WO2005019377A1 - Compounds for use in liquid crystal media - Google Patents
Compounds for use in liquid crystal media Download PDFInfo
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- WO2005019377A1 WO2005019377A1 PCT/EP2004/008439 EP2004008439W WO2005019377A1 WO 2005019377 A1 WO2005019377 A1 WO 2005019377A1 EP 2004008439 W EP2004008439 W EP 2004008439W WO 2005019377 A1 WO2005019377 A1 WO 2005019377A1
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- alkyl
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- 0 Cc1ccc(C=C(C)*(*)C=C2)c2c1 Chemical compound Cc1ccc(C=C(C)*(*)C=C2)c2c1 0.000 description 19
- BONABWUGSAWHJS-VHYPUYLQSA-N C/C=C/c1ccc(/C=C/c(cc2F)ccc2N=C=S)cc1 Chemical compound C/C=C/c1ccc(/C=C/c(cc2F)ccc2N=C=S)cc1 BONABWUGSAWHJS-VHYPUYLQSA-N 0.000 description 1
- MQFMUEUQQNNEBV-UHFFFAOYSA-N CC(CC1)CCC1c(cc1F)ccc1C#N Chemical compound CC(CC1)CCC1c(cc1F)ccc1C#N MQFMUEUQQNNEBV-UHFFFAOYSA-N 0.000 description 1
- GJMWJHPFQOALFX-UHFFFAOYSA-N Cc(cc1F)cc(F)c1C1=SCCCS1 Chemical compound Cc(cc1F)cc(F)c1C1=SCCCS1 GJMWJHPFQOALFX-UHFFFAOYSA-N 0.000 description 1
- YIAWVEYKLJFZBS-UHFFFAOYSA-N Cc(cc1F)ccc1N=C=S Chemical compound Cc(cc1F)ccc1N=C=S YIAWVEYKLJFZBS-UHFFFAOYSA-N 0.000 description 1
- ITWKQSNDENWZBB-UHFFFAOYSA-N Fc(cc(cc1F)-c(cc2)ccc2-c2ccccc2)c1N=C=S Chemical compound Fc(cc(cc1F)-c(cc2)ccc2-c2ccccc2)c1N=C=S ITWKQSNDENWZBB-UHFFFAOYSA-N 0.000 description 1
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- 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
- C09K19/16—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 double bonds, e.g. stilbenes
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- 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
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- C09K19/10—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings
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- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
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- C09K2019/0459—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 -CF=CF- chain, e.g. 1,2-difluoroethen-1,2-diyl
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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 is related to compounds for use in liquid crystal media, liquid crystal media comprising said compounds, the use of said media in electro-optical devices, said electro-optical devices, and the use of said compounds in mesogenic media for use in electro-optical devices that may be operated in an optically isotropic state.
- Electro-optical devices based on liquid crystals are extremely well known to the person skilled in the art and can be based on various effects. Examples of such devices are cells having dynamic scattering, DAP (deformation of aligned phases) cells, guest/host cells, TN cells having a twisted nematic structure, STN (supertwisted nematic) cells, SBE (superbirefringence effect) cells and
- OMI optical mode interference
- the liquid crystal materials must have good chemical and thermal stability and good stability to electric fields and electromagnetic radiation. Furthermore, the liquid crystal materials should have low viscosity and produce short addressing times, low threshold voltages and high contrast in the cells.
- a suitable mesophase for example a nematic or cholesteric mesophase for the above-mentioned cells, at the usual operating temperatures, i.e. in the broadest possible range above and below room temperature.
- liquid crystals are generally used as mixtures of a plurality of components, it is important that the components are readily miscible with one another.
- Further properties, such as the electrical conductivity, the dielectric anisotropy and the optical anisotropy have to satisfy various requirements depending on the cell type and area of application. For example, materials for cells having a twisted nematic structure should have positive dielectric anisotropy and low electrical conductivity.
- MLC displays matrix liquid crystal displays with integrated non-linear elements for switching individual pixels
- media having large positive dielectric anisotropy, broad nematic phases, relatively low birefringence, very high specific resistance, good UV and temperature stability and low vapour pressure are desired.
- Matrix liquid crystal displays of this type are known.
- Non-linear elements which can be used for individual switching of the individual pixels are, for example, active elements (i.e. transistors).
- active matrix is then used, where a distinction can be made between two types:
- MOS metal oxide semiconductor
- TFTs Thin-film transistors
- the electro-optical effect used is usually the TN effect.
