Polycyclo Ring System Patents (Class 570/183)
  • Patent number: 7270856
    Abstract: The invention relates to novel cyclobutane derivatives of the formula (I), in which R1, R2, A, Z, m, n and o have the meaning indicated in claim 1, to the use thereof as components of liquid-crystalline media, and to liquid-crystal and electro-optical display elements which contain the liquid-crystalline media according to the invention
    Type: Grant
    Filed: November 5, 2003
    Date of Patent: September 18, 2007
    Assignee: Merck Patent GmbH
    Inventors: Andreas Taugerbeck, Michael Heckmeier, Peer Kirsch, Georg Luessem, Eike Poetsch
  • Patent number: 7255900
    Abstract: In the compound of the formula (I), where: R1, R2 are each independently, for example, H or a straight-chain or branched alkyl radical p, q are each independently 0 or 1, i.e. at the value zero, —H is present at the appropriate position instead of —F M1 is —CO—O—, —O—CO—, —CH2—O—, —O—CH2—, —CF2—O—, —O—CF2—, —CH?CH—, —CF?CF—, —C?C—, —CH2—CH2—CO——O—, —O—CO—CH2—CH2—, —CH2—CH2—, —CF2—CF2—, —(CH2)4—, —OC(?O)CF?CF— or a single bond A1 is, for example, 1,4-phenylene R5 has the same possible definitions as specified for R1 and R2, with the exception of —M1—A1—R5, but independently of the definition of R1 and R2 X is H, F, OF3, CF3, OCF2H with the following provisos: a) at least one of p, q has to be 1 b) R1 and R2 must not at the same time be H c) R2 and X must not at the same time be H.
    Type: Grant
    Filed: April 28, 2005
    Date of Patent: August 14, 2007
    Assignee: Merck Patent GmbH
    Inventors: Wolfgang Schmidt, Rainer Wingen, Barbara Hornung
  • Patent number: 7232592
    Abstract: The present invention provides a nematic liquid crystal composition using a 4,6-difluoroindane-based compound that has a low lower limit temperature (T?N) of the liquid crystal phase, high upper limit temperature (TN-I) of the liquid crystal phase, and wide liquid crystal phase temperature range without impairing response speed, threshold voltage and other liquid crystal characteristics within a the range of the optimal ?n as a nematic liquid crystal, and a 4,6-difluoroindane-based compound that is used in said liquid crystal composition. The nematic liquid crystal composition contains at least one type of compound having a 4,6-difluoroindan-2,5-diyl group, and the refractive index anisotropy is within the range of 0.08 to 0.15, the liquid crystal phase upper limit temperature is 70° C. or higher, the liquid crystal phase lower limit temperature is ?20° C. or lower, and the difference between the liquid crystal phase upper limit temperature and liquid crystal phase lower limit temperature is 90° C. or more.
    Type: Grant
    Filed: November 27, 2003
    Date of Patent: June 19, 2007
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Yasuo Umezu, Shotaro Kawakami, Kiyofumi Takeuchi, Tetsuo Kusumoto, Shinji Ogawa
  • Patent number: 7214835
    Abstract: The present invention provides 1,7,8-trifluoro-2-naphthol and a derivative thereof as intermediates for efficiently producing a trifluoronaphthalene liquid crystal material. A method for efficiently producing a trifluoronaphthalene liquid crystal material using such intermediates is also disclosed. A naphthol derivative having the following general formula (I) is disclosed.
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: May 8, 2007
    Assignee: Dainippon Ink & Chemicals, Inc.
    Inventors: Tetsuo Kusumoto, Yutaka Nagashima, Sadao Takehara, Takashi Matsumoto
  • Patent number: 7157124
    Abstract: A compound represented by formula (1) or (2) and a polymer obtained by polymerizing the compound are provided: wherein Ra is one of the groups represented by Formulas (3-1) to (3-5); Rb is hydrogen, halogen, or a side chain such as —CN, —NCO, —NCS or alkyl having a carbon number of 1 to 20; A is a cyclic diyl group such as 1,4-cyclohexylene, 1,4-cyclohexenylene, 1,4-phenylene, naphthalene-2,6-diyl, tetrahydronaphthalene-2,6-diyl, fluorene-2,7-diyl, bicyclo[2.2.2]oct-1,4-diyl or bicyclo[3.1.0]hex-3,6-diyl, wherein at least one A is substituted 1,4-phenylene represented by Formula (4-1) or (4-2); Z is a single bond or a bonding group such as alkylene having a carbon number of 1 to 20; Rc is hydrogen, halogen, —CF3 or alkyl having a carbon number of 1 to 5; m is an integer of 1 to 6, and q is 0 or 1.
