CN109575953B - Liquid crystal composition and liquid crystal display device thereof - Google Patents

Liquid crystal composition and liquid crystal display device thereof Download PDF

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CN109575953B
CN109575953B CN201710894138.4A CN201710894138A CN109575953B CN 109575953 B CN109575953 B CN 109575953B CN 201710894138 A CN201710894138 A CN 201710894138A CN 109575953 B CN109575953 B CN 109575953B
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crystal composition
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CN109575953A (en
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王立威
马文阳
徐海彬
张文琦
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Jiangsu Hecheng Display Technology 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
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • 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
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    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
    • C09K2019/0448—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate
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    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
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    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
    • C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
    • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
    • C09K2019/121—Compounds containing phenylene-1,4-diyl (-Ph-)
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Abstract

The invention discloses a liquid crystal composition, which comprises the following components in part by weight: at least one polymerizable compound of the general formula I; and at least one compound of the general formula II. The liquid crystal composition provided by the invention has suitable optical anisotropy and dielectric anisotropy, maintains a relatively high clearing point, and has good low-temperature storage stability. The invention also provides a liquid crystal display device comprising the liquid crystal composition, and the liquid crystal composition has excellent display effect when being applied to the liquid crystal display device.

Description

Liquid crystal composition and liquid crystal display device thereof
Technical Field
The invention relates to the field of liquid crystal materials, in particular to a liquid crystal composition and a liquid crystal display device thereof.
Background
Liquid crystal display devices have been used in various household electric appliances, measuring devices, panels for automobiles, word processors, electronic notepads, printers, computers, televisions, and the like, from clocks and calculators. Typical examples of the liquid crystal display mode include TN (twisted nematic) mode, STN (super twisted nematic) mode, DS (dynamic light scattering) mode, GH (guest host) mode, IPS (in-plane switching) mode, OCB (optically compensated birefringence) mode, ECB (voltage controlled birefringence) mode, VA (vertically aligned) mode, CSH (color super homeotropic) mode, and FLC (ferroelectric liquid crystal) mode. Further, as a driving method of the liquid crystal display device, a static driving, a multiplex driving, a simple matrix method, an Active Matrix (AM) method of driving by a TFT (thin film transistor), a TFD (thin film diode), or the like may be mentioned.
Among these display systems, the IPS mode, ECB mode, VA mode, CSH mode, and the like have a characteristic that a liquid crystal composition having a negative dielectric anisotropy Δ ∈ is used. Among these display systems, the VA display system driven by AM is used for a display element (for example, a television) which requires high-speed response and a wide viewing angle.
Liquid crystal materials need to have suitably high absolute values of dielectric anisotropy, optical anisotropy, and good low-temperature mutual solubility and thermal stability. In addition, the liquid crystal material should also have low viscosity and short response time, low threshold voltage and high contrast. The performance indexes of the composition are further described based on commercially available liquid crystal display elements. The temperature range of the nematic phase is associated with the operating temperature range of the element. The upper limit temperature of the nematic phase is preferably 70 ℃ or higher, and the lower limit temperature of the nematic phase is preferably-10 ℃ or lower. The viscosity of the composition correlates to the response time of the element. In order to display animation in the element, it is preferable that the response time of the element is short. Therefore, it is preferable that the viscosity of the composition is small, and it is more preferable that the viscosity of the composition is small at a low temperature.
The optical anisotropy of the composition correlates with the contrast of the element. In order to maximize the contrast ratio of the liquid crystal display element, the product value (Δ n × d) of the optical anisotropy (Δ n) of the liquid crystal composition and the thickness (d) of the liquid crystal layer may be designed to be a fixed value. The appropriate product value depends on the kind of operation mode. A suitable value for an element like TN mode is about 0.45 μm. In this case, a composition having a large optical anisotropy is preferable for an element having a small liquid crystal layer thickness.
A liquid crystal display element containing a liquid crystal composition having a large absolute value of dielectric anisotropy can reduce the base voltage value, reduce the driving voltage, and further reduce the power consumption.
The liquid crystal display element containing the liquid crystal composition with lower threshold voltage can effectively reduce the power consumption of display, and has longer endurance time particularly in consumables, such as portable electronic products like mobile phones, tablet computers and the like.
The liquid crystal composition with low viscosity can improve the response speed of the liquid crystal display element. When the response speed of the liquid crystal display element is high, the liquid crystal display element is applicable to animation display. In addition, when the liquid crystal composition is injected into the cell of the liquid crystal display device, the injection time can be shortened, and the workability can be improved.
On the other hand, the viscosity of the liquid crystal material affects the yield of the product during the manufacturing process, and when the viscosity of the liquid crystal material is high, the liquid crystal material is not well diffused, which easily causes uneven display of the device during the manufacturing process of the liquid crystal display device, thereby affecting the yield of the display device and affecting the display quality.
The prior art discloses a liquid crystal composition with low power consumption and fast response, such as patent document CN102858918A, but the prior art has environmental problems (such as use of chlorine-containing compounds), short service life (such as poor UV or thermal stability), low contrast (such as whitening of display screen under sunlight), and cannot satisfy all the performance balance problems of requiring appropriate optical anisotropy, appropriate dielectric anisotropy, high voltage holding ratio, UV stability and high temperature stability in lcd televisions, tablet computers, etc., and cannot satisfy all the indexes at the same time.
