CN111748357A - Liquid crystal composition and liquid crystal display device - Google Patents

Liquid crystal composition and liquid crystal display device Download PDF

Info

Publication number
CN111748357A
CN111748357A CN201910249913.XA CN201910249913A CN111748357A CN 111748357 A CN111748357 A CN 111748357A CN 201910249913 A CN201910249913 A CN 201910249913A CN 111748357 A CN111748357 A CN 111748357A
Authority
CN
China
Prior art keywords
liquid crystal
carbon atoms
formula
crystal composition
group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201910249913.XA
Other languages
Chinese (zh)
Other versions
CN111748357B (en
Inventor
李佳明
梁志安
员国良
康素敏
张璇
张宁
鲜义芬
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
Original Assignee
Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shijiazhuang Chengzhi Yonghua Display Material Co Ltd filed Critical Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
Priority to CN201910249913.XA priority Critical patent/CN111748357B/en
Publication of CN111748357A publication Critical patent/CN111748357A/en
Application granted granted Critical
Publication of CN111748357B publication Critical patent/CN111748357B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • G02F1/137—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 characterised by the electro-optical or magneto-optical effect, e.g. field-induced phase transition, orientation effect, guest-host interaction or dynamic scattering

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Nonlinear Science (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

The present invention relates to a liquid crystal composition and a liquid crystal display device including the same. The invention provides a liquid crystal composition which comprises one or more compounds shown as a formula I and one or more compounds shown as a formula II,

