CN1613965A - Nematic liquid crystal mixture and display therewith - Google Patents
Nematic liquid crystal mixture and display therewith Download PDFInfo
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- CN1613965A CN1613965A CN 200410078718 CN200410078718A CN1613965A CN 1613965 A CN1613965 A CN 1613965A CN 200410078718 CN200410078718 CN 200410078718 CN 200410078718 A CN200410078718 A CN 200410078718A CN 1613965 A CN1613965 A CN 1613965A
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- 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
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- 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
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
- C09K2019/183—Ph-Ph-C≡C-Ph
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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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Abstract
The invention relates to a nematic liquid crystal admixture which comprises a compound or compound with various general forms. The invention is characterized in that the compound at least comprises the general form III b<*> compound with the weight is less than 10 percent and the general form III c<*> with the weight is less than 10 percent, wherein, the ring R and R<1> is defined according to the right requirement 1 and comprise the liquid crystal display of the liquid crystal admixture.
Description
The present invention relates to new liquid crystal compound and the application in liquid-crystal display thereof, especially twisted nematic (TN) and super-twist nematic (STN) liquid-crystal display, they have very short time of response and good steepness (steepnesses) and dependence of angle, and the liquid-crystal display that contains described new blend.
The TN indicating meter for example can be from M.Schadt and W.Helfrich, and Appl. Phys.Lett. is known in 18,127 (1971).The STN indicating meter for example can be from EP 0 131 216 B1; DE 34 23993 A1; EP 0 098 070 A2; M.Schadt and F.Leenhouts, 17th FreiburgCongress on Liquid Crystals (8.-10.04.87); People such as K.Kawasaki, SID 87Digest 391 (20.6); M.Schadt and F.Leenhouts, SID 87 Digest 372 (20.1); People such as K.Katoh, Japanese Journal of Applied Physics, Vol.26, No.11, L1784-L 1786 (1987); People such as F.Leenhouts, Appl.Phys.Lett.50 (21), 1468 (1987); H.A.van Sprang and H.G.Koopman, J.Appl.Phys.62 (5), 1734 (1987); T.J.Scheffer and J.Nehring, Appl.Phys.Lett.45 (10), 1021 (1984), M.Schadt and F.Leenhouts, Appl.Phys.Lett.50 (5), 236 (1987) and E.P.Raynes, Mol.Cryst.Liq.Cryst.Letters Vol.4 (1), pp.1-8 (1986) is known.This term STN covers any relative height distortion display element of the twist angle that has between 160 ° and 360 ° here, for example according to the display element (C.M.Waters etc. of Waters etc., Proc.Soc.Inf.Disp. (New York) (1985) (3rd Intern.Display Conference, Kobe, Japan), STN-LCDs (DE-A 35 03 259), SBE-LCDs (T.J.Scheffer and J.Nehring, Appl.Phys.Lett.45 (1984) 1021), OMI-LCDs (M.Schadt and F.Leenhouts, Appl.Phys.Lett.50 (1987), 236, DST-LCDs (EP-A 0 246 842) or BW-STN-LCDs (K.Kawasaki etc., SID 87 Digest 391 (20.6)).
The difference that the STN indicating meter is compared with standard TN indicating meter is the much better steepness of electrooptics characteristic curve, and medium and higher, for example better contrast value under 32-64 or the higher multipath conversion rate.With regard to contrast gradient, because opacity value preferably, the contrast gradient of TN indicating meter is higher usually, and the dependence of angle of contrast gradient then will be lower than and have low multipath conversion rate (multichannel than), for example is lower than 32 tunnel STN indicating meter.
It is desirable to have TN and the STN indicating meter of very short time of response especially, especially also at a lower temperature.In order to realize the short time of response, the monotropic additive that the rotary viscosity of liquid crystal compound has had a high steam pressure by main use is so far optimized.Yet the time of response of being realized is not suitable for each application scenario.
In order to realize steep electrooptics characteristic curve in indicating meter according to the present invention, this liquid crystal compound should have for the ratio K between the elastic constant
33/ K
11Higher value and for Δ ε/ε
⊥Smaller value, wherein Δ ε is dielectric anisotropy and ε
⊥Be and the vertical specific inductivity of vertical element axle.
Except the optimization of contrast gradient and time of response, further important requirement is constituting by this type:
1. wide d/p window
2. high long-term chemical stability
3. high resistance
4. the low frequency of threshold voltage and temperature dependency.
It is far from being enough that the parameters combination that is realized remains so far, especially for height-multipath conversion STN indicating meter (having multipath conversion rate), and also be like this for low multipath conversion STN indicating meter (having multipath conversion rate respectively) and the TN indicating meter of neutralization at about 1/64 and 1/16 near zone in about zone of about 1/400.This part ground is owing to the following fact, that is, various requirement is the influence that is subjected to material parameter in opposite mode.
Therefore, for having the very short time of response of satisfying above-mentioned requirements, has big operating temperature range simultaneously, high characteristic curve steepness, the good dependence of angle of contrast gradient and the liquid crystal compound of low threshold voltage, in particular for the liquid crystal compound that neutralizes multipath conversion STN indicating meter low, continuing has huge demand.
WO 01/64814 discloses and has contained formula IA compound and the end that end has alkenyl and have 4-cyano group-3-fluorophenyl or 4-cyano group-3, the STN indicating meter of the formula IB compound of 5-difluorophenyl.Yet the threshold voltage of these mixtures and frequency dependent form remain unsafty for some application scenario.
Therefore, the purpose of this invention is to provide and be used for liquid-crystal display, the liquid crystal compound in TN and the STN indicating meter particularly, it does not have above-mentioned shortcoming or only has above-mentioned shortcoming on than low degree, it has lower threshold voltage, especially compare with the mixture of prior art, the frequency dependence that has identical or improved operating voltage simultaneously, and have especially at low temperatures the short time of response.
Have now found that if use nematic liquid crystal mixtures, then this purpose can realize, this mixture comprises one or more compounds of general formula I:
R wherein
1Be alkyl, alkoxyl group or alkenyl with 1 to 12 carbon atom, one of them or two non-conterminous CH
2Group in addition also can be by-O-,-CH=CH-,-CO-,-OCO-or-COO-replaces, but requires the O atom directly not to be connected with each other,
Be characterised in that described mixture comprises the general formula III b that is less than 10% weight
*Compound and the general formula III c that is less than 10% weight
*Compound
Wherein R is alkyl, alkenyl or the alkoxyl group with 1 to 12 carbon atom.
