Title:
STABILIZER COMPOUND, LIQUID CRYSTAL COMPOSITION, AND DISPLAY ELEMENT
Document Type and Number:
WIPO Patent Application WO/2017/038552
Kind Code:
A1
Abstract:
The present invention provides a compound represented by general formula (I). The compound pertaining to the present invention prevents degradation of a liquid crystal composition by light, has high compatibility with a liquid crystal composition, and does not compromise the storage stability of a liquid crystal composition, and is therefore useful as a constituent member of a liquid crystal composition. A liquid crystal composition and liquid crystal display element containing this compound exhibit UV-resistant properties and have high VHR, and a liquid crystal display element is therefore obtained which has excellent display quality and in which display defects such as ghosting or uneven display do not occur or are suppressed.
Inventors:
AOKI YOSHIO (JP)
HOSONO AYAKI (JP)
HOSONO AYAKI (JP)
Application Number:
PCT/JP2016/074474
Publication Date:
March 09, 2017
Filing Date:
August 23, 2016
Export Citation:
Assignee:
DAINIPPON INK & CHEMICALS (JP)
International Classes:
C07D207/08; C07D207/16; C07D207/46; C09K19/54
Domestic Patent References:
| WO2014066230A1 | 2014-05-01 | |||
| WO2014045783A1 | 2014-03-27 | |||
| WO1993022662A1 | 1993-11-11 |
Foreign References:
| JP2016132678A | 2016-07-25 | |||
| JP2004524259A | 2004-08-12 | |||
| JPS60190786A | 1985-09-28 | |||
| US5567411A | 1996-10-22 | |||
| JPS4897780A | 1973-12-12 | |||
| JP2012515206A | 2012-07-05 | |||
| JPS60500668A | 1985-05-09 | |||
| JPS60500669A | 1985-05-09 | |||
| JPH02265966A | 1990-10-30 | |||
| US3020288A | 1962-02-06 |
Other References:
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MATSUMOTO, K. ET AL.: "Modification of nitroxyl contrast agents with multiple spins and their proton Tl relaxivity", MAGNETIC RESONANCE IMAGING, vol. 26, no. 1, 2008, pages 117 - 121, XP022455470
BOSMAN, A. W. ET AL.: "Five Generations of Nitroxyl-Functionalized Dendrimers", MACROMOLECULES, vol. 30, no. 12, 1997, pages 3606 - 3611, XP000700749
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VALERA, S. ET AL.: "A Modular Approach for the Synthesis of Nanometer-Sized Polynitroxide Multi-Spin Systems", JOURNAL OF ORGANIC CHEMISTRY, vol. 79, no. 17, 2014, pages 8313 - 8323, XP055367785
SCHUETZ, D. ET AL.: "4,4',4''-(Methanetriyl) triphenyltris (2,2,5,5-tetramethyl-1-oxyl-3- pyrroline-3-carboxylate) benzene trisolvate", ACTA CRYSTALLOGRAPHICA, SECTION E: STRUCTURE REPORTS ONLINE, vol. 66, no. 4, 2010, pages o729 - o730, XP055367787
SEN', V. D. ET AL.: "Synthesis and structure of products of hydroxylamine acylation with 3- carboxy-2,2,5,5-tetramethylpyrrolinoxyl derivatives", RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, vol. 45, no. 8, 2009, pages 1189 - 1199, XP055367789
JASZBERENYI, Z. ET AL.: "Synthesis, equilibrium and kinetic properties of Gd3+ complexes of three DTPA-bis(amide) derivatives containing stable nitroxide free radical substituents", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, vol. 19, 2003, pages 3601 - 3608
MARTIN, V. V. ET AL.: "Novel pH-sensitive nitroxide di- and tri-radical spin labels, Journal of the Chemical Society", CHEMICAL COMMUNICATIONS, 1995, pages 723 - 4, XP055367793
BRIK, M. E.: "Synthesis of di and polynitroxides by Favorskii rearrangement of polyamines on cis-3,5-dibromo-4-oxo-2,2,6,6- tetramethylpiperidin-1-oxyl", SYNTHETIC COMMUNICATIONS, vol. 20, no. 10, 1990, pages 1487 - 95
BRIK, M. E. ET AL.: "Evaluation of MRI contrast by using polynitroxides: application to magnetic resonance imaging of lungs and liver", ANALUSIS, vol. 18, no. 3, 1990, pages 179 - 84
SHAPIRO, A. B. ET AL.: "Iminoxyl biradicals with polyene bridges, Izvestiya Akademii Nauk SSSR", SERIYA KHIMICHESKAYA, 1976, pages 2124 - 7
FERRUTI, P. ET AL.: "Synthesis of mono-, di-, and polynitroxides. Classification of electron spin resonance spectra of flexible dinitroxides dissolved in liquids and glasses", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 92, no. 12, 1970, pages 3704 - 13, XP002260936
KRINITSKAYA, L. A. ET AL.: "Individual iminoxyl polyradicals of hydrogenated pyrrole", ZHURNAL ORGANICHESKOI KHIMII, vol. 2, no. 7, 1966, pages 1301 - 5
CORVAJA, C. ET AL.: "Electron spin resonance studies of nitroxide radicals and biradicals in nematic solvents", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 92, no. 13, 1970, pages 3919 - 3924
