CN111471469A - Liquid crystal composition, liquid crystal display element and liquid crystal display - Google Patents

Liquid crystal composition, liquid crystal display element and liquid crystal display Download PDF

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CN111471469A
CN111471469A CN202010349627.3A CN202010349627A CN111471469A CN 111471469 A CN111471469 A CN 111471469A CN 202010349627 A CN202010349627 A CN 202010349627A CN 111471469 A CN111471469 A CN 111471469A
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carbon atoms
liquid crystal
group
formula
crystal composition
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李佳明
康素敏
李洪峰
张璇
员国良
梁志安
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • 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
    • G02F1/1337—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers
    • G02F1/133711—Surface-induced orientation of the liquid crystal molecules, e.g. by alignment layers by organic films, e.g. polymeric films
    • G02F1/133723—Polyimide, polyamide-imide
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3483—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a non-aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
    • C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring

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Abstract

The invention relates to a liquid crystal composition, a liquid crystal display element comprising the liquid crystal composition and a liquid crystal display, belonging to the field of liquid crystal display. The liquid crystal composition comprises one or more compounds shown as a formula I, one or more compounds shown as a formula II and one or more compounds shown as a formula III, has high dielectric anisotropy and good ultraviolet and high temperature resistance, and can improve the afterimage defect.

Description

Liquid crystal composition, liquid crystal display element and liquid crystal display
Technical Field
The invention belongs to the technical field of liquid crystal display, and particularly relates to a liquid crystal composition and a liquid crystal display element or a liquid crystal display containing the liquid crystal composition.
Background
With the development of Display technology, flat panel Display devices such as liquid Crystal displays (L liquid Crystal displays, L CDs) have advantages of high image quality, power saving, thin body, and wide application range, and thus are widely used in various consumer electronics products such as mobile phones, televisions, personal digital assistants, digital cameras, notebook computers, desktop computers, and the like, and become the mainstream of Display devices.
In the process of using the liquid crystal display, the liquid crystal composition is constantly influenced by light radiation and heat radiation, and meanwhile, in the process of manufacturing the liquid crystal display or the liquid crystal composition, the liquid crystal composition is inevitably contacted by light and heat, and the light and heat contact, especially the light and high temperature in an ultraviolet band, can cause that liquid crystal molecules are negatively influenced on the aspect of impurities, so that the change of anchoring capability of the liquid crystal molecules is influenced, and further the display effect of the liquid crystal display is influenced.
Therefore, it is a problem to be solved in the art to provide a liquid crystal composition having good uv and high temperature resistance and capable of improving the afterimage defect.
Disclosure of Invention
The present inventors have conducted extensive studies to solve the problems of the prior art, and found that the liquid crystal composition of the present invention can improve the afterimage defect, and has high dielectric anisotropy and good uv and high temperature resistance.
The invention also provides a liquid crystal display element or a liquid crystal display containing the liquid crystal composition.
Specifically, the present invention comprises the following:
in a first aspect of the present invention, there is provided a liquid crystal composition comprising: one or more compounds of formula I, one or more compounds of formula II, and one or more compounds of formula III,
Figure BDA0002471482990000021
in the formula I, Z1Represents an alkylene group having 1 to 20 carbon atoms, wherein any one or more hydrogens of the alkylene group are optionally substituted by a halogen atom, and any one or more non-adjacent-CH2-optionally substituted by-O-;
in the formula II, R represents alkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkenyl with 2-10 carbon atoms or alkenyloxy with 3-8 carbon atoms;
in the formula III, R1Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms; and R is1Any one or more non-adjacent-CH in the group2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
y represents-F, -CF3or-OCF3；
Figure BDA0002471482990000022
Each independently represent
Figure BDA0002471482990000023
Figure BDA0002471482990000024
o represents 1, 2 or 3, and when o represents 2 or 3,
Figure BDA0002471482990000025
may be the same or different;
p represents 0 or 1.
In another aspect of the present invention, there is provided a liquid crystal display element or a liquid crystal display comprising the liquid crystal composition of the present invention, the liquid crystal display element being an active matrix display element or a passive matrix display element, and the liquid crystal display being an active matrix display or a passive matrix display.
