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Patent 2035862 Summary

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(12) Patent: (11) CA 2035862
(54) English Title: SUPERTWIST LIQUID CRYSTAL DISPLAY
(54) French Title: ECRAN A CRISTAUX LIQUIDES A ROTATION COMPLETE
Status: Expired
Bibliographic Data
(52) Canadian Patent Classification (CPC):
  • 31/105
  • 345/8
(51) International Patent Classification (IPC):
  • C09K 19/42 (2006.01)
  • C09K 19/02 (2006.01)
  • C09K 19/30 (2006.01)
  • C09K 19/44 (2006.01)
  • G02F 1/137 (2006.01)
(72) Inventors :
  • SCHEUBLE, BERNHARD (Germany)
  • OYAMA, TAKAMASA (Japan)
  • WEBER, GEORG (Germany)
  • PLACH, HERBERT (Germany)
  • KURMEIER, HANS-ADOLF (Germany)
  • REIFFENRATH, VOLKER (Germany)
(73) Owners :
  • MERCK PATENT GESELLSCHAFT MIT BESCHRAENKTER HAFTUNG (Germany)
(71) Applicants :
  • MERCK PATENT GESELLSCHAFT MIT BESCHRAENKTER HAFTUNG (Germany)
(74) Agent: FETHERSTONHAUGH & CO.
(74) Associate agent:
(45) Issued: 2004-03-30
(86) PCT Filing Date: 1990-06-15
(87) Open to Public Inspection: 1991-01-24
Examination requested: 1997-05-15
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): Yes
(86) PCT Filing Number: PCT/EP1990/000936
(87) International Publication Number: WO1991/000898
(85) National Entry: 1991-03-11

(30) Application Priority Data:
Application No. Country/Territory Date
P 39 23 064.3 Germany 1989-07-13

Abstracts

English Abstract



Supertwist liquid crystal displays having out-
standing properties are obtained if the nematic liquid
crystal mixture is based on components selected from
group A comprising compounds of the formulae IIa to IIk;
(See formula IIa, IIb, IIc, IId, IIe, IIf, IIg, IIh, IIi, IIj and IIk)


Claims

Note: Claims are shown in the official language in which they were submitted.



50

CLAIMS:

1. ~Supertwist liquid crystal display with two plane-
parallel carrier plates which, with a frame, form a cell,
a nematic liquid crystal mixture, located in the
cell, having a positive dielecric anisotropy,
electrode layers with superposed orientation layers
on the insides of the carrier plates,
a tilt angle of about 1 degree to 30 degrees between
the longitudinal axis of the molecules at the surface of the
carrier plates and the carrier plates, and
a twist angle of the liquid crystal mixture in the
cell from orientation layer to orientation layer of an amount
between 100 and 600°,
wherein the nematic liquid crystal mixture comprises:
component A containing one or more compounds selected
from group A consisting of compounds of the formulae IIa to
IIk:
Image


51

Image

in which R is n-alkyl or n-alkenyl having up to 9 C atoms,
X is F, Cl, -CF3, -CHF2, -OCF3, or -OCHF2, and the
rings A1, A2 and A3 each independently of one another are
1,4-phenylene, 2- or 3-fluoro-1,4-phenylene or trans-1,4-
cyclohexylene, or one of the rings A1, A2 and A3 is
1,4-cyclohexenylene, 2,3-difluoro-1,4-phenylene, pyridine-2,5-
diyl or pyrimidine-2,5-diyl, and
an optically active component D in such a quantity
that the ratio of cell thickness (spacing of the plane-parallel
carrier plates) to the natural pitch of the chiral nematic
liquid crystal mixture is about 0.2 to 1.3,
wherein the nematic liquid crystal mixture has a
nematic phase range of at least 60°C, a viscosity of not more
than 35 mPa.cndot.s and a dielectric anisotropy of at least +1, the
dielectric anisotropies of the compounds and the parameters


52

relating to the nematic liquid crystal mixture referring to a
temperature of 20°C.

2. ~The display according to claim 1, wherein component A
further contains one or more compounds selected from Group A'
consisting of compounds of formulae II'a to II'k:
Image


53

Image
wherein R, A1, A2 and A3 are as defined above and X'
is -NCS or cyano;
further wherein when component A contains compounds
of the formulae II'a to II'f, in which X' is cyano, and
compounds of the formulae IIa to IIf, in which X is F, Cl,
-CF3, -CHF2, -OCF3, or -OCHF2, the proportion of the cyano
compounds in component A is up to 50% by weight.

3. ~The display according to claim 1, wherein the crystal
mixture further comprises up to 20% by weight of a liquid-
crystalline component C consisting of one or more compounds
having a dielectric anisotropy below -1.5.

4. ~The display according to claim 2, wherein the crystal
mixture further comprises up to 20% by weight of a liquid-
crystalline component C consisting of one or more compounds
having a dielectric anisotropy below -1.5.

5. ~The display according to claim 1, wherein the crystal
mixture further comprises up to 40% by weight of a liquid-
crystalline component B, consisting of one or more compounds
having a dielectric anisotropy from -1.5 to +1.5, of the
general formula I
Image
in which R1 and R2 each independently of one another are
n-alkyl, n-alkoxy, n-oxaalkyl, .omega.-fluoroalkyl or n-alkenyl
having up to 9 C atoms, the rings A1, A2 and A3 each
independently of one another are 1,4-phenylene, 2- or 3-fluoro-



54

1,4-phenylene, trans-1,4-cyclohexylene or 1,4-cyclohexenylene,
Z1 and Z2 each independently of one another are -CH2CH2-, -C.ident.C-
or a single bond, and m is 0, 1 or 2.

6. ~The display according to claim 2 or 4, wherein the
crystal mixture further comprises up to 40% by weight of a
liquid-crystalline component B, consisting of one or more
compounds having a dielectric anisotropy from -1.5 to +1.5, of
the general formula I
Image~
in which R1 and R2 each independently of one another are
n-alkyl, n-alkoxy, n-oxaalkyl, .omega.-fluoroalkyl or n-alkenyl
having up to 9 C atoms, the rings A1, A2 and A3 each
independently of one another are 1,4-phenylene, 2- or 3-fluoro-
1,4-phenylene, trans-1,4-cyclohexylene or 1,4-cyclohexenylene,
Z1 and Z2 each independently of one another are -CH2CH2-, -C.ident.C-
or a single bond, and m is 0, 1 or 2.

7. ~The display according to claim 2 or 4, wherein
component A contains one or more compounds of the formulae II'a
to II'f in which X' is cyano.

8. ~The display according to claim 6, wherein component A
contains one or more compounds of the formulae II'a to II'f in
which X' is cyano.

9. ~Display according to any one of claims 5, 6 and 8,
characterized in that component B contains one or more
compounds selected from the group consisting of compounds of
formulae II1 to II7:
Image


55

Image
in which R1 and R2 have the meanings defined in claim 5, and in
which thick dots on the cyclohexane rings indicate that the
carbon atom is trans-substituted at that spot on the ring.

10. The display according to claim 9, wherein component B
contains one or more compounds selected from the group
consisting of compounds of formulae II8 to II20:
Image



56

Image
in which R1 and R2 have the meanings defined in claim 5, the
thick dots have the meaning defined in claim 9, and the
1,4-phenylene groups in II8 to II17 each independently of one
another can also be mono- or poly-substituted by fluorine.


57

11. The display according to claim 9 or 10, wherein
component B contains one or more compounds selected from the
group consisting of compounds of formulae II21 to II25:

Image

in which R1 and R2 have the meanings given in claim 5, the
thick dots have the meaning defined in claim 9, and the
1,4-phenylene groups in II21 to II25 each independently of one
another can also be mono- or poly-substituted by fluorine.

12. The display according to any one of claims 9 to 11,
wherein component B contains one or more compounds selected
from the group consisting of compounds of formulae II26 and
II27:

Image



58

in which C r H2r+1 is a straight-chain alkyl group having up to
7 C atoms and the thick dots have the meaning defined in
claim 9.

13. The display according to any one of claims 9 to 12,
wherein component B contains one or more compounds selected
from the group consisting of compounds of formulae III and IV:

Image

in which R1 and R2 have the meanings defined in claim 5, and
the thick dots have the meaning defined in claim 9.

14. The display according to any one of claims 9 to 13,
wherein component B contains one or more compounds selected
from the group consisting of compounds of formulae XII to XIV:

Image

in which R1 and R2 have the meanings defined in claim 5, and
the thick dots have the meaning defined in claim 9.

15. The display according to any one of claims 1 to 13,
wherein the liquid crystal mixture additionally contains one or
more compounds selected from the group consisting of compounds
of formulae V and VI:


59

Image

in which R1 and R2 have the meanings defined in claim 5.

16. The display according to claim 3 or 4, wherein
component C contains one or more compounds selected from the
group consisting of compounds of the formulae VII to XI:

Image

in which R1 and R2 have the meanings defined in claim 5, the
thick dots have the meaning defined in claim 9, and s is 0
or 1.

17. The nematic liquid crystal mixture of the composition
defined in any one of claims 1 to 16.

Description

Note: Descriptions are shown in the official language in which they were submitted.



2035~6~
- 1 -
Supertwist liquid crystal display
The invention relates to supertwist liquid


crystal displays (SLD) having very short switching times


and good steepness and angle dependence, and also to the


novel nematic liquid crystal mixtures used therein.


SLD according to the preamble are known, for


example from EP 0,131,216 B1; DE 3,423,993 A1; EP


0,098,070 A2; M. Schadt and F. Leenhouts, 17th Freiburger


Arbeitstagung Fliissigkristalle (Freiburg Working Meeting


on Liquid Crystals] (8.-10.04.87); K. Kawasaki et al.,


SID 87 Digest 391 (20.6); M. Schadt and F. Leenhouts,
SID


87 Digest 372 (20.1); R. Katoh et al., Japanese Journal


of Applied Physics, volume 26, No. 11, L 1784-L 1786


(1987); F. Leenhouts et al., Appl. Phys. Lett. 50 (21),


1468 (1987); H.A. van Sprang and H.G. Koopman, J. Appl.


Phys. 62 (5), 1734 (1987); T.J. Scheffer and J. Nehring,


Appl. Phys. Lett. 45 (10), 1021 (1984), M. Schadt and
F.


Leenhouts, Appl. Phys. Lett. 50 (5), 236 (1987) and E.P.


Raynes, Mol. Cryst. Liq. Cryst. Letters volume 4 (1),


pages 1-8 (1986). The term SLD here comprises any more


highly twisted display element with an amount of twist


angle between 100 and 600, such as, for example, the


display elements according to Waters et al. (C. M. Waters


( et al., Proc. Soc. Inf. Disp. (New York) (1985) (3rd


Intern. Display Conference, Robe, Japan), the STN-LCD


(German Offenlegungsschrift 3,503,259), SBE-LCD


(T.J. Scheffer and J. Nehring, Appl. Phys. Lett. 45


(1984) 1021), OMI-LCD (M. Schadt and F. Leenhouts, Appl.


Phys. Lett. 50 (1987), 236, DST-LCD (European Published


Application 0,246,842) or BW-STN-LCD (R. Kawasaki et al.,


SID 87 Digest 391 (20.6)).


