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WO2008013427A1 - Tfts organiques et procédé de fabrication correspondant - Google Patents

Tfts organiques et procédé de fabrication correspondant Download PDF

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Publication number
WO2008013427A1
WO2008013427A1 PCT/KR2007/003630 KR2007003630W WO2008013427A1 WO 2008013427 A1 WO2008013427 A1 WO 2008013427A1 KR 2007003630 W KR2007003630 W KR 2007003630W WO 2008013427 A1 WO2008013427 A1 WO 2008013427A1
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WIPO (PCT)
Prior art keywords
group
ether
formula
ester
independently
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PCT/KR2007/003630
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English (en)
Inventor
Jae-Min Moon
Min-Jeong Lee
Jae-Min Lee
Hyeon Choi
Seok-Hee Yoon
In-Ho Hwang
Se-Hwan Son
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Lg Chem, Ltd.
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Publication of WO2008013427A1 publication Critical patent/WO2008013427A1/fr

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Classifications

    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H10K10/40—Organic transistors
    • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
    • H10K10/462—Insulated gate field-effect transistors [IGFETs]
    • H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • a thin film type field-effect transistor is a basic structure in micro-electronics.
  • the FET includes three electrodes such as source electrodes, drain electrodes, and gate electrodes, an insulating layer, and a semiconductor layer.
  • the semiconductor layer is a conductive channel between the source electrode and the drain electrode, the FET functions as a capacitor.
  • the concentration of charge carrier is controlled by using voltage applied through the gate electrode, and thus the flow of electric charges between the source electrode and the drain electrode can be controlled by using voltage applied through the gate electrode.
  • organic semiconductor substances are used in the FETs
  • electronic devices may be manufactured by using a printing method such as screen printing, ink-jet printing, and micro-contact printing.
  • a printing method such as screen printing, ink-jet printing, and micro-contact printing.
  • an organic semiconductor substance may be used at a very low substrate temperature and no or little vacuum. Therefore, in respects to electronic devices, such as FETs, using an organic semiconductor substance, the manufacturing is easily achieved and manufacturing cost is low as compared to the case of when the inorganic semiconductor substance is used.
  • Organic substances such as small molecules, polymers, and oligomers as that are used as organic semiconductor substances of FETs have been studied since the year 1980s. With respect to this, performance such as charge carrier mobility of the FETs is increased from 10 ⁇ 5 cmWs to 1 cnf/Vs (J. M. Shaw, P. F. Seidler, IBM J. Res. & Dev. , Vol. 45, 3 (2001)). Performance of the current organic transistor is higher than that of the amorphous silicon transistor. Thus, the organic transistor may be used in electronic papers, smart cards, memory devices, and display devices.
  • a basic function of a field-effect transistor is to control the amount of current flowing between a source and a drain by using voltage appl ied to a gate.
  • an organic semiconductor layer has crystal Unity.
  • Most of known semiconductor substances that are used in an organic semiconductor layer have crystal Unity resulting from bonding force of van der Waals' force between organic semiconductor substance molecules.
  • the van der Waals' force is very weak bonding force, which prevents desirable crystal Unity from being ensured or desirable organic films from being formed.
  • the present invention provides anorganic thin film transistor that comprises an organic semiconductor layer containing an organic semiconductor substance having a functional group that can form a hydrogen bond.
  • the present invention provides a method of manufacturing an organic thin film transistor, which comprises forming a gate electrode, an insulating layer, a source electrode, a drain electrode, and an organic semiconductor layer, wherein an organic semiconductor layer is formed by using a compound having a functional group that can form a hydrogen bond.
  • the present invention provides a method of manufacturing an organic thin film transistor, which comprises forming a gate electrode, an insulating layer, a source electrode, a drain electrode, and an organic semiconductor layer wherein the organic semiconductor layer is formed by using a process that comprises forming a thin film by using the organic semiconductor substance in which a substituent group which is to be removed by using heat treatment or light treatment is added to the functional group of the organic semiconductor substance that can form the hydrogen bond, and then performing the heat treatment or the light treatment.
