WO2002045184A1 - Field effect transistors and materials and methods for their manufacture - Google Patents

Field effect transistors and materials and methods for their manufacture Download PDF

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Publication number
WO2002045184A1
WO2002045184A1 PCT/GB2001/005145 GB0105145W WO0245184A1 WO 2002045184 A1 WO2002045184 A1 WO 2002045184A1 GB 0105145 W GB0105145 W GB 0105145W WO 0245184 A1 WO0245184 A1 WO 0245184A1
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Prior art keywords
binder
organic
field effect
semiconductor
layer
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PCT/GB2001/005145
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English (en)
French (fr)
Inventor
Beverley Anne Brown
Domenico Carlo Cupertino
Stephen William Leeming
John David Schofield
Janos Veres
Stephen George Yeates
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Avecia Limited
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Application filed by Avecia Limited filed Critical Avecia Limited
Priority to AU2081802A priority Critical patent/AU2081802A/xx
Priority to DE60125819T priority patent/DE60125819T2/de
Priority to JP2002547243A priority patent/JP4429603B2/ja
Priority to AU2002220818A priority patent/AU2002220818B2/en
Priority to CA2427222A priority patent/CA2427222C/en
Priority to EP01999012A priority patent/EP1340270B1/en
Priority to KR1020037006957A priority patent/KR100824026B1/ko
Priority to US10/416,005 priority patent/US7095044B2/en
Publication of WO2002045184A1 publication Critical patent/WO2002045184A1/en

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    • 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
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L29/00—Semiconductor devices adapted for rectifying, amplifying, oscillating or switching, or capacitors or resistors with at least one potential-jump barrier or surface barrier, e.g. PN junction depletion layer or carrier concentration layer; Details of semiconductor bodies or of electrodes thereof  ; Multistep manufacturing processes therefor
    • H01L29/02—Semiconductor bodies ; Multistep manufacturing processes therefor
    • H01L29/06—Semiconductor bodies ; Multistep manufacturing processes therefor characterised by their shape; characterised by the shapes, relative sizes, or dispositions of the semiconductor regions ; characterised by the concentration or distribution of impurities within semiconductor regions
    • H01L29/08—Semiconductor bodies ; Multistep manufacturing processes therefor characterised by their shape; characterised by the shapes, relative sizes, or dispositions of the semiconductor regions ; characterised by the concentration or distribution of impurities within semiconductor regions with semiconductor regions connected to an electrode carrying current to be rectified, amplified or switched and such electrode being part of a semiconductor device which comprises three or more electrodes
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L29/00—Semiconductor devices adapted for rectifying, amplifying, oscillating or switching, or capacitors or resistors with at least one potential-jump barrier or surface barrier, e.g. PN junction depletion layer or carrier concentration layer; Details of semiconductor bodies or of electrodes thereof  ; Multistep manufacturing processes therefor
    • H01L29/66—Types of semiconductor device ; Multistep manufacturing processes therefor
    • H01L29/68—Types of semiconductor device ; Multistep manufacturing processes therefor controllable by only the electric current supplied, or only the electric potential applied, to an electrode which does not carry the current to be rectified, amplified or switched
    • H01L29/76—Unipolar devices, e.g. field effect transistors
    • H01L29/772—Field effect transistors
    • H01L29/78—Field effect transistors with field effect produced by an insulated 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 a potential-jump barrier or a surface barrier
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
    • H10K10/488—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising a layer of composite material having interpenetrating or embedded materials, e.g. a mixture of donor and acceptor moieties, that form a bulk heterojunction
    • 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
    • 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
    • H10K85/151—Copolymers
    • 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 a potential-jump barrier or a surface barrier
    • 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
    • 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
    • H10K85/115—Polyfluorene; Derivatives thereof
    • 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
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine

Definitions

  • This invention relates to Field Effect Transistors (FETs) and materials and methods for their manufacture.
  • FETs are electronic devices which are capable of modulating the current between two electrodes called the drain and the source by the application of a voltage on a third electrode called the gate.
  • the current is modulated by accumulating or depleting charge carriers in a semiconductor channel between the drain and the source.
  • inorganic semiconductors such as Si or GaAs have been used for the channel material.
  • FETs find use in a number of applications at present such as in the active drive matrix for large area displays.