' Compared with standard twisted nematic displays,


SLD of this type are distinguished by substantially


better steepness of the electro-optical characteristic


and thus associated better contrast values and by a


substantially smaller angle dependence of the contrast.
SLD with very short switching times are here of par-


2U3~8fi?
- 2 -
ticular interest, especially also at relatively low
temperatures. To achieve short switching times, the
viscosities of the liquid crystal mixtures have hitherto
been optimized with the use of, in most cases, monotropic
additives having a relatively high vapour pressure.
However, the switching times achieved were not adequate
for some applications.
To achieve a steep electro-optical characteris
tic, the liquid crystal mixtures should have relatively
high wide (sic) values for K3/K1 and relatively small
values for oE/E1.
Beyond the optimization of the contrast and
switching times, mixtures of this type have to meet
further important demands:
1. a wide d/p window
2. a high chemical fatigue stability
3. a high electrical resistance
4. a low frequency dependence of the threshold voltage.
The parameter combinations achieved are not yet
nearly sufficient, in particular for high-multiplex STN
(1/400). In part, this is to be ascribed to the fact that
the various demands are affected in opposite directions
by material parameters.
There is thus still a great demand for SLD which
have very short switching times coupled with, at the same
n time, a wide range of working temperatures, high steep
ness of the characteristic, good angle dependence of the
contrast and low threshold voltage and which meet the
demands given above.
The invention is based on the object of providing
SLD which show the above-indicated disadvantages only to
a smaller extent or not at all and, at the same time,
have very short switching times.
It has now been found that this object can be
achieved if the nematic liquid crystal mixture
a) is based on component A containing one or more
compounds seleted from group A comprising compounds
of the formulae IIa to IIk~c

9ep-29-00 05:3fipm From-SbB/FbCo, +2328440 T-4fi3 P 05
F-15T
26474-221
3
R A~ As X B
R A~ CH~C~ A= X
R ~ v Az A~ ;~ ~Ic
R Al Az ~t A~ X
R ~ CFi CHZ Ai C~z A~ X
R A1 CH~fiz A= A3 X
R A~ C=C AI X
R A~ C-C A
R Ai A= C = C A3 X
R al ~~h A= C=C A3 X
R A~ C = C ~ y A~ X
in which R is n-alkyl or n-alkenyl having up to 9 C m oms,
1' Y is cyano, -NCS, F, C1, -CF3, -CHF2, -OCF3, -OCHFz,
-OCFzCF~H or -OC~F;, and the rings Al, A2 and A3 each
independently of one another are 1,4-phenylene~2- or 3-fluoro-
1,4-phenylene or tra-a-1,4-cyclohexylene, or one of the rings
Al, A~ and A3 can also be 1,4-cyclohexenylene, 2,3-difluoro-1,4-
20 phenylene, pyridine-2,5-diyl or pyrimidine-2,5-diyl,
(b) contains 0-40~ by weight of a liquid-crystalline component
B, consisting of one or more compounds having a dielectric
anisotropy of -1.S to *1.5, of the general formula I
CA 02035862 2000-09-29

CA 02035862 2002-07-30
26474-221
4
R1 A1 Z1- ~ - A2 ZZ-~-m A3 R2 I
in which Rl and Rz each independently of one another
are n-alkyl, n-alkoxy, n-oxaalkyl, w-fluoroalkyl or n-alkenyl
having up to 9 C atoms, the rings Al, A2 and A3 each
independently of one another are 1,4-phenylene, 2- or 3-fluoro-
1,4-phenylene, trans-1,4-cyclohexylene or 1,4-cyclohexenylene,
Z1 and Z2 each independently of one another are
-CHZCH2-, -C--_C- or a single bond, and m is 0, 1 or 2,
c) contains 0 to 20% by weight of a liquid-
crystalline component C consisting of one or more compounds
having a dielectric anistropy below -1.5, and
d) contains an optically active component D in such a
quantity that the ratio of cell thickness (spacing of the
plane-parallel carrier plates) to the natural pitch of the
chiral nematic liquid crystal mixture is approximately 0.2 to
1.7 and in particular approximately 0.2 to 1.3,
the nematic liquid crystal mixture has a nematic
phase range of at least 60°C, a viscosity of not more than 35
mPa.s and a dielectric anisotropy of at least +1, the
dielectric anisotropies of the compounds and the parameters
relating to the nematic liquid crystal mixture referring to a
temperature of 20°C.
According to one aspect of the present invention,
there is provided supertwist liquid crystal display with two
plane-parallel carrier plates which, with a frame, form a cell,
a nematic liquid crystal mixture, located in the
cell, having a positive dielecric anisotropy,

CA 02035862 2002-07-30
264?4-221
4a
a tilt angle of about 1 degree to 30 degrees between
the longitudinal axis of the molecules at the surface of the
on the insides of the carrier plates,
carrier plates and the carrier plates, and
a twist angle of the liquid crystal mixture in the
cell from orientation layer to orientation layer of an amount
between 100 and 600°,
IIk:
component A containing one or more compounds selected
from group A consisting of compounds of the formulae IIa to
electrode layers with superposed orientation layers
wherein the nematic liquid crystal mixture comprises:
R A1 Az X IIa
R A1 CHZCH2 AZ X Iib
R A1 A2 A3 X IIc
R A1 AZ CH2CHz A3 X IId
R AZ CH2CH2 AZ CHZCH2 A3 X IIe
R A1 CH2CH2 A2 A3 X IIf
R A1 C=C A2 X IIg

CA 02035862 2002-07-30
26474-221
4b
R A1 C=C A2 A3 X zIh
R A1 AZ C=C A3 X IIi
R A1 CH2CH2 AZ C=C A3 X IIj
R A1 C=C AZ CHZCHZ A3 X zIk
in which R is n-alkyl or n-alkenyl having up to 9 C atoms,
X is F, C1, -CF3, -CHFz, -OCF3, or -OCHF2, and the
rings Al, A2 and A3 each independently of one another are
1,4-phenylene, 2- or 3-fluoro-1,4-phenylene or traps-1,4-
cyclohexylene, or one of the rings Al, A2 and A3 is
1,4-cyclohexenylene, 2,3-difluoro-1,4-phenylene, pyridine-2,5-
diyl or pyrimidine-2,5-diyl, and
an optically active component D in such a quantity
that the ratio of cell thickness (spacing of the plane-parallel
carrier plates) to the natural pitch of the chiral nematic
liquid crystal mixture is about 0.2 to 1.3,
wherein the nematic liquid crystal mixture has a
nematic phase range of at least 60°C, a viscosity of not more
than 35 mPa.s and a dielectric anisotropy of at least +1, the
dielectric anisotropies of the compounds and the parameters
relating to the nematic liquid crystal mixture referring to a
temperature of 20°C.
The invention thus relates to an SLD with

CA 02035862 2002-07-30
26474-221
4c
two plane-parallel carrier plates which, with a
frame, form a cell,
a nematic liquid crystal mixture, located in the
cell, having a positive dielectric anisotropy,
electrode layers with superposed orientation layers
on the insides of the carrier plates,
a tilt angle of about 1 degree to 30 degrees between
the longitudinal axis of the molecules at the



203586?
-5-
surface of the carrier plates and the carrier
plates, and
a twist angle of the liquid crystal mixture in the
cell from orientation layer to orientation layer of
an absolute valve between 100 and 600°, charac
terized in that the nematic liquid crystal mixture
a) is based on component A containing one or more
compounds selected from croup A comprising compounds
of the formulae IIa to IIk:
R-~ A1 A2 -X IIa


R- Al\~ CH2 CH2 -~ -X I I
- b


R- ~ - A2'\ - ~ -X I I
c


R- A1 ~-CH2CH2- A3 -X IId
-


R- A2~- CH2CH2-~ -CH2CH2- A3\ -X IIe


R- Al CH2CH2- A2 - A3 -X IIf
-


R1 - A1 -C=C- A -X IIg


R1 - A1 -C=C- A2 A -X IIh


I.
R1 - A1 - A2 -C--__C- A'3 -X IIi


Rl - A1 -CH2CH2- A2 -C=C- A3 -X IIj


R1 - A1 -C-C- A2 -CH2CH2- A3 -X IIk


~ in which R is n-alkyl or n-alkenyl having up to 9
C atoms,
X is cyano, -NCS, F, C1, -CF3, -CHF2,
-OCF3, -OCHF2, -OCF2CFZH or -OCZFS, and
the rings Al, A2 .and A3 each independently
of one another are 1,4-phenylene, 2- or



203586?
- 6 -
3-fluoro-1,4-phenylene or traps-1,4
cyclohexylene, or one of the rings A1, A2
and A3 can also be 1,4-cyclohexenylene,
2,3-difluoro-1,4-phenylene, pyridine-2,5
diyl or pyrimidine-2,5-diyl,
b) contains 0-40~ by weight of a liquid-crystalline
component B, consisting of one or more compounds
having a dielectric anisotropy from -1.5 to +1.5, of
the general formula I
R1- .~-Z1_f-<~,~ -Z2-~m-~~ -R2 I
in which Rl and R2 each independently of one another


are n-alkyl, n-alkoxy, n-oxaalkyl,


w-fluoroalkyl or n-alkenyl having up to 9


C atoms , the rings Al, AZ and A3 each


independently of one another are


1,4-phenylene, 2- or 3-fluoro-1,4-pheny-


lene, traps-1,4-cyclohexylene or 1,4-


cyclohexenylene,


Z1 and ZZ each independently of one another


are -CHZCH2-, -C~C- or a single bond, and


m is 0, 1 or 2,


c) contains 0-20% by weight of a liquid-crystalline


component C consisting of one or more compounds


f having a dielectric anisotropy below -1.5, and


d) contains an optically active component D in such a


quantity that the ratio of cell thickness (spacing


of the plane-parallel carrier plates) to the natural


pitch of the chiral nematic liquid crystal mixture


is about 0.2 to 1.7, and in particular 0.2 to 1.3,


and


in that the nematic liquid crystal mixture has a


nematic phase range of at least 60C, a viscosity of


not more than 35 mPa.s and a dielectric anisotropy


of at least +1, the dielectric anisotropies of the


compounds and the parameters relating to the nematic


liquid crystal mixture referring to a temperature


of 20C.



