light and backlight, depending on the type of light source.
In low information content, passive driving is generally used, but as the information content increases, the display size and the number of display paths increase, and the crosstalk and contrast reduction phenomenon become serious, so that Active Matrix (AM) driving is generally used, and Thin Film Transistors (TFTs) are often used for driving at present. In an AM-TFT element, the TFT switching devices are addressed in a two-dimensional grid, charge up the pixel electrodes for a finite time on, and then turn off until they are addressed again in the next cycle. Therefore, between two addressing periods, it is not desirable to change the voltage on the pixel, otherwise the transmittance of the pixel will change, resulting in unstable display. The rate of discharge at a pixel depends on the electrode capacity and the resistivity of the dielectric material between the electrodes. Therefore, the liquid crystal material is required to have higher resistivity, appropriate optical anisotropy Δ n (the Δ n value is generally about 0.08-0.13) and lower threshold voltage, so as to achieve the purposes of reducing driving voltage and reducing power consumption; it is also required to have a low viscosity to meet the demand for a rapid response. Such liquid crystal compositions have been reported in many documents, for example, WO9202597, WO9116398, WO9302153, WO9116399, CN1157005A and the like.
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), 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.
The liquid crystal display element containing the liquid crystal composition having a large absolute value of dielectric anisotropy can reduce the base voltage value, reduce the driving voltage, and further reduce the power consumption.
The liquid crystal display element containing the liquid crystal composition with the lower threshold voltage can effectively reduce the power consumption of display, and has longer endurance time particularly in consumables, such as portable electronic products like mobile phones, tablet computers and the like. However, the liquid crystal composition having a lower threshold voltage (generally containing a large dielectric polar group) has a low degree of order of liquid crystal molecules, and K reflecting the degree of order of the liquid crystal moleculesaveThe value also decreases, affecting the light leakage and contrast of the liquid crystal material, which are generally difficult to achieve simultaneously.
The liquid crystal composition with low viscosity can improve the response speed of the liquid crystal display element. When the response speed of the liquid crystal display element is high, it can be applied to animation display. In addition, when the liquid crystal composition is injected into the cell of the liquid crystal display device, the injection time can be shortened, and the workability can be improved.
The prior art discloses a liquid crystal composition with lower power consumption and faster response speed, such as patent document CN102858918A, but the liquid crystal composition in the prior art has the problems of environmental protection (such as use of chlorine-containing compounds), short service life (such as poor stability to UV or heat), low contrast (such as whitening of a display screen under sunlight), and incapability of simultaneously satisfying performance balance problems of appropriate optical anisotropy, appropriate dielectric anisotropy, high voltage holding ratio, good UV resistance stability and high temperature stability in liquid crystal televisions, tablet computers, and the like, and cannot simultaneously satisfy all indexes.
From the preparation angle of the liquid crystal material, various performances of the liquid crystal material are mutually influenced by the influence, and other performances may be changed by improving a certain performance index. Therefore, creative efforts are often required to prepare liquid crystal materials having suitable properties in all aspects.
The liquid crystal material is an important component of the liquid crystal display, and the liquid crystal display has great market demand at present, is mostly used in electronic and electric products, but has a short life cycle. The problem of waste pollution naturally exists in a short life cycle, and under the condition that the current green environmental protection problem is increasingly emphasized by various social circles, if the problem can be controlled from a source, namely, an environment-friendly green material is selected in the modulation process of the liquid crystal material, the environmental cost for treating the waste liquid crystal display can be greatly reduced. Therefore, creative labor is often required to prepare the liquid crystal material with proper performance in all aspects and economic, green and environment-friendly properties.
