CN102585840B - Liquid crystal composition containing cyclopentyl compounds - Google Patents
Liquid crystal composition containing cyclopentyl compounds Download PDFInfo
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- CN102585840B CN102585840B CN201110439042.1A CN201110439042A CN102585840B CN 102585840 B CN102585840 B CN 102585840B CN 201110439042 A CN201110439042 A CN 201110439042A CN 102585840 B CN102585840 B CN 102585840B
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Abstract
The invention provides a liquid crystal composition containing cyclopentyl compounds. The liquid crystal composition containing the cyclopentyl compounds comprises a compound as a first component represented by a general formula I, a compound as a second component represented by a general formula II, compounds as a third component represented by general formulas III and IV, any one or more of compounds as a fourth component represented by general formulas V, VI and VII, and an optically active component. The liquid crystal composition is used for manufacturing a fast-response TN-TFT (Twisted Nematic-Thin film Transistor) LCD (Liquid Crystal Display).
Description
Technical field
The present invention relates to a kind of liquid-crystal composition, specifically, relate to a kind of liquid-crystal composition that contains cyclopentyl class liquid crystalline cpd.
Background technology
As far back as 19th-century second half, variant field comprises that many scholars in the fields such as physics, chemistry, biology have observed some compounds and varied with temperature the unusual appearance showing.Assert afterwards that the formal time of finding liquid crystal was 1888.This year Austrian botanist Friedrich Reinitzer, in the time studying cholesterol to plant action, found the first liquid crystal material M-nitro benzoic acid cholesterol (cholesteryl benzoate).Between more than 100 year of discovery liquid crystal phenomenon, people are not interrupted the research to it all the time.
In early days, the 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.Echoing mutually with liquid crystal theoretical investigation, is the golden period of development of liquid crystal science and technology in phase later 1960s.The nineteen sixty-eight R.Williams of RCA Corp. of the U.S. finds that nematic liquid crystal forms striped farmland under electric field action, and has light scattering phenomenon.G.H.Heilmeir is with develop into dynamic scattering display format by 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 are made display device (TN-LCD), for wide prospect has been opened up in the application of liquid crystal.Since the seventies, due to the development of large-scale integrated circuit and liquid crystal material, the people such as the application of liquid crystal aspect demonstration obtained breakthrough development, 1983～1985 years T.Scheffer successively propose super-twist nematic (Super Twisred Nematic:STN) pattern and P.Brody is adopted again in active matrix (Active matrix:AM) mode of proposition in 1972.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.
TFT-LCD technology and initial product are in Europe and produced in USA, but its extensive commercial application is completed by Japan, within 1993, Korea S starts to get involved TFT-LCD industry, and obtain very soon stronger competitive power, the Taiwan of China in 1998 starts to have added the sector, on industry size, almost occupied half of the country by 2005, but from integral layout, the critical role of China in this industry constantly manifests at present.
At present, although TFT-LCD product technology is day by day ripe, can successfully solve the technical barriers such as visual angle, resolving power, fullness of shade and brightness, its display performance has approached or has exceeded 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 subject to the restriction of liquid crystal material itself, and it is fast not that TFT-LCD still exists response speed, voltage is low not, the high not many defects of electric charge conservation rate.Therefore from liquid crystal material, the focus that developing the TFT liquid crystal compound of quick response, high electric charge conservation rate becomes in industry is also difficult point.
Making a general survey of the liquid crystal material evolution showing for TFT can find, the exploitation of liquid crystalline cpd is all towards the future development of high electric charge conservation rate, high dielectric anisotropy, excellent low temperature mutual solubility, substitute onto last polyfluoro from initial single fluorine and replace, so afterwards-CF
2the liquid crystalline cpds such as the super polyfluoro replacement of O-bridged bond, ripe liquid crystalline cpd is with stable hexa-atomic aromatic nucleus (as phenyl ring) and hexa-atomic alkyl ring (as hexamethylene ring) composition, its end bit substituent is mostly alkyl or alkenyl, use for cyclopentyl ring is actually rare, in European patent EP 0821049B1, disclose the compound that a class contains cyclopentyl, shown for ferroelectric liquid crystals; Show very rare for TFT.
Cyclopentyl lopps compound has good chemistry and thermostability, and it is qualitative that electric field and magnetic field are had to high temperature, has in addition wider mesomorphous phase, and also rationality very of low temperature mutual solubility, is suitable for mixed liquid crystal compound.