CA 02035862 2002-07-30
26474-221
7
The invention also relates to corresponding liquid
crystal mixtures for use in SLD.
The individual compounds of, for example, the
formulae I and IIa to TIk or also other compounds which can be
used in the SLD according to the invention are either known or
can be prepared analogously to the known compounds.
Preferred liquid crystal mixtures contain
a) at least one component selected from group B4 comprising
compounds of the formulae AI to AVI:
R1 0 CH2CH2 0 R2 AI
R1 0 CHZCH2 RZ All
R1 CHZCHZ 0 RZ AIII
R1 CHZCHZ 0 Rz AIV
R1 0 RZ AV
2o Ri 0 Rz
AVI
in which R1 and R2 each independently of one another
are R and

CA 02035862 2002-07-30
26474-221
7a
R is alkyl having 1-12 C atoms, and in which one or
two non-adjacent CH2 groups can also be replaced by -O-,
-CH-CH-, -CO-, -O-CO- or -CO-0-, and wherein the thick dot
indicates that the cyclohexane ring is tran-substituted at that
spot. This is a conventional form of notation and the notation
is used herein consistently with this meaning,
b) and/or at least one component selected from group B1
comprising the compounds of the formulae BI to BIV:
0
R1 ~---Z Z RZ B I
0
0
R1 ZZ ~-R2 BII
0
R1 ZZ RZ BI II
R1 g R2 BIV



203586
_8_
in which R1 and RZ each independently of one another
have the meaning given for R,
ZZ is -CHZCHZ-, -CO-O-, -0-CO- or a single bond, and
is- B ~,_ ~_, _ ~~~._or ~_
and/or at least one component selected from group B2
comprising the compounds of the formulae BV to BVII:
R1- \ H~ '~-Z~- ~ COO-Q BV
Y
R1 H \'~-/ H ~~-CH2CH2- O '>-X BVI
-_
Y
__
R1- ~ H ~y-CH2CH2- H '-- ~~ -X BVI Z
,,
in which R1 has the meaning given for R,
Z° is -CH2CH2- or a single bond and
/Y
Q is -~ -CnH2n+1, ~-R or -~y -X
n being 1 to 9, X being CN or F and Y being H or F,
t and/or at least one component selected from croup B3
compris ing the compounds o f the formulae BVI I I and BIX
N ~
R1-~l-C O ~-R2 BVIII
N --
N
R1-~~-~~-R2 BIX
in which R1 and R2 each independently of one another
have the meaning given for R, and
,, , _~/ _, _
is -~ J -
or
_ ~, _


~035~62
g _
Particularly preferred compounds of the formula
BIII are those of the following partial formulae:
-.,
R1_,~ ~...~ '~R2
R ' CH2CH2-~ ,e..R2
in which
R1 is CH3- ( CH2 ) n-0-, CH3- ( CHZ ) t-, trans-H- ( CH2 ) r
CH=CH- ( CHZCHZ ) g-CH20- or trans-H- ( CH2 ) t )
CH=CH- ( CHzCH2 ) g-,
RZ is CH3- ( CH2 ) t-,
n is 1, 2, 3 or 4,
r is 0, 1, 2 or 3,
' s is 0 or 1 and
t is 1, 2, 3 or 4.
Those compounds of the partial formula
R1- COO-( r-R2
in which R1 and R2 have the meanings given above, are also
preferred.
The proportion of the compounds of the formula
BIII of the above-indicated partial formulae is prefer-
ably about 5% to 45%, especially preferably about 10% to
t 35%. Particularly preferred compounds of the formula BIV
are those-of the following partial formula:
R1_ ~~_~'~R2
in which
R1 i S CH3- ( CH2 ) n-O- Or
trans-H- ( CHZ ) r-CH=CH- ( CHZCH2 ) 5-CH20- and R2 is
CH3- ( CHZ ) t-,
' n being 1, 2, 3 or 4,
r being 0, 1, 2 or 3,
s being 0 or 1 and
t being 1, 2, 3 or 4.
The proportion of these compounds or of the
compounds of the formula BIV is preferably about 5% to



_. ~~3~~~~
- 10 -
40%, especially preferably about 10% to 35%.
Preferably, the mixtures contain compounds of the
formula III, in particular those of the partial formula
R1 ~~ ~/~R2
In a particularly preferred embodiment, the
mixtures simultaneously contain compounds of the formulae
BIII and BIV, the total proportion of components of group
B1 remaining unchanged.
If compounds of the formulae BI and/or BIII are
present, R1 and R2 preferably each independently of one
another are n-alkyl having 1 to 7 C atoms or
(traps)-n-alkenyl having 3 to 7 C atoms. Z2 is preferably
a single bond. BI is particularly preferred.
Those mixtures according to the invention are
also preferred which contain one or more compounds of the
formula BIV, in which
is - ~~ - , - ~> - or - ~~~ - and R1 and RZ have
i ,
one of the preferred meanings given above, especially
preferably n-alkyl having 1 to 7 C atoms.
In any case, the total proportion of components
of group B1 remains unchanged.
The proportion of compounds of group B2 is
preferably about 5% to 45%, especially preferably 5% to
20%. The proportion (preferred ranges) of BV to BVII is
as follows:
BV about 5% to 30%, preferably about 5% to 15%
total of BVI and BVII: about 5% to 25%, preferably about
10% to 20~.
Preferred compounds of group B2 are indicated
below:
a




_ 11 - 20358?
,.
R1- ~ H \~~-.Z~_ ~~~COO- ~~~C H BV1
- n 2a+1
R1-~y-Z~-~~COO- ~~-R BV2
i .~,
Y
R1- H \~Z~- ti tCOO-~> -F BV3
v -/
Y
--,
R1-~ H '~- H CH CH - ~-F BVI1
2 2 ~/
Y
R1 H ~s-CH CH / H \~- O ~ -F BVI I1
~' 2 2 ~_-..
R1 is preferably n-alkyl having 1 to 7 C atoms or
(trans)-n-alkenyl having 3 to 7 C atoms. Z° is preferably
a single bond. R preferably has the preferred meaning
given above for R1 or is fluorine. Y is preferably
fluorine.
Preferably, the mixtures according to the inven-
tion contain one or more compounds selected from the
group comprising BV3, BVI1 and BVII1 in a total
proportion of about 5 to 35$.
In a particularly preferred embodiment, the
mixtures according to the invention contain, in addition
to BV3, BVI1, BVII1 and BV2 (R = A), further terminally
fluorinated compounds selected, for example, from the
group comprising: ~ Y
R1- ( H ~~COO- a O >-F
i
/Y
R1-~-~' )-~~-F
x
and/or polar heterocycles selee~ted from the group com-
prising



20356?
- 12 -
R1- ~/ O N_f'_ .~~ O )_~'- ~ O vYXo
,, N v ;
~. .
- N Y
~1- O ) -\ 0 ) -CH2CH2- 0 ~, _Xo
N '-,
1 ~N ~~Y
t? ~. ~ _ ~~ p , ~~~ _ X o
~- N ~ ~ Y
rZl-.' p ~_,~~,-~,~_Xo
...,. ~ ~/
in which R1 is preferably n-alkyl having 1 to 7 C atoms or
(trans)-n-alkenyl having 3 to 7 C atoms, x is 1 or 2, x°
is F, C1, CF3, -OCF3 or -OCHFZ, y is 0 or 1 and Y is H
or F.
The total proportion of all the terminally
fluorinated compounds is preferably about 5% to 65%,
especially about 15% to 40%.
The proportion of the compounds from group B3 is
preferably about 5% to 30%, especially preferably about
10% to 20%. R1 is preferably n-alkyl or n-alkoxy each
having 1 to 9 C atoms. R2 is preferably n-alkyl having 1
to 9 C atoms. However, analogous compounds with alkenyl
or alkenyloxy groups can also be used. Compounds of the
formula BVIII are preferred.
' -~ - is preferably 1,4-phenylene.
The mixtures according to the invention contain
compounds from at least one of groups B1, B2 and B3.
Preferably, they contain one or more compounds from group
B1 and one or more compounds from group B2 and/or B3.
Isothiocyanates, for example of the formula

Sap-29-00 05:36pm From-Sd,B/FaCo, +2328440 T-463 P 06 F-15T
2E~_'14-221
13
y
~NCS in which R1 is n-alkyl having 1 to 7 C
aLOms or n-alkenyl having 3 to 7 C atoms, are also preferred.
In a particularly preferred embodiment, the mixtures
«ccording to the inven:.ion contain preferably about 5~s to 20%
of one or more compounds having a dielectric anisotropy below
-1.5 (component D). Compounds of this type are known, for
example derivatives of 2,3-cicyanohydroquinor~e or cyclohexane
derivatives having the structural element
CN
---~~~~ according to German Of fenlegungssc:~rifc
'y
~.0 3,231,707 or 3,407,013.
Preferably, however, compounds having the structural
element 2,3-difluoro-1,4-phenylene are selected, for example
compounds according ~.o German Offenlegungsschriften 3,807,801,
;,807,861, 3,8C7,863, 3,807,864 or 3,907,908. Particularly
preferred are tolans having the structural element according Lo
ynternational PaLenL Publicac;:on W088/07514, in particular
those of the formu:~ae
F~/F
R ; -~ ~,,%-C ~C -~~ ,i--0 R2
F F
. /
R~ H ~~ Z~ ~ ACC~ ~OR2
,~-- ~ ,,
in which Rl and RZ each independently of one another are
preferably n-alkyl having 1 to 7 C aLOms or n-alkenyl having 3
to 7 C atoms and Z° is -C~:2CH2- or a single bond, and
F"F
phenylpyrimidine of t~:e formul ~a
R~~~~ ~ ~R2
~~ N
corresponding to German. Offenlegungsschrift 3,807,871.
CA 02035862 2000-09-29


Sep-29-00 05:36pm From-S&B/F&Co, +2329440 T-463 P O7 F-157
254'14-221
13a
In a particularly preferred embodiment, the mixtures
contain about 5% to 35%, especially preferably about 10% to
20a, of liquid-crystalline tolan compounds.
CA 02035862 2000-09-29




- 14 - 2~3~~~ s~
As a result, it is possible to use smaller cell thick-
nesses (about 5-6 ~sm), whereby the switching times are
markedly shortened. Particularly preferred tolanes are
shown below:
R1 _( p _C=C-Sz
_ ~~
R1 _ ~~-Z~ _ ~~, _C=C-Q
Rl is preferably n-alkyl or n-alkoxy having 1 to 7
C


atoms,


Z is -CHZCH2- a single nd,
or bo


--. ~ F
-
O
R


Q is -~~ -X or -~ ;-X~ ,
~ i
~'-
'


X being F, C1
or OCF3,


R2 being n-alkyl or n-alkoxy each having 1 to 7 C atoms


or n-alkenyl or n-alkenyloxy each having 3 to 7 C
atoms.
Further particularly preferred embodiments are
given below:
- component A contains compounds of the formulae IIa
to I I f , in which X is cyano , and compounds o f the
formulae IIa to IIf, in which X is -NCS, F, C1, -CF3,
-CHF2, -OCF3, -OCHFZ, -OCF2CF2H or -OC2F5, and the
proportion of the cyano compounds in component A is
0 to 50$ by weight,
- component A contains one or more compounds of the
formulae IIal-IIa3 and IIcl-IIc8
R_/'~_ ~~~-X Ilal
F
R-~ ~- ~ O -X IIa2
F
I I a3
R- ~ - O -X
R-, O -; O _<\'~-X IIcl



.a 2035862
- 15 -
F


i
R ~ ~ ~-( O ~-X


I Ic2
~
i


F
_ ~ IIc3
---_j
R ~~- (~ O /)- ~~-X
F


__


R I I c 4
Ji ~
~
~
X


..
.-- IcS
F
F
_ _, _
R-c, O~'-C O -%. O~-X I
~


/ F ,
,..
~,


.-
F
i-'
R-(/ O\
~
~


-(\ IIc6
- O
-X


~ F F


~
\


R_~ I Ic7
_ O '~- ~
)_X


F --~F ~F
R
~~
~
i
~


-t IIc8
-<
O
-
-X
J , ~~


-


in which R is n-alkyl, n-alkoxy or n-alkenyl having


1-9 C atoms and X is F, C1 or OCF3.


