EP1817804A2 - Procede pour synthetiser des derives d'acide phosphonique a chaine longue et des derives de thiol - Google Patents

Procede pour synthetiser des derives d'acide phosphonique a chaine longue et des derives de thiol

Info

Publication number
EP1817804A2
EP1817804A2 EP05823798A EP05823798A EP1817804A2 EP 1817804 A2 EP1817804 A2 EP 1817804A2 EP 05823798 A EP05823798 A EP 05823798A EP 05823798 A EP05823798 A EP 05823798A EP 1817804 A2 EP1817804 A2 EP 1817804A2
Authority
EP
European Patent Office
Prior art keywords
compound
general formula
radical
chain
alkyl
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Withdrawn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
EP05823798A
Other languages
German (de)
English (en)
Inventor
Franz Effenberger
Steffen Maisch
Steffen Seifritz
Günter Schmid
Marcus Halik
Hagen Klauk
Ute Zschieschang
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.)
Qimonda AG
Original Assignee
Qimonda 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 Qimonda AG filed Critical Qimonda AG
Publication of EP1817804A2 publication Critical patent/EP1817804A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/28—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
    • H—ELECTRICITY
    • H03—ELECTRONIC CIRCUITRY
    • H03K—PULSE TECHNIQUE
    • H03K3/00—Circuits for generating electric pulses; Monostable, bistable or multistable circuits
    • 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
    • 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]
    • H10K10/468—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics
    • H—ELECTRICITY
    • H03—ELECTRONIC CIRCUITRY
    • H03K—PULSE TECHNIQUE
    • H03K17/00—Electronic switching or gating, i.e. not by contact-making and –breaking

