CN103351876B - Liquid crystal composition and liquid crystal display device thereof - Google Patents
Liquid crystal composition and liquid crystal display device thereof Download PDFInfo
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- CN103351876B CN103351876B CN201310260867.6A CN201310260867A CN103351876B CN 103351876 B CN103351876 B CN 103351876B CN 201310260867 A CN201310260867 A CN 201310260867A CN 103351876 B CN103351876 B CN 103351876B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 133
- 239000000203 mixture Substances 0.000 title claims abstract description 110
- 150000001875 compounds Chemical class 0.000 claims abstract description 108
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 8
- 230000002349 favourable effect Effects 0.000 abstract 2
- 238000012360 testing method Methods 0.000 description 18
- 239000000463 material Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 5
- 0 *C(CC1)COC1c(cc1)ccc1-c1cc(F)c(C(Oc(cc2F)cc(F)c2F)(F)F)c(F)c1 Chemical compound *C(CC1)COC1c(cc1)ccc1-c1cc(F)c(C(Oc(cc2F)cc(F)c2F)(F)F)c(F)c1 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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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
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
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- 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
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- C09K19/00—Liquid crystal materials
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- 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
- C09K2019/0466—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 linking chain being a -CF2O- chain
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- C09K19/00—Liquid crystal materials
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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-)
- C09K2019/122—Ph-Ph
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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
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3003—Compounds containing at least two rings in which the different rings are directly linked (covalent bond)
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
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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
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
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- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
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- 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
- G02F1/0009—Materials therefor
- G02F1/0045—Liquid crystals characterised by their physical properties
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Abstract
The invention provides a liquid crystal composition which comprises 1-20 wt% of compound disclosed as Formula I, 5-35 wt% of compound selected from Formula II-1, Formula II-2, Formula II-3 and combination thereof, 25-50 wt% of compound disclosed as Formula III, 5-25 wt% of compound composed of Formula IV-1, Formula IV-2 and combination thereof, and 5-25 wt% of compound composed of Formula V-1, Formula V-2 and combination thereof. The liquid crystal composition provided by the invention has the advantages of appropriate optical anisotropy, appropriate dielectric anisotropy, high response speed, high low-temperature storage stability, favorable ultraviolet irradiation resistance and favorable heat stability, and is suitable for IPS (in-plane switching), FFS (fringe field switching) and other display modes. The invention also provides a liquid crystal display device comprising the liquid crystal composition.
Description
Technical Field
The invention relates to a liquid crystal composition, in particular to a liquid crystal composition with proper optical anisotropy, proper dielectric anisotropy, higher response speed, good low-temperature storage stability, good ultraviolet irradiation resistance and thermal stability and application thereof in a liquid crystal display device.
Background
Liquid crystal display devices operate by utilizing optical anisotropy and dielectric anisotropy of liquid crystal materials themselves, and have been widely used at present. The device can be designed into various operation modes by utilizing different characteristics and operation modes of the liquid crystal material, wherein the conventional display commonly uses a TN mode (i.e. twisted nematic mode-liquid crystal mixture has a nematic structure twisted by about 90 degrees), STN (i.e. super twisted nematic mode), SBE mode (i.e. super twisted birefringence mode), EBC mode (i.e. electrically controlled birefringence mode), VA mode (and vertically aligned mode), IPS mode (i.e. in-plane switching mode), and the like, and contains a plurality of improved modes made according to the modes. The devices operating in TN, STN, and SBE modes generally use positive dielectric anisotropy liquid crystals, the EBC and VA modes use negative dielectric anisotropy liquid crystals, and the IPS mode may use either positive or negative dielectric anisotropy liquid crystals.
The liquid crystal material must have good chemical and thermal stability and good stability to electric fields and electromagnetic radiation. Furthermore, the liquid crystal material should have low viscosity and short response time, low threshold voltage and high contrast. However, since liquid crystals are usually used as a mixture of a plurality of components, mutual solubility of the components is important, and liquid crystals have to meet different requirements, such as electrical conductivity, dielectric anisotropy, and optical anisotropy, depending on the application, but the prior art has significant disadvantages, such as long response time, low resistivity, and high operating voltage, such as EP0673986, DE19528106, and DE 19528107. In addition, poor low-temperature storage stability is also a defect of many existing liquid crystal materials.
None of the series of compounds having liquid crystalline mesophases disclosed so far includes monomer compounds satisfying all of these requirements, and therefore, in the field of liquid crystal materials, novel liquid crystal compositions having improved properties are required. In particular, for many types of applications, the liquid crystal composition must have a suitably wide nematic phase range, a suitable refractive index, dielectric anisotropy, and low-temperature storage stability.
Disclosure of Invention
The invention aims to provide a liquid crystal composition which has the characteristics of proper optical anisotropy, proper dielectric anisotropy, higher response speed, good low-temperature storage stability, good ultraviolet irradiation resistance, thermal stability and the like. The liquid crystal composition can be suitably used in display modes such as IPS and FFS.
One aspect of the present invention provides a liquid crystal composition for IPS or FFS, comprising:
1-25% by weight of the total liquid crystal composition of at least one compound of formula I
5-35% by total weight of the liquid crystal composition of at least one compound selected from the group consisting of formula II-1, formula II-2, formula II-3, and combinations thereof
25-50% by weight of the total liquid crystal composition of at least one compound of formula III
5-25% by total weight of the liquid crystal composition of at least one compound selected from the group consisting of formula IV-1, formula IV-2, and combinations thereof
5-25% by total weight of the liquid crystal composition of at least one compound selected from the group consisting of formula V-1, formula V-2, and combinations thereof
Wherein,
R1、R2、R3、R4、R5and R6The same or different, each independently represents an alkyl group or an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group or an alkenyloxy group having 2 to 7 carbon atoms;
L1、L2and L3The same or different, each independently represents H or F.
The liquid crystal composition of the present invention further comprises:
0-20% by total weight of the liquid crystal composition of at least one compound selected from the group consisting of formula VI-1, formula VI-2, and combinations thereof:
wherein,
R7、R8and R9The same or different, each independently represents an alkyl group or an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group or an alkenyloxy group having 2 to 7 carbon atoms;
L4and L5The same or different, each independently represents H or F.
In some embodiments of the invention, it is preferred that R is1、R2、R3、R4、R5、R6、R7、R8And R9Is alkyl with 2-5 carbon atoms.
In some embodiments, the compound of formula ii-1 is selected from one or more compounds in the group consisting of:
the compound of formula II-2 is selected from one or more compounds of the group consisting of:
the compound of formula II-3 is selected from one or more compounds of the group consisting of:
in some embodiments, the compound of formula iii is selected from one or more compounds in the group consisting of:
in some embodiments, the compound of formula iv-1 is selected from one or more of the group consisting of:
the compound of formula IV-2 is selected from one or more compounds of the group consisting of:
in some embodiments, the compound of formula VI-1 is selected from one or more of the group consisting of:
the compound of formula VI-2 is selected from one or more compounds from the group consisting of:
in an embodiment of the present invention, it is preferred that the compound of formula i comprises 3 to 15% by weight of the total liquid crystal composition; the compounds of the group consisting of formula II-1, formula II-2, formula II-3 and combinations thereof account for 8-25% of the total weight of the liquid crystal composition; the compound of the formula III accounts for 25-40% of the total weight of the liquid crystal composition; the compounds of the group consisting of formula IV-1, formula IV-2 and combinations thereof account for 5-20% of the total weight of the liquid crystal composition; the compound of formula V-1, formula V-2 and the combination thereof accounts for 5-20% of the total weight of the liquid crystal composition; and the compound of the group consisting of the formula VI-1, the formula VI-2 and the combination thereof accounts for 1 to 15 percent of the total weight of the liquid crystal composition.
Another aspect of the present invention provides a liquid crystal display device comprising the liquid crystal composition of the present invention.
The liquid crystal composition comprising the liquid crystal compound is determined to have the characteristics of proper optical anisotropy, proper dielectric anisotropy, higher response speed, good low-temperature storage stability, good ultraviolet irradiation resistance, thermal stability and the like by performing a combination experiment on the compounds and comparing with a control. The liquid crystal composition can be applied to IPS, FFS and other display modes.
In the present invention, unless otherwise specified, the proportions are weight ratios, all temperatures are in degrees centigrade, and the thickness of the box selected for the response time data test is 7 μm.
Detailed Description
The invention will be illustrated below with reference to specific embodiments. It should be noted that the following examples are illustrative of the present invention, and are not intended to limit the present invention. Other combinations and various modifications within the spirit or scope of the present invention may be made without departing from the spirit or scope of the present invention.
For convenience of expression, in the following examples, the group structure of the liquid crystal composition is represented by the code listed in Table 1:
TABLE 1 radical structural code of liquid crystal compounds
Compounds of the following formula are exemplified:
the structural formula is represented by the code listed in Table 1, and can be expressed as: nCCGF, wherein n in the code represents the number of C atoms of the left alkyl group, for example, n is 3, namely, the alkyl group is-C3H7(ii) a C in the code represents cyclohexane.
The abbreviated codes of the test items in the following examples are as follows:
cp (. degree. C.): clearing points (nematic-isotropic phase transition temperature)
Δ n: optical anisotropy (589 nm, 20 ℃ C.)
Δ: dielectric anisotropy (1 KHz, 25 ℃ C.)
γ 1: torsional viscosity (mPas at 20 ℃ C.)
t-30℃: low temperature storage time (at-30 ℃ C.)
The components used in the following examples can be synthesized by a known method or obtained commercially. These synthesis techniques are conventional, and the resulting liquid crystal compounds were tested to meet the standards for electronic compounds.
Liquid crystal compositions were prepared according to the compounding ratios of the liquid crystal compositions specified in the following examples. The liquid crystal composition is prepared according to the conventional method in the field, such as heating, ultrasonic wave, suspension and the like, and is mixed according to the specified proportion.
Liquid crystal compositions given in the following examples were prepared and studied. The composition of each liquid crystal composition and the results of the performance parameter test thereof are shown below.
Comparative example 1
The liquid crystal composition of comparative example 1, which was filled between two substrates of a liquid crystal display and subjected to a performance test, was prepared with each compound and weight percentage as listed in table 2, and the test data are shown in the following table:
TABLE 2 liquid crystal composition formulations and their test properties
Example 1
The liquid crystal composition of example 1 was prepared according to the compounds and weight percentages listed in table 3, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 3 liquid crystal composition formula and its test performance
Example 2
The liquid crystal composition of example 2 was prepared according to the compounds and weight percentages listed in table 4, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 4 liquid crystal composition formula and its test performance
Example 3
The liquid crystal composition of example 3 was prepared according to the compounds and weight percentages listed in table 5, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 5 liquid crystal composition formulations and their test properties
Example 4
The liquid crystal composition of example 4 was prepared according to the compounds and weight percentages listed in table 6, and filled between two substrates of a liquid crystal display for performance testing, and the test data are shown in the following table:
TABLE 6 liquid crystal composition formula and its test performance
Referring to comparative example 1, as can be seen from the test data of examples 1, 2, 3 and 4 above, the liquid crystal composition provided by the present invention has suitable optical anisotropy and suitable dielectric anisotropy, has advantages of fast response, good display effect, low temperature storage stability, ultraviolet irradiation resistance and thermal stability, and is suitable for use in liquid crystal display devices for display modes such as IPS, FFS and the like.
Claims (8)
1. A liquid crystal composition for IPS or FFS comprising:
3-15% by weight of at least one compound of formula I based on the total weight of the liquid crystal composition
8-25% by total weight of the liquid crystal composition of at least one compound selected from the group consisting of formula II-1, formula II-2, formula II-3, and combinations thereof
25-40% by weight of at least one compound of formula III based on the total weight of the liquid crystal composition
5-20% by total weight of the liquid crystal composition of at least one compound selected from the group consisting of formula IV-1, formula IV-2, and combinations thereof
And
5-20% by total weight of the liquid crystal composition of at least one compound selected from the group consisting of formula V-1, formula V-2, and combinations thereof
Wherein,
R1、R2、R3、R4、R5and R6The same or different, each independently represents an alkyl group or an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group or an alkenyloxy group having 2 to 7 carbon atoms;
L1、L2and L3The same or different, each independently represents H or F;
1-15% by total weight of the liquid crystal composition of at least one compound selected from the group consisting of formula VI-1, formula VI-2, and combinations thereof:
and
wherein,
R7、R8and R9The same or different, each independently represents an alkyl group or an alkoxy group having 1 to 7 carbon atoms, or an alkenyl group or an alkenyloxy group having 2 to 7 carbon atoms;
L4and L5The same or different, each independently represents H or F.
2. The liquid crystal composition of claim 1, wherein R is1、R2、R3、R4、R5、R6、R7、R8And R9The alkyl groups may be the same or different and each independently represents an alkyl group having 2 to 5 carbon atoms.
3. The liquid crystal composition of claim 2, wherein the compound of formula ii-1 is selected from one or more compounds of the group consisting of:
and
the compound of formula II-2 is selected from one or more compounds of the group consisting of:
and
and is
The compound of formula II-3 is selected from one or more compounds of the group consisting of:
and
4. liquid crystal composition according to claim 2, characterized in that the compound of formula iii is selected from one or more compounds of the group consisting of:
and
5. the liquid crystal composition of claim 2, wherein the compound of formula iv-1 is selected from one or more compounds of the group consisting of:
and
and is
The compound of formula IV-2 is selected from one or more compounds of the group consisting of:
and
6. the liquid crystal composition of claim 2, wherein the compound of formula vi-1 is selected from one or more compounds of the group consisting of:
and
and is
The compound of formula VI-2 is selected from one or more compounds from the group consisting of:
and
7. the liquid crystal composition of claim 6, wherein the liquid crystal composition comprises:
a compound IV-1-2 accounting for 9 percent of the total weight of the liquid crystal composition;
compound III-1 in an amount of 40% by weight based on the total weight of the liquid crystal composition;
a compound V-1 accounting for 10 percent of the total weight of the liquid crystal composition;
6 percent of compound V-2 in the total weight of the liquid crystal composition;
a compound IV-2-2 accounting for 5 percent of the total weight of the liquid crystal composition;
a compound VI-1-2 accounting for 2 percent of the total weight of the liquid crystal composition;
5% of compound I based on the total weight of the liquid crystal composition;
compound II-1-4 accounting for 5 percent of the total weight of the liquid crystal composition;
compound II-1-5 accounting for 5 percent of the total weight of the liquid crystal composition;
compound II-1-6 accounting for 5 percent of the total weight of the liquid crystal composition;
compound II-2-3 accounting for 3 percent of the total weight of the liquid crystal composition;
compound II-2-4 accounting for 3 percent of the total weight of the liquid crystal composition; and
2-5 of a compound II accounting for 2 percent of the total weight of the liquid crystal composition,
alternatively, the liquid crystal composition comprises:
a compound IV-1-2 accounting for 6 percent of the total weight of the liquid crystal composition;
a compound IV-2-2 accounting for 3 percent of the total weight of the liquid crystal composition;
37% by weight of compound III-1, based on the total weight of the liquid crystal composition;
a compound V-1 accounting for 5 percent of the total weight of the liquid crystal composition;
a compound V-2 accounting for 5 percent of the total weight of the liquid crystal composition;
a compound VI-2-4 accounting for 3 percent of the total weight of the liquid crystal composition;
a compound VI-2-2 accounting for 3 percent of the total weight of the liquid crystal composition;
a compound VI-1-2 accounting for 5 percent of the total weight of the liquid crystal composition;
12% by weight of compound I based on the total weight of the liquid crystal composition;
compound II-1-4 accounting for 3 percent of the total weight of the liquid crystal composition;
compound II-1-5 accounting for 3% of the total weight of the liquid crystal composition;
compound II-1-6 accounting for 3 percent of the total weight of the liquid crystal composition;
compound II-2-3 accounting for 4% of the total weight of the liquid crystal composition;
compound II-2-4 accounting for 4% of the total weight of the liquid crystal composition; and
compound II-2-5 accounting for 4 percent of the total weight of the liquid crystal composition,
alternatively, the liquid crystal composition comprises:
a compound IV-1-2 accounting for 11 percent of the total weight of the liquid crystal composition;
a compound IV-2-2 accounting for 8 percent of the total weight of the liquid crystal composition;
compound III-1 accounting for 30 percent of the total weight of the liquid crystal composition;
a compound V-1 accounting for 8 percent of the total weight of the liquid crystal composition;
6 percent of compound V-2 in the total weight of the liquid crystal composition;
a compound VI-2-4 accounting for 3 percent of the total weight of the liquid crystal composition;
a compound VI-2-2 accounting for 3 percent of the total weight of the liquid crystal composition;
a compound VI-1-2 accounting for 3 percent of the total weight of the liquid crystal composition;
10% of compound I based on the total weight of the liquid crystal composition;
compound II-1-4 accounting for 3 percent of the total weight of the liquid crystal composition;
compound II-1-5 accounting for 3% of the total weight of the liquid crystal composition;
compound II-1-6 accounting for 3 percent of the total weight of the liquid crystal composition;
compound II-2-3 accounting for 3 percent of the total weight of the liquid crystal composition;
compound II-2-4 accounting for 3 percent of the total weight of the liquid crystal composition; and
and (3) the compound II-2-5 accounts for the total weight of the liquid crystal composition.
8. A liquid crystal display device comprising the liquid crystal composition of any one of claims 1 to 7.
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| CN201310260867.6A CN103351876B (en) | 2013-06-25 | 2013-06-25 | Liquid crystal composition and liquid crystal display device thereof |
| PCT/CN2014/079923 WO2014206209A1 (en) | 2013-06-25 | 2014-06-16 | Liquid crystal composition and liquid crystal display device thereof |
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| JP2959526B2 (en) * | 1996-07-15 | 1999-10-06 | チッソ株式会社 | Phenyldioxane derivative, liquid crystal composition and liquid crystal display device |
| EP1721307B1 (en) * | 2004-02-24 | 2013-04-17 | Merck Patent GmbH | Zenithal bistable nematic liquid crystal device |
| EP1862526B1 (en) * | 2006-05-31 | 2009-10-14 | Chisso Corporation | Liquid crystal compositions and liquid crystal display device |
| KR101572257B1 (en) * | 2006-08-25 | 2015-11-26 | 메르크 파텐트 게엠베하 | Liquid crystalline medium |
| JP5564833B2 (en) * | 2009-05-27 | 2014-08-06 | Ｊｎｃ株式会社 | Liquid crystal composition and liquid crystal display element |
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