CN111117657A - Liquid crystal composition and liquid crystal display device thereof - Google Patents
Liquid crystal composition and liquid crystal display device thereof Download PDFInfo
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- CN111117657A CN111117657A CN201811272267.0A CN201811272267A CN111117657A CN 111117657 A CN111117657 A CN 111117657A CN 201811272267 A CN201811272267 A CN 201811272267A CN 111117657 A CN111117657 A CN 111117657A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 266
- 239000000203 mixture Substances 0.000 title claims abstract description 225
- 150000001875 compounds Chemical class 0.000 claims abstract description 214
- 125000004432 carbon atom Chemical group C* 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 2
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000002834 transmittance Methods 0.000 abstract description 18
- 230000004044 response Effects 0.000 abstract description 14
- 230000003287 optical effect Effects 0.000 abstract description 11
- 238000000149 argon plasma sintering Methods 0.000 abstract description 10
- 238000012360 testing method Methods 0.000 description 29
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 13
- 239000000758 substrate Substances 0.000 description 12
- 238000009472 formulation Methods 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 239000004611 light stabiliser Substances 0.000 description 7
- 230000006872 improvement Effects 0.000 description 6
- 125000003302 alkenyloxy group Chemical group 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000004988 Nematic liquid crystal Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 1
- 239000004986 Cholesteric liquid crystals (ChLC) Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
Classifications
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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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- 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
-
- 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
- G02F1/13706—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 the liquid crystal having positive dielectric anisotropy
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The present invention provides a liquid crystal composition comprising: at least one compound of the general formula I; at least one compound of the general formula II-1 and/or II-2; and at least one compound of the general formula M. The invention also provides a liquid crystal display device comprising the liquid crystal composition. The liquid crystal composition provided by the invention has suitably high dielectric anisotropy, suitably high optical anisotropy, suitably high clearing point, high transmittance and larger average elastic constant KaveSo that the liquid crystal display device comprising the liquid crystal composition has faster response speed, high contrast ratio, higher transmittance and relatively less light scattering.
Description
Technical Field
The invention relates to the field of liquid crystal materials, in particular to a liquid crystal composition and a liquid crystal display device thereof.
Background
The liquid crystal material is a mixture of organic rod-shaped small molecular compounds which have liquid fluidity and crystal anisotropy at a certain temperature. Liquid crystal display devices operate by utilizing optical anisotropy and dielectric anisotropy of liquid crystal materials themselves, and are currently widely used. The liquid crystal display device is classified into: phase Change (PC), Twisted Nematic (TN), Super Twisted Nematic (STN), Dynamic Scattering (DS), Ferroelectric (FLC), guest-host (GH), Electrically Controlled Birefringence (ECB), Optically Compensated Bend (OCB), in-plane switching (IPS), Vertical Alignment (VA), Fringe Field Switching (FFS), field-induced photo-reactive alignment (FPA), and the like.
These liquid crystal display elements include a liquid crystal composition having appropriate physical properties. General physical properties required for a liquid crystal compound as a component of a liquid crystal composition are as follows:
(1) stable chemical properties and stable physical properties;
(2) has a high clearing point (nematic phase-isotropic phase transition temperature);
(3) the lower limit temperature of a liquid crystal phase (such as an optically isotropic liquid crystal phase including a nematic phase, a cholesteric phase, a lamellar phase, and a blue phase);
(4) excellent compatibility with other liquid crystal compounds;
(5) dielectric anisotropy with appropriate magnitude; and
(6) having an optical anisotropy of suitable magnitude.
In modern technology, Liquid Crystal Displays (LCDs) have been rapidly developed due to their small size, light weight, low power consumption and excellent Display quality, and are widely used in portable electronic information products. As the size of a liquid crystal screen for a portable computer, an office application, a video application increases, in order to enable the liquid crystal display to be used for a large screen display and eventually replace a Cathode Ray Tube (CRT), there are still some problems to be solved, such as improvement of viewing angle characteristics, improvement of response speed, increase of contrast, improvement of transmittance, improvement of low temperature stability, and the like. The narrow viewing angle of the LCD means that the contrast ratio is significantly reduced when viewed from a direction perpendicular to the normal of the liquid crystal cell, and the phenomenon of gray scale and color inversion occurs when the viewing angle is large, which seriously affects the display quality of the LCD.
In the early 70 s of the last century, experimental studies have been conducted on the basic electro-optical characteristics of the IPS mode of nematic liquid crystals, both uniformly aligned and twisted, characterized in that a pair of electrodes is made on the same substrate, while the other substrate has no electrode, and the alignment of the liquid crystal molecules is controlled by a transverse electric field applied between the pair of electrodes, and thus this mode can also be called lateral field mode. In the IPS mode, nematic liquid crystal molecules are uniformly arranged in parallel between two substrates, and two polarizing plates are orthogonally arranged. In the IPS mode, when no electric field is applied, incident light is blocked by two orthogonal polarizing plates to be in a dark state, and when an electric field is applied, liquid crystal molecules rotate to cause retardation, so that light leaks from the two orthogonal polarizing plates. The IPS mode panel has advantages of large viewing angle and accurate color restoration, but has disadvantages of severe light leakage, slow response speed, and large power consumption.
With the wide application of TFT-type LCDs, the performance requirements of TFT-type LCDs are continuously increasing, and high display image quality requires faster response speed, lower power consumption, and higher low-temperature reliability, and in addition, higher contrast and transmittance are required, especially for IPS-type liquid crystal display modes. This means that liquid crystal materials are required to have higher contrast and transmittance, higher elastic modulus, faster response speed, higher dielectric constant and low temperature reliability, and improvement of these properties is required.
The skilled person finds, based on the conventional IPS-LCD light leakage test, that the main factors causing the light leakage problem of the liquid crystal display device are: light scattering (LC scattering), rubbing uniformity (rubbing uniformity), color filter light leakage (CF/TFT scattering), and polarization ability (polarization ability), wherein light scattering accounts for 63% of the factors affecting light leakage.
According to the following relationship:
in order to improve the light scattering of the liquid crystal material, it is necessary to increase the average elastic constant Kave(wherein,
) To improve light scattering; at the increase of KaveIn the case of (2), light leakage of the liquid crystal material can be reduced.
Further, the Contrast (CR) and the luminance (L) are related as follows:
CR＝L255/L0×100％，
wherein L is255Is at on-state brightness, L0Is off state brightness. It can be seen that what significantly affects CR should be L0A change in (c). In the off state, L0The smaller the light scattering (LC scattering), L, is, independent of the dielectric of the liquid crystal molecules, in relation to the light scattering (LC scattering) of the liquid crystal material itself0The smaller the Contrast Ratio (CR) will be, the more significantly the contrast ratio will be.
In view of the above, the transmittance of the liquid crystal material can be increased by increasing the average elastic constant K of the liquid crystal compositionaveThe value of (b) makes the degree of order of the liquid crystal molecules better and the light leakage less, thereby improving the transmittance.
