Stock material or miscellaneous articles – Liquid crystal optical display having layer of specified...
Reexamination Certificate
1999-03-25
2001-07-03
Wu, Shean C. (Department: 1756)
Stock material or miscellaneous articles
Liquid crystal optical display having layer of specified...
C252S299010, C252S299660, C570S127000, C570S129000, C570S132000
Reexamination Certificate
active
06254941
ABSTRACT:
This application is a 371 of PCT/JP97/03404 filed Sep. 25, 1997.
TECHNICAL FIELD
The present invention relates to new liquid crystalline compounds and liquid crystal compositions, more particularly, it relates to liquid crystalline compounds having alkyl groups, alkoxy groups and alkoxyalkyl groups, which are substituted by fluorines, liquid crystal compositions containing them, and liquid crystal display devices constituted by using the liquid crystal composition.
BACKGROUND ART
The liquid crystal display devices using the liquid crystalline compound (in this description, the term of a 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 broadly 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 properties such as a high contrast and a wide viewing 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 depending on temperature, broad temperature range of liquid crystal phase and low viscosity. Further, the compositions having a high optical anisotropy (&Dgr;n) are useful for improving the response speed.
For these reasons, compounds of fluorine types 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 and (6) DE4301700, many synthesis methods and researches have been done.
DISCLOSURE OF INVENTION
The present invention aims to provide liquid crystalline compounds having 1) a very high voltage holding ratio, 2) very little variation of these properties depending on temperature, 3) high &Dgr;n, and 4) good compatibility with other liquid crystal materials particularly under a low temperature, liquid crystal compositions containing these crystalline compounds, and liquid crystal display devices constituted by using the liquid crystal compositions.
The present inventors have earnestly studied to resolve the above problems and have completed the studies by obtaining the liquid crystalline compounds having the above properties. The compounds are represented by general formula (1);
wherein R represents an alkyl, alkoxy or alkoxyalkyl group of 2-20 carbon atoms, and in each group, any 1-3 hydrogen atoms may be replaced by fluorine atoms; X shows a halogen atom or an alkyl group of 1-20 carbon atoms, any methylene groups (—CH
2
—) not adjacent each other in the alkyl group may be replaced by oxygen atoms, and any one or more hydrogen atoms in the alkyl group may be replaced by fluorine atoms; Z
1
, Z
2
and Z
3
, each independently, represents —(CH
2
)
2
—, —(CH
2
)
4
—, —CH
2
O—, —OCH
2
—, —(CH
2
)
3
O—, —O(CH
2
)
3
— or a covalent bond; Y
1
-Y
16
each independently represent hydrogen atoms or fluorine atoms, but at least two represent fluorine atoms; m represents 0 or 1, and any atom constituting 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 having general formula described in the above references (5) and (6). 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) can be classified as follows.
In the following, R, X and Z
1
-Z
3
have the same meaning as described above, P represents a 1,4-phenylene group in which any one or more hydrogen atoms may be replaced by fluorine atoms.
Compounds having 3 six-membered rings:
R-P-P-P-X (1a)
R-P-Z
1
-P-P-X (1b)
R-P-P-Z
2
-P-X (1c)
R-P-Z
1
-P-Z
2
-P-X (1d)
Compounds having 4 six-membered rings:
R-P-P-P-P-X (1e)
R-P-Z
1
-P-P-P-X (1f)
R-P-P-Z
2
-P-P-X (1g)
R-P-P-P-Z
3
-P-X (1h)
R-P-Z
1
-P-Z
2
-P-P-X (1i)
R-P-Z
1
-P-P-Z
3
-P-X (1j)
R-P-P-Z
2
-P-Z
3
-P-X (1k)
R-P-Z
1
-P-Z
2
-P-Z
3
-P-X (1l)
In these compounds, particularly, the compounds represented by formulae (1a)-(1c) and formulae (1e)-(1h) are preferably used for attaining the objects of the present invention.
In these formulas, R is an alkyl, alkoxy or alkoxyalkyl group of 2-20 carbon atoms, and in each group, any 1-3 hydrogen atoms may be replaced by fluorine atoms. And specifically, fluoroalkyl groups of straight chain such as 1-fluoroethyl, 2-fluoroethyl, 1-fluoropropyl, 2-fluoropropyl, 3-fluoropropyl, 1-fluorobutyl, 2-fluorobutyl, 3-fluorobutyl, 4-fluorobutyl, 1-fluoropentyl, 2-fluoropentyl, 3-fluoropentyl, 4-fluoropentyl, 5-fluoropentyl, 6-fluorohexyl, 7-fluoroheptyl, 10-fluorodecyl, 15-fluoropentadecyl, 20-fluoroicosyl, 1,1-difluoroethyl, 1,2-difluoroethyl, 2,2-difluoroethyl, 1,1-difluoropropyl, 2,2-difluoropropyl, 3,3-difluoropropyl, 1,2-difluoropropyl, 1,3-difluoropropyl, 2,3-difluoropropyl, 3,3-difluoropentyl, 5,5-difluoropentyl, 15,15-difluoropentadecyl, 1,1,2-trifluoroethyl, 1,2,2-trifluoroethyl, 2,2,2-trifluoroethyl, 1,1,2-trifluoropropyl, 1,1,3-trifluoropropyl, 1,2,2-trifluoropropyl, 1,3,3-trifluoropropyl, 2,2,3-trifluoropropyl, 1,2,3-trifluoropropyl, 3,3,5-trifluoropentyl and 16,17,17-trifluoroheptadecyl; and fluoroalkyl groups of branched chains such as 1-methyl-2-fluoroethyl, 2-ethyl-3-fluoropropyl, 2-methyl-4-fluorobutyl, 2,4-dimethyl-5-fluoropentyl, 3-ethyl-5-fluorohexyl and 5-trifluoro-methyldecyl can be exemplified.
As the fluoroalkoxy groups, 1-fluoroethoxy, 2-fluoroethoxy, 1-fluoropropoxy, 2-fluoropropoxy, 3-fluoropropoxy, 1-fluorobutoxy, 2-fluorobutoxy, 3-fluorobutoxy, 4-fluorobutoxy, 1-fluoropentyloxy, 2-fluoropentyloxy, 3-fluoropentyloxy, 4-fluoropentyloxy, 5-fluoropentyloxy, 13-fluorotridecyloxy, 1,1-difluoroethoxy, 2,2-difluoroethoxy, 1,2-difluoroethoxy, 1,1-difluoropropoxy, 2,2-difluoropropoxy, 3,3-difluoropropoxy, 1,2-difluoropropoxy, 1,3-difluoropropoxy, 1,1-difluorobutoxy, 2,2-difluorobutoxy, 3,3-difluorobutoxy, 4,4-difluorobutoxy, 1,2-difluorobutoxy, 1,3-difluorobutoxy, 1,4-difluorobutoxy, 2,3-difluorobutoxy, 2,4-difluorobutoxy, 3,4-difluorobutoxy, 1,1-difluoropentyloxy, 2,2-difluoropentyloxy, 3,3-difluoropentyloxy, 4,4-difluoropentyloxy, 5,5-difluoropentyloxy, 1,2-difluoropentyloxy, 1,3-difluoropentyloxy, 1,4-difluoropentyloxy, 1,5-difluoropentyloxy, 2,3-difluoropentyloxy, 2,4-difluoropentyloxy, 2,5-difluoropentyloxy, 3,4-difluoropentyloxy, 3,5-difluoropentyloxy, 4,5-difluoropentyloxy, 16,16-difluorohexadecyloxy, 1,1,2-trifluoroethoxy, 2,2,2-trifluoroethoxy, 1,1,2-trifluoropropoxy, 1,1,3-trifluoropropoxy, 1,2,2-trifluoropropoxy, 1,3,3-trifluoropropoxy, 2,2,3-trifluoropropxy, 1,2,3-trifluoropropxy, 3,3,3-trifluoropropxy, 2,4,4-trifluorobutoxy, 3,4,4-trifluorobutoxy, 4,4,4-trifluorobutoxy and 11,11,11-trifluoroundecyloxy can be exemplified.
As the alkoxy alkyl groups replaced by fluorines, fluoromethoxy methyl, 1-fluoro-1-methoxymethyl, (1-fluoroethoxy)methyl, (2-fluoro ethoxy)methyl, 1-fluoro-1-ethoxymethyl, (1-fluoropropoxy)methyl, (2-fluoropropoxy) methyl, (3-fluoropropoxy)methyl, 1-fluoro-1-propoxymethyl, (1-fluorobutoxy) methyl, (2-fluorobutoxy)methyl, (3-fluorobutoxy)methyl, (4-fluorobutoxy) methyl, 1-fluoro-1-butoxymethyl, 1-(fluoromethoxy)ethyl, 2-(fluoromethoxy) ethyl, 1-fluoro-2-methoxyethyl, 2-(1-fluoroethoxy)ethyl, 2-(2-fluoroethoxy)ethyl, 2-(1-fluoropropoxy)ethyl, 2-(2-fluoropropoxy) ethyl, 2-(3-fluoropropoxy)ethyl, 2-(fluoromethoxy)propyl, 3-(fluoro-methoxy)propyl, 2-(1-fluoroethoxy) propyl, 3-(1-fluoroethoxy)propyl, 3-(2-fluoroethoxy)propyl, 3-(3-fluoroethoxy)propyl, (difluoro-methoxy) methyl, 1-fluoro-1-(fluoromethoxy)methyl, (1,1-difluoroethoxy)methyl, (1,2-difluoroethoxy)methyl, (2,2-difluoroethox
Kondou Tomoyuki
Kubo Yasuhiro
Matsui Shuichi
Miyazawa Kazutoshi
Nakagawa Etsuo
Browdy & Neimark
Chisso Corporation
Wu Shean C.
LandOfFree
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