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Electro-optical liquid crystal display element

Assignee: Merck Patent GmbH
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Filing: 1988-04-21
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Granted: 1993-03-23
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Expires: 2008-04-21
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Abstract

Abstract PCT No. PCT/EP88/00335 Sec. 371 Date Dec. 23, 1988 Sec. 102(e) Date Dec. 23, 1988 PCT Filed Apr. 21, 1988 PCT Pub. No. WO88/08441 PCT Pub. Date Nov. 3, 1988.The invention relates to an electro-optical liquid crystal display element containing a dielectric with at least two liquid-crystalline components, wherein the dielectric, for shortening the switching times, contains at least one fluorine-containing compound of the formula I R1-(A1-Z1)m-A2-R2 I wherein the radicals R1, R2, A1, A2, Z1 and m have the meaning given in claim 1.

Inventors

  • 👤 Eike Poetsch
  • 👤 Hans A. Kurmeier
  • 👤 Rudolf Eidenschink
  • 👤 Georg Weber
  • 👤 Andreas Wachtler

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 05:11
CPC Classifications
C; C09; C09K; C09K19/00; C09K19/04; C09K19/06; C09K19/34; C09K19/3441; C09K19/345; C09K19/3458; C09K19/3469; C09K19/08; C09K19/30; C09K19/3001

