CN111139085B - Compound, liquid crystal composition, liquid crystal display element and liquid crystal display - Google Patents

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

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CN111139085B
CN111139085B CN201811312605.9A CN201811312605A CN111139085B CN 111139085 B CN111139085 B CN 111139085B CN 201811312605 A CN201811312605 A CN 201811312605A CN 111139085 B CN111139085 B CN 111139085B
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carbon atoms
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fluorine
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CN111139085A (en
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员国良
梁志安
李明
孟劲松
李正强
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/46—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
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods

Abstract

The invention relates to a compound, a liquid crystal composition, a liquid crystal display element and a liquid crystal display. The compounds of the present invention are as followsA compound of formula I. By adopting the liquid crystal composition containing the compound shown in the formula I, a liquid crystal display element or a liquid crystal display which can ensure that liquid crystal molecules are aligned according to a certain direction without using an alignment layer can be manufactured, so that the manufacturing process of the liquid crystal display element or the liquid crystal display is simplified, the cost is saved, the defects of poor display effect caused by poor preparation yield, poor heat resistance and poor aging resistance of the alignment layer are avoided, and the performance and the production efficiency of the liquid crystal display element or the liquid crystal display are further improved.

Description

Compound, liquid crystal composition, liquid crystal display element and liquid crystal display
Technical Field
The invention belongs to the technical field of liquid crystal display, and particularly relates to a compound for a liquid crystal composition, a liquid crystal composition containing the compound, and a liquid crystal display element or a liquid crystal display containing the compound or the liquid crystal composition.
Background
With the development of Display technology, flat panel Display devices such as Liquid Crystal Display (LCD) devices have advantages of high image quality, power saving, thin body, and wide application range, and thus are widely used in various consumer electronics products such as mobile phones, televisions, personal digital assistants, digital cameras, notebook computers, and desktop computers, and are becoming the mainstream of Display devices.
Currently, in a commonly used Liquid Crystal Display (LCD), a color film substrate and a TFT substrate are respectively provided with a layer of thin film material, which mainly functions to align liquid crystal molecules in a certain direction, and is called as an alignment layer (PI). Such alignment layers are mainly classified into a rubbing alignment type and a photo alignment type. The alignment layer has the characteristics of uniformity, adherence and stability.
However, alignment layers also have certain disadvantages. Firstly, the rubbing alignment layer is easy to cause the problems of dust particles, static residues, brush marks and the like in the display process of the liquid crystal display device so as to reduce the manufacturing yield of the liquid crystal display device, while the photo-alignment layer can avoid the problems, but the photo-alignment layer is limited in material characteristics, poor in heat resistance and ageing resistance and weak in liquid crystal molecule anchoring capability, so that the display effect of the liquid crystal display device is influenced; secondly, the process of forming the alignment layer on the TFT-LCD is also complicated, which results in an increase in the production cost of the liquid crystal display device.
Disclosure of Invention
The present inventors have conducted intensive studies in order to overcome the problem of high manufacturing costs due to the manufacture of an alignment layer and to obtain a liquid crystal composition for aligning liquid crystal molecules in a certain direction without using an alignment layer, and have found that the problem can be solved by containing the compound of the present invention in a liquid crystal composition, thereby completing the present invention. The invention also provides a liquid crystal composition containing the compound, and a liquid crystal display element or a liquid crystal display containing the liquid crystal composition. The present invention provides, inter alia, self-aligning liquid crystal compositions suitable for use in display or TV applications. By using the liquid crystal composition containing the compound, a liquid crystal display element or a liquid crystal display which can enable liquid crystal molecules to be aligned according to a certain direction without using an alignment layer can be manufactured, so that the manufacturing process of the liquid crystal display element or the liquid crystal display is simplified, the cost is saved, the defects of poor display effect caused by poor manufacturing yield, poor heat resistance and poor aging resistance of the alignment layer are avoided, and the performance and the production efficiency of the liquid crystal display element or the liquid crystal display are further improved.
