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  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
  • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
  • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
  • C07D309/06—Radicals substituted by oxygen atoms
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  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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  • C07C31/27—Polyhydroxylic alcohols containing saturated rings
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  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
  • C07C31/27—Polyhydroxylic alcohols containing saturated rings
  • C07C31/278—Polycyclic with condensed rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
  • C07C33/05—Alcohols containing rings other than six-membered aromatic rings
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
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  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2601/00—Systems containing only non-condensed rings
  • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
  • C07C2601/14—The ring being saturated
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2602/00—Systems containing two condensed rings
  • C07C2602/50—Spiro compounds
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • C09K19/06—Non-steroidal liquid crystal compounds
  • C09K19/34—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
  • C09K2019/3416—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a four-membered ring, e.g. oxetane
  • C09K2019/3419—Four-membered ring with oxygen(s), e.g. oxetane, in fused, bridged or spiro ring systems
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  • C09K19/00—Liquid crystal materials
  • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
  • 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
  • C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-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
  • C09K2323/00—Functional layers of liquid crystal optical display excluding electroactive liquid crystal layer characterised by chemical composition

Definitions

• the present invention relates to dioxane derivatives containing both a dioxane ring and a spiro [3.3] heptyl group as part of their
• the dioxane derivatives according to the invention can be used as component (s) of liquid-crystalline media, in particular for displays based on the principle of the twisted cell, the guest-host effect, the effect of the deformation of upright phases DAP or ECB (Electrically Controlled Birefringence), the IPS Effect (In Plane Switching) or the effect of dynamic scattering.
• the invention was thus based on the object of finding new stable compounds which are suitable as component (s) of liquid-crystalline media, in particular for TN, STN, IPS and TFT displays.
• Another object of the present invention was to provide compounds which have a low rotational viscosity, have a positive dielectric anisotropy ⁇ and are easy to synthesize. In particular, by reducing the rotational viscosity significantly lower switching times should be realized.
• the dioxane derivatives according to the invention are excellent as component (s) of liquid-crystalline media are suitable. With their help, it is possible to obtain stable, liquid-crystalline media, in particular suitable for TFT or STN displays.
• the physical properties of the dioxane derivatives according to the invention can be varied within wide limits.
• the dioxane derivatives according to the invention are distinguished both by low optical anisotropy values and by unexpectedly low rotational viscosities.
• Liquid crystalline media with very low levels of optical anisotropy are particularly important for reflective and transflective applications, i. Such applications in which the respective LCD experiences no or only supportive backlight.
• the range of liquid-crystalline substances which are suitable for the preparation of liquid-crystalline mixtures from a variety of application-technical points of view is considerably broader.
• the dioxane derivatives of the invention have a broad
• these compounds may serve as base materials from which liquid crystalline media are predominantly composed.
• liquid-crystalline base materials from other classes of compounds to the dioxane derivatives according to the invention in order, for example, to influence the dielectric and / or optical anisotropy of such a dielectric and / or to optimize its threshold voltage and / or its viscosity.
• the dioxane derivatives according to the invention are colorless in the pure state. Chemically, thermally and against light, they are stable.
• the present invention thus relates to dioxane derivatives of the formula I.
• a 1 , A 2 are each independently, the same or different
• trans-1,4-cyclohexylene in which also one or more non-adjacent CH 2 groups may be replaced by -O- and / or -S- and in which also one or more H atoms may be replaced by F
• 1,4-phenylene in which one or two CH groups may be replaced by N and in which also one or more H atoms are represented by halogen (F, Cl, Br, I), -CN, -CH 3 , -CHF 2 , -CH 2 F, -CF 3 , -OCH 3 , -OCHF 2 or -OCF 3 may be replaced,
• Each of Z 1 , Z 2 is independently, identically or differently -O-, -CH 2 O-, -OCH 2 -, -CO-O-, -O-CO-, -CF 2 O-, -OCF 2 -, -CF 2 CF 2 -,
• Another object of the present invention is the use of compounds of formula I as component (s) in liquid-crystalline media.
