CN104003852B - A kind ofly contain three or the liquid crystalline cpd of quaterphenyl structure and application thereof - Google Patents
A kind ofly contain three or the liquid crystalline cpd of quaterphenyl structure and application thereof Download PDFInfo
- Publication number
- CN104003852B CN104003852B CN201410250461.4A CN201410250461A CN104003852B CN 104003852 B CN104003852 B CN 104003852B CN 201410250461 A CN201410250461 A CN 201410250461A CN 104003852 B CN104003852 B CN 104003852B
- Authority
- CN
- China
- Prior art keywords
- liquid crystalline
- crystalline cpd
- liquid
- nitrae
- isosorbide
- 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
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
- C09K19/06—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
-
- 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
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
-
- 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
- C09K19/06—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-)
- C09K2019/123—Ph-Ph-Ph
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Nonlinear Science (AREA)
- Mathematical Physics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a kind of liquid crystalline cpd containing three or quaterphenyl structure, described liquid crystalline cpd has such as formula structure shown in I: R-A
1-A
2-A
3-A
4-O (CH
2) nF (I) this compound has the large and constitutionally stable feature of optical anisotropy, the optical anisotropy of existing customary liquid-crystal composition can be improved after being applied to liquid-crystal composition further, there is the technique effect realizing response fast.
Description
Technical field
The present invention relates to liquid crystal display material field, be specifically related to a kind ofly contain three or the liquid crystalline cpd of quaterphenyl structure and application thereof.
Background technology
At present, liquid crystal is used widely in field of information display, and the application simultaneously in optical communication also makes some progress (S.T.Wu, D.K.Yang.ReflectiveLiquidCrystalDisplays.Wiley, 2001).In recent years, the Application Areas of liquid crystalline cpd significantly widened kinds of displays part, electro-optical device, electronic component, sensor.For this reason, proposed many different structures, particularly in nematic liquid crystal field, nematic liquid crystal compound has obtained applying the most widely so far in flat-panel monitor.Especially in the system of tft active matrix.
Liquid-crystal display experienced by very long road for development with the discovery of liquid crystal.Within 1888, Austrian botanist FriedrichReinitzer has found the first liquid crystal material M-nitro benzoic acid cholesterol (cholesterylbenzoate).Within 1917, Manguin has invented rubbing, in order to make single domain liquid crystal and Optical anisotropy.E.Bose in 1909 establishes and collects together (Swarm) theory, and obtains the experiment support (1918) of the people such as L.S.Ormstein and F.Zernike, is discussed as statistical fluctuation by DeGennes.G.W.Oseen and H.Zocher1933 foundes continuum theory, and obtains F.C.Frank perfect (1958).M.Born (1916) and K.Lichtennecker (nineteen twenty-six) finds and have studied the dielectric anisotropy of liquid crystal.1932, nematic phase was divided into the large class of positive and negative property two by W.Kast accordingly.Nineteen twenty-seven, V.Freedericksz and V.Zolinao finds that nematic liquid crystal is under electric field (or magnetic field) effect, deformation occurs and there is voltage threshold (Freederichsz transformation).This making being found to be liquid-crystal display provides foundation.
Nineteen sixty-eight RCA Corp. of U.S. R.Williams finds that nematic liquid crystal forms striped farmland under electric field action, and has light scattering phenomenon.G.H.Heilmeir develops into dynamic scattering display format with by it, and makes first liquid-crystal display (LCD) in the world.Early seventies, Helfrich and Schadt has invented TN principle, and people utilize TN photovoltaic effect and unicircuit to combine, and is made display device (TN-LCD), and wide prospect has been opened up in the application for liquid crystal.Since the seventies, due to the development of large-scale integrated circuit and liquid crystal material, the people such as the application of liquid crystal in display achieves breakthrough development, 1983 ~ 1985 years T.Scheffer successively propose super-twist nematic (SuperTwisredNematic:STN) pattern and P.Brody is adopted again in active matrix (Activematrix:AM) mode that 1972 propose.Traditional TN-LCD technology has developed into STN-LCD and TFT-LCD technology, although the number of scanning lines of STN can reach more than 768 row, still there is the problems such as response speed, visual angle and gray scale when the temperature increases, therefore big area, high information quantity,
Colored display adopts Active Matrix LCD At mode mostly.TFT-LCD has been widely used in direct viewing type TV, large-curtain projecting TV set, terminal display and some military instrument display, believes that TFT-LCD technology has more wide application prospect.
Wherein " active matrix " comprises two types: 1, as the OMS (metal-oxide semiconductor (MOS)) on the silicon wafer of substrate or other diode.2, as the thin film transistor (TFT) on the sheet glass of substrate.