    Type: Grant
    Filed: January 5, 2004
    Date of Patent: January 2, 2007
    Assignees: Chisso Petrochemical Corporation, Chisso Corporation
    Inventors: Yasuyuki Sasada, Kazuhiko Saigusa
  • Patent number: 7145047
    Abstract: Disclosed in a novel liquid-crystalline compound which is a naphthalene derivative useful as an electro-optical liquid crystal display material, a liquid crystal composition containing such naphthalene derivatives and a liquid crystal display device comprising the same. The naphthalene derivative provided by the present invention exhibits an excellent liquid-crystallinity and miscibility with currently widely used liquid crystal compositions or compositions. The addition of the naphthalene derivative makes it possible to drastically lower the threshold voltage of the liquid crystal composition while maintaining its high response. The naphthalene derivative of the present invention is characterized by a large birefringence index. Further, most of the naphthalene derivative of the present invention has no strongly polar group in its molecule and thus can also be used for active matrix driving.
    Type: Grant
    Filed: August 21, 2002
    Date of Patent: December 5, 2006
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Sadao Takehara, Masashi Osawa, Haruyoshi Takatsu, Makoto Negishi
  • Patent number: 7125589
    Abstract: A compound represented by the following formula (1), a composition comprising the composition and an element comprising the composition: Ra is alkyl having 1 to 15 carbons and so forth; A1, A2 and A3 are 1,4-cyclohexylene and so forth; Z1, Z2 and Z3 are a single bond and so forth; n and m are 0 or 1; and phenyl having (F)p is phenyl, 2-fluorophenyl and so forth.
    Type: Grant
    Filed: April 9, 2003
    Date of Patent: October 24, 2006
    Assignees: Chisso Corporation, Chisso Petrochemical Corporation
    Inventors: Keiji Kimura, Shuichi Matsui
  • Patent number: 7122228
    Abstract: The invention relates to indanes having negative ?? of the formula Ia or Ib in which R, A, Z, X, Y, V, W, n and m are as defined in claim 1. The compounds are particularly suitable for producing VA-TFT displays.
    Type: Grant
    Filed: July 19, 2002
    Date of Patent: October 17, 2006
    Assignee: Merck Patent GmbH
    Inventors: Volker Reiffenrath, Michael Heckmeier, Matthias Bremer
  • Patent number: 7102023
    Abstract: One aspect of the present invention relates to optionally substituted halogenated benzyl halides and the like. These compounds are useful as halogenated benzyl ether-based protecting groups for a variety of functional groups. Another aspect of the present invention relates to use of said protecting groups in an orthogonal protecting group strategy for the synthesis of complex molecules that comprise a number of suitable functional groups. Another aspect of the present invention relates to saccharides bearing various arrays of protecting groups of the present invention. Another aspect of the present invention relates to a method of synthesizing an oligosaccharide or glycoconjugate, comprising the steps of: using a saccharide bearing at least one protecting group of the present invention to glycosylate a second molecule to give a product comprising said saccharide; and removing a protecting group of the present invention from said product.
    Type: Grant
    Filed: February 6, 2004
    Date of Patent: September 5, 2006
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Obadiah J. Plante, Peter H. Seeberger
  • Patent number: 7087272
    Abstract: The invention relates to fluorinated fluorene derivatives of negative DC anisotropy, of the formula I R1—(—A1—Z1—)k1—(—A2—Z2—)k2—W—(—Z3—A3—)k3—(—Z4—A4—)k4—R2I in which W denotes the sub-formula L1 and L2, independently of one another, are H, F, Cl, —CH2F, —CHF2 or —CF3, with the proviso that L1 and L2 are not both H, L3 and L4, independently of one another, are H or F, and R1, R2, A1, A2, A3, A4, Z1, Z2, Z3, Z4, k1, k2, k3 and k4 are as defined above. The invention furthermore relates to liquid-crystalline media and to optical and electro-optical display elements.
    Type: Grant
    Filed: March 7, 2002
    Date of Patent: August 8, 2006
    Assignee: Merck Patent GmbH
    Inventors: Matthias Bremer, Detlef Pauluth, Melanie Klasen-Memmer
  • Patent number: 7070838
    Abstract: The present invention provides a compound represented by formula (1) defined in the specification and a liquid crystal composition comprising the compound. The invention further provides a polymer obtained by polymerization of compound or composition above, and further the present invention provides a film, an optical anisotropic material, A ¼ or ½ wavelength functional plate, an optical compensation element, an optical element and a liquid crystal display element employing the polymer.
    Type: Grant
    Filed: June 23, 2004
    Date of Patent: July 4, 2006
    Assignees: Chisso Petrochemical Corporation, Chisso Corporation
    Inventors: Yasuyuki Sasada, Motoki Yanai
  • Patent number: 7067179
    Abstract: A novel compound represented by the general formula (I), and a nematic liquid crystal composition incorporating the same. A compound represented by the general formula (I) can be produced industrially extremely easily, as shown in the examples, displays superior compatibility with current general purpose host liquid crystals as a nematic phase, and also shows little crystal precipitation at low temperatures. Moreover, by addition of a small amount of such a compound to a host liquid crystal, the liquid crystal temperature range at low temperatures can be effectively widened without any significant worsening of the various characteristics of the liquid crystal material. Consequently, a compound of the present invention is an extremely useful liquid crystal material which is suitable for various liquid crystal display elements which require a broad operating temperature range.
