CN101681073B - Method for producing liquid crystal composition - Google Patents
Method for producing liquid crystal composition Download PDFInfo
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- CN101681073B CN101681073B CN2008800194368A CN200880019436A CN101681073B CN 101681073 B CN101681073 B CN 101681073B CN 2008800194368 A CN2008800194368 A CN 2008800194368A CN 200880019436 A CN200880019436 A CN 200880019436A CN 101681073 B CN101681073 B CN 101681073B
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 133
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 54
- 239000000203 mixture Substances 0.000 title abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 238000013459 approach Methods 0.000 claims description 23
- 230000006837 decompression Effects 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000012298 atmosphere Substances 0.000 claims description 5
- 239000011261 inert gas Substances 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 4
- 238000000034 method Methods 0.000 abstract description 13
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 13
- 235000002597 Solanum melongena Nutrition 0.000 description 12
- 244000061458 Solanum melongena Species 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 10
- 230000014759 maintenance of location Effects 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- -1 fluoro-1,4-phenylene Chemical group 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 101000585157 Homo sapiens CST complex subunit STN1 Proteins 0.000 description 6
- 239000004988 Nematic liquid crystal Substances 0.000 description 6
- 102100021683 Stonin-1 Human genes 0.000 description 6
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical group OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012491 analyte Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 230000033228 biological regulation Effects 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000002769 thiazolinyl group Chemical group 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 2
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 2
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- AYDQIZKZTQHYIY-UHFFFAOYSA-N OC(=O)C1(C)CC(C(O)=O)=CC=C1 Chemical compound OC(=O)C1(C)CC(C(O)=O)=CC=C1 AYDQIZKZTQHYIY-UHFFFAOYSA-N 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 description 2
- 238000009434 installation Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/02—Liquid crystal materials characterised by optical, electrical or physical properties of the components, in general
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/14—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain
- C09K19/18—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a carbon chain the chain containing carbon-to-carbon triple bonds, e.g. tolans
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
- C09K19/20—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers
- C09K19/2007—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings linked by a chain containing carbon and oxygen atoms as chain links, e.g. esters or ethers the chain containing -COO- or -OCO- groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3059—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon triple bonds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
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- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Disclosed is a method for producing a liquid crystal composition which is useful as a constituting member of a liquid crystal display device. This method for producing a liquid crystal composition is characterized in that two or more kinds of liquid crystal compounds, at least one of which has a melting point higher than 30 DEG C, are irradiated with a microwave. This method for producing a liquid crystal composition enables to efficiently produce a liquid crystal composition wherein two or more kinds of liquid crystal compounds are mixed in a short time. A liquid crystal composition produced by this method has high reliability from the viewpoint of specific resistance.
Description
Technical field
The present invention relates to manufacturing approach as the useful liquid-crystal compsn of the component parts of liquid crystal display cells.
Background technology
Liquid crystal display cells, being used for clock and watch, desk top computer is that the meter device, automobile of representative is with display panel, word processor, electronic notebook, printer, computer, televisor etc.As the liquid crystal display mode, can enumerate TN (twisted nematic) type, STN (STN Super TN) type, DS (dynamic light scattering) type, GH (host and guest) type of its representative or FLC (ferroelectric liquid crystals) that can high-speed responsive etc.And, as type of drive, also from before static drive become general multichannel and drive; Further, simple matrix mode, nearest active-matrix mode are just in practicability.
The liquid-crystal compsn that is used for these occasions; Normally two or more compound is processed; Make the characteristic (abruptness of response time, threshold voltage, V-T curve etc.) of rerum natura (nematic temperature range, refractive index anisotropy (Δ n), dielectric constant anisotropy (Δ ε), viscosity, elastic constant etc.) and the electric optics of liquid-crystal compsn meet various values for the display mode of adaptation to end liquid crystal cell or type of drive and confirm mixing ratio, but in most cases all require reliability high heat, light, moisture etc.In addition, particularly in the occasion of active matrix drive mode, except above-mentioned requirements, importantly voltage retention (VHR) wants enough high.For the reliability that improves liquid-crystal compsn, than resistance and voltage retention (VHR),, need to realize high reliability and voltage retention (VHR) for the various liquid-crystal compoundss that constitute composition.But, even dependability, than resistance and the high liquid-crystal compounds of voltage retention (VHR) when making as their liquid-crystal compsn of potpourri, also can make quality badness sometimes.