Silicon single crystal limits display size as substrate material because each several part display device even module assembled there is many problems in its junction.Thus, the second thin film transistor is the promising active matrix type of tool, and the photovoltaic effect utilized is TN effect normally.TFT comprises compound semiconductor, as Cdse, or the TFT based on polycrystalline or amorphous silicon.
At present, TFT-LCD product technology is ripe, successfully solves the technical barriers such as visual angle, resolving power, fullness of shade and brightness, its display performance close to or exceed CRT monitor.Large size and small-medium size TFT-LCD indicating meter occupy the dominant position of flat-panel monitor gradually in respective field.But because of the restriction by liquid crystal material itself, it is fast not that TFT-LCD still also exists response, and voltage is low not, the high not many defects of electric charge conservation rate.Therefore find low viscosity, high dielectric anisotropy single crystal compound particularly important.
The monomer liquid crystal that end is-O (CH2) nF is set forth in patent DE4222371 as far back as Merck KGaA company in 1992.
Summary of the invention
For above-mentioned background, the invention provides a kind of novel liquid crystalline cpd, this compound has three or quaterphenyl and-O (CH simultaneously
2) nF modular construction.This compound has the large and constitutionally stable feature of optical anisotropy, has such as formula shown structure I:
R-A
1-A
2-A
3-A
4-O(CH
2)nF
(Ⅰ)
Wherein, R is selected from H and the alkyl separately containing 1-12 carbon atom that do not replace or replace or alkoxyl group; One or more CH in the alkyl separately containing 1-12 carbon atom replaced or alkoxyl group
2group is separately independently of one another by-C ≡ C-,-CF
2o-,-CH=CH-,-O-,-CO-O-or-O-CO-with O atom each other directly the mode of keyed jointing replace, and wherein one or more H atom can be optionally substituted by halogen;
A
1, A
2, A
3and A
4be selected from independently of one another: singly-bound or Isosorbide-5-Nitrae-phenyl, wherein the hydrogen of Isosorbide-5-Nitrae-phenyl can independently of one another by one or more halogen substiuted; And A
1, A
2, A
3and A
4one is singly-bound at the most;
N is 2,3 or 4.
Halogen of the present invention is preferably F.
The liquid crystalline cpd containing three or quaterphenyl structure of the present invention, due to tool in structure three or quaterphenyl structure, therefore, have optical anisotropy large advantage, be conducive to liquid crystal indicator reduce box thick, improve response speed.
Wherein, liquid crystalline cpd of the present invention is preferred:
R is selected from H or the unsubstituted alkyl containing 1-5 carbon atom;
A
1, A
2, A
3and A
4be selected from independently of one another: singly-bound or Isosorbide-5-Nitrae-phenyl, wherein the hydrogen of Isosorbide-5-Nitrae-phenyl can be replaced by one or more fluorine atom independently of one another; And A
1, A
2, A
3and A
4one is singly-bound at the most;
N is 2,3 or 4.
And more preferably described liquid crystalline cpd is selected from following formula compound:
Wherein, R is selected from the alkyl containing 2-5 carbon atom;
N is 2,3 or 4, preferably 2 or 3.
As the most preferred technical scheme of the present invention, described liquid crystalline cpd is:
or
Above-claimed cpd has larger optical anisotropy, can improve its optics opposite sex, reduce box thick, realize responding fast after being applied to composition.
The second object of the present invention is to provide a kind of preparation method of liquid crystalline cpd containing three or quaterphenyl structure, and the synthetic route of described preparation method is as follows:
R-A
1-A
2-A
3-I+F（CH
2）nO-A
4-B(OH)
2→R-A
1-A
2-A
3-A
4-O(CH
2)nF
Ⅱ-1Ⅱ-2
Starting raw material R-A
1-A
2-A
3-I (II-1) and F (CH
2) nO-A
4-B (OH)
2, close palladium for catalyzer with four triphenylphosphines, sodium carbonate is acid binding agent, refluxes and is obtained by reacting R-A in 4-8 hour
1-A
2-A
3-A
4-O (CH
2) nF (II-2), wherein, R, A
1, A
2, A
3, A
4and n refer to the same, I is iodine, and B is boron.
Wherein, the reaction times is preferably 6 hours.
Wherein, described reaction with toluene, ethanol or its mixture for solvent.
Adopt above-mentioned preparation method can stablize the liquid crystalline cpd obtained containing three or quaterphenyl structure by mass, there is the advantage that optical anisotropy is large.