    Type: Grant
    Filed: September 10, 1999
    Date of Patent: June 27, 2006
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Shinji Ogawa, Tatsuo Kawara, Sadao Takehara, Hiroyuki Ohnishi, Kiyofumi Takeuchi, Haruyoshi Takatsu, Gerwald Grahe, Rainer Bruno Frings, Christine Fugger, Cornelia Pithart
  • Patent number: 7026021
    Abstract: Compounds of the general formula (I) where: R1, R2 are each independently a) H b) -M1-A1-R5 c) a straight-chain or branched alkyl radical having from 1 to 16 carbon atoms or a straight-chain or branched alkenyl radical having from 2 to 16 carbon atoms, where c1) one or more nonadjacent and nonterminal CH2 groups may be replaced by —O—, —C(?O)O—, —O—C(?O)—, —O—C(?O)—O—, —C(?O)— or —Si(CH3)2—, and/or c2) one CH2 group may be replaced by —C?C—, cyclopropane-1,2-diyl, cyclobutane-1,3-diyl, cyclohexane-1,4-diyl or phenylene-1,4-diyl, and/or c3) one or more hydrogen atoms may be replaced by F and/or Cl, p, q are each independently 0 or 1 G1-G2 is —CH2CH—, —CH?C—, —CH2CH2CH— or —CH?CH—CH— M1 is —CO—O—, —O—CO—, —CH2—O—, —O—CH2—, —CF2—O—, —O—CF2—, —CH?CH—, —CF?CF—, —C?C—, —CH2—CH2—CO—O—, —O—CO—CH2—CH2—, —CH2—CH2—, —CF2—CF2—, —(CH2)4—, —OC(?O)CF?CF— or a single bond, A1 is 1,4-phenylene where one or two hydrogen atoms may be replaced by F, Cl, CN and/or OCF3, or up to three hydrogen atoms may be replaced by
    Type: Grant
    Filed: July 30, 2004
    Date of Patent: April 11, 2006
    Assignee: Merck Patent GmbH
    Inventors: Rainer Wingen, Barbara Hornung, Wolfgang Schmidt
  • Patent number: 7014890
    Abstract: Compounds of the formula (I) in which the parameters are as defined herein, are suitable for use in liquid-crystal media and liquid-crystal displays which contain these media.
    Type: Grant
    Filed: June 9, 2003
    Date of Patent: March 21, 2006
    Assignee: Merck Patent GmbH
    Inventors: Matthias Bremer, Melanie Klasen-Memmer, Barbara Hornung, Wolfgang Schmidt, Rainer Wingen
  • Patent number: 6974877
    Abstract: A process for preparing substituted pentacene compounds comprises the step of cyclizing substituted bis(benzyl)phthalic acids using an acid composition comprising trifluoromethanesulfonic acid, the substituted bis(benzyl)phthalic acids being represented by the following general formulas: wherein each R (that is, each of the groups R1 through R8) is independently an electron-donating group, a halogen atom, a hydrogen atom, or a combination thereof.
    Type: Grant
    Filed: September 27, 2002
    Date of Patent: December 13, 2005
    Assignee: 3M Innovative Properties Company
    Inventors: Dennis E. Vogel, Kim M. Vogel
  • Patent number: 6963017
    Abstract: A process for the preparation of indanones of the formula II from indanones of the formula I or of indanones of the formula IIa from indanones of the formula Ia comprises reacting an indanone of the formula I or Ia with a coupling component.
    Type: Grant
    Filed: July 22, 2002
    Date of Patent: November 8, 2005
    Assignee: Basell Polyolefine GmbH
    Inventors: Carsten Bingel, Markus Goeres, Volker Fraaije, Andreas Winter
  • Patent number: 6943257
    Abstract: The present invention provides a process for preparing an aromatic bromide or aromatic iodide from an aromatic amine derivative using nitrite anion and halodimethylsulfonium halide generated in situ from hydrobromic acid/DMSO or hydriodic acid/DMSO. The process for producing compounds of the formula (1) is disclosed (1) wherein X is bromine or iodine: Y is carbon or nitrogen; R1, R2, R3, R4 and R5 which may be the same or different and are selected independently from the group consisting of a hydrogen, a hologen, a C1-C8 alkyl, a C1-C10 alkoxy, a nitro, a formyl, an aryl, a benzyl, a C2-C10 alkylcarbonyl and an arylcarbonyl, provided that adjacent groups as selected from R1, R2, R3, R4 and R5 may combine to form a ring.
