WO2005019378A1 - Mesogenic compounds, medium for electro-optical displays and electro-optical display - Google Patents
Mesogenic compounds, medium for electro-optical displays and electro-optical display Download PDFInfo
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- WO2005019378A1 WO2005019378A1 PCT/EP2004/008942 EP2004008942W WO2005019378A1 WO 2005019378 A1 WO2005019378 A1 WO 2005019378A1 EP 2004008942 W EP2004008942 W EP 2004008942W WO 2005019378 A1 WO2005019378 A1 WO 2005019378A1
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- 0 *CC1C=CCCC1 Chemical compound *CC1C=CCCC1 0.000 description 16
- QEELHTIXYIXYPM-UHFFFAOYSA-N CC(CC1)CCC1C1COc2ccc(cccc3)c3c2-c(c2ccccc2cc2)c2OC1 Chemical compound CC(CC1)CCC1C1COc2ccc(cccc3)c3c2-c(c2ccccc2cc2)c2OC1 QEELHTIXYIXYPM-UHFFFAOYSA-N 0.000 description 1
- GIENEBNYQIDPAQ-UHFFFAOYSA-N N#Cc(cc1)ccc1-c(c(F)c1)ccc1-c1ccccc1 Chemical compound N#Cc(cc1)ccc1-c(c(F)c1)ccc1-c1ccccc1 GIENEBNYQIDPAQ-UHFFFAOYSA-N 0.000 description 1
- GFXFYICUYXJGBM-UHFFFAOYSA-N N#Cc(cc1)ccc1-c(cc1)cc(F)c1-c1ccccc1 Chemical compound N#Cc(cc1)ccc1-c(cc1)cc(F)c1-c1ccccc1 GFXFYICUYXJGBM-UHFFFAOYSA-N 0.000 description 1
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- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
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- 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
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- 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
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- 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
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- 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
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
- C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
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- 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
- C09K2019/0444—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group
- C09K2019/0466—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a linking chain between rings or ring systems, a bridging chain between extensive mesogenic moieties or an end chain group the linking chain being a -CF2O- chain
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- C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition
Definitions
- the present invention relates to mesogenic compounds, media for electro- optical displays comprising these and to electro-optical displays comprising these media, in particular to displays using mesogenic modulation media which are in an optically isotropic state at the temperature of operation of the light modulation elements and to respective modulation elements and displays.
- Liquid Crystal Displays are widely used to display information.
- Electro-optical modes employed are e.g. the twisted nematic (TN)-, the super twisted nematic (STN)- and the electrically controlled birefringence (ECB)-mode with their various modifications, as well as others.
- TN twisted nematic
- STN super twisted nematic
- EBC electrically controlled birefringence
- electro-optical modes employing an electrical field substantially parallel to the substrates, respectively the liquid crystal layer like e.g. the in-pjane switching (IPS)-mode (compare e.g. DE 40 00 451 and EP 0 588 568).
- IPS in-pjane switching
- liquid crystal medium as such, oriented on surfaces, which typically are pre-treated to achieve uniform alignment of the liquid crystal material
- composite systems of liquid crystal materials of low molecular weight together with polymeric materials such as e.g. p_olymer dispersed liquid crystal (PDLC)-, nematic curvilinearily aligned phase (NCAP)- and polymer network (PN)-systems, as disclosed for example in WO 91/05 029.
- PDLC p_olymer dispersed liquid crystal
- NCAP nematic curvilinearily aligned phase
- PN polymer network
- LCDs especially LCDs comprising composite systems like PDLCs and in particular so called holographic PDLC (HPDLC) systems are used in practical applications.
- HPDLCs are described e.g. in Date, Takeuchi, Tanaka, and Kato, Journal of the SID 7/1
- HPDLC displays are generating three bright colours, preferably primary colors, utilizing Bragg reflection. This technique results in excellent bright colours, as it does neither need polarizers, nor color filters.
- a single layer of the periodic structure of polymer and liquid crystal controls the reflection of one particular colour. To realise three primary colors consequently three layers, one for each colour are required.
- Each of the three layers has to be addressed independently. This requires three sets of HPDLC films, each with corresponding electrodes. This large number of layers and corresponding electrodes, which is difficult to realize with a good yield in mass production, can remediiously be reduced when the "two-frequency" drive method is applied.