- TFTs comprising compound semiconductors, such as, for example, CdSe, or TFTs based on polycrystalline or amorphous silicon. Intensive work is being carried out world-wide on the latter technology.
- the TFT matrix is applied to the inside of one glass plate of the display, while the other glass plate carries the transparent counterelectrode on its inside. Compared with the size of the pixel electrode, the TFT is very small and has virtually no adverse effect on the image.
- This technology can also be extended to fully colour-capable displays, in which a mosaic of red, green and blue filters is arranged in such a way that a filter element is opposite each switchable pixel.
- the TFT displays usually operate as TN cells with crossed polarisers in transmission and are illuminated from the back.
- MLC displays of this type are particularly suitable for TV applications (for example pocket TVs) or for high-information displays for computer applications (laptops) and in automobile or aircraft construction.
- TV applications for example pocket TVs
- high-information displays for computer applications (laptops) and in automobile or aircraft construction.
- difficulties also arise in MLC displays due to insufficiently high specific resistance of the liquid crystal mixtures [TOGASHI, S., SEKIGUCHI, K., TANABE, H., YAMAMOTO, E., SORIMACHI, K., TAJIMA, E., WATANABE, H., SHIMIZU, H., Proc. Eurodisplay 84, Sept. 1984: A 210-288 Matrix LCD Controlled by Double Stage Diode Rings, p. 141 ff, Paris; STROMER, M., Proc. Eurodisplay 84, Sept. 1984: Design of Thin Film Transistors for Matrix
- VHR voltage holding ratio
- a, b, c and d are independently of each other 0, 1 or 2, whereby a + b + c + d ⁇ 4;
- L 13 and L 14 are hydrogen, if at least one of L 11 and L 12 is not hydrogen; L 11 and L 12 are hydrogen, if at least one of L 13 and L 14 is not hydrogen; at least one of L 11 , L 12 , L 13 and L 14 is not hydrogen; and L 11 and L 12 are
- X 11 is H, halogen, -CN, -NCS, -SF 5 , -S-R z , -SO 2 -R z , an alkyl or alkoxy radical having from 1 to 15 carbon atoms, wherein one or more methylene groups of said alkyl or alkoxy radical may be replaced independently
- R x and R y are independently of each other hydrogen or an alkyl radical having from 1 to 7 carbon atoms;
- R z is an alkyl radical having from 1 to 7 carbon atoms, said alkyl radical being unsubstituted or mono- or poly-substituted with halogen;
- 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 -trifluoro-2-aikyl and 1 ,1 ,1-trifluoro-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.
- At least one 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 PG-SG wherein SG is a spacer group and PG is a polymerisable or reactive group.
- 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.
- R x has the meaning given above and preferably is n-alkyl and most preferably methyl.
- L 12 is F, a straight-chain alkyl, alkenyl, alkoxy, alkenyloxy or -O-alkylene-O-alkyl radical or a -O-alkylene-Si(alkyr) 2 -O-Si(alkyF) 3 radical with up to 10 carbon atoms which radicals may be additionally substituted with fluorine whereby alkyl' is preferably a straight-chain alkyl radical with 1 , 2, 3 or 4 carbon atoms.
- L 2 is either F or one of the following radicals: perfluoroalkyl; C n H 2r , + i-O- with n being 1, 2, 3, 4, 5, 6, 7 or 8 whereby one or more of the H atoms may be replaced by F; C m H 2 m-rO- with m being 2, 3, 4, 5, 6, 7 or 8 whereby one or more of the H atoms may be replaced by F; C p H 2p+1 - O-C q H 2q -O- with p being 1 , 2, 3, 4 or 5 and q being 1 , 2, 3, 4 or 5; (C t H 2t+ ⁇ ) 3 Si-O-Si(C s H 2 s + ⁇ ) 2 -C r H 2r O- with r being 1 , 2, 3 or 4 and s and t being independently of each other 1 , 2, 3 or 4.
- L 1 and L 12 have the same meaning.
- L 11 and L 12 are both hydrogen
- L 13 and L 14 are both not hydrogen and have the same meaning as L 11 and L 12 in the case L 11 and L 12 are not hydrogen.
- X 11 is a polar substituent.
- X 11 is -NCS, -SF 5 , -S-R 2 or -SO 2 -R z , with R 2 being a straight-chain alkyl radical that is mono- or poly-substituted with fluorine, especially -CF 3 , - C 2 F 5 or n-C 4 F 9 .
