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  • 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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  • C09K19/08—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
  • C09K19/12—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing at least two benzene rings at least two benzene rings directly linked, e.g. biphenyls
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  • 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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  • C09K19/0403—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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  • C09K2019/0477—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by the positioning of substituents on phenylene
  • C09K2019/0481—Phenylene substituted in meta position
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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
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
  • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
  • C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
  • C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
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  • C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
  • C09K2019/343—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a seven-membered ring
  • C09K2019/3433—Seven-membered ring with oxygen(s) in fused, bridged or spiro ring systems

Definitions

• Liquid Crystal Compounds Liquid Crystal Medium and Liquid Crystal Display
• the present invention relates to mesogenic compounds, mesogenic media and to electro-optical displays comprising these mesogenic media as light modulation media, in particular to displays which are operated at a temperature at which the mesogenic modulation media are in an optically isotropic phase, preferably in a blue phase.
• Electro-optical displays and mesogenic light modulation media, which are in the isotropic phase when being operated in the display are described in DE 102 17273 A. Electro-optical displays, and mesogenic light modulation media, which are in the optically isotropic blue phase, when being operated in the display are described in DE 103 13 979.6, which is not yet laid open.
• the mesogenic media and displays described in these references provide several significant advantages compared to well-known and widely used displays using liquid crystals in the nematic phase, like for example liquid crystal displays (LCDs) operating in the twisted nematic (TN)-, the super twisted nematic (STN)-, the electrically controlled birefringence (ECB)- mode with its various modifications and the in-pjane switching (IPS)-mode.
• LCDs liquid crystal displays
• STN super twisted nematic
• ECB electrically controlled birefringence
• IPS in-pjane switching
• the displays of DE 102 17 273.0 and DE 103 13 979 are much easier to be produced. For example, they do not require a very thin cell gap in the first place and the electro-optical effect is not very sensitive to small variations of the cell gap as well.
• the liquid crystal media described in these mentioned patent applications still require operating voltages, which are not low enough for some applications. Further the operating voltages of these media vary with temperature, and it is generally observed, that at a certain temperature the voltage dramatically increases with increasing temperature. This limits the applicability of liquid crystal media in the blue phase for display applications.
• a further disadvantage of the liquid crystal media described in these patent applications is their moderate reliability which is insufficient for very demanding applications. This moderate reliability may be for example expressed in terms of the voltage holding ratio parameter (VHR), which in liquid crystal media as described above may be below 90%.
• VHR voltage holding ratio parameter
• the light modulation medium to be used has to be in the blue phase over a broad range of temperatures encompassing ambient temperature, however.
• a light modulation medium possessing a blue phase which is as wide as possible and conveniently located is required.
• a modulation medium with a blue phase with a wide phase range which may be achieved either by an appropriate mixture of mesogenic compounds themselves or, preferably by mixing a host mixture with appropriate mesogenic properties with a single dopant or a mixture of dopants that stabilises the blue phase over a wide temperature range.
• mesogenic compounds with a molecular structure comprising of a phenyl ring, which is bearing two mesogenic groups in otho position to each other, which are preferably identical to each other, and preferably the mesogenic compounds are substituted by one cyclic group or by two noncyclic groups on the opposite side of the two mesogenic groups mentioned, are suitable to considerably enhance the range of temperatures over which the blue phase is stable or even induce a blue phase in respective mesogenic hosts, which do not show such a phase on their own.
• the mesogenic hosts are liquid crystalline hosts.
• the two mesogenic groups do each contain at least one ring element, which is preferably selected from the group of four -, five -, six - or seven -, preferably of five - or six -, membered rings, which optionally are linked to one or more ring elememts selected from this group of ring elements by a direct bond or a linking group.
• the compounds according to the present invention are chiral compounds, preferably they comprise at leasrt one chirally substituted atom and most preferably a chirally substituted C-atom.
• R 13 and R 14 have, independently of each other, one of the meanings ggiivveenn ffoorr RR 1111 oorr aalltteerrnnaattiivveellyy together form one of the cyclic groups CG-1 to CG-6
• p is an integer from 1 to 6
• R 15 and R 16 have, independently of each other, one of the meanings given for R 11 or alternativeatively, again independently of each other, have one of the meanings given for and — ⁇ A 12 > are, independently of each other occurring more than once, also these are in each occurrence independently of each other, an aromatic and/or alicyclic ring, or a group comprising two or more fused aromatic or alicyclic rings, wherein these rings optionally contain one or more hetero atoms selected from N, O and/or S, and are optionally monosubstituted or polysubstituted by R, wherein
• R has one of the meanings given for R 11 and preferably is
• H. F, Cl, CN or alkyl preferably H, F or alkyl with 1 to 10 C-atoms,
• Z 11 and Z 12 are, independently of each other, and in case Z 11 and/or
• Y 0 and Y 02 are, independently of each other, F, Cl or CN, and alternatively one of them may be H,
• R 01 and R 02 are, independently of each other, H or alkyl with 1 to 12
• Y 11 and Y 2 are, independently of each other, H, F, Cl, CN or NCS, preferably H or F and n and m are, independently of each other 1 , 2, 3 or 4, preferably
• R 13 and R 14 are identical with each other or
• R 13 and R 14 together form one of the cyclic groups CG-1 to CG-6, preferably CG-2, CG-3 or CG-4.