The third object of the present invention be to protect above-mentioned contain three or the liquid crystalline cpd of quaterphenyl structure in the application of field of liquid crystal display.
Specifically, application claims protection is containing the above-mentioned liquid-crystal composition of liquid crystalline cpd containing three or quaterphenyl structure.Wherein add with reasonable manner containing three or the liquid crystalline cpd of quaterphenyl structure, the add-on of liquid crystalline cpd namely containing three or quaterphenyl structure is advisable with 1-80%, more preferably 3-50%.Those skilled in the art will envision that, based on adding of above-mentioned liquid crystalline cpd, the optical anisotropy of existing customary liquid-crystal composition can be improved further that there is the technique effect realizing response fast.
As the preferred technical solution of the present invention, described composition by weight percentage, has following proportioning:
The present invention asks the application of protection above-mentioned composition in liquid crystal indicator further, and described liquid crystal indicator is including but not limited to TN, ADS, FFS or IPS liquid-crystal display.After liquid-crystal composition is applied to liquid crystal indicator, there is the advantage of response fast.
In the present invention, each performance test parameter shorthand is as follows:
Δ ε represents the dielectric anisotropy under 25 DEG C and 1kHz;
γ 1 represents the rotary viscosity (mPas) at 25 DEG C.
△ n is optical anisotropy, and no is specific refractory power (589nm, 25 DEG C);
C.p is the clearing point (DEG C) of liquid-crystal composition;
VHR electric charge conservation rate (%): injected by mixed liquid crystal in liquid crystal cell, put into thermostat container, after temperature-stable, enters test procedure, manually gets and a little obtains electric charge conservation rate numerical value.Measuring voltage is 5V, and power-up time is 5ms, HoldingTime is 500ms.
Embodiment
Embodiment 1
the fluoro-4-of 3,5,2'-tri-(3-fluorine propoxy-)-4 "-propyl group-[1,1'; 4', the synthesis of 1 "] terphenyl (compound 3)
26mL dehydrated alcohol is added in 200mL there-necked flask, 50mL toluene and 50mL water, start stirring, add 12.9g3, the fluoro-4-of 5-bis-(3-fluorine propoxy-) phenylo boric acid (compound 1), the iodo-4'-pentylbiphenyl of the fluoro-4-of 17.0g3-(compound 2) and 11.7g anhydrous sodium carbonate.Empty substitution nitrogen three times, adds 0.25g tetra-(triphenylphosphine) and closes palladium.When being heated to liquid phase 60 DEG C, be slowly heated to backflow, back flow reaction 6 hours.
Reflux complete, add 40mL water in reactor, stir 10 minutes, leave standstill separatory, organic phase 40mL × 2 are washed twice.Add 3 times of sherwood oils and 1 times of ethyl acetate heating for dissolving, column chromatography.Be spin-dried for solvent 3 times of ethyl alcohol recrystallizations three times, suction filtration dries white solid.
Theoretical yield: 20.1g, actual output: 16.5g, yield 82.1%.
Gas phase purity (GC) 99.9%,
Fusing point: 43.9 DEG C, clearing point: 116.9 DEG C,
Δ n is 0.215,
Δ ε is 11.50,
γ 1 is 138mPas.
Mass spectroscopy fragment: 313,342,373,402 (molecular ion peaks);
H-NMR nuclear magnetic spectrogram (CDCl
3, 300mhZ): δ H:0.90-2.60 (m, 9H), 3.90-4.10 (m, 4H), 6.80-7.50 (m, 9H).
Embodiment 2
the fluoro-4-of 3,5,2'-tri-(2-fluorine oxyethyl group)-4 "-propyl group-[1,1'; 4', the synthesis of 1 "] terphenyl (compound 5)
26mL dehydrated alcohol is added in 200mL there-necked flask, 50mL toluene and 50mL water, start stirring, add 12.0g3, the fluoro-4-of 5-bis-(2-fluorine oxyethyl group) phenylo boric acid (compound 4), the iodo-4'-pentylbiphenyl of the fluoro-4-of 17.0g3-(compound 2) and 11.7g anhydrous sodium carbonate.Empty substitution nitrogen three times, adds 0.25g tetra-(triphenylphosphine) and closes palladium.When being heated to liquid phase 60 DEG C, be slowly heated to backflow, back flow reaction 6 hours.
Reflux complete, add 40mL water in reactor, stir 10 minutes, leave standstill separatory, organic phase 40mL × 2 are washed twice.Add 3 times of sherwood oils and 1 times of ethyl acetate heating for dissolving, column chromatography.Be spin-dried for solvent 3 times of ethyl alcohol recrystallizations three times, suction filtration dries white solid.
