CN101338199A - Nematic phase liquid crystal composition - Google Patents
Nematic phase liquid crystal composition Download PDFInfo
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- CN101338199A CN101338199A CNA2008100255039A CN200810025503A CN101338199A CN 101338199 A CN101338199 A CN 101338199A CN A2008100255039 A CNA2008100255039 A CN A2008100255039A CN 200810025503 A CN200810025503 A CN 200810025503A CN 101338199 A CN101338199 A CN 101338199A
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Abstract
The invention relates to a nematic liquid crystal combination used for TN, STN, TFT displaying devices, which comprises one of a general formula (I) or / and (II) or a plurality of bicyclo system derivatives. X' is selected from F and Cl, and F is optimized. Ra, Rb, Ra' and Rb' are respectively and independently selected from alkyl, alkoxy, alkenyl, alkenoxy, fluoroalkyl, fluoroalkoxy, fluoroalkenyl or fluoroalkenoxy. The combination is characterized in that difluoro chain hydrocarbon derivatives are used for various displays to result in the lowered low temperature FNP and increased low temperature stability of the combination. Especially under low temperature, the responding time is very fast. In STN displaying, the gradient performance can be improved, and the information capacity of the display can be improved. In the displaying of TN caproic TN type TFT, the gray scale display can be improved and the color expression ability can be enriched.
Description
Technical field
The present invention relates to the liquid-crystal composition as liquid crystal material, particularly nematic phase liquid crystal composition.
Background technology
At present, liquid-crystal display is widely used, and the development of liquid crystal material is rapid, and particularly the nematic liquid crystal material is with fastest developing speed.Nematic phase twisted-nematic (be called for short TN) indicating meter is from M.Helfrich, and Appl.Phys.Lett. is known in 18,127 (1971).In the TN display format, the TN indicating meter is simple relatively with technology making flow process, technology controlling and process is relatively easy, and the liquid crystal material range of choice is general more greatly and comparatively.The liquid crystal kind that TN type display format uses comprises ester class, biphenyl nitrile, miazines, dioxane class, cyclohexyl biphenyl class etc.All kinds of liquid crystal monomers have following performance characteristics:
(1), biphenyls liquid crystal: viscosity is lower, (Δ n) is bigger for degree of birefringence;
(2), Santosol 360 class liquid crystal: viscosity is lower than biphenyls liquid crystal, and (Δ n) is smaller relatively for degree of birefringence;
(3), (Δ n) is bigger for miazines liquid crystal birefringence rate, viscosity is bigger, low-temperature performance is bad;
(4), the esters monomer kind is very many, can carry out the specific aim combination according to different needs, but that shortcoming is a viscosity is higher.
Along with the development of lcd technology, require the capacity of display of display device to increase.Traditional TN indicating meter is owing to be subjected to the restriction of liquid crystal material performance, and number of scanning lines is no more than 32, again because the existence of cross-effect diminishes contrast gradient decline, visual angle.So people have invented the STN technique of display, the twist angle that it makes liquid crystal molecule increases to 180～270 ° from 90 °, and the steepness of photoelectric curve is increased, and the capacity of display increases, and contrast gradient improves, and requires employed nematic liquid crystal material electro-optical properties better.TN type liquid crystalline cpd far can not satisfy the display requirement of STN-LCD.Thereby developed diphenyl acetylene class, ethyl bridged bond class and alkenyl class liquid crystalline cpd as the STN liquid crystal material, the capacity of display is enlarged, the electro-optical characteristic curves steepening has changed the display performance of STN-LCD.
(1), (diphenyl) acetylene compounds: the response speed of STN-LCD is brought up to 120～130ms from 300ms, the STN-LCD performance is significantly improved, thereby use morely in current STN-LCD, existing STN-LCD contains (diphenyl) acetylene compounds with having approximately in the liquid crystal material in 70% the prescription.
(2), ethyl bridged bond class liquid crystal: compare with corresponding other class liquid crystal, the viscosity ratio of this class liquid crystal is lower; The transformation temperature scope and the fusing point of respective compound are relatively low, are the important component of regulating low temperature TN and STN mixed liquid crystal material at low temperature performance.
