EP1436850A1 - Insulator for an organic electronic component - Google Patents

Insulator for an organic electronic component

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Publication number
EP1436850A1
EP1436850A1 EP02769910A EP02769910A EP1436850A1 EP 1436850 A1 EP1436850 A1 EP 1436850A1 EP 02769910 A EP02769910 A EP 02769910A EP 02769910 A EP02769910 A EP 02769910A EP 1436850 A1 EP1436850 A1 EP 1436850A1
Authority
EP
European Patent Office
Prior art keywords
insulator
poly
base polymer
organic
styrene
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Withdrawn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
EP02769910A
Other languages
German (de)
French (fr)
Inventor
Erwann Guillet
Peter Bonzani
Walter Fix
Henning Rost
Andreas Ullmann
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.)
PolyIC GmbH and Co KG
Original Assignee
Siemens AG
PolyIC GmbH and Co KG
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 Siemens AG, PolyIC GmbH and Co KG filed Critical Siemens AG
Publication of EP1436850A1 publication Critical patent/EP1436850A1/en
Withdrawn legal-status Critical Current

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
    • H01G4/00—Fixed capacitors; Processes of their manufacture
    • H01G4/002—Details
    • H01G4/018—Dielectrics
    • H01G4/06—Solid dielectrics
    • H01G4/14—Organic dielectrics
    • H01G4/18—Organic dielectrics of synthetic material, e.g. derivatives of cellulose
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/44—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins
    • H01B3/442—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins from aromatic vinyl compounds
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
    • H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
    • H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
    • H01B3/44—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins
    • H01B3/447—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes vinyl resins; acrylic resins from acrylic compounds
    • 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
    • H10K10/471—Insulated gate field-effect transistors [IGFETs] characterised by the gate dielectrics the gate dielectric comprising only organic materials
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
    • H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
    • H01L21/02118—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
    • H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
    • H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
    • H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
    • H01L21/312—Organic layers, e.g. photoresist

Definitions

  • the invention relates to an insulator for an organic electronic component, in particular for an organic field-effect transistor (OFET) and / or an organic capacitor.
  • OFET organic field-effect transistor
  • PHS polyhydroxystyrene
  • Polyimide was also presented as an insulator material (JA Rogers et al., IEEE Electron Devices Letters, Vol 21, No 3, 2000, p. 100). Even if this material is used, there is a risk of damage to the already finished layers of an OFET, since this material can only be processed at extremely high temperatures (-400 ° C). Because organic semi- If the conductor or conductor typically only withstands significantly lower temperatures ( «200 ° C), polyimide cannot be used in fully organic OFETs.
  • the object of the present invention is therefore to provide an isolator for a field-effect transistor which is at least partially constructed from organic material and which overcomes the disadvantages of the prior art.
  • the invention relates to an insulator for an organic electronic component, in particular for an organic field-effect transistor and / or a capacitor based at least in part on organic material, the dielectric constant of the insulator layer remaining essentially constant in a frequency range between 1 Hz and 100 kHz ,
  • the insulator comprises polyisobutylene or uncrosslinked EPDM (ethylene propylene diene monomer), as the base polymer (main component), which are only soluble in nonpolar hydrocarbons (hexane, heptane).
  • EPDM ethylene propylene diene monomer
  • the achievable homogeneous layer thickness with the material lies between approx. 2 ⁇ m-250 nm, whereby these layers still have a sufficiently high insulation property.
  • Another important advantage of this material is that it is very easy to structure in order to enable through contacts (eg by means of lithography).
  • the insulator material comprises commercially available PVDC-PAN-PMMA copolymer of the general formula
  • x, y, and z each, independently of one another, values between 0 and 1, preferably those given in the examples
  • the PVDC-PAN-PMMA copolymer is preferably used together with crosslinker components HMMM (hexamethoxymethalmelamine) and / or Cymel, the ratio of which can be varied widely (dissolved in dioxane).
  • HMMM hexamethoxymethalmelamine
  • Cymel the ratio of which can be varied widely (dissolved in dioxane).
  • This material also enables very simple structuring, although it is not yet networked. Due to very low temperatures (approx. 70 ° C), this material can be networked and then becomes resistant to all subsequent steps that are necessary to complete an OFET and to build an integrated circuit.
  • an insulator mixture comprises a base polymer of the general formula
  • A e.g. Polyhydroxystyrene and B poly (styrene-co-allyl alcohol) e.g. Is polyvinyltoluene, poly-alpha-methylstyrene.
  • an insulator which comprises a mixture of two copolymers, according to the general formula
  • a mixture of poly (vinyltoluene-co-alphamethylstyrene) / poly (styrene-co-allyl alcohol) is particularly suitable.
  • the indices x and y can be the same or different and assume values between 0.5 and 1.
  • X and y are particularly preferably the same.
  • the mixture is again preferably dissolved in polar solvents, especially in dioxane.