Compound of Formula I has reduced, especially, and the time of response and the threshold voltage of TN and STN mixture, and meanwhile keep or even the frequency dependence of the operating voltage of having improved (that is, reducing) and threshold voltage.
Specifically, now had surprisingly been found that, in case in TN and STN mixture, use the compound of general formula I and reduce general formula III b simultaneously
*And/or general formula III c
*The amount of compound just can reduce time of response and threshold voltage, and meanwhile can not damage significantly or or even improved the frequency dependence of operating voltage and threshold voltage.
Further get on very well, mixture according to the present invention protrudes in following advantage:
-they have the short time of response, especially at low temperatures,
-have a low rotary viscosity,
-they have low threshold voltage and operating voltage,
-they have good electrical-optical characteristic curve steepness,
-they have the low operating voltage and the frequency dependence of threshold voltage,
-they make the LC indicating meter have long work-ing life and number of operations at low temperatures.
Therefore, the present invention relates to a kind of liquid crystal compound, comprise one or more compounds of general formula I
R wherein
1Be alkyl, alkoxyl group or alkenyl with 1 to 12 carbon atom, one of them or two non-conterminous CH
2Group in addition also can be by-O-,-CH=CH-,-CO-,-OCO-or-COO-replaces, but requires the O atom directly not to be connected with each other,
Be characterised in that described mixture comprises the general formula III b that is less than 10% weight
*Compound and the general formula III c that is less than 10% weight
*Compound
Wherein R is alkyl, alkenyl or the alkoxyl group with 1 to 12 carbon atom.
The invention still further relates to and be used for liquid-crystal display, especially TN and STN indicating meter, especially in-to the TN of height-multipath conversion scope and the corresponding liquid crystal compound in the STN indicating meter.
The present invention relates to liquid-crystal display in addition, has:
-two outside plates, they form the crystal pond with framework,
-be arranged in the nematic liquid crystal mixtures of the positivity dielectric anisotropy in crystal pond,
-electrode layer of oriented layer (alignment layers) arranged on the inboard of outside plate,
-between the longitudinal axis of the lip-deep molecule of outside plate and outside plate 0 spend to the inclination angles of 30 degree and
The twist angle from the oriented layer to the oriented layer (twist angle) of liquid crystal compound in-the crystal pond between 22.5 ° and 600 °,
-nematic liquid crystal mixtures, composed of the following components:
A) liquid crystal of 15-80wt%
Component A, it is made up of one or more compounds that have greater than+1.5 dielectric anisotropy;
B) liquid crystal of 20-85wt%
B component, it by have-1.5 and+one or more compounds of dielectric anisotropy between 1.5 form;
C) liquid crystal of 0-20wt%
Component D, it is lower than one or more compounds of-1.5 dielectric anisotropy and forms by having; With
D) if necessary, optically active
Component C, its consumption makes that the ratio between the natural pitch of layer thickness (gap of outside plate (separation)) and chiral nematic liquid crystal mixture is about 0.2 to 1.3,
Be characterised in that described nematic liquid crystal mixtures is according to mixture of the present invention.
Especially preferred these compound of Formula I, wherein R
1It is the alkenyl that has the alkyl of 1-8 carbon atom or have 2-7 carbon atom.Particularly preferred radicals R
1Be ethyl, n-propyl and n-pentyl, and vinyl and propylene-1-base.
Except the compound of general formula I, also preferably contain one or more alkenyl compounds of general formula I I according to mixture of the present invention:
Wherein
A
4Be 1,4-phenylene or trans (trans)-1, the 4-cyclohexylidene,
R
3Be alkenyl with 2-7 carbon atom,
R
4Be alkyl, alkoxyl group or alkenyl with 1 to 12 carbon atom, one of them or two non-conterminous CH
2Group in addition also can be by-O-,-CH=CH-,-CO-,-OCO-or-COO-replaces, but require the O atom directly not to be connected with each other and
A is 0 or 1.
Especially preferred wherein a is 1 general formula I I compound.
Particularly preferred general formula I I compound is selected from general formula I Ia to IIg
R wherein
3aAnd R
4aBe H independently of one another, CH
3, C
2H
5Or n-C
3H
7, and alkyl is the alkyl with 1-8 carbon atom.
Especially preferred formula IIa compound, especially wherein R
3aAnd R
4aBe CH
3Those compounds, and general formula I Ie, IIf, IIg, IIh and IIi compound, especially wherein R
3aBe H or CH
3Those compounds.
In liquid crystal compound according to the present invention, the use of general formula I I compound has caused low especially rotary viscosity value and has obtained to have the TN and the STN indicating meter of high steepness and fast response time (especially at low temperatures).
Except the neutral alkenyl compound of the dielectric of general formula I I, mixture of the present invention also preferably comprises general formula I I
*One or more dielectric positivity alkenyl compounds
Wherein
R
3It is alkenyl with 2 to 7 carbon atoms;
Q is CF
2, OCF
2, CFH, OCFH or singly-bound;
Y is F or Cl; With
L
1And L
2Be H or F independently of one another.
Preferred general formula I I
*Compound is L wherein
1And/or L
2Be that F and Q-Y are F or OCF
3Those compounds.
Further preferred these general formula Is I
*Compound, wherein R
3Be have 2 to 7, especially the 1E-alkenyl or the 3E-alkenyl of 2,3 or 4 carbon atoms.
Especially preferred formula II
*The a compound
R wherein
3aBe H, CH
3, C
2H
5Or n-C
3H
7, especially H or CH
3
Have compound of Formula I and general formula I I greater than+1.5 dielectric anisotropy
*Polar compound should be classified as defined above
Component A
Under the condition of claim 1,
Component A, except the compound of general formula I, also can wrap
One or more cyano compounds that contain following general formula:
Wherein
R is alkyl, alkoxyl group or the alkenyl with 1 to 12 carbon atom, one of them or two non-conterminous CH
2Group in addition also can be by-O-,-CH=CH-,-CO-,-OCO-or-COO-replaces, but requires the O atom directly not to be connected with each other, preferably have the alkyl or the alkoxyl group of 1-8 carbon atom or have 2-7 carbon atom alkenyl and
L
1-4Be H or F independently of one another,
Here, L wherein
1And L
2Be that F and R are that the general formula III b and the ratio of IIIc compound in mixture of the present invention of alkyl, alkenyl or alkoxyl group is less than 10% in each case.