  • FETs using inorganic materials are often difficult and expensive to manufacture due to the high temperature processing conditions and vacuum required to give uniform devices over large areas.
  • organic compounds J. Mater. Chem..
  • EP 0910100A2 (Xerox) describes compositions for conductive coatings, which comprise of a polymer binder, charge transport molecules and an oxidising agent.
  • the oxidising agent is used to increase the carrier concentration.
  • Such coatings may be envisaged as conductive electrodes for electronic devices, e.g. transistors such as gate, drain and source contacts or conductive tracks between them.
  • the disclosure does not relate to the semiconductor channel material for FETs.
  • US 5,500,537 (Mitsubishi) claims FETs with at least two different organic channel materials, both of which are semiconductors, one compound having a higher conductivity than the other and used to supply carriers in the channel, thus achieving better current modulation.
  • the application also mentions that a further "electrically insulating material" can be mixed in but without reference what such material may be or how it is applied.
  • the carrier supply function of the first material can also be achieved when it forms a layer next to the second material.
  • EP0478380A1 (Toshiba) describes organic thin film elements consisting of a mixed stacked charge-transfer (CT) complex using a mixture of donor and acceptor like materials.
  • CT charge-transfer
  • the complex film can be affected to change its state from neutral to ionic by the application of an electric field.
  • FET field-effect transistor
  • Multi-stack channels are also described using several double-layers of a CT complex layer followed by an insulating polyvinylidene fluoride (PVDF) layer.
  • PVDF polyvinylidene fluoride
  • EP 0528 662 A1 discloses an FET with a first organic layer constituting the FET channel and a second, adjacent layer with a different carrier concentration.
  • the role of the second layer is to inject carriers into the channel when a voltage is applied to the gate.
  • the second organic layer can be made as a photoreceptor consisting of photogeneration and charge transport layers.
  • the charge transport layer may consist of a charge transport material in a binder polymer.
  • the invention uses such charge generating/charge transporting layers solely as a second layer supplying excess carriers into the first organic layer (the channel) and does not suggest using binder compositions as the active channel layer itself.
  • EP 0981165 A1 (Lucent) describes thin film transistor integrated circuits with inverted structures.
  • semiconductor materials used may be 4,4'-diaminobisphenyls in polymer matrices.
  • US 5,625,199 (Lucent) discloses complementary circuits with p and n type organic transistors. It also mentions that p- channel elements may be made of p,p'-diaminobisphenyl in polymer matrices.
  • neither document teaches what the polymer matrices may be and does not consider any other compounds than p,p'-diaminobisphenyls.
  • a field effect transistor in which a continuous semiconductor layer comprises: a) an organic semiconductor; and b) an organic binder which has an inherent conductivity of less than 10 "6 Scm "1 and a permittivity, ⁇ , at 1 ,000 Hz of less than 3.3.
  • the organic binder is preferably one in which at least 95%, more preferably at least 98% and especially all of the atoms are hydrogen, fluorine and carbon atoms.
  • Preferred binders are materials of low permittivity.
  • the organic binder preferably has a permittivity at 1 ,000 Hz of less than 3.0, more preferably less than 2.8 and preferably greater than 1.7, especially a permittivity from 2.0 to 2.8.
  • organic binder is a homopolymer of polystyrene its molecular weight is preferably less than 20,000 daltons, more preferably less than 15,000 daltons, and especially greater than 1 ,000 daltons.
  • the organic semiconductor has a field effect mobility of more than 10 "5 cm 2 V “1 s "1 and an inherent (i.e. when not exposed to an electric field) conductivity of less than 10 ⁇ 6 Scm "1 .
  • a preferred sub-group of field effect transistors comprise a continuous semiconductor layer which has a field effect mobility of more than 10 "5 cmW 1 and an inherent (i.e. when not exposed to an electric field) conductivity of less than 10 "6 Son "1 which layer comprises: a) an organic semiconductor having an inherent conductivity of less than 10 ⁇ 6 Scm “1 and preferably a field effect mobility of more than 10 "5 cm 2 V “1 s "1 and b) an organic binder which has an inherent conductivity of less than 10 6 Scm “1 and a permittivity at 1 ,000 Hz of less than 3 and more preferably less than 2.8 and preferably greater than 1.7, especially from 2.0 to 2.8 with the proviso that if the binder is a homopolymer of polystyrene its molecular weight is less than 20,000 daltons and preferably less than 15,000 daltons, and is preferably greater than 1 ,000 daltons.