  • an insulator layer made of one or a mixture of several of the materials mentioned fulfills the following process, electrical and mechanical requirements and is at the same time a very inexpensive material system:
  • the insulator layer has good solubility in conventional organic solvents such as e.g. Dioxane, butanol other alcohols etc.
  • the insulator layer can be structured after application.
  • the structuring also does not negatively influence existing layers.
  • the structurability is absolutely necessary in order to produce integrated circuits which consist of several OFETs, since only with the structuring the connection lines between the gate electrode of one OFET and the source or drain electrode of another OFET is possible.
  • the insulator layer is chemically and thermally stable with respect to the process steps which are necessary to apply and structure subsequent layers of the OFET (e.g. the gate electrode)
  • the relative dielectric constant of the insulator layer is approximately constant in a frequency range between 1 Hz and 100 kHz.
  • the "relative dielectric constant” is referred to here as “approximately constant” if its change is less than or equal to 50%.
  • the relative dielectric constant of the insulator layer preferably has at least a value of about 2 in the systems mentioned. This makes it possible to implement OFETs that operate at low voltages.
  • the leakage currents through the insulator layer are advantageously negligibly small compared to the source-drain currents, even with very thin layers, i.e. they are preferably below 1 nA (depends on the 0-FET geometry).
  • the dielectric strength of the insulator layer is high, preferably has a value of at least 5 * 10 5 V / cm.
  • the insulator material should preferably not contain any movable contaminants (eg ions).
  • the threshold voltage of the OFET is preferably not shifted by the isolator system.
  • the insulator layer is resistant to mechanical loads such as bending, stretching or upsetting.
  • the insulator layer is applied by spinning, knife coating, printing or spraying in such a way that a plane-parallel, smooth, homogeneous and defect-free layer is produced.
  • structurable layers of either photoresist or metal are applied to the insulator layer.
  • the insulator layer can be removed in a defined manner with suitable solvents and thus also structured. In this way, the insulator layer is always structured at temperatures below 100 ° C, so that this processing has no negative impact on the existing functional layers (e.g. semiconductors).
  • organic material or "organic functional polymer” here encompasses all types of organic, metal-organic and / or organic-inorganic plastics (hybrids), in particular those which are referred to in English as “plastics". They are all types of substances with the exception of the semiconductors that form the classic diodes (germanium, silicon) and the typical metallic conductors. A restriction in the dogmatic sense to organic material as carbon-containing material is therefore not provided, rather the broad use of, for example, silicones is also contemplated. Furthermore, the term should not be subject to any restriction with regard to the molecular size, in particular to polymeric and / or oligomeric materials, but the use of "small molecules” is also entirely possible.
  • the word component "polymer” in the functional polymer is historical and therefore contains no information about the presence of an actually polymeric compound.
  • Example 1 Use of polyisobutylene (PIB) as an insulator - 0.4 g of PIB (Aldrich) are dissolved in 9.6 g of hexane at room temperature;
  • PIB polyisobutylene
  • PVDC-co-PAN-co-PMMA Aldrich
  • 9 g dioxane 40 - 50 ° C - then 0.5 g Cymel 327 (Cytec Industries Inc.) and 0.1 g camphorsulfonic acid added and shaken for a few seconds;
  • the solution is spin-coated (8000 rpm / 20 sec) onto the substrate already provided with source / drain electrodes and semiconductors (top gate structure) and a very homogeneous, approx. 400 nm thick layer is obtained;
  • the sample is dried for about 30 minutes at room temperature in a dynamic vacuum; -
  • the layer is then vapor-deposited with a thin gold layer, which in turn is structured by means of photolithography (photoresist, then etching with a KJ / J 2 solution)
  • This applied metal mask allows the structuring of the insulator layer by removing the now exposed insulator surfaces with a cloth soaked in toluene
  • the last step is the cross-linking of the isolator (10 min at 90 ° C)
  • Example 3 Use of [50% polyhydroxystyrene / 50% poly (styrene-co-allyl alcohol)] as an insulator. This polymer mixture is then dissolved using dioxane and filtered using a 0.2 ⁇ m filter. Then the insulator layer is "baked" on a hot plate at approx. 100 ° C for 30 minutes. The structuring is also carried out using "metal masks" as in Example 2.
  • the insulator material according to the invention shows no significant frequency-dependent change in the relative dielectric constant. Alignment of existing anisotropic molecules can be responsible for this phenomenon, or a lack of mobile charge carriers such as mobile ion NEN. In any case, no significant change in the dielectric constant, that is to say approx. 50%, is found over a frequency range of almost 100 kHz.

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  • Engineering & Computer Science (AREA)
  • Power Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Manufacturing & Machinery (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • Formation Of Insulating Films (AREA)
  • Thin Film Transistor (AREA)
  • Organic Insulating Materials (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Fixed Capacitors And Capacitor Manufacturing Machines (AREA)
  • Semiconductor Integrated Circuits (AREA)

Abstract

The invention concerns an insulator for an organic electronic component, in particular for an organic field-effect transistor (OFET) or for an organic capacitor. The insulating material is characterized in that it includes an almost constant relative dielectric constant, even in case of frequency variation in wide ranges, for example between 1 Hz and 100 Hz.

