Pentafluorosulfuranylbenzene derivatives

Details Pentafluorosulfuranylbenzene derivatives Pentafluorosulfuranylbenzene derivatives

2001-06-27

2003-10-07

Wu, Shean C. (Department: 1756)

Stock material or miscellaneous articles

Liquid crystal optical display having layer of specified...

C252S299610, C252S299620, C252S299630, C252S299660, C549S369000, C568S074000, C568S077000, C570S129000, C570S131000

Reexamination Certificate

active

06630210

ABSTRACT:

The invention includes novel pentafluorosulfuranylbenzene derivatives of the formula I
in which
R
1
is H or an alkyl or alkylene radical having 1 to 15 carbon atoms which is unsubstituted or monosubstituted by CN or CF
3
or optionally monosubstituted to perhalo-substituted by halogen and in which, in addition, one or more non-adjacent CH
2
groups may each, independently of one another, be replaced by —O—, —S—, —CO—, C≡C—,
—CO—O—, —O—CO— or —O—CO—O— in such a way that oxygen atoms are not linked directly to one another,
A
1
and A
2
are, independently of one another,
a) a trans-cyclohexane-1,4-diyl radical, in which, in addition, one or more non-adjacent CH
2
groups may be replaced by —O— and/or —S—,
b) a 1,4-phenylene radical, in which, in addition, one or two CH groups may be replaced by N,
c) a radical selected from the group consisting of 1,4-bicyclo[2.2.2]-octylene, piperidine-1,4-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl and 1,2,3,4-tetrahydronaphthalene-2,6-diyl,
d) a cyclohexylene-1,4-diyl radical,
where the radicals a), b), c) and d) may be substituted by CN, CH
3
, Cl or F,
L
1
, L
2
, L
3
are H, CN, F or Cl,
Z
1
is —CO—O—, —O—CO—, —CH
2
O—, —O—, —OCH
2
—, —CH
2
CH
2
—, —CHFCH
2
—, —CH═CH—, —CH
2
CF
2
—, —CF
2
CH
2
—, —CF
2
—CHF—, —CHFCF
2
—, —C≡C—, —C
2
F
4
—, —CF═CF—, —OCF
2
—, —CF
2
O— or a single bond, and
n is 0, 1, 2 or 3.
The invention furthermore includes the use of these compounds as components of liquid-crystalline media, and to liquid-crystal and electro-optical display elements which contain the liquid-crystalline media according to the invention.
The compounds of the formula I can be used as components of liquid-crystalline media, in particular for displays based on the principle of the twisted cell, the guest-host effect, the effect of deformation of aligned phases (DAP) or electrically controlled birefringence (ECB) or the effect of dynamic scattering. The substances employed hitherto for this purpose all have certain disadvantages, for example inadequate stability to exposure to heat, light or electric fields, or unfavorable elastic and/or dielectric properties.
It has now been found that the compounds of the formula I are very suitable as components of liquid-crystalline media. They can be used to obtain stable liquid-crystalline media, in particular suitable for TFT or STN displays. The novel compounds of the formula I are notable for having a high clearing point in combination with relatively high &Dgr;∈ values at the same time as broad nematic phases.
Generally, the provision of compounds of the formula I considerably broadens the range of liquid-crystalline substances which are suitable, from various applicational points of view, for the preparation of liquid-crystalline mixtures.
The compounds of the formula I have a broad range of applications. Depending on the choice of substituents, these compounds can serve as base materials of which liquid-crystalline media are predominantly composed; however, it is also possible to add compounds of the formula I to liquid-crystalline base materials from other classes of compounds in order, for example, to modify the dielectric and/or optical anisotropy of a dielectric of this type and/or to optimize its threshold voltage and/or its viscosity. The formula I furthermore encompasses all isotopes of the elements present in compounds of the formula I.
In the pure state, the compounds of the formula I are colorless and form liquid-crystalline mesophases in a temperature range which is favorably located for electro-optical use. They are stable chemically, thermally and to light.
The invention thus also includes the compounds of the formula I and use of these compounds as components of liquid-crystalline media. The invention furthermore includes liquid-crystalline media comprising at least one compound of the formula I, and to liquid-crystal display elements, in particular electro-optical display elements, which contain media of this type.
