CN112538006B - Compound, liquid crystal composition and display device - Google Patents
Compound, liquid crystal composition and display device Download PDFInfo
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- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
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Abstract
The application relates to the field of liquid crystals, and discloses a compound, a liquid crystal composition and a display device. The compounds have the structure of formula (I):
Description
Technical Field
The application relates to the field of liquid crystal display, in particular to a compound, a liquid crystal composition and a display device.
Background
According to the display mode, the liquid crystal display element is classified into the following modes: twisted Nematic (TN) mode, super Twisted Nematic (STN) mode, in-plane mode (IPS), vertical Alignment (VA) mode. Whatever the display mode, the liquid crystal composition is required to have the following characteristics: stable chemical and physical properties, low viscosity, proper delta epsilon and resolution delta n, and good compatibility with other liquid crystal compounds. The application discloses a compound, a liquid crystal composition and a display device, wherein the compound can be used as a novel liquid crystal compound, and the liquid crystal composition using the compound has a good display effect.
Disclosure of Invention
The application discloses a compound, a liquid crystal composition and a display device, wherein the compound can be used as a novel liquid crystal compound, and the liquid crystal composition using the compound has a good display effect.
In order to achieve the above purpose, the present application provides the following technical solutions:
a compound having the structure of formula (I):
wherein R is 2 Presence or absence, when R 2 R, when present, is 1 、R 2 Each independently selected from hydrogen, fluorine, chlorine, C1-C15 alkyl, C1-C15 alkoxy, C3-C15 cycloalkyl, C2-C15 alkenyl, C2-C15 alkenyloxy, C2-C15 alkynyl, ether, thioether, ester, cyano, cyanooxy, thiocyano or isothiocyano;
Z 1 、Z 2 each independently present or absent; z is Z 1 、Z 2 When each independently exists, Z 1 、Z 2 Each independently selected from linear C1-C5 alkyl, linear C2-C5 alkenyl, linear C2-C5 alkynyl, ester group and ether group;
the hydrogen in the C1-C15 alkyl, C1-C15 alkoxy, C3-C15 cycloalkyl, C2-C15 alkenyl, C2-C15 alkenyloxy, C2-C15 alkynyl, ether group, thioether group, ester group, cyano group, cyanooxy group, thiocyano group, isothiocyano group, linear C1-C5 alkyl, linear C2-C5 alkenyl and linear C2-C5 alkynyl is unsubstituted or part of hydrogen or all hydrogen is substituted by at least one of fluorine and chlorine;
each independently selected from the group consisting of alicyclic, aryl, and heteroaryl, wherein the hydrogen on the alicyclic, aryl, or heteroaryl is unsubstituted, or a portion or all of the hydrogen is substituted with fluorine;
m, n each independently represents 0, 1 or 2, and m+n.gtoreq.1.
Further, the method comprises the steps of,each independently selected from:
further, the Z 1 、Z 2 Each independently selected from-CH 2 -、-CH 2 -CH 2 -、-(CH 2 ) 3 -、-(CH 2 ) 4 -、 -CH＝CH-、-C≡C-、-COO-、-OOC-、-CF 2 O-、-OCH 2 -、-CH 2 O-、-OCF 2 -、-CF 2 -CH 2 -、 -CH 2 -CF 2 -、-C 2 F 4 -or-cf=cf.
Further, the compound represented by formula (I) is selected from:
a liquid crystal composition comprising 0.5% to 50% by weight of a compound according to the application.
Further, the liquid crystal composition further comprises 30 to 99 percent of a compound shown in a formula (II):
wherein R is 3 And R is 4 Each independently selected from hydrogen, halogen, C1-C15 alkyl, C1-C15 alkoxy, C2-C15 alkenyl, C2-C15 alkynyl, ether, ester or cyano; the hydrogen in the C1-C15 alkyl, C1-C15 alkoxy, C2-C15 alkenyl, C2-C15 alkynyl, ether group, ester group and cyano is unsubstituted or part of hydrogen or all of hydrogen is substituted by at least one of fluorine and chlorine;
Z 3 selected from an alkylene bridge, an alkyleneoxy bridge, an alkenylene bridge, an alkynyl bridge, an ester bridge, or an alkyleneoxy bridge; wherein the hydrogen on the alkylene bridge, alkyleneoxy bridge, alkenylene bridge, alkynyl bridge, ester bridge, or alkyleneoxy bridge is unsubstituted or part or all of the hydrogen is substituted with at least one of fluorine, chlorine;
each independently selected from the group consisting of alicyclic, aryl, and heteroaryl, wherein the hydrogen on the alicyclic, aryl, or heteroaryl is unsubstituted, or a portion or all of the hydrogen is substituted with fluorine;
p and q are each independently selected from 0, 1 or 2.