Description

Beschreibungdescription
Isolator für ein organisches ElektronikbauteilIsolator for an organic electronic component
Die Erfindung betrifft einen Isolator für ein organisches E- lektronikbauteil, insbesondere für einen organischen Feld- Effekt-Transistor (OFET) und/oder einen organischen Kondensator.The invention relates to an insulator for an organic electronic component, in particular for an organic field-effect transistor (OFET) and / or an organic capacitor.
Bekannt ist aus C.J. Dury et al., Appl . Phys . Lett. 73 1998, p. 108) dass Polyhydroxystyrol (PHS) als Isolator in OFETs eingesetzt wird. Hauptnachteil dieses Materials ist, dass bisher keine Möglichkeit bekannt ist, diesen Isolator wirtschaftlich zu strukturieren. Ein weiteres Problem mit diesem Material sind bewegliche Ionen, die zu einem extrem langsamen Schaltverhalten führen. Außerdem ist das PHS relativ teuer.It is known from C.J. Dury et al., Appl. Phys. Lett. 73 1998, p. 108) that polyhydroxystyrene (PHS) is used as an insulator in OFETs. The main disadvantage of this material is that no way is known to structure this insulator economically. Another problem with this material are mobile ions, which lead to extremely slow switching behavior. In addition, the PHS is relatively expensive.
In einer neueren Veröffentlichung wurde kommerziell verfügbarer Fotolack (SC100, Olin Hunt) als Isolator verwendet (G.H. Gelinck et al., Appl. Phys. Lett. 77^ 2000, p. 1487). Wesentlicher Nachteil dieses Verfahrens ist, dass durch die Strukturierung des Fotolacks darunterliegende Schichten stark angegriffen oder zerstört werden. Damit ist es praktisch nicht möglich, diesen Isolator auf schon bestehenden Halblei- terschichten, wie z.B. Polyalkythiophen, zu verwenden. Für die Herstellung eines OFETs wird jedoch die Isolatorschicht über der halbleitenden Schicht, in die die Source und/oder Drain Elektroden eingebettet sind, aufgebracht. Eine Beschädigung der bereits bestehenden halbleitenden Schicht ist im Herstellungsprozess nicht tolerierbar.In a recent publication, commercially available photoresist (SC100, Olin Hunt) was used as the isolator (G.H. Gelinck et al., Appl. Phys. Lett. 77 ^ 2000, p. 1487). A major disadvantage of this method is that the structuring of the photoresist underneath severely attacks or destroys it. It is practically not possible to use this insulator on existing semiconductor layers, e.g. Polyalkythiophene. For the production of an OFET, however, the insulator layer is applied over the semiconducting layer in which the source and / or drain electrodes are embedded. Damage to the already existing semiconducting layer cannot be tolerated in the manufacturing process.
Es wurde auch Polyimid als Isolatormaterial vorgestellt (J.A. Rogers et al., IEEE Electron Devices Letters, Vol 21, No 3, 2000, p. 100) . Auch bei Verwendung dieses Materials ist eine Beschädigung der bereits fertigen Schichten eines OFETs zu befürchten, da dieses Materials nur bei extrem hoher Temperatur (-400 °C) verarbeitet werden kann. Da organische Halblei- ter bzw. Leiter typischerweise nur deutlich niedrigere Temperaturen unbeschadet überstehen (« 200 °C) , kann Polyimid nicht in vollorganischen OFETs eingesetzt werden.Polyimide was also presented as an insulator material (JA Rogers et al., IEEE Electron Devices Letters, Vol 21, No 3, 2000, p. 100). Even if this material is used, there is a risk of damage to the already finished layers of an OFET, since this material can only be processed at extremely high temperatures (-400 ° C). Because organic semi- If the conductor or conductor typically only withstands significantly lower temperatures («200 ° C), polyimide cannot be used in fully organic OFETs.
Unabhängig von den Verarbeitungseigenschaften der bekannten Materialien ist es bisher noch nicht gelungen, einen Isolator zu finden, dessen Dielektrizitätskonstante bei Änderung der eingestrahlten Frequenz grundsätzlich konstant bleibt. Vielmehr zeigen alle diese Materialien eine frequenzabhängige Än- derung der Dielektrizitätskonstante, die ganze Größenordnungen betrifft.Regardless of the processing properties of the known materials, it has not yet been possible to find an insulator whose dielectric constant basically remains constant when the irradiated frequency changes. Rather, all of these materials show a frequency-dependent change in the dielectric constant, which affects entire orders of magnitude.
Aufgabe der vorliegenden Erfindung ist es daher, einen Isolator für einen zumindest teilweise aus organischem Material aufgebauten Feld-Effekt-Transistor zur Verfügung zu stellen, der die Nachteile des Standes der Technik überwindet.The object of the present invention is therefore to provide an isolator for a field-effect transistor which is at least partially constructed from organic material and which overcomes the disadvantages of the prior art.