Therefore, there is a need for a liquid crystal composition that can ensure a high transmittance of the liquid crystal composition and that has properties such as a suitably high clearing point, a fast response speed, a high optical anisotropy, and a high dielectric anisotropy at the same time.
Disclosure of Invention
The purpose of the invention is as follows: the object of the present invention is to provide a transparent resin composition having suitably high dielectric anisotropy, suitably high optical anisotropy, suitably high clearing point, high transmittance, and large average elastic constantKaveThe liquid crystal composition of (1). The invention also aims to provide a liquid crystal display device comprising the liquid crystal composition.
The technical scheme of the invention is as follows:
in order to achieve the above object, the present invention provides a liquid crystal composition comprising:
at least one compound of the general formula I
At least one compound of the general formulae II-1 and/or II-2
at least one compound of the formula M
Wherein,
R1represents a linear or branched alkyl group having 1 to 12 carbon atoms, 1 or not adjacent 2 or more-CH in the linear or branched alkyl group having 1 to 12 carbon atoms2-may be independently replaced by-C-, -C ≡ C-, -O-, -CO-O-, or-O-CO-, respectively, and one or more-H of said linear or branched alkyl groups containing 1 to 12 carbon atoms may be independently substituted by-F or-Cl, respectively;
RA1and RA2Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
1 or non-adjacent 2 or more-CH in the linear or branched alkyl containing 1 to 12 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-, respectively, and one or more-H present in these groups may be independently substituted by-F or-Cl, respectively;
RM1and RM2Each independently represents-H, a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkenyl group having 2 to 12 carbon atoms,
1 or non-adjacent 2 or more-CH in the straight chain or branched chain alkyl containing 1 to 12 carbon atoms2-may be independently replaced by-C.ident.C-, -O-, -CO-O-or-O-CO-;
ring (C)
To represent
Wherein,
may be substituted by-CN, -F or-Cl, and one or more rings may be substituted by-CH ═ by-N;
ring (C)
Ring (C)
Ring (C)
And ring
Each independently represent
Wherein,
one or more-CH2-may be replaced by-O-, one or more of the ring single bonds may be replaced by double bonds,
wherein one or more-H may be substituted by-CN, -F or-Cl, and one or more ring-CH may be substituted by-N ═ N;
ring (C)
Ring (C)
And ring
Each independently represent
Wherein,
one or more-CH of2-can be replaced by-O-,
at most one-H in (a) may be substituted by halogen;
ZA11represents a single bond, -CH2CH2-、-CF2CF2-、-CF2O-、-OCF2-、-CO-O-、-O-CO-、-O-CO-O-、 -CH＝CH-、-C≡C-、-CF＝CF-、-CH2O-or-OCH2-；
ZA21And ZA22Each independently represents a single bond, -CH2CH2-、-CF2CF2-、-CO-O-、-O-CO-、-O-CO-O-、 -CH＝CH-、-C≡C-、-CF＝CF-、-CH2O-or-OCH2-；
ZM1And ZM2Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-、-OCH2-、-CH＝CH-、 -C≡C-、-CH2CH2-or- (CH)2)4-；
LA11、LA12、LA13、LA21、LA22、LA23And LA24Each independently represents-H, -F, -CH3or-Cl;
XA1and XA2Each independently represents halogen, haloalkyl or haloalkoxy having 1 to 5 carbon atoms, haloalkenyl or haloalkenyloxy having 2 to 5 carbon atoms;
nA1and nA2Each independently represents 0, 1, 2 or 3, when nA1When 2 or 3, ring
May be the same or different, ZA11May be the same or different, and when n isA2When 2 or 3, ring
May be the same or different, ZA21May be the same or different;
nM1represents 0, 1, 2 or 3, and when nM1When 2 or 3, ring
May be the same or different, ZM2May be the same or different;
when Z isA21And ZA22Represents a single bond and nA2When 1, a ring
And ring
Is not simultaneously represented
And is
The compounds of formula II-2 do not comprise the compounds of formula I.
In some embodiments of the present invention, the dielectric anisotropy of the compounds of formula I and of the compounds of formula II-1 and/or II-2 is positive.
In some embodiments of the invention, the chemical structures of the compound of formula I and the compound of formula II-2 are different.
In some embodiments of the invention, the absolute value of the dielectric anisotropy of the compound of formula M is not more than 3; preferably, the absolute value of the dielectric anisotropy of the compound of the formula M does not exceed 2.
In some embodiments of the invention, the compound of formula i has a strong rigid biphenyl structure, which can effectively adjust the birefringence, elastic constant, contrast, etc. of the liquid crystal composition; the content of the compound of the formula I is desirably adjusted depending on the desired properties such as transmittance, contrast, birefringence, process adaptability, dropping marks, burn-in, dielectric anisotropy, and the like.
The compounds of the general formula I preferably represent the liquid crystal compositions according to the invention in a weight ratio: the preferred lower limit of the weight percentage of the compound of formula i in the liquid crystal composition of the present invention relative to the total weight of the liquid crystal composition of the present invention is 0.1%, 0.5%, 1%, 2%, 3%, 4%, 5%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 20% or 30%; the upper limit of the weight percentage of the compound of formula I in the liquid crystal composition of the present invention is preferably 50%, 45%, 40%, 35%, 30%, 28%, 27%, 26%, 25.5%, 25%, 24.5%, 24%, 22%, 20%, 18%, 16% or 15% relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the invention, the compound of formula I is present in an amount of from 0.1% to 50% by weight of the liquid crystal composition.
In some embodiments of the invention, in the compounds of formula I, R1Preferably a linear or branched alkyl or alkoxy group having 1 to 8 carbon atoms, a linear or branched alkenyl or alkenyloxy group having 2 to 8 carbon atoms.
In some embodiments of the invention, the ring
Can be expressed as
Preferably, it is
Further preferred is
Particularly preferably
In some embodiments of the invention, the compound of formula i is selected from the group consisting of:
in some embodiments of the present invention, the liquid crystal compositions of the present invention preferably comprise at least one compound of formula I; more preferably at least one compound of the formula I-1; particular preference is given to compounds of the formula I-1 which contain from 2 to 10 species.
In some embodiments of the invention, in the compounds of formula I, R1Preferably a linear or branched alkyl or alkoxy group having 2 to 8 carbon atoms, a linear or branched alkenyl or alkenyloxy group having 2 to 8 carbon atoms; in particular, in the compounds of the formula I R1The compound, preferably a linear or branched alkyl group having 2 to 8 carbon atoms, may provide a liquid crystal composition comprising the compound of formula i with high optical anisotropy.
In some embodiments of the invention, the ring
Ring (C)
Ring (C)
And ring
Each independently represent
In some embodiments of the present invention, the compound of formula II-1 is selected from the group consisting of:
wherein,
RA1represents a straight-chain or straight-chain alkyl group having 1 to 12 carbon atoms, 1 or not adjacent 2 or more-CH in the straight-chain or straight-chain alkyl group having 1 to 12 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-, respectively.