- X 11 is also selected from F, Cl, CN, an alkyl, alkenyl or alkoxy radical having up to 8 carbon atoms said alkyl or alkenyl radical being mono- or poly-substituted with fluorine and said alkoxy radical being unsubstituted or mono- or poly- substituted with fluorine.
- Y 11 is one of the following radicals: H; F; perfluoroalkyl; C n H 2n+ rO- with n being 1 , 2, 3, 4, 5, 6, 7 or 8 whereby one or more of the H atoms may be replaced by F; CmH 2 m- O- with m being 2, 3, 4, 5,
- Y 11 is F, CF 3 , -O-CH 3 , -O-C 2 H 5 , -O-C 3 H 7 , -O-n-C 4 H 9 , -O-n-C 5 Hn, O-n-C 6 H 13 , -O-CF 3 , -O-CHF 2 ,
- Y 12 is hydrogen or has the same meaning as the preferred definitions of Y 11 above. Especially, Y 12 is H. Furthermore, is also preferred that
- compounds of formula I comprising a tetrahydropyranyl-2,5-diyl ring that bears two stereogenic centers on C-2 and C-5, respectively, may be obtained, if desired, in stereochemically pure form by way of, e.g., methods for separating stereoisomers that are well known to the skilled person, for instance, HPLC on a chiral phase.
- At least one of A 11 and A 12 and especially A 11 is a tetrahydropyran-2,5-diyl ring.
- at least one of A 13 and A 14 and particularly only one of A 13 and A 14 is of the formula with f and g being independently of each other 0, 1 , 2 or 3. It is highly preferred that f is 1 and g is 2 or 3 and the fluorine substituents are located in the 1-, 3-, 4- and 8-position, respectively, of the naphthyl moiety.
- one of A 11 and A 12 is a tetrahydropyran- 2,5-diyl moiety and one of A 13 and A 14 is an optionally fluorinated naphthyl-2,6- diyl moiety.
- R 11 is H, an alkyl or alkoxy radical having from 1 to 15 carbon atoms or an alkenyl or alkenyloxy or -O-alkylene-O-alkyl radical having from 2 to 15 carbon atoms, wherein one or more methylene groups of each of said radicals may be replaced independently of each other by -S-, -SiR x R y -, -C ⁇ C-, -CO-O- and/or -O-CO- such that oxygen and/or sulfur atoms are not linked directly to each other, said radicals being unsubstituted or mono-substituted with a -CN group or mono- or poly-substituted with halogen; preferably R 11 is a straight-chain alkyl, alkoxy, alkenyl, alkenyloxy or -O-alkylene-O-alkyl radical with up to 10 carbon atoms, said radicals being unsubstituted or mono- or poly-substitute
- One preferred subgroup of compounds according to formula IA are compounds in which c is zero. Examples of compounds of said subgroup are the following ones:
- n and m are independently of each other integers from 1 to 10, preferably 1 , 2, 3, 4, 5, 6, 7 or 8; p is an integer from 1 to 5, preferably 1 , 2 or 4; q and r are independently of each other integers from 2 to 8, preferably 3, 4, 5, 6; s and t are independently of each other 1 , 2, 3, 4, preferably 2 or 3; and u and v are independently of each other 1 , 2, 3, 4, preferably 1 or 4.
- C n H 2n + ⁇ O and CmH 2m+1 O represent independently of each other methoxy, ethoxy, propoxy, n-butoxy, n-pentoxy and n-hexoxy.
- both C m H 2 m + ⁇ O substituents may have the same value for m or different ones; preferably m in two CmH 2 m + ⁇ O substituents have the same meaning.
- -SO 2 -C p H 2p+ ⁇ represents -SO 2 -CF 3 , -SO 2 -C 2 F 5 , -SO 2 - C 4 F 9 .
- (C v H 2v+1 ) 3 SiOSi(CuH 2 u + ⁇ ) 2 CsH 2s O represents (CH 3 ) 3 SiOSi(CH 3 ) 2 CH 2 CH 2 O- and (CH 3 ) 3 SiOSi(CH 3 ) 2 CH 2 CH 2 CH 2 O-.
- Another preferred subgroup of compounds according to formula IA are compounds in which c is 1.
- Examples of compounds of said subgroup are the following ones:
- L a and L b are independently of each other H or F; n and m are independently of each other integers from 1 to 10, preferably 1 , 2, 3, 4, 5, 6, 7 or 8; p is an integer from 1 to 5, preferably 1 , 2 or 4; q and r are independently of each other integers from 2 to 8, preferably 3, 4, 5, 6; s and t are independently of each other 1 , 2, 3, 4, preferably 2 or 3; and u and v are independently of each other 1, 2, 3, 4, preferably 1 or 4.