Gegenstand der Erfindung ist ein Isolator für ein organisches Elektronikbauteil, insbesondere für einen organischen Feld- Effekt-Transistor und/oder einen zumindest teilweise auf organischem Material basierenden Kondensator, wobei die Dielektrizitätskonstante der Isolatorschicht im wesentlichen konstant bleibt in einem Frequenzbereich zwischen 1 Hz und 100 kHz.The invention relates to an insulator for an organic electronic component, in particular for an organic field-effect transistor and / or a capacitor based at least in part on organic material, the dielectric constant of the insulator layer remaining essentially constant in a frequency range between 1 Hz and 100 kHz ,
Nach einer Ausführungsform umfasst der Isolator Polyisobuty- len oder unvernetztes EPDM (Ethylen-Propylen-Dien-Monomer) , als Basispolymer (Hauptkomponente) die nur in unpolaren Kohlenwasserstoffen (Hexan, Heptan) löslich sind. Die erreichba- re homogene Schichtdicke mit dem Material liegt zwischen ca. 2 μm-250 nm, wobei diese Schichten eine noch hinreichend hohe Isolationseigenschaft besitzen. Ein weiterer wichtiger Vorteil dieses Materials liegt in der sehr einfachen Struktu- rierbarkeit um Durchkontakte zu ermöglichen (z.B. mittels Li- thographie) . Nach einer weiteren Ausführungsform umfasst das Isolatormaterial handelsübliches PVDC-PAN-PMMA-Copolymer der allgemeinen FormelAccording to one embodiment, the insulator comprises polyisobutylene or uncrosslinked EPDM (ethylene propylene diene monomer), as the base polymer (main component), which are only soluble in nonpolar hydrocarbons (hexane, heptane). The achievable homogeneous layer thickness with the material lies between approx. 2 μm-250 nm, whereby these layers still have a sufficiently high insulation property. Another important advantage of this material is that it is very easy to structure in order to enable through contacts (eg by means of lithography). According to a further embodiment, the insulator material comprises commercially available PVDC-PAN-PMMA copolymer of the general formula
(-CH2Cl2-)χ-(-CH2CH(CN)-)y-(-CH2C(CH3) (C0CH3) -)(-CH 2 Cl 2 -) χ - (- CH 2 CH (CN) -) y - (- CH 2 C (CH 3 ) (C0CH 3 ) -)
wobei x, y, und z jeweils, unabhängig voneinander, Werte zwischen 0 und 1, bevorzugt die in den Beispielen angegebenenwhere x, y, and z each, independently of one another, values between 0 and 1, preferably those given in the examples
Werte annehmen können.Can assume values.
Das PVDC-PAN-PMMA-Copolymer wird bevorzugt zusammen mit Vernetzerkomponenten HMMM (Hexamethoxymethalmelamin) und/oder Cymel eingesetzt, deren Verhältnis breit variiert werden kann (gelöst in Dioxan) . Dieses Material ermöglicht ebenfalls eine sehr einfache Ξtrukturierung, wobei es dabei noch nicht vernetzt ist. Durch sehr geringe Temperaturen (ca. 70°C) lässt sich dieses Material vernetzen und wird dann resistent gegen alle nachfolgenden Schritte, die nötig sind um einen OFET fertigzustellen und eine integrierte Schaltung aufzubauen.The PVDC-PAN-PMMA copolymer is preferably used together with crosslinker components HMMM (hexamethoxymethalmelamine) and / or Cymel, the ratio of which can be varied widely (dissolved in dioxane). This material also enables very simple structuring, although it is not yet networked. Due to very low temperatures (approx. 70 ° C), this material can be networked and then becomes resistant to all subsequent steps that are necessary to complete an OFET and to build an integrated circuit.
Nach einer Ausführungsform umfasst eine Isolatormischung ein Basispolymer der allgemeinen FormelIn one embodiment, an insulator mixture comprises a base polymer of the general formula
eingesetzt, wobei A z.B. Polyhydroxystyrol und B Poly (styrol-co- allylalkohol) z.B. Polyvinyltoluol, Poly-alpha-methylstyrol ist.used, where A e.g. Polyhydroxystyrene and B poly (styrene-co-allyl alcohol) e.g. Is polyvinyltoluene, poly-alpha-methylstyrene.