Component A contains at least one compound of the


formulae IIdl-IIdS


F
R- ~-~ -CH2CH2- O -X I Id5
i
~F F .
in which R is CaH~+1 or CnH~,+1 -~. with n = 1-10
and X is F, C1 or OCF3 and very especially F.
- Component A contains no compounds of the formulae
IIa to IIf, in which X is cyano,
- Component A contains one or more compounds of the
formula
R- ~ N-~~ -Z- O-F
N
R - O ,-CH2CH2 O ~-X IIdl
.-.~ ~ F
R- ~-~ -CH2CH2- O~ -X I Id2
R- O ~,-~ -CH2GH2-~~-X IId3
F
R- ~~~ - O -CH2 CH2 - ~ -X I I d4

Sep-29-00 05:36pm From-Sd,B/F~Co, X2328440 T-463 P 08 F-157
26474-221
16
in which
R is n-alkyl, n-alkoxy or n-alkenyl having 1-9 C
atoms,
2 is -CH2CH~- or a single bond and
A j~-- is 1,4-phenylene, 2- or 3-fluoro-1,4-phenylene or
1,4-cyclohexylene.
-X is F, C1, CF3, -OCF3, OCHF~ or CHF2, component B
conr,ains one cr more compounds selected from the group
comprising II1 to II7:
II1
1 o R? ~~ ~(~ RZ
II2
'', ~'
R --rt H ~-C H 2 C H Z ~Or 2 I 3
U
R~ w ~\ ~~ RZ II4
R~~ H \ R2 II5
~W.J '~,
n~
R~~~~r--~ H ~--R2 _ II6
R'---~ H \~ C H 2 C H 2 H \'~ R 2 I I 7
CA 02035862 2000-09-29

8ep-29-00 05:36pm From-Sd8/FbCo, +2328440 T-d63 P 09 F-15T
26474-221
17
in which R1 arid R' each independently of one another are n-
alkyl, n-alkoxy, n-oxalkyl, r~-fluoro«lkyl or n-alkenyl having
up to 9 C atoms, the rings A1, Az and A~ each independently oz
one another are 1,4-phenylene, 2- or 3-fluoro-1,4-phenylene,
traps-1,4-cyclohexylene or 1,4-cyclohexenylene, Z1 and ZZ each
independently of one another are -CHICHI-, -C--__C- or a single
bond, and m is 0, 1 or 2.
Component B additionally contains one or mare
compounds selected from the group comprising II8 to II20:
1 Q R, H ~ H 6:=
8 R=
IT10
Ri H ~ R:
D11
R~ 0 0 o RI
al:
a' H a~~,
ass
R' H ~CZi7 ~ Ra
Bts
R' H 8 ~ Ri
ms
R~ H Qt~h H ~ Rz
X16
R' H H Qi~ ~ g~
a17
R H g
CA 02035862 2000-09-29

Sep-29-00 05:36pm From-S&B/F&Co, +2326440 T-463 P 10 F-157
26474-221
is
ala
~


R~ x x R


a19
~


Ri rZ ' Rx
8


~0.


R~ H ~ l Ra


'..r J


in which R1 and RZ each independently of one another are n-
alkyl, n-alkoxy, n-oxaalkyl, w-fluoroalkyl or n-alkenyl having
up to 9 C atoms, the rings A1, A2 and A' each independently of
l0 one another are 1,4-phenylene, 2- or 3-fluoro-1,4-phenylene,
traps-1,4-cyclohexylene or 1,4-cyclohexenylene, Z1 and ZZ each
independently of one another are -CHZCH~-, -C=C- or a single
bond, and m iq 0, 1 or 2 and the 1,4-phenylene groups in II8 to
II17 each independently of one another can also be mono- or
poly-substituted by fluoryne.
Component B additionally contains one or more
~ompouncs selected from the group comprising II21 to II25:
R' \ H \~ ,,'~ '' .' O'~~ H ~~ R 2 I I21
s
~/'~ v
R~~~--CH2CH2~~) ~~ '' \~ R2 TI22
y '.
R ~ "~ H ~ H ''' ~~ H R ~
', . II23
i~ ~~ v
R'-- \ H ~r--~\ H C H 2 C H z ,~~ H R 2 I I 2 4
,~ '
CA 02035862 2000-09-29

8ep-29-~0 05:3Tpm From-S~B/FaCo, +2328440 T-463 P 11/26 F-15T
2674-221
19
R'---c,~,y H \ ~ R 2
/ \ 'v ~ II25
in which Rl and R~ have the meanings given in claim 1 and the
1,4-phenylene groups in II21 to II25 each independently of one
another can also be mono- or poly-substituted by fluorine.
Component B contains one or mare compounds selected
from the group cornprising II26 and II27:
C rH2r+~~~\ ,\ H ~CH2-F II26
y
~ rH2r+~-"r H ,\ H ;-CH2CH2-F II27
~.n which CrHar+~ is a straight-chain alkyl group having up to 7 C
atom9.
The liquid crystal mixture additionally contains,
apart from components A, B and C, one or more compounds
selected from the group comprising III and IV:
R'---( H ~~ H '~ p R 2 W I
R \ H ,~~.--CH20R2
~_. / I V
in which R1 and R' each independently of one another are n-
a:.kyl, n-alkoxy, n-oxaalkyl, w-fluoroalkyl or n-alkenyl having
up to 9 C atoms, the rings Al, Az and A~ each independently of
one another are 1,4-phenylene, 2- or 3-fluoro-1,~-phenylene,
traps-1,4-cyclohexylene or 1,4-cyclohexenylene, Z1 and Z~ each
independently of one another are -Ci32CH~-, -C---C- or a single
bond, and m is 0, 1 or 2.
CA 02035862 2000-09-29

