Classifications

• • 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
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
  • C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
  • C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
  • C08L61/14—Modified phenol-aldehyde condensates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F8/00—Chemical modification by after-treatment
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D129/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Coating compositions based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Coating compositions based on derivatives of such polymers
  • C09D129/02—Homopolymers or copolymers of unsaturated alcohols
  • C09D129/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F2810/00—Chemical modification of a polymer
  • C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
  • C08G2261/10—Definition of the polymer structure
  • C08G2261/14—Side-groups
  • C08G2261/142—Side-chains containing oxygen
  • C08G2261/1422—Side-chains containing oxygen containing OH groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
  • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
  • C08G2261/33—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain
  • C08G2261/334—Monomer units or repeat units incorporating structural elements in the main chain incorporating non-aromatic structural elements in the main chain containing heteroatoms
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
  • C08G2261/40—Polymerisation processes
  • C08G2261/42—Non-organometallic coupling reactions, e.g. Gilch-type or Wessling-Zimmermann type
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
  • C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/04—Oxygen-containing compounds
  • C08K5/05—Alcohols; Metal alcoholates
  • C08K5/053—Polyhydroxylic alcohols
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
  • C08K5/41—Compounds containing sulfur bound to oxygen
  • C08K5/42—Sulfonic acids; Derivatives thereof