Theoretical yield: 19.4g, actual output: 16.0g, yield 82.4%.
Gas phase purity (GC) 99.9%,
Δ n is 0.226,
Δ ε is 12.60,
γ 1 is 125mPas.
Mass spectroscopy fragment: 299,328,359,388 (molecular ion peaks);
H-NMR nuclear magnetic spectrogram (CDCl
3, 300mhZ): δ H:0.90-2.60 (m, 7H), 3.90-4.10 (m, 4H), 6.80-7.50 (m, 9H).
According to the technical scheme of embodiment 1, the raw material provided for simple replacement of containing corresponding group can synthesize following compound:
Embodiment 3 mixed crystal composition
The liquid crystal monomer used in following composition is all provided by Beijing Bayi Space LCD Materials Technology Co., Ltd..Except specified otherwise, in embodiment, the content of each component all represents mass percent.
Get the liquid crystalline cpd of following parts by weight and prepare liquid-crystal composition, the performance perameter of concrete proportioning and the liquid-crystal composition of gained is by shown in following table.
There is three or quaterphenyl and-O (CH
2) application of liquid crystalline cpd in TN, IPS, FFS, ADS, VA-TFT pattern of nF structure, the results are shown in Table 1-2.
The parts by weight of each component and performance perameter in table 1, liquid-crystal composition of the present invention
The parts by weight of each component and performance perameter in table 2, available liquid crystal composition
As can be seen from table 1-2: the liquid-crystal composition adding the compounds of this invention, the time of response is short, Δ n numerical value large, electric charge conservation rate is high, and has larger dielectric anisotropy.The add-on of compound is advisable with 1-80%, more preferably 3-50%.
Except the composition that test example exemplifies, add provided by the invention other and there is three or quaterphenyl and-O (CH
2) other liquid-crystal compositions of liquid crystalline cpd of nF structure can obtain optics excellent equally and electric property.
Although above the present invention is described in detail with a general description of the specific embodiments, on basis of the present invention, can make some modifications or improvements it, this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to the scope of protection of present invention.
Claims (9)
1. contain a liquid crystalline cpd for three or quaterphenyl structure, it is characterized in that: described liquid crystalline cpd has such as formula structure shown in I:
（Ⅰ）
Wherein, R is selected from H or the unsubstituted alkyl containing 1-5 carbon atom;
A
1and A
2be selected from independently of one another: singly-bound or Isosorbide-5-Nitrae-phenyl, wherein one or more hydrogen of Isosorbide-5-Nitrae-phenyl can be replaced by fluorine atoms independently of one another; And A
1and A
2one is singly-bound at the most;
A
3for Isosorbide-5-Nitrae-phenyl, wherein one or more hydrogen of Isosorbide-5-Nitrae-phenyl are replaced by fluorine atoms independently of one another;
A
4for Isosorbide-5-Nitrae-phenyl, wherein one or more hydrogen of Isosorbide-5-Nitrae-phenyl can be replaced by fluorine atoms independently of one another;
N is 2,3 or 4.
2. liquid crystalline cpd according to claim 1, is characterized in that: described liquid crystalline cpd is selected from following formula compound:
Wherein, R is selected from the alkyl containing 2-5 carbon atom;
N is 2,3 or 4.
3. liquid crystalline cpd according to claim 2, is characterized in that: described liquid crystalline cpd is:
4., containing three or the preparation method of liquid crystalline cpd of quaterphenyl structure, it is characterized in that:
Ⅱ-1Ⅱ-2
Starting raw material
with
, close palladium for catalyzer with four triphenylphosphines, sodium carbonate is acid binding agent, refluxes and is obtained by reacting for 4-8 hour
, wherein, R, A
1, A
2, A
3, A
4and n refer to same any one of claim 1-3.
5. preparation method according to claim 4, is characterized in that: described reaction with toluene, ethanol or its mixture for solvent.
6. the application of liquid crystalline cpd in field of liquid crystal display described in any one of claim 1-3.
7. the liquid-crystal composition containing liquid crystalline cpd described in any one of claim 1-3.
8. composition according to claim 7, is characterized in that, by weight, described in any one of claim 1-3, liquid crystalline cpd add-on is in the composition 1-80%.