    Type: Grant
    Filed: September 21, 2001
    Date of Patent: September 13, 2005
    Inventors: Woon Phil Baik, Jung Min Kim, Young Sam Kim, Cheol Hun Yoon, Shin Jong Kim, Seok Woo Lee
  • Patent number: 6933063
    Abstract: Provided are spirobifluorene compounds which can provide excellent processibility with improved solubility in organic solvents, an electroluminescence (EL) polymer obtained therefrom and an EL element having the same. The EL polymer comprising repeating units of the following formula: wherein R1 and R2 are identical or different and are independently a straight-chain or branched alkyl group having from 1 to 22 carbon atoms or an aryl group substituted by C1-C22 alkyl, and at least one of the R1 and R2 contains one or more atoms selected from the group consisting of O, N, S, Si and Ge.
    Type: Grant
    Filed: November 30, 2001
    Date of Patent: August 23, 2005
    Assignee: Electronics and Telecommunications Research Institute
    Inventors: Jeong Ik Lee, Hyoyoung Lee, Jiyoung Oh, Hye Yong Chu, Lee-Mi Do, Seong Hyun Kim, Taehyoung Zyung
  • Patent number: 6887533
    Abstract: Compounds of the formula (I) where: X1 is H or F G1-G2 is —CH2—CH— or CH?C— R1, R2 are a) H b) the M2-A2-R5 moiety c) for example, a straight-chain or branched alkyl radical having from 1 to 16 carbon atoms R3 and R4 are each, for example, H, the M2-A2-R5 moiety or a straight-chain or branched alkyl or alkyloxy radical having from 1 to 16 carbon atoms A2 is, for example, 1,4-phenylene, with the provisos that a) when R2 is not H, R1 and R3 have to be H, b) when R2 is H, R4 must not have the definitions c) or d), c) R1, R2, R3 and R4 must not at the same time be H.
    Type: Grant
    Filed: March 24, 2004
    Date of Patent: May 3, 2005
    Assignee: Clariant International, Ltd.
    Inventors: Wolfgang Schmidt, Barbara Hornung, Rainer Wingen
  • Patent number: 6875895
    Abstract: Provided is a bis(diphenylvinyl)arene compound having a reactive functional group on phenyl group, represented by below formula (1), wherein, Ar is an arylene group and has one or more substituents; R1-R22 each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, etc., and at least one of R1-R20 is a halogen atom, etc. The arene compound has sufficient solubility in an organic solvent and excellent reactivity.
    Type: Grant
    Filed: August 20, 2002
    Date of Patent: April 5, 2005
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takahiro Ueoka, Hideyuki Ikehira, Yoshiaki Tsubata
  • Patent number: 6864396
    Abstract: Substituted pentacene compounds comprise at least one substituent selected from the group consisting of electron-donating substituents, halogen substituents, and combinations thereof; the substituent(s) each being bonded to a carbon atom of a terminal ring of pentacene, and being the only substituent(s); with the proviso that when the compound has only two substituents, both of which are methyl or alkoxy, and one substituent is bonded to the number 2 carbon atom, the other substituent, if methyl, is bonded to the number 1, 3, 4, 8, or 11 carbon atom and, if alkoxy, is bonded to the number 1, 3, 4, 8, 9, or 11 carbon atom; and with the further proviso that when the compound has only four substituents, all of which are alkoxy, the substituents are bonded to the numbers 2, 3, 9, and 10 carbon atoms.
    Type: Grant
    Filed: September 27, 2002
    Date of Patent: March 8, 2005
    Assignee: 3M Innovative Properties Company
    Inventors: Terrance P. Smith, Dennis E. Vogel, Kim M. Vogel
  • Patent number: 6812311
    Abstract: A method of producing a highly stable packaging substrate in which are provided a first precursor having a first backbone and a first ethynyl group, and a second precursor having a second backbone and a second ethynyl group. Furthermore provided is a crosslinker having a first and a second reactive group. The first precursor, the second precursor, the crosslinker, and a solvent are applied onto a surface to form an electrically insulating layer. The first ethynyl group is reacted with the first reactive group in a first carbon-carbon bond formation reaction and the second ethynyl group is reacted with the second reactive group in a second carbon-carbon bond formation reaction to crosslink the first backbone with the second backbone, thereby forming the packaging substrate. The solvent is removed in a further step.
    Type: Grant
    Filed: October 18, 2001
    Date of Patent: November 2, 2004
    Assignee: Honeywell International Inc.
    Inventors: Thomas McCarthy, Michael Wagaman, David Schwind
  • Patent number: 6759103
    Abstract: The invention relates to compounds of the formula (I) and also liquid-crystal mixtures comprising these compounds, and their use in liquid-crystal displays: in which R1 is H, F, CF3, OCF3, OCF2H, OCFH2, an alkyl radical or alkyloxy radical or an alkenyl radical or alkenyloxy radical, R2 is H, an alkyl radical or alkyloxy radical or an alkenyl radical or alkenyloxy radical, M1 and M2 are —C(═O)O—, —OC(═O)—, —CH2O—, —OCH2—, —OCF2—, —CF2O—, —C≡C—, —CH2CH2—, —CF2CF2—, —CF═CF—C(═O)O— or a single bond A1 and A2 are &agr;-1,4-diyl, unsubstituted or mono- or disubstituted by F; where &agr; is: phenylene cyclohexane, 1-cyclohexene, or 1,3-dioxane-2,5-diyl m and n are zero or 1; m+n=0 or 1 L1, L2, L3, L4 and L5 are H or F.