Summary of the invention
The object of this invention is to provide a kind of liquid-crystal composition that contains cyclopentyl compounds of the TN-TFT of can be used for liquid-crystal display.
In order to realize the object of the invention, the invention provides a kind of liquid-crystal composition that contains cyclopentyl compounds, the component that it contains following weight percent:
The compound that (1) first component comprises general formula I representative, its content is 1-40%;
(2) compound that second component comprises general formula II representative, its content is 1-70%;
The compound that (3) the 3rd components comprise general formula III and IV representative, its content is 2-70%;
The compound that (4) the 3rd components comprise general formula V, VI and VII representative any one or multiple, its content is 0-50%;
(5) account for the opticity component of above-mentioned each component total content 0.05-0.5%.
The represented liquid crystalline cpd of general formula I that liquid-crystal composition the first component of the present invention comprises is following structure:
Wherein, Z represents the alkyl of 1-12 carbon atom, wherein part CH
2group can be substituted by-O-, or represents the thiazolinyl of 2-12 carbon atom, can also represent-CF of Z in addition
2o-,-C
2h
4-,-COO-or singly-bound; Trans Isosorbide-5-Nitrae-the cyclohexyl of A, B expression independent of each other or Isosorbide-5-Nitrae-phenylene; 0≤m+n≤2; L
1and L
3expression-H independent of each other or-F; L
2expression-H ,-F ,-OCF
3or-OCF
2h;
Preferably, the compound that the first component formula of I is lower array structure:
Wherein, Z represents the alkyl of 1-8 carbon atom, wherein part CH
2group can be substituted by-O-, or represents the thiazolinyl of 2-8 carbon atom, and Z can also represent singly-bound in addition; Trans Isosorbide-5-Nitrae-the cyclohexyl of A, B expression independent of each other or Isosorbide-5-Nitrae-phenylene; L
1and L
3expression-H independent of each other or-F; L
2expression-H ,-F ,-OCF
3or-OCF
2h;
The alkyl that in liquid crystalline cpd shown in general formula I, indication Z represents and thiazolinyl ideal situation are short alkyl or alkenyl chain group, are less than five carbon atom groups; L
1, L
2, L
3expression-H independent of each other or-F; In liquid-crystal composition involved in the present invention, the first component concentration is 1-40%, is further 5-30%.
Most preferably, the liquid crystalline cpd shown in liquid-crystal composition general formula I of the present invention is specially following structure:
Liquid-crystal composition the first component of the present invention is chief component, this compounds has very strong polarity, large electrical anisotropy, and there is higher clearing point, in mixed liquid crystal system, there is the effect of good reduction threshold voltage, meanwhile, in the time dissolving each other with other compounds, also show the represented structural viscosity of excellent performance, particularly general formula I A little, after adding, can improve the response speed of mixed liquid crystal.
In liquid-crystal composition second component of the present invention, comprise the represented liquid crystalline cpd of general formula II, structure is as follows:
Wherein, R
1, R
2the alkyl of 1-12 carbon atom of expression independent of each other, wherein part CH
2group can be substituted by-O-; Preferably, R
1, R
2at least one represents the thiazolinyl of 2-5 carbon atom; Another represents the alkyl of 1-5 carbon atom.
More preferably, it is specially following compound the represented liquid crystalline cpd of second component comprises general formula II:
Wherein, R
1' represent the alkyl of 1-5 carbon atom; In liquid-crystal composition involved in the present invention, second component content is 1-70%, and better content is 5-55%.
The represented compound of general formula I I is the allotment requisite compounds of liquid crystal compound of response fast, each display format is with generally using this compounds in liquid crystal compound now, addition is very large, this compounds does not almost have polarity, the structure of bis cyclohexane makes compound have extremely low viscosity and little optical anisotropy, reduce to play the effect can not be substituted for the viscosity of whole mixed system, thereupon remarkable for the raising effect of the response speed of mixed crystal.
The 3rd group of liquid-crystal composition of the present invention comprises the liquid crystalline cpd that general formula III and IV represent, structure is as follows:
Wherein, R
3, R
4the alkyl of 1-12 carbon atom of expression independent of each other, wherein part CH
2group can be substituted by-O-; L
4expression-H or-F; O, p independently represent 1 or 2 separately; Trans Isosorbide-5-Nitrae-the cyclohexyl of C, D expression independent of each other or Isosorbide-5-Nitrae-phenylene;
Preferably, represented its structure of liquid crystalline cpd of the general formula III that the 3rd component comprises and IV is:
Wherein, R
3', R
4' alkyl that represents 1-5 carbon atom independent of each other, wherein part CH
2group can be substituted by-O-.