Further, the liquid crystal composition further comprises at least one of 0.01-1% of chiral dopants and 0.01-20% of polymer monomer orienting agents by weight.
A display device comprising the liquid crystal composition as in the present application.
By adopting the technical scheme of the application, the beneficial effects are as follows:
the compound shown in the formula (I) is a novel liquid crystal compound, comprises the compound shown in the formula (I), can be a positive liquid crystal composition or a negative liquid crystal composition, has wide temperature range of liquid crystal phase, high clearing point and small viscosity, has proper refractive index anisotropy constant, can improve the performance of liquid crystal composition materials and displays, and has important significance in realizing quick response of the displays.
Detailed Description
The technical solutions of the embodiments of the present application will be clearly and completely described below in conjunction with the embodiments of the present application, and it is apparent that the described embodiments are only some embodiments of the present application, not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the application without making any inventive effort, are intended to be within the scope of the application.
It should be noted that: in the present application, all embodiments and preferred methods of implementation mentioned herein may be combined with each other to form new solutions, unless otherwise specified. In the present application, all technical features mentioned herein and preferred features may be combined with each other to form new technical solutions, unless otherwise specified. In the present application, the percentage (%) or parts refer to weight percentage or parts by weight relative to the composition unless otherwise specified. In the present application, the components or preferred components thereof may be combined with each other to form a new technical solution, unless otherwise specified. In the present application, unless otherwise indicated, the numerical ranges "a-b" represent shorthand representations of any combination of real numbers between a and b, where a and b are both real numbers. For example, the numerical range "6-22" means that all real numbers between "6-22" have been listed throughout, and "6-22" is only a shorthand representation of a combination of these values. The "range" disclosed herein may take the form of a lower limit and an upper limit, which may be one or more lower limits and one or more upper limits, respectively. In the present application, each reaction or operation step may be performed sequentially or sequentially unless otherwise indicated. Preferably, the reaction processes herein are performed sequentially.
Unless otherwise defined, the technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. In addition, any method or material similar or equivalent to those described may be used in the present application.
In a first aspect, the present application provides a compound having the structure of formula (I):
wherein R is 2 Presence or absence, when R 2 R, when present, is 1 、R 2 Each independently selected from hydrogen, fluorine, chlorine, C1-C15 alkyl, C1-C15 alkoxy, C3-C15 cycloalkyl, C2-C15 alkenyl, C2-C15 alkenyloxy, C2-C15 alkynyl, ether, thioether, ester, cyano, cyanooxy, thiocyano or isothiocyano;
Z 1 、Z 2 each independently present or absent; z is Z 1 、Z 2 When each independently exists, Z 1 、Z 2 Each independently selected from linear C1-C5 alkyl, linear C2-C5 alkenyl, linear C2-C5 alkynyl, ester group and ether group;
the hydrogen in the C1-C15 alkyl, C1-C15 alkoxy, C3-C15 cycloalkyl, C2-C15 alkenyl, C2-C15 alkenyloxy, C2-C15 alkynyl, ether group, thioether group, ester group, cyano group, cyanooxy group, thiocyano group, isothiocyano group, linear C1-C5 alkyl, linear C2-C5 alkenyl and linear C2-C5 alkynyl is unsubstituted or part of hydrogen or all hydrogen is substituted by at least one of fluorine and chlorine;
m, n each independently represents 0, 1 or 2, and m+n.gtoreq.1.
The compound shown in the formula (I) is a novel liquid crystal compound, comprises the compound shown in the formula (I), can be a positive liquid crystal composition or a negative liquid crystal composition, has wide temperature range of liquid crystal phase, high clearing point and small viscosity, has proper refractive index anisotropy constant, can improve the performance of liquid crystal composition materials and displays, and has important significance in realizing quick response of the displays.
