Classifications

• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
  • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
  • H01G9/20—Light-sensitive devices
  • H01G9/2004—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte
  • H01G9/2018—Light-sensitive devices characterised by the electrolyte, e.g. comprising an organic electrolyte characterised by the ionic charge transport species, e.g. redox shuttles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
  • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
  • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
  • C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
  • C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
  • C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/56—Ring systems containing three or more rings
  • C07D209/80—[b, c]- or [b, d]-condensed
  • C07D209/82—Carbazoles; Hydrogenated carbazoles
  • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
  • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
  • H01G9/20—Light-sensitive devices
  • H01G9/2027—Light-sensitive devices comprising an oxide semiconductor electrode
• • H—ELECTRICITY
  • H01—ELECTRIC ELEMENTS
  • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
  • H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
  • H01G9/20—Light-sensitive devices
  • H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
  • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
  • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/649—Aromatic compounds comprising a hetero atom
  • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
  • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
  • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
  • Y02E10/00—Energy generation through renewable energy sources
  • Y02E10/50—Photovoltaic [PV] energy
  • Y02E10/542—Dye sensitized solar cells

Definitions

• Dye-sensitized solar cells are a promising photovoltaic technology for the production of renewable and low-cost energy. These cells consist of a nanocrystalline oxide with a large energy gap, for example TiO 2 deposited on a transparent conductive oxide glass support. Molecular sensitizers, bonded through wide-gap oxide anchoring groups, inject electrons into the conduction band of the semiconductor under solar exposure. Usually, a liquid electrolyte comprising a redox system provides regeneration of the photoexcited dye.
• liquid electrolyte based DSSCs achieve conversion efficiencies of more than 12%. However, they can cause problems of leakage and corrosion of the electrodes.
• ssDSSC solid state DSSC
• PDOT poly (3,4-ethylenedioxythiophene)
• P3HT poly-3-hexylthiophene
• the present invention relates to a process for synthesizing ⁇ -conjugated materials comprising a step of implementing a synthon of formula (I)
• Ari and Ar 2 which are identical or different, each independently represent an aryl group, optionally substituted with one or more identical or different substituents chosen from:
• Ci-Ci 2 alkyl groups straight or branched Ci-Ci 2 alkyl groups, said alkyl groups being able to be saturated or unsaturated and possibly containing one or more heteroatoms chosen from O and S,
• said groups may be substituted by at least one alkyl group-Ci 2 straight or branched, in particular methyl, or by alkoxy, Ci-Ci 2 straight or branched, in particular methoxy,
• C 1 -C 12 or straight or branched (C 1 -C 2 ) alkyl said alkyl group may be saturated or unsaturated and may comprise one or more heteroatoms chosen from O and S , a saturated or unsaturated linear or branched chain of 1 to 15 carbons said carbon atoms may be replaced by one or more heteroatoms selected from O and S.
• R 1 and R 2 are respectively in position 3 and 6 or in position 2 and 7 of the ring and are chosen independently of each other in the group comprising
• R 6 represents either an alkyl group Ci-2 straight or branched, or an aryl group of C 6 -C 8, in particular a benzene group or methoxybenzene (anisole), or an amine protecting group, in particular a group benzyl, optionally substituted alkoxy C 1 -C 5 or an aryl group of C 6 -C 8 alkyl substituted by halogen, in particular fluorine or substituted by an alkyl group Ci-Ci 2 straight or branched fluorinated, in especially trifluoromethyl (CF3), or bistral, tri or tetracyclic group comprising from 10 to 18 carbon atoms, such as for example a naphthyl, tetrahydronaphthyl, anthracenyl or pyrenyl group.
• the process of the invention also makes it possible to prepare ⁇ -conjugated materials corresponding to formula (Ia) or (Ib)
• polyfunctional central unit means a unit carrying functions for grafting in position 9 of the carbazole ring or the fluorene ring.
• functions that allow grafting mention may be made of iodine, bromine, chlorine atoms, tosylates, mesylates, etc.
• polyfunctional central units it may be noted - C 6 H 4 -, biphenylene, terphenyl, fluorenyl, carbazolyl, oligooxyethylene derivative, these polyfunctional central units may or may not be substituted by one or more linear or branched C1-C12 alkyls.
• a very promising application of the present invention is the field of organic photovoltaics and particularly photovoltaic cells with dye or dye sensitized solar cell (DSSC).
• the process according to the invention has already allowed the synthesis of a number of ⁇ -conjugated organic molecules, semiconductors whose use instead of the liquid electrolyte in the DSSC has given preliminary results very promising.
• the best materials used under the same conditions as the market's reference molecule (spiro-OMeTAD) give comparable photovoltaic performances.
• the product is obtained in the form of a low-density white solid.
• the four molecular glasses are The four molecular glasses:
• the characterizations were performed in the dark and under illumination (AM 1.5 G).
• the four devices show a diode characteristic in the dark and a photovoltaic effect under illumination by the appearance of a photogenerated current (see Figures 1 and 2).
• the short-circuit current densities obtained are between 4.17 mA.cm -2 and 7.45 mA.cm -2 and the values of the open circuit voltages are between 0.73V and 0.82V.
• Photovoltaic conversion efficiencies range from 1.34% to 2.36%.
• Compound 5 is the one which made it possible to obtain the best conversion yield which is 2.36%.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Power Engineering (AREA)
• Materials Engineering (AREA)
• Physics & Mathematics (AREA)
• Spectroscopy & Molecular Physics (AREA)
• Microelectronics & Electronic Packaging (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Electrochemistry (AREA)
• Indole Compounds (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Priority Applications (4)

Applications Claiming Priority (2)

Publications (1)

Family

ID=51987249

Family Applications (1)

Country Status (6)

Cited By (2)

Families Citing this family (7)

Citations (5)

Family Cites Families (16)

• 2014
  • 2014-07-28 FR FR1457308A patent/FR3024144B1/fr active Active
• 2015
  • 2015-07-28 US US15/329,731 patent/US10403445B2/en not_active Expired - Fee Related
  • 2015-07-28 JP JP2017505229A patent/JP2017523196A/ja active Pending
  • 2015-07-28 WO PCT/EP2015/067232 patent/WO2016016221A1/fr not_active Ceased
  • 2015-07-28 KR KR1020177005744A patent/KR20170040301A/ko not_active Withdrawn
  • 2015-07-28 EP EP15749754.6A patent/EP3174850A1/fr not_active Withdrawn

Patent Citations (5)

Non-Patent Citations (19)

Also Published As

Similar Documents

Legal Events