As the manufacturing approach of liquid-crystal compsn, the method for proposition has: be mixed in the method (with reference to patent documentation 1) of removing organic solvent afterwards in the organic solvent through the heating for dissolving method of mixing with the liquid-crystal compounds dissolving.But, adopt the method for these propositions how quality badness can take place.For example, utilize the dissolving of heating to mix, oxygen makes the liquid-crystal compounds oxygenolysis during heating, and the ratio resistance of liquid-crystal compsn and voltage retention (VHR) be decline significantly.And make that sometimes liquid crystal upper limit transition temperature reduces, the rerum natura or the electric changes in optical properties of liquid-crystal compsn.In addition, be dissolved in the method for organic solvent, sometimes because the impurity of organic solvent and alloy make the ratio resistance of liquid-crystal compsn and voltage retention (VHR) significantly reduce.In addition, residual to some extent if organic solvent can not be removed fully, can become ratio resistance that reduces liquid-crystal compsn or the reason that significantly reduces voltage retention equally.On the other hand, also propose under decompression state and the lower temperature to disclose manufacturing (with reference to patent documentation 2) about liquid-crystal compsn with low-resistance value through the manufacturing approach of heating.But, though the method that this citing document is put down in writing can be made, need heating under lower temperature, heat caused baneful influence and can not get rid of fully, the support equipment of heating also is necessary.
In addition, the method for this citing document record has such problem: the large-scale device of following decompression is necessary.In other words, decompression needs the container of anti-decompression in order to dissolve liquid-crystal compounds simultaneously, and manufacturing installation must be the extensiveization manufacturing installation of anti-decompression.In addition, it is common that general vacuum pump is adopted in decompression, the coagulating air valve, be used to cool off with fixed attention that the cooling device of air valve also is necessary as supporting device of the adverse current of the mist of oil that is used for preventing that vacuum pump from using.Like this, liquid-crystal compsn is made down in decompression, for the demand of the liquid-crystal compsn of adaptation hugeization of equipment and increase, invests and excessively also has no way out.
As stated, the simple more equipment of expectation development and use, effectively make the method for high-quality liquid-crystal compsn.
Patent documentation 1: japanese kokai publication hei 5-105876 communique (5 pages of right hurdles)
Patent documentation 2: TOHKEMY 2002-194356 communique (4 pages of embodiment)
Summary of the invention
Technical matters to be solved by this invention
Technical matters to be solved by this invention is, the manufacturing approach that provides two or more liquid-crystal compoundss to mix the liquid-crystal compsn that constitutes, and the reliability of the liquid-crystal compsn of manufacturing is high, and can make efficiently.
The means of technical solution problem
About the solution of above-mentioned technical matters, the present inventor has accomplished the present invention through research with keen determination.The present invention provides a kind of manufacturing approach of liquid-crystal compsn, it is characterized in that, to the two or more liquid-crystal compounds irradiating microwaves of at least a fusing point greater than 30 ℃.
The effect of invention
Manufacturing approach of the present invention does not need large-scale equipment such as reliever, heating arrangement, can the high high-quality liquid-crystal compsn of fabrication reliability.That is, require for manufacturing rejection ratio resistance reduction, impurity generation less, the change of physics value less, the liquid-crystal compsn of high reliability, be very practical.
Embodiment
Below an example of the present invention is described.
Manufacturing approach of the present invention, equal solvent with an organic solvent through microwave irradiation is being comprised on the liquid-crystal compounds of at least a fusing point greater than 30 ℃ two or more liquid-crystal compounds, does not come the efficient liquid-crystal compsn of making.Special, using two kinds fusing point to make liquid-crystal compsn greater than 30 ℃ two or more liquid-crystal compounds is effectively, uses the fusing point more than five kinds more effective greater than 30 ℃ two or more liquid-crystal compounds manufacturing liquid-crystal compsn.
Fusing point is preferably more than 60% at the containing ratio of the compound more than 30 ℃, more preferably more than 70%, is preferably more than 80% especially.
In the liquid-crystal compsn, can contain the adjuvant except liquid-crystal compounds.As adjuvant, can use anti-oxidant, ultraviolet light absorber, antistatic agent, surfactant etc.The optically-active compound that can contain in addition, liquid crystal liquid crystal property or non-liquid crystal liquid crystal property.The compound that does not have the liquid crystal skeleton if addition is too big, will produce ill effect to the characteristic of liquid crystal, therefore, adds when not having the compound of liquid crystal skeleton, adds up to containing ratio preferred below 5%, and is further preferred below 3%, preferred especially below 1%.