  • a further preferred sub-group of field effect transistors comprise a continuous semiconductor layer which comprises: a) an organic semiconductor and b) a binder of which at least 95% and preferably at least 98% and preferably all of the atoms are hydrogen, fluorine and carbon atoms with the proviso that if the hydrocarbon binder is a homopolymer of polystyrene its molecular weight is less than 20,000 daltons and preferably less than 15,000 daltons, and is preferably greater than 1 ,000 daltons.
  • the semiconductor may be an n or p type.
  • the organic semiconductor may be any conjugated aromatic molecule containing at least three aromatic rings. Preferred organic semiconductors contain 5, 6 or 7 membered aromatic rings, especially preferred organic semiconductors contain 5 or 6 membered aromatic rings.
  • Each of the aromatic rings may optionally contain one or more hetero atoms selected from Se, Te, P, Si, B, As, N, O or S, preferably from N, O or S.
  • the rings may be optionally substituted with alkyl, alkoxy, polyalkoxy, thioalkyl, acyl, aryl or substituted aryl groups, a fluorine atom, a cyano group, a nitro group or an optionally substituted secondary or tertiary alkylamine or arylamine -N(R 3 )(R 4 ), where R 3 and R 4 each independently is H, optionally substituted alkyl, optionally substituted aryl, alkoxy or polyalkoxy groups.
  • the alkyl and aryl groups may be optionally fluorinated.
  • T, and T 2 each independently represent H, Cl, F, -C ⁇ N or lower alkyl groups particularly C ⁇ alkyl groups;
  • R' represents H, optionally substituted alkyl or optionally substituted aryl.
  • the alkyl and aryl groups may be optionally fluorinated.
  • organic semi-conducting materials that can be used in this invention include soluble compounds and soluble derivatives of compounds of the following list : conjugated hydrocarbon polymers such as polyacene, polyphenylene, poly(phenylene vinylene), polyfluorene including oligomers of those conjugated hydrocarbon polymers; condensed aromatic hydrocarbons such as tetracene, chrysene, pentacene, pyrene, perylene, coronene; oligomeric para substituted phenylenes such as p-quaterphenyl (p- 4P), p-quinquephenyl (p-5P), p-sexiphenyl (p-6P); conjugated heterocyclic polymers such as poly(3-substituted thiophene), poly(3,4-bisubstituted thiophene), polybenzothiophene, polyisothianapthene, poly( ⁇ /-substituted pyrrole), poly(3-
  • each Y 1 is independently selected from P, S, As, N and Se and preferably Y 1 is N; Ar 1 and Ar 2 are aromatic groups and Ar 3 is present only if Y 1 is N, P, or As in which case it too is an aromatic group.
  • Ar 1 , Ar 2 and Ar 3 may be the same or different and represent, independently if in different repeat units, a multivalent (preferably bivalent) aromatic group (preferably mononuclear but optionally polynuclear) optionally substituted by at least one optionally substituted 0,- 40 carbyl-derived groups and/or at least one other optional substituent, and Ar 3 represents, independently if in different repeat units, a mono or multivalent (preferably bivalent) aromatic group (preferably mononuclear but optionally polynuclear) optionally substituted by at least one: optionally substituted C M0 carbyl- derived group and/or at least one other optional substituent; where at least one terminal group is attached in the polymer to the Ar 1 , Ar 2 and optionally Ar 3 groups located at the
  • WO 99/32537 is a patent application of the applicants which describes certain novel oligomers and polymers which have repeat units of formula 1.
  • polymers of this type are prepared by the addition of an end capping reagent to control the molecular weight of the final polymer and hence its desirable properties as a charge transport material.
  • end capping reagent to control the molecular weight of the final polymer and hence its desirable properties as a charge transport material.
  • the disclosure of this application is incorporated herein by reference, as these materials are particularly useful as semiconductors in the present invention.
  • the number of repeat units of Formula 1 which may be present per molecule in the invention may be from 2 to 1 ,000, preferably from 3 to 100 and more preferably from 3 to 20 inclusive.