Wherein Z is 1 、Z 2 Each independently present or absent as a bridge. When Z is 1 、Z 2 When each independently exists, Z 1 、Z 2 Each independently selected from the group consisting of linear C1-C5 alkyl, linear C2-C5 alkenyl, linear C2-C5 alkynyl, ester group, and ether group. At this time, Z 1 、Z 2 Each independently selected from an alkylene bridge, an alkyleneoxy bridge, an alkenylene bridge, an alkynylalkyl bridge, an ester-based bridge, or an alkyleneoxy bridge; wherein the hydrogen on the alkylene bridge, alkyleneoxy bridge, alkenylene bridge, alkynylene bridge, ester bridge, or alkyleneoxy bridge is unsubstituted or part or all of the hydrogen is substituted with at least one of fluorine, chlorine.
In one embodiment of the present application,each independently selected from:
in one embodiment of the application, the Z 1 、Z 2 Each independently selected from-CH 2 -、-CH 2 -CH 2 -、 -(CH 2 ) 3 -、-(CH 2 ) 4 -、-CH＝CH-、-C≡C-、-COO-、-OOC-、-CF 2 O-、-OCH 2 -、-CH 2 O-、 -OCF 2 -、-CF 2 -CH 2 -、-CH 2 -CF 2 -、-C 2 F 4 -or-cf=cf.
The compound shown in the formula (I) is selected from:
in a second aspect, the present application provides a liquid crystal composition comprising 0.5% to 50% by weight of the compound of formula (I) according to the present application.
The liquid crystal phase of the liquid crystal composition has the advantages of wide temperature range, high clearing point, small viscosity and proper refractive index anisotropy constant, can improve the performances of liquid crystal composition materials and displays, and has important significance for realizing the quick response of the displays.
In the embodiment of the application, the mass ratio of the compound shown in the formula (I) in the liquid crystal composition can be, for example, 0.5%, 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% or 50%.
In one embodiment of the present application, the liquid crystal composition further comprises 30% to 99% by weight of a compound represented by formula (II):
wherein R is 3 And R is 4 Each independently selected from hydrogen, halogen, C1-C15 alkyl, C1-C15 alkoxy, C2-C15 alkenyl, C2-C15 alkynyl, ether, ester or cyano; the hydrogen in the C1-C15 alkyl, C1-C15 alkoxy, C2-C15 alkenyl, C2-C15 alkynyl, ether group, ester group and cyano is unsubstituted or part of hydrogen or all of hydrogen is at least one of fluorine and chlorineSubstituted by (A) and (B);
Z 3 selected from an alkylene bridge, an alkyleneoxy bridge, an alkenylene bridge, an alkynyl bridge, an ester bridge, or an alkyleneoxy bridge; wherein the hydrogen on the alkylene bridge, alkyleneoxy bridge, alkenylene bridge, alkynyl bridge, ester bridge, or alkyleneoxy bridge is unsubstituted or part or all of the hydrogen is substituted with at least one of fluorine, chlorine;
each independently selected from the group consisting of alicyclic, aryl, and heteroaryl, wherein the hydrogen on the alicyclic, aryl, or heteroaryl is unsubstituted, or a portion or all of the hydrogen is substituted with fluorine;
p and q are each independently selected from 0, 1 or 2.
In the embodiment of the present application, the mass ratio of the compound represented by the formula (II) in the liquid crystal composition may be, for example, 0.5%, 1%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45% or 50%.
In one embodiment of the present application,each independently selected from:
in one embodiment of the present application, the liquid crystal composition further includes at least one of 0.01% to 1% by weight of a chiral dopant and 0.01% to 20% by weight of a polymer monomer alignment agent.
