Fluorinated cyclopenta[b]naphthalenes and their...

Stock material or miscellaneous articles – Liquid crystal optical display having layer of specified...

Reexamination Certificate

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C252S299610, C252S299620, C252S299630, C252S299670, C570S183000, C570S187000, C549S369000

Reexamination Certificate

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06759103

ABSTRACT:

More and more applications of LCDs—for example, use in automobiles, where temperatures across a range from −40° C. to 100° C. may readily occur, and also for portable devices such as cell phones and notebook PCs—are requiring liquid-crystal mixtures combining a very wide range of operating temperatures with a very low threshold voltage.
Consequently there is an ongoing demand for new, appropriate liquid-crystal mixtures and components of such mixtures. As described in Ichinose et al. (IDW,00, Abstr. LCT4-3) or in DE-A-100 50 071, the search is on for materials possessing at the same time both high optical anisotropy (&Dgr;n) and low rotational viscosity, along with other parameters such as, for example, high absolute dielectric anisotropy (&Dgr;&egr;) values, in addition to further application-relevant parameters.
It is an object of the present invention, therefore, to provide novel components for use in nematic or cholesteric or chiral smectic liquid-crystal mixtures which possess high absolute dielectric anisotropy values in combination with a favorable viscosity/clearing point relationship. Moreover, the compounds should be highly stable to light and UV and also to heat. Furthermore, they should be suitable for realizing high voltage holding ratios (VHRs). In addition, they should be readily available synthetically and thus potentially inexpensive.


REFERENCES:
patent: 4798680 (1989-01-01), Nohira et al.
patent: 5384065 (1995-01-01), Geelhaar et al.
patent: 5550236 (1996-08-01), Schlosser et al.
patent: 5744060 (1998-04-01), Tarumi et al.
patent: 5800734 (1998-09-01), Buchecker et al.
patent: 5997766 (1999-12-01), Kirsch et al.
patent: 6083573 (2000-07-01), Tarumi et al.
patent: 6159561 (2000-12-01), Schmidt et al.
patent: 6406761 (2002-06-01), Tarumi et al.
patent: 2001/0050352 (2001-12-01), Wingen et al.
patent: 44 27 266 (1995-02-01), None
patent: 195 28 085 (1996-02-01), None
patent: 195 28 665 (1997-02-01), None
patent: 196 29 812 (1997-02-01), None
patent: 195 32 292 (1997-03-01), None
patent: 196 07 996 (1997-09-01), None
patent: 196 54 487 (1998-07-01), None
patent: 198 40 447 (2000-03-01), None
patent: 198 57 352 (2000-06-01), None
patent: 100 50 071 (2001-06-01), None
patent: 100 26 661 (2001-11-01), None
patent: 0 318 423 (1989-05-01), None
patent: 0 343 830 (1989-11-01), None
patent: 0 474 062 (1992-03-01), None
patent: 0 665 825 (1995-08-01), None
patent: 0 736 513 (1996-10-01), None
patent: 0 952 135 (1999-10-01), None
patent: WO 92/11241 (1992-07-01), None
patent: WO 94/26692 (1994-11-01), None
patent: WO 96/00710 (1996-01-01), None
patent: WO 96/30344 (1996-10-01), None
CAPLUS 2003: 257327.*
English abstract for EP 0318423, May 31, 1989.
English abstract for WO 92/11241, Jul. 9, 1992.
English abstract for DE 4427266, Feb. 9, 1995.
English abstract for DE 19528085, Feb. 8, 1996.
English Abstract for DE 19607996, Sep. 11,1997.
English abstract for DE 19840447, Mar. 9, 2000.
English abstract for DE 19857352, Jun. 15, 2000.
English abstract for DE 10050071, Jun. 28, 2001.
Ichinose, H., et al., “High optical anisotrophy and small rotational viscosity LC mixture for field-sequential color TN-LCDs”, Seventh International Display Workshop, Nov. 25-Dec. 1, 2000, Kobe, Japan, IDW '00, pp. 77-80.
Meyer, A.Y., et al., “Planar and nonplanar unsaturation, preparation, properties, and molecular-orbital characterization of some fluoro-derivative of anthracene and anthraquinone”, Israel Journal of Chemistry, vol. 11, No. 6, 1973, pp. 791-804.
Olsen, Robert J., et al., “A photoannulation route to naphthalenes from cyclic ketones”, J. Org. Chem., 1991, 56; pp. 989-991.
Sakagami Sakumitsu, et al., “Mesomorphic properties of 2-(4-n-Alkoxybenzylideneamino)anthracenes”, Bulletin of the Chemical Society of Japan, vol. 50(4), pp. 1009-1010 (1977).
Sigreist, A.E. von, et al., “Uber die darstellung von styryl-derivaten aus methyl-substituierten carbocyclischen aromaten”, Helvatica Chimica Acta, vol. 52, fasc. 8 (1969), No. 253-254, pp. 2521-2554.
Haenel, Matthias W., et al., “Facile syntheses of 1,8-Bis(diphenylphosphino)anthracene and 1,8-Bis(dimethylamino)anthracene by nucleophilic substitution of 1,8-difluoroanthracene”, Synlett, Mar. 1998, pp. 301-303.
Cantrell, Gary L., “Synthesis of 1,2,3,4-tetrafluoro- and 1,2,3,4,5,6,7,8-octafluoroanthracenes via cycloaddition-revision”, Journal of Fluorine Chemistry, 29 (1985), pp. 417-424.
Hankinson, B., et al., “Aryne chemistry, Part XXX, Approaches to the synthesis of 9-alkyl and 9,10-dialkyl-1,2,3,4,5,6,7,8-octafluoro-9,10-dihydro-9,10-o-benzenoanthracenes (9-alkyl- and 9,10-dialkyl-1,2,3,4,5,6,7,8-octafluorotriptycenes)”, J.C.S. Perkin I, 1972, pp. 2372-2377.
Kiefer, R., et al., “P2-30 In-Plane switching of nematic liquid crystrals”, Japan Display, 1992, pp. 547-550.
Organikum, Organisch-Chemisches Grundpraktikum, Berlin 1984, pp. 612-616.
Cushman, Mark, et al., “Synthesis and evaluation of a series of benzylaniline hydrochlorides as potential cytotoxic and antimitotic agents acting by inhibition of tubulin polymerization”, J. Med. Chem., 1993, 36, pp. 2817-2821.
Gray, G.W., et al., “The synthesis of several lateral difluoro-substituted 4,4″-dialkyl- and 4,4″-alkoxyalkyl-terphenyls and a rationalisation of the effect of such substitution on mesophase type and transition temperatures”, Mol. Cryst. Liq. Cryst., 1991, vol. 204, pp. 43-64.
Bezborodov, V.S., et al., “The synthesis and properties of some mesomorphic cyclohexene derivatives” Liquid Crystals, 1997, vol. 23, No. 1, pp. 69-75.
Hird, Michael, et al., “The relationship between molecular structure and mesomorphic properties of 2,2′ — and 3,2 -difluoroterphenyls synthesized by palladium-catalysed cross-couplings”, Liquid Crystals 1995, vol. 18, No. 1, pp. 1-11.
Schlosser, Manfred, “Superbase reactions: the expedient and selective metalation of fluorino- or trifluoromethyl-substituted benzenes”, Synlett, Dec. 1990, pp. 747-748.
Butera, John, et al., “Computer-assisted design and synthesis of novel aldose reductase inhibitors”, J. Med. Chem., 1989, 32, pp. 757-795.
Cha, Jin Soon, et al., “Preparations of aldehydes from carboxylic esters by reductive oxidations with lithium aluminum hydride and pryidinium chlorochromate or pyridinium dichromate”, Bull. Korean Chem. Soc., 1999, vol. 20, No. 11, pp. 1373-1374.
Kanie, Kiyoshi, et al., “A convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithicarbonates”, Bull. Chem. Soc. Jpn., 73, (2000), pp. 471-484.
Collins, J.C., “Dipyridine-chromium(VI) oxide oxidation of alcohols in dichloromethane”, Tetrahedron Letter, No. 30, 1968, pp. 3363-3366.
Mongin, Florence, et al., “Regioselective ortho-lithiation of chloro and bromo substituted fluroarenes”, Tetrahedron Letters, vol. 37, No. 36, pp. 6551-6554.
Colley, Robert A., “Linear and network polymer electrolytes based on low melting prepolymers”, J. Mater. Chem., 1999, 9, pp. 1661-1667.
Gensler, Walter J., “Decarboxylative condensation. &agr;-alkylcinnamic acids from aromatic aldehydes and alkylmalonic acids”, J. American Chem. Soc., 80, Sep. 20, 1958, pp. 4949-4954.
Adcock, W., et al., “Substituent effects. VIII. Synthesis of substituted &agr;- and &bgr;-fluoronaphthalenes”, J. American Chem. Soc., 89:2, Jan. 18, 1967, pp. 386-390.
Mallory, Frank B., et al., “Substituent effects on through-space19F-19F Coupling in the 1,8-difluoronaphthalene system”, J. American Chem. Soc., 96:11, May 29, 1974, pp. 3536-3542.
Mitchell, Riginald H., et al., “Syntheses and reactions of the first dithia [3.1.3.1]metacyclophanes, [2.1.2.1]metacyclophanes, and [2.1.2.1]metacyclophanedienes”, J. Org. Chem., 1984, 49, pp. 2534-2540.
Sucrow, Wolfgang, et al., “Einige nematische derivate des all-trans-perhydrophenanthrens”, Chem. Ber., 118, 1985, pp. 3332-3349.
Coe, Paul Leslie, et al., “The lithiation of fluorinated benzenes and its dependence on solvent and temperature”, J. Chem. Soc. Perkin Trans., 1995, pp. 2729-2737.
Li, Min-Hui, et al., “Blue phases and twist grain boundary phases (TGBA and TGBC) in a series of fluoro-s

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