    Type: Grant
    Filed: September 12, 2002
    Date of Patent: July 6, 2004
    Assignee: Clariant Financi (BVI) Limited
    Inventors: Barbara Hornung, Wolfgang Schmidt, Rainer Wingen
  • Patent number: 6746728
    Abstract: A tetrahydronaphthalene derivative represented by the general formula (I) and a liquid crystal composition containing the same. A compound represented by the general formula (I) shows superior liquid crystallinity and co-solubility with conventional liquid crystal compounds and compositions. Furthermore, addition of such a compound enables the threshold voltage to be significantly reduced with almost no deleterious effect on the responsiveness. In addition, a compound of the present invention can also be easily produced industrially, is colorless, and is chemically stable. Consequently, liquid crystal compositions containing such a compound are extremely useful as liquid crystals, and are particularly suitable for liquid crystal displays requiring a wide operating temperature range, low voltage driving and a high response speed.
    Type: Grant
    Filed: December 28, 2001
    Date of Patent: June 8, 2004
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Tetsuo Kusumoto, Yoshitaka Saito, Makoto Negishi, Yutaka Nagashima, Sadao Takehara, Haruyoshi Takatsu, Gerwald Grahe, Rainer Bruno Frings, Cornelia Pithart
  • Patent number: 6740263
    Abstract: The present invention discloses an anthracene compound represented by the following formula 4 and chemiluminescent composition comprising the compound: wherein R is an alkyl group having 1-8 carbon atoms, and X1 and X2 are independently hydrogen or halogen.
    Type: Grant
    Filed: February 7, 2002
    Date of Patent: May 25, 2004
    Inventors: Koon Ha Park, Yong Fan Kim, Min Seob Park
  • Patent number: 6737125
    Abstract: Compounds of the formula (I), liquid-crystal mixtures comprising these compounds, and their use in liquid-crystal displays: in which R1 is H, F, CF3, OCF3, OCF2H, OCFH2, an alkyl radical or alkyloxy radical or an alkenyl radical or alkenyloxy radical; R2 is H, an alkyl radical or alkyloxy radical or an alkenyl radical or alkenyloxy radical M1 is —C(═O)O—, —OC(═O)—, —CH2O—, —OCH2—, —OCF2—, —CF2O—, —C≡C—, —CH2CH2—, —CF2CF2—, —CF═CFC(═O)O— or a single bond M2 is —C(═O)O—, —OC(═O)—, —CH2O—, —OCH2—, —CH2CH2—, —CF2CF2— or a single bond; A1 and A2 are &agr;-1,4-diyl, unsubstituted or mono- or disubstituted by F; where &agr; is: phenylene, cyclohexane, 1-cyclohexene or 1,3-dioxane-2,5-diyl; m and n are zero or 1; m+n=0 or 1 L1, L2, L3, L4 and L5 are H or F.
    Type: Grant
    Filed: September 12, 2002
    Date of Patent: May 18, 2004
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Barbara Hornung, Wolfgang Schmidt, Rainer Wingen
  • Patent number: 6716491
    Abstract: A liquid-crystalline medium based on a mixture of polar compounds of positive dielectric anisotropy, which comprises one or more compounds of the formula I where R1, A1, A2, Z1, Z2, L1, L2 and n are as defined herein, is suitable for use in, for example, MLC, TN and STN displays.
    Type: Grant
    Filed: May 8, 2001
    Date of Patent: April 6, 2004
    Assignee: Merck Patent GmbH
    Inventors: Kazuaki Tarumi, Brigitte Schuler, Matthias Bremer, Ulrich Finkenzeller, Eike Poetsch, Heike Kniel
  • Publication number: 20040041125
    Abstract: Compounds of the formula (I) 1
    Type: Application
    Filed: June 9, 2003
    Publication date: March 4, 2004
    Applicant: Merck Patent GmbH
    Inventors: Matthias Bremer, Melanie Klasen-Memmer, Barbara Hornung, Wolfgang Schmidt, Rainer Wingen
  • Patent number: 6682785
    Abstract: The invention relates to compounds of the formula (I) having a fluorinated anthracene or fluorinated tetrahydroanthracene core structure and to liquid-crystal mixtures comprising these compounds and to the use thereof in liquid-crystal displays.
    Type: Grant
    Filed: September 12, 2002
    Date of Patent: January 27, 2004
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Rainer Wingen, Barbara Hornung, Wolfgang Schmidt
  • Patent number: 6610219
    Abstract: Functional optical materials for optical systems that are typically useful in optical waveguides, optical switching systems, optical modulators, optical computing systems and the like. Included are polymer systems and electrooptical chromophores. Polymers are thermoplastic and/or thermosetting polymers and are blended or co-polymerized with the electrooptic chromophore. The thermoplastic or thermosetting polymer selected from an acrylic/methacrylic, polyester, polyurethane, polyimide, polyamide, epoxy resin, or hybrid (organic-inorganic) or nanocomposite polyester polymer. The electrooptic chromophore is selected from a substituted aniline, substituted azobenzene, substituted stilbene, or substituted imine. Methods for improving adhesion promotion for the various novel materials are also provided.