In liquid-crystal composition involved in the present invention, the 3rd component concentration is 2-70%, and preferred content is 10-55%.Wherein the content of general formula III is 1-30%, is preferably 5-25%, and the content of general formula I V is 1-40%, and preferred content is respectively 5-30%.
The liquid crystalline cpd that in liquid-crystal composition of the present invention, the 3rd component comprises plays vital effect for the threshold voltage that reduces whole system, meanwhile the represented liquid crystalline cpd of general formula III and IV has higher specific inductivity, moderate optical anisotropy, higher nematic temperature range, excellent combination property, in mixed liquid crystal, add this type of component can effectively reduce threshold voltage, the properties of stabilising system.
Liquid-crystal composition of the present invention the 4th component comprises that its structure of the represented liquid crystalline cpd of general formula V, VI and VII is following listed:
Wherein, R
5～R
9the alkyl of 1-12 carbon atom of expression independent of each other, wherein part CH
2group can be substituted by-O-, or the thiazolinyl of 2-12 carbon atom of expression independent of each other; L
5, L
6expression-F independent of each other ,-H ,-OCF
2h or-OCF
3.
Preferably, in the 4th component, comprise the represented liquid crystalline cpd of general formula V and be specially following structure:
Wherein, R
5' represent the alkyl of 1-5 carbon atom, wherein part CH
2group can be substituted by-O-, or represents the thiazolinyl of 2-5 carbon atom.
Preferably, R in the liquid crystalline cpd shown in general formula VI
6, R
7the expression alkyl of 1-5 carbon atom independent of each other or the thiazolinyl of 2-5 carbon atom.
R in the compound that general formula VII represents
9represent alkyl or the alkoxyl group of 1-5 carbon atom, R
8represent the thiazolinyl of 2-5 carbon atom.
In liquid-crystal composition involved in the present invention, the 4th component concentration is 0-30%, and preferred content is 5-40%.
The low-temperature performance effect that liquid crystal compound shown in the 4th component general formula V improves mixed system for liquid crystal is remarkable, other performance is played the effect of auxiliary adjustment simultaneously, special most important for the fine setting of parameter; The represented liquid crystalline cpd of general formula VI and VII has higher clearing point and larger optical anisotropy, can be used for clearing point and the Δ n numerical value of the system of adjusting.
Opticity component of the present invention in addition, S811, R811, S1011, R1011, S2011 and R2011 all derive from Beijing Bayi Space Liquid Crystal Materials Sci-tech Co., Ltd., and its structure is:
If show that for TN-TFT mode liquid crystal adding the effect of opticity component is to make liquid crystalline cpd 90 ° of distortions in liquid crystal cell for liquid crystal compound of the present invention, unlikelyly owe to turn round and affect display effect, its content is 0.05-0.5%, is preferably 0.07-0.3%.
Liquid-crystal composition of the present invention can adopt ordinary method that two or more liquid crystalline cpds are mixed and produced, as the method preparation that at high temperature mixes different components and dissolve each other, wherein, liquid-crystal composition is dissolved in to solvent the mixing for this compound, then under reduced pressure distills out this solvent; Or liquid-crystal composition of the present invention can be prepared in a conventional manner, as the component that wherein content is less is dissolved in the main ingredient that content is larger at higher temperature, or component under each is dissolved in organic solvent, as acetone, chloroform or methyl alcohol etc., after then solution being mixed, after removal solvent, obtain.
The liquid-crystal composition excellent performance obtaining by the present invention, has lower voltage, lower viscosity, high resistivity and voltage retention, and liquid-crystal composition of the present invention can be used for liquid crystal indicator.Described liquid crystal indicator is TN type TFT liquid-crystal display.Be applicable in the TFT-LCD of various quick responses.
Embodiment
Following examples are used for illustrating the present invention, but are not used for limiting the scope of the invention.
