WO2018004093A1 - Dispositif à semi-conducteur organique et procédé permettant de préparer ce dernier - Google Patents

Dispositif à semi-conducteur organique et procédé permettant de préparer ce dernier Download PDF

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Publication number
WO2018004093A1
WO2018004093A1 PCT/KR2017/000461 KR2017000461W WO2018004093A1 WO 2018004093 A1 WO2018004093 A1 WO 2018004093A1 KR 2017000461 W KR2017000461 W KR 2017000461W WO 2018004093 A1 WO2018004093 A1 WO 2018004093A1
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group
organic semiconductor
semiconductor layer
solution
organic
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PCT/KR2017/000461
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English (en)
Korean (ko)
Inventor
김도환
강문성
황해중
박한울
신지혜
Original Assignee
숭실대학교산학협력단
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Priority to KR1020170079382A priority Critical patent/KR102038124B1/ko
Priority to PCT/KR2017/006734 priority patent/WO2018004219A2/fr
Priority to US15/578,483 priority patent/US10529937B2/en
Priority to CN201780052766.6A priority patent/CN109643760B/zh
Publication of WO2018004093A1 publication Critical patent/WO2018004093A1/fr
Priority to US16/192,399 priority patent/US10991894B2/en

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    • 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
    • C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
    • 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]