Besonders bevorzugt sind dabei Mischungen, wie z.B. [50 % Polyhydroxystyrol / 50 % Poly (styrol-co-allylalkohol) ] , gelöst in polaren Lösungsmitteln wie z.B. Dioxan. Ein großer Vorteil dieses Materials ist die sehr defektarme Schichtaufbringung auf P3AT. Schließlich wird nach einer weiteren Ausführungsform ein Isolator eingesetzt, der ein Gemisch zweier Copolymere umfasst, nach der allgemeinen FormelMixtures, such as [50% polyhydroxystyrene / 50% poly (styrene-co-allyl alcohol)], dissolved in polar solvents such as dioxane, are particularly preferred. A great advantage of this material is the very defect-free layer application on P3AT. Finally, according to a further embodiment, an insulator is used which comprises a mixture of two copolymers, according to the general formula
[A./By][A./B y ]
wobei insbesondere eine Mischung von Poly (vinyltoluol-co- alphamethylstyrol) /Poly (styrol-co-allylalkohol) geeignet ist. Die Indizes x und y können dabei gleich oder ungleich sein und Werte zwischen 0,5 und 1 annehmen. Besonders bevorzugt sind x und y gleich. Das Gemisch ist wiederum bevorzugt in polaren Lösungsmitteln gelöst, insbesondere in Dioxan.a mixture of poly (vinyltoluene-co-alphamethylstyrene) / poly (styrene-co-allyl alcohol) is particularly suitable. The indices x and y can be the same or different and assume values between 0.5 and 1. X and y are particularly preferably the same. The mixture is again preferably dissolved in polar solvents, especially in dioxane.
Die genannten Materialien erfüllen überraschenderweise Eigen- Schaftsprofile, die insbesondere ihre Verwendung als Isolatorschicht in OFETs ermöglicht:The materials mentioned surprisingly fulfill property profiles, which in particular enable their use as an insulator layer in OFETs:
Dies insbesondere, weil eine Isolatorschicht aus einem oder einer Mischung mehrerer der genannten Materialien folgende prozesstechnische, elektrische und mechanische Anforderungen erfüllt und gleichzeitig ein sehr preiswertes Materialsystem ist :This is particularly so because an insulator layer made of one or a mixture of several of the materials mentioned fulfills the following process, electrical and mechanical requirements and is at the same time a very inexpensive material system:
a) Prozesstechnische Anforderungen: b)a) Process requirements: b)
Die Isolatorschicht hat eine gute Löslichkeit in herkömmlichen organischen Lösungsmitteln wie z.B. Dioxan, Butanol andere Alkohole etc.The insulator layer has good solubility in conventional organic solvents such as e.g. Dioxane, butanol other alcohols etc.
- Das Aufbringen der Isolatorschicht auf schon bestehende Schichten des OFETs (z.B. die Halbleiterschicht) schädigt diese Schichten weder durch Angreifen, Anlösen noch durch Veränderung ihrer Eigenschaften.- Applying the insulator layer to existing layers of the OFET (e.g. the semiconductor layer) does not damage these layers by attacking, dissolving or changing their properties.
- Die Isolatorschicht ist nach dem Aufbringen strukturierbar. Das Strukturieren beeinflusst ebenfalls bestehende Schichten nicht negativ. Die Strukturierbarkeit ist unabdingbar nötig, um integrierte Schaltungen herzustellen, die aus mehreren OFETs bestehen, da erst mit der Strukturierung die Verbindungsleitungen zwischen der Gate-Elektrode eines OFETs und der Source- bzw. Drain-Elektrode eines anderen OFETs möglich wird.- The insulator layer can be structured after application. The structuring also does not negatively influence existing layers. The structurability is absolutely necessary in order to produce integrated circuits which consist of several OFETs, since only with the structuring the connection lines between the gate electrode of one OFET and the source or drain electrode of another OFET is possible.
Nach dem Strukturieren ist die Isolatorschicht chemisch und thermisch stabil gegenüber den Prozessschritten, die nötig sind um nachfolgende Schichten des OFETs aufzubringen und zu strukturieren (z.B. die Gate- Elektrode)After structuring, the insulator layer is chemically and thermally stable with respect to the process steps which are necessary to apply and structure subsequent layers of the OFET (e.g. the gate electrode)
b) Elektrische Anforderungen:b) Electrical requirements:
- Die relative Dielektrizitätskonstante der Isolatorschicht ist in etwa konstant in einem Frequenzbereich zwischen 1 Hz und 100 kHz. Als "in etwa konstant" wird die relative Dielektrizitätskonstante hier bezeichnet, wenn ihre Änderung kleiner gleich 50% beträgt.- The relative dielectric constant of the insulator layer is approximately constant in a frequency range between 1 Hz and 100 kHz. The "relative dielectric constant" is referred to here as "approximately constant" if its change is less than or equal to 50%.
Die relative Dielektrizitätskonstante der Isolatorschicht hat bevorzugt mindestens einen Wert von etwa 2 bei den genannten Systemen. Damit lassen sich OFETs realisieren, die bei niedrigen Spannungen arbeiten.The relative dielectric constant of the insulator layer preferably has at least a value of about 2 in the systems mentioned. This makes it possible to implement OFETs that operate at low voltages.
Die Leckströme durch die Isolatorschicht sind vorteilhafterweise auch bei sehr dünnen Schichten vernachlässigbar klein gegenüber den Source-Drain-Strömen, d.h. sie liegen bevorzugt unter 1 nA (hängt von der 0- FET-Geometrie ab) .The leakage currents through the insulator layer are advantageously negligibly small compared to the source-drain currents, even with very thin layers, i.e. they are preferably below 1 nA (depends on the 0-FET geometry).