  • the preferred polymeric materials are obtainable by polymerisation controlled by the addition of at least one end capping reagent in an amount sufficient to reduce substantially further growth of the polymer chain.
  • the asterisks extending from Ar 1 and Ar 2 in Formula 1 are intended to indicate that these groups may be multivalent (including divalent as shown in Formula 1 ).
  • amine materials that may be useful in this invention are tetrakis(N,N ' -aryl)biaryldiamines, bis(N,N'-[substitutedphenyl]), bis(N,N'-phenyl)-1 ,1 ' -bi- phenyl-4,4 ' -diamines including 4-methyl, 2,4-dimethyl and/or 3-methyl derivatives thereof; triphenylamine and its alkyl and aryl derivatives and poly(N-phenyl-1 ,4-phenyleneamine); N-dibenzo[a,d]cycloheptene-5-ylidene-N',N'-di-p-tolyl-benzene-1 ,4-diamine, (9,9-dimethyl- 9H-fluorene-2-yl)-di-p-tolyl-amine and their derivatives.
  • Conjugated oligomeric and polymeric heterocyclic semiconductors may comprise a repeat unit of an optionally substituted 5 membered ring and terminal groups Y 1 and Y 2 as shown in Formula 2:
  • X may be Se, Te or preferably O, S, or -N(R)- where R represents H, optionally substituted alkyl or optionally substituted aryl;
  • R 1 , R 2 , A 1 and A 2 may be independently H, alkyl, alkoxy, thioalkyl, acyl, aryl or substituted aryl, a fluorine atom, a cyano group, a nitro group or an optionally substituted secondary or tertiary alkylamine or arylamine -N(R 3 )(R 4 ), where R 3 and R 4 are as defined above.
  • the alkyl and aryl groups represented by R ⁇ R 2 , R 3 , R 4 , A 1 and A 2 may be optionally fluorinated.
  • the number of recurring units in the conjugated oligomer of Formula 2 is represented by an integer n , where n is preferably 2 to 14.
  • Oligomers containing a conjugated linking group may be represented by Formula 3:
  • Polymers may have repeat units of the general Formula 4:
  • the sub units may be polymerised in such a way as to give a regio regular or a regio random polymer comprising repeat units as shown in Formulae 4 to 6:
  • Polymers may have repeat units of the general Formula 7:
  • Polymers may have repeat units of general Formula 8:
  • R 1 and R 2 are defined as above.
  • one of R 1 or R 2 is an alkoxide of general formula C n H 2n+1 O-, and the other of R 1 or R 2 is H, poly('- dodecyloxy- ⁇ , ⁇ ',- ⁇ , ⁇ " terthienyl) i.e. polyDOT 3 .
  • Polymers may have repeat units of general Formula 9:
  • R 5 and R 6 may be independently H, alkyl, aryl or substituted aryl.
  • the alkyl and aryl groups may be optionally fluorinated.
  • Polymers may have repeat units of general Formula 10 in which R 5 and R 6 are as defined in Formula 9:
  • Copolymers comprising repeat units as above described and also other repeat units comprising two or more of the repeat units could be used.
  • the binder normally contains conjugated bonds especially conjugated double bonds and/or aromatic rings. It should preferably form a film, more preferably a flexible film. Copolymers of styrene and alpha methyl styrene, for example copolymers of styrene, alpha methyl styrene and butadiene may suitably be used.
  • Binder materials of low permittivity have few permanent dipoles which could otherwise lead to random fluctuations in molecular site energies.
  • the permittivity (dielectric constant) can be determined by the ASTM D150 test method.
  • polymers include poly(4-methylstyrene), poly(1 ,3-butadiene) or polyphenylene.
  • Copolymers containing the repeat units of the above polymers are also suitable. Copolymers offer the possibility of improving compatibility with the organic semiconductor, modifying the morphology and the glass transition temperature of the final composition. It will be appreciated that in the above table certain materials are insoluble in commonly used solvents. In these cases analogues can be used as copolymers. Some examples of copolymers are given in Table 2 (without limiting to these examples). Both random or block copolymers can be used. It is also possible to add some more polar monomer components as long as the overall composition remains low in polarity. Table 2
  • copolymers may include branched or non-branched polystyrene-block- polybutadiene, polystyrene-block(polyethylene-ran-butylene)-block-polystyrene, polystyrene-block-polybutadiene-block-polystyrene, polystyrene-(ethylene-propylene)- diblock-copolymers (e.g. KRATON®-G1701E, Shell), poly(propylene-co-ethylene) and poly(styrene-co-methylmethacrylate).