Definitions

  • the present invention relates to an organic semiconductor device and a method of manufacturing the same.
  • a reactor in order to form a self-assembled monolayer on the organic semiconductor, a reactor must exist on the surface of the organic semiconductor.
  • the organic semiconductor has a problem that physical adsorption must be used because such a reactor does not exist or a large amount thereof.
  • the performance of the semiconductor in the case of forming a self-assembled monolayer through the reactor synthesized by introducing a reactor in the organic semiconductor, it is known that the performance of the semiconductor is reduced by the synthesized reactor.
  • the organic semiconductor is damaged by the solvent used to proceed the solution process to form the self-assembled monolayer.
  • the present invention it is possible to increase the chemical resistance of the organic semiconductor and thereby to improve the electrical properties of the organic electronic device, and to effectively control the physicochemical or electro-optical properties of the organic semiconductor surface or bulk. It is intended to provide a semiconductor manufacturing method.
  • Korean Patent Laid-Open Publication No. 10-2010-0006294 name of the invention: an organic nanofiber structure based on a self-assembled organic gel, an organic nanofiber transistor using the same, and a method of manufacturing the same
  • a method for producing an organic thin film transistor which can be formed, has excellent transistor characteristics, good adhesion, and excellent durability is disclosed.
  • the present invention is to solve the above-mentioned problems of the prior art, to laminate a gelled semiconductor solution containing a hydroxyl group (M-OH, M (metal)), such as silanol group (silanol group (Si-OH)) It provides a method of manufacturing a high-performance or high-sensitivity organic semiconductor device by effectively controlling the surface or bulk properties of the organic semiconductor thin film through a solution process.
  • a hydroxyl group M-OH, M (metal)
  • silanol group silanol group
  • a method of manufacturing an organic semiconductor device is a hydroxyl group (M, such as silanol group (Si-OH) on a substrate on which a dielectric is formed (M) Stacking a semiconductor solution comprising -OH, M (metal)).
  • M hydroxyl group
  • Si-OH silanol group
  • the organic semiconductor device includes a gate electrode, a dielectric layer formed on the gate electrode, a semiconductor layer formed on the dielectric layer, and a source electrode and a drain electrode formed on the semiconductor layer.
  • the semiconductor layer is formed by gelling a semiconductor solution containing a hydroxyl group (M-OH, M (metal)) such as silanol group (Si-OH).
  • the silanol group of the self-assembled thin film layer compound and the silanol group of the organic semiconductor solution used to control the surface or bulk physical properties of the organic semiconductor undergo a condensation reaction, thereby eliminating the hole trap.
  • the transistor element characteristics can be improved.
  • FIG. 1 is a flowchart illustrating a method of manufacturing an organic semiconductor device according to an embodiment of the present invention.
  • FIGS. 2A and 2B are diagrams for describing a method of manufacturing an organic semiconductor device according to an embodiment of the present invention.
  • FIG 3 is a view illustrating an organic semiconductor switching device manufactured using a semiconductor layer according to an embodiment of the present invention.
  • FIG. 4 is a diagram illustrating an organic semiconductor switching device manufactured using a semiconductor layer according to an embodiment of the present invention.
  • 5A and 5B illustrate experimental characteristics of an organic semiconductor device according to an embodiment of the present invention.
  • 6A and 6B illustrate experimental characteristics of an organic semiconductor device according to an embodiment of the present invention.
  • the organic semiconductor used in the present invention is characterized by having a ⁇ -conjugated structure in which a single bond and a double bond between constituent carbon atoms are alternately repeated.
  • Representative ⁇ -conjugated polymer materials include polyacetylene, polypyrrole, polyaniline, polythiophene (PTh), and polyphenylenevinylene (PPV). ), And derivatives thereof.
  • Examples of ⁇ -conjugated structural small molecules include pentacene, perylene, rubrene, and phthalocyanine. .
  • FIGS. 2A and 2B are diagrams for describing a method of manufacturing an organic semiconductor device according to an embodiment of the present invention.
  • an organic semiconductor solution for forming a semiconductor layer is prepared (S100).
  • the organic metal compound precursor stock solution is added and stirred to produce an organic semiconductor solution.
  • the material used as the organic solvent may include one of chloroform, dichloromethane, acetone, pyridine, tetrahydrofuran, chlorobenzene, dichlorobenzene, xylene, toluene, or a mixture thereof.
  • the polymer semiconductor is not particularly limited as a generally used organic semiconductor material, but a material having high carrier mobility is preferable.
  • Specific examples include polythiophenes such as poly-3-hexylthiophene and polybenzothiophene, poly (p-phenylenevinylene) such as polypyrroles and poly (p-phenylenevinylene), polyaniline, Nitrogen-containing aromatic rings such as polyacetylenes, polydiacetylenes, polycarbazoles, polyfurans such as polyfuran and polybenzofuran, pyridine, quinoline, phenanthroline, oxazole and oxadiazole as structural units Condensed polycyclic aromatic compounds such as polyheteroaryls, anthracene, pyrene, naphthacene, pentacene, hexacene, rubrene, furan, thiophene, benzothiophene, dibenzofuran, pyridine, quinoline,
