GB2330139A - Polymerizable chiral dopants based on chiral tetrahydrofuran or hexahydrofuro[3,2-b]furan substituted by at least two mesogenic groups - Google Patents

Polymerizable chiral dopants based on chiral tetrahydrofuran or hexahydrofuro[3,2-b]furan substituted by at least two mesogenic groups Download PDF

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GB2330139A
GB2330139A GB9821817A GB9821817A GB2330139A GB 2330139 A GB2330139 A GB 2330139A GB 9821817 A GB9821817 A GB 9821817A GB 9821817 A GB9821817 A GB 9821817A GB 2330139 A GB2330139 A GB 2330139A
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compound
ocoo
chiral
handed
oco
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GB2330139B (en
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Frank Meyer
Hiroki Ishida
Peter Schuhmacher
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/38—Polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
    • C09K19/58—Dopants or charge transfer agents
    • C09K19/586—Optically active dopants; chiral dopants
    • C09K19/588—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—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

Abstract

Chiral compounds are disclosed of the formula (Z-Y-[A] m -Y-M-Y-) n X I, where, independently of one another, A is a spacer, M is a mesogenic group containing two phenylene radicals which are unsubstituted or substituted by C 1 - to C 4 -alkyl, methoxy, ethoxy, fluorine, chlorine, bromine, C 1 -to C 20 -alkoxycarbonyl or C 1 - to C 20 -alkylcarbonyl and are linked via O, CO, OCO, OCOO or COO, Y is a direct bond, O, S, COO, OCO, OCOO, CON(R) or N(R)CO, and Z is a polymerizable group, m is 0 or 1, n is from 2 to 6, and X is a chiral radical of the formula R is C 1 - to C 4 -alkyl or hydrogen, and their use as polymerizable, chiral high-twisting-power dopants for the production of cholesteric networks. These compounds are suitable for use in electro-optical displays or as chiral dopants for nematic or cholesteric liquid crystals for producing layers which reflect in color. They may also be used as chiral dopants in optical polarizers and optical filters.