Specifically, the present invention comprises the following:
in a first aspect of the invention, there is provided a compound of formula I:
Figure BDA0001855400210000021
wherein R is 0 Represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted carbon atomIs an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R is 0 Any one or more non-adjacent-CH of the group 2 -may each independently be replaced by-O-or cycloalkylene;
q represents 1, 2 or 3;
K 1 、K 2 each independently represents an aromatic, heteroaromatic, aliphatic or fused ring wherein any one or more of the non-adjacent-CH's on the aromatic, heteroaromatic, aliphatic or fused ring 2 Optionally substituted by-O-, -S-, K 1 、K 2 Optionally one or more H on the ring of (a) is substituted by L or-Sp 1 -P 5 Substitution;
l represents F, -Sp 2 -X 1 An alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, wherein any one or more of the groups represented by L is not adjacent to-CH 2 -optionally substituted by cyclopentylene, cyclobutyl, cyclopropylene;
P 5 represents H or a polymerizable group;
Sp 1 、Sp 2 each independently represents a single bond or a spacer;
X 1 each independently represents an alkyl-substituted carbonyl group having 1 to 10 carbon atoms or an alkyl-substituted ester group having 1 to 10 carbon atoms; any H in the alkyl with the carbon number of 1-10 is optionally substituted by F, and any one or more non-adjacent-CH 2 -optionally substituted by-O-, -S-;
Z 0 represents a single bond, -O-) -S-, -CO-) -COO-, -OCO-) -OCOO-, -OCH 2 -、-CH 2 O-、-SCH 2 -、-CH 2 S-、-CF 2 O-、-OCF 2 -、-CF 2 S-、-SCF 2 -、-(CH 2 )n 1 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-(CF 2 )n 2 -、-CH＝CH-、-C≡C-、-CF＝CF-、-CH＝CH-COO-、-OCO-CH＝CH-、-(CR Y R Z )n 3 -、-CH(-Sp-P 6 )-、-CH 2 CH(-Sp-P 6 ) -, or, -CH (-Sp-P) 6 )CH(-Sp-P 6 )-；
n 1 、n 2 、n 3 Each independently represents 1, 2, 3 or 4;
R Y 、R Z each independently represents H or an alkyl group having 1 to 5 carbon atoms, and R Y 、R Z At least one of the alkyl is alkyl with 1-5 carbon atoms;
sp each independently represents a single bond or a spacer;
P 6 each independently represents H or a polymerizable group;
R x represents (a), (b) or (c):
Figure BDA0001855400210000031
m 1 represents 1, 2, 3 or 4;
Figure BDA0001855400210000032
denotes an aromatic, aliphatic or fused ring wherein any one or more of the rings of the aromatic, aliphatic or fused ring are non-adjacent-CH 2 -optionally substituted by-O-, -S-, one or more H on the ring optionally being replaced by L 1 or-Sp 5 -P 4 Substitution;
Sp 3 、Sp 4 、Sp 5 each independently represents a single bond or a spacer;
P 4 represents H or a polymerizable group;
L 1 represents F, -Sp 3 -X 2 Alkyl group having 1 to 10 carbon atoms, fluorine-substituted carbon atom number1-10 alkyl group, alkoxy group having 1-10 carbon atoms, fluorine-substituted alkoxy group having 1-10 carbon atoms, alkenyl group having 2-10 carbon atoms, fluorine-substituted alkenyl group having 2-10 carbon atoms, alkenyloxy group having 3-8 carbon atoms or fluorine-substituted alkenyloxy group having 3-8 carbon atoms, and L 1 Any one or more non-adjacent-CH in the group 2 -optionally substituted by cyclopentylene, cyclobutyl, cyclopropylene;
X 2 each independently represents an alkyl-substituted carbonyl group having 1 to 10 carbon atoms or an alkyl-substituted ester group having 1 to 10 carbon atoms; any H in the alkyl with the carbon number of 1-10 is optionally substituted by F, and any one or more non-adjacent-CH 2 -optionally substituted by-O-, -S-;
S 1 represents a trivalent radical, S 2 Represents a tetravalent group.
In a second aspect of the invention, there is provided a liquid crystal composition comprising a compound of the first aspect of the invention as hereinbefore described.
In a third aspect of the present invention, there is provided a liquid crystal display element or a liquid crystal display comprising the aforementioned compound or the aforementioned liquid crystal composition, the display element or display being an active matrix display element or display or a passive matrix display element or display.
The compound shown in the formula I provided by the invention has the advantages of high solubility and good ultraviolet resistance. The Reactive Mesogen (RM) has the advantage of high charge retention rate (VHR), can be used as a self-alignment agent of a liquid crystal composition independently, can also be used as a self-alignment agent of a liquid crystal composition in modes of PSA, PS and the like by copolymerizing a vertical alignment material and other RMs, can avoid a PI process, and improves the production efficiency.
The liquid crystal composition containing the compound shown in the formula I has the advantages of high charge retention rate (VHR), low viscosity, capability of realizing quick response, moderate dielectric anisotropy delta epsilon, moderate optical anisotropy delta n and high stability to heat and light.
The liquid crystal display element or the liquid crystal display comprising the compound or the liquid crystal composition does not need to be additionally provided with a traditional alignment layer, so that the problems of poor yield of the liquid crystal display device, poor heat resistance and aging resistance and the like caused by dust particles, static residues, brush marks and the like caused by the alignment layer can be avoided, the preparation process of the liquid crystal display element or the liquid crystal display can be effectively simplified, the production efficiency can be improved, and the production cost can be reduced. In addition, the liquid crystal display element or the liquid crystal display obtained by the liquid crystal composition has the characteristics of wide nematic phase temperature range, proper or higher birefringence anisotropy delta n and high charge retention rate.