    Type: Grant
    Filed: February 6, 2001
    Date of Patent: August 26, 2003
    Assignee: Battelle Memorial Institute
    Inventors: Vincent D. McGinniss, Steven M. Risser
  • Publication number: 20030136944
    Abstract: Disclosed in a novel liquid-crystalline compound which is a naphthalene derivative useful as an electro-optical liquid crystal display material, a liquid crystal composition containing such naphthalene derivatives and a liquid crystal display device comprising the same. The naphthalene derivative provided by the present invention exhibits an excellent liquid-crystallinity and miscibility with currently widely used liquid crystal compositions or compositions. The addition of the naphthalene derivative makes it possible to drastically lower the threshold voltage of the liquid crystal composition while maintaining its high response. The naphthalene derivative of the present invention is characterized by a large birefringence index. Further, most of the naphthalene derivative of the present invention has no strongly polar group in its molecule and thus can also be used for active matrix driving.
    Type: Application
    Filed: August 21, 2002
    Publication date: July 24, 2003
    Applicant: Dainippon Ink and Chemicals, Inc.
    Inventors: Sadao Takehara, Masashi Osawa, Haruyoshi Takatsu, Makoto Negishi
  • Publication number: 20030065226
    Abstract: A method for preparing bromofluorenes includes a step of dispersing a compound selected from the group consisting of fluorene, fluorenone, and derivatives of fluorene and fluorenone in water to prepare a disperse system. Bromination is initiated by adding bromine Br2 into the disperse system. Thus, bromofluorenes can be efficiently and economically prepared without using any environmentally harmful organic solvent requiring a high cost to dispose of.
    Type: Application
    Filed: September 17, 2002
    Publication date: April 3, 2003
    Applicant: ADCHEMCO Corporation
    Inventors: Tetsuo Hachiya, Naoyuki Kitamura, Hiroaki Mori, Toshiyuki Yasuda
  • Patent number: 6534135
    Abstract: The invention relates to a process of preparing a discotic liquid crystalline compound by intramolecular oxidative cyclisation of a diaryl compound in an organic solvent in the presence of a strong acid, characterized in that an oxidative agent comprising a chrom(VI)oxide derivative is used, to discotic liquid crystalline compounds obtainable from said process, to liquid crystalline media, (co)polymers or polymer networks with columnar phases comprising said discotic liquid crystalline compounds, and to the use of said discotic liquid crystalline compounds, liquid crystalline media or liquid crystalline (co)polymers with columnar phases for liquid crystal displays, optical elements like polarizers, compensators or colour filters, chemical sensors, charge transport materials, optical storage media, nonlinear optics, decorative pigments, adhesive or synthetic resins with anisotropic mechanical properties.
    Type: Grant
    Filed: September 14, 2000
    Date of Patent: March 18, 2003
    Assignee: Merck Patent Gesellschaft
    Inventor: Mohammed Cherkaoui
  • Patent number: 6509507
    Abstract: A process for preparing polymerizable biaryl derivatives comprises reacting an aromatic comprising a 6-membered ring which bears ester or benzylic OH groups in the 1,4 position with a second aromatic in a palladium-catalyzed cross-coupling reaction to give a biaryl and converting the ester or benzylic OH groups into polymerizable groups in one or more steps. The biaryls obtained are suitable for preparing polymers which are used as electroluminescence materials.
    Type: Grant
    Filed: October 16, 2001
    Date of Patent: January 21, 2003
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Jochen Krause
  • Patent number: 6491847
    Abstract: A novel class of discotic liquid crystals represented by the following formula was synthesized, and a layer thereof was incorporated in an organic electroluminescence device.
    Type: Grant
    Filed: September 20, 2000
    Date of Patent: December 10, 2002
    Assignee: Canon Kabushiki Kaisha
    Inventors: Takao Takiguchi, Shinjiro Okada, Akira Tsuboyama, Shinichi Nakamura, Takashi Moriyama
  • Patent number: 6491989
    Abstract: Fluorinated naphthalene derivatives of the formula (I) R1(—A1—M1)a(—A2—M2)b—B—(—M3—A3)c—(M4—A4)d—R2  (I) where B is  having the meaning  and R1(—A1—M1)a(—A2—M2) and (—M3—A3)(M4—A4)R2 are mesogenic radicals, are suitable as components of liquid-crystal mixtures, in particular ferroelectric liquid-crystal mixtures.
