Polymerizable mesogenic fluorophenylenes

Details Polymerizable mesogenic fluorophenylenes Polymerizable mesogenic fluorophenylenes

1999-07-15

2001-02-06

Wu, Shean C. (Department: 1756)

Stock material or miscellaneous articles

Liquid crystal optical display having layer of specified...

C428S001550, C252S299630, C252S299670, C570S128000, C570S131000, C570S133000, C349S002000, C560S065000

Reexamination Certificate

active

06183822

ABSTRACT:

SUMMARY OF THE INVENTION
The invention relates to polymerizable mesogenic fluorophenylenes of formula I
wherein P, Sp, X, n, L, Z
1
, Z
2
, A, B, m and R are defined below.
The invention also relates to a polymerizable liquid crystalline composition comprising at least one polymerizable mesogenic compound of formula I, and to the use of the inventive mesogenic compounds and compositions for the preparation of linear or crosslinked liquid crystalline polymers, in particular for the preparation of oriented linear or crosslinked liquid crystalline polymer films.
The invention further relates to the use of inventive compounds, compositions and polymers in liquid crystal displays, such as STN, TN, AMD-TN, temperature compensation, guest-host, phase change, reflective or surface stabilized or polymer stabilized cholesteric texture (SSCT, PSCT) displays, in active and passive optical elements like polarizers, compensators, alignment layers, color filters or holographic elements, in adhesives, synthetic resins with anisotropic mechanical properties, cosmetics, diagnostics, liquid crystal pigments, for decorative and security applications, in nonlinear optics, optical information storage or as chiral dopants.
Polymerizable mesogenic compounds, which are also known as reactive mesogenic compounds, have been described in prior art for various purposes. For example, they can be polymerized in situ whilst being macroscopically oriented in the liquid crystalline state to give anisotropic linear or crosslinked polymers or polymer films with uniform orientation of high quality. These films can be used for example as optical elements like broad band cholesteric polarizers (see EP 0 606 940) or polarization filters (EP 0 397 263).
The WO 93/22397, DE 195 04 224 and WO 97/34862 for example disclose polymerizable mesogenic compounds with mesogenic cores of various structures.
The polymerizable mesogenic compounds described in prior art, however, often exhibit liquid crystalline phases only in a small temperature range or do not show mesophase behavior at all. Another drawback for specific applications is that prior art compounds often exhibit high values of the birefringence.
In particular where polymerizable mesogenic compounds are used in optical phase retardation, compensation or alignment layers or films for liquid crystal displays, it is desirable to have available materials of which the optical properties, such as the birefringence, phase retardation (i.e. the product of birefringence and layer thickness) and dispersion (i.e. the wavelength dependence of the birefringence) are adapted to those of the liquid crystal mixture in the display cell, so that optimum compensation can be achieved.
Thus, there is still a demand for polymerizable mesogenic compounds with a broad liquid crystalline phase and a low value of birefringence.
Furthermore, regarding the broad range of applications for polymerizable mesogenic compounds it is desirable for the expert to have available further compounds of this type which are easy to synthesize and fulfill the various requirements as described above.
It was an aim of the invention to provide new polymerizable mesogenic compounds with advantageous properties, thus extending the pool of reactive liquid crystal compounds available to the expert. Other aims of the present invention are immediately evident to the person skilled in the art from the following detailed description.
It was now found that these aims can be achieved by providing polymerizable mesogenic fluorophenylenes of formula I.