Disclosure of Invention
The purpose of the invention is as follows: in view of the defects of the prior art, the present invention provides a liquid crystal display device having optical anisotropy of proper size, high clearing point, large dielectric anisotropy, low driving voltage, good low temperature compatibility, and large KaveA liquid crystal composition of value. 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, the present invention provides a liquid crystal composition comprising:
one or more compounds of formula (I)
One or more compounds of the general formula II
One or more compounds of the formula M
One or more compounds of formula A-1
one or more compounds of formula A-2
Wherein the content of the first and second substances,
R1、RA1and RA2Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
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,
Each of one or more-H may be independently substituted with-F or-Cl;
R2represents-H, a linear alkyl or alkoxy group containing from 1 to 12 carbon atoms, an alkenyl or alkenyloxy group containing from 2 to 12 carbon atoms;
RM1and RM2Each independently represents-H, a linear or branched alkyl group having 1 to 12 carbon atoms,
1 or non-adjacent 2 or more-CH in the linear or branched alkyl containing 1 to 12 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-;
Z1、Z2and Z3Each independently represents a single bond, -CH2CH2-、-CF2CF2-、-CO-O-、-O-CO-、-O-CO-O-、-CH＝CH-、-CF＝CF-、-CH2O-or-OCH2-；
ZA11、ZA21And ZA22Each independently represents a single bond, -CH2CH2-、-CF2CF2-、-CO-O-、-O-CO-、-O-CO-O-、-CH＝CH-、-CF＝CF-、-CH2O-or-OCH2-；
ZM1And ZM2Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-or- (CH)2)4-；
L1、L2、L3、L4、LA11、LA12、LA13、LA21And LA22Each independently represents-H, an alkyl group having 1 to 3 carbon atoms, or a halogen;
X、XA1and XA2Each independently represents halogen, haloalkyl or haloalkoxy having 1 to 5 carbon atoms, haloalkenyl or haloalkenyloxy having 2 to 5 carbon atoms;
ring (C)
And ring
Each independently represent
Wherein the content of the first and second substances,
wherein one or more-CH 2-may be replaced by-O-, one or more single bonds in the ring may be replaced by double bonds,
may be substituted by-CN, -F or-Cl, and one or more rings may be substituted by-CH ═ by-N;
ring (C)
Ring (C)
And ring
Each independently represent
Wherein
One or more of-CH 2-may be replaced by-O-,
at most one-H in (a) may be substituted by halogen;
ring (C)
And ring
Each independently represent
Wherein the content of the first and second substances,
one or more-CH2-may be replaced by-O-, one or more of the ring single bonds may be replaced by double bonds,
may be substituted by-CN, -F or-Cl, and one or more rings may be substituted by-CH ═ by-N;
ring (C)
And ring
Each independently represent
Wherein the content of the first and second substances,
up to 1-CH in2-may be replaced by-O-, one or more of the ring single bonds may be replaced by double bonds,
may be substituted by-CN, -F or-Cl, and one or more rings may be substituted by-CH ═ by-N;
n1 and n2 each independently represent 0, 1 or 2, and 0. ltoreq. n1+ n2 ≦ 3, and when n1 ═ 2, the ring
May be the same or different, Z1Which may be the same or different, when n2 is 2, the ring
May be the same or different, Z2May be the same or different;
nM1、nA11and nA2Each independently represents 0, 1, 2 or 3, and when nM1When 2 or 3, ring
May be the same or different, ZM2May be the same or different; when n isA11When 2 or 3, ring
May be the same or different, ZA11May be the same or different; when n isA21 and ZA21And ZA22When all represent single bonds, a ring
And ring
Can also represent each independently
When n isA2When 2 or 3, ring
May be the same or different, ZA21May be the same or different;
nA12represents 1 or 2, and when nA12When representing 2, a ring
May be the same or different; and is
The compounds of formula I do not include the compounds of formula A-2; the compound of the general formula II is not included in the compound of the general formula A-2.
In some embodiments of the present invention, the content of the compound of formula i is desirably adjusted according to the required properties of solubility at low temperature, transition temperature, electrical reliability, transmittance, contrast, birefringence, process adaptability, dropping marks, burn-in, dielectric anisotropy, and the like.
The compounds of the general formula I preferably represent the liquid crystal compositions according to the invention in a weight ratio: the lower limit of the weight percentage of the compound of formula i in the liquid crystal composition of the present invention is preferably 0.1%, 0.5%, 1%, 2%, 3%, 4%, 5%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 20%, 30% or 40% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the weight percentage of the compound of formula I in the liquid crystal composition of the present invention is preferably 60%, 55%, 50%, 45%, 40%, 35%, 30%, 28%, 27%, 26%, 25.5%, 25%, 24.5%, 24%, 22%, 20%, 18%, 16% or 15% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the invention, the compound of formula I is present in an amount of 1% to 60% by weight of the liquid crystal composition.
In the liquid crystal composition of the present invention, in the compound of the general formula i, when n1 is 0 and n2 is 1, Z is2And Z3At least one of which is not a single bond; when n1 is 1 and n2 is 0, Z is1And Z3At least one of which is not a single bond.
In some embodiments of the invention, in the compounds of formula I, R1Preferably a linear or branched alkyl or alkoxy group having 1 to 8 carbon atoms, a linear or branched alkenyl or alkenyloxy group having 2 to 8 carbon atoms; further preferred is a linear or branched alkyl group or alkoxy group having 1 to 5 carbon atoms, a linear or branched alkenyl group or alkenyloxy group having 2 to 5 carbon atoms.