In some embodiments of the present invention, the compound of formula II-2 is selected from the group consisting of:
wherein,
RA2represents a linear or branched alkyl group having 1 to 8 carbon atoms, 1 or not adjacent 2 or more-CH in the linear or branched alkyl group having 1 to 8 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-, respectively, and one or more-H present in these groups may be independently substituted by-F or-Cl, respectively.
As to the weight percentage of the compound of the formula II-1 and/or the formula II-2 to the liquid crystal composition of the present invention, it is preferable: the lower limit of the preferred weight percentage of the compound of formula II-1 and/or II-2 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 1%, 3%, 5%, 7%, 9%, 10%, 12%, 15%, 18%, 20%, 30% or 40%; the upper limit of the weight percentage of the compound of the formula II-1 and/or the formula II-2 in the liquid crystal composition of the present invention is preferably 75%, 70%, 65%, 60%, 55%, 50%, 45%, 35% or 25% with respect to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the present invention, the compounds of formula II-1 and/or formula II-2 comprise from 1% to 75% by weight of the total liquid crystal composition.
In some embodiments of the present invention, the compound of formula II-1 is preferably a compound having an absolute value of dielectric anisotropy of greater than 4.
In some embodiments of the present invention, preferably, the compound of formula II-1 is preferably selected from the group consisting of at least one compound of formulae II-1-1, II-1-3, II-1-5, II-1-6, II-1-8 to II-1-10, II-1-12 to II-1-20, II-1-22 to II-1-25, II-1-27, II-1-30, II-1-31, II-1-33, II-1-35, II-1-40, II-1-42, II-1-44, and II-1-50 to II-1-57; further preferably, the compound of the formula II-1 is selected from the group consisting of at least two compounds of the formulae II-1-1, II-1-3, II-1-5, II-1-6, II-1-8 to II-1-10, II-1-12 to II-1-20, II-1-22 to II-1-25, II-1-27, II-1-30, II-1-31, II-1-33, II-1-35, II-1-40, II-1-42, II-1-44, and II-1-50 to II-1-57; still further preferably, the compound of the formula II-1 is selected from the group consisting of at least three compounds of the formulae II-1-1, II-1-3, II-1-5, II-1-6, II-1-8 to II-1-10, II-1-12 to II-1-20, II-1-22 to II-1-25, II-1-27, II-1-30, II-1-31, II-1-33, II-1-35, II-1-40, II-1-42, II-1-44, and II-1-50 to II-1-57.
In some embodiments of the present invention, the compound of formula II-1 is preferably selected from the group consisting of formula II-1-1, formula II-1-3, formula II-1-5, formula II-1-6, formula II-1-16, formula II-1-22, formula II-1-24, formula II-1-29, formula II-1-33, compounds of the general formula II-1-36, the general formula II-1-37, the general formula II-1-50, the general formula II-1-51, the general formula II-1-52, the general formula II-1-53, the general formula II-1-54, the general formula II-1-55, the general formula II-1-56 and the general formula II-1-57.
In some embodiments of the present invention, it is preferred that the liquid crystal composition of the present invention comprises at least one compound of formula II-2; more preferably at least one compound of the general formulae II-2-1 to II-2-3, II-2-15 to II-2-20, II-2-24, II-2-26, II-2-28 to II-2-33; further preferably 2 to 12 compounds of the general formulae II-2-1 to II-2-3, II-2-15 to II-2-20, II-2-24, II-2-26, II-2-28 to II-2-33; further preferably 2 to 10 compounds of the general formulae II-2-1 to II-2-3, II-2-15 to II-2-20, II-2-24, II-2-26, II-2-28 to II-2-33; still more preferably 2 to 8 kinds of compounds of the general formulae II-2-1 to II-2-3, II-2-15 to II-2-20, II-2-24, II-2-26, II-2-28 to II-2-33.
In some embodiments of the present invention, the compound of formula II-2 is preferably selected from the group consisting of compounds of formula II-2-1, formula II-2-2, formula II-2-3, formula II-2-5, formula II-2-10, formula II-2-15, formula II-2-16, formula II-2-17, formula II-2-19, formula II-2-20, formula II-2-24, formula II-2-26, formula II-2-28, formula II-2-29, formula II-2-30, and formula II-2-32.
The weight percentage of the compound of formula II-1 in the liquid crystal composition of the present invention is preferably: the lower limit of the preferred weight percentage of the compound of formula II-1 to the liquid crystal composition of the present invention is 1%, 3%, 5%, 7%, 10%, 13%, 14%, 15%, 18%, 20%, 23%, 25%, 28% or 30%, 33%, 35%, 38% or 40% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the amount of the compound of the formula II-1 in the liquid crystal composition of the present invention is preferably 55%, 52%, 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15% or 10% by weight relative to the total weight of the liquid crystal composition of the present invention.
The weight percentage of the compound of formula II-2 in the liquid crystal composition of the present invention is preferably: the lower limit of the preferred weight percentage of the compound of formula II-2 to the liquid crystal composition of the present invention is 0%, 1%, 3%, 5%, 10%, 13%, 14%, 15%, 18%, 20%, 23%, 25%, 28%, 30%, 33%, 35% or 38% relative to the total weight of the liquid crystal composition of the present invention; the upper limit of the amount of the compound of the general formula II-2 in the liquid crystal composition of the present invention is preferably 50%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23%, 20%, 18%, 15% or 10% by weight relative to the total weight of the liquid crystal composition of the present invention.
In some embodiments of the present invention, when it is desired to keep the viscosity of the liquid crystal composition of the present invention low and the response time short, it is preferable that the lower limit value and the upper limit value of the total weight percentage of the compounds of formula II-1 and/or formula II-2 are slightly lower, wherein the lower limit value is preferably: 3%, 5%, 10%, 13%, 14%, 15%, 18%, 20%, 23%, 25%, 28%, 30%, 33%, 35%, 38% or 40%, and the upper limit value is preferably: 50%, 48%, 46%, 43%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23% or 20%; further, when it is desired to maintain the liquid crystal composition of the present invention having a high clearing point and good temperature stability, it is preferable that the lower limit value and the upper limit value of the total weight percentage of the compounds of the general formula II-1 and/or the general formula II-2 are slightly lower, wherein the lower limit value is preferably: 5%, 10%, 13%, 14%, 15%, 18%, 20%, 23%, 25%, 28% or 30%, and the upper limit value is preferably: 50%, 45%, 40%, 38%, 35%, 33%, 30%, 28% or 25%. In addition, when the dielectric anisotropy is increased in order to keep the driving voltage low, the lower limit of the total weight percentage of the compounds of the general formula II-1 and/or the general formula II-2 is preferably increased, and the upper limit thereof is preferably increased, wherein the lower limit is preferably: 10%, 13%, 14%, 15%, 18%, 20%, 23%, 25%, 28% or 30%, and the upper limit value is preferably: 70%, 68%, 65%, 63%, 60%, 55%, 50%, 40%, 38%, 35%, 33%, 30%, 28% or 25%.