Description

Polymerizable chiral compounds, and their use It is known that molecules which are anisotropic in shape can form liquid-crystalline phases, known as mesophases, on warming.
The individual phases differ through the spatial arrangement of the major parts of the molecules on the one hand and through the molecular arrangement with respect to the long axes on the other hand (G.W. Gray, P.A. Winsor, Liquid Crystals and Plastic Crystals, Ellis Horwood Limited, Chichester 1974). The nematic liquid-crystalline phase is distinguished by the fact that there is only one alignment long-distance ordering die to the long molecular axes lining up in parallel. Under the prerequisite that the molecules making up the nematic phase are chiral, a cholesteric phase forms, in which the long axes of the molecules form a helical superstructure perpendicular thereto (H. Baessler, Festkorperprobleme XI, 1971). The chiral moiety may be present either in the liquid-crystalline molecule itself or added to the nematic phase as a dopant. Phases produced by doping are referred to as induced cholesteric phases. This phenomenon was first studied on cholesterol derivatives (H. Baessler, M.M. Labes, J.
Chem. Phys. 52 (1970) 631; H. Beassler, T.M. Laronge, M.M. Labes.
J. Chem. Phys. 51 (1969) 3213; H. Filkelmann, H. Stegemeyer, Z.
Naturforschg. 28a (1973) 799). It later also became possible to induce cholesteric phases by adding other chiral substances which are not themselves liquid-crystalline (H. Stegemeyer, K.J.
Mainusch, Naturwiss. 58 (1971) 599; H. Finkelmann, H. Stegemeyer, Ber. Bunsenges. Phys. Chem. 78 (1974) 869).
The cholesteric phase has remarkable optical properties: large optical rotation and pronounced circular dichroism caused by selective reflection of circular-polarized light within the cholesteric layer. The different colors observed depending on the veering angle depend on the pitch of the helical superstructure, which is itself dependent on the twisting power of the chiral component. The pitch and thus the wavelength range of the selectively reflected light of a cholesteric layer can be varied, in particular, by changing the concentration of a chiral dopant (J.E. Adams, W.E.L. Haas, Mol. Cryst. Liq. Cryst. 16 (1972) 33).
Such cholesteric systems offer interesting opportunities for practical use. Thus, incorporation of chiral moieties into mesogenic acrylic esters after alignment in the cholesteric phase and photocrosslinking allows the production of a stable, colored network, but the concentration of the chiral component therein cannot be changed (G. Galli, M. Laus, A. Angeloni, Makromol.
Chem. 187 (1986) 289). Furthermore, admixing of non-crosslinkable, chiral compounds with nematic acrylic esters allows, after photocrosslinking, the production of a colored polymer (I. Heyndericks, D.J. Broer, Mol. Cryst. Liq. Cryst. 203 (1991) 113), but this still contains volatile constituents which are prohibitive for use, EP-A-739403 describes chiral compounds which firstly have a high twisting power and secondly can be incorporated into the cholesteric phase in a stable manner in any desired concentration without diffusing or crystallizing out of the phase.
We have now found a group of compounds which has even better properties than those described above.
Accordingly, the present invention provides compounds of the formula I (Z-Y-lA]m-Y~M~Y~)n X I, where, independently of one another, A is a spacer, M is a mesogenic group containing two phenylene radicals which are unsubstituted or substituted by C1- to C4-alkyl, methoxy, ethoxy, fluorine, chlorine, bromine, C1- to C20-alkoxycarbonyl or C1- to C20-alkylcarbonyl and are linked via 0, CO, OCO, OCOO or COO, Y is a direct bond, 0, S, COO, OCO, OCOO, CON(R) or N(R)CO, and Z is a polymerizable group, m is O or 1, n is from 2 to 6, and X is a chiral radical of the formula
R is C1- to C4-alkyl or hydrogen.
The spacer A can be any group known for this purpose; the spacer. are usually linked to X via ester or ether groups or a direct bond. The spacers generally contain from 1 to 30, preferably fre 1 to 12, carbon atoms and may be interrupted in the chain by, fo: example, 0, S, NH or NCH3. Suitable substituents for the spacer chain are fluorine, chlorine, bromine, cyano, methyl and ethyl.
Examples of representative spacers are the following: ( CH2 ) (CH2CH2O)qCH2CH2,
where p is from 1 to 12, and q is from 1 to 3.
Particularly preferred mesogenic groups M are, for example:
The groups necessary for the novel compounds are linked to one another via bridges Y, such as 0, S, COO, OCO, OCOO, CONH, NHCO, CON(R), N(R)CO or a direct bond, where R is C1- to C4-alkyl or hydrogen. Y is preferably 0, OCO, COO or OCCO. n is preferably 2.
Polymerizable groups which may be mentioned in particular are vinyl radicals, which are present, for example, in acrylic compounds, vinyl ethers and styrene derivatives. Epoxides are also suitable.
Examples of preferred radicals Z are the following:
where R is as defined above.
Z is particularly
sC}52=w .CHa * The units Z-Y[A]=-Y-M-Y according to the invention, where Z, Y, m, A and M are as defined above, can be obtained by generally known synthetic methods, as described, for example, in EP-A 739403 and DE-A 39 17 196.
The chiral moieties can be purchased commercially and are thus available.
The novel compounds are suitable as high-twisting-power dopants for producing cholesteric liquid crystals. Using very small amounts, the reflection wavelength of the cholesteric mixture can be shifted into the visible region. It is advantageous here that the dopants form a stable mixture with the nematic host system, from which mixture the dopant does not crystallize out. The novel compounds are particularly suitable for this purpose.