Description

Liquid crystal composition and liquid crystal display device
Technical Field
The invention belongs to the field of liquid crystal compounds. And more particularly, to a liquid crystal composition and a liquid crystal display device including the same.
Background
With the development of Display technology, flat panel Display devices such as Liquid Crystal Displays (LCDs) 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, and desktop computers, and become the mainstream of Display devices. The demand for the liquid crystal flat panel display is increasing. Therefore, higher requirements are also placed on the quality characteristics of the liquid crystal materials used in liquid crystal flat panel displays.
The liquid crystal material is one of important photoelectronic materials for liquid crystal displays, and plays an important role in improving the performance of the liquid crystal displays. Any of the liquid crystal compositions for display is required to have a wide liquid crystal state temperature, high stability, low rotational viscosity, and a fast response speed to an electric field. Therefore, it is important to develop a liquid crystal material having excellent properties and to obtain a liquid crystal composition satisfying the requirements.
Disclosure of Invention
The present inventors have conducted extensive studies to obtain a liquid crystal composition having a low rotational viscosity and a high response speed, and as a result, have found that the liquid crystal compound and the liquid crystal composition provided by the present invention can achieve the above object, and have completed the present invention.
The first purpose of the invention is to provide a liquid crystal composition which has lower rotational viscosity, larger elastic constant, moderate optical anisotropy delta n, good low-temperature solubility, lower threshold voltage and good ultraviolet and high temperature resistance.
The second object of the invention is to provide a liquid crystal display device comprising the liquid crystal composition.
In order to achieve the first purpose, the invention adopts the following technical scheme:
a liquid crystal composition comprising one or more compounds of formula I and one or more compounds of formula II,
Figure BDA0002012102890000011
in the formula I, 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; wherein R is1Any one or more-CH of the groups shown2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene;
R2represents F, -CF3、-OCF3；
Figure BDA0002012102890000021
Each independently represent
Figure BDA0002012102890000022
Figure BDA0002012102890000023
m represents 1, 2 or 3;
n represents 0 or 1;
in the formula II, R3Represents an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms, wherein R is3Any one or more-CH of the groups shown2-may optionally be replaced by cyclopentylene, cyclobutyl or cyclopropylene.
In the liquid crystal composition provided by the invention, the compounds shown in the formula I and the formula II have the characteristics of low rotational viscosity and high solubility. The lower rotational viscosity is more beneficial to improving the response speed of the liquid crystal composition, and the high solubility can be mutually dissolved with other compounds more easily and is not easy to precipitate. In addition, the compound shown in the formula I has larger positive dielectric anisotropy, which is beneficial to reducing threshold voltage, and the compound shown in the formula II has larger elastic constant, which is beneficial to improving response speed. Therefore, the liquid crystal composition composed of the liquid crystal compounds shown in the formula I and the formula II has lower rotational viscosity, larger elastic constant, moderate optical anisotropy delta n, good low-temperature solubility, lower threshold voltage and good ultraviolet and high-temperature resistance.
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 addition amount (mass fraction) of the compounds represented by the formulae i and ii in the liquid crystal composition is not particularly limited;
preferably, in the liquid crystal composition, the mass fraction of the compound shown as the formula I is 1-50%, and the mass fraction of the compound shown as the formula II is 1-50%;
preferably, in the liquid crystal composition, the mass fraction of the compound shown as the formula I is 1-30%, and the mass fraction of the compound shown as the formula II is 5-20%.
Preferably, in the liquid crystal composition of the present invention, the one or more compounds represented by formula I are selected from compounds represented by formula I-1 to formula I-10,
Figure BDA0002012102890000024
Figure BDA0002012102890000031
Figure BDA0002012102890000041
wherein R is101Represents an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms; r2Represents F, -CF3、-OCF3(ii) a Wherein R is101Any one or more-CH of the groups shown2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene.
As the aforementioned R101One or more non-adjacent-CH in the alkyl with 1-10 carbon atoms2Examples of the group substituted by cyclopropylene, cyclobutylene or cyclopentylene include cyclopropyl, cyclobutyl, cyclopentyl, methylcyclopropylene and ethylideneethyleneCyclopropyl, propylcyclopropylene, isopropylcyclopropylene, n-butylcyclopropylene, isobutylcyclopropylene, tert-butylcyclopropylene, methylcyclobutylene, ethylcyclobutylene, propylcyclobutylene, isopropylcyclobutylene, n-butylcyclobutylene, isobutylcyclobutylene, tert-butylcyclobutylene, methylcyclopentylene, ethylcyclopentylene, propylcyclopentylene, isopropylcyclopentylene, n-butylcyclopentylene, isobutylcyclopentylene and the like. R101Among the groups shown, preferred from the viewpoint of the rotational viscosity, solubility and clearing point of the liquid crystal compound is cyclopropyl or cyclopentyl.