From the preparation angle of the liquid crystal material, various performances of the liquid crystal material are mutually influenced by the influence, and other performances may be changed by the improvement of a certain performance index. Therefore, creative efforts are often required to prepare liquid crystal materials having suitable properties in all aspects.
In addition, LCD panels are widely used throughout the world from a frigid zone such as a polar region to a tropical zone such as the equator. For this reason, the stability of the liquid crystal composition at low and high temperatures is very important. In particular, in the case where the panel is exposed to an extremely low temperature below zero, thereby causing crystal precipitation, the panel is not suitable. The crystal precipitation phenomenon occurs when the mutual solubility of individual liquid crystals in a liquid crystal composition deteriorates at low temperatures.
Disclosure of Invention
The purpose of the invention is as follows: in view of the drawbacks of the prior art, an object of the present invention is to provide a liquid crystal composition having a large optical anisotropy, a large absolute value of dielectric anisotropy, a wide nematic phase, and a high low-temperature storage stability, and a liquid crystal display device including the same.
The technical scheme of the invention is as follows:
one aspect of the present invention provides a liquid crystal composition comprising:
at least one polymerizable compound of the general formula I
Figure GDA0003552296920000031
And
at least one compound of the general formula II
Figure GDA0003552296920000032
Wherein the content of the first and second substances,
Rp2represent
Figure GDA0003552296920000033
P1、P2And P2' each independently represent
Figure GDA0003552296920000034
Figure GDA0003552296920000035
Figure GDA0003552296920000036
or-SH;
r1represents 1, 2 or 3;
r2、r3、r3' and r3"each independently represents a positive integer of 0 to 6;
r4and r5Each independently represents 0, 1, 2, 3 or 4;
Z1and Z2Each independently represents a single bond, -CH2CH2-、-COO-、-OCO-、-CH2O-、-OCH2-or-CH ═ CH-COO-;
Zp1and Zp2Each independently selected from the group consisting of a single bond, -O-, -S-, -NH-, -NHCOO-, -OCONH-, -CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH2CH2-、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CF＝CH-、-CH＝CF-、-CF＝CF-、-CO-、-COO-、-OCO-、-OCOO-、-CH2-、-OCH2-、-SCH2-、-CH2S-, -CH ═ CH-, -C ≡ C-, -CH ═ CH-COO-, and-OCO-CH ═ CH-;
Y1and Y2Each independently represents H, halogen, alkyl or alkoxy with 1-3C atoms;
R1and R2Each independently represents-H, alkyl OR alkoxy containing 1-12 carbon atoms, alkenyl OR alkenyloxy containing 2-12 carbon atoms, -OR3OR4、
Figure GDA0003552296920000037
And R is1And R2At least one of them is-OR3OR4；
R3Represents an alkylene group having 1 to 12 carbon atoms or an alkenylene group having 2 to 12 carbon atoms;
R4represents an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms;
ring (C)
Figure GDA0003552296920000038
Ring(s)
Figure GDA0003552296920000039
And a ring
Figure GDA00035522969200000310
Each independently represent
Figure GDA00035522969200000311
Figure GDA00035522969200000312
m represents 0, 1 or 2, and when m is 2, a ring
Figure GDA0003552296920000041
May be the same or different, Z2May be the same or different.
In some embodiments of the present invention, the compound of formula I comprises 0.001 to 5 wt% of the total weight of the liquid crystal composition; further preferably, the compound of the general formula I accounts for 0.003 to 1 wt% of the total weight of the liquid crystal composition; still more preferably, the compound of formula I accounts for 0.005-0.5 wt% of the total weight of the liquid crystal composition.
In some embodiments of the present invention, the compound of formula II comprises 1 to 70 wt% of the total weight of the liquid crystal composition; further preferably, the compound of the general formula II accounts for 1-60 wt% of the total weight of the liquid crystal composition; still more preferably, the compound of formula II accounts for 2-40 wt% of the total weight of the liquid crystal composition.
Preferably, in said formula I, P1And P2Each independently represent
Figure GDA0003552296920000042
Preferably, the compound of formula i is selected from the group consisting of:
Figure GDA0003552296920000043
Figure GDA0003552296920000051
Figure GDA0003552296920000061
Figure GDA0003552296920000071
Figure GDA0003552296920000081
Figure GDA0003552296920000082
and
Figure GDA0003552296920000083
preferably, the compound of formula ii is selected from the group consisting of:
Figure GDA0003552296920000084
Figure GDA0003552296920000091
Figure GDA0003552296920000092
and
Figure GDA0003552296920000093
wherein the content of the first and second substances,
R11and R21Each independently represents H, alkyl OR alkoxy having 1 to 7 carbon atoms, alkenyl OR alkenyloxy having 2 to 7 carbon atoms, -OR31OR41、
Figure GDA0003552296920000094
And R is11And R21At least one of them is-OR31OR41；
R31Represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms;
R41represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.
