Compositions – Liquid crystal compositions – Containing nonsteryl liquid crystalline compound of...
Reexamination Certificate
2000-12-22
2004-01-06
Huff, Mark F. (Department: 1756)
Compositions
Liquid crystal compositions
Containing nonsteryl liquid crystalline compound of...
C252S299610, C252S299630, C252S299010, C558S425000
Reexamination Certificate
active
06673267
ABSTRACT:
FIELD OF ART
The present invention relates to phenylacetylene compounds having a phenylacetylene structure and an acryl or methacryl group on both ends of the structure via a spacer, which compounds are useful for preparing optical, display, and recording materials, and also for preparing optical compensators, polarizers, reflector plates, and scattering plates, which are used for liquid crystal devices, or films having coloring effect, or useful as a material for preparing the above products or as a component of liquid crystal materials used for preparing liquid crystal display elements. The present invention also relates to liquid crystal compositions, polymers, optically anisotropic products, all containing such phenylacetylene compounds, and liquid crystal or optical elements utilizing the above.
BACKGROUND ART
There have recently been discussed possible applications of liquid crystalline materials not only to a switching element of a display for switching the display modes such as TN or STN mode, but also to retarder plates, polarizing plates, polarizing prisms, beam splitters, reflectors, holographic elements, color separators, or various optical filters, which make use of the optical anisotropy of the materials such as alignment and refractive index. Improvement in performance of display elements has become essential with the recent development in information-oriented society.
As techniqued for realizing production of optically anisotropic products from liquid crystalline materials, there are known, for example, methods of photopolymerizing a liquid crystalline compound having a polymerizable functional group or a polymerizable liquid crystal composition containing such a compound, by irradiating the compound or the composition in a liquid crystal state with ultra-violet or visible irradiation. These methods intend to, in other words, to produce a polymer wherein the alignment of liquid crystal molecules in a liquid crystal state is semipermanently fixed for achieving stable optical functions. As such liquid crystalline compounds having a polymerizable functional group, JP-A-11 116 534 and JP-A-11 80 081 propose mainly a compound having a phenylbenzoate core and a compound having a core including phenylbenzoate, cyclohexylphenyl, and tolan. The core structures of these compounds, however, do not give a high refractive index anisotropy (&Dgr;n).
On the other hand, as liquid crystalline compounds having a relatively high refractive index anisotropy, JP-A-2 83 340 and JP-A-9 216 841 propose conjugate compounds. However, such conjugate compounds do not have a sufficiently high refractive index anisotropy, have problems such as low solubility in other liquid crystals, and do not have a photopolymerizability.
DISCLOSURE OF THE INVENTION
It is therefore an object of the present invention to provide novel phenylacetylene compounds, liquid crystal compositions containing such a compound, polymers obtained from such a composition, and optically anisotropic products, which are expected to exhibit high refractive index anisotropy, easy to mix with other liquid crystal compounds, and has advantageous stability against light, and which may be used for preparation of optical compensators, polarizer materials, reflectors, scattering plates, or films having coloring effect.
It is another object of the present invention to provide liquid crystal or optical elements useful for producing optical shutters, display elements, or the like devices, which utilizes a novel phenylacetylene compound, a liquid crystal composition containing such a compound, a polymer obtained from such a composition, and an optically anisotropic product, which are expected to exhibit high refractive index anisotropy, easy to mix with other liquid crystal compounds, and has advantageous stability against light, and which may be used for preparation of optical compensators, polarizer materials, reflectors, scattering plates, or films having coloring effect.
According to the present invention, there is provided a phenylacetylene compound represented by the formula (1):
wherein A
1
to A
12
each independently stands for a hydrogen atom, a fluorine atom, or an alkyl or alkoxy group having 1 to 10 carbon atoms optionally substituted with at least one fluorine atom; B
1
and B
2
each stands for a hydrogen atom or a methyl group; p, q, r, s, and t each denotes 0 or 1, provided that when q is 0, at least one of A
2
and A
4
to A
10
stands for an alkyl or alkoxy group having 1 to 10 carbon atoms optionally substituted with at least one fluorine atom; m and n each denotes an integer of 0 to 14, provided that when s is 1, n is not 0, and when t is 1, m is not 0; W stands for a single bond, —CH
2
CH
2
—, or —C≡C—.
According to the present invention, there is also provided a liquid crystal composition comprising a phenylacetylene compound represented by the above formula (1).
According to the present invention, there is also provided a polymer obtained by polymerization of the above liquid crystal composition.
According to the present invention, there is further provided an optically anisotropic product produced using the above polymer.
According to the present invention, there is further provided a liquid crystal or optical element produced using at least one material selected from the group consisting of the phenylacetylene compound, the liquid crystal composition, the polymer, the optically anisotropic product.
Preferred Embodiments of the Invention
Phenylacetylene compounds of the present invention are represented by the formula (1) In the formula (1) A
1
to A
12
each independently stands for a hydrogen atom, a fluorine atom, or an alkyl or alkoxy group having 1 to 10 carbon atoms optionally substituted with at least one fluorine atom. B
1
and B
2
each stands for a hydrogen atom or a methyl group. p, q, r, s, and t each denotes 0 or 1, provided that when q is 0, at least one of A
2
and A
4
to A
10
stands for an alkyl or alkoxy group having 1 to 10 carbon atoms optionally substituted with at least one fluorine atom. m and n each denotes an integer of 0 to 14, provided that when s is 1, n is not 0, and when t is 1, m is not 0. W stands for a single bond, —CH
2
CH
2
—, or —C≡C—.
Examples of the phenylacetylene compounds represented by the formula (1) may include those represented by the formulae below, wherein m and n each denotes an integer of 1 to 14. Particularly preferred are phenylacetylene compounds represented by the formula (1 ) wherein at least one of A
4
, A
5
, A
9
and A
10
stands for an alkyl or alkoxy group having 1 to 10 carbon atoms optionally substituted with at least one fluorine atom, or phenylacetylene compounds represented by the formula (1 ) wherein s and t both denote 1.
The phenylacetylene compounds of the present invention may be synthesized through ordinary organic synthesizing processes, for example, in accordance with the synthesizing process mentioned below, which is a combination of known unit processes.
Compounds represented by the formula (1) wherein (p, q, r, s, t)=(0, 0, 0, 0, 0), referred to as compound (1aa) hereinbelow, may be produced, for example, according to the following synthesizing process.
In the formulae above, A
2
, A
4
to A
10
, B
1
, B
2
, m, and n mean the same as in the formula (1). X
1
, X
2
, and X
6
to X
8
each independently stands for a halogen atom, and X
3
to X
5
each independently stands for a halogen atom, —OSO
2
CF
3
, or —OSO
2
C
4
F
9
. Y
1
stands for —CF
3
or —C
4
F
9
, and P
1
to P
3
each independently stands for a protecting group for a hydroxyl group.
The reaction for preparing the compound represented by the formula (7) from the compound represented by the formula (6) in the above example of synthesis may be effected, for example, through the following Method (A1) or (B1):
Method (A1): Reacting the compound represented by the formula (6) with 1,1-dimethyl-2-propynol in the presence of copper iodide, a palladium catalyst, or a base such as triethylamine, followed by reaction with a base such as an alkali hydroxide;
Met
Fujisawa Koichi
Iwakura Kazunori
Minai Masayoshi
Sekine Chizu
Huff Mark F.
Sadula Jennifer R
Sumitomo Chemical Company Limited
LandOfFree
Phenylacetylene compound, liquid crystal composition,... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Phenylacetylene compound, liquid crystal composition,..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Phenylacetylene compound, liquid crystal composition,... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3240947