CN103242861A - Liquid crystal composition and application thereof - Google Patents

Liquid crystal composition and application thereof Download PDF

Info

Publication number
CN103242861A
CN103242861A CN2013101938109A CN201310193810A CN103242861A CN 103242861 A CN103242861 A CN 103242861A CN 2013101938109 A CN2013101938109 A CN 2013101938109A CN 201310193810 A CN201310193810 A CN 201310193810A CN 103242861 A CN103242861 A CN 103242861A
Authority
CN
China
Prior art keywords
liquid
compound
crystal composition
formula
representative
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.)
Granted
Application number
CN2013101938109A
Other languages
Chinese (zh)
Other versions
CN103242861B (en
Inventor
陈海光
杭德余
齐秀梅
姜天孟
贺树芳
陈卯先
田会强
储士红
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Beijing Bayi Space LCD Technology Co Ltd
Original Assignee
BEIJING JINXUNYANGGUANG ELECTRONIC MATERIALS TECHNOLOGY Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BEIJING JINXUNYANGGUANG ELECTRONIC MATERIALS TECHNOLOGY Co Ltd filed Critical BEIJING JINXUNYANGGUANG ELECTRONIC MATERIALS TECHNOLOGY Co Ltd
Priority to CN201310193810.9A priority Critical patent/CN103242861B/en
Publication of CN103242861A publication Critical patent/CN103242861A/en
Application granted granted Critical
Publication of CN103242861B publication Critical patent/CN103242861B/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Landscapes

  • Liquid Crystal Substances (AREA)

Abstract

The invention relates to a liquid crystal composition which contains a pentafluoropropylene ether end group structure liquid crystal compound. The invention further relates to an application of the liquid crystal composition. The liquid crystal composition is excellent in property, has high dielectric anisotropy and low rotary viscosity, and is applicable to liquid crystal displays with display modes of IPS, FFS (fringe field switching), ADS and the like and TN-TFT (twisted nematic-thin film transistor) liquid crystal displays with low driving voltage.