In some embodiments of the present invention, preferably, the compound of formula II-1 is selected from the group consisting of:
Figure GDA0003552296920000095
Figure GDA0003552296920000096
wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-；
Figure GDA00035522969200000913
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-or- (CH)2)3-；
Figure GDA0003552296920000098
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-or- (CH)2)4-；
Figure GDA0003552296920000099
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-or- (CH)2)5-；
Figure GDA00035522969200000910
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5-or- (CH)2)6-；
And
Figure GDA00035522969200000914
wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5-、-(CH2)6-or- (CH)2)8-，
The compound of formula II-2 is selected from the group consisting of:
Figure GDA00035522969200000912
Figure GDA0003552296920000101
Figure GDA0003552296920000102
and
Figure GDA0003552296920000103
the compound of formula II-3 is selected from the group consisting of:
Figure GDA0003552296920000104
Figure GDA0003552296920000105
wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-；
Figure GDA0003552296920000106
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-or- (CH)2)3-；
Figure GDA0003552296920000107
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-or- (CH)2)4-；
Figure GDA0003552296920000108
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-or- (CH)2)5-；
Figure GDA0003552296920000109
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5-or- (CH)2)6-；
And
Figure GDA00035522969200001010
wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5-、-(CH2)6-or- (CH)2)8-，
The compound of formula II-4 is selected from the group consisting of:
Figure GDA00035522969200001011
Figure GDA0003552296920000111
Figure GDA0003552296920000112
and
Figure GDA0003552296920000113
the compound of formula II-5 is selected from the group consisting of:
Figure GDA0003552296920000114
Figure GDA0003552296920000115
and
Figure GDA0003552296920000116
the compound of formula II-6 is selected from the group consisting of:
Figure GDA0003552296920000117
Figure GDA0003552296920000118
and
Figure GDA0003552296920000119
the compound of formula II-7 is selected from the group consisting of:
Figure GDA00035522969200001110
Figure GDA00035522969200001111
wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-；
Figure GDA00035522969200001112
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-or- (CH)2)3-；
Figure GDA00035522969200001113
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-or- (CH)2)4-；
Figure GDA0003552296920000121
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-or- (CH)2)5-；
Figure GDA0003552296920000122
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5-or- (CH)2)6-；
And
Figure GDA0003552296920000123
wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5-、-(CH2)6-or- (CH)2)8-，
The compound of formula II-8 is selected from the group consisting of:
Figure GDA0003552296920000124
Figure GDA0003552296920000125
and
Figure GDA0003552296920000126
the compounds of formula II-9 are selected from the group consisting of:
Figure GDA0003552296920000127
Figure GDA0003552296920000128
wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-；
Figure GDA0003552296920000129
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-or- (CH)2)3-；
Figure GDA00035522969200001210
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-or- (CH)2)4-；
Figure GDA00035522969200001211
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-or- (CH)2)5-；
Figure GDA00035522969200001212
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5-or- (CH)2)6-；
Figure GDA0003552296920000131
Wherein, if R11represents-OR31OR41Then R is31Is not- (CH)2)2-、-(CH2)3-、-(CH2)4-、-(CH2)5-、-(CH2)6-or- (CH)2)8-，
The compounds of formula II-10 are selected from the group consisting of:
Figure GDA0003552296920000132
Figure GDA0003552296920000133
and
Figure GDA0003552296920000134
the compounds of formula II-11 are selected from the group consisting of:
Figure GDA0003552296920000135
Figure GDA0003552296920000141
Figure GDA0003552296920000142
and
Figure GDA0003552296920000143
the compounds of formula II-12 are selected from the group consisting of:
Figure GDA0003552296920000144
Figure GDA0003552296920000151
Figure GDA0003552296920000152
and
Figure GDA0003552296920000153
the compounds of formula II-13 are selected from the group consisting of:
Figure GDA0003552296920000154
Figure GDA0003552296920000161
and
Figure GDA0003552296920000162
the compounds of formula II-14 are selected from the group consisting of:
Figure GDA0003552296920000163
Figure GDA0003552296920000164
and
Figure GDA0003552296920000165
the compounds of formula II-15 are selected from the group consisting of:
Figure GDA0003552296920000166
Figure GDA0003552296920000171
Figure GDA0003552296920000172
and
Figure GDA0003552296920000173
further, the liquid crystal composition further comprises at least one compound of the general formula II':
Figure GDA0003552296920000174
wherein, the first and the second end of the pipe are connected with each other,
R1' and R2' independently of one another represent-H, an alkyl or alkoxy group having 1 to 12 carbon atoms, an alkenyl or alkenyloxy group having 2 to 12 carbon atoms,
Figure GDA0003552296920000175
Ring (C)
Figure GDA0003552296920000176
Ring (C)
Figure GDA0003552296920000177
And a ring
Figure GDA0003552296920000178
Each independently represent
Figure GDA0003552296920000179
Figure GDA00035522969200001710
Z2' represents a single bond, -CH2CH2-、-COO-、-OCO-、-CH2O-、-OCH2-or-CH ═ CH-COO-;
m 'represents 0, 1 or 2, and when m' is 2, a ring
Figure GDA0003552296920000181
May be the same or different, Z2' may be the same or different.