- at least one of L a and L b is F, and especially preferably, both L a and L b are F.
- both CmH 2 m+ ⁇ O substituents may have the same value for m or different ones; preferably m in two C m H 2rn + ⁇ O substituents have the same meaning.
- C n H 2n+ ⁇ O and C m H 2m+1 O represent independently of each other methoxy, ethoxy, propoxy, n-butoxy, n-pentoxy and n-hexoxy.
- -SO 2 -C p H 2p+ ⁇ represents -SO 2 -CF 3 , -SO 2 -C 2 F 5 , - SO 2 -C 4 F 9 .
- -OC S HZ S OQH ZM represents CH 3 OCH 2 CH 2 O- and CH 3 CH 2 OCH 2 CH 2 O-.
- (CvH 2v + ⁇ ) 3 SiOSi(C u H 2u+ ⁇ ) 2 C s H 2s O represents (CH 3 ) 3 SiOSi(CH 3 ) 2 CH 2 CH 2 O- and (CH 3 ) 3 SiOSi(CH 3 ) 2 CH 2 CH 2 CH 2 O-.
- Still another preferred subgroup of compounds according to formula IA are compounds of formulas lAc and lAd.
- n and m are the same number and equal to 1 , 2, 3, 4, 5 or 6. If present twice in the same compound, both C m H 2m + ⁇ O substituents may have the same value for m or different ones; preferably m in two C m H m + ⁇ O substituents have the same meaning. Furthermore, one or more of the hydrogen atoms of the C n H 2n + ⁇ , the OC n H 2n+ ⁇ and the OCmH 2 m + ⁇ moiety, respectively, may be replaced by a halogen atom, preferably a fluorine atom. Particularly preferred are compounds of formulas IB-1 to IB-21 with X 11 being F, CF 3 or OCF 3l especially F.
- R 11 is H, an alkyl or alkoxy radical having from 1 to 15 carbon atoms or an alkenyl or alkenyloxy or -O-alkylene-O-alkyl radical having from 2 to 15 carbon atoms, wherein one or more methylene groups of each of said radicals may be replaced independently of each other by -S-, -SiR x R y -, -C ⁇ C-, -CO-O- and/or -O-CO- such that oxygen and/or sulfur atoms are not linked directly to each other, said radicals being unsubstituted or mono-substituted with a -CN group or mono- or poly-substituted with halogen; preferably R 11 is a straight-chain alkyl, alkoxy, alkenyl, alkenyloxy or -O-alkylene-O-alkyl radical with up to 10 carbon atoms, said radicals being unsubstituted or mono- or poly-substitute
- L 11 is an alkyl or alkoxy radical having from 1 to 15 carbon atoms or an alkenyl or alkenyloxy or -O-alkylene-O-alkyl radical having from 2 to 15 carbon atoms, wherein one or more methylene groups of each of said radicals may be replaced independently of each other by -S-, -SiR x R y -, -C ⁇ C-, -CO-O- and/or -O-CO- such that oxygen and/or sulfur atoms are not linked directly to each other, said radicals being unsubstituted or mono-substituted with a -CN group or mono- or poly-substituted with halogen; preferably, L 11 is a straight-chain alkyl, alkoxy, alkenyl, alkenyloxy or -O-alkylene-O-alkyl radical with up to 10 carbon atoms, said radicals being unsubstituted or mono- or poly-substituted
- both CmH 2m+ iO substituents may have the same value for m or different ones; preferably in two CmH 2m+ ⁇ O substituents m is the same integer.
- both C q H 2q . ⁇ O substituents may have the same value for q or different ones; preferably in two C q H 2q . ⁇ O substituents q is the same integer.
- n and m are the same number and equal to 1 , 2, 3, 4, 5 or 6.
- R 11 is H, an alkyl or alkoxy radical having from 1 to 15 carbon atoms or an alkenyl or alkenyloxy or -O-alkylene-O-alkyl radical having from 2 to 15 carbon atoms, wherein one or more methylene groups of each of said radicals may be replaced independently of each other by -S-, -SiR x R y -, -C ⁇ C-, -CO-O- and/or -O-CO- such that oxygen and/or sulfur atoms are not linked directly to each other, said radicals being unsubstituted or mono-substituted with a -CN group or mono- or poly-substituted with halogen; preferably R 11 is a straight-chain alkyl, alkoxy, alkenyl, alkenyloxy or -O-alkylene-O-alkyl radical with up to 10 carbon atoms, said radicals being unsubstituted or mono- or poly-substitute
- both C m H 2m +iO substituents may have the same value for m or different ones; preferably in two C m H 2 ⁇ +1 O substituents m is the same integer.