  • the present invention provides an electronic device including the organic thin film transistor. [Advantageous Effects]
  • an organic thin film transistor of the present invention According to a method of manufacturing an organic thin film transistor of the present invention, a solution process can be performed and an organic semiconductor layer that has strong bonding force due to hydrogen bonding and excellent crystal Unity can be formed. Therefore, an organic thin film transistor having high field effect mobility can be manufactured using the same.
  • FIG.1 is a sectional view illustrating a bottom contact structure of an organic thin film transistor (101: substrate and gate, 102: source electrode, 103: drain electrode, 104: insulating layer (gate insulator), and 105: organic semiconductor layer);
  • FIG. 2 is a sectional view illustrating a top contact structure of the organic thin film transistor (101: substrate and gate, 102: source electrode, 103: drain electrode, 104: insulating layer (gate insulator), and 105: organic semiconductor layer);
  • FIG.3 illustrates an output curve when a compound of Formula 1 is deposited in a vacuum to form an organic semiconductor layer in the organic thin film transistor structure of FIG. 1
  • FIG.4 illustrates an output curve when a compound of Formula 4 is subjected to spin coating to form an organic semiconductor layer in the organic thin film transistor structure of FIG. 1;
  • FIG.5 is a UV-VIS spectrum of a thin film comprising the compound of Formula 4 which is prepared by using a solution process before and after heat treatment;
  • FIG.6 is a graph illustrating the thermogravimetric analysis (TGA) results of the compound of Formula 4. [Best Mode]
  • an organic semiconductor substance that is used to manufacture an organic thin film transistor is subjected to a packing process using interaction due to van der Waals 1 energy. Therefore, attraction force between molecules is not strong, thus bonding force between the molecules is weak, and the molecules are not sufficiently close to each other, so that movement of carriers between the molecules is not desirable on the transistor. Furthermore, air or moisture easily moves from the external into the semiconductor layer due to the undesirable packing between the molecules, thus reducing stability of devices.
  • the organic semiconductor layer is formed by using a compound that can form a hydrogen bond having bonding force which is stronger than that of a van der Waals' bond between the molecules of the organic semiconductor substance in manufacturing the organic thin film transistor.
  • hydrogen that is bonded to an atom having high electronegativity such as 0, N, S, and F interacts with unshared electron pairs of atoms such as 0, N, S, and F of adjacent other molecules to form a hydrogen bond.
  • the hydrogen atom Since the electronegativity of each of 0, N, S, F and the like is much higher than that of a hydrogen atom, the hydrogen atom partially has a positive charge, and negative charges are partially generated in the atoms such as O, N, S, andF.
  • the hydrogen atoms partially having the positive charge strongly attract the atoms having the negative charge such as oxygen, nitrogen, sulfur, and fluorine.
  • packing is sufficiently performed between the molecules so that the different types of molecules are very close to each other, and the molecules are regularly arranged.
  • the packing between the molecules reduces the distance between the molecules to desirably move carriers in the semiconductor layer.
  • the organic semiconductor having the hydrogen bond can increase stability of electronic devices in respects to air or moisture.
  • the organic semiconductor layer may be formed by using the compound having the functional group that can form the hydrogen bond according to a process known in the related art.
  • examples of the process of forming the semiconductor layer during manufacturing of the organic thin film transistor include a vacuum deposition process and a solution coating process.
  • the vacuum deposition process requires high temperatures and vacuum, which is difficult to form the layer having large area. Furthermore, equipment cost is relatively high and the process is relatively complicated.
  • the solution coating process such as a spin coating process, an inkjet printing process, a dip coating process, a roll coating process, and a screen printing process can form the thin film layer having large area and be performed at normal temperature and pressure, thus reducing manufacturing cost.