In some embodiments of the invention, the compound of formula ii' is selected from the group consisting of:
Figure GDA0003552296920000182
Figure GDA0003552296920000183
and
Figure GDA0003552296920000191
wherein the content of the first and second substances,
R11' and R21' independently of one another represent-H, an alkyl or alkoxy group having 1 to 7 carbon atoms, an alkenyl or alkenyloxy group having 2 to 7 carbon atoms,
Figure GDA0003552296920000192
In some embodiments of the present invention, the compound of formula II' comprises 20 to 80 wt% of the total weight of the liquid crystal composition; further preferably, the compound of the general formula II' accounts for 20-75 wt% of the total weight of the liquid crystal composition; still more preferably, the compound of formula II' accounts for 25-70 wt% of the total weight of the liquid crystal composition.
Further, the liquid crystal composition further comprises at least one compound of formula III or at least one compound of formula IV:
Figure GDA0003552296920000193
wherein the content of the first and second substances,
R5and R6Each independently represents-H, alkyl OR alkoxy containing 1-12 carbon atoms, alkenyl OR alkenyloxy containing 2-12 carbon atoms, -OR3OR4、
Figure GDA0003552296920000194
R7represents-H, -F, alkyl OR alkoxy containing 1-12 carbon atoms, alkenyl OR alkenyloxy containing 2-12 carbon atoms, -OR3OR4、
Figure GDA0003552296920000195
Wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted by F;
x represents-F, a fluoroalkyl or fluoroalkoxy group having 1 to 12 carbon atoms, a fluoroalkenyl or fluoroalkenyloxy group having 2 to 12 carbon atoms;
Z3and Z4Each independently represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-；
Z5Represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-、-CF2O-、-OCF2-or-CH2CH2-；
L1And L2Each independently represents-F, -Cl, -CN or-NCS;
L3represents-H or-CH3；
L4And L5Each independently represents-H or-F;
ring (C)
Figure GDA0003552296920000196
And ring
Figure GDA0003552296920000197
Each independently represent
Figure GDA0003552296920000198
Wherein the content of the first and second substances,
Figure GDA0003552296920000199
in one or more-CH2-can be replaced by-O-,
Figure GDA00035522969200001910
wherein one or more H may be substituted by halogen;
ring (C)
Figure GDA0003552296920000201
Represent
Figure GDA0003552296920000202
Wherein
Figure GDA0003552296920000203
In one or more-CH2-may be replaced by-O-, single bonds in one or more rings may be replaced by double bonds,
Figure GDA0003552296920000204
wherein one or more H may be substituted by halogen, and one or more rings-CH-may be replaced by-N-;
n1 and n2 each independently represent 0, 1, 2 or 3, and when n1 is 2 or 3, the ring
Figure GDA0003552296920000205
May be the same or different, Z3May be the same or different; when n2 is 2 or 3, the ring
Figure GDA0003552296920000206
May be the same or different, Z4May be the same or different;
q represents 1, 2, 3 or 4, and when q is 2, 3, 4, a ring
Figure GDA0003552296920000207
May be the same or different, Z5May be the same or different.
In some embodiments of the invention, the compound of formula iii is selected from the group consisting of:
Figure GDA0003552296920000208
Figure GDA0003552296920000211
Figure GDA0003552296920000212
and
Figure GDA0003552296920000213
wherein the content of the first and second substances,
R51and R61Each independently represents-H, alkyl OR alkoxy containing 1-7 carbon atoms, alkenyl OR alkenyloxy containing 2-7 carbon atoms, -OR31OR41、
Figure GDA0003552296920000214
R31Represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms;
R41represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.
In some embodiments of the invention, the compound of formula III is 20 to 70 wt% of the total weight of the liquid crystal composition; further preferably, the compound of formula III accounts for 25-60 wt% of the total weight of the liquid crystal composition; still more preferably, the compound of formula iii accounts for 25-55 wt% of the total weight of the liquid crystal composition.
In some embodiments of the invention, the compound of formula iv is selected from the group consisting of:
Figure GDA0003552296920000215
Figure GDA0003552296920000221
Figure GDA0003552296920000231
Figure GDA0003552296920000241
Figure GDA0003552296920000251
Figure GDA0003552296920000261
Figure GDA0003552296920000271
Figure GDA0003552296920000281
Figure GDA0003552296920000282
and
Figure GDA0003552296920000283
wherein the content of the first and second substances,
R71represents-H, -F, alkyl OR alkoxy containing 1-7 carbon atoms, alkenyl OR alkenyloxy containing 2-7 carbon atoms, -OR31OR41Wherein one or more H of said alkyl or alkoxy and said alkenyl or alkenyloxy may be substituted by F;
R31represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms;
R41represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.
In some embodiments of the present invention, the compound of formula IV comprises 20 to 70 wt% of the total weight of the liquid crystal composition; further preferably, the compound of the general formula IV accounts for 20-60 wt% of the total weight of the liquid crystal composition; still more preferably, the compound of the general formula IV accounts for 25-55 wt% of the total weight of the liquid crystal composition.