  • polystyrene-block- polybutadiene polystyrene-block(polyethylene-ran-butylene)-block-polystyrene, polystyrene-block-polybutadiene-block-polystyrene, polystyrene-(ethylene-propylene)- diblock-copolymers (e.g. KRATON®
  • the binder material should have a higher ionisation potential than the semiconductor, otherwise the binder may form hole traps.
  • the binder In n-channel materials the binder should have lower electron affinity than the n-type semiconductor to avoid electron trapping.
  • the binder may be formed in situ by dissolving the semiconductor in a liquid monomer, oligomer or crosslinkable polymer and depositing the solution for example by dipping, spraying, painting or printing it on a substrate to form a film and then curing the liquid monomer, oligomer or crosslinkable polymer, for example by exposure to radiation, heat or electron beams to produce a solid layer.
  • a preformed binder it may be dissolved together with the semiconductor in a suitable solvent, and the solution deposited for example by dipping, spraying, painting or printing it on a substrate to form a film and then removing the solvent to leave a solid layer.
  • suitable solvents are chosen from those classes which are a good solvent for both the binder and organic semiconductor, and which upon evaporation from the solution blend give a coherent defect free film.
  • Suitable solvents for the resin or organic semiconductor can be determined by preparing a contour diagram for the material as described in ASTM Method D 3132 at the concentration at which the mixture will be employed. The material is added to a wide variety of solvents as described in the ASTM method.
  • organic solvents which may be considered are: CH 2 CI 2 , CHCI 3 , monochlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1 ,4-dioxane, acetone, methylethylketone, 1 ,2- dichloroethane, 1 ,1 ,1-trichloroethane, 1 ,1 ,2,2-tetrachloroethane, ethyl acetate, n-butyl acetate, dimethylformamide, dimethylacetamide, dimethylsulfoxide, tetralin, decalin and/or mixtures thereof.
  • solutions are evaluated as one of the following categories: complete solution, borderline solution or insoluble.
  • the contour line is drawn to outline the solubility parameter-hydrogen bonding limits dividing solubility and insolubility.
  • Solvent blends may also be used and can be identified as described in "Solvents, W.H.Ellis, Federation of Societies for Coatings Technology, p9-10, 1986". Such a procedure may lead to a blend of 'non' solvents that will dissolve both the binder and organic semi-conductor, although it is desirable to have at least one true solvent in a blend.
  • the proportions of binder to semiconductor are preferably 20:1 to 1:20, more preferably 10:1 to 1 :10 and especially 5:1 to 1:5.
  • a process for producing a field effect transistor which comprises the step of coating a substrate with a liquid layer which comprises an organic semiconductor, a binder and a solvent or which comprises an organic semiconductor and a material capable of reacting to form a binder and converting the liquid layer to a solid layer comprising the semiconductor and the binder by evaporating the solvent or by reacting the material to form the binder as the case may be, the binder being a film forming binder of which at least 95% and preferably least 98%) and preferably all of the atoms are hydrogen, fluorine and carbon atoms or being an organic binder which has an inherent conductivity of less than 10 "6 S/cm and a permittivity of less than 3.3, preferably less than 3 and more preferably less than 2.8 and preferably greater than 1.7, for example 2.0
  • Patterning may be carried out by photolithography or electron beam lithography. Liquid coating of organic field effect transistors is more desirable than vacuum deposition techniques.
  • the semiconductor compositions of the present invention enable the use of a number of liquid coating techniques.
  • the organic semiconductor layer may be incorporated into the final device structure by dip coating, spin coating, ink jet printing, letter-press printing, screen printing, doctor blade coating; roller printing, reverse-roller printing; offset lithography printing, flexographic printing, web printing, spray coating, brush coating or pad printing.
  • Selected compositions of the present invention may be applied to prefabricated transistor substrates by ink jet printing or microdispensing.
