CN109988583B - Liquid crystal composition and liquid crystal display device - Google Patents

Liquid crystal composition and liquid crystal display device Download PDF

Info

Publication number
CN109988583B
CN109988583B CN201810005598.1A CN201810005598A CN109988583B CN 109988583 B CN109988583 B CN 109988583B CN 201810005598 A CN201810005598 A CN 201810005598A CN 109988583 B CN109988583 B CN 109988583B
Authority
CN
China
Prior art keywords
carbon atoms
group
liquid crystal
formula
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201810005598.1A
Other languages
Chinese (zh)
Other versions
CN109988583A (en
Inventor
张兴
李明
孟劲松
赵磊
梁志安
邵哲
王健
侯泽峰
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
Original Assignee
Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shijiazhuang Chengzhi Yonghua Display Material Co Ltd filed Critical Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
Priority to CN201810005598.1A priority Critical patent/CN109988583B/en
Publication of CN109988583A publication Critical patent/CN109988583A/en
Application granted granted Critical
Publication of CN109988583B publication Critical patent/CN109988583B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
    • C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked

Landscapes

  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Liquid Crystal Substances (AREA)

Abstract

The invention discloses a liquid crystalThe liquid crystal composition comprises at least one compound with a structural formula shown as a formula I, at least one compound with a structural formula shown as a formula II and at least one compound with a structural formula shown as a formula III:

