Polycyclo Ring System Patents (Class 570/183)
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Patent number: 7270856Abstract: 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 inventionType: GrantFiled: November 5, 2003Date of Patent: September 18, 2007Assignee: Merck Patent GmbHInventors: Andreas Taugerbeck, Michael Heckmeier, Peer Kirsch, Georg Luessem, Eike Poetsch
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Patent number: 7255900Abstract: 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: GrantFiled: April 28, 2005Date of Patent: August 14, 2007Assignee: Merck Patent GmbHInventors: Wolfgang Schmidt, Rainer Wingen, Barbara Hornung
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Patent number: 7232592Abstract: 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: GrantFiled: November 27, 2003Date of Patent: June 19, 2007Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Yasuo Umezu, Shotaro Kawakami, Kiyofumi Takeuchi, Tetsuo Kusumoto, Shinji Ogawa
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Patent number: 7214835Abstract: 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: GrantFiled: September 26, 2003Date of Patent: May 8, 2007Assignee: Dainippon Ink & Chemicals, Inc.Inventors: Tetsuo Kusumoto, Yutaka Nagashima, Sadao Takehara, Takashi Matsumoto
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Patent number: 7157124Abstract: 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: GrantFiled: January 5, 2004Date of Patent: January 2, 2007Assignees: Chisso Petrochemical Corporation, Chisso CorporationInventors: Yasuyuki Sasada, Kazuhiko Saigusa
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Patent number: 7145047Abstract: 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: GrantFiled: August 21, 2002Date of Patent: December 5, 2006Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Sadao Takehara, Masashi Osawa, Haruyoshi Takatsu, Makoto Negishi
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Patent number: 7125589Abstract: 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: GrantFiled: April 9, 2003Date of Patent: October 24, 2006Assignees: Chisso Corporation, Chisso Petrochemical CorporationInventors: Keiji Kimura, Shuichi Matsui
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Patent number: 7122228Abstract: 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: GrantFiled: July 19, 2002Date of Patent: October 17, 2006Assignee: Merck Patent GmbHInventors: Volker Reiffenrath, Michael Heckmeier, Matthias Bremer
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Patent number: 7102023Abstract: 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: GrantFiled: February 6, 2004Date of Patent: September 5, 2006Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Obadiah J. Plante, Peter H. Seeberger
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Patent number: 7087272Abstract: 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: GrantFiled: March 7, 2002Date of Patent: August 8, 2006Assignee: Merck Patent GmbHInventors: Matthias Bremer, Detlef Pauluth, Melanie Klasen-Memmer
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Patent number: 7070838Abstract: 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: GrantFiled: June 23, 2004Date of Patent: July 4, 2006Assignees: Chisso Petrochemical Corporation, Chisso CorporationInventors: Yasuyuki Sasada, Motoki Yanai
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Patent number: 7067179Abstract: 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: GrantFiled: September 10, 1999Date of Patent: June 27, 2006Assignee: 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
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Patent number: 7026021Abstract: 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 byType: GrantFiled: July 30, 2004Date of Patent: April 11, 2006Assignee: Merck Patent GmbHInventors: Rainer Wingen, Barbara Hornung, Wolfgang Schmidt
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Patent number: 7014890Abstract: 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: GrantFiled: June 9, 2003Date of Patent: March 21, 2006Assignee: Merck Patent GmbHInventors: Matthias Bremer, Melanie Klasen-Memmer, Barbara Hornung, Wolfgang Schmidt, Rainer Wingen
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Patent number: 6974877Abstract: 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: GrantFiled: September 27, 2002Date of Patent: December 13, 2005Assignee: 3M Innovative Properties CompanyInventors: Dennis E. Vogel, Kim M. Vogel
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Patent number: 6963017Abstract: 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: GrantFiled: July 22, 2002Date of Patent: November 8, 2005Assignee: Basell Polyolefine GmbHInventors: Carsten Bingel, Markus Goeres, Volker Fraaije, Andreas Winter
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Patent number: 6943257Abstract: 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: GrantFiled: September 21, 2001Date of Patent: September 13, 2005Inventors: Woon Phil Baik, Jung Min Kim, Young Sam Kim, Cheol Hun Yoon, Shin Jong Kim, Seok Woo Lee
