CN109097067B - Liquid crystal composition and application thereof in liquid crystal display device - Google Patents

Liquid crystal composition and application thereof in liquid crystal display device Download PDF

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CN109097067B
CN109097067B CN201710470825.3A CN201710470825A CN109097067B CN 109097067 B CN109097067 B CN 109097067B CN 201710470825 A CN201710470825 A CN 201710470825A CN 109097067 B CN109097067 B CN 109097067B
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CN109097067A (en
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丁文全
王盼盼
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Jiangsu Hecheng Display Technology Co Ltd
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—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
    • G02F1/139—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 based on orientation effects in which the liquid crystal remains transparent
    • G02F1/1391—Bistable or multi-stable liquid crystal cells

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Abstract

The invention providesA liquid crystal composition comprising: one or more compounds of formula I; the liquid crystal composition is matched with an ionic compound for driving, so that a smectic phase liquid crystal composition with good reliability, good ion driving capability and low driving voltage is obtained. The power consumption of the display device comprising the smectic liquid crystal of the present invention is reduced compared to the conventional display device comprising nematic liquid crystal. The transmission and color selection of a display device comprising the smectic liquid crystal according to the present invention is better compared to a display device comprising bistable cholesteric liquid crystal.

Description

Liquid crystal composition and application thereof in liquid crystal display device
Technical Field
The present invention relates to a liquid crystal composition, to the use thereof for electro-optical purposes and to a liquid crystal display comprising such a composition, in particular to an application mode in which the light transmittance characteristics are adjusted by driving with ions, using a liquid crystal smectic phase as the steady-state characteristic.
Background
Liquid crystals are mainly divided into different phases: nematic phase, smectic phase, cholesteric phase, smectic phase is again separated into smectic A, B, C, D, E, F, G, H, I, G, etc. Nematic and cholesteric liquid crystals have low viscosity and remarkable fluidity, while smectic liquid crystals have high viscosity. The liquid crystals have dielectric anisotropy, and the liquid crystal molecules can be driven by an electric field. After the liquid crystal molecules with low viscosity are driven by the electric signals, the molecular arrangement can not be maintained after the electric signals are cut off due to low viscosity, and the original arrangement state can be recovered; however, since the liquid crystal molecules having high viscosity are driven by an electric signal and have high viscosity, the molecular alignment state is maintained after the electric signal is cut off, and the liquid crystal molecules cannot be restored to the original alignment state and can be maintained only in the current state. Therefore, the smectic phase liquid crystal is used for displaying, and the display content can be still maintained when the electric signal is driven to be removed, thereby having the memory effect.
In 1978 D.Coates et al, in the text "Electrically induced morphologically treated proteins in semiconducting A phases and the electrical reverse" describe the electro-optical drive properties of a smectic A phase compound 8 CB. At that time, smectic A phase materials such as 8CB and 8OCB have a significant disadvantage as smectic A phase liquid crystals: the driving voltage is high (generally about 200V), and the driving circuit needs a period of aging before use to be stably driven and can only be driven in a narrow temperature interval (about 10 ℃).
GB2274649A patent of Dow Corning company in 1994 finds that siloxane smectic phase A liquid crystal material can reduce driving voltage (about 70-100V), can stably work without long-time aging, and has wider driving temperature range. In WO2010/070606 in Cambridge industry, the siloxane liquid crystal material and a nematic phase are mixed to obtain a wide-temperature smectic phase A material, and the use temperature of the smectic phase A material is further widened. In WO2011/115611a1, the cambridge industry also mentions the compounding of smectic a liquid crystal formulations using siloxane polymers. The siloxane smectic phase A material not only has smectic phase A, but also can induce other non-smectic phase A materials, so that the mixed material mixed with the siloxane liquid crystal material has smectic phase A. Therefore, siloxane smectic A phase liquid crystal materials are an important class of materials in smectic A phase formulations.
However, the siloxane smectic A phase liquid crystal has a strong memory effect, and the displayed image cannot be erased completely, and the afterimage of the displayed image is easily left. In addition, the birefringence of the siloxane smectic A phase material is small (delta n is approximately equal to 0.08), and the use amount of siloxane liquid crystal in the formula is large, so that the birefringence of the smectic A phase liquid crystal formula mainly containing siloxane is not high. In the scattering display mode, the contrast is related to the birefringence of the liquid crystal material, and the higher the birefringence, the lower the contrast when the siloxane smectic A phase material is used for display.
In the prior art, in order to solve the above problems, researchers have optimized the ion driving capability and the viscosity of the liquid crystal and improved the problem of image sticking by using a mode of generating a smectic phase by heteroatom induction, for example, CN103666482B adopts a heterocyclic liquid crystal material with a structure such as boron and the like to induce a smectic phase to eliminate the display image sticking of a siloxane liquid crystal smectic phase a formula system and improve the contrast, but the heterocyclic liquid crystal material with a structure such as boron and the like has the problems of high driving voltage, large viscosity and low reaction speed caused by a monomer with a negative structure, and the driving voltage is still high as a whole.