• rings A 11 to A 13 are, independently of each other, an aromatic or alicyclic ring, preferably a 5-, 6- or 7-membered ring, or a group comprising two or more, preferably two or three, fused aromatic or alicyclic rings, wherein these rings optionally contain one or more hetero atoms selected from N, O and/or S, and are optionally mono- or polysubstituted with L, wherein L is F, Cl, Br, CN, OH, N0 2 , and/or an alkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl group with 1 to 12 C atoms, wherein one or more H atoms are optionally replaced by F or Cl.
• L is preferably F, Cl, CN, OH, N0 2 , CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , COCH 3 ,
• Preferred rings A 11 and A 12 are for example furane, pyrrol, thiophene, oxazole, thiazole, thiadiazole, imidazole, phenylene, cyclohexylene, cyclohexenylene, pyridine, pyrimidine, pyrazine, azulene, indane, naphthalene, tetrahydronaphthalene, decahydronaphthalene, tetrahydropyrane, anthracene, phenanthrene and fluorene.
• one or more of these rings A 11 and A 12 is, respectively are, selected from furane-2,5-diyl, thiophene-2,5-diyl, thienothiophene-2,5-diyl, dithienothiophene-2,6-diyl, pyrrol-2,5-diyl, 1 ,4- phenylene, azulene-2,6-diyI, pyridine-2,5-diyl, pyrimidine-2,5-diyl, naphthalene-2,6-diyl, 1 ,2,3,4-tetrahydro-naphthalene-2,6-diyl, indane-2,5- diyl, or 1 ,4-cyclohexylene wherein one or two non-adjacent CH 2 groups are optionally replaced by O and/or S, wherein these groups are unsubstituted, mono- or polysubstituted by L as
• both of them contains only monocyclic rings A 11 and A 12 .
• this is a group containing one or two 5- and/or 6-membered rings.
• Phe in these groups is 1 ,4-phenylene
• PheL is a 1 ,4-phenylene group which is substituted by 1 to 4 groups L as defined above
• Cyc is 1 ,4- cyclohexylene
• Pyd is pyridine-2,5-diyl
• Pyr is pyrimidine-2,5-diyl.
• the following list of preferred groups is comprising the sub formulae A-1 to A-20 as well as their mirror images,
• Z has the meaning of Z 1 as given in formula
• Z is -CF 2 -0- or -0-CF 2 - or a single bond.
• L has the meaning given above and r and s are independently of each other, 0, 1 , 2, 3 or 4, preferably 0, 1 or 2.
• Especially preferred compounds of formula I comprise at least one group each in rings A 11 and A 12 of the formula
• r is 1 or 2.
• r is 2 and/or at least one group each of the formula At wherein r is 0, 1 or 2.
• 1 ,4-phenylene rings may optionally be substituted by R or L, preferably by alkyl, preferably by methyl, and/or by alkoxy and/or by halogen, preferably F.
• R 13 and R ⁇ 1'4 together are forming a divalent radical selected from the following group of formulae
• An alkyl or an alkoxy radical i.e. an alkyl where the terminal CH 2 group is replaced by -0-, in this application may be straight-chain or branched. It is preferably straight-chain, has 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms and accordingly is preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, or octoxy, furthermore nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, nonoxy, decoxy, undecoxy, dodecoxy, tridecoxy or tetradecoxy, for example.
• alkenyl groups are C 2 -C 7 -1 E-alkenyl, C 4 -C 7 -3E- alkenyl, C 5 -C 7 -4-alkenyl, C 6 -C 7 -5-alkenyl and C 7 -6-alkenyl, in particular C 2 -C -1 E-alkenyl, C 4 -C 7 -3 E-alkenyl and C 5 -C 7 -4-alkenyl.
• Examples for particularly preferred alkenyl groups are vinyl, 1 E-propenyl, 1 E-butenyl,
• a alkyl or alkenyl group that is monosubstituted by CN or CF 3 is preferably straight-chain.
• the substitution by CN or CF 3 can be in any desired position.
• alkyl or alkenyl group that is at least monosubstituted by halogen it is preferably straight-chain.
• Halogen is preferably F or Cl, in case of multiple substitution preferably F.
• the resulting groups include also perfluorinated groups.
• the F or Cl substituent can be in any desired position, but is preferably in ⁇ -position.