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 402 words
An electro-optical liquid crystal display element, based on an effect from the group consisting of the twisted cell, guest-host, deformation of aligned phase, dynamic scattering, SBE and STN effects, containing a dielectric with at least two liquid-crystalline components, characterized in that, for shortening the switching times, the dielectric contains at least one fluorine-containing compound of the formula I R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --R.sup.2 I wherein one of the radicals R 1 and R 2 is H, F, Cl, Br, --CN, --NCS or an unsubstituted straight-chain alkyl group having 1-15 C atoms, in which one or two CH 2 groups can also be replaced by a grouping selected from the group comprising --O--, --CO--, --O--CO--, --CO--O--, --C.tbd.C-- and --CH═CH--, no 2 heteroatoms being directly linked to one another, the other radical R 1 or R 2 has the formula --X'--Q'--Y'--R.sup.5 in which X' is --CO--, --O--CO--, --O--, or a single bond, Q' is alkylene having 2 to 5 C atoms, Y' is perfluoroalkylene having 2 to 15 C atoms, in which one or more CF 2 groups can also be replaced by --CHF-- or --CF═CF--, and R 5 is H, F, or an alkyl group having 1 to 5 C atoms, with the proviso that the group of the formula --X'--Q'--Y'--R 5 does not contain more than 15 C atoms in total and contains at least two CF 2 groups, A 1 and A 2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH 3 groups and/or CN groups and in which one or two CH groups can also be replaced by N atoms, 1,4-cyclohexylene in which one or two non-adjacent CH 2 groups can also be replaced by O atoms and/or S atoms, piperidine-1,4-diyl, 1,4-bicyclo-[2.2.2]octylene, unsubstituted or CN-substituted decahydronaphthalene-2,6-diyl or 1,2,3,4,-tetrahydronaphthalene-2,6-diyl, and A 2 is optionally a single bond, m is 0, 1, 2 or 3 and Z 1 is --CO--O--, --O--CO--, --OCH 2 --, --CH 2 O--, --CH 2 --CH 2 --, substituted ethylene or a single bond, it being possible for the groups A 1 to be identical or different and the groups Z 1 to be identical or different in the case of m=2 or 3, with the proviso that, in the case of m=0, the sum of the number of C atoms in the two groups R 1 and R 2 is at least 8.
Claim 2
Dependent Claim 402 words
An electro-optical liquid crystal display element, based on an effect from the group consisting of the twisted cell, guest-host, deformation of aligned phase, dynamic scattering, SBE and STN effects, containing a dielectric with at least two liquid-crystalline components, characterized in that, for shortening the switching times, the dielectric contains at least one fluorine-containing compound of the formula I R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --R.sup.2 I wherein one of the radicals R 1 and R 2 is H, F, Cl, Br, --CN, --NCS or an unsubstituted straight-chain alkyl group having 1-15 C atoms, in which one or two CH 2 groups can also be replaced by a grouping selected from the group comprising --O--, --CO--, --O--CO--, --CO--O--, --C.tbd.C-- and --CH═CH--, no 2 heteroatoms being directly linked to one another, the other radical R 1 or R 2 has the formula --X'--Q'--Y'--R.sup.5 in which X' is --CO--, --O--CO--, --O--, or a single bond, Q' is alkylene having 2 to 5 C atoms, Y' is perfluoroalkylene having 2 to 15 C atoms, in which one or more CF 2 groups can also be replaced by --CHF-- or --CF═CF--, and R 5 is H, F, or an alkyl group having 1 to 5 C atoms, with the proviso that the group of the formula --X'--Q'--Y'--R 5 does not contain more than 15 C atoms in total and contains at least two CF 2 groups, A 1 and A 2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH 3 groups and/or CN groups and in which one or two CH groups can also be replaced by N atoms, 1,4-cyclohexylene in which one or two non-adjacent CH 2 groups can also be replaced by O atoms and/or S atoms, piperidine-1,4-diyl, 1,4-bicyclo-[2.2.2]octylene, unsubstituted or CN-substituted decahydronaphthalene-2,6-diyl or 1,2,3,4,-tetrahydronaphthalene-2,6-diyl, and A 2 is optionally a single bond, m is 0, 1, 2 or 3 and Z 1 is --CO--O--, --O--CO--, --OCH 2 --, --CH 2 O--, --CH 2 --CH 2 --, substituted ethylene or a single bond, it being possible for the groups A 1 to be identical or different and the groups Z 1 to be identical or different in the case of m=2 or 3, with the proviso that, in the case of m=0, the sum of the number of C atoms in the two groups R 1 and R 2 is at least 8.
Claim 3
Dependent Claim 23 words
A liquid crystalline dielectric with at least two liquid-crystalline components, containing at least one compound of the formula I according to claim 1.
Claim 4
Dependent Claim 225 words
A display element according to claim 1, of Formula IV R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --R.sup.2 IV wherein R 1 is a straight chain alkyl group having 1-15 C atoms, in which one or two CH 2 groups can also be replaced by a grouping selected from the group comprising --O--, --CO--, --O--CO--, --CO--O--, --C.tbd.C-- and --CH═CH--, no 2 heteroatoms being directly linked to one another, R 2 has the formula --X'--Q'--Y'--R.sup.5 in which X' is --CO--O, --O--CO--, --O--, or a single bond, Q' is alkylene having 2 to 5 C atoms, Y' is perfluoroalkylene having 2 to 15 C atoms, in which one or more CF 2 groups can also be replaced by --CHF-- or --CF═CF--, and R 5 is H, F, or an alkyl group having 1 to 5 C atoms, with the proviso that the group of the formula --X'--Q'--Y'--R 5 does not contain more than 15 C atoms in total and contains at least two CF 2 groups, A 1 is 1,4-cyclohexylene in which one or two non-adjacent CH 2 groups can also be replaced by O atoms and/or S atoms, A 2 is 1,4-phenylene which is unsubstituted or substituted by one or two F atoms, m is 1 or 2 and Z 1 is --CO--O--, --O--CO--, --OCH 2 --, --OCH 2 O--, --CH 2 --CH 2 -- or a single bond.