In some embodiments of the inventionIn embodiments, the ring
And ring
Each independently represent
In some embodiments of the invention, L1、L2、L3And L4Each independently represents-H, -CH3-F or-Cl.
In some embodiments of the invention, the compound of formula i is selected from the group consisting of:
wherein the content of the first and second substances,
L1、L2and L5Each independently represents-H or-F; and is
RxAnd RyEach independently represents-CH2-or-O-.
In some embodiments of the invention, in the compounds of formula I-1 through formula I-8, L5Preferably represents-H.
In some embodiments of the present invention, the compound of formula I is preferably selected from the group consisting of compounds of formula I-1, formula I-2, formula I-3, formula I-4, formula I-5, formula I-6, formula I-7, and formula I-8.
In some embodiments of the present invention, the liquid crystal composition of the present invention preferably comprises at least two compounds of formula I, wherein at least one compound of formula I is selected from the group consisting of compounds of formula I-1, formula I-2, formula I-3, formula I-4, formula I-5, formula I-6, formula I-7, and formula I-8.
In some embodiments of the present invention, the liquid crystal composition of the present invention preferably comprises at least three compounds of formula I, wherein at least one compound of formula I is selected from the group consisting of compounds of formula I-1, formula I-2, formula I-3, formula I-4, formula I-5, formula I-6, formula I-7, and formula I-8; further preferably at least two compounds selected from the group consisting of compounds of the general formula I-1, the general formula I-2, the general formula I-3, the general formula I-4, the general formula I-5, the general formula I-6, the general formula I-7 and the general formula I-8.
The weight percentage of the compound of formula II in the liquid crystal composition of the present invention is preferably: the lower limit of the weight percentage of the compound of formula ii in the liquid crystal composition of the present invention is preferably 0.1%, 0.5%, 1%, 2%, 3%, 4%, 5%, 7%, 8%, 9% or 10% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the weight percentage of the compound of the general formula ii in the liquid crystal composition of the present invention is preferably 30%, 28%, 27%, 26%, 25.5%, 25%, 24.5%, 24%, 22%, 20%, 18%, 16% or 15% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the invention, the compound of formula II is present in an amount of 0.1% to 30% by weight of the liquid crystal composition.
In some embodiments of the invention, in the compounds of formula II, R2Preferably an alkyl or alkoxy group containing 1 to 8 carbon atoms, an alkenyl or alkenyloxy group containing 2 to 8 carbon atoms; further preferred are alkyl or alkoxy groups having 1 to 5 carbon atoms, alkenyl or alkenyloxy groups having 2 to 5 carbon atoms.
In some embodiments of the invention, the absolute value of the dielectric anisotropy of the compound of formula M is not more than 3; preferably, the absolute value of the dielectric anisotropy of the compound of formula M does not exceed 2.
In some embodiments of the invention, in the compound of formula M, RM1And RM2Each independently preferably 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 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; still more preferably 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 preferably a linear alkenyl group having 2 to 8 carbon atoms; more preferably a linear alkenyl group having 2 to 5 carbon atoms.
In some embodiments of the invention, preferably, RM1And RM2One 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 RM2Both independently of each other are preferably a linear alkyl group having 1 to 8 carbon atoms or a linear alkoxy group having 1 to 7 carbon atoms; more preferably 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, preferably, RM1And RM2One 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 independently are a linear alkyl group having 1 to 5 carbon atoms.
The alkenyl group in the present invention is preferably selected from groups represented by any one of formulae (V1) to (V9), and particularly preferably formula (V1), formula (V2), formula (V8), or (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 selected from groups 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, the compound of formula M is selected from the group consisting of:
in some embodiments of the present invention, the content of the compound of formula M must be appropriately adjusted depending on the desired properties of solubility at low temperatures, transition temperature, electrical reliability, birefringence, process adaptability, dripping trace, burn-in, dielectric anisotropy, and the like.
Regarding the preference of the compound of the general formula M in weight percentage of the liquid crystal composition of the present invention: the lower limit of the compound of formula M in the weight percentage of the liquid crystal composition of the present invention is preferably 0.1%, 1%, 10%, 20%, 30%, 40% or 50% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the preferred weight percentage of the compound of formula M in the liquid crystal composition of the present invention is 90%, 85%, 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 35% or 25% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the present invention, the compound of formula M is present in an amount of 0.1% to 90% by weight of the liquid crystal composition.