In some embodiments of the invention, the compound of formula I is preferably selected from the group consisting of: i-1, I-24, I-64 and I-76.
In some embodiments of the invention, the compound of formula II is preferably selected from the group consisting of: II-6-3, II-5-3, II-9-3, II-3-3, II-1-2 and II-2-2.
In some embodiments of the invention, the compound of formula III is preferably selected from the group consisting of: III-3, III-6, III-2, III-8 and III-5.
In some embodiments of the invention, the compound of formula IV is preferably selected from the group consisting of: IV-6, IV-9, IV-39, IV-2, IV-1 and IV-7.
In some embodiments of the invention, the compound of formula II' is preferably selected from the group consisting of: II ' -10, II ' -1, II ' -3, II ' -12, II ' -6, II ' -5 and II ' -2.
In another aspect, the present invention provides a liquid crystal composition further comprising one or more additives known to those skilled in the art and described in the literature. For example, pleochroic dyes and/or chiral dopants may be added in an amount of 0 to 15 wt% based on the total weight of the liquid crystal composition.
The following shows possible dopants which are preferably added to the mixtures according to the invention.
Figure GDA0003552296920000291
Figure GDA0003552296920000301
Figure GDA0003552296920000302
And
Figure GDA0003552296920000303
in the embodiment of the present invention, preferably, the dopant accounts for 0 to 5 wt% of the total weight of the liquid crystal composition; more preferably, the dopant constitutes 0-1 wt% of the total weight of the liquid crystal composition.
The stabilizers which may be added to the mixtures according to the invention are mentioned below, for example.
Figure GDA0003552296920000304
Figure GDA0003552296920000311
Figure GDA0003552296920000321
Figure GDA0003552296920000331
Preferably, the stabilizer is selected from the group consisting of the stabilizers shown below.
Figure GDA0003552296920000332
In some embodiments of the present invention, preferably, the stabilizer comprises 0 to 5 wt% of the total weight of the liquid crystal composition; more preferably, the stabilizer is 0-1 wt% of the total weight of the liquid crystal composition; as a particularly preferred embodiment, the stabilizer is 0 to 0.1 wt% of the total weight of the liquid crystal composition.
In another aspect, the present invention also provides a liquid crystal display device comprising the above liquid crystal composition.
Has the beneficial effects that:
the liquid crystal composition provided by the invention has suitable optical anisotropy and dielectric anisotropy, maintains a relatively high clearing point, and has good low-temperature storage stability. When the liquid crystal composition is applied to a liquid crystal display, the liquid crystal composition has an excellent display effect.
Detailed Description
The invention will be illustrated 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.
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 GDA0003552296920000333
Figure GDA0003552296920000341
Compounds of the following formula are exemplified:
Figure GDA0003552296920000342
the structural formula is represented by the code listed in Table 1, and can be expressed as: nCCGF, wherein n in the code represents the number of C atoms of the left alkyl group, for example, n is 3, namely, the alkyl group is-C3H7(ii) a C in the code represents cyclohexane, G represents 2-fluoro-1, 4-phenylene and F represents fluorine.
The abbreviated codes of the test items in the following examples are as follows:
cp (. degree. C.) clearing Point (nematic-isotropic phase transition temperature)
Δ n optical anisotropy (589nm, 25 ℃ C.)
Delta epsilon dielectric anisotropy (1KHz, 25 ℃ C.)
Wherein the content of the first and second substances,
the optical anisotropy is obtained by testing an Abbe refractometer under a sodium lamp (589nm) light source at 25 ℃;
Δε＝ε‖-ε⊥wherein, epsilon‖Is a dielectric constant parallel to the molecular axis,. epsilon⊥For the dielectric constant perpendicular to the molecular axis, test conditions: at 25 ℃ and 1KHz, comparative examples 1-2 and examples 1-6 were tested using a VA type test cell having a cell thickness of 7 μm, and comparative example 3 and examples 7-9 were tested using a TN90 type test cell having a cell thickness of 7 μm;
test conditions for low temperature stability: the liquid crystal was poured into a low temperature storage box (cell) having a cell thickness of 7 μm and stored at a low temperature of-40 ℃ or stored at a low temperature of-20 ℃ or-30 ℃ after being placed in a 5mL liquid crystal storage bottle (bottle).
The components used in the following examples can be synthesized by a known method or obtained commercially. These synthesis techniques are conventional, and the resulting liquid crystal compounds were tested to meet the standards for electronic compounds.
Liquid crystal compositions were prepared according to the compounding ratios of the liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared according to the conventional method in the field, such as heating, ultrasonic wave, suspension and the like, and is mixed according to the specified proportion.
Liquid crystal compositions given in the following examples were prepared and studied. The composition of each liquid crystal composition and the results of the performance parameter test thereof are shown below.
Comparative example 1
The liquid crystal composition of comparative example 1, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared by using the respective compounds and weight percentages listed in tables 2 and 3.