In addition, the heterocyclic liquid crystal material with a structure such as boron and oxygen also has the problems of poor stability and poor reliability, and in view of the problem that the heterocyclic liquid crystal material with a sulfur-containing structure has better reliability compared with the heterocyclic liquid crystal material with a boron and oxygen structure, the prior art tries to replace the heterocyclic liquid crystal material with a boron and oxygen structure with the heterocyclic liquid crystal material with a sulfur-containing structure, but the prior art also has the problem of high driving voltage, and meanwhile, the stability and reliability of the heterocyclic liquid crystal material with a sulfur-containing structure are still difficult to meet the requirements of increasingly updated display devices.
Therefore, it is needed to solve the problems of poor stability, high driving voltage, high viscosity, slow reaction speed and after-driving image sticking existing in the smectic phase liquid crystal material in the prior art.
Disclosure of Invention
The invention aims to obtain a liquid crystal material with a wide smectic phase temperature range by adopting a mode of inducing smectic phase monomers to be fused with the traditional nematic phase monomers. By optimizing the large dielectric nematic monomer containing esters, the driving voltage is reduced, and the response speed is optimized. The smectic phase liquid crystal material which is good in reliability, good in ion driving capability and low in driving voltage is obtained by matching ions for driving.
It is another object of the present invention to provide a display device comprising said smectic liquid crystal composition, said display device being particularly useful for regulating light passage characteristics, the display device comprising said smectic liquid crystal of the present invention having a bistable state of a hazy state and a transparent state, and the power consumption of the display device comprising said smectic liquid crystal of the present invention is reduced compared to the conventional display device comprising nematic liquid crystal. The transmission and color selection of a display device comprising the smectic liquid crystal according to the present invention is better compared to a display device comprising bistable cholesteric liquid crystal.
In order to accomplish the above object of the invention, the present invention provides a liquid crystal composition comprising:
one or more compounds of the formula I
Figure BDA0001327053400000021
One or more compounds of the formula II
Figure BDA0001327053400000022
Wherein,
the R is1represents-H, -F,
Figure BDA0001327053400000031
Alkyl or alkoxy of 1 to 15 carbon atoms, alkenyl or alkenyloxy of 2 to 15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
the R is2Represents an alkyl or alkoxy group of 3 to 15 carbon atoms, an alkenyl or alkenyloxy group of 3 to 15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
Said X1And X2The same or different, each independently represents-F or-Cl;
the ring A and the ring B are the same or different and each independently represents
Figure BDA0001327053400000032
Wherein,
Figure BDA0001327053400000033
wherein one or more H may be substituted by-F or methyl;
the ring C, the ring D and the ring E are the same or different and each independently represents
Figure BDA0001327053400000034
Wherein,
Figure BDA0001327053400000035
wherein one or more-H may be substituted with-F, provided that: at least one of ring C, ring D and ring E represents
Figure BDA0001327053400000036
Wherein one or more-CH-is substituted with-N-; or represents
Figure BDA0001327053400000037
In which one or more-CH2-is substituted by-O-or-S-;
the Z, Z1And Z2The same or different, each independently represents a bridge bond of-, -CH, or a single bond2O-、-OCH2-、-COO-、-OCO-、-CF2O-or-OCF2-；
Said Y is1And Y2The same or different, each independently represent-H, -F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 1-15 carbon atoms, alkenyl or alkenyloxy of 1-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
said a represents 0, 1 or 2;
b, c, d are identical or different and each independently represents 0, 1 or 2, with the proviso that: b + c + d is more than or equal to 2.
In some embodiments of the invention, the compound of formula I is preferably selected from the group consisting of one or more of the following formulae I-1 to I-2:
Figure BDA0001327053400000038
Wherein,
in some embodiments of the present invention, the percentage of the compound of formula i to the total weight of the smectic liquid crystal composition is 1 to 60%, preferably 5 to 60%, and more preferably: 10 to 60 percent.
In some embodiments of the invention, the compound of formula I-1 is preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000041
wherein,
said Y is1represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 1-15 carbon atoms, alkenyl or alkenyloxy of 1-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, the compound of formula I-2 is preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000042
Figure BDA0001327053400000051
wherein,
said Y is1represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 1-15 carbon atoms, alkenyl or alkenyloxy of 1-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, R is1To represent
Figure BDA0001327053400000052
Alkyl or alkoxy of 3 to 15 carbon atoms, alkenyl or alkenyloxy of 3 to 15 carbon atoms, wherein one or more-CH 2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, R is1To represent
Figure BDA0001327053400000053
Alkyl or alkoxy of 4 to 15 carbon atoms, alkenyl or alkenyloxy of 4 to 15 carbon atoms, one or more of themmultiple-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, Y is1represents-F, -OCF3、-CF3、-CN、-NCSAlkyl or alkoxy of 3 to 15 carbon atoms, alkenyl or alkenyloxy of 3 to 15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, Y is1represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-15 carbon atoms, alkenyl or alkenyloxy of 4-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, the compound of formula i-a is preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000054
Figure BDA0001327053400000061
in some embodiments of the invention, in particular in the compounds I-a-1 to I-a-10, the group-CN may also be replaced by-F, -OCF3、-CF3or-NCS.