Hereinbefore and hereinafter, R
1
, A
1
, A
2
, Z
1
, L
1
, L
2
, L
3
and n are as defined above, unless expressly stated otherwise.
For simplicity, hereinafter A
3
is
Cyc is a 1,4-cyclohexylene radical, Che is a 1,4-cyclohexenylene radical, Dio is a 1,3-dioxane-2,5-diyl radical, Dit is a 1,3-dithiane-2,5-diyl radical, Phe is a 1,4-phenylene radical, Pyd is a pyridine-2,5-diyl radical, Pyr is a pyrimidine-2,5-diyl radical, Bco is a bicyclo[2.2.2]-octylene radical, and Dec is a decahydronaphthalene radical, where Cyc and Phe may be unsubstituted or mono- or polysubstituted by CH
3
, Cl, F or CN.
The formula I encompasses the preferred compounds Ia to Ic having two or three rings, respectively:
R
1
-A
2
-CF
2
O-A
3
-SF
5
  Ia
R
1
-A
1
-A
2
-CF
2
O-A
3
-SF
5
  Ib
R
1
-A
1
-Z
1
-A
2
-CF
2
O-A
3
-SF
5
  Ic
in which R
1
, A
1
, A
2
, A
3
and Z
1
are as defined above.
R
1
is preferably straight-chain alkyl or alkoxy having 1 to 10 carbon atoms or alkenyl or alkenyloxy having 2 to 10 carbon atoms. n is preferably 1 or 2.
A
1
is preferably Phe, Cyc, Che, Pyd, Pyr or Dio, in particular Phe, Cyc or Dio. The compounds of the formula I preferably comprise not more than one of the radicals Bco, Dec, Pyd, Pyr or Dit.
The cyclohexene-1,4-diyl group is preferably of the following structures:
If the radical A
1
(n=2 or 3) occurs more than once, the two rings can have the same or different meanings. The same applies to the bridge Z
1
and to all other groups which occur more than once in the compounds of the formula I.
A
1
is preferably trans-cyclohexane-1,4-diyl or 1,4-phenylene.
Preference is likewise given to compounds of the formula I and all sub-formulae in which A
1
and/or A
2
are/is 1,4-phenylene which is mono- or disubstituted by F or CN.
A
1
and A
2
are preferably, independently of one another,
Z
1
is preferably —CH
2
CH
2
—, —CH═CH—, —C≡C—, —CF
2
CF
2
—, —CF═CF—, —CF
2
O—, —OCF
2
— or a single bond, in particular a single bond, —CH
2
CH
2
— or —CF
2
CF
2
—.
Preference is given to compounds of the formula I which are characterized in that R
1
is straight-chain alkyl or alkoxy having 1 to 10 carbon atoms or alkenyl having 2 to 10 carbon atoms and Z is —CF
2
CF
2
— or —CF═CF—.
Compounds of the formula I in which A
2
is
represent a preferred embodiment of the invention.
Particular preference is given to those compounds of the formula I which are characterized in that R
1
is straight-chain alkyl or alkenyloxy having 1 to 10 carbon atoms or alkenyl or alkenyloxy having 2 to 10 carbon atoms
and A
1
is
The following group of compounds of the sub-formulae I1 to I71 represents another preferred embodiment of the invention.
in which R
1
is as defined above.
If R
1
in the formulae above and below is an alkyl and/or alkoxy radical, this can be straight-chain or branched. It is preferably straight-chain, has 2, 3, 4, 5, 6 or 7 carbon atoms and accordingly is preferably ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy or heptyloxy, furthermore methyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy or tetradecyloxy.
Oxaalkyl is preferably straight-chain 2-oxapropyl (=methoxymethyl), 2-(=ethoxymethyl) or 3-oxabutyl (=2-methoxyethyl), 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, 2-, 3-, 4-, 5-, 6- or 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, or 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl.
If R
1
is an alkyl radical in which one CH
2
group has been replaced by —CH═CH—, this can be straight-chain or branched. It is preferably straight-chain and has 2 to 10 carbon atoms. Accordingly, it is in particular vinyl, prop-1- or -2-enyl, but-1-, -2- or -3-enyl, pent-1-, -2-, -3- or -4-enyl, hex-1-, -2-, -3-, -4- or -5-enyl, hept-1-, -2-, -3-, -4-, -5- or -6-enyl, oct-1-, -2-, -3-, -4-, -5-, -6- or -7-enyl, non-1-, -2-, -3-, -4-, -5-, -6-, -7- or -8-enyl,

Affiliated with

Also associated with

Rating

Pentafluorosulfuranylbenzene derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Pentafluorosulfuranylbenzene derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Pentafluorosulfuranylbenzene derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3118174