- both CqH ⁇ O substituents may have the same value for q or different ones; preferably in two C q H 2q . ⁇ O substituents q is the same integer.
- n and m are the same number and equal to 1 , 2, 3, 4, 5 or 6.
- both q and p are the same number and equal to 3, 4, 5, 6.
- one or more of the hydrogen atoms of the C n H 2n+ ⁇ , the OC n H 2n+1 , the OC m H 2 m +1 , the OC p H 2p- ⁇ and the OC q H 2q - ⁇ moiety, respectively, may be replaced by a halogen atom, preferably a fluorine atom.
- a halogen atom preferably a fluorine atom.
- Particularly preferred are compounds of formulas IE-1 to IE-51 with X 11 being NCS, SF 5 , SO 2 CF 3 , SO 2 C 2 F 5 , SO 2 C 4 F 9 .
- both CmH 2m+ ⁇ O substituents may have the same value for m or different ones; preferably in two C m H 2m+1 O substituents m is the same integer.
- both C q H 2q . ⁇ O substituents may have the same value for q or different ones; preferably in two C q H 2q- ⁇ O substituents q is the same integer.
- n and m are the same number and equal to 1 , 2, 3, 4, 5 or 6.
- both q and p are the same number and equal to 3, 4, 5, 6.
- »11 is an alkyl or alkoxy radical having from 1 to 15 carbon atoms or an alkenyl or alkenyloxy or -O-alkylene-O-alkyl radical having from 2 to 15 carbon atoms, wherein one or more methylene groups of each of said radicals may be replaced independently of each other by -S-, -SiR x R y -, -C ⁇ C-, -CO-O- and/or -O-CO- such that oxygen and/or sulfur atoms are not linked directly to each other, said radicals being unsubstituted or mono-substituted with a -CN group or mono- or poly-substituted with halogen; preferably R 11 is a straight-chain alkyl, alkoxy, alkenyl, alkenyloxy or -O-alkylene-O-alkyl radical with up to 10 carbon atoms, said radicals being unsubstituted or mono- or poly-substituted with
- L 15 and L 16 are independently of each other H, CF 3 or F; preferably both L 15 and L 16 are F or CF 3 ;
- X 11 is F, Cl, -CN, -NCS, -SF 5 , -S-R z , -SO 2 -R z , an alkyl or alk
- C n H 2n+ ⁇ O, C m H 2m+ ⁇ O and C w H 2w + ⁇ O represent independently of each other methoxy, ethoxy, propoxy, n-butoxy, n-pentoxy and n-hexoxy.
- C q H 2 q- ⁇ O, C y H 2y- ⁇ O and C r H 2r - ⁇ O represent
- -OC s H 2s OC t H 2t+ ⁇ represents CH 3 OCH 2 CH 2 O- and CH 3 CH 2 OCH 2 CH 2 O-.
- Another preferred subgroup of compounds according to formula IG are compounds in which d is 1. Examples of compounds of said subgroup are the
- C n H 2n+ ⁇ O, C H 2m + ⁇ O and C w H 2w + ⁇ O represent independently of each other methoxy, ethoxy, propoxy, n-butoxy, n-pentoxy and n-hexoxy.
- -OC s H 2s OC t H 2t+1 represents CH 3 OCH 2 CH 2 O- and CH 3 CH 2 OCH 2 CH 2 O-.
- (C v H 2v+ ⁇ ) 3 SiOSi(C u H 2u+ ⁇ ) 2 C s H 2s O represents (CH 3 ) 3 SiOSi(CH 3 ) 2 CH 2 CH 2 O- and (CH 3 ) 3 SiOSi(CH 3 ) 2 CH 2 CH 2 O-.
- Particularly preferred are compounds of formulas IGb-1 to IGb-51 with X 11 being F, CF 3 or OCF 3 , especially F.
- liquid crystal media comprising at least one compound of formula I.
- Said media may further comprise from 2 to 40, in particular from 4 to 30, components as further constituents besides one or more compounds according to the invention.
- These media very particularly preferably comprise from 7 to 25 components besides one or more compounds according to the invention.