The content of the compound of the formula M is preferably higher in the lower limit value and higher in the upper limit value 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 is good, it is preferable that the lower limit value is high and the upper limit value is high; in order to keep the driving voltage low and increase the absolute value of the dielectric anisotropy, it is preferable to lower the lower limit and lower the upper limit.
In some embodiments of the invention, R is preferred where reliability is a concernM1And RM2Are all alkyl; in the case where importance is attached to reduction in volatility of the compound, R is preferablyM1And RM2Are both alkoxy groups; 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 present invention, the compound of formula M is particularly preferably selected from the group consisting of compounds of formula M1, formula M2, formula M3, formula M4, formula M7, formula M8, formula M9, formula M10, formula M11, formula M13, formula M15, formula M16, formula M17, formula M18, formula M19, formula M20, formula M21, formula M22, formula M23 and formula M24.
In some embodiments of the present invention, the compound of formula M is preferably selected from the group consisting of compounds of formula M1, formula M2, formula M4, formula M9, formula M10, formula M11, formula M15, formula M16, formula M20, formula M21, formula M22, formula M23, and formula M24.
In some embodiments of the invention, in the compound of formula M1, RM1Preferably containing 1 to 7 carbon atomsLinear or branched alkyl or alkoxy; further preferably a straight-chain or branched alkyl group or alkoxy group having 1 to 5 carbon atoms.
Preference with respect to the compounds of the formula M1 in weight percent of the liquid crystal composition of the invention: the preferred lower limit of the weight percentage of the compound of formula M1 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 1%, 3%, 5%, 7%, 10%, 13%, 15%, 17%, 20%, 23%, 25% or 30%; the preferred upper limit of the weight percentage of the compound of formula M1 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 60%, 55%, 50%, 45%, 40%, 37%, 35%, 33%, 30%, 27%, 25%, 23%, 20%, 17%, 15%, 13% or 10%.
In order to improve in particular the response times of the liquid-crystal compositions according to the invention, preference is given to R in the compounds of the formula M1M1Is ethyl, n-propyl, butyl or pentyl, and RM2A compound of the formula M1, wherein R is methyl or methoxyM1Is ethyl, n-propyl, butyl or pentyl, and RM2Compounds which are ethyl or ethoxy, or compounds of the formula M1 in which R isM1Is n-propyl, butyl or pentyl, and RM2A compound that is n-propyl or propoxy.
R in the compound of formula M1 relative to the total weight of the liquid crystal composition of the inventionM1Is n-propyl and RM2The preferred lower limit of the weight percentage of the compound which is an ethyl group in the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18% or 20%; r in the compound of formula M1 relative to the total weight of the liquid crystal composition of the inventionM1Is n-propyl and RM2The upper limit of the preferred weight percentage of the compound which is an ethyl group in the liquid crystal composition of the present invention is 20%, 17%, 15%, 13%, 10%, 8%, 7% or 6%.
The weight percentage of the compound of formula M2 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M2 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 1%, 2%, 3%, 5%, 7% or 10%; the upper limit of the preferred weight percentage of the compound of formula M2 in the liquid crystal composition of the invention is 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5% or 3% relative to the total weight of the liquid crystal composition of the invention.
The weight percentage of the compound of formula M4 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M4 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 1%, 2%, 3%, 5%, 7% or 10%; the upper limit of the preferred weight percentage of the compound of formula M4 in the liquid crystal composition of the invention is 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5% or 3% relative to the total weight of the liquid crystal composition of the invention.
The weight percentage of the compound of formula M9 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M9 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35% or 40%; the upper limit of the preferred weight percentage of the compound of formula M9 in the liquid crystal composition of the invention is 50%, 40%, 35%, 30%, 20%, 15%, 10% or 5% relative to the total weight of the liquid crystal composition of the invention.
In some embodiments of the present invention, it is preferable to contain R in the compound of the formula M9 in view of required properties of solubility at low temperature, transition temperature, electrical reliability, birefringence and the likeM1Is a linear or branched alkenyl radical having 2 to 4 carbon atoms, and RM2Is CH3The compound of (a), the straight-chain or branched alkenyl group having 2 to 4 carbon atoms is more preferably
Compounds of the formula M9 relative to the total weight of the liquid-crystal composition of the inventionIn which R isM1Is composed of
And R isM2Is CH3The lower limit of the weight percentage of the compound of (a) to the liquid crystal composition of the present invention is preferably 1%, 3%, 5%, 7%, 9%, 11%, 12%, 13%, 18% or 21%, and the upper limit is preferably 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10% or 8%. When both the two compounds are contained, the lower limit of the weight percentage of the two compounds in the liquid crystal composition of the present invention is preferably 3%, 5%, 7%, 9%, 11%, 13%, 15%, 19%, 24%, or 30%, and the upper limit thereof is preferably 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 11%, or 9%, with respect to the total weight of the liquid crystal composition of the present invention.
