JP5308532B2 - 有機半導体材料、有機半導体薄膜および有機薄膜トランジスタ - Google Patents
有機半導体材料、有機半導体薄膜および有機薄膜トランジスタ Download PDFInfo
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- JP5308532B2 JP5308532B2 JP2011534958A JP2011534958A JP5308532B2 JP 5308532 B2 JP5308532 B2 JP 5308532B2 JP 2011534958 A JP2011534958 A JP 2011534958A JP 2011534958 A JP2011534958 A JP 2011534958A JP 5308532 B2 JP5308532 B2 JP 5308532B2
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 107
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- 125000001424 substituent group Chemical group 0.000 claims description 7
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- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
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- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000000788 chromium alloy Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003353 gold alloy Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000379 polypropylene carbonate Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
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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
- C07D495/12—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 three hetero rings
- C07D495/14—Ortho-condensed systems
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- 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
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- 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
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- 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
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- 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
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- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Thin Film Transistor (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Indole Compounds (AREA)
Description
(式中のAは1個またはそれ以上の芳香族環からなる環状共役系骨格構造を表し、R1、R2は各々独立に、置換基を有してもよい、炭素数1から18の直鎖アルキル基または分岐アルキル基、或いは、炭素数1から18の直鎖アルキル基または分岐アルキル基の水素原子の一部がフッ素原子で置換された、置換基を有してもよいアルキル基を表す。)
以下、本発明による有機薄膜トランジスタについてより詳細に説明するが、本発明はこれら構造には限られない。
[化合物Aの合成]
2,5−[1,4−ビス(N,N’−オクチルジフタルイミド)]−2,2’−ビチオフェン(前記式(III)の構造を有し、DPIBTと以降呼ぶことがある)の合成
4−ブロモ−N−オクチルフタルイミドと5,5’−ビス(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−2,2’−ビチオフェンとをパラジウム触媒の存在下、スズキ−ミヤウラカップリング反応により結合させて、標題化合物を合成した。得られたクルード生成物をカラムクロマトグラフィーにて分取し、さらに、再結晶法により精製した。精製後の標題化合物の収率は83%であった。
M.S.(EI):計算値 C40H44N2O4S2:680.92、実測値:682
分解温度:437℃、ガラス転移温度103℃、融点224℃
2,5−[1,4(N,N’−オクチルジフタルイミド)]ベンゼン(前記式(I)の構造を有し、DPIBenと以降呼ぶことがある)の合成
4−ブロモ−N−オクチルフタルイミドと1,4−ビス(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−ベンゼンとをパラジウム触媒の存在下、スズキ−ミヤウラカップリング反応により結合させて、標題化合物を合成した。得られたクルード生成物をカラムクロマトグラフィーを用いて分取し、さらに、再結晶法により精製した。精製後の標題化合物の収率は53%であった。
M.S.(EI):計算値 C38H44N2O4:592.79、実測値:593
分解温度:433℃、ガラス転移温度101℃、融点223℃
2,5−[1,4−ビス(N,N’−オクチルジフタルイミド)]シアノベンゼン(前記式(II)の構造を有し、DPITNと以降呼ぶことがある)の合成
4−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−N−オクチルフタルイミドと1,4−ジクロロ−2,5−ジシアノベンゼンとをパラジウム触媒の存在下、スズキ−ミヤウラカップリング反応により結合させて、標題化合物を合成した。得られたクルード生成物をカラムクロマトグラフィーを用いて分取し、さらに、再結晶法により精製した。精製後の標題化合物の収率は33%であった。
M.S.(EI):計算値 C40H42N2O4:642.81、実測値:643
分解温度:420℃、融点286℃
2,5−[1,4−ビス(N,N’−オクチルジフタルイミド)]チエノチオフェン(前記式(IV)の構造を有し、DPITTと以降呼ぶことがある)の合成
4−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−N−オクチルフタルイミドと2,5−ジブロモチエノ(3,2−b)チオフェンとをパラジウム触媒の存在下、スズキ−ミヤウラカップリング反応により結合させて、標題化合物を合成した。得られたクルード生成物をカラムクロマトグラフィーを用いて分取し、さらに、再結晶法により精製した。精製後の標題化合物の収率は56%であった。
M.S.(EI):計算値 C40H42N2O4S2:654.89、実測値:655
2,6−[1,4−ビス(N,N’−オクチルジフタルイミド)アントラセン](前記式(V)の構造を有し、DPIAnと以降呼ぶことがある)の合成
4−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)−N−オクチルフタルイミドと2,6−ジブロモアントラセンとをパラジウム触媒の存在下、スズキ−ミヤウラカップリング反応により結合させて、標題化合物を合成した。得られたクルード生成物をカラムクロマトグラフィーを用いて分取し、さらに、再結晶法により精製した。精製後の標題化合物の収率は56%であった。
M.S.(EI):計算値 C46H48N2O4:692.89、実測値:693
化合物A(DPIBT)を用いた有機薄膜トランジスタの作製
ゲート絶縁層となる酸化シリコン膜(厚さ300nm)を表面に有するシリコン基板をゲート電極、ゲート絶縁層として準備した。さらにHMDSトルエン溶液(1.0質量%)に8時間浸漬し、酸化シリコン膜表面にHMDS−SAM層(ヘキサメチルジシラザン−自己組織化単分子膜)を形成した。DPIBTからなる有機半導体薄膜は、HMDS−SAM層上に真空蒸着法(蒸着レート0.05[nm/sec])により成膜した(厚さ50nm)。次に、シャドーマスクを介して、ソース/ドレイン電極として金電極のパターンを形成し(30nm)、トップコンタクト型有機薄膜トランジスタを作成した。このときの、チャネル長、チャネル幅は、それぞれ50μm、5500μmとした。前記のとおり作製した電界効果トランジスタの特性を評価した。
次に、実施例1で使用した化合物Aに変えて化合物B(DPIBen)を使用した。
ゲート絶縁層となる酸化シリコン膜(厚さ300nm)を表面に有するシリコン基板をゲート電極、ゲート絶縁層として準備した。さらにHMDSトルエン溶液(1.0質量%)に8時間浸漬し、酸化シリコン膜表面にHMDS−SAM層を形成した。DPIBenからなる有機半導体薄膜は、HMDS−SAM層上に真空蒸着法(蒸着レート0.05[nm/sec]:基板温度120℃)により成膜した(厚さ50nm)。電極のパターニングは、実施例1と同様に実施し、実施例2の有機薄膜トランジスタを得た。このトランジスタについて、異なるゲート電圧毎でのドレイン電圧とドレイン電流とを測定した。ドレイン電流−ドレイン電圧曲線に明澄な飽和領域が認められたことから、典型的なn型特性を有する電界効果トランジスタとして駆動することが示された。ドレイン電流−ドレイン電圧曲線から算出したトランジスタ特性値を表1に示す。
次に、実施例2で使用した化合物Bに変えて化合物C(DPITN)を使用する以外は実施例2に従って、有機薄膜トランジスタを作成した。このトランジスタについて、異なるゲート電圧毎でのドレイン電圧とドレイン電流とを測定した。ドレイン電流−ドレイン電圧曲線に明澄な飽和領域が認められたことから、典型的なn型特性を有する電界効果トランジスタとして駆動することが示された。ドレイン電流−ドレイン電圧曲線から算出したトランジスタ特性値を表1に示す。
次に、実施例2で使用した化合物Bに変えて化合物A(DPIBT)を使用する以外は実施例2に従って、有機薄膜トランジスタを作成した。このトランジスタについて、異なるゲート電圧毎でのドレイン電圧とドレイン電流とを測定した。ドレイン電流−ドレイン電圧曲線に明澄な飽和領域が認められたことから、典型的なn型特性を有する電界効果トランジスタとして駆動することが示された。ドレイン電流−ドレイン電圧曲線から算出したトランジスタ特性値を表1に示す。
実施例1の方法を準用した。ゲート絶縁層となる酸化シリコン膜(厚さ300nm)を表面に有するシリコン基板をゲート電極、ゲート絶縁層として準備した。さらにHMDSトルエン溶液(1.0質量%)に8時間浸漬し、酸化シリコン膜表面にHMDS−SAM層を形成した。実施例1で使用した化合物A(DPIBT)をクロロホルムに濃度1質量%となるように溶解し、スピンコーターにて有機半導体膜を120℃に加温したシリコン基板上に形成されたHMDS−SAM膜上に形成した。電極のパターニングは、実施例1と同様に実施し、実施例5の有機薄膜トランジスタを得た。このトランジスタについて、異なるゲート電圧毎でのドレイン電圧とドレイン電流とを測定した。ドレイン電流−ドレイン電圧曲線に明澄な飽和領域が認められたことから、典型的なn型特性を有する電界効果トランジスタとして駆動することが示された。ドレイン電流−ドレイン電圧曲線から算出したトランジスタ特性値を表1に示す。
化合物A(DPIBT)、化合物B(DPIBen)、化合物C(DPITN)、化合物D(DPITT)、化合物E(DPIAn)を使用し、加温したHMDS−SAM膜を有するシリコン基板を用いて、実施例1と同様に有機薄膜トランジスタを得た。このトランジスタは、典型的なn型特性を有する電界効果トランジスタとして駆動することが示された。ドレイン電流−ドレイン電圧曲線から算出したトランジスタ特性値を表2に示す。
12:ソース電極
13:ドレイン電極
14:ゲート電極
15:有機半導体層
16:基板
Claims (9)
- Aが、ベンゼン環、ナフタレン環、アントラセン環、フェナントレン環、ピレン環、トリフェニレン環、ナフタセン環、ペンタセン環、ビフェニル環、チオフェン環、ビチオフェン環、ターチオフェン環、クオターチオフェン環、キンキチオフェン環、セキシチオフェン環、セプチチオフェン環、オクチチオフェン環、ベンゾチオフェン環、チエノチオフェン環またはジチエノチオフェン環である請求項1又は2に記載の有機半導体材料。
- Aが、置換基としてフッ素原子、臭素原子、塩素原子またはシアノ基を1個またはそれ以上有する請求項1又は2に記載の有機半導体材料。
- Aが、1〜4個の芳香族環よりなる請求項1又は2に記載の有機半導体材料。
- 請求項1〜6のいずれか1項に記載された有機半導体材料を含むことを特徴とする有機半導体薄膜。
- 基板上に形成され、ゲート電極、ゲート絶縁層、有機半導体層ならびにソース電極およびドレイン電極を有する有機薄膜トランジスタにおいて、上記有機半導体層が、請求項7に記載された有機半導体薄膜からなることを特徴とするn型有機薄膜トランジスタ。
- 電子移動度が0.001〜5.0cm2/Vsである請求項8に記載のn型有機薄膜トランジスタ。
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