Sep-29-00 05:3Tpm From-S&B/FaCo, *2328440 T-463 P 12/26 F-15T
26474-221
The liquid crystal mixture additionally contains,
apart from components A, B and C, one or more compounds
selected from the group comprising V and VI:
N ~,
R--(~,r-~~ ~-R2 v
~N
R~~ ~ /~ ~R2
~'~-i VI
.n which i~c= and R2 each independently of one another are n-
alkyl, n-alkoxy, n-oxaal?~yl, c~-fluoroalkyl or n-alkenyl having
up to 9 C atoms, the rings Al, A' and A' each independently of
10 one another are 1,4-phenylene, 2- or 3-fluoro-1,4-phenylene,
traps-1,4-cyclohexylene or 1,4-cyclohexenylene, Z1 and 22 each
independently of one another are -CH2CHz-, -C._-C- or a sino_le
bond, and m is 0, 1 or 2. '
Component C contains one or more compounds selected
15 from the group comprising 'till to XI:
F F
VII
~~~-S CN2CH2 ,~R
~/ ~/,
F. F
R? ~~~- S ~~~R2 VIII
F F
2o R-----~:--(CH2CH2)s ~\\~' z
\~ ~ ~~ \~R IX
F F
R~~~CHzCH2~'-.-(CH2CH ~ 2
\~ z )s ,\~ R X
F F
t
CH2CH2 ' ~-(CH2CH2)s H R2
XI
CA 02035862 2000-09-29

Sep-29-70 05:37pm From-S&B/F&Cc, +2328440 T-463 P 13/26 F-157
26474-221
20a
::n which R1 and R2 each independently of one another are n-
alkyl, n-alkoxy, n-oxaalkyl, c~-fluoroalkyl or n-alltenyl having
up to 9 C atoms, the rings Al, Az and A3 each independently of
one another are 1,4-phenylene, 2- or 3-fluoro-1,4-phenylene,
trans-1,4-cyclohexylene or 1,4-cyclohexenylene, 21 and Z~ each
independently of one another are -CH2CHz-, -C=C- or a single
bond, and m is 0, 1 or 2 and S (sic) is 0 or 1.
Component H contains one or more compounds selected
from the group comprising XI. to XIV;
R~ \(~~C~C ~ R2 XII
R y\,. ~---. 2
\~~C C ~y R XI I I
/~~
R~ H r--CH2CHZ .~~ j--C-C~;--R2 XIV
v \'/
vn which R1 and R~ each independently of one another are n-
alkyl, n-alkoxy, n-oxaal~:yl, ca-fluoroalkyl or n-alkenyl having
up Lo 9 C atoms, the rings A1, A~ and A3 each independently of
one another are 1,4-phenylene, 2- or 3-fluoro-1,4-phenylene,
trans-1,4-cyclohexylene or 1,4-cyclohexenylene, Zl and Zz each
~~ndependently of one another are -CHzCH=-, -C=C- or a single
bend, and m is 0, 1 or 2.
Those mixtures are preferred which exclusively
contain compounds of the formulae IIa to IIh (group A) and
component C, i.e. no compounds of component B.
The preferred mixtures containing terminally
h alogenated compounds of the formulae IIa to IIk (X = F, C1,
-CF3, -CHF2, -OCF3 cr -OCHFz) shows (sic) particularly
advantageous parameter combinations and, at the same time, a
wide d/p window.
CA 02035862 2000-09-29

Sep-29-00 05:31pm From-S&B/F&Cc, +2328440 T-463 P.14/26 F-151
2674-221
20b
Liguid crystal mixtures according to the invention
whcse component A contains at least one compound of Lhe formula
Y
R~\, C-C ~yX
v
S in which
R i s -CnH~n,,l , -OCnH2n+1 i CnH2n+1
or CnFi2n,.l~~ CH2CH3,
n is an integer of I-15,
Y is H or F and
X is F, C1 or OCF3,
and/or contains a compound of the formulae IId2-IId5,
IIal-IIa3 and/or IIc1-IIcB, have advantageous values of the
threshold voltage vlo~ciao and of the flow viscosity r~ and are
diatinguis_rled by fairly high or high values of the optical
anisotropy. These mixtures are preferred.
For component D, a large number of chiral doping
substances, some of which are commercially obtainable, are
a~Tailable to those skilled in the art. The choice of these is
not critical per se.
The liquid crystal mixtures used in the SLD according
to the inven~l.ion are dielectrically positive with ~F z 1.
Liquid cry9tal mixtures with Ds _> 3 are particularly preferred,
and very particularly those with a~ ? 5.
The liquid crystal mixtures according to the
invention have advantageous values of the threshold
CA 02035862 2000-09-29



.~. zo3~~s~
- 21 -
voltage Vloioiao and of the flow viscosity n. If the value


of the optical path difference den is given, the value


.of the layer thickness d is determined by the optical


anisotropy en. Using i.a. liquid crystal mixtures accord-


s ing to the invention with a relatively high or high value


of the optical anisotropy is preferred, especially in the


case of relatively high or high values of don, since the


value of d can then be selected to be relatively small,


which brings about more advantageous values of the


switching times. However, those liquid crystal displays


according to the invention which contain liquid crystal


mixtures according to the invention having smaller values


of en are also characterized by advantageous values of



the switching times. The liquid crystal mixtures accord-


ing to the invention are characterized further by advan-


tageous values of the steepness of the electro-optical


characteristic and can be operated at high multiplex


rates. Moreover, the liquid crystal mixtures according to


the invention have high stability and advantageous values


of electrical resistance and of frequency dependence of


the threshold voltage. The liquid crystal displays


according to the invention have a wide range of working


temperatures and good angle dependence of the contrast.


The structure of the liquid crystal display


elements according to the invention from polarizers,


,' electrode base plates and electrodes with such a surface


treatment that the preferential orientation (director) of


the adjoining liquid crystal molecules from one electrode


to the other is in each case twisted usually by an amount


of 160 to 360 relative to one another, corresponds to


the type of construction which is conventional for such


display elements . The term co~entional type of construc-


tion is here used in a wide meaning and also comprises


all variations and modifications of the supertwist cell,


and in particular also matrix display elements and the


display elements containing additional magnets according


to German Offenlegungsschrift 2,748,738. The surface tilt


angles at the two carrier plates can be equal or dif-


ferent. Equal tilt angles are preferred.




2035~6a
- 22 -
However, an essential difference between the
display elements according to the invention and the
.hitherto conventional ones on the basis of the twisted
nematic cell resides in the choice of the liquid crystal
components of the liquid crystal layer.
The liquid crystal mixtures which can be used
according to the invention are prepared in a manner
conventional per se.
As a rule, the desired quantity of the components
used in a smaller amount is dissolved in the components
representing the main constituent, advantageously at an
elevated temperature. It is also possible to mix
solutions of the components in an organic solvent, for
example in acetone, chloroform or methanol, and, after
thorough mixing, to remove the solvent again, for example
- by distillation.
The dielectrics can also contain further addi
tives known to those skilled in the art and described in
the literature. For example, 0-15% of pleochroic dyes can
be added.
The examples which follow are intended to explain
the invention, without limiting it.
In the examples:
S-N is the smectic/nematic phase transition
temperature,
c.p. is the clearing point,
visc. is the viscosity (mPa.s),
Ton is the time from switching on until 90% of the
maximum contrast is reached, and
Tuff is the time from switching off until 10% of the
maximum contrast is reached.
The SLD is activated in multiplex operation
(multiplexing ratio 1:100, bias 1:11, operating voltage
18.5 volt).
Above and below, all temperatures are given in
°C. The percentage figures are percent by weight. The
values of the switching times and viscosities refer to
20°C. ~-.



203582
- 23 -
Example 1
An SLD of the STN type having the following
parameters:
twist angle 240°
tilt angle 5°
d/p 0.54
d.en 0.860,
containing a liquid crystal mixture having the following
parameters:
clearing point: 91°
en: 0.1254
eE: +8.1
viscosity (20°C): 16 mPa.s
and consisting of a base mixture of
18% of p-traps-4-propylcyclohexane-benzonitrile,
8% of traps-1-p-methoxyphenyl-4-propylcyclohexane,
5% of 2-p-fluorophenyl-5-propylpyrimidine,
5% of 2-p-trifluoromethoxyphenyl-5-pentylpyrimidine,
5% of 2-p-trifluoromethoxyphenyl-5-heptylpyrintidine,
- 9% of p-[traps-4-(traps-4-propylcyclohexyl)-cyclohexyl]
trifluoromethoxybenzene,
8% of p-[traps-4-(traps-4-pentylcyclohexyl)-cyclo-
hexyl]-trifluoromethoxybenzene,
8% of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-
hexyl]-2-(p-trifluoromethoxyphenyl)-ethane,
(~ 7% of 1-[traps-4-(traps-4-pentylcyclohexyl)-cyclo-
hexyl]-2-(p-trifluoromethoxyphenyl)-ethane,
5% of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-
hexyl]-2-(3,4-difluorophenyl)-ethane,
5% of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-
hexyl]-2-(p-fluorophenyl)-ethane,
7% of 4-trifluoromethoxy-4'-(traps-4-propylcyclohexyl)-
biphenyl,
3% of 4-(traps-4-propylcyclohexyl)-4'-methoxytolan,
3% of 4-(traps-4-propylcyclohexyl)-4'-ethoxytolan and
4% of 4-(traps-4-propylcyclohexyl)-4'-propoxytolan
and a chiral component (2-octyl p-(p-n-hexylbenzoyloxy)-
benzoate) shows the following switching timess 105 ms