The chiral dopant may be, for example:
the polymeric monomer directing agent (for alignment) may be, for example:
the preparation method of the liquid crystal composition comprises the following steps: (1) Heating, mixing and stirring various monomer liquid crystal compounds uniformly, and filtering to obtain a liquid crystal material; (2) Dissolving various monomer liquid crystal compounds with a solvent, uniformly mixing, and then pumping the solvent under a vacuum condition to obtain a liquid crystal material; (3) Mixing various monomer liquid crystal compounds uniformly by using vibration mixing or ultrasonic mixing and the like, and then filtering to obtain the liquid crystal material. The proportions of the various monomer liquid crystal materials are formulated according to specific display performance requirements. The mixed liquid crystal material can be prepared by the method.
In a second aspect, the present application provides a display device comprising a liquid crystal composition as in the present application.
The display device may be a liquid crystal display device or an electro-optical display device, and specifically is a device for displaying such as a TN type display, a VA type display, an IPS type display, or a blue phase display.
The display device comprises a liquid crystal display panel, wherein the liquid crystal display panel comprises a first substrate and a second substrate which are arranged in a box, and a liquid crystal layer which is poured between the first substrate and the second substrate, and the liquid crystal layer comprises the liquid crystal composition.
Synthesis of intermediate I
220g of p-dibutyric acid is dissolved by 600ml of toluene, 5g of p-toluenesulfonic acid is added, reflux is carried out for 5h to 6h, water washing is carried out for neutralization to obtain toluene solution of the compound 2, 200ml of ethanol is added, pd/C5 g is used as a hydrogenation catalyst, palladium carbon is filtered after hydrogen absorption is not carried out, and the compound 3 is obtained through column concentration;
adding Jones reagent into the compound 3 to oxidize the compound 3 to obtain a compound 4;
200g of compound 4 is dissolved in Tetrahydrofuran (THF), 60g of ethylene glycol is added by using cationic resin as a catalyst, the reaction is heated for 4 to 6 hours, and the reaction solution is treated to obtain compound 5;
the compound 5 reacts with propyl magnesium bromide in tetrahydrofuran solution, and after acidolysis, the compound 6 is obtained by dehydration with p-toluenesulfonic acid;
the compound 6 is hydrogenated by palladium carbon to obtain the compound 7, and then hydrochloric acid is used for deprotection to obtain an intermediate I.
Example 1
Compound S12:
the synthetic route of the compound is as follows:
200g of 3, 5-difluorobromobenzene and 24g of metallic magnesium are used for preparing a Grignard reagent in THF, 230g of an intermediate I is dropwise added, after reflux reaction is carried out for 3h, dilute hydrochloric acid is added under the ice bath condition for acidolysis, toluene is extracted to obtain an organic phase, then 5g of p-toluenesulfonic acid is added into the organic phase, reflux dehydration reaction is carried out for 4-5h, silica gel is used for adsorption, 5g of palladium carbon is added, normal pressure hydrogenation is carried out, after GC detection hydrogenation reaction is finished, palladium carbon is filtered, and the reaction solution is concentrated to obtain the compound 8.
Dissolving 30g of a compound 8 with THF, cooling to-60-70 ℃, dropwise adding 0.1mol of n-BuLi solution, performing temperature control reaction for 1h, dropwise adding 25g of difluoromethane, performing temperature control reaction for 1h, heating to room temperature, performing acidolysis, extracting an organic phase with toluene, and neutralizing and spin-drying to obtain a compound 9;
45g of compound 9 is taken as a solvent, 20g of sodium carbonate, 15g of 3,4, 5-trifluorophenol, 10g of water are added, reflux reaction is carried out for 12 hours, the reaction liquid is extracted by toluene, neutralization and spin drying are carried out, and the product compound S12 is obtained by recrystallisation by ethanol toluene.
Compound S12 assay:
nuclear magnetism detection junctionThe method comprises the following steps: 1 H NMR(400MHz，Chloroform-d)δ：7.20(s，2H)， 6.89(q，2H)，6.54(d，2H)，3.32(m，3H)，3.05(m，4H)，2.75(q，2H),2.03 (m，1H)，1.27(m，4H)，0.90(t，3H)
mass spectral data m/z: m+508
Example 2
Compound S14:
the synthetic route of the compound is as follows:
compound 8 was prepared by reference to the same route as in the preparation of compound S12;
dissolving 320g of compound 8 in 600ml of THF, dropwise adding 1.2mol of n-BuLi solution at-60 ℃, reacting for 1h, dropwise adding 150g of trimethyl borate, reacting for 1h again under controlled temperature, heating to room temperature, performing acidolysis with hydrochloric acid, and filtering to obtain compound 10;
360g of compound 10, 4-ethoxy-2, 3-difluorobromobenzene 270g, toluene 800ml, ethanol 600ml and water 500ml are stirred and refluxed for 6 hours, filtered, toluene is used for extracting filter residues, organic phases are combined, neutralized and concentrated to obtain crude product, and ethanol and toluene are used for recrystallization to obtain a final product compound S14.