The irradiation time of microwave was preferably below 1 hour, more preferably below 30 minutes.Temperature during microwave irradiation, if too high, the quality of the composition of manufacturing reduces, if too low, makes the more time of cost, therefore has only temperature.So the scope of liquid crystal phase ceiling temperature+50 from 40 ℃ to the liquid-crystal compsn of making ℃ is preferred ,+30 ℃ scope is preferred.
The frequency of the microwave that uses is preferably below the above 3THz of 300MHz, more preferably more than the 500MHz.Exposure intensity is preferably more than the 100W, more preferably more than the 1kW.
Manufacturing approach of the present invention is because can make liquid-crystal compsn, so even under common atmospheric atmosphere, also can make high-quality liquid-crystal compsn under lower temperature.Yet, in order to make more high-quality liquid-crystal compsn, preferably carry out microwave irradiation in confined conditions, more preferably under atmosphere of inert gases, carry out microwave irradiation.As inert gas, rare gas such as helium, neon, argon, nitrogen etc. can suit to use.
Manufacturing approach of the present invention need not used the decompression means, yet, also can the composition of making be used down in decompression state.
In the manufacturing approach of the present invention, the liquid-crystal compsn of making is had no particular limits, the occasion of under reduced pressure making especially preferably contains the manufacturing of the liquid-crystal compsn of the relatively little liquid-crystal compounds of the molecular weight of a large amount of volatilizations.
The molecular weight that preferably contains liquid-crystal compounds is the compound below 300, and the molecular weight that more preferably contains liquid-crystal compounds is the compound below 250.
In order to make liquid-crystal compsn more efficiently, preferably, constituting liquid crystal molecule has polarization.Concrete, when the formation liquid-crystal compounds has specific structure or functional group, just can make more efficiently.As preferred construction, preferably, has at least one aromatic rings in the molecule of liquid-crystal compounds.In addition,, be preferably electrophilic functional groups such as halogen, cyanic acid, have the compound of these functional groups on the preferred molecule, more preferably have the compound of aforementioned electrophilic functional group on the aromatic rings as preferred functional group.
As constituting compound, concrete, the compound shown in the preferred formula (I).
[changing 1]
(in the formula, R
1And R
2Expression can be by the alkenyloxy of the thiazolinyl of the alkoxy of the alkyl of the substituted carbon number 1～16 of fluorine, carbon number 1～16, carbon number 2～16, carbon number 3～16, fluorine atom, chlorine atom or cyanic acid independently of one another, and A, B and C represent 1 independently of one another, 4-phenylene, 2 or 3-fluoro-1,4-phenylene, 2,3-two fluoro-1; 4-phenylene, 3,5-two fluoro-1,4-phenylene, 2 or 3-chloro-1,4-phenylene, 2,3-two chloro-1; 4-phenylene, 3,5-two chloro-1,4-phenylene, 2-methyl isophthalic acid, 4-phenylene, 3-methyl isophthalic acid, 4-phenylene, naphthalene-2; 6-two bases, phenanthrene-2,7-two bases, fluorenes-2,7-two bases, anti--1,4-cyclohexylidene, 1,2; 3,4-naphthane-2,6-two bases, decahydronaphthalene-2,6-two bases, anti--1,3-diox-2; 5-two bases, pyridine-2,5-two bases, pyrimidine-2,5-two bases, pyrazine-2,5-two base or pyridazines-2; 5-two bases, these groups can be replaced by 1～3 fluorine atom further, and m representes 1 or 2, Z
1And Z
2Represent independently of one another singly-bound ,-CH
2CH
2-,-(CH
2)
4-,-OCH
2-,-CH
2O-,-COO-,-CH=CH-,-CF=CF-,-CH=N-N=CH-perhaps-C ≡ C-.But, when m is 2, two Z
2With C can be identical independently of one another or different.)