The terms polymerizable mesogenic compound as used in the foregoing and the following comprise compounds with a rod-shaped, board-shaped or disk-shaped mesogenic group, i.e. a group with the ability to induce mesophase behavior in a compound comprising said group. These compounds do not necessarily have to exhibit mesophase behavior by themselves. It is also possible that these compounds show mesophase behavior only in mixtures with other compounds or when the polymerizable mesogenic compounds or the mixtures comprising them are polymerized.
Thus, one object of the invention are polymerizable mesogenic fluorophenylenes of formula I
wherein
is CH
2
═CW—COO—, WCH═CH—O—,
 or CH
2
═CH-Phenyl-(O)
k
— with W being H, CH
3
or Cl and k being 0 or 1,
Sp is a spacer group having 1 to 25 C atoms,
X is —O—, —S—, —CO—, —COO—, —OCO—, —CO—NH—, —NH—CO—, —CH
2
CH
2
—, —OCH
2
—, —CH
2
O—, —SCH
2
—, —CH
2
S—, —CH═CH—, —CH═CH—COO—, —OCO—CH═CH—, —C≡C—, or a single bond,
n is 0 or 1,
L is H or F,
Z
1
and Z
2
are in each case independently —COO—, —OCO—, —CH
2
CH
2
—, —OCH
2
—, —CH
2
O—, —OCH
2
—O— or a single bond,
A and B are each independently
L
1
and L
2
are H or F,
m is 0, 1 or 2, and
R is H, CN, halogen or a straight-chain or branched alkyl radical with up to 25 C atoms which may be unsubstituted, mono- or polysubstituted by halogen or CN, it being also possible for one or more non-adjacent CH
2
groups to be replaced, in each case independently from one another, by —O—, —S—, —NH—, —N(CH
3
)—, —CO—, —COO—, —OCO—, —OCO—O—, —S—CO—, —CO—S— or —C≡C— in such a manner that oxygen atoms are not linked directly to one another, or alternatively R is P—(Sp—X)
n
—.
Another object of the present invention is a polymerizable liquid crystalline composition comprising at least two polymerizable compounds, at least one of which is a compound of formula I.
Another object of the present invention is the use of compounds of formula I and compositions comprising them for the preparation of linear or crosslinked liquid crystalline polymers, in particular for the preparation of oriented linear or crosslinked liquid crystal polymer films.
A further object of the invention is a linear or crosslinked polymer that is obtainable by polymerization of one or more compounds of formula I or by polymerization of a composition comprising at least one polymerizable mesogenic compound of formula I and optionally further comprising one or more other polymerizable or non-polymerizable mesogenic or non-mesogenic compounds.
Particularly preferably the inventive polymerizable mesogenic fluorophenylenes are selected of the following formulae
wherein P, Sp, X, n and R have the meanings of formula I.
In particular preferred are compounds of formulae Ic, Id, Ie and If.
Further preferred are compounds wherein L is F, and compounds wherein
m is 1 or 2 and Z
1
and Z
2
are a single bond,
R has one of the meanings given for P—(S—X)
n
—,
X is —O—, —CO—, —COO—, —OCO—, —CH
2
O— or —CH═CH—COO—,
P is acrylate or methacrylate,
R is halogen, cyano or an optionally fluorinated achiral or chiral alkyl or alkoxy group with 1 to 15 C atoms,
n is 0,
n is 1 and Sp is alkylene with 1 to 15, in particular 1 to 7, C atoms.
If R in formula I is an alkyl or alkoxy radical, i.e. where the terminal CH
2
group is replaced by —O—, this may be straight-chain or branched. It is preferably straight-chain, has 2, 3, 4, 5, 6, 7 or 8 carbon atoms and accordingly is preferably ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy, heptoxy, or octoxy, furthermore methyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, methoxy, nonoxy, decoxy, undecoxy, dodecoxy, tridecoxy or tetradecoxy, for example.
Oxaalkyl, i.e. where one CH
2
group is replaced by —O—, 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, for example.
In the compounds of formula I R may be an achiral or a chiral group. In case of a chiral group they are preferably selected according to the following formula III:
wherein
X
1
is —O—, —CO—, —COO—, —OCO—, —OCOO— or a single bond,
Q
1
is an alkylene or alkylene-oxy group with 1 to 10 C atoms or a single bond, in which the oxy group is preferably adjacent to the

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