Claim 5
Dependent Claim 255 words
A fluorine-containing compound of the formula: R 1 --(A 1 --Z 1 ) m --A 2 --R 2 I wherein one of the radicals R 1 and R 2 is F, Cl, Br, --CN, --NCS, or a straight-chain alkyl group having 1-5 C atoms, in which one or two CH 2 groups can also be replaced by a grouping selected from the group comprising --O-- and --CH═CH--, no two oxygen atoms being directly linked to one another, the other radical R 1 or R 2 is of the formula --X'--Q'--Y'--R.sup.5 in which X' is --CO--O--, --O--CO--, --O--, or a single bond, Q' is alkylene having 2-5 C atoms, Y' is perfluoroalkylene having 2-15 C atoms, and R 5 is H or F, with the proviso that the group of the formula --X'--Q'--Y'--R 5 does not contain more than 15 C atoms in total, A 1 and A 2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two F atoms and in which one or two CH groups can also be replaced by N atoms, 1,4-cyclohexylene in which one or two non-adjacent CH 2 groups can also be replaced by O atoms, m is 1, 2, or 3, and Z 1 is [--CO--O--, --O--CO--, --OCH 2 --, --CH 2 O--,] --CH 2 --CH 2 --, or a single bond, it being possible for the groups A 1 to be identical or different and the groups Z 1 to be identical or different in the case of m=2 or 3.
Claim 6
Dependent Claim 255 words
A fluorine-containing compound of the formula: R 1 --(A 1 --Z 1 ) m --A 2 --R 2 I wherein one of the radicals R 1 and R 2 is F, Cl, Br, --CN, --NCS, or a straight-chain alkyl group having 1-5 C atoms, in which one or two CH 2 groups can also be replaced by a grouping selected from the group comprising --O-- and --CH═CH--, no two oxygen atoms being directly linked to one another, the other radical R 1 or R 2 is of the formula --X'--Q'--Y'--R.sup.5 in which X' is --CO--O--, --O--CO--, --O--, or a single bond, Q' is alkylene having 2-5 C atoms, Y' is perfluoroalkylene having 2-15 C atoms, and R 5 is H or F, with the proviso that the group of the formula --X'--Q'--Y'--R 5 does not contain more than 15 C atoms in total, A 1 and A 2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two F atoms and in which one or two CH groups can also be replaced by N atoms, 1,4-cyclohexylene in which one or two non-adjacent CH 2 groups can also be replaced by O atoms, m is 1, 2, or 3, and Z 1 is [--CO--O--, --O--CO--, --OCH 2 --, --CH 2 O--,] --CH 2 --CH 2 --, or a single bond, it being possible for the groups A 1 to be identical or different and the groups Z 1 to be identical or different in the case of m=2 or 3.
Claim 7
Dependent Claim 205 words
A compound according to claim 4, of the formula IV R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --R.sup.2 IV wherein R 1 is an alkyl group having 1-15 C atoms, in which one or two CH 2 groups can also be replaced by --O-- or --CH═CH--, no two oxygen atoms being directly linked to one another R 2 has the formula --X'--Q'--Y'--R 5 in which X' is --CO--O, --O--CO--, --O--, or a single bond, Q' is alkylene having 2 to 5 C atoms, Y' is perfluoroalkylene having 2 to 15 C atoms, in which one or more CF 2 groups can also be replaced by --CHF-- or --CF═CF--, and R 5 is H, F, or an alkyl group having 1 to 5 C atoms, with the proviso that the group of the formula --X'--Q'--Y'--R 5 does not contain more than 15 C atoms in total and contains at least two CF 2 groups, A 1 is 1,4-cyclohexylene, A 2 is 1,4-phenylene which is unsubstituted or substituted by one or two F atoms, m is 1 or 2, and Z 1 is --CH 2 --CH 2 --, or a single bond, it being possible for the groups Z 1 to be identical or different in the case of m=2.
Claim 8
Dependent Claim 191 words
A fluorine-containing compound of the formula: R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --R.sup.2 I wherein one of the radicals R 1 and R 2 is a straight-chain alkyl group having 1-15 C atoms, in which one or two CH 2 groups can also be replaced by --O--, no two oxygen atoms being directly linked to one another, the other radical R 1 or R 2 is of the formula --X'--Q'--Y'--R.sup.5 in which X' is --CO--O--, --O--, or a single bond, Q' is alkylene having 2-5 C atoms, Y' is perfluoroalkylene having 2-15 C atoms, and R 5 is H or F, with the proviso that the group of the formula --X'--Q'--Y'--R 5 does not contain more than 15 C atoms in total, A 1 and A 2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one F atom and in which one or two CH groups can also be replaced by N atoms or 1,4-cyclohexylene, m is 1 or 2, and Z 1 is a single bond, it being possible for the groups A 1 and Z 1 to be identical or different in the case of m=2.
Claim 9
Dependent Claim 191 words