In some embodiments of the present invention, the compound of formula M is effective in improving clearing point, response time, contrast and low temperature stability of the liquid crystal composition.
In some embodiments of the invention, in the compound of formula M, RM1And RM2Each independently preferably a linear or branched alkyl group having 1 to 10 carbon atoms, a linear or branched alkoxy group having 1 to 9 carbon atoms, a linear or branched alkenyl group having 2 to 10 carbon atoms, or a linear or branched alkenyloxy group having 2 to 10 carbon atoms; further preferably a linear or branched alkyl group having 1 to 8 carbon atoms, a linear or branched alkoxy group having 1 to 7 carbon atoms, or a linear or branched alkenyl group having 2 to 8 carbon atoms; still more preferably a linear or branched alkyl group having 1 to 5 carbon atoms, a linear or branched alkoxy group having 1 to 5 carbon atoms, or a linear or branched alkenyl group having 2 to 5 carbon atoms.
In some embodiments of the invention, preferably, RM1And RM2One or both of which are linear or branched alkenes containing 2 to 8 carbon atomsA group; further preferably, RM1And RM2One or both of them are straight chain or branched chain alkenyl groups having 2 to 5 carbon atoms.
In some embodiments of the invention, preferably, RM1And RM2One is a linear or branched alkenyl group having 2 to 5 carbon atoms, and the other is a linear or branched alkyl group having 1 to 5 carbon atoms.
In some embodiments of the invention, preferably, RM1And RM2Both are a linear or branched alkyl group having 1 to 8 carbon atoms or a linear or branched alkoxy group having 1 to 7 carbon atoms; more preferably a linear or branched alkyl group having 1 to 5 carbon atoms or a linear or branched alkoxy group having 1 to 4 carbon atoms.
In some embodiments of the invention, preferably, RM1And RM2One is a linear or branched alkyl group having 1 to 5 carbon atoms, and the other is a linear or branched alkyl group having 1 to 5 carbon atoms, or a linear or branched alkoxy group having 1 to 4 carbon atoms; further preferably, RM1And RM2Both are straight-chain or branched alkyl groups having 1 to 5 carbon atoms.
The alkenyl group in the present invention is preferably selected from groups represented by any one of formulae (V1) to (V9), and particularly preferably formula (V1), formula (V2), formula (V8), or formula (V9). The groups represented by formulae (V1) to (V9) are shown below:
wherein denotes the carbon atom in the ring structure to which it is bonded.
The alkenyloxy group in the present invention is preferably selected from groups represented by any one of formulae (OV1) to (OV9), and particularly preferably formula (OV1), formula (OV2), formula (OV8), or formula (OV 9). The groups represented by formulae (OV1) to (OV9) are as follows:
wherein denotes the carbon atom in the ring structure to which it is bonded.
In some embodiments of the invention, the compound of formula M is selected from the group consisting of:
in some embodiments of the present invention, the content of the compound of formula M must be properly adjusted depending on desired properties such as solubility at low temperature, transition temperature, electrical reliability, birefringence, process adaptability, drop trace, burn-in, dielectric anisotropy, and the like.
The weight percentage of the compound of formula M in the liquid crystal composition of the present invention is preferably: the lower limit of the preferred weight percentage of the compound of formula M in the liquid crystal composition of the present invention with respect to the total weight of the liquid crystal composition of the present invention is 1%, 2%, 3%, 5%, 7%, 10%, 12%, 14%, 16%, 18%, 20%, 22%, 24%, 26%, 28%, 30%, 32%, 34%, 36%, 38%, 40%, 42%, 45%, 48% or 50%; the upper limit of the percentage by weight of the compound of formula M in the liquid crystal composition of the invention is preferably 80%, 75%, 70%, 65%, 60%, 55%, 50%, 45%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 22% or 20% relative to the total weight of the liquid crystal composition of the invention.
In some embodiments of the present invention, the compound of formula M is particularly preferably selected from the group consisting of compounds of formula M1, formula M2, formula M3, formula M7, formula M8, formula M9, formula M11, formula M12, formula M13, formula M14, formula M17, formula M18, formula M19, formula M20 and formula M21.
In some embodiments of the invention, the compound of formula M is preferably selected from the group consisting of compounds of formula M1, formula M2, formula M3, formula M7, formula M8, formula M9, formula M11, formula M12, formula M14, formula M17, formula M18, formula M19, and formula M20.
In case reliability is important, R is contained in the group consisting of compounds of formula M1, formula M2, formula M3, formula M7, formula M8, formula M9, formula M11, formula M12, formula M13, formula M14, formula M17, formula M18, formula M19, formula M20 and formula M21M1And RM2Compounds which are all alkyl; in the case where importance is attached to the reduction of the volatility of the compound, R is contained in a group consisting of compounds of formula M1, formula M2, formula M3, formula M7, formula M8, formula M9, formula M11, formula M12, formula M13, formula M14, formula M17, formula M18, formula M19, formula M20 and formula M21M1And RM2Compounds which are all alkoxy groups; and when importance is attached to the reduction in viscosity, R is contained in a group consisting of compounds of formula M1, formula M2, formula M3, formula M7, formula M8, formula M9, formula M11, formula M12, formula M13, formula M14, formula M17, formula M18, formula M19, formula M20 and formula M21M1And RM2A compound in which at least one is alkenyl.
In some embodiments of the present invention, the compound of formula M1 is particularly preferably selected from the group consisting of:
wherein,
RM1represents a linear or branched alkyl or alkoxy group having 1 to 8 carbon atoms, or a linear or branched alkenyl or alkenyloxy group having 2 to 8 carbon atoms; and is
RM11And RM21Each independently represents a linear or branched alkyl or alkoxy group containing 1 to 8 carbon atoms.
The weight percentage of the compound of formula M1 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M1 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 1%, 2%, 3%, 5%, 7%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50% or 55%; the upper limit of the preferred weight percentage of the compound of formula M1 in the liquid crystal composition according to the invention is 70%, 65%, 60%, 55%, 50%, 45%, 40%, 35%, 30% or 25% relative to the total weight of the liquid crystal composition according to the invention.
In some embodiments of the invention, the compound of formula M1 is preferably selected from the group consisting of compounds of formula M1-a and formula M1-b.
In some embodiments of the invention, the compound of formula M1 is preferably selected from the group consisting of compounds of formula M1-a, formula M1-b, and formula M1-h.
In some embodiments of the invention, RM1Preferably a linear or branched alkyl group having 1 to 5 carbon atoms or a linear or branched alkenyl group having 2 to 5 carbon atoms; further preferably a linear or branched alkyl or alkenyl group having 2 to 5 carbon atoms.