Description

A kind of liquid-crystal composition and application thereof
Technical field
The present invention relates to the liquid-crystal composition field, specifically, relate to a kind of the contain liquid-crystal composition of five fluorine propylene ethers end-group structure liquid crystalline cpds and the application in field of liquid crystal display thereof.
Background technology
As far back as 19th-century second half, the many scholars that comprise each field such as physics, chemistry, biology have observed some compounds and have varied with temperature the unusual appearance that shows.The time of assert formal discovery liquid crystal afterwards is 1888.Austrian botanist Friedrich of this year Reinitzer does the time spent at the research cholesterol to plant, has found first kind of liquid crystal material: M-nitro benzoic acid cholesterol (cholesteryl benzoate).Between more than 100 year after the discovery liquid crystal phenomenon, people do not have interruption all the time to its research.
In early days, people such as O.Wiener have found the fresenl theory of double refraction of liquid crystal, and E.Bose has proposed the phase theory of liquid crystal, and V.Grandiean etc. have studied liquid crystal molecular orientation mechanism and texture, etc.Echo mutually with the liquid crystal theoretical investigation, phase later 1960s is the golden period of development of liquid crystal science and technology.The nineteen sixty-eight R.Williams of U.S. RCA Corp. finds that nematic liquid crystal forms the striped farmland under electric field action, and light scattering phenomenon is arranged.G.H.Heilmeir develops into the dynamic scattering display format with being about to it, and makes first liquid-crystal display (LCD) in the world.
Helfrich in 1971 and Schadt have invented TN(Twisred Nematic, twisted nematic) principle, people utilize TN photovoltaic effect and unicircuit to combine, and it is made display device (TN-LCD), for wide prospect has been opened up in the application of liquid crystal.Since the seventies, because the development of large-scale integrated circuit and liquid crystal material, the application of liquid crystal aspect demonstration obtained breakthrough development, and people such as T.Scheffer successively proposed super-twist nematic (Super Twisred Nematic:STN) pattern in 1983～1985 years; Active matrix (Active matrix:AM) mode that P.Brody proposed in 1972 is adopted again.Since 1980, the invention of Thin Film Transistor-LCD technology makes liquid-crystal display become the outstanding person of digital information epoch technique of display, has fundamentally changed the looks of liquid crystal industry.The R.A.SOREF of the U.S. in 1973 proposes liquid crystal photoelectric characteristic under the transverse electric field; 1992, German G.Baur research team proposed noun In-Plane Switching first in paper, and proposing IPS has the visual angle of improvement viewpoint, and IPS-LCD panel in 1996 is at first by Japanese Hitachi(Hitachi) company succeeds in developing.The first-generation IPS of Hitachi indicating meter, visual angle can be promoted to 160 degree, and the reaction times can foreshorten to 40ms.FFS(Fringe Field Switching) technique of display is by the Korea S Hydis(modern times the earliest) research and development of technique of display department, be the innovation to IPS, also be the Development Technology of IPS.Similar with IPS, the electrode of FFS also is to be in same substrate, but the selection of the design of counter electrode and material is optimized: change the IPS opaque electrode into transparency electrode, and dwindle electrode width and spacing, increased transmittance, the visual angle also reaches 180 degree maximizations.
TFT-LCD technology and initial product are in Europe and produced in USA, but its extensive commercial application is finished by Japan, Korea S began to get involved the TFT-LCD industry in 1993, and obtained stronger competitive power very soon, the Taiwan of China in 1998 begins to have added the sector, almost occupied the half of the country by 2005 on industry size, from integral layout, the critical role of China in this industry constantly manifests at present.
At present, though the TFT-LCD product technology is day by day ripe, can successfully solve technical barriers such as visual angle, resolving power, fullness of shade and brightness, its display performance has approached or has surpassed CRT monitor, large size and small-medium size TFT-LCD indicating meter occupy the dominant position of flat-panel monitor gradually in field separately, but are subjected to the restriction of liquid crystal material itself, and it is fast inadequately that TFT-LCD still exists response speed, voltage is low inadequately, and the electric charge conservation rate is high many defectives inadequately.Therefore, from liquid crystal material itself, develop the TFT liquid crystal compound of quick response, high electric charge conservation rate, become focus and difficult point in the industry.
Making a general survey of the liquid crystal material evolution that shows for TFT can find, the exploitation of liquid crystalline cpd all is that the direction towards high electric charge conservation rate, high dielectric anisotropy, excellent low temperature mutual solubility develops, substitute onto last polyfluoro from initial single fluorine and replace, and even afterwards-CF 2Liquid crystalline cpds such as the super polyfluoro replacement of O-bridged bond, ripe liquid crystalline cpd is formed with stable hexa-atomic aromatic nucleus (as phenyl ring) and hexa-atomic alkyl ring (as the hexamethylene ring), and its end bit substituent mostly is alkyl or alkenyl greatly.The end bit substituent is that the compound of polyfluoro thiazolinyl has good chemistry and thermostability, and electric field and magnetic field are had high stability, and the low temperature mutual solubility is also very desirable, is suitable for the mixed liquid crystal compound.
The compound that contains polyfluoro thiazolinyl ethers end-group structure involved in the present invention, be first disclosed as the Japanese Patent JP2003015547 of the electrochemical worker of Japanese rising sun Co., Ltd., this type of structural compounds has higher dielectric anisotropy and lower rotary viscosity, is suitable for the TFT liquid-crystal display and uses.Liquid-crystal composition involved in the present invention is applied to the TFT liquid-crystal display, and it is fast inadequately to solve its response speed, and voltage is low inadequately, and the electric charge conservation rate is high many defectives inadequately.
Summary of the invention
(1) technical problem that will solve
