Manual Low Molecular Weight Organic Semiconductors

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Where a semiconductor thin film is formed using a conventional precursor solution, the thin film may crack due to the emission of gas created by the intermolecular bonding or solvent during the heat treatment. However, the organic semiconductor thin film of example embodiments may be polymerized through the radical reaction using the increased reactivity of the active mechanism of enediyne, thereby preventing or retarding the thin film from cracking, which may occur due to the generation of gas during a continuous process.

The crosslinking reaction may progress without the use of an additive, thus preventing or reducing the negative effect of interrupting the molecular arrangement due to the use of the additive, which acts as an impurity. In addition, example embodiments provide an electronic device, comprising the organic semiconductor thin film as a carrier transport layer.

The organic semiconductor thin film thus formed may maintain improved transistor properties due to intermolecular packing based on the regular arrangement of a monomolecular aromatic enediyne derivative and intermolecular cross-network formation, and may also assure chemical and electrical stability and reliability upon formation into a polymeric thin film.

Where the organic semiconductor thin film is applied as the carrier transport layer to electronic devices, improved properties may be provided and the cost reduction effect may be maximized or increased by realizing a solution process at about room temperature. The aromatic enediyne derivative of example embodiments may be applied to the above devices using a conventional process known in the art.

A better understanding of example embodiments may be obtained in light of the following examples which are set forth to illustrate, but are not to be construed to limit example embodiments. About 1 equivalent of dialdehyde and about 0. After being allowed to stand overnight, the precipitate was filtered and dried.

About 3 equivalents of trimethylsilyl acetylene, about 0. The tetraethynyl compound in THF was slowly added with a Grignard reagent made using about 3 equivalents of trimethylsilyl acetylene, and then refluxed for about 3 hours. Aqueous SnCl 2 was added to the reactor, and then stirred at about room temperature for about 1 hour. The resultant organic layer was washed with water and chloroform, dried, and then purified through silica column chromatography, thus yielding product 1.

The resultant reaction product was washed with water, and the organic layer was dried and then purified via silica column chromatography, thus yielding a compound 2. Before being coated with the organic semiconductor material, the substrate was washed using isopropyl alcohol for about 10 min and then dried.

The sample was dipped into a about 10 mM octadecyltrichlorosilane solution in hexane for about 30 sec, washed with acetone, and then dried. Thereafter, the aromatic enediyne derivative of Preparative Example 1 was dissolved to about 0. The results are shown in FIG. As shown in FIG. As is apparent from these results, the aromatic enediyne derivative of example embodiments may be formed into a semiconductor thin film through a low-temperature wet process.

As seen in FIG. Therefore, where the semiconductor thin film was formed using the aromatic enediyne derivative of example embodiments, the problem of cracking of the thin film attributable to the generation of gas may be prevented or reduced. In order to evaluate the electrical properties of the OTFTs fabricated in Examples 1 and 2, the current transfer properties thereof were measured using a semiconductor characterization system SCS , available from KEITHLEY, and then charge mobility and cut-off leakage current were calculated.

The results are given in Table 1 below. The charge mobility was calculated from the following current equation for the saturation region using the current transfer curve. Therefore, when applied to various electronic devices, e. As described hereinbefore, example embodiments may provide an aromatic enediyne derivative, an organic semiconductor thin film using the same, and an electronic device using the organic semiconductor thin film. The aromatic enediyne derivative of example embodiments, which is a low-molecular-weight organic semiconductor material having a structure, may be applied using a wet process at about room temperature and may be applicable to the processing of semiconductors having relatively large area.

A chemically and electrically stable and reliable semiconductor thin film that has a regular molecular arrangement and does not crack may be provided. The organic semiconductor thin film of example embodiments may be effectively used in various fields, including OTFTs, EL devices, solar cells, and memory. Although example embodiments have been disclosed for illustrative purposes, those skilled in the art will appreciate that various modifications, additions and substitutions are possible, without departing from the scope and spirit of example embodiments as disclosed in the accompanying claims.

