Title:
COLORLESS AND LOW VISCOSITY COMPOUNDS FOR LOW VOLTAGE LIQUID CRYSTAL OPERATION
Document Type and Number:
WIPO Patent Application WO2002008356
Kind Code:
A3
Abstract:
A colorless dopant is provided that has a viscosities approximately the same as that of liquid crystal compositions and supports low voltage operation. The dopants have one of three structures (1) byphenyl; (2) diphenyl-diacetylene; and (3) double tolane, and in each case, have an amino group (secondary or tertiary) attached at one end of the molecule, with at least one polar group at the other end of the molecule. Schematically, the generic structure may be illustrated as: (Formula 1) where R1 is an alkyl having from 1 to 12 carbon atoms, R2 is hydrogen or, independently of R1, an alkyl having from 1 to 12 carbon atoms, M is a polar group, X and Y are independently hydrogen or a polar group not necessarily the same as M, and (A) is (1) a single bond (biphenyl); (2) -CC-CC-(diphenyl-diacetylene); or (3) (Formula 2) (double tolane), where Z is hydrogen, F, or alkyl.
Inventors:
WU SHIN-TSON
Application Number:
PCT/US2001/023024
Publication Date:
April 18, 2002
Filing Date:
July 20, 2001
Export Citation:
Assignee:
RAYTHEON CO (US)
International Classes:
C07C211/52; C07C255/58; C09K19/18; C09K19/54; G02F1/13; C09K19/58; (IPC1-7): C09K19/58; C07C25/18; C07C25/24; C07C255/58
Domestic Patent References:
| WO1990001723A1 | 1990-02-22 |
Foreign References:
| GB2092169A | 1982-08-11 |
Other References:
SHENOY R A ET AL: "SYNTHESIS AND MESOMORPHIC PROPERTIES OF 4-ALKYLAMINO-4'-SUBSTITUTEDDI PHENYLDIACETYLENES", LIQUID CRYSTALS, TAYLOR AND FRANCIS LTD, LONDON, GB, vol. 27, no. 6, June 2000 (2000-06-01), pages 801 - 812, XP000932293, ISSN: 0267-8292
Q-Y CHEN ET AL: "Photo-induced electron-transfer reaction of aryl perfluoroalkanesulphonates with anilines", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER SEQUOIA. LAUSANNE, CH, vol. 66, no. 1, January 1994 (1994-01-01), pages 59 - 62, XP002161119, ISSN: 0022-1139
RUOLIENE, J. ET AL: "Liquid crystalline 4-alkylamino-4'-cyanobiphenyls", MOL. CRYST. LIQ. CRYST. (1981), 78(1-4), 211-16, XP002188948
WU, SHIN-TSON ET AL: "Colorless high dielectric compounds for low voltage liquid crystal application", MATER. RES. SOC. SYMP. PROC. (1999), 559(LIQUID CRYSTAL MATERIALS AND DEVICES), 235-242, XP008000156
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; MATSUMOTO, SHOICHI ET AL: "Nematic liquid crystal compositions for electrooptical display devices", XP002188949, retrieved from STN Database accession no. 89:120940
NGUYEN P ET AL: "SECOND-ORDER NONLINEAR OPTICAL PROPERTIES OF PUSH-PULL BIS(PHENYLETHYNYL)BENZENES AND UNSYMMETRIC PLATINUM BIS(PHENYLACETYLIDE) COMPLEXES", CHEMISTRY OF MATERIALS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 9, 1997, pages 406 - 408, XP001059403, ISSN: 0897-4756
FU, WEI ET AL: "Theoretical study on second-order nonlinear optical properties of unsymmetric bis(phenylethynyl)benzene series derivatives", CHIN. J. CHEM. (2000), 18(2), 175-181, XP008000155
FIALKOV, YU. A. ET AL: "Fluorine-containing liquid crystals. VIII. 4-Perfluoroalkyl-4'- alkylaminobiphenyls", ZH. ORG. KHIM. (1983), 19(5), 1048-53, XP008000157
MAUS, MICHAEL ET AL: "Monitoring pH and solvent proticity with donor-acceptor-substituted biphenyls: a new approach towards highly sensitive and powerful fluorescent probes by tuning the molecular structure", NEW J. CHEM. (2000), 24(9), 677-686, XP008000158
SHUJI OKADA ET AL: "PREPARATION AND NONLINEAR OPTICAL PROPERTY OF POLYDIACETYLENES FROM UNSYMMETRICAL DIPHENYLBUTADIYNES WITH TRIFLUOROMETHYL SUBSTITUENTS", MOLECULAR CRYSTALS AND LIQUID CRYSTALS (INC. NONLINEAR OPTICS ), GORDON AND BREACH SCIENCE PUBLISHERS, READING, GB, vol. 183, 1 June 1990 (1990-06-01), pages 81 - 90, XP000149409
Q-Y CHEN ET AL: "Photo-induced electron-transfer reaction of aryl perfluoroalkanesulphonates with anilines", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER SEQUOIA. LAUSANNE, CH, vol. 66, no. 1, January 1994 (1994-01-01), pages 59 - 62, XP002161119, ISSN: 0022-1139
RUOLIENE, J. ET AL: "Liquid crystalline 4-alkylamino-4'-cyanobiphenyls", MOL. CRYST. LIQ. CRYST. (1981), 78(1-4), 211-16, XP002188948
WU, SHIN-TSON ET AL: "Colorless high dielectric compounds for low voltage liquid crystal application", MATER. RES. SOC. SYMP. PROC. (1999), 559(LIQUID CRYSTAL MATERIALS AND DEVICES), 235-242, XP008000156
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; MATSUMOTO, SHOICHI ET AL: "Nematic liquid crystal compositions for electrooptical display devices", XP002188949, retrieved from STN Database accession no. 89:120940
NGUYEN P ET AL: "SECOND-ORDER NONLINEAR OPTICAL PROPERTIES OF PUSH-PULL BIS(PHENYLETHYNYL)BENZENES AND UNSYMMETRIC PLATINUM BIS(PHENYLACETYLIDE) COMPLEXES", CHEMISTRY OF MATERIALS, AMERICAN CHEMICAL SOCIETY, WASHINGTON, US, vol. 9, 1997, pages 406 - 408, XP001059403, ISSN: 0897-4756
FU, WEI ET AL: "Theoretical study on second-order nonlinear optical properties of unsymmetric bis(phenylethynyl)benzene series derivatives", CHIN. J. CHEM. (2000), 18(2), 175-181, XP008000155
FIALKOV, YU. A. ET AL: "Fluorine-containing liquid crystals. VIII. 4-Perfluoroalkyl-4'- alkylaminobiphenyls", ZH. ORG. KHIM. (1983), 19(5), 1048-53, XP008000157
MAUS, MICHAEL ET AL: "Monitoring pH and solvent proticity with donor-acceptor-substituted biphenyls: a new approach towards highly sensitive and powerful fluorescent probes by tuning the molecular structure", NEW J. CHEM. (2000), 24(9), 677-686, XP008000158
SHUJI OKADA ET AL: "PREPARATION AND NONLINEAR OPTICAL PROPERTY OF POLYDIACETYLENES FROM UNSYMMETRICAL DIPHENYLBUTADIYNES WITH TRIFLUOROMETHYL SUBSTITUENTS", MOLECULAR CRYSTALS AND LIQUID CRYSTALS (INC. NONLINEAR OPTICS ), GORDON AND BREACH SCIENCE PUBLISHERS, READING, GB, vol. 183, 1 June 1990 (1990-06-01), pages 81 - 90, XP000149409
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