A fluorine-containing compound of the formula: R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --R.sup.2 I wherein one of the radicals R 1 and R 2 is a straight-chain alkyl group having 1-15 C atoms, in which one or two CH 2 groups can also be replaced by --O--, no two oxygen atoms being directly linked to one another, the other radical R 1 or R 2 is of the formula --X'--Q'--Y'--R.sup.5 in which X' is --CO--O--, --O--, or a single bond, Q' is alkylene having 2-5 C atoms, Y' is perfluoroalkylene having 2-15 C atoms, and R 5 is H or F, with the proviso that the group of the formula --X'--Q'--Y'--R 5 does not contain more than 15 C atoms in total, A 1 and A 2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one F atom and in which one or two CH groups can also be replaced by N atoms or 1,4-cyclohexylene, m is 1 or 2, and Z 1 is a single bond, it being possible for the groups A 1 and Z 1 to be identical or different in the case of m=2.
Claim 10
Dependent Claim 200 words
A compound according to claim 6, of the formula IV R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --R.sup.2 IV wherein R 1 is an alkyl group having 1-15 C atoms, in which one or two CH 2 groups can also be replaced by --O--, no two oxygen atoms being directly linked to one another, R 2 has the formula --X'--Q'--Y'--R.sup.5 in which X' is --CO--O, --O--CO--, --O--, or a single bond, Q' is alkylene having 2 to 5 C atoms, Y' is perfluoroalkylene having 2 to 15 C atoms, in which one or more CH 2 groups can also be replaced by --CHF-- or --CF═CF--, and R 5 is H, F, or an alkyl group having 1 to 5 C atoms, with the proviso that the group of the formula --X'--Q'--Y'--R 5 does not contain more than 15 C atoms in total and contains at least two CF 2 groups, A 1 is 1,4-cyclohexylene, A 2 is 1,4-phenylene which is unsubstituted or substituted by one F atom, m is 1 or 2, and Z 1 is --CH 2 --CH 2 -- or a single bond, it being possible for the group Z 1 to be identical or different in the case of m=2.
Claim 11
Dependent Claim 294 words
An electro-optical liquid crystal element, based on an effect from the group consisting of the twisted cell, guest-host, deformation of aligned phase, dynamic scattering, SBE and STN effects, containing a dielectric with at least two liquid-crystalline components, characterized in that, for shortening the switching times, the dielectric contains at least one fluorine-containing compound of the formula I R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --R.sup.2 I wherein one of the radicals R 1 and R 2 is H, F, Cl, Br, --CN, --NCS or an unsubstituted or substituted straight-chain alkyl group having 1-15 C atoms, in which one or two CH 2 groups can also be replaced by a grouping selected from the group comprising --O--, --CO--, --O--CO--, --CO--O--, --CH--halogen--, --CHCN--, --CCH 3 CN--, --C.tbd.C-- and --CH═CH--, no 2 heteroatoms being directly linked to one another, the other radical R 1 or R 2 is --OCF 2 CF 2 H or --CF 2 CF 2 H, and A 1 and A 2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH 3 groups and/or CN groups and in which one or two CH groups can also be replaced by N atoms, 1,4-cyclohexylene in which one or two non-adjacent CH 2 groups can also be replaced by O atoms and/or S atoms, piperidine-1,4-diyl, 1,4-bicyclo-[2.2.2]octylene, unsubstituted or CN-substituted decahydronaphthalene-2,6-diyl or 1,2,3,4,-tetrahydronaphthalene-2,6-diyl, and A 2 is a single bond, m is 0, 1, 2 or 3 and Z 1 is --CO--O--, --O--CO--, --OCH 2 --, --CH 2 --CH 2 --, substituted ethylene or a single bond, it being possible for the groups A 1 to be identical or different and for the groups Z 1 to be identical or different in the case of m=2 or 3.
Claim 12
Dependent Claim 294 words
An electro-optical liquid crystal element, based on an effect from the group consisting of the twisted cell, guest-host, deformation of aligned phase, dynamic scattering, SBE and STN effects, containing a dielectric with at least two liquid-crystalline components, characterized in that, for shortening the switching times, the dielectric contains at least one fluorine-containing compound of the formula I R.sup.1 --(A.sup.1 --Z.sup.1).sub.m --A.sup.2 --R.sup.2 I wherein one of the radicals R 1 and R 2 is H, F, Cl, Br, --CN, --NCS or an unsubstituted or substituted straight-chain alkyl group having 1-15 C atoms, in which one or two CH 2 groups can also be replaced by a grouping selected from the group comprising --O--, --CO--, --O--CO--, --CO--O--, --CH--halogen--, --CHCN--, --CCH 3 CN--, --C.tbd.C-- and --CH═CH--, no 2 heteroatoms being directly linked to one another, the other radical R 1 or R 2 is --OCF 2 CF 2 H or --CF 2 CF 2 H, and A 1 and A 2 independently of one another are each 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH 3 groups and/or CN groups and in which one or two CH groups can also be replaced by N atoms, 1,4-cyclohexylene in which one or two non-adjacent CH 2 groups can also be replaced by O atoms and/or S atoms, piperidine-1,4-diyl, 1,4-bicyclo-[2.2.2]octylene, unsubstituted or CN-substituted decahydronaphthalene-2,6-diyl or 1,2,3,4,-tetrahydronaphthalene-2,6-diyl, and A 2 is a single bond, m is 0, 1, 2 or 3 and Z 1 is --CO--O--, --O--CO--, --OCH 2 --, --CH 2 --CH 2 --, substituted ethylene or a single bond, it being possible for the groups A 1 to be identical or different and for the groups Z 1 to be identical or different in the case of m=2 or 3.

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