- OBC optically compensated bent
- DE 10252250.2 all yet to be laid open except the first one, describe light controlling elements using modulation media which are in the isotropic state at the operation temperature of the elements, whereas DE 103 13 979.6, also yet to be laid open, describes elements using modulation media which are in the optically isotropic blue phase, when operated.
- This type of light modulation elements is characterised by very fast response times and by an excellent contrast with minimal viewing angle dependence.
- the temperature range of operation has not been sufficiently wide so far and the temperature dependence of the operation voltages still is quite high and has to be reduced in order to allow easier addressing over a wider range of temperatures.
- the compounds should be suitable for use in mesogenic media in electro- optical displays, in particular as control media of these displays.
- they should be soluble in base media with a mesogenic phase, e.g. a nematic, cholesteric, smectic or even a medium having an optically isotropic phase, e.g. a blue phase.
- a mesogenic phase e.g. a nematic, cholesteric, smectic
- a medium having an optically isotropic phase e.g. a blue phase.
- they even should exhibit one or more of these phases as single compounds.
- Liquid crystalline or mesogenic compounds with very high values of the dielectric anisotropy so far have mostly (with only very few exceptions) been realised by incorporation of strongly polar terminal groups especially such as a cyano (-CN) group or also a isothiocyanato (-NCS) group as e.g. in EP 01 101 157.
- a cyano (-CN) group or also a isothiocyanato (-NCS) group as e.g. in EP 01 101 157.
- Use of compounds of these types leads to mesogenic media, especially for use in TN type displays, with rather low specific resistivity, which in turn do not match the demanding requirements for the voltage holding ratio of the media in displays driven by an active matrix, as e.g.
- the respective functional or modulation media used for the displays are disclosed in DE 102 17 273 A1.
- mesogenic media consisting predominantly or even entirely of mesogenic compounds with a terminal fluorine substitution or with a fluorinated terminal group, so far, do not provide a dielectric anisotropy, which is high enough to realise low operation voltages, especially if they are used in light modulation media for the displays disclosed in DE 102 17273 which are most demanding in this respect.
- mesogenic media with high ⁇ especially useful for displays disclosed in DE 102 17273 A1 and in particular in DE 103 13 979.6 can be realised, which do not exhibit the drawbacks of the materials of the prior art, or at least do exhibit them to a significantly lesser degree.
- the compounds of the instant invention are particularly well suited for use in light modulation elements and displays using a modulation medium which is in an optically isotropic state, preferably in the blue phase, as disclosed in DE 103 13979.6.
- the inventive compounds do lead to a significant decrease of the temperature dependence of the characteristic voltages and hence of the operation voltages and/or to a significant increase of the temperature range over which the temperature dependence is rather small.
- component A a first liquid crystal component comprising compounds of formula I, which are strongly dielectrically positive compounds with very high values of ⁇ and also ⁇ n
- a, b, c and d are independently of each other 0, 1 or 2, whereby a + b + c + d ⁇ 4;
- a 11 , A 12 , A 13 and A 14 may be the same ring or two
- R 11 , R 12 and R 13 independently of each other, are n-alkyl or n-alkoxy with 1 to 20, preferably 1 to 10, preferably 1 to 8, preferably 2 to 8, preferably 2 to 6 C-atoms, alkenyl, alkenyloxy or alkoxyalkyl with 2 to 20, preferably 2 to 8, preferably 2 to 6, preferably 2 to 5 C-atoms or CN, NCS, halogen, preferably F, Cl, halogenated alkyl, alkenyl or alkoxy, preferably mono-, di- or oligo-fluorinated alkyl, alkenyl or alkoxy, especially preferred CF 3 OCF 2 H or OCF 3 , preferably R 11 , R 12 and R 13 are alkoxy, preferably with 1 to 10 C-atoms,
- one or more of the groups R 11 , L 11 , L 12 , L 13 , L 14 , Y 11 , Y 12 , Y 13 , Y 14 and X 11 which are present in the compounds of formula I, is/are a chiral group, which preferably is a group of formula I * -Q 1 -CH-Q 2 I Q 3 , *
- Q 1 is an alkylene or alkylene-oxy group with 1 to 9 C atoms or a single bond
- Q 2 is an alkyl or alkoxy group with 1 to 10 C atoms which may be unsubstituted, mono- or polysubstituted by F, Cl, Br or CN, it being also possible for one or more non-adjacent CH 2 groups to be replaced, in each case independently from one another, by -C ⁇ C-, -0-, -S-, -NH-, -N(CH 3 )-, -CO-, -COO-, -OCO-, -OCO-0-, -S-CO- or -CO-S- in such a manner that oxygen atoms are not linked directly to one another,
- Q 3 is F, Cl, Br, CN or an alkyl or alkoxy group as defined for Q 2 but being different from Q 2 .