Definitions

  • the present invention relates to two new processes for preparing low molecular weight organic compounds which can be used in the field of microelectronics, in particular in the field of polymer electronics, in electronic components, such as organic field effect transistors (OFETs), for the production of thin dielectric layers.
  • the organic compounds can be applied to a suitable substrate in the form of a self-assembled monolayer (SAM).
  • SAM self-assembled monolayer
  • Microelectronics was based only a few years ago on the use of inorganic semiconductors, such as silicon or gallium arsenide. These inorganic materials necessitate expensive and costly processes for the production of structured electronic components containing them. This had, among other things means that microelectronics was essentially limited to the manufacture navalwer ⁇ tiger products. In recent years, a large number of new electronic applications have been proposed which, on the one hand, should make use of the technical achievements of silicon-based microelectronics, but on the other hand are intended for mass production.
  • Examples of such mass products are large active matrix screens, which are increasingly the established tubes ⁇ to replace equipment, or RFID systems (abbr. For "rapid dio frequency identification "), which are used for the active identification and identification of goods and merchandise.
  • Active matrix displays such as TFT LC displays, typically include field effect transistors based on amorphous or polycrystalline silicon layers. For the production of these high-quality transistors temperatures are necessary, which are usually above 250 ° C. Such high temperatures necessitate the use of rigid and fragile glass or quartz substrates.
  • Transponders as used in RFID technology, are usually produced using integrated circuits based on monocrystalline silicon. This leads u.a. at considerable cost in the assembly and connection technology. Passive RF-ID systems draw their energy from the radiated alternating field. The maximum permissible distance between the reader and the transponder for the reading process depends on the radiated power of the reader and the energy consumption of the transponder. Silicon-based transponders therefore operate at supply voltages of 3 V. Products containing a silicon-based chip are too expensive for many applications. Therefore, for example, silicon-based identification tags are used for the
  • Examples of microelectronic components based on organic components are the organic field effect Transistors (abbr .: "OFETs”) in z. B. bottom-gate bottom-contact architecture.
  • the gate electrode is deposited on a substrate in the first step, after which the gate dielectric (ie the insulator layer) is applied.
  • the next step is the deposition and patterning of the source and drain electrodes.
  • the semiconductor is deposited between the source and drain electrodes on the gate dielectric.
  • the last layer is followed by the deposition of a passivation layer.
  • Such a transistor is referred to as OFET, if at least the active semiconductor layer consists of an organic semiconductor.
  • the aim is to produce OFETs in which further layers, such as the substrate and / or the gate dielectric, consist of organic materials with tailor-made properties.
  • the basic structure of an OFET or polymer transistor with "bottom-gate" structure is shown in FIG.
  • OFETs can be used for the fabrication of transistors and integrated circuits over large active areas, e.g. B. as pixel controls in the above-mentioned active matrix screens. In addition, they provide access to extremely low-cost integrated circuits, such as those required for transponders in RFID systems.
  • An advantage of organic microelectronic devices is that they use organic materials that can be processed at relatively low temperatures, which are usually below 200 ° C. Therefore, it is possible to use cheap, flexible, transparent and unbreakable polymer films instead of rigid and fragile glass or quartz substrates.
  • the organic materials also allow the practitioner ⁇ dung faster, easier and less expensive manufacturing techniques.
  • cheap printing techniques can can be set to apply the polymers used for the various layers and / or low molecular weight organic materials to the flexible substrate and to structure.
  • the gate potential for the control of transistors can be selected the smaller, the thinner the gate dielectric is produced.
  • High-quality, extremely thin dielectric layers made of organic materials are therefore of great interest for a large number of applications, such as the realization of the above-mentioned low-cost, possibly battery-operated and optionally on large-area flexible substrates.
  • the thickness of the gate dielectric is generally optimized by throwing or printing the solution of a polymer thinner and thinner (top-down). This method, however, reaches its limits when layer thicknesses below 50 nm are to be achieved.
  • the generation of organic gate dielectrics with a thickness below 50 nm is made possible by the use of long-chain organic molecules, which consist of an anchor group, a ⁇ lectric unit and an optional head group. By correctly coordinating the chemical composition and structure of the anchor group on the chemical properties of the surface on which the organic dielectric is to be formed, a self - organization of the long ⁇ chain organic molecules on the surface, in which the molecules on their anchor group on the Surface anchored.
  • the layers thus obtainable consist of monolayers of the long-chain organic compound and are accordingly designated as self-assembled monolayers (abbr .: SAM, of "self-assembled monolayer”).
  • SAMs have excellent insulating properties and can be used as a gate dielectric in the transistor architecture sketched in FIG. They have a thickness of less than 5 nm on special preferably between 1.5 nm and 3 nm. This method can be referred to as a bottom-up approach.
  • T-SAMs top-linked self-assembled monolayers
  • Molecules for T-SAMs additionally have a head group in addition to the anchor group and the dielectric unit.
  • the head groups of the ⁇ ser molecules provide for a particular stability of the SAMs to chemical and physical attacks by ver ⁇ various processes such as wet chemical etching or metal evaporation by the layer additionally by from ⁇ form a binding ⁇ - ⁇ -interaction stabilize ( top link).
  • the top link has enabled the production of gate dielectrics of corresponding quality and thus the production of OFETs.
  • the molecules with silane anchor group described in these two patent applications are particularly well suited for the formation of monolayers on silicon substrates with silicon dioxide natural layer.
  • the compounds with silane anchor group described in DE 103 28 810 and DE 103 28 811 also form SAMs.
  • the leakage currents of the gate dielectrics are too high for real applications obtained with these SAMs, for example by precipitation of 18-phenoxyoctadecyl-1-trichlorosilane on aluminum.
  • organic molecules are described with phosphonic acid anchor group, which can serve to form SAMs in OFETs.
  • Phosphonic acids with a long alkyl chain and terminal methyl group can be prepared by nucleophilic substitution (S H 2 mechanism) of a long-chain alkyl bromide with a trialkyl phosphite in the manner of a Michaelis-Arbuzow reaction.
  • S H 2 mechanism nucleophilic substitution
  • 1-octadecyl bromide with triethylphosphite the commercially available octadecylphosphonic acid is produced in good yield.
  • SAMs self-assembled monolayer
  • X is a radical which is selected from a) the alkyl chains having 2 to 20 carbon atoms, which may be straight-chain or branched and / or substituted and / or may contain one or more unsaturated bonds;
