JP5733612B2 - 有機半導体薄膜用材料、該材料を用いた有機半導体薄膜の形成方法および有機薄膜トランジスタ - Google Patents
有機半導体薄膜用材料、該材料を用いた有機半導体薄膜の形成方法および有機薄膜トランジスタ Download PDFInfo
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- JP5733612B2 JP5733612B2 JP2011050792A JP2011050792A JP5733612B2 JP 5733612 B2 JP5733612 B2 JP 5733612B2 JP 2011050792 A JP2011050792 A JP 2011050792A JP 2011050792 A JP2011050792 A JP 2011050792A JP 5733612 B2 JP5733612 B2 JP 5733612B2
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- SDWGBHZZXPDKDZ-UHFFFAOYSA-N 2,6-dichloronaphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=C(Cl)C(C(O)=O)=C2C(C(=O)O)=CC(Cl)=C(C(O)=O)C2=C1C(O)=O SDWGBHZZXPDKDZ-UHFFFAOYSA-N 0.000 description 1
- IMUFGGNVUSMXHT-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol ethene Chemical group C(CCC)OCCOCCO.C=C IMUFGGNVUSMXHT-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- YPFNIPKMNMDDDB-UHFFFAOYSA-K 2-[2-[bis(carboxylatomethyl)amino]ethyl-(2-hydroxyethyl)amino]acetate;iron(3+) Chemical compound [Fe+3].OCCN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O YPFNIPKMNMDDDB-UHFFFAOYSA-K 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- CRWNQZTZTZWPOF-UHFFFAOYSA-N 2-methyl-4-phenylpyridine Chemical compound C1=NC(C)=CC(C=2C=CC=CC=2)=C1 CRWNQZTZTZWPOF-UHFFFAOYSA-N 0.000 description 1
- HPJFXFRNEJHDFR-UHFFFAOYSA-N 22291-04-9 Chemical group C1=CC(C(N(CCN(C)C)C2=O)=O)=C3C2=CC=C2C(=O)N(CCN(C)C)C(=O)C1=C32 HPJFXFRNEJHDFR-UHFFFAOYSA-N 0.000 description 1
- ZRJOUVOXPWNFOF-UHFFFAOYSA-N 3-dodecoxypropan-1-amine Chemical compound CCCCCCCCCCCCOCCCN ZRJOUVOXPWNFOF-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910001020 Au alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910000599 Cr alloy Inorganic materials 0.000 description 1
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- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
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- 229910004140 HfO Inorganic materials 0.000 description 1
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- 229910021193 La 2 O 3 Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
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- 239000006087 Silane Coupling Agent Substances 0.000 description 1
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- 229910006404 SnO 2 Inorganic materials 0.000 description 1
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- 125000001204 arachidyl 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])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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 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
- 125000002511 behenyl 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])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])[H] 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- 239000006229 carbon black Substances 0.000 description 1
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- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
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- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
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- 239000003245 coal 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
- 238000004440 column chromatography Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
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- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
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- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- AZHSSKPUVBVXLK-UHFFFAOYSA-N ethane-1,1-diol Chemical compound CC(O)O AZHSSKPUVBVXLK-UHFFFAOYSA-N 0.000 description 1
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- 238000001125 extrusion Methods 0.000 description 1
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- 230000006870 function Effects 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
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 125000000755 henicosyl 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])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
- KAJZYANLDWUIES-UHFFFAOYSA-N heptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCN KAJZYANLDWUIES-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