- the O atom is preferably adjacent to the chiral C atom.
- Preferred chiral groups of formula I* are 2-alkyl, 2-alkoxy, 2-methylalkyl, 2- methylalkoxy, 2-fluoroalkyl, 2-fluoroalkoxy, 2-(2-ethin)-alkyl, 2-(2-ethin)-alkoxy, 1 ,1 ,1 -trif luoro-2-alkyl and 1 ,1 ,1 -trif luoro-2-alkoxy.
- achiral branched alkyl group may occasionally be of importance, for example, due to a reduction in the tendency towards crystallization.
- Branched groups of this type generally do not contain more than one chain branch.
- At least one and preferably one of the rings A 11 , A 12 , A 13 and A 14 , which are present in the compound of formula 1 is a chiral moiety, preferably selected from the group of cholesterine-diyl, pinimenthol-diyl and tetrahydropyrane-diyl and most preferably tetrahydropyrane-diyl.
- one or more of the groups R 11 , L 11 , L 12 , L 13 , L 14 , Y 11 , Y 12 , Y 13 , Y 14 and X 11 which are - present in the compounds of formula I, is/are PG-SG wherein SG is a spacer group and
- PG is a polymerisable or reactive group.
- the polymerisable or reactive group PG is preferably selected from
- PG is a vinyl group, an acrylate group, a methacrylate group, an oxetane group or an epoxy group, especially preferably an acrylate or methacrylate group.
- the spacer group SG all groups can be used that are known for this purpose to those skilled in the art.
- the spacer group SG is preferably of formula SG'-X, such that PG-SG- is PG-SG'-X-, wherein
- R 01 , R 02 , Y 01 and Y 02 have one of the respective meanings given above.
- Typical groups SG' are, for example, -(CH 2 ) P -, -(CH 2 CH 2 0) q -CH 2 CH 2 -, -CH 2 CH 2 -S-CH 2 CH 2 - or -CH 2 CH2-NH-CH 2 CH 2 - or -(SiR°R 00 -O) p -, with p being an integer from 2 to 12, q being an integer from 1 to 3 and R°, R 00 and the other parameters having the meanings given above.
- Preferred groups SG' are ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, octadecylene, ethyleneoxyethylene, methyleneoxybutylene, ethylene-thioethylene, ethylene-N-methyl-iminoethylene, 1 -methylalkylene, ethenylene, propenylene and butenylene for example.
- SG' is a chiral group of formula I*': * 4
- Q 4 is an alkylene or alkylene-oxy group with 1 to 10 C atoms or a single bond, being different from Q 1 ,
- each of the two polymerisable groups PG and the two spacer groups SG can be identical or different.
- a preferred embodiment of the instant are compounds of formula I wherein at one or more, preferably two, three or more, of the radicals
- R 1 ⁇ L 11 , L 12 , L 13 , L 14 ,Y 1 ⁇ Y 12 , Y 13 , Y 14 and X 11 which are resent, is/are aryl, aryloxy, alkylaryl, alkylaryloxy, alkylarylalkyl, alkylarylalkoxy, cycloalkyl, cycloalkyloxy, cycloalkylalkenyloxy, alkylcycloalkyl, alkylcycloalkyloxy or alkylcycloalkylalkenyloxy, preferably aryloxy, alkylaryloxy, cycloalkyloxy, cycloalkylalkenyloxy, alkylcycloalkyloxy or alkylcycloalkylalkenyloxy, each with up to 15 carbon atoms, wherin said in radicals being unsubstituted or mono- substituted with a -CN group or mono- or poly-substituted with halogen
- radicals Preferably one or more, preferably two, three or more, of the radicals
- R x has the meaning given above and preferably is n-alkyl and most preferably methyl.
