Fluorine-substituted benzene derivative, liquid-crystal...

Details Fluorine-substituted benzene derivative, liquid-crystal... Fluorine-substituted benzene derivative, liquid-crystal...

1999-05-28

2001-04-03

Kelly, C. H. (Department: 1756)

Compositions

Liquid crystal compositions

Containing nonsteryl liquid crystalline compound of...

C252S299600, C252S299610, C252S299670, C570S144000, C568S626000, C568S647000

Reexamination Certificate

active

06210603

ABSTRACT:

TECHNICAL FIELD
The present invention relates to novel liquid crystalline compounds, liquid crystal compositions, and liquid crystal display devices fabricated by using the liquid crystal composition. More specifically, the invention relates to liquid crystalline compounds having fluorine substituted 1,4-phenylene group, liquid crystal composition comprising the liquid crystalline 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 compound(s)” 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 TFT type displays having characteristics such as a high contrast and wide visual angle are extensively conducted.
For liquid crystal compositions used for TFT, physical properties such as voltage holding ratio is high, threshold voltage (Vth) is low, their alteration caused by the change of temperature is small, temperature range of liquid crystal phase is wide, miscibility with other liquid crystal materials is excellent, and viscosity is low have been sought. Further, liquid crystal compositions having a high optical anisotropy (&Dgr;n) are useful for increasing response speed.
For these purposes, fluorine containing compounds are suitable. Many researches have been conducted up to now and for example, (1) Japanese Patent Publication No. Sho 63-13411, (2) Japanese Patent Publication No. Sho 63-44132, (3) Laid-open Japanese Patent Publication No. Hei 2-233626, (4) Laid-open PCT Japanese Publication (Tokuhyo) No. Hei 2-501311, (5) Laid-open PCT Japanese Publication No. Hei 3-500413, (6) Laid-open PCT Japanese Publication No. Hei 2-501071, (7) Laid-open PCT Japanese Publication No. Hei 3-503711, (8) Laid-open Japanese Patent Publication No. Hei 4-217930, (9) Laid-open PCT Japanese Publication No. Hei 4-501575, (10) Laid-open PCT Japanese Publication No. Hei 6-504032, and (11) EP-439089 are published.
A part of the compounds of the present invention are formally included in the general formula disclosed in the publications (6) to (11) mentioned above. However, data such as physical property values of the compounds which correspond to the ones of the present invention are not disclosed at all and their specific characteristics are not specifically described in any one of the publications mentioned above. Accordingly, those publications have not suggested the present invention.
DISCLOSURE OF THE INVENTION
In view of the required characteristics described above in relation to liquid crystal compositions for TFT, an object of the present invention is to provide (a) liquid crystalline compounds which have an extremely high voltage holding ratio, are small in its alteration caused by the change of temperature, have a low threshold voltage and high &Dgr;n; (b) liquid crystal compositions comprising the compound; and (c) liquid crystal display devices fabricated by using the liquid crystal composition.
As a result of a diligent investigation by the present inventors, it has been found out that the liquid crystalline compounds expressed by the following general formula (1) have intended properties, leading to the accomplishment of the present invention:
wherein R represents an alkyl group having 1 to 20 carbon atoms in which alkyl group any not-adjacent methylene group (—CH
2
—) may be replaced by oxygen (—O—) atom; Y
1
to Y
16
independently represent hydrogen atom or fluorine atom, but at least three of them are fluorine atoms, provided that in no case three or more hydrogen atoms of one 1,4-phenylene group are replaced by fluorine atom; X represents a halogen atom or an alkyl group having 1 to 20 carbon atoms in which alkyl group any not-adjacent methylene group may be replaced by oxygen atom, and any hydrogen atom in the alkyl group may be replaced by fluorine atom; Z
1
, Z
2
, and Z
3
independently represent —(CH
2
)
2
—, —(CH
2
)
4
—, —CH
2
O—, —OCH
2
—, —(CH
2
)
3
O—, —O(CH
2
)
3
—, or single bond; and any atom which constitutes this compound may be replaced by its isotope; provided that
when X=—OCF
2
CF
2
H, Z
1
=Z
3
=single bond, and Z
2
=—(CH
2
)
2
—, in no case
Y
6
=Y
10
=Y
12
F, and Y
1
to Y
5
=Y
7
to Y
9
=Y
11
=Y
13
to Y
16
=H,
Y
2
=Y
10
=Y
12
=F, and Y
1
=Y
3
to Y
9
=Y
11
=Y
13
to Y
16
=H, or
Y
2
=Y
4
=Y
10
=Y
12
=F, and Y
1
=Y
3
=Y
5
to Y
9
=Y
11
=Y
13
to Y
16
=H.
Compounds expressed by the general formula (1) are classified as follows:
In the following formulas (1a) to (1h), R and X have the same meaning as described above, Za to Zc independently represent —(CH
2
)
2
—, —(CH
2
)
4
—, —CH
2
O—, —OCH
2
—, —(CH
2
)
3
O—, or —O(CH
2
)
3
—, and P represents 1,4-phenylene group in which any one or two hydrogen atoms may be replaced by fluorine atom.
R—P—P—P—P—X  (1a)
R—P—Za—P—P—P—X  (1b)
R—P—P—Zb—P—P—X  (1c)
R—P—P—P—Zc—P—X  (1d)
R—P—Za—P—Zb—P—P—X  (1e)
R—P—Za—P—P—Zc—P—X  (1f)
R—P—P—Zb—P—Zc—P—X  (1g)
R—P—Za—P—Zb—P—Zc—P—X  (1h)
Among these compounds, compounds expressed by one of the formulas (1a) to (1d) are especially preferable for achieving the purpose of the present invention.
Among these formulas, R is a straight chain or branched alkyl group having 1 to 20 carbon atoms. As the straight chain alkyl group, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, decyl, pentadecyl, and icosyl; and as branched alkyl group, isopropyl, sec-butyl, tert-butyl, 2-methyl-butyl, isopentyl, isohexyl, 3-ethyloctyl, and 3,8-dimethyltetradecyl can specifically be mentioned.
In these alkyl groups, any methylene group (—CH
2
—) may be replaced by oxygen (—O—) unless oxygen atom continues. As examples of alkyl groups in which methylene group is replaced by oxygen, alkoxy groups and alkoxyalkyl groups can be mentioned.
As more specific examples of these groups, alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, and nonyloxy; 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 can be mentioned.
X represents a halogen atom or an alkyl group having 1 to 20 carbon atoms. In this alkyl group, any methylene group (—CH
2
—) may be replaced by oxygen (—O—) unless oxygen atom continues, and hydrogen atom in the group may be replaced by fluorine atom. Specifically, the alkyl groups, alkoxy groups, and alkoxyalkyl groups described above can be mentioned as examples.
Further, as fluoroalkyl group, fluoromethyl, difluoromethyl, trifluoromethyl, 1,1,2,2-tetrafluoroethyl, perfluoroethyl, 1,1,2,2-tetrafluoropropyl, 1,1,3,3-tetrafluoropropyl, 2,2,3,3-tetrafluoropropyl, 1,1,2,3-tetrafluoropropyl, 1,2,2,3-tetrafluoropropyl, 1,2,3,3-tetrafluropropyl, 1,1,3,3,3-pentafluoropropyl, 1,1,2,3,3,3-hexafluoropropyl, 1,1,4,4,4-pentafluoro-butyl, 1,2,5,5-tetrafluoropentyl, and perfluoroicosyl;
as fluoroalkoxy group, difluoromethoxy, trifluoromethoxy, 1,1,2,2-tetrafluoroethoxy, perfluoroethoxy, 1,1,2,2-tetrafluoropropoxy, 1,1,3,3-tetrafluoropropoxy, 1,1,3,3,3-pentafluoropropoxy, 1,1,2,3,3,3-hexafluoropropoxy, 1,1,4,4,4-pentafluorobutoxy, and 1,1,2,3,5,5,5-heptafluoropentyloxy; and
as alkoxyalkyl group replaced by fluorine, (trifluoromethoxy)fluoromethyl, (1,1,2,2-tetrafluoroethoxy)methyl, 1,2,2,2-tetrafluroethoxy)methyl, (perfluoroethoxy)methyl, (1,1,3,3-tetra

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