WO2010038252A3 - Carbonyl derivatives having a c3 symmetry, their preparation and uses thereof - Google Patents

Carbonyl derivatives having a c3 symmetry, their preparation and uses thereof Download PDF

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Publication number
WO2010038252A3
WO2010038252A3 PCT/IT2009/000449 IT2009000449W WO2010038252A3 WO 2010038252 A3 WO2010038252 A3 WO 2010038252A3 IT 2009000449 W IT2009000449 W IT 2009000449W WO 2010038252 A3 WO2010038252 A3 WO 2010038252A3
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WO
WIPO (PCT)
Prior art keywords
fluoranthene
symmetry
preparation
group chosen
relates
Prior art date
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PCT/IT2009/000449
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French (fr)
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WO2010038252A2 (en
Inventor
Liliana Bagala^ Rampazzo
Leonardo Matiello
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Università Degli Studi Di Roma La Sapienza
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Publication date
Application filed by Università Degli Studi Di Roma La Sapienza filed Critical Università Degli Studi Di Roma La Sapienza
Priority to EP09760016A priority Critical patent/EP2334630A2/en
Publication of WO2010038252A2 publication Critical patent/WO2010038252A2/en
Publication of WO2010038252A3 publication Critical patent/WO2010038252A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/28—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of CHx-moieties
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
    • C07C49/675—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having three rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C07C49/788—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic with keto groups bound to a condensed ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C07C49/792—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic containing rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • 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
    • Y02E10/549—Organic PV cells
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)

Abstract

The invention relates to 1,3,5-benzene derivatives and corresponding radical-anions and radical-cations of the general formula (I): wherein: Z is a group chosen from among C=O, CONH, CONR, CONAr; m is an integer >0, preferably m = 1; A is a group chosen from among the radicals of: biphenylene, carbazole, fluoranthene, fluorene, dibenzothiofene, dibenzofurane, fluorenone, bifluorenylidene, triphenylene, cyclooctatetraene (COT), dibenzocyclooctatetraene (DBCOT), coronene, acenaphtylene, triptycene, azulene, benzo(ghi)fluoranthene, 2-phenyl-l,3,4-oxadiazole, anthracene. R and Ar are alkyl and aryl respectively and have the meaning indicated herein below. The invention also relates to the method for synthesizing said compounds and to their use in particular as components of matrices in the molecular electronics, spintronics and telecom fields.
PCT/IT2009/000449 2008-10-02 2009-10-02 Carbonyl derivatives having a c3 symmetry, their preparation and uses thereof WO2010038252A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP09760016A EP2334630A2 (en) 2008-10-02 2009-10-02 Carbonyl derivatives having a c3 symmetry, their preparation and uses thereof

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
ITRM2008A000523A IT1391474B1 (en) 2008-10-02 2008-10-02 CARBONYL DERIVATIVES AT C3 SYMMETRY, THEIR PREPARATION AND THEIR USE
ITRM2008A000523 2008-10-02

Publications (2)

Publication Number Publication Date
WO2010038252A2 WO2010038252A2 (en) 2010-04-08
WO2010038252A3 true WO2010038252A3 (en) 2010-05-27

Family

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EP (1) EP2334630A2 (en)
IT (1) IT1391474B1 (en)
WO (1) WO2010038252A2 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103922915B (en) * 2014-04-14 2016-05-11 国家纳米科学中心 A kind of two pyrene compounds, preparation method and application thereof with piezallochromy character
US9475777B2 (en) * 2014-05-16 2016-10-25 University Of Houston System Thermally robust, highly porous, and partially fluorinated organic framework with affinity for hydrocarbons, fluorocarbons and freons
EP3275865A1 (en) * 2016-07-29 2018-01-31 Ludwig-Maximilians-Universität München Amide-based hole-transporting or hole-injecting materials
EP3477722B1 (en) * 2017-10-31 2023-09-27 Samsung Display Co., Ltd. Light absorber and organic electroluminescence device including the same
KR101981294B1 (en) 2017-10-31 2019-05-23 삼성디스플레이 주식회사 Light absorber and organic electroluminescence device including the same

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020103183A1 (en) * 2000-09-07 2002-08-01 Louise Robinson Benzene tricarboxylic acid derivatives as insulin receptor activators
WO2006005627A1 (en) * 2004-07-15 2006-01-19 Merck Patent Gmbh Oligomeric derivatives of spirobifluorene, their preparation and use
WO2007137725A1 (en) * 2006-05-31 2007-12-06 Merck Patent Gmbh New materials for organic electroluminescent devices

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020103183A1 (en) * 2000-09-07 2002-08-01 Louise Robinson Benzene tricarboxylic acid derivatives as insulin receptor activators
WO2006005627A1 (en) * 2004-07-15 2006-01-19 Merck Patent Gmbh Oligomeric derivatives of spirobifluorene, their preparation and use
WO2007137725A1 (en) * 2006-05-31 2007-12-06 Merck Patent Gmbh New materials for organic electroluminescent devices

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
PIGGE F C ET AL: "Mono-, Bis-, and Tris(crown ether)s Assembled around 1,3,5-Triaroylbenzene Scaffolds", JOURNAL OF ORGANIC CHEMISTRY, vol. 73, no. 7, 2008, pages 2760 - 2767, XP002544701 *
PIGGE F C ET AL: "Synthesis of linked 1,3,5-triaroylbenzenes via enamine-directed alkyne cyclotrimerization", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, vol. 41, no. 34, 19 August 2000 (2000-08-19), pages 6545 - 6549, XP004215811, ISSN: 0040-4039 *
PIGGE F C ET AL: "The preparation of 1,3,5-tris(1,1'-binaphthoyl)benzene via amine-catalyzed alkyne trimerization", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM, vol. 42, no. 47, 19 November 2001 (2001-11-19), pages 8259 - 8261, XP004311296, ISSN: 0040-4039 *
YAMAGUCHI Y ET AL: "Rigid Molecular Architectures That Comprise a 1,3,5-Trisubstituted Benzene Core and Three Oligoaryleneethynylene Arms: Light-Emitting Characteristics and "p" Conjugation between the Arms", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 128, no. 14, 2006, pages 4504 - 4505, XP002544702 *

Also Published As

Publication number Publication date
IT1391474B1 (en) 2011-12-23
EP2334630A2 (en) 2011-06-22
ITRM20080523A1 (en) 2010-04-03
WO2010038252A2 (en) 2010-04-08

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