  • organometallic precursors using the material of the formula (1).
  • the precursor may comprise a metal (M) and a reactor (X).
  • the reactor may be formed by synthesizing various materials to suit the purpose.
  • Y in Formula 1 is an alkyl group, a cycloalkyl group, a heterocyclic group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an arylether group, an arylthioether group, an aryl group, a heteroaryl group, a halogen atom, Cyano group, formyl group, alkylcarbonyl group, arylcarbonyl group, carboxyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylcarbonyloxy group, arylcarbonyloxy group, carbamoyl group, amino group or silyl group.
  • the metal (M) is Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Si, Cu, Zn, Pd, Ag, Au, Hg, Pt, Ta, Mo, Zr, Ta, Mg, Sn , Ge, Y, Nb, Tc, Ru, Rh, Lu, Hf, W, Re, Os, Ir, Lr, Rf, Db, Sg, Bh, Hs, Mt, Ds, Rg and Uub
  • the reactor (X) is each hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, arylether group, arylthioether group, aryl group, heteroaryl group , Halogen atom, cyano group, formyl group, alkylcarbonyl group, arylcarbonyl group, carboxyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylcarbonyloxy group, arylcarbonyloxy group, carbamoyl group, amino group or silyl group can be selected. .
  • the organic semiconductor solution includes a hydroxyl group (M-OH, M (metal)) such as a silanol group (Si-OH).
  • the solvated semiconductor solution thus produced is applied to the surface of the object, and then gelled by a sol-gel method to form a gelled organic semiconductor layer (S110).
  • an organic semiconductor solution containing a hydroxyl group (M-OH, M (metal)), such as a silanol group (Si-OH), is laminated and gelled. Therefore, there are a large number of hydroxyl groups (M-OH, M (metal)) such as silanol groups (Si-OH) on the surface and bulk of the organic semiconductor, which functions as a reactor. Meanwhile, an annealing process may be added during the gelation process of the organic semiconductor layer 10.
  • the self-assembled monolayer 20 is formed (S120).
  • the self-assembled monolayer 16 can be formed through a solution process rather than a gas phase process.
  • surface and internal physical properties can be controlled through chemical bonding between the self-assembled monolayer and the gelled organic semiconductor layer.
  • the organometallic precursor when the initial heat treatment is not performed, the organometallic precursor is bonded in a shape into the organic semiconductor bulk, and when the initial heat treatment is performed as shown in FIG. 2B, the organometallic precursor is It may be formed in a form bonded to the surface of the organic semiconductor layer 10.
  • a compound of Chemical Formula 2 is used as the compound for forming the self-assembled monolayer.
  • X is selected from the group consisting of non-aromatic substances such as -NH 2 , -CH 3 , -SH, -COOH, -CF 3 , Cl and any aromatics, and in addition to the electron acceptor group for attracting electrons and electron donor for pushing electrons We include all groups.
  • Y may comprise a metal and a reactor.
  • the reactor may be formed by synthesizing various materials to suit the purpose.
  • the metals are Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Si, Cu, Zn, Pd, Ag, Au, Hg, Pt, Ta, Mo, Zr, Ta, Mg, Sn, Ge,
  • One or more metals selected from the group consisting of Y, Nb, Tc, Ru, Rh, Lu, Hf, W, Re, Os, Ir, Lr, Rf, Db, Sg, Bh, Hs, Mt, Ds, Rg and Uub It may include, but is not limited to these.
  • the reactor is hydrogen, alkyl group, cycloalkyl group, heterocyclic group, alkenyl group, cycloalkenyl group, alkynyl group, alkoxy group, alkylthio group, arylether group, arylthioether group, aryl group, heteroaryl group, halogen atom, respectively , Cyano group, formyl group, alkylcarbonyl group, arylcarbonyl group, carboxyl group, alkoxycarbonyl group, aryloxycarbonyl group, alkylcarbonyloxy group, arylcarbonyloxy group, carbamoyl group, amino group or silyl group.
  • R in Formula 2 may be selected from aliphatic groups including alkyl chains, or aromatic groups including benzene, thiophene, and the like, and n may be a natural number.
  • organometallic precursors may be used.
  • Octyltrichlorosilane OTS
  • Octyltrimethoxysilane OTMS
  • Octyltriethoxysilane OCT
  • Hexamethyldisilazane HMDS
  • Octadecyltrichlorosilane Octadecyltrichlorosilane
  • ODTS octadecyltrimethoxysilane
  • OTMS octadecyltriethoxysilane
  • OTE 3-aminopropyl) trichlorosilane [(3-Aminopropyl) trichlorosilane]
  • (3-aminopropyl ) Trimethoxysilane (3-Aminopropyl) trimethoxysilane; APTMS], (3-aminopropyl) triethoxysilane [(3-Aminopropyl) trimethoxysilane; APTES], Perfluorode
  • various organic semiconductor devices may be manufactured by performing an additional process based on a solution process on top of a semiconductor layer on which a self-assembled monolayer according to an embodiment of the present invention is formed to manufacture an organic semiconductor device.
  • an organic semiconductor device is manufactured by additionally forming various electrodes such as an insulating layer or a source electrode and a drain electrode on the organic semiconductor layer 10 on which the self-assembled monolayer 20 is formed (S130).
  • an insulating layer and various electrodes are additionally formed to manufacture an organic semiconductor device.
  • a detailed configuration will be described with reference to the drawings.
