Direactive mesogenic compounds and intermediates

Details Direactive mesogenic compounds and intermediates Direactive mesogenic compounds and intermediates

2000-05-22

2002-11-05

Wu, Shean C. (Department: 1756)

Stock material or miscellaneous articles

Liquid crystal optical display having layer of specified...

C252S299650, C252S299660, C252S299670, C560S066000, C560S095000, C526S072000

Reexamination Certificate

active

06475574

ABSTRACT:

The invention relates to
direactive mesogenic compounds or mixtures thereof obtainable by
a) treating a mesogenic diol of formula I,
HO—MG—OH  (I)
 in which
MG is a mesogenic group,
with a mixture of the halides of formula II and III,
X
1
—(CH
2
)
m
—R
a
  (II)
X
2
—(CH
2
)
n
—R
b
  (III)
 in which
X
1
and X
2
are each independently Cl, Br or I,
m and n are different integers between 1 and 20
R
a
and R
b
are each independently groups selected from
—CH
2
OH or —CH═CWH
 wherein
W is H, CH
3
or Cl,
in the presence of a base, and
b) treating the resulting intermediate
in the case of R
a
and R
b
being —CH
2
OH, with a vinyl derivative of formula CH
2
═CW—(CO)
a
—O— or a reactive derivative thereof, in which a is 0 or 1
in the case of R
a
and R
b
being —CH═CWH with a perbenzoic acid.
The invention furthermore relates to the preparation of such compounds and to their use in electrooptical scattering systems and for the preparation of oriented liquid crystal polymers.
Reactive liquid crystal compounds can be polymerized in situ, whilst in their liquid crystal phase, to give highly crosslinked anisotropic films which can be used, for example, as polarizing beam splitters (see, for example, EP 0,428,213). Reactive liquid crystal compounds have furthermore been proposed for electrooptical scattering systems (see, for example, EP 0,451,905), cholesteric polarizers (e.g. EP 0,606,940) and compensation films for STN displays (e.g. EP 0,423,881).
Reactive liquid crystal diesters of formula
are mentioned in EP 0,261,712 (n=0), EP 0,331,233 (n=1). Reactive liquid crystal biphenyls of formula
are disclosed by EP 0,405,713.
The International Patent application WO 93122397 discloses a compound of formula
These reactive liquid crystalline compounds often exhibit, however, rather high melting points disadvantageous values of the birefringence and comparable narrow mesophase ranges.
In view of the broad range of applications of reactive liquid crystal compounds it was desirable to have available further compounds of this type which fulfill the various requirements such as a reasonably low melting point, a high birefringence, a broad mesogenic range and preferably an enantiotropic nematic range to a high degree.
It was an object of the present invention to provide new reactive liquid crystalline compounds with advantageous properties thus extending the pool of reactive liquid crystal compounds available to the expert. Other objects of the present invention can be taken from the following detailed specification.
The present invention thus relates to reactive mesogenic compounds or mixtures thereof obtainable by treating mesogenic diols of formula I, in particular those having a symmetric structure unit with a mixture of halides of formula II and III and to their use in electrooptical systems of scattering type and for the preparation of oriented liquid crystal polymers. The invention furthermore relates to the preparation of compounds according to formula I.
Preferred embodiments of the present invention are:
a) Composition of direactive compounds comprising at least one compound of each formula IV, V and VI,
R
1
—(CH
2
)
m
—O—MG—O—(CH
2
)
n
—R
2
  IV
 R
1
—(CH
2
)
m
—O—MG—O—(CH
2
)
m
—R
1
  V
R
2
—(CH
2
)
n
—O—MG—O—(CH
2
)
n
—R
2
  VI
 in which MG, m and n have the meaning given, and
R
1
and R
2
are each independently
—CH
2
—O—(CO)
a
—CW═CH
2
or
b) Direactive compound or mixture thereof
 in which
m—n>1, in particular 2, 3 or 4.
c) Direactive compound or mixture thereof in which
MG is a mesogenic group of formula VIII,
—(A
1
—Z
1
)
o
—A
2
—  VIII
 in which
A
1
and A
2
are each independently
(a) 1,4-phenylene in which one or two CH groups may be replaced by N;
(b) 1,4-cyclohexylene in which one or two non-adjacent CH