Preferably, in the liquid crystal composition of the present invention, the aforementioned one or more compounds represented by formula II are selected from the group consisting of compounds represented by formula II-1 to formula II-4,
Figure BDA0002012102890000042
preferably, the liquid crystal composition of the invention further comprises one or more compounds shown in the following formula III,
Figure BDA0002012102890000043
in the formula III, R4、R5Each 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 BDA0002012102890000044
each independently represent
Figure BDA0002012102890000045
The compound shown in the formula III has the characteristics of low rotational viscosity and good intersolubility with other compounds. The liquid crystal composition of the present invention containing the compound represented by the formula III is advantageous for further improving the response speed of the liquid crystal composition.
In the liquid crystal composition of the present invention, the addition amounts (mass fractions) of the compounds represented by formulae i, ii and iii in the liquid crystal composition are not particularly limited;
preferably, in the liquid crystal composition, the mass fraction of the compound shown as the formula III is 10-70%; further preferably 20 to 60%;
preferably, the mass fraction of the compound shown in the formula I in the liquid crystal composition is 1-50%, the mass fraction of the compound shown in the formula II in the liquid crystal composition is 1-50%, and the mass fraction of the compound shown in the formula III in the liquid crystal composition is 10-70%;
preferably, the mass fraction of the compound shown in the formula I in the liquid crystal composition is 1-30%, the mass fraction of the compound shown in the formula II is 5-20%, and the mass fraction of the compound shown in the formula III is 20-60%.
Preferably, the compound represented by the formula III is selected from compounds represented by the formulae III-1 to III-16,
Figure BDA0002012102890000051
preferably, the liquid crystal composition of the invention further comprises one or more compounds shown in the following formula IV,
Figure BDA0002012102890000052
in the formula IV, R6、R7Each 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, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 8 carbon atoms;
Figure BDA0002012102890000053
each independently represent
Figure BDA0002012102890000054
The compounds of formula IV have high clearing point and elastic constants, especially splay elastic constant K11By the liquid crystal composition of the present inventionThe compound shown in the formula IV is contained in the compound, which is beneficial to improving the clearing point and the splay elastic constant K of the liquid crystal composition11。
In the liquid crystal composition of the present invention, the addition amounts (mass fractions) of the compounds represented by the formulae i, ii, iii and IV in the liquid crystal composition are not particularly limited;
preferably, the mass fraction of the compound shown in the formula IV in the liquid crystal composition is 1-30%; further preferably 5 to 20%;
preferably, the mass fraction of the compound shown in the formula I in the liquid crystal composition is 1-50%, the mass fraction of the compound shown in the formula II is 1-50%, the mass fraction of the compound shown in the formula III is 10-70%, and the mass fraction of the compound shown in the formula IV is 1-30%;
preferably, the liquid crystal composition contains 1-30% of the compound shown in the formula I, 5-20% of the compound shown in the formula II, 20-60% of the compound shown in the formula III and 5-20% of the compound shown in the formula IV.
Preferably, the compound represented by the formula IV is selected from the group consisting of compounds represented by the formulae IV-1 to IV-4,
Figure BDA0002012102890000061
wherein R is61、R71Each independently represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms; r72Represents an alkoxy group having 1 to 5 carbon atoms.
Preferably, said R is61、R71The alkenyl group having 2 to 6 carbon atoms is a vinyl group, a 2-propenyl group or a 3-pentenyl group.
Preferably, the liquid crystal composition of the invention further comprises one or more compounds shown in the following formula V,
Figure BDA0002012102890000062
in the formula V, R8、R9Each independently represents an alkyl group having 1 to 10 carbon atoms or a fluorine-substituted carbon atomAlkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms substituted with fluorine, alkenyl having 2 to 10 carbon atoms substituted with fluorine, alkenyloxy having 3 to 8 carbon atoms or alkenyloxy having 3 to 8 carbon atoms substituted with fluorine;
Figure BDA0002012102890000063
to represent
Figure BDA0002012102890000064
F1、F2、F3Each independently represents H or F, and F2、F3Not simultaneously F.
The compounds of formula V have a high clearing point. By containing the compound shown in the formula V in the liquid crystal composition, the clearing point of the liquid crystal composition can be remarkably improved.