The weight percentage of the compound of formula M10 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M10 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 1%, 2%, 3%, 4%, 5%, 7%, 10%, 14%, 16% or 20%; the preferred upper limit value of the weight percentage of the compound of formula M10 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 45%, 40%, 35%, 30%, 20%, 15%, 10% or 5%.
In some embodiments of the present invention, it is preferable to contain R in the compound of the formula M10 in view of required properties of solubility at low temperature, transition temperature, electrical reliability, birefringence and the likeM1Is a linear or branched alkenyl radical having 2 to 4 carbon atoms, and RM2Is CH3The compound of (a), the straight-chain or branched alkenyl group having 2 to 4 carbon atoms is more preferably
R in the compound of formula M10 relative to the total weight of the liquid crystal composition of the inventionM1Is composed of
And R isM2Is CH3The lower limit of the weight percentage of the compound of (a) to the liquid crystal composition of the present invention is preferably 1%, 3%, 4%, 5%, 7%, 9%, 11%, 12%, 13%, 18% or 20%, and the upper limit is preferably 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10% or 8%. When both the two compounds are contained, the lower limit value of the weight percentage of the two compounds in the liquid crystal composition of the present invention is preferably 3%, 5%, 7%, 9%, 11%, 13%, 15%, 19%, 24% or 30%, and the upper limit value is preferably 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15% or 13%, with respect to the total weight of the liquid crystal composition of the present invention.
The weight percentage of the compound of formula M11 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M11 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35% or 40%; the upper limit of the preferred weight percentage of the compound of formula M11 in the liquid crystal composition of the invention is 50%, 40%, 35%, 30%, 20%, 15%, 10% or 5% relative to the total weight of the liquid crystal composition of the invention.
Compounds of the formula M11 are preferably RM1Is n-propyl or n-pentyl, and RM2Is C2H5A compound of (a), or preferably RM1Is composed of
And R isM2Compounds which are n-propyl, or preferably RM1Is n-propyl, n-butyl or n-pentyl, and RM2Is CH3Compounds of O-, particularly preferably RM1Is n-propyl and RM2Is C2H5-a compound of (a).
The weight percentage of the compound of formula M13 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M13 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35% or 40%; the upper limit of the preferred weight percentage of the compound of formula M13 in the liquid crystal composition of the invention is 50%, 40%, 35%, 30%, 20%, 15%, 10% or 5% relative to the total weight of the liquid crystal composition of the invention.
In some embodiments of the invention, the compound of formula M13 is preferably RM1And RM2Each independently represents a linear or branched alkyl group having 2 to 5 carbon atoms, or preferably RM1And RM2One of them is
And the other is CH3-or C2H5-a compound of (a).
The weight percentage of the compound of formula M15 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M15 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 1%, 2%, 3%, 5%, 7%, 10%, 12%, 14%, 16%, 18%, 20%, 23%, 26%, 30%, 35% or 40%; the upper limit of the preferred weight percentage of the compound of formula M15 in the liquid crystal composition of the invention is 50%, 40%, 35%, 30%, 25%, 22%, 20%, 18%, 15%, 12%, 10%, 8% or 5% relative to the total weight of the liquid crystal composition of the invention.
The weight percentage of the compound of formula M16 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M16 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 1%, 2%, 3%, 5%, 7%, 10%, 12%, 14%, 16%, 18%, 20%, 23%, 26%, 30%, 35% or 40%; the upper limit of the preferred weight percentage of the compound of formula M16 in the liquid crystal composition of the invention is 50%, 40%, 35%, 30%, 25%, 22%, 20%, 18%, 15%, 12%, 10%, 8% or 5% relative to the total weight of the liquid crystal composition of the invention.
The weight percentage of the compounds of formulae M20 to M24 in the liquid crystal composition of the present invention is preferably: the lower limit of the preferred total weight percentage of the compounds of formulae M20 to M24 relative to the total weight of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16% or 20%; the upper limit value of the preferred total weight percentage of the compounds of formulae M20 to M24 relative to the total weight of the liquid crystal composition of the present invention is 30%, 25%, 23%, 20%, 18%, 15%, 12%, 10% or 5%.