Year of fee payment : 4. Disclosed are a novel aromatic enediyne derivative, an organic semiconductor thin film using the same, and an electronic device. Example embodiments pertain to an aromatic enediyne derivative which enables the formation of a chemically and electrically stable and reliable semiconductor thin film using a solution process, e. A thin film having a relatively large area may be formed through a solution process, therefore simplifying the manufacturing process and decreasing the manufacturing cost. Moreover, it is possible to provide an organic semiconductor that may be effectively applied to various fields including organic thin film transistors, electroluminescent devices, solar cells, and memory.

Field Example embodiments relate to an aromatic enediyne derivative, an organic semiconductor thin film, an electronic device and methods of manufacturing the same. Description of the Related Art In general, flat display devices, e. SUMMARY Accordingly, example embodiments have been made keeping in mind the above problems occurring in the related art, and example embodiments provide an aromatic enediyne derivative, which enables the preparation of a chemically and electrically stable and reliable organic semiconductor through a solution process, e.

An aromatic enediyne derivative, which is represented by Formula 3 below:. Ar is selected from the group consisting of a substituted or unsubstituted C 2 -C 30 fused arylene group and a substituted or unsubstituted C 2 -C 30 fused heteroarylene group, and is condensed with acetylene-substituted rings on both sides thereof.

The enediyne derivative as set forth in claim 1 , wherein the Ar is selected from a group consisting of Formula 4 below, and is condensed with acetylene-substituted rings on both sides thereof:. An organic semiconductor thin film comprising the aromatic enediyne derivative of claim 1. An electronic device, comprising the organic semiconductor thin film of claim 3 as a carrier transport layer.

The electronic device as set forth in claim 4 , wherein the electronic device is a thin film transistor, an electroluminescent device, a solar cell, or memory. A method of manufacturing an organic semiconductor thin film, comprising: i applying a precursor solution, including an aromatic enediyne derivative represented by Formula 3 below:. Ar is selected from the group consisting of a substituted or unsubstituted C 2 -C 30 fused arylene group and a substituted or unsubstituted C 2 -C 30 fused heteroarylene group, and is condensed with acetylene-substituted rings on both sides thereof, and an organic solvent, on a substrate to thus form a coating film; and.

The method as set forth in claim 6 , wherein the precursor solution is prepared by mixing two or more aromatic enediyne derivatives represented by Formula 3. The method as set forth in claim 6 , wherein the aromatic enediyne derivative is included in the precursor solution in an amount of about 0.

The method as set forth in claim 6 , wherein the organic solvent is at least one selected from the group consisting of an aliphatic hydrocarbon solvent, including hexane or heptane, an aromatic hydrocarbon solvent, including toluene, pyridine, quinoline, anisol, mesitylene, xylene or chlorobenzene, a ketone-based solvent, including methyl isobutyl ketone, 1-methylpyrrolidinone, cyclohexanone or acetone, an ether-based solvent, including tetrahydrofuran or isopropyl ether, an acetate-based solvent, including ethyl acetate, butyl acetate or propyleneglycol methyl ether acetate, an alcohol-based solvent, including isopropyl alcohol or butyl alcohol, an amide-based solvent, including dimethylacetamide or dimethylformamide, a halogen-based solvent, including dichloromethane or trichloromethane, a silicon-based solvent, and mixtures thereof.

The method as set forth in claim 6 , wherein applying the precursor solution is performed using spin coating, dip coating, roll coating, screen coating, spray coating, spin casting, flow coating, screen printing, ink jetting, or drop casting. A method of manufacturing an electronic device comprising: manufacturing the organic semiconductor thin film according to claim 6. The method as set forth in claim 12 , wherein the organic semiconductor thin film is a carrier transport layer.

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The method as set forth in claim 12 , wherein the electronic device is a thin film transistor, an electroluminescent device, a solar cell, or memory. Aromatic enediyne derivative, organic semiconductor thin film, electronic device and methods of manufacturing the same. USB2 en. KRB1 en. Organic thin film transistor compounds and organic thin film transistor using the same. Novel organic semiconductor compound, its production method, and an organic semiconductor composition containing the same organic semiconductor thin film and element.

