Fluorinated anthracenes, and their use in liquid-crystal...

Details Fluorinated anthracenes, and their use in liquid-crystal... Fluorinated anthracenes, and their use in liquid-crystal...

2002-09-12

2004-01-27

Wu, Shean C. (Department: 1756)

Stock material or miscellaneous articles

Liquid crystal optical display having layer of specified...

C252S299620, C570S183000, C570S187000, C570S188000

Reexamination Certificate

active

06682785

ABSTRACT:

For an increasing number of applications of LCDs—for example for use in automobiles, in which a temperature range of from −40° C. to 100° C. can readily occur, but also for portable equipment, such as mobile telephones and notebook PCs—there is a need for liquid-crystal mixtures which on the one hand have a very broad working-temperature range and on the other hand have the lowest possible threshold voltage.
There is therefore a continuing demand for novel, suitable liquid-crystal mixtures and mixture components. As described in Ichinose et al. (IDW 00, Abstr. LCT4-3) or in DE-A-10 050 071, materials are being sought in which high optical anisotropy (&Dgr;n) and low rotational viscosity coexist—with other parameters, such as, for example, high absolute values of the dielectric anisotropy (&Dgr;&egr;), likewise being required in addition to further applicationally relevant parameters.
The object of the present invention is therefore to provide novel components for use in nematic or cholesteric or chiral-smectic liquid-crystal mixtures which have high absolute values of the dielectric anisotropy combined with a favorable ratio of viscosity and clearing point. In addition, the compounds should to a large extent be light- and UV-stable and thermally stable. Furthermore, they should be suitable for achieving a high “voltage holding ratio (VHR)”. They should furthermore be readily accessible synthetically and therefore potentially inexpensive.
The anthracene derivatives having 2-(4-subst.)styryl substituents (Helv. Chim. Acta 52, 2521 (1969)) or 2-(4-subst.)benzylidenamino substituents (Bull. Chem. Soc. Jpn. 50, 1009 (1977)), the known derivatives of 1,2,3,4-tetrahydroanthracene (J. Org. Chem. 56, 989 (1991)), the known mono- and difluoroanthracenes {Isr. J. Chem. 11, 791 (1973); Synlett 1998, 301}, tetrafluorotetrahydroanthracenes (J. Chem. Soc. Perkin Trans. 1 1972, 2372), tetrafluoroanthracenes (J. Fluorine Chem. 29, 417, 1985), the 9,10-diphenylanthracenes (JP-A 61 281 193), substituted anthracene (EP 915 144) and the cholesterol esters of anthracene (WO 88/00938), do not suggest to the person skilled in the art that fluorine-substituted derivatives of these ring systems are suitable as a component of liquid-crystal mixtures.
The present invention relates to compounds of the formula (I) and to liquid-crystal mixtures comprising these compounds
in which:
L
1
, L
2
, L
3
, L
4
and L
5
are identical or different and are H or F, with the provisos that
a) at least one of L
1
, L
2
, L
3
L
4
and L
5
must be F
b) if L
1
is F, L
3
, L
4
and L
5
must be H
c) if L
4
or L
5
is F, L
1
and L
2
must be H,
R
1
is a straight-chain or branched alkyl radical having from 1 to 16 carbon atoms or a straight-chain or branched alkenyl radical having from 2 to 16 carbon atoms, in which
a) one or more non-adjacent and non-terminal CH
2
groups may be replaced by —O—, —C(═O)O—, —O—C(═O)—, —O—C(═O)—O—, —C(═O)— or —Si(CH
3
)
2
—, and/or
b) one CH
2
group may be replaced by —C≡C—, cyclopropane-1,2-diyl, cyclobutane-1,3-diyl, cyclohexan-1,4-diyl or phenylene-1,4-diyl, and/or
c) one or more H atoms may be replaced by F and/or Cl,
R
2
is hydrogen, F, Cl, CN, —NCS, CF
3
, CHF
2
, CH
2
F, OCF
3
, OCHF
2
, OCH
2
F, OCH
2
CF
3
, OCH═CF
2
or a straight-chain or branched alkyl radical having from 1 to 12 carbon atoms or a straight-chain or branched alkenyl radical having from 2 to 12 carbon atoms, in which
a) one or more non-adjacent and non-terminal CH
2
groups may be replaced by —O—, —C(═O)O—, —O—C(═O)—, —O—C(═O)—O—, —C(═O)— or —Si(CH
3
)
2
—, and/or
b) one CH
2
group may be replaced by —C≡C—, cyclopropane-1,2-diyl or cyclobutane-1,3-diyl, and/or
c) one or more H atoms may be replaced by F and/or Cl and/or the -M