• liquid-crystalline media having at least two liquid-crystalline components which contain at least one compound of the formula I.
• the subject of the present invention is also liquid crystal
• Display elements in particular electro-optical display elements, which contain a liquid crystalline medium according to the invention as a dielectric.
• reflective and transflective liquid crystal display elements and other low birefringence liquid crystal displays .DELTA.n, so-called “low ⁇ n mode displays", such. reflective and transflective TN displays.
• the meaning of the formula I includes all isotopes of the chemical elements bound in the compounds of the formula I.
• the compounds of the formula I are also suitable as chiral dopants and generally for the achievement of chiral mesophases.
• R 1 , R 2 , A 1 , A 2 , Z 1 , Z 2 , G, m and n have the meaning given, unless expressly stated otherwise. If the radicals A 1 and A 2 or Z 1 and Z 2 more than once, so they can assume independently of one another identical or different meanings.
• Preferred compounds of the formula I are compounds of the partial formula Ia
• R 1 , R 2 , A 1 , A 2 , Z 1 , Z 2 , m and n have the meanings given above.
• R 1 is H or a linear alkyl radical having 1 to 10 C atoms.
• R 2 is H, a linear alkoxy radical having 1 to 10 C atoms, -F, -Cl, -CF 3 , -OCF 3 , -OCHF 2 , -CN, -NCS or -SF 5 , more preferably -F, -CF 3 , -OCF 3 or -CN.
• -CF CF-, -CF 2 O-, -OCF 2 - or a single bond, more preferably a single bond.
• -CF CF-, -CF 2 O-, -OCF 2 - or a single bond, more preferably -CF 2 O- or a single bond.
• Cyc denotes a 1,4-cyclohexylene radical
• Che denotes a 1,4-cyclohexenylene radical
• Dio denotes a 1,3-dioxane-2,5-diyl radical
• diyl radical Phe a 1,4-phenylene radical, Pyd a pyridine-2,5-diyl radical, Pyr a pyrimidine-2,5-diyl radical, Bco a bicyclo- (2,2,2) -octylene radical, Dec a decahydronaphthalene-2, 6-diyl, Nap is a naphthalene-2,6-diyl or naphthalene-2,7-diyl radical, Thn is a 1 ⁇ .S ⁇ -tetrahydronaphthalene ⁇ ...
• O-diyl radical pip is a piperidine-1, 4-diyl radical
• Phe is a Phenanthrene-2,7-diyl
• Flu is a fluorene-2,7-diyl
• Ant is an anthracene-2,6-diyl or anthracene-2,7-diyl
• Ind is an indan-2,5-diyl, wherein Cyc and or Phe can be unsubstituted or monosubstituted or polysubstituted by CH 3 , Cl, F or CN.
• a 1 and A 2 are preferably Phe, Cyc, Che, Pyd, Pyr or Dio, and particularly preferably Phe or Cyc.
• the cyclohexene-1,4-diyl group preferably has the following structures:
• Particularly preferred compounds of formula Ia include the following formulas:
• R 1 and R 2 have the meanings given above and L 1 , L 2 ,
• LL 33 and LL 44 L independently of one another, identically or differently, denote H or F.
• Particularly preferred compounds of formula Ib include the following formulas:
• R 1 and R 2 have the meanings given above and L 1 , L 2 , L 3 and L 4 independently, identically or differently mean H or F.
• R 1 is H or a linear alkyl or alkoxy radical having 1 to 10 C atoms or alkenyl or alkenyloxy having 2 to 10 C atoms.
• R 2 is -F, -CF 3 , -OCF 3 or -CN.
• R 2 is -F, -CF 3 , -OCF 3 or -CN, L 1 , L 2 , L 3 and L 4 independently of one another, identical or different or H mean.
• R 1 has the meaning given above.
• R 1 has the meaning given above.
• R 1 is H or a linear alkyl or alkoxy radical having 1 to 10 C atoms or alkenyl or alkenyloxy having 2 to 10 C -Atomen, more preferably a linear alkyl radical having 1 to 10 carbon atoms, means.