Description

Liquid crystal composition and liquid crystal display device
Technical Field
The invention relates to the technical field of liquid crystal materials. And more particularly, to a liquid crystal composition and a liquid crystal display device.
Background
Since the first synthesis of liquid crystal by the austria scientist leinzel in 1888, the real development of the liquid crystal industry is over 30 years, and as the liquid crystal display material has obvious advantages, such as low driving voltage, small power consumption, high reliability, large display information amount, color display, no flicker, flat panel display realization and the like, the liquid crystal monomer and the liquid crystal display are subjected to huge development, and the development is from TN and STN of black and white small screens before 30 years to TN-TFT, VA-TFT, IPS-TFT, PDLC and the like of the existing color large screens.
The dielectric properties of the liquid crystal are represented by a dielectric constant ∈. The dielectric constant of the electric field parallel to the liquid crystal director is represented by ε/and the dielectric constant of the electric field perpendicular to the liquid crystal director is represented by ε ×, the dielectric anisotropy constant being Δ ε = ε/ε ×. If the direction of the permanent dipole moment of the polar group of the liquid crystal molecule coincides with the direction of the long axis of the molecule, the degree of electron shift in the direction of the long axis of the liquid crystal molecule is the largest, and thus, the dipole moment in the direction parallel to the long axis of the molecule is large, the dielectric anisotropy is positive, Δ ∈ > 0, and such a liquid crystal is called a positive liquid crystal. If the direction of the permanent dipole moment of the polar group of the liquid crystal molecule is perpendicular to the direction of the long axis of the molecule, the degree of electron shift in the direction of the short axis of the liquid crystal molecule is the largest, and thus, the liquid crystal having a small dipole moment in the direction perpendicular to the long axis of the molecule and a negative dielectric anisotropy, Δ ∈ < 0, is called a negative liquid crystal.
Currently, in the liquid crystal display market, the display modes with competitiveness are mainly in-plane switching, IPS, fringe-field switching, FFS, and vertical alignment, VA. Based on the pursuit of dynamic response by people, new display requirements such as VR and AR require higher and higher response speed, and the improvement of the response speed of the liquid crystal material is an urgent problem to be solved.
Therefore, it is desirable to provide a liquid crystal composition and a liquid crystal display device that solve at least one of the above problems.
Disclosure of Invention
A first object of the present invention is to provide a liquid crystal composition.
A second object of the present invention is to provide a liquid crystal display device.
In order to achieve the first purpose, the invention adopts the following technical scheme:
a liquid crystal composition comprises at least one compound liquid crystal compound with a structural formula shown as a formula I, at least one compound with a structural formula shown as a formula II and at least one compound with a structural formula shown as a formula III:
Figure BDA0001538520980000021
wherein the content of the first and second substances,
R 1 、R 2 each independently represents an alkyl group having 1 to 5 carbon atoms, and optionally one or more unconnected CH groups 2 An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 3 to 5 carbon atoms, which is substituted with a cyclopentyl group, a cyclobutyl group or a cyclopropyl group; r 1 And R 2 The hydrogens on any carbon atom in (a) may each independently be replaced by fluorine;
x represents S, O, -CH 2 CH 2 -or-CH 2 O-；
R 3 、R 4 、R 5 、R 6 Each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 3 to 5 carbon atoms; r 3 、R 4 、R 5 And R 6 Each hydrogen on any carbon atom in (a) is independently substituted with fluorine;
Z 1 represents a single bond or-CH 2 O-；
m, o, p each independently represent 0,1 or 2;
Figure BDA0001538520980000022
each independently represents any one or more of the following groups:
Figure BDA0001538520980000023
the compound with the structural formula I in the liquid crystal composition can greatly improve the dielectric property of the composition, the compound with the structural formula II can improve the viscosity and the clearing point, and the compound with the structural formula III can provide the basic dielectric property and the clearing point of the composition; in addition, the three components have mutual matching and synergistic effects, so that the balance effect of the composition in viscosity, clearing point and dielectric property is better, namely, the composition can provide a larger dielectric effect compared with the composition without the formula I.