2
groups may be replaced by —O— or one —CH— group may be replaced by —C(CN)—;
(c) naphthaline-2,6-diyl;
it being possible that group (a) is substituted by halogen cyano or alkyl, alkoxy or alkanoyl with 1 to 6 C atoms,
Z
1
is each independently —COO—, —O—CO—, —CH
2
—CH
2
—, —C≡C—, —CH
2
O—, —OCH
2
— or a single bond, and
o is 1, 2 or 3.
d) Direactive compound or mixture thereof in which MG is selected from the structure elements (1) to (6).
 in which
L is CH
3
, Cl, F, OCH
3
or —CO—CH
3
, and
r is 0, 1, 2 or 4.
e) Direactive compound or mixture thereof in which
n and m are given by the following table:
m 5 5 5 4 4
n 2 3 4 2 3
A further aspect of the present invention is direactive compounds of formula IV A
R
1
—(CH
2
)
m
O—MG—O—(CH
2
)
n
—R
2
  (IVA)
in which
R
1
and R
2
have the meaning given,
m and n are different integers between 2 and 10, and
MG is a mesogenic group, the core of which being symmetrical, preferably a structure element of formula (1), (5) or (6), in particular
direactive compounds of the formula IVA1
 in which
R
1
, R
2
,
L and r have the meaning given,
m and n are different integers between 2 and 10, and
t is 0 or 1.
Other aspect of the invention are the polymers prepared by polymerizing a monomer as described above and chemical intermediate compounds or mixtures thereof useful in preparing direactive compounds or mixtures thereof as described above, comprising mesogene-containing molecules, said mesogenes having two side chains attached thereto that contain hydroxyl or vinyl group at the end thereof, said mesogenes and said functional groups being separated by at least two to twenty spacer atoms, wherein both spacer groups have different chain length.
Above and below, the term reactive mesogenic compounds refers to reactive rod-like molecules which may be enantiotropic, monotropic or isotropic, preferably, however, enantiotropic or monotropic.
In the inventive compounds in which MG is a mesogenic group of formula VIII, A
1
and A
2
can be independently from each other an unsubstituted or a substituted 1,4-phenylene group of formula
X
2
, X
3
, X
5
and X
6
can be independently from each other H, F, Cl, methyl or CN.
In the following, for the sake of simplicity, the following notation will be used:
Phe. 2 X
2
3 X
3
5 X
5
6 X
6
is a 1,4-phenylene group carrying in 2-position the group X
2
, in 3-position the group X
3
etc.; in case X
2
, X
3
, X
5
and/or X
6
, denote H, this will not be specified in above notation, i.e. only true substitutions will be listed. Thus Phe, for example, is an unsubstituted 1,4-phenylene group while Phe.2F 5 Cl is a 2-fluoro-5-chloro-1,4-phenylene group. Furthermore, Pyr is pydmidine-2,5diyl, Pyd is pyrdine-2,5diyl and Nap is a naphthalene-2,6-diyl group. The notation Pyr and Pyd in each case include the 2 possible positional isomers.
The compounds according to formula IV comprise 2- and 3-ring compounds (n=1 or 2) of formulae IV2 and IV3:
R
1
—(CH
2
)
m
—O—A
1
—Z
1
—A
2
—O—(CH
2
)
n
—R
2
  IV2
R
1
(CH
2
)
m
—O—A
1
—Z
1
—A
1
—Z
1
—A
2
—O—(CH
2
)
n
—R
2
  IV3
In the 3-ring compounds of formula IV3, the ring groups A
1
can be chosen independently from each other.
Especially preferred is a smaller group of 2-ring compounds exhibiting the following structures for —A
1
—Z
1
—A
2
—:
—Phe.2CH
3
—Phe— IV2-1
—Phe.3CH
3
—Phe— IV2-2
—Phe.2Cl—Phe— IV2-3
—Phe.3Cl—Phe— IV2-4
—Phe.2CN—Phe— IV2-5
—Phe.3CN—Phe— IV2-6
—Phe.2Cl3Cl—Phe— IV2-7
—Phe.2Cl3F—Phe— IV2-8
—Phe.2F—Phe— IV2-9
—Phe.3F—Phe— IV2-10
—Phe.—Phe— IV2-11
—Phe.F—Nap— IV2-12
—Phe.2Cl—Nap— IV2-13
—Phe.F—Nap— IV2-14
—Phe.3Cl—Nap— IV2-15
—Phe.2F—Pyr— IV2-16
—Phe.2F—Pyr— IV2-17
—Phe.2CH
3
—Pyd— IV2-18
—Phe.2Cl—Pyd— IV2-19
—Phe.F—CH
2
CH
2
—Phe— IV2-20
—Phe.3F—CH
2
CH
2
—Phe— IV2-21
—Phe.2Cl—CH
2
CH
2
—Phe— IV2-22
—Phe.3Cl—CH
2
CH
2
—Phe— IV2-23
—Phe.2CN—CH
2
CH
2
—Phe— IV2-24
—Phe.3CN—CH
2
CH
2
—Phe— IV2-25
—Phe.2Cl3Cl—CH
2
CH
2
—Phe— IV2-26
—Phe.2Cl3F—CH
2
CH
2
—Phe— IV2-27
The 3-ring compounds according to formula IV3 preferably exhibit the following structures for —A
1
—Z
1
—A
1
—Z
1
—A
2
:
In these structures, IV3-a to IV3-d, L
1
and L
2
denote independently from each oth

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