In some embodiments of the invention, the compound of formula A-1 is selected from the group consisting of:
wherein the content of the first and second substances,
RA1represents a straight-chain or branched alkyl group having 1 to 8 carbon atoms,
1 or non-adjacent 2 or more-CH in the linear or branched alkyl group containing 1 to 8 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-or-O-CO-, respectively, and are present in these groupsEach of one or more-H may be independently substituted with-F or-Cl;
Rvand RwEach independently represents-CH2-or-O-;
LA11、LA12、LA11’、LA12’、LA14、LA15and LA16Each independently represents-H or-F;
LA13and LA13' independently of each other represents-H or-CH3；
XA1represents-F, -CF3or-OCF3(ii) a And is
v and w each independently represent 0 or 1.
Regarding the preference of the compound of the formula A-1 in terms of the weight percentage of the liquid crystal composition of the present invention: the preferred lower limit of the weight percentage of the compound of formula a-1 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0.1%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 12%, 14%, 15%, 17%, 18% or 20%; the preferred upper limit value of the weight percentage of the compound of the general formula a-1 to the liquid crystal composition of the present invention is 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30% or 25% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the present invention, the compound of formula A-1 comprises 0.1% to 80% by weight of the liquid crystal composition.
The preferable content of the compound of the general formula A-1 is preferably such that the lower limit value is slightly lower and the upper limit value is slightly lower, when the viscosity of the liquid crystal composition of the present invention is kept low and the response speed is high; further, when the clearing point of the liquid crystal composition of the present invention is kept high and the temperature stability is good, it is preferable to make the lower limit value slightly lower and the upper limit value slightly lower; in order to increase the absolute value of the dielectric anisotropy while keeping the driving voltage low, it is preferable to increase the lower limit and the upper limit slightly.
In some embodiments of the present invention, the compound of formula A-1 is preferably selected from the group consisting of compounds of formula A-1-2, formula A-1-3, formula A-1-4, formula A-1-5, formula A-1-7, formula A-1-9, formula A-1-11, formula A-1-13, formula A-1-15, formula A-1-16, and formula A-1-17.
In some embodiments of the invention, the compound of formula a-2 is selected from the group consisting of:
wherein the content of the first and second substances,
RA2represents a linear or branched alkyl group having 1 to 8 carbon atoms, 1 or not adjacent 2 or more-CH 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 more-H present in these groups may be independently substituted by-F or-Cl, respectively;
LA21、LA22、LA23、LA24and LA25Each independently represents-H or-F; and is
XA2represents-F, -CF3、-OCF3or-CH2CH2CH＝CF2。
The weight percentage of the compound of formula A-2 to the liquid crystal composition of the present invention is preferably: the preferred lower limit of the weight percentage of the compound of formula a-2 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0.1%, 1%, 2%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 12%, 14%, 15%, 17%, 18% or 20%; the preferred upper limit value of the weight percentage of the compound of a-2 to the liquid crystal composition of the present invention is 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30% or 25% with respect to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the invention, the compound of formula A-2 comprises 0.1% to 80% by weight of the liquid crystal composition.
The preferable content of the compound of the general formula a-2 is preferably such that the lower limit value is slightly lower and the upper limit value is slightly lower, when the viscosity of the liquid crystal composition of the present invention is kept low and the response speed is high; further, when the clearing point of the liquid crystal composition of the present invention is kept high and the temperature stability is good, it is preferable to make the lower limit value slightly lower and the upper limit value slightly lower; in order to increase the absolute value of the dielectric anisotropy while keeping the driving voltage low, it is preferable to increase the lower limit and the upper limit slightly.
In some embodiments of the present invention, the compound of formula A-2 is preferably selected from the group consisting of compounds of formula A-2-4, formula A-2-8, formula A-2-11, and formula A-2-12.
In addition to the above compounds, the liquid crystal composition of the present invention may contain a conventional nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, antioxidant, ultraviolet absorber, infrared absorber, polymerizable monomer, light stabilizer, and the like.
Possible dopants which are preferably added to the liquid crystal composition according to the invention are shown below.
In some embodiments of the present invention, preferably, the dopant comprises 0-5% by weight of the liquid crystal composition; more preferably, the dopant is present in an amount of 0-1% by weight of 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;
preferably, the light stabilizer is selected from the group consisting of the light stabilizers shown below:
in some embodiments of the present invention, preferably, the light stabilizer is 0-5% by weight of the liquid crystal composition; more preferably, the light stabilizer accounts for 0 to 1 percent of the weight of the liquid crystal composition; particularly preferably, the light stabilizer is 0.01 to 0.1% by weight of the liquid crystal composition.
