Liquid crystal mixture

Patent metadata

Field	Value
Publication number	US-9388338-B2
Application number	US-20160505-A
Country	US
Kind code	B2
Filing date	Aug 11, 2005
Priority date	Aug 30, 2000
Publication date	Jul 12, 2016
Grant date	Jul 12, 2016

Abstract

Liquid crystal mixture comprising one or several compounds of formula (I)

wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , M 1 , M 2 , X, A, and m are defined herein.

First claim

The invention claimed is:

1. A liquid crystal mixture comprising a compound of formula (I)

wherein
R 1 is H or a linear or branched alkyl group of 1 to 20 C atoms, or a linear or branched alkenyl group of 2 to 20 C atoms, wherein in either case optionally one —CH 2 — group is replaced by cyclohexylen-1,4-diyl, or one or two —CH 2 — groups optionally are replaced by —O—, if non-adjacent to N, or by —C(═O)—, or —Si(CH 3 ) 2 —, and/or one or more H of the alkyl or alkenyl group optionally is replaced by F or CH 3 ;
R 2 stands for
a) F,
b) a linear or branched alkyl group of 1 to 20 C atoms, or a linear or branched alkenyl group of 2 to 20 C atoms, wherein in either case one or two —CH 2 — groups optionally are replaced by —O—, —C(═O)O—, or —Si(CH 3 ) 2 —, and/or one or more H of the alkyl or alkenyl group is replaced by F or CH 3 ,
c) a radical

wherein independently from the respective meanings in (I)
R 3 , R 4 , R 5 , R 6 are, independently from another, an alkyl group of 1 to 8 C atoms;
M 1 , M 2 represent, independently from another, a single bond, —OC(═O)—, —C(═O)O—, —OCH 2 —, or —NH—;
A is
i) —C(═Y)—, wherein Y is CH—Z, wherein Z is phenylen-1,4-diyl, optionally substituted by one to three halogen atoms, alkyl or alkyloxy groups of 1 to 4 C atoms, with the proviso that M 1 and M 2 are —C(═O)O— and —OC(═O)—,
ii) —CHY—, wherein Y is CH 2 —Z, wherein Z is phenylen-1,4-diyl, optionally substituted by one to three halogen atoms, alkyl or alkyloxy groups of 1 to 4 C atoms, with the proviso that M 1 and M 2 are —C(═O)O— and —OC(═O)—,
iii)

wherein
p and q are 0, 1 or 2, wherein the sum of p+q is 1;
M 3 is a single bond or —OC(═O)—, —C(═O)O—, —OCH 2 —, —CH 2 O—, —C≡C—, —CH 2 CH 2 —, or —CH 2 CH 2 CH 2 CH 2 —;

are, independently from another, phenylen-1,4-diyl, which is optionally substituted by one, two or three F, or cyclohexan-1,4-diyl, which is optionally substituted by one CN, CH 3 or F, or pyrimidin-2,5-diyl, which is optionally substituted by one F, pyridine-2,5-diyl, which is optionally substituted by one F, or naphthalene-2,6-diyl, which is optionally substituted by one, two or three F, or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, wherein the aromatic ring is optionally substituted by one, two or three F, or decahydronaphthalene-2,6-diyl, or indane-2,5(6)-diyl, or fluorene-2,7-diyl, or phenanthrene-2,7-diyl, or 9,10-dihydrophenanthrene-2,7-diyl, or (1,3,4)thiadiazol-2,5-diyl, or (1,3)thiazol,2,5-diyl, or (1,3)thiazol-2,4-diyl, or thiophen-2,4-diyl, or thiophen-2,5-diyl, or (1,3)dioxan-2,5-diyl, or piperidin-1,4-diyl, or piperazin-1,4-diyl;
X is H, OH, a linear or branched alkyl or alkyloxy group of 1 to 20 C atoms, wherein one or two —CH 2 — groups are optionally replaced by —O—, —C(═O)O—, or —Si(CH 3 ) 2 —, and optionally one or more H are replaced by F or CH 3 ; and
m is 0 or 1; or
X and M 1 -(A) m -M 2 -R 2 together are
a) a ring of 4 to 16 members, optionally substituted by an alkyl radical of 1 to 15 C atoms,
b) a combination of two either directly linked or spiro-linked rings of, independently from another, 4 to 16 members, optionally substituted by an alkyl radical of 1 to 15 C atoms, wherein the rings, independently from another, are carbocycles or carbocycles comprising B, N, O or S heteroatoms.

2. A liquid crystal mixture according to claim 1 , comprising 0.01 wt.-% to 10 wt.-% of one or several compounds of formula (I).

