Stock material or miscellaneous articles – Liquid crystal optical display having layer of specified...
Reexamination Certificate
2001-07-30
2003-06-17
Wu, Shean C. (Department: 1756)
Stock material or miscellaneous articles
Liquid crystal optical display having layer of specified...
C252S299010, C252S299660, C570S127000, C570S129000, C570S184000
Reexamination Certificate
active
06579577
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel liquid crystalline compound and a liquid crystal composition. In particular, the present invention relates to a compound having fluorine-substituted 1,4-phenylene groups, a liquid crystal composition containing such a compound, and a liquid crystal display element constituted from such a liquid crystal composition.
BACKGROUND ART
Display elements produced from liquid crystalline compounds have been used widely in displays for watches and clocks, electronic calculators, word processors, and the like. (The term “liquid crystalline compound”
0
used herein is a generic designation for compounds that exhibit a liquid crystal phase, as well as compounds that do not exhibit a liquid crystal phase but are useful as constituting components for liquid crystal compositions.) In recent years, TFT displays having characteristics such as high contrast and wide viewing angle have been actively studied.
For liquid crystal compositions for TFT displays, there are demanded such properties as a high voltage holding ratio which has a very small degree of temperature dependence, a low threshold voltage (Vth) which has a very small degree of temperature dependence, wide range of mesophase, excellent miscibility with other liquid crystal materials, and low viscosity. Further demanded are improved response speed and contrast when they are used as a constitutional component of liquid crystal components. For example, compositions having a high &Dgr;n or a low threshold voltage is useful for improving response speed.
Fluorine-substituted liquid crystalline compounds are suitable as components constituting liquid crystal compositions having such properties, and a large number of such compounds have been examined as described in (1) Japanese Patent Publication No. 63-13411, (2) Japanese Patent Publication No. 63-44132, (3) Japanese Patent Application Laid Open No. 2-233626, (4) Japanese-translated PCT Patent Application Laid-open No. 2-501311, (5) Japanese-translated PCT Patent Application Laid-open No. 3-500413, (6) Japanese-translated PCT Patent Application Laid-open No. 3-503771, (7) Japanese-translated PCT Patent Application Laid-open No. 3-504018, (8) Japanese Patent Application Laid Open No. 4-217930, (9) Japanese-translated PCT Patent Application Laid-open No. 4-501575, (10) Japanese-translated PCT-Patent Application Laid-open No. 5-502676, (11) Japanese-translated PCT Patent Application Laid-open No. 6-504032, and (12) EP 436089.
DISCLOSURE OF INVENTION
An object of the present invention is to provide a liquid crystalline compound having a high voltage holding ratio which has a very small degree of temperature dependence, a low threshold voltage which has a very small degree of temperature dependence, a high &Dgr;n, and excellent miscibility with other liquid crystal materials at low temperature; liquid crystal compositions produced from these compounds having especially improved response speed and contrast; and liquid crystal display elements constituted from such liquid crystal compositions. The present inventors found that the above object is achieved by substituted benzene derivatives represented by general formula (1), thus completing the present invention.
where, R represents a straight chain or branched alkyl group having 1 to 20 carbon atoms, in which each of optional and nonadjacent methylene groups (—CH
2
—) may be substituted by an oxygen atom; X represents a halogen atom, —CF
3
, —CF
2
H, —CFH
2
, —OCF
3
or —OCF
2
H; each of Z
1
and Z
2
independently represents —(CH
2
)
2
—, —(CH
2
)
4
—, —CH
2
O—, —OCH
2
— or a covalent bond, but Z
1
and Z
2
are not covalent bonds simultaneously; each of Y
1
, Y
2
, Y
3
, Y
4
, Y
5
and Y
6
independently represents H or F, but at least one of Y
1
, Y
2
, Y
3
and Y
4
represents F; and,
1) when Z
1
=—(CH
2
)
2
—, Z
2
=a covalent bond, and
a) when Y
1
=F and Y
2
=Y
3
=Y
4
=H, Y
5
=F,
b) when Y
3
=F and Y
1
=Y
2
=Y
4
=H, Y
5
=Y
6
=F,
c) when Y
1
=Y
2
=F, Y
3
=Y
4
=H and X=F or —CF
3
, Y
5
=F,
d) when Y
1
=Y
2
=F, Y
3
=Y
4
=H and X=—CF
2
H, Y
6
=H,
e) when Y
1
=Y
3
=F and Y
2
=Y
4
=H, Y
5
=Y
6
=F or Y
5
=Y
6
=H,
f) when Y
3
=Y
4
=F, Y
1
=Y
2
=H and X=—OCF
3
or —OCF
2
H, Y
5
=F,
g) when Y
3
=Y
4
=F, 1=Y
2
=H and X=—CF
3
or —CF
2
H, Y
5
=Y
6
=F,
h) when Y
1
=Y
2
=Y
3
=F, Y
4
=H and X=F, —OCF
3
, —OCF
2
H, —CF
3
or —CF
2
H, Y
6
=H,
i) when Y
1
=Y
2
=Y
3
=F, Y
4
=H and X=Cl, Y
5
=F,
j) when Y
1
=Y
3
=Y
4
=F, Y
2
=H and X=F, Y
6
=F,
k) when Y
1
=Y
2
=Y
3
=Y
4
=F and X=F, —OCF
3
, —OCF
2
H, —CF
3
or —CF
2
H, Y
6
=H, and
l) when Y
1
=Y
2
=Y
3
=Y
4
=F and X=Cl, Y
5
=F,
2) when Z
1
=a covalent bond, Z
2
=—(CH
2
)
2
—, and
m) when Y
1
=F and Y
2
=Y
3
=Y
4
H, Y
5
=F and Y
6
=H,
n) when Y
3
=F and Y
1
=Y
2
=Y
4
=H, Y
5
=Y
6
=F or Y
5
=Y
6
=H,
o) when Y
1
=Y
3
=F and Y
2
=Y
4
=H, Y
5
=Y
6
=F or Y
5
=Y
6
=H,
p) when Y
3
=Y
4
=F, Y
1
=Y
2
=H and X=F, Cl, —OCF
3
, —OCF
2
H or —CF
2
H, Y
6
=H,
q) when Y
1
=Y
3
=Y
4
=F and Y
2
=H, Y
6
=H,
r) when Y
1
=Y
2
=Y
3
=Y
4
=F, Y
6
=H,
with the proviso that when Z
1
=—(CH
2
)
2
—, Z
2
=a covalent bond, Y
3
=Y
4
=F and Y
1
=Y
2
=H, X is neither F nor Cl; when Z
1
is a covalent bond, Z
2
is —(CH
2
)
2
—, Y
1
=F and Y
2
=Y
3
=Y
4
H, X is neither F, Cl nor CF
3
; and any atom constituting this compound may be substituted by an isomer thereof.