The liquid crystal composition has high dielectric anisotropy and good ultraviolet resistance and high temperature resistance, and can improve the afterimage defect.
The liquid crystal display element and the liquid crystal display provided by the invention have the advantages that no residual image exists or the residual image is not obvious, and the liquid crystal display element and the liquid crystal display have high voltage holding ratio, good ultraviolet resistance and high temperature resistance and low threshold voltage.
Detailed Description
[ liquid Crystal composition ]
The liquid crystal composition of the present invention comprises: one or more compounds of formula I, one or more compounds of formula II, and one or more compounds of formula III,
Figure BDA0002471482990000031
in the formula I, Z1Represents an alkylene group having 1 to 20 carbon atoms, wherein any one or more hydrogens of the alkylene group are optionally substituted by a halogen atom, and any one or more non-adjacent-CH2-optionally substituted by-O-;
in the formula II, R represents alkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkenyl with 2-10 carbon atoms or alkenyloxy with 3-8 carbon atoms;
in the formula III, R1Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms; and R is1Any one or more non-adjacent-CH in the group2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
y represents-F, -CF3or-OCF3；
Figure BDA0002471482990000032
Each independently represent
Figure BDA0002471482990000033
Figure BDA0002471482990000034
o represents 1, 2 or 3, and when o represents 2 or 3,
Figure BDA0002471482990000041
may be the same or different;
p represents 0 or 1.
Z of the foregoing1The alkylene group having 1 to 20 carbon atoms may be a straight chain or a branched chain. In addition, the aforementioned alkylene group optionally has a ring structure.
The liquid crystal composition of the invention has high dielectric anisotropy, good ultraviolet resistance and high temperature resistance and can improve the afterimage defect by using the combination of the compound shown in the formula I, the compound shown in the formula II and the compound shown in the formula III.
Optionally, the one or more compounds of formula I are selected from the group consisting of compounds of formula I1 to formula I13,
Figure BDA0002471482990000042
Figure BDA0002471482990000051
optionally, the one or more compounds represented by the formula II are selected from the group consisting of compounds represented by the formulae II 1 to II 4,
Figure BDA0002471482990000052
optionally, the one or more compounds shown in the formula III are selected from the group consisting of compounds shown in formulas III 1 to III 20,
Figure BDA0002471482990000053
Figure BDA0002471482990000061
Figure BDA0002471482990000071
wherein R is1Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms; and R is1Any one or more non-adjacent-CH in the group2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene; y represents-F, -CF3or-OCF3。
The liquid crystal composition of the present invention is preferably a positive dielectric anisotropic liquid crystal composition.
In the liquid crystal composition of the present invention, the amount (mass ratio) of the compound represented by formula i added to the liquid crystal composition is not particularly limited, and may be 0.001 to 1%, preferably 0.05 to 0.1%, relative to the total amount of other components of the liquid crystal composition excluding the compound represented by formula i; the amount (mass ratio) of the compound represented by the formula II added to the liquid crystal composition is not particularly limited, and may be 1 to 60%, preferably 1 to 25%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I; the amount (mass ratio) of the compound represented by the formula III added to the liquid crystal composition is not particularly limited, and may be 1 to 60%, preferably 1 to 30%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
The liquid crystal composition of the invention optionally further comprises one or more compounds shown in the following formula IV,
Figure BDA0002471482990000072
in the formula IV, R2、R3Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms;
Figure BDA0002471482990000081
each independently represent
Figure BDA0002471482990000082
The compound shown in the formula IV has the characteristics of low rotational viscosity and good intersolubility with other compounds. The liquid crystal composition contains the compound shown in the formula IV, so that the response speed of the liquid crystal composition is further improved.
