Stock material or miscellaneous articles – Liquid crystal optical display having layer of specified...
Reexamination Certificate
1999-05-28
2001-12-11
Wu, Shean C. (Department: 1756)
Stock material or miscellaneous articles
Liquid crystal optical display having layer of specified...
C252S299630, C252S299660, C544S242000, C544S335000, C544S336000, C546S001000, C549S356000, C549S369000, C549S377000, C556S406000, C570S127000, C570S129000, C570S144000
Reexamination Certificate
active
06329027
ABSTRACT:
TECHNICAL FIELD
The present invention relates to liquid crystalline compounds and liquid crystal compositions. More specifically, the invention relates to liquid crystalline compounds having chlorine substituted 1,4-phenylene group, liquid crystal compositions comprising the compound, and liquid crystal display devices fabricated by using the liquid crystal composition.
BACKGROUND ART
Display devices produced by using liquid crystalline compounds (the term “liquid crystalline compounds” is used in this specification as a general term for the compounds which exhibit a liquid crystal phase and for the compounds which do not exhibit a liquid crystal phase but are useful as component of liquid crystal compositions) have widely been utilized for the display of watches, tabletop calculators, word processors, or the likes. In recent years, researches on in-plane switching (IPS) mode and vertical alignment (VA) mode by which viewing angle can be improved at a moderate cost have extensively been conducted.
For the liquid crystal compositions used in these modes, such physical properties as a high voltage holding ratio, low threshold voltage, small their dependency on temperature, low optical anisotropy value (&Dgr;n), wide temperature range of liquid crystal phase, excellent miscibility with other liquid crystal materials, and low viscosity have been sought.
As the component of liquid crystal compositions having such characteristics, many liquid crystalline compounds in which fluorine atom substituted at a lateral position were investigated, and patents disclosing, for example, the following compounds are published:
1) (Laid-open Japanese Patent Publication No. Hei 2-233626)
2) (Tokuhyo (Laid-open Japanese WO publication) No. Hei 2-503441)
3) (Tokuhyo (Laid-open Japanese WO publication) No. Hei 6-504032)
4) (DE 3,839,213 A1)
Whereas the compounds of the formula 1) or 2) have a low &Dgr;n, their threshold voltage is high. Whereas the compounds of the formula 3) or 4) have a low threshold voltage, their &Dgr;n is high. Thus, these compounds can not be said to have satisfied the requirements mentioned above.
Chlorine substituted compounds are disclosed, for example in 5) DE 2,933,563 and 6) DE 4,219,819.
A part of the compounds expressed by the general formula (1) are formally included in the prior literature 5) or 6) mentioned above. However, as to the compounds of the present invention, data such as physical properties are not described at all and their characteristics are not specifically mentioned in the prior publications. Thus, the publications have not suggested the utility of the compounds of the present invention.
DISCLOSURE OF THE INVENTION
In view of the required characteristics described above, an object of the present invention is to provide liquid crystalline compounds having an extremely high voltage holding ratio and a low threshold voltage, being considerably small in their dependency on temperature, having a low &Dgr;n, and being excellent in miscibility with other liquid crystal materials besides; to provide liquid crystal compositions comprising the compound, and to provide liquid crystal display devices fabricated by using the liquid crystal composition.
As a result of diligent investigations by the present invention to solve the problems described above, it has been found out that the chlorobenzene derivatives expressed by the following general formula (1) have desired properties, leading to the accomplishment of the present invention:
Ra—A
1
—Z
1
—A
2
&Parenopenst;Z
2
—A
3
&Parenclosest;
m
&Parenopenst;Z
3
—A
4
&Parenclosest;
n
Rb (1)
wherein Ra represents a straight chain or branched alkyl group having 1 to 20 carbon atoms in which group, any methylene group (—CH
2
—) may be replaced by —O—, —CO—, —CH═CH—, —C≡C—, —SiH
2
—, or cyclobutane-1,3-diyl, but in no case continues —O—, and one or more hydrogen atoms in the Ra may be replaced by a halogen atom or cyano group; Rb represents a group selected from the Ra, a halogen atom, or cyano group; A
1
, A
2
, A
3
, and A
4
independently represent trans-1,4-cyclohexylene or 1,4-phenylene in which ring any —CH
2
— may be replaced by —O—, >CH— may be replaced by >SiH—, and —CH═ may be represented by —N═, respectively, and one or two hydrogen atoms on the six-membered ring may be replaced by a halogen atom provided that at least two hydrogen atoms among all hydrogen atoms on the six-membered rings which constitute the compound are replaced by a halogen atom including chlorine atom; Z
1
, Z
2
, and Z
3
independently represent single bond or an alkylene group in which one or more hydrogen atoms may be replaced by a halogen atom, any methylene group (—CH
2
—) in the alkylene group may be replaced by —O—, —CO—, —CH═CH—, —C≡C—, or —SiH
2
— but in no case continues —O—; m and n are independently 0 or 1; provided that when m=1, n=0, A
1
is trans-1,4-cyclohexylene, A
2
and A
3
are 1,4-phenylene, and Z
1
and Z
2
are single bond, or when m+n=1, and at least one of Z
1
and Z
2
is —COO or —OCO—, then at least three hydrogen atoms in all hydrogen atoms on the six-membered rings which constitute the compound are replaced by a halogen atom including chlorine atom; and provided that when m=1, n=0, A
1
and A
2
are trans-1,4-cyclohexylene, and A
3
is 1,4-phenylene, then in no case are Z
1
and Z
2
single bond; and an atom which constitutes the compound may be replaced by its isotope.
In the general formula (1), while Ra represents a straight chain or branched alkyl group having 1 to 20 carbon atoms, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, decyl, pentadecyl, and icosyl can specifically be mentioned as straight chain alkyl group; and isopropyl, sec-butyl, tert-butyl, 2-methylbutyl, isopentyl, isohexyl, 3-ethyloctyl, 3,8-dimethyltetradecyl, and 5-ethyl-5-methylnonadecyl can be mentioned as branched alkyl group.
In these alkyl groups, any methylene group (—CH
2
—) may be replaced by —O—, —CO—, —CH═CH—, —C≡C—, —SiH
2
—, or cyclobutane-1,3-diyl provided that —O— does not continue.
As examples of these groups, alkoxy group, alkoxyalkyl group, alkenyl group, alkadienyl group, alkenyloxy group, alkoxyalkenyl group, alkynyl group, alkynyloxy group, alkoxyalkynyl group, silanyl group, alkylsilyl group, alkoxysilyl group, alkylsilylalkyl group, alkoxysilylalkyl group, alkyldisilanyl group, alkyldisilanylalkyl group, and alkyltrisilanyl group can be mentioned. Further, one or more hydrogen atoms in these groups may be replaced by a halogen atom, and as its examples, a halogen substituted alkyl group, halogen substituted alkoxy group, halogen substituted alkenyl group, and halogen substituted alkynyl group can be mentioned.
Among them, examples of preferable groups are mentioned as follows:
As groups in which —CH
2
— is replaced by —O—, 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; and as branched alkoxy groups, 2-methylpropoxy, 2-methylpentoxy, and 1-methylheptoxymethyl can be mentioned.
As groups in which —CH
2
— is replaced by —CH═CH—, alkenyl groups such as vinyl, propenyl, butenyl, pentenyl, hexenyl, and decenyl, alkoxyalkenyl groups such as methoxypropenyl, ethoxypropenyl, pentyloxypropenyl, methoxybutenyl, ethoxybutenyl, pentyloxybutenyl, methoxypentenyl, propoxypentenyl, methoxyhexenyl, propoxyhexenyl, methoxyheptenyl, and methoxyoctenyl, alkenyloxy groups such as propenyloxy, butenyloxy, pentenyloxy, octenyloxy, and propenyloxymethyl, groups such as propenyloxyethyl, propenyloxybutyl, butenyloxymethyl, butenyloxyethyl, butenyloxypentyl, pentenyloxymethyl, pentenyloxypropyl, hexenyloxymethyl, hexeny
Kondo Tomoyuki
Matsui Shuichi
Miyazawa Kazutoshi
Nakagawa Etsuo
Takeshita Fusayuki
Chisso Corporation
Wenderoth , Lind & Ponack, L.L.P.
Wu Shean C.
LandOfFree
Chlorobenzene derivatives, liquid-crystal composition, and... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Chlorobenzene derivatives, liquid-crystal composition, and..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Chlorobenzene derivatives, liquid-crystal composition, and... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2591017