  • industrial piezoelectric print heads such as but not limited to those supplied by Aprion, Hitachi-Koki, InkJet Technology, On Target Technology, Picojet, Spectra, Trident, Xaar are used to apply the organic semiconductor layer.
  • semi-industrial heads such as those manufactured by Brother, Epson, Konica, Seiko Instruments Toshiba TEC or single nozzle microdispensers such as those produced by Microdrop and Microfab may be used.
  • solvents In order to be applied by ink jet printing or microdispensing compositions must first be dissolved in a suitable solvent. Solvents must fulfil the requirements previously stated in this document and must not have any detrimental effect on the chosen print head.
  • solvents should have boiling points >100°C, more preferably >150°C in order to prevent operability problems caused by the solution drying out inside the print head.
  • Suitable solvents include substituted and non-substituted xylene derivatives, di-C ⁇ -alkyl formamide, substituted and non-substituted anisoles and other phenol-ether derivatives, substituted heterocycles such as substituted pyridines, pyrazines, pyrimidines, pyrrolidinones, substituted and non-substituted /V./V-di-C ⁇ -alkylanilines arid other fluorinated or chlorinated aromatics.
  • a polymeric binder in the organic semiconductor composition allows the viscosity of the coating solution to be tuned to meet the requirements of the particular print head.
  • Preferred viscosities for ink jet printing are 1 to 25 mPa, more preferably 8 to 15 mPa, especially 3 to 15 mPa.
  • Direct patterning (printing) to form the features of the semiconductor device may be possible using liquid coating. This is simpler and less wasteful than subtractive methods such as photolithography.
  • a summary of suitable non-lithographic techniques for fabricating high quality micro-structures are detailed in Table 3 (without limiting to these examples) below (An ⁇ ew. Chem. Int. Ed.. 1998, 37, 550-575).
  • the substrates, types of insulation and the electrodes may be of conventional type it is preferred that the transistors should be made of flexible organic materials for the sake of robustness and resistance to physical stress.
  • the film in the transistor is suitably a continuous monolayer but may be thicker, preferably at most 50 microns and more preferably at most 1 micron thick.
  • the transistors may be of conventional design.
  • the ratio of the current flowing between the source and drain when no gate voltage is applied (off state) and the current flowing when a gate voltage is applied (on state) is preferably at least 1 :10 and more preferably 1 :1 , 000.
  • the film be amorphous. It may be a single phase, bicontinuous, phase separated or a dispersion of one or more component(s) in other(s). It may consist of one or more phases which may interpenetrate one another so that each is itself continuous phase.
  • a first component a) may be a mixture of semiconductors as described in US 5,500,537 and a second component b) may be a mixture of binders.
  • the transistors of this invention may be integrated into more complex devices as component parts.
  • Nickel(ll) chloride (0.97g), zinc powder (59.1 g), triphenyl phosphine (39.3g), 2,2'bipyridyl (1.76g) and anhydrous N,N-dimethylacetamide (1000 ml) were charged to a 2 litre flask and heated with stirring to 80°C and a deep red/brown solution was produced l o characteristic of formation of the catalyst.
  • Example A The final product prepared above (Sample A) was fractionated as follows: It was dissolved in tetrahydrofuran (THF)(1 part) and added dropwise to stirred methanol (2 parts), the precipitate was filtered off and the filtrate concentrated to yield fraction one. Fractions two and three were similarly obtained by dissolving the first precipitate in THF (1 part) and precipitating into methanol (1.5 and 1 parts respectively).
  • the reaction mixture was allowed to cool to room temperature and poured into a beaker containing distilled water (500 ml) and then extracted with dichloromethane (DCM) (4 x 300 ml). The aqueous fraction was discarded and the organic solution was washed successively with distilled water (4 x 300 ml), hydrochloric acid (2 M, 300 ml) and distilled water (300 ml). The organic extract was dried with anhydrous magnesium sulfate, concentrated under reduced pressure to yield a red oil. This was purified by dry flash, column chromatography (silica gel), to yield a yellow oil. Bulb-to-bulb distillation (200-215 °C, 1.5 mm of Hg) failed to remove an unknown impurity, and the impure title compound was collected as a lime yellow oil (49.5 g, purity of 90 area% as determined by HPLC).
