Difluorovinyl compound, liquid crystal composition and...

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Reexamination Certificate

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C252S299610, C252S299630, C252S299660, C549S428000, C549S356000, C549S369000, C549S370000, C549S380000, C570S128000

Reexamination Certificate

active

06649227

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a liquid crystalline compound and a liquid crystal composition. More specifically, it relates to a novel liquid crystalline compound which has a hetero ring structure and which has a difluorovinyl group at a terminal of the compound, a liquid crystal composition comprising the same, a liquid crystal display which is constituted with this liquid crystal composition and a synthetic intermediate for the liquid crystalline compound. In the present invention, the term of the liquid crystalline compound is used as a general term of a compound showing a liquid crystal phase and a compound that does not show a liquid crystal phase but is useful as a structural component for a liquid crystal composition.
BACKGROUND ART
Many display elements making use of characteristics of a nematic liquid crystal compound have so far been produced. In recent years, a liquid crystal display (LCD) is widely used for various uses including not only watches and portable electric calculators but also monitors for personal computers and portable telephones, and demand therefor has been growing large year by year. In accordance with it, improvement items for performances required for LCD have come to extend over many divergences such as an expansion in an operable temperature range, a shift to high density and coloring of the display, an acceleration in response and an expansion in a viewing angle. It is known that various display modes using electro-optical effects, such as a DS (dynamic scattering) mode, a TN (twist nematic) mode, a GH (guest host) mode, an STN (super twist nematic) mode, an IPS (in-plane switching) mode and a VA (vertical alignment) mode have been proposed in order as means for solving them.
In such situation, various characteristics are required to a liquid crystal composition used for LCD according to the respective display modes. First, the physical property values such as optical anisotropy (&Dgr;n), dielectric anisotropy (&Dgr;&egr;), viscosity (&eegr;), conductivity and elastic constant ratio K
33
/K
11
(K
33
: bend elastic constant and K
11
: spray elastic constant) of a liquid crystal composition are required to have values which are optimum for a display mode and a form of an element. In LCD may be used in outdoor at low temperature as a portable telephone and a mobile personal computer, a liquid crystal composition that is stably operated at low temperature is required. In order to meet this, a liquid crystalline compound constituting it has to be excellent in solubility at low temperature. Further, a portable telephone tends to be always increased, though it has a small display, in an information amount displayed thereon, so that display having high contrast is desired. In an STN mode that is mainly used for the LCD, a liquid crystalline compound having a high K
33
/K
11
value is required in order to obtain high contrast ratio. Further, in order to achieve quick response in any of the LCD's shown above, a liquid crystal composition having low viscosity is required, and a liquid crystalline compound has to be indispensably reduced as well in viscosity. In addition thereto, given as common items of characteristics required to a liquid crystal composition are stability against moisture, light, heat and air that are usually present under use environment and stability against an electric field and electromagnetic irradiation. Further, the respective components of a liquid crystalline compound constituting a liquid crystal composition have to be chemically stable to each other in a use environment, and it is important as well that they have good solubility with each other.
In the existing state, however, it is very difficult to solve these problems only with the existing liquid crystal compounds and liquid crystal compositions, and it is an urgent matter to develop a novel liquid crystalline compound and liquid crystal composition which can meet the various requirements described above.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a liquid crystalline compound which has particularly a wide liquid crystal phase temperature range, low viscosity, a large elastic constant ratio K
33
/K
11
and solubility improved at low temperature so that the problems of conventional techniques can be overcome, a liquid crystal composition comprising the same, a liquid crystal display which is constituted with the above liquid crystal composition and an intermediate useful for producing the liquid crystalline compound having excellent characteristics.
In order to achieve the objects described above, the following inventions are claimed for the grant of a patent in the present application.
(1) A difluorovinyl compound represented by Formula (1):
wherein Y
1
represents H or straight chain or branched alkyl group having 1 to 10 carbon atoms, and optional —CH
2
— in the above alkyl group may be replaced by —O— or —CH═CH—, but —O— is not adjacent to each other, and at least one H in Y
1
may be substituted with halogen or a cyano group; A
1
, A
2
, A
3
and A
4
each independently represent 1,4-cyclohexylene in which optional —CH
2
— which is not adjacent to each other may be replaced by —O—, 1,4-phenylene in which optional H may be substituted with halogen, and a single bond, in which at least two of A
1
, A
2
, A
3
and A
4
have the ring structure described above, and at least one of them is 1,4-cyclohexylene in which —CH
2
— is replaced by —O—; Z
1
, Z
2
and Z
3
each independently represent a single bond, —(CH
2
)
2
—, —CH═CH—, —(CH
2
)
4
—, —O(CH
2
)
3
— or —(CH
2
)
3
O—; n represents 0 or an integer of 1 to 10, provided that when any of A
1
, A
2
, A
3
and A
4
is 1,4-phenylene, Z
1
, Z
2
and Z
3
are single bonds, and among them, when A
1
is 1,3-dioxane-2,5-diyl and A
2
is 1,4-phenylene and when A
3
is 4,cyclohexylene and A
4
is a single bond, Y
1
is H, and n is not 0.
(2) A difluorovinyl compound as described in the above item [1], wherein A
1
, A
2
, A
3
and A
4
each independently represent 1,4-cyclohexylene in which optional —CH
2
— which is not adjacent to each other may be replaced by —O—, 1,4-phenylene and a single bond, in which at least two of A
1
, A
2
, A
3
and A
4
have the ring structure described above, and at least one of them is 1,4-cyclohexylene in which —CH
2
— is replaced by —O—; Z
1
, Z
2
and Z
3
each independently represent a single bond, —(CH
2
)
2
— or —(CH
2
)
4
—, provided that when any of A
1
, A
2
, A
3
and A
4
is 1,4-phenylene, Z
1
, Z
2
and Z
3
are single bonds, and among them, when A
1
is 1,3-dioxane-2,5-diyl and A
2
is 1,4-phenylene and when A
3
is 1,4-cyclohexylene and A
4
is a single bond, Y
1
is H, and n is not 0.
(3) A difluorovinyl compound as described in the above item (1), wherein A
1
is 1,3-dioxane-2,5-diyl; A
2
is 1,4-cyclohexylene; and A
3
, A
4
, Z
1
, Z
2
and Z
3
are single bonds.
(4) A difluorovinyl compound as described in the above item (1), wherein either one of A
1
and A
2
is 1,3-dioxane-2,5-diyl, and the other is 1,4-cyclohexylene; A
3
is 1,4-cyclohexylene; and A
4
, Z
1
, Z
2
and Z
3
are single bonds.
(5) A difluorovinyl compound as described in the above item (1), wherein either one of A
1
, A
2
and A
3
is 1,3-dioxane-2,5-diyl, and the remaining two are 1,4-cyclohexylenes; A
4
is 1,4-cyclohexylene; and Z
1
, Z
2
and Z
3
are single bonds.
(6) A difluorovinyl compound as described in the above item (1), wherein A
1
is 1,3-dioxane-2,5-diyl; A
2
is 1,4-cyclohexylene; Z
1
is —(CH
2
)
2
— or —(CH
2
)
4
—; and A
3
, A
4
, Z
2
and Z
3
are single bonds.
(7) A difluorovinyl compound as described in the above item (1), wherein either one of A
1
and A
2
is 1,3-dioxane-2,5-diyl, and the other is 1,4-cyclohexylene; A
3
is 1,4-cyclohexylene; either one of Z
1
and Z
2
is —(CH
2
)
2
— or —(CH
2
) 4-, and the other is a single bond; and A
4
, Z
1
, Z
2
and Z
3
are single bonds.
(8) A difluorovinyl compound as described in the above item (1), wherein either one of A
1
, A
2
and A
3
is 1,3-dioxane-2,5-diyl, and the

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