  • the present invention provides a method of forming an organic semiconductor layer by using a vacuum deposition process, wherein the organic semiconductor layer is formed by using the organic semiconductor substance containing the functional group that can form the hydrogen bond to increase packing between the molecules and crystal Unity, or a method of forming an organic semiconductor layer by using a solution process using anorganic semiconductor substance in which a bulky substituent is added to the functional group that can form the hydrogen bond to allow the organic solvent to easily penetrate the substance, thus increasing solubility of the organic semiconductor substance.
  • the organic semiconductor layer of the organic thin fi Im transistor according to the present invention may be formed by using the organic semiconductor substance having the functional group that can form the hydrogen bond.
  • the substituent group that is removed due to heat or light is added to the functional group of the compound, in which the functional group is bonded to a N, 0, S, or F atom and forms the hydrogen bond, so as to remove the hydrogen bond, thus reducing the interaction between the molecules.
  • the substituent group can increase solubility, for example, the substituent group is bulky, solubility of the compound is increased, accordingly, the compound can be easily prepared in a solution form.
  • the solution is used to form the thin film according to the solution coating process.
  • the thin film is subjected to heat or light treatment to remove the substituent group, thereby producing the organic semiconductor substance which is capable of forming the hydrogen bond and has strong bonding force. Therefore, in the method of manufacturing the organic thin film transistor according to the present invention, even though the thin film is formed by using the solution process, the thin film has excellent packing between the molecules, crystal Unity, and stability to moisture or air due to the hydrogen bond.
  • any type of compound may be used as the organic semiconductor substance having the functional group that can form the hydrogen bond as long as the compound can form the hydrogen bond and be used as a semiconductor substance.
  • a detailed description will be given of examples of the compound that is used in the present invention, which are set forth to illustrate but are not to be construed to limit the present invention.
  • the functional group may be a functional group of any one compound of compounds represented by Formulas 1,2, and 3.
  • the compounds which are represented by Formulas 1 to 3, all have a ketone group and a NH group that can form a hydrogen bond.
  • the groups form hydrogen bonds as shown in the following Structural formula 1 or 2, incurring strong interaction.
  • the compounds having strong bonding force or the organic semiconductor substances containing the compounds may be used to form the organic semiconductor layer by using vacuum deposition.
  • Ar and Ar 1 are each independently selected from the group consisting of an aryl group and ahetero aryl group, and may be subst ituted by an alkyl group, an alkoxy group, an acetyl group, a thioalkoxy group, an imine group, an ether group, an ester group, a nitrile group, an amino group, a thioester group, a nitro group or the like.
  • Ar and Ar' are each independently selected from the group consisting of an aryl group and ahetero aryl group, and may be substituted by an alkyl group, an alkoxy group, an acetyl group, a thioalkoxy group, an imine group, an ether group, a nitrile group, an amino group, an ester group, a nitro group or the like.
  • the compounds, which are represented by Formulas 4 and 5 do not form a hydrogen bond due to a very bulky substituent group. Thus, bonding force between the molecules is reduced and solubility is significantly increased, accordingly, the compounds can be prepared in a solution form. Therefore, the compounds can be used to form a thin film by using a solution process.
  • the hydrogen atom is substituted by a t-butoxy carbonyl group and the bonds between the molecules may be broken due to heat or light treatment to form the substances of Formulas 1 and 3 again.
  • Reaction Schemes 1 and 2 will explain the substitution of the compound represented by Formula 1 by the t-butoxy carbonyl group and the conversion of the substituted compound into the compound having the hydrogen bond due to heat.
  • Reaction schemes are set forth to illustrate, but are not to be construed to limit the present invention.
  • the product of Reaction Scheme 1 has solubi 1 ity that is much higher than that of quinacridone used as a starting substance.
  • the product can be obtained in a solution form.
  • the product is used to produce the solution and the thin film is formed by using the solution according to the solution process.
