WO2012136675A3 - Kontrolliertes verfahren zur herstellung von konjugierten polymeren - Google Patents

Kontrolliertes verfahren zur herstellung von konjugierten polymeren Download PDF

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Publication number
WO2012136675A3
WO2012136675A3 PCT/EP2012/056109 EP2012056109W WO2012136675A3 WO 2012136675 A3 WO2012136675 A3 WO 2012136675A3 EP 2012056109 W EP2012056109 W EP 2012056109W WO 2012136675 A3 WO2012136675 A3 WO 2012136675A3
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WO
WIPO (PCT)
Prior art keywords
naphthalenide
bisimide
thiophene
reducing agent
tetracarboxylic acid
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PCT/EP2012/056109
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English (en)
French (fr)
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WO2012136675A2 (de
Inventor
Volodymyr Senkovskyy
Anton Kiriy
Michael Sommer
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Leibniz-Institut Für Polymerforschung Dresden E.V.
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Application filed by Leibniz-Institut Für Polymerforschung Dresden E.V. filed Critical Leibniz-Institut Für Polymerforschung Dresden E.V.
Priority to EP12717628.7A priority Critical patent/EP2694567A2/de
Publication of WO2012136675A2 publication Critical patent/WO2012136675A2/de
Publication of WO2012136675A3 publication Critical patent/WO2012136675A3/de

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/141—Side-chains having aliphatic units
    • C08G2261/1412—Saturated aliphatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
    • C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
    • C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/344—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/40—Polymerisation processes
    • C08G2261/41—Organometallic coupling reactions
    • C08G2261/416—Organometallic coupling reactions zinc-based, e.g. Rieke reactions
    • 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
    • H10K50/15—Hole transporting layers

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Die Aufgabe wird gelöst durch ein Verfahren, bei dem zu einer Lösung eines metallorganischen Komplexes ein Nickel- oder Palladium-Katalysator zugegeben wird, wobei der metallorganische Komplex hergestellt ist - durch die Zugabe von metallischem Zn oder Mg zu einer Monomerlösung, oder - durch Zugabe von einem Reduktionsmittel zu einer Monomerlösung und entweder Zn2+- oder Mg2+-Salz, wobei, als Reduktionsmittel Lithium-Naphthalenid oder Natrium-Naphthalenid oder Kalium-Naphthalenid eingesetzt wird, und wobei als Monomer ein π-konjugiertes System der Formel X-B-A-B-X eingesetzt wird, wobei - als A ein Kern auf Elektronenakzeptortmaterialbasis eingesetzt wird, welches Naphthalin-1, 4, 5, 8-tetracarbonsäure-bisimid (NDI) oder Perylentetracarbonsäure-bisimid (PDI) oder Pyromellitic bisimid (PMI) oder Diketopyrrolopyrrol (DPP) beinhaltet, und - als B eine aromatische oder heteroaromatische oder eine kondensierte aromatische oder eine kondensierte heteroaromatische Gruppe eingesetzt wird, auf der Basis von substituierten oder unsubstituierten Benzol-, Fluoren-, Thiophen-, Bithiophen-, Pyrrol-, Thieno[2,3-b]thiophen-, 4H-cyclopenta[2,1-b:3,4-b']dithiophen- oder Dithieno[3,2-b:2',3'-d]silol-Derivaten, und - als X ein Halogen eingesetzt wird.
PCT/EP2012/056109 2011-04-06 2012-04-03 Kontrolliertes verfahren zur herstellung von konjugierten polymeren WO2012136675A2 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP12717628.7A EP2694567A2 (de) 2011-04-06 2012-04-03 Kontrolliertes verfahren zur herstellung von konjugierten polymeren

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102011006885.6 2011-04-06
DE102011006885A DE102011006885A1 (de) 2011-04-06 2011-04-06 Verfahren zur Herstellung von konjugierten Polymeren

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WO2012136675A2 WO2012136675A2 (de) 2012-10-11
WO2012136675A3 true WO2012136675A3 (de) 2012-12-06

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DE (1) DE102011006885A1 (de)
WO (1) WO2012136675A2 (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103012755B (zh) * 2012-12-14 2015-03-11 中国科学院化学研究所 乙烯双键桥连ndi基共轭聚合物及其制备方法与应用
EP2808373A1 (de) * 2013-05-29 2014-12-03 Solvay SA Halbleitermaterialien auf der Basis von Rylendiimid-Derivaten oder Naphthalin-Derivaten, sowie diese enthaltende Polymere und Halbleitergeräte
WO2015108374A1 (ko) * 2014-01-17 2015-07-23 주식회사 엘지화학 유기 태양 전지 및 이의 제조방법
EP3790918A4 (de) 2018-05-05 2022-03-16 Jason D. Azoulay Konjugierte polymerleiter mit offener schale, verbundwerkstoffe und zusammensetzungen
EP3853288A4 (de) 2018-09-21 2022-07-27 Joshua Tropp Thiolbasierte nachträgliche modifikation von konjugierten polymeren
CN109553757B (zh) * 2018-12-21 2021-03-02 福州大学 一种二维结构的萘二酰亚胺类受体聚合物及其制备方法与应用
US11781986B2 (en) 2019-12-31 2023-10-10 University Of Southern Mississippi Methods for detecting analytes using conjugated polymers and the inner filter effect
CN113896865A (zh) * 2021-10-21 2022-01-07 福州大学 含多巴胺衍生侧链的萘酰亚胺聚合物半导体及其制备方法

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WO2012136675A2 (de) 2012-10-11
EP2694567A2 (de) 2014-02-12
DE102011006885A1 (de) 2012-10-11

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