    Type: Grant
    Filed: July 10, 2000
    Date of Patent: December 10, 2002
    Assignee: Aventis Reseach & Technologies GmbH & Co. KG
    Inventors: Javier Manero, Wolfgang Schmidt, Barbara Hornung
  • Patent number: 6485797
    Abstract: A ferroelectric liquid crystal mixture, especially useful for operation in the &tgr;Vmin−mode, comprises a 5-Arylindane derivative of the formula (I), wherein Y is CH, CF or N and R1(—A1—M1)a(—A2—M2)b—, (M3—A3—)cR2 are mesogenic groups.
    Type: Grant
    Filed: August 31, 2000
    Date of Patent: November 26, 2002
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Wolfgang Schmidt, Javier Manero, Barbara Hornung, Rainer Wingen, Ayako Ogawa
  • Patent number: 6482478
    Abstract: Fluorinated derivatives of phenanthrene, and their use in liquid-crystal mixtures Fluorinated phenanthrene derivatives of the formula (I)  in which G1 is —CH═CH— or —CH2CH2— X is H or F Y is H or F, and R1 and M1—A1—R2 are mesogenic radicals, are suitable as components of liquid-crystalline mixtures.
    Type: Grant
    Filed: September 5, 2000
    Date of Patent: November 19, 2002
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventor: Rainer Wingen
  • Patent number: 6468607
    Abstract: Disclosed is a novel liquid-crystalline compound which is a naphthalene derivative useful as an electro-optical liquid crystal display material, a liquid crystal composition containing such naphthalene derivatives and a liquid crystal display device comprising the same. The naphthalene derivative provided by the present invention exhibits an excellent liquid-crystallinity and miscibility with currently widely used liquid crystal compositions or compositions. The addition of the naphthalene derivative makes it possible to drastically lower the threshold voltage of the liquid crystal composition while maintaining its high response. The naphthalene derivative of the present invention is characterized by a large birefringence index. Further, most of the naphthalene derivative of the present invention has no strongly polar group in its molecule and thus can also be used for active matrix driving.
    Type: Grant
    Filed: April 22, 1999
    Date of Patent: October 22, 2002
    Assignee: Dainippon Ink and Chemicals, Inc.
    Inventors: Sadao Takehara, Masashi Osawa, Haruyoshi Takatsu, Makoto Negishi
  • Patent number: 6465700
    Abstract: Novel 2-substituted 7-haloindenes and methods for synthesizing such indenes are described. The 2-substituted 7-haloindenes may be coupled with any aryl group to produce a metallocene catalyst intermediate.
    Type: Grant
    Filed: August 3, 1998
    Date of Patent: October 15, 2002
    Assignee: Boulder Scientific Company
    Inventors: Jeffrey M. Sullivan, Hamlin H. Barnes
  • Patent number: 6380445
    Abstract: Soluble poly(bis-9,9′-fluorenes) comprise identical or different structural repeating units of the formula I, where the two R1s are, independently of one another, H, C1-C18alkyl, C6-C14aryl, C7-C15aralkyl, C1-C18alkoxy, R2—(O—CnH2n)m—O—, C1-C18alkylthio, C1-C18dialkylamino, —C(O)OH, —C(O)O—C1-C18alkyl, —C(O)—N(C1-C18alkyl)2, —SO3H, —SO3—C1-C18alkyl, —SO2—N(C1-C18alkyl)2, C1-C17alkyl-C(O)—O— or C1-C17alkyl-C(O)—, R2 is H or C1-C12alkyl, n is from 2 to 6 and m is from 1 to 12. The polymers can be used either alone or in admixture with at least one additional fluorophore whose absorption band overlaps the emission band (fluorescent emission) of the polymer of the formula I as active radiative layer for light-emitting diodes, VDUs and display elements.
    Type: Grant
    Filed: May 9, 2000
    Date of Patent: April 30, 2002
    Assignee: Vantico Inc.
    Inventors: Ralf-Roman Rietz, Wolfgang Wernet
  • Patent number: 6350875
    Abstract: The synthesis of asymmetric tetrasubstituted cyclooctatetraenes (“COTs”) and the use of said compounds in organic light emitting diodes is reported, wherein said COTs represent a class of wide gap electron transporters that are readily deposited in vacuum.
    Type: Grant
    Filed: March 23, 2001
    Date of Patent: February 26, 2002
    Assignee: The University of Southern California
    Inventors: William P. Weber, Ping Lu, Mark E. Thompson, Haiping Hong
  • Patent number: 6323373
    Abstract: A process for preparing polymerizable biaryl derivatives comprises reacting an aromatic comprising a 6-membered ring which bears ester or benzylic OH groups in the 1,4 position with a second aromatic in a palladium-catalyzed cross-coupling reaction to give a biaryl and converting the ester or benzylic OH groups into polymerizable groups in one or more steps. The biaryls obtained are suitable for preparing polymers which are used as electroluminescence materials.