In some embodiments of the present invention, R in the compounds of the formula M1-a and of the formula M1-b is particularly preferred for the particular improvement of the response timesM1A compound which is ethyl or n-propyl.
R in the compound of the formula M1-a relative to the total weight of the liquid crystal composition of the inventionM1The lower limit value of the compound representing an ethyl group or an n-propyl group in the weight percentage of the liquid crystal composition of the present invention is preferably 0%, 1%, 5%, 10%, 15%, 17%, 20%, 23%, 25%, 27% or 30%; r in the compound of the formula M1-a relative to the total weight of the liquid crystal composition of the inventionM1The upper limit of the compound representing an ethyl group or an n-propyl group in the liquid crystal composition of the present invention is preferably 60%, 55%, 50%, 45%, 42%, 40%, 38%, 35%, 33%, 30%, 28% or 25% by weight.
R in the compound of the formula M1-b relative to the total weight of the liquid crystal composition of the inventionM1The lower limit value of the compound representing the n-propyl group, which is preferably 0%, 1%, 2%, 3%, 5%, 7% or 10% by weight of the liquid crystal composition of the present invention; r in the compound of the formula M1-b relative to the total weight of the liquid crystal composition of the inventionM1The upper limit value of the compound representing the n-propyl group in the liquid crystal composition of the present invention is preferably 30%, 25%, 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5% or 3% by weight.
In some embodiments of the invention, it is preferred for the clearing point that R in the compound of formula M1 is R when it is desired to obtain a higher clearing point by the compound of formula M1M1A compound represented by butyl or pentyl; further preferred is R in the compound of formula M1M1A compound represented by n-butyl or n-pentyl.
R in the compounds of the formula M1-a and/or M1-b relative to the total weight of the liquid-crystal composition of the inventionM1The preferred lower limit value of the weight percentage of the compound representing n-butyl or n-pentyl group to the liquid crystal composition of the present invention is 0%, 1%, 3%, 5%, 8%, 10%, 15%, 17%, 20%, 23%, 25%, 27% or 30%; r in the compounds of the formula M1-a and/or M1-b relative to the total weight of the liquid-crystal composition of the inventionM1The upper limit value of the compound representing n-butyl or n-pentyl group preferably accounts for 60%, 55%, 50%, 45%, 42%, 40%, 38%, 35%, 33%, 30%, 28%, 25%, 23% or 20% by weight of the liquid crystal composition of the present invention.
The preferred lower limit of the weight percentage of the compound of formula M1-c in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 5%, 10%, 13%, 15%, 17% or 20%; the upper limit value of the compound of the formula M1-c in the weight percent of the liquid crystal composition of the invention is preferably 25%, 23%, 20%, 17%, 15%, 13% or 10% relative to the total weight of the liquid crystal composition of the invention.
The preferred lower limit of the weight percentage of the compound of formula M1-d in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 5%, 10%, 13%, 15%, 17% or 20%; the upper limit value of the compound of the formula M1-d in a weight percentage of the liquid crystal composition of the invention is preferably 25%, 23%, 20%, 17%, 15%, 13% or 10% relative to the total weight of the liquid crystal composition of the invention.
The preferred lower limit of the weight percentage of the compound of formula M1-e to the liquid crystal composition of the invention is 0%, 1%, 5%, 10%, 13%, 15%, 17% or 20% relative to the total weight of the liquid crystal composition of the invention; the upper limit of the preferred weight percentage of the compound of formula M1-e to the liquid crystal composition of the invention is 25%, 23%, 20%, 17%, 15%, 13% or 10% relative to the total weight of the liquid crystal composition of the invention.
The preferred lower limit of the weight percentage of the compound of formula M1-f in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 5%, 10%, 13%, 15%, 17% or 20%; the upper limit value of the compound of formula M1-f in the weight percent of the liquid crystal composition of the invention is preferably 25%, 23%, 20%, 17%, 15%, 13% or 10% relative to the total weight of the liquid crystal composition of the invention.
The preferred lower limit of the weight percentage of the compound of formula M1-g to the liquid crystal composition of the invention is 0%, 1%, 5%, 10%, 13%, 15%, 17% or 20% relative to the total weight of the liquid crystal composition of the invention; the upper limit of the preferred weight percentage of the compound of formula M1-g to the liquid crystal composition of the invention is 25%, 23%, 20%, 17%, 15%, 13% or 10% relative to the total weight of the liquid crystal composition of the invention.
In some embodiments of the invention, R in compounds of formula M1-f and formula M1-g is preferredM1A compound which is ethyl or n-propyl.
R in the compounds of the formula M1-f and/or M1-g relative to the total weight of the liquid-crystal composition of the inventionM1The preferred lower limit of the weight percentage of the compound being ethyl or n-propyl in the liquid crystal composition of the present invention is 0%, 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18% or 20%; r in the compounds of the formula M1-f and/or M1-g relative to the total weight of the liquid crystal composition of the inventionM1The upper limit of the preferred weight percentage of the compound which is ethyl or n-propyl in the liquid crystal composition of the present invention is 20%, 17%, 15%, 13%, 10%, 8%, 7% or 6%.
In some embodiments of the invention, in the compounds of formula M1-h, RM11Preferably a linear or branched alkyl or alkoxy group having 1 to 7 carbon atoms; further preferably a straight-chain or branched alkyl group or alkoxy group having 1 to 5 carbon atoms.
The preferred lower limit of the weight percentage of the compound of formula M1-h to the liquid crystal composition of the invention is 0%, 1%, 3%, 5%, 7%, 10%, 13%, 15%, 17%, 20%, 23%, 25% or 30% relative to the total weight of the liquid crystal composition of the invention; the preferred upper limit of the weight percentage of the compound of formula M1-h to the liquid crystal composition of the invention is 60%, 55%, 50%, 45%, 40%, 37%, 35%, 33%, 30%, 27%, 25%, 23%, 20%, 17%, 15%, 13% or 10% relative to the total weight of the liquid crystal composition of the invention.
In order to improve the response times of the liquid-crystal compositions according to the invention in particular, preference is given to R in the compounds of the formula M1-hM11Is ethyl, n-propyl, butyl or pentyl, and RM21A compound that is methyl or methoxy; r in the compounds of the formula M1-hM11Is ethyl, n-propyl, butyl or pentyl, and RM21A compound that is ethyl or ethoxy; r in the compounds of the formula M1-hM11Is n-propyl, butyl or pentyl, and RM21A compound that is n-propyl or propoxy.
R in the compounds of the formula M1-h relative to the total weight of the liquid-crystal composition of the inventionM11Is n-propyl and RM21The weight percentage of the compound which is an ethyl group in the liquid crystal composition of the present invention is preferablyThe lower limit value is selected to be 0%, 1%, 2%, 3%, 5%, 7%, 10%, 13%, 15%, 18% or 20%; r in the compounds of the formula M1-h relative to the total weight of the liquid-crystal composition of the inventionM11Is n-propyl and RM21The upper limit of the preferred weight percentage of the compound which is an ethyl group in the liquid crystal composition of the present invention is 20%, 17%, 15%, 13%, 10%, 8%, 7% or 6%.