• R 1 and / or R 2 in the above and following formulas denotes an alkyl radical, this may be straight-chain or branched. It is particularly preferably straight-chain, has 2, 3, 4, 5, 6 or 7 carbon atoms and thus means ethyl, propyl, butyl, pentyl, hexyl or heptyl, furthermore methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl , Tetradecyl or pentadecyl.
• R 1 and / or R 2 is an alkyl radical in which a Chfe group is replaced by -O-, this may be straight-chain or branched. It is preferably straight-chain and has 1 to 10 C atoms. Particularly preferably, the first Ch ⁇ group of this alkyl radical is replaced by -O-, so that the radical R 1 and / or R 2 is alkoxy and in particular methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy or Nonyloxy means.
• Preferred alkenyl groups are C 2 -C 7 -I E-alkenyl, C 4 -C 7 -EE-alkenyl,
• alkenyl groups are vinyl, 1E-propenyl, 1E-butenyl, 1E-pentenyl, 1E-hexenyl, 1E-heptenyl, 3-butenyl, 3E-pentenyl, 3E-hexenyl, 3E-heptenyl, 4-pentenyl, 4Z Hexenyl, 4E-hexenyl, 4Z-heptenyl, 5-hexenyl and 6-heptenyl. Groups of up to 5 carbon atoms are especially preferred.
• R 1 and / or R 2 is an alkyl radical in which one CH 2 group has been replaced by -O- and one by -CO-, these are preferably adjacent.
• these include an acyloxy group -CO-O- or an oxycarbonyl group -O-CO-. These are particularly preferably straight-chain and have 2 to 6 C atoms.
• R 1 and / or R 2 is a monosubstituted by CN or CF 3 alkyl or alkenyl radical, this radical is preferably straight-chain and the substitution by CN or CF 3 in ⁇ -position.
• R 1 and / or R 2 is an alkyl radical which is at least monosubstituted by halogen, this radical is preferably straight-chain.
• Halogen is preferably F or Cl. In the case of multiple substitution, halogen is preferably F.
• the resulting radicals also include perfluorinated radicals. For single substitution, the fluoro or chloro substituent may be in any position, but preferably in the ⁇ position.
• Branched groups of this type usually contain no more than one chain branch.
• Formula I comprises both the racemates of these compounds and the optical antipodes and mixtures thereof.
• the compounds of the formula I are prepared by methods known per se, as described in the literature (for example in the standard works, such as Houben-Weyl, Methods of Organic Chemistry, Georg-Thieme-Verlag, Stuttgart), specifically under reaction conditions suitable for the said reactions are known and suitable. One can make use of known per se, not mentioned here variants.
• the compounds of formula I can e.g. be prepared according to the following reaction schemes or in analogy thereto. Further synthetic methods can be found in the examples.
• R 1 , R 2 , A 1 , A 2 , Z 1 , Z 2 , m and n are as defined above.
• the present invention also relates to the in
• R 1 , A 1 , Z 1 and m have the meanings given in relation to formula I.
• the other starting materials are either known or can be used in
• the starting materials can also be formed in situ, such that they are not isolated from the reaction mixture, but immediately further reacted to the compounds of formula I.
• the liquid-crystalline media according to the invention preferably contain, in addition to one or more compounds according to the invention, as further constituents 2 to 40, particularly preferably 4 to 30 components.
• these media contain, in addition to one or more compounds according to the invention 7 to 25 components.