EPB1 en. Sulfur atom-containing soluble pentacene derivative and its preparation method and Application of a linear. Triphenylene compounds, process for production thereof, and organic electroluminescent devices made by using the same.

Low-molecular Weight Organic Semiconductors for Organic and Perovskite Solar Cells

Triphenylene compounds, method of manufacturing the same and organic electroluminescent devices employing the same. Jiang et al JOC, , 71, Palmer, et al. USA1 en. KRA en. Li et al. Carbon nanotube composite, organic semiconductor composite, and field-effect transistor. Some semiconductor devices have an optional surface treatment layer between the gate dielectric layer 16 and the semiconductor layer An optional substrate can be included in the organic thin-film transistors. For example, the optional substrate 12 can be adjacent to the gate electrode 14 as shown schematically in FIG.

The OTFT can include an optional surface treatment layer between the substrate 12 and the semiconductor layer Another embodiment of an organic thin-film transistor is shown schematically in FIG. This organic thin-film transistor includes a gate electrode 14 , a gate dielectric layer 16 disposed on the gate electrode 14 , a semiconductor layer 20 , and a source electrode 22 and a drain electrode 24 disposed on the semiconductor layer In this embodiment, the semiconductor layer 20 is between the gate dielectric layer 16 and both the source electrode 22 and the drain electrode Both the source electrode 22 and the drain electrode 24 are in contact with the semiconducting layer such that a portion of the semiconductor layer is positioned between the source electrode and the drain electrode.

The channel 21 is the portion of the semiconductor layer that is positioned between the source electrode 22 and the drain electrode One or more optional surface treatment layers can be included in the semiconductor device. For example, an optional surface treatment layer can be included between the gate dielectric layer 16 and the semiconductor layer For example, the optional substrate 12 can be in contact with the gate electrode 14 as shown schematically in FIG.

OTFT can include an optional surface treatment layer between the substrate 12 and the semiconductor layer In operation of the semiconductor device configurations shown in FIGS. However, at least ideally, no charge i. That is, unless voltage is applied to the gate electrode 14 , the channel 21 in the semiconductor layer 20 remains in a non-conductive state. Upon application of voltage to the gate electrode 14 , the channel 21 becomes conductive and charge flows through the channel 21 from the source electrode 22 to the drain electrode Optionally, the substrate can provide an electrical function for the OTFT.

For example, the backside of the substrate can provide electrical contact. Useful substrate materials include, but are not limited to, inorganic glasses, ceramic materials, polymeric materials, filled polymeric materials e. The gate electrode 14 can include one or more layers of a conductive material.

For example, the gate electrode can include a doped silicon material, a metal, an alloy, a conductive polymer, or a combination thereof. Suitable metals and alloys include, but are not limited to, aluminum, chromium, gold, silver, nickel, palladium, platinum, tantalum, titanium, indium tin oxide ITO , fluorine tin oxide FTO , antimony doped tin oxide ATO , or a combination thereof.

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In some organic thin film transistors, the same material can provide both the gate electrode function and the support function of the substrate. For example, doped silicon can function as both the gate electrode and as the substrate. The gate electrode in some embodiments is formed by coating a substrate surface with a dispersion that contains conductive materials such as nanoparticles that are conductive or polymeric materials that are conductive.

Organic and Polymeric Semiconductors

Conductive nanoparticles include, but are not limited to, ITO nanoparticles, ATO nanoparticles, silver nanoparticles, gold nanoparticles, or carbon nanotubes. The gate dielectric layer 16 is disposed on the gate electrode This gate dielectric layer 16 electrically insulates the gate electrode 14 from the balance of the OTFT device. Useful materials for the gate dielectric include, for example, an inorganic dielectric material, a polymeric dielectric material, or a combination thereof.