- the mesogenic media according to the present invention simultaneously comprise a second mesogenic, liquid crystalline component (called component B), which is a dielectrically positive component comprising, and preferably consisting of terminally polar substituted bi- or terphenyl compounds, which or some of which optionally are laterally fluorinated, preferably of formula II
- component B is a dielectrically positive component comprising, and preferably consisting of terminally polar substituted bi- or terphenyl compounds, which or some of which optionally are laterally fluorinated, preferably of formula II
- n 2 is O, 1 , 2 or 3,
- R ⁇ has the meaning given for R 11 under formula I, preferably under formula 1-1 above, but preferably is alkyl or alkenyl,
- X 2 is CN, SF 5 , SO2CF3, NCS, CF 3 , OCF 3> F or Cl, preferably CN, NCS or Cl, most preferably CN or NCS.
- the mesogenic media according to the instant invention contain a component A comprising, preferably predominantly consisting of and most preferably entirely consisting of compounds of formula I.
- Liquid crystal compounds in this application embrace compounds with a liquid crystalline phase by themselves as well as compounds, which are compatible with mesogenic phases, especially with the nematic phase, without decreasing the clearing point unacceptably.
- the latter compounds have a mesogenic structure and are also called mesogenic compounds.
- R, R' and R" independently from each other, are alkyl, alkoxy, alkenyl, alkenyloxy or oxaalkyl, preferably alkoxy, preferably R' and R" and most preferably R, R' and R" are identical to each other, and Y 11 and Y 12 , independently of each other, are as defined hereinbefore.
- R and X-11 is as defined above and R'" is other, alkyl, alkenyl, alkenyloxy, oxaalkenyl or oxaalkyl. It should be noted that -OR"' radicals having different meanings for R'" can easily be introduced by stepwise
- R 11 , L 11 , L 12 have the same meaning as given above for general formula I.
- Comprising in this application means in the context of compositions that the entity referred to, e.g. the medium or the component, contains the compound or compounds in question, preferably in a total concentration of 10 % or more and most preferably of 20 % or more.
- Predominantly consisting, in this context, means that the entity referred to contains 80 % or more, preferably 90 % or more and most preferably 95 % or more of the compound or compounds in question.
- Entirely consisting, in this context, means that the entity referred to contains 98 % or more, preferably 99 % or more and most preferably 100.0 % of the compound or compounds in question.
- the compounds of formula I are preferably selected from the group of sub- formulae 1-1.1 to 1-1.15, especially 1-1.1 , 1-1.2, 1-1.3, 1-1.4 and/or 1-1.5:
- R 11 to R 13 are identical to each other and preferably are alkoxy, alkenyloxy, halogenated alkoxy or oxaalkoxy, and
- Y 11 and Y 12 are independently of each other H, CF 3 or F.
- the compounds of formulae 1-1.1 to 1-1.5 preferably are selected from the group of compounds of formula 1-1 A
- R, R', R" X, Y 11 and Y 12 are as defined above, preferably
- X is F, CF 3 , SF 5 , SO 2 CF 3 , OCF3 or CN and
- Y 11 and Y 12 are independently of each other H, CF 3 or F.
- liquid crystalline media according to the instant invention contains a component B comprising, preferably predominantly consisting of compounds of formula II as defined hereinbefore.
- R 2 is alkyl or alkoxy, wherein one or more methylene groups of said alkyl may be replaced -C ⁇ C-, and for sub-formulae lib and lie preferably alkyl.
- the media according to the present invention may contain a component C.
- This component C may be dielectrically neutral or dielectrically negative, depending upon the relative amounts of compounds with positive and negative dielectrical anisotropy contained therein.
- Component C is used in a concentration of 0 to 40 %, preferably 0 to 20 % and most preferably from 0 to 10 % of the total mixture.
- the inventive liquid crystal medium contains a further component D, which is a dielectrically neutral component and preferably comprises and more preferably consists of dielectrically neutral compounds.
- Component D is used to adjust especially the phase range and the optical anisotropy of the inventive liquid crystal media.