Detailed Description
[ Compound ]
A compound as one aspect of the present invention is a compound represented by formula I:
Figure BDA0001855400210000051
wherein R is 0 Represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R is 0 Any one or more non-adjacent-CH in the group 2 -may each independently be replaced by-O-or cycloalkylene;
q represents 1, 2 or 3;
K 1 、K 2 each independently represents an aromatic, heteroaromatic, aliphatic or fused ring wherein any one or more of the non-adjacent-CH's on the aromatic, heteroaromatic, aliphatic or fused ring 2 Optionally substituted by-O-, -S-, K 1 、K 2 Optionally one or more H on the ring of (a) is substituted by L or-Sp 1 -P 5 Substitution;
l represents F, -Sp 2 -X 1 Alkyl group having 1 to 10 carbon atoms, fluorine-substitutedAn alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, wherein any one or more of the groups represented by L are not adjacent to each other 2 -optionally substituted by cyclopentylene, cyclobutyl, cyclopropylene;
P 5 represents H or a polymerizable group;
Sp 1 、Sp 2 each independently represents a single bond or a spacer;
X 1 each independently represents an alkyl-substituted carbonyl group having 1 to 10 carbon atoms or an alkyl-substituted ester group having 1 to 10 carbon atoms; any H in the alkyl with the carbon number of 1-10 is optionally substituted by F, and any one or more non-adjacent-CH 2 -optionally substituted by-O-, -S-;
Z 0 represents a single bond, -O-) -S-, -CO-) -COO-, -OCO-) -OCOO-, -OCH 2 -、-CH 2 O-、-SCH 2 -、-CH 2 S-、-CF 2 O-、-OCF 2 -、-CF 2 S-、-SCF 2 -、-(CH 2 )n 1 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-(CF 2 )n 2 -、-CH＝CH-、-C≡C-、-CF＝CF-、-CH＝CH-COO-、-OCO-CH＝CH-、-(CR Y R Z )n 3 -、-CH(-Sp-P 6 )-、-CH 2 CH(-Sp-P 6 ) -, or, -CH (-Sp-P) 6 )CH(-Sp-P 6 ) -; preferably, Z 0 Represents a single bond;
n 1 、n 2 、n 3 each independently represents 1, 2, 3 or 4;
R Y 、R Z each independently represents H or an alkyl group having 1 to 5 carbon atoms, and R Y 、R Z At least one of the alkyl is alkyl with 1-5 carbon atoms;
sp each independently represents a single bond or a spacer;
P 6 each independently represents H orA polymerizable group;
R x represents (a), (b) or (c):
Figure BDA0001855400210000061
m 1 represents 1, 2, 3 or 4;
Figure BDA0001855400210000062
denotes an aromatic, aliphatic or fused ring wherein any one or more of the rings of the aromatic, aliphatic or fused ring are non-adjacent-CH 2 -optionally substituted by-O-, -S-, one or more H on the ring optionally being replaced by L 1 or-Sp 5 -P 4 Substitution;
Sp 3 、Sp 4 、Sp 5 each independently represents a single bond or a spacer;
P 4 represents H or a polymerizable group;
L 1 represents F, -Sp 3 -X 2 An alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and L 1 Any one or more non-adjacent-CH in the group 2 -optionally substituted by cyclopentylene, cyclobutyl, cyclopropylene;
X 2 each independently represents an alkyl-substituted carbonyl group having 1 to 10 carbon atoms or an alkyl-substituted ester group having 1 to 10 carbon atoms; any H in the alkyl with the carbon number of 1-10 is optionally substituted by F, and any one or more non-adjacent-CH 2 -optionally substituted by-O-, -S-;
S 1 represents a trivalent radical, S 2 Represents a tetravalent group.
As the trivalent group, S may be mentioned 1 Represents carbonOr trivalent groups of silicon; as the tetravalent group, S may be mentioned 2 Represents the case of a tetravalent group of phosphorus.
The compound shown in the formula I has better solubility in the liquid crystal composition, and when the addition amount of the compound in the liquid crystal composition is usually 0.5-5% by mass, preferably 1-3% by mass, the compound is easy to absorb UV and quickly polymerize to form a polymer with an alignment function.
The compound shown in the formula I contains a group selected from carbonyl groups substituted by alkyl with 1-10 carbon atoms and ester groups substituted by alkyl with 1-10 carbon atoms as an anchoring group. After the ODF process, the anchoring groups are spontaneously vertically arranged on the surface of a panel made of glass, ITO or polyimide, and a stable pretilt angle is formed after UV illumination polymerization under the condition of voltage application.
P 4 、P 5 、P 6 Represents a polymerizable group, the compound represented by the formula I has P 4 、P 5 Or P 6 In the case of (1), P 4 、P 5 、P 6 Each independently is preferably a methacrylate group, an acrylate group, a vinyl group or an oxirane group, and more preferably a methacrylate group.
The spacer in the compound shown in the formula I refers to a chain group, preferably a branched or straight-chain alkyl group with 1-10 carbon atoms, and any one or more non-adjacent-CH in the alkyl group 2 -optionally substituted by-O-, optionally-CH 2 -optionally substituted by cyclopropylene, cyclobutylene or cyclopentylene.
K 1 、K 2 Represents an aromatic, heteroaromatic, aliphatic or fused ring wherein any one or more of the non-adjacent-CH's on the aromatic, heteroaromatic, aliphatic or fused ring is 2 -optionally substituted by-O-, -S-; k 1 、K 2 One or more of H in (a) is optionally substituted by L 1 And (4) substitution. The aromatic ring is preferably a benzene ring or a naphthalene ring, the heteroaromatic ring is preferably a benzene ring or a naphthalene ring in which at least one-CH-is substituted with-N-, and the aliphatic ring is preferably selected from cyclohexane and cyclohexene, and at least one-CH 2 -substituted by-O-or-S-)Cyclohexane, and at least one-CH 2 -cyclohexene substituted by-O-or-S-, the aforementioned K 1 、K 2 Can be a spiro ring or a bridged ring, preferably selected from the group consisting of bicyclo (1, 1) pentane, bicyclo (2, 2) octane, bicyclo (3, 0) octane, spiro (3, 3) heptane, decahydronaphthalene, and tetrahydronaphthalene. The aforementioned fused rings are preferably selected from indane rings, indene rings, indane rings in which at least one C of the rings is replaced by-O-or-S-, and an indene ring in which at least one C of the rings is replaced with-O-or-S-, and further preferably a benzene ring or cyclohexane.