The gate dielectric can be a single layer or multiple layers of suitable dielectric materials. Each layer in a single or multilayer dielectric can include one or more dielectric materials. The organic thin film transistors can include an optional surface treatment layer disposed between the gate dielectric layer 16 and at least a portion of the organic semiconductor layer 20 or disposed between the substrate 12 and at least a portion of the organic semiconductor layer In some embodiments, the optional surface treatment layer serves as an interface between the gate dielectric layer and the semiconductor layer or between the substrate and the semiconductor layer.

The surface treatment layer can be a self-assembled monolayer as described in U. Some of these materials are appropriate for use with n-type semiconductor materials and others are appropriate for use with p-type semiconductor materials, as is known in the art. The thin film electrodes e. The patterning of these electrodes can be accomplished by known methods such as shadow masking, additive photolithography, subtractive photolithography, printing, microcontact printing, and pattern coating.

In yet another aspect, a method of making a semiconductor device is provided. Although any suitable method can be used to provide the semiconductor layer, this layer is often provided using a coating composition. The coating composition can be the same as described above. In some exemplary methods of preparing a semiconductor device, the method involves providing a first layer selected from a dielectric layer or a conductive layer and disposing a semiconductor layer adjacent to the first layer.

No specific order of preparing or providing is necessary; however, the semiconductor layer is often prepared on the surface of another layer such as the dielectric layer, the conductive layer, or a substrate. The conductive layer can include, for example, one or more electrodes such as a gate electrode or a layer that includes both the source electrode and the drain electrode. The step of disposing a semiconductor layer adjacent to the first layer includes often includes 1 preparing a coating composition that includes the small molecule semiconductor of Formula I , the insulating polymer, and an organic solvent that dissolves at least a portion of both the small molecule semiconductor and the insulating polymer, 2 applying the coating composition to the first layer to form a coating layer, and 3 removing at least a portion of the organic solvent from the coating layer.

Some of the methods of preparing semiconductor devices are methods of preparing organic thin film transistors. One method of preparing an organic thin film transistor involves arranging multiple layers in the following order: a gate electrode; a gate dielectric layer; a layer having a source electrode and a drain electrode that are separated from each other; and a semiconductor layer in contact with both the source electrode and the drain electrode.

The semiconductor layer includes an insulating polymer and a small molecule semiconductor of Formula I. Exemplary organic thin film transistors according to this method are shown schematically in FIGS. For example, the organic thin film transistor shown schematically in FIG. The semiconductor layer 20 contacts both the source electrode 22 and the drain electrode The portion of the semiconductor layer that is positioned in the area between the source electrode and the drain electrode defines a channel.

The organic thin film transistor shown schematically in FIG. Both the source electrode 22 and the drain electrode 24 contact the semiconductor layer A portion of the semiconductor layer is positioned between the source electrode 22 and the drain electrode This portion of the semiconductor layer defines a channel. The organic thin film transistors shown schematically in FIGS.


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In some embodiments, a surface treatment layer can be positioned between the gate dielectric layer and the semiconductor layer. A substrate can be positioned adjacent to the gate electrode or adjacent to the layer containing the source electrode and the drain electrode. The source electrode 22 and the drain electrode 24 are separated from each other and both electrodes are in contact with the semiconductor layer A portion of the semiconductor layer is positioned between the source and drain electrodes.

A portion of the semiconductor layer 20 is positioned between the source electrode 22 and the drain electrode In any of the organic thin film transistors shown schematically in FIGS. All reagents were purchased from commercial sources and used without further purification unless otherwise noted. The NBS was further recrystallized from acetic acid before use. After sublimation, it was further purified by recrystallization from dimethylformamide DMF.

Substituted 2-bromothiophenes are either commercially available or were prepared through a NBS bromination reaction of the respondent substituted thiophene. For a similar reaction, see Vidal et al. The precursor 2,6-bis- 4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl -9,bis-[ triisopropylsilyl ethynyl]anthracene was synthesized according to Reaction Scheme 1, as described in Preparatory Examples 1 and 2.