• Examples for especially preferred straight-chain groups with a terminal F substituent are fluoromethyl, 2-fluoroethyl, 3-fluoropropyl, 4-fluorobutyl, 5-fluoropentyl, 6-fluorohexyl and 7-fluoroheptyl. Other positions of F are, however, not excluded.
• Halogen means F, Cl, Br and 1 and is preferably F or Cl, most preferably F.
• Each of R 11 to R 16 , R, R ⁇ R 01 and R 02 may be a polar or a non-polar group.
• a polar group it is preferably selected from CN, SF 5 , halogen, OCH 3 , SCN, COR 5 , COOR 5 or a mono- oligo- or polyfluorinated alkyl or alkoxy group with 1 to 4 C atoms.
• R 5 is optionally fluorinated alkyl with 1 to 4, preferably 1 to 3 C atoms.
• polar groups are selected of F, Cl, CN, OCH 3 , COCH 3 , COC 2 H 5 , COOCH 3 , COOC 2 H 5 , CF 3 , CHF 2 , CH 2 F, OCF 3 , OCHF 2 , OCH 2 F, C 2 F 5 and OC 2 F 5( in particular F, Cl, CN, CF 3 , OCHF 2 and OCF 3 .
• a non-polar group it is preferably alkyl with up to 15 C atoms or alkoxy with 2 to 15 C atoms.
• R 11 to R 16 , R, R', R 01 and R 02 may be an achiral or a chiral group. In case of a chiral group it is preferably of formula I * :
• 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-trifluoro-2-alkyl 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.
• one or more of R 11 to R 16 , R, FT, R 0 and R 02 are preferably one of R 13 and R 14 or both, are -SG-PG.
• 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.
• X is preferably -0-, -S-, -OCH 2 -, -CH 2 0-, -SCH 2 -, -CH 2 S-, -CF 2 0-, -OCF 2 -, -CF 2 S-, -SCF 2 -, -CH 2 CH 2 -, -CF 2 CH 2 -, -CH 2 CF 2 -, -CF 2 CF 2 -,
• 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 CH 2 -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 * ':
• Q 1 and Q 3 have the meanings given in formula I*, and Q « 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.
• liquid crystalline 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.
• the compounds of formula I preferably are prepared according to the following scheme.
• non-symmetric compounds e.g. wherein -(Z 11 -A 11 ) n -R 11 is different from -(Z 12 -A 12 ) m -R 12 are prepared by two subsequent couplings.
• 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 concentration of the compounds according to the present application are contained in the media according to the present application preferably is in the range from 0.5% or more to 30% or less, more preferably in the range from 1 % or more to 20% or less and most preferably in the range from 5% or more to 12% or less.
• the compounds of formula I are preferably selected from the group of sub- formulae 1-1 to 1-11
• R 11 and R 12 are, independently of each other, F, Cl, CN, NCS, CF 3 , OCF 3 , alkyl, alkoxy, alkenyl or alkynyl, preferably F, Cl, alkyl or alkoxy, and in formulae 1-1 to I-6 are preferably F, Cl, CN, NCS, CF 3 or OCF 3 , and in formulae 1-1 to I-6 are preferably alkyl, alkoxy, alkenyl or alkynyl,
• R and R are, independently of each other, alkyl, alkoxy, alkenyl or alkynyl and in case they are linkrd to a C-atom also may be H, preferably they are alkyl or H,
• L 11 to L 11"' and L 12 to L 12"' are, independently of each other, H or F, preferably F and
• X 11 and X 12 are, independently of each other, F, Cl, CN, CF 3 , OCF 3 or NCS, preferably F, CF 3 or CN, most preferably the are identical with each other,
• dielectrically positive component B comprising, preferably 1 o predominantly consisting of and most preferably entirely consisting of one compound or of more compounds of formula II
• R 2 has the meaning given under formula I for R 11 ,
• a 21 , A 22 and A 23 are, each independently of each other,
• each of A 21 and A 22 may have the same or a
• X 2 is halogen, -CN, -NCS, -SF 5 , -S0 2 CF 3 , alkyl, alkenyl, aikenyloxy or alkylalkoxy or alkoxy radical each mono- or polysubstituted by CN and/or halogen,
• L 21 and L 22 are, each independently of each other, H or F, and
• n O, 1 or 2
• o 0, 1 or 2, preferably 0 or 1 and
• m + n + o is 3 or less, preferably 2 or less
• component C preferably in a concentration of 1 % to 25 %, generally up to 10 % by weight, comprising, preferably predominantly consisting of and most preferably entirely consisting of one compound or of more compounds of formula III
• a, b, c and d are each independently of each other 0, 1 or 2, whereby
• a + b + c + d is 4 or less
• a 31 A 32 A 33 and A are, each independently of each other
• each of A 31 , A 32 , A 33 and A 34 may have the same or a different meaning if present twice,
• L 31 , L 32 , L 3 and L 34 are each independently of each other hydrogen, halogen, a CN group, 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 of each other by -0-, -S-,
• X 3 is F, Cl, CF 3 , OCF 3 , CN, NCS, -SF 5 or -S0 2 -R z ,
• R x and R y are independently of each other hydrogen or an alkyl radical having from 1 to 7 carbon atoms; preferably R x and R y are both methyl, ethyl, propyl or butyl, and
• R z is an alkyl radical having from 1 to 7 carbon atoms, said alkyl radical being unsubstituted or mono- or polysubstituted with halogen; preferably R 2 is CF 3 , C 2 F 5 or
• component D comprising one chiral compound or more chiral compounds with a HTP of ⁇ 20 ⁇ m.