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- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- YMFPNHNDKLBSTC-UHFFFAOYSA-N naphthalene;thiophene Chemical class C=1C=CSC=1.C1=CC=CC2=CC=CC=C21 YMFPNHNDKLBSTC-UHFFFAOYSA-N 0.000 description 1
- YTVNOVQHSGMMOV-UHFFFAOYSA-N naphthalenetetracarboxylic dianhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=C2C(=O)OC(=O)C1=C32 YTVNOVQHSGMMOV-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001196 nonadecyl 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])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
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- KJOLVZJFMDVPGB-UHFFFAOYSA-N perylenediimide Chemical compound C=12C3=CC=C(C(NC4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)NC(=O)C4=CC=C3C1=C42 KJOLVZJFMDVPGB-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 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
- 229920006267 polyester film 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
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene 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
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 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
- 230000003068 static effect Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002076 thermal analysis method Methods 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
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 229960002415 trichloroethylene Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 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
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thin Film Transistor (AREA)
Description
[製造例1:化合物Aの合成]
ナフタレンテトラカルボン酸無水物2.23gと、トリデシルアミン4.15gとを、ジメチルホルムアミド20ml中に分散させ、窒素気流下、還流下で6時間撹拌する。冷却後、濾過し、濾物をメタノール・希塩酸、次いで水の順に洗浄する。洗浄後、乾燥して3.27gのN,N’−ジトリデシル−1,4,5,8−ナフタレンテトラカルボキシジイミドを得た(収率62%)。得られた化合物は、カラムクロマトを用いて分取し、再結晶により精製し、NTCDI−C13(化合物A)を得た。示差走査熱量測定熱分析(DSC)による吸熱ピーク(室温〜250℃まで測定)は、109℃、145℃、161℃に存在した(図7参照)。
製造例1のトリデシルアミンに変えて、ウンデシルアミン、ドデシルアミン、ヘプタデシルアミン、オクタデシルアミン、3−(ドデシルオキシ)プロピルアミン、及び、オクチルアミンをおのおの用いて化合物B、C、D、E、F、Gを得た。得られた化合物A〜Fを実施例に、化合物Gを比較例の化合物として用いた。得られた化合物の相転移温度を表1に示した。
薄膜トランジスタの電気特性は、Agilent社製半導体デバイスアナライザー(B1500A)で室温・真空下にて測定した。ID(ドレイン電流)−VD(ソース−ドレイン間電圧)特性(伝達特性)は、VG(ゲート電圧)を、100V、80V、60V、40V、20V、それぞれ印加した各条件において、ドレイン電圧VDを0から100Vへと掃引して測定した。また、ID−VG特性(出力特性)は、VD=100Vにおいて、VGを0から100Vまで掃引して測定した。
(ID)1/2−VG特性の直線領域と式(1)から移動度を算出した。
なお、上記式(1)中、Ciはゲート誘電体の静電容量(nF/cm2)、VTは閾電圧である。電界効果移動度(μ)は、(ID)1/2−VG特性の傾きから式(1)を用いて求め、フィッティング直線のX切片から、閾電圧(VT)を算出した。
「化合物A(NTCDI−C13)を用いた有機薄膜トランジスタの作製」
ゲート絶縁体層となる酸化シリコン膜(厚さ200nm)を表面に有するシリコン基板を用意し、ITO(150nm)をスパッタ成膜し、フォトリソグラフィとウェットエッチングを用いて、ソース電極、およびドレイン電極をパターニングした。このときのチャネル長、チャネル幅はそれぞれ100μm、2,000μmであった。その後、製造例1で得た化合物Aをクロロホルムに濃度0.50%となるように溶解し、該溶液を用いて、スピンコーター(1,500r.p.m./60s)にてシリコン基板上に有機半導体薄膜を形成し、真空中において1時間の減圧乾燥を行った。
参考例1で作成したデバイスを用い、真空雰囲気下(2,000Pa)において、表1に示した所定の温度でそれぞれ熱処理を2時間行い、処理したものを実施例1〜3のデバイスとした。得られた各デバイスの(ID)1/2−VG特性より算出したトランジスタ特性を表2に示した。
「化合物A(NTCDI−C13)を用いた有機薄膜トランジスタの作製」
参考例1と同様に作成した有機薄膜トランジスタを、窒素雰囲気下(高純度ガス:G3)において、表3に示す所定の温度でそれぞれ1時間の熱処理し、有機薄膜トランジスタを作成し、これらをデバイスとした。得られた各デバイスの(ID)1/2−VG特性より算出したトランジスタ特性を表3に示した。
「化合物C(NTCDI−C12)を用いた有機薄膜トランジスタの作製」
ゲート絶縁体層となる酸化シリコン膜(厚さ200nm)を表面に有するシリコン基板を用意し、ITO(150nm)をスパッタ製膜し、フォトリソグラフィとウェットエッチングを用いてソース電極、およびドレイン電極をパターニングした。このときのチャネル長、チャネル幅は100μm、2,000μmであった。その後、合成例3で得た化合物Cをクロロホルムに濃度1.0%となるように溶解し、スピンコーター(1,500r.p.m./60s)にてシリコン基板上に有機半導体薄膜を形成した。そして、常温において減圧乾燥した後、真空中において150℃で、それぞれ1時間の熱処理を行った。
その結果、ID−VD特性において、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。(ID)1/2−VG特性から算出した電子移動度は、1.72×10-1cm2/Vs、閾電圧値は24V、ON/OFF比:105であった。
「化合物F(NTCDI−C12−O−C3−)を用いた有機薄膜トランジスタの作製」
実施例3の化合物Aを化合物Fに代えた以外は、実施例3と同様に有機薄膜トランジスタを作製した。得られた有機薄膜トランジスタは高い移動度と高いオンオフ比を示し、バランスのよいトランジスタ特性を示した。
「化合物G(NTCDI−C8)を用いた有機薄膜トランジスタの作製」
実施例1の化合物Aを化合物Fに代えた以外は、実施例1と同様にして、比較例1の有機薄膜トランジスタを作製した。得られた有機薄膜トランジスタを真空オーブンで2時間乾燥した。得られたトランジスタについて、トランジスタ特性を実施例1と同様に測定した。その結果、実施例と比較すると、移動度及びオン/オフ比の値は、共に小さかった。本有機薄膜トランジスタは、熱処理を行わなかった。表1に、(ID)1/2−VG特性から算出した電子移動度は、0.005cm2/Vs、閾電圧は43Vであった。
本発明を特徴づける、一般構造式(1)で表わされるナフタレンテトラカルボキシジイミド誘導体によれば、簡便な方法である印刷法によって、良好な有機半導体薄膜の形成が可能となった。本発明の有機半導体薄膜により作成された有機薄膜トランジスタは液晶状態への転移温度付近での熱処理を行うことで、電子移動度を一桁以上増大させることが、良好なトランジスタ特性を