At the response speed of LCD that exists in the prior art fast, voltage low, the not high enough problem of electric charge conservation rate inadequately inadequately, the invention provides a kind of liquid-crystal composition that contains five fluorine propenyl ethers end-group structure compounds, have higher dielectric anisotropy and lower rotary viscosity, be applicable to the liquid crystal indicator of quick response.
Another object of the present invention provides the application of described liquid-crystal composition in liquid crystal indicator.
(2) technical scheme
In order to realize the object of the invention, liquid-crystal composition provided by the invention must comprise one or more of compound of logical formula I and logical formula II representative, i.e. 2%≤I+II≤100%.For the requirement of the liquid-crystal display that is fit to various size and specification, also can contain in the compound of logical formula III, (IV), (V), (VI) and (VII) representative one or more in the liquid-crystal composition, its each composition weight percentage composition is as follows:
The compound of (1) 1～90% logical formula I representative;
The compound of (2) 1～60% logical formula II representatives;
The compound of (3) 0～70% logical formula III and/or (IV) representative;
The compound of one or more representatives in (4) 0～30% general formulas (V), (VI) and (VII);
Described liquid-crystal composition also comprises by weight the optically-active component that accounts for (1)～(4) component gross weight 0～0.5%.
Wherein, the compound of described logical formula I representative is following structure:
Figure BDA00003228308900041
（Ⅰ）
In the formula I, R is selected from C 1～C 12Alkyl, wherein one or more-CH 2-group can be substituted by-O-; Z is selected from-CF 2O-,-C 2H 4-or the C-C singly-bound; It is trans 1 that the ring texture substituent A is selected from, 4-cyclohexyl, 1,4-phenylene or 1,4-pyranyl; L 1～L 5Be independently selected from F or H atom; M, n, p are integer independent of each other, and 0≤m≤2, and n, p are 0 or 1.
The compound of described logical formula II representative is following structure:
（Ⅱ）
In the formula II, R aAnd R bBe independently selected from C 1～C 12Alkyl, wherein one or more-CH 2-group can be substituted by-O-;
The compound of described logical formula III and (IV) representative is respectively following structure:
Figure BDA00003228308900043
（Ⅲ）
Figure BDA00003228308900051
（Ⅳ）
In formula III and (IV), R cAnd R dBe independently selected from C 1～C 12Alkyl, wherein one or more-CH 2-group can be substituted by-O-; L 6Be selected from F or H atom; O, s, t represent 1 or 2 independently of one another; It is trans 1 that ring texture substituent B and C are independently selected from, 4-cyclohexyl or 1,4-phenylene;
The compound of described general formula (V), (VI) and (VII) representative is respectively following structure:
Figure BDA00003228308900052
（Ⅴ）
（Ⅵ）
Figure BDA00003228308900054
（Ⅶ）
In formula (V), (VI) and (VII), R e～R jBe independently selected from C 1～C 12Alkyl, wherein one or more-CH 2-group can be substituted by-O-, and one or more H atoms can be substituted by the F atom, or R e～R jBe independently selected from C 1～C 12Thiazolinyl; L 7Be selected from F or H atom.
In the structural formula of each component of liquid-crystal composition of the present invention, the ring texture substituent A is represented one 1, and the six-membered cyclic substituting group that 4-replaces is in particular: trans 1, and 4-cyclohexyl, 1,4-phenylene or 1,4-pyranyl, its structure is as follows:
Figure BDA00003228308900061
Trans 1, the 4-cyclohexyl
Figure BDA00003228308900062
1,4-phenylene
Figure BDA00003228308900063
1,4-pyranyl
Ring texture substituent B, C represent one 1, and the six-membered cyclic substituting group that 4-replaces is in particular: trans 1, and 4-cyclohexyl or 1,4-phenylene.
In the liquid-crystal composition of the present invention, each component preferred weight percentage composition is as follows:
The compound of (1) 5～85% logical formula I representative;
The compound of (2) 14～55% logical formula II representatives;
The compound of (3) 10～65% logical formula III and/or (IV) representative;
The compound of one or more representatives in (4) 2～21% general formulas (V), (VI) and (VII);
Described liquid-crystal composition also comprises by weight the optically-active component that accounts for (1)～(4) component gross weight 0.07～0.3%.
Preferably, in the liquid-crystal composition of the present invention, the compound of logical formula I representative be formula (I a), in the represented compound of (I b), (I c), (I d), (I e), (I f), (I g), (I h), (I i) one or more:
Figure BDA00003228308900064
（Ⅰa）
（Ⅰb）
Figure BDA00003228308900072
（Ⅰc）
Figure BDA00003228308900073
（Ⅰd）
Figure BDA00003228308900074
（Ⅰe）
Figure BDA00003228308900075
（Ⅰf）
Figure BDA00003228308900081
（Ⅰg）
Figure BDA00003228308900082
（Ⅰh）
Figure BDA00003228308900083
（Ⅰi）
Formula (I a)～(I i) in, R 1～R 8And R ' is independently selected from C 1～C 8Alkyl, wherein one or more-CH 2-group can be substituted by-O-; Z represents-CF 2O-or C-C singly-bound; L 1～L 4Be F or H atom independently.
(indication Z in the liquid crystalline cpd of I shown in a)～(I i) is preferably-CF general formula 2O-compound low temperature mutual solubility is improved, but nematic temperature range narrows down accordingly, therefore also can be the C-C singly-bound and directly links to each other, and improves the clearing point of compound effectively.
More preferably, in the liquid-crystal composition of the present invention, the compound of logical formula I representative is specially one or more in following formula (I a-1), (I b-1), (I b-2), (I c-1), (I c-2), (I d-1), (I d-2), (I e-1), (I f-1), (I g-1), (I h-1), (I i-1) represented compound:
Figure BDA00003228308900091
（Ⅰa-1）
Figure BDA00003228308900092
（Ⅰb-1）
Figure BDA00003228308900093
（Ⅰb-2）
Figure BDA00003228308900094
（Ⅰc-1）
（Ⅰc-2）
Figure BDA00003228308900101
（Ⅰd-1）
（Ⅰd-2）
Figure BDA00003228308900103
（Ⅰe-1）
Figure BDA00003228308900104
（Ⅰf-1）
（Ⅰg-1）
Figure BDA00003228308900111
（Ⅰh-1）
Figure BDA00003228308900112
（Ⅰi-1）
Among formula (I a-1), (I b-1), (I b-2), (I c-1), (I c-2), (I d-1), (I d-2), (I e-1), (I f-1), (I g-1), (the I h-1) and (I i-1), R 9～R 20Be independently selected from C 1～C 5Alkyl, wherein one or more-CH 2-group can be substituted by-O-; Z is selected from-CF 2O-or C-C singly-bound.
Most preferably, in the liquid-crystal composition of the present invention, the compound of logical formula I representative is specially one or more in the represented compound of formula (I-1)～(I-40):
Figure BDA00003228308900113
（Ⅰ-1）
Figure BDA00003228308900114
（Ⅰ-2）
Figure BDA00003228308900121
（Ⅰ-3）
Figure BDA00003228308900122
（Ⅰ-4）
Figure BDA00003228308900123
（Ⅰ-5）
Figure BDA00003228308900124
（Ⅰ-6）
（Ⅰ-7）
Figure BDA00003228308900131
（Ⅰ-8）