• 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 azoxybenzenes, benzylideneanilines, biphenyls, terphenyls, phenyl or cyclohexyl benzoates, cyclohexane-carboxylic acid phenyl or cyclohexyl esters, phenyl or cyclohexyl esters Cyclohexylbenzoic acid, phenyl or cyclohexyl esters of cyclohexylcyclohexanecarboxylic acid, cyclohexylphenyl esters of benzoic acid, cyclohexanecarboxylic acid or cyclohexylcyclohexanecarboxylic acid, phenylcyclohexanes, cyclohexylb
• L and E which may be the same or different, each independently represents a bivalent radical selected from the group consisting of -Phe-, -Cyc-, -Phe-Phe-, -Phe- Cyc, -Cyc-Cyc, -Pyr-, -Dio, -G-Phe- and -G-Cyc- and their mirror images formed group, wherein Phe is unsubstituted or substituted by fluorine 1, 4-phenylene, cyc trans- 1,4-cyclohexylene or 1,4-cyclohexenylene, Pyr pyrimidine-2,5-diyl or pyridine-2,5-diyl, dio 1, 3-dioxane-2,5-diyl and G 2- (trans-1, 4-cyclohexyl) -ethyl.
• one of L and E is Cyc, Phe or Pyr.
• E is preferably Cyc, Phe or Phe-Cyc.
• the media according to the invention preferably comprise one or more components selected from the compounds of the formulas 1, 2, 3, 4 and 5, in which L and E are selected from the group Cyc, Phe and Pyr and simultaneously one or more components selected from the compounds of the Formulas 1, 2, 3, 4 and 5, wherein one of the radicals L and E is selected from the group Cyc, Phe and Pyr and the other radical is selected from the group -Phe- Phe-, -Phe-Cyc-, - Cyc-Cyc, -G-Phe and -G-Cyc-, and optionally one or more components selected from the compounds of formulas 1, 2, 3, 4 and 5, wherein the radicals L and E are selected from the group -Phe-Cyc, -Cyc-Cyc, -G-Phe and -G-Cyc-.
• R 1 and / or R are each independently of one another alkyl, alkenyl, alkoxy, alkoxyalkyl, alkenyloxy or alkanoyloxy having up to 8 C atoms, -F, -Cl, -CN, -NCS, - (O) iCH 3- ( k + i) F k Cl, where i is 0 or 1, k and I are independent are equal to or different from 0, 1, 2 or 3 and for the sum (k + I): 1 ⁇ (k + I) ⁇ 3.
• R 1 and R "in a smaller subgroup of the compounds of the formulas 1, 2, 3, 4 and 5 in each case independently of one another are alkyl, alkenyl,
• Alkoxy, alkoxyalkyl, alkenyloxy or alkanoyloxy with up to 8 carbon atoms In the following, this smaller subgroup will be called Group A and the compounds will be referred to as Partial Formulas 1a, 2a, 3a, 4a and 5a. In most of these compounds, R 1 and R "are different from one another, one of these radicals usually being alkyl, alkenyl, alkoxy or alkoxyalkyl.
• R " is -F, -Cl, -NCS or - (O) j CH3 - (k + i ) F k Cl
• k and I are independently, identically or differently 0, 1, 2 or 3 and for the sum (k + I): 1 ⁇ (k + I) ⁇ 3.
• the compounds in which R "has this meaning, are denoted by the subformulae 1 b, 2b, 3b, 4b and 5b.
• R has the meaning -F, -Cl, -NCS, -CF 3 , -OCHF 2 or -OCF 3 .
• R 1 has the meaning given for the compounds of sub-formulas 1a to 5a and is preferably alkyl, alkenyl, alkoxy or alkoxyalkyl.
• R denotes -CN.
• This subgroup is referred to below as group C and the compounds of this subgroup are correspondingly reacted with partial formulas 1c, 2c, 3c, 4c and
• R 1 has the meaning given for the compounds of sub-formulas 1a to 5a and is preferably alkyl, alkoxy or alkenyl.
• the media according to the invention preferably comprise one or more compounds which are selected from groups A, B and / or C.
• the mass fractions of the compounds from these groups on the media according to the invention are preferably:
• Group A preferably 0 to 90%, particularly preferably 20 to 90%, in particular 30 to 90%;
• Group B preferably 0 to 80%, particularly preferably 10 to 80%, in particular 10 to 65%;
• Group C preferably 0 to 80%, particularly preferably 5 to 80%, in particular 5 to 50%;
• the sum of the mass fractions of the compounds of the groups A, B and / or C contained in the respective inventive media is preferably 5 to 90% and particularly preferably 10 to 90%.