- the concentration of component D in the liquid crystal medium according to the present invention is preferably 0 % to 40 %, more preferably 0 % to 25 %, most preferably 0 % to 15 % and in particular 3 to 10 %.
- the inventive liquid crystal medium contains a further component E, which is a chiral component and preferably comprises and more preferably consists of chiral compounds. It is preferred that the liquid crystal medium according to the invention contains that further chiral component E.
- the inventive media can comprise further liquid crystal compounds in order to adjust the physical properties.
- Such compounds are known to the expert.
- Their concentration in the media according to the instant invention is preferably 0 to 30 %, more preferably 0 to 20 % and most preferably 5 to15 %.
- the liquid crystal medium contains 50 % to 100 %, more preferably 70 % to 100 % and most preferably 80 % to 100 % and in particular 90 % to 100 % totally of components A and B which contain, preferably predominantly consist of and most preferably entirely consist of one or more of compounds of formulae I and II, respectively.
- dielectrically positive compounds describes compounds with ⁇ > 1 ,5, dielectrically neutral compounds are compounds with -1 ,5 ⁇ ⁇ ⁇ 1 ,5 and dielectrically negative compounds are compounds with ⁇ ⁇ -1 ,5.
- ⁇ is determined at 1 kHz and 20 °C.
- the dielectrical anisotropies of the compounds is determined from the results of a solution of 10 % of the individual compounds in a nematic host mixture.
- the capacities of these test mixtures are determined both in a cell with homeotropic and with homogeneous alignment.
- the cell gap of both types of cells is approximately 10 ⁇ m.
- the voltage applied is a rectangular wave with a frequency of 1 kHz and a root mean square value typically of 0.1 V or 0.5 V to 1.0 V, however, it is always selected to be below the capacitive threshold of the respective test mixture.
- the mixture ZLI-4792 and for dielectrically neutral, as well as for dielectrically negative compounds are used as host mixture, respectively.
- the dielectric permittivities of the compounds are determined from the change of the respective values of the host mixture upon addition of the compounds of interest and are extrapolated to a concentration of the compounds of interest of 100 %.
- threshold voltage refers in the instant application to the optical threshold and is given for 10 % relative contrast (V- t o) and the term saturation voltage refers to the optical saturation and is given for 90 % relative contrast (Vgo) both, if not explicitly stated otherwise.
- the capacitive threshold voltage V 0 , also called Freedericks-threshold V Fr ) is only used if explicitly mentioned.
- the threshold voltages, as well as all other electro- optical properties have been determined with test cells prepared at Merck KGaA, Germany.
- the test ceils for the determination of ⁇ had a cell gap of 22 ⁇ m.
- the electrode was a circular ITO electrode with an area of 1.13 cm 2 and a guard ring.
- the orientation layers were lecithin for homeotropic orientation ( ⁇
- the capacities were determined with a frequency response analyser Solatron 1260 using a sine wave with a voltage of 0.3 V rms .
- the light used in the electro-optical measurements was white light.
- the set up used was a commercially available equipment of Otsuka, Japan.
- the characteristic voltages have been determined under perpendicular observation.
- the threshold ( ⁇ o) - mid grey (V 5 o) - and saturation (V 90 ) voltages have been determined for 10 %, 50
- the liquid crystal media according to the present invention may contain further additives and chiral dopants. It is especially preferred that they contain chiral dopants.
- the total concentration of these further constituents is in the range of 0 % to 20 %, preferably 0.1 % to 15 %, more preferably 1 to 15 %, especially 1 to 6 %, based in the total mixture.
- the concentrations of the individual compounds used each are preferably in the range of 0.1 to 3 %. The concentration of these and of similar additives is not taken into consideration for the values and ranges of the concentrations of the liquid crystal components and compounds of the liquid crystal media in this application.
- the inventive liquid crystal media according to the present invention consist of several compounds, preferably of 3 to 30, more preferably of 5 to 20 and most preferably of 6 to 14 compounds. These compounds are mixed in conventional way. As a rule, the required amount of the compound used in the smaller amount is dissolved in the compound used in the greater amount. In case the temperature is above the clearing point of the compound used in the higher concentration, it is particularly easy to observe completion of the process of dissolution. It is, however, also possible to prepare the media by other conventional ways, e. g. using so called pre-mixtures, which can be e. g. homologous or eutectic mixtures of compounds or using so called multi-bottle-systems, the constituents of which are ready to use mixtures themselves.
