Family of conducting liquid crystals

Details Family of conducting liquid crystals Family of conducting liquid crystals

2003-01-13

2004-02-10

Huff, Mark F. (Department: 1756)

Compositions

Liquid crystal compositions

Containing nonsteryl liquid crystalline compound of...

C252S299610, C252S299620, C252S299010, C544S343000, C585S026000, C546S070000, C568S632000, C532S001000

Reexamination Certificate

active

06689290

ABSTRACT:

This invention relates to novel mixtures of compounds and, in particular, novel mixtures that exist as discotic liquid crystals and which have significantly improved liquid crystal and conductive properties. The invention also relates to certain novel compounds per se.
Several potential applications of discotic liquid crystals which are based on a combination of their processability and their ability to act as semiconductors have already been described. These include their use as (1) conducting interconnects in stacked silicon chip systems (2) as conducting layers in photoreproductive and electrophotographic systems (3) as active elements in electronic ‘nose’ arrays (4) as conductive elements in spatial light modulators and many others and as (5) electron/hole transporting materials in light emitting diodes.
Thus according to the main feature of the invention we provide a mixture comprising a molecule of formula I;
in which A
1
, A
2
, A
3
, A
4
, A
5
and A
6
, which may be the same or different, are each N or —CH;
Y
1
, Y
2
, Y
3
, Y
4
, Y
5
and Y
6
, which may be the same or different, are each hydrogen or C
1
to C
12
alkoxy;
X
1
, X
2
, X
3
, X
4
, X
5
and X
6
, which may be the same or different, are each hydrogen, C
1
to C
12
alkoxy or alkyl C
1
to C
12
; and
R
7
, R
8
, R
9
, R
10
, R
11
and R
12
are each hydrogen, or each of R
7
and R
8
, R
9
and R
10
and R
11
, and R
12
may form a bond;
and a molecule of formula II;
in which R
1
, R
2
, R
3
, R
4
, R
5
and R
6
, which may be the same or different, are each alkyl or substituted (and/or chiral) alkyl C
1
to C
16
, acyl C
1
to C
16
, polyethyleneoxy, a flexible connection to a polymer backbone or part of a polymer backbone in homopolymers, copolymers or block copolymers; and
B
1
, B
2
, B
3
, B
4
, B
5
and B
6
a, which may be the same or different, are each, hydrogen, alkyl C
1
to C
16
, alkoxy C
1
to C
16
, nitro, halogeno, cyano, amido, diazo or ester, e.g. alkyl C
1
to C
16
ester.
By the term “mixture” we mean a combination of compounds of formula I and formula II. In such combinations, quadrupolar attractions and van der Waals forces, between compounds of formula I and compounds of formula II suggests that the mixtures exist as compounds per se. Thus, any reference to mixtures of compounds of formula I and II should be construed accordingly.
In a preferred mixture of the invention, in the compound of formula I each of A
1
, A
2
, A
3
, A
4
, A
5
and A
6
are the same.
When each of A
1
, A
2
, A
3
, A
4
, A
5
and A
6
is N, then each of Y
1
, Y
2
, Y
3
, Y
4
, Y
5
and Y
6
preferentially represents hydrogen or alkoxy C
3
to C
8
. Further, when each of A
1
, A
2
, A
3
, A
4
, A
5
and A
6
is N, then each of X
1
, X
2
, X
3
, X
4
, X
5
and X
6
is preferably C
2
to C
12
alkyl or C
4
to C
12
alkoxy, more preferably C
6
to C
9
alkyl or C
6
to C
9
alkoxy. Most preferably, when each of A
1
, A
2
, A
3
, A
4
, A
5
and A
6
is N, then each of X
1
, X
2
, X
3
, X
4
, X
5
and X
6
is either C
9
alkyl or C
6
alkoxy. We especially prefer each of X
1
, X
2
, X
3
, X
4
, X
5
and X
6
to be the same C
9
alkyl or each of X
1
, X
2
, X
3
, X
4
, X
5
and X
6
to be the same C
6
alkoxy.
When each of A
1
, A
2
, A
3
, A
4
, A
5
and A
6
is N, especially preferred mixtures are those in which each of Y
1
, Y
2
, Y
3
, Y
4
, Y
5
and Y
6
is hydrogen and each of X
1
, X
2
, X
3
, X
4
, X
5
and X
6
is C
9
alkyl, or, alternatively, each of Y
1
, Y
2
, Y
3
, Y
4
, Y
5
and Y
6
is C
6
alkoxy and each of X
1
, X
2
, X
3
, X
4
, X
5
and X
6
is C
6
alkoxy.
When each of A
1
, A
2
, A
3
, A
4
, A
5
and A
6
is C—H, then each of Y
1
, Y
2
, Y
3
, Y
4
, Y
5
and Y
6
preferentially represents hydrogen or alkoxy C
3
to C
8
, preferably hydrogen or alkoxy C
5
to C
7
and most preferably hydrogen or alkoxy C
6
.
When each of A
1
, A
2
