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Organic optical material

Foreign code F210010322
File No. AF29-06WO
Posted date Feb 1, 2021
Country United States of America
Application number 201816641112
Gazette No. 20200284946
Date of filing Aug 24, 2018
Gazette Date Sep 10, 2020
International application number JP2018031419
International publication number WO2019039597
Date of international filing Aug 24, 2018
Date of international publication Feb 28, 2019
Priority data
  • P2017-161912 (Aug 25, 2017) JP
  • P2018-037356 (Mar 2, 2018) JP
  • 2018JP31419 (Aug 24, 2018) WO
Title Organic optical material
Abstract Provided is a novel donor-acceptor type compound which emits light even in a solid state. The present invention provides an organic optical material comprising a complex formed from (1) a conjugated molecule having (a) at least one electron donating site, (b) at least one electron accepting site, and (c) at least one conjugated site in the same molecule and (2) a compound having a proton donating property or an electron pair accepting property, the complex having a non-covalent interaction at the electron accepting site, wherein the complex is solid at ordinary temperature; and the organic optical material has a property of emitting light having a maximum fluorescence wavelength which causes a Stokes shift having a value corresponding to 5% or more of the value of a maximum absorption wavelength from the maximum absorption wavelength toward the long wavelength side.
Outline of related art and contending technology BACKGROUND OF THE INVENTION
Light emitting organic compounds are used in a wide range of fields such as biological labeling materials, organic electronics materials, chemical sensors, and organic lasers. Novel light emitting materials are under active research and development. In particular, fluorescent organic compounds which emit light by irradiation with X-ray, ultraviolet ray, or visible light may be utilized in organic fluorescent coatings, etc., in addition to the purposes described above.
However, most of molecules generally used as light emitting organic materials are robust and highly planar molecules. Therefore, such molecules intensely emit light in a solution because of less contact or interference between the molecules. By contrast, the molecules in a solid state such as a crystalline state often drastically reduce light emission efficiency because the energy of a released electromagnetic wave is attenuated by the influence of its neighboring planar molecules. Since the light emitting organic materials may be used in a solid state in terms of application, an important challenge thereto is to develop materials which intensely emit light not only in a solution but in a solid state.
Many donor-acceptor type compounds have been reported and are known to exhibit diverse characteristics.
Patent Literature 1 discloses a fluorescence emitting compound comprising a nitrogen-containing aromatic ring having high light emission efficiency not only in a solution state but in a solid state.
Non Patent Literature 1 states that the fluorescence wavelength of a so-called donor-acceptor type compound in which the donor and the acceptor are conjugated with each other can be controlled by causing hydrochloric acid, trifluoroacetic acid, or boron tribromide as an activator to react with the compound.
Non Patent Literature 2 describes various analyses conducted by allowing a boron-containing compound to act on a compound consisting of a dimethylamino group and a pyridine ring, which results in a finding that a dipole moment is increased through the reaction of the nitrogen atom of the pyridine ring with the boron atom. However, the literature does not disclose influence on a fluorescence wavelength.
Scope of claims [claim1]
1: An organic optical material comprising a complex formed from (1) a conjugated molecule having (a) at least one electron donating site, (b) at least one electron accepting site, and (c) at least one conjugated site in the same molecule and (2) a compound having a proton donating property or an electron pair accepting property, the complex having a non-covalent interaction at the electron accepting site, wherein
the complex is solid at ordinary temperature; and the organic optical material exhibits a property of emitting light having a maximum fluorescence wavelength which causes a Stokes shift of 5% or more of the value of a maximum absorption wavelength from the maximum absorption wavelength toward the long wavelength side when the conjugated molecule and the compound having a proton donating property or an electron pair accepting property form the complex.
2-34. (canceled)
  • Inventor, and Inventor/Applicant
  • KUNINOBU YOICHIRO
  • KANAI MOTOMU
  • YAMAKAWA TAKESHI
  • YOSHIGOE YUSUKE
  • WANG ZIJIA
  • NAGASHIMA HIDEO
  • TAHARA ATSUSHI
  • JAPAN SCIENCE AND TECHNOLOGY AGENCY
IPC(International Patent Classification)
Reference ( R and D project ) CREST Creation of Innovative Functions of Intelligent Materials on the Basis of the Element Strategy AREA
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