• the inventive mixtures contain 1-25 wt.%, preferably 2-20 wt.% and most preferably 3-15 wt.% of component A.
• Preferred compounds of formula II are compounds selected of the group of formulae 11-1 to II-8, preferably of formulae II-4 and/or II-5:
• R is straight chain alkyl or alkoxy with up to six carbon atoms
• X 2 is F, CN, NCS, CF 3 , SF 5 or OCF 3 , preferably F or CN.
• the inventive mixtures contain 20-80 wt.% of the pyrane compounds of the formulae II, preferably 25-70 wt.% and especially preferred 30-60 wt.%.
• the compounds of formula III are selected from the group of compounds of the formulae 111-1 to III-7
• d is 0, 1 or 2, preferably 0 or 1 , especially preferred 1 ;
• R 3 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 ⁇ D-, -CO-O- and/or -O-CO- such that oxygen and/or sulfur and/or Si atoms are not linked .
• R 3 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 halogen,
• L 31 independently, has one of the meanings given for R 3 and preferably 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 halogen,
• L 32 independently, has one of the meanings given for R 3 or alternatively is hydrogen, halogen and preferably is
• H F
• F 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 polysubstituted with halogen,
• L 39b are, independently of each other, H or F and in formulae 111-1 to III-4 preferably at least L 35 is F and in formulae III-3 and III-4 preferably additionally L 38 is F, whereas in formula III-7 preferably additionally L 36 is F and in formulae III-5 and III-6 preferably at least both L and L 39b are F,
• Y 3 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 polysubstituted with halogen, preferably Y 31 is an alkoxy, alkenyloxy or -O-alkylene-O-alkyl radical with up to 10 carbon atoms, said radicals being unsubstituted or mono- or poly-substituted with halogen; in particular Y 31 has the same meaning as L
• Y 32 is hydrogen, halogen, 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 polysubstituted with halogen, preferably Y 32 is H,
• Z 33 and Z 34 are, independently of each other, a single bond
• Z 34 is a single bond, -C ⁇ C-, -CF 2 0- or -C0 2 -, in particular a single bond or -CF 2 0-, and in formulae III-3 and III-4 preferably one or both of Z 33 and Z 34 is a single bond, more preferably Z 33 and Z 34 are both a single bond or one of Z 33 and Z 34 alternatively is
• R x and R y are independently of each other hydrogen or an alkyl radical having from 1 to 7 carbon atoms; preferably both R x and R y are methyl, ethyl, propyl or butyl;
• R z is an alkyl radical having from 1 to 7 carbon atoms, said alkyl radical being unsubstituted or mono- or polysubstituted with halogen; preferably R z is CF 3 , C 2 F 5 or
• R 3 , L 31 and L 32 is one of said straight-chain alkyl, alkoxy, alkenyl, alkenyloxy or -O-alkylene-O-alkyl radicals.
• Suitable chiral compounds of component D are those which have an absolute value of the helical twisting power of 20 ⁇ m or more, preferably of 40 ⁇ m or more and most preferably of 60 ⁇ m or more.
• the HTP is measured in MLD-6260 at a temperature of 20°C.
• the chiral component D comprises preferably one or more chiral compounds which have a mesogenic structure und exhibit preferably one or more mesophases themselves, particularly at least one cholesteric phase.
• Preferred chiral compounds being comprised in the chiral component D are, inter alia, well known chiral dopants like cholesteryl- nonanoate (CN), R/S-811 , R/S-1011 , R/S-2011 , R/S-3011 , R/S-401 1 , R/S-5011 , CB-15 (Merck KGaA, Darmstadt, Germany).
• chiral dopants having one or more chiral moieties and one or more mesogenic groups or having one or more aromatic or alicyclic moieties forming, together with the chiral moiety, a mesogenic group. More preferred are chiral moieties and mesogenic chiral compounds disclosed in DE 34 25 503, DE 35 34 777, DE 35 34 778, DE 35 34 779, DE 35 34 780, DE 43 42 280, EP 01 038 941 and DE 195 41 820 that disclosure is incorporated within this application by way of reference.
• chiral binaphthyl derivatives as disclosed in EP 01 111 954.2, chiral binaphthol 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.