In the general formula (I), at least one among A, B and the C is preferably aromatic rings, and more preferably 1,4-phenylene, 2 or 3-fluoro-1,4-phenylene, 2,3-two fluoro-1; 4-phenylene, 3,5-two fluoro-1,4-phenylene, 2 or 3-chloro-1,4-phenylene, 2,3-two chloro-1,4-phenylene, 3; 5-two chloro-1,4-phenylene, 2-methyl isophthalic acid, 4-phenylene, 3-methyl isophthalic acid, 4-phenylene, naphthalene-2,6-two bases, phenanthrene-2,7-two bases, fluorenes-2; 7-two bases, 1,2,3,4-naphthane-2,6-two bases, pyridine-2,5-two bases, pyrimidine-2; 5-two bases, pyrazine-2,5-two base or pyridazines-2,5-two bases are preferably 1 especially, 4-phenylene, 2 or 3-fluoro-1; 4-phenylene, 2,3-two fluoro-1,4-phenylene, 3,5-two fluoro-1,4-phenylene.
Preferably, R
1And R
2In one be fluorine atom, chlorine atom or cyanic acid, another is the compound of alkene oxygen base of thiazolinyl, the carbon number 3～16 of alkoxy, the carbon number 2～16 of alkyl, the carbon number 1～16 of carbon number 1～16.
Make the occasion of TFT in manufacturing method according to the invention with liquid-crystal compsn, in the compound of general formula (I) expression, preferred R
1And R
2The compound of the alkyl of independent separately expression fluorine atom, carbon number 1～16 or the thiazolinyl of carbon number 2～16.The liquid-crystal compsn that obtains like this has high voltage retention.
Embodiment
Below, enumerating embodiment the present invention further is detailed, the present invention does not receive the qualification of these embodiment.In the following embodiment and the composition of comparative example, " % " meaning is " quality % ".
The irradiation of microwave is carried out (high-frequency output: 6kW, oscillation frequency number: 2450MHz ± 50MHz) with the microwave applicator of electric wave worker machine society of Fuji system (special articles made to order).With following device the liquid-crystal compsn of preparation is analyzed.
Gas chromatograph: the system HP6890 of HEWLETT PACKARD (Hewlett-Packard) society
For confirming of reliability, the ratio resistance through measuring liquid-crystal compsn, adopt gas chromatograph confirm impurity generation and cooperation compound decomposition, adopt the mensuration of voltage retention and current value, physics value to carry out.
The manufacturing of (embodiment 1) liquid-crystal compsn
The manufacturing of the liquid-crystal compsn (95.1 ℃ of STN1, liquid crystal ceiling temperatures) that carries out constituting by following compound.[changing 2]
Above-mentioned each compound of weighing record amount, placing capacity is 150 milliliters removable flask.This removable flask is placed microwave generating apparatus, with power irradiating microwaves, the heating of 1kW.Shine after 10 minutes, stop the irradiation of microwave, cool off removable flask, from microwave applicator, take out, obtain the STN1 of 100g nematic liquid crystal state.
Measuring the ratio resistance of the liquid-crystal compsn of preparation, is 1.1 * 10
11Ω cm.After the liquid-crystal compsn of processing with the gas chromatograph analysis in addition, do not sneak into and generate the material beyond the compound of cooperation, also find the compound decomposition that cooperates.Measure the rerum natura of the liquid-crystal compsn of preparation, obtain desired characteristics.This liquid crystal is injected the STN panel, measure electric optical characteristics, obtain desired characteristic.Can find out that according to above content the liquid-crystal compsn of embodiment 1 has extreme high reliability.
Manufacturing approach of the present invention can not need large-scale equipment, utilizes 40 minutes and just can produce high-quality liquid-crystal compsn.
(comparative example 1) decompression is the manufacturing of liquid-crystal compsn down
According to the method for TOHKEMY 2002-194356 communique record, carry out the manufacturing of the liquid-crystal compsn (STN1) identical with embodiment 1.
The liquid-crystal compounds of First Astronautic Research Institute for Measurement and Test's regulation places eggplant type flask.This eggplant type flask is installed in the rotary evaporator.Eggplant type flask immersed in 50 ℃ the oil bath and make its rotation.Through vacuum pump rotary evaporator is vacuumized and slowly to be decompressed to 20kPa in 5 minutes.The temperature of oil bath is set at 110 ℃, heats up with 5 ℃/minute speed.Liquid crystal is changed to liquid condition, after becoming transparent 30 minutes, oil bath is become water-bath, cooling.Temperature drops to after the room temperature, stops the rotation, and stops decompression.Through with after replacing to nitrogen in the flask and returning to atmospheric pressure, eggplant type flask is taken out from rotary evaporator, obtain the STN1 of 100g nematic liquid crystal state.