2
-A
2
-R
3
group, in which
M
2
is —CO—O—, —O—CO—, —CH
2
—O—, —O—CH
2
—, —CF
2
—O—, —CH═CH—, —CF═CF—, —C≡C—, —CH
2
—CH
2
—CO—O—, —O—CO—CH
2
—CH
2
—, —CH
2
—CH
2
—, —CF
2
—CF
2
—, —(CH
2
)
4
—,
—OC(═O)CF═CF— or a single bond,
A
2
is 1,4-phenylene, in which one or two H atoms may be replaced by F, Cl, CN and/or OCF
3
or up to three H atoms may be replaced by fluorine, 1,4-cyclohexylene, in which one or two H atoms may be replaced by CH
3
and/or F, 1-cyclohexene-1,4-diyl, in which one H atom may be replaced by CH
3
or F, or 1,3-dioxane-2,5-diyl,
R
3
has the same possible meanings as R
2
, with the exception of -M
2
-A
2
-R
3
,
Preference is given to the compounds of the formulae (Ia) to (It):
in which
R
4
is a straight-chain or branched alkyl radical having from 1 to 16 carbon atoms or a straight-chain or branched alkenyl radical having from 2 to 16 carbon atoms, in which one non-terminal CH
2
group may be replaced by —O— and/or one CH
2
group may be replaced by cyclohexane-1,4-diyl or phenylene-1,4-diyl,
R
5
is hydrogen, a straight-chain or branched alkyl radical having from 1 to 12 carbon atoms or a straight-chain or branched alkenyl radical having from 2 to 12 carbon atoms, in which
a) one or more non-adjacent and non-terminal CH
2
groups may be replaced by —O—, —C(═O)O—, —O—C(═O)— or —Si(CH
3
)
2
—, and/or
b) one CH
2
group may be replaced by —C≡C—, cyclopropane-1,2-diyl or cyclobutane-1,3-diyl, and/or
c) one or more H atoms may be replaced by F and/or Cl, or the -M
2
-A
2
-R
3
group, in which
M
2
is —CO—O—, —O—CO—, —CH
2
—O—, —O—CH
2
—, —CF
2
—O—, —O—CF
2
—, —CH
2
—CH
2
—CO—O—, —O—CO—CH
2
—CH
2
—, —CH
2
—CH
2
—, —CF
2
—CF
2
—, —(CH
2
)
4
—, —OC(═O)CF═CF—, or a single bond,
A
2
is 1,4-cyclohexylene, in which one or two H atoms may be replaced by CH
3
and/or F, 1-cyclohexene-1,4-diyl, in which one H atom may be replaced by CH
3
or F, or 1,3-dioxane-2,5-diyl,
R
3
is hydrogen, a straight-chain or branched alkyl radical having from 1 to 12 carbon atoms or a straight-chain or branched alkenyl radical having from 2 to 12 carbon atoms, in which
a) one or more non-adjacent and non-terminal CH
2
groups may be replaced by —O—, —C(═O)O—, —O—C(═O)—, or —Si(CH
3
)
2
—, and/or
b) one CH
2
group may be replaced by —C≡C—, cyclopropane-1,2-diyl or cyclobutane-1,3-diyl, and/or
c) one or more H atoms may be replaced by F and/or Cl,
R
6
is a straight-chain or branched alkyl radical having from 1 to 12 carbon atoms, in which
a) one or more non-adjacent and non-terminal CH
2
groups may be replaced by —O—, —C(═O)O—, —O—C(═O)—, or —Si(CH
3
)
2
—, and/or
b) one CH
2
group which is not adjacent to the ring system may be replaced by —C≡C— or —CH═CH—, and/or
c) one —CH
2
— group may be replaced by cyclopropane-1,2-diyl, cyclobutane-1,3-diyl or cyclohexane-1,4-diyl or 1,3-dioxane-2,5-diyl, and/or
d) one or more H atoms may be replaced by F and/or Cl,
R
7
is a straight-chain or branched alkyl radical having from 1 to 16 carbon atoms or a straight-chain or branched alkenyl radical having from 2 to 16 carbon atoms, in which one non-terminal CH
2
group may be replaced by —O— and/or one CH
2
group may be replaced by cyclohexane-1,4-diyl or phenylene-1,4-diyl,
R
8
is hydrogen, a straight-chain or branched alkyl radical having from 1 to 12 carbon atoms or a straight-chain or branched alkenyl radical having from 2 to 12 carbon atoms, in which
a) one or more non-adjacent and non-terminal CH
2
groups may be replaced by —O—, —C(═O)O—, —O—C(═O)— or —Si(CH
3
)
2
—, and/or
b) one CH
2
group may be replaced by —C≡C—, cyclopropane-1,2-diyl or cyclobutane-1,3-diyl, and/or
c) one or more H atoms may be replaced by F and/or Cl, or the -M
3
-A
3
-R
10
group, in which
M
3
is —CO—O—, —O—CO—, —CH
2
—O—, —O—CH
2
—, —CF
2
—O—, —O—CF
2
—, —CH
2
—CH
2
—CO—O—, —O—CO—CH
2
—CH
2
—, —CH
2
—CH
2
—, —CF
2
—CF
2
—, —(CH
2
)
4
—, —OC(═O)CF═CF— or a single bond,
A
3
is 1,4-cyclohexylene, in which one or two H atoms may be replaced by CH
3
and/or F, 1-cyclohexene-1,4-diyl, in which one H atom may be replaced by CH
3
or F, or 1,3-dioxane-2,5-diyl,
R
10
is hydrogen, a straight-chain or branched alkyl radical having from 1 to 12 c

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