TABLE 2 liquid crystal composition formula
Component code Weight percent (wt.%) of
3CPP2 3
3CGPC3 5
3C1OWO2 9
2CC1OWO2 9
3CC1OWO2 9
3CC2 15.5
3CCP1 2
5PP1 10
3PPO2 4
3CCV1 12
2C1OWO2 9
4C1OWO2 4.5
2PGPC3 4
3PGPC2 4
Total of 100
The polymerizable components in table 3 were added to 100 parts by weight of the liquid crystal composition:
TABLE 3 polymerizable Components
Figure GDA0003552296920000361
The results of the performance parameter tests of the resulting composition are given in table 4 below:
table 4 performance parameter testing
Figure GDA0003552296920000362
Example 1
The liquid crystal composition of example 1, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared from the compounds and weight percentages listed in Table 5 and the polymerizable components of comparative example 1.
TABLE 5 liquid Crystal composition formulations
Figure GDA0003552296920000363
Figure GDA0003552296920000371
The contents and components of the polymerizable components were the same as in comparative example 1.
The results of the performance parameter tests of the resulting composition are given in table 6 below:
TABLE 6 Performance parameter testing
Figure GDA0003552296920000372
Example 2
The liquid crystal composition of example 2, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared from the respective compounds and weight percentages listed in Table 7, and the polymerizable components of comparative example 1.
TABLE 7 liquid crystal composition formulations
Figure GDA0003552296920000373
Figure GDA0003552296920000381
The contents and components of the polymerizable components were the same as in comparative example 1.
The results of the performance parameter tests of the resulting composition are given in table 8 below:
TABLE 8 Performance parameter testing
Figure GDA0003552296920000382
Example 3
The liquid crystal composition of example 3 was prepared by using the compounds and weight percentages listed in tables 9 and 10, and filled between two substrates of a liquid crystal display to perform a performance test.
TABLE 9 liquid Crystal composition formulations
Component code Weight percent (wt.%) of
3CPP2 4
3CPPCO4O1 5
3C1OWO2 9
2CC1OWO2 9
3CC1OWO2 9
3CC2 15.5
3CCP1 4
5PP1 9
3PPO2 5
3CCV1 11
2C1OWO2 9
4C1OWO2 4.5
2PGPC3 2
3PGPC2 4
Total of 100
The polymerizable components in table 10 were added to 100 parts by weight of the above liquid crystal composition:
TABLE 10 polymerizable Components
Figure GDA0003552296920000391
The results of the performance parameter tests of the resulting composition are given in table 11 below:
TABLE 11 Performance parameter testing
Figure GDA0003552296920000392
As can be seen from comparison between comparative example 1 and examples 1 to 3, the low-temperature storage stability of the liquid crystal composition is significantly improved by incorporating the component of the general formula II of the present invention.
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 by using the respective compounds and weight percentages listed in tables 12 and 13.
TABLE 12 liquid crystal composition formulations
Figure GDA0003552296920000393
Figure GDA0003552296920000401
To 100 parts by weight of the above liquid crystal composition were added polymerizable components in table 13:
TABLE 13 polymerizable Components
Figure GDA0003552296920000402
The results of the performance parameter tests of the resulting composition are given in table 14 below:
TABLE 14 Performance parameter testing
Figure GDA0003552296920000403
Example 4
The liquid crystal composition of example 4, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was formulated with each compound and weight percentage as listed in tables 15 and 16.
TABLE 15 liquid crystal composition formulations
Figure GDA0003552296920000404
Figure GDA0003552296920000411
To 100 parts by weight of the above liquid crystal composition were added polymerizable components in table 16:
TABLE 16 polymerizable Components
Figure GDA0003552296920000412
The results of the performance parameter tests of the resulting composition are given in table 17 below:
TABLE 17 Performance parameter testing
Figure GDA0003552296920000413
Example 5
The liquid crystal composition of example 5, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was formulated with each compound and weight percentage as listed in tables 18 and 19.
TABLE 18 liquid crystal composition formulations
Figure GDA0003552296920000414
Figure GDA0003552296920000421
To 100 parts by weight of the above liquid crystal composition were added polymerizable components in table 19:
TABLE 19 polymerizable Components
Figure GDA0003552296920000422
The results of the performance parameter tests of the resulting composition are given in table 20 below:
TABLE 20 Performance parameter testing
Figure GDA0003552296920000423
Example 6
The liquid crystal composition of example 6, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was formulated with each compound and weight percentage as listed in tables 21 and 22.
TABLE 21 liquid Crystal composition formulations
Component code Weight percent (wt.%) of
3CPO1 7
3CPO2 8
3CPPO4O1 4
2CPPO4O1 4
3CWO2 8
2CPWO2 6.5
3CPWO2 7
3CPWO4 6.5
3CWO4 8
3CCWO2 6
3PWP4 7.5
3CC2 11
4CC3 10.5
3CCV1 6
Total of 100
To 100 parts by weight of the above liquid crystal composition, polymerizable components in table 22 were added:
TABLE 22 polymerizable Components
Figure GDA0003552296920000431
The results of the performance parameter tests on the resulting compositions are given in table 23 below:
TABLE 23 Performance parameter testing
Figure GDA0003552296920000432
Figure GDA0003552296920000441
As can be seen from comparison between comparative example 2 and examples 4 to 6, the low-temperature storage stability of the liquid crystal composition is significantly improved by incorporating the component of the general formula II of the present invention.