Compound S14 assay:
nuclear magnetic detection data: 1 H NMR(400MHz，Chloroform-d)δ：7.45(m，2H)， 7.20(s，2H)，7.09(m，2H)，4.06(t，2H)，3.33(m，3H)，3.03(m，4H)， 2.75(q，2H)，2.03(m，1H),1.76(m，2H)，1.45(m，2H)，1.28(m，4H)， 0.90(t，6H)
mass spectral data m/z: m+496.
Example 3
Compound S15:
the synthetic route of the compound is as follows:
160g of bromobenzene and 24g of magnesium metal are used for preparing a Grignard reagent in THF, 230g of intermediate I is dropwise added, after reflux reaction is carried out for 3 hours, dilute hydrochloric acid is added in home under the ice bath condition for acidolysis, toluene is extracted to obtain an organic phase, 5g of p-toluenesulfonic acid is added in the organic phase, reflux dehydration reaction is carried out for 4-5 hours, silica gel adsorption is carried out, 5g of palladium carbon is added, normal pressure hydrogenation is carried out, after the GC detection hydrogenation reaction is finished, palladium carbon is filtered, and the reaction liquid is concentrated to obtain a compound 11;
reacting the compound 11 with 1.5 times equivalent NBS in carbon tetrachloride at room temperature to obtain a compound 12;
300g of compound 12, 4-butoxy-2, 3-difluorobromobenzene 270g, toluene 800ml, ethanol 600ml and water 500ml, stirring and refluxing for 6h, filtering, extracting filter residues by toluene, combining organic phases, neutralizing and concentrating to obtain a crude product, and recrystallizing by using ethanol and toluene to obtain a final product compound S15.
Compound S15 assay:
nuclear magnetic detection results: 1 H NMR(400MHz，Chloroform-d)δ：7.43(m，1H)， 7.36(m，4H)，7.20(s，2H)，7.08(m，1H)，4.06(t，2H)，3.33(m，3H)， 3.04(m，4H)，2.75(q，2H)，2.03(m，1H),1.76(m，2H)，1.45(m，2H)， 1.28(m，4H)，0.90(t，6H)
mass spectral data m/z: m+460.
Among them, the preparation methods of the above-mentioned compounds are merely illustrative, and other compounds according to the present application can be performed with reference to the preparation methods of the compounds provided in examples 1 to 3. In the preparation process, the raw materials can be correspondingly replaced according to the target product.
Example 4
This example is a liquid crystal composition whose component composition of the compound monomer is shown in Table 1.
TABLE 1
Example 5
This example is a liquid crystal composition whose component composition of the compound monomer is shown in Table 2.
TABLE 2
The liquid crystal compositions of example 4 and example 5 were respectively tested for clearing point Cp, optical anisotropy Δn, and dielectric constant anisotropy ΔΣ, and the test results are shown in table 3.
The method for testing the optical anisotropy comprises the following steps: the measurement was performed at 25℃and a wavelength of 589nm using an Abbe refractometer. Rubbing the surface of the main prism in the same direction, and dripping the sample onto the main prism after rubbing. Refractive index n 11 Measuring when the polarization direction is parallel to the rubbing direction; refractive index n ⊥ Measuring when the polarization direction is perpendicular to the rubbing direction; the optical anisotropy Δn is calculated by the formula Δn=n 11 -n ⊥ And (5) calculating to obtain the product.
The method for testing dielectric anisotropy is as follows: the measurement was carried out using an instrument of the type HP4284a from Hewlett-packard. Measuring the dielectric constant Sigma of the liquid crystal molecules in the axial direction at 25 DEG C 11 And dielectric constant sigma in the short axis direction of the liquid crystal molecules ⊥ Dielectric constant anisotropy passes through the formula delta sigma = Σ 11 -∑ ⊥ And (5) calculating to obtain the product.