In the liquid crystal composition of the present invention, the addition amount (mass fraction) of the compounds represented by the formulae I, II, III, IV and V in the liquid crystal composition is not particularly limited;
preferably, in the liquid crystal composition, the mass fraction of the compound shown in the formula V is 1-10%; further preferably 2 to 5%;
preferably, the mass fraction of the compound shown in the formula I in the liquid crystal composition is 1-50%, the mass fraction of the compound shown in the formula II is 1-50%, the mass fraction of the compound shown in the formula III is 10-70%, the mass fraction of the compound shown in the formula IV is 1-30%, and the mass fraction of the compound shown in the formula V is 1-10%;
preferably, the liquid crystal composition contains 1-50% of the compound shown in the formula I, 5-20% of the compound shown in the formula II, 20-60% of the compound shown in the formula III, 5-20% of the compound shown in the formula IV and 2-5% of the compound shown in the formula V.
Preferably, the compound represented by the formula V is selected from compounds represented by the formulae V-1 to V-3,
Figure BDA0002012102890000065
Figure BDA0002012102890000071
wherein R is81、R91Each independently preferably represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms.
Preferably, the liquid crystal composition of the invention further comprises one or more compounds shown in the formula VI,
Figure BDA0002012102890000072
in formula VI, R10Represents 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; wherein R is10Any one or more of-CH2-may optionally be replaced by cyclopentylene, cyclobutyl or cyclopropylene;
Figure BDA0002012102890000073
each independently represent
Figure BDA0002012102890000074
Figure BDA0002012102890000075
Z1Represents 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；
q represents 0, 1 or 2.
The compound shown in the formula VI is positive dielectric anisotropy, and the threshold voltage of the liquid crystal composition is further adjusted by the compound shown in the formula VI. In the liquid crystal composition of the present invention, the addition amount (mass fraction) of the compounds represented by the formulae I, II, III, IV, V and VI in the liquid crystal composition is not particularly limited;
preferably, in the liquid crystal composition, the mass fraction of the compound shown in the formula VI is 1-50%; further preferably 10 to 30%;
preferably, the mass fraction of the compound shown in the formula I in the liquid crystal composition is 1-50%, the mass fraction of the compound shown in the formula II is 1-50%, the mass fraction of the compound shown in the formula III is 10-70%, the mass fraction of the compound shown in the formula IV is 1-30%, the mass fraction of the compound shown in the formula V is 1-10%, and the mass fraction of the compound shown in the formula VI is 1-50%;
preferably, the mass fraction of the compound shown in the formula I is 1-30%, the mass fraction of the compound shown in the formula II is 5-20%, the mass fraction of the compound shown in the formula III is 20-60%, the mass fraction of the compound shown in the formula IV is 5-20%, the mass fraction of the compound shown in the formula V is 2-5%, and the mass fraction of the compound shown in the formula VI is 10-30%.
Preferably, the one or more compounds shown in the formula VI are selected from compounds shown in the formula VI-1 to VI-23,
Figure BDA0002012102890000081
Figure BDA0002012102890000091
r in the formulae VI-1 to VI-2, VI 4 to VI 2310Each 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 a C3-8 alkenyloxy; wherein R is10Any one or more-CH of the groups shown2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene;
(F) in the formulae VI 1 to VI 6 each independently represents H or F;
- (O) CF in the formula VI 73represents-CF3or-OCF3；
R in the formula VI-3102Represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, or an alkenyloxy group having 3 to 8 carbon atoms; wherein R is102Any one or more-CH of the groups shown2-optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene.
As R in the aforementioned formula VI10One 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. R10Among the groups shown, preferred from the viewpoint of the rotational viscosity, solubility and clearing point of the liquid crystal compound is cyclopropyl or cyclopentyl.
Preferably, the liquid crystal composition of the present invention further comprises one or more compounds represented by the following formula VII,
Figure BDA0002012102890000101
in the formula VII, R11、R12Each 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, fluorineA 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; wherein R is11、R12Any one or more non-adjacent-CH2-optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z2represents a single bond, -CF2O-、-CH2CH2-or-CH2O-；Z3Represents a single bond, -CH2CH2-or-CH2O-；
Figure BDA0002012102890000102
Each independently represent
Figure BDA0002012102890000103
Figure BDA0002012102890000104
r represents 1 or 2; s represents 0, 1 or 2.
The compound shown in the formula VII 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 addition amount (mass fraction) of the compounds represented by the formulae I, II, III, IV, V, VI and VII in the liquid crystal composition is not particularly limited;
preferably, in the liquid crystal composition, the mass fraction of the compound shown in the formula VII is 1-30%; further preferably 10 to 25%;