Comparative example 3
The liquid crystal composition of comparative example 3, which was filled between two substrates of a liquid crystal display for performance test, was prepared from the polymerizable components of comparative example 1 in the respective compounds and weight percentages listed in Table 24.
TABLE 24 liquid Crystal composition formulations
Component code Weight percent (wt.%) of
3CPUF 12
5PP1 6.5
3CCV 34
2PGPC3 3.5
3PGPC2 4
3PGPF 4
4PGPF 1
2PGU1(2F)OPOCF3 5
3PGU1(2F)OPOCF3 6.5
4PGU1(2F)OPOCF3 6.5
3CCGF 7
3CCPOCF3 10
Total of 100
The contents and components of the polymerizable components were the same as in comparative example 1.
The results of the performance parameter tests on the resulting composition are given in table 25 below:
TABLE 25 Performance parameter testing
Figure GDA0003552296920000442
Figure GDA0003552296920000451
Example 7
The liquid crystal composition of example 7, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared from the respective compounds and weight percentages listed in Table 26 and the polymerizable components of comparative example 1.
TABLE 26 liquid Crystal composition formulations
Component code Weight percent of
3CPUF 12
5PPO4O1 6.5
3CCV 34
2PGPC3 3.5
3PGPC2 4
3PGPF 4
4PGPF 1
2PGU1(2F)OPOCF3 5
3PGU1(2F)OPOCF3 6.5
4PGU1(2F)OPOCF3 6.5
3CCGF 7
3CCPOCF3 10
Total of 100
The contents and components of the polymerizable components were the same as in comparative example 1.
The results of the performance parameter tests of the resulting composition are given in table 27 below:
TABLE 27 Performance parameter testing
Figure GDA0003552296920000452
Example 8
The liquid crystal composition of example 8, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared from the respective compounds and weight percentages listed in Table 28 and the polymerizable components of comparative example 1.
TABLE 28 liquid Crystal composition formulations
Component code Weight percent (wt.%) of
3CPUF 12
5PP1 6.5
3CCV 46
2PGPC3 3.5
3PGPC2 4
3PGPF 4
4PGPF 1
2PGU1(2F)OPOCF3 5
3PGU1(2F)OPOCF3 6.5
4PGU1(2F)OPOCF3 6.5
3CCO3O2 3
3CPO3O2 2
Total of 100
The contents and components of the polymerizable components were the same as in comparative example 1.
The results of the performance parameter tests of the resulting composition are given in table 29 below:
TABLE 29 Performance parameter testing
Figure GDA0003552296920000461
Example 9
The liquid crystal composition of example 9, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared according to the compounds and the weight percentage shown in Table 30 and the polymerizable composition of comparative example 1.
TABLE 30 liquid crystal composition formulations
Figure GDA0003552296920000462
Figure GDA0003552296920000471
The contents and components of the polymerizable components were the same as in comparative example 1.
The results of the performance parameter tests of the resulting composition are given in table 31 below:
TABLE 31 Performance parameter testing
Figure GDA0003552296920000472
As can be seen from comparison between comparative example 3 and examples 7 to 9, the low-temperature storage stability of the liquid crystal composition is significantly improved by incorporating the component of the general formula II of the present invention.
The above embodiments are merely illustrative of the technical concept and features of the present invention, and the present invention is not limited thereto, and equivalent changes and modifications made according to the spirit of the present invention should be covered thereby.

Claims (6)

1. A liquid crystal composition, comprising:
at least one polymerizable compound of the general formula I
Figure FDA0003552296910000011
At least one compound of the general formula II
Figure FDA0003552296910000012
At least one compound of formula II':
Figure FDA0003552296910000013
and
at least one compound of formula III:
Figure FDA0003552296910000014
wherein the content of the first and second substances,
Rp2to represent
Figure FDA0003552296910000015
P1、P2And P2' each independently represent
Figure FDA0003552296910000016
Figure FDA0003552296910000017
Figure FDA0003552296910000018
or-SH;
r1represents 1, 2 or 3;
r2、r3、r3' and r3"each independently represents a positive integer of 0 to 6;
r4and r5Each independently represents 0, 1, 2, 3 or 4;
Z1and Z2Each independently represents a single bond, -CH2CH2-、-COO-、-OCO-、-CH2O-、-OCH2-or-CH ═ CH-COO-;
Zp1and Zp2Each independently selected from the group consisting of a single bond, -O-, -S-, -NH-, -NHCOO-, -OCONH-, -CF2O-、-OCF2-、-CF2S-、-SCF2-、-CH2CH2-、-CF2CH2-、-CH2CF2-、-CF2CF2-、-CF＝CH-、-CH＝CF-、-CF＝CF-、-CO-、-COO-、-OCO-、-OCOO-、-CH2-、-OCH2-、-SCH2-、-CH2S-, -CH ═ CH-, -C ≡ C-, -CH ═ CH-COO-, and-OCO-CH ═ CH-;
Y1and Y2Each independently represents H, halogen, alkyl or alkoxy with 1-3C atoms;
R1and R2Each independently represents-H, alkyl OR alkoxy containing 1-12 carbon atoms, alkenyl OR alkenyloxy containing 2-12 carbon atoms, -OR3OR4、
