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US 7,923,079 B2Granted
Liquid-crystalline medium and liquid-crystal display comprising 1,2-difluoroethene compounds
AssigneeMerck Patent GmbH
InventorsMichael Wittek, Markus Czanta, Harald Hirschmann, Volker Reiffenrath
Life of this patent
Estimating the term…
Abstract
The present invention relates to a liquid-crystalline medium comprising 1,2-difluoroethene compounds of the general formula I, in which R1, ring A, Z1, Z2, m, X and L1-6 are as defined in Claim 1. The invention also relates to the use of the medium for electro-optical purposes and to displays containing this medium. Novel 1,2-difluoroethene compounds having 3 or more rings are disclosed.
Claims25
A liquid-crystalline medium of positive dielectric anisotropy based on a mixture of compounds comprising:
- one or more compounds of the formula I
- in which
- R1 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals are each, independently of one another, replaced by —C≡C—, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
- ring A denotes a ring system of the formulae
- pointing to the left or right,
- Z1, Z2 denote a single bond, —C≡C—, —CF═CF—, —CH═CH—, —CF2O— or —CH2CH2—, where at least one group from Z1 and Z2 denotes the group —CF═CF—,
- X denotes F, Cl, CN, SF5 or a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals are each, independently of one another, replaced by —C≡C—, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
- L1, L2, L3, L4, L5 and L6 each, independently of one another, denote H or F, and
- m 1;
- and
- one or more compounds of formulae XIV and XV:
- in which
- R0 is in each case independently n-alkyl having up to 9 C atoms, oxaalkyl having up to 9 C atoms, fluoroalkyl having up to 9 C atoms, or alkenyl having up to 9 C atoms,
- X0 is F, Cl, halogenated alkyl having up to 6 C atoms, halogenated alkenyl having up to 6 C atoms, halogenated alkenyloxy having up to 6 C atoms, or halogenated alkoxy having up to 6 C atoms, and
- rings B and C, independently of one another, are each 1,4-phenylene which is substituted by 0, 1 or 2 fluorine, wherein at least one of the 1,4-phenylene rings is mono- or polysubstituted by fluorine;
- and
- further comprising one or more compounds of formulae Z-1 to Z-9
- and/or one or more compounds of formulae II, III, IV, V and VI
- wherein
- R1a and R2a each, independently of one another, denote H, CH3, C2H5 or n-C3H7,
- R0 denotes n-alkyl having up to 9 C atoms, oxaalkyl having up to 9 C atoms, fluoroalkyl having up to 9 C atoms, or alkenyl having up to 9 C atoms,
- alkyl, alkyl* denote an unsubstituted n-alkyl radical having 1 to 7 C atoms,
- alkenyl denotes an unsubstituted alkenyl radical having 2-7 C atoms,
- X0 denotes F, Cl, halogenated alkyl having up to 9 C atoms, halogenated alkenyl having up to 9 C atoms, halogenated alkenyloxy having up to 9 C atoms, or halogenated alkoxy having up to 6 C atoms,
- Z0 denotes —C2F4—, —CF═CF—, —C2H4—, —(CH2)4—, —OCH2—, —CH2O—, —CF2O— or —OCF2—,
- Y1 to Y4 each, independently of one another, denote H or F,
- r denotes 0 or 1, and
- t denotes 0, 1 or 2.
25 more elements
A liquid-crystalline medium of positive dielectric anisotropy based on a mixture of compounds comprising:
- one or more compounds of the formula I
- in which
- R1 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals are each, independently of one another, replaced by —C≡C—, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
- ring A denotes a ring system of the formulae
- pointing to the left or right,
- Z1, Z2 denote a single bond, —C≡C—, —CF═CF—, —CH═CH—, —CF2O— or —CH2CH2—, where at least one group from Z1 and Z2 denotes the group —CF═CF—,
- X denotes F, Cl, CN, SF5 or a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals are each, independently of one another, replaced by —C≡C—, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
- L1, L2, L3, L4, L5 and L6 each, independently of one another, denote H or F, and
- m 1;
- and
- one or more compounds of formulae XIV and XV:
- in which
- R0 is in each case independently n-alkyl having up to 9 C atoms, oxaalkyl having up to 9 C atoms, fluoroalkyl having up to 9 C atoms, or alkenyl having up to 9 C atoms,
- X0 is F, Cl, halogenated alkyl having up to 6 C atoms, halogenated alkenyl having up to 6 C atoms, halogenated alkenyloxy having up to 6 C atoms, or halogenated alkoxy having up to 6 C atoms, and
- rings B and C, independently of one another, are each 1,4-phenylene which is substituted by 0, 1 or 2 fluorine, wherein at least one of the 1,4-phenylene rings is mono- or polysubstituted by fluorine;
- and
- further comprising one or more compounds of formulae O1 and O2
- and/or one or more compounds of formulae D1 and D2
- in which
- alkyl and alkyl* each, independently of one another, denote a straight-chain or branched alkyl group having 1-7 carbon atoms, and
- R0 denotes n-alkyl having up to 9 C atoms, oxaalkyl having up to 9 C atoms, fluoroalkyl having up to 9 C atoms, or alkenyl having up to 9 C atoms.
18 more elements
A liquid-crystalline medium of positive dielectric anisotropy based on a mixture of compounds comprising:
- one or more compounds of the formula I
- in which
- R1 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals are each, independently of one another, replaced by —C≡C—, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
- ring A denotes a ring system of the formulae
- pointing to the left or right,
- Z1, Z2 denote a single bond, —C≡C—, —CF═CF—, —CH═CH—, —CF2O— or —CH2CH2—, where at least one group from Z1 and Z2 denotes the group —CF═CF—,
- X denotes F, Cl, CN, SF5 or a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals are each, independently of one another, replaced by —C≡C—, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
- L1, L2, L3, L4, L5 and L6 each, independently of one another, denote H or F, and
- m 1;
- and
- one or more compounds selected from compounds of formulas XIV-1, XIV-2, and XIV-3:
- wherein R0 is n-alkyl having up to 9 C atoms, oxaalkyl having up to 9 C atoms, fluoroalkyl having up to 9 C atoms, or alkenyl having up to 9 C atoms.