In mixture according to the present invention, general formula III b
*And IIIc
*The ratio of compound in each case≤8%, especially preferably in each case≤5%.
Preferred general formula III a and IIIb compound are as follows:
Preferred such mixture, it neither comprises general formula III b
*Compound, do not comprise general formula III c yet
*Compound.Particularly preferably be such compound, it neither comprises the compound of general formula III b, does not also comprise the compound of general formula III c, wherein L
1Be F, L
2Be that H or F and R are alkyl, alkenyl or alkoxyl group.Especially particularly preferredly neither comprise the mixture that general formula III b compound does not comprise general formula III c compound yet.
In a preferred embodiment,
Component APreferably include following general formula one or more 3,4,5-trifluorophenyl compound:
And/or one or more of following general formula contain the compound of terminal polar group:
Wherein the definition of R as mentioned above, and L
3And L
4Be H or F independently of one another.R in these compounds especially preferably has the alkyl or the alkoxyl group of 1-8 carbon atom.
Preferred liquid crystal compound comprises
Component AOne or more compounds, ratio is preferably 15% to 80%, preferred especially 20% to 70%.These compounds have the dielectric anisotropy of Δ ε 〉=+3, especially Δ ε 〉=+8, especially preferably Δ ε 〉=+12.
Preferred liquid crystal compound comprises
B componentOne or more compounds, preferred proportion is 20 to 85%, is preferably 30% to 75% especially.The compound of B group, particularly those contain the compound of alkenyl, especially embody the low rotary viscosity value γ that is characterised in that them
1
Except one or more compounds of general formula I I,
B componentPreferred one or more compounds that also comprise in the bicyclic compound that is selected from following general formula:
And/or be selected from one or more compounds in the tricyclic compound of following general formula:
And/or be selected from one or more compounds in the tetracyclic compound of following general formula:
Wherein
R
1And R
2Be alkyl, alkoxyl group or alkenyl independently of one another with 1 to 12 carbon atom, one of them or two non-conterminous CH
2Group in addition also can be by-O-,-CH=CH-,-CO-,-OCO-or-COO-replaces, but require the O atom directly not to be connected with each other and
L is H or F.
At general formula I V10 to IV19 and IV23 to 1 described in the IV33, the 4-phenylene group can also be replaced by the fluorine list independently of one another or be polysubstituted.
Particularly preferably be the compound of general formula I V27, wherein R to I31
1Be alkyl and R
2Be alkyl or alkoxyl group, especially alkoxyl group has 1 to 7 carbon atom separately.Further preferably wherein L is the general formula I V27 of F and the compound of IV29.
The compound of general formula I V2, IV27 and IV28 very particularly preferably.
The R of general formula I V1 in the IV33 compound
1And R
2Especially preferably the straight chained alkyl or the alkoxyl group that have 1 to 12 carbon atom.
The optional optically active that comprises of this liquid crystal compound
Component C, its content makes ratio between the natural pitch of layer thickness (gap of outside plate) and chiral nematic liquid crystal mixture greater than 0.2.For described component, multiple chiral dopant, wherein some can have been bought from the market, can be obtained by the person skilled in the art, cholesteryl nonanoate for example, S-811 can be from Merck KGaA, and Darmstadt is purchased, and CB15 (BDH, Poole, UK).The selection of doping agent itself is not crucial.
The ratio of the compound of component C preferably 0 to 10%, especially 0 to 5%, preferred especially 0 to 3%.
Preferably comprise one or more liquid crystal tolane (tolan) compounds according to mixture of the present invention.Because the high birefringence Δ n of described tolane compound makes and can adopt relatively little layer thickness, thereby the time of response is significantly shortened.Described tolane compound is preferably selected from the group of being made up of following general formula:
R wherein
1And R
2As hereinbefore defined,
Z
4Be-CO-O--CH
2CH
2-or singly-bound; With
L
1-L
6Be H or F independently of one another.
Special preferred formula Ta, Tb and Th compound.
Especially preferred general formula Te compound is these, that is, and and group L wherein
1-L
6In one,
Two or three are F, other be H, L wherein
1And L
2Or L
3And L
4Or L
5And L
6All not F simultaneously.
Be selected from ratio preferably 5-50%, the especially 10-40% of the compound of the group that comprises Ta, Tb and Th.
The ratio of general formula Ta-Th compound is 2-55%, especially 5-35% preferably.
According to mixture of the present invention also can optionally comprise at the most 20% have one or more compounds of being lower than-2 dielectric anisotropy (
Component D).
If mixture comprises
Component DCompound, then these preferably contain structural unit 2,3-two fluoro-1, one or more compounds of 4-phenylene, for example at DE-A 38 07 801, the compound of describing in 3807861,3,807 863,3,807 864 or 3,807 908.Particularly preferably be tolane (tolans) compound that contains this structural unit, it is described among International Patent Application PCT/DE 88/00133.
Other known compound of component D is, for example, 2, the derivative of 3-dicyano quinhydrones or contain structural unit
Or
Cyclohexane derivant, it is on the books in DE-A 32 31707 or DE-A 34 07 013.
Liquid-crystal display according to the present invention does not preferably comprise
Component DCompound.
R, R
1, R
2, R
3And R
4Term in the definition " alkenyl " comprises straight chain and branched alkenyl, at R, R
1And R
2Situation under, have 2-12 carbon atom, at R
3And R
4Situation under have 2-7 carbon atom, especially straight chain group.Preferred kiki alkenyl group is C
2-C
7-1E-alkenyl, C
4-C
7-3E-alkenyl, C
5-C
7-4-alkenyl, C
6-C
7-5-alkenyl and C
7-6-alkenyl, especially C
2-C
7-1E-alkenyl, C
4-C
7-3E-alkenyl and C
5-C
7-4-alkenyl.
The example of preferred kiki alkenyl group is a vinyl, 1E-propenyl, 1E-butenyl, the 1E-pentenyl, 1E-hexenyl, 1E-heptenyl, the 3-butenyl, 3E-pentenyl, 3E-hexenyl, the 3E-heptenyl, 4-pentenyl, 4Z-hexenyl, the 4E-hexenyl, the 4Z-heptenyl, 5-hexenyl, 6-heptenyl or the like.Having at the most, the group of 5 carbon atoms generally is preferred.