Triisopropylsilylacetylene Butyl lithium 2. After addition, the mixture was stirred at room temperature for 2 hours. This colorless solution, was then added to a suspension of 2,6-dibromoanthraquinone 5. The solution turned red immediately and the 2,6-dibromoanthraquininone dissolved in minutes. The mixture was stirred at room temperature overnight and the solution became dark red. When deionized DI water 6. Tin II chloride 8. The organic solvent was removed by rotary evaporation. The hexane solution was washed with DI water until neutral. A bright yellow solid 8.

A yellow solution with suspended KOAc was obtained. The suspension was degassed to remove traces of oxygen. The solution turned orange. The solid residue was purified by column chromatography silica gel, CHCl 3 and recrystallized from ethyl acetate. Orange needle crystals were obtained 3. A Suzuki coupling reaction was used to synthesize the substituted acene-thiophene derivatives Table 1 of Examples , as shown in Reaction Scheme 2. The following general procedure was used in this reaction.

A mL Schlenk flask was charged with 2,6-bis- 4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl -9,bis-[ triisopropylsilyl ethynyl]anthracene 2. The mixture was degassed under a Schlenk line to remove oxygen. Tetrakis triphenylphosphine palladium 0 0. The precipitate was collected by filtration and was purified by zone sublimation or column chromatography silica gel, chloroform or hexane. The solid was further purified by recrystallization from ethyl acetate or toluene.

The solubility of the small molecule semiconductor was measured in n-butylbenzene at room temperature. The results are summarized in Table 1. The weight percent is based on the total solution weight. Typically, the solubility is lower in n-butylbenzene compared to halogenated solvents such as chloroform, chlorobenzene, and dichlorobenzene. A liquid crystal phase transition was observed for Example 1 at A liquid crystal phase transition was observed for this example at The melting points for Examples 1 to 9 are summarized in Table 1.

Orange product was collected in the middle zone. The vacuum was 1. Red needle like crystals in the middle zone were obtained as product. Orange crystals were obtained as product. Red crystal was obtained as product. Red crystals were obtained as product. Orange needle-like crystals were obtained as product. A mL Schlenk flask is charged with 2,6-bis- 4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl -9,bis-[ triisopropylsilyl ethynyl]anthracene 2. The mixture is degassed under a Schlenk line to remove oxygen.

The precipitate is collected by filtration and is purified by zone sublimation or column chromatography silica gel, chloroform or hexane. The wafers were then rinsed with DI water. After being dried under N 2 flow, 1,1,1,3,3,3-hexamethyldisilazane HMDS was spin-coated on top at rpm for 30 seconds. The substrates were stored under N 2 before use. The following general procedure was used for fabricating OTFT devices.

The solution was then knife coated on the HMDS-treated silicon wafers. The resulting solution was then knife coated on a HMDS-treated substrate, which was at room temperature. The resulting solution was then knife coated on a HMDS-treated substrate at room temperature. Effective date : Year of fee payment : 4. The coating compositions include a small molecule semiconductor, an insulating polymer, and an organic solvent that can dissolve both the small molecule semiconductor material and the insulating polymer.

SUMMARY Semiconductor devices, methods of making semiconductor devices, and coating compositions that can be used to provide a semiconductor layer within a semiconductor device are described. A coating composition comprising: a a small molecule semiconductor of Formula I. The coating composition of claim 1 , wherein the small molecule semiconductor of Formula I comprises.

The coating composition of claim 1 , wherein each R 2 is an alkyl having up to 10 carbon atoms. The coating composition of claim 1 , wherein each R 1 is an alkyl having up to 10 carbon atoms and each R 2 is an alkyl having up to 10 carbon atoms. The coating composition of claim 1 , wherein each R 1 is a formyl group or an acyl having up to 10 carbon atoms, wherein the acyl group is unsubstituted or substituted with a halo.

The coating composition of claim 1 , wherein the organic solvent comprises a benzene that is unsubstituted or substituted with at least one alkyl group, b an alkane that is substituted with at least one halo group, c benzene that is substituted with at least one halo group, d a ketone, e an ether, f an amide, or g benzene that is substituted with at least one alkoxy group. A semiconductor device comprising a semiconductor layer comprising: a a small molecule semiconductor of Formula I.

