High transverse dipole moment aryl compounds

Details High transverse dipole moment aryl compounds High transverse dipole moment aryl compounds

2000-04-05

2002-05-21

Wu, Shean C. (Department: 1756)

Stock material or miscellaneous articles

Liquid crystal optical display having layer of specified...

C252S299660, C570S127000, C570S129000, C570S131000

Reexamination Certificate

active

06391397

ABSTRACT:

BACKGROUND TO THE INVENTION
This invention relates to high transverse dipole moment aryl compounds and their use in liquid crystal compositions and liquid crystal devices wherein a high transverse dipole moment is required.
U.S. Pat. No. 4,784,793 discloses terpenoid derivatives for incorporation into ferroelectric liquid crystal mixtures, such terpenoid derivatives including aromatic esters of terpenoid alcohols in which the aromatic group includes two or three phenyl groups which may be biphenyl or terphenyl groups. The possibility of providing lateral substituents on one or more of these phenyl groups is disclosed with the object of fixing the orientation of such groups to add to the total lateral dipole moment of the molecule. The use of methyl, methoxy, trifluoromethyl, cyano, halogeno and acetyl groups as such lateral substituents is mentioned. U.S. Pat. No. 4,952,337 discloses similar types of compound to those disclosed in above-mentioned U.S. Pat. No. 4,784,793.
U.S. Pat. No. 4,852,977 discloses compounds which may be used as a host or dopant in ferroelectric chiral smectic liquid crystal mixtures, the compounds being derivatives of an &agr;-hydroxycarboxylic acid containing a chiral unit in which the asymmetric carbon atom is linked to a hydrogen atom, a phenyl or phenyl alkyl group where the phenyl ring may be substituted with one or more alkyl, alkoxy, halogen or cyano groups, and two other moieties linked to the asymmetric carbon atom by carbonyloxy groups. The compound may include bi- or ter-phenyl groups which may or may not be substituted by one or more fluorine atoms to assist in sterically hindering rotation of the chiral centre relative to the core of the molecule.
It is an object of the present invention to provide a compound having an improved transverse dipole moment.
SUMMARY OF THE INVENTION
According to a first aspect of the present invention, there is provided a fluorinated aryl compound having the general formula [1]:
wherein
A, B and C are independently selected from conjugated cyclic moieties including heterorings and fused rings;
the fluoro substituent on ring A is at the ortho position relative to the attached end chain;
R
1
=straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
1
-C
12
)alkyl, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
1
-C
12
)alkoxy, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
1
-C
11
)alkoxycarbonyl, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
1
-C
11
)alkylcarbonyloxy, cyano, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
2
-C
12
)alkenyl, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
2
-C
12
)alkenyloxy, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
2
-C
11
)alkenyloxycarbonyl, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
2
-C
11
)alkenylcarbonyloxy, or R
6
—(CHF—CH
2
)
a
—(CF
2
—CH
2
)
b
—CF
2
—(CH
2
)
c
—;
R
2
=H or F;
R
3
=straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
1
-C
12
)alkyl, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
1
-C
12
)alkoxy, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
1
-C
11
)alkoxycarbonyl, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
1
-C
11
)alkylcarbonyloxy, cyano, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
2
-C
12
)alkenyl, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
2
-C
12
)alkenyloxy, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
2
-C
11
)alkenyloxycarbonyl, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
2
-C
11
)alkenylcarbonyloxy;
R
4
=H or F;
R
5
=H or F;
R
6
=straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
1
-C
12