  • FIG 3 is a view illustrating an organic semiconductor switching device manufactured using a semiconductor layer according to an embodiment of the present invention.
  • the illustrated organic semiconductor switching device 300 illustrates an organic FET (OFET) having a top gate structure.
  • the organic semiconductor switching device 300 includes a substrate 310, a drain electrode 320, a source electrode 322, a semiconductor layer 330, a dielectric layer 340, and a gate electrode 350.
  • the organic semiconductor layer 330 is formed by gelling the organic semiconductor solution containing the silanol group described above, and then forming a self-assembled monolayer.
  • the organic semiconductor layer 330 is in a gelled state and has chemical resistance, and includes a plurality of reactors to form a self-assembled monolayer, thereby controlling the surface and bulk physical properties of the dielectric layer.
  • the present invention can be applied to various types of dielectric layers, and to various types of chemical sensors or biosensors.
  • the organic semiconductor layer 330 is formed through the processes of FIGS. 1 and 2.
  • the dielectric layer 340 may be formed and the gate electrode 350 may be formed on the organic semiconductor switching device 300 having a top gate structure.
  • FIG. 4 is a diagram illustrating an organic semiconductor switching device manufactured using a semiconductor layer according to an embodiment of the present invention.
  • the illustrated organic semiconductor switching device 500 illustrates an organic FET having a bottom gate structure.
  • the organic semiconductor switching device 400 includes a gate electrode 410, a dielectric layer 420, an organic semiconductor layer 430, a drain electrode 440, and a source electrode 442.
  • the gate electrode 410 is formed through the processes of FIGS. 1 and 2, the dielectric layer 420 is formed, the organic semiconductor layer 430 is formed, and then a self-assembled monolayer is formed.
  • the drain electrode 440 and the source electrode 442 are formed on the upper portion 430 through a vapor phase process.
  • the semiconductor solution is produced by placing a polymer semiconductor (diketopyrrolo-pyrrole-dithiophene-thienothiophene (DPP-DTT)) in a chlorobenzene solution at 80 ° C. and maintaining a stirring state for about 1 hour and 30 minutes.
  • the precursor stock solution (1,8-bead (trichlorosilyl) octane (1,8-BIS (TRICHLOROSILYL) OCTANE) was added to the polymer semiconductor solution thus prepared, and the mixture was stirred for about 1 hour while maintaining a temperature of about 80 ° C. .
  • the semiconductor solution thus produced is stacked on the silicon substrate by performing at least one of various printing methods such as spin coating, spray coating, inkjet printing, dip coating, drop casting, and bar coating on the silicon substrate on which the dielectric is formed.
  • FIGS. 6A and 6B illustrate experimental characteristics of an organic semiconductor device according to an embodiment of the present invention. to be.
  • octadecyltrichlorosilane as a self-assembled monolayer in the case where the initial heat treatment was not performed (upper figure) and the substrate coated with the organic semiconductor thin film was subjected to the initial heat treatment at 180 ° C. (lower figure).
  • the contact angles of the octadecyltrichlorosilane were not increased.
  • FIG. 5B when the initial heat treatment is not performed (upper figure) and the substrate coated with the organic semiconductor thin film is subjected to an initial heat treatment at 180 ° C.
  • the self-assembled monolayer (3- Aminopropyl (triethoxysilane)) [3-Aminopropyl (triethoxysilane); APS], it can be seen that the contact angle is reduced respectively compared to the case where (3-aminopropyl (triethoxysilane)) is not laminated.
  • This phenomenon may be attributed to the fact that the self-assembled monolayer is combined with the reactor of the semiconductor layer and the characteristics of the surface of the organic semiconductor have changed.
  • FIG. 6A after the organic semiconductor layer according to the present invention is laminated on a SiO 2 substrate and before the initial heat treatment is performed (left graph), before octadecyltrichlorosilane is deposited and octadecyltrichloro Looking at the graph after laminating the silane, it can be seen that the threshold voltage is shifted (-). In the case of the initial heat treatment (right graph), the graphs before stacking octadecyltrichlorosilane and after stacking octadecyltrichlorosilane can be seen that the threshold voltage is shifted positively and hysteresis increases.
  • the silanol group of the organometallic precursor octadecyltrichlorosilane or (3-aminopropyl (triethoxysilane)) is bonded to the silanol group of the organic semiconductor surface and the bulk layer,
  • the octadecyl trichlorosilane or (3-aminopropyl (triethoxysilane)) is combined to change the surface contact angle of the organic semiconductor layer, and the effect of changing the threshold voltage and off current.
  • octadecyltrichlorosilane is bonded to the silanol group of octadecyltrichlorosilane or (3-aminopropyl (triethoxysilane)), which is an organometallic precursor, on the surface of the organic semiconductor.
  • (3-aminopropyl (triethoxysilane)) is bonded to change the surface contact angle of the organic semiconductor layer, the effect of changing the threshold voltage and hysteresis occurs.
  • the initial heat treatment is not performed, the prominent effect occurs because the organometallic precursor is bonded not only to the surface but also to the bulk layer.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Thin Film Transistor (AREA)

