Glass-forming liquid crystalline compositions and optical...

Compositions – Liquid crystal compositions

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C252S299610, C252S299620, C252S299660, C252S299670, C560S008000

Reexamination Certificate

active

06730242

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to glass-forming liquid crystals (GLC) and, more particularly, to liquid crystalline compositions comprising compounds having a molecular weight in the range of about 1000 to 5000 grams per mole, and to optical devices formed therefrom.
BACKGROUND OF THE INVENTION
Liquid crystallinity is a consequence of spontaneous molecular self-assembly into a uniaxial, lamellar, helical, or columnar arrangement on a macroscopic scale. Because of their unique optical properties, liquid crystals are potentially useful as optical, photonic and optoelectronic devices (see for example Collings, P. J., and Patel, J. S.,
Handbook of Liquid Crystal Research
, Oxford University Press, New York, 1997). In some of these applications, such as liquid crystal displays, the material functions in the fluid state where an applied field induces molecular reorientation with a response time on the order of milliseconds. With judiciously designed structural moieties, liquid crystals may also function in the solid state via a photonic or electronic stimulus with a much shorter response time. In addition, liquid crystals can be employed as passive devices in which no switching is involved. With the exception of applications in which molecular reorientation with an applied field is the basis, vitrified liquid crystals with an elevated glass transition temperature, T
g
, offer long-term mesomorphic stability as well as environmental durability. Whereas glass formation appears to be a privilege of liquid crystalline polymers, their generally high melt viscosity presents a major challenge to processing into large-area thin films. To combine ease of material processing with glass-forming ability in discrete molecular systems, extensive efforts have been made over the last two decades to develop glass-forming liquid crystals (GLCs) with well-defined structures having low to medium molecular weights (see for example Wedler, W. et al., 1991,
J. Mater. Chem.,
1, 347; Attard, G. S. et al., 1992,
Chem. Mater.,
4, 1246; Neumann, B. et al., 1997,
Adv. Mater.,
9, 241; and Gresham, K. D. et al., 1994,
J. Polym. Sci: Part A: Polym. Chem.,
32, 2039). Applications that have been explored with various GLCs include: optical data storage (see for example Ortler, R. et al., 1989,
Marromol. Chem., Rapid Commun,
10, 189; and Tamaoki, N. et al., 1997,
Adv. Mater.,
9, 1102), optical nonlinearity (see for example Wang, H. et al., 1996,
Nature,
384, 244; and Loddoch, M. et al., 1994,
Appl. Phys. B,
59, 591), photochromism (see for example Natarajan, L. V. et al., 1991,
Macromolecules,
24, 6554), tunable filters for optical communication (see for example Morita, Y. et al., 1999,
Jpn. J. Appl. Phys.,
38, Part. 1, 95), and viewing angle compensation for displays (see for example Van de Witte, P. et al., 1999,
Liquid Crystals,
26, 1039).
SUMMARY OF THE INVENTION
The present invention is directed to a glass-forming liquid crystal composition comprising a compound having a molecular weight in the range of about 1000 to 5000 grams per mole, and having the formula
(NEM)
x
—CYC—(CHI)
y
wherein CYC is a substituted cycloaliphatic core moiety containing about 24 to about 60 carbon atoms or a substituted aromatic core moiety containing about 6 to about 36 carbon atoms, NEM is a nematogenic pendant moiety, CHI is a chiral pendant moiety, x is 3 to 9, and y is 0 to 4. The invention is further directed to an optical device formed from the liquid crystal composition.


REFERENCES:
patent: 5332522 (1994-07-01), Chen et al.
patent: 5378393 (1995-01-01), Chen et al.
patent: 5417882 (1995-05-01), Bach et al.
patent: 5514296 (1996-05-01), Chen et al.
patent: 6248259 (2001-06-01), Izumi et al.
Collings, P.J. et al., Handbook of Liquid Crystal Research, Oxford University Press, New York (1997).
Wedler, W. et al., “Vitrification in Low-Molecular-Weight Mesogenic Compounds”, J. Mater. Chem. vol. 1, No. 3, 347-356 (1991).
Attard, G.S. et al., “Low Molar Mass Liquid-Crystalline Glasses: Preparation and Properties of the &agr;-(4-Cyanobiphenyl-4′-oxy)- -(1-pyreniminebenzylidene-4′-oxy)alkanes”, Chem. Mater., vol. 4, No. 6, 1246-1253 (1992).
Neumann, B. et al., “Liquid Crystalline Macrocycles: Novel Glass-Forming Nematic Materials That Can Undergo Charge Transfer Induced Phase Transitions”, Adv. Mater., vol. 9, No. 3, 241-244 (1997).
Gresham, K.D. et al., “Phase Behavior of Cyclic Siloxane-Based Liquid Crystalline Compounds”, Journal of Polymer Science: Part A: Polymer Chemistry, vol. 32, 2039-2047 (1994).
Ortler, R. et al., “Reversible Holographic-Optical Data Storage in Cholesteric Liquid-Crystalline Siloxanes”, Makromol. Chem., Rapid Commun., vol. 10, 189-194 (1989).
Tamaoki, N. et al., “Rewritable Full-Color Recording on a Thin Solid Film of a Cholesteric Low-Molecular-Weight Compound”, Adv. Mater., vol. 9, No. 14, 1102-1104 (1997).
Wang, H. et al., “Thermally Stable Nonlinear Optical Activity in a Smetic-A Liquid Crystal”, Nature, vol. 384, No. 21, 244-247 (1996).
Loddoch, M. et al., “Novel Glass-Forming Ferroelectric Liquid-Crystal Material of High Second-Order Nonlinearity”, Appl. Phys. B 59, 591-595 (1994).
Natarajan, L. V. et al., “Novel Photochromic Cholesteric Liquid Crystal Siloxane”, Macromolecules, vol. 24, No. 24, 6554-6556 (1991).
Morita, Y. et al., “Active Liquid Crystal Devices Incorporating Liquid Crystal Polymer Thin Film Waveplates”, Jpn. J. Appl. Phys. vol. 38, Pt. 1, No. 1A, 95-100 (1999).
Van De Witte, P. et al., “Optical Components From a New Vitrifying Liquid Crystal”, Liquid Crystals, vol. 26, No. 7, 1039-1046 (1999).
Chen, S. H. et al., “Novel Vitrifiable Liquid Crystals as Optical Materials”, Adv. Mater., vol. 8, No. 12, 998-1001 (1996).
Chen, S. H. et al., “Novel Glass-Forming Organic Materials. 1. Adamantane with Pendant Cholesteryl, Disperse Red 1, and Nematogenic Groups”, Macromolecules, vol. 28, No. 23, 7775-7778 (1995).
Chen, S. H. et al., “Novel Glass-Forming Organic Materials. 3. Cubane with Pendant Nematogens, Carbazole, and Disperse Red 1”, Macromolecules, vol. 30, No. 1, 93-97 (1997).
Chen, S. H. et al., “Novel Glass-Forming Liquid Crystals. IV. Effects of Central Core and Pendant Group on Vitrification and Morphological Stability”, Liquid Crystals, vol. 21, No. 5, 683-694 (1996).
Shi, H. et al., “Dynamic Mechanical Properties of Cyclohexane-Based Glass-Forming Liquid Crystals and a Linear Side Chain Polymer Analogue”, Liquid Crystals, vol. 20, No. 3, 277-282 (1996).
Shi, H. et al., “Dynamics of Defect Annihilation in Vitrified Liquid Crystalline (VLC) Thin Films Upon Thermal Annealing”, Mat. Res. Soc. Symp. Proc., vol. 425, 27-32 (1996).
Shi, H. et al., “Effects of Stereochemistry, Mesogenic Core and Spacer Length on Crystallization from Nematic and Isotropic Melts of Cyclohexane-Based Glass-Forming Liquid Crystals”, Liquid Crystals, vol. 19, No. 6, 785-790 (1995).
Katsis, D. et al., “Vitrified Chiral-Nematic Liquid Crystalline Films for Selective Reflection and Circular Polarization”, Chem. Mater., vol. 11, No. 6, 1590-1596 (1999).
Chen, S. H. et al., “Circularly Polarized Light Generated by Photoexcitation of Luminophores in Glassy Liquid-Crystal Films”, Nature, vol. 397, 506-508 (1999).
Collington, E. et al., “Selective Deprotection of Alcoholic and Phenolic Silyl Ethers”, Tetrahedron Letters, vol. 26, No. 5, 681-684 (1985).
Moore, J. S. et al., “Room Temperature Polyesterification”, Macromolecules, vol. 23, No. 1, 65-70 (1990).
Mastrangelo, J. et al., “Glass-Forming Ability and Morphological Stability of Cyclohexane and Biocyclooctene Rings Containing Disperse Red 1”, Chem. Mater., vol. 7, No. 10, 1904-1908 (1995).
Iordache, F. et al., “Bicyclo[2,2,2,]Octane Derivatives, I Stereoisomeric 5,6,7,8-Tetracarbomethoxybicyclo[2,2,2]Oct-2-Enes”, Revue Roumaine de Chimie, vol. 20, No. 2, 233-240 (1975).
Shi, H. et al., “Novel Glass-Forming Liquid Crystals. III Helical Sense and Twisting Power in Chiral Nematic Systems”, Liquid Crystals, vol. 19, No. 6, 849-861 (1995).
Chen, S.H. et al., “Circularly Polarized Light Produced with Gl

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Glass-forming liquid crystalline compositions and optical... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Glass-forming liquid crystalline compositions and optical..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Glass-forming liquid crystalline compositions and optical... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3228226

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.