The amount (mass ratio) of the compound represented by the formula IV added to the liquid crystal composition is not particularly limited, and may be, for example, 10 to 70%, preferably 20 to 60%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
Optionally, the compound shown in the formula IV is selected from the group consisting of compounds shown in formulas IV 1 to IV 16,
Figure BDA0002471482990000083
the liquid crystal composition of the present invention may optionally further comprise one or more compounds represented by the following formula V in addition to the aforementioned compound represented by the formula II,
Figure BDA0002471482990000091
in formula V, R4Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and R4Any one or more non-adjacent-CH2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene;
Figure BDA0002471482990000092
each independently represent
Figure BDA0002471482990000093
Figure BDA0002471482990000094
Z2Represents a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF ═ CF —;
X1、X2、X3each independently represents H or F;
Y1represents-F, -CF3、-OCF3、-OCF2H or-OCH2F；
m represents 0, 1 or 2, and when m represents 2,
Figure BDA0002471482990000095
may be the same or different.
The compound shown in the formula V is a positive dielectric anisotropy compound, and the threshold voltage of the liquid crystal composition can be further adjusted by the compound shown in the formula V.
The amount (mass ratio) of the compound represented by the formula V added to the liquid crystal composition is not particularly limited, and may be 1 to 50%, preferably 5 to 30%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
As R in the aforementioned formula V4One or more non-adjacent-CH in the alkyl with 1-10 carbon atoms2Examples of the group substituted with a cyclopropylene group, a cyclobutylene group or a cyclopentylene group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a methylcyclopropylidene group, an ethylcyclopropylidene group, a propylcyclopropylidene group, an isopropylcyclopropylidene group, a n-butylcyclopropylidene group, an isobutylcyclopropylidene group, a tert-butylcyclopropylidene group, a methylcyclobutylene group, an ethylcyclobutylidene group, a propylcyclobutylidene group, an isopropylidene group, a n-butylidene group, an isobutylcyclobutylidene group, a tert-butylidene group, a methylcyclopentylene group, an ethylcyclopentylidene group, a propylcyclopentylidene group, an isopropylcyclopentylidene group, a n-butylcyclopentylidene group and an isobutylcyclopentylidene group.
Optionally, the one or more compounds shown as the formula V are selected from the group consisting of compounds shown as the formulas V1 to V21,
Figure BDA0002471482990000101
Figure BDA0002471482990000111
r in the formulae V1 to V214With R in the compounds of the formula V4Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and R4Any one or more-CH of the groups shown2-non-adjacent is optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene; (F) in the formulae V1 to V6 each independently represents H or F; - (O) CF in the formula V73represents-CF3or-OCF3。
The liquid crystal composition of the invention optionally further comprises one or more compounds shown in the formula VI,
Figure BDA0002471482990000121
in formula VI, R5、R6Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
Figure BDA0002471482990000122
each independently represent
Figure BDA0002471482990000123
Formula VIThe compounds of (A) have a high clearing point and elastic constant, in particular a splay elastic constant K11The liquid crystal composition of the invention contains the compound shown in the formula VI, which is beneficial to improving the clearing point and the splay elastic constant K of the liquid crystal composition11。
When the compound represented by the formula VI is contained in the liquid crystal composition of the present invention, the amount (mass ratio) of the compound represented by the formula V to be added to the liquid crystal composition is not particularly limited, and may be 1 to 30%, preferably 5 to 20%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
Optionally, the compound shown in the formula VI is selected from the group consisting of compounds shown in formulas VI 1 to VI 4,
Figure BDA0002471482990000124
wherein R is51、R61Each independently represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms; examples of the alkenyl group having 2 to 6 carbon atoms include a vinyl group, a 2-propenyl group and a 3-pentenyl group. R62Represents an alkoxy group having 1 to 5 carbon atoms.
The liquid crystal composition of the present invention optionally further comprises one or more compounds represented by the following formula VII,
Figure BDA0002471482990000125
in the formula VII, R7、R8Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
Figure BDA0002471482990000126
to represent
Figure BDA0002471482990000127
F1、F2、F3Each independently represents a H atom or a F atom, and F2、F3Not simultaneously being F atoms.
The compounds of formula VII have a high clearing point. By containing the compound represented by the formula VII in the liquid crystal composition of the present invention, the clearing point of the liquid crystal composition of the present invention can be significantly improved.