Measuring the ratio resistance of the liquid-crystal compsn of preparation, is 1.2 * 10
11Ω cm.With the result of the liquid-crystal compsn of gas chromatograph analyte preparation, do not sneak into and generate the material beyond the compound of cooperation, also find the compound decomposition that cooperates.Measure the rerum natura of the liquid-crystal compsn of preparation, obtain desired characteristics.But, confirming that the part volatilization takes place the low relatively compound of molecular weight, composition changes.In addition, except the reliever of necessary request for utilization large-scale equipment with the heating arrangement, also need long manufacturing time in the manufacturing.
The manufacturing of liquid-crystal compsn under (comparative example 2) atmosphere
According to the method for japanese kokai publication hei 5-105876 communique record, carry out the manufacturing of the liquid-crystal compsn (STN1) identical with embodiment 1.
The liquid-crystal compounds of First Astronautic Research Institute for Measurement and Test's regulation places eggplant type flask.In eggplant type flask, put into the magneto stirrer, place on 50 ℃ the hot plate, with 5 ℃/minute speed the temperature of hot plate be warming up to 110 ℃ on one side, stir through the rotation stirrer on one side.Liquid crystal is changed to liquid condition, after becoming transparent back 30 minutes, stop to hot plate heating, slowly return to room temperature.Obtain the STN1 of 100g nematic liquid crystal state.
Measuring the ratio resistance of the liquid-crystal compsn of preparation, is 1.1 * 10
9Ω cm.Learn after the liquid-crystal compsn with the gas chromatograph analyte preparation, the compound material in addition of more cooperation occurs, the liquid-crystal compounds generation oxygenolysis of component analysis result's liquid-crystal compsn.Measure liquid crystal upper change point transition temperature, be low to moderate 94.0 ℃, the article qualitative change is bad big.In the manufacturing approach of comparative example 2, from the reliability of the liquid-crystal compsn made, than embodiment difference.
The manufacturing of (embodiment 2) liquid-crystal compsn
The manufacturing of the liquid-crystal compsn (68.0 ℃ of TFT1, liquid crystal ceiling temperatures) that carries out constituting by following compound.
[changing 3]
Above-mentioned each compound of weighing record amount, placing capacity is 150 milliliters removable flask.This removable flask is placed microwave generating apparatus, with power irradiating microwaves, the heating of 1kW.Shine after 10 minutes, stop the irradiation of microwave, cool off removable flask, from microwave applicator, take out, obtain the TFT1 of 100g nematic liquid crystal state.
Measuring the ratio resistance of the liquid-crystal compsn of preparation, is 1.5 * 10
14Ω cm.Use the liquid-crystal compsn of gas chromatograph analyte preparation in addition, the result does not sneak into and generates the compound material in addition of cooperation, also finds the compound decomposition that cooperates.Measure the rerum natura of the liquid-crystal compsn of preparation, obtain desired characteristics.This liquid crystal is injected the TFT panel, measure electric optical characteristics, obtain desired characteristic.And the voltage retention of occasion of using it for the TFT panel is also very high.
Manufacturing approach of the present invention can not need large-scale equipment, utilizes 40 minutes and produces high-quality liquid-crystal compsn.Can find out that according to above content the liquid-crystal compsn of embodiment 2 has extreme high reliability.
(comparative example 3) decompression is the manufacturing of liquid-crystal compsn down
According to the method for TOHKEMY 2002-194356 communique record, carry out the manufacturing of the liquid-crystal compsn (TFT1) identical with embodiment 2.
The liquid-crystal compounds of First Astronautic Research Institute for Measurement and Test's regulation places eggplant type flask.Eggplant type flask is installed in the rotary evaporator.Eggplant type flask immersed in 50 ℃ the oil bath and make its rotation.Through vacuum pump rotary evaporator is vacuumized and slowly to be decompressed to 20kPa in 5 minutes.The temperature of oil bath is set at 85 ℃, with 5 ℃/minute the speed temperature so far that heats up.Liquid crystal is changed to liquid condition, become transparent after, after 30 minutes, oil bath is become water-bath, cooling.Temperature drops to after the room temperature, stops the rotation, and stops decompression.Through with after replacing to nitrogen in the flask and returning to atmospheric pressure, eggplant type flask is taken out from rotary evaporator, obtain the TFT1 of 100g nematic liquid crystal state.