Definitions

• the invention relates to an integrated circuit according to the preamble of claim 1 and a method for producing an integrated circuit with an organic semiconductor according to claim 8.
• a field-effect transistor is especially considered organic if the semiconductive layer is made of an organic material.
• RF-ID radio frequency identification
• thermo distortion of most eligible inexpensive substrates eg polyethylene terephthalate (PET), polyethylene naphthalate (PEN)
• PET polyethylene terephthalate
• PEN polyethylene naphthalate
• this temperature limit can be up to 200 ° C. increase, but with the restriction that the distortion of the substrate is indeed reduced, but not prevented.
• a critical process step in electronic components is the deposition of the dielectric layer, in particular the gate dielectric layer of an OFET.
• Very high demands are placed on the quality of dielectrics in OFETs in terms of thermal, chemical, mechanical and electrical properties.
• Silicon dioxide (Si0 2 ) is currently the most commonly used gate dielectric in OFETs, based on the broad availability in semiconductor technology. Thus, transistor structures are described in which a doped silicon wafer serves as the gate electrode, and thermal SiO 2 grown thereon forms the gate dielectric. This Si0 2 is prepared at temperatures of about 800 -1000 ° C. Other processes (eg CVD) for the deposition of Si0 2 on different substrates also work at temperatures above 400 ° C. A group at PennState University has developed a process (ion beam sputtering) that allows to deposit high quality Si0 2 at process temperatures of 80 ° C. This is illustrated in the articles by CD Sheraw, JA Nichols, DJ Gundlach, JR Huang, CC Kuo, H.
• inorganic nitrides such as SiN x .
• TaN x Similar to the preparation of inorganic oxides, the deposits require inorganic Nitrides high temperatures or high process costs. For example, see the article by BK Crone, A. Dodabalapur, R. Sarpeshkar, RW Filas, YY Lin, Z. Bao, JH O'Neill, W.Li, and HE Katz, J. Appl. Phys. 89, 512 (2001).
• organic polymers such as poly-4-vinylphenol (PVP), poly-4-vinylphenol-co-2-hydroxyethyl methacrylate or polyimide (PI) have been used. These polymers are characterized by their comparatively simple processability. So they are e.g. from the
• the present invention has for its object to provide an integrated circuit with an organic semiconductor and a method, wherein the production of dielectric layers of OEFT's at low temperatures is possible.
• the integrated circuit with an organic semiconductor is composed of a polymer formulation
• the integrated circuits according to the invention are, in particular, OFETs with organic layers which have outstanding dielectrical properties.
• the integrated circuits can be easily produced at low temperatures (up to 150 ° C) due to the specific polymer formulation used. In principle, this polymer formulation can also be used in conjunction with other electronic components.
• At least one base polymer is a phenol-containing polymer or copolymer, in particular poly-4-vinylphenol, poly-4-vinylphenol-co-methacrylic acid-2 - hydroxyethyl ester or poly-4-vinylphenol-co-methacrylic acid methyl ester.
• At least one electrophilic crosslinker component is a di- or tribenzyl alcohol compound, in particular 4-hydroxymethylbenzyl alcohol.
• the thermal acid catalyst used is at least one sulfonic acid, in particular 4-toluenesulfonic acid, since it is capable of transferring a proton to the hydroxy group of a benzyl alcohol below 150 ° C.
• Advantageous solvents are an alcohol, in particular n-butanol, propylene glycol monomethyl ether acetate (PGMEA), dioxane, N-methylpyrrolidone (NMP), ⁇ -butyrolactone, xylene or a mixture.
• PMEA propylene glycol monomethyl ether acetate
• NMP N-methylpyrrolidone
• ⁇ -butyrolactone xylene or a mixture.
• the proportion of base polymer, crosslinking component and acid generator has a proportion of between 5 and 20% by mass.
• the object is also achieved by a method for producing an integrated circuit, in particular an OFET with a dielectric layer, having the features of claim 1. According to the invention
• At least one further structuring of the OFET is then advantageously carried out.
• Polymer formulation by spin coating, printing or spraying.
• the crosslinking reaction is advantageously carried out under an inert gas, in particular a N 2 atmosphere.
• an active layer for forming an OFET in particular from the semiconducting pentacene, is applied to the source-drain layer.
• a passivation layer is arranged on the active layer.
• Fig. 1 is a schematic representation of an organic field effect transistor
• FIG. 2 shows an example of a crosslinking reaction of a polymeric gate dielectric with PVP and 4-hydroxymethylbenzyl alcohol as crosslinker
• FIG. 3a shows an output characteristic of an OFET with an electrophilically networked gate dielectric
• FIG. 3b shows a characteristic curve of an OFET with electrophilically networked gate dielectric
• OFETs are electronic components consisting of multiple layers (layers), all of which are structured to generate integrated circuits through interconnections of individual layers.
• 1 shows the basic structure of such a transistor in a bottom-contact architecture.
• a gate electrode 2 is arranged, which is covered by a gate dielectric layer 3.
• the substrate 1 with the gate electrode 2 already arranged thereon is the starting material to which the gate dielectric layer 3 is applied.
• the gate dielectric layer 3 there are disposed a drain layer 4a and a source layer 4b, both connected to the active semiconducting layer 5 in FIG.
• a passivation layer 6 is arranged above the active layer 5.
• circuits according to the invention and their manufacture solve the problem of providing OFETs with gate dielectric layers, in particular with organic ICs having excellent mechanical, chemical and electrical properties at simultaneously low process temperatures.
• an OFET has a dielectric layer which can be produced from a mixture (polymer formulation) with basically four constituents: a base polymer, a crosslinking component, a thermal acid generator and a solvent.
• a mixture polymer formulation
• An embodiment of the circuit according to the invention cited here by way of example has a polymer formulation with the following constituents
• a solvent e.g. Alcohols, PGMEA.
• This polymer formulation is applied to a suitably prepared substrate 1 (gate structures 2 are already defined on the substrate 1).
• Polymer formulation may e.g. printed, spin-coated or sprayed on. By subsequent drying at moderate temperatures (about 100 ° C), the polymer formulation is fixed to the substrate and then converted into its final structure in a thermal crosslinking step.
• Fig. 2 is shown schematically how PVP is cross-linked with 4-hydroxymethylbenzyl alcohol at a temperature of 150 ° C with elimination of water.
• the compounds shown below can be used as electrophilic crosslinkers:
• R 2 alkyl having 1 to 10 Kohl ⁇ stoHatom ⁇ n or aryl
• the crucial step for the production of gate dielectric layers 3 with the required properties is this crosslinking reaction and its initiation at temperatures which are not critical for the substrate. These are temperatures from 20 ° C to a maximum of 150 ° C.
• the use of the method reduces the required crosslinking temperature by more than 50 ° C compared to the previously known methods (see article by Halik et al. (2002)).
• the base polymer determines the basic properties of the gate dielectric layer 3.
• the basic polymers are in principle suitable for all phenol-containing polymers and their copolymers, such as e.g. Poly-4-vinyl-phenol, poly-4-vinylphenol - co-methacrylic acid-2-hydroxyethyl ester or poly-4-vinylphenol-co-methacrylic acid methyl ester.
• the mechanical properties of the polymer layer and the resistance to chemicals can be significantly controlled.
• the temperature of the initiation of the crosslinking reaction can be controlled.
• the choice of solvent determines the film forming properties of the formulation.
• Formulation 1 is a 10% solution in
• PMEA Propylene glycol monomethyl ether acetate
• Formulation 2 is a 10% solution in PGMEA. There are 100 parts of base polymer, 20 parts of crosslinker and 2.5 parts of acid generator. The proportion of crosslinker is therefore twice as high as in Formulation 1.
• a photoresist is applied to the cross-linked polymer layer (gate dielectric layer 3) (S 1813, 3000 rpm, 30 seconds) and dried at 100 ° C. for 2 minutes. Subsequently, the later contact holes are defined by exposure and development of the photoresist. The Opening of the contact holes by means of oxygen plasma (2 times 45s at 100W).
• the source-drain layer 4 is deposited and patterned by standard methods (30 nm Au thermally evaporated, photolithographic structuring and wet-chemical etching with I / KI solution).
• the layer thickness of the gate dielectric layers 2 for formulation 1 210 nm.
• the roughness of the layer is 0.5 nm to 50 ⁇ m.
• the roughness of the layer is 0, 6 nm to 50 microns.
• the transistors or circuits are completed by the active component 5 (pentacene here) is thermally evaporated. Apart from the passivation layer 6, the structure of an OFET according to FIG. 1 is thus produced.
• FIG. 3 a shows an output characteristic family of a pentacene OFET with electrophilically crosslinked gate dielectric.
• Fig. 3b shows for the same structure
• FIG. 4 shows a drawing of an oscilloscope representation. The characteristic of a 5 Stages of the ring oscillator, wherein the ring oscillator operates with a signal delay of 120 microseconds per stage.
• the invention is not limited in its execution to the above-mentioned preferred embodiments. Rather, a number of variants are conceivable which make use of the device according to the invention and the method according to the invention even in fundamentally different embodiments.

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• Chemical & Material Sciences (AREA)
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• Medicinal Chemistry (AREA)
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• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Materials Engineering (AREA)
• Wood Science & Technology (AREA)
• General Chemical & Material Sciences (AREA)
• Thin Film Transistor (AREA)
• Formation Of Insulating Films (AREA)
• Compositions Of Macromolecular Compounds (AREA)

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• 2003
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• 2004
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