( 1/16 D, 1/5 b) , 198 ms ( 1/240 D, 1/14 . 5 b) , Vla~o~za



203586?
- 24 -
2.31 volt, Vg0/0/20 2.51 volt and a o d/p (d/p window) of
0.21.
.Example 2
An SLD of the STN type having the following
parameters:


twist 240
angle


tilt _;~
angle 5


d/p 0.56


d.nn 0.85,


containing
a liquid
crystal
mixture
having
the
following


parameters:


clearing
point:
87


on; 0.1222


AE:
+8.5


viscosity
{20C):
16
mPa.s


' and
consisting
of
a base
mixture
of


18% of p-traps-4-prooylcyclohexane-benzonitrile,


8% of traps-1-p-methoxyphenyl-4-propylcyclohexane,


5% of 2-p-fluorophenyl-5-propylpyrimidine,


5% of 2-p-trifluoromethoxyphenyl-5-pentylpyrimidine,


5% of 2-p-trifluoromethoxyphenyl-5-heptylpyrimidine,


9% of p-[traps-4-(traps-4-propylcyclohexyl)-cyclo-


hexyl]-trifluoromethoxybenzene,


8% of p-[traps-4-(traps-4-pentylcyclohexyl)-cyclo-


hexyl]-trifluoromethoxybenzene,


8% of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-


hexyl]-2-(p-trifluoromethoxyphenyl)-ethane,


7% of 1-[traps-4-(traps-4-pentylcyclohexyl)-cyclo-


hexyl]-2-(p-trifluoromethoxyphenyl)-ethane,


5% of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-


hexyl]-2-(3,4-difluorophenyl)-ethane,


5% of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-


hexyl]-2-(p-fluorophenyl)-ethane,


7% of 4-trifluoromethoxy-4'-(traps-4-propylcyclohexyl)-


biphenyl,


5% of 4-(traps-4-propylcyclohexyl)-2',3'-difluoro-4'-


ethoxytolan and


5$ of 4-(traps-4-pentylcyloh~xyl)-2',3'-difluoro-4'-


ethoxytolan





203~~62
- 25 -
and a chiral component (2-octyl p-(p-n-hexylbenzoyloxy)-


benz oate) shows the following switching times:


114 ms (1/16 D, 1/5 b), 236 ms (1/240 D, 1/14.5 b), v10/o/20


2.35 volt, V9o~oizo 2.53 volt and a a d/p (d/p window)
of


0.20 .


Example
3


An SLD of the STN type containing a liquid


crys tal mixture having the following parameters:


clea ring point: 106


en: 0.1322


eE: +6.9


and consisting of a base mixture of


18% of p-traps-4-propylcyclohexane-benzonitrile,


8% of traps-1-p-methoxyphenyl-4-propylcyclohexane,


9% of p-[traps-4-(traps-4-propylcyclohexyl)-cyclo-


hexyl]-trifluoromethoxybenzene,


8% of p-[traps-4-(traps-4-pentylcyclohexyl)-cyclo-


hexyl]-trifluoromethoxybenzene,


8% of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-


hexyl]-2-(p-trifluoromethoxyphenyl)-ethane,


7% of 1-[traps-4-(traps-4-pentylcyclohexyl)-cyclo-


hexyl]-2-(p-trifluoromethoxyphenyl)-ethane,


7% of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-


hexyl]-2-(3,4-difluorophenyl)-ethane,


6% of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-


hexyl]-2-(p-fluorophenyl)-ethane,


7% of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-


hexyl]-2-(p-trifluoromethylphenyl)-ethane,


7% of 4-trifluoromethoxy-4'-(traps-4-propylcyclohexyl)-


biphenyl,


2% of 4-(traps-4-propylcyclohexyl)-4'-methoxytolan,


2% of 4-(traps-4-propylcyclohexyl)-4'-ethoxytolan,


3% of 4-(traps-4-propylcyclohexyl)-4'-propoxytolan,


4% of 4-methyl-4'-ethoxytolan and


4% of 4-ethyl-4'-methoxytolan


and a chiral component (2-octyl p-(p-n-hexylbenzoyloxy)-


benzoate)
shows
short
switching
times.


Example
4


An SLD of the STN type containing a liquid





- 26 - 203586
crystal mixture having the following parameters:
clearing point: 81°
on: 0.1130
0E: +6.5
and consisting of a base mixture of
20% of p-traps-4-propylcyclohexane-benzonitrile,
10% of traps-1-p-methoxyphenyl-4-propylcyclohexane,
5.6%of traps-1-p-trifluoromethoxyphenyl-4-propylcyclo-
hexane,
5.6%of traps-1-p-trifluoromethoxyphenyl-4-butylcyclo-
hexane,
5.6%of traps-1-p-trifluoromethoxyphenyl-4-pentylcyclo-
hexane,
7% of p-[traps-4-(traps-4-propylcyclohexyl)-cyclo-
hexyl]-trifluoromethoxybenzene,
6.3%of p-[traps-4-(traps-4-pentylcyclohexyl)-cyclo-
hexyl]-trifluoromethoxybenzene,
6.3%of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-
hexyl]-2-(p-trifluoromethoxyphenyl)-ethane,
5.6%of 1-[traps-4-(traps-4-pentylcyclohexyl)-cyclo-
hexyl]-2-(p-trifluoromethoxyphenyl)-ethane,
5.6%of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-
hexyl]-2-(3,4-difluorophenyl)-ethane,
5.6%of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-
hexyl]-2-(p-trifluoromethyl)-ethane,
7% of 4-trifluoromethoxy-4'-(traps-4-propylcyclohexyl)-
biphenyl,
3.5%of 4-(traps-4-propylcyclohexyl)-4'-methoxytolan,
2.8%of 4-(traps-4-propylcyclohexyl)-4'-ethoxytolan and
3.5%of 4-(traps-4-propylcyclohexyl)-4'-propoxytolan
and a chiral component (2-octyl p-(p-n-hexylbenzoyloxy)-
benzoate) shows short switching times.
Example 5
An SLD of the STN type, containing a liquid crystal
mixture having the following parameters:
clearing point: 73°
on; 0.1252
nE: ,. +8.7
and consisting of a base mixture of



.,. - 27 - ~03~~~~
20$ of p-traps-4-propylcyclohexane-benzonitrile,
10~ of traps-1-p-methoxyphenyl-4-propylcyclohexane,
5.6~of 2-p-fluorophenyl-5-propylpyrimidine,
5.6~of 2-p-fluorophenyl-5-pentylpyrimidine,
5.6$of 2-p-trifluoromethoxyphenyl-5-pentylpyrimidine,
5.6~of 2-p-trifluoromethoxyphenyl-5-heptylpyrimidine,
7$ of p-[traps-4-(traps-4-propylcyclohexyl)-cyclo-
hexyl]-trifluoromethoxybenzene,
6.3~of p-[traps-4-(traps-4-pentylcyclohexyl)-cyclo-
hexyl]-trifluoromethoxybenzene,
6.3~of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-
hexyl]-2-(p-trifluoromethoxyphenyl)-ethane,
5.6$of 1-[traps-4-(traps-4-pentylcyclohexyl)-cyclo-
hexyl]-2-(p-trifluoromethoxyphenyl)-ethane,
5.6~ of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-
hexyl]-2-(3,4-difluorophenyl)-ethane,
5.6~of 1-[traps-4-(traps-4-propylcyclohexyl)-cyclo-
hexyl]-2-(p-trifluoromethyl)-ethane,
3.5~of 4-(traps-4-propylcyclohexyl)-4'-methoxytolan,
3.5~af 4-(traps-4-propylcyclohexyl)-4'-ethoxytolan and
4.2~of 4-(traps-4-propylcyclohexyl)-4'-propoxytolan
and a chiral component (2-octyl p-(p-n-hexylbenzoyloxy)-
benzoate) shows short switching times.
In the following table, physical data of further
mixtures M1 to M41 according to the invention are given,
the composition of which is to be found after the table:
c . p . Vlo~o~zo on D a
89-263 M1 120 5.1 0.1267 1.09


89-220 M2 89 3.0 0.1173


89-172 M3 110 3.3 0.0905 2.3


89-83 M4 93 2.1 0.1049 5.0


89-70 M5 97 0.1057


89-25 M6 90 3.7 0.1159 1.6


89-15 M7 80 3.5 0.0922 1.7


89-470 M8 90


ZLI-4582 M9 98 2.5 0.1008 3.2


ZLI-4581 M10 94 2.2 ., 0.1006 4.1


ZLI-4580 M11 95 2.0 0.1050 5.2



v. 2035862


- 28 -


c ' p' Vio~oizoon


'89-438 M12 92 0.1044 5.7
89-374 M13 92 4.7 0.1132 1.2
89-348 M14 93 0.0704
89-337 M15 79 0.1174 1.6
89-425 M16 107 0.1213 5.0
89-254 M17 92
2.5
89-796 M18 91.2 .153 6.2
89-1081 M19 94 0.1242 8.0
90-205 M20 87 0.1250 6.4
90-442 M21 87 0.1435 g,6
89/1018 M22 85 2 0.1480
89/1020 M23 84 1.82 0.1458
I 89/1034 M24 86 1.94 0.1531
89/1036 M25 96 2.24 0.1645
89/1037 M26 95 2.18 0.1648
89-733 M27 80
89-789 0.1255 5
M28


90-81 M29 90 2.06 0.1403
11.1
90-499 M30 82 1.93 0.1427
90-502 M31 84 2.01 0.1401 10.3
90-515 M32 83 1.77 0.1405 12.3
90-602 M33 86 1.8 0.14
90-604 M34 81 2.0 0.137
90-605 M35 94 1.9 0.15
90-606 M36 80 1.8 0.14
90-607 M37 87 1.8 0.14
90-608 M38 80 1.8 0.14
ZLI-4720-100 M39 91 2.3 0.1299 6
90-609 M40 85 2.2 0.125
90/2008 M41 76 2.15 0.1115
90/370 M42 76 1.63 0.1345
90/371 M43 70
1.44 0.1065
90/373 M44 2.12 0.1678
90/409 M45 8 1.42 0.1306
90/414 M46 74 1.44 0.1136
90/416 M47 63 I:66 0.1617
90/411 M48 72 1.89 0.1306



2035862
- 29 -


W o~o~zo on


90/415 M49 78 2.07 0.1193
90/417 M50 g0
186 0.1609


90/2014 M51 71 1.70 0.1401 10.
5
90/2015 M52 76 1.91 0.1152 8.6
90/487 M53 g7 1.90 0.1401 11.4


.:.r"


w 203~~62
- 30 -
89-263 (M1) 89-220 (M2)
G-50CF2 30 % PYP-50CF3 18


PCH-53 11 % PYP-70CF3 18


I32 16 % PCH-301 13 o


I35 10 % CCH-303 13


BCH-32 9 % CH-35 4


CBC-33 4 % CH-43 4


CBC-53 4 % CH-45 4


CBC-55 4 % CBC-33 4


CBC-33F 4 % CBC-53 5


CBC-53F 5 % CBC-55 4


CBC-55F 3 % CBC-33F 4


CBC-53F 5


CBC-55F 4


89-172 (M3) 89-83 (M4)
CCP-30CF3 20 % PCH-3 14


CCP-50CF3 20 % PCH-SF 10


PCH-301 15 % PCH-7F 10


PCH-302 10 % PCH-50CF2 20


CCH-303 10 % ECCP-3F 6


O CCH-501 9 % ECCP-5F 6


CBC-33 3 % ECCP-33 5


CBC-53 4 % CBC-33 5


CBC-33F 3 % CBC-53 5


CBC-53F 3 % CBCt55 4


CBC-55F 3 % CBC-33F 5


CBC-53F 5


CBC-55F 5





m 203586 2
- 31 -
89-70 (MS) 89-25 (M6)
PCH-3 14 % PCH-5F 14 ,a


PCH-5F 14 % PCH-6F 13 ,,o


PCH-7F 14 % PCH-7F 14 a


PCH-SOCF2 10 % I32 16


ECCP-3F 6 % I35 10


ECCP-5F 6 % BCH-32 9


ECCP-33 5 % CBC-33 4


CBC-33 5 % CBC-53 4


CBC-53 5 % CBC-55 4


CBC-55 5 % CBC-33F 4


CBC-33F 5 % CBC-53F 5


CBC-53F 6 % CBC-55F 3


CBC-55F 5


89-15 (M7) 89-470 (M8)
PCH-30CF2 20 % PCH-3 18


PCH-50CF2 10 % PCH-5F 12


CCH-303 13 % PCH-6F 12


CCH-502 13 % PCH-7F 10


ECCP-31 4 % ECCP-3F.F 7


( ECCP-32 4 % ECCP-SF.F 7


ECCP-33 4 % ECCP-33 5


ECCP-35 4 % CBC-33 5


BCH-32 9 % CBC-53 5


BCH-52 9 % CBC-55 4


CBC-33F 4 % CBC-33F 5


CBC-53F 3 % CBC-53F 5


CBC-55F 3 % CBC-55F 5





203862
- 32 -
ZLI-4582 (M9) ZLI-4581 (M10)
PCH-3 7 o PCH-3 10


PCH-5F 12 o PCH-5F 18


PCH-6F 12 % PCH-6F 14
0


PCH-7F 10 % PCH-7F 10


ECCP-3F 7 % ECCP-3F 9


ECCP-5F 7 % ECCP-5F 7


PCH-53 8 % ECCP-33