preferably, the mass fraction of the compound shown in the formula I in the liquid crystal composition is 1-50%, the mass fraction of the compound shown in the formula II is 1-50%, the mass fraction of the compound shown in the formula III is 10-70%, the mass fraction of the compound shown in the formula IV is 1-30%, the mass fraction of the compound shown in the formula V is 1-10%, the mass fraction of the compound shown in the formula VI is 1-50%, and the mass fraction of the compound shown in the formula VII is 1-30%;
preferably, the mass fraction of the compound shown in the formula I is 1-30%, the mass fraction of the compound shown in the formula II is 5-20%, the mass fraction of the compound shown in the formula III is 20-60%, the mass fraction of the compound shown in the formula IV is 5-20%, the mass fraction of the compound shown in the formula V is 2-5%, the mass fraction of the compound shown in the formula VI is 10-30%, and the mass fraction of the compound shown in the formula VII is 10-25%.
Preferably, the one or more compounds of formula VII are selected from compounds of formulae VII-1 to VII-21,
Figure BDA0002012102890000111
Figure BDA0002012102890000121
wherein R is111、R121Each 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; wherein R is111、R121Any one or more of the radicals indicated being unconnected-CH2-optionally each independently substituted with cyclopentylene, cyclobutyl or cyclopropylene.
Preferably, the liquid crystal composition of the present invention further comprises one or more compounds represented by formula VIII,
Figure BDA0002012102890000122
in the formula VIII, R13、R14Each 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 groupA substituted alkenyloxy group having 3 to 8 carbon atoms; w represents-O-, -S-or-CH2O-; wherein R is13、R14Any one or more non-adjacent-CH2-may optionally be replaced by cyclopentylene, cyclobutyl or cyclopropylene.
The compound shown in the formula VIII has larger vertical dielectric compared with the compound shown in the formula VII, and the larger vertical dielectric can be obtained by adding a small amount of the compound shown in the formula VIII, so that the transmittance of the liquid crystal composition is further improved.
In the liquid crystal composition of the present invention, the addition amount (mass fraction) of the compounds represented by the formulae I, II, III, IV, V, VI, VII and VIII in the liquid crystal composition is not particularly limited;
preferably, in the liquid crystal composition, the mass fraction of the compound shown as the formula VIII is 1-15%; more preferably 2 to 10%.
Preferably, the mass fraction of the compound shown in the formula I in the liquid crystal composition is 1-50%, the mass fraction of the compound shown in the formula II is 1-50%, the mass fraction of the compound shown in the formula III is 10-70%, the mass fraction of the compound shown in the formula IV is 1-30%, the mass fraction of the compound shown in the formula V is 1-10%, the mass fraction of the compound shown in the formula VI is 1-50%, the mass fraction of the compound shown in the formula VII is 1-30%, and the mass fraction of the compound shown in the formula VIII is 1-15%;
preferably, the mass fraction of the compound shown in the formula I is 1-30%, the mass fraction of the compound shown in the formula II is 5-20%, the mass fraction of the compound shown in the formula III is 20-60%, the mass fraction of the compound shown in the formula IV is 5-20%, the mass fraction of the compound shown in the formula V is 2-5%, the mass fraction of the compound shown in the formula VI is 10-30%, the mass fraction of the compound shown in the formula VII is 10-25%, and the mass fraction of the compound shown in the formula VIII is 2-10%.
Preferably, the compound represented by the aforementioned formula VIII is selected from the group consisting of compounds represented by the formulae VIII-1 to VIII-6,
Figure BDA0002012102890000123
Figure BDA0002012102890000131
wherein R is141Represents an alkyl group having 2 to 6 carbon atoms.
Preferably, a dopant having various functions may be added to the liquid crystal composition of the present invention, 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.
Examples of the antioxidant and ultraviolet absorber include:
Figure BDA0002012102890000132
t represents an integer of 1 to 10.
The third aspect of the present invention provides a liquid crystal display device comprising the liquid crystal composition of the present invention.
The liquid crystal display device of the present invention includes a liquid crystal display and a liquid crystal display element.
Preferably, the liquid crystal display element is an active matrix display element or a passive matrix display element.
The liquid crystal display component comprises the liquid crystal composition, and has the advantages of high response speed, wide nematic phase temperature range, moderate optical anisotropy, high voltage holding ratio, good ultraviolet resistance and high temperature resistance, and low threshold voltage.
The invention has the following beneficial effects:
the compound shown in the formula I and the compound shown in the formula II have the characteristics of low rotational viscosity and high solubility. The liquid crystal composition composed of the liquid crystal compounds shown in the formula I and the formula II has lower rotational viscosity, larger elastic constant, moderate optical anisotropy delta n, good low-temperature solubility and difficult precipitation; lower threshold voltage and good ultraviolet resistance and high temperature resistance. The liquid crystal display component containing the liquid crystal composition has the advantages of high response speed, wide nematic phase temperature range, moderate optical anisotropy, high voltage holding ratio, good ultraviolet resistance and high temperature resistance, and low threshold voltage.
Detailed Description
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 also becomes a 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 of DEG C, and is measured by an Abbe refractometer;
Δ represents dielectric anisotropy, Δ ═/-, where/is the dielectric constant parallel to the molecular axis,/-is the dielectric constant perpendicular to the molecular axis, the test conditions were 25 ± 0.5 ℃, 20 micron parallel cells, INSTEC: ALCT-IR1 test;
γ 1 represents rotational viscosity (mPas) under 25. + -. 0.5 ℃ in a 20 μm parallel cell INSTEC: ALCT-IR 1;
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 of 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.
Corresponding code of the ring structure of Table 1
Figure BDA0002012102890000141
Figure BDA0002012102890000151
TABLE 2 corresponding codes for end groups and linking groups
Figure BDA0002012102890000152
Figure BDA0002012102890000161
Examples are:
Figure BDA0002012102890000162
the code is CC-Cp-V1;
Figure BDA0002012102890000163
the code is PGP-Cpr 1-2;
Figure BDA0002012102890000164
the code is CPUP-3-OT;
Figure BDA0002012102890000165
the code is DPUQK-3-F;
Figure BDA0002012102890000166
the code is CPY-2-O2;
Figure BDA0002012102890000167
the code is CCY-3-O2;
Figure BDA0002012102890000168
the code is COY-3-O2;
Figure BDA0002012102890000171
the code is CCOY-3-O2;
Figure BDA0002012102890000172
the code is Sb-Cp 1O-O4;
Figure BDA0002012102890000173
the code is Sc-Cp 1O-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 BDA0002012102890000174
Figure BDA0002012102890000181
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 BDA0002012102890000182
Figure BDA0002012102890000191
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 BDA0002012102890000192
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 BDA0002012102890000201
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 BDA0002012102890000202
Figure BDA0002012102890000211
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 BDA0002012102890000212
Figure BDA0002012102890000221
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 BDA0002012102890000222
Figure BDA0002012102890000231
Comparative example 1
The formulation and corresponding properties of the liquid crystal composition are shown in table 10 below.
TABLE 10 formulation and corresponding Properties of the comparative example 1 liquid Crystal composition
Figure BDA0002012102890000232
Figure BDA0002012102890000241
By comparing example 6 with comparative example 1, the rotational viscosity γ of the liquid crystal composition of example 6 is compared with that of comparative example 1 which does not contain the compound represented by the formula I or II1Coefficient of elasticity K of splay11Are all smaller than the liquid crystal composition of comparative example 1, due to the response speed and gamma of the liquid crystal composition1/K11Is related by the ratio of (a) (-), γ1/K11The smaller the ratio of (a) is, the faster the response speed is, and thus the liquid crystal composition of example 6 has a faster response speed than the liquid crystal composition of comparative example 1. Also, when left to stand at the same temperature of-30 ℃ for 480 hours, the liquid crystal composition of example 6 did not crystallize, whereas the composition of comparative example 1 crystallized after 408 hours. As can be seen, the liquid crystal composition of example 6 has better low temperature intersolubility and is not easy to crystallize.
Comparative example 2
The formulation and corresponding properties of the liquid crystal compositions are shown in Table 11 below.
TABLE 11 formulation and corresponding Properties of the comparative example 2 liquid Crystal composition
Figure BDA0002012102890000242
Figure BDA0002012102890000251
Comparative example 2 using the compound represented by the formula VI instead of the compound represented by the formula I, the liquid crystal composition of comparative example 2 was decreased in Delta and crystallization occurred upon standing at-30 ℃ for 408 hours, relative to example 6. As can be seen, the liquid crystal composition of example 6 has a lower threshold voltage, better low temperature intersolubility, and is less prone to crystallization.
Comparative example 3
The formulation and corresponding properties of the liquid crystal compositions are shown in table 12 below.
TABLE 12 formulation and corresponding Properties of comparative example 3 liquid Crystal composition
Figure BDA0002012102890000252
Figure BDA0002012102890000261
Comparative example 3 Using CCP-2-OT of the formula IV instead of CCP-V-OT of the formula II, the liquid crystal composition γ of comparative example 3 being compared with example 61/K11The ratio of (a) to (b) is larger relative to example 6, and therefore, the response speed of the liquid crystal composition of example 6 is faster relative to the liquid crystal composition of comparative example 3.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.