• the controlling medium of the present invention has a characteristic temperature, preferably a clearing point, in the range from about -30 °C to about 80 °C, especially up to about 55 °C.
• Preferred chiral compounds of the component D are selected from the group of the compounds D-l to D-lll.
• R a11 , R a12 are each independently from each other alkyl, oxalkyl,
• R a11 , R a12 , R a21 , R a22 , R a31 and R a32 are an alkyl group, especially a straight chain alkyl group.
• binaphthyl derivatives of the formulae D-IV-1 a to D-IV-1 c are especially preferred.
• R L is hydrogen, 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 of each other by -0-.
• -S-, -SiR Xr R>Y -, -CH CH-, -C ⁇ D-, -CO-O- and/or -O-CI- such that oxygen and/or sulfur atoms are not linked directly to each other, said alkyl or alkoxy radical being unsubstituted or mono- or poly-substituted with halogen,
• R° ⁇ R 2* and R 1* are each independently is F, Cl, OCF 3 , CF 3 , CN and L 1 , L 2 , L 3 and L 4 are each H or F.
• chiral binaphthyl derivatives of the formulae D- V-2a to D-V-2f are chiral binaphthyl derivatives of the formulae D- V-2a to D-V-2f :
• the inventive mixtures contain one ore more (two, three, four or more) chiral compounds in the range of 1-25 wt.%, preferably 2-20 wt.%. Especially preferred are mixtures containing 3-15 wt.% of a chiral compound.
• the medium comprises one, two or more compounds of formula I;
• Component B preferably contains besides one compound ore more compounds of formula II one ester compound or more ester compounds of the formula Z
• R z has the meaning given under formula I for R 11 ,
• X z is F, Cl, CN, NCS, OCF 3 , CF 3 or SF 5 .
• Preferred compounds of the formula Z are selected from the group of compounds of formulae Z-1 to Z-14
• R has the meaning given under formula Z for R ⁇ Especially preferred are mixtures containing 5 % to 35 %, preferably 10 % to 30 % and especially preferred 10 % to 20 % of compounds of formula Z, preferably selected from the group of formulae Z-1 to Z-14.
• the component B preferably contains additionally one or more compounds selected from the group of ester compounds of formulae N-1 to N-10
• Alkyl is alkyl with 1 to 7 C-atoms, preferably n-alkyl.
• the medium component B additionally comprises one or more compounds selected from the group consisting of the general formulae IV to VIII
• R L is n-alkyl, alkoxy, oxaalkyl, fluoroalkyl or alkenyl, each having up to 9 carbon atoms,
• X u is CN, SF 5 , NCS, S0 2 CF 3 , F, Cl, halogenated alkyl, halogenated alkenyl, halogenated alkenyloxy or halogenated alkoxy having up to 6 carbon atoms,
• Y 1 to Y 4 are each, independently of one another, H or F and r is 0 or 1 and
• the compounds of the formula VI are preferably selected from the group of compounds of formulae VI-1 to VI-5, preferably of VI-1 and/or VI-2 and /or VI-4, most preferably of VI-2 and/or Vl-4,
• the component B preferably additionally comprises one compound or more compounds with four six-membered rings selected from the group consisting of the general formulae IX to XVI:
• R°, X° and Y 1 to Y 4 have the respective meanings given under formulae IV to VIII and preferably
• X° is F, Cl, CF 3l OCF 3 or OCHF 2 ,
• R° is alkyl, oxaalkyl, fluoroalkyl or alkenyl, each having up to 6 carbon atoms.
• the component B preferably additionally comprises one or more compounds selected from the group of ester compounds of formulae E-1 to E-4
• the proportion of the compounds of the formulae E-1 to E-4 is preferably 10-30% by weight, in particular 15 % to 25 %.
• the proportion of compounds of the formulae III to Vlll in the mixture as a whole is preferably from 1 % to 30 %.
• the medium comprises compounds of the formulae II, III, IV, V, VI, VH and/or Vlll.
• R° preferably is straight-chain alkyl or alkenyl having from 2 to 7 carbon atoms.
• Component B preferably comprises further compounds, preferably selected from the following group consisting of the general formulae XVII to XXI:
• R° and X° are as defined under formulae IV to VII and the 1 ,4-phenylene rings optionally may additionally be substituted by CN, Cl or Fluorine, preferably by F.
• the 1 ,4-phenylene rings are preferably monosubstituted or polysubstituted by F atoms.
• the medium preferably additionally comprises one compound, two, three or more, preferably two or three, compounds selected from the group of compounds of the formulae 0-1 and 0-2
• Alkyl and Alkyl ' are as defined under formulae N-1 to N-6.
• the proportion of the compounds of the formulae 0-1 and/or 0-2 in the mixtures according to the invention is preferably 5 % to 10 % by weight.
• the medium preferably comprises one compound, two or three compounds of formula VII-4 in which X° is F or OCF 3 .
