US2018163134A1PendingUtilityA1
Liquid crystal medium and liquid crystal display
Est. expiryJun 5, 2032(~5.9 yrs left)· nominal 20-yr term from priority
C09K 2019/0466C09K 2019/3422C09K 19/20C09K 19/3458C09K 19/54C09K 19/3444C09K 19/3001C09K 19/3402C09K 19/3098C09K 19/3483C09K 2019/0459G02F 1/13
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Claims
Abstract
The present invention relates to dielectrically positive liquid-crystalline media comprising one or more compounds of the formula I and/or TINUVIN 770®, in which the parameters have the respective meanings indicated in the specification, and optionally one or more further dielectrically positive compounds and optionally one or more further dielectrically neutral compounds, and to liquid-crystal displays, especially active-matrix displays and in particular TN, IPS and FFS displays, containing these media.
Claims
exact text as granted — not AI-modified1 . Liquid-crystal medium having positive dielectric anisotropy, characterised in that
a) one or more compounds selected from the group of the compounds of the formula I,
in which
n denotes an integer from 1 to 4,
m denotes (4-n),
denotes an organic radical having 4 bonding sites, in which, in addition to the m groups R 12 present in the molecule, but independently thereof, a further H atom may be replaced by R 12 or a plurality of further H atoms may be replaced by R 12 , in which one —CH 2 — group or a plurality of —CH 2 — groups may be replaced by —O— or —(C═O)— in such a way that two O atoms are not bonded directly to one another, or denotes a substituted or unsubstituted aromatic or heteroaromatic hydrocarbon radical having 1 to 4 valences, in which, in addition to the m groups R 12 present in the molecule, but independently thereof, a further H atom may be replaced by R 12 or a plurality of further H atoms may be replaced by R 12 ,
Z 11 and Z 12 , independently of one another, denote —O—, —(C═O)—, —(N—R 14 )— or a single bond, but do not both simultaneously denote —O—,
r and s, independently of one another, denote 0 or 1,
Y 11 to Y 14 each, independently of one another, denote alkyl having 1 to 4 C atoms and alternatively, independently of one another, one or both of the pairs (Y 11 and Y 12 ) and (Y 13 and Y 14 ) together also denote a divalent group having 3 to 6 C atoms,
R 11 denotes O—R 13 , O ⋅ or OH,
R 12 on each occurrence, independently of one another, denotes H, F, OR 14 , NR 14 R 15 , a straight-chain or branched alkyl chain having 1-20 C atoms, in which one —CH 2 — group or a plurality of —CH 2 — groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, or denotes a hydrocarbon radical which contains a cycloalkyl or alkylcycloalkyl unit, and in which one —CH 2 — group or a plurality of —CH 2 — groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, and in which one H atom or a plurality of H atoms may be replaced by OR 14 , N(R 14 )(R 15 ) or R 16 , or denotes an aromatic or heteroaromatic hydrocarbon radical, in which one H atom or a plurality of H atoms may be replaced by OR 14 , N(R 14 )(R 15 ) or R 16 ,
R 13 on each occurrence, independently of one another, denotes a straight-chain or branched alkyl chain having 1-20 C atoms, in which one —CH 2 — group or a plurality of —CH 2 — groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, or denotes a hydrocarbon radical which contains a cycloalkyl or alkylcycloalkyl unit, and in which one —CH 2 — group or a plurality of —CH 2 — groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, and in which one H atom or a plurality of H atoms may be replaced by OR 14 , N(R 14 )(R 15 ) or R 16 , or denotes an aromatic or heteroaromatic hydrocarbon radical, in which one H atom or a plurality of H atoms may be replaced by OR 14 , N(R 14 )(R 15 ) or R 16 ,
or can be
(1,4-cyclohexylene), in which one or more —CH 2 — groups may be replaced by —O—, —CO— or —NR 14 —, or an acetophenyl, isopropyl or 3-heptyl radical,
R 14 on each occurrence, independently of one another, denotes a straight-chain or branched alkyl or acyl group having 1 to 10 C atoms or an aromatic hydrocarbon or carboxyl radical having 6-12 C atoms,
R 15 on each occurrence, independently of one another, denotes a straight-chain or branched alkyl or acyl group having 1 to 10 C atoms or an aromatic hydrocarbon or carboxyl radical having 6-12 C atoms,
R 16 on each occurrence, independently of one another, denotes a straight-chain or branched alkyl group having 1 to 10 C atoms, in which one —CH 2 — group or a plurality of —CH 2 — groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—,
with the provisos that,
in the case where n=1, R 11 ═O ⋅ and
[Z 11 —] r —[Z 12 ] s —=—O—, —(CO)—O—, —O—(CO)—, —O—(CO)—O—, —NR 14 — or —NR 14 —(CO)—,
does not denote
straight-chain or branched alkyl having 1 to 10 C atoms, also cycloalkyl, cycloalkylalkyl or alkylcycloalkyl, where in all these groups one or more —CH 2 — groups may be replaced by —O— in such a way that no two O atoms in the molecule are bonded directly to one another,
in the case where n=2 and R 11 ═O ⋅ ,
does not denote
and
in the case where n=2 and R 11 ═O—R 3 ,
R 13 does not denote n-C 1-9 -alkyl,
and
b) one or more compounds selected from the group of the compounds of the formulae II and II
in which
R 2 and R 3 , independently of one another, denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms, and R 2 and R 3 preferably denote alkyl or alkenyl,
on each appearance, independently of one another, denote
L 21 , L 22 , L 31 and L 32 , independently of one another, denote H or F,
X 2 and X 3 , independently of one another, denote halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms,
Z 3 denotes —CH 2 CH 2 —, —CF 2 CF 2 —, —COO—, trans-CH═CH—, trans-CF═CF—, —CH 2 O— or a single bond, and
m and n, independently of one another, denote 0, 1, 2 or 3,
and/or
c) one or more compounds of the formula IV
in which
R 41 and R 42 , independently of one another, have the meaning indicated for R 2 above under formula II, preferably R 41 denotes alkyl and R 42 denotes alkyl or alkoxy or R 41 denotes alkenyl and R 42 denotes alkyl,
independently of one another and, if
occurs twice, also these independently of one another, denote
preferably one or more of
denote(s)
Z 41 and Z 42 , independently of one another and, if Z 41 occurs twice, also these independently of one another, denote —CH 2 CH 2 —, —COO—, trans-CH═CH—, trans-CF═CF—, —CH 2 O—, —CF 2 O—, —C≡C— or a single bond, preferably one or more of them denote(s) a single bond, and
p denotes 0, 1 or 2, preferably 0 or 1.