(3), alkenyl class liquid crystal:, for this reason, have only the elastic constant ratio (K33/K11) that increases liquid crystal material just can achieve the goal because STN-LCD requires to have steep threshold property.Alkene end group class liquid crystalline cpd has unusual big elastic constant ratio (K33/K11), is used for STN-LCD, obtains very satisfied result.
Along with thin film transistor (Thin Film Transistor, TFT) array drives the develop rapidly of liquid-crystal display (TET LCD) technology, TFT LCD has not only occupied high-grade monitor markets such as portable notebook computer in recent years, and, substitute traditional indicating meter at present just fast along with the improving and the reduction of cost of manufacturing process.Owing to adopt thin film transistor (TFT) array directly to drive liquid crystal molecule, eliminated the monkey chatter effect, thereby shown that information content is big; Be used low viscous liquid crystal material, response speed greatly improves, and can satisfy the needs that video image shows.Therefore, TFT LCD has been shown with qualitative leap than TN type, STN type liquid crystal, becomes one of the most rising technique of display of 21 century.The desired liquid crystal material of TFT-LCD must be to heat, chemistry, electricity, good light stability, electric charge conservation rate height, viscosity is low, the high performance compound of resistivity (ρ 〉=1.0 * 1013 Ω cm), these conditions are that traditional cyano-containing compound and ester compound can't satisfy, and Kai Fa fluorinated liquid crystal material then more was applicable to system TFT-LCD in the last few years.Over past ten years, the exploitation of nearly all nematic phase material all is the fluorinated liquid crystal compound, and its mixed liquid crystal exploitation also mostly is the fluorinated liquid crystal component.These fluorine-containing liquid crystal materials also can be made the liquid crystal material of high-grade TN, wide temperature TN, STN-LCD simultaneously.TFT LCD possesses the operating temperature range of good materialization stability, broad except requiring with liquid crystal material, also must possess following characteristic:
(1), low viscosity, viscosity should be less than 35mPas in the time of 20 ℃, to satisfy the needs of response fast;
(2), high voltage holding ratio (V.H.R), this meaning liquid crystal material must possess higher resistivity, general requirement is at least greater than 10
12Ω cm;
(3), lower threshold voltage (Vth), to reach low voltage drive, reduce the purpose of power consumption;
(4), the optical anisotropy (Δ n) that is complementary with TFT-LCD, to eliminate the rainbow effect, obtain bigger contrast gradient and wide-angle view.Δ n value scope should be preferably in about 0.080～0.110 between 0.060～0.125.
Widely used end group is the liquid crystal material of cyano group in TN, stn liquid crystal show already, biphenyl class, Santosol 360 class liquid crystal as cyano-containing, although it has higher Δ ε and good electro-optical properties, but studies show that, contain the compound of holding cyano group and be easy to introduce ionic impurity, voltage retention is low; Its viscosity is compared still higher with the fluorinated liquid crystal with same molecular structure, these unfavorable factors have limited the application of this compounds in TFT LCD.Ester liquid crystal has simple, the miscellaneous characteristics of synthetic method, and broad between the phase change zone, and consumption greatly reduces in the TFT-LCD prescription but its higher viscosity causes.Therefore, the above novel liquid crystal compound that requires is satisfied in exploitation becomes liquid crystal chemistry main research work.
But, the novel liquid crystal molecule is synthetic more and more difficult at present, and the compound that possesses actual application value is also less relatively, and single compound has been difficult to satisfy the harsh requirement in the practical application, then can remedy the deficiency on the mutual performance by the different liquid crystal monomer science of carrying out is mixed.Like this, by synthesizing the liquid crystalline cpd that on some performance, has distinctive feature, be applied to also can reach the purpose that improves display performance in the mixed liquid crystal prescription.
Summary of the invention
The purpose of this invention is to provide the novel nematic phase liquid crystal composition that is applicable to that TN, STN or TFT indicating meter also can improve the liquid crystal low temperature viscosity and have the low temperature cosolvency.
This nematic phase liquid crystal composition comprises as general formula (I) or/and one or more compounds (II),
Wherein,
X ' is selected from F or Cl, is preferably to be F.