ECCP-33 5 % CBC-33 5


CBC-33 5 % CBC-53 6


CBC-53 6 % CBC-55 5


CBC-55 5 % CBC-33F 5


'CBC-33F 5 % CBC-53F 6


CBC-53F 6 % CBC-55F 5


CBC-55F 5


LLI-4580 (M11) 89-438 (M12)
PCH-3 18 % PCH-3 18


PCH-5F 12 % PCH-5F 12


PCH-6F 12 % PCH-6F 12


PCH-7F 10 % PCH-7F 10


ECCP-3F 7 % ECCP-3CF3 7


ECCP-5F 7 % ECCP-5CF3 7


ECCP-33 5 % ECCP-33 5


CBC-33 5 % CBC-33 5


CBC-53 5 % CBC-53 5


CBC-55 4 % CBC-55 4


CBC-33F 5 % CBC-33F 5


CBC-53F 5 % CBC-53F 5


CBC-55F 5 % CBC-55F 5





203586
- 33 -
89-374 (M13) 89-348 (M14)
PCH-5F 15 % PCH-5F 10


PCH-7F 15 % PCH-6F 5


PCH-53 20 % PCH-7F 10


BCH-32 14 % ECCP-3CF3 10


BCH-52 11 % ECCP-5CF3 10


CBC-33 3 % CCP-30CF3 10


CBC-53 4 % CCP-30CF3 10


CBC-55 4 % CCP-50CF3 10


CBC-33F S % ECCP-30CF3 10



CBC-53F 6 % ECCP-50CF3 10


CBC-55F 3 % CBC-53F 5


89-227 (M15) 89-425 (M16)


EPCH-20CF3 20 % PCH-3 15


EPCF~-30CF3 5 % PCH-5F 12


EPCH-50CF3 5 % PCH-6F 12


PCH-53 11 % PCH-7F 10


I32 16 % ECCP-3F 6


I35 10 % ECCP-5F 6


BCH-32 9 % CPTP-301 3


CBC-33 4 % CPTP-302 3


CBC-53 4 % CPTP-303 3


CBC-55 4 % CBC-33 5


CBC-33F 4 % CBC-53 5


CBC-53F 5 % CBC-55 4


CBC-55F 3 % CBC-33F 5


CBC-53F 5


CBC-55F 5





2o3~ssz
- 34 -
3,9-254 (M1?) 89-796 (M18)
PCH-3 6 o PCH-3 15


PCH-Y 4 % PCH-4 10
0


CCP-30CF3 7.5 % PCH-301 16


CCP-50CF3 2.5 % PCH-302 10


PCH-302 15 % PTP-40F 23
0


PCH-304 13 % CBC-33F 4
0


PCH-402 8 % CBC-53F 5


PCH-501 9 % CBC-55F 4


PCH-502 5 % CBC-33 4


CP-33 5 % CBC-53 5


CP-35 5 % CBC-55 4


CP-43 5


CP-45 5


CBC-33 3
0


CBC-53 5


CBC-55 2


89-1081 (M19) 90-205 (M20)
PCH-3 16 % PCH-3 16


- PTP-40F 9 % PTP-40F 9


PTP-50F 10 % PTP-50F 10


ECCP-3F 5 % CCP-20CF3 7


ECCP-5F 7 % CCP-30CF3 7


CCP-20CF3 7 % CCP-40CF3 7


CCP-30CF3 7 % CCP-50CF3 7


CCP-40CF3 7 % ECCP-30CF3 4


CCP-50CF3 7 % ECCP-50CF3 4


ECCP-30CF3 6 % ECCP-3F.F 5


~ECCP-50CF3 6 % ECCP-SF.F 4


ECCP-3F.F 8 % D-302FF 7


ECCP-SF.F 7 % D-502FF 6


CP-302FF 7




203586,
- 35 -
90-442 (M21) 89/1018 (M22)
PCH-2 4 % PCH-3 22


PCH-3 17 % PCH-4 18


PCH-4 12 % PTP-70F 6


PCH-5 11 % PTP-102 5


CCP-30CF3 7 % PTP-201 7


CCP-50CF3 6 % CP-3F 10


ECCP-31 4 % CP-5F 8


ECCP-32 4 % ECCP-3F 4


ECCP-3F 6 % BCH-32 10


ECCP-5F 6 % BCH-5.F2 10


CPTP-301 5


CPTP-302 5


PTP-40F 7


PTP-SOF 6


89/1020 (M23) 89/1034 (M24)
PCH-3 22 % PCH-3 22


PCH-4 17 % PCH-4 16


K6 9 % K6 2


K9 3 % PTP-40F 8


PTP-70F 6 % PTP-102 4


CP-3F 10 % PTP-201 5


CP-5F 9 % CP-3F 10


ECCP-3F 9 % CP-5F 8


CPTP-301 5 % ECCP-3F 5


CPTP-302 4 % BCH-32 8


BCH-5.F2 10


CPTP-301 2




20358~~
- 36 -
8G;~1036 (M25) 89/1037 (M26)
PCH-3 21 % PCH-3 15


K6 6 % K6 6


PTP-40F 8 % K9 6


PTP-102 6 % PTP-40F 8


PTP-201 7 % PTP-102 4


CP-3F 10 % PTP-201 6


CP-5F 10 % PCH-302 3


ECCP-3F 11 % CP-3F 10


BCH-32 10 % CP-5F 10


BCH-5.F2 11 % ECCP-3F 11


BCH-32 10


BCH-5.F2 11


89-733 (M27) 89-789 (M28)
PCH-3 21 % PCH-3 18


K6 6 % PCH-5F 12


PTP-40F 8 % PCH-6F 12


PTP-35 7 % PCH-7F 10


PTP-201 7 % PTP-40F 14


CP-3F 10 % ECCP-33 5


CP-5F 8 % CBC-33 5


ECCP-3F 12 % CBC-53 5


BCH-32 10 % CBC-55 4


BCH-5.F2 11 % CBC-55 4


CBC-33F 5


CBC-53F 5


CBC-55F 5





203~86~
- 37 -
9081 (M29) 90-499 (M30)
PCH-2 7 % PCH-3 18


PCH-3 18 % PCH-4 8


PCH-4 14 % PCH-S 10


PCH-5 15 % PCH-301 13


PCH-7 7 % ME2N.F 3


BCH-32 10 % ME3N.F 3


CPTP-301 4 % PTP-102 3


CPTP-302 3 % PTP-201 4


CPTP-303 3 % CPTP-301 4


ECCP-3 7 % CPTP-302 4


ECCP-3F 6 % CPTP-303 4


ECCP-5F 6 % ECCP-3F 6


ECCP-SF 6


ECCP-31 3


ECCP-32 2


CCP-30CF3 5


CCP-SOFF3 4


C



203~~6 2
- 38 -
90502 (M31) 90-515 (M32)
PCH-3 18 % PCH-3 18


PCH-4 8 % PCH-4 8


PCH-5 10 % PCH-5 10


PCH-301 11 % PCH-301 8


rlE2N.F 3 % ME2N.F 3


ME3N.F 3 % ME3N.F 3


PTP-102 4 % MESN.F 5


PTP-201 3 % PTP-102 5


CPTP-301 3 % CPTP-301 3


CPTP-302 4 % CPTP-302 4


CPTP-303 3 % CPTP-303 3


ECCP-3F 6 % ECCP-3F 6


ECCP-5F 6 % ECPP-5F 6


ECCP-31 5 % ECCP-31 5


ECCP-32 4 % ECCP-32 4


CCP-30CF3 5 % CCP-30CF3 5


CCP-50CF3 4 % CCP-50CF3 4


90-602 (M33) 90-604 (M34)
PCH-2 5 % PCH-2 5


PCH-3 15 % PCH-3 15


PCH-4 11 % PCH-4 11


PCH-5 21 % PCH-5 21


PCH-7 11 % PCH-32 5


PCH-32 5 % FET-3F I4


CFET-3F 12 % FET-5F 11


CFET-5F 10 % CBC-33 6


CBC-33 4 % CBC-53 6


CBC-53 6 % CBC-55 6




~03~$~~
- 39 -
90-605 (:~I35 ) 90-606 (M36 )
PCH-3 15 % PCH-3 15


PCH-4 11 % PCH-4 11


PCH-5 21 % PCH-5 21


PCH-7 11 % PCH-7 11


CFET-3F 12 % PCH-32 5


CFET-5F 10 % CFET-3F 8


FET-3F 5 % CFET-5F 6


FET-5F 5 % FET-3F 7


CBC-33 4 % FET-5F 7
0


CBC-53 6 % CBC-33 4
0


CBC-53 5


90-607 (M37) 90-608 (M38)
PCH-2 5 % PCH-2 5


PCH-3 15 % PCH-3 15


PCH-4 11 % PCH-4 11


PCH-5 21 % PCH-5 21


PCH-7 11 % PCH-7 11


PCH-32 5 % PCH-32 5


CFET-3F 12 % CPTP-30CF3 12


CFET-3F.F 10 % CPTP-50CF3 10.


CBC-33 4 % CBC-33 4


CBC-53 6 % CBC-53 6





203862
- 40 -
ZLI-4720-100 (M 39) 90609 (M 40)
PCH-3 18 % PCH-3 18


PCH-4 14 % PCH-4 14


PCH-5 12 % PCH-5 12


PCH-7 8 % PCH-7 8


PTP-102 3 % PTP-20F 3


PTP-201 3 % PTP-40F 3


CPTP-302 3 % CPTP-30CF3 3


ECCP-31 4 % ECCP-31 4


ECCP-32 5 % ECCP-32 5


ECCP-33 5 % ECCP-33 5


ECC1~-35 4 % ECCP-35 4


ECCP-3 7 % ECCP-3 7


ECCP-3F 7 % ECCP-3F 7


ECCP-5F 7 % ECCP-5F 7


90/2008 (M 41) 90/370 (M 42)
PCH-3 10 % PYP-3F 7


PYP-3F 10 % PCH-3 11


PYP-5F 9 % PCH-5 10


', PCH-5F 9 % PCH-7 10


PCH-7F 9 % PTP-35 16


ECCP-3F 13 % CPTP-303 4


ECCP-SF 12 % CCP-20CF3 15


CP-3F 9 % CCP-30CF3 21


CP-5F 9 % CCP-50CF3 6


CPTP-301 5


CPTP-303 5
i






- 41 - 2035862
90/371 (a'1 43) 90/373 (M 44)
PYP-3F 7 % PYP-3F 7


PCH-3 11 % PCH-3 9


PCH-5 10 % PCH-5 10


PCH-7 10 % PCH-7 9


PCH-301 16 % PTt'-35 15


CPTP-303 4 % PTP-45 19


CCP-20CF3 15 % CPTP-303 4


CCP-30CF3 21 % BCH-32 14


CCP-50CF3 6 % BCH-52F 13


90/409 (M 45) 90/414 (M 46)
PYP-3 F 7 % PYP-3 F 7


PCH-3 21 % PCH-3 11


:CH-5 10 % PCH-5 10


PCH-7 10 % PCH-7 10


PCH-301 10 % PCH-301 13


PTP-102 4 % CPTP-303 4


PTP-201 4 % PTP-102 3



CPTP-303 6 % CCP-20CF3 10


CCP-20CF3 8
CCP-30CF3 11


CCP-30CF3 8 % CCP-40CF3 10


CCP-40CF3 6 % CCP-50CF3 11


CCP-50CF3 6


a




- 42 - 203~~6?
90,'4'15 ( M 47 ) 90/411 ( M 48 )
?YP-3F 10 % PYP-3F 7


T~6 10 % PCH-3 21


PCH-3 11 % PCH-5 10


PCH-5 10 % PCH-7 10


PCH-7 10 % PCH-301 10


PCH-301 12 % PTP-102 4


PTP-35 5 % PTP-201 3


PTP-102 5 % CPTP-303 6


CPTP-302 5 % CCP-30CF3 10


CPTP-303 5 % CCP-50CF3 10


BCH-32 8 % ECCP-32 4


BCH-52F 9 % ECCP-33 5


90/415 (M 49) 90/417 (M 50)
PYP-3F 6 % PYP-3F 4


PCH-3 14 % PCH-3 22


PCH-5 10 % PCH-5 11


PCH-7 10 % PCH-7 13


PCH-301 13 % PCH-301 11


CPTP-303 4 % PTP-102 5


PTP-102 4
PTP-201 4


CCP-30CF3 11 % CPTP-301 4


CCP-50CF3 11 % CPTP-302 3


ECCP-32 9 % CPTP-303 5


ECCP-33 8 % BCH-32 10


BCH-52F 8





203586
- 43 -
90/2014 (M51) 90/2015 (M52)
K5 7.0 PCH-3 21,0


PCH-3 28.0 PCH-5 10.0


PCH-5 13,0 PCH-7F 15,0


PCH-301 11,0 CCP-20CF3 12.0


CCP-20CF3 8.0 CCP-30CF3 13.0


CCP-30CF3 8,0 CCP-40CF3 10,0


CCP-40CF3 5,0 CCP-50CF3 8.0


CCP-50CF3 6,0 PTP-102 . 7,0


PTP-102 3.0 CPTP-301 4.0


CPTP-301 6,,0


90/487 (M53)
PCH-3 18,0


PCH-4 14,0


PCH-5 11,0


ME2N.F 3,0


ME3N.F 4,0


0-302 5,0


D-402 5,0


PTP-102 4,0


CPTP-301 4,0


CPTP-302 4,0


CPTP-303 3,0


ECCP-3F ~ 6,0


ECCP-5F 6,0


ECCP-31 6,0


ECCP-32 7,0





_. . 203~8~;
- 44 -
PCH-53: traps-1-p-propylphenyl-4-pentylcyclohexane
I-32: 1-(traps-4-propylcyclohexyl)-2-(4'-ethyl
2'-fluorobiphenyl-4-yl)-ethane
I-35: 1-(traps-4-propylcyclohexyl)-2-(4'-pentyl-
2'-fluorobiphenyl-4-yl)-ethane
BCH-32: 4-ethyl-4'-(traps-4-propylcyclohexyl)-
biphenyl
BCH-52: 4-ethyl-4'-(traps-4-pentylcylcohexyl)-
biphenyl (sic)
CCH-303: traps,traps-4-propoxy-4'-propylcyclohexyl-


cyclohexane


CCH-501: traps,traps-4-methoxy-4'-pentylcyclohexyl-


cyclohexane
C


CH-35: traps-4-pentylcyclohexyl trans,trans-4-


propylcyclohexylcyclohexanecarboxylate


CH-43: traps-4-propylcyclohexyl trans,trans-4-


butylcyclohexylcyclohexanecarboxylate


CH-45: traps-4-pentylcyclohexyl trans,trans-4-


butylcyclohexylcyclohexanecarboxylate


PCH-302: traps-1-p-ethoxyphenyl-4-propylcyclohexane


PCH:303: traps-1-p-propoxyphenyl-4-propylcyclo-


hexane
PCH-304: traps-1-p-butoxyphenyl-4-propylcyclohexane


CCH-502: traps,traps-4-ethoxy-4'-pentylcyclohexyl-


cyclohexane


ECCP-32: 1-[traps-4-(traps-4-propylcyclohexyl)-


cyclohexyl]-2-(p-ethylphenyl)-ethane


ECCP-31: 1-[traps-4-(traps-4-propylcyclohexyl)-


cyclohexyl]-2-(p-methylphenyl)-ethane


ECCP-35: 1-[traps-4-(traps-4-propylcyclohexyl)-


cyclohexyl]-2-(p-pentylphenyl)-ethane


PCH-501: traps-1-p-methoxyphenyl-4-pentylcyclo-


hexane
PCH-502: traps-1-p-ethoxyphenyl-4-pentylcyclohexane
CP-33: p-propylphenyl trans,trans-4-propylcyclo
hexylcyclohexanecarboxylate
CP-35: p-pentylphenyl trans,trans-4-propylcyclo-
hexylcyclohexanecarboxylate



2o3~~sz
- 45 -
CP-43: p-propylphenyl trans,trans-4-butylcyclo-
hexylcyclohexanecarboxylate
,CP-45: p-pentylphenyl trans,trans-4-butylcyclo-
hexylcyclohexanecarboxylate
PTP-40F: 4-butoxy-4'-fluorotolan
PTP-50F: 4-pentoxy-4'-fluorotolan
PTP-70F: 4-heptoxy-4'-fluorotolan
PCH-301: traps-1-p-methoxyphenyl-4-propylcyclo-