Claims (9)

1. A liquid crystal composition comprising one or more compounds of formula I and one or more compounds of formula II,
Figure FDA0002012102880000011
in the formula I, 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; wherein R is1Any one or more-CH of the groups shown2-may optionally be replaced by cyclopentylene, cyclobutyl or cyclopropylene;
R2represents F, -CF3、-OCF3；
Figure FDA0002012102880000012
Each independently represent
Figure FDA0002012102880000013
Figure FDA0002012102880000014
m represents 1, 2 or 3;
n represents 0 or 1;
in the formula II, R3Represents an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms; wherein R is3Any one or more-CH of the groups shown2-may optionally be replaced by cyclopentylene, cyclobutyl or cyclopropylene.
2. The liquid crystal composition of claim 1, further comprising one or more compounds of formula III,
Figure FDA0002012102880000015
in the formula III, R4、R5Each independently represents an alkyl group having 1 to 10 carbon atoms, a C1-An alkoxy group having 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms or an alkenyloxy group having 3 to 8 carbon atoms;
Figure FDA0002012102880000016
each independently represent
Figure FDA0002012102880000017
3. The liquid crystal composition of claim 1, further comprising one or more compounds of formula IV,
Figure FDA0002012102880000018
in the formula IV, R6、R7Each 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, an alkenyl group having 2 to 10 carbon atoms, or an alkenyloxy group having 3 to 8 carbon atoms;
Figure FDA0002012102880000021
each independently represent
Figure FDA0002012102880000022
Or
Figure FDA0002012102880000023
4. The liquid crystal composition of claim 1, further comprising one or more compounds of formula V,
Figure FDA0002012102880000024
in the formula V, R8、R9Each 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;
Figure FDA0002012102880000025
to represent
Figure FDA0002012102880000026
Or
Figure FDA0002012102880000027
F1、F2、F3Each independently represents H or F, and F2、F3Not simultaneously F.
5. The liquid crystal composition of claim 1, further comprising one or more compounds of formula VI,
Figure FDA0002012102880000028
in formula VI, R10Represents 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; wherein R is10Any one or more of-CH2-may optionally be replaced by cyclopentylene, cyclobutyl or cyclopropylene;
Figure FDA0002012102880000029
each independently represent
Figure FDA00020121028800000210
Figure FDA00020121028800000211
Z1Represents 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；
q represents 0, 1 or 2.
6. The liquid crystal composition of claim 1, further comprising one or more compounds of formula VII,
Figure FDA0002012102880000031
in the formula VII, R11、R12Each 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; wherein R is11、R12Any one or more non-adjacent-CH2-may be optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene;
Z2represents a single bond, -CF2O-、-CH2CH2-or-CH2O-；Z3Represents a single bond, -CH2CH2-or-CH2O-；
Figure FDA0002012102880000032
Each independently represent
Figure FDA0002012102880000033
Figure FDA0002012102880000034
r represents 1 or 2; s represents 0, 1 or 2.
7. The liquid crystal composition of claim 1, further comprising one or more compounds of formula VIII,
Figure FDA0002012102880000035
in the formula VIII, R13、R14Each 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; w represents-O-, -S-or-CH2O-; wherein R is13、R14Any one or more non-adjacent-CH2-may optionally be replaced by cyclopentylene, cyclobutyl or cyclopropylene.
8. A liquid crystal display device comprising the liquid crystal composition according to any one of claims 1 to 7.
9. A liquid crystal display device as claimed in claim 8, wherein the display device is an active matrix display device or a passive matrix display device.
CN201910249913.XA 2019-03-29 2019-03-29 Liquid crystal composition and liquid crystal display element Active CN111748357B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910249913.XA CN111748357B (en) 2019-03-29 2019-03-29 Liquid crystal composition and liquid crystal display element