In the following embodiments, the structure of the each component of liquid crystalline cpd represents by following acronym:
Except as otherwise noted, in context, per-cent is weight percentage, and all temperature are degree Celsius to provide.Use following abbreviation: c.p=clearing point, Δ n is optical anisotropy, n
0for specific refractory power (589nm, 20 DEG C).η (mm
2/ s, 20 DEG C) be volume viscosity.Δ ε is dielectric constant anisotropy (20 DEG C, 1000Hz).The character voltage of V10 threshold voltage=in the time of relative 10% contrast gradient (V, 20 DEG C), the character voltage of V90 saturation voltage=in the time of relative 90% contrast gradient (V, 20 DEG C).Ton is until the time while connecting while reaching maximum countrast 90%, and toff is until the time while cutting off while reaching maximum countrast 10%, τ be ton+toff (time of response) (ms).Except as otherwise noted, all optical datas are all measured at 20 DEG C.
Compound and opticity component used in the present invention are all commercially available, as purchased from from Beijing Bayi Space Liquid Crystal Materials Sci-tech Co., Ltd..
Embodiment 1
The liquid crystalline cpd preparation liquid-crystal composition of getting following weight percent, the character of concrete proportioning and the liquid-crystal composition of gained is in table 1.
Preparation method is as follows:
Evenly the preparation of liquid crystal adopts the heat of solution method generally using in the industry, first weigh by weight percentage liquid crystalline cpd with balance, wherein weigh addition sequence without particular requirement, conventionally weigh successively mixing with liquid crystalline cpd fusing point order from high to low, at 60-100 DEG C, heated and stirred melts evenly each component, again after filtration, revolve steaming, finally encapsulate and obtain target sample.In addition, also can carry out the preparation of even liquid crystal by the related method of patent CN101502767A.
The proportioning of the liquid-crystal composition of table 1 embodiment 1 and performance perameter
Embodiment 2
The liquid crystalline cpd preparation liquid-crystal composition of getting following weight percent, the character of concrete proportioning and the liquid-crystal composition of gained is in table 2.
Preparation method is as follows:
Evenly the preparation of liquid crystal adopts the heat of solution method generally using in the industry, first weigh by weight percentage liquid crystalline cpd with balance, wherein weigh addition sequence without particular requirement, conventionally weigh successively mixing with liquid crystalline cpd fusing point order from high to low, at 60-100 DEG C, heated and stirred melts evenly each component, again after filtration, revolve steaming, finally encapsulate and obtain target sample.In addition, also can carry out the preparation of even liquid crystal by the related method of patent CN101502767A.
The proportioning of the liquid-crystal composition of table 2 embodiment 2 and performance perameter
Embodiment 3
The liquid crystalline cpd preparation liquid-crystal composition of getting following weight percent, the character of concrete proportioning and the liquid-crystal composition of gained is in table 3.
Preparation method is as follows:
Evenly the preparation of liquid crystal adopts the heat of solution method generally using in the industry, first weigh by weight percentage liquid crystalline cpd with balance, wherein weigh addition sequence without particular requirement, conventionally weigh successively mixing with liquid crystalline cpd fusing point order from high to low, at 60-100 DEG C, heated and stirred melts evenly each component, again after filtration, revolve steaming, finally encapsulate and obtain target sample.In addition, also can carry out the preparation of even liquid crystal by the related method of patent CN101502767A.
The proportioning of the liquid-crystal composition of table 3 embodiment 3 and performance perameter
Embodiment 4
The liquid crystalline cpd preparation liquid-crystal composition of getting following weight percent, the character of concrete proportioning and the liquid-crystal composition of gained is in table 4.
Preparation method is as follows:
Evenly the preparation of liquid crystal adopts the heat of solution method generally using in the industry, first weigh by weight percentage liquid crystalline cpd with balance, wherein weigh addition sequence without particular requirement, conventionally weigh successively mixing with liquid crystalline cpd fusing point order from high to low, at 60-100 DEG C, heated and stirred melts evenly each component, again after filtration, revolve steaming, finally encapsulate and obtain target sample.In addition, also can carry out the preparation of even liquid crystal by the related method of patent CN101502767A.
The proportioning of the liquid-crystal composition of table 4 embodiment 4 and performance perameter
Embodiment 5
The liquid crystalline cpd preparation liquid-crystal composition of getting following weight percent, the character of concrete proportioning and the liquid-crystal composition of gained is in table 5.