Measuring the ratio resistance of the liquid-crystal compsn of preparation, is 1.2 * 10
14Ω cm.Liquid-crystal compsn result with the gas chromatograph analyte preparation is, do not sneak into and generate the material beyond the compound of cooperation, also finds the compound decomposition that cooperates.Measure the rerum natura of the liquid-crystal compsn of preparation, obtain desired characteristics.But, confirm that the low relatively compound of molecular weight partly volatilizees, form to change.In addition, except the reliever of necessary request for utilization large-scale equipment with the heating arrangement, also need long manufacturing time in the manufacturing.
The manufacturing of liquid-crystal compsn under (comparative example 4) atmosphere
According to the method for japanese kokai publication hei 5-105876 communique record, carry out the manufacturing of the liquid-crystal compsn (TFT1) identical with embodiment 2.
The liquid-crystal compounds of First Astronautic Research Institute for Measurement and Test's regulation places eggplant type flask.In eggplant type flask, put into the magneto stirrer, place on 50 ℃ the hot plate, with 5 ℃/minute speed the temperature of hot plate be warming up to 85 ℃ on one side, through being rotated, stirs stirrer on one side.Liquid crystal is changed to liquid condition, after becoming transparent back 30 minutes, stop to hot plate heating, slowly return to room temperature.Obtain the TFT1 of 100g nematic liquid crystal state.
Measuring the ratio resistance of the liquid-crystal compsn of preparation, is 1.3 * 10
13Ω cm.Learn after the liquid-crystal compsn with the gas chromatograph analyte preparation, the compound material in addition of more cooperation occurs, the liquid-crystal compounds oxygenolysis of component analysis result's liquid-crystal compsn.Measure liquid crystal upper change point transition temperature, be low to moderate 66.8 ℃, the article qualitative change is bad big.In the manufacturing approach of comparative example 4, from the reliability of the liquid-crystal compsn made, than embodiment difference.
Utilizability on the industry
Manufacturing approach of the present invention, require for manufacturing rejection ratio resistance reduction, impurity generation less, the change of physics value less, the liquid-crystal compsn of high reliability, be very practical.
Claims (7)
1. the manufacturing approach of a liquid-crystal compsn is characterized in that, not with an organic solvent, and to the two or more liquid-crystal compounds irradiating microwaves of at least a fusing point greater than 30 ℃.
2. manufacturing approach according to claim 1 is characterized in that, in the liquid-crystal compounds, at least two kinds fusing point is greater than 30 ℃.
3. manufacturing approach according to claim 1 is characterized in that, the irradiation time of microwave is below 1 hour.
4. manufacturing approach according to claim 1 is characterized in that, under reduced pressure carries out the irradiation of microwave.
5. manufacturing approach according to claim 1 is characterized in that, in inert gas atmosphere, carries out the irradiation of microwave.
6. manufacturing approach according to claim 1 is characterized in that, the temperature during microwave irradiation does, the scope of liquid crystal phase ceiling temperature+50 from 40 ℃ to the liquid-crystal compsn of making ℃.
7. manufacturing approach according to claim 4 is characterized in that, uses inert gas when decompression state is returned to atmospheric pressure.
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| CN1597727A (en) * | 2004-08-26 | 2005-03-23 | 复旦大学 | Solid state polymerization preparation method of liquid crystal copolyester |
| JP2007039414A (en) * | 2005-08-05 | 2007-02-15 | Chisso Corp | Axially asymmetric optically active cyclohexane compound, liquid crystal composition, liquid crystal display element and formed article |
| CN1974672A (en) * | 2005-10-28 | 2007-06-06 | 株式会社上野科技 | Liquid-crystalline polymer blend and composition comprising the same |
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| CN1597727A (en) * | 2004-08-26 | 2005-03-23 | 复旦大学 | Solid state polymerization preparation method of liquid crystal copolyester |
| JP2007039414A (en) * | 2005-08-05 | 2007-02-15 | Chisso Corp | Axially asymmetric optically active cyclohexane compound, liquid crystal composition, liquid crystal display element and formed article |
| CN1974672A (en) * | 2005-10-28 | 2007-06-06 | 株式会社上野科技 | Liquid-crystalline polymer blend and composition comprising the same |
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