Die elektrische Durchschlagsfestigkeit der Isolatorschicht ist hoch, hat bevorzugt einen Wert von mindestens 5*105 V/cm.The dielectric strength of the insulator layer is high, preferably has a value of at least 5 * 10 5 V / cm.
Das Isolatormaterial soll bevorzugt keine beweglichen Verunreinigungen enthalten (z.B. Ionen). Die Schwellwertspannung des OFETs wird bevorzugt durch das Isolatorsystem nicht verschoben.The insulator material should preferably not contain any movable contaminants (eg ions). The threshold voltage of the OFET is preferably not shifted by the isolator system.
mechanische Anforderungen:Mechanical Requirements:
Die Isolatorschicht ist in Grenzen beständig gegenüber mechanischen Belastungen wie Verbiegen, Dehnen o- der Stauchen.The insulator layer is resistant to mechanical loads such as bending, stretching or upsetting.
Das Aufbringen der Isolatorschicht durch Aufschleudern, Rakeln, Drucken oder Aufsprühen erfolgt so, dass eine planparallele, glatte, homogene und defektfreie Schicht entsteht.The insulator layer is applied by spinning, knife coating, printing or spraying in such a way that a plane-parallel, smooth, homogeneous and defect-free layer is produced.
Zur Herstellung des fertigen OFETs werden auf die Isolatorschicht strukturierbare Schichten aus entweder Photolack oder Metall aufgebracht. Nach deren Strukturierung kann die Isolatorschicht mit geeigneten Lösungsmitteln definiert entfernt und somit ebenfalls strukturiert werden. Die Isolatorschicht wird auf diese Weise stets bei Temperaturen unter 100 °C strukturiert, so dass diese Prozessierung keinen negativen Einfluss auf die bereits vorhandenen Funktionsschichten (z.B. Halbleiter) hat.To produce the finished OFET, structurable layers of either photoresist or metal are applied to the insulator layer. After structuring, the insulator layer can be removed in a defined manner with suitable solvents and thus also structured. In this way, the insulator layer is always structured at temperatures below 100 ° C, so that this processing has no negative impact on the existing functional layers (e.g. semiconductors).
Die exzellenten elektrischen Eigenschaften, d.h. hohe Dielektrizitätskonstante, hohe Durchschlagsspannung und niedrige Leckströme der betrachteten Materialsysteme erlauben weiterhin die Erzeugung von relativ dünnen Isolatorschichten, was zu einer drastischen Reduzierung der benötigten Gate-Spannung auf bevorzugte Werte unter 10 V führt.The excellent electrical properties, i.e. High dielectric constant, high breakdown voltage and low leakage currents of the material systems under consideration continue to allow the production of relatively thin insulator layers, which leads to a drastic reduction in the required gate voltage to preferred values below 10 V.
Der Begriff "organisches Material" oder "organisches Funktionspolymer" umfasst hier alle Arten von organischen, metall- organischen und/oder organisch-anorganischen Kunststoffen (Hybride), insbesondere die, die im Englischen z.B. mit "plastics" bezeichnet werden. Es handelt sich um alle Arten von Stoffen mit Ausnahme der Halbleiter, die die klassischen Dioden bilden (Germanium, Silizium) , und der typischen metallischen Leiter. Eine Beschränkung im dogmatischen Sinn auf organisches Material als Kohlenstoff-enthaltendes Material ist demnach nicht vorgesehen, vielmehr ist auch an den breiten Einsatz von z.B. Siliconen gedacht. Weiterhin soll der Term keiner Beschränkung im Hinblick auf die Molekülgröße, insbesondere auf polymere und/oder oligomere Materialien unterliegen, sondern es ist durchaus auch der Einsatz von "small molecules" möglich. Der Wortbestandteil "polymer" im Funktionspolymer ist historisch bedingt und enthält insofern keine Aussage über das Vorliegen einer tatsächlich polymeren Verbindung.The term "organic material" or "organic functional polymer" here encompasses all types of organic, metal-organic and / or organic-inorganic plastics (hybrids), in particular those which are referred to in English as "plastics". They are all types of substances with the exception of the semiconductors that form the classic diodes (germanium, silicon) and the typical metallic conductors. A restriction in the dogmatic sense to organic material as carbon-containing material is therefore not provided, rather the broad use of, for example, silicones is also contemplated. Furthermore, the term should not be subject to any restriction with regard to the molecular size, in particular to polymeric and / or oligomeric materials, but the use of "small molecules" is also entirely possible. The word component "polymer" in the functional polymer is historical and therefore contains no information about the presence of an actually polymeric compound.
