WO2014115749A1 - Matériau semiconducteur organique de dissolution et dispositif semi-conducteur organique - Google Patents

Matériau semiconducteur organique de dissolution et dispositif semi-conducteur organique Download PDF

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Publication number
WO2014115749A1
WO2014115749A1 PCT/JP2014/051213 JP2014051213W WO2014115749A1 WO 2014115749 A1 WO2014115749 A1 WO 2014115749A1 JP 2014051213 W JP2014051213 W JP 2014051213W WO 2014115749 A1 WO2014115749 A1 WO 2014115749A1
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organic semiconductor
dntt
compound
semiconductor material
alkyl group
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PCT/JP2014/051213
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English (en)
Japanese (ja)
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和男 瀧宮
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日本化薬株式会社
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Priority to KR1020157022803A priority Critical patent/KR102101242B1/ko
Priority to CN201480005535.6A priority patent/CN104956508B/zh
Priority to JP2014558587A priority patent/JP6080870B2/ja
Publication of WO2014115749A1 publication Critical patent/WO2014115749A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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]
    • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions

Definitions

  • the present invention relates to an organic semiconductor material for solution process and an organic semiconductor device.
  • DNTT dinaphthothienothiophene
  • the DNTT derivatives disclosed in Patent Documents 1 and 2 have poor solubility in organic solvents. For this reason, the subject that the organic-semiconductor layer cannot be manufactured by solution processes, such as the apply
  • the present invention has been made in view of the above matters, and provides an organic semiconductor material and an organic semiconductor device for solution process that are excellent in solubility in an organic solvent and can be used for manufacturing an organic semiconductor layer by a solution process such as a coating method.
  • the purpose is to do.
  • the organic semiconductor material for solution process according to the first aspect of the present invention Including a compound represented by Formula 1, (In Formula 1, Y 1 and Y 2 are each independently a chalcogen atom, one of R 1 and R 2 is a branched alkyl group, and the other is hydrogen.) It is characterized by that.
  • the main chain of the branched alkyl group is preferably C3 or more.
  • the main chain of the branched alkyl group is preferably C6 or more.
  • the side chain of the branched alkyl group is preferably C2 or more.
  • the side chain of the branched alkyl group is bonded to the carbon at the 2-position or more of the main chain.
  • the side chain of the branched alkyl group is bonded to the carbon at the 3-position or more of the main chain.
  • the Y 1 and Y 2 is a sulfur atom or a selenium atom.
  • the organic semiconductor device is Including an organic semiconductor material for solution processing according to the first aspect of the present invention, It is characterized by that.
  • the organic semiconductor material for solution process according to the present invention is excellent in solubility in an organic solvent. For this reason, it is possible to produce an organic semiconductor layer by a solution process such as a coating method.
  • FIG. 2 is a graph showing an absorption spectrum (FIG. 1A), a photoelectron spectrum (FIG. 1B), and an out-of-plane XRD (FIG. 1C) of a 2,9-EH-DNTT thin film.
  • 2 is a graph showing an absorption spectrum (FIG. 2A), a photoelectron spectrum (FIG. 2B), and an out-of-plane XRD (FIG. 2C) of a 2-2EH-DNTT thin film.
  • 2-2 is a graph showing transfer characteristics (FIG. 3A) and output characteristics (FIG. 3B) of an EH-DNTT transistor element. It is a graph which shows the transfer characteristic (FIG. 4 (A)) and output characteristic (FIG. 4 (B)) of an ODTS processing element.
  • Organic semiconductor material for solution process includes a compound represented by Formula 1.
  • Y 1 and Y 2 are each independently a chalcogen atom (oxygen, sulfur, selenium, tellurium). Y 1 and Y 2 are preferably a sulfur atom or a selenium atom. Y 1 and Y 2 are preferably the same.