Abstract

La présente invention porte, selon un aspect, sur un procédé de préparation de dispositif à semi-conducteur organique qui comprend une étape consistant à stratifier une solution de semi-conducteur organique, qui comprend un groupe hydroxyle (M-OH, M (métal)) tel qu'un groupe silanol (Si-OH), sur un substrat sur lequel est formé un corps diélectrique. Un nouveau dispositif à semi-conducteur organique est préparé au moyen de l'utilisation en tant que réacteur comprenant un groupe hydroxyle (M-OH, M (métal)) tel qu'un groupe silanol (Si-OH) présent sur un substrat et la surface d'une couche de semi-conducteur organique, et de la formation d'une couche monomoléculaire auto-assemblée présentant diverses propriétés.
PCT/KR2017/000461 2015-03-19 2017-01-13 Dispositif à semi-conducteur organique et procédé permettant de préparer ce dernier WO2018004093A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
KR1020170079382A KR102038124B1 (ko) 2016-06-27 2017-06-22 유기 반도체 소자의 제조 방법
PCT/KR2017/006734 WO2018004219A2 (fr) 2016-06-27 2017-06-26 Procédé de fabrication de dispositif à semi-conducteur organique
US15/578,483 US10529937B2 (en) 2016-06-27 2017-06-26 Method of manufacturing organic semiconductor device
CN201780052766.6A CN109643760B (zh) 2016-06-27 2017-06-26 有机半导体器件的制造方法
US16/192,399 US10991894B2 (en) 2015-03-19 2018-11-15 Compound of organic semiconductor and organic semiconductor device using the same

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KR20160082390 2016-06-30
KR10-2016-0082390 2016-06-30

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WO2018004093A1 true WO2018004093A1 (fr) 2018-01-04

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Citations (4)

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Publication number Priority date Publication date Assignee Title
KR20040029143A (ko) * 2001-09-06 2004-04-03 쓰리엠 이노베이티브 프로퍼티즈 컴파니 유기 박막 트랜지스터용 표면 개질층
KR100708720B1 (ko) * 2005-10-19 2007-04-17 삼성에스디아이 주식회사 유기 박막 트랜지스터, 이의 제조 방법 및 이를 구비한평판 표시 장치
KR20120095965A (ko) * 2009-11-18 2012-08-29 스미또모 가가꾸 가부시키가이샤 디바이스, 박막 트랜지스터 및 그의 제조 방법
KR20160055334A (ko) * 2014-11-07 2016-05-18 서울시립대학교 산학협력단 유기 전계 효과 트랜지스터의 제조방법

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Publication number Priority date Publication date Assignee Title
KR20040029143A (ko) * 2001-09-06 2004-04-03 쓰리엠 이노베이티브 프로퍼티즈 컴파니 유기 박막 트랜지스터용 표면 개질층
KR100708720B1 (ko) * 2005-10-19 2007-04-17 삼성에스디아이 주식회사 유기 박막 트랜지스터, 이의 제조 방법 및 이를 구비한평판 표시 장치
KR20120095965A (ko) * 2009-11-18 2012-08-29 스미또모 가가꾸 가부시키가이샤 디바이스, 박막 트랜지스터 및 그의 제조 방법
KR20160055334A (ko) * 2014-11-07 2016-05-18 서울시립대학교 산학협력단 유기 전계 효과 트랜지스터의 제조방법

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