9 more elements
A liquid-crystalline medium of positive dielectric anisotropy based on a mixture of compounds comprising:
- one or more compounds of the formula I
- in which
- R1 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals are each, independently of one another, replaced by —C≡C—, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
- ring A denotes a ring system of the formulae
- pointing to the left or right,
- Z1, Z2 denote a single bond, —C≡C—, —CF═CF—, —CH═CH—, —CF2O— or —CH2CH2—, where at least one group from Z1 and Z2 denotes the group —CF═CF—,
- X denotes F, Cl, CN, SF5 or a halogenated alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals are each, independently of one another, replaced by —C≡C—, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
- L1, L2, L3, L4, L5 and L6 each, independently of one another, denote H or F, and
- m denotes 0 or 1;
- and
- one or more compounds of formulae XIV and XV:
- in which
- R0 is in each case independently n-alkyl having up to 9 C atoms, oxaalkyl having up to 9 C atoms, fluoroalkyl having up to 9 C atoms, or alkenyl having up to 9 C atoms,
- X0 is F, Cl, halogenated alkyl having up to 6 C atoms, halogenated alkenyl having up to 6 C atoms, halogenated alkenyloxy having up to 6 C atoms, or halogenated alkoxy having up to 6 C atoms, and
- rings B and C, independently of one another, are each 1,4-phenylene which is substituted by 0, 1 or 2 fluorine, wherein at least one of the 1,4-phenylene rings is mono- or polysubstituted by fluorine, and
- further comprising one or more compounds of formulae Z-1 to Z-9
- and/or one or more compounds selected from formulae II, III, IV, V and VI
- in which
- R1a and R2a each, independently of one another, denote H, CH3, C2H5 or n-C3H7,
- R0 denotes n-alkyl having up to 9 C atoms, oxaalkyl having up to 9 C atoms, fluoroalkyl having up to 9 C atoms, or alkenyl having up to 9 C atoms, in which
- alkyl, alkyl* denote an unsubstituted n-alkyl radical having 1 to 7 C atoms, and
- alkenyl denotes an unsubstituted alkenyl radical having 2-7 C atoms,
- X0 denotes F, Cl, halogenated alkyl having up to 9 C atoms, halogenated alkenyl having up to 9 C atoms, halogenated alkenyloxy having up to 9 C atoms, or halogenated alkoxy having up to 6 C atoms,
- Z0 denotes —C2F4—, —CF═CF—, —C2H4—, —(CH2)4—, —OCH2—, —CH2O—, —CF2O— or —OCF2—,
- Y1 to Y4 each, independently of one another, denote H or F,
- r denotes 0 or 1, and
- t denotes 0, 1 or 2.
24 more elements
A liquid-crystalline medium of positive dielectric anisotropy based on a mixture of compounds comprising:
- one or more compounds of the formula I
- in which
- R1 denotes a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals are each, independently of one another, replaced by —C≡C—, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
- ring A denotes a ring system of the formulae
- pointing to the left or right,
- Z1, Z2 denote a single bond, —C≡C—, —CF═CF—, —CH═CH—, —CF2O— or —CH2CH2—, where at least one group from Z1 and Z2 denotes the group —CF═CF—,
- X denotes F, Cl, CN, SF5 or a halogenated or unsubstituted alkyl or alkoxy radical having 1 to 15 C atoms, where, in addition, one or more CH2 groups in these radicals are each, independently of one another, replaced by —C≡C—, —CH═CH—, —O—, —CO—O— or —O—CO— in such a way that O atoms are not linked directly to one another,
- L1, L2, L3, L4, L5 and L6 each, independently of one another, denote H or F, and
- m denotes 0 or 1;
- and
- one or more compounds of formula XV:
- in which
- R0 is n-alkyl having up to 9 C atoms, oxaalkyl having up to 9 C atoms, or alkenyl having up to 9 C atoms, and
- rings C, independently of one another, are each 1,4-phenylene which is substituted by 0, 1 or 2 fluorine, wherein at least one of the 1,4-phenylene rings is mono- or polysubstituted by fluorine, and
- further comprising one or more compounds of formulae Z-1 to Z-9
- and/or one or more compounds selected from formulae II, III, IV, V and VI:
- in which
- R1a and R2a each, independently of one another, denote H, CH3, C2H5 or n-C3H7,
- R0 denotes n-alkyl having up to 9 C atoms, oxaalkyl having up to 9 C atoms, fluoroalkyl having up to 9 C atoms, or alkenyl having up to 9 C atoms,
- alkyl, alkyl* denote an unsubstituted n-alkyl radical having 1 to 7 C atoms, and
- alkenyl denotes an unsubstituted alkenyl radical having 2-7 C atoms,
- X0 denotes F, Cl, halogenated alkyl having up to 9 C atoms, halogenated alkenyl having up to 9 C atoms, halogenated alkenyloxy having up to 9 C atoms, or halogenated alkoxy having up to 6 C atoms,
- Z0 denotes —C2F4—, —CF═CF—, —C2H4—, —(CH2)4— —OCH2—, —CH2O—, —CF2O— or —OCF2—,
- Y1 to Y4 each, independently of one another, denote H or F,
- r denotes 0 or 1, and
- t denotes 0, 1 or 2.
23 more elements
Dependencies are inferred from the claim text.