- pre-mixtures which can be e. g. homologous or eutectic mixtures of compounds or using so called multi-bottle-systems, the constituents of which are ready to use mixtures themselves.
- the liquid crystal media according to the instant invention can be modified in such a way, that they are usable in all known types of liquid crystal displays, either using the liquid crystal media as such, like TN-, TN-AMD, ECB-, VAN-AMD and in particular in composite systems, like PDLC-, NCAP- and PN-LCDs and especially in HPDLCs.
- the LC media of the present invention are especially suitable for use in light modulation elements and displays using a modulation (or controlling) medium which is in an optically isotropic state, preferably in the blue phase.
- the melting point T(C,N) or T(C;I), the transition from the smectic (S) to the nematic (N) phase T(S,N) and the clearing poin T(N,l) of the liquid crystals are given in degrees centigrade. ln the present application and especially in the following examples, the structures of the liquid crystal compounds are represented by abbreviations also called acronyms. The transformation of the abbreviations into the corresponding structures is straight forward according to the following two tables A and B. All groups C n H 2n+ ⁇ and
- the liquid crystal media according to the instant invention do contain preferably four or more compounds selected from the group of compounds of tables A and B and/or five or more compounds selected from the group of compounds of table B and/or two or more compounds selected from the group of compounds of table A.
- Example 1 the physical data especially of the compounds illustrate to the expert which properties can be achieved in which ranges. Especially the combination of the various properties, which can be preferably achieved, is thus well defined.
- Example 1 the physical data especially of the compounds illustrate to the expert which properties can be achieved in which ranges. Especially the combination of the various properties, which can be preferably achieved, is thus well defined.
- the compound is prepared analogously to example 1.
- the compound has a melting point of 66°C and a melting enthalpy of 7.5 kcal/mol. It is melting from the crystalline glass phase into the isotropic phase.
- the compound is prepared analogously to example 1.
- the compound has a glass transition temperature of -23°C, a melting point of 50°C and a melting enthalpy of 6.8 kcal/mol. It is melting from the glass phase into the isotropic phase.
- the compound has a glass transition temperature of -31 °C. It is melting from the glass phase into the isotropic phase.
- the compound has a melting point of 16°C, a melting enthalpy of 11.0 kcal/mol and an enthalpy of crystallisation of 3.7 kcal/mol. It is melting from the crystalline phase into the isotropic phase.
- the compound has a glass transition temperature of -14°C and a melting point of 89°C. It is melting from the glass phase into the isotropic phase.
- a liquid crystal mixture, host mixture A is realised consisting of:
- This mixture has the following properties:
- T g , T (K,l) and T(g,l) given in Tables 1a, 1b below are determined by means of DSC (differential scanning calorimetry) and microscopy.
- test cell is an electro-optical cell with interdigital electrodes having a distance of electrodes of 10 ⁇ m, a width of electrodes of 10 ⁇ m, and a cell thickness of 10 ⁇ m.
- the height of the electrodes - that are made out of chromium and without a polyimid layer - can be ignored in comparison to the cell thickness.
- Ttrans is the characteristic temperature which is defined as follows: - If the characteristic voltage as a function of temperature has a minimum, the temperature at this minimum is denoted as characteristic temperature; - If the characteristic voltage as a function of temperature has no minimum and if the controlling medium has one or more blue phases, the transistion temperature to the blue phase is denoted as characteristic temperature; in case there are more than one blue phase, the lowest transition temperature to a blue phase is denoted as characteristic temperature; - If the characteristic voltage as a function of temperature has no minimum and if the controlling medium has no blue phase, the transistion temperature to the isotropic phase is denoted as characteristic temperature.
- characteristic voltage refers to a specific voltage, e.g. the threshold voltage V 10 at which a light transmission of 10% is observed or the saturation voltage Vg 0 at which a transmission of 90% is observed.
- the concentration of the compound of example 47 in the host mixture A is varied from 3% over 5% and 7% to 15%
- the data are compiled in table 2.
- Tt r ans. is the transition temperature from the cholesteric phase into the optically isotropic phase. It can be observed in electro-optical cells with cross-polarisers.