Figure BDA00003228308900132
（Ⅰ-9）
Figure BDA00003228308900133
（Ⅰ-10）
Figure BDA00003228308900134
（Ⅰ-11）
Figure BDA00003228308900135
（Ⅰ-12）
Figure BDA00003228308900141
（Ⅰ-13）
Figure BDA00003228308900142
（Ⅰ-14）
Figure BDA00003228308900143
（Ⅰ-15）
Figure BDA00003228308900144
（Ⅰ-16）
Figure BDA00003228308900145
（Ⅰ-17）
（Ⅰ-18）
（Ⅰ-19）
Figure BDA00003228308900152
（Ⅰ-20）
（Ⅰ-21）
Figure BDA00003228308900154
（Ⅰ-22）
Figure BDA00003228308900155
（Ⅰ-23）
Figure BDA00003228308900161
（Ⅰ-24）
Figure BDA00003228308900162
（Ⅰ-25）
Figure BDA00003228308900163
（Ⅰ-26）
Figure BDA00003228308900164
（Ⅰ-27）
Figure BDA00003228308900165
（Ⅰ-28）
Figure BDA00003228308900171
（Ⅰ-29）
Figure BDA00003228308900172
（Ⅰ-30）
Figure BDA00003228308900173
（Ⅰ-31）
（Ⅰ-32）
Figure BDA00003228308900175
（Ⅰ-33）
Figure BDA00003228308900181
（Ⅰ-34）
Figure BDA00003228308900182
（Ⅰ-35）
Figure BDA00003228308900183
（Ⅰ-36）
Figure BDA00003228308900184
（Ⅰ-37）
Figure BDA00003228308900185
（Ⅰ-38）
Figure BDA00003228308900186
（Ⅰ-39）
Figure BDA00003228308900191
（Ⅰ-40）
In the liquid-crystal composition of the present invention, the compound of logical formula I representative is chief component, this compounds has very strong polarity, big electricity anisotropy, and higher clearing point is arranged, the effect that good reduction threshold voltage is arranged in the mixed liquid crystal system, meanwhile, when dissolving each other with other compounds, also showed excellent performance.
Preferably, in the liquid-crystal composition of the present invention, the logical represented compound of formula II be specially formula (II a) or the compound of (II b) representative:
Figure BDA00003228308900192
（Ⅱa）
Figure BDA00003228308900193
（Ⅱb）
Formula (II a) and (II b) in, R A 'Be C 1～C 5Alkyl.
The compound of logical formula II representative is the allotment requisite compounds of liquid-crystal composition of response fast, generally uses this compounds in the used liquid-crystal composition of each display format liquid-crystal display now, and addition is very big.This compounds does not almost have polarity, and the structure of bis cyclohexane makes it that extremely low viscosity and little optical anisotropy be arranged, and reduces to play the effect that can not be substituted for the viscosity of whole mixed system, and is remarkable for the raising effect of the response speed of mixed crystal thereupon.
Preferably, in the liquid-crystal composition of the present invention, the structure of the compound of logical formula III and (IV) representative is respectively:
Figure BDA00003228308900201
（Ⅲa）
Figure BDA00003228308900202
（Ⅲb）
（Ⅲc）
Figure BDA00003228308900204
（Ⅲd）
Figure BDA00003228308900205
（Ⅳa）
Figure BDA00003228308900211
（Ⅳb）
Formula (III a)～(III d), (IV a) and (IV b) in, R C 'And R D 'Be independently selected from C 1～C 5Alkyl, wherein one or more-CH 2-group can be substituted by-O-.
In the liquid-crystal composition of the present invention, the compound weight content of logical formula III and (IV) representative is 0～70%, and preferred content is 1～65%, and optimum content is 10～65%.The compound weight content of its formula of (III) representative is 0～30%, and preferred content is 2～25%, and optimum content is 5～25%; The compound weight content of logical formula IV representative is 0～40%, and preferred content is 5～40%.
In the liquid-crystal composition of the present invention, the compound of logical formula III and (IV) representative has higher dielectric constant, moderate optical anisotropy, higher nematic temperature range, excellent combination property, add this type of component in the mixed liquid crystal and can effectively reduce threshold voltage, every performance of stabilising system.
Preferably, in the liquid-crystal composition of the present invention, R in the compound of described general formula (V) representative eAnd R fBe independently selected from C 1～C 5Alkyl or C 2～C 5Thiazolinyl; R in the compound of described logical formula VI representative hBe selected from C 1～C 5Alkyl, C 1～C 5Alkoxyl group or C 1～C 5Fluoroalkyl, R gBe selected from C 2～C 5Alkyl or C 2～C 5Thiazolinyl; R in the compound of described general formula (VII) representative iAnd R jBe selected from C 1～C 5Alkyl.
The compound of general formula (V), (VI) and (VII) representative plays the effect of auxiliary adjustment for the performance of improving the liquid crystal mixed system, particularly most important for the fine setting of parameter: it has higher clearing point and bigger optical anisotropy, can be used for clearing point and the Δ n(optical anisotropy of the system of adjusting) numerical value.
For liquid-crystal composition of the present invention, if be used for IPS, FFS or the demonstration of ADS mode liquid crystal, then the opticity component concentration is 0%.
For liquid-crystal composition of the present invention, show that if be used for the TN-TFT mode liquid crystal effect that adds the opticity component is to make liquid-crystal composition twist 90 ° in liquid crystal cell, unlikelyly owe to turn round and influence display effect, then its content is 0.05～0.5%, is preferably 0.07～0.3%.
In addition, in order to improve liquid-crystal composition for heat and the light stability of UV-light particularly, also UV light absorber can be added according to circumstances, for example: benzotriazole category, benzophenone, triazines, benzoates; Hindered amine light stabilizer; Hindered phenol anti-oxidants.
Liquid-crystal composition of the present invention can adopt the ordinary method preparation, for example two or more liquid crystalline cpds are at high temperature mixed and dissolving each other, soon liquid crystalline cpd is dissolved in solvent and the mixing for this compound, under reduced pressure distills out this solvent then; Perhaps wherein the less component of content is dissolved under higher temperature in the bigger main ingredient of content, or component under each is dissolved in organic solvent, solution is mixed to obtain after solvent is removed in the back then.Wherein, solvent for use can be organic solvents commonly used such as acetone, chloroform or methyl alcohol.
(3) beneficial effect
The liquid-crystal composition excellent performance that obtains by the present invention, have lower voltage, lower viscosity, high resistivity and voltage retention, liquid-crystal composition of the present invention can be used for liquid crystal indicator, the TFT indicating meter that is particularly useful for various quick responses is as TN type, IPS type, FFS type or ADS type TFT liquid-crystal display.Liquid-crystal composition of the present invention has solved the TFT liquid-crystal display response speed that exists in the prior art fast, voltage low, the not high enough problem of electric charge conservation rate inadequately inadequately.
Embodiment