When the liquid crystal composition of the present invention contains the compound represented by the formula VII, the amount (mass ratio) of the compound represented by the formula VII added to the liquid crystal composition is not particularly limited, and may be 1 to 10%, preferably 2 to 5%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
Alternatively, the compound represented by the formula VII is selected from the group consisting of compounds represented by formulas VII 1 to VII 3,
Figure BDA0002471482990000131
wherein R is71、R81Each independently preferably represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms.
The liquid crystal composition of the invention optionally further comprises one or more compounds shown in the following formula VIII,
Figure BDA0002471482990000132
in the formula VIII, R9、R10Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R9、R10Any one or more non-adjacent-CH2-optionally isCyclopentyl, cyclobutyl, or cyclopropylene substitution;
Z3represents a single bond, -CF2O-、-CH2CH2-or-CH2O-；Z4Represents a single bond, -CH2CH2-or-CH2O-；
Figure BDA0002471482990000133
Each independently represent
Figure BDA0002471482990000134
Figure BDA0002471482990000135
q represents 1 or 2, and when q represents 2,
Figure BDA0002471482990000136
may be the same or different;
n represents 0, 1 or 2, and when n represents 2,
Figure BDA0002471482990000141
may be the same or different.
The compound shown in the formula VIII has larger vertical dielectric constant, the vertical dielectric constant of the liquid crystal composition can be adjusted according to different use conditions, the liquid crystal composition can keep low rotational viscosity, so that the vertical dielectric constant of the liquid crystal composition is further improved on the premise of slightly sacrificing the response speed, and the transmittance of the liquid crystal composition is improved on the basis of maintaining a certain response speed.
In the liquid crystal composition of the present invention, the amount (mass ratio) of the compound represented by the formula VIII added to the liquid crystal composition is not particularly limited, and may be 1 to 35%, preferably 5 to 30%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
Optionally, the one or more compounds shown in the formula VIII are selected from the group consisting of compounds shown in formulas VIII 1 to VIII 21,
Figure BDA0002471482990000142
Figure BDA0002471482990000151
wherein R is91、R101Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and R91、R101Any one or more of the radicals indicated being unconnected-CH2-optionally each independently substituted with cyclopentylene, cyclobutyl or cyclopropylene.
The liquid crystal composition of the present invention optionally further comprises one or more compounds represented by formula IX,
Figure BDA0002471482990000152
in the formula IX, R11、R12Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R11、R12Any one or more non-adjacent-CH2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene; w represents-O-, -S-or-CH2O-。
The compound shown in the formula IX has larger vertical dielectric constant compared with the compound shown in the formula VIII, and the larger vertical dielectric constant can be obtained by adding a small amount of the compound shown in the formula IX, so that the transmittance of the liquid crystal composition is further improved.
In the liquid crystal composition of the present invention, the amount (mass ratio) of the compound represented by the formula ix added to the liquid crystal composition is not particularly limited, and may be, for example, 1 to 15%, preferably 2 to 10%, based on the total amount of other components of the liquid crystal composition excluding the compound represented by the formula I.
Alternatively, the compound of formula IX is selected from the group consisting of compounds of formula IX 1 through formula IX 8,
Figure BDA0002471482990000161
wherein R is111、R121Each independently represents an alkyl group having 2 to 6 carbon atoms.
In the liquid crystal composition of the present invention, a dopant having various functions may be optionally added, and when a dopant is contained, the content of the dopant is preferably 0.01 to 1% by mass in the liquid crystal composition, and examples of the dopant include an antioxidant, an ultraviolet absorber, and a chiral agent.
The antioxidant may be exemplified by the group consisting of,
Figure BDA0002471482990000162
Figure BDA0002471482990000171
wherein t represents an integer of 1 to 10.
[ liquid Crystal display element, liquid Crystal display ]
The present invention also relates to a liquid crystal display element or a liquid crystal display comprising the liquid crystal composition of the present invention, wherein the display element is an active matrix display element or a passive matrix display element, and the display is an active matrix display or a passive matrix display.
