EP1575932A2 - Molecules octupolaires utilisees comme semiconducteurs organiques - Google Patents

Molecules octupolaires utilisees comme semiconducteurs organiques

Info

Publication number
EP1575932A2
EP1575932A2 EP03766287A EP03766287A EP1575932A2 EP 1575932 A2 EP1575932 A2 EP 1575932A2 EP 03766287 A EP03766287 A EP 03766287A EP 03766287 A EP03766287 A EP 03766287A EP 1575932 A2 EP1575932 A2 EP 1575932A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
applies
fluoroalkyl
perfluoroalkyl
aryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP03766287A
Other languages
German (de)
English (en)
Inventor
Marcus Halik
Hagen Klauk
Günter Schmid
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Infineon Technologies AG
Original Assignee
Infineon Technologies AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Infineon Technologies AG filed Critical Infineon Technologies AG
Publication of EP1575932A2 publication Critical patent/EP1575932A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/464—Lateral top-gate IGFETs comprising only a single gate
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate

Definitions

  • the mobility of charge carriers in organic semiconductors is currently at a maximum of 1-2 cm 2 / Vs.
  • the maximum operating frequency of transistors and thus the electronic circuit is limited by the mobility of the charge carriers (holes or electrons).
  • mobilities of the order of 10 ° cm 2 / Vs are sufficient for driver applications in the production of TFT active matrix displays, high-frequency applications are generally ruled out.
  • Novel compounds for use as organic semiconductors are described in this invention.
  • the molecular structure of these compounds enables a high one Mobility of the load carriers in appropriately prepared films.
  • octupolar compounds of the following general formula are provided, the octupolar molecules being in the form of stacks or molecular clusters:
  • R is with respect to n-alkyl, sec-alkyl, tert-alkyl, cycloalkyl, fluoroalkyl, perfluoroalkyl, aryl, fluoroaryl, perfluoroaryl, alkoxy, fluoroalkoxy, aryloxy, Fluoraryloxy, perfluoroalkoxy and Perfluoraryloxy as R 2 defined, in terms of the preferred embodiments of R In a preferred embodiment, however, R 3 is H.
  • the chemical nature of the R 3 radical is, according to current knowledge, less critical for the present invention than the R 1 and R 2 radicals, in particular Ri.
  • the halogen radical can be Cl, Br, and / or I. Preferred halides are Br and I.
  • the compounds according to the invention can be prepared by known processes, for example in ref. [4] (triple ketolization and dehydration of three equivalents of acetyl aromatic molecules with tetrachlorosilane-ethanol (1: 1)), [5] (aryl aryl Coupling) and [6] (aryl-aryl coupling).
  • Triazine compounds according to the invention can e.g. be prepared by nucleophilic substitution of the corresponding lithium salts with cyanuric chloride.
  • Both p-type semiconductors and n-type semiconductors can be represented.
  • the compounds of the present invention can be used as organic semiconductors, and can be used as n- and p-semiconductors.
  • the connections of the present invention can be used in electronic components such as transistors, preferably field-effect transistors.
  • Connection (3) can be represented by at least two alternative routes:
  • Compound (_6) was prepared by nucleophilic aromatic substitution of 2- [(5 ⁇ - ethyl) - 2, 2: 5 2 ⁇ -terthienyl] - lithium salt with cyanuric chloride in THF.
  • a solution prepared as in Example 7 was spun onto a suitable substrate on which transistors and / or circuit structures had previously been defined (e.g. Si wafer, glass or flexible film) (1000 - 5000 rpm, 20s, nitrogen atmosphere). The substrate was then dried under protective gas at 80 ° C. for 2 minutes.
  • a suitable substrate e.g. Si wafer, glass or flexible film
  • a compound (Examples 1-6) was placed under high vacuum (10 ⁇ 6 -10 "7 torr) by means of an evaporator on a substrate such as under Ex. 15, steamed.
  • the evaporation times and substrate temperatures depended on the properties of the compounds and the desired layer thickness.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Thin Film Transistor (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne de nouveaux composés octupolaires ainsi que leur production et leur utilisation comme semiconducteurs organiques, notamment pour des transistors à effet de champ organiques.
EP03766287A 2002-07-26 2003-07-24 Molecules octupolaires utilisees comme semiconducteurs organiques Withdrawn EP1575932A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10234188 2002-07-26
DE10234188A DE10234188B4 (de) 2002-07-26 2002-07-26 Oktupolare Moleküle als organische Halbleiter
PCT/EP2003/008157 WO2004013122A2 (fr) 2002-07-26 2003-07-24 Molecules octupolaires utilisees comme semiconducteurs organiques

Publications (1)

Publication Number Publication Date
EP1575932A2 true EP1575932A2 (fr) 2005-09-21

Family

ID=30128434

Family Applications (1)

Application Number Title Priority Date Filing Date
EP03766287A Withdrawn EP1575932A2 (fr) 2002-07-26 2003-07-24 Molecules octupolaires utilisees comme semiconducteurs organiques

Country Status (4)

Country Link
EP (1) EP1575932A2 (fr)
DE (1) DE10234188B4 (fr)
TW (1) TW200403238A (fr)
WO (1) WO2004013122A2 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4738034B2 (ja) 2004-08-12 2011-08-03 富士フイルム株式会社 液晶性化合物、組成物および薄膜
TWI422876B (zh) 2004-09-27 2014-01-11 Fujifilm Corp 遲滯板、橢圓偏光板及液晶顯示器
KR101151082B1 (ko) * 2004-11-29 2012-06-01 삼성전자주식회사 스타형 (올리고티오펜-아릴렌) 유도체 및 이를 이용한유기박막 트랜지스터
CN101258433B (zh) 2005-09-07 2010-12-22 富士胶片株式会社 光学补偿薄膜、其制造方法、以及使用其的偏振片和液晶显示装置
US7989037B2 (en) 2006-10-06 2011-08-02 Fujifilm Corporation Composition, retardation plate, and liquid-crystal display device
CN104119517B (zh) * 2014-05-15 2016-03-30 杭州师范大学 一种星形含硅聚合物及其制备方法与应用
CN109020948A (zh) * 2018-08-03 2018-12-18 浙江工业大学 一种苯-二联噻吩衍生物及其制备方法与应用
CN113061237B (zh) * 2021-03-29 2022-08-30 安庆师范大学 一种苯基噻咯基共轭微孔聚合物及其制备方法、应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001085713A (ja) * 1999-09-14 2001-03-30 Fuji Photo Film Co Ltd 光電変換素子および太陽電池
JP2002322173A (ja) * 2001-04-27 2002-11-08 Nippon Hoso Kyokai <Nhk> 有機化合物、半導体装置、有機ｅｌ素子並びに表示装置

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DAUST G.; LECLERC M.: "Structure-Property Relationships in Alkoxy-Substituted Polythiophenes", MACROMOLECULES, vol. 24, no. 2, 1991, pages 455 - 459, XP000215563 *
KIMURA M. ET AL: "Star-Shaped Stilbenoid Phthalocyanines", CHEM. MATER., vol. 14, no. 6, 2002, pages 2711 - 2717 *

Also Published As

Publication number Publication date
TW200403238A (en) 2004-03-01
WO2004013122A2 (fr) 2004-02-12
DE10234188B4 (de) 2008-04-17
DE10234188A1 (de) 2004-02-12
WO2004013122A3 (fr) 2009-11-05

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