In some embodiments of the invention, the compounds of formula i-b are preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000062
In some embodiments of the invention, in particular in the compounds I-b-1 to I-b-10, the group-CN may also be replaced by-F, -OCF3、-CF3or-NCS.
In some embodiments of the invention, the compounds of formula i-c are preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000071
in some embodiments of the invention, in particular in the compounds I-c-1 to I-c-10, the group-CN may also be replaced by-F, -OCF3、-CF3or-NCS.
In some embodiments of the invention, the compounds of formulae i-d are preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000072
Figure BDA0001327053400000081
in some embodiments of the invention, in particular in the compounds I-d-1 to I-d-10, the group-CN may also be replaced by-F, -OCF3、-CF3or-NCS.
In some embodiments of the invention, the compounds of formulae i-e are preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000082
in some embodiments of the invention, in particular in the compounds I-e-1 to I-e-10, the group-CN may also be replaced by-F, -OCF3、-CF3or-NCS.
In some embodiments of the invention, the compounds of formulae i-f are preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000083
Figure BDA0001327053400000091
In some embodiments of the invention, in particular in the compounds I-F-1 to I-F-10, the group-CN may also be replaced by-F, -OCF3、-CF3or-NCS.
In some embodiments of the invention, the compounds of formulae I-g are preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000092
in some embodiments of the invention, in particular in the compounds I-g-1 to I-g-10, the group-CN may also be replaced by-F, -OCF3、-CF3or-NCS.
In some embodiments of the invention, the compounds of formulae i-h are preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000093
Figure BDA0001327053400000101
in some embodiments of the invention, in particular in the compounds I-h-1 to I-h-10, the group-CN may also be replaced by-F, -OCF3、-CF3or-NCS.
In some embodiments of the invention, the compounds of formula i-i are preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000102
in some embodiments of the invention, in particular in the compounds I-i-1 to I-i-10, the group-CN may also be replaced by-F, -OCF3、-CF3or-NCS.
In some embodiments of the present invention, the application of the general formula I in the smectic phase liquid crystal composition of the present invention has the effect of reducing the driving voltage.
In some embodiments of the invention, the compound of formula ii is preferably in the group consisting of one or more of the following formulae:
Figure BDA0001327053400000111
wherein,
the P is1And P2The same or different, each independently represents-O-or-S-;
m1 and m2 are the same or different and each independently represents 0, 1 or 2.
In some embodiments of the invention, the compound of formula ii is particularly preferred from the group consisting of one or more of the following formulae:
Figure BDA0001327053400000121
in some embodiments of the invention, the compound of formula ii is further preferably in the group consisting of one or more of the following formulae:
Figure BDA0001327053400000122
in some embodiments of the present invention, the percentage of the compound of formula ii to the total weight of the smectic phase liquid crystal composition is 1 to 70%, preferably 5 to 70%, more preferably 10 to 70%, more preferably 15 to 70%, more preferably 20 to 70%, more preferably: 30 to 70%, more preferably: 30 to 60%, more preferably: 30-55 percent.