The novel compounds are particularly suitable for use in electro-optical display elements or as chiral dopants for nematic or cholesteric liquid-crystal mixtures for producing layers which reflect in color.
The novel compounds are also suitable for use as chiral dopants in optical polarizers and optical filters.
Particular preference is given here to mixtures of the novel compounds with nematic compounds of the formula (Z)m-Y-A-Y-M-Y-A-Y-(Z)mv II where, in each case independently of one another, A, m, Y and Z are as defined above, and M1 is a mesogenic group.
Compounds of the formula II are described, for example, in DE-OS 195 32 408, GB-A-22 79 659, (EP-A-749 466) and EP-A-648 827.
Also claimed are solid compositions comprising the novel compounds in copolymerized form.
Also claimed are solid compositions comprising the novel compounds and nematic compounds of the above formula II, in each case in copolymerized form.
Solid compositions of this type may be, for example, polymers which can contain partly uncross linked or non-copolymerized constituents. Non-copolymerized constituents of this type can be, for example, unreactive organic molecules having a wide variety of molecular weights or alternatively inorganic or organic pigments. They may furthermore also be additives, for example rheology auxiliaries or light and/or oxidation stabilizers.
It is of course also possible for solid compositions of this type to be the polymerization products of the claimed liquidcrystalline mixtures containing the novel compounds, and of the claimed liquid-crystalline mixtures containing nematic compounds of the above formula II in addition to the novel compounds.
Example 1
Procedure: 3.84g (0.01 mol) of bis(4'-hydroxybenzoyl)-1,4:3,6-dianhydrosorbitol are dissolved in 30 ml of DMF and 5.08 g (0.04 mol) of N,N-dimethylcyclohexylamine, and 8.0 g (0.024 mol) of 4-acryloxybutoxycarbonyloxybenzoyl chloride are then added dropwise at 0 - 5 C. The mixture is stirred at 0-5 C for one hour, at 40 C for 3 hours and then at RT overnight. The reaction mixture is poured into water and acidified using conc. hydrochloric acid. Ethyl acetate is added, and the organic phase is washed with water, dried over sodium sulfate and evaporated in a rotary evaporator.
Yield: 11.3 g The crude product is chromatographed over 1.1 kg of silica gel using the eluent petroleum ether/ethyl acetate (2:1).
Yield: 9.3 g (96%) [NMR] HTP in ZLI 1840 63 m-1 Melting point: 109 C (DTA) The compound has a right-handed twist.
Further compounds prepared by this and similar processes are the following: HTP = helical twisting power
Ex. Y1 Y2 R1 R2 m1 m2 HTP Twist m-1 in ZLI 1840 2 OCOO OCOO OMe OMe 2 4 right-handed 3 OCOO OCOO OMe OMe 4 4 50 right-handed 4 OCOO OCOO OMe OMe 6 6 right-handed 5 OCOO OCOO OMe OMe 4 6 right-handed 6 OCOO OCOO OMe OMe 6 4 right-handed 7 OCOO OCOO H H 2 2 right-handed 8 OCOO OCOO H H 4 2 right-handed 9 OCOO OCOO H H 2 4 right-handed 10 OCOO OCOO H H 6 6 right-handed 11 OCOO OCOO H H 6 4 right-handed 12 O O H H 2 2 right-handed 13 O O H H 4 2 right-handed 14 O O H H 4 4 63 right-handed 15 O O H H 4 6 right-handed 16 O O H H 6 6 right-handed 17 OCOO O H H 4 4 right-handed 18 O OCOO H H 4 4 right-handed 19 OCOO O H H 6 6 right-handed
Ex. Y1 Y2 R1 R2 m1 m2 HTP Twist m-1 in ZLI 1840 20 O OCOO H H 6 6 right-handed 21 OCO COO H H 4 4 right-handed 22 OCO COO H H 6 6 right-handed 23 OCO O H H 4 4 right-handed 24 OCO O H H 6 6 right-handed
Ex. Y1 Y2 R1 R2 m1 m2 HTP Twist m-1 in ZLI 1840 25 OCOO OCOO OMe OMe 4 4 11 left-handed 26 OCOO OCOO OMe OMe 6 6 left-handed 27 OCOO OCOO OMe OMe 2 2 left-handed 28 O O H H 2 2 left-handed 29 O O H H 4 2 left-handed 30 O O H H 4 4 63 left-handed 31 O O H H 6 6 left-handed 32 COO OCO H H 2 2 left-handed 33 COO OCO H H 4 4 left-handed 34 COO OCO H H 6 6 left-handed 35 COO OCO H H 6 4 left-handed 36 OCOO OCOO H H 2 2 left-handed 37 OCOO OCOO H H 2 4 left-handed 38 OCOO OCOO H H 4 4 13 left-handed 39 OCOO OCOO H H 6 6 left-handed 40 OCOO OCOO H H 4 6 left-handed 41 OCOO OCOO H H 6 4 left-handed 42 O O OMe OMe 4 4 left-handed
Ex. Y1 Y2 R1 R2 43 O O H H 44 O O OMe OMe 45 O O Me Me 46 OCOO OCOO H H 47 OCO OCO H H 48 OCO OCO H H Mixtures with liquid-crystalline substances Example 49 x mol% of Example 1 are dissolved in the nematic mixture
by mixing the melts. After cooling to RT, cholesteric phases with the following reflection wavelengths - depending on X - are obtained: x (mol%) hi (nm) 2.0 701 3.0 482 4.0 341 Example 50 x mol% of Example 1 are dissolved in the nematic compound
by mixing the melts. After cooling to RT, cholesteric phases with the following reflection wavelengths are obtained: x (mol%) ## (nm) 3.05 660 3.51 565 4.28 465 5.46 365 Example 51 x molt of Example 1 are dissolved in the nematic mixture
by mixing the melts. After cooling to RT, cholesteric phases with the following reflection wavelengths - depending on X - are obtained: x (mol$) hi (nm) 2.0 854 2.5 696 3.0 575 3.5 498 Example 52 x mol% of Example 1 are dissolved in the nematic mixture
by mixing the melts. After cooling to RT, cholesteric phases with the following reflection wavelengths - depending on X - are obtained: x (mol%) k1 (nm) 1.5 974 2.0 736 2.5 588 3.0 493 Comparative Example 53 4 mol% of both the compound from Example 1 and the compound of the formula III (corresponding to EP-A-739 403)
are added to the nematic compound
The two substances are melted and their spectrum measured at RT.
The compound from claim 1 gives a reflection at 431 nm, while the compound of Formula III gives a reflection at 1087 nm.