  • Y is oxygen, sulfur, selenium or NH, when X is a partially or completely fluorinated alkyl chain and (CH 2 ) m O,
  • Ar is an optionally substituted aromatic group, and - the radicals Ri to R 4 independently of one another hydrogen,
  • Alkyl radicals having 1 to 20 carbon atoms which may be straight-chain or branched and / or substituted and / or contains unsaturated bond, a per-fluroalkyl radical;
  • R 5 and R 6 are an alkyl radical having 1 to 20 carbon atoms, which may be straight-chain or branched and / or monosubstituted or polysubstituted and / or may contain one or more unsaturated bonds or a perfluoroalkyl radical.
  • the radical X is an n-alkyl chain of the formula - (CHa) x -, in which x represents an integer in the range of 1 and 19.
  • Ar represents the following radicals:
  • the phenyl group is particularly preferred. It has been found, quite surprisingly, that the compound of the general formula I can be reacted virtually quantitatively with a thiocarboxylic acid of the general formula II without addition of a catalyst to obtain a thioester. The thioester can then be reduced with a reducing agent, especially with lithium aluminum hydride LiAlH 4 , to the corresponding thiol. The resulting thiol binds to metallic components and surfaces, in particular of noble metal, such as Au, Ag, Pt, Pd, Rh, Ru, etc. but also to some semiconductors such as GaAs or indium phosphide and forms a SAM, which is additionally stabilized by the head group ,
  • thioester is not necessary in some cases.
  • Many thioesters such as the thioacetic acid ester, add with elimination of the corresponding carboxylic acid, such as acetic acid to the surface of a noble metal r in particular of gold, and then form a self-assembled monolayer.
  • AIBN azobisisobutyrodinitrile
  • the synthetic routes described above for the preparation of thiols and phosphonic acids and their derivatives are very flexible and allow the preparation of a large class of compounds which have an anchor group (thiol radical or phosphonic acid radical) which can interact with the surface, and a omega-permanent group (the head group). These compounds form on their surface self-assembled monolayers via their anchor group, which are stabilized by the head groups.
  • the compounds having a phosphonic acid residue prepared by the process according to the invention bind particularly well to layers of a material selected from aluminum, silicon and titanium. These materials are always coated with a thin layer of oxide because of their non-noble character in an oxygen-containing atmosphere.
  • alloys containing the said metals are particularly preferred.
  • the compounds prepared by the process according to the invention with a thiol radical bind particularly well to noble metal surfaces, for.
  • electrodes consisting of silver, gold, platinum, rhodium, ruthenium, palladium or mercury or an alloy of one or more of these precious metals.
  • alloys containing the said metals are also alloys containing the said metals to a proportion greater than 30%.
  • Particularly preferred are surfaces which consist of gold or gold.
  • Fig. 1 shows the basic structure of a polymer transistor with a bottom-gate bottom-contact structure
  • FIG. 2 illustrates a bottom-gate top-contact structure that examines the suitability of the organic materials for microelectronics produced in the following embodiments, the gate electrode being made of aluminum or gold;
  • FIG. 3 shows the characteristic curves of the test transistor whose gate dielectric consists of a self-organized layer of the organic compound according to Example 2;
  • FIG. 4 contains a schematic representation of the five-stage ring oscillator from Example 9, a snapshot of the oscillation on the oscilloscope and the dependence of the step delay on the supply voltage.
  • Example 2 The reaction is carried out as in Example 1 with the difference that diethyl phosphite is used instead of dimethyl phosphite. In this case, the corresponding diethyl ester is obtained. Subsequently, the diethyl ester is hydrolyzed to 18-phenoxyoctadecylphosphonic acid under the reaction conditions indicated in Example 2.
  • Example 7 Production of an organic field effect transistor with a gate electrode made of aluminum
  • Aluminum is vapor-deposited on a glass plate with a layer thickness of 100 nits in a vacuum.
  • the self-assembled monolayer is deposited from the liquid phase or the gas phase or in the ⁇ -contact pressure as described in DE 10 2004 00 960.7.
  • 30 nm of pentacene are vapor-deposited from the gas phase.
  • the transistor test structure shown in Fig. 2 is completed by vapor deposition of gold electrodes through a shadow mask. The transistor characteristics obtained for this transistor are shown in FIG.
  • Example 8 Production of a component for the food packaging industry
  • Example 7 The manufacturing method shown in Example 7 is carried out with the difference that a polyester film, as used for example in the food packaging industry, is coated with aluminum instead of a glass plate.
  • the finished component can be used in the food packaging industry for labeling foods.
  • the glass plate from Example 7 is provided with a photoresist and exposed at a wavelength of 365 nm through a chromium-on-glass mask.
  • the photoresist is developed with an aqueous KOH solution, which simultaneously etches the aluminum layer.
  • a bottom Contact transistor structure of FIG. 2 completed.
  • the individual masks were matched to each other or the transistors interconnected so that a ring oscillator according to FIG. 4 is formed.
  • An oscilloscope recording of the ring oscillator and the dependence of the step delay of the supply voltage of the ring oscillator are also shown in Fig. 4.
  • Example 11 Production of an organic field-effect transistor with a gate electrode made of platinum or palladium
  • the OFETs are prepared as in Example 10 with the difference that in the first process step platinum or palladium is vapor-deposited on the glass plate to produce the gate electrode.
  • platinum or palladium is vapor-deposited on the glass plate to produce the gate electrode.
  • very stable Top-link SAMs are obtained when the organic compound obtained in Example 5 is used.
  • Example 12 Production of a component for the food packaging industry The manufacturing process shown in Example 10 is carried out with the difference that a polyester film, as used for example in the food packaging industry, is vapor-deposited instead of a glass plate with a very thin layer of gold.
  • the obtained substrate is suitable for the production of polymer electronic circuits, such as an organic field effect transistor for labeling foodstuffs in the food packaging industry.
  • Example 13 Production of a ring oscillator
  • the glass plate of Example 10 is provided with a photoresist and exposed at a wavelength of 365 nm through a chromium-on-glass mask.
  • the photoresist is developed with an aqueous KOH solution.
  • the etching of the gold layer takes place in highly diluted aqua regia (1:30).
  • a bottom-contact transistor structure according to FIG. 2 is completed in the further structure analogously to Example 10.
  • the individual masks have been matched to one another or the transistors are interconnected in such a way that a ring oscillator is produced which corresponds to the ring oscillator depicted in FIG. 4.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Nanotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Condensed Matter Physics & Semiconductors (AREA)
  • General Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Composite Materials (AREA)
  • Physics & Mathematics (AREA)
  • Thin Film Transistor (AREA)