2 . Medium according to claim 1 , characterised in that it comprises
one or more compounds selected from the group of the compounds of the formulae II and III
in which
R 2 and R 3 , independently of one another, denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms,
on each appearance, independently of one another, denote
L 21 , L 22 , L 31 and L 32 , independently of one another, denote H or F,
X 2 and X 3 , independently of one another, denote halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms,
Z 3 denotes —CH 2 CH 2 —, —CF 2 CF 2 —, —COO—, trans-CH═CH—, trans-CF═CF—, —CH 2 O— or a single bond, and
m and n, independently of one another, denote 0, 1, 2 or 3.
3 . Medium according to claim 1 , characterised in that it comprises
one or more compounds of the formula IV
in which
R 41 and R 42 , independently of one another, denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 carbon atoms,
independently of one another and, if
occurs twice, also these independently of one another, denote
Z 41 and Z 42 , independently of one another and, if Z 41 occurs twice, also these independently of one another, denote —CH 2 CH 2 —, —COO—, trans-CH═CH—, trans-CF═CF—, —CH 2 O—, —CF 2 O—, —C≡C— or a single bond, and
p denotes 0, 1 or 2.
4 . Medium according to claim 1 , characterised in that the total concentration of the compounds of the formula I and in the medium is in the range from 1 ppm to 2000 ppm.
5 . Medium according to claim 1 , characterised in that the compounds of the formula I are compounds selected from the group of the compounds of the formulae I-1 to I-9
and
t denotes an integer from 1 to 12,
R 7 denotes a straight-chain or branched alkyl chain having 1-12 C atoms, in which one —CH 2 — group or a plurality of —CH 2 — groups may be replaced by —O— or —C(═O)—, but two adjacent —CH 2 — groups cannot be replaced by —O—, or denotes an aromatic or heteroaromatic hydrocarbon radical, in which one H atom or a plurality of H atoms may be replaced by OR 14 , N(R 14 )(R 15 ) or R 16 .
6 . Medium according to claim 2 , characterised in that it comprises one or more compounds of the formula II.
7 . Medium according to claim 2 , characterised in that it comprises one or more compounds of the formula III.
8 . Medium according to claim 1 , characterised in that it comprises one or more dielectrically neutral compounds of the formula V
in which
R 51 and R 52 , independently of one another, denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 carbon atoms,
on each occurrence, independently of one another, denotes
Z 51 and Z 52 , independently of one another and, if Z 51 occurs twice, also these independently of one another, denote
—CH 2 CH 2 —, —COO—, trans-CH═CH—, trans-CF═CF—,
—CH 2 O—, —CF 2 O— or a single bond, and
r denotes 0, 1 or 2.
9 . Liquid-crystal display, characterised in that it contains a medium according to claim 1 .
10 . Display according to claim 9 , characterised in that it is addressed by an active matrix.
11 . A method of using a medium according to claim 1 comprising operating said medium in a liquid-crystal display to generate a image in said display.
12 . Process for the preparation of a medium according to claim 1 , characterised in that one or more compounds of the formula I, are mixed with one or more compounds of formula II, one or more compounds of formula III, one or more compounds of formula IV, one or more further mesogenic compounds, one or more additives or a combination thereof,
in which
R 2 and R 3 , independently of one another, denote alkyl, alkoxy, fluorinated alkyl of fluorinated alkoxy having 1 to 7 C atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 C atoms,
on each appearance, independently of one another, denote
L 21 , L 22 , L 31 and L 32 , independently of one another, denote H or F,
X 2 and X 3 , independently of one another, denote halogen, halogenated alkyl or alkoxy having 1 to 3 C atoms or halogenated alkenyl or alkenyloxy having 2 or 3 C atoms,
Z 3 denotes —CH 2 CH 2 —, —CF 2 CF 2 —, —COO—, trans-CH═CH—, trans-CF═CF—, —CH 2 O— or a single bond, and
m and n, independently of one another, denote 0, 1, 2 or 3,
in which
R 41 and R 42 , independently of one another, denote alkyl, alkoxy, fluorinated alkyl or fluorinated alkoxy having 1 to 7 carbon atoms, alkenyl, alkenyloxy, alkoxyalkyl or fluorinated alkenyl having 2 to 7 carbon atoms,
independently of one another and, if
occurs twice, also these independently of one another, denote
Z 41 and Z 42 , independently of one another and, if Z 41 occurs twice, also these independently of one another, denote —CH 2 CH 2 —, —COO—, trans-CH═CH—, trans-CF═CF—, —CH 2 O—, —CF 2 O—, —C≡C— or a single bond, and
p denotes 0, 1 or 2.Join the waitlist — get patent alerts
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