In some embodiments of the invention, R is2Represents an alkyl or alkoxy group of 4 to 15 carbon atoms, an alkenyl or alkenyloxy group of 4 to 15 carbon atoms, wherein one or more-CH 2-may be substituted by-O-, provided that-O-is not directly attached;
in some embodiments of the invention, Y is2represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 3-15 carbon atoms, alkenyl or alkenyloxy of 3-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, Y is2represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-15 carbon atoms, alkenyl or alkenyloxy of 4-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the present invention, in the compound of formula II-1, R is2Represents an alkyl or alkoxy group of 4 to 10 carbon atoms, an alkenyl or alkenyloxy group of 4 to 10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached; z is1represents-COO-, -OCO-or a single bond; said Y is2represents-OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-10 carbon atoms, alkenyl or alkenyloxy of 4-10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, the compound of formula II-1 is preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000131
Figure BDA0001327053400000141
in some embodiments of the present invention, in the compound of formula II-3, R is2Represents an alkyl or alkoxy group of 4 to 10 carbon atoms, an alkenyl or alkenyloxy group of 4 to 10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached; z is1And Z2The same or different, each independently represents-COO-, -OCO-, or a single bond; said Y is2represents-OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-10 carbon atoms, alkenyl or alkenyloxy of 4-10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, the compound of formula II-3 is preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000142
Figure BDA0001327053400000151
Figure BDA0001327053400000161
in some embodiments of the present invention, in the compound of formula II-5, R is2Represents an alkyl or alkoxy group of 4 to 10 carbon atoms, an alkenyl or alkenyloxy group of 4 to 10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached; z is 1And Z2The same or different, each independently represents-COO-, -OCO-, or a single bond; what is needed isY is2represents-OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-10 carbon atoms, alkenyl or alkenyloxy of 4-10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, the compound of formula II-5 is preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000171
Figure BDA0001327053400000181
in some embodiments of the invention, the compound of formula II-6 is preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000182
wherein,
the R is2Represents an alkyl or alkoxy group of 4 to 10 carbon atoms, an alkenyl or alkenyloxy group of 4 to 10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
z is1And Z2The same or different, each independently represents-COO-, -OCO-, or a single bond;
said Y is2represents-OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-10 carbon atoms, alkenyl or alkenyloxy of 4-10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
in some embodiments of the invention, the compounds of formula II-11 are preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000183
Wherein,
the R is2Represents an alkyl or alkoxy group of 4 to 10 carbon atoms, an alkenyl or alkenyloxy group of 4 to 10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
z is1And Z2The same or different, each independently represents-COO-, -OCO-, or a single bond;
said Y is2represents-OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-10 carbon atoms, alkenyl or alkenyloxy of 4-10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
in some embodiments of the invention, the compounds of formulas II-12 are preferably selected from the group consisting of one or more of the following compounds:
Figure BDA0001327053400000184
wherein,
the R is2Represents an alkyl or alkoxy group of 4 to 10 carbon atoms, an alkenyl or alkenyloxy group of 4 to 10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
z is1And Z2The same or different, each independently represents-COO-, -OCO-, or a single bond;
said Y is2represents-OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-10 carbon atoms, alkenyl or alkenyloxy of 4-10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
In some embodiments of the present invention, the application of the general formula II in the smectic phase liquid crystal composition of the present invention has the effect of broadening the smectic phase temperature range of the liquid crystal composition.
In some embodiments of the present invention, the smectic phase liquid crystal composition further comprises:
from 0 to 55% by weight, based on the total weight of the composition, of one or more compounds of the group consisting of compounds of the formula III
Figure BDA0001327053400000191
The R is3represents-F,
Figure BDA0001327053400000192
Alkyl or alkoxy of 3 to 15 carbon atoms, alkenyl or alkenyloxy of 3 to 15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
said ring F represents
Figure BDA0001327053400000193
Said Y is3represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 1-15 carbon atoms, alkenyl or alkenyloxy of 1-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
m3 and m4 are the same or different and each independently represents 0, 1 or 2;
said e represents 0, 1 or 2.
In some embodiments of the present invention, the percentage of the compound of formula iii to the total weight of the smectic liquid crystal composition is from 0 to 50%, preferably from 0 to 30%, more preferably from 0 to 25%, even more preferably from 1 to 25%.
In some embodiments of the invention, R is3represents-F,
Figure BDA0001327053400000194
Alkyl or alkoxy of 4 to 15 carbon atoms, of 4 to 15 carbon atomsAlkenyl or alkenyloxy, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, R is3Represents an alkyl or alkoxy group of 4 to 15 carbon atoms, an alkenyl or alkenyloxy group of 5 to 15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, Y is3represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 3-15 carbon atoms, alkenyl or alkenyloxy of 3-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, Y is3represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-15 carbon atoms, alkenyl or alkenyloxy of 4-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
In some embodiments of the invention, R is3To represent
Figure BDA0001327053400000201
Alkyl or alkoxy of 4 to 15 carbon atoms, alkenyl or alkenyloxy of 4 to 15 carbon atoms, wherein one or more-CH 2-may be substituted by-O-, provided that-O-is not directly attached; said ring F represents
Figure BDA0001327053400000202
Said Y is3represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-15 carbon atoms, alkenyl or alkenyloxy of 4-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached; said e represents 0 or 1.
In some embodiments of the invention, the compound of formula iii is in the group preferably consisting of one or more of the following compounds:
Figure BDA0001327053400000203
Figure BDA0001327053400000211
Figure BDA0001327053400000221
in some embodiments of the present invention, the application of the general formula iii in the smectic phase liquid crystal composition of the present invention has the effect of increasing the birefringence of the liquid crystal composition, thereby increasing the contrast of the device.
In some embodiments of the present invention, the smectic phase liquid crystal composition further comprises:
from 0 to 50% by weight of the total composition of one or more compounds of formula IV
Figure BDA0001327053400000222
Wherein,
the R is4represents-H,
Figure BDA0001327053400000223
Alkyl or alkoxy of 1 to 15 carbon atoms, alkenyl or alkenyloxy of 2 to 15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
y represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 1-15 carbon atoms, alkenyl or alkenyloxy of 2-15 carbon atoms, wherein one or more-CH 2-may be substituted by-O-, provided that-O-is not directly attached.