In some embodiments of the present invention, the clearing point Cp of the liquid crystal composition is in the range of 80 to 120 ℃, preferably 90 to 110 ℃, and more preferably 95 to 105 ℃; the absolute value of the dielectric anisotropy Δ ∈ is in the range of 5 to 10, preferably 5.5 to 8.5, and further preferably 5.5 to 7.5; the optical anisotropy Δ n is in the range of 0.08 to 0.12, preferably 0.085 to 0.115, and more preferably 0.09 to 0.11; average elastic constant KaveNot less than 12.5; transmittance T is not less than 12.9Percent; the low-temperature storage time is more than 500h at minus 30 ℃.
In another aspect, the invention further provides a liquid crystal display device comprising the liquid crystal composition provided by the invention.
Has the advantages that:
the liquid crystal composition provided by the invention maintains optical anisotropy of proper size, and has higher clearing point, larger dielectric anisotropy, lower driving voltage, better low-temperature intersolubility, larger transmittance and larger KaveThe liquid crystal display device containing the liquid crystal composition has small light scattering and high contrast, and is particularly suitable for liquid crystal display elements driven by active matrix thin film transistors (AM-TFTs).
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, the proportions are by weight and all temperatures are in degrees centigrade, unless otherwise specified.
For convenience of expression, in the following examples, the group structure of the liquid crystal composition is represented by the code 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 cyclohexane, G represents 2-fluoro-1, 4-phenylene and F represents fluorine.
The abbreviated codes of the test items in the following examples are as follows:
cp clearing Point (nematic phase-transition temperature of isotropic phase,. degree.C.)
Δ n optical anisotropy (589nm, 25 ℃ C.)
Delta epsilon dielectric anisotropy (1KHz, 25 ℃ C.)
t-20℃Or t-30℃Low temperature storage time (h, at-20 ℃ or-30 ℃)
K11Elasticity constant of splay
K22Torsional elastic constant
K33Flexural elastic constant
KaveAverage elastic constant
Vth threshold voltage (V, characteristic voltage at 10% relative transmittance)
T transmittance (DMS 505 tester, box thickness 3.5 μm)
Wherein the content of the first and second substances,
the optical anisotropy was measured using an Abbe refractometer under a sodium lamp (589nm) light source at 25 ℃.
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: the test box is TN90 type at 25 deg.C and 1KHz, and has a thickness of 7 μm.
Test conditions for T transmittance: the DMS505 tester is used for testing the transmittance of a dimming device at a clearing point +/-10 ℃, and the dimming device is an IPS type liquid crystal testing box with the box thickness of 3.5 microns.
Test conditions for Vth: the 3.5 μm IPS mode liquid crystal cell was square wave tested using DMS505 tester.
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 compounds were tested to meet the standards for electronic compounds.
Liquid crystal compositions were prepared according to the compounding ratios of the liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared according to the conventional method in the field, such as heating, ultrasonic wave, suspension and the like, and is mixed according to the specified proportion.
Liquid crystal compositions given in the following examples were prepared and studied. The composition of each liquid crystal composition and the results of the performance parameter test thereof are shown below.
Comparative example 1
The liquid crystal composition of comparative example 1, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared with each compound and weight percentage as listed in table 2, and the test data are shown in the following table:
TABLE 2 liquid crystal composition formulations and their test properties
Example 1
The liquid crystal composition of example 1 was prepared according to the compounds and weight percentages listed in table 3, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 3 liquid crystal composition formula and its test performance
Example 2
The liquid crystal composition of example 2 was prepared according to the compounds and weight percentages listed in table 4, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 4 liquid crystal composition formula and its test performance
Example 3
The liquid crystal composition of example 3 was prepared according to the compounds and weight percentages listed in table 5, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 5 liquid crystal composition formulations and their test properties
Example 4
The liquid crystal composition of example 4 was prepared according to the compounds and weight percentages listed in table 6, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 6 liquid crystal composition formula and its test performance
Example 5
The liquid crystal composition of example 5 was prepared according to the compounds and weight percentages listed in table 7, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 7 liquid crystal composition formulations and their test properties
Example 6
The liquid crystal composition of example 6 was prepared according to the compounds and weight percentages listed in table 8, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 8 liquid crystal composition formulations and their test properties
Example 7
The liquid crystal composition of example 7 was prepared according to the compounds and weight percentages listed in table 9, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 9 liquid crystal composition formulations and their test properties
In order to highlight the liquid crystal group of the present inventionThe beneficial effects of the composition, the inventor selects a comparative example similar to the system of the embodiment of the invention. As can be seen from the above comparative example 1 and examples 1 to 7, the liquid crystal composition provided by the present invention has a higher clearing point, a larger dielectric anisotropy, a lower driving voltage, a better low temperature compatibility, a larger transmittance, and a larger K, while maintaining an appropriate amount of optical anisotropyaveThe liquid crystal display device containing the liquid crystal composition has small light scattering and high contrast, and is particularly suitable for liquid crystal display elements driven by active matrix thin film transistors (AM-TFTs).