An anchoring group R x Preferably selected from the following groups:
Figure BDA0001855400210000081
optionally, the compound shown in formula I is selected from the group consisting of compounds shown in formulas I1 to I35,
Figure BDA0001855400210000091
/>
Figure BDA0001855400210000101
/>
Figure BDA0001855400210000111
/>
Figure BDA0001855400210000121
/>
Figure BDA0001855400210000131
the compound shown in the formula I contains carbonyl and ester structures as anchoring groups, and after a panel ODF (optical surface film) manufacturing process, due to the acting force between the anchoring groups and molecules on the surface of a panel (glass surface and ITO electrode surface), the anchoring groups can be spontaneously and vertically arranged on panel glass or an ITO transparent electrode substrate, so that liquid crystal molecules close to the compound shown in the formula I are vertically arranged, and under the irradiation of UV light, a layer of polymer with rough surface can be polymerized on the substrate, and the effects of PI insulation and vertical alignment of the liquid crystal molecules are achieved. The amount of the compound represented by the formula I added is preferably 1% or more, whereby the compound represented by the formula I can be polymerized to form a thin film having a thickness of 50nm to 120nm which is equivalent to that of a normal PI. On the other hand, since the compound represented by the formula I has good solubility, the storage stability at low temperatures required as a liquid crystal composition can be satisfied even when the amount added is 1% or more.
Hydroxyl groups are generally used as anchoring groups of the compounds serving as reactive mesogens because the hydroxyl groups are easy to form hydrogen bonds and have strong anchoring capability, but because the hydrogen atoms of the hydroxyl groups are almost exposed protons, the phenomenon that the Voltage Holding Ratio (VHR) of the liquid crystal composition is reduced after heat and UV irradiation is easily caused when the hydroxyl groups are excessively used in the liquid crystal composition, the afterimage defect is easily caused, and the display effect of the panel is not facilitated. The compound shown in the formula I provided by the invention uses carbonyl and ester groups with more stable properties relative to hydroxyl as anchoring groups, plays an anchoring role between the compound shown in the formula I and a panel, is favorable for a liquid crystal composition to show better stability to heat and UV, and reduces the probability of the occurrence of afterimage defects in panel display.
The compound shown in the formula I has the advantages of high solubility and good ultraviolet resistance. The Reactive Mesogen (RM) has the advantage of high charge retention rate (VHR), can be used as a self-alignment agent of a liquid crystal composition independently, can also be used as a self-alignment agent of a liquid crystal composition in modes of PSA, PS and the like by copolymerizing a vertical alignment material and other RMs, can avoid a PI process, and improves the production efficiency.
[ liquid Crystal composition ]
A liquid crystal composition according to an embodiment of the present invention contains the compound represented by the formula I. The liquid crystal composition may contain a liquid crystal compound other than the compound represented by formula I and other additive materials in addition to the compound represented by formula I. The compound of formula I is added to a liquid crystal composition, and after being poured into a display element, the liquid crystal molecules can be given a pre-tilt by UV photopolymerization or crosslinking under application of a voltage between electrodes. The liquid crystal composition containing the compound shown in the formula I has the advantages of high charge retention rate (VHR), low viscosity, capability of realizing quick response, moderate dielectric anisotropy delta epsilon, moderate optical anisotropy delta n and high stability to heat and light.
The liquid crystal composition of the present invention may optionally further comprise one or more compounds represented by the following formula II, and one or more compounds represented by the following formula III,
Figure BDA0001855400210000141
Figure BDA0001855400210000151
in the formula II, R 1 、R 2 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms,
Figure BDA0001855400210000152
each independently represents->
Figure BDA0001855400210000153
Or->
Figure BDA0001855400210000154
In the formula III, R 3 、R 4 Each independently represents a carbon number of 1 to 10An alkyl group, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, a carbon-1 to 10 alkoxy group, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, a carbon-2 to 10 alkenyl group, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, a carbon-3 to 8 alkenyloxy group or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more non-adjacent-CH 2 Optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene,
Z 1 、Z 2 each independently represents a single bond, -CH 2 CH 2 -or-CH 2 O-，
Figure BDA0001855400210000155
Each independently represent
Figure BDA0001855400210000156
Or->
Figure BDA0001855400210000157
/>
m represents 1 or 2; n represents 0, 1 or 2.
The compound shown in the formula II has the characteristics of low rotational viscosity and good intersolubility with other compounds. The lower rotational viscosity is more advantageous for improving the response speed of the liquid crystal composition. The compound shown in the formula III has negative dielectric anisotropy, and the driving voltage of the liquid crystal composition is adjusted by the compound shown in the formula III.