Said ring G represents
Figure BDA0001327053400000224
Wherein,
Figure BDA0001327053400000225
wherein one or more-H may be substituted by-F,
Figure BDA0001327053400000226
wherein one or more-H may be substituted by-F, one or more CH may be substituted by N,
Figure BDA0001327053400000227
one or more-CH2-may be substituted by-O-or-S-;
the rings H and I are the same or different and each independently represents
Figure BDA0001327053400000231
Wherein,
Figure BDA0001327053400000232
wherein one or more-H may be substituted by-F,
Figure BDA0001327053400000233
wherein one or more-H may be substituted by-F, one or more CH may be substituted by N,
Figure BDA0001327053400000234
one or more-CH2-may be substituted by-O-or-S-;
said X3-X6The same or different, each independently represent-H, -F or-CH3；
And f represents 0 or 1.
In some embodiments of the invention, the compound of formula IV is preferably selected from the group consisting of compounds of formulae IV-1 to IV-22 as follows:
Figure BDA0001327053400000235
Figure BDA0001327053400000241
Figure BDA0001327053400000251
wherein,
the R is4represents-H, alkyl or alkoxy of 1-15 carbon atoms, alkenyl or alkenyloxy of 2-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
in some embodiments of the invention, X in the general formulae IV-1 to IV-22 is3preferably-H or-CH3Said X is4And X5preferably-H or-F.
In some embodiments of the invention, X in the general formulae IV-1 to IV-22 is3preferably-H, X4And X5preferably-H or-F.
In some embodiments of the invention, X in the general formulae IV-1 to IV-22 is3Is preferably-CH3，X4And X5preferably-H or-F.
In some embodiments of the present invention, the percentage of the compound of formula iv to the total weight of the smectic phase liquid crystal composition is 0 to 45%, more preferably 3 to 40%, more preferably 5 to 35%, more preferably 10 to 30%.
In some embodiments of the present invention, the application of the general formula iv in the smectic phase liquid crystal composition of the present invention has the effects of reducing driving voltage, reducing viscosity and increasing response speed.
In some embodiments of the present invention, the smectic phase liquid crystal composition further comprises one or more ionic compounds.
In some embodiments of the invention, the ionic compound is selected from sodium dodecyl sulfate, ethyltriphenylphosphonium iodide, (ferrocenylmethyl) trimethylammonium iodide, 1, 2-dimethyl-3-butylimidazolium hexafluorophosphate, tetraethylammonium p-toluenesulfonate, phenyltriethylammonium iodide, 1-octyl-3-methylimidazolium hexafluorophosphate, bis (tetra-n-butylamine) bis (1, 3-dithiacyclopentadiene-2-thione-4, 5-dithiol) palladium, tetra-n-butylbis (1, 3-dithiacyclopentadiene-2-thione-4, 5-dithiol) nickel, bis (tetra-n-butylammonium) bis (1, 3-dithiacyclopentene-2-thione-4, 5-dithiol) zinc, zinc, One or more of bis (tetra-n-butylammonium) tetracyanodiphenoquinone dimethane, tetrabutylammonium bromide, tetraoctadecylammonium bromide, hexadecylammonium perchlorate, hexadecylammonium bromide, 1-butyl-3-methylimidazolium tetrachloroferrate, methyltriphenylphosphonium iodide, tetraphenylphosphonium iodide, hexadecyltrimethylammonium bromide, hexadecyltrimethylammonium perchlorate, hexadecyldimethylbenzylammonium chloride, dodecylpyridinium bromide, hexadecylpyridinium bromide, chlorohexadecylpyridinium, hexadecyltributylammonium bromide, octadecyltributylammonium bromide and octadecyltrimethylammonium bromide.
In another aspect, the present invention provides a smectic liquid crystal composition further comprising one or more additives known to those skilled in the art and described in the literature. For example, 0-15% pleochroic dyes and/or chiral dopants may be added.
The following shows possible dopants which are preferably added to the mixtures according to the invention.
Figure BDA0001327053400000261
Figure BDA0001327053400000271
The stabilizers which may be added to the mixtures according to the invention are mentioned below, for example.
Figure BDA0001327053400000281
Figure BDA0001327053400000291
Figure BDA0001327053400000301
Preferably, the stabilizer is selected from the group consisting of the stabilizers shown below.
Figure BDA0001327053400000302
In the embodiment of the present invention, it is preferable that the stabilizer accounts for 0 to 5% by weight of the total weight of the liquid crystal composition; more preferably, the stabilizer accounts for 0-1% of the total weight of the liquid crystal composition; as a particularly preferred embodiment, the stabilizer is 0 to 0.1% by weight of the total weight of the liquid crystal composition.