Although some of the compounds represented by general formula (1) disclosed herein are included only perfunctorily in the above references (6) through (12) and other references, these references provide neither data on the compounds of the present invention nor specific descriptions of properties thereof, nor do they suggest the present invention.
Compounds represented by general formula (1) are classified into the following (a-1) through (a-32), and (b-1) through (b-32):
R—B(F)—(CH
2
)
2
—B—Q
(a-1)
R—B—(CH
2
)
2
—B(F)—Q
(a-2)
R—B(F,F)—(CH
2
)
2
—B—Q
(a-3)
R—B(F)—(CH
2
)
2
—B(F)—Q
(a-4)
R—B—(CH
2
)
2
—B(F,F)—Q
(a-5)
R—B(F,F)—(CH
2
)
2
—B(F)—Q
(a-6)
R—B(F)—(CH
2
)
2
—B(F,F)—Q
(a-7)
R—B(F,F)—(CH
2
)
2
—B(F,F)—Q
(a-8)
R—B(F)—(CH
2
)
4
—B—Q
(a-9)
R—B—(CH
2
)
4
—B(F)—Q
(a-10)
R—B(F,F)—(CH
2
)
4
—B—Q
(a-11)
R—B(F)—(CH
2
)
4
—B(F)—Q
(a-12)
R—B—(CH
2
)
4
—B(F,F)—Q
(a-13)
R—B(F,F)—(CH
2
)
4
—B(F)—Q
(a-14)
R—B(F)—(CH
2
)4—B(F,F)—Q
(a-15)
R—B(F,F)—(CH
2
)
4
—B(F,F)—Q
(a-16)
R—B(F)—CH
2
O—B—Q
(a-17)
R—B—CH
2
O—B(F)—Q
(a-18)
R—B(F,F)—CH
2
O—B—Q
(a-19)
R—B(F)—CH
2
O—B(F)—Q
(a-20)
R—B—CH
2
O—B(F,F)—Q
(a-21)
R—B(F,F)—CH
2
O—B(F)—Q
(a-22)
R—B(F)—CH
2
O—(F,F)—Q
(a-23)
R—B(F,F)—CH
2
O—B(F,F)—Q
(a-24)
R—B(F)—OCH
2
—B—Q
(a-25)
R—B—OCH
2
—B(F)—Q
(a-26)
R—B(F,F)—OCH
2
—B—Q
(a-27)
R—B(F)—OCH
2
—B(F)—Q
(a-28)
R—B—OCH
2
—B(F,F)—Q
(a-29)
R—B(F,F)—OCH
2
—B(F)—Q
(a-30)
R—B(F)—OCH
2
—B(F,F)—Q
(a-31)
R—B(F,F)—OCH
2
—B(F,F)—Q
(a-32)
R—B(F)—B—(CH
2
)
2
—Q
(b-1)
R—B—B(F)—(CH
2
)
2
—Q
(b-2)
R—B(F,F)—B—(CH
2
)
2
—Q
(b-3)
R—B(F)—B(F)—(CH
2
)
2
—Q
(b-4)
R—B—B(F,F)—(CH
2
)
2
—Q
(b-5)
R—B(F,F)—B(F)—(CH
2
)
2
—Q
(b-6)
R—B(F)—B(F,F)—(CH
2
)
2
—Q
(b-7)
R—B(F,F)—B(F,F)—(CH
2
)
2
—Q
(b-8)
R—B(F)—B—(CH
2
)
4
—Q
(b-9)
R—B—B(F)—(CH
2
)
4
—Q
(b-10)
R—B(F,F)—B—(CH
2
)
4
—Q
(b-11)
R—B(F)—B(F)—(CH
2
)
4
—Q
(b-12)
R—B—B(F,F)—(CH
2
)
4
—Q
(b-13)
R—B(F,F)—B(F)—(CH
2
)
4
—Q
(b-14)
R—B(F)—B(F,F)—(CH
2
)
4
—Q
(b-15)
R—B(F,F)—B(F,
Kondo Tomoyuki
Kubo Yasuhiro
Matsui Shuichi
Miyazawa Kazutoshi
Nakagawa Etsuo
Chisso Corporation
McDermott & Will & Emery
Wu Shean C.
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