Following examples are used for explanation the present invention, but are not used for limiting the scope of the invention.
Opticity component of the present invention, S811, R811, S1011, R1011, S2011 and R2011 all derive from Beijing Bayi Space LCD Materials Technology Co., Ltd., and its structure is:
Figure BDA00003228308900221
R/S811
Figure BDA00003228308900231
R/S1011
Figure BDA00003228308900232
R/S2011
Ubiquitous method in liquid-crystal composition employing of the present invention this area--the thermal solution retorting process preparation.At first with each liquid crystalline cpd of balance weighing by weight percentage, wherein the weighing addition sequence does not have particular requirement, usually mix with liquid crystalline cpd fusing point order from high to low weighing successively, make each component fusion evenly 60～100 ℃ of following heated and stirred, again after filtration, the degassing, encapsulation at last namely gets target sample.In addition, also the disclosed method of available patent CN101502767A is carried out the preparation of even liquid crystal.
Except as otherwise noted, in the context, per-cent is weight percentage, and all temperature are degree centigrade to provide.Use following abbreviation among the embodiment:
△ n is optical anisotropy, and η is volume viscosity (mm 2/ s, 20 ℃), Δ ε be dielectric constant anisotropy (20 ℃, 1000Hz);
V 90Being threshold voltage, is the character voltage (V, 20 ℃) when relative 90% transmitance;
C.p be liquid-crystal composition clearing point (℃);
τ OnTime during for making alive during from 90% transmitance to 10% transmitance, τ OffTime when returning to 90% transmitance from 10% transmitance when cutting off voltage, τ is τ On+ τ Off(time of response) (ms);
Except as otherwise noted, all optical datas are all measured down at 20 ℃.
In the following embodiments, each structural unit abbreviation is as shown in table 1.
The abbreviation of table 1 structural unit
Figure BDA00003228308900233
Figure BDA00003228308900241
For example: nC-P-PF.X.F represents C nH 2n+1
Figure BDA00003228308900242
OCF 2-CF=CF 2
Embodiment 1
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 2:
The proportioning of the liquid-crystal composition of table 2 embodiment 1 and performance perameter
Figure BDA00003228308900243
Figure BDA00003228308900251
Embodiment 2
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 3:
The proportioning of the liquid-crystal composition of table 3 embodiment 2 and performance perameter
Figure BDA00003228308900252
Embodiment 3
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 4:
The proportioning of the liquid-crystal composition of table 4 embodiment 3 and performance perameter
Figure BDA00003228308900261
Embodiment 4
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 5:
The proportioning of the liquid-crystal composition of table 5 embodiment 4 and performance perameter
Figure BDA00003228308900262
Figure BDA00003228308900271
Embodiment 5
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 6:
The proportioning of the liquid-crystal composition of table 6 embodiment 5 and performance perameter
Figure BDA00003228308900272
Figure BDA00003228308900281
Embodiment 6
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 7:
The proportioning of the liquid-crystal composition of table 7 embodiment 6 and performance perameter
Embodiment 7
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 8:
The proportioning of the liquid-crystal composition of table 8 embodiment 7 and performance perameter
Figure BDA00003228308900291
Embodiment 8
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 9:
The proportioning of the liquid-crystal composition of table 9 embodiment 8 and performance perameter
Figure BDA00003228308900292
Figure BDA00003228308900301
Embodiment 9
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 10:
The proportioning of the liquid-crystal composition of table 10 embodiment 9 and performance perameter
Embodiment 10
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 11:
The proportioning of the liquid-crystal composition of table 11 embodiment 10 and performance perameter
Figure BDA00003228308900311
Embodiment 11
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 12:
The proportioning of the liquid-crystal composition of table 12 embodiment 11 and performance perameter
Figure BDA00003228308900312
Embodiment 12
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 13:
The proportioning of the liquid-crystal composition of table 13 embodiment 12 and performance perameter
Embodiment 13
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the performance perameter of concrete proportioning and gained liquid-crystal composition is as shown in table 14:
The proportioning of the liquid-crystal composition of table 14 embodiment 13 and performance perameter
Figure BDA00003228308900323
Figure BDA00003228308900331
Comparative Examples
Get the liquid crystalline cpd of following weight percentage and prepare liquid-crystal composition with method described in the present invention, the relativity of proportioning is as shown in Table 15 among concrete proportioning and the embodiment 1:
The composition proportioning of table 15 comparative example and embodiment 1
Figure BDA00003228308900341
According to proportioning described in the table 15, the performance perameter that makes prepared liquid-crystal composition among the performance perameter of liquid-crystal composition and the embodiment 1 with method described in the present invention forms contrast, and is as shown in table 16:
The performance perameter of table 16 comparative example and embodiment 1
Performance perameter Embodiment 1 The comparative example
V 90[V，20℃] 1.36 1.58
η[mm 2/s，20℃] 14 18
C.p[℃] 105 103
Δn[20℃，589nm] 0.102 0.102
τ[ms] 6.0 9.0
Δε[20℃] 7.5 6.2
By table 15 and table 16 as can be known, compare with embodiment 1, because not using the represented compound of logical formula I as one of component among the comparative example, under the substantially the same situation of other components, among the comparative example among prepared liquid-crystal composition and the embodiment 1 prepared liquid-crystal composition compare, the driving voltage height, the time of response is slow.Illustrate that the compound of logical formula I representative has the effect of good reduction threshold voltage and raising response speed in the mixed liquid crystal system.
Though, above used general explanation, embodiment and test, the present invention is described in detail, on basis of the present invention, can make some modifications or improvements it, and this will be apparent to those skilled in the art.Therefore, these modifications or improvements all belong to the scope of protection of present invention without departing from theon the basis of the spirit of the present invention.