Ra, Rb, Ra ', Rb ' are independently selected from alkyl, alkoxyl group, thiazolinyl, alkene oxygen base, fluoro-alkyl, fluoroalkyl, fluoro thiazolinyl or fluoro alkene oxygen base respectively;
The carbonatoms of Ra, Rb is respectively 1～10, and preferred 1～8;
The carbonatoms of Ra ', Rb ' is respectively 0～8, is preferably 0～5, is preferably 0～2 especially.
This nematic phase liquid crystal composition also comprise general formula III-1～III-4 in one or more compounds:
Wherein,
R
1, R
2Be independently selected from C respectively
1～C
10Alkyl, alkoxyl group or oxyalkyl, or C
2～C
10Alkenyl, alkenyloxy or oxygen alkenyl, be preferably C
1～C
7Alkyl or C
2～C
7Alkenyl; Wherein more be preferably R
1And R
2The carbon number sum be less than or equal to 10.
X be selected from halogen ,-OCF
3,-OCHF
2, C
1～C
7Alkyl, alkoxyl group or oxyalkyl or C
2～C
7Alkenyl, alkenyloxy or oxygen alkenyl;
Y is selected from halogen or CN, and wherein halogen is preferably F;
L
1, L
2Be independently selected from H or halogen respectively, wherein halogen is preferably F;
Z be singly-bound ,-COO-,-C
2H
4-,-CH
2O-,-CH=CH-,-CF
2O-or-C ≡ C-, wherein be preferably singly-bound ,-COO-,-CH=CH-or-CF
2O-;
N, m are independently selected from 0 or 1 respectively.
Said III-2 compounds is at least a compound in III-2-a to III-2-r preferably:
Said III-3 compound, at least a compound among preferred self-drifting III-3-a～III-3-n:
When X was F, L1 also was F.
Said III-4 compound is at least a compound in formula III-4-a～III-4-d preferably:
At least a compound among wherein preferred III-4-a and III-4-b, the III-4-d, at least a compound, particularly 1-2 kind compound among preferred especially III-4-b, the III-4-d.
This nematic phase liquid crystal composition also contains additive, and said additive is selected from least a in the following compound:
The C15 type
The CB15 type
The CM21 type
The R/S811 type
The CM44 type
The CM45 type
The CM47 type
The R/S1011 type
The R/S3011 type
The R/S2011 type
The weight percentage of said nematic phase liquid crystal composition each component is as follows:
I compounds 1%～80%,
II compounds 1%～80%,
III-1 compounds 0%～40% is preferably 5-40% and is preferably 5-35% especially;
III-2 compounds 0%～70%, preferred 0-50% is preferably 5-40% especially;
III-3 compounds 0%～60%, preferred 5-60% is preferably 10-50% especially;
III-4 compounds 0%～80%, preferred 1-60%, particularly 5-50%;
Additive 0.05～10%; Preferred 0.05-2%, preferred especially 0.05-1.5%.
The general formula (I) and (II) derivative of these class two member ring systems, particularly difluoro chain hydrocarbon derivative wherein has low-down viscosity and extremely low fusing point, in the mixed liquid crystal prescription, can be used as the viscosity reduction component, increase the mutual solubility of mixed crystal, and raising electric charge conservation rate (V.H.R), non-fluorinated liquid crystal more of the same type further reduces threshold voltage (Vth), and can further reduce optical anisotropy (Δ n).It is used for all kinds of demonstrations, makes a low temperature reduction of dissolving each other, and the composition low-temperature stability increases, and particularly at low temperatures, the time of response is very fast; At STN with in showing, can improve and improve the steepness performance, improve the information content that shows, in the own TN type of TN TFT shows, can improve gray scale and show the ability to express of rich colors.
In addition, formula (I) or formula (II) compound are used for the composition of STN, TN or TN type TFT demonstration, can make electric light curve steepness steepening, increase to show way; The temperature dependency of improvement threshold voltage; Can make the frequency dependence of the voltage of STN improvement threshold voltage.Be used for the composition of the TFT demonstration of TN type TFT or other display type, can also effectively improve electric charge conservation rate (V.H.R.).
Embodiment
The following examples are used to illustrate the present invention, rather than limitation of the present invention.All temperature of embodiment are degree centigrade that all per-cents are weight percentage, except as otherwise noted.