As R in the aforementioned formula III 3 、R 4 One or more non-adjacent-CH in the alkyl with 1-10 carbon atoms 2 Examples of the group substituted with a cyclopropylene group, a cyclobutylene group or a cyclopentylene group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a methylcyclopropylidene group, an ethylcyclopropylidene group, a propylcyclopropylidene group, an isopropylidene group, a n-butylcyclopropylidene group, an isobutylcyclopropylidene group, a tert-butylcyclopropylidene group, a methylcyclobutylidene group, an ethylcyclobutylidene group, a propylcyclobutylidene group, an isopropylcyclobutylidene group, a n-butylidene group, an isobutylcyclobutylidene group, a tert-butylidene groupA cyclobutyl group, a methylcyclopentylene group, an ethylcyclopentylene group, a propylcyclopentylene group, an isopropylcyclopentylene group, an n-butylcyclopentylene group, an isobutylcyclopentylene group, etc. R is 3 、R 4 Among the groups shown, preferred from the viewpoint of rotational viscosity, solubility and clearing point of the liquid crystal compound is cyclopropyl, cyclobutyl or cyclopentyl.
The liquid crystal composition of the present invention is preferably a negative dielectric anisotropic liquid crystal composition.
In the liquid crystal composition, the addition amount (mass ratio) of the compound shown in the formula I in the liquid crystal composition is 0.5-5%, preferably 1-3%; the addition amount (mass ratio) of the compound shown in the formula II in the liquid crystal composition is 15-60%, and preferably 20-40%; the amount (mass ratio) of the compound represented by the formula III added to the liquid crystal composition is 20 to 60%, preferably 30 to 50%.
Optionally, the one or more compounds of formula II are preferably selected from the group consisting of compounds of formulae II1-II 16.
Figure BDA0001855400210000161
/>
Figure BDA0001855400210000171
Optionally, the aforementioned one or more compounds of formula III are preferably selected from the group consisting of compounds of formulae III1-III 14.
Figure BDA0001855400210000172
/>
Figure BDA0001855400210000181
Wherein R in the compounds represented by the formulas III1 to III14 3 、R 4 With R in the compound of the formula III 3 、R 4 Are as defined in (1), each independentlyRepresents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more non-adjacent-CH of the group 2 -optionally substituted with cyclopentylene, cyclobutyl or cyclopropylene.
In one embodiment of the liquid crystal composition of the present invention, optionally, the liquid crystal composition may further comprise one or more compounds represented by formula iv.
Figure BDA0001855400210000191
Wherein R is 5 、R 6 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 5 、R 6 Any one or more non-adjacent-CH 2 -optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene;
w represents-O-, -S-or-CH 2 O-。
By containing the compound shown in the formula IV in the liquid crystal composition, the liquid crystal composition has larger negative dielectric anisotropy, and is favorable for reducing the driving voltage of a device. In the case where the compound represented by the formula IV is contained in the liquid crystal composition of the present invention, the amount (mass percentage) of the compound represented by the formula IV added to the liquid crystal composition may be 1 to 15%, preferably 2 to 10%.
Preferably, the aforementioned one or more compounds of formula IV are selected from the group consisting of compounds of formulae IV 1-IV 6:
Figure BDA0001855400210000192
Figure BDA0001855400210000201
wherein R is 61 Represents an alkyl group having 2 to 6 carbon atoms.
In some embodiments, the liquid crystal composition of the present invention may further comprise one or more compounds represented by formula v.
Figure BDA0001855400210000202
Wherein R is 7 、R 8 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
Figure BDA0001855400210000203
each independently represents 1, 4-phenylene, 1, 4-cyclohexylene or 1, 4-cyclohexenylene.
Optionally, the one or more compounds of formula v are selected from the group consisting of compounds of formulae v 1-v 4:
Figure BDA0001855400210000204
wherein R is 71 、R 81 Each independently represents an alkyl group having 2 to 6 carbon atoms or an alkenyl group having 2 to 6 carbon atoms; among them, the aforementioned alkenyl group having 2 to 6 carbon atoms is exemplified byVinyl, 2-propenyl or 3-pentenyl. R is 82 Represents an alkoxy group having 1 to 5 carbon atoms;
the amount (mass percentage) of the compound represented by the formula V added to the liquid crystal composition may be 1 to 40%, preferably 5 to 30%.
The compound shown in the formula V has high clearing point and elastic constant, especially splay elastic constant K33, and is beneficial to improving the parameter performance of the liquid crystal composition.
In some embodiments, the liquid crystal composition of the present invention may further comprise one or more polymerizable compounds represented by formula VI,
Figure BDA0001855400210000211
Figure BDA0001855400210000212
each independently represents phenylene, fluorinated phenylene or indanyl;
P 1 、P 2 、P 3 each independently represents a methacrylate group or an acrylate group. In the formula VI
Figure BDA0001855400210000213
The connection to P3 is indicated by a dotted line, indicating P 3 And/or>
Figure BDA0001855400210000214
Can be attached at any possible location.
Optionally, one or more of the compounds of formula VI above is selected from the group consisting of compounds of formulae VI 1-VI 3:
Figure BDA0001855400210000215
the compounds of formula VI have a slightly lower UV sensitivity and a slightly slower rate of polymerization than the compounds of formula I, and are relatively superficial when the polymer is actually formed. Under the condition that the compound shown in the formula VI and the compound shown in the formula I are added for copolymerization, the display effect can be improved, the polymer layer provides continuous and stable pre-tilt, and the pre-tilt of liquid crystal molecules is very favorable for improving the response speed of liquid crystals under an electric field. When the compound shown in the formula VI is added to be copolymerized with the compound shown in the formula I, the compound shown in the formula VI can be added in an amount of 0.1-1% by mass, and preferably 0.2-0.5% by mass.