hexane
CCH-301: traps,traps-4-methoxy-4'-propylcyclohexyl-
cyclohexane
CBC-33F: 4,4'-bis-(traps-4-propylcyclohexyl)-2-
fluorobiphenyl
CBE-55F: 4,4'-bis-(traps-4-pentylcyclohexyl)-2-
fluorobiphenyl
CBC-53F: 4-(traps-4-pentylcyclohexyl)-4'-(traps-4-
propylcyclcohexyl)-2-fluorobiphenyl (sic)
CBC-33: 4,4'-bis-(traps-4-propylcyclohexyl)-
biphenyl
CBC-55: 4,4'-bis-(traps-4-pentylcyclohexyl)-
biphenyl
CBC-53: 4-(traps-4-pentylcyclohexyl)-4'-(traps-4
propylcyclohexyl)-biphenyl
ECCP-33: 1-[traps-4-(traps-4-propylcyclohexyl)
cyclohexyl~-2-(p-propylphenyl)-ethane
CCH-51F: traps,traps-4-fluoromethyl-4'-pentyl-
cyclohexylcyclohexane
CCH-31F: traps,traps-4-fluoromethyl-4'-propyl-
cyclohexylcyclohexane
PTP-102: 4-methyl-4'-ethoxy-tolan
PTP-201: 4-methoxy-4'-ethyl-tolan
CPTP-301: 4-(traps-4-propylcyclohexyl)-4'-methoxy-
tolan
CPTP-302: 4-(traps-4-propylcyclohexyl)-4'-ethoxy-
tolan
CPTP-303: 4-(traps-4-propylcyclohexyl)-4'-propoxy-
tolan
PCH-5F: traps-1-p-fluorophenyl-4-pentylcyclohexane
PCH-6F: traps-1-p-fluorophenyl-4-hexylcyclohexane


203586?
- 46 -
PCH-7F: traps-1-p-fluorophenyl-4-heptylcyclohexane


EPCH-20CF3: 1-(traps-4-ethylcyclohexyl)-2-(p-tri-


fluoromethoxyphenyl)-ethane


EPCH-30CF3: 1-(traps-4-propylcyclohexyl)-2-(p-tri-


fluoromethoxyphenyl)-ethane


EPCH-50CF3: 1-(traps-4-pentylcyclohexyl)-2-(p-tri-


fluoromethoxyphenyl)-ethane


EPCH-70CF3: 1-(traps-4-heptylcyclohexyl)-2-(p-tri-


fluoromethoxyphenylj-ethane


PCH-30CF3: traps-1-p-trifluoromethoxyphenyl-4-propyl-


cyclohexane
PCH-50CF3: traps-1-p-trifluoromethoxyphenyl-4-pentyl-
cyclohexane
ECCP-30CF3: 1-[traps-4-(traps-4-propylcyclohexyl)-
cyclohexyl]-2-(p-trifluoromethoxyphenyl)-
ethane
ECCP-50CF3: 1-[traps-4-(traps-4-pentylcyclohexyl)-
cyclohexyl]-2-(p-trifluoromethoxyphenyl)-
ethane
CCP-20CF3: p-[traps-4-(traps-4-ethylcyclohexyl)-


cyclohexyl]-trifluoromethoxybenzene


CCP-30CF3: p-[traps-4-(traps-4-propylcyclohexyl)-


cyclohexyl]-trifluoromethoxybenzene


CCP-40CF3: p-[traps-4-(traps-4-butylcyclohexyl)-


cyclohexyl]-trifluoromethoxybenzene


CCP-50CF3: p-[traps-4-(traps-4-pentylcyclohexyl)-


cyclohexyl]-trifluoromethoxybenzene


BCH-30CF3: 4-trif luoromethoxy-4'-(traps-4-propyl-


cyclohexyl)-biphenyl


ECCP-3F. F: 1-[traps-4-(traps-4-propylcyclohexyl)-


cyclohexyl]-2-(3,4-difluorophenyl)-ethane


ECCP-5F. F: 1-[traps-4-(traps-4-pentylcyclohexyl)-


cyclohexyl]-2-(3,4-difluorophenyl)-ethane


CCP-3F. F: 4-[traps-4-(traps-4-propylcyclohexyl)-


cyclohexyl]-1,2-difluorobenzene


CCP-5F. F: 4-[traps-4-(traps-4-pentylcyclohexyl)-


cyclohexyl]-1,2-difluorobenzene


D-302FF: 2,3-difluoro-4-,~sthoxyphenyl traps-4-


propylcyclohexylcarboxylate




203586'
- 47 -
D-502FF: 2,3-difluoro-4-ethoxyphenyl traps-4-


pentylcyclohexylcarboxylate


CCP-3F: 4-[traps-4-(traps-4-propylcyclohexyl)-


cyclohexyl]-fluorobenzene


ECCP-3F: 1-[traps-4-(traps-4-propylcyclohexyl)-


cyclohexyl]-2-(p-fluorophenyl)-ethane


ECCP-5F: 1-[traps-4-(traps-4-pentylcyclohexyl)-


cyclohexyl]-2-(p-fluorophenyl)-ethane


CP-3F: p-fluorophenyl traps-4-(traps-4-propyl-


cyclohexyl)-cyclohexanecarboxylate
CP-5F: p-fluorophenyl traps-4-(traps-4-pentyl-
cyclohexyl)-cyclohexanecarboxylate
PYP-5F: 2-p-fluorophenyl-5-pentylpyrimidine
- PYP-6F: 2-p-fluorophenyl-5-hexylpyrimidine
PYP-7F: 2-p-fluorophenyl-5-heptylpyrimidine
PYP-30CF3: 2-p-trifluoromethoxyphenyl-5-propyl-
pyrimidine
PYP-50CF3: 2-p-trifluoromethoxyphenyl-5-pentyl-
pyrimidine
PYP-70CF3: 2-p-trifluoromethoxyphenyl-5-heptyl-
pyrimidine
PCH-3: p-traps-4-propylcyclohexyl-benzonitrile


PCH-4: p-traps-4-butylcyclohexyl-benzonitrile


PCH-5: p-traps-4-pentylcyclohexyl-benzonitrile


ECCP-3: 1-[traps-4-(traps-4-propylcyclohexyl)-


cyclohexyl]-2-(p-cyanophenyl)-ethane


ECCP-3CF3: 1-[traps-4-(traps-4-propylcyclohexyl)-


cyclohexyl]-2-(p-trifluoromethylphenyl)-


ethane


ECCP-5CF3: 1-[traps-4-(traps-4-pentylcyclohexyl)-
cyclohexyl]-2-(p-trifluoromethylphenyl)-
ethane
PYP-SN.F: 2-(3-fluoro-4-cyanophenyl)-5-pentyl-
pyrimidine
PYP-7N. F: 2-(3-fluoro-4-cyanophenyl)-5-heptyl-
pyrimidine
PCH-30CF2: traps-1-p-difluoromethoxyphenyl-4-propyl-
cyclohexane ,


203586?
- 48 -
PCH-50CFz: traps-1-p-difluoromethoxyphenyl-4-pentyl-
cyclohexane
PCH-3-OCFZ: traps-1-p-difluoromethoxyphenyl-4-propyl-
cyclohexane
BCH-5.F2: 4-(traps-4-pentylcyclohexyl)-2'-fluoro-4'-


ethylbiphenyl


K6: 4-ethyl-4'-cyanobiphenyl


K9: 4-propyl-4'-cyanobiphenyl


PTP-35: 4-propyl-4'-pentyltolane


ME2N.F: 3-fluoro-4-cyanophenyl 4-ethylbenzoate


ME3N.F: 3-fluoro-4-cyanophenyl 4-propylbenzoate


MESN.~': 3-fluoro-4-cyanophenyl 4-pentylbenzoate


PCH-2: p-traps-4-ethylcyclohexylbenzonitrile


PCH-7: p-traps-4-heptylcyclohexylbenzonitrile


PCH-32: traps-1-p-ethylphenyl-4-propylcyclohexane


CFET-3F: 1-(4-(traps-4-propylcyclohexyl)-2-fluoro-


4'-yl-biphenyl)-2-(4-fluorophenyl)-ethane


CFET-5F: 1-(4-(traps-4-pentylcyclohexyl)-2-fluoro-


4'-yl-biphenyl)-2-(4-fluorophenyl)-ethane


FET-3F: 1-(2-fluoro-4-propyl-4'-yl-biphenyl)-2-(4-


fluorophenyl)-ethane


FET-5F: 1-(2-fluoro-4-pentyl-4'-yl-biphenyl)-2-(4-


fluorophenyl)-ethane
CPTP-30CF3: 4-(traps-4-propylcylcohexyl)-4'-trifluoro-
methoxy-ethane (sic)
CPTP-50CF3: 4-(traps-4-pentylcylcohexyl)-4'-trifluoro-
methoxy-ethane (sic)
PTP-20F: 4-ethoxy-4'-fluorotolane
PYP-3F: 2-(4-fluorophenyl)-5-propylpyrimidine
PTP35: 4-propyl-4'-pentyltolane
PTP45: 4-butyl-4'-pentyltolane
BCH-52F: 4-(traps-4-pentylcyclohexyl)-2-fluoro-4'-
ethylbiphenyl
CP-302FF: 2,3-difluoro-4-ethoxyphenyl traps-4-
(traps-4-propylcyclohexyl)-cyclohexane-
carboxylate
PCH-301: traps-1-p-methoxyphenyl-4-propylcyclo-
hexane .
PCH-401: traps-1-p-methoxyphenyl-4-butylcyclohexane



20358 2
- 49 -
D-302: 4-ethoxyphenyl traps-4-propylcyclohexyl-
carboxylate
D-402: 4-ethoxyphenyl traps-4-butylcyclohexyl-
carboxylate

Representative Drawing

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Administrative Status

For a clearer understanding of the status of the application/patent presented on this page, the site Disclaimer , as well as the definitions for Patent , Administrative Status , Maintenance Fee  and Payment History  should be consulted.

Administrative Status

Title Date
Forecasted Issue Date 2004-03-30
(86) PCT Filing Date 1990-06-15
(87) PCT Publication Date 1991-01-24
(85) National Entry 1991-03-11
Examination Requested 1997-05-15
(45) Issued 2004-03-30
Expired 2010-06-15

Abandonment History

There is no abandonment history.

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $0.00 1991-03-11
Registration of a document - section 124 $0.00 1991-07-26
Maintenance Fee - Application - New Act 2 1992-06-15 $100.00 1992-05-25
Maintenance Fee - Application - New Act 3 1993-06-15 $100.00 1993-05-11
Maintenance Fee - Application - New Act 4 1994-06-15 $100.00 1994-05-24
Maintenance Fee - Application - New Act 5 1995-06-15 $150.00 1995-05-25
Maintenance Fee - Application - New Act 6 1996-06-17 $150.00 1996-05-24
Request for Examination $400.00 1997-05-15
Maintenance Fee - Application - New Act 7 1997-06-16 $150.00 1997-05-23
Maintenance Fee - Application - New Act 8 1998-06-15 $150.00 1998-06-10
Maintenance Fee - Application - New Act 9 1999-06-15 $150.00 1999-05-17
Maintenance Fee - Application - New Act 10 2000-06-15 $200.00 2000-05-17
Maintenance Fee - Application - New Act 11 2001-06-15 $200.00 2001-05-03
Maintenance Fee - Application - New Act 12 2002-06-17 $200.00 2002-05-07
Maintenance Fee - Application - New Act 13 2003-06-16 $200.00 2003-05-05
Final Fee $300.00 2004-01-14
Maintenance Fee - Patent - New Act 14 2004-06-15 $250.00 2004-05-04
Maintenance Fee - Patent - New Act 15 2005-06-15 $450.00 2005-05-09
Maintenance Fee - Patent - New Act 16 2006-06-15 $450.00 2006-05-04
Maintenance Fee - Patent - New Act 17 2007-06-15 $450.00 2007-05-07
Maintenance Fee - Patent - New Act 18 2008-06-16 $450.00 2008-05-08
Maintenance Fee - Patent - New Act 19 2009-06-15 $450.00 2009-05-12
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
MERCK PATENT GESELLSCHAFT MIT BESCHRAENKTER HAFTUNG
Past Owners on Record
KURMEIER, HANS-ADOLF
OYAMA, TAKAMASA
PLACH, HERBERT
REIFFENRATH, VOLKER
SCHEUBLE, BERNHARD
WEBER, GEORG
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
Documents

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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Abstract 1994-06-11 1 20
Description 2002-07-30 56 1,546
Description 1994-06-11 49 2,363
Description 2000-09-29 52 2,305
Claims 2002-07-30 10 268
Cover Page 1994-06-11 1 52
Claims 1994-06-11 7 351
Claims 2000-09-29 8 209
Cover Page 2004-02-24 1 28
Assignment 1991-03-11 6 241
PCT 1991-03-11 4 149
Prosecution-Amendment 1997-05-15 1 40
Prosecution-Amendment 2000-03-29 2 82
Prosecution-Amendment 2000-09-29 21 607
Prosecution-Amendment 2002-01-30 2 88
Prosecution-Amendment 2002-07-30 19 538
Fees 2003-02-12 1 26
Correspondence 2004-01-14 1 31
Prosecution Correspondence 1991-03-11 1 69
Fees 1997-05-23 1 73
Fees 1996-05-24 1 74
Fees 1995-05-25 2 78
Fees 1994-05-24 1 69
Fees 1993-05-11 1 38
Fees 1992-05-25 1 30