• the media according to the invention preferably contain 1 to 40%, more preferably 5 to 30% of the compounds of the formula I. Further preferred are media containing more than 40%, particularly preferably 45 to 90% of compounds of the formula I.
• the media preferably three, four or five compounds according to the invention.
• the preparation of the liquid-crystal mixtures according to the invention is carried out in a conventional manner.
• the desired amount of the components used in lesser amount is dissolved in the components making up the main component, preferably at elevated temperature. It is also possible to use solutions of the components in an organic solvent, e.g. In acetone, chloroform or methanol " , _
• the dielectrics may also contain further additives known to the person skilled in the art and described in the literature. For example, 0 to 15%, preferably 0 to 10%, of pleochroic dyes and / or chiral dopants may be added. The individual, added
• Compounds are preferably used in concentrations of from 0.01 to 6%, particularly preferably from 0.1 to 3%.
• concentration data of the other constituents of the liquid-crystal mixtures ie the liquid-crystalline or mesogenic compounds are given, without taking into account the concentration of these additives.
• N nematic phase
• Sm smectic phase
• I isotropic phase.
• ⁇ n optical anisotropy (589 nm, 2O 0 C) and ⁇ the dielectric anisotropy (IkHz, 20 0 C).
• ⁇ n and ⁇ values of the compounds according to the invention are obtained by extrapolation from liquid-crystalline mixtures which consist of 10% of the particular compound according to the invention and 90% of the commercially available liquid crystal ZLI 4792 (Merck, Darmstadt).
• Conventional workup means: water is optionally added, extracted with methylene chloride, diethyl ether or toluene, separated, the organic phase is dried, evaporated and the product is purified by distillation under reduced pressure or crystallization and / or chromatography.
• the following abbreviations are used above and below:
• the ketone 11 is prepared.
• the corresponding Grignard reagent is prepared in 75 ml of THF from 3.2 g (130 mmol) of magnesium turnings and 15.5 ml (130 mmol) of the bromide 2. Subsequently, a solution of the ketone 1 in 25 ml of THF is added to the reagent. The batch is heated to boiling for 1 hour. The cooled mixture is hydrolyzed to pH 1 with hydrochloric acid adjusted and extracted with MTB ether. The organic phase is washed with saturated sodium bicarbonate solution and concentrated. The residue obtained is purified on silica gel (toluene). Yield: 22.0 g (68%)
• reaction mixture was added to water and diluted with n-heptane.
• organic phase is concentrated and the residue obtained is passed through silica gel. The residue is used without further purification in the subsequent stage.
• Example 145 Analogously to Example 145, the following compounds according to the invention are obtained using the appropriate precursors: Examples 146-162
• Example 201 The compound of Example 201 is obtained as follows.
• the product has the following properties:
• the ketone 10 is prepared analogously to the above procedure.
• a boiling suspension of 2.9 g (80 mmol) of lithium aluminum hydride in 50 ml of THF is treated with a solution of 18 g (70% strength, 60 mmol) of malonate 17 in 50 ml of THF and then refluxed for 1 h.
• the cooled mixture is hydrolyzed, acidified and diluted with MTB ether and filtered with suction through Celite.
• the organic phase is washed with water and sat. NaHC03 soln. washed, dried and concentrated. The residue is used without further purification in the subsequent stage.
• the product has the following properties:
• the precursor of the compound compound is obtained according to the following reaction scheme.
• 16 g of the product of the precursor are dissolved in 60 ml of toluene and mixed with 36 ml of formic acid and stirred at RT for 18 h. The mixture is then added to 200 ml of water. The aqueous phase was extracted with MTB ether, the organic phase with sat. NaHCO 3 -sol. washed and concentrated. The residue was used without further purification in the subsequent stage.
• reaction was hydrolyzed and treated with a hot solution of 93.2 g of sodium bicarbonate decahydrate in 30 ml of water. After stirring for 30 minutes, the solid is separated off. The filtrate is concentrated. The residue is used without further purification in the subsequent stage.
• the product has the properties:

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