Embodiment 1: as the formula (e) of I compounds and as the preparation of formula (f) compound of II compound compound
With formula (a) compound is raw material, gets formula (e) compound by following chemical reaction, and further gets formula (f) compound by formula (e):
Preparation process is as follows:
Wherein, raw material (a), available known method is synthetic, also can directly buy on market.
Formula (b) compound synthetic: add the chloromethyl ether salt 262g that sees in the 2L there-necked flask, THF 600ml under the nitrogen protection, adds potassium tert.-butoxide 86g in batches, is stirred to reaction solution and becomes scarlet.After stirring 30min, slowly drip the mixing solutions of (a) 127.5g/THF 200ml, stirring at normal temperature is more than 4 hours.The ethyl acetate extraction oil reservoir is used in the separatory washing, and drying, column chromatography, concentrated obtain product 135.1g, and yield is 95.0%.
Formula (c)) compound is synthetic: add concentrated hydrochloric acid 500ml/H in the 5L beaker
2The mixing solutions of O 1L adds 135.1g (b) in the beaker while stirring, is washed to neutrality, uses the ethyl acetate extraction oil reservoir, and dry, concentrated, recrystallization obtain product 108.3g, and yield is 84.7%.
Synthesizing of formula (d) compound: add an amount of KOH and MeOH in the 1L there-necked flask, add (c) 108.3g, slowly drip and remain KOH/MeOH mixing solutions (KOH 11.5g/MeOH 500ml altogether), low temperature stirs more than 4 hours below 0 ℃.In the 5L beaker, add 1L CH
2Cl
2With 1L H
2O adds reaction solution while stirring, leaves standstill, and the separatory washing obtains product 88.3g with dichloromethane extraction oil reservoir, drying, recrystallization, and productive rate is 81.5%.
Synthesizing of formula (e) compound: add (d) 80g, PPh in the 1L there-necked flask
391.2g and DMF100ml, heating for dissolving drips ClF
2The mixed solution of CCOONa 92.4g/DMF 200ml after dropwising, continues heated and stirred more than 4 hours.Reactants water is washed till neutrality, and usefulness methylbenzene extraction oil reservoir, drying, mistake chromatography column, concentrated, recrystallization obtain product 90.3g, and GC purity is 99.8%, productive rate 49%.
Formula (f) compound synthetic: add e 90g in the 1L hydrogenation still, dehydrated alcohol 200ml, 5%Pd/C 5g, atmospheric hydrogenation finishes by detecting to hydrogenation, obtains target product formula (f) after the filtering and concentrating.
Following embodiment 2-5 is the performance test of liquid-crystal composition of the present invention, and every example has corresponding Comparative Examples:
Be simplified illustration, among below the embodiment and Comparative Examples, the structural unit of liquid crystalline cpd is pressed table 1 coded representation:
The unitary corresponding code of table 1 compound structure
Annotate: go up in the table, code n represents the key alkyl, and in the liquid crystalline cpd code below, n represents that with concrete digital form this numeral is the carbonatoms of alkyl chain.Be numeral " 2 " as the n among the 2PEMN, this numeral " 2 " is represented alkyl C
2H
5-.
The liquid crystalline cpd that with the code is 2PEMN is an example, table in the contrast, and this code specifically is expressed as following structural formula:
And R wherein
1Promptly be C
2H
5-.
In the last table, code Vn and nV all represent alkenyl, and different is that Vn represents thiazolinyl preceding, alkyl after; Code nV then represents alkyl preceding, thiazolinyl after.Wherein n still occurs with digital form.