In the liquid crystal composition of the present invention, a dopant having various functions may be optionally added, and when a dopant is contained, the content of the dopant is preferably 0.01 to 1% by mass in the liquid crystal composition, and examples of the dopant include an antioxidant, an ultraviolet absorber, and a chiral agent.
Examples of the antioxidant and ultraviolet absorber include:
Figure BDA0001855400210000221
t represents an integer of 1 to 10.
The invention also relates to a liquid crystal display element or a liquid crystal display comprising any one of the liquid crystal compositions; the display element or display is an active matrix display element or display or a passive matrix display element or display.
Optionally, the liquid crystal display element or liquid crystal display is preferably an active matrix addressed liquid crystal display element or liquid crystal display.
Optionally, the active matrix display element or display is a PSVA-TFT liquid crystal display element or display without a PI alignment layer.
Optionally, the active matrix display element or the display is a PSVA-TFT liquid crystal display element or a display having a PI alignment layer on one side and no PI alignment layer on the other side.
The liquid crystal display element or the liquid crystal display comprising the compound or the liquid crystal composition does not need to be additionally provided with a traditional alignment layer, so that the problems of poor yield, poor heat resistance and poor aging resistance of a liquid crystal display device and the like caused by dust particles, static residues, brush marks and the like caused by the arrangement of the alignment layer can be avoided, the preparation process of the liquid crystal display element or the liquid crystal display is effectively simplified, the production efficiency can be improved, and the production cost can be reduced. In addition, the liquid crystal display element or the liquid crystal display obtained by the liquid crystal composition has the characteristics of wide nematic phase temperature range, proper or higher birefringence anisotropy delta n and high charge retention rate.
Examples
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In the invention, the preparation method is a conventional method unless otherwise specified, the used raw materials can be obtained from a public commercial way unless otherwise specified, the percentages refer to mass percentages, the temperature is centigrade (DEG C), the liquid crystal compound also becomes a liquid crystal monomer, and the specific meanings and test conditions of other symbols are as follows:
cp represents a liquid crystal clearing point (DEG C), and is measured by a DSC quantitative method;
Δ n denotes optical anisotropy, Δ n = n e -n o Wherein n is o Refractive index of ordinary light, n e The refractive index of the extraordinary ray is measured under the conditions of 25 +/-2 ℃ and 589nm, and the Abbe refractometer is used for testing;
Δ ε represents the dielectric anisotropy, Δ ε = ε// - ε ″, where ε// is the dielectric constant parallel to the molecular axis, ε ″ ″ is the dielectric constant perpendicular to the molecular axis, the test conditions were 25 ± 0.5 ℃,20 micron parallel box, INSTEC: ALCT-IR1 test;
VHR represents the voltage holding ratio (%), and the test conditions are 20 +/-2 ℃, voltage +/-5V, pulse width 10ms and voltage holding time 16.7ms. The test equipment is a TOYO Model6254 liquid crystal performance comprehensive tester;
γ 1 represents rotational viscosity (mPas) and the test conditions are 25. + -. 0.5 ℃ in 20 μm parallel cells, INSTEC: ALCT-IR1 test.
The preparation method of the liquid crystal composition comprises the following steps: weighing each liquid crystal monomer according to a certain proportion, putting the liquid crystal monomers into a stainless steel beaker, putting the stainless steel beaker filled with each liquid crystal monomer on a magnetic stirring instrument for heating and melting, adding a magnetic rotor into the stainless steel beaker after most of the liquid crystal monomers in the stainless steel beaker are melted, uniformly stirring the mixture, and cooling to room temperature to obtain the liquid crystal composition.
The liquid crystal monomer structure used in the embodiment of the invention is represented by codes, and the code representation methods of the liquid crystal ring structure, the end group and the connecting group are shown in the following tables 1 and 2.
Corresponding code of the ring structure of Table 1
Figure BDA0001855400210000241
TABLE 2 corresponding codes for end groups and linking groups
Figure BDA0001855400210000242
Figure BDA0001855400210000251
Examples are:
Figure BDA0001855400210000252
the code is CC-Cp-V1;
Figure BDA0001855400210000253
the code is PGP-Cpr1-2;
Figure BDA0001855400210000254
the code is CPY-2-O2;
Figure BDA0001855400210000255
the code is CCY-3-O2;
Figure BDA0001855400210000256
the code is COY-3-O2;
Figure BDA0001855400210000257
the code is CCOY-3-O2; />
Figure BDA0001855400210000258
The code is Sb-Cp1O-O4;
Figure BDA0001855400210000259
the code is Sc-Cp1O-O4.
[ Compound ]
The compounds of formula I can be prepared by the following illustrative synthetic routes:
the synthesis method of the patent refers to the synthesis methods related to patents CN105001879A and CN 108026448A. CN105001879A, CN108026448A are incorporated herein by reference in their entirety.