• the medium preferably comprises one compound or more compounds of the formulae 1V-1 to IV-7
• R has the meaning given under formula IV and preferably is methyl, ethyl, n-propyl, n-butyl, n-pentyl or vinyl.
• the medium preferably comprises one compound or more compounds selected from the group of formulae Q-1 to Q-9
• R ⁇ 0 has the meaning given under formulae IV to Vlll.
• the proportion of the compounds of the formula VI-1 and/or VI-12, in which X° preferably is fluorine, and R° preferably is CH 3 , C 2 H 5 , n-C 3 H7, n-C 4 H9, n-CsHn or vinyl, in the mixture as a whole is from 2 % to 20 %, in particular from 2 % to 15 %.
• the medium preferably comprises one compound or more compounds selected from the group of compounds of formulae II to VII in which R° is methyl.
• the medium particularly preferably comprises one compound or more compounds selected from the group of compounds of formulae IV- 1a, IV-2a and Q-7a
• the medium preferably comprises one dioxane compound, two or more dioxane compounds, preferably one dioxane compound or two dioxane compounds, selected from the group of formulae Dx-1 and Dx-2
• the medium preferably additionally comprises one, two or more compounds with two cyclohexane rings selected from the group of formulae Z-1 to Z-6
• R° has the meaning given under formulae IV to Vlll
• Alkyl and “Alkyl '” have the respective meanings given under formulae 0-1 and 0-2 and
• R 1a and R 2a are, each independently of each other, H, CH 3] C 2 H 5 or n-C 3 H 7 ,
• the medium preferably additionally comprises one, two or more compounds having fused rings, of the formulae AN-1 to AN-11
• R ⁇ 0 has the meaning given under formulae IV to Vlll.
• the optimum mixing ratio of the compounds of the formulae I and II + III + IV + V + VI + VII + Vlll depends substantially on the desired properties, on the choice of the components of the formulae I, II, III, IV, V, VI, VII and/or Vlll, and on the choice of any other components that may be present. Suitable mixing ratios within the range given above can easily be determined from case to case.
• the total amount of compounds of the formulae I to XXI in the mixtures according to the invention is not crucial.
• the mixtures can therefore comprise one or more further components for the purposes of optimisation of various properties. However, the observed effect on the operating voltage and the operating temperature range is generally greater, the higher the total concentration of compounds of the formulae I to XXI.
• the construction of the MLC display according to the invention from polarisers, electrode base plates and surface-treated electrodes corresponds to the conventional construction for displays of this type.
• the term conventional construction is broadly drawn here and also covers all derivatives and modifications of the MLC display, in particular including matrix display elements based on poly-Si TFT or MIM, however, particularly preferred are displays, which have electrodes on just one of the substrates, i.e. so called interdigital electrodes, as those used in IPS displays, preferably in one of the established structures.
• a significant difference between the displays according to the invention and the conventional displays based on the twisted nematic cell consists, however, in the choice of the liquid-crystal parameters of the liquid-crystal layer.
• the media according to the invention are prepared in a manner conventional per se. In general, the components are dissolved in one another, advantageously at elevated temperature.
• the liquid-crystalline phases in accordance with the invention can be modified in such a way that they can be used in all types of liquid crystal display elements that have been disclosed hitherto. Additives of this type are known to the person skilled in the art and are described in detail in the literature (H. Kelker and R. Hatz, Handbook of Liquid Crystals, Verlag Chemie, Weinheim, 1980).
• pleochroic dyes can be added for the preparation of coloured guest-host systems or substances can be added in order to modify the dielectric anisotropy, the viscosity and/or the alignment of the nematic phases.
• stabilisers and antioxidants can be added.
• the mixtures according to the invention are suitable for TN, STN, ECB and IPS applications and isotropic switching mode (ISM) applications.
• ISM isotropic switching mode
• the inventive mixtures are highly suitable for devices which operate in an optically isotropic state.
• the mixtures of the invention are surprisingly found to be highly suitable for the respective use.
• Electro-optical devices that are operated or operable in an optically isotropic state recently have become of interest with respect to video, TV, and multi-media applications. This is because conventional liquid crystal displays utilizing electro-optical effects based on the physical properties of liquid crystals exhibit a rather high switching time which is undesired for said applications. Furthermore most of the conventional displays show a significant viewing angle dependence of contrast that in turn makes necessary measures to compensate this undesired property.
• German Patent Application DE 102 17273 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.
• the driving or operating voltages of said elements are very often unsuitably high for some applications.
• German Patent Application DE 10241 301 describes specific structures of electrodes allowing a significant reduction of the driving voltages. However, these electrodes make the process of manufacturing the light controlling elements more complicated.
• the light controlling elements for example, disclosed in both DE 102 17273 A1 and DE 10241 301 show a significant temperature dependence.