The invention also provides a display device comprising the smectic phase liquid crystal composition.
Compared with the prior art, the smectic phase liquid crystal composition is matched with ions for driving, so that the smectic phase liquid crystal material with good reliability, good ion driving capability and low driving voltage is obtained.
The power consumption of the display device comprising the smectic liquid crystal of the present invention is reduced compared to the conventional display device comprising nematic liquid crystal. The transmission and color selection of a display device comprising the smectic liquid crystal according to the present invention is better compared to a display device comprising bistable cholesteric liquid crystal.
In the present invention, the proportions are by weight and all temperatures are in degrees centigrade, unless otherwise specified.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
The liquid crystal displays used in the following embodiments are all ITO liquid crystal display devices having no alignment layer, and the cell thickness d is 13 μm, and is composed of a polarizer (polarizer), an electrode substrate, and the like. The display device is in a normally white mode, i.e. when no voltage difference is applied between the row and column electrodes, a viewer perceives a pixel color that is white. The axes of the upper and lower polarizers on the substrate are at an angle of 90 degrees to each other. The space between the two substrates is filled with an optical liquid crystal material.
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
Figure BDA0001327053400000311
Figure BDA0001327053400000321
Compounds of the following formula are exemplified:
Figure BDA0001327053400000322
the structural formula is represented by the code listed in Table 1, and can be expressed as: nCGUF, wherein n in the code represents the number of carbon atoms of the left alkyl group, for example, n is "2", that is, the alkyl group is-C 2H5(ii) a C in the code represents a "1, 4-cyclohexylene group", G in the code represents a "2-fluoro-1, 4-phenylene group", U in the code represents a "2, 5-difluoro-1, 4-phenylene group", and F in the code represents a "fluoro substituent".
The abbreviated codes of the test items in the following examples are as follows:
U1: driving voltage (V) for ordered state to disordered state of liquid crystal molecules
U2: driving of liquid crystal molecules from disordered to ordered statesPress (V)
C: existence of afterimage
HFog mist: haze value of fog state
HTransparent film: haze value of clear state
IUV: current value after UV (mA)
Wherein, U1The driving voltage from the ordered state to the disordered state of the liquid crystal molecules is generally that the ordered state test box shows a transparent disordered state test box shows a fog state;
U2the driving voltage from the liquid crystal molecule unordered state to the ordered state is adopted, and the general ordered state test box shows that the transparent unordered state test box shows a fog state;
c, repeatedly electrifying and switching for 200 times, and observing with naked eyes whether the ghost phenomenon exists or not
HFog mistTesting the fog degree value of the fog state of the test box by using a test machine WGT-S;
Htransparent filmTesting the transparent haze value of the test box by using a test machine WGT-S;
IUVand irradiating the test box with SY-60A and 5mw UV light for 20s to test the current value of the test box after UV.
The components used in the following examples can be synthesized by a known method or obtained commercially. These synthesis techniques are conventional, and the resulting liquid crystal compounds were tested to meet the standards for electronic compounds.
Liquid crystal compositions were prepared according to the compounding ratios of the liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared according to the conventional method in the field, such as heating, ultrasonic wave, suspension and the like, and is mixed according to the specified proportion.
Liquid crystal compositions given in the following examples were prepared and studied. The composition of each liquid crystal composition and the results of the performance parameter test thereof are shown below.
Comparative example 1
The liquid crystal composition of comparative example 1, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared with each compound and weight percentage as listed in table 2, and the test data are shown in the following table:
TABLE 2 liquid crystal composition formulations and their test properties
Figure BDA0001327053400000331
Comparative example 2
The liquid crystal composition of comparative example 2, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared with each compound and weight percentage as listed in table 3, and the test data are shown in the following table:
TABLE 3 liquid crystal composition formula and its test performance
Figure BDA0001327053400000332
Figure BDA0001327053400000341
Comparative example 3
The liquid crystal composition of comparative example 3, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared with each compound and weight percentage as listed in table 4, and the test data are shown in the following table:
TABLE 4 liquid crystal composition formula and its test performance
Figure BDA0001327053400000342
Example 1
The liquid crystal composition of example 1 was prepared according to the compounds and weight percentages listed in table 5, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 5 liquid crystal composition formulations and their test properties
Figure BDA0001327053400000343
Example 2
The liquid crystal composition of example 2 was prepared according to the compounds and weight percentages listed in table 6, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 6 liquid crystal composition formula and its test performance
Figure BDA0001327053400000351
Example 3
The liquid crystal composition of example 3 was prepared according to the compounds and weight percentages listed in table 7, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 7 liquid crystal composition formulations and their test properties
Figure BDA0001327053400000352
Referring to comparative examples 1, 2 and 3, it can be seen from the test data of examples 1, 2 and 3 above that examples 1, 2 and 3 according to the present invention are advantageous in that there is no afterimage and have a lower driving voltage, relative to the conventional CB-type smectic liquid crystal composition of comparative example 1.