  • the substituent t-butoxy carbonyl group may be decomposed into carbon dioxide and isopropene due to heat to be completely removed, and a quinacridone compound is produced again.
  • the organic semiconductor substance in which other type of substituent group is added to the functional group of the organic semiconductor substance that can form the hydrogen bond, can convert into the compound that can form the hydrogen bond by light treatment as well as heat treatment.
  • a photo acid generator PAG
  • the photo acid generator is a substance that is used to perform patterning by using a photolithography process.
  • the compound containing the t-butoxy carbonyl group or the like and the photo acid generator are mixed with each other to form the thin film and the thin film is then exposed to light by using a photomask, an acid is generated at an exposed portion of the thin film to remove the subst ituent group such as the t-butoxy carbonyl group.
  • the hydrogen bond is regenerated and a difference in solubility of the thin film occurs due to the hydrogen bond. Therefore, the thin film can be patterned due to the difference in solubility.
  • the compound, in which the other type of substituent group is added to the functional group forming the hydrogen bond is mixed with the photo acid generator to form the thin film and the thin film is then exposed to light to form the organic semiconductor layer including the compound that forms the hydrogen bond.
  • the light treatment using the photo acid generator is useful to form patterned electronic devices.
  • the content of the photo acid generator is not limited, but preferably less than 10% in respects to the organic semiconductor compound.
  • Examples of the photo acid generator include, but are not limited to diaryliodonium salts, triarylsulfonium salts, imido sulfonates, 4-nitrobenzenesulfonic acid derivatives, disulphone compounds, sulfonyl substituted diazomethanes, and dibenzyl sulfones aryl-bis-trichloromethyl-s-triazine. They are decomposed due to light to generate protic acids.
  • examples of the substituent group that is used instead of the functional group forming the hydrogen bond include, but are not limited to t-butoxy carbonyl which is the substituent group of the compounds represented by Formulas 4 and 5.
  • an alcohol group, a phenol group, a catechol group, a carbonyl group, a thiol group, an amine group or the like that forms a hydrogen bond may be protected by using an ether bond, an ester bond, a thioether bond, a thioester bond, an amide bond or the like.
  • the temperature and time of the heat treatment are not limited but selected according to the type of substituent groups.
  • the temperature is preferably in the range of 20 to 350°C and the time is preferably in the range of 1 min to 2 hours. More preferably, the treatment is performed at the temperature of 150°C or less for 30 min or less.
  • the exposure time is not limited but preferably less than 30 min.
  • ultraviolet rays or visible rays are used as a light source.
  • the wavelength thereof is not limited, but preferably in the range of 180 to 700 nm which is typically used.
  • the heat treatment may be additionally performed.
  • the temperature of the heat treatment is relatively low as compared to the case of when only the heat treatment is performed.
  • examples of the substituent group that substitute for the alcohol group include methyl ether, methoxymethyl ether, methoxythiomethyl ether, 2-methoxyethoxymethyl ether, bis(2-chloroethoxy)methyl ether, tetrahydropyranyl ether, 4-methoxytetrahydropyranyl ether, tetrahydrothiopyranyl ether, 4-methoxytetrahydropyranyl ether, 4-methoxythetrahydrothiopyranyl ether, tetrahydrofuranyl ether, tetrahydrothiofuranyl ether, 1-ethoxyethyl ether, 1-methyl-l-methoxyethyl ether, 2-( ⁇ henylselenyl)ethyl ether, t-butyl ether, allyl ether, benzyl ether, o-nitrobenzyl ether, triphenylmethyl ether
  • the functional group forming the hydrogen bond is an alcohol group
  • substituent group that substitute for the alcohol group include trichloroacetate ester, methyl carbonate, 2,2,2-trichloroethyl carbonate, allyl carbonate, p-nitrophenyl carbonate, benzyl carbonate, s-benzyl thiocarbonate, nitrate ester, and 2,4-dinitrophenylsulfenate ester.