• the electro-optical effect that can be induced by the electrical field in the controlling medium being in an optical isotropic state is most pronounced at temperatures close to the clearing point of the controlling medium.
• the light controlling elements have the lowest values of their characteristic voltages and, thus, require the lowest operating voltages.
• Typical values of the temperature dependence are in the range from about a few volts per centigrade up to about ten or more volts per centigrade.
• DE 102 41 301 describes various structures of electrodes for devices operable or operated in the isotropic state
• DE 102 17 273 A1 discloses isotropic media of varying composition that are useful in light controlling elements operable or operated in the isotropic state.
• the relative temperature dependence of the threshold voltage in these light controlling elements is at a temperature of 1 centigrade above the clearing point in the range of about 50%/centigrade. That temperature dependence decreases with increasing temperature so that it is at a temperature of 5 centigrade above the clearing point of about 10%/centigrade.
• the temperature dependence of the electro-optical effect is too high.
• the operating voltages are independent from the operating temperature over a temperature range of at least some centigrades, preferably of about 5 centigrades or more, even more preferably of about 10 centigrades or more and especially of about 20 centigrades or more.
• inventive mixtures are highly suitable as controlling media in the light controlling elements as described above and in DE 102 17 273 A1 , DE 10241 301 and DE 102 536 06 and broaden the temperature range in which the operating voltages of said electro-optical operates.
• the optical isotropic state or the blue phase is almost completely or completely independent from the operating temperature.
• Liquid crystals having an extremely high chiral twist may have one or more optically isotropic phases. If they have a respective cholesteric pitch, these phases might appear bluish in a cell having a sufficiently large cell gap. Those phases are therefore also called “blue phases” (Gray and Goodby, “Smectic Liquid Crystals, Textures and Structures", Leonhard Hill, USA, Canada (1984)). Effects of electrical fields on liquid crystals existing in a blue phase are described for instance in H.S. Kitzerow, "The Effect of Electric Fields on Blue Phases", Mol. Cryst. Liq.
• inventive mixtures can be used in an electro-optical light controlling element which comprises
• said light controlling element is operated (or operable) at a temperature at which the controlling medium is in an optically isotropic phase when it is in a non-driven state.
• the controlling medium of the present invention has a characteristic temperature, preferably a clearing point, in the range from about -30 °C to about 80 °C, especially up to about 55 °C.
• the operating temperature of the light controlling elements is preferably above the characteristic temperature of the controlling medium said temperature being usually the transition temperature of the controlling medium to the blue phase; generally the operating temperature is in the range of about 0.1 ° to about 50 °, preferably in the range of about 0.1 ° to about 10 ° above said characteristic temperature. It is highly preferred that the operating temperature is in the range from the transition temperature of the controlling medium to the blue phase up to the transition temperature of the controlling medium to the isotropic phase which is the clearing point.
• the light controlling elements may also be operated at temperatures at which the controlling medium is in the isotropic phase.
• characteristic temperature is defined as follows:
• characteristic temperature the temperature at this minimum is denoted as characteristic temperature.
• the transition 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.
• characteristic temperature the transition temperature to the isotropic phase
• alkyl means, as long as it is not defined in a different manner elsewhere in this description or in the claims, straight-chain and branched hydrocarbon (aliphatic) radicals with 1 to 15 carbon atoms.
• the hydrocarbon radicals may be unsubstituted or substituted with one or more substituents being independently selected from the group consisting of F, Cl, Br, I or CN.
• the dielectrics may also comprise further additives known to the person skilled in the art and described in the literature. For example, 0 to 5% of pleochroic dyes, antioxidants or stabilizers can be added.
• C denotes a crystalline phase
• S a smectic phase S c a smectic C phase
• N a nematic phase
• I the isotropic phase
• BP the blue phase.
• V x denotes the voltage for X% transmission.
• V 10 denotes the voltage for 10% transmission
• V 100 denotes the voltage for 100% transmission (viewing angle perpendicular to the plate surface).
• ⁇ on denotes the switch-on time and t off (respectively ⁇ 0 ⁇ f ) the switch-off time at an operating voltage corresponding the value of V 100 , respectively of V max .
• ⁇ n denotes the optical anisotropy.
• the electro-optical data are measured in a TN cell at the 1 st minimum of transmission (i.e. at a (d • ⁇ n) value of 0.5 ⁇ m) at 20°C, unless expressly stated otherwise.
• the optical data are measured at 20°C, unless expressly stated otherwise.
• the light modulation media according to the present invention 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 inventive media have a range of the blue phase or, in case of the occurrence of more than one blue phase, a combined range of the blue phases, with a width of 9° or more, preferably of 10° or more, more preferably of 15° or more and most preferably of 20° or more.
• This range may include biphasic systems in which two phases are coexisting with each other.
• this phase range at least from 10°C to 30°C, most preferably at least from 10°C to 40°C and most preferably at least from 0°C to 50°C, wherein at least means, that preferably the phase extends to temperatures below the lower limit and at the same time, that it extends to temperatures above the upper limit.