The weight percentage of the compound of formula M2 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M2 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 2%, 3%, 5%, 7% or 10%; the upper limit value of the compound of formula M2 in a preferred weight percentage of the liquid crystal composition of the invention is 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5% or 3% relative to the total weight of the liquid crystal composition of the invention.
The weight percentage of the compound of formula M3 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M3 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 2%, 3%, 5%, 7% or 10%; the upper limit value of the compound of formula M3 in a preferred weight percentage of the liquid crystal composition of the invention is 20%, 15%, 13%, 10%, 8%, 7%, 6%, 5% or 3% relative to the total weight of the liquid crystal composition of the invention.
The weight percentage of the compound of formula M7 in the liquid crystal composition of the invention is preferably: the preferred lower limit value of the weight percentage of the compound of formula M7 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35% or 40%; the upper limit of the preferred weight percentage of the compound of formula M7 in the liquid crystal composition of the invention is 50%, 40%, 35%, 30%, 20%, 15%, 10% or 5% relative to the total weight of the liquid crystal composition of the invention.
In some embodiments of the present invention, it is preferable to contain R in the compound of the formula M7 in view of required properties of solubility at low temperature, transition temperature, electrical reliability, birefringence and the likeM1Is a linear or branched alkenyl radical having 2 to 4 carbon atoms, and RM2Is CH3The compound of (a), the straight-chain or branched alkenyl group having 2 to 4 carbon atoms is more preferably
R in the compound of formula M7 relative to the total weight of the liquid crystal composition of the inventionM1Is composed of
And R isM2Is CH3The lower limit of the weight percentage of the compound of (a) to the liquid crystal composition of the present invention is preferably 0%, 1%, 3%, 5%, 7%, 9%, 11%, 12%, 13%, 18% or 21%, and the upper limit is preferably 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10% or 8%. When both compounds are contained, the lower limit of the weight percentage of the two compounds in the liquid crystal composition of the present invention is preferably 2%, 3%, 5%, 7%, 9%, 11%, 13%, 15%, 19%, 24% or 30%, and the upper limit thereof is preferably 45%, 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 11%, 9%, 7% or 5%, with respect to the total weight of the liquid crystal composition of the present invention.
The weight percentage of the compound of formula M8 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M8 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 2%, 3%, 4%, 5%, 7%, 10%, 14%, 16% or 20%; the preferred upper limit of the weight percentage of the compound of formula M8 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 40%, 35%, 30%, 20%, 15%, 10% or 5%.
In some embodiments of the present invention, it is preferable to contain R in the compound of the formula M8 in view of required properties of solubility at low temperature, transition temperature, electrical reliability, birefringence and the likeM1Is a linear or branched alkenyl radical having 2 to 4 carbon atoms, and RM2Is CH3The compound of (a), the straight-chain or branched alkenyl group having 2 to 4 carbon atoms is more preferably
R in the compound of formula M8 relative to the total weight of the liquid crystal composition of the inventionM1Is composed of
And R isM2Is CH3The lower limit of the weight percentage of the compound of (a) to the liquid crystal composition of the present invention is preferably 0%, 1%, 3%, 4%, 5%, 7%, 9%, 11%, 12%, 13%, 18% or 20%, and the upper limit is preferably 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15%, 13%, 10% or 8%. When both the two compounds are contained, the weight percentage of the two compounds in the liquid crystal composition of the present invention is preferably 3%, 5%, 7%, 9%, 11%, 13%, 15%, 19%, 24% or 30% in the lower limit, and is preferably 40%, 35%, 30%, 25%, 23%, 20%, 18%, 15% or 13% in the upper limit, relative to the total weight of the liquid crystal composition of the present invention.
The weight percentage of the compound of formula M9 in the liquid crystal composition of the invention is preferably: the preferred lower limit value of the weight percentage of the compound of formula M9 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35% or 40%; the upper limit of the preferred weight percentage of the compound of formula M9 in the liquid crystal composition of the invention is 50%, 40%, 35%, 30%, 20%, 15%, 10% or 5% relative to the total weight of the liquid crystal composition of the invention.
In some embodiments of the invention, the compound of formula M9 is preferably RM1Is ethyl, propyl, butyl or pentyl, and RM2A compound that is methyl or ethyl; or preferably RM1Is composed of
And R isM2A compound that is methyl, ethyl or n-propyl; or preferably RM1Is n-propyl, n-butyl or n-pentyl, and RM2Is CH3A compound of O-.
The weight percentage of the compound of formula M11 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M11 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16%, 20%, 23%, 26%, 30%, 35% or 40%; the upper limit value of the compound of formula M11 in the weight percent of the liquid crystal composition of the invention is preferably 50%, 40%, 35%, 30%, 20%, 15%, 10% or 5% relative to the total weight of the liquid crystal composition of the invention.
In some embodiments of the invention, the compound of formula M11 is preferably RM1And RM2Each independently represents a linear or branched alkyl group containing 2 to 5 carbon atoms, or preferably RM1And RM2One of them is
And the other is CH3-or C2H5-a compound of (a).
The weight percentage of the compound of formula M12 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M12 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 2%, 3%, 5%, 7%, 10%, 12%, 14%, 16%, 18%, 20%, 23%, 26%, 30%, 35% or 40%; the upper limit of the preferred weight percentage of the compound of formula M12 in the liquid crystal composition of the invention is 50%, 40%, 35%, 30%, 25%, 22%, 20%, 18%, 15%, 12%, 10%, 8% or 5% relative to the total weight of the liquid crystal composition of the invention.
The weight percentage of the compound of formula M13 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M13 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 2%, 3%, 5%, 7%, 10%, 12%, 14%, 16%, 18%, 20%, 23%, 26%, 30%, 35% or 40%; the upper limit of the preferred weight percentage of the compound of formula M13 in the liquid crystal composition of the invention is 50%, 40%, 35%, 30%, 25%, 22%, 20%, 18%, 15%, 12%, 10%, 8% or 5% relative to the total weight of the liquid crystal composition of the invention.
The weight percentage of the compound of formula M14 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M14 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 2%, 3%, 5%, 7%, 10%, 12%, 14%, 16%, 18%, 20%, 23%, 26%, 30%, 35% or 40%; the upper limit of the preferred weight percentage of the compound of formula M14 in the liquid crystal composition of the invention is 50%, 40%, 35%, 30%, 25%, 22%, 20%, 18%, 15%, 12%, 10%, 8% or 5% relative to the total weight of the liquid crystal composition of the invention.