- nematic or nematogenic (monotropic or isotropic) substances are preferably selected from nematic or nematogenic (monotropic or isotropic) substances, in particular substances from the classes of the azoxybenzenes, benzylideneanilines, biphenyls, terphenyls, phenyl or cyclohexyl benzoates, phenyl or cyclohexyl esters of cydohexanecarboxylic acid, phenyl or cyclohexyl esters of cyclohexyl- benzoic acid, phenyl or cyclohexyl esters of cyclohexylcyclohexanecarboxylic acid, cyclohexylphenyl esters of benzoic acid, of cydohexanecarboxylic acid or of cyclohexylcyclohexanecarboxylic acid, phenylcydohe
- R' is as defined for the compounds of the sub-formulae 1 a-5a and is preferably alkyl, alkenyl, alkoxy or alkoxyalkyl.
- R' is as defined for the compounds of the sub-formulae 1a-5a and is preferably alkyl, alkoxy or alkenyl.
- the media according to the invention preferably comprise one or more compounds selected from group A and/or group B and/or group C.
- the proportions by weight of the compounds from these groups in the media according to the invention are preferably group A: from 0 to 90%, preferably from 20 to 90%, in particular from 30 to 90% group B: from 0 to 80%, preferably from 10 to 80%, in particular from 10 to 65% group C: from 0 to 80%, preferably from 5 to 80%, in particular from 5 to 50%,
- the sum of the proportions by weight of the group A and/or B and/or C compounds present in the respective media according to the invention is pref- erably from 5 to 90% and in particular from 10 to 90%.
- German Patent Application DE 102 17 273 A1 discloses light controlling (light modulation) elements in which the mesogenic controlling medium for modulation is in the isotropic phase at the operating temperature. These light controlling elements have a very short switching time and a good viewing angle dependence of contrast. However, the driving or operating voltages of said elements are very often unsuitably high for some applicatons.
- chiral binaphthyl derivatives as disclosed in EP 01 111 954.2, chiral binaphtol derivatives as disclosed in WO 02/34739, chiral TADDOL derivatives as disclosed in WO 02/06265 as well as chiral dopants having at least one fluorinated linker and one end chiral moiety or one central chiral moiety as disclosed in WO 02/06196 and WO 02/06195.
- chiral component (A) may also comprise a chiral compound of formula I.
- alkyl in “O-alkyl” means methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, neopentyl, n-hexyl, n-heptyl or n-octyl, whereby alkyl is optionally substituted with F.
- alkoxy comprises methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy and octoxy that all may be substituted with one or more F atoms.
- oxaalkyl comprises alkyl moieties in which at least one non-terminal CH 2 group is replaced by O in such a way that there are no adjacent oxygen atoms.
- oxaalkyl comprises straight-chain radicals of the formula C t H 2t+ rO-(CH 2 ) u - in which t and u are independently of each other 1 , 2, 3, 4, 5 or 6; especially t is 1 or 2 and u is an integer from 1 to 6.
- -O-alkylene-O-alkyl is meant to comprise an alkyl moiety in which a first oxygen atom is directly linked to the atom, group and ring, respectively, that is substituted with -O-alkylene-O-alkyl, and in which said first oxygen atom is linked to an O-alkyl group via an alkylene linker, i.e. an divalent aliphatic hydrocarbon moiety such as -CH 2 -, -CH 2 -CH 2 -, -CH 2 -CH 2 -CH 2 - or
- Thioalkyl comprises alkyl moieties in which at least one terminal or non-terminal CH 2 group is replaced by S (sulphur) in such a way that there are no adjacent sulphur atoms.
- thioalkyl comprises straight-chain radicals of the formula C t H 2t+ rS-(CH 2 ) u - in which t is 1 , 2, 3, 4, 5 or 6 and u is 0, 1 , 2, 3, 4, 5 or 6; especially t is 1 or 2 and u is zero or an integer from 1 to 6.
- An alkenyl radical may comprise 2 to 15 carbon atoms and may be straight-chain or branched. It can be unsubstituted or mono- or polysubstituted with F, Cl, Br, I or CN; one or more of its CH 2 groups may be replaced independently of each other by -O-, -S-, -C ⁇ C-, -CO-O-, -OC-O- such that there are no hetero atoms adjacent to each other.
- alkenyl is vinyl, 1E-propenyl, 3E-butenyl.
- alkenyloxy means an "-O- alkenyl" radical in which an alkenyl moiety that is as defined above is linked to an atom, group or ring to be substituted via an oxygen atom; one or more of the hydrogen atoms of the alkenyl moiety may be replaced by halogen, preferably fluorine. It is preferred that the carbon-carbon double bond of the alkenyloxy radical is a terminal double bond.