)alkyl, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
1
-C
12
)alkoxy, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
1
-C
11
)alkoxycarbonyl, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
1
-C
11
)alkylcarbonyloxy, cyano, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
2
-C
12
)alkenyl, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
2
-C
12
)alkenyloxy, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
2
-C
11
i)alkenyloxycarbonyl, straight or branched, fluoro- and/or cyano-substituted or unsubstituted (C
2
-C
11
)alkenylcarbonyloxy;
a=0, 1 or 2;
b=0, 1 or 2;
c=0 or 1;
s=0 or 1;
t=1, 2 or 3;
u=1, 2 or 3;
v=0 or 1;
x=0 or 1;
y=0, 1 or 2; and
z=0, 1 or 2;
More specifically, the compound of a fluorinated aryl compound may have the general formula [1a]:
wherein u=1, 2 or 3, v=0 or 1, x=0, 1 or 2; y=0, 1 or 2; z=0, 1 or 2; A and B are independently selected from conjugated cyclic moieties including heterorings and fused rings; the fluoro substituent on ring A is at the ortho position relative to the chain containing R
3
; R
1
=(C
1
-C
12
)alkyl, (C
1
-C
12
)alkoxy, (C
1
-C
11
)alkoxycarbonyl, (C
1
-C
11
)alkylcarbonyloxy, or cyano; R
2
=H or F, R
3
=(C
1
-C
11
)alkyl, (C
1
-C
11
)alkoxy, (C
1
-C
10
)alkoxycarbonyl or (C
1
-C
10
)alkyl carbonyloxy; and R
4
=H or F.
A, B and C are preferably aryl moieties, and are more preferably independently selected from phenyl, pyridinyl and pyrimidinyl.
Examples of compounds within the scope of the present invention are in accordance with the general formulae [2] to [12] below, wherein R is (C
1
-C
10
)alkyl and R′ is (C
1
-C
12
)alkyl:
wherein a is 0 or 1, b is 0 or 1 and v is 0 or 1
wherein a is 0 or 1, b is 0 or 1 and v is 0 or 1
wherein a is 0 or 1, b is 0 or 1 and v is 0 or 1
wherein a is 0 or 1, b is 0 or 1 and v is 0 or 1
wherein a is 0 or 1, b is 0 or 1 and v is 0 or 1
where a is 0 or 1, v is 0 or 1 and R
2
and R
4
are as defined above
where a is 0 or 1, v is 0 or 1 and R
2
and R
4
are as defined above
In all of the above examples v=0 or 1, but in the case of terphenyl compounds, those compounds where v=0, i.e. where the side chain CF
2
group is at the alpha position relative to the adjacent ring, may be preferred.
Compounds of the general formulae [11] and [12] above are examples of nematics having a high positive dielectric biaxiality, i.e. nematics in which the liquid crystal molecules align parallel to the direction of an applied electrical field.
Compounds within the scope of the present invention also include compounds of the general formula:
where R
1
is (C
1
-C
12
)alkyl or (C
1
-C
12
)alkoxy and R
3
is (C
1
-C
12
)alkyl
A particular example of a compound of the general formula [1] above is the compound having the formula [13] below:
The measured dipole moment (following the procedure of E. P. Raynes (1984) Mol. Cryst. Liq. Cryst. Lett., v1 p 69) of compound [13] is 16.48×10
−30
Cm. Based on dipole moment calculations for a compound containing the moieties, R′O-phenyl-phenyl-3,4-difluorophenyl- and RCF
2
CH
2
—, the measured dipole moment for compound [13] is closest to the value predicted for a substantially parallel arrangement of the dipoles of these two moieties rather than an anti-parallel or random orientation. The estimated change of the nematic &Dgr;&egr; and SmC(*) &dgr;⊥≈&mgr;
⊥
2
, where &egr;
⊥
is the dipole moment perpendicular to the long axis of the molecule. Since the measured dipole moment of a similar compound having no RCF
2
CH
2
— moiety was 10.9×10
−30
Cm, the compound [13] may represent an improvement of a factor of greater than 2 over the latter compound.
It is also considered that any tendenc

Affiliated with

Also associated with

Rating

High transverse dipole moment aryl compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with High transverse dipole moment aryl compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and High transverse dipole moment aryl compounds will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2909948