YAMAOKA, K. ET AL.: "Spin-labeled metachromatic dyes. I. ESR and some optical properties of spin-labeled proflavine in solution, liquid crystal, and stretched film", CHEMISTRY LETTERS, vol. 12, 1976, pages 1351 - 1354, XP055367804
SETAKA, M. ET AL.: "Orientation of some nitroxide spin labels in the lamellar mesophases of Aerosol-OT-water and decanol-decanoate-water systems", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 97, no. 21, 1975, pages 6013 - 6018, XP055367810
HATANO, B. ET AL.: "Facile synthesis of 3- methoxycarbonyl-2,2,5,5-tetramethylpyrrolidin- 1-oxyland derivatives", HETEROCYCLES, vol. 81, no. 2, 2010, pages 349 - 356
MATSUMOTO, K. ET AL.: "Modification of nitroxyl contrast agents with multiple spins and their proton Tl relaxivity", MAGNETIC RESONANCE IMAGING, vol. 26, no. 1, 2008, pages 117 - 121, XP022455470
BOSMAN, A. W. ET AL.: "Five Generations of Nitroxyl-Functionalized Dendrimers", MACROMOLECULES, vol. 30, no. 12, 1997, pages 3606 - 3611, XP000700749
GALLEZ, B. ET AL.: "Evaluation of nonionic nitroxyl lipids as potential organ-specific contrast agents for magnetic resonance imaging", MAGNETIC RESONANCE IMAGING, vol. 10, no. 3, 1992, pages 445 - 455, XP026297448
VALERA, S. ET AL.: "A Modular Approach for the Synthesis of Nanometer-Sized Polynitroxide Multi-Spin Systems", JOURNAL OF ORGANIC CHEMISTRY, vol. 79, no. 17, 2014, pages 8313 - 8323, XP055367785
SCHUETZ, D. ET AL.: "4,4',4''-(Methanetriyl) triphenyltris (2,2,5,5-tetramethyl-1-oxyl-3- pyrroline-3-carboxylate) benzene trisolvate", ACTA CRYSTALLOGRAPHICA, SECTION E: STRUCTURE REPORTS ONLINE, vol. 66, no. 4, 2010, pages o729 - o730, XP055367787
SEN', V. D. ET AL.: "Synthesis and structure of products of hydroxylamine acylation with 3- carboxy-2,2,5,5-tetramethylpyrrolinoxyl derivatives", RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, vol. 45, no. 8, 2009, pages 1189 - 1199, XP055367789
JASZBERENYI, Z. ET AL.: "Synthesis, equilibrium and kinetic properties of Gd3+ complexes of three DTPA-bis(amide) derivatives containing stable nitroxide free radical substituents", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, vol. 19, 2003, pages 3601 - 3608
MARTIN, V. V. ET AL.: "Novel pH-sensitive nitroxide di- and tri-radical spin labels, Journal of the Chemical Society", CHEMICAL COMMUNICATIONS, 1995, pages 723 - 4, XP055367793
BRIK, M. E.: "Synthesis of di and polynitroxides by Favorskii rearrangement of polyamines on cis-3,5-dibromo-4-oxo-2,2,6,6- tetramethylpiperidin-1-oxyl", SYNTHETIC COMMUNICATIONS, vol. 20, no. 10, 1990, pages 1487 - 95
BRIK, M. E. ET AL.: "Evaluation of MRI contrast by using polynitroxides: application to magnetic resonance imaging of lungs and liver", ANALUSIS, vol. 18, no. 3, 1990, pages 179 - 84
SHAPIRO, A. B. ET AL.: "Iminoxyl biradicals with polyene bridges, Izvestiya Akademii Nauk SSSR", SERIYA KHIMICHESKAYA, 1976, pages 2124 - 7
FERRUTI, P. ET AL.: "Synthesis of mono-, di-, and polynitroxides. Classification of electron spin resonance spectra of flexible dinitroxides dissolved in liquids and glasses", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 92, no. 12, 1970, pages 3704 - 13, XP002260936
KRINITSKAYA, L. A. ET AL.: "Individual iminoxyl polyradicals of hydrogenated pyrrole", ZHURNAL ORGANICHESKOI KHIMII, vol. 2, no. 7, 1966, pages 1301 - 5
CORVAJA, C. ET AL.: "Electron spin resonance studies of nitroxide radicals and biradicals in nematic solvents", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 92, no. 13, 1970, pages 3919 - 3924
YAMAOKA, K. ET AL.: "Spin-labeled metachromatic dyes. I. ESR and some optical properties of spin-labeled proflavine in solution, liquid crystal, and stretched film", CHEMISTRY LETTERS, vol. 12, 1976, pages 1351 - 1354, XP055367804
SETAKA, M. ET AL.: "Orientation of some nitroxide spin labels in the lamellar mesophases of Aerosol-OT-water and decanol-decanoate-water systems", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 97, no. 21, 1975, pages 6013 - 6018, XP055367810
HATANO, B. ET AL.: "Facile synthesis of 3- methoxycarbonyl-2,2,5,5-tetramethylpyrrolidin- 1-oxyland derivatives", HETEROCYCLES, vol. 81, no. 2, 2010, pages 349 - 356
Attorney, Agent or Firm:
KONO Michihiro (JP)
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