• this phase range at least from 20°C to 40°C, most preferably at least from 30°C to 80°C and most preferably at least from 30°C to 90°C.
• This embodiment is particularly suited for displays with a strong back light, dissipating energy and thus heating the display.
• 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 20 ⁇ m.
• the voltage applied is a rectangular wave with a frequency of 1 kHz and a root mean square value typically of 0.5 V to 1.0 V, however, it is always selected to be below the capacitive threshold of the respective test mixture and thus may be as small as 0.1 V.
• the mixture ZLI-4792 and for dielectrically neutral, as well as for dielectrically negative compounds the mixture ZLI-3086, both of Merck KGaA, Germany 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 %.
• Components having a nematic phase at the measurement temperature of 20 °C are measured as such, all others are treated like compounds.
• threshold voltage refers in the instant application to the optical threshold and is given for 10 % relative contrast (V ⁇ 0 ) and the term saturation voltage refers to the optical saturation and is given for 90 % relative contrast (V go ) both, if not explicitly stated otherwise.
• the capacitive threshold voltage V 0 , also called Freedericksz-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 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 or 0.1 ⁇ / 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 voltage (V 10 ), mid-grey voltage (V 50 ) and saturation voltage (V 90 ) have been determined for 10 %, 50 % and
• the mesogenic modulation material has been filled into an electro optical test cell prepared at the respective facility of Merck KGaA.
• the test cells had inter-digital electrodes on one substrate side.
• the electrode width was 10 ⁇ m
• the distance between adjacent electrodes was 10 ⁇ m
• the cell gap was also 10 ⁇ m.
• This test cell has been evaluated electro-optically between crossed polarisers.
• the filled cells showed the typical texture of a chiral nematic mixture, with an optical transmission between crossed polarisers without applied voltage.
• T-i first temperature
• the mixtures turned optically isotropic, being dark between the crossed polarisers. This indicated the transition from the chiral nematic phase to the blue phase at that temperature.
• T 2 second temperature
• the cell showed an electro-optical effect under applied voltage, typically of some tens of volts, a certain voltage in that range leading to a maximum of the optical transmission.
• the voltage needed for a visible electro-optical effect increased strongly, indicating the transition from the blue phase or from a biphasic sytem to the isotropic phase at this second temperature (T 2 ).
• the temperature range ( ⁇ T(BP)), where the mixture can be used electro- optically in the blue phase most beneficially has been identified as ranging from T to T 2 .
• This temperature range ( ⁇ T(BP)) is the temperature range given in the examples of this application.
• the electro-optical displays can also be operated at temperatures beyond this range, i.e. at temperatures above T 2 , albeit only at significantly increased operation voltages.
• the liquid crystal media according to the present invention can contain further additives and chiral dopants in usual concentrations.
• the total concentration of these further constituents is in the range of 0 % to 10 %, preferably 0.1 % to 6 %, based on 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.
• 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 PDLD-, NCAP- and PN-LCDs and especially in HPDLCs.
• the melting point T(C,N), the transition from the smectic (S) to the nematic (N) phase T(S,N) and the clearing point T (N,l) of the liquid crystals are given in degrees centigrade.
• 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+1 and C m H 2m+1 are straight chain alkyl groups with n respectively m D-atoms. The interpretation of table B is self evident.
• Table A does only list the abbreviations for the cores of the structures. The individual compounds are denoted by the abbreviation of the core followed by a hyphen and a code specifying the substituents Ri, R2, Li and L ⁇ follows:
• liquid-crystalline mixtures which, besides the compounds of the formula I, comprise at least one, two, three or four compounds from Table B.
• Table C shows possible dopants according to component D which are generally added to the mixtures alone or in combination two, three or more) according to the invention.
• Stabilisers which can be added, for example, to the mixtures according to the invention are mentioned below.
• liquid crystal media according to the instant invention do contain preferably
• the compound (3) is prepared according to the following reaction scheme:
• a mixture of 3 g of (1), 10.5 g of (2), 233 mg PdCI 2 (dppf), 34 ml dioxane and 12.6 ml 2 molar aquous solution of Na 2 C0 3 is heated under reflux for 18 h.
• the product is purified according to standard procedures.
• the crude product is purified over silicagel with a solvent mixture of heptane and CH 2 CI 2 in the mixing ratio of 1 :1 and subsequently and re-crystallized from toluene.
• the yield is 3.8 g of (3), i.e. 47% of the theoretical yield.
• the product has a phase sequence of T g 15°C C 154°C
• the product has a phase sequence of T g 18°C C 145°C I.
• the product has a phase sequence of T g 15°C C 148°C I.
• the product has a phase sequence of C 172°C Example 6
• the product has a phase sequence of T g 23°C C 105°C I. Examples 7 to 58

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