The weight percentage of the compound of formula M15 in the liquid crystal composition of the invention is preferably: the preferred lower limit of the weight percentage of the compound of formula M15 in the liquid crystal composition of the invention relative to the total weight of the liquid crystal composition of the invention is 0%, 1%, 2%, 3%, 5%, 7%, 10%, 12%, 14%, 16%, 18%, 20%, 23%, 26%, 30%, 35% or 40%; the upper limit of the preferred weight percentage of the compound of formula M15 in the liquid crystal composition of the invention is 50%, 40%, 35%, 30%, 25%, 22%, 20%, 18%, 15%, 12%, 10%, 8% or 5% relative to the total weight of the liquid crystal composition of the invention.
The weight percentage of the compounds of formulae M17 to M21 in the liquid crystal composition of the present invention is preferably: the lower limit of the preferred total weight percentage of the compounds of formulae M17 to M21 relative to the total weight of the liquid crystal composition of the present invention is 0%, 1%, 2%, 3%, 5%, 7%, 10%, 14%, 16% or 20%; the upper limit value of the preferred total weight percentage of the compounds of formulae M17 to M21 relative to the total weight of the liquid crystal composition of the present invention is 30%, 25%, 23%, 20%, 18%, 15%, 12%, 10% or 5%.
In addition to the above compounds, the liquid crystal composition of the present invention may contain a conventional nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, antioxidant, ultraviolet absorber, infrared absorber, polymerizable monomer, light stabilizer, and the like.
Possible dopants which are preferably added to the liquid crystal composition according to the invention are shown below.
In some embodiments of the present invention, preferably, the dopant comprises 0-5% by weight of the liquid crystal composition; more preferably, the dopant is present in an amount of 0-1% by weight of the liquid crystal composition.
Further, additives such as an antioxidant and a light stabilizer used in the liquid crystal composition of the present invention are preferably as follows:
wherein n represents a positive integer of 1 to 20.
Preferably, the light stabilizer is selected from the group consisting of the light stabilizers shown below:
in some embodiments of the present invention, preferably, the light stabilizer is 0-5% by weight of the liquid crystal composition; more preferably, the light stabilizer accounts for 0 to 1 percent of the weight of the liquid crystal composition; particularly preferably, the light stabilizer is 0 to 0.1% by weight of the liquid crystal composition.
In another aspect, the present invention also provides a liquid crystal display device comprising the above liquid crystal composition.
Has the advantages that:
the liquid crystal composition provided by the invention has suitably high dielectric anisotropy, suitably high optical anisotropy, suitably high clearing point, high transmittance and larger average elastic constant KaveSo that the liquid crystal display device comprising the liquid crystal composition has faster response speed, high contrast ratio, higher transmittance and relatively less light scattering. In particular, in the liquid crystal composition of the present invention, when the compound of formula i is added, the liquid crystal composition has high optical anisotropy and high average elastic constant, so that the compound of formula i can achieve the technical effect of effectively adjusting transmittance, and further the liquid crystal display device of the present invention can obtain relatively less light scattering, and thus the liquid crystal display device using the liquid crystal composition of the present invention can obtain good display effectAnd (5) fruit.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. The following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
For convenience of expression, in the following examples, the group structure of the liquid crystal composition is represented by the code listed in Table 1:
TABLE 1 radical structural code of liquid crystal compounds
Compounds of the following formula are exemplified:
the structural formula is represented by the code listed in Table 1, and can be expressed as: nCCGF, wherein n in the code represents the number of C atoms of the left alkyl group, for example, n is 3, namely, the alkyl group is-C3H7(ii) a C in the code represents cyclohexane, G represents 2-fluoro-1, 4-phenylene and F represents fluorine.
The abbreviated codes of the test items in the following examples are as follows:
cp clearing Point (nematic phase-transition temperature of isotropic phase,. degree.C.)
TS→NLow temperature transformation Point (smectic-nematic transition temperature,. degree.C.)
Δ n optical anisotropy (589nm, 25 ℃ C.)
Delta epsilon dielectric anisotropy (1KHz, 25 ℃ C.)
ε⊥Dielectric constant perpendicular to molecular axis
ε⊥Ratio of/delta epsilon vertical dielectric to dielectric
K11Elastic constant ("splay", pN at 20 ℃ C.)
K22Elastic constant ("distortion", pN at 20 ℃ C.)
K33Elastic constant ("bending", pN at 20 ℃ C.)
KaveAverage elastic constant (K)11+K22+K33Average value of (1)
T transmittance (DMS 505 tester, box thickness 3.5 μm)
Tau response time (ms)
LTS Low temperature stability
Wherein,
the optical anisotropy was measured using an Abbe refractometer under a sodium lamp (589nm) light source at 25 ℃.
Δε＝ε‖-ε⊥Wherein, epsilon‖Is a dielectric constant parallel to the molecular axis,. epsilon⊥For the dielectric constant perpendicular to the molecular axis, test conditions: the test box is TN90 type at 25 deg.C and 1KHz, and has a thickness of 7 μm.
K11、K22、K33The liquid crystal display device is obtained by using an LCR instrument and an antiparallel friction box to test a C-V curve of liquid crystal and calculating the following test conditions: a 7-micron antiparallel friction box, wherein V is 0.1-20V;
test conditions for T transmittance: the DMS 505 tester is used for testing the transmittance of a dimming device at a clearing point +/-10 ℃, and the dimming device is an IPS type liquid crystal testing box with the box thickness of 3.5 microns. .
The response time of tau is measured by using a DMS 505 tester at 25 ℃; the test box is a VA 4.0 test box, the thickness of the box is 4 mu m, the frequency is 1000Hz, and the driving voltage is 90V.
The components used in the following examples can be synthesized by a known method or obtained commercially. These synthesis techniques are conventional, and the resulting liquid crystal compounds were tested to meet the standards for electronic compounds.
Liquid crystal compositions were prepared according to the compounding ratios of the liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared according to the conventional method in the field, such as heating, ultrasonic wave, suspension and the like, and is mixed according to the specified proportion.
Liquid crystal compositions given in the following examples were prepared and studied. The composition of each liquid crystal composition and the results of the performance parameter test thereof are shown below.
Comparative example 1
The liquid crystal composition of comparative example 1, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared by the respective compounds and weight percentages listed in table 2.
TABLE 2 liquid crystal composition formulation and Performance parameter testing
Example 1
The liquid crystal composition of example 1 was prepared according to the compounds and weight percentages listed in table 3, and filled between two substrates of a liquid crystal display for performance testing.
TABLE 3 liquid crystal composition formulation and Performance parameter testing
Example 2
The liquid crystal composition of example 2 was prepared according to the compounds and weight percentages listed in table 4, and filled between two substrates of a liquid crystal display for performance testing.
TABLE 4 liquid crystal composition formulation and Performance parameter testing
Example 3
The liquid crystal composition of example 3 was prepared according to the compounds and weight percentages listed in table 5, and filled between two substrates of a liquid crystal display for performance testing.