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Patent number: 6933063Abstract: 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: GrantFiled: November 30, 2001Date of Patent: August 23, 2005Assignee: Electronics and Telecommunications Research InstituteInventors: Jeong Ik Lee, Hyoyoung Lee, Jiyoung Oh, Hye Yong Chu, Lee-Mi Do, Seong Hyun Kim, Taehyoung Zyung
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Patent number: 6887533Abstract: 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: GrantFiled: March 24, 2004Date of Patent: May 3, 2005Assignee: Clariant International, Ltd.Inventors: Wolfgang Schmidt, Barbara Hornung, Rainer Wingen
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Patent number: 6875895Abstract: 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: GrantFiled: August 20, 2002Date of Patent: April 5, 2005Assignee: Sumitomo Chemical Company, LimitedInventors: Takahiro Ueoka, Hideyuki Ikehira, Yoshiaki Tsubata
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Patent number: 6864396Abstract: 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: GrantFiled: September 27, 2002Date of Patent: March 8, 2005Assignee: 3M Innovative Properties CompanyInventors: Terrance P. Smith, Dennis E. Vogel, Kim M. Vogel
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Patent number: 6812311Abstract: 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: GrantFiled: October 18, 2001Date of Patent: November 2, 2004Assignee: Honeywell International Inc.Inventors: Thomas McCarthy, Michael Wagaman, David Schwind
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Patent number: 6759103Abstract: 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: GrantFiled: September 12, 2002Date of Patent: July 6, 2004Assignee: Clariant Financi (BVI) LimitedInventors: Barbara Hornung, Wolfgang Schmidt, Rainer Wingen
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Patent number: 6746728Abstract: 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: GrantFiled: December 28, 2001Date of Patent: June 8, 2004Assignee: 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
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Patent number: 6740263Abstract: 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: GrantFiled: February 7, 2002Date of Patent: May 25, 2004Inventors: Koon Ha Park, Yong Fan Kim, Min Seob Park
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Patent number: 6737125Abstract: 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: GrantFiled: September 12, 2002Date of Patent: May 18, 2004Assignee: Clariant Finance (BVI) LimitedInventors: Barbara Hornung, Wolfgang Schmidt, Rainer Wingen
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Patent number: 6716491Abstract: 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: GrantFiled: May 8, 2001Date of Patent: April 6, 2004Assignee: Merck Patent GmbHInventors: Kazuaki Tarumi, Brigitte Schuler, Matthias Bremer, Ulrich Finkenzeller, Eike Poetsch, Heike Kniel
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Publication number: 20040041125Abstract: Compounds of the formula (I) 1Type: ApplicationFiled: June 9, 2003Publication date: March 4, 2004Applicant: Merck Patent GmbHInventors: Matthias Bremer, Melanie Klasen-Memmer, Barbara Hornung, Wolfgang Schmidt, Rainer Wingen
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Patent number: 6682785Abstract: 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: GrantFiled: September 12, 2002Date of Patent: January 27, 2004Assignee: Clariant Finance (BVI) LimitedInventors: Rainer Wingen, Barbara Hornung, Wolfgang Schmidt
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Patent number: 6610219Abstract: 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: GrantFiled: February 6, 2001Date of Patent: August 26, 2003Assignee: Battelle Memorial InstituteInventors: Vincent D. McGinniss, Steven M. Risser
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Publication number: 20030136944Abstract: 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: ApplicationFiled: August 21, 2002Publication date: July 24, 2003Applicant: Dainippon Ink and Chemicals, Inc.Inventors: Sadao Takehara, Masashi Osawa, Haruyoshi Takatsu, Makoto Negishi
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Publication number: 20030065226Abstract: 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: ApplicationFiled: September 17, 2002Publication date: April 3, 2003Applicant: ADCHEMCO CorporationInventors: Tetsuo Hachiya, Naoyuki Kitamura, Hiroaki Mori, Toshiyuki Yasuda
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Patent number: 6534135Abstract: 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: GrantFiled: September 14, 2000Date of Patent: March 18, 2003Assignee: Merck Patent GesellschaftInventor: Mohammed Cherkaoui