- a liquid crystal mixture, host mixture B, is realised consisting of:
- This mixture has the following properties:
- a liquid crystal mixture, host mixture C, is realised consisting of:
- This mixture has the following properties:
- a liquid crystal mixture is realised consisting which has the following composition and properties. Table 6
- a liquid crystal mixture is realised, which has the following composition and properties.
- a liquid crystal mixture is realised, which has the following composition and properties.
- a liquid crystal mixture, host mixture D is realised consisting of:
- This mixture has the following properties:
- host mixture D now 5% of the compound of example 47 (P(O3) 2 UQU-3O-T), and 5% of the chiral dopant R-5011 and 2% of its enantiomer S-5011 (equivalent to the addition of 3% of R-5011 and 4% of the racemate) are added, as shown in the following table, table 9, and the properties of the resulting mixture are determined. The results are compiled in table 9.
- a liquid crystal mixture, host mixture E, is realised consisting of:
- a liquid crystal mixture, host mixture F, is realised consisting of:
- host mixture F various concentrations of the compound of example 47 (P(O3) 2 UQU-3O-T) and various concentrations of the chiral dopant R-5011 are added and the properties of the resulting mixtures are determined.
- concentrations and the data are compiled in tables 13a and13b.
- a liquid crystal mixture, host mixture G is realised consisting of:
- This mixture has the following properties: Clearing point (T(N,I))/°C: 75.0.
- host mixture G alternatively 5% (use-example 14.1), 7% (use-example 14.2), and 10% (use-example 14.3), respectively, of the compound of example 47 (P(O3) 2 UQU-3O-T) and 5% of the chiral dopant R-5011 are added and the properties of the resulting mixtures are determined.
- concentrations and the data are compiled in table 14.
- host mixtures H to I consisting of:
- a liquid crystal mixture, host mixture K, is realised consisting of:
- host mixture K 5% of the compound of example 47 (P(O3) 2 UQU-3O-T) is addded together with 9% of the chiral dopant BO2C*H-C-5 (which is a homologue of S-5011 (also: BO2C*H-C-3) with an n-pentyl terminal chain instead of an n-propyl group and which has an HTP in MLC-6260, available from Merck KGaA, at 20°C of -71.7 ⁇ m "1 ) and the property of the resulting mixture is determined.
- the results are compiled in table 16.
Abstract
Description
Claims
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AT04763959T ATE447001T1 (en) | 2003-08-25 | 2004-08-10 | MESOGENIC COMPOUNDS, MEDIUM FOR ELECTROOPTICAL DISPLAY AND ELECTROOPTICAL DISPLAY |
JP2006524270A JP2007503487A (en) | 2003-08-25 | 2004-08-10 | Mesogenic compound, medium for electro-optic display and electro-optic display |
DE602004023857T DE602004023857D1 (en) | 2003-08-25 | 2004-08-10 | MESOGENIC COMPOUNDS, MEDIUM FOR ELECTROOPTICAL DISPLAY AND ELECTROOPTICAL DISPLAY |
EP04763959A EP1658351B1 (en) | 2003-08-25 | 2004-08-10 | Mesogenic compounds, medium for electro-optical displays and electro-optical display |
KR1020067003696A KR101198452B1 (en) | 2003-08-25 | 2004-08-10 | Mesogenic compounds, medium for electro-optical displays and electro-optical display |
US10/569,459 US7531106B2 (en) | 2003-08-25 | 2004-08-10 | Mesogenic compounds, medium for electro-optical displays and electro-optical display |
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JP (1) | JP2007503487A (en) |
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AT (1) | ATE447001T1 (en) |
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Also Published As
Publication number | Publication date |
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TW200526763A (en) | 2005-08-16 |
KR101198452B1 (en) | 2012-11-06 |
ATE447001T1 (en) | 2009-11-15 |
TWI387638B (en) | 2013-03-01 |
US20060286308A1 (en) | 2006-12-21 |
US7531106B2 (en) | 2009-05-12 |
EP1658351A1 (en) | 2006-05-24 |
JP2007503487A (en) | 2007-02-22 |
EP1658351B1 (en) | 2009-10-28 |
DE602004023857D1 (en) | 2009-12-10 |
KR20060119877A (en) | 2006-11-24 |
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