TABLE 3 Table 3
| Sequence number | Clearing point/°c | Optical anisotropy | Dielectric constant anisotropy |
| Example 4 | 80 | 0.1 | 4.3 |
| Example 5 | 95 | 0.102 | -5.5 |
The liquid crystal composition prepared by the compound can obtain a positive liquid crystal composition and a negative liquid crystal composition by adjusting the proportion of the compounds, the obtained liquid crystal composition has higher clearing point which can reach more than 80, and the optical anisotropy and the dielectric constant anisotropy can meet the display requirement of a liquid crystal display panel, so that a novel optional compound is provided for the development of VA type displays.
It will be apparent to those skilled in the art that various modifications and variations can be made to the embodiments of the present application without departing from the spirit and scope of the application. Thus, it is intended that the present application also include such modifications and alterations insofar as they come within the scope of the appended claims or the equivalents thereof.
Claims (5)
1. A compound, characterized in that the compound has the structure:
wherein R is 1 、R 2 Each independently selected from hydrogen, C1-C15 alkyl, C1-C15 alkoxy, C3-C15 cycloalkyl, C2-C15 alkenyl, or C2-C15 alkenyloxy.
2. A liquid crystal composition comprising 0.5% to 50% by weight of the compound according to claim 1.
3. The liquid crystal composition according to claim 2, further comprising 30 to 99% by weight of a compound represented by formula (II):
wherein R is 3 And R is 4 Each independently selected from hydrogen, halogen, C1-C15 alkyl, C1-C15 alkoxy, C2-C15 alkenyl, C2-C15 alkynyl, ether, ester or cyano; the hydrogen in the C1-C15 alkyl, C1-C15 alkoxy, C2-C15 alkenyl, C2-C15 alkynyl, ether group or ester group is unsubstituted or part of hydrogen or all of hydrogen is substituted by at least one of fluorine and chlorine;
Z 3 selected from an alkylene bridge, an alkenylene bridge, an alkynyl bridge, an ester bridge, or an alkyleneoxy bridge; wherein the hydrogen on the alkylene, alkenylene, ester, or alkyleneoxy bridge is unsubstituted or part or all of the hydrogen is replaced with at least one of fluorine, chlorine;
each independently selected from the group consisting of alicyclic, aryl, and heteroaryl, wherein the hydrogen on the alicyclic, aryl, or heteroaryl is unsubstituted, or a portion or all of the hydrogen is substituted with fluorine;
p and q are each independently selected from 0, 1 or 2.
4. The liquid crystal composition according to claim 2, further comprising at least one of 0.01 to 1% by weight of a chiral dopant and 0.01 to 20% by weight of a polymer monomer alignment agent.
5. A display device comprising the liquid crystal composition according to any one of claims 2 to 4.
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| CN202011566129.0A CN112538006B (en) | 2020-12-25 | 2020-12-25 | Compound, liquid crystal composition and display device |
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| CN112538006B true CN112538006B (en) | 2023-08-22 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1507427A (en) * | 2001-07-20 | 2004-06-23 | Ĭ��ר���ɷ�����˾ | Indane compounds with negative dielectric anisotropy |
| KR20060081909A (en) * | 2005-01-11 | 2006-07-14 | 주식회사 엘지화학 | Liquid crystal composition comprising novel indane compounds and liquid crystal display device using the same |
| CN109970562A (en) * | 2019-04-30 | 2019-07-05 | 西安瑞立电子材料有限公司 | Polymerizable compound and liquid crystal media and its application |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1507427A (en) * | 2001-07-20 | 2004-06-23 | Ĭ��ר���ɷ�����˾ | Indane compounds with negative dielectric anisotropy |
| KR20060081909A (en) * | 2005-01-11 | 2006-07-14 | 주식회사 엘지화학 | Liquid crystal composition comprising novel indane compounds and liquid crystal display device using the same |
| CN109970562A (en) * | 2019-04-30 | 2019-07-05 | 西安瑞立电子材料有限公司 | Polymerizable compound and liquid crystal media and its application |
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