Each compound of general formula I, II, III, IV, V, VI and T or its inferior general formula, or can be used in according to other compound in TN of the present invention and the STN indicating meter and be known or can prepare similarly with known compound.
In preferred embodiments, described mixture comprises:
A kind of, two or three compound of-general formula I;
-3 to 45%, especially 5 to 35%, the compound of preferred especially one or more general formula Is of 10 to 30%;
-≤8%, preferred≤5% does not especially preferably contain general formula III b
*Compound;
-≤8%, preferred≤5%, the preferred especially compound that does not contain general formula III b, wherein L
1Be F, L
2Be that H or F and R are alkyl, alkenyl or alkoxyl group;
-≤8%, preferred≤5%, the preferred especially compound that does not contain general formula III b, wherein R is alkyl, alkenyl or alkoxyl group;
-≤8%, preferred≤5% does not especially preferably contain general formula III c
*Compound;
-≤8%, preferred≤5%, the preferred especially compound that does not contain general formula III c, wherein L
1Be F, L
2Be that H or F and R are alkyl, alkenyl or alkoxyl group;
-≤8%, preferred≤5%, the preferred especially compound that does not contain general formula III c, wherein R is alkyl, alkenyl or alkoxyl group;
-3 to 40%, especially 6 to 35%, preferred especially 8 to 25% general formula Ta, Tb and one or more compounds of Th;
-25 to 75%, especially 35 to 65% general formula I I, II
*, IV9 and IV24 one or more alkenyl compounds,
-be selected from general formula I If, IIg, IIh, IIi and II
*One or more alkenyl compounds of a, wherein alkyl is the alkyl with 1-8 carbon atom, R
3aBe H or CH
3,
One or more compounds of-general formula I V9 and/or IV24, wherein R
1Be alkenyl with 2-7 carbon atom, R
2As hereinbefore defined and especially one or more compounds of the alkyl or the alkoxyl group that have 1-6 carbon atom, especially general formula I V9a and/or IV24a
R wherein
3aBe H, CH
3, C
2H
5Or n-C
3H
7, especially H or CH
3, R
2As hereinbefore defined, preferably have the alkyl or the alkoxyl group of 1-6, especially 1,2 or 3 carbon atom, preferred especially methoxyl group, oxyethyl group or just-propoxy-.The ratio of these compounds in described liquid crystal compound is preferably 2-30%, 3-20% especially,
One or more compounds of-general formula I V2, wherein R
1And R
2The alkyl or the alkoxyl group that preferably have 1-6 carbon atom, especially wherein R
1Be alkyl, and R
2Be alkoxyl group with 1-6 carbon atom,
One or more compounds of-general formula I V27 and/or IV28, wherein the L among the general formula I V27 is H or F, especially preferred F.The ratio of these compounds in described liquid crystal compound is preferably 10
-45%, 15-40% especially;
-the compound of positive dielectric anisotropy more than 20% especially has the compound of Δ ε 〉=+12.
According to mixture according to the present invention embody feature in, especially when TN that is used for high layer thickness and STN indicating meter, extremely low overall response time (t
s=t
On+ t
Off).
Be used for having the dielectric positivity of Δ ε 〉=1 according to the liquid crystal compound in TN of the present invention and STN pond.Particularly preferably be wherein Δ ε 〉=3, especially the liquid crystal compound of Δ ε 〉=5.
Liquid crystal compound according to the present invention has for threshold voltage V
10/0/20With for rotary viscosity γ
1Desired value.If the value of path difference d Δ n is predesignated, then the value of layer thickness d is determined by optical anisotropy Δ n.Especially under higher d Δ n value, the use with liquid crystal compound of the present invention of the high value for optical anisotropy generally is preferred, because therefore the value of d can be chosen as smaller value, this has caused the more suitably value of time of response.Yet, even if according to liquid-crystal display of the present invention-it contain have less Δ n value according to liquid crystal compound of the present invention-also embody feature in the ideal value of this time of response.
Embody the ideal value of feature in addition according to liquid crystal compound of the present invention, and can operate, especially be higher than under 20 ℃ the temperature with high multipath conversion rate in the steepness of electrooptics characteristic curve.
In addition, liquid crystal compound according to the present invention has high stability and the ideal value for the frequency dependence of resistance and threshold voltage.Liquid-crystal display according to the present invention has the good dependence of angle of big work-temperature range and contrast gradient.
LCD element according to the present invention is from the conventional structure of the formed structure of polarizing, electrode base board and electrode corresponding to the display element of this type, and wherein electrode has carried out surface treatment so that the prioritization of the liquid crystal molecule that is adjacent (orientor) is caused the value of twisting 160 ° to 720 ° from an electrode to another electrode usually under each situation.The term here " conventional structure " is the whole derivations and the improvement of broadly drawing and covering TN and STN pond, especially matrix display element and the display element that contains additional magnets.
Can be identical or different at two outside plate upper surface inclination angles.Identical inclination angle is preferred.The longitudinal axis and the tilt angle between the outside plate that preferred TN indicating meter has molecule on the plate surface outside are 0 ° to 7 °, preferred 0.01 ° to 5 °, and especially 0.1 ° to 2 °.In the STN indicating meter, the inclination angle is 1 ° to 30 °, preferred 1 ° to 12 ° and especially 3 ° to 10 °.
The twist angle of TN mixture has between 22.5 ° and 170 ° in this pond, preferably in the value between 80 ° and 115 ° between 45 ° and 130 ° and especially.The twist angle from the oriented layer to the oriented layer of STN mixture has between 100 ° and 600 ° in this pond, preferably in the value between 180 ° and 270 ° between 170 ° and 300 ° and especially.
Spendable liquid crystal compound can prepare according to conventional method itself according to the present invention.Usually, the component of aequum is used with low amount, be dissolved in the component that constitutes principal constituent, advantageously carry out at elevated temperatures.Also the solution of component might be sneaked into organic solvent, for example sneak into acetone, remove once more in chloroform or the methyl alcohol and after mixing and desolvate, for example by distillation.
Also be suitable as cholesteryl liquid crystal (CLC) indicating meter according to liquid crystal compound of the present invention, especially the liquid crystal media in SSCT (" surface stabilised cholesteric texture " (surface stabilization courage steroid texture)) and PSCT (the polymer stabilising courage steroid texture) indicating meter, for example WO 92/19695, US 5,384,067, US 5,453,863, US 6,172, and 720 or US5, described in 661,533.The CLC indicating meter contains the CLC medium of being made up of nematic component and optically active component usually, and it is compared with STN with TN has significantly higher helically twistedly, shows the selective reflection of circularly polarized light.Reflection wavelength is corresponding to the pitch of described cholesteric helix and the average reflection exponential product of described CLC medium.
For this reason, in liquid crystal compound of the present invention, add one or more chiral dopants, select their distortion power and concentration, make described liquid crystal media at room temperature have cholesteryl phase and have preferably at visible, the UV of electromagnetic spectrum or reflection wavelength, the especially 400-800nm in IR zone.
Suitable doping agent is known to those skilled in the art and can obtains from commercial channels, for example, cholesteryl nonanoate (CN), CB15, R/S-811, and R/S-1011, R/S-2011, R/S-3011 or R/S-4011 (Merck KGaA, Darmstadt).The doping agent that especially preferably has the high distortion of chirality glycosyl group, especially two anhydrohexose alcohol derivate, the for example derivative of isosorbide, different mannitol or different iditol (isoiditol), the preferably sorbitol derivatives described in WO 98/00428.Also preferred chirality glycol derivative, phenylbenzene-1 for example, 1 of 2-dihydroxyl ethane (benzylidene two pure and mild benzyleneglycols), the 2-derivative preferably as GB-A-2, causes meso benzyleneglycol derivative described in 328,207.Doping agent very particularly preferably is as at the chiral binaphthyl derivative described in the WO 02/94805, as at the chiral binaphthol acetal derivative described in the WO 02/34739, as the chirality TADDOL derivative described in the WO02/06265 and as at the chiral dopant that at least one fluoridizes bridge linkage group and end or central chirality group that contains described in WO 02/06196 and the WO02/06195.
If add two or more doping agents, then these can have identical or opposite sense of rotation, the temperature dependency of identical or opposite described distortion.
The invention still further relates to the CLC medium, comprise as the nematic component according to liquid crystal compound of the present invention with as one or more chiral dopants of optically active component.The invention still further relates to CLC indicating meter, the especially SSCT and the PSCT indicating meter that contain CLC medium as indicated above.
This dielectric medium also can be included as the person skilled in the art known with other additive of describing in the literature.For example, can add the pleochroism dyestuff of 0-15%.
In the application and in the following embodiments, the structure of liquid crystalline cpd is to utilize acronym to represent, according to hereinafter Table A and B are transformed into chemical formula.Whole group C
nH
2n+1And C
mH
2m+1It is the straight chained alkyl that has n and m carbon atom respectively.This kiki alkenyl group has transconfiguration.Decoding in table B is self-explantory.In Table A, only provided the acronym of precursor structure.Under each situation, after the acronym of precursor structure then be, by dash separate in following table for substituent R
1, R
2, L
1, L
2And L
3Given code.
R
1，R
2，L
1，L
2， R
1 R
2 L
1?L
2?L
3
L
3Code
nm C
nH
2n+1 C
mH
2m+1 H H H
nOm OC
nH
2n+1 C
mH
2m+1 H H H
nO.m C
nH
2n+1 OC
mH
2m+1 H H H
n C
nH
2n+1 CN H H H
nN.F C
nH
2n+1 CN H H F
nN.F.F C
nH
2n+1 CN H F F
nF C
nH
2n+1 F H H H
nOF OC
nH
2n+1 F H H H
nF.F C
nH
2n+1 F H H F
nmF C
nH
2n+1 C
mH
2m+1 F H H
nOCF
3 C
nH
2n+1 OCF
3 H H H
n-Vm C
nH
2n+1 -CH＝CH-C
mH
2m+1?H H H
nV-Vm C
nH
2n+1-CH＝CH- -CH＝CH-C
mH
2m+1?H H H
This TN and STN indicating meter preferably contain the liquid crystal compound of being made up of one or more compounds of Table A and B.
Table A: (L
1, L
2, L
3=H or F)
Table B:
Table C:
Table C has provided the possible doping agent that joins usually according to the present invention in the mixture.
Table D:
Can join, for example, the stablizer in the mixture of the present invention is as follows.
The following example is used to illustrate the present invention but does not represent the restriction meaning.Use following abbreviation:
Cl.p. clear point (nematic-isotropic phase transition temperature),
S-N smectic shape liquid crystal-nematic Phase temperature,
Δ n optical anisotropy (589nm, 20 ℃)
n
oCommon refractive index (589nm, 20 ℃)
Δ ε dielectric anisotropy (1kHz, 20 ℃)
S characteristic curve steepness=V
90/ V
10
V
10(frequency is 80 to the character voltage of threshold voltage=under 10% relative contrast
Hz, except as otherwise noted)
V
90Character voltage under 90% relative contrast
t
OnFrom connecting the time till power supply reaches 90% high-contrast,
t
OffReach the time till 10% the high-contrast from powered-down,
T
TotTotal time of response t
On+ t
Off
Above and hereinafter, all temperature are ℃ to provide.Per-cent is weight percent, except as otherwise noted.All value is based on 20 ℃, except as otherwise noted.Except as otherwise noted, this indicating meter addressing under the bias voltage of 1/128 multipath conversion rate and 1/12.Except as otherwise noted, this distortion is 240 °.
Comparing embodiment 1
According to TN and the STN mixture (mixture V1) of the embodiment 2 of WO 01/64814, form by following component
ME2N.F 8.00％ Cl.p.： 86.5℃
ME3N.F 9.00％ Δn： 0.1376
ME4N.F 12.00％ V
10：
CC-3-V1 3.00％
CCG-V-F 15.00％
CCP-V-1 6.00％
CCPC-33 5.00％
CCPC-34 5.00％
CCPC-35 5.00％
CBC-33F 4.00％
CBC-53F 4.00％
PPTUI-3-2 6.00％
PCH-3N.F.F 10.00% (general formula III b
*)
DU-5-N 8.00% (general formula I)
Embodiment 1
According to TN of the present invention and STN mixture (mixture M 1), form by following component
ME2N.F 8.00％ Cl.p.： 85.0℃
ME3N.F 9.00％ Δn： 0.1307
ME4N.F 6.00％
CC-3-V1 3.00％
CCG-V-F 15.00％
CCP-V-1 6.00％
CCPC-33 5.00％
CCPC-34 5.00％
CCPC-35 5.00％
CBC-33F 4.00％
CBC-53F 4.00％
PPTUI-3-2 6.00％
PCH-3N.F.F 5.00% (general formula III b
*)
DU-5-N 8.00% (general formula I)
DU-2-N 6.00% (general formula I)
DU-3-N 5.00% (general formula I)
For mixture V1 and M1, measure threshold voltage V
10, as the function (dV of rectangular voltage frequency
10/ df).The results are shown in the accompanying drawing 1.