  • the functional group forming the hydrogen bond is an alcohol group
  • substituent group that substitute for the alcohol group include nitrate ester and 2,4-dinitrophenylsulfenate ester.
  • examples of the substituent group that substitute for the phenol group or the catechol group include methyl ether, methoxymethyl ether, 2-methoxyethoxymethyl ether, methoxythiomethyl ether, penacyl ether, allyl ether, cyclohexyl ether, t-butyl ether, benzyl ether, o-nitrobenzyl ether, 9-anthrylmethyl ether, 4- ⁇ icolyl ether, t-butyldimethylsilyl ether, aryl acetate, aryl pivaloate, aryl benzoate, aryl 9-fluorenecarboxylate, aryl methyl carbonate, aryl 2,2,2-
  • examples of the substituent group that substitute for the carbonyl group include dimethyl acetal and ketal , bis(2,2,2-trichloroethyl) acetal and ketal, 1,3-dioxanes, 5-methylene-l,3-dioxanes, 5,5-dibromo-l,3-dioxanes, 1,3—dioxo1anes, 4-bromomethy1-1,3—dioxo1anes,
  • examples of the substituent group that substitute for the thiol group include s-benzyl thioether, s-p-methoxybenzyl thioether, s-p-nitrobenzyl thioether, s-4-picolyl thioether, s-2-picolyl N-oxide thioether, s-9-anthrylmethyl thioether, s-diphenylmethyl thioether, s-di(p-methoxyphenyl)methyl dithioether, s-triphenylmethyl thioether, s-2,4-dinitrophenyl thioether, s-t-butyl thioether, s-isobutoxymethyl monothioacetal , s-2-tetrahydropiranyl monothioacetal , s-acetamidomethyl aminothioacetal , s-cyanomethyl thioether,
  • examples of the substituent group that substitute for the amine group include methyl carbamate, 9-fluorenylmethyl carbamate, 2,2,2-trichloroethyl carbamate, 2-trimethylsilylethyl carbamate, 1,1-dimethylpropynyl carbamate, 1-methyl-l-phenylethyl catbamate, l-methyl-l-(4-biphenylyl)ethyl carbamate, l,l-dimethyl-2-haloethyl carbamate, l,l-dimethyl-2-cyanoethyl carbamate, t-butyl carbamate, cyclobutyl carbamate, 1-methylcyclobutyl carbamate, 1-adamantyl carbamate, vinyl carbamate, al IyI carbamate, cinnamyl carbamate, 8-quinolyl carbamate, N-hydroxypiperidinyl carbamate
  • the functional group forming the hydrogen bond is the amine group
  • the substituent group that substitute for the amine group include l,l-dimethyl-2-haloethyl carbamate, l,l-dimethyl-2-cyanoethyl carbamate, t-butyl carbamate, and (N-(N'-acetylmethiony1)) .
  • the functional group forming the hydrogen bond is the amine group
  • substituent group that substitute for the amine group include l,l-dimethyl-2-haloethyl carbamate and t-butyl carbamate.
  • the functional group forming the hydrogen bond is the amine group
  • most preferable examples of the substituent group include t-butyl carbamate.
  • the compound having the functional group that forms the hydrogen bond protected by the above-mentioned substituent group may be used as the organic semiconductor substance in itself.
  • preferable examples of the compound having the functional group that forms the hydrogen bond include a compound containing thiophene derivatives, acene derivatives, and porphyrinic derivatives having organic semiconductor properties.
  • the compounds represented by Formulas 6 to 16 may be used to improve the organic semiconductor properties. The following examples are set forth to illustrate, but are not to be construed to limit the present invention.
  • n andm are each independently 0 or a positive integer
  • R and R 1 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
  • n and m are in the range of 0 to 10.
  • n and n 1 are each independently 0 or a positive integer
  • m is a positive integer
  • R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
  • n and n' are each independently in the range of 0 to 10 and m is in the range of 1 to 100.
  • n andm are each independently 0 or a positive integer
  • Rl to R18 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialky1si 1y1 acetyl group, an ether group, an amino group, an imine group, an ester group, a nitrile group, a thioalkoxy group, a thioester group, a vinyl group, an aryl group, and a hetero group.
  • n and m are each independently in the range of 0 to 3.
  • n andm are each independently 0 or a positive integer
  • R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
  • n and m are each independently in the range of 0 to 10.
  • n and m are each independently 0 or a positive integer
  • Rl to R18 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
  • n and m are each independently in the range of 0 to 3.
  • n is 0 or a positive integer.
  • n is in the range of 0 to 10.
  • n O or a positive integer
  • Rl to R8 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group, anitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
  • n is in the range of 0 to 3.
  • n is 0 or a positive integer
  • m is a positive integer
  • Rl to R8 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
  • n is in the range of 0 to 3 and m is in the range of 1 to 100.
  • n and m are each independently 0 or a positive integer
  • R and R' are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, an imine group, an ester group, an ether group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
  • n and m are in the range of 0 to 10.
  • n and m are each independently 0 or a positive integer
  • Rl to R18 are each independently any one selected from the group consisting of an alkyl group, an alkoxy group, an acetyl group, a trialkylsilyl acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, and a hetero group.
  • n and m are each independently in the range of 0 to 3.
  • R and R' are each independently any one selected from the group consisting of a hydrogen atom, an alkyl group having 1 to
  • A is a connection group and any one selected from the group consisting of an alkyl group having 1 to 20 carbon atoms, an ether group having 1 to 20 carbon atoms, a thioether group, an aryl group, a hetero aryl group, a vinyl group, and an acetyl group, n is a positive integer and preferably in the range of 1 to 10, 1 and m are each independently 0 or a positive integer and preferably in the range of 0 to 10, and k is a positive integer and preferably in the range of 1 to 100.
  • the compounds representd by Formulas 6 to 16 may form monomer compounds or polymer compounds.
  • the thiophene derivatives or the acene derivatives may be substituted by an alkyl group, an alkoxy group, an acetyl group, an imine group, an ether group, an ester group, a nitrile group, a thioalkoxy group, an amino group, a thioester group, a vinyl group, an aryl group, a hetero group, etc.
  • the alkyl group, the alkoxy group, the ether group, the ester group, the thioalkoxy group, the vinyl group, the aryl group, and the hetero group that are used in the present invention may be each an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an ether group having 1 to 20 carbon atoms, an ester group having 1 to 20 carbon atoms, a thioalkoxy group having 1 to 20 carbon atoms, a thioester group having 1 to 20 carbon atoms, a vinyl group having 2 to 20 carbon atoms, an aryl group having 6 to 60 carbon atoms and preferably 6 to 16 carbon atoms, and a heterocyclic compound having 4 to 60 carbon atoms and preferably 4 to 12 carbon atoms.
  • the organic thin film transistor according to the present invention may be manufactured by using a material, a structure, and a process that are known in the related art, except the above-mentioned material and process.
  • the OTFT according to the present invention includes an organic semiconductor layer, a gate electrode, a gate insulating film, a source electrode, and a drain electrode.
  • the organic thin film transistor may further include a substrate on a lower surface of the gate electrode.
  • FIGS. 1 and 2 illustrate the structure of the organic thin film transistor according to the present invention.
  • the organic thin film transistor of FIG.1 is provided herein for purpose of illustration only and is not intended to be limiting unless otherwise specified, and the organic thin film transistor of the present invention may have various types of structures without departing from the spirit of the present invention.
  • Examples of the substrate include, but are not limited to flexible materials such as plastics and papers and inorganic material such as silicon and glass.
  • the gate electrode may be made of a conductive substance.
  • Illustrating, but non-limiting examples of the conductive substance include carbon, aluminium, vanadium, chrome, copper, zinc, silver, gold, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, tin, lead, similar metals, alloys of the metals, p- or n-doped silicon, zinc oxides, indium oxides, indium tin oxides (ITO), indium zinc oxides, and similar tin oxides, mixtures of oxides and metals such as tin oxide indium-based complex compounds, ZnO:Al and Sn(VSb, and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-l,2-dioxy)thiophene] , polypyrrole, and polyaniline.
  • the gate insulating film may be made of the insulating substance.
  • Illustrating, but non-limiting examples of the insulating substance include silicon oxides, silicon nitrides, and plastic insulators such as polyimide, poly(2-vinylpyridine), poly(4-vinylphenol), and polymethylmethacrylate.
  • Examples of the material used to manufacture the source, drain, and gate electrodes include, but are not limited to metal such as gold (Au), platinum (Pt), silver (Ag), palladium (Pd), aluminium (Al), nickel (Ni), and chrome (Cr), conductive metal oxides such as indium tin oxides, indium zinc oxides, and nickel oxides, and conductive polymers such as polyaniline, polypyrrole, and polyethylenedioxythiophene.
  • the present invention provides an electronic device that includes the organic thin film transistor. Examples of the electronic device include electronic papers, smart cards, memory devices, and display devices.
  • FIG.6 illustrates the thermogravimetric analysis (TGA) results of the compound of Formula 4, and it can be seen that the substituent suppressing the hydrogen bond is removed due to heat at 200°C or less.
  • the n-type dopped silicon wafer having low resistance was used as the gate electrode, and the gate insulating film that was made of SiU2 and had a thickness of 3000 A was layered thereon by using a heat oxidation process.
  • gold was applied to a thickness of 500 A by using a photol ithography process to form a source-drain electrode having a channel length of 10 ⁇ m and a channel width of 300 ⁇ m.
  • the substrate was subjected to surface treatment by using a UV-ozone plasma, HMDS (hexamethyldisilazane) was applied thereon by spin coating at 3000 rpm for 30 sec, and baking was performed at 120"C for 2 min.
  • HMDS hexamethyldisilazane
  • quinacridone represented by Formula 1 was deposited in a vacuum at a rate of 0.3 A/s to produce a channel substance in a thickness of 500 A.
  • the organic thin film transistor which was manufactured by using the above-mentioned procedure had field effect mobility of 7.94 x 10 ⁇ 5 cmVVs. This is shown in FIG.3.
  • the n ⁇ type doped silicon wafer having low resistance was used as the gate electrode, and the gate insulating film that was made of Si ⁇ 2 and had a thickness of 3000 A was layered thereon by using a heat oxidation process.
  • gold was applied to a thickness of 500 A by using a photo1ithographyprocess to form a source-drain electrode having a channel length of 10 ⁇ m and a channel width of 300 ⁇ m.
  • the substrate was subjected to surface treatment by using a UV-ozone plasma, HMDS (hexamethyldisilazane) was applied thereon by spin coating at 3000 rpm for 30 sec, and baking was performed at 120°C for 2 min.
  • HMDS hexamethyldisilazane
  • the solution that was prepared by dissolving the compound represented by Formula 4 of Preparation Example 1 in tetrachloroethane to have a concentration of 2 w/w% was applied by spin coating at 1500 rpm for 20 sec and drying was performed at 50 ° C for 1 min and at 180°C for 2 min to manufacture the organic thin film transistor.
  • the organic thin film transistor which was manufactured by using the above-mentioned procedure had field effect mobility of 1.84 x 10 ⁇ 5 cmVVs. This is shown in FIG. 4.
  • the field effect mobility of the organic thin film transistor that was manufactured by using the organic semiconductor layer formed through the solution process were relatively lower than that of the organic thin film transistor that was manufactured by using the semiconductor layer formed through the vacuum deposition, but a difference in properties was not significant. Therefore, it can be seen that the organic thin film transistor can be efficiently manufactured by regenerating the hydrogen bond.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Thin Film Transistor (AREA)

Abstract

La présente invention concerne un transistor à film mince organique qui comprend une couche de semi-conducteur organique contenant une substance semi-conductrice organique comportant un groupe fonctionnel qui peut former une liaison hydrogène, et un procédé de fabrication de ce dernier. Dans le transistor à film mince organique, une substance semi-conductrice comportant un groupe fonctionnel qui peut former une liaison hydrogène est utilisée en tant que substance semi-conductrice organique, ce qui améliore ainsi une propriété de conditionnement du fait de l'interaction maximisée entre les molécules. Étant donné que la couche de semi-conducteur organique est formée au moyen d'un processus de dissolution, le coût de fabrication est réduit.
PCT/KR2007/003630 2006-07-27 2007-07-27 Tfts organiques et procédé de fabrication correspondant WO2008013427A1 (fr)

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KR1020060070933A KR100918362B1 (ko) 2006-07-27 2006-07-27 유기 박막 트랜지스터 및 이의 제조방법
KR10-2006-0070933 2006-07-27

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WO2011150137A3 (fr) * 2010-05-28 2012-01-12 Corning Incorporated Dispositifs à semi-conducteur améliorés faisant appel à des matériaux organiques photoactifs et leurs procédés de fabrication
WO2012041849A1 (fr) 2010-09-29 2012-04-05 Basf Se Semi-conducteurs à base de dicétopyrrolopyrroles
CN103430293A (zh) * 2011-03-30 2013-12-04 索尼公司 制备有机晶体管的方法、有极晶体管、制备半导体器件的方法、半导体器件和电子装置
US8946376B2 (en) 2010-09-29 2015-02-03 Basf Se Semiconductors based on diketopyrrolopyrroles
US12227613B2 (en) 2020-10-16 2025-02-18 Corning Incorporated Photo-patternable organic semiconductor (OSC) polymers and methods of formation and applications thereof

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KR101100647B1 (ko) * 2009-06-24 2012-01-03 포항공과대학교 산학협력단 고분자 게이트 절연막의 제조방법

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KR101304697B1 (ko) * 2006-06-07 2013-09-06 삼성전자주식회사 적층 유도 화합물을 사용한 유기 반도체 소재, 이를포함하는 조성물, 이를 이용한 유기 반도체 박막 및 유기전자 소자

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US6555840B1 (en) * 1999-02-16 2003-04-29 Sharp Kabushiki Kaisha Charge-transport structures
US6753245B2 (en) * 2000-06-29 2004-06-22 Board Of Trustees, The University Of Illinois Organometallic compounds and their use as precursors for forming films and powders of metal or metal derivatives
US7005672B2 (en) * 2002-10-17 2006-02-28 Xerox Corporation Thin film transistor with a semiconductor layer that includes a gelable self-organizable polymer

Cited By (8)

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WO2011150137A3 (fr) * 2010-05-28 2012-01-12 Corning Incorporated Dispositifs à semi-conducteur améliorés faisant appel à des matériaux organiques photoactifs et leurs procédés de fabrication
JP2013531884A (ja) * 2010-05-28 2013-08-08 コーニング インコーポレイテッド 光活性有機材料を用いる強化半導体素子及びその作製方法
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JP2014501695A (ja) * 2010-09-29 2014-01-23 ビーエーエスエフ ソシエタス・ヨーロピア ジケトピロロピロール系の半導体
US8946376B2 (en) 2010-09-29 2015-02-03 Basf Se Semiconductors based on diketopyrrolopyrroles
CN103430293A (zh) * 2011-03-30 2013-12-04 索尼公司 制备有机晶体管的方法、有极晶体管、制备半导体器件的方法、半导体器件和电子装置
US12227613B2 (en) 2020-10-16 2025-02-18 Corning Incorporated Photo-patternable organic semiconductor (OSC) polymers and methods of formation and applications thereof

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