Claims (14)

  1. Claims 1.- A Compound of the formula (Z-Y-CAm-Y-M-Y-)n X I, where, independently of one another, A is a spacer, M is a mesogenic group containing two phenylene radicals which are unsubstituted or substituted by C1- to C4-alkyl, methoxy, ethoxy, fluorine, chlorine, bromine, C1- to C20-alkoxycarbonyl or C1- to C20-alkylcarbonyl and are linked via 0, CO, OCO, OCOO or COO, Y is a direct bond, 0, S, COO, OCO, OCOO, CON(R) or N(R)CO, and Z is a polymerizable group, m is O or 1, n is from 2 to 6, and X is a chiral radical of the formula
    R is C1- to C4-alkyl or hydrogen.
  2. 2. A compound as claimed in claim 1, where n = 2.
  3. 3. A compound as claimed in claim 1, where M is
  4. 4. A compound as claimed in claim 1, where Y is 0, OCO, COO, OCOO or a direct bond.
  5. 5. A compound as claimed in claim 1, where
  6. 6. A compound as claimed in claim 1, where
    p is from 1 to 12 and q is from 1 to 3.
  7. 7. A compound as claimed in claim 1, where
  8. 8. A compound as claimed in claim 1 and referred to in any of the foregoing Examples 1 to 52.
  9. 9. A liquid-crystalline mixture comprising one or more compounds as claimed in any of claims 1 to 8.
  10. 10. A liquid-crystalline mixture comprising one or more compounds as claimed in any of claims 1 to 8 and one or more nematic compounds of the formula II (Z)=-Y-A-Y-Ml-Y-A-Y-(z) l II where, in each case independently of one another, A, m, Y and Z are as defined in claim 1, and Ml is a mesogenic group.
  11. 11. A solid composition comprising a compound as claimed in any of claims 1 to 8 in copolymerized form.
  12. 12. A solid composition comprising a compound as claimed in any of claims 1 to 8 and a nematic compound of the formula II defined in claim 10, in each case in copolymerized form.
  13. 13. The use of a compound as claimed in any of claims 1 to 8 in electro-optical displays or as a chiral dopant for nematic or cholesteric liquid crystals for producing layers which reflect in color.
  14. 14. The use of a compound as claimed in any of claims 1 to 8 as a chiral dopant in optical polarizers and optical filters.
GB9821817A 1997-10-08 1998-10-07 Polymerizable chiral compounds,and their use Expired - Lifetime GB2330139B (en)

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US6605235B1 (en) 1999-08-27 2003-08-12 Basf Aktiengesellschaft Cholesteric layered material having an improved color impression, and the production thereof
US6723395B2 (en) * 2001-07-02 2004-04-20 Merck Patent Gmbh Chiral compounds
US6773766B2 (en) * 1998-12-22 2004-08-10 Basf Aktiengesellschaft Utilization of polymerizable liquid crystal substances for the production of optical components
US6850310B1 (en) 1999-08-27 2005-02-01 Basf Aktiengesellschaft Cholesteric layered material having improved color stability, and the production thereof
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WO2000037585A1 (en) * 1998-12-22 2000-06-29 Basf Aktiengesellschaft Utilization of polymerizable liquid crystal substances for the production of optical components
US6773766B2 (en) * 1998-12-22 2004-08-10 Basf Aktiengesellschaft Utilization of polymerizable liquid crystal substances for the production of optical components
US6605235B1 (en) 1999-08-27 2003-08-12 Basf Aktiengesellschaft Cholesteric layered material having an improved color impression, and the production thereof
US6850310B1 (en) 1999-08-27 2005-02-01 Basf Aktiengesellschaft Cholesteric layered material having improved color stability, and the production thereof
US6905739B2 (en) * 1999-12-23 2005-06-14 Rolic Ag Optically active materials
EP1160304A2 (en) * 2000-05-26 2001-12-05 Basf Aktiengesellschaft Liquid crystalline substance mixture
EP1160304A3 (en) * 2000-05-26 2002-06-05 Basf Aktiengesellschaft Liquid crystalline substance mixture
US6712992B2 (en) 2000-05-26 2004-03-30 Basf Aktiengesellschaft Liquid-crystalline composition of matter
US7108801B2 (en) 2001-01-23 2006-09-19 Southwest Reasearch Institute Methods and blends for controlling rheology and transition temperature of liquid crystals
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GB9821817D0 (en) 1998-12-02
DE19843724A1 (en) 1999-04-15
JPH11193287A (en) 1999-07-21
CH692985A5 (en) 2003-01-15
GB2330139B (en) 2002-06-12

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