Claims (10)

1. a liquid-crystal composition is characterized in that, contains following components in weight percentage content:
The compound of (1) 1～90% logical formula I representative;
The compound of (2) 1～60% logical formula II representatives;
The compound of (3) 0～70% logical formula III and/or (IV) representative;
The compound of one or more representatives in (4) 0～30% general formulas (V), (VI) and (VII);
Described liquid-crystal composition also comprises by weight the optically-active component that accounts for (1)～(4) component gross weight 0～0.5%;
Wherein, the compound of described logical formula I representative is following structure:
Figure FDA00003228308800011
（Ⅰ）
In the formula I, R is selected from C 1～C 12Alkyl, wherein one or more-CH 2-group can be substituted by-O-; Z is selected from-CF 2O-,-C 2H 4-or the C-C singly-bound; It is trans 1 that the ring texture substituent A is selected from, 4-cyclohexyl, 1,4-phenylene or 1,4-pyranyl; L 1～L 5Be independently selected from F or H atom; M, n, p are integer independent of each other, and 0≤m≤2, and n, p are 0 or 1;
The compound of described logical formula II representative is following structure:
（Ⅱ）
In the formula II, R aAnd R bBe independently selected from C 1～C 12Alkyl, wherein one or more-CH 2-group can be substituted by-O-;
The compound of described logical formula III and (IV) representative is respectively following structure:
Figure FDA00003228308800021
（Ⅲ）
Figure FDA00003228308800022
（Ⅳ）
In formula III and (IV), R cAnd R dBe independently selected from C 1～C 12Alkyl, wherein one or more-CH 2-group can be substituted by-O-; L 6Be selected from F or H atom; O, s, t represent 1 or 2 independently of one another; It is trans 1 that ring texture substituent B and C are independently selected from, 4-cyclohexyl or 1,4-phenylene;
The compound of described general formula (V), (VI) and (VII) representative is respectively following structure:
Figure FDA00003228308800023
（Ⅴ）
（Ⅵ）
Figure FDA00003228308800025
（Ⅶ）
In formula (V), (VI) and (VII), R e～R jBe independently selected from C 1～C 12Alkyl, wherein one or more-CH 2-group can be substituted by-O-, and one or more H atoms can be substituted by the F atom, or R e～R jBe independently selected from C 1～C 12Thiazolinyl; L 7Be selected from F or H atom.
2. liquid-crystal composition according to claim 1 is characterized in that, described liquid-crystal composition comprises following components in weight percentage content:
The compound of (1) 5～85% logical formula I representative;
The compound of (2) 14～55% logical formula II representatives;
The compound of (3) 10～65% logical formula III and/or (IV) representative;
The compound of one or more representatives in (4) 2～21% general formulas (V), (VI) and (VII);
Described liquid-crystal composition also comprises by weight the optically-active component that accounts for (1)～(4) component gross weight 0.07～0.3%.
3. liquid-crystal composition according to claim 1 and 2, it is characterized in that, the compound of described general formula (I) representative be selected from formula (I a), among (I b), (I c), (I d), (I e), (I f), (I g), (I h), (the I i) one or more:
（Ⅰa）
Figure FDA00003228308800032
（Ⅰb）
Figure FDA00003228308800033
（Ⅰc）
Figure FDA00003228308800041
（Ⅰd）
Figure FDA00003228308800042
（Ⅰe）
Figure FDA00003228308800043
（Ⅰf）
Figure FDA00003228308800044
（Ⅰg）
Figure FDA00003228308800045
（Ⅰh）
Figure FDA00003228308800051
（Ⅰi）
Formula (I a)～(I i) in, R 1～R 8And R ' is independently selected from C 1～C 8Alkyl, wherein one or more-CH 2-group can be substituted by-O-; Z represents-CF 2O-or C-C singly-bound; L 1～L 4Be independently selected from F or H atom.
4. liquid-crystal composition according to claim 1 and 2 is characterized in that, the structural formula of described logical formula II representative compound be formula (II a) or (II b):
Figure FDA00003228308800052
（Ⅱa）
Figure FDA00003228308800053
（Ⅱb）
Formula (II a) and (II b) in, R A 'Be selected from C 1～C 5Alkyl or C 2～C 5Thiazolinyl.
5. liquid-crystal composition according to claim 1 and 2 is characterized in that, the compound of described logical formula III representative be selected from formula (III a), among (III b), (the III c) and (III d) one or more; The compound of described logical formula IV representative be selected from formula (IV a) or (IV b):
Figure FDA00003228308800054
（Ⅲa）
Figure FDA00003228308800061
（Ⅲb）
Figure FDA00003228308800062
（Ⅲc）
Figure FDA00003228308800063
（Ⅲd）
Figure FDA00003228308800064
（Ⅳa）
Figure FDA00003228308800065
（Ⅳb）
Formula (III a)～(III d), (IV a) and (IV b) in, R C 'And R D 'Be independently selected from C 1～C 5Alkyl, wherein one or more-CH 2-group can be substituted by-O-.
6. liquid-crystal composition according to claim 1 and 2 is characterized in that, in the compound of described general formula (V) representative, and R eAnd R fBe independently selected from C 1～C 5Alkyl or C 2～C 5Thiazolinyl.
7. liquid-crystal composition according to claim 1 and 2 is characterized in that, in the compound of described logical formula VI representative, and R hBe selected from C 1～C 5Alkyl, C 1～C 5Alkoxyl group or C 1～C 5Fluoroalkyl, R gBe selected from C 2～C 5Thiazolinyl or C 2～C 5Alkyl.
8. liquid-crystal composition according to claim 1 and 2 is characterized in that, in the compound of described general formula (VII) representative, and R iAnd R jBe independently selected from C 1～C 5Alkyl.
9. the application of each described liquid-crystal composition of claim 1～8 in the preparation liquid crystal indicator.
10. the application of each described liquid-crystal composition of claim 1～8 in the indicating meter of preparation TN, IPS, FFS or ADS display format.
CN201310193810.9A 2013-05-22 2013-05-22 Liquid crystal composition and application thereof Expired - Fee Related CN103242861B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201310193810.9A CN103242861B (en) 2013-05-22 2013-05-22 Liquid crystal composition and application thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201310193810.9A CN103242861B (en) 2013-05-22 2013-05-22 Liquid crystal composition and application thereof