Figure BDA0001855400210000261
Wherein Xa represents-CH 2 -or-O-, two-O-cannot be directly linked, r represents an integer from 1 to 10; r a 、R b Represents an alkyl group or an alkoxy group having 1 to 10 carbon atoms. R 0 、K 1 、Z 0 、q、K 2 Are as defined in formula I. Wherein R is 0 Represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atomsA C3-C8 alkenyloxy group substituted with a fluorine group or a group represented by the formula 0 Any one or more non-adjacent-CH in the group 2 -may each independently be replaced by-O-or cycloalkylene;
q represents 1, 2 or 3;
K 1 、K 2 each independently represents an aromatic ring, a heteroaromatic ring, an aliphatic ring or a fused ring, wherein any one or more of the non-adjacent-CH's on the aromatic, heteroaromatic, aliphatic or fused ring 2 Optionally substituted by-O-, -S-, K 1 、K 2 Optionally one or more H on the ring of (a) is substituted by L or-Sp 1 -P 5 Substitution;
l represents F, -Sp 2 -X 1 An alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, wherein any one or more of the groups represented by L is not adjacent to-CH 2 -optionally substituted by cyclopentylene, cyclobutyl, cyclopropylene;
P 5 represents H or a polymerizable group;
Sp 1 、Sp 2 each independently represents a single bond or a spacer;
X 1 each independently represents an alkyl-substituted carbonyl group having 1 to 10 carbon atoms or an alkyl-substituted ester group having 1 to 10 carbon atoms; any H in the alkyl with the carbon number of 1-10 is optionally substituted by F, and any one or more non-adjacent-CH 2 -optionally substituted by-O-, -S-;
Z 0 represents a single bond, -O-) -S-, -CO-) -COO-, -OCO-) -OCOO-, -OCH 2 -、-CH 2 O-、-SCH 2 -、-CH 2 S-、-CF 2 O-、-OCF 2 -、-CF 2 S-、-SCF 2 -、-(CH 2 )n 1 -、-CF 2 CH 2 -、-CH 2 CF 2 -、-(CF 2 )n 2 -、-CH＝CH-、-C≡C-、-CF＝CF-、-CH＝CH-COO-、-OCO-CH＝CH-、-(CR Y R Z )n 3 -、-CH(-Sp-P 6 )-、-CH 2 CH(-Sp-P 6 ) -, or, -CH (-Sp-P) 6 )CH(-Sp-P 6 )-；
n 1 、n 2 、n 3 Each independently represents 1, 2, 3 or 4;
R Y 、R Z each independently represents H or an alkyl group having 1 to 5 carbon atoms, and R Y 、R Z At least one of the alkyl is alkyl with 1-5 carbon atoms;
sp each independently represents a single bond or a spacer;
P 6 each independently represents H or a polymerizable group.
Example 1:
Figure BDA0001855400210000271
step 1
Figure BDA0001855400210000272
38.2g (0.10 mol) (1-a), 0.12mol triphenylphosphine, and 0.12mol imidazole were added into a 1L three-necked flask, 500ml dichloromethane was added, and the mixture was dissolved under stirring and cooled. At 0 ℃, under the protection of nitrogen, 17.6g (0.11 mol) of liquid bromine is added dropwise, the reaction releases heat, the protective gas is removed, the addition is finished for about 30 minutes, and the stirring is carried out for 2 hours at room temperature after the addition is finished. Dropwise adding a sodium bisulfite aqueous solution into a reaction system to quench and react, washing with water, drying, concentrating to obtain a viscous solid, adding 2 times of petroleum ether to dissolve the viscous solid, passing clear liquid through a silica gel column, washing with petroleum ether, concentrating a pure solvent, and recrystallizing with absolute ethyl alcohol to obtain 35.5g of white crystals (1-b), wherein GC:99.2%, yield: 80 percent
Step 2
Figure BDA0001855400210000281
200ml of methanol was added to a 1L three-necked flask, and 2.3g (0.1 mol) of sodium thread was carefully added under ice-water bath until the sodium thread completely disappeared. Continuously dropwise adding 0.1mol of methyl acetoacetate in the ice water bath to obtain a methyl acetoacetate sodium salt solution. 35.5g of the white crystals (1-b) obtained in the above step 1 were added in small portions, and after the addition was completed, the mixture was refluxed for 4 hours. Slowly dropwise adding water to quench and react, separating ethyl acetate for extraction, washing with water, concentrating, and recrystallizing with methanol and toluene to obtain 23g of white crystals (1-c) with a structural formula shown as formula I35, and performing HPLC:99.0%, yield: 60%, melting point: and 59.9 ℃.
Example 2:
Figure BDA0001855400210000282
step 1
Figure BDA0001855400210000283
Synthetic methods, reaction conditions referring to step 1 of example 1, one skilled in the art can prepare compound (2-b).
Step 2
Figure BDA0001855400210000291
Synthetic methods, reaction conditions referring to step 2 of example 1, one skilled in the art can prepare compound I14.
Example 3:
Figure BDA0001855400210000292
step 1
Figure BDA0001855400210000301
Synthesis method, reaction conditions referring to step 1 of example 1, one skilled in the art can prepare Compound (3-b)
Step 2
Figure BDA0001855400210000302
Synthetic methods, reaction conditions referring to example 1, step 2, one skilled in the art can prepare compound I26.
Example 4:
Figure BDA0001855400210000311
step 1
Figure BDA0001855400210000312
Synthesis method, reaction conditions referring to step 1 of example 1, one skilled in the art can prepare Compound (4-b)
Step 2
Figure BDA0001855400210000313
Synthetic methods, reaction conditions referring to step 2 of example 1, one skilled in the art can prepare compound I28.