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 (4)
1. A liquid crystal composition, comprising:
3% -30% of one or more compounds selected from the group consisting of compounds of the formulae I-2 to I-5 and I-7 to I-9
4-20% of one or more compounds of general formula II
20-65% of one or more compounds of general formula M
12-40% of one or more compounds of general formula A-1
And 6% -40% of one or more compounds selected from the group consisting of compounds of the general formulae A-2-1 to A-2-7, A-2-9 and A-2-11 to A-2-15
Wherein the content of the first and second substances,
R1and RA1Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
Or
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,
Each of one or more-H may be independently substituted with-F or-Cl;
RA2represents a linear or branched alkyl group having 1 to 8 carbon atoms, 1 or not adjacent 2 or more-CH in the linear or branched alkyl group having 1 to 8 carbon atoms2-may be independently substituted by-CH ═ CH-, -C ≡ C-, -O-, -CO-, (C ≡ C-),-CO-O-or-O-CO-substituted, and one or more-H present in these groups may each independently be substituted by-F or-Cl;
R2represents-H, a linear alkyl or alkoxy group containing from 1 to 12 carbon atoms, an alkenyl or alkenyloxy group containing from 2 to 12 carbon atoms;
RM1and RM2Each independently represents-H, a linear or branched alkyl group having 1 to 12 carbon atoms,
1 or non-adjacent 2 or more-CH in the linear or branched alkyl containing 1 to 12 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-;
ZA11represents a single bond, -CH2CH2-、-CF2CF2-、-CO-O-、-O-CO-、-O-CO-O-、-CH＝CH-、-CF＝CF-、-CH2O-or-OCH2-；
ZM1And ZM2Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-or- (CH)2)4-；
L1、L2And L5Each independently represents-H or-F;
Rxand RyEach independently represents-CH2-or-O-;
LA11、LA12and LA13Each independently represents-H, an alkyl group having 1 to 3 carbon atoms, or a halogen;
LA21、LA22、LA23、LA24and LA25Each independently represents-H or-F;
x and XA1Each independently represents halogen, haloalkyl or haloalkoxy having 1 to 5 carbon atoms, having 2 to 5 carbon atomsHaloalkenyl or haloalkenyloxy of (a);
XA2represents-F, -CF3、-OCF3or-CH2CH2CH＝CF2；
Ring (C)
Ring (C)
And ring
Each independently represent
Wherein
One or more-CH of2-can be replaced by-O-,
at most one-H in (a) may be substituted by halogen;
ring (C)
And ring
Each independently represent
Wherein the content of the first and second substances,
one or more-CH2-may be replaced by-O-, one or more of the ring single bonds may be replaced by double bonds,
may be substituted by-CN, -F or-Cl, and one or more rings may be substituted by-CH ═ by-N;
nM1and nA11Each independently represents 0, 1, 2 or 3, and when nM1When 2 or 3, ring
May be the same or different, ZM2May be the same or different; when n isA11When 2 or 3, ring
May be the same or different, ZA11May be the same or different;
nA12represents 1 or 2, and when nA12When representing 2, a ring
May be the same or different; and is
The compounds of the general formula II are not included in the compounds of the general formula A-2-11.
2. The liquid crystal composition of claim 1, wherein the compound of formula M is selected from the group consisting of:
3. the liquid crystal composition of claim 1, wherein the compound of formula a-1 is selected from the group consisting of:
wherein the content of the first and second substances,
RA1represents a straight-chain or branched alkyl group having 1 to 8 carbon atoms,
1 or non-adjacent 2 or more-CH in the linear or branched alkyl group containing 1 to 8 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-, respectively, and one or more-H present in these groups may be independently substituted by-F or-Cl, respectively;
Rvand RwEach independently represents-CH2-or-O-;
LA11、LA12、LA11’、LA12’、LA14、LA15and LA16Each independently represents-H or-F;
LA13and LA13' independently of each other represents-H or-CH3；
XA1represents-F, -CF3or-OCF3(ii) a And is
v and w each independently represent 0 or 1.
4. A display device comprising the liquid crystal composition according to any one of claims 1 to 3.
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