TABLE 5 liquid Crystal composition formulations and Performance parameter testing
Example 4
The liquid crystal composition of example 4 was prepared according to the compounds and weight percentages listed in table 6, and filled between two substrates of a liquid crystal display for performance testing.
TABLE 6 liquid crystal composition formulation and Performance parameter testing
Example 5
The liquid crystal composition of example 5 was prepared according to the compounds and weight percentages listed in table 7, and filled between two substrates of a liquid crystal display for performance testing.
TABLE 7 liquid Crystal composition formulations and Performance parameter testing
Example 6
The liquid crystal composition of example 6 was prepared according to the compounds and weight percentages listed in Table 8, and filled between two substrates of a liquid crystal display for performance testing.
TABLE 8 liquid crystal composition formulation and Performance parameter testing
Example 7
The liquid crystal composition of example 7 was prepared according to the compounds and weight percentages listed in Table 9, and filled between two substrates of a liquid crystal display for performance testing.
TABLE 9 liquid Crystal composition formulations and Performance parameter testing
Example 8
The liquid crystal composition of example 8 was prepared according to the compounds and weight percentages listed in Table 10, and filled between two substrates of a liquid crystal display for performance testing.
TABLE 10 liquid Crystal composition formulations and Performance parameter testing
As is clear from the above comparative example 1 and examples 1 to 8, the liquid crystal composition provided by the present invention has suitably high dielectric anisotropy, suitably high optical anisotropy, suitably high clearing point, high transmittance, and large average elastic constant KaveThe liquid crystal display device containing the liquid crystal composition has the advantages of higher response speed, high contrast ratio, higher transmittance and relatively less light scattering, so that the liquid crystal composition can obtain good display effect of the liquid crystal display device containing the liquid crystal composition.
The above embodiments are merely illustrative of the technical concept and features of the present invention, and the present invention is not limited thereto, and any equivalent changes or modifications made according to the spirit of the present invention should be included in the scope of the present invention.
Claims (10)
1. A liquid crystal composition, comprising:
at least one compound of the general formula I
At least one compound of the general formula II-1 and/or II-2
at least one compound of the formula M
Wherein,
R1represents a linear or branched alkyl group having 1 to 12 carbon atoms, 1 or not adjacent 2 or more-CH in the linear or branched alkyl group having 1 to 12 carbon atoms2-may be independently replaced by-C-, -C ≡ C-, -O-, -CO-O-, or-O-CO-, respectively, and one or more-H of said linear or branched alkyl groups containing 1 to 12 carbon atoms may be independently substituted by-F or-Cl, respectively;
RA1and RA2Each independently represents a linear or branched alkyl group having 1 to 12 carbon atoms,
1 or non-adjacent 2 or more-CH in the linear or branched alkyl containing 1 to 12 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-, respectively, and one or more-H present in these groups may be independently substituted by-F or-Cl, respectively;
RM1and RM2Each independently represents-H, a linear or branched alkyl group having 1 to 12 carbon atoms, a linear or branched alkenyl group having 2 to 12 carbon atoms,
1 or non-adjacent 2 or more-CH in the linear or branched alkyl containing 1 to 12 carbon atoms2-may be independently replaced by-C.ident.C-, -O-, -CO-O-or-O-CO-;
ring (C)
To represent
Wherein,
may be substituted by-CN, -F or-Cl, and one or more rings may be substituted by-CH ═ by-N;
ring (C)
Ring (C)
Ring (C)
And ring
Each independently represent
Wherein,
one or more-CH2-may be replaced by-O-, one or more of the ring single bonds may be replaced by double bonds,
wherein one or more-H may be substituted by-CN, -F or-Cl, and one or more ring-CH may be substituted by-N ═ N;
ring (C)
Ring (C)
And ring
Each independently represent
ZA11represents a single bond, -CH2CH2-、-CF2CF2-、-CF2O-、-OCF2-、-CO-O-、-O-CO-、-O-CO-O-、-CH＝CH-、-C≡C-、-CF＝CF-、-CH2O-or-OCH2-；
ZA21And ZA22Each independently represents a single bond, -CH2CH2-、-CF2CF2-、-CO-O-、-O-CO-、-O-CO-O-、-CH＝CH-、-C≡C-、-CF＝CF-、-CH2O-or-OCH2-；
ZM1And ZM2Each independently represents a single bond, -CO-O-, -O-CO-, -CH2O-、-OCH2-、-CH＝CH-、-C≡C-、-CH2CH2-or- (CH)2)4-；
LA11、LA12、LA13、LA21、LA22、LA23And LA24Each independently represents-H, -F, -CH3or-Cl;
XA1and XA2Each independently represents halogen, haloalkyl or haloalkoxy having 1 to 5 carbon atoms, haloalkenyl or haloalkenyloxy having 2 to 5 carbon atoms;
nA1and nA2Each independently represents 0, 1, 2 or 3, when nA1When 2 or 3, ring
May be the same or different, ZA11May be the same or different, and when n isA2When 2 or 3, ring
May be the same or different, ZA21May be the same or different;
nM1represents 0, 1, 2 or 3, and when nM1When 2 or 3, ring
May be the same or different, ZM2May be the same or different;
when Z isA21And ZA22Represents a single bond and nA2When 1, a ring
And ring
Is not simultaneously represented
The compounds of formula II-2 do not comprise the compounds of formula I.
2. The liquid crystal composition of claim 1, wherein the ring is
Can be expressed as
3. The liquid crystal composition of claim 2, wherein the compound of formula i is selected from the group consisting of:
4. the liquid crystal composition according to any one of claims 1 to 3, wherein the compound of formula I is present in an amount of 0.1% to 50% by weight of the liquid crystal composition.
5. The liquid crystal composition of claim 1, wherein the ring is
Ring (C)
Ring (C)
And ring
Each independently represent
6. The liquid crystal composition of claim 5, wherein the compound of formula ii-1 is selected from the group consisting of:
wherein,
RA1represents a linear or branched alkyl group having 1 to 12 carbon atoms, 1 or not adjacent 2 or more-CH in the linear or branched alkyl group having 1 to 12 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-, respectively.
7. The liquid crystal composition of claim 5, wherein the compound of formula ii-2 is selected from the group consisting of:
wherein,
RA2represents a linear or branched alkyl group having 1 to 8 carbon atoms, 1 or not adjacent 2 or more-CH in the linear or branched alkyl group having 1 to 8 carbon atoms2-may be independently replaced by-CH ═ CH-, -C ≡ C-, -O-, -CO-O-, or-O-CO-, respectively, and one or more-H present in these groups may be independently substituted by-F or-Cl, respectively.
8. Liquid crystal composition according to any one of claims 1 and 5 to 7, characterized in that the compound of formula II-1 and/or II-2 represents from 1% to 75% of the total weight of the liquid crystal composition.
9. The liquid crystal composition of claim 1, wherein the compound of formula M is selected from the group consisting of:
10. a liquid crystal display device comprising the liquid crystal composition according to any one of claims 1 to 9.
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