[ liquid Crystal composition ]
Example 5: the components and their mass percentages in the liquid crystal composition are shown in the following table.
Figure BDA0001855400210000321
Example 6: the components and their mass percentages of the liquid crystal composition are shown in the following table.
Figure BDA0001855400210000322
/>
Figure BDA0001855400210000331
Example 7: the components and their mass percentages in the liquid crystal composition are shown in the following table.
Figure BDA0001855400210000332
Figure BDA0001855400210000341
Example 8: the components and their mass percentages in the liquid crystal composition are shown in the following table.
Figure BDA0001855400210000342
Figure BDA0001855400210000351
Comparative example 1
I-14 in example 8 was replaced by the existing reactive mesogen (A) having a dihydroxy structure
Figure BDA0001855400210000352
Figure BDA0001855400210000353
/>
Figure BDA0001855400210000361
Examples of the invention8 the liquid crystal composition was poured into a test cell (no polyimide alignment layer, cell thickness 4 μm, ITO electrode on the substrate surface, no passivation layer), voltage 15V was applied to both sides of the test cell, UV (dominant wavelength 313 nm) was irradiated for 200s,0.55mw/cm 2 Then the voltage was removed at 0.20mw/cm 2 And (3) irradiating for 100min by using light intensity, and completely polymerizing the compound shown in the formula I and the compound shown in the formula VI to form a polymerization layer with stable pretilt. After the treatment of the application of electricity and the irradiation of UV light, the liquid crystal molecules in the test cell are spontaneously vertically aligned, and the vertical alignment of the liquid crystal molecules can be maintained stable in an environment of 0 to 80 ℃.
The test box is under 78-80 ℃ temperature environment, through continuously applying voltage and switching dark state and light state, the pre-tilt of the polymeric layer still exists stably after 1000 hours of test.
Example 8 compared with comparative example 1, the compound shown in formula I in the liquid crystal composition provided by example 8 of the present invention has better low temperature solubility, higher VHR and is more favorable for improving the afterimage defect.
In summary, the compound shown in formula I can achieve the insulating effect of PI after polymerization, and can realize vertical alignment, and the polymer layer can provide a continuous and stable pre-tilt after the voltage is removed, so that the liquid crystal molecules have a stable pre-tilt, and the pre-tilt of the liquid crystal molecules is very favorable for improving the response speed of the liquid crystal under the electric field.

Claims (7)

1. A liquid crystal composition comprising one or more compounds of formulae I1 to I35, and a compound of formula VI-1 or VI-3:
Figure FDA0003775484210000011
/>
Figure FDA0003775484210000021
/>
Figure FDA0003775484210000031
/>
Figure FDA0003775484210000041
/>
Figure FDA0003775484210000051
/>
Figure FDA0003775484210000061
2. the liquid crystal composition according to claim 1, further comprising one or more compounds represented by the following formula II and one or more compounds represented by the following formula III,
Figure FDA0003775484210000062
in the formula II, R 1 、R 2 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms,
Figure FDA0003775484210000071
each independently represents->
Figure FDA0003775484210000072
In the formula III, R 3 、R 4 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more non-adjacent-CH 2 Optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene,
Z 1 、Z 2 each independently represents a single bond, -CH 2 CH 2 -or-CH 2 O-，
Figure FDA0003775484210000073
Each independently represents>
Figure FDA0003775484210000074
Figure FDA0003775484210000075
m represents 1 or 2; n represents 0, 1 or 2.
3. The liquid crystal composition of claim 2, wherein the one or more compounds of formula II are selected from the group consisting of compounds of formulae II1-II 16,
Figure FDA0003775484210000076
/>
Figure FDA0003775484210000081
4. the liquid crystal composition of claim 2, wherein the one or more compounds of formula III are selected from the group consisting of compounds of formulae III1 to III14,
Figure FDA0003775484210000082
/>
Figure FDA0003775484210000091
in the formulae III1 to III14, R 3 、R 4 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 3 、R 4 Any one or more non-adjacent-CH in 2 -optionally substituted by cyclopentylene, cyclobutyl or cyclopropylene.
5. The liquid crystal composition according to any one of claims 1 to 4, wherein the liquid crystal composition is a negative dielectric anisotropy liquid crystal composition further comprising one or more compounds represented by formula IV,
Figure FDA0003775484210000101
wherein R is 5 、R 6 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms, and R 5 、R 6 Any one or more non-adjacent-CH 2 -optionally substituted by a sub-ringPentyl, cyclobutyl or cyclopropylene substitution; w represents-O-, -S-or-CH 2 O-。
6. The liquid crystal composition of any one of claims 1 to 4, wherein the liquid crystal composition is a negative dielectric anisotropy liquid crystal composition further comprising one or more compounds of formula V,
Figure FDA0003775484210000102
wherein R is 7 、R 8 Each independently represents an alkyl group having 1 to 10 carbon atoms, a fluorine-substituted alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a fluorine-substituted alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, a fluorine-substituted alkenyl group having 2 to 10 carbon atoms, an alkenyloxy group having 3 to 8 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 8 carbon atoms;
Figure FDA0003775484210000103
each independently represents->
Figure FDA0003775484210000104
7. A liquid crystal display element or a liquid crystal display comprising the liquid crystal composition according to any one of claims 1 to 6, which is an active matrix display element or a display or a passive matrix display element or a display.
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