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910249913.XA CN111748357B (en) 2019-03-29 2019-03-29 Liquid crystal composition and liquid crystal display element

Publications (2)

Publication Number Publication Date
CN111748357A true CN111748357A (en) 2020-10-09
CN111748357B CN111748357B (en) 2023-09-05

Family

ID=72672148

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910249913.XA Active CN111748357B (en) 2019-03-29 2019-03-29 Liquid crystal composition and liquid crystal display element

Country Status (1)

Country Link
CN (1) CN111748357B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115678569A (en) * 2021-07-30 2023-02-03 晶美晟光电材料（南京）有限公司 Liquid crystal composition and application thereof

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110260104A1 (en) * 2010-04-27 2011-10-27 Chisso Petrochemical Corporation Liquid crystal composition and liquid crystal display device
CN104449761A (en) * 2014-11-20 2015-03-25 蒋战英 Liquid crystal compound containing difluoromethoxy bridged bonds and application thereof
CN104610983A (en) * 2015-01-21 2015-05-13 北京八亿时空液晶科技股份有限公司 Liquid crystal composition containing 2-methyl-3,4,5-trifluorobenzene liquid crystal compound and application of liquid crystal composition
CN104673323A (en) * 2015-02-04 2015-06-03 北京八亿时空液晶科技股份有限公司 Liquid crystal composition containing 2-methyl-3,4,5-trifluorophenyl liquid crystal compound and application thereof
CN105038815A (en) * 2015-07-13 2015-11-11 石家庄诚志永华显示材料有限公司 Liquid crystal composition
CN105130767A (en) * 2015-09-02 2015-12-09 石家庄诚志永华显示材料有限公司 Liquid crystal compound containing methylbenzene and difluoro methyleneoxy linking group and preparing method and application thereof
CN107406768A (en) * 2016-01-22 2017-11-28 东进世美肯株式会社 Liquid-crystal composition

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110260104A1 (en) * 2010-04-27 2011-10-27 Chisso Petrochemical Corporation Liquid crystal composition and liquid crystal display device
CN104449761A (en) * 2014-11-20 2015-03-25 蒋战英 Liquid crystal compound containing difluoromethoxy bridged bonds and application thereof
CN104610983A (en) * 2015-01-21 2015-05-13 北京八亿时空液晶科技股份有限公司 Liquid crystal composition containing 2-methyl-3,4,5-trifluorobenzene liquid crystal compound and application of liquid crystal composition
CN104673323A (en) * 2015-02-04 2015-06-03 北京八亿时空液晶科技股份有限公司 Liquid crystal composition containing 2-methyl-3,4,5-trifluorophenyl liquid crystal compound and application thereof
CN105038815A (en) * 2015-07-13 2015-11-11 石家庄诚志永华显示材料有限公司 Liquid crystal composition
CN105130767A (en) * 2015-09-02 2015-12-09 石家庄诚志永华显示材料有限公司 Liquid crystal compound containing methylbenzene and difluoro methyleneoxy linking group and preparing method and application thereof
CN107406768A (en) * 2016-01-22 2017-11-28 东进世美肯株式会社 Liquid-crystal composition

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115678569A (en) * 2021-07-30 2023-02-03 晶美晟光电材料（南京）有限公司 Liquid crystal composition and application thereof
CN115678569B (en) * 2021-07-30 2024-09-10 晶美晟光电材料（南京）有限公司 Liquid crystal composition and application thereof

Also Published As

Publication number Publication date
CN111748357B (en) 2023-09-05

Similar Documents

Publication Publication Date Title
CN103254906B (en) Liquid crystal composition containing difluoro methoxyl ether compounds
CN103254911B (en) Positive dielectric anisotropy liquid crystal combination with rapid response
CN111484857B (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN110358548B (en) Liquid crystal composition and liquid crystal display device
CN111484855A (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN111484856A (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN112980464A (en) Negative liquid crystal composition, liquid crystal display element and liquid crystal display
CN112079687A (en) Compound, liquid crystal composition, liquid crystal display element and liquid crystal display
CN112940754B (en) Negative liquid crystal composition, liquid crystal display element and liquid crystal display
CN112980462A (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN112940752A (en) Liquid crystal composition, liquid crystal display element or liquid crystal display
CN112920811B (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN111748357B (en) Liquid crystal composition and liquid crystal display element
CN103805210B (en) A kind of liquid-crystal composition for responding TFT-LCD fast
CN110964539B (en) Liquid crystal composition, high molecular liquid crystal alignment polymer, liquid crystal display element and liquid crystal display
CN103820128B (en) A kind of positive dielectric anisotropy liquid crystal composition
CN112080289A (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN113122272B (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN112080287B (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN111471468A (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN103351880B (en) Liquid crystal composition containing difluoromethoxy bridge polar monomer compound
CN111196928A (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN111334312A (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
WO2021134961A1 (en) Liquid crystal composition, liquid crystal display element, and liquid crystal display
CN112940750A (en) Liquid crystal composition, liquid crystal display element and liquid crystal display

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant