CN113072954A - Polymerizable compound-containing liquid crystal composition and application thereof - Google Patents
Polymerizable compound-containing liquid crystal composition and application thereof Download PDFInfo
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Abstract
本发明提供一种含可聚合化合物的液晶组合物及其应用，包含通式I所代表的可聚合化合物中的一种或多种，及向列相液晶组合物。本发明通过在向列相液晶组合物中引入含有三个可聚合基团的反应性介晶(RM)，三个可聚合基团可以加快反应速度时间，降低制程时间，使得液晶组合物的配向效果更好，聚合更完全，残留更低，并且能有效改善液晶组合物的低温互溶性，降低成角时间。特别是对于现有PSVA液晶来说，在对其他参数没有明显损害的情况下，能缩短在测试盒中可测量的预倾斜相关的响应时间，具有重要的应用价值。 The present invention provides a liquid crystal composition containing a polymerizable compound and an application thereof, comprising one or more of the polymerizable compounds represented by the general formula I, and a nematic liquid crystal composition. In the present invention, a reactive mesogen (RM) containing three polymerizable groups is introduced into the nematic liquid crystal composition, and the three polymerizable groups can speed up the reaction time and reduce the process time, so that the alignment of the liquid crystal composition can be achieved. The effect is better, the polymerization is more complete, the residue is lower, and the low temperature mutual solubility of the liquid crystal composition can be effectively improved, and the angle-forming time can be reduced. Especially for the existing PSVA liquid crystal, the response time of the measurable pre-tilt in the test box can be shortened without obvious damage to other parameters, which has important application value. 
Description
Technical Field
The invention relates to the technical field of liquid crystal materials, in particular to a liquid crystal composition containing a polymerizable compound and application thereof.
Background
A PSVA (polymer stabilized vertically aligned liquid crystal) type liquid crystal display element forms a polymer structure in a liquid crystal cell to control a structure of a pretilt angle of liquid crystal molecules, and is used as a liquid crystal display element due to its high-speed response and high contrast. The PSVA type display element is manufactured by injecting a polymerizable composition containing a liquid crystal compound and a polymerizable compound between substrates, irradiating with ultraviolet light, and polymerizing the polymerizable compound in a state in which liquid crystal molecules are aligned. The polymerizable compound serving as the main material has important significance, and the contrast is improved and the problem of display residual image is solved by matching with a proper liquid crystal composition.
Especially for monitor and especially TV applications, shortening the process time and optimizing the response time have been important issues in the research and development field. In view of the above, the present invention is particularly proposed.
Disclosure of Invention
Therefore, the invention provides a liquid crystal composition containing a polymerizable compound and application thereof. According to the invention, the Reactive Mesogen (RM) containing three polymerizable groups is introduced into the nematic liquid crystal composition, and the three polymerizable groups can accelerate the reaction speed and shorten the processing time, so that the liquid crystal composition has better alignment effect, more complete polymerization and lower residue, and the low-temperature intersolubility of the liquid crystal composition can be effectively improved, and the angle forming time is shortened. Particularly, for the existing PSVA liquid crystal, the response time related to the measurable pretilt in the test box can be shortened under the condition of no obvious damage to other parameters, and the PSVA liquid crystal has important application value.
Specifically, the invention provides a polymerizable compound-containing liquid crystal composition, which comprises one or more polymerizable compounds represented by a general formula I and a nematic phase liquid crystal composition,
wherein L is1Represents H, -F, -Cl, -CH3、-C2H5、-OCH3、-OC2H5、-CF3Or OCF3；
P1、P2、P3Independently of one another, acrylate, methacrylate, fluoroacrylate, chloroacrylate, vinyloxy, oxetane or epoxy;
Z1、Z2、Z3independently of one another, represents a single bond, -O-, -S-, -CO-O-, -O-CO-O-, -CH ═ N-, -N ═ CH-, -N ═ N-, C1-C12Alkylene or C2-C12Alkenyl of (a); or, said C1-C12Alkylene or C2-C12At least one hydrogen atom in the alkenyl group of (a) is independently of each other substituted by F, Cl or CN; or, said C1-C12Alkylene or C2-C12One of alkenyl groups of (2) -CH2-or at least two non-adjacent-CHs2-independently of each other by-O-, -S-, -NH-, -CO-O-, -OCO-, -OCOO-, -SCO-, -COS-or-C-in a manner not directly linked to each other.
Further, in the formula I, L1Represents H, -F, -CH3or-OCH3；
And/or, P1、P2、P3Independently of one another, a methacrylate, acrylate, fluoroacrylate or chloroacrylate group, preferably P1、P2、P3Independently of one another, a methacrylate group or an acrylate group;
and/or, Z1、Z2、Z3Independently of one another, represents a single bond, -O-, -S-, -CO-O-, -O-CO-, C1-C6Alkylene or C2-C6Alkenyl of (a); or, said C1-C6Alkylene or C2-C6Chain of (2)At least one hydrogen atom in the alkenyl group is substituted by F; or, said C1-C6Alkylene or C2-C6One of alkenyl groups of (2) -CH2-or at least two non-adjacent-CHs2-is substituted by-O-in a manner not directly linked to each other; preferably, Z1、Z2、Z3Independently of one another, represents a single bond, -O-, C1-C6An alkylene group of (a);
more preferably, the polymerizable compound represented by the general formula I is selected from one or more of the formulas I1 to I4:
further, the nematic liquid crystal composition comprises one or more compounds represented by the general formula II and one or more compounds represented by the general formula III,
wherein R is1、R2Each independently represents C1-C12Linear alkyl, linear alkoxy or C2-C12Linear alkenyl of (A)1、A2Each independently of the other represents trans-1, 4-cyclohexyl or 1, 4-phenylene, Z4Is a single bond, -CH2CH2-or-CH2O-; a is 0 or 1;
wherein R is3、R4Each independently represents C1-C12Linear alkyl, linear alkoxy or C2-C12Linear alkenyl of (A)3、A4Each independently represents trans-1, 4-cyclohexyl or 1, 4-phenylene.
Further, the compound represented by the general formula II is selected from one or more of IIA to IIF:
preferably, the compound represented by formula II is selected from one or more of formulae IIA-1 to IIF-16:
more preferably, the compound represented by the general formula II is selected from one or more of the compounds of the formulas IIA-9-IIA-24, IIB-19-IIB-38, IIC-9-IIC-24, IID-9-IID-24, IIE-1-IIE-20 and IIF-1-IIF-16;
most preferably, the compound represented by the general formula II is selected from one or more of the compounds represented by the formulas IIA-13-IIA-24, IIB-23-IIB-38, IIC-13-IIC-24, IID-13-IID-24, IIE-1, IIE-2, IIE-5, IIE-6, IIE-9, IIE-10, IIE-13, IIE-14, IIE-17, IIE-18, IIF-1, IIF-2, IIF-5, IIF-6, IIF-9, IIF-10, IIF-13 and IIF-14.
Further, the compound represented by the general formula III is selected from one or more of formulas IIIA to IIIC:
preferably, the compound represented by formula III is selected from one or more of formulae IIIA1 to IIIC 24:
more preferably, the compound represented by the general formula III is selected from one or more of the compounds in the formulas IIIA-1 to IIIA-22, IIIB-1 to IIIB-24 and IIIC-1 to IIIC-22;
most preferably, the compound represented by the general formula III is selected from one or more of the compounds in the formulas IIIA-1 to IIIA-12, IIIB-17 to IIIB-24, IIIC-1 to IIIC-4 and IIIC-15 to IIIC-18.
Further, the nematic liquid crystal composition further comprises one or more of the compounds represented by the general formula IV:
wherein R is5、R6Each independently represents C1-C12Linear alkyl, linear alkoxy or C2-C12Linear alkenyl of (A)5Represents trans-1, 4-cyclohexyl or 1, 4-phenylene;
preferably, the compound represented by formula IV is selected from one or more of IVA to IVB:
wherein R is5、R6Each independently represents C1-C7Linear alkyl, linear alkoxy or C2-C7A linear alkenyl group of (a);
more preferably, the compound represented by formula IV is selected from one or more of IVA 1-IVB 25:
most preferably, the compound represented by formula IV is selected from one or more of IVA-11 to IVA-15, IVB-11 to IVB-15.
Further, the nematic liquid crystal composition comprises the following components in percentage by mass:
(1) 1-80% of a compound represented by the general formula II;
(2) 1 to 70% of a compound represented by the general formula III;
(3) 0 to 40% of a compound represented by the general formula IV;
preferably, the nematic liquid crystal composition comprises the following components in percentage by mass:
(1) 5-70% of a compound represented by the general formula II;
(2) 20-60% of a compound represented by the general formula III;
(3) 0 to 35% of a compound represented by the general formula IV;
more preferably, the nematic liquid crystal composition comprises the following components in percentage by mass:
(1) 10-70% of a compound represented by the general formula II;
(2) 25 to 60% of a compound represented by the general formula III;
(3) 0 to 30% of a compound represented by the general formula IV;
further preferably, the nematic liquid crystal composition comprises the following components in percentage by mass:
(1) 20-70% of a compound represented by the general formula II;
(2) 25 to 50% of a compound represented by the general formula III;
(3) 0 to 20% of a compound represented by the general formula IV.
Further, the liquid crystal composition further comprises an antioxidant, and the antioxidant comprises one or more compounds represented by the general formula V:
wherein R is7Represents C1-C7Linear alkyl, linear alkoxy or C2-C7Linear alkenyl of (A)6Represents trans-1, 4-cyclohexyl or 1, 4-phenylene; b is 0 or 1;
preferably, the compound represented by the general formula V is one or two selected from V-1 to V-2:
and/or the amount of the compound represented by the general formula V is 0.005 to 1%, preferably 0.005 to 0.1%, and more preferably 0.005 to 0.05% based on the weight of the nematic liquid crystal composition.
Further, the polymerizable compound represented by the general formula I is 0.01 to 5%, preferably 0.05 to 1%, more preferably 0.1 to 0.5%, and still more preferably 0.25 to 0.37% by weight of the nematic liquid crystal composition.
The invention also provides the application of the liquid crystal composition containing the polymerizable compound in a PSVA type liquid crystal display device, and the liquid crystal composition can shorten the response time related to the measurable pretilt in a test box under the condition of no obvious damage to other parameters, and has important application value.
The method for preparing the liquid crystal composition of the present invention is not particularly limited, and two or more compounds may be mixed and produced by a conventional method, for example, by mixing the different components at a high temperature and dissolving each other.
Detailed Description
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
Unless otherwise indicated, percentages in the present invention are weight percentages; the temperature units are centigrade; Δ n represents optical anisotropy (25 ℃); epsilon∥And ε⊥Respectively represent the parallel and perpendicular dielectric constants (25 ℃, 1000 Hz); Δ ε represents the dielectric anisotropy (25 ℃, 1000 Hz); γ 1 represents rotational viscosity (mpa.s, 25 ℃); cp represents the clearing point (. degree. C.) of the liquid crystal composition; k11、K22、K33Respectively representing the splay, twist and bend elastic constants (pN, 25 ℃). ρ represents resistivity (Ω · cm) and the test conditions are 25 ± 2 ℃.
In the following examples, the group structures in the liquid crystal compounds are represented by codes shown in Table 1.
Table 1: radical structure code of liquid crystal compound
Take the following compound structure as an example:
expressed as: 3PWO2
Expressed as: 3CCWO2
In the following examples, the liquid crystal composition was prepared by a thermal dissolution method, comprising the steps of: weighing the liquid crystal compound by a balance according to the weight percentage, wherein the weighing and adding sequence has no specific requirements, generally weighing and mixing the liquid crystal compound in sequence from high melting point to low melting point, heating and stirring at 60-100 ℃ to uniformly melt all the components, filtering, performing rotary evaporation, and finally packaging to obtain the target sample.
The weight percentages of the components of the nematic liquid crystal composition and the performance parameters of the liquid crystal composition are given in the following table.
Nematic liquid crystal composition LC1
Table 2: the weight percentage and performance parameters of each component in the liquid crystal composition
Nematic liquid crystal composition LC 2:
table 3: the weight percentage and performance parameters of each component in the liquid crystal composition
Nematic liquid crystal composition LC3
Table 4: the weight percentage and performance parameters of each component in the liquid crystal composition
Nematic liquid crystal composition LC4
Table 5: the weight percentage and performance parameters of each component in the liquid crystal composition
Nematic liquid crystal composition LC5
Table 6: the weight percentage and performance parameters of each component in the liquid crystal composition
Nematic liquid crystal composition LC6
Table 7: the weight percentage and performance parameters of each component in the liquid crystal composition
Nematic liquid crystal composition LC7
Table 8: the weight percentage and performance parameters of each component in the liquid crystal composition
Nematic liquid crystal composition LC8
Table 9: the weight percentage and performance parameters of each component in the liquid crystal composition
Nematic liquid crystal composition LC9
Table 10: the weight percentage and performance parameters of each component in the liquid crystal composition
Nematic liquid crystal composition LC10
Table 11: the weight percentage and performance parameters of each component in the liquid crystal composition
In the following examples, the weight% of the RM monomer I and the antioxidant are based on the weight of the nematic liquid crystal composition, and are added separately from the nematic liquid crystal composition in percentage by mass.
The examples are shown in Table 12.
TABLE 12
A liquid crystal composition containing a polymerizable compound was injected into a PSVA test cell having a cell gap of 3.2 μm by a vacuum injection method. Then, a color filter for filtering ultraviolet rays having a wavelength of 310nm or less is interposed,the liquid crystal cell is irradiated with ultraviolet rays using a fluorescent lamp. At this time, the illuminance measured under the condition that the central wavelength was 365nm was adjusted to 100mW/cm2Irradiation cumulative light quantity of 30J/cm2Ultraviolet rays (irradiation condition 1). Subsequently, the illuminance measured under the condition of a central wavelength of 313nm was adjusted to 3mW/cm using a fluorescent UV lamp2Cumulative quantity of light irradiated 10J/cm2(ultraviolet irradiation condition 2). UV1 is an ultraviolet irradiation process through irradiation condition 1, and UV2 is a process through irradiation condition 1 and irradiation condition 2.
Comparative example 1
A liquid crystal composition containing a polymerizable compound was obtained as comparative example 1 by adding 0.3 part by mass of the compound represented by the formula RM-1 and 0.01 part by mass of the compound represented by the formula V-2 to 100 parts by mass of the nematic liquid crystal composition LC 1.
A liquid crystal composition containing a polymerizable compound was injected into a PSVA test cell having a cell gap of 3.2 μm by a vacuum injection method. Then, the liquid crystal cell was irradiated with ultraviolet rays using a fluorescent lamp through a color filter that filters ultraviolet rays of 310nm or less. At this time, the illuminance measured under the condition that the central wavelength was 365nm was adjusted to 100mW/cm2Irradiation cumulative light quantity of 30J/cm2Ultraviolet rays (irradiation condition 1). Subsequently, the illuminance measured under the condition of a central wavelength of 313nm was adjusted to 3mW/cm using a fluorescent UV lamp2Cumulative quantity of light irradiated 10J/cm2(ultraviolet irradiation condition 2). UV1 is an ultraviolet irradiation process through irradiation condition 1, and UV2 is a process through irradiation condition 1 and irradiation condition 2.
Effect testing
1. Conversion of polymerizable Compounds
A polymerizable compound is added to the composition, which is consumed by polymerization to form a polymer. The conversion of this reaction is preferably a large conversion.
This is because: from the viewpoint of image sticking, the residual amount of the polymer compound (the amount of unreacted polymerizable compound) is preferably small.
2. Response time
The response time Toff test, the addition of a trifunctional RM monomer, the reduction in response time associated with the measurable pre-tilt in the test cell can be achieved without significant detriment to other parameters, thereby increasing response speed and decreasing response time.
The test results are shown in tables 13-18.
Watch 13
TABLE 14
Watch 15
TABLE 16
TABLE 17
Watch 18
Compared with the comparative example 1, the reaction speed time can be increased, the process time can be reduced, the response speed can be increased, the response time can be reduced, the RM monomer containing three polymerizable groups can be added, the response time of the comparative example 1 is 5.7ms, the response time of the embodiment is 5.5ms at most and 5.1ms at least, compared with the comparative example 1, the response time is increased by 4-10% after the RM monomer containing three polymerizable groups is added, and the response time is obviously increased.
Finally, it should be noted that: the above examples are only intended to illustrate the technical solution of the present invention, but not to limit it; although the present invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; and such modifications or substitutions do not depart from the spirit and scope of the corresponding technical solutions of the embodiments of the present invention.
Claims (10)
1. A polymerizable compound-containing liquid crystal composition characterized by comprising one or more polymerizable compounds represented by the general formula I and a nematic liquid crystal composition,
wherein L is1Represents H, -F, -Cl, -CH3、-C2H5、-OCH3、-OC2H5、-CF3Or OCF3；
P1、P2、P3Independently of one another, acrylate, methacrylate, fluoroacrylate, chloroacrylate, vinyloxy, oxetane or epoxy;
Z1、Z2、Z3independently of one another, represents a single bond, -O-, -S-, -CO-O-, -O-CO-O-, -CH ═ N-, -N ═ CH-, -N ═ N-, C1-C12Alkylene or C2-C12Alkenyl of (a); or, said C1-C12Alkylene or C2-C12At least one hydrogen in the alkenyl group of (a)Atoms are independently from each other substituted with F, Cl or CN; or, said C1-C12Alkylene or C2-C12One of alkenyl groups of (2) -CH2-or at least two non-adjacent-CHs2-independently of each other by-O-, -S-, -NH-, -CO-O-, -OCO-, -OCOO-, -SCO-, -COS-or-C-in a manner not directly linked to each other.
2. The polymerizable compound-containing liquid crystal composition according to claim 1, wherein in the formula I, L is1Represents H, -F, -CH3or-OCH3；
And/or, P1、P2、P3Independently of one another, a methacrylate, acrylate, fluoroacrylate or chloroacrylate group, preferably P1、P2、P3Independently of one another, a methacrylate group or an acrylate group;
and/or, Z1、Z2、Z3Independently of one another, represents a single bond, -O-, -S-, -CO-O-, -O-CO-, C1-C6Alkylene or C2-C6Alkenyl of (a); or, said C1-C6Alkylene or C2-C6At least one hydrogen atom in the alkenyl group of (a) is substituted by F; or, said C1-C6Alkylene or C2-C6One of alkenyl groups of (2) -CH2-or at least two non-adjacent-CHs2-is substituted by-O-in a manner not directly linked to each other; preferably, Z1、Z2、Z3Independently of one another, represents a single bond, -O-, C1-C6An alkylene group of (a);
more preferably, the polymerizable compound represented by the general formula I is selected from one or more of the formulas I1 to I4:
3. the polymerizable compound-containing liquid crystal composition according to claim 1 or 2, wherein the nematic liquid crystal composition comprises one or more compounds represented by the general formula II and one or more compounds represented by the general formula III,
wherein R is1、R2Each independently represents C1-C12Linear alkyl, linear alkoxy or C2-C12Linear alkenyl of (A)1、A2Each independently of the other represents trans-1, 4-cyclohexyl or 1, 4-phenylene, Z4Is a single bond, -CH2CH2-or-CH2O-; a is 0 or 1;
wherein R is3、R4Each independently represents C1-C12Linear alkyl, linear alkoxy or C2-C12Linear alkenyl of (A)3、A4Each independently represents trans-1, 4-cyclohexyl or 1, 4-phenylene.
4. The polymerizable compound-containing liquid crystal composition according to claim 3, wherein the compound represented by the general formula II is one or more selected from IIA to IIF:
preferably, the compound represented by formula II is selected from one or more of formulae IIA-1 to IIF-16:
more preferably, the compound represented by the general formula II is selected from one or more of the compounds of the formulas IIA-9-IIA-24, IIB-19-IIB-38, IIC-9-IIC-24, IID-9-IID-24, IIE-1-IIE-20 and IIF-1-IIF-16;
most preferably, the compound represented by the general formula II is selected from one or more of the compounds represented by the formulas IIA-13-IIA-24, IIB-23-IIB-38, IIC-13-IIC-24, IID-13-IID-24, IIE-1, IIE-2, IIE-5, IIE-6, IIE-9, IIE-10, IIE-13, IIE-14, IIE-17, IIE-18, IIF-1, IIF-2, IIF-5, IIF-6, IIF-9, IIF-10, IIF-13 and IIF-14.
5. The polymerizable compound-containing liquid crystal composition according to claim 3 or 4, wherein the compound represented by the general formula III is selected from one or more of formulas IIIA to IIIC:
preferably, the compound represented by formula III is selected from one or more of formulae IIIA1 to IIIC 24:
more preferably, the compound represented by the general formula III is selected from one or more of the compounds in the formulas IIIA-1 to IIIA-22, IIIB-1 to IIIB-24 and IIIC-1 to IIIC-22;
most preferably, the compound represented by the general formula III is selected from one or more of the compounds in the formulas IIIA-1 to IIIA-12, IIIB-17 to IIIB-24, IIIC-1 to IIIC-4 and IIIC-15 to IIIC-18.
6. The polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 5, wherein the nematic liquid crystal composition further comprises one or more compounds represented by the general formula IV:
wherein R is5、R6Each independently represents C1-C12Linear alkyl, linear alkoxy or C2-C12Linear alkenyl of (A)5Represents trans-1, 4-cyclohexyl or 1, 4-phenylene;
preferably, the compound represented by formula IV is selected from one or more of IVA to IVB:
wherein R is5、R6Each independently represents C1-C7Linear alkyl, linear alkoxy or C2-C7A linear alkenyl group of (a);
more preferably, the compound represented by formula IV is selected from one or more of IVA 1-IVB 25:
most preferably, the compound represented by formula IV is selected from one or more of IVA-11 to IVA-15, IVB-11 to IVB-15.
7. The polymerizable compound-containing liquid crystal composition according to any one of claims 3 to 6, wherein the nematic liquid crystal composition comprises the following components in percentage by mass:
(1) 1-80% of a compound represented by the general formula II;
(2) 1 to 70% of a compound represented by the general formula III;
(3) 0 to 40% of a compound represented by the general formula IV;
preferably, the nematic liquid crystal composition comprises the following components in percentage by mass:
(1) 5-70% of a compound represented by the general formula II;
(2) 20-60% of a compound represented by the general formula III;
(3) 0 to 35% of a compound represented by the general formula IV;
more preferably, the nematic liquid crystal composition comprises the following components in percentage by mass:
(1) 10-70% of a compound represented by the general formula II;
(2) 25 to 60% of a compound represented by the general formula III;
(3) 0 to 30% of a compound represented by the general formula IV;
further preferably, the nematic liquid crystal composition comprises the following components in percentage by mass:
(1) 20-70% of a compound represented by the general formula II;
(2) 25 to 50% of a compound represented by the general formula III;
(3) 0 to 20% of a compound represented by the general formula IV.
8. The polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 7, further comprising an antioxidant comprising one or more compounds represented by the general formula V:
wherein R is7Represents C1-C7Linear alkyl, linear alkoxy or C2-C7Linear alkenyl of (A)6Represents trans-1, 4-cyclohexyl or 1, 4-phenylene; b is 0 or 1;
preferably, the compound represented by the general formula V is one or two selected from V-1 to V-2:
and/or the amount of the compound represented by the general formula V is 0.005 to 1%, preferably 0.005 to 0.1%, and more preferably 0.005 to 0.05% based on the weight of the nematic liquid crystal composition.
9. The polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 8, wherein the polymerizable compound represented by the general formula I is 0.01 to 5%, preferably 0.05 to 1%, more preferably 0.1 to 0.5%, and still more preferably 0.25 to 0.37% by weight of the nematic liquid crystal composition.
10. Use of the polymerizable compound-containing liquid crystal composition according to any one of claims 1 to 9 in a PSVA-type liquid crystal display device.
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| TW110116605A TW202132253A (en) | 2021-03-24 | 2021-05-07 | Liquid crystal composition containing polymerizable compound and application thereof shortening the pre-tilt related response time that can be measured in the test box without obvious damage to other parameters |
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| CN114349586A (en) * | 2021-12-29 | 2022-04-15 | 阜阳欣奕华材料科技有限公司 | Preparation method of trans-alkyl bicyclohexyl liquid crystal monomer |
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| KR102628589B1 (en) * | 2014-11-25 | 2024-01-25 | 메르크 파텐트 게엠베하 | Liquid crystal medium |
| EP3067405B1 (en) * | 2015-03-10 | 2019-03-27 | Merck Patent GmbH | Liquid crystalline medium |
| JPWO2016170948A1 (en) * | 2015-04-23 | 2018-02-15 | Jnc株式会社 | Liquid crystal composition and liquid crystal display element |
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| DE102017002925A1 (en) * | 2016-04-21 | 2017-10-26 | Merck Patent Gmbh | Liquid crystalline medium |
| KR20190024868A (en) * | 2016-06-28 | 2019-03-08 | 제이엔씨 주식회사 | Method for manufacturing liquid crystal display element and liquid crystal display element |
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