  • DCM dichloromethane
  • a 500 ml, 5-neck reaction flask was charged with nickel (II) chloride (0.1 g), zinc powder (6.0 g), 2,2'-bipyridyl (0.2 g), triphenylphosphine (3.9 g) and anhydrous N,N- dimethylacetamide (120 ml).
  • the reaction mixture was heated to 70°C, and after 40 minutes, a deep red/brown solution was observed which is characteristic of formation of the catalyst.
  • the amine monomer and bis( ⁇ /-4'-chlorophenyl)-(9,9-dimethyl-9H-fluoren-2- yl)-amine (12.6 g) was added and the resulting cardboard brown mixture was stirred and maintained at 75-80°C for 3.5 hours.
  • the reaction mixture was then poured into a beaker containing distilled water (300 ml) and extracted with diethyl ether (400 ml).
  • the organic extract was washed successively with saturated aqueous sodium chloride solution (100 ml) and distilled water (2 x 100 ml).
  • the extract was dried with anhydrous magnesium sulfate and then concentrated to yield a yellow syrup, which solidified upon standing.
  • the solid was crystallised from a mixture of acetone and methanol to yield the product (109.0 g).
  • the resulting mixture was stirred at -78°C for a further 1.5 hours before it was allowed to warm to room temperature and stirred for a further 18 hours.
  • the reaction mixture was then poured into a beaker containing hydrochloric acid (2 M, 540 ml) at -5°C and stirred for 1 hour.
  • the reaction mixture was then extracted with diethyl ether (500 ml).
  • the organic extract was separated, washed with saturated aqueous sodium chloride solution (250 ml) and dried with anhydrous magnesium sulfate.
  • the solution was concentrated to yield a gelatinous residue (19.2 g).
  • a test field effect transistor was manufactured by using a silicon crystal serving as substrate and also as the gate electrode.
  • the silicon wafer was highly doped, conductive and had an insulating 200nm thick SiO 2 layer which acts as the gate dielectric.
  • Two gold electrodes are formed on the surface of the semiconductor to serve as the drain and the source.
  • Appropriate mixtures of semiconductor and binder were dissolved in an appropriate solvent (toluene unless otherwise stated in the footnotes to the Table) and the solution was spin-coated onto such a prefabricated transistor substrate to yield a layer of 100-200 nm upon drying, achieved by baking at 100 °C in an oven for complete drying (see Table). Binders were all commercial grade as follows:
  • Custom made silicon-based transistor substrates were used for testing all material compositions. Typically one part organic semiconductor composition was dissolved in 99 parts toluene or THF by weight. The solution was spin coated onto the Si wafer and left to dry for 1 minute. Further drying followed at 100°C for 20 minutes. After this the device was ready for electrical tests. The voltages applied to the transistor are relative to the potential of the source electrode. In the case of an p type gate material, when a negative potential is applied to the gate, positive charge carriers (holes) are accumulated in the semiconductor on the other side of the gate dielectric. (For an n channel FET, positive voltages are applied). This is called the accumulation mode. The capacitance/area ( ) of the gate dielectric determines the amount of the charge thus induced.
  • V DS negative potential
  • / DS source-drain current
  • Field effect mobilities may be measured directly in the case of organic semiconductors which form films. If they do not do so they may be estimated by forming a series of films containing differing amounts of the organic semiconductor and binder, measuring the field effect mobility for each film and extrapolating the results to a composition of 100% ⁇ organic semiconductor. In three cases in the Table a method of measuring the mobility was used as described by Dimitrakopoulos et al. in Synthetic Metals 1998 pp. 47-52. The drain, source and gate electrodes were connected to the Hewlett-Packard 4155B parameter analyser.
  • V D was held at -20V and V G was scanned from 0 to -20V and back again, and in the third V D was held at +40V and V G was scanned from 0 to +40V and back again.
  • V D more negative than V G , l D tends to saturate (saturation regime) due to the pinch-off in the accumulation layer, and is modelled by equation 3.
  • V ⁇ is a threshold voltage (see reference above). The other parameters have been described previously. For this case ⁇ can be calculated from the slope of the plot of
  • solvent used for deposition was chlorobenzene; method used for measurement was that described by Dimitrakopoulos
  • solvent used for deposition was anisole.
  • the solution was ink jet printed through an industrial drop-on-demand peizoelectric print head onto a prefabricated transistor substrate.
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