3. A liquid crystal mixture comprising a compound of formula (IV)

wherein
R 1 is H or a linear or branched alkyl group of 1 to 20 C atoms, or a linear or branched alkenyl group of 2 to 20 C atoms, wherein in either case optionally one —CH 2 — group is replaced by cyclohexylen-1,4-diyl, or one or two —CH 2 -groups optionally are replaced by —O—, if non-adjacent to N, or by —C(═O)—, or —Si(CH 3 ) 2 —, and/or one or more H of the alkyl or alkenyl group optionally is replaced by F or CH 3 ;
R 2 stands for
a) H or F,
b) a linear or branched alkyl group of 1 to 20 C atoms, or a linear or branched alkenyl group of 2 to 20 C atoms, wherein in either case one or two —CH 2 — groups optionally are replaced by —O—, —C(═O)O—, or —Si(CH 3 ) 2 —, and/or one or more H of the alkyl or alkenyl group is replaced by F or CH 3 ,
c) a radical

wherein independently from the respective meanings in (I)
R 3 , R 4 , R 5 , R 6 are, independently from another, an alkyl group of 1 to 8 C atoms;
M 2 represents a single bond, —OC(═O)—, —C(═O)O—, —OCH 2 —, or —NH—;
A is
a) a linear or branched alkan-α,ω-diyl group of 1 to 20 C atoms or alkene-α,ω-diyl group of 2 to 20 C atoms, optionally, if non-adjacent to M 1 and M 2 , one or two non-adjacent —CH 2 — groups are replaced by —O—, or
b)

wherein
p and q are 0, 1 or 2, wherein the sum of p+q is 1;
M 3 is a single bond or —OC(═O)—, —C(═O)O—, —OCH 2 —, —CH 2 O—, —C≡C—, —CH 2 CH 2 —, or —CH 2 CH 2 CH 2 CH 2 ;

are, independently from another, phenylen-1,4-diyl, which is optionally substituted by one, two or three F, or cyclohexan-1,4-diyl, which is optionally substituted by one CN, CH 3 or F, or pyrimidin-2,5-diyl, which is optionally substituted by one F, pyridine-2,5-diyl, which is optionally substituted by one F, or naphthalene-2,6-diyl, which is optionally substituted by one, two or three F, or 1,2,3,4-tetrahydronaphthalene-2,6-diyl, wherein the aromatic ring is optionally substituted by one, two or three F, or decahydronaphthalene-2,6-diyl, or indane-2,5(6)-diyl, or fluorene-2,7-diyl, or phenanthrene-2,7-diyl, or 9,10-dihydrophenanthrene-2,7-diyl, or (1,3,4)thiadiazol-2,5-diyl, or (1,3)thiazol,2,5-diyl, or (1,3)thiazol-2,4-diyl, or thiophen-2,4-diyl, or thiophen-2,5-diyl, or (1,3)dioxan-2,5-diyl, or piperidin-1,4-diyl, or piperazin-1,4-diyl;
X is H, OH, a linear or branched alkyl or alkyloxy group of 1 to 20 C atoms, wherein one or two —CH 2 — groups are optionally replaced by —O—, —C(═O)O—, or —Si(CH 3 ) 2 —, and optionally one or more H are replaced by F or CH 3 ;
m is 0 or 1; and
M 1 is a single bond.

4. A liquid crystal mixture according to claim 1 , further comprising one or several antioxidants.

5. A liquid crystal mixture according to claim 4 , wherein the mixture comprises 0.01 to 10 wt.-% of one or several antioxidants.

6. A liquid crystal mixture according to claim 4 , further comprising one or several UV-stabilizers.

7. A liquid crystal mixture according to claim 1 , which is chiral smectic.

8. A liquid crystal display device comprising a liquid crystal mixture according to claim 1 .

9. A liquid crystal display device according to claim 8 , wherein the device is operated in an activ

Assignees

• Li Ji
• Nonaka Toshiaki
• Ogawa Ayako
• Dübal Hans-Rolf
• Hornung Barbara
• Schmidt Wolfgang
• Wingen Rainer
• Merck Patent Gmbh

Inventors

• Li Ji
• Nonaka Toshiaki
• Ogawa Ayako
• Dübal Hans-Rolf
• Hornung Barbara
• Schmidt Wolfgang
• Wingen Rainer

Classifications

• C09K19/0225

  Ferroelectric · CPC title

• C09K19/0266

  Antiferroelectrics · CPC title

• C09K19/58 Primary

  Dopants or charge transfer agents · CPC title

• C07D211/08

  with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms · CPC title

• C09K19/3483

  the heterocyclic ring being a non-aromatic ring · CPC title