    Type: Grant
    Filed: June 9, 1999
    Date of Patent: November 27, 2001
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Jochen Krause
  • Patent number: 6309561
    Abstract: Fluorine-containing, chiral liquid crystal compounds comprise (a) a chiral fluorochemical terminal portion comprising (i) at least one chiral center, which can optionally be heteroatom-substituted; (ii) a terminal fluoroalkyl, fluoroether, perfluoroalkyl, or perfluoroether group; and (iii) an alkylene or fluoroalkylene group optionally containing at least one catenary ether oxygen atom; (b) a chiral or achiral terminal portion consisting of a hydrocarbon or hydrocarbon ether group, and, when chiral, comprising at least one chiral center, which can optionally be heteroatom-substituted; and (c) a central core connecting the terminal portions; the alkylene or fluoroalkylene group of the chiral fluorochemical terminal portion having at least 3 in-chain atoms and being located between the chiral center of the chiral fluorochemical terminal portion and the central core. The compounds have smectic mesophases or latent smectic mesophases and are useful, for example, in liquid crystal display devices.
    Type: Grant
    Filed: December 24, 1997
    Date of Patent: October 30, 2001
    Assignee: 3M Innovative Properties Company
    Inventors: Masakazu Hasegawa, Michael P. Keyes, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
  • Patent number: 6252001
    Abstract: Compounds of ethynyl aromatic compounds form polymers which have high thermal stability. The monomers are useful for coating a wide variety of substances such as dielectric coatings where high thermal resistance is desirable including electronic components such as computer chips.
    Type: Grant
    Filed: January 13, 2000
    Date of Patent: June 26, 2001
    Assignee: The Dow Chemical Company
    Inventors: David A. Babb, Dennis W. Smith, Jr., Steven J. Martin, James P. Godschalx
  • Patent number: 6217793
    Abstract: Provided are novel acetylene compounds which are useful as a component for a liquid crystal composition used for a liquid crystal element, a liquid crystal composition containing said compounds and a liquid crystal element using said liquid crystal composition. The acetylene compound is represented by Formula (1): n-CmH2m+1—C≡C—A—Z1—B—Y1—R1  (1) wherein m represents an integer of 2 to 24; R1 represents a linear or branched alkyl group, a linear or branched alkoxyalkyl group, a linear or branched alkenyl group, or a linear or branched alkenyloxyalkyl group each of which may be substituted with a halogen atom; R1 may have an asymmetric carbon atom, and the asymmetric carbon atom may be optically active; A and B represents a cyclic group such as a phenylene group, a biphenylene group, a naphthylene group and the like each of which may be substituted with a halogen atom.
    Type: Grant
    Filed: May 17, 1999
    Date of Patent: April 17, 2001
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Yoshiyuki Totani, Hiroe Kayashima, Tsutomu Ishida, Masakatsu Nakatsuka
  • Patent number: 6215008
    Abstract: Fluorescent dyes which fluoresce a variety of colors are prepared from substituted isoviolanthrone and substituted isoviolanthrone by reductive alkylation with alkyl halides in the presence of zinc.
    Type: Grant
    Filed: December 3, 1999
    Date of Patent: April 10, 2001
    Assignee: Rohm and Haas Company
    Inventor: Peter J. Heffron
  • Patent number: 6168838
    Abstract: Fluorinated phenanthrene derivatives and their use in liquid-crystalline mixtures Fluorinated phenanthrene derivatives of the formula (I) in which G is —CHF—CH2— or —CF═CH—, E1, E2, E3, E4, E5 and E6 are identical or different and are —CH—, —CF— or —N— and R1(—A1—M1)a(—A2—M2)b, (M3—A3—)c(M4—A4—)d R2 denote mesogenic radicals are suitable as components for liquid-crystalline mixtures, especially ferroelectric mixtures.
    Type: Grant
    Filed: August 19, 1999
    Date of Patent: January 2, 2001
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Wolfgang Schmidt, Javier Manero
  • Patent number: 6121495
    Abstract: Compounds of ethynyl aromatic compounds form polymers which have high thermal stability. The monomers are useful for coating a wide variety of substances such as dielectric coatings where high thermal resistance is desirable including electronic components such as computer chips.
    Type: Grant
    Filed: September 12, 1996
    Date of Patent: September 19, 2000
    Assignee: The Dow Chemical Company
    Inventors: David A. Babb, Dennis W. Smith, Jr., Steven J. Martin, James P. Godschalx
  • Patent number: RE39532
    Abstract: The novel metallocenes of the formula I in which, preferably, M1 is Zr or Hf, R1 and R2 are alkyl or halogen, R3 and R4 are hydrogen, R5 and R6 are alkyl or haloalkyl, —(CR8R9)m—R7—(CR8R9)n— is a single- or multi-membered chain in which R7 may also be a (substituted) hetero atom, m+n is zero or 1, and R10 is hydrogen, form, together with aluminoxanes as cocatalysts, a very effective catalyst system for the preparation of polyolefins of high stereospecificity and high melting point.
    Type: Grant
    Filed: July 17, 1997
    Date of Patent: March 27, 2007
    Assignee: Basell Polyolefine GmbH
    Inventors: Andreas Winter, Martin Antberg, Walter Spaleck, Jürgen Rohrmann, Volker Dolle