Figure FDA0003552296910000021
And R is1And R2At least one of them is-OR3OR4；
R3Represents an alkylene group having 1 to 12 carbon atoms or an alkenylene group having 2 to 12 carbon atoms;
R4represents an alkyl group having 1 to 12 carbon atoms or an alkenyl group having 2 to 12 carbon atoms;
ring(s)
Figure FDA0003552296910000022
Ring (C)
Figure FDA0003552296910000023
And ring
Figure FDA0003552296910000024
Each independently represent
Figure FDA0003552296910000025
Figure FDA0003552296910000026
m represents 0, 1 or 2, and when m is 2, a ring
Figure FDA0003552296910000027
May be the same or different, Z2May be the same or different;
R1' and R2' each independently represents-H, an alkyl or alkoxy group having 1 to 12 carbon atoms, an alkenyl or alkenyloxy group having 2 to 12 carbon atoms,
Figure FDA0003552296910000028
Ring (C)
Figure FDA0003552296910000029
Ring(s)
Figure FDA00035522969100000210
And ring
Figure FDA00035522969100000211
Each independently represent
Figure FDA00035522969100000212
Figure FDA00035522969100000213
Z2' represents a single bond, -CH2CH2-、-COO-、-OCO-、-CH2O-、-OCH2-or-CH ═ CH-COO-;
m 'represents 0, 1 or 2, and when m' is 2, a ring
Figure FDA00035522969100000214
May be the same or different, Z2' may be the same or different;
R5and R6Each independently represents-H, alkyl OR alkoxy containing 1-12 carbon atoms, alkenyl OR alkenyloxy containing 2-12 carbon atoms, -OR3OR4、
Figure FDA00035522969100000215
Z3And Z4Each independently represents a single bond, -COO-, -OCO-, -CH2O-、-OCH2-or-CH2CH2-；
L1And L2Each independently represents-F, -Cl, -CN or-NCS;
ring (C)
Figure FDA00035522969100000216
And ring
Figure FDA00035522969100000217
Each independently represent
Figure FDA00035522969100000218
Wherein the content of the first and second substances,
Figure FDA00035522969100000219
in one or more-CH2-can be replaced by-O-,
Figure FDA00035522969100000220
wherein one or more H may be substituted by halogen;
n1 and n2 each independently represent 0, 1, 2 or 3, and when n1 is 2 or 3, the ring
Figure FDA00035522969100000221
May be the same or different, Z3May be the same or different; when n2 is 2 or 3, the ring
Figure FDA00035522969100000222
May be the same or different, Z4May be the same or different;
the compound of the general formula I accounts for 0.001-5 wt% of the total weight of the liquid crystal composition, the compound of the general formula II accounts for 1-40 wt% of the total weight of the liquid crystal composition, the compound of the general formula II' accounts for 20-80 wt% of the total weight of the liquid crystal composition, and the compound of the general formula III accounts for 20-70 wt% of the total weight of the liquid crystal composition;
the liquid crystal composition exhibits a negative dielectric anisotropy.
2. The liquid crystal composition of claim 1, wherein in the formula II, P is1And P2Each independently represent
Figure FDA0003552296910000031
3. The liquid crystal composition of claim 2, wherein the compound of formula i is selected from the group consisting of:
Figure FDA0003552296910000032
Figure FDA0003552296910000041
Figure FDA0003552296910000051
Figure FDA0003552296910000061
Figure FDA0003552296910000071
Figure FDA0003552296910000081
Figure FDA0003552296910000082
and
Figure FDA0003552296910000083
4. the liquid crystal composition of claim 1, wherein the compound of formula ii is selected from the group consisting of:
Figure FDA0003552296910000084
Figure FDA0003552296910000091
Figure FDA0003552296910000092
and
Figure FDA0003552296910000093
wherein the content of the first and second substances,
R11and R21Each independently represents H, alkyl OR alkoxy having 1 to 7 carbon atoms, alkenyl OR alkenyloxy having 2 to 7 carbon atoms, -OR31OR41、
Figure FDA0003552296910000094
And R is11And R21At least one of them is-OR31OR41；
R31Represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms;
R41represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.
5. The liquid crystal composition of claim 1, wherein the compound of formula iii is selected from the group consisting of:
Figure FDA0003552296910000095
Figure FDA0003552296910000101
Figure FDA0003552296910000111
and
Figure FDA0003552296910000112
wherein, the first and the second end of the pipe are connected with each other,
R51and R61Each independently represents-H, -F, alkyl OR alkoxy containing 1-7 carbon atoms, alkenyl OR alkenyloxy containing 2-7 carbon atoms, -OR31OR41、
Figure FDA0003552296910000113
R31Represents an alkylene group having 1 to 10 carbon atoms or an alkenylene group having 2 to 10 carbon atoms;
R41represents an alkyl group having 1 to 10 carbon atoms or an alkenyl group having 2 to 10 carbon atoms.
6. A liquid crystal display device comprising the liquid crystal composition according to any one of claims 1 to 5.
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