Publications (2)

Publication Number Publication Date
CN103242861A true CN103242861A (en) 2013-08-14
CN103242861B CN103242861B (en) 2014-08-20

Family

ID=48922743

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201310193810.9A Expired - Fee Related CN103242861B (en) 2013-05-22 2013-05-22 Liquid crystal composition and application thereof

Country Status (1)

Country Link
CN (1) CN103242861B (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103642503A (en) * 2013-12-03 2014-03-19 北京八亿时空液晶科技股份有限公司 Liquid crystal composition containing pyranyl/pentafluoroallyloxy structure compounds and application thereof
CN103756688A (en) * 2014-01-27 2014-04-30 北京八亿时空液晶科技股份有限公司 Pentafluoropropylene ether liquid crystal compound as well as preparation method and application thereof
CN103772335A (en) * 2014-01-27 2014-05-07 北京八亿时空液晶科技股份有限公司 Liquid crystal compound containing pentafluoropropene and pyranoid ring and liquid crystal composition of liquid crystal compound
CN103773390A (en) * 2013-12-27 2014-05-07 北京八亿时空液晶科技股份有限公司 Liquid-crystal composition containing pentafluoropropenyl ether type monomers and application thereof
CN104354646A (en) * 2014-11-07 2015-02-18 高辉（天津）科技有限公司 Large automobile liquid crystal anti-dazzling rearview mirror
CN104673326A (en) * 2015-02-04 2015-06-03 北京八亿时空液晶科技股份有限公司 Liquid crystal composition containing fluoroterphenyl compound and pentafluoropropenyl ester compound and application thereof
JP2015110531A (en) * 2013-12-06 2015-06-18 Dic株式会社 Polymerizable compound and optical anisotropic body
WO2015093193A1 (en) * 2013-12-16 2015-06-25 Dic株式会社 Alkenyl ether compound and liquid crystal composition using same
CN107955629A (en) * 2016-10-14 2018-04-24 石家庄诚志永华显示材料有限公司 A kind of positive dielectricity liquid-crystal composition
CN108531197A (en) * 2018-05-31 2018-09-14 烟台显华化工科技有限公司 A kind of liquid-crystal composition and its application
CN110452710A (en) * 2018-05-08 2019-11-15 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 (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003015547A (en) * 2001-04-16 2003-01-17 Seiko Epson Corp Optoelectronic device, manufacturing method therefor and electronic equipment
US20050161637A1 (en) * 2002-12-24 2005-07-28 Hirokatsu Shinano Perfluoroallyloxy compound and liquid crystal composition containing the compound
CN101061202A (en) * 2004-12-10 2007-10-24 株式会社艾迪科 Liquid crystal composition
JP2007277127A (en) * 2006-04-04 2007-10-25 Adeka Corp Halogen-containing compound, liquid crystal composition and electrooptical display element
CN101747904A (en) * 2008-12-16 2010-06-23 大立高分子工业股份有限公司 Liquid crystal composition
CN102643653A (en) * 2012-03-21 2012-08-22 北京八亿时空液晶科技股份有限公司 Liquid crystal composition
CN103013535A (en) * 2012-12-28 2013-04-03 北京八亿时空液晶科技股份有限公司 Liquid crystal composition and application thereof
CN103146392A (en) * 2013-02-27 2013-06-12 北京八亿时空液晶科技股份有限公司 Liquid crystal composition for liquid crystal display
CN103194243A (en) * 2013-02-27 2013-07-10 北京八亿时空液晶科技股份有限公司 Liquid crystal composition for TFT display

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003015547A (en) * 2001-04-16 2003-01-17 Seiko Epson Corp Optoelectronic device, manufacturing method therefor and electronic equipment
US20050161637A1 (en) * 2002-12-24 2005-07-28 Hirokatsu Shinano Perfluoroallyloxy compound and liquid crystal composition containing the compound
CN101061202A (en) * 2004-12-10 2007-10-24 株式会社艾迪科 Liquid crystal composition
JP2007277127A (en) * 2006-04-04 2007-10-25 Adeka Corp Halogen-containing compound, liquid crystal composition and electrooptical display element
CN101747904A (en) * 2008-12-16 2010-06-23 大立高分子工业股份有限公司 Liquid crystal composition
CN102643653A (en) * 2012-03-21 2012-08-22 北京八亿时空液晶科技股份有限公司 Liquid crystal composition
CN103013535A (en) * 2012-12-28 2013-04-03 北京八亿时空液晶科技股份有限公司 Liquid crystal composition and application thereof
CN103146392A (en) * 2013-02-27 2013-06-12 北京八亿时空液晶科技股份有限公司 Liquid crystal composition for liquid crystal display
CN103194243A (en) * 2013-02-27 2013-07-10 北京八亿时空液晶科技股份有限公司 Liquid crystal composition for TFT display