Preparation method is as follows:
Evenly the preparation of liquid crystal adopts the heat of solution method generally using in the industry, first weigh by weight percentage liquid crystalline cpd with balance, wherein weigh addition sequence without particular requirement, conventionally weigh successively mixing with liquid crystalline cpd fusing point order from high to low, at 60-100 DEG C, heated and stirred melts evenly each component, again after filtration, revolve steaming, finally encapsulate and obtain target sample.In addition, also can carry out the preparation of even liquid crystal by the related method of patent CN101502767A.
The proportioning of the liquid-crystal composition of table 5 embodiment 5 and performance perameter
Embodiment 6
Get the liquid crystalline cpd preparation liquid-crystal composition of following weight percent, the character of concrete proportioning and the liquid-crystal composition of gained is in table 6:
Preparation method is as follows:
Evenly the preparation of liquid crystal adopts the heat of solution method generally using in the industry, first weigh by weight percentage liquid crystalline cpd with balance, wherein weigh addition sequence without particular requirement, conventionally weigh successively mixing with liquid crystalline cpd fusing point order from high to low, at 60-100 DEG C, heated and stirred melts evenly each component, again after filtration, revolve steaming, finally encapsulate and obtain target sample.In addition, also can carry out the preparation of even liquid crystal by the related method of patent CN101502767A.
The proportioning of the liquid-crystal composition of table 6 embodiment 6 and performance perameter
Embodiment 7
The liquid crystalline cpd preparation liquid-crystal composition of getting following weight percent, the character of concrete proportioning and the liquid-crystal composition of gained is in table 7.
Preparation method is as follows:
Evenly the preparation of liquid crystal adopts the heat of solution method generally using in the industry, first weigh by weight percentage liquid crystalline cpd with balance, wherein weigh addition sequence without particular requirement, conventionally weigh successively mixing with liquid crystalline cpd fusing point order from high to low, at 60-100 DEG C, heated and stirred melts evenly each component, again after filtration, revolve steaming, finally encapsulate and obtain target sample.In addition, also can carry out the preparation of even liquid crystal by the related method of patent CN101502767A.
The proportioning of the liquid-crystal composition of table 7 embodiment 7 and performance perameter
Although above the present invention is described in detail with a general description of the specific embodiments, on basis of the present invention, can make some modifications or improvements it, this will be apparent to those skilled in the art.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, all belong to the scope of protection of present invention.
Claims (2)
1. a liquid-crystal composition that contains cyclopentyl compounds, is characterized in that, is made up of the each component that comprises following weight percent:
Account for the S2011 of above-mentioned each component total content 0.3%.
2. liquid-crystal composition claimed in claim 1 is in the application of preparing in liquid crystal indicator.
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| CN103074073B (en) * | 2012-12-20 | 2015-03-11 | 石家庄诚志永华显示材料有限公司 | Negative dielectric anisotropic liquid crystal mixture |
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| CN103289709B (en) * | 2013-06-04 | 2015-01-07 | 石家庄诚志永华显示材料有限公司 | Quick-response nematic phase type liquid crystal composite |
| CN103289708B (en) * | 2013-06-09 | 2015-04-08 | 石家庄诚志永华显示材料有限公司 | Positive dielectric anisotropic liquid crystal composition |
| CN103265959B (en) * | 2013-06-09 | 2015-06-03 | 石家庄诚志永华显示材料有限公司 | TFT (Thin Film Transistor) liquid crystal composite |
| CN103289707B (en) * | 2013-06-09 | 2015-07-01 | 石家庄诚志永华显示材料有限公司 | Quick-response liquid crystal composition |
| CN103351878B (en) * | 2013-07-09 | 2015-05-20 | 石家庄诚志永华显示材料有限公司 | Liquid crystal composition containing cyclopentyl and difluoromethoxy ether compound |
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| CN104513665A (en) * | 2014-12-31 | 2015-04-15 | 石家庄诚志永华显示材料有限公司 | Liquid crystal medium containing triphenyl series compounds and application thereof |
| CN104628541A (en) * | 2015-02-09 | 2015-05-20 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound and liquid crystal medium containing same |
| CN104591982A (en) * | 2015-02-09 | 2015-05-06 | 石家庄诚志永华显示材料有限公司 | Liquid crystal compound and liquid crystal medium comprising compound |
| JP6866583B2 (en) * | 2016-07-05 | 2021-04-28 | Dic株式会社 | Liquid crystal compound |
| CN110229678B (en) * | 2018-03-06 | 2020-10-27 | 北京八亿时空液晶科技股份有限公司 | Self-alignment additive and preparation method and application thereof |
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