Abstract

La présente invention concerne un procédé pour synthétiser des composés organiques qui peuvent former une couche monomoléculaire auto-organisée. Ces composés sont obtenus en mettant en réaction une oléfine avec un acide thiocarboxylique, puis en mettant en oeuvre une hydrogénation afin d'obtenir un thiol, ou avec un phosphite, puis en mettant en oeuvre une hydrolyse afin d'obtenir de l'acide phosphonique.
EP05823798A 2004-11-30 2005-11-23 Procede pour synthetiser des derives d'acide phosphonique a chaine longue et des derives de thiol Withdrawn EP1817804A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004057760A DE102004057760A1 (de) 2004-11-30 2004-11-30 Methode zur Synthese von langkettigen Phosphonsäurederivaten und Thiolderivaten
PCT/EP2005/056176 WO2006058858A2 (fr) 2004-11-30 2005-11-23 Procede pour synthetiser des derives d'acide phosphonique a chaine longue et des derives de thiol

Publications (1)

Publication Number Publication Date
EP1817804A2 true EP1817804A2 (fr) 2007-08-15

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EP05823798A Withdrawn EP1817804A2 (fr) 2004-11-30 2005-11-23 Procede pour synthetiser des derives d'acide phosphonique a chaine longue et des derives de thiol

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US (1) US20080275273A1 (fr)
EP (1) EP1817804A2 (fr)
DE (1) DE102004057760A1 (fr)
WO (1) WO2006058858A2 (fr)

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WO2009000820A2 (fr) * 2007-06-28 2008-12-31 Siemens Aktiengesellschaft Additif anticorrosion pour liquides
DE102008006374B4 (de) * 2007-09-27 2018-12-06 Osram Oled Gmbh Elektrisches organisches Bauelement und Verfahren zu seiner Herstellung
US7657999B2 (en) * 2007-10-08 2010-02-09 Advantech Global, Ltd Method of forming an electrical circuit with overlaying integration layer
KR20110043675A (ko) 2008-07-18 2011-04-27 조지아 테크 리서치 코포레이션 개질된 일함수를 갖는 안정적인 전극 및 유기 전자 소자의 제조 방법
JP6258569B2 (ja) * 2008-08-04 2018-01-10 ザ、トラスティーズ オブ プリンストン ユニバーシティ 薄膜トランジスタ用のハイブリッド誘電体材料
US8846978B2 (en) 2009-04-06 2014-09-30 Imperial Innovations Ltd. Electronic devices comprising novel phosphonic acid surface modifiers
US8124485B1 (en) 2011-02-23 2012-02-28 International Business Machines Corporation Molecular spacer layer for semiconductor oxide surface and high-K dielectric stack
US9701698B2 (en) * 2014-06-13 2017-07-11 The Chinese University Of Hong Kong Self-assembled monolayers of phosphonic acids as dielectric surfaces for high-performance organic thin film transistors

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Also Published As

Publication number Publication date
WO2006058858A3 (fr) 2006-09-21
US20080275273A1 (en) 2008-11-06
WO2006058858A2 (fr) 2006-06-08
DE102004057760A1 (de) 2006-06-08

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