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Patent number: 6509507Abstract: 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: GrantFiled: October 16, 2001Date of Patent: January 21, 2003Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Jochen Krause
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Patent number: 6491847Abstract: 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: GrantFiled: September 20, 2000Date of Patent: December 10, 2002Assignee: Canon Kabushiki KaishaInventors: Takao Takiguchi, Shinjiro Okada, Akira Tsuboyama, Shinichi Nakamura, Takashi Moriyama
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Patent number: 6491989Abstract: 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: GrantFiled: July 10, 2000Date of Patent: December 10, 2002Assignee: Aventis Reseach & Technologies GmbH & Co. KGInventors: Javier Manero, Wolfgang Schmidt, Barbara Hornung
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Patent number: 6485797Abstract: 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: GrantFiled: August 31, 2000Date of Patent: November 26, 2002Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Wolfgang Schmidt, Javier Manero, Barbara Hornung, Rainer Wingen, Ayako Ogawa
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Patent number: 6482478Abstract: 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: GrantFiled: September 5, 2000Date of Patent: November 19, 2002Assignee: Aventis Research & Technologies GmbH & Co. KGInventor: Rainer Wingen
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Patent number: 6468607Abstract: 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: GrantFiled: April 22, 1999Date of Patent: October 22, 2002Assignee: Dainippon Ink and Chemicals, Inc.Inventors: Sadao Takehara, Masashi Osawa, Haruyoshi Takatsu, Makoto Negishi
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Patent number: 6465700Abstract: 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: GrantFiled: August 3, 1998Date of Patent: October 15, 2002Assignee: Boulder Scientific CompanyInventors: Jeffrey M. Sullivan, Hamlin H. Barnes
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Patent number: 6380445Abstract: 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: GrantFiled: May 9, 2000Date of Patent: April 30, 2002Assignee: Vantico Inc.Inventors: Ralf-Roman Rietz, Wolfgang Wernet
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Patent number: 6350875Abstract: 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: GrantFiled: March 23, 2001Date of Patent: February 26, 2002Assignee: The University of Southern CaliforniaInventors: William P. Weber, Ping Lu, Mark E. Thompson, Haiping Hong
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Patent number: 6323373Abstract: 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: GrantFiled: June 9, 1999Date of Patent: November 27, 2001Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Jochen Krause
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Patent number: 6309561Abstract: 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: GrantFiled: December 24, 1997Date of Patent: October 30, 2001Assignee: 3M Innovative Properties CompanyInventors: Masakazu Hasegawa, Michael P. Keyes, Marc D. Radcliffe, Patricia M. Savu, Daniel C. Snustad, Terence D. Spawn
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Patent number: 6252001Abstract: 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: GrantFiled: January 13, 2000Date of Patent: June 26, 2001Assignee: The Dow Chemical CompanyInventors: David A. Babb, Dennis W. Smith, Jr., Steven J. Martin, James P. Godschalx
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Patent number: 6217793Abstract: 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: GrantFiled: May 17, 1999Date of Patent: April 17, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Yoshiyuki Totani, Hiroe Kayashima, Tsutomu Ishida, Masakatsu Nakatsuka
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Patent number: 6215008Abstract: 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: GrantFiled: December 3, 1999Date of Patent: April 10, 2001Assignee: Rohm and Haas CompanyInventor: Peter J. Heffron
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Patent number: 6168838Abstract: 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: GrantFiled: August 19, 1999Date of Patent: January 2, 2001Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Wolfgang Schmidt, Javier Manero
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Patent number: 6121495Abstract: 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: GrantFiled: September 12, 1996Date of Patent: September 19, 2000Assignee: The Dow Chemical CompanyInventors: David A. Babb, Dennis W. Smith, Jr., Steven J. Martin, James P. Godschalx
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Patent number: RE39532Abstract: 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: GrantFiled: July 17, 1997Date of Patent: March 27, 2007Assignee: Basell Polyolefine GmbHInventors: Andreas Winter, Martin Antberg, Walter Spaleck, Jürgen Rohrmann, Volker Dolle