The semiconductor device of claim 8 , further comprising a conducting layer, a dielectric layer, or a combination thereof adjacent to the semiconductor layer. The semiconductor device of claim 8 , wherein the semiconductor device comprises an organic thin film transistor. The semiconductor device of claim 8 , further comprising an electrode layer comprising a source electrode and a drain electrode that are separated from each other and that are both in contact with the semiconductor layer.

The semiconductor device of claim 8 , further comprising a conducting layer adjacent to one surface of the semiconducting layer and a dielectric layer adjacent to an opposite surface of the semiconducting layer. The semiconductor device of claim 8 , wherein the small molecule semiconductor of Formula I comprises. A method of making a semiconductor device, the method comprising: providing a semiconductor layer comprising.

The method of claim 15 , further comprising providing a first layer adjacent to the semiconductor layer, the first layer comprising a conducting layer or a dielectric layer. The method of claim 15 , wherein the semiconductor device comprises an organic thin film transistor comprising multiple layers arranged in the following order: a gate electrode;.

The method of claim 15 , wherein providing the semiconductor layer comprises applying a coating composition to a surface of another layer of the semiconductor device, the coating composition comprising the small molecule semiconductor of Formula I , the insulating polymer, and an organic solvent that dissolves at least a portion of both the small molecule semiconductor and the insulating polymer.

The method of claim 20 , wherein the small molecule semiconductor of Formula I and the insulating polymer each have a concentration of at least 0. The method of claim 20 , further comprising removing at least a portion of the organic solvent after applying the coating composition. USP true USB2 en.

PhD Thesis

EPA1 en. JPA en. CNB en.

WOA1 en. Organic semiconductor comosition, organic thin-film transistor, electronic paper, and display device. Silylethynyl pentacene compounds and compositions and methods of making and using the same. SGA1 en. Fluorinated silylethynyl pentacene compounds and compositions and methods of making and using the same.

Aryl-substituted anthracene compound, preparation method thereof, and organic thin film transistor comprising the same. Anthraquinone-based copolymer material for solar cell and its preparation method and application. The organic semiconductor composition, an organic thin film transistor, and a display device and an electronic paper.

JPB2 en. USB1 en. New organic compounds for electroluminescence and organic electroluminescent devices using the same. USA1 en. Method for forming a bottom gate thin film transistor using a blend solution to form a semiconducting layer and an insulating layer. Substituted anthracenes and electronic devices containing the substituted anthracenes. Organic semiconductor material, organic semiconductor film, organic semiconductor device, and organic thin-film transistor.

EPA2 en. Organic semiconducting layer formulations comprising polyacenes and organic binder polymers. Electronic devices containing acene-thiophene copolymers with silylethynyl groups. Novel organic semiconductor compound, and organic thin film transistor using the same. Photosensitive adhesive composition, and obtained using the same, adhesive film, adhesive sheet, semiconductor wafer with adhesive layer, semiconductor device and electronic part. Chung, " All-organic solution-processed two-terminal transistors fabricated using the photoinduced p-channels ", Applied Physics Letters, , vol.

Yamada, " Effective photochemical synthesis of an air-stable anthracene-based organic semiconductor from its diketone precursor ", Tetrahedron Letters, Oct. Organic semiconductor composition comprising organic semiconductor material and polymer compound. CNA en. Poly oligothiophene - arylene derivative, an organic semiconductor copolymer, a semiconductor multilayer structure, and poly oligothiophene - arylene method for producing a derivative. Novel organic semiconductor polymers and organic thin film transistor using the same. Thin film transistor with a semiconductor layer that includes a gelable self-organizable polymer.

Li et al. EPB1 en. Carbon nanotube composite, organic semiconductor composite, and field-effect transistor. Compound with indolocarbazole moieties and electronic devices containing such compound. Bilge et al. Organic semiconductor polymer for organic thin film transistor containing quinoxaline ring in the backbone chain.