9. composition described in claim 7 or 8 is manufacturing the application in liquid crystal indicator, it is characterized in that: described liquid crystal indicator is TN, ADS, FFS or IPS liquid-crystal display.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410250461.4A CN104003852B (en) | 2014-06-06 | 2014-06-06 | A kind ofly contain three or the liquid crystalline cpd of quaterphenyl structure and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410250461.4A CN104003852B (en) | 2014-06-06 | 2014-06-06 | A kind ofly contain three or the liquid crystalline cpd of quaterphenyl structure and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104003852A CN104003852A (en) | 2014-08-27 |
| CN104003852B true CN104003852B (en) | 2016-04-06 |
Family
ID=51364789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410250461.4A Active CN104003852B (en) | 2014-06-06 | 2014-06-06 | A kind ofly contain three or the liquid crystalline cpd of quaterphenyl structure and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104003852B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104087312B (en) * | 2014-06-17 | 2016-07-06 | 北京八亿时空液晶科技股份有限公司 | A kind of liquid-crystal composition and application thereof |
| WO2018015321A1 (en) * | 2016-07-20 | 2018-01-25 | Merck Patent Gmbh | Liquid crystal compounds |
| CN108659854A (en) * | 2017-03-29 | 2018-10-16 | 北京八亿时空液晶科技股份有限公司 | A kind of liquid-crystal composition and its application |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101193846A (en) * | 2005-06-09 | 2008-06-04 | 株式会社艾迪科 | Novel compound and liquid-crystal composition |
| CN102399117A (en) * | 2010-09-16 | 2012-04-04 | 石家庄诚志永华显示材料有限公司 | Method for synthesis of 2'-fluoro terphenyl liquid crystal |
| CN103459554A (en) * | 2011-03-29 | 2013-12-18 | 默克专利股份有限公司 | Liquid-crystalline medium |
-
2014
- 2014-06-06 CN CN201410250461.4A patent/CN104003852B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101193846A (en) * | 2005-06-09 | 2008-06-04 | 株式会社艾迪科 | Novel compound and liquid-crystal composition |
| CN102399117A (en) * | 2010-09-16 | 2012-04-04 | 石家庄诚志永华显示材料有限公司 | Method for synthesis of 2'-fluoro terphenyl liquid crystal |
| CN103459554A (en) * | 2011-03-29 | 2013-12-18 | 默克专利股份有限公司 | Liquid-crystalline medium |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104003852A (en) | 2014-08-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI589556B (en) | Liquid crystal compound containing difluoromethoxy bridge and application thereof | |
| CN104130781B (en) | A kind of liquid-crystal composition and application thereof | |
| JP6093862B2 (en) | Smectic A phase liquid crystal material | |
| CN104059674B (en) | A kind of liquid crystalline cpd and application thereof containing difluoro-methoxy bridged bond | |
| CN104087312A (en) | Liquid crystal composition and its application | |
| CN104263382B (en) | Containing liquid-crystal composition and the application thereof of 1,3-diox and difluoro-methoxy bridged bond compound | |
| CN103146392B (en) | Liquid crystal composition for liquid crystal display | |
| CN106318402B (en) | A kind of negative liquid crystal compound, composition and its application | |
| CN103525429B (en) | Liquid crystalline cpd, its preparation method, the liquid crystal compound comprising it and application | |
| CN104003964B (en) | A kind of liquid-crystal compounds containing amylene oxide ring and application thereof | |
| CN103642502B (en) | A kind of liquid-crystal composition containing dioxygen heterocycle structure compound and application thereof | |
| CN104099105A (en) | Liquid crystal chemical compound containing dioxane ring and application thereof | |
| CN109206400A (en) | A kind of liquid-crystal compounds containing dibenzothiophenes structure and its application | |
| CN104003852B (en) | A kind ofly contain three or the liquid crystalline cpd of quaterphenyl structure and application thereof | |
| TW201704451A (en) | Liquid crystal display device and liquid crystal composition used therefor | |
| CN104087313B (en) | A kind of liquid-crystal composition and application thereof | |
| CN102851035B (en) | Nematic liquid crystal compound and applications thereof | |
| CN103553873B (en) | A kind of cyclopentylidene cyclohexyl compounds and its preparation method and application | |
| CN109722256A (en) | A kind of liquid-crystal composition and its application | |
| CN112980461A (en) | Negative dielectric liquid crystal compound and preparation and application thereof | |
| CN103740378B (en) | A kind of liquid-crystal composition and application thereof containing tetrahydrofurans | |
| CN109082281B (en) | Liquid crystal compound with negative dielectric anisotropy as well as preparation method and application thereof | |
| CN113149839B (en) | Self-aligned liquid crystal medium compound and application thereof | |
| WO2018107911A1 (en) | Liquid crystal compound having negative dielectric anisotropy, and application therefor | |
| CN102140349A (en) | Pyridine liquid crystal composition for TFT display |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant |