Stock material or miscellaneous articles – Liquid crystal optical display having layer of specified...
Reexamination Certificate
2001-04-18
2003-04-29
Wu, Shean C. (Department: 1756)
Stock material or miscellaneous articles
Liquid crystal optical display having layer of specified...
C252S299660, C252S299010, C570S127000, C570S129000
Reexamination Certificate
active
06555185
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to new liquid crystalline compounds and liquid crystal compositions. More particularly, the present invention relates to terphenyl derivatives having a fluorine-substituted-1,4-phenylene group, liquid crystal compositions containing them, and liquid crystal display devices made using the liquid crystal compositions.
BACKGROUND OF THE INVENTION
Liquid crystal display devices using liquid crystalline compounds (in this description, the term “liquid crystalline compound” is used as a generic term for a compound exhibiting a liquid crystal phase or a compound not exhibiting a liquid crystal phase but useful as a constituent of a liquid crystal composition) are widely used in displays of clocks, watches, electronic calculators, word processors and the like. Lately, much research has been conducted for a TFT type display having characteristics such as a high contrast and a broad visual field angle.
Liquid crystal compositions for TFT need physical properties, such as a high voltage holding ratio, low threshold voltage (Vth), little variation of these properties with temperature, broad temperature range of liquid crystal layers, excellent compatibility with other liquid crystal materials and low viscosity. Further, the compositions having a high optical anisotropy (&Dgr;n) are useful for improving the response speed.
For these reasons, as a component of liquid crystalline compounds having such characteristics, fluorine-substituted liquid crystalline compounds are preferably used, as described in (1) Japanese Patent Publication 63-13411, (2) Japanese Patent Publication 63-44132, (3) Japanese Patent Laid-open 2-233626, (4) Japanese Patent Laid-open 2-501311, (5) Japanese Patent Laid-open 3-500413, (6) Japanese Patent Laid-open 3-504018, (7) Japanese Patent Laid-open 5-502676, (8) Japanese Patent Laid-open 6-504032, (9) GB2257701 and (10) EP439089, many synthesis methods and researches have been done.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide liquid crystalline compounds having a very little variation of these properties with temperature change, high &Dgr;n, and good compatibility with other liquid crystal materials particularly at low temperatures, liquid crystal compositions containing these compounds, and liquid crystal display devices made using the liquid crystal compositions.
The present inventors have earnestly studied to resolve the above problems and have completed the studies by obtaining the merphenyl derivatives having the above properties. The compounds are represented by general formula (1);
wherein R represents a straight or branched alkyl group of 1-20 carbon atoms, and any methylene groups (—CH
2
—) not adjacent each other in each alkyl group may be replaced by oxygen atoms; X shows an halogen atom, —OCF
3
, —OCF
2
H, —CF
3
, —CF
2
H or —CFH
2
; Y
1
, Y
2
, Y
3
, Y
4
, Y
5
and Y
6
independently represents H or F, but at least two of Y
1
, Y
2
, Y
3
and Y
4
represent F;
in which
a) in case of Y
1
═Y
2
═Y
3
═Y
4
═H and X═F, Y
5
═Y
6
═F,
b) in case of Y
1
═Y
2
═F, Y
3
═Y
4
═H and X=—CF
3
or —CF
2
H, Y
5
═Y
6
═F or Y
5
═Y
6
═H,
c) in case of Y
1
═Y
3
═F, Y
2
═Y
4
═H and X═—CF
3
, Y
5
═Y
6
═F,
d) in case of Y
1
═Y
3
═F, Y
2
═Y
4
═H and X═—OCF
3
, Y
5
═F,
e) in case of Y
3
═Y
4
═F, Y
1
═Y
2
═H and X═F, Y
5
═Y
6
═F,
f) in case of Y
3
═Y
4
═F, Y
1
═Y
2
═H and X═—OCF
3
or —CF
3
, Y
5
═F,
g) in case of Y
1
═Y
2
═Y
3
═F, Y
4
═H and X═CL, Y
5
═Y
6
═F,
h) in case of Y
1
═Y
2
═Y
3
═F, Y
4
═H and X═F, —CF
3
or —CF
2
H, Y
5
═F, and
i) in case of Y
1
═Y
2
═Y
3
═Y
4
═F and X═Cl or —OCF
3
, Y
5
═F, however, in case of Y
1
═Y
2
═F and Y
3
═Y
4
═H, in case of Y
1
═Y
3
═F and Y
2
═Y
4
═H, and in case of Y
3
═Y
4
═F and Y
1
═Y
2
═H, not X═Cl,
and any atom in the compound may be replaced by an isotope thereof.
A part of the compounds represented by general formula (1) are formally included in the compounds described in the above references (6) to (10). However, in these references, there is no description of data such as values of physical properties of the compounds of the present invention, and definite or embodied characteristics of these compounds, so that the present invention is not suggested.
The compounds represented by general formula (1) and be classified as follows into (a-1) to (a-6).
R—B(F,F)—B—Q (a-1)
R—B—(F)—B(F)—Q (a-2)
R—B—B(F,F)—Q (a-3)
R—B(F,F)—B(F)—Q (a-4)
R—B(F)—B(F,F)—Q (a-5)
R—B(F,F)—B(F,F)—Q (a-6)
In the formula, R represents as the same meaning as described above, B represents a 1,4-phenylene group, B(F) represents a 3-fluoro-1,4-phenylene, B(F,F) represents a 3,5-difluoro-1,4-phenylene group, and Q represents the following group:
wherein Y
5
, Y
6
and X represent as the same meaning as described above.
As described above, in the formula, R represents a straight or branched alkyl group of 1-20 carbon atoms. As a straight alkyl group, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, decyl, pentadecyl or eicosyl can be exemplified. As a branched alky group, isopropyl, secbutyl, tert-butyl, 2-methyl-butyl, isopentyl, isohexyl, 3-ethyloctyl, 3,8-dimethyltetradecyl or 5-ethyl-5-methylnonadecyl can be exemplified. Further, the branched alkyl group may be optionally active group, and compounds having such a group are useful as chiral doping agents.
Any methylene groups not adjacent each other in the alkyl groups may be replaced by oxygen atoms, and alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, pentyloxy and nonyloxy, and alkoxyalkyl groups such as methoxymethyl, methoxyethyl, methoxypropyl, methoxybutyl, methoxypentyl, methoxyoctyl, ethoxymethyl, ethoxyethyl, ethoxypropyl, ethoxyhexyl, propoxymethyl, propoxyethyl, propoxypropyl, propoxypentyl, butoxymethyl, butoxyethyl, butoxybutyl, pentyloxymethyl, pentyloxybutyl, hexyloxymethyl, hexyloxyethyl, hexyloxypropyl, heptyloxymethyl and octyloxymethyl are examples thereof.
DETAILED DESCRIPTION OF THE INVENTION
Although the liquid crystalline compounds of the present invention represented by general formula (1) may be prepared by a method of common organic synthesis, as an example, the compounds may be easily prepared by the following method.
wherein R, Y
1
-Y
6
and X have the same meaning as described above, Xa and Xb are halogen atoms.
Namely, as shown in scheme 1, in mixed solvent of three ingredients; toluene, xylene or the like, alcohol such as ethanol, and water; halogen compound (2) and dihydroxyborane derivative (3) can be reacted in the presence of a base such as K
2
CO
3
or Na
2
CO
3
and a catalyst such as carbon-carried palladium (Pd—C), Pd(PPh
3
)
4
or PdCl
2
(PPh
3
)
2
to produce compound (1) of the present invention. Further, as shown in scheme 2, after reacting halogen compound (2) with a lithium compound such as n-BuLi or sec-BuLi and a zinc compound such as ZnCl
2
or ZnBr
2
, the reactant may be reached with halogen compound (4) to obtain the above compound (1).
To introduce substituent X in to the benzene ring, a raw material, in which X has been previously introduced can be used, or, X can be easily introduced by a well-known reaction at any step. Embodied examples are shown in the following. (In the following formulas, Rx shows the following group).
wherein R, and Y
1
-Y
4
show the same meaning as described above.
wherein Y
5
and Y
6
have the same meaning as described above.
Namely, as shown in scheme 3, compound (5) and a lithium compound such as n-butyllithium and iodine are reacted to obtain compound (6). Compound (6) and sodim trifluoroacetate/copper iodine (I) (G. E. Carr et al., Journal of the Chemical Society Perkin Trans Actions I, 921 (1988
Kondou Tomoyuki
Kubo Yasuhiro
Matsui Shuichi
Miyazawa Kazutoshi
Nakagawa Etsuo
Browdy & Neimark PLLC
Chisso Corporation
Wu Shean C.
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