Preferably, the structural formula of the compound with the structural formula I is at least one of formulas I-1 to I-4:
Figure BDA0001538520980000031
wherein R is 21 、R 22 Each independently represents an alkyl group having 1 to 5 carbon atoms, and optionally one or more unconnected CH groups 2 An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 3 to 5 carbon atoms, which is substituted with a cyclopentyl group, a cyclobutyl group or a cyclopropyl group; r 21 And R 22 The hydrogens on any carbon atom in (a) may each independently be replaced by fluorine.
Preferably, the structural formula of the compound with the structural formula II is at least one of formulas II-1 to II-5:
Figure BDA0001538520980000032
wherein the content of the first and second substances,
R 23 、R 24 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 3 to 5 carbon atoms; r 23 And R 24 The hydrogens on any carbon atom in (a) may each independently be replaced by fluorine.
Preferably, the compound of formula III has a formula of at least one of formulae III-1 to III-10:
Figure BDA0001538520980000041
wherein the content of the first and second substances,
R 23 、R 24 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 3 to 5 carbon atoms; r is 23 And R 24 The hydrogens on any carbon atom in (a) may each independently be replaced by fluorine.
Preferably, in the liquid crystal composition, the mass percent content of the compound with the structural formula I is 1-15%, the mass percent content of the compound with the structural formula II is 20-80%, and the mass percent content of the compound with the structural formula III is 10-70%.
Preferably, the liquid crystal composition further comprises one or more compounds of formula IV for the modulation of positive and negative dielectric:
Figure BDA0001538520980000051
wherein the content of the first and second substances,
R 7 、R 8 each independently represents F, an alkyl group having 1 to 5 carbon atoms, and optionally one or more unconnected CH 2 An alkyl group having 1 to 5 carbon atoms substituted with a cyclopentyl group, a cyclobutyl group or a cyclopropyl group, an alkyl group having 1 to 5 carbon atoms substituted with fluorine, an alkoxy group having 1 to 5 carbon atoms substituted with fluorine, an alkenyl group having 2 to 5 carbon atoms substituted with fluorine, an alkenyloxy group having 3 to 5 carbon atoms or an alkenyloxy group having 3 to 5 carbon atoms substituted with fluorine, provided that R is a substituent selected from the group consisting of a cyclopentyl group, a cyclobutyl group and a cyclopropyl group 7 And R 8 F is not simultaneously obtained;
Figure BDA0001538520980000052
each independently represent
Figure BDA0001538520980000053
Figure BDA0001538520980000054
n represents 1 or 2;
Z 2 、Z 3 each independently represents a single bond, -CF 2 O-、-CH 2 CH 2 -or-CH 2 O-。
Preferably, the structural formula of the compound with the structural formula IV is at least one of the following formulas IV-1 to IV-22:
Figure BDA0001538520980000055
Figure BDA0001538520980000061
Figure BDA0001538520980000071
wherein X 1 、X 2 Each independently represents H or F, but X in the same formula 1 、X 2 Not H at the same time, not F at the same time;
(F) Represents H or F;
R 51 ，R 52 each independently represents an alkyl group having 1 to 5 carbon atoms, and optionally one or more unconnected CH groups 2 An alkyl group having 1 to 5 carbon atoms substituted with a cyclopentyl group, a cyclobutyl group or a cyclopropyl group, an alkyl group having 5 carbon atoms substituted with fluorine, an alkoxy group having 1 to 5 carbon atoms substituted with fluorine, an alkenyl group having 2 to 5 carbon atoms substituted with fluorine, an alkenyloxy group having 3 to 5 carbon atoms or an alkenyloxy group having 3 to 5 carbon atoms substituted with fluorine.
Preferably, in the liquid crystal composition, the mass percentage content of the compound with the structural formula I is 1-15%, the mass percentage content of the compound with the structural formula II is 20-80%, the mass percentage content of the compound with the structural formula III is 5-70%, and the mass percentage content of the compound with the structural formula IV is 5-50%.
Preferably, the liquid crystal composition further comprises one or more compounds of formula V for the modulation of positive and negative dielectric:
Figure BDA0001538520980000081
wherein, the first and the second end of the pipe are connected with each other,