It can be seen that the inventive examples 1, 2 and 3 have significantly lower driving voltages relative to comparative example 2.
Compared with the heterocyclic smectic phase liquid crystal composition containing a sulfur structure adopted in comparative example 3, the smectic phase liquid crystal composition described in comparative example 3 has the problems of large current and poor reliability after being irradiated by UV light. The smectic phase liquid crystal compositions of examples 1, 2 and 3 according to the present invention all had lower current after UV light irradiation, and thus had good stability against UV light, relative to the heterocyclic smectic phase liquid crystal composition of comparative example 3, which had a sulfur-containing structure.
In conclusion, the smectic phase liquid crystal composition has lower driving voltage and good UV light resistance stability, so that a liquid crystal display device comprising the smectic phase liquid crystal composition has lower current consumption and good reliability.

Claims (12)

1. A liquid crystal composition, comprising:
10-60% by weight of the total composition of one or more compounds of formula I
Figure FDA0003314434320000011
One or more compounds of the formula II
Figure FDA0003314434320000012
1-55% by weight of the total composition of one or more compounds of formula III
Figure FDA0003314434320000013
3-40% by weight of the total composition of one or more compounds of formula IV
Figure FDA0003314434320000014
Wherein,
the R is1represents-H, -F,
Figure FDA0003314434320000015
Alkyl or alkoxy of 1 to 15 carbon atoms, alkenyl or alkenyloxy of 2 to 15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
the R is2Represents an alkyl or alkoxy group of 3 to 15 carbon atoms, an alkenyl or alkenyloxy group of 3 to 15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
said X1And X2The same or different, each independently represents-F or-Cl;
the ring A and the ring B are the same or different and each independently represents
Figure FDA0003314434320000016
Wherein,
Figure FDA0003314434320000017
wherein one or more H may be substituted by-F or methyl;
the ring C, the ring D and the ring E are the same or different and each independently represents
Figure FDA0003314434320000018
Wherein,
Figure FDA0003314434320000019
wherein one or more-H may be substituted with-F, provided that: at least one of ring C, ring D and ring E represents
Figure FDA00033144343200000110
Wherein one or more-CH-is substituted with-N-; or represents
Figure FDA00033144343200000111
In which one or more-CH2-is substituted by-O-or-S-;
z represents a bridge bond or a single bond, and the bridge bond is-, -identical to ≡ CH2O-、-OCH2-、-COO-、-OCO-、-CF2O-or-OCF2-；
Z is1And Z2Each independently represents a single bond;
said Y is1And Y2Are identical to each otherOr different, each independently represents-H, -F, -OCF 3、-CF3CN, -NCS, alkyl or alkoxy of 1-15 carbon atoms, alkenyl or alkenyloxy of 1-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
said a represents 0, 1 or 2;
b, c, d are identical or different and each independently represents 0, 1 or 2, with the proviso that: b + c + d is more than or equal to 2;
the R is4represents-H,
Figure FDA0003314434320000021
Alkyl or alkoxy of 1 to 15 carbon atoms, alkenyl or alkenyloxy of 2 to 15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
y represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 1-15 carbon atoms, alkenyl or alkenyloxy of 2-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
said ring G represents
Figure FDA0003314434320000022
Wherein,
Figure FDA0003314434320000023
wherein one or more-H may be substituted by-F,
Figure FDA0003314434320000024
wherein one or more-H may be substituted by-F, one or more CH may be substituted by N,
Figure FDA0003314434320000025
one or more-CH2-may be substituted by-O-or-S-;
the rings H and I are the same or different and each independently represents
Figure FDA0003314434320000026
Wherein,
Figure FDA0003314434320000027
wherein one or more-H may be substituted by-F, one or more CH may be substituted by N,
Figure FDA0003314434320000028
One or more-CH2-may be substituted by-O-or-S-;
said X3And X6The same or different, each independently represent-H, -F or-CH3；
Said X4And X5Both represent F;
said f represents 0 or 1;
the R is3represents-F,
Figure FDA0003314434320000029
Alkyl or alkoxy of 3 to 15 carbon atoms, alkenyl or alkenyloxy of 3 to 15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
said ring F represents
Figure FDA00033144343200000210
Said Y is3represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 1-15 carbon atoms, alkenyl or alkenyloxy of 1-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached;
m3 and m4 are the same or different and each independently represents 0, 1 or 2;
said e represents 0, 1 or 2;
the liquid crystal composition further comprises one or more ionic compounds.