From accompanying drawing 1, be clear that, V1 compares with control mixture, and mixture M 1 according to the present invention has significantly lower threshold voltage and the significantly lower threshold voltage dependency to frequency, has meanwhile kept other favourable character, for example, clear point and birefringence.
In addition, control mixture V1 (demonstrates under＞5kHz) the situation and can form low temperature region, consequently will no longer can record threshold voltage under these frequencies in relative high frequency.In contrast, do not demonstrate low temperature region according to mixture M 1 of the present invention even under the frequency of 10kHz yet.
Comparing embodiment 2
TN and the STN mixture (V2) formed by following component
PCH-301 16.00％ Cl.p.： 79.5℃
CCP-V-1 12.00％ Δn： 0.1466
CCP-V2-1 12.00％ n
o： 1.5036
CVCP-V-1 5.00％ V
10： 1.92V
CVCP-V-O1 5.00％ S： 1.042
CVCP-1V-O1 5.00％ t
tot： 304ms
PPTUI-3-2 20.00％
PCH-2N.F.F 25.00% (general formula III b
*)
Embodiment 2
By following component form according to TN of the present invention and STN mixture (M2)
PCH-301 16.00％ Cl.p.： 85.0℃
CCP-V-1 12.00％ Δn： 0.1502
CCP-V2-1 12.00％ n
o： 1.5002
CVCP-V-1 5.00％ V
10： 1.56V
CVCP-V-O1 5.00％ S： 1.058
CVCP-1V-O1 5.00％ t
tot： 252ms
PPTUI-3-2 20.00％
DU-2-N 25.00% (general formula I)
V2 compares with mixture, and described mixture M 2 has significantly higher clear point, significantly more
Low threshold voltage, better steepness and total faster time of response.
Comparing embodiment 3
TN and the STN mixture (V3) formed by following component
PCH-301 16.00％ Cl.p.： 93.5℃
CCP-V-1 12.00％ Δn： 0.1552
CCP-V2-1 12.00％ n
o： 1.5009
CVCP-V-1 5.00％ V
10： 2.07V
CVCP-V-O1 5.00％ S： 1.040
CVCP-1V-O1 5.00％ t
tot： 243ms
PPTUI-3-2 20.00％
PCH-3N.F.F 25.00% (general formula III b
*)
Embodiment 3
By following component form according to TN of the present invention and STN mixture (M3)
PCH-301 16.00％ Cl.p.： 92.5℃
CCP-V-1 12.00％ Δn： 0.1561
CCP-V2-1 12.00％ n
o： 1.4996
CVCP-V-1 5.00％ V
10： 1.72V
CVCP-V-O1 5.00％ S： 1.061
CVCP-1V-O1 5.00％ t
tot： 228ms
PPTUI-3-2 20.00％
DU-3-N 25.00% (general formula I)
V3 compares with mixture, and described mixture M 3 has significantly higher clear point, significantly lower threshold voltage, better steepness and total faster time of response.
Comparing embodiment 4
TN and the STN mixture (V4) formed by following component
PCH-301 16.00％ Cl.p.： 97.5℃
CCP-V-1 12.00％ Δn： 0.1554
CCP-V2-1 12.00％ n
o： 1.4992
CVCP-V-1 5.00％ V
10： 2.16V
CVCP-V-O1 5.00％ S： 1.041
CVCP-1V-O1 5.00％ t
tot： 261ms
PPTUI-3-2 20.00％
PCH-5N.F.F 25.00% (general formula III b
*)
By following component form according to TN of the present invention and STN mixture (M4)
PCH-301 16.00％ Cl.p.： 90.0℃
CCP-V-1 12.00％ Δn： 0.1512
CCP-V2-1 12.00％ n
o： 1.5003
CVCP-V-1 5.00％ V
10： 1.86V
CVCP-V-O1 5.00％ S： 1.062
CVCP-1V-O1 5.00％ t
tot： 273ms
PPTUI-3-2 20.00％
DU-5-N 25.00% (general formula I)
V4 compares with mixture, and described mixture M 4 has significantly lower threshold voltage and better steepness.
Comparing embodiment 5
TN and the STN mixture (V5) formed by following component
CC-3-V 21.00％ Cl.p.： 96.5℃
CCG-V-F 5.00％ Δn： 0.1314
CCP-V-1 14.00％ n
o： 1.4954
CCP-V2-1 15.00％ V
10： 2.13V
CVCP-1V-O1 5.00％ S： 1.054
CVCP-V-O1 5.00％ t
tot： 275ms
PPTUI-3-2 14.00％
PZU-V2-N 5.00% (general formula III c
*)
PCH-2N.F.F 8.00% (general formula III b
*)
PCH-3N.F.F 8.00% (general formula III b
*)
Embodiment 5
By following component form according to TN of the present invention and STN mixture (M5)
CC-3-V 21.50％ Cl.p.： 98.0℃
CCG-V-F 3.00％ Δn： 0.1308
CCP-V-1 14.00％ n
o： 1.4944
CCP-V2-1 15.00％ V
10： 2.02V
CVCP-1V-O1 5.00％ S： 1.059
CVCP-V-O1 5.00％ t
tot： 278ms
PPTUI-3-2 14.50％
CCPC-33 2.00％
PZU-V2-N 4.00% (general formula III c
*)
PCH-2N.F.F 8.00% (general formula III b
*)
DU-2-N 8.00% (general formula I)
V5 compares with mixture, and described mixture M 5 has higher clear point, lower threshold voltage and better steepness, and they have suitable total time of response.
Accompanying drawing 2 has shown the frequency dependence of the threshold voltage of M5 and V5.Compare with V5, M5 according to the present invention has significantly lower frequency dependence.
Comparing embodiment 6
TN and the STN mixture (V6) formed by following component
CP-1V-N 10.00％ Cl.p.： 91.5℃
CC-3-V 16.00％ Δn： 0.1425
CCP-V-1 12.00％ n
o： 1.4970
CCP-V2-1 13.50％ V
10： 1.72V
CVCP-1V-O1 5.00％ S： 1.071
PPTUI-3-2 15.50％ t
tot： 278ms
CCPC-33 5.00％
PCH-2N.F.F 15.00% (general formula III b
*)
PZU-V2-N 8.00% (general formula III c
*)
Embodiment 6a
By following component form according to TN of the present invention and STN mixture (M6a)
CP-1V-N 10.00％ Cl.p.： 87.0℃
CC-3-V 20.00％ Δn： 0.1406
CC-5-V 9.00％ n
o： 1.4921
CCP-V2-1 4.00％ V
10： 1.72V
CVCP-V-1 5.00％ S： 1.061
CVCP-V-O1 5.00％ t
tot： 251ms
CVCP-1V-O1 5.00％
PPTUI-3-2 19.00％
CCPC-33 5.00％
PZU-V2-N 3.00% (general formula III c
*)
DU-2-N 15.00% (general formula I)
V6 compares with mixture, and described mixture has total faster time of response, has identical threshold voltage.
Embodiment 6b
By following component form according to TN of the present invention and STN mixture (M6b)
CP-1V-N 10.00％ Cl.p.： 92.5℃
CC-3-V 20.00％ Δn： 0.1400
CC-5-V 10.00％ n
o： 1.4932
CCP-V2-1 6.00％ V
10： 1.76V
CVCP-V-1 5.00％ S： 1.071
CVCP-V-O1 5.00％ t
tot： 238ms
CVCP-1V-O1 5.00％
PPTUI-3-2 17.00％
CCPC-33 5.00％
PZU-V2-N 8.00% (general formula III c
*)
DU-2-N 9.00% (general formula I)
V6 compares with mixture, and described mixture has significantly total faster time of response and the clear point of Geng Gao, and they have suitable threshold voltage.
Accompanying drawing 3 has shown the frequency dependence of the threshold voltage of M6a, M6b and V6.Compare with V6, have significantly lower frequency dependence according to M6a of the present invention and M6b.
Claims (10)
1. liquid crystal compound comprises the compound of at least a general formula I,
R wherein
1Be alkyl, alkoxyl group or alkenyl with 1 to 12 carbon atom, one of them or two non-conterminous CH
2Group in addition also can be by-O-,-CH=CH-,-CO-,-OCO-or-COO-replaces, but requires the O atom directly not to be connected with each other,
Be characterised in that described mixture comprises the general formula III b that is less than 10% weight
*Compound and the general formula III c that is less than 10% weight
*Compound
Wherein R is alkyl, alkenyl or the alkoxyl group with 1 to 12 carbon atom.
2. according to the liquid crystal compound of claim 1, be characterised in that it contains at least a general formula I I and/or II
*Compound
Wherein
A
4Be 1,4-phenylene or anti-form-1, the 4-cyclohexylidene,
R
3Be alkenyl with 2-7 carbon atom,
R
4Be alkyl, alkoxyl group or alkenyl with 1 to 12 carbon atom, one of them or
Two non-conterminous CH
2Group in addition also can be by-O-,-CH=CH-, and-CO-,
-OCO-or-COO-replaces, but requires the O atom directly not to be connected with each other,
A is 0 or 1,
L
1And L
2Be H or F independently of one another,
Q is CF
2, OCF
2, CFH, OCFH or singly-bound and
Y is F or Cl.
3. according to the liquid crystal compound of one of claim 1 and 2, be characterised in that it comprises one or more compounds of following general formula:
R wherein
3aBe H, CH
3, C
2H
5Or n-C
3H
7, R
2Suc as formula among the I to R
1Define.
4. according to the liquid crystal compound of one of claim 1-3, be characterised in that it comprises one or more compounds of following general formula:
R wherein
1And R
2Independently of one another suc as formula among the I to R
1Define.
5. according to the liquid crystal compound of one of claim 1-4, be characterised in that it comprises one or more compounds that are selected from following general formula:
R wherein
3aAnd R
4aBe H, CH independently of one another
3, C
2H
5Or n-C
3H
7And alkyl is the alkyl with 1-8 carbon atom.
6. according to the liquid crystal compound of one of claim 1-5, be characterised in that it comprises one or more compound of Formula I of 3-45%.
7. according to the liquid crystal compound of one of claim 1-6, be characterised in that general formula III b
*And IIIc
*The ratio of compound in each case≤8%.
8. the liquid-crystal display that contains the liquid crystal compound of one of with good grounds claim 1-7.
9.TN or the stn liquid crystal indicating meter, have
-two outside plates, they form the crystal pond with framework,
-be arranged in the nematic liquid crystal mixtures of the positivity dielectric anisotropy in crystal pond,
-electrode layer of oriented layer arranged on the inboard of outside plate,
-between the longitudinal axis of the lip-deep molecule of outside plate and outside plate 0 spend to the inclination angles of 30 degree and
The twist angle from the oriented layer to the oriented layer of liquid crystal compound in-the crystal pond between 22.5 ° and 600 °,
-nematic liquid crystal mixtures, composed of the following components:
A) liquid crystal of 15-80wt%
Component A, it is made up of one or more compounds that have greater than+1.5 dielectric anisotropy;
B) liquid crystal of 20-85wt%
B component, it by have-1.5 and+one or more compounds of dielectric anisotropy between 1.5 form;
C) liquid crystal of 0-20wt%
Component D, it is lower than one or more compounds of-1.5 dielectric anisotropy and forms by having; With
D) if necessary, optically active
Component C, its consumption makes that the ratio between the natural pitch of layer thickness (gap of outside plate) and chiral nematic liquid crystal mixture is about 0.2 to 1.3,
Be characterised in that described nematic liquid crystal mixtures is the liquid crystal compound according to one of claim 1-7.
10. cholesteric liquid crystal display, SSCT or PSCT indicating meter comprise as one or more chiral dopants of optically active component with as the liquid crystal compound according to one of claim 1-7 of nematic component.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10343574.3 | 2003-09-19 | ||
| DE10343574 | 2003-09-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1613965A true CN1613965A (en) | 2005-05-11 |
Family
ID=34305971
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 200410078718 Pending CN1613965A (en) | 2003-09-19 | 2004-09-17 | Nematic liquid crystal mixture and display therewith |
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| Country | Link |
|---|---|
| JP (1) | JP5312723B2 (en) |
| CN (1) | CN1613965A (en) |
| DE (1) | DE102004039276B4 (en) |
| TW (1) | TWI399425B (en) |
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| CN1908117A (en) * | 2005-08-03 | 2007-02-07 | 默克专利股份有限公司 | LC-mixtures with low frequency dependence for TFT-displays |
| CN102858917A (en) * | 2010-04-28 | 2013-01-02 | 默克专利股份有限公司 | Optical switch element comprising a liquid-crystalline medium |
| CN102899050A (en) * | 2012-10-13 | 2013-01-30 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and displayer having same |
| CN101421375B (en) * | 2006-04-15 | 2013-07-24 | 默克专利股份有限公司 | Liquid-crystalline mixtures and liquid-crystal displays |
| CN103215047A (en) * | 2005-08-09 | 2013-07-24 | 默克专利股份有限公司 | Liquid-crystal medium |
| CN108884389A (en) * | 2016-03-25 | 2018-11-23 | 捷恩智株式会社 | Liquid-crystal composition and liquid crystal display element |
| CN114437738A (en) * | 2020-11-05 | 2022-05-06 | 江苏和成显示科技有限公司 | Liquid crystal composition and liquid crystal display device thereof |
| CN114787318A (en) * | 2019-12-24 | 2022-07-22 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition capable of adapting to wider working temperature and application thereof in device |
| CN115029142A (en) * | 2021-03-04 | 2022-09-09 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5646827B2 (en) * | 2008-07-25 | 2014-12-24 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Liquid crystal medium and liquid crystal display having high twist |
| TR201903813T4 (en) * | 2011-09-05 | 2019-04-22 | Merck Patent Gmbh | Liquid crystal medium and high frequency components containing it. |
| JP2016102222A (en) * | 2016-02-24 | 2016-06-02 | Dic株式会社 | Nematic liquid crystal composition |
| JP2018035371A (en) * | 2017-11-13 | 2018-03-08 | Dic株式会社 | Nematic liquid crystal composition |
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|---|---|---|---|---|
| JPH03223276A (en) * | 1989-10-12 | 1991-10-02 | Seiko Epson Corp | 1,3-dioxane derivative and liquid crystal composition containing the same |
| JPH10512914A (en) * | 1995-02-03 | 1998-12-08 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | Electro-optical liquid crystal display |
| DE19537802A1 (en) * | 1995-10-11 | 1997-04-17 | Merck Patent Gmbh | Electro-optical liquid crystal display |
| DE10111139A1 (en) * | 2000-04-07 | 2001-10-11 | Merck Patent Gmbh | Electro-optical liquid crystal display with orientation reversal layer, useful for in-plane switching displays, having liquid crystal medium containing 4-cyclohexyl-cyclohexane-1-carboxylic acid ester derivative |
| DE10111142A1 (en) * | 2000-04-07 | 2001-10-11 | Merck Patent Gmbh | Electro-optical liquid crystal display with orientation reversal layer, useful for in-plane switching displays, having liquid crystal medium containing mesogenic 2-cyano-5-phenyl-pyrimidine derivative |
| DE10254602B4 (en) * | 2001-12-21 | 2015-10-22 | Merck Patent Gmbh | Liquid-crystalline medium and its use |
| ATE353097T1 (en) * | 2002-12-21 | 2007-02-15 | Merck Patent Gmbh | LIQUID CRYSTALLINE MEDIUM |
-
2004
- 2004-08-13 DE DE102004039276A patent/DE102004039276B4/en not_active Expired - Fee Related
- 2004-09-17 CN CN 200410078718 patent/CN1613965A/en active Pending
- 2004-09-17 TW TW93128286A patent/TWI399425B/en not_active IP Right Cessation
- 2004-09-21 JP JP2004273264A patent/JP5312723B2/en not_active Expired - Fee Related
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1908117A (en) * | 2005-08-03 | 2007-02-07 | 默克专利股份有限公司 | LC-mixtures with low frequency dependence for TFT-displays |
| CN1908117B (en) * | 2005-08-03 | 2013-03-27 | 默克专利股份有限公司 | LC-mixtures with low frequency dependence for TFT-displays |
| CN103215047A (en) * | 2005-08-09 | 2013-07-24 | 默克专利股份有限公司 | Liquid-crystal medium |
| CN101421375B (en) * | 2006-04-15 | 2013-07-24 | 默克专利股份有限公司 | Liquid-crystalline mixtures and liquid-crystal displays |
| CN102858917B (en) * | 2010-04-28 | 2015-02-18 | 默克专利股份有限公司 | Optical switch element comprising a liquid-crystalline medium |
| CN102858917A (en) * | 2010-04-28 | 2013-01-02 | 默克专利股份有限公司 | Optical switch element comprising a liquid-crystalline medium |
| US9416314B2 (en) | 2010-04-28 | 2016-08-16 | Merck Patent Gmbh | Optical switch element comprising a liquid-crystalline medium |
| CN102899050A (en) * | 2012-10-13 | 2013-01-30 | 江苏和成显示科技股份有限公司 | Liquid crystal composition and displayer having same |
| CN108884389A (en) * | 2016-03-25 | 2018-11-23 | 捷恩智株式会社 | Liquid-crystal composition and liquid crystal display element |
| CN114787318A (en) * | 2019-12-24 | 2022-07-22 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition capable of adapting to wider working temperature and application thereof in device |
| CN114437738A (en) * | 2020-11-05 | 2022-05-06 | 江苏和成显示科技有限公司 | Liquid crystal composition and liquid crystal display device thereof |
| CN114437738B (en) * | 2020-11-05 | 2024-07-30 | 江苏和成显示科技有限公司 | Liquid crystal composition and liquid crystal display device thereof |
| CN115029142A (en) * | 2021-03-04 | 2022-09-09 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition and application thereof |
| WO2022184098A1 (en) * | 2021-03-04 | 2022-09-09 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition and application thereof |
| CN115029142B (en) * | 2021-03-04 | 2023-10-24 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5312723B2 (en) | 2013-10-09 |
| JP2005089759A (en) | 2005-04-07 |
| TW200513515A (en) | 2005-04-16 |
| DE102004039276A1 (en) | 2005-04-14 |
| DE102004039276B4 (en) | 2013-03-07 |
| TWI399425B (en) | 2013-06-21 |
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