  • any one of R 1 and R 2 is a branched alkyl group, and the other is hydrogen.
  • the main chain of the branched alkyl group is preferably C3 or more, and more preferably C6 or more.
  • the side chain of the branched alkyl group is C1 or more, and more preferably C2 or more. Further, the side chain is preferably bonded to the carbon at the 2-position or more of the main chain, and more preferably bonded to the carbon at the 3-position or more of the main chain. By separating the side chain from the condensed ring, the intermolecular interaction is increased and the carrier mobility is improved.
  • the branched alkyl group is preferably a saturated branched alkyl group.
  • the main chain carbon number is C6, indicating sufficiently good solubility, If the branched alkyl group is long, the packing at the time of producing the organic semiconductor layer is deteriorated and the semiconductor characteristics may be deteriorated. Therefore, the carbon number of the main chain may be C10 or less.
  • the compound represented by the above formula 1 can be synthesized with reference to known methods disclosed in Patent Document 1 and Patent Document 2.
  • Patent Document 1 and Patent Document 2 For example, although it can synthesize
  • 6-halogeno-2-methoxynaphthalene or 7-halogeno-2-methoxynaphthalene compound (A)
  • 6-alkyl-2-methoxynaphthalene or 7-alkyl- 2-methoxynaphthalene compound (B)
  • a Grignard reagent such as an alkylmagnesium bromide having a branched alkyl group.
  • the compound (C) is synthesized.
  • the compound (C) can be synthesized by reacting the compound (B) with dimethyl sulfide or the like.
  • the compound (D) is synthesized. It can be synthesized by reacting compound (C) with tribromoborane or the like.
  • the compound (E) is synthesized. It can be synthesized by reacting compound (D) with trifluoromethanesulfonic acid.
  • one of X 1 and X 2 is a halogen atom, and the other is hydrogen.
  • one of R 1 and R 2 is a branched alkyl group, and the other is hydrogen.
  • compound (I) is synthesized from 2-methoxynaphthalene (compound (F)) via compound (G) and compound (H).
  • the compounds (G), (H) and (I) can be synthesized in the same manner as the compounds (C), (D) and (E), respectively.
  • the compound (J) is synthesized by condensing the above two compounds (compounds (E) and (I)). Furthermore, compound (K) which is a target compound is synthesize
  • one of R 1 and R 2 is a branched alkyl group, and the other is hydrogen.
  • the organic semiconductor material for solution process contains the compound represented by Formula 1, and the compound represented by Formula 1 has high solubility in an organic solvent. Therefore, an organic semiconductor material for solution process containing the compound represented by Formula 1 is used and a solution process such as a coating method such as a spin coating method, an ink jet method, a screen printing method, an offset printing method, or a micro contact printing method is used. Thus, an organic semiconductor layer can be manufactured. In the solution process, it is not necessary to use a vacuum or a high temperature state unlike the vapor deposition method, and a large-area organic semiconductor layer can be realized at low cost.
  • organic solvents in which organic semiconductor materials for solution process are soluble include halogeno hydrocarbon solvents such as chloroform, methylene chloride, and dichloroethane, alcohol solvents such as methanol, ethanol, propyl alcohol, and butanol, octafluoropentanol, and pentane.
  • halogeno hydrocarbon solvents such as chloroform, methylene chloride, and dichloroethane
  • alcohol solvents such as methanol, ethanol, propyl alcohol, and butanol, octafluoropentanol, and pentane.
  • Fluorinated alcohol solvents such as fluoropropanol, ester solvents such as ethyl acetate, butyl acetate, ethyl benzoate and diethyl carbonate, toluene, hexylbenzene, xylene, mesitylene, chlorobenzene, dichlorobenzene, methoxybenzene, chloronaphthalene, methylnaphthalene , Aromatic hydrocarbon solvents such as tetrahydronaphthalene, ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexane, dimethylform Bromide, dimethyl acetamide, amide solvents such as N- methyl pyrrolidone, tetrahydrofuran, diisobutyl ether, ether solvents diphenyl ether, octane, decane,
  • the organic semiconductor material for solution process may be mixed with additives and other semiconductor materials for improving the film forming property of the organic semiconductor layer, doping, and the like.
  • the organic semiconductor device according to the present embodiment is a device using the above-described organic semiconductor material for solution process.
  • Examples of the organic semiconductor device include a field effect transistor having an organic semiconductor layer and a light emitting device having an organic carrier transport layer and / or a light emitting layer.
  • the organic semiconductor device can be manufactured using various conventionally known manufacturing methods, and is not particularly limited.
  • stepwise 2- (2-ethylhexyl) dinaphtho [2,3-b: 2 ′, 3′-f] thieno [2,3-b] thiophene (hereinafter, referred to as 2-2EH- DNTT) was synthesized.
  • a THF solution of 2-ethylhexylmagnesium bromide was prepared by adding 1-bromo-2-ethylhexasil bromide (9.0 mL, 45 mmol) and magnesium (1.17 g, 48 mmol) to THF (7.5 mL). did. After cooling, the mixture was diluted with water (30 mL) and unreacted magnesium and the resulting solid was filtered off. The filtrate was extracted with ether (15 mL ⁇ 3). The extracted composite was washed with brine (30 mL ⁇ 3) and dried over magnesium sulfate. This was dried under reduced pressure to obtain pale yellow oily compound 1 (5.4 g, yield 50%).
  • 2,9-di (2-ethylhexyl) dinaphtho [2,3-b: 2 ′, 3′-f] thieno [2,3-b] thiophene (stepwise as described below)
  • 2,9-EH-DNTT 2,9-EH-DNTT
  • 2-decyl-dinaphtho [2,3-b: 2 ′, 3] was prepared in the same manner as the synthesis of 2-2EH-DNTT, except that 2-ethylhexylmagnesium bromide was replaced with decylmagnesium bromide.
  • 2-D-DNTT thieno [2,3-b] thiophene
  • 2,9-D-DNTT As a comparative example, 2,9-didecyldinaphtho [2,3-b: 2 ′, 3] was prepared in the same manner as the synthesis of 2,9-EH-DNTT, except that 2-ethylhexylmagnesium bromide was replaced with decylmagnesium bromide. '-F] thieno [2,3-b] thiophene (hereinafter, 2,9-D-DNTT) was synthesized.
  • Thin films were prepared using 2-2EH-DNTT and 2,9-EH-DNTT, which had good solubility in solvents, and their physical properties were evaluated.
  • the absorption spectrum of the 2,9-EH-DNTT thin film is shown in FIG.
  • DNTT dinaphtho [2,3-b: 2 ′, 3′-f] thieno [2,3-b] thiophene
  • the photoelectron spectrum of the 2,9-EH-DNTT thin film is shown in FIG.
  • the ionization potential in the 2,9-EH-DNTT thin film estimated from the photoelectron spectrum is 5.7 eV, which is larger than 5.4 eV of unsubstituted DNTT. This can be explained by the weak intermolecular interaction.
  • the out-of-plane X-ray diffraction result of the 2,9-EH-DNTT thin film is shown in FIG. Although a crystal peak can be seen in FIG. 1C, the estimated interlayer distance is as short as 16 angstroms, and the molecular orientation is not desirable.
  • the absorption spectrum of the 2-2EH-DNTT thin film is shown in FIG.
  • the absorption spectrum of the 2-2-EH-DNTT thin film showed an absorption peak similar to that of DNTT, and a clear long wavelength shift was observed as compared with the 2,9-EH-DNTT thin film. This indicates that the intermolecular interaction in the thin film state is recovered as compared with the 2,9-EH-DNTT thin film.
  • FIG. 2C shows the out-of-plane X-ray diffraction result of the 2-2EH-DNTT thin film.
  • the peak observed by out-of-plane X-ray diffraction suggests that the crystal structure is oriented with the molecular long axis on the substrate surface, and the estimated interlayer distance is 26 ⁇ , including alkyl groups. Corresponds to the length of the molecular long axis.
  • a bottom-gate transistor element was fabricated using 2-2EH-DNTT and 2,9-EH-DNTT, which had good solubility as described above, and their characteristics were evaluated.
  • the surface of the silicon oxide film of the n-type silicon substrate is perfluorodecyltriethoxysilane (FDTS).
  • FDTS perfluorodecyltriethoxysilane
  • Silane-treated. 2-2 EH-DNTT was dissolved in chloroform to prepare a 0.3 g / L solution, filtered through a membrane filter, and then spin-coated on the surface-treated n-type silicon substrate to a thickness of about 100 nm.
  • 2-2-EH-DNTT thin film was prepared. This thin film was heated at 200 ° C. for 30 minutes in a nitrogen atmosphere.
  • transistor element 2-2EH-DNTT was vacuum-deposited on the EH-DNTT thin film to form a source electrode and a drain electrode.
  • a bottom gate / top contact transistor element having a channel length of 50 ⁇ m and a channel width of 1.5 mm was produced.
  • this transistor element is referred to as a transistor element 2-2EH-DNTT.
  • transistor element 2 9-EH-DNTT.
  • the transistor characteristics were changed by changing the gate voltage Vg from 20 to -60 V and the source-drain voltage Vd from 0 to -60 V in the fabricated transistor element 2-2-EH-DNTT. It was measured.
  • FIG. 3A shows transfer characteristics
  • FIG. 3B shows output characteristics. From these characteristics, the mobility was calculated to be 0.3 cm 2 / Vs.
  • the transistor element 2 and 9-EH-DNTT have been tried to measure the transistor characteristics in the same manner as described above. became.
  • the above-mentioned physical property analysis of the 2,9-EH-DNTT thin film strongly suggests that the two ethylhexyl groups are sterically bulky, thus preventing the packing of dense molecules and significantly reducing intermolecular interactions. Yes. This also confirms that the transistor element 2,9-EH-DNTT has no response, that is, the carriers injected into the thin film cannot move.
  • 2-3-3-EH-DNTT was used to fabricate a bottom gate / top contact transistor element, and its characteristics were evaluated.
  • a highly doped n-type silicon substrate having a 200 nm thick silicon oxide film to be a gate electrode was sufficiently washed.
  • 2-3EH-DNTT was dissolved in chloroform to prepare a 0.3 g / L solution, filtered through a membrane filter, and then spin-coated onto the surface-treated n-type silicon substrate.
  • 2-3-3-EH-DNTT thin films were prepared. This thin film was heated at 100 ° C. for 30 minutes in a nitrogen atmosphere. Gold was vacuum-deposited on a 2-3-3-EH-DNTT thin film to form a source electrode and a drain electrode. In this way, a bottom-gate / top-contact transistor element (an integrated element) having a channel length of 40 ⁇ m and a channel width of 3 mm was produced.
  • the surface of the silicon oxide film is treated with silane with 1,1,1,3,3,3-hexamethyldisilazane (HMDS), and the bottom gate / top contact type transistor is formed in the same manner as described above.
  • HMDS processing element 1,1,1,3,3,3-hexamethyldisilazane
  • ODTS processing element octadecyltrichlorosilane
  • the surface of the silicon oxide film was treated with octyltrichlorosilane (OTS) to produce a bottom gate / top contact type transistor element (OTS process element) in the same manner as described above.
  • OTS octyltrichlorosilane
  • the transistor characteristics were measured by changing the gate voltage Vg to 20 to ⁇ 60 V and the source-drain voltage Vd to 0 to ⁇ 60 V.
  • Table 2 shows carrier mobility ( ⁇ [cm 2 V ⁇ 1 s ⁇ 1 ]), threshold voltage (V th [V]), and on / off ratio (I on / off ) of each transistor element.
  • FIG. 4A shows the transfer characteristics
  • FIG. 4B shows the output characteristics of a transistor element manufactured by silane treatment of the substrate with ODTS.
  • 15 or more transistor elements are respectively produced, and the carrier mobility in Table 2 shows the average value and the maximum value (in parentheses).
  • the carrier mobility is improved as compared with the transistor element 2-2-EH-DNTT.
  • an ODTS element manufactured by subjecting a substrate to ODTS treatment had a maximum carrier mobility of 1.6 cm 2 / Vs (average: 1.02 cm 2 / Vs), and showed good transistor characteristics. This is probably because the ethyl group in the side chain of the ethyl heptyl group is separated from the DNTT skeleton, and the intermolecular interaction is increased.
  • an organic semiconductor layer can be formed using a solution process such as a coating method, so that a semiconductor such as a field effect transistor can be formed. It can be used to manufacture the device.

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  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Thin Film Transistor (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Dans la présente invention, un matériau semi-conducteur organique de dissolution est représenté par la formule (1). Dans la formule (1), chacun de (Y1) et (Y2) représente séparément un atome de chalcogène, l'un de R1 et R2 représente un alkyle ramifié, et l'autre représente un hydrogène.
PCT/JP2014/051213 2013-01-22 2014-01-22 Matériau semiconducteur organique de dissolution et dispositif semi-conducteur organique WO2014115749A1 (fr)

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KR1020157022803A KR102101242B1 (ko) 2013-01-22 2014-01-22 용액 프로세스용 유기 반도체 재료 및 유기 반도체 디바이스
CN201480005535.6A CN104956508B (zh) 2013-01-22 2014-01-22 溶液工艺用有机半导体材料和有机半导体设备
JP2014558587A JP6080870B2 (ja) 2013-01-22 2014-01-22 溶液プロセス用有機半導体材料及び有機半導体デバイス

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JP2017228622A (ja) * 2016-06-21 2017-12-28 山本化成株式会社 有機トランジスタ
JP2018026559A (ja) * 2016-08-03 2018-02-15 日本化薬株式会社 有機光電変換素子、有機光電変換素子用材料及びこれらを用いた有機撮像素子
JP2018190754A (ja) * 2017-04-28 2018-11-29 日本化薬株式会社 撮像素子用光電変換素子
WO2019101569A1 (fr) * 2017-11-21 2019-05-31 Basf Se Sels de sulfonium de dntt et composés apparentés en tant que précurseurs solubles photoclivables pour semi-conducteurs organiques destinés à être utilisés dans des transistors organiques à effet de champ
JP2020189793A (ja) * 2019-05-21 2020-11-26 国立大学法人東北大学 芳香族化合物の製造方法
JP2021075510A (ja) * 2019-11-13 2021-05-20 日本化薬株式会社 有機半導体化合物及びその用途
WO2021117622A1 (fr) * 2019-12-10 2021-06-17 日本化薬株式会社 Composé aromatique polycyclique condensé
US11296290B2 (en) 2018-03-07 2022-04-05 Clap Co., Ltd. Patterning method for preparing top-gate, bottom-contact organic field effect transistors
KR20220063189A (ko) 2019-09-17 2022-05-17 닛뽄 가야쿠 가부시키가이샤 축합 다환 방향족 화합물
US11355715B2 (en) 2017-10-19 2022-06-07 Clap Co., Ltd. Substituted benzonaphthathiophene compounds for organic electronics
WO2023189381A1 (fr) * 2022-03-30 2023-10-05 ソニーグループ株式会社 Élément électroluminescent et dispositif électronique

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JP2018190755A (ja) * 2017-04-28 2018-11-29 日本化薬株式会社 撮像素子用光電変換素子
CN110849252B (zh) * 2019-11-14 2021-06-18 东北师范大学 一种制备大面积可贴合半导体型接近传感器的方法

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Cited By (21)

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Publication number Priority date Publication date Assignee Title
JP2017228622A (ja) * 2016-06-21 2017-12-28 山本化成株式会社 有機トランジスタ
JP2018026559A (ja) * 2016-08-03 2018-02-15 日本化薬株式会社 有機光電変換素子、有機光電変換素子用材料及びこれらを用いた有機撮像素子
JP2018190754A (ja) * 2017-04-28 2018-11-29 日本化薬株式会社 撮像素子用光電変換素子
US11355715B2 (en) 2017-10-19 2022-06-07 Clap Co., Ltd. Substituted benzonaphthathiophene compounds for organic electronics
WO2019101569A1 (fr) * 2017-11-21 2019-05-31 Basf Se Sels de sulfonium de dntt et composés apparentés en tant que précurseurs solubles photoclivables pour semi-conducteurs organiques destinés à être utilisés dans des transistors organiques à effet de champ
KR20200070289A (ko) * 2017-11-21 2020-06-17 주식회사 클랩 유기 전계효과 트랜지스터에 사용되는 유기 반도체용 가용성 광절단 전구체로서의 dntt의 설포늄염 및 관련 화합물
JP2021504323A (ja) * 2017-11-21 2021-02-15 クラップ カンパニー リミテッドＣｌａｐ Ｃｏ．， Ｌｔｄ． 有機電界効果トランジスタに用いられる有機半導体用可溶性光切断性前駆体としてのｄｎｔｔのスルホニウム塩及び関連化合物
US11152578B2 (en) 2017-11-21 2021-10-19 Clap Co., Ltd. Sulfonium salts of DNTT and related compounds as soluble photocleavable precursors for organic semiconductors for use in organic field-effect transistors
KR102330923B1 (ko) 2017-11-21 2021-12-01 주식회사 클랩 유기 전계효과 트랜지스터에 사용되는 유기 반도체용 가용성 광절단 전구체로서의 dntt의 설포늄염 및 관련 화합물
US11296290B2 (en) 2018-03-07 2022-04-05 Clap Co., Ltd. Patterning method for preparing top-gate, bottom-contact organic field effect transistors
US11690236B2 (en) 2018-03-07 2023-06-27 Clap Co., Ltd. Patterning method for preparing top-gate, bottom-contact organic field effect transistors
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JP7241346B2 (ja) 2019-05-21 2023-03-17 国立大学法人東北大学 芳香族化合物の製造方法
KR20220063189A (ko) 2019-09-17 2022-05-17 닛뽄 가야쿠 가부시키가이샤 축합 다환 방향족 화합물
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WO2023189381A1 (fr) * 2022-03-30 2023-10-05 ソニーグループ株式会社 Élément électroluminescent et dispositif électronique

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