- Alkenyloxy may have 2 to 15 carbon atoms, preferably 2 to 10 carbon atoms and more preferably 3, 4, 5, 6, 7 or 8 carbon atoms.
- an alkinyl radical is obtained.
- the replacement of one or more CH 2 alkyl groups by - CO-O- or -O-CO- is possible.
- the following of these radicals are preferred: acetyloxy, propionyloxy, butyryloxy, pentanoyloxy, hexanoyloxy, acetyloxymethyl, propionyloxymethyl, butyryloxymethyl, pentanoyloxymethyl, 2- acetyloxyethyl, 2-propionyloxyethyl, 2-butyryloxyethyl, 2-acetyloxypropyl, 3- propionyloxypropyl, 4-acetyloxybutyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl,
- halogen denotes F, Cl, Br and/or I, preferably F.
- C denotes a crystalline phase
- S a smectic phase S c a smectic C phase
- SB a smectic B phase N a nematic phase
- I the isotropic phase.
- V xx denotes the voltage for xx% transmission (viewing angle perpendicular to the plate surface), e.g. V 10 denotes the voltage at for 10% transmission.
- t on denotes the switch-on time and t off the switch-off time at an operating voltage corresponding to the value of V 10 o.
- ⁇ n denotes the optical anisotropy and n 0 the refractive index.
- the orientation layers were lecithin for homeotropic orientation ( ⁇ 1 1 ) and polyimide AL-1054 from Japan Synthetic Rubber for homogeneuous orientation ( ⁇ j . ).
- the capacities were determined with a frequency response analyser Solatron 1260 using a sine wave with a voltage of 0.3 ⁇ / ms .
- 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 (V ⁇ 0 ) - mid grey (V 50 ) - and saturation (V 90 ) voltages have been determined for 10 %, 50 % and 90 % relative contrast, respectively.
- Table B is self-evident. In Table A, only the acronym for the parent structure is indicated. In individual cases, the acronym for the parent structure is followed, separated by a dash, by a code for the substituents R 1 , R2, Li and L2:
- a suspension of 0.1 mol of 1 (prepared according to the procedures given in WO 01/64667) in 300 ml methylenechloride was cooled to -70 °C and treated dropwise with a mixture of 0.15 mol 4-pentafluorosulfuranylphenol, 0.17 mol triethylamine and 100 ml methylenechloride. After 5 min a first portion of 0.5 mol NEt 3 -3HF was added dropwise, and after additional 5 min 0.5 mol bromine were added. After stirring for 1 h at -70 °C, the mixture was allowed to warm up to room temperature and poured into ice-cold 0.1 N NaOH.
- a liquid crystal mixture, host mixture A is realised consisting of:
- 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 V 90 at which a transmission of 90% is observed.
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Abstract
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US10/569,462 US8129002B2 (en) | 2003-08-25 | 2004-07-28 | Compounds for use in liquid crystal media |
KR1020067003729A KR101198471B1 (en) | 2003-08-25 | 2004-07-28 | Compounds for use in liquid crystal media |
AT04763558T ATE455833T1 (en) | 2003-08-25 | 2004-07-28 | COMPOUNDS FOR USE IN LIQUID CRYSTALLINE MEDIA |
EP04763558A EP1658350B1 (en) | 2003-08-25 | 2004-07-28 | Compounds for use in liquid crystal media |
JP2006524249A JP2007503405A (en) | 2003-08-25 | 2004-07-28 | Compounds for use in liquid crystal media |
DE602004025254T DE602004025254D1 (en) | 2003-08-25 | 2004-07-28 | COMPOUNDS FOR USE IN LIQUID CRYSTALLINE MEDIA |
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Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1986006372A1 (en) * | 1985-05-02 | 1986-11-06 | MERCK Patent Gesellschaft mit beschränkter Haftung | Benzonitrile |
US5352381A (en) * | 1990-06-11 | 1994-10-04 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal thiol compounds |
US5358663A (en) * | 1987-10-19 | 1994-10-25 | The Secretary Of State For Defence In Her Britannic Majesty'3 S Government Of U.K. Of Gt. Britain And N. Ireland | Laterally cyano- and fluoro-substituted terphenyls |
JPH08143498A (en) * | 1994-11-17 | 1996-06-04 | Dainippon Ink & Chem Inc | 5-substituted alkoxybenzene derivative |