Im folgenden wird die Erfindung noch anhand einiger Beispiele, die Ausführungsformen der Erfindung beschreiben, erläutert :In the following, the invention will be explained with reference to a few examples that describe embodiments of the invention:
Beispiel 1: Verwendung von Polyisobutylen (PIB) als Isolator - 0,4 g PIB (Aldrich) werden in 9,6 g Hexan bei Raumtemperatur gelöst;Example 1: Use of polyisobutylene (PIB) as an insulator - 0.4 g of PIB (Aldrich) are dissolved in 9.6 g of hexane at room temperature;
- die Lösung wird durch einen 0,45 μm PTFE-Spritzenfilter filtriert;- The solution is filtered through a 0.45 μm PTFE syringe filter;
- die Lösung wird dann durch spin-coating (4000 U/min; 20 sec) auf das bereits mit Source/Drain-Elektroden und Halbleiter versehene Substrat aufgeschleudert (top-Gate Aufbau) und man erhält eine sehr homogene, ca. 260 n dicke Schicht- The solution is then spin-coated (4000 rpm; 20 sec) onto the substrate that has already been provided with source / drain electrodes and semiconductors (top-gate structure) and a very homogeneous, approximately 260 nm thick layer is obtained layer
- die Probe wird ca. 30 min bei Raumtemperatur im dynamischen Vakuum getrocknet - anschließend wird eine dicke Schicht Photolack auf den Isolator aufgebracht, belichtet und unter normalen Bedingungen entwickelt;- The sample is dried for approx. 30 min at room temperature in a dynamic vacuum - Then a thick layer of photoresist is applied to the insulator, exposed and developed under normal conditions;
- die Probe wird in ein Hexanbad getaucht und an den vom Photolack befreiten Stellen wird der Isolator abgelöst - der restliche Photolack wird durch ein geeignetes Lösungsmittel entfernt Beispiel 2: Verwendung von PVDC-PAN-PMMA (x = 0.89, y = 0.03, z 0.08) als Isolator- The sample is immersed in a hexane bath and the insulator is removed from the areas where the photoresist has been removed - the remaining photoresist is removed with a suitable solvent Example 2: Use of PVDC-PAN-PMMA (x = 0.89, y = 0.03, z 0.08) as an insulator
- 0,4 g PVDC-co-PAN-co-PMMA (Aldrich) werden in 9 g Dioxan bei 40 - 50 °C gelöst - dann werden 0,5 g Cymel 327 (Cytec Industries Inc.) und 0,1 g Kamphersulfonsäure zugesetzt und noch einige Sekunden geschüttelt;- 0.4 g PVDC-co-PAN-co-PMMA (Aldrich) are dissolved in 9 g dioxane at 40 - 50 ° C - then 0.5 g Cymel 327 (Cytec Industries Inc.) and 0.1 g camphorsulfonic acid added and shaken for a few seconds;
- die Lösung wird durch einen 0,45 um PTFE-Filter gefiltert;- The solution is filtered through a 0.45 µm PTFE filter;
- die Lösung wird durch Aufschleudern (8000 ü/min; 20 sec) auf das bereits mit Source/Drain-Elektroden und Halbleiter versehene Substrat aufgeschleudert (top-Gate Aufbau) und man erhält eine sehr homogene, ca. 400 nm dicke Schicht;- The solution is spin-coated (8000 rpm / 20 sec) onto the substrate already provided with source / drain electrodes and semiconductors (top gate structure) and a very homogeneous, approx. 400 nm thick layer is obtained;
- die Probe wird ca. 30 min bei Raumtemperatur im dynamischen Vakuum getrocknet; - die Schicht wird dann mit einer dünnen Goldschicht bedampft, die wiederum mittels Photolithographie strukturiert wird (Photolack, dann Ätzen mit KJ/J2-Lösung)- The sample is dried for about 30 minutes at room temperature in a dynamic vacuum; - The layer is then vapor-deposited with a thin gold layer, which in turn is structured by means of photolithography (photoresist, then etching with a KJ / J 2 solution)
- diese aufgebrachte Metallmaske erlaubt die Strukturierung der Isolatorschicht, indem die nun freiliegenden Isolatorflä- chen mit einem mit Toluol getränkten Tuch entfernt werden- This applied metal mask allows the structuring of the insulator layer by removing the now exposed insulator surfaces with a cloth soaked in toluene
- dann erfolgt die Entfernung der Goldreste mit KJ/J2-Lösung- Then the gold residues are removed with KJ / J 2 solution
- letzter Schritt ist die Vernetzung des Isolators (10 min bei 90 °C)- the last step is the cross-linking of the isolator (10 min at 90 ° C)
Beispiel 3: Verwendung von [50 % Polyhydroxystyrol / 50 % Poly (styrol-co-allylalkohol) ] als Isolator. Diese Polymermischung wird anschließend mittels Dioxan gelöst und mit einem 0,2μm Filter gefiltert. Anschließend wird die Isolatorschicht 30 Minuten bei ca. 100°C auf einer Heizplatte "ausgebacken". Die Strukturierung erfolgt ebenfalls mittels "Metallmasken" wie in Beispiel 2.Example 3: Use of [50% polyhydroxystyrene / 50% poly (styrene-co-allyl alcohol)] as an insulator. This polymer mixture is then dissolved using dioxane and filtered using a 0.2 μm filter. Then the insulator layer is "baked" on a hot plate at approx. 100 ° C for 30 minutes. The structuring is also carried out using "metal masks" as in Example 2.