2. The liquid crystal composition of claim 1, wherein the compound of formula i is selected from the group consisting of one or more of the following compounds of formulae i-1 to i-2:
Figure FDA0003314434320000031
and
Figure FDA0003314434320000032
3. the liquid crystal composition of claim 2, wherein the compound of formula i-1 is selected from the group consisting of one or more of the following compounds:
Figure FDA0003314434320000033
Figure FDA0003314434320000034
And
Figure FDA0003314434320000035
wherein,
said Y is1represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 1-15 carbon atoms, alkenyl or alkenyloxy of 1-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
4. The liquid crystal composition of claim 2, wherein the compound of formula i-2 is selected from the group consisting of one or more of the following compounds:
Figure FDA0003314434320000036
Figure FDA0003314434320000041
Figure FDA0003314434320000042
and
Figure FDA0003314434320000043
wherein,
said Y is1represents-F, -OCF3、-CF3CN, -NCS, alkyl or alkoxy of 1-15 carbon atoms, alkenyl or alkenyloxy of 1-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
5. The liquid crystal composition of claim 1, wherein the compound of formula ii is selected from the group consisting of one or more of:
Figure FDA0003314434320000044
Figure FDA0003314434320000051
Figure FDA0003314434320000052
and
Figure FDA0003314434320000053
wherein,
the P is1And P2The same or different, each independently represents-O-or-S-;
m1 and m2 are the same or different and each independently represents 0, 1 or 2.
6. The liquid crystal composition of claim 5, wherein R is2Represents an alkyl or alkoxy group of 4 to 15 carbon atoms, an alkenyl or alkenyloxy group of 4 to 15 carbon atoms, wherein one or more-CH 2-may be substituted by-O-, provided that-O-is not directly attached.
7. The liquid crystal composition of claim 6, wherein in the compound of formula II-1, R is2Represents an alkyl or alkoxy group of 4 to 10 carbon atoms, an alkenyl or alkenyloxy group of 4 to 10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached; said Y is2represents-OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-10 carbon atoms, alkenyl or alkenyloxy of 4-10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
8. The liquid crystal composition of claim 6, wherein in the compound of formula II-3, R is2Represents an alkyl or alkoxy group of 4 to 10 carbon atoms, an alkenyl or alkenyloxy group of 4 to 10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached; said Y is2represents-OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-10 carbon atoms, alkenyl or alkenyloxy of 4-10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
9. The liquid crystal composition of claim 6, wherein in the compound of formula II-5, R is 2Represents an alkyl or alkoxy group of 4 to 10 carbon atoms, an alkenyl or alkenyloxy group of 4 to 10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached; said Y is2represents-OCF3、-CF3CN, -NCS, alkyl or alkoxy of 4-10 carbon atoms, alkenyl or alkenyloxy of 4-10 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
10. The liquid crystal composition of claim 1, wherein the compound of formula iv is selected from the group consisting of compounds of formulae iv-1 to iv-4 and iv-8 to iv-22:
Figure FDA0003314434320000061
Figure FDA0003314434320000071
Figure FDA0003314434320000081
and
Figure FDA0003314434320000082
wherein,
the R is4represents-H, alkyl or alkoxy of 1-15 carbon atoms, alkenyl or alkenyloxy of 2-15 carbon atoms, wherein one or more-CH2-may be substituted by-O-, provided that-O-is not directly attached.
11. The liquid crystal composition of claim 1, wherein the ionic compound is selected from the group consisting of sodium dodecyl sulfate, ethyltriphenylphosphonium iodide, (ferrocenylmethyl) trimethylammonium iodide, 1, 2-dimethyl-3-butylimidazolium hexafluorophosphate, tetraethylammonium p-toluenesulfonate, phenyltriethylammonium iodide, 1-octyl-3-methylimidazolium hexafluorophosphate, bis (tetra-n-butylamine) bis (1, 3-dithiacyclopentadiene-2-thione-4, 5-dithiol) palladium, tetra-n-butylbis (1, 3-dithiacyclopentadiene-2-thione-4, 5-dithiol) nickel, bis (tetra-n-butylammonium) bis (1, 3-dithiacyclopentene-2-thione-4, 5-dithiol) zinc, bis (tetra-n-butylammonium) tetracyanodiphenoquinone dimethane, tetrabutylammonium bromide, tetraoctadecylammonium bromide, hexadecylammonium perchlorate, hexadecylammonium bromide, 1-butyl-3-methylimidazol tetrachloroferrate, methyltriphenylphosphonium iodide, tetraphenylphosphonium iodide, hexadecyltrimethylammonium bromide, hexadecyltrimethylammonium perchlorate, hexadecyldimethylbenzylammonium chloride, dodecylpyridinium bromide, hexadecylpyridinium bromide, chlorohexadecylpyridinium, hexadecyltributylammonium bromide, octadecyltributylammonium bromide and octadecyltrimethylammonium bromide.
12. Use of the liquid crystal composition of any of claims 1 to 11 in a liquid crystal display device.
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