R 9 、R 10 each independently represents an alkyl group having 1 to 5 carbon atoms, a fluorine-substituted alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a fluorine-substituted alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a fluorine-substituted alkenyl group having 2 to 5 carbon atoms, an alkenyloxy group having 3 to 5 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 5 carbon atoms;
Z 4 represents a single bond or-CF 2 O-；
q represents 2 or 3;
Figure BDA0001538520980000082
represent
Figure BDA0001538520980000083
Figure BDA0001538520980000084
Preferably, the structural formula of the compound with the structural formula V is at least one of the following formulas V-1 to IV-28:
Figure BDA0001538520980000085
Figure BDA0001538520980000091
Figure BDA0001538520980000101
Figure BDA0001538520980000111
wherein the content of the first and second substances,
R 71 、R 72 each independently represents an alkyl group having 1 to 5 carbon atoms, a fluorine-substituted alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a fluorine-substituted alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a fluorine-substituted alkenyl group having 2 to 5 carbon atoms, an alkenyloxy group having 3 to 5 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 5 carbon atoms.
Preferably, in the liquid crystal composition, the mass percentage content of the compound with the structural formula I is 1-15%, the mass percentage content of the compound with the structural formula II is 20-80%, the mass percentage content of the compound with the structural formula III is 5-70%, the mass percentage content of the compound with the structural formula IV is 0-50%, and the mass percentage content of the compound with the structural formula V is 5-50%.
Preferably, in order to improve the UV resistance and the oxidation resistance, an additive can be added into the liquid crystal composition to serve as an antioxidant and ultraviolet resistant additive; more preferably, the additive is one or more of the following formulae S-1 to S-4:
Figure BDA0001538520980000112
Figure BDA0001538520980000121
in order to achieve the third object, the present invention provides a liquid crystal display device prepared from the liquid crystal composition as described above.
Preferably, the liquid crystal display device is a liquid crystal display element or a liquid crystal display.
Preferably, the liquid crystal display device is an active matrix display device or a passive matrix display device.
The invention has the following beneficial effects:
the liquid crystal composition has lower viscosity, larger dielectric anisotropy delta epsilon and moderate optical anisotropy delta n; the liquid crystal display device containing the liquid crystal composition has good reliability, and the liquid crystal composition has the advantages of high response speed and capability of prolonging the working time of mobile equipment.
Detailed Description
In order to more clearly illustrate the invention, the invention is further described below in connection with preferred embodiments. It is to be understood by persons skilled in the art that the following detailed description is illustrative and not restrictive, and is not to be taken as limiting the scope of the invention.
In the present invention, the preparation methods are all conventional methods unless otherwise specified. The percentages are mass percentages unless otherwise specified.
The liquid crystal composition of the present invention can be produced by mixing the liquid crystal compounds, for example, by mixing the different components at a high temperature and dissolving them in each other, or by other conventional methods, for example, by heating, ultrasonic wave, suspension, etc.
The percentages in the specification are mass percentages, the temperature is centigrade (DEG C), 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;
S-N represents the crystalline to nematic melting point (. Degree. C.) of the liquid crystal;
Δ n represents optical anisotropy, n o Refractive index of ordinary rays, 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 dielectric anisotropy, Δ ε = ε ∥ -ε ⊥ Wherein epsilon ∥ Is a dielectric constant parallel to the molecular axis,. Epsilon ⊥ Dielectric constant perpendicular to molecular axis, test conditions of 25 + -0.5 deg.C, 20 μm parallel box, INSTEC: ALCT-IR1 test;
gamma.1 represents rotational viscosity (mPas) under the test conditions of 25 + -0.5 ℃ in a 20-micron parallel box, INSTEC: ALCT-IR1 test;
rho represents resistivity (omega cm), the test condition is 25 +/-2 ℃, and the test instrument is a TOYO SR6517 high-impedance instrument and an LE-21 liquid electrode.
VHR represents the voltage holding ratio (%), the test conditions are 20 + -2 deg.C, voltage + -5V, pulse width 10ms, and voltage holding time 16.7ms. The test equipment is a TOYO Model6254 liquid crystal performance comprehensive tester.
Tau represents response time (ms), the test instrument is DMS-501, the test condition is 25 +/-0.5 ℃, the test box is a 3.3-micrometer IPS test box, the electrode spacing and the electrode width are both 10 micrometers, and the included angle between the friction direction and the electrode is 10 degrees.
T (%) represents transmittance, T (%) =100% bright state (Vop) luminance/light source luminance, test device DMS501, test conditions 25 ± 0.5 ℃, test cell is 3.3 μm IPS test cell, electrode pitch and electrode width are both 10 μm, and rubbing direction and electrode angle are 10 °.
The liquid crystal monomer structure 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 BDA0001538520980000131
Figure BDA0001538520980000141
TABLE 2 corresponding codes for end groups and linking groups
Figure BDA0001538520980000142
Figure BDA0001538520980000151
Examples are:
Figure BDA0001538520980000152
the code is VCCV1;
Figure BDA0001538520980000153
the code is C (5) BB (3F) B (3F, 5F) CF 2 OB(3F,4F,5F)。
The present invention will be described in further detail with reference to specific examples.
Example 1
The formulation of example 1 was as shown in table 3 below, and liquid crystal compositions were prepared and filled in test cells for performance tests, and the test results are also shown in table 3.
TABLE 3 examples 1 preparation of liquid crystal compositions starting Compounds for the formula classes, codes, contents and Properties
Figure BDA0001538520980000154
Figure BDA0001538520980000161
Comparative example 1
Formulation of comparative example 1 as shown in table 4 below, a liquid crystal composition was prepared, and the obtained liquid crystal composition was filled in a test cell for performance test, and the test results are also shown in table 4.
TABLE 4 structural formula class, code, content and properties of raw material compounds for preparing liquid crystal composition of comparative example 1
Figure BDA0001538520980000162
In contrast to example 1, comparative example 1 replaced compound 5OSaO2 of formula I in example 1 with the common 3CB B (2f, 3f) O2. Through test data, it can be found that, compared with example 1, under the condition that other parameters are basically consistent, Δ ∈ of comparative example 1 is reduced by 14%, and the reduction of Δ ∈ causes the increase of driving voltage, increases the energy consumption of the display device, and reduces the working time.
Example 2
The formulation of example 2 was as shown in table 5 below, and liquid crystal compositions were prepared and filled in test cells for performance tests, and the test results are also shown in table 5.
In this case, the ratio was adjusted so that Δ ∈ in example 2 was identical to that in comparative example 1, while keeping the kind of the monomer in example 1 unchanged.
TABLE 5 example 2 raw material compound structural formula classification, code, content and properties for preparing liquid crystal composition
Figure BDA0001538520980000163
Figure BDA0001538520980000171
It can be found from the test data that when the Δ ∈ values, Δ n values, and Cp values of example 2 and comparative example 1 are all equivalent, γ is expressed 1 Decrease by nearly 10%, gamma 1 The drop in (c) is particularly effective in reducing the response time τ.
This is also demonstrated through the test of response time τ of three sets of liquid crystals, as shown in table 6 below:
TABLE 6 response times of different test groups
Test set Example 1 Comparative example 1 Example 2
Response time tau 15ms 16ms 12ms
Of these, the response time of comparative example 1 is slow, approaching 33% for example 2.
Tests prove that the combination of the formula I, the formula II and the formula III can effectively improve the response speed, reduce the response time and save the energy consumption.
Example 3
The formulation of example 3 was as shown in table 7 below, and liquid crystal compositions were prepared and filled in test cells for performance tests, and the test results are also shown in table 7.
Example 3 the composition of formula ii was adjusted on the basis of example 2 to obtain a formulation with a more excellent clearing point.
TABLE 7 EXAMPLE 3 starting Compounds for preparing liquid Crystal compositions having the structural formula Classification, code, content and Properties
Figure BDA0001538520980000172
Figure BDA0001538520980000181
Example 4
The formulation of example 4 was as shown in table 8 below, and liquid crystal compositions were prepared and filled in test cells for performance tests, and the test results are also shown in table 8.
TABLE 8 example 4 raw material compounds for preparing liquid crystal composition structural formula classes, codes, contents and properties
Figure BDA0001538520980000182
Comparative example 2
Formulation of comparative example 2 as shown in table 9 below, a liquid crystal composition was prepared, and the obtained liquid crystal composition was filled in a test cell for performance test, and the test results are also shown in table 9.
Example 4 is a high penetration formulation, having requirements for both Δ ε and ε ″, removing formula I based on example 4, and (3) adjusting the proportion of other components to obtain a comparative example 2, wherein the formula is obtained when the delta epsilon and epsilon of the comparative example 2 are consistent with those of the example 4:
TABLE 9 structural formula class, code, content and properties of raw material compounds for preparing liquid crystal composition of comparative example 2
Figure BDA0001538520980000191
It can be seen from the comparison that gamma of comparative example 2 is consistent with the other parameters 1 Compared with the embodiment 4, the response time tau is measured to be 10% slower by 6%.
Tests prove that the combination of the formula I, the formula II and the formula III can effectively improve the response speed of the high-penetration formula and reduce the response time.
Example 5
The formulation of example 5 is shown in table 10 below, and liquid crystal compositions were prepared and filled in test cells for performance tests, and the test results are also shown in table 10.
Example 5 the composition of compound II was optimized on the basis of example 4 to increase its clearing point.
TABLE 10 examples 5 raw material compounds for preparing liquid crystal compositions structural formula classes, codes, contents and properties
Figure BDA0001538520980000192
Figure BDA0001538520980000201
Example 6
The formulation of example 6 was as shown in table 11 below, and liquid crystal compositions were prepared and filled in test cells for performance tests, and the test results are also shown in table 11.
TABLE 11 EXAMPLE 6 raw Material Compound formula Classification, code, content and Properties of liquid Crystal composition preparation
Figure BDA0001538520980000202
Example 7
The formulation of example 7 was as shown in table 12 below, and liquid crystal compositions were prepared and filled in test cells for performance tests, and the test results are also shown in table 12.
TABLE 12 EXAMPLE 7 raw Material Compound formula Classification, code, content and Properties of liquid Crystal composition preparation
Figure BDA0001538520980000211
The structure of the formula I and part of the structure of the formula III in example 1 are replaced, and the obtained parameters are also excellent
Example 8
The formulation of example 8 was as shown in table 13 below, and liquid crystal compositions were prepared and filled in test cells for performance tests, and the test results are also shown in table 13.
TABLE 13 examples 8 preparation of liquid crystal compositions starting Compounds for formula classes, codes, contents and Properties
Figure BDA0001538520980000212
Figure BDA0001538520980000221
Example 9
The formulation of example 9 was as shown in table 14 below, and liquid crystal compositions were prepared and filled in test cells for performance tests, and the test results are also shown in table 14.
TABLE 14 formula class, code, content and Properties of the starting Compounds for preparing liquid Crystal compositions in example 9
Figure BDA0001538520980000222
Some examples of the invention
The formulations of examples 10 to 11 are shown in tables 15 to 16 below, respectively, to prepare liquid crystal compositions, which were filled in test cells for performance tests, and the test results are also shown in tables 15 to 16, respectively.
TABLE 15 EXAMPLE 10 raw Material Compound formula classes, codes, contents and Properties for preparation of liquid Crystal compositions
Figure BDA0001538520980000223
Figure BDA0001538520980000231
TABLE 16 formula types, codes, contents and properties of the starting compounds for preparing liquid crystal compositions of example 11
Figure BDA0001538520980000232
And (4) conclusion: the liquid crystal composition has the advantages of low viscosity, good stability to light and heat, moderate refractive index and nematic phase temperature range, suitability for adjusting a fast response liquid crystal display device, and favorable characteristic of moving the working time of the liquid crystal display device.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.

Claims (10)

1. A liquid crystal composition, comprising at least one compound having a structural formula shown in formula I-1, at least one compound having a structural formula shown in formula II, and at least one compound having a structural formula shown in formula III:
Figure FDA0003937900330000011
wherein, the first and the second end of the pipe are connected with each other,
wherein R is 21 、R 22 Each independently represents an alkyl group having 1 to 5 carbon atoms, and optionally one or more unconnected CH groups 2 An alkyl group having 1 to 5 carbon atoms or an alkenyl group having 3 to 5 carbon atoms, which is substituted with a cyclopentyl group, a cyclobutyl group or a cyclopropyl group; r 21 And R 22 Each hydrogen on any carbon atom in (a) is independently substituted with fluorine;
R 3 、R 4 、R 5 、R 6 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, or an alkenyloxy group having 3 to 5 carbon atoms; r 3 、R 4 、R 5 And R 6 Each hydrogen on any carbon atom in (a) is independently substituted with fluorine;
Z 1 represents a single bond or-CH 2 O-；
m, o, p each independently represent 0,1 or 2;
Figure FDA0003937900330000012
each independently represents any one or more of the following groups:
Figure FDA0003937900330000013
2. the liquid crystal composition of claim 1, wherein the compound of formula II has a formula of at least one of formulae II-1 to II-5:
Figure FDA0003937900330000014
Figure FDA0003937900330000021
wherein the content of the first and second substances,
R 23 、R 24 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 3 to 5 carbon atoms; r 23 And R 24 The hydrogens on any carbon atom in (a) may each independently be replaced by fluorine.
3. The liquid crystal composition of claim 1, wherein the compound of formula III has a formula of at least one of formulae III-1 to III-10:
Figure FDA0003937900330000022
Figure FDA0003937900330000031
wherein the content of the first and second substances,
R 23 、R 24 each independently represents an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms or an alkenyloxy group having 3 to 5 carbon atoms; r 23 And R 24 The hydrogens on any carbon atom in (a) may each independently be replaced by fluorine.
4. The liquid crystal composition of claim 1, wherein the liquid crystal composition comprises 1 to 15% by mass of the compound of formula I-1, 20 to 80% by mass of the compound of formula II, and 5 to 70% by mass of the compound of formula III.
5. The liquid crystal composition of claim 1, further comprising one or more compounds of formula IV:
Figure FDA0003937900330000032
wherein the content of the first and second substances,
R 7 、R 8 each independently represents F, an alkyl group having 1 to 5 carbon atoms, and optionally one or more unconnected CH 2 An alkyl group having 1 to 5 carbon atoms substituted with a cyclopentyl group, a cyclobutyl group or a cyclopropyl group, an alkyl group having 1 to 5 carbon atoms substituted with fluorine, an alkoxy group having 1 to 5 carbon atoms substituted with fluorine, an alkenyl group having 2 to 5 carbon atoms substituted with fluorine, an alkenyloxy group having 3 to 5 carbon atoms or an alkenyloxy group having 3 to 5 carbon atoms substituted with fluorine, provided that R is a substituent selected from the group consisting of a cyclopentyl group, a cyclobutyl group and a cyclopropyl group 7 And R 8 F is not simultaneously obtained;
Figure FDA0003937900330000033
each independently represent
Figure FDA0003937900330000034
Figure FDA0003937900330000035
n represents 1 or 2;
Z 2 、Z 3 each independently represents a single bond, -CF 2 O-、-CH 2 CH 2 -or-CH 2 O-。
6. The liquid crystal composition of claim 5, wherein the compound of formula IV has a formula of at least one of formulae IV-1 to IV-22:
Figure FDA0003937900330000041
Figure FDA0003937900330000051
Figure FDA0003937900330000061
wherein X 1 、X 2 Each independently represents H or F, but X in the same formula 1 、X 2 Not H at the same time, not F at the same time;
(F) Represents H or F;
R 51 ，R 52 each independently represents an alkyl group having 1 to 5 carbon atoms, and optionally one or more unconnected CH groups 2 An alkyl group having 1 to 5 carbon atoms substituted with a cyclopentyl group, a cyclobutyl group or a cyclopropyl group, an alkyl group having 5 carbon atoms substituted with fluorine, an alkoxy group having 1 to 5 carbon atoms substituted with fluorine, an alkenyl group having 2 to 5 carbon atoms substituted with fluorine, an alkenyloxy group having 3 to 5 carbon atoms or an alkenyl group having 3 to 5 carbon atoms substituted with fluorineAn oxy group.
7. The liquid crystal composition of claim 5, wherein the liquid crystal composition comprises 1-15% by mass of the compound of formula I-1, 20-80% by mass of the compound of formula II, 5-70% by mass of the compound of formula III, and 5-50% by mass of the compound of formula IV.
8. The liquid crystal composition according to claim 1 or 5, further comprising at least one of the following formulas V-1 to V-28:
Figure FDA0003937900330000062
Figure FDA0003937900330000071
Figure FDA0003937900330000081
wherein the content of the first and second substances,
R 71 、R 72 each independently represents an alkyl group having 1 to 5 carbon atoms, a fluorine-substituted alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a fluorine-substituted alkoxy group having 1 to 5 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, a fluorine-substituted alkenyl group having 2 to 5 carbon atoms, an alkenyloxy group having 3 to 5 carbon atoms or a fluorine-substituted alkenyloxy group having 3 to 5 carbon atoms.
9. The liquid crystal composition of claim 8, wherein the liquid crystal composition comprises 1 to 15% by mass of the compound of formula I-1, 20 to 80% by mass of the compound of formula II, 5 to 70% by mass of the compound of formula III, 0 to 50% by mass of the compound of formula IV, and 5 to 50% by mass of the compound of formula V.
10. A liquid crystal display device produced from the liquid crystal composition according to any one of claims 1 to 9.
CN201810005598.1A 2018-01-03 2018-01-03 Liquid crystal composition and liquid crystal display device Active CN109988583B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201810005598.1A CN109988583B (en) 2018-01-03 2018-01-03 Liquid crystal composition and liquid crystal display device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201810005598.1A CN109988583B (en) 2018-01-03 2018-01-03 Liquid crystal composition and liquid crystal display device

Publications (2)

Publication Number Publication Date
CN109988583A CN109988583A (en) 2019-07-09
CN109988583B true CN109988583B (en) 2023-02-03

Family

ID=67128462

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201810005598.1A Active CN109988583B (en) 2018-01-03 2018-01-03 Liquid crystal composition and liquid crystal display device

Country Status (1)

Country Link
CN (1) CN109988583B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108587646A (en) * 2018-06-20 2018-09-28 烟台丰蓬液晶材料有限公司 A kind of liquid-crystal compounds containing four fluoro dihydro phenanthrene structures and its application
CN112300811B (en) * 2019-08-01 2022-07-15 江苏和成显示科技有限公司 Liquid crystal composition and liquid crystal display device
CN112391173B (en) * 2019-08-14 2023-07-18 江苏和成显示科技有限公司 Liquid crystal composition having positive dielectric anisotropy and liquid crystal display device thereof
CN112391171B (en) * 2019-08-14 2023-07-18 江苏和成显示科技有限公司 Liquid crystal composition having positive dielectric anisotropy and liquid crystal display device thereof
CN112920812B (en) * 2021-02-01 2023-04-07 烟台显华科技集团股份有限公司 Negative dielectric anisotropy liquid crystal composition and liquid crystal display device
CN113403088B (en) * 2021-06-17 2022-12-30 烟台显华科技集团股份有限公司 Negative dielectric anisotropy liquid crystal composition and liquid crystal display device
CN116814277B (en) * 2023-08-29 2023-12-26 烟台显华科技集团股份有限公司 High-gradient high-brightness negative dielectric anisotropy liquid crystal composition and application thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10236992A (en) * 1997-02-25 1998-09-08 Chisso Corp Liquid crystal compound having negative anisotropic value of dielectric constant, liquid crystal composition containing the same and liquid crystal display element using the composition
WO2015007173A1 (en) * 2013-07-16 2015-01-22 江苏和成显示科技股份有限公司 Liquid crystal composition with high transmittance and display device thereof
CN105969403A (en) * 2016-05-12 2016-09-28 石家庄诚志永华显示材料有限公司 Liquid crystal composition

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104168971B (en) * 2013-03-25 2018-02-02 Dic株式会社 Liquid-crystal composition, liquid crystal display cells and liquid crystal display

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10236992A (en) * 1997-02-25 1998-09-08 Chisso Corp Liquid crystal compound having negative anisotropic value of dielectric constant, liquid crystal composition containing the same and liquid crystal display element using the composition
WO2015007173A1 (en) * 2013-07-16 2015-01-22 江苏和成显示科技股份有限公司 Liquid crystal composition with high transmittance and display device thereof
CN105969403A (en) * 2016-05-12 2016-09-28 石家庄诚志永华显示材料有限公司 Liquid crystal composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
VA-TFT用负介电各向异性液晶材料研究进展;胡明刚等;《化工新型材料》;20070515;第35卷(第05期);第5-7页 *

Also Published As

Publication number Publication date
CN109988583A (en) 2019-07-09

Similar Documents

Publication Publication Date Title
CN109988583B (en) Liquid crystal composition and liquid crystal display device
JP6908669B2 (en) Liquid crystal medium
TWI731324B (en) Positive dielectric anisotropic liquid crystal composition and liquid crystal display element
CN111484858B (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN107142116B (en) Liquid crystal composition
JP6896368B2 (en) Liquid crystal medium
TWI596200B (en) Liquid-crystalline medium and electro-optical display
JP2021143346A (en) Liquid crystal medium and liquid crystal display comprising the same
CN110577834B (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN108219802B (en) Liquid crystal composition and application thereof
CN103254906A (en) Liquid crystal composition containing difluoro methoxyl ether compounds
KR101982119B1 (en) Positive dielectric liquid crystal composition
CN109575943B (en) Liquid crystal composition and liquid crystal display device thereof
CN110577835A (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN110655927B (en) Liquid crystal composition and liquid crystal display element or liquid crystal display
CN113403088B (en) Negative dielectric anisotropy liquid crystal composition and liquid crystal display device
CN109593531B (en) Liquid crystal composition
CN112480938A (en) Negative dielectric anisotropy liquid crystal composition and liquid crystal display device
CN107286947B (en) Polymerizable liquid crystal composition and liquid crystal display device
CN112920809B (en) Liquid crystal composition, liquid crystal display element and liquid crystal display
CN104479690A (en) Nematic phase liquid crystal composition
CN113736479A (en) Negative dielectric anisotropy liquid crystal composition and liquid crystal display device
CN108690638A (en) Liquid-crystal composition
CN109825308B (en) Negative liquid crystal compound, negative liquid crystal composition and application
CN104593013A (en) Novel liquid crystal medium

Legal Events

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