Das Isolatormaterial nach der Erfindung zeigt keine wesentliche frequenzabhängige Änderung der relativen Dielektrizi- tätskonstante. Für dieses Phänomen kann zum einen eine Ausrichtung vorhandener anisotroper Moleküle verantwortlich sein oder ein Fehlen beweglicher Ladungsträger wie beweglicher Io- nen. Jedenfalls wird über einen Frequenzbereich von nahezu 100 kHz keine wesentliche, also ca. 50 % übersteigende, Änderung der Dielektrizitätskonstante festgestellt. The insulator material according to the invention shows no significant frequency-dependent change in the relative dielectric constant. Alignment of existing anisotropic molecules can be responsible for this phenomenon, or a lack of mobile charge carriers such as mobile ion NEN. In any case, no significant change in the dielectric constant, that is to say approx. 50%, is found over a frequency range of almost 100 kHz.

Claims

Patentansprüche claims
1. Isolator für ein organisches Elektronikbauteil, insbesondere für einen organischen Feld-Effekt-Transistor und/oder einen zumindest teilweise auf organischem Material basierenden Kondensator, wobei die Dielektrizitätskonstante der Isolatorschicht im wesentlichen konstant bleibt in einem Frequenzbereich zwischen 1 Hz und 100 kHz.1. Insulator for an organic electronic component, in particular for an organic field-effect transistor and / or a capacitor based at least in part on organic material, the dielectric constant of the insulator layer remaining essentially constant in a frequency range between 1 Hz and 100 kHz.
2. Isolator nach Anspruch 1, der Polyisobutylen oder unver- netztes EPDM (Ethylen-Propylen-Dien-Monomer) als Basispolymer umfasst.2. Insulator according to claim 1, which comprises polyisobutylene or uncrosslinked EPDM (ethylene-propylene-diene monomer) as the base polymer.
3. Isolator nach Anspruch 1, der handelsübliches PVDC-PAN- PMMA-Copolymer der allgemeinen Formel3. Insulator according to claim 1, the commercially available PVDC-PAN-PMMA copolymer of the general formula
(-CH2Cl2-)χ-(-CH2CH(CN)-)y-(-CH2C(CH3) (C02CH3)-)z ,(-CH 2 Cl 2 -) χ - (- CH 2 CH (CN) -) y - (- CH 2 C (CH 3 ) (C0 2 CH 3 ) -) z ,
wobei x, y, und z jeweils, unabhängig voneinander, Werte zwi- sehen 0 und 1 annehmen kann, als Basispolymer umfasst.where x, y, and z each, independently of one another, can assume values between 0 and 1, as the base polymer.
4. Isolator nach Anspruch 1, der ein Basispolymer der allgemeinen Formel4. Insulator according to claim 1, which is a base polymer of the general formula
umfasst, wobei A z.B. Polyhydroxystyrol und B Poly (styrol-co- allylalkohol) , Polyvinylalkohol, und/oder Poly- - methylstyrol ist.where A e.g. Polyhydroxystyrene and B is poly (styrene-co-allyl alcohol), polyvinyl alcohol, and / or poly- methyl styrene.
5. Isolator nach Anspruch 4, bei dem das Basispolymer eine Mischung aus 50 % Polyhydroxystyrol / 50 % Poly (styrol-co- allylalkohol) ] ist.5. The insulator of claim 4, wherein the base polymer is a blend of 50% polyhydroxystyrene / 50% poly (styrene-co-allyl alcohol)].
6. Isolator nach Anspruch 1, der als Basispolymer ein Gemisch zweier Polymerer umfasst, nach der allgemeinen Formel mit A gleich Poly (vinyltoluol-co-alphamethylstyrol) und B gleich Poly (styrol-co-allylalkohol) , wobei die Werte von x und y gleich oder ungleich sind und Werte zwischen 0,5 und 1 haben.6. Insulator according to claim 1, which comprises a mixture of two polymers as the base polymer, according to the general formula where A is poly (vinyltoluene-co-alphamethylstyrene) and B is poly (styrene-co-allyl alcohol), where the values of x and y are the same or different and have values between 0.5 and 1.
7. Isolator nach Anspruch 6, bei dem die Werte von x und y gleich sind.7. The isolator of claim 6, wherein the values of x and y are the same.
8. Isolator nach einem der Ansprüche 3 bis 7, bei dem das Basispolymer gelöst in einem polaren Lösungsmittel wie z.B. Dioxan oder einem polaren Gemisch aus zumindest zwei Lösungs- mittel vorliegt. Insulator according to any one of claims 3 to 7, in which the base polymer is dissolved in a polar solvent such as e.g. Dioxane or a polar mixture of at least two solvents is present.
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US20050048803A1 (en) 2005-03-03
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