Every test event is described as follows:
T
N-I(℃) clearing point (to row-isotropic phase transition temperature)
Visc. kinetic viscosity (mm
2/ s
-1, 20 ℃, except as otherwise noted),
n
oCommon specific refractory power (589nm, 20 ℃)
Δ n
20 ℃Optical anisotropy (589nm, 20 ℃)
The common specific refractory power of no (589nm, 60 ℃)
Δ n
60 ℃Optical anisotropy (589nm, 60 ℃)
D Δ n/ Δ n
20 ℃The % specific refractory power is with dependence on temperature (Δ n
20 ℃-Δ n
60 ℃/ Δ n
20 ℃* 100%
A=(V
10/ V
90-1) 100 (%) characteristic curve steepness=Vsat/Vth,
V
90,0,25 (V)The character voltage of threshold voltage=when relative contrast 90% (normal white mode)
V
10,0,25 (V)Character voltage when relative contrast 10% (normal white mode)
Annotate: Vth and characteristic curve steepness a value are measured by square wave addressing (100Hz), and probe temperature is 25 ± 2 ℃; Viscosity is kinetic viscosity; Specific refractory power and specific refractory power anisotropy are under the sodium lamp (589nm), 20 ℃ and 60 ℃ of results that test obtains.
Below each table respectively expression each implement or the test result of the weight percentage of the chemical composition (representing) of Comparative Examples liquid-crystal composition, each component and the liquid-crystal composition formed by these components with structural code.
Embodiment 2
Comparative Examples 2
Embodiment 3
Comparative Examples 3
Embodiment 4
Comparative Examples 4
Embodiment 5
Comparative Examples 5
Claims (10)
1. nematic phase liquid crystal composition is characterized in that comprising as general formula (I) or/and one or more compounds (II),
Wherein,
X ' is selected from F, Cl;
Ra, Rb, Ra ', Rb ' are independently selected from alkyl, alkoxyl group, thiazolinyl, alkene oxygen base, fluoro-alkyl, fluoroalkyl, fluoro thiazolinyl or fluoro alkene oxygen base respectively;
Wherein: the carbonatoms of Ra, Rb is respectively 1～10;
The carbonatoms of Ra ', Rb ' is respectively 0～8.
2. nematic phase liquid crystal composition according to claim 1, it is characterized in that general formula (I) and (II) in,
The carbonatoms of Ra, Rb is respectively 1～8;
The carbonatoms of Ra ', Rb ' is preferably 0～2 for difference 0～5;
X ' is F.
3. nematic phase liquid crystal composition according to claim 1, it is characterized in that also comprising general formula III-1～III-4 in one or more compounds:
Wherein,
R
1, R
2Be independently selected from C respectively
1～C
10Alkyl, alkoxyl group or oxyalkyl, or C
2～C
10Alkenyl, alkenyloxy or oxygen alkenyl;
X be selected from halogen ,-OCF
3,-OCHF
2, C
1～C
7Alkyl, alkoxyl group or oxyalkyl or C
2～C
7Alkenyl, alkenyloxy or oxygen alkenyl;
Y is selected from halogen or CN;
L
1, L
2Be independently selected from H or halogen respectively;
Z be singly-bound ,-COO-,-C
2H
4-,-CH
2O-,-CH=CH-,-CF
2O-or-C ≡ C-;
N, m are independently selected from 0 or 1 respectively.
4. nematic phase liquid crystal composition according to claim 3 is characterized in that
R
1, R
2Be independently selected from C respectively
1～C
7Alkyl or C
2～C
7Alkenyl,
Y is F or CN,
Z be singly-bound ,-COO-,-CH=CH-or-CF
2O-,
L
1, L
2Be independently selected from H or F respectively.
5. nematic phase liquid crystal composition according to claim 3 is characterized in that said III-1 compounds is selected from least a in III-1-a to the III-1-j compound:
Wherein: the R1 among formula III-1-h, R2 are alkyl or are alkenyl,
R1, R2 among formula III-1-j are alkyl.
6. according to the described nematic phase liquid crystal composition of claim 3, it is characterized in that the III-2 compounds is selected from compound at least a among the III-2-a to III-2-r:
Wherein,
R
1, R
2Be independently selected from C respectively
1～C
10Alkyl, alkoxyl group or oxyalkyl, or C
2～C
10Alkenyl, alkenyloxy or oxygen alkenyl, be preferably C
1～C
7Alkyl or C
2～C
7Alkenyl; Wherein more be preferably R
1And R
2The carbon number sum be less than or equal to 10.
X be selected from halogen ,-OCF
3,-OCHF
2, C
1～C
7Alkyl, alkoxyl group or oxyalkyl or C
2～C
7Alkenyl, alkenyloxy or oxygen alkenyl;
Y is selected from halogen or CN, and wherein halogen is preferably F;
L
1, L
2Be independently selected from H or halogen respectively, wherein halogen is preferably F;
Z be singly-bound ,-COO-,-C
2H
4-,-CH
2O-,-CH=CH-,-CF
2O-or-C ≡ C-, wherein be preferably singly-bound ,-COO-,-CH=CH-or-CF
2O-;
N, m are independently selected from 0 or 1 respectively.
Said III-2 compounds is at least a compound in III-2-a to III-2-r preferably:
7. nematic phase liquid crystal composition according to claim 3 is characterized in that said III-3 compound, comprises at least a compound among general formula III-3-a～III-3-n:
When X was F, L1 also was F.
8. nematic phase liquid crystal composition according to claim 3 is characterized in that said III-4 compound is selected from least a compound among formula III-4-a～III-4-d:
9. according to any one described nematic phase liquid crystal composition in the claim 3～8, it is characterized in that also containing additive, said additive is selected from least a in the following compound:
The C15 type
The CB15 type
The CM21 type
The R/S811 type
The CM44 type
The CM45 type
The CM47 type
The R/S1011 type
The R/S3011 type
The R/S2011 type
The weight percentage of each component is as follows:
I compounds 1%～80%,
II compounds 1%～80%,
III-1 compounds 0%～40%,
III-2 compounds 0%～70%,
III-3 compounds 0%～60%,
III-4 compounds 0%～80%,
Additive 0.05～10%.
10. according to any one described nematic phase liquid crystal composition in the claim 9, it is characterized in that also containing additive, the weight percentage of each component is as follows:
I compounds 1%～80%,
II compounds 1%～80%,
III-1 compounds 5～40%,
III-2 compounds 0～50%,
III-3 compounds 5～60%,
III-4 compounds 1～60%,
Additive 0.05～2%.
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|---|---|---|---|
| CNA2008100255039A CN101338199A (en) | 2008-05-06 | 2008-05-06 | Nematic phase liquid crystal composition |
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Family
ID=40212371
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102890355A (en) * | 2012-10-13 | 2013-01-23 | 江苏和成显示科技股份有限公司 | Ultra-high temperature liquid crystal display |
| CN102899052A (en) * | 2012-10-13 | 2013-01-30 | 江苏和成显示科技股份有限公司 | Superwide-temperature TN liquid crystal composition |
| CN102929021A (en) * | 2012-10-13 | 2013-02-13 | 江苏和成显示科技股份有限公司 | Liquid crystal light valve and light valve electric-welding protective mask |
| CN102977895A (en) * | 2012-11-30 | 2013-03-20 | 石家庄诚志永华显示材料有限公司 | Twisted nematic first polar small liquid crystal composition |
| CN108003893A (en) * | 2016-11-02 | 2018-05-08 | 石家庄诚志永华显示材料有限公司 | A kind of high vertical dielectric liquid-crystal compounds, liquid-crystal composition, liquid crystal display device |
-
2008
- 2008-05-06 CN CNA2008100255039A patent/CN101338199A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102890355A (en) * | 2012-10-13 | 2013-01-23 | 江苏和成显示科技股份有限公司 | Ultra-high temperature liquid crystal display |
| CN102899052A (en) * | 2012-10-13 | 2013-01-30 | 江苏和成显示科技股份有限公司 | Superwide-temperature TN liquid crystal composition |
| CN102929021A (en) * | 2012-10-13 | 2013-02-13 | 江苏和成显示科技股份有限公司 | Liquid crystal light valve and light valve electric-welding protective mask |
| CN102899052B (en) * | 2012-10-13 | 2014-08-13 | 江苏和成显示科技股份有限公司 | Superwide-temperature TN liquid crystal composition |
| CN102977895A (en) * | 2012-11-30 | 2013-03-20 | 石家庄诚志永华显示材料有限公司 | Twisted nematic first polar small liquid crystal composition |
| CN108003893A (en) * | 2016-11-02 | 2018-05-08 | 石家庄诚志永华显示材料有限公司 | A kind of high vertical dielectric liquid-crystal compounds, liquid-crystal composition, liquid crystal display device |
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Open date: 20090107 |