Optionally, the liquid crystal display element or the liquid crystal display of the invention includes a first substrate and a second substrate, and the first substrate and the second substrate are arranged in parallel relatively. The first substrate comprises a pixel electrode, a first alignment layer is arranged on the pixel electrode, the second substrate comprises a common electrode, and a second alignment layer is arranged on the common electrode. The liquid crystal composition is poured between the first substrate and the second substrate, and a One Drop Fill (ODF) method may be used.
Optionally, the liquid crystal display element or the liquid crystal display comprises an alignment layer formed by a PI with medium and high resistivity. By medium to high resistivity PI is meant a resistivity higher than 1013PI (polyimide) of Ω · m.
The liquid crystal display element and the liquid crystal display provided by the invention have the advantages that no residual image exists or the residual image is not obvious, and the liquid crystal display element and the liquid crystal display have high voltage holding ratio, good ultraviolet resistance and high temperature resistance and low threshold voltage.
The liquid crystal display element and the liquid crystal display of the present invention are not limited in structure as long as they contain the liquid crystal composition of the present invention, and those skilled in the art can select an appropriate structure of the liquid crystal display element and the liquid crystal display according to the desired performance.
Examples
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In the invention, the preparation method is a conventional method if no special description is provided, the used raw materials can be obtained from a public commercial way if no special description is provided, the percentages refer to mass percentage, the temperature is centigrade (DEG C), the liquid crystal compound is also called liquid crystal monomer, and the specific meanings and test conditions of other symbols are as follows:
cp represents a liquid crystal clearing point (DEG C), and is measured by a DSC quantitative method;
Δ n represents optical anisotropy, and Δ n ═ ne-noWherein n isoRefractive index of ordinary light, neThe refractive index of the extraordinary ray is measured under the conditions of 25 +/-2 ℃ and 589nm, and the Abbe refractometer is used for testing;
Δ represents dielectric anisotropy, Δ ═∥-⊥Wherein, in the step (A),∥is the dielectric constant parallel to the molecular axis,⊥the dielectric constant perpendicular to the molecular axis is measured under the conditions of 25 +/-0.5 ℃ and 20-micron antiparallel box, and the INSTEC is A L CT-CUST-4C test;
VHR represents the voltage holding ratio (%), and the test conditions are 60 +/-2 ℃, voltage +/-5V, pulse width 10ms and voltage holding time 16.7 ms. The testing equipment is a TOYO Model6254 liquid crystal performance comprehensive tester;
K11the test conditions for the splay elastic constant are 25 +/-2 ℃, INSTEC A L CT-CUST-4C and 20 micron parallel box;
γ1representing rotational viscosity (mPas) at 25. + -. 0.5 ℃ in a 20 micron antiparallel box, INSTEC: A L CT-CUST-4C test.
Afterimage: the residual image of the liquid crystal display device was evaluated by visually observing the residual level of the fixed pattern in the case of performing uniform display in the full screen, on a 4-scale basis as follows, after displaying the fixed pattern for 1000 hours in the display region:
◎ has no residue
○ has very little residue and is acceptable level
△ has residue at an unacceptable level
× remained, quite bad.
The preparation method of the liquid crystal composition comprises the following steps: weighing each liquid crystal monomer according to a certain proportion, putting the liquid crystal monomers into a stainless steel beaker, putting the stainless steel beaker filled with each liquid crystal monomer on a magnetic stirring instrument for heating and melting, adding a magnetic rotor into the stainless steel beaker after the liquid crystal monomers in the stainless steel beaker are melted, uniformly stirring the mixture, and cooling to room temperature to obtain the liquid crystal composition.
The liquid crystal monomer structure used in the embodiment of the invention is represented by codes, and the code representation methods of the liquid crystal ring structure, the end group and the connecting group are shown in the following tables 1 and 2.
Table 1: corresponding code of ring structure
Figure BDA0002471482990000181
Figure BDA0002471482990000191
Table 2: corresponding codes for end groups and linking groups
Figure BDA0002471482990000192
Figure BDA0002471482990000201
Examples are:
Figure BDA0002471482990000202
the code is CC-Cp-V1;
Figure BDA0002471482990000203
the code is PGP-Cpr 1-2;
Figure BDA0002471482990000204
the code is CPUP-3-OT;
Figure BDA0002471482990000205
the code is DPUQK-3-F;
Figure BDA0002471482990000211
the code is CPY-2-O2;
Figure BDA0002471482990000212
the code is CCY-3-O2;
Figure BDA0002471482990000213
the code is COY-3-O2;
Figure BDA0002471482990000214
the code is CCOY-3-O2;
Figure BDA0002471482990000215
the code is Sb-CpO-O4;
Figure BDA0002471482990000216
the code is Sc-CpO-O4.
Example 1:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 3 below.
Table 3: formulation and corresponding Properties of the liquid Crystal composition of example 1
Figure BDA0002471482990000217
Figure BDA0002471482990000221
Example 2:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 4 below.
Table 4: formulation and corresponding Properties of the liquid Crystal composition of example 2
Figure BDA0002471482990000222
Figure BDA0002471482990000231
Example 3:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 5 below.
Table 5: formulation and corresponding Properties of the liquid Crystal composition of example 3
Figure BDA0002471482990000232
Example 4:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 6 below.
Table 6: formulation and corresponding Properties of the liquid Crystal composition of example 4
Figure BDA0002471482990000241
Example 5:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 7 below.
Table 7: formulation and corresponding Properties of the liquid Crystal composition of example 5
Figure BDA0002471482990000242
Figure BDA0002471482990000251
Example 6:
the formulation and corresponding properties of the liquid crystal compositions are shown in Table 8 below.
Table 8: formulation and corresponding Properties of the liquid Crystal composition of example 6
Figure BDA0002471482990000261
Example 7:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 9 below.
Table 9: formulation and corresponding Properties of the liquid Crystal composition of example 7
Figure BDA0002471482990000271
Figure BDA0002471482990000281
Example 8:
the formulation and corresponding properties of the liquid crystal composition are shown in table 10 below.
Table 10: formulation and corresponding Properties of the liquid Crystal composition of example 8
Figure BDA0002471482990000282
Figure BDA0002471482990000291
Liquid crystal compositions obtained by replacing the compound represented by the formula I7 in example 8 with compounds represented by the formulae I2, I6 and I11 in equal amounts were prepared as examples 9, 10 and 11, respectively.
Comparative example 1:
the formulation and corresponding properties of the liquid crystal compositions are shown in Table 11 below.
Table 11: formulation and corresponding Properties of the liquid Crystal composition of comparative example 1
Figure BDA0002471482990000292
Figure BDA0002471482990000301
In contrast to example 6, comparative example 1, which did not contain the compounds of formula I, formula II and formula III, used the compound PGUQU-3-F, PGUQU-4-F in place of the compound DPUQU-3-F, DPUQU-4-F and the compound APUQU-3-F, CPPQU-5-F in place of the compound APUQK-3-F, CPPQK-5-F.
Comparative example 2:
the formulation and corresponding properties of the liquid crystal compositions are shown in table 12 below.
Table 12: formulation and corresponding Properties of the liquid Crystal composition of comparative example 2
Figure BDA0002471482990000302
Figure BDA0002471482990000311
In contrast to example 6, comparative example 2 does not contain the compound of formula I, and the compound of formula T-1 below is used in place of the compound of formula I in equal amounts.
Figure BDA0002471482990000312
Comparative example 3:
the formulation and corresponding properties of the liquid crystal compositions are shown in Table 13 below.
Table 13: formulation and corresponding Properties of the liquid Crystal composition of comparative example 3
Figure BDA0002471482990000313
Figure BDA0002471482990000321
In contrast to example 6, in comparative example 3, which does not contain the compound of formula II, the compound DGUQU-3-F, DGUQU-4-F is used in equal amounts instead of the compound DPUQU-3-F, DPUQU-4-F of formula II. Example 6 provides a liquid crystal composition1/K11Comparative example 3 provides liquid crystal composition γ of 5.561/K116.00, response speed of liquid crystal composition and gamma thereof1/K11Ratio dependent, γ1/K11The smaller the ratio, the faster the response speed, and thus, the liquid crystal composition provided by example 6 has a faster response speed relative to comparative example 3.
The reliability of the liquid crystal composition can be evaluated by testing the change of VHR by ultraviolet and high temperature aging tests. The smaller the VHR data change before and after the ultraviolet and high temperature test of the liquid crystal composition, the stronger the ultraviolet and high temperature resistance of the liquid crystal composition. Therefore, the stronger the capability of the liquid crystal composition to resist the damage of the external environment in the working process, the higher the reliability of the liquid crystal composition. Therefore, the ultraviolet and high temperature resistance can be judged by comparing the change of VHR data of the liquid crystal compositions provided by each example and comparative example before and after the aging test.
First, before the ultraviolet and high-temperature aging test, VHR data of the liquid crystal composition was measured as initial VHR data, and then, the ultraviolet and high-temperature aging test was performed on the liquid crystal composition, and after the test, VHR data of the liquid crystal composition was measured again.
The aging test is divided into two stages,
the first stage aging test conditions are as follows. Ultraviolet aging test: placing the liquid crystal composition at a wavelength of 365nm and an irradiance of 50mw/cm2Under an ultraviolet lamp, irradiating 5000mJ energy; high-temperature aging test: the liquid crystal composition was placed in an oven at 100 ℃ for 1 hour.
The second stage aging test conditions are as follows. Ultraviolet aging test: the liquid crystal composition is placed under 20000nit backlight for 1000 hours; high-temperature aging test: the liquid crystal composition was placed in an oven at 60 ℃ for 120 hours.
The liquid crystal compositions provided in examples and comparative examples were tested for VHR and afterimage after being subjected to the first-stage and second-stage aging tests, respectively.
The liquid crystal compositions provided in examples and comparative examples were poured into liquid crystal test cells containing two different PI (polyimide) -formed alignment layers, respectively, to perform an afterimage test, liquid crystal test cell a contained an alignment layer formed of a PI of medium to high resistivity, for example, Nissan SE-7492, Nissan SE-6414, and liquid crystal test cell B contained an alignment layer formed of a PI of low resistivity, for example, Nissan SE-5414, JSR a L16301, and the test results are shown in tables 14 and 15 below.
In tables 14 and 15, VHR1 is the test data after the first stage aging test, VHR2 is the test data after the second stage aging test, afterimage a is the afterimage test result of the liquid crystal composition in liquid crystal test cell a, and afterimage B is the afterimage test result of the liquid crystal composition in liquid crystal test cell B.
Table 14: data for testing reliability of examples and comparative examples after first stage aging test
Figure BDA0002471482990000331
Figure BDA0002471482990000341
As can be seen from Table 14, the liquid crystal compositions provided in the examples of the present invention have very small VHR decrease after UV and high temperature aging test as compared with the comparative examples 1-2. In addition, the improvement on the afterimage defect is very obvious. Compared with the comparative example 3, after the first-stage aging test, although the residual image improvement effect is consistent when the middle-high resistivity PI liquid crystal test box is used, the residual image improvement effect is better when the low resistivity PI liquid crystal test box is used.
Table 15: data for testing reliability of examples and comparative examples after second stage aging test
Figure BDA0002471482990000342
Figure BDA0002471482990000351
As can be seen from Table 15, the VHR of the liquid crystal compositions provided in examples after UV and high temperature aging test was reduced less and the improvement of the afterimage was more significant than that of the comparative examples. In particular, the liquid crystal composition of the example using the compound represented by formula I7 can achieve a better afterimage improvement effect in combination with high-resistivity PI.

Claims (9)

1. A liquid crystal composition comprising one or more compounds of formula I, one or more compounds of formula II, and one or more compounds of formula III,
Figure FDA0002471482980000011
in the formula I, Z1Represents an alkylene group having 1 to 20 carbon atoms, wherein any one or more hydrogen atoms in the alkylene group are optionally substituted by halogen, and any one or more non-adjacent-CH2-optionally substituted by-O-;
in the formula II, R represents alkyl with 1-10 carbon atoms, alkoxy with 1-10 carbon atoms, alkenyl with 2-10 carbon atoms or alkenyloxy with 3-8 carbon atoms;
in the formula III, R1Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms; and R is1Any one or more non-adjacent-CH in the group2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
y represents-F, -CF3or-OCF3；
Figure FDA0002471482980000012
Each independently represent
Figure FDA0002471482980000013
Figure FDA0002471482980000014
o represents 1, 2 or 3, and when o represents 2 or 3,
Figure FDA0002471482980000015
may be the same or different;
p represents 0 or 1.
2. The liquid crystal composition of claim 1, further comprising one or more compounds of formula IV,
Figure FDA0002471482980000021
in the formula IV, R2、R3Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms;
Figure FDA0002471482980000022
each independently represent
Figure FDA0002471482980000023
3. The liquid crystal composition according to any one of claims 1 or 2, further comprising one or more compounds represented by the following formula V, in addition to the compound represented by the formula II,
Figure FDA0002471482980000024
in formula V, R4Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, and R4Any one or more non-adjacent-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Figure FDA0002471482980000025
each independently represent
Figure FDA0002471482980000026
Figure FDA0002471482980000027
Z2Represents a single bond, -CH2-、-CH2-CH2-、-(CH2)3-、-(CH2)4-、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CF2O-、-OCH2-、-CH2O-、-OCF2-、-CF2CH2-、-CH2CF2-、-C2F4-or-CF ═ CF —;
X1、X2、X3each independently represents H or F;
Y1represents-F, -CF3、-OCF3、-OCF2H or-OCH2F；
m represents 0, 1 or 2, and when m represents 2,
Figure FDA0002471482980000028
may be the same or different.
4. The liquid crystal composition according to any one of claims 1 to 3, further comprising one or more compounds represented by the following formula VI,
Figure FDA0002471482980000029
in formula VI, R5、R6Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
Figure FDA0002471482980000031
each independently represent
Figure FDA0002471482980000032
5. The liquid crystal composition according to any one of claims 1 to 4, further comprising one or more compounds represented by the following formula VII,
Figure FDA0002471482980000033
in the formula VII, R7、R8Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
Figure FDA0002471482980000034
to represent
Figure FDA0002471482980000035
F1、F2、F3Each independently represents H or F, and F2、F3Not simultaneously F.
6. The liquid crystal composition according to any one of claims 1 to 5, further comprising one or more compounds represented by the following formula VIII,
Figure FDA0002471482980000036
in the formula VIII, R9、R10Each independently represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R9、R10Any one or more non-adjacent-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z3represents a single bond, -CF2O-、-CH2CH2-or-CH2O-；
Z4Represents a single bond, -CH2CH2-or-CH2O-；
Figure FDA0002471482980000037
Each independently represent
Figure FDA0002471482980000038
Figure FDA0002471482980000039
q represents 1 or 2, and when q represents 2,
Figure FDA0002471482980000041
may be the same or different;
n represents 0, 1 or 2, and when n represents 2,
Figure FDA0002471482980000042
may be the same or different.
7. The liquid crystal composition according to any one of claims 1 to 6, further comprising one or more compounds represented by formula IX,
Figure FDA0002471482980000043
in the formula IX, R11、R12Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R11、R12Any one or more non-adjacent-CH2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene;
w represents-O-),-S-or-CH2O-。
8. A liquid crystal display element or a liquid crystal display, comprising the liquid crystal composition according to any one of claims 1 to 7, wherein the display element is an active matrix display element or a passive matrix display element, and the display is an active matrix display or a passive matrix display.
9. The liquid crystal display element or the liquid crystal display according to claim 8, wherein the liquid crystal display element or the liquid crystal display comprises an alignment layer formed of a PI with a medium-high resistivity.
CN202010349627.3A 2020-04-28 2020-04-28 Liquid crystal composition, liquid crystal display element and liquid crystal display Pending CN111471469A (en)

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