, A
3
, A
4
, A
5
and A
6
is C—H, then each of X
1
, X
2
, X
3
, X
4
, X
5
and X
6
is C
2
to C
12
alkyl or C
2
to C
12
alkoxy. When each of X
1
, X
2
, X
3
, X
4
, X
5
and X
6
is alkoxy, they are preferably C
6
to C
12
alkoxy.
Preferred mixtures are those in which compounds of formula I are compounds of formula III;
in which X
1
, X
2
, X
3
, X
4
, X
5
and X
6
are each the same and are selected from —C
9
H
19
, —C
12
H
25
, —OC
6
H
13
and —OC
11
H
23
; and
each of Y
1
, Y
2
, Y
3
, Y
4
, Y
5
and Y
6
are each the same and are selected from hydrogen and —OC
6
H
13
.
Further preferred mixtures are those in which the compounds of formula I are compounds of formula IV;
in which X
1
, X
2
, X
3
, X
4
, X
5
and X
6
are each the same and are selected from —C
9
H
19
, and —OC
6
H
13
; and
each of Y
1
, Y
2
, Y
3
, Y
4
, Y
5
and Y
6
are each the same and are selected from hydrogen and —OC
6
H
13
.
In a preferred mixture of the invention, in the molecule of formula II each of R
1
, R
2
, R
3
, R
4
, R
5
and R
6
are the same and B
1
, B
2
, B
3
, B
4
, B
5
and B
6
are hydrogen. Preferably, each of R
1
, R
2
, R
3
, R
4
, R
5
and R
6
are alkyl C
3
to C
16
, more preferably alkyl C
4
to C
11
and most preferably C
6
or C
11
alkyl. The most preferred compounds of formula II are 2,3,6,7,10,11-hexahexyloxytriphenylene and 2,3,6,7,10,11-hexaundecyloxytriphenylene.
A further preferred mixture of the invention, contains the compound of formula II in which each of R
1
, R
2
, R
3
, R
4
, R
5
and R
6
are the same and are alkyl C
3
-C
16
, more preferably C
4
-C
11
alkyl and most preferably C
6
alkyl. B
1
, B
2
, B
3
, and B
4
are hydrogen and B
5
and B
6
are the same or different and are each or both hydrogen or fluorine. Most preferable is the compound formed by the mixture of formula I with formula II in which formula II is 1,4-difluoro-2,3,6,7,10,11-hexahexyloxytriphenylene. These mixtures are advantages in that the mesophase persists well below room temperature.
Liquid crystal phases can be induced in non-mesogenic materials such as those of formula II in which each of R
1
, R
2
, R
3
, R
4
, R
5
and R
6
are the same or different and are alkyl C
2
-C
11
or ethyleneoxy C
3
-C
9
. More preferably when R
1
, R
2
, R
3
, R
4
, R
5
and R
6
are the same and ethyleneoxy C
5
, and when R
1
, R
2
, R
3
, R
4
, R
5
and R
6
are a combination of ethyleneoxy C
5
and alkyl C
6
. Most preferably when formula II is 2-(1,4,7-Trioxaoctyl)-3,6,7,10,11-pentahexyloxytriphenylene, 2,7-Di(1,4,7-trioxaoctyl)-3,6,10,11-tetrahexyloxytriphenylene, 2,7,10-Tri(1,4,7-trioxaoctyl)-3,6,11-trihexyloxytriphenylene or 2,3,6,7,10,11-Hexa(1,4,7-trioxaoctyl)triphenylene.
A preferred mixture contains a polythene main chain polymer with formula II as a side chain substituent in the form shown in formula V. X is alkyl C
1
-C
10
or an ether oxygen linkage (—O—), and R is hydrogen or methyl. Addition of molecules of formula I to polymers such as those in Formula V produces a liquid crystal polymer which shows much better alignment properties than the polymer of formula V alone.
A further preferred mixture contains formula II as a functionality in polystyrene block copolymers of the form shown in formula VI. The ratio of n:m is from 6-18:1. The compound formed with formula I is again easier to align than the polymer of formula V alone with the added advantage that the blocks comprising the copolymer undergo micro-phase separation.
Another preferred mixture contains the formula I as a constituent part of the polymer backbone, the length of the flexible spacer n is between 6 and 18, most preferably 6, 12, and 18 and the number of molecules of formula II per polymer formula VII, m, is between 2 and 1000.
Block copolymers containing blocks of polyethylene oxide and blocks of formula VII can also be made to undergo micro-phase separation and further preferred mixtures contain the polymer of formula VIII. Where the number of molecules of formula I (m) is 10-100 and the number of ethyleneoxide groups in the side chains (n) is 200-500
In the mixture of the invention, specific compounds of formula I which may be mentioned include the following;
2,3,6,7,10,11-hexakis(4-n-nonylphenyl)dipy

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