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103642503A (en) * 2013-12-03 2014-03-19 北京八亿时空液晶科技股份有限公司 Liquid crystal composition containing pyranyl/pentafluoroallyloxy structure compounds and application thereof
CN103642503B (en) * 2013-12-03 2015-09-23 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 containing pyranyl and five fluorine allyloxy structural compounds
JP2015110531A (en) * 2013-12-06 2015-06-18 Dic株式会社 Polymerizable compound and optical anisotropic body
JP5862996B2 (en) * 2013-12-16 2016-02-16 Dic株式会社 Alkenyl ether compound and liquid crystal composition using the same
WO2015093193A1 (en) * 2013-12-16 2015-06-25 Dic株式会社 Alkenyl ether compound and liquid crystal composition using same
US9822301B2 (en) 2013-12-16 2017-11-21 Dic Corporation Alkenyl ether compound and a liquid crystal composition using the same
JPWO2015093193A1 (en) * 2013-12-16 2017-03-16 Dic株式会社 Alkenyl ether compound and liquid crystal composition using the same
CN105849075A (en) * 2013-12-16 2016-08-10 Dic株式会社 Alkenyl ether compound and liquid crystal composition using same
CN103773390A (en) * 2013-12-27 2014-05-07 北京八亿时空液晶科技股份有限公司 Liquid-crystal composition containing pentafluoropropenyl ether type monomers and application thereof
CN103773390B (en) * 2013-12-27 2015-07-15 北京八亿时空液晶科技股份有限公司 Liquid-crystal composition containing pentafluoropropenyl ether type monomers and application thereof
CN103772335A (en) * 2014-01-27 2014-05-07 北京八亿时空液晶科技股份有限公司 Liquid crystal compound containing pentafluoropropene and pyranoid ring and liquid crystal composition of liquid crystal compound
CN103772335B (en) * 2014-01-27 2016-02-10 北京八亿时空液晶科技股份有限公司 A kind of liquid crystalline cpd and liquid-crystal composition thereof containing five fluorine propylene and pyranoid ring
CN103756688A (en) * 2014-01-27 2014-04-30 北京八亿时空液晶科技股份有限公司 Pentafluoropropylene ether liquid crystal compound as well as preparation method and application thereof
CN103756688B (en) * 2014-01-27 2015-05-27 北京八亿时空液晶科技股份有限公司 Pentafluoropropylene ether liquid crystal compound as well as preparation method and application thereof
CN104354646A (en) * 2014-11-07 2015-02-18 高辉（天津）科技有限公司 Large automobile liquid crystal anti-dazzling rearview mirror
CN104673326A (en) * 2015-02-04 2015-06-03 北京八亿时空液晶科技股份有限公司 Liquid crystal composition containing fluoroterphenyl compound and pentafluoropropenyl ester compound and application thereof
CN107955629A (en) * 2016-10-14 2018-04-24 石家庄诚志永华显示材料有限公司 A kind of positive dielectricity liquid-crystal composition
CN110452710A (en) * 2018-05-08 2019-11-15 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
CN108531197A (en) * 2018-05-31 2018-09-14 烟台显华化工科技有限公司 A kind of liquid-crystal composition and its application

Also Published As

Publication number Publication date
CN103242861B (en) 2014-08-20

Similar Documents

Publication Publication Date Title
CN103242861B (en) Liquid crystal composition and application thereof
CN103254906B (en) Liquid crystal composition containing difluoro methoxyl ether compounds
CN102585840B (en) Liquid crystal composition containing cyclopentyl compounds
JP5460004B2 (en) Liquid crystal media
CN103289708B (en) Positive dielectric anisotropic liquid crystal composition
CN103275735B (en) Dielectric positive liquid crystal composition
CN108865175B (en) Liquid crystal composition containing dibenzofuran and application thereof
JP6972103B2 (en) Liquid crystal medium
CN103146392B (en) Liquid crystal composition for liquid crystal display
JP2016113440A (en) Liquid crystal compound and liquid crystal mixture containing cyclopropyl
KR20140002800A (en) Liquid-crystal medium
CN103289707B (en) Quick-response liquid crystal composition
TW201026823A (en) Liquid-crystalline medium
KR20100017812A (en) Liquid crystalline medium
JP6973996B2 (en) Liquid crystal medium
CN103642502A (en) Liquid crystal composition containing compound with dioxygen heterocyclic structure and application of liquid crystal composition
CN103773382B (en) Liquid-crystalline medium
CN103525431B (en) A kind of liquid-crystal composition of quick response
CN109880635B (en) Liquid crystal compound containing dibenzofuran-oxygen-containing heterocyclic ring, composition and application
CN103013535B (en) Liquid crystal composition and application thereof
JP2014025025A (en) Liquid crystal composition including a liquid crystal compound and a triplet quencher
CN103254908B (en) Positive dielectric liquid crystal mixture containing (3,3,0) bicycle-octane monomer
CN103265959A (en) TFT (Thin Film Transistor) liquid crystal composite
CN103351879B (en) Positive dielectric anisotropic liquid crystal composition
JP6006038B2 (en) Liquid crystal composition

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
TR01 Transfer of patent right
TR01 Transfer of patent right

Effective date of registration: 20180821

Address after: Block B2-36-01, East District, New Petrochemical Material Science and Technology Industrial Base, Fengjie District, Yanshan District, Fangshan District, Beijing

Patentee after: BEIJING BAYI SPACE LCD TECHNOLOGY Co.,Ltd.

Address before: 102205 Yang Fang village, Changping District, Beijing

Patentee before: BEIJING JINXUNYANGGUANG ELECTRONIC MATERIALS TECHNOLOGY Co.,Ltd.

CF01 Termination of patent right due to non-payment of annual fee
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20140820

Termination date: 20210522