US5536442A (en) * | 1987-09-25 | 1996-07-16 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Fluorinated liquid crystal compounds and liquid crystal medium containing same |
WO1996031576A1 (en) * | 1995-04-07 | 1996-10-10 | The Secretary Of State For Defence, Defence Evaluation & Research Agency | Polysiloxanes |
US6177154B1 (en) * | 1996-09-17 | 2001-01-23 | Chisso Corporation | Alkoxybenzene derivative, liquid-crystal composition, and liquid-crystal display element |
GB2367057A (en) * | 2000-06-28 | 2002-03-27 | Merck Patent Gmbh | Benzonitriles with both chloro and fluoro lateral substituents for use as components of liquid crystalline media |
GB2379442A (en) * | 2001-07-25 | 2003-03-12 | Merck Patent Gmbh | Liquid crystalline isothiocyanates |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4949027B2 (en) * | 2003-08-25 | 2012-06-06 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | Liquid crystal media |
EP1658351B1 (en) * | 2003-08-25 | 2009-10-28 | MERCK PATENT GmbH | Mesogenic compounds, medium for electro-optical displays and electro-optical display |
-
2004
- 2004-07-28 DE DE602004025254T patent/DE602004025254D1/en not_active Expired - Fee Related
- 2004-07-28 KR KR1020067003729A patent/KR101198471B1/en not_active IP Right Cessation
- 2004-07-28 WO PCT/EP2004/008439 patent/WO2005019377A1/en active Application Filing
- 2004-07-28 AT AT04763558T patent/ATE455833T1/en not_active IP Right Cessation
- 2004-07-28 US US10/569,462 patent/US8129002B2/en not_active Expired - Fee Related
- 2004-07-28 JP JP2006524249A patent/JP2007503405A/en active Pending
- 2004-07-28 EP EP04763558A patent/EP1658350B1/en not_active Expired - Lifetime
- 2004-08-26 TW TW093125430A patent/TWI362410B/en not_active IP Right Cessation
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1986006372A1 (en) * | 1985-05-02 | 1986-11-06 | MERCK Patent Gesellschaft mit beschränkter Haftung | Benzonitrile |
US5536442A (en) * | 1987-09-25 | 1996-07-16 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Fluorinated liquid crystal compounds and liquid crystal medium containing same |
US5358663A (en) * | 1987-10-19 | 1994-10-25 | The Secretary Of State For Defence In Her Britannic Majesty'3 S Government Of U.K. Of Gt. Britain And N. Ireland | Laterally cyano- and fluoro-substituted terphenyls |
US5352381A (en) * | 1990-06-11 | 1994-10-04 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Liquid crystal thiol compounds |
JPH08143498A (en) * | 1994-11-17 | 1996-06-04 | Dainippon Ink & Chem Inc | 5-substituted alkoxybenzene derivative |
WO1996031576A1 (en) * | 1995-04-07 | 1996-10-10 | The Secretary Of State For Defence, Defence Evaluation & Research Agency | Polysiloxanes |
US6177154B1 (en) * | 1996-09-17 | 2001-01-23 | Chisso Corporation | Alkoxybenzene derivative, liquid-crystal composition, and liquid-crystal display element |
GB2367057A (en) * | 2000-06-28 | 2002-03-27 | Merck Patent Gmbh | Benzonitriles with both chloro and fluoro lateral substituents for use as components of liquid crystalline media |
GB2379442A (en) * | 2001-07-25 | 2003-03-12 | Merck Patent Gmbh | Liquid crystalline isothiocyanates |
Non-Patent Citations (2)
Title |
---|
BEZBORODOV ET AL: "SYNTHESIS AND PROPERTIES OF SOME LATERALLY SUBSTITUTED LIQUID CRYSTALS", LIQUID CRYSTALS, TAYLOR AND FRANCIS LTD, LONDON, GB, vol. 21, no. 6, 1 December 1996 (1996-12-01), pages 801 - 806, XP000639773, ISSN: 0267-8292 * |
PATENT ABSTRACTS OF JAPAN vol. 1996, no. 10 31 October 1996 (1996-10-31) * |
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Also Published As
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EP1658350A1 (en) | 2006-05-24 |
US20060263542A1 (en) | 2006-11-23 |
KR20060119879A (en) | 2006-11-24 |
ATE455833T1 (en) | 2010-02-15 |
KR101198471B1 (en) | 2012-11-06 |
EP1658350B1 (en) | 2010-01-20 |
TWI362410B (en) | 2012-04-21 |
US8129002B2 (en) | 2012-03-06 |
DE602004025254D1 (en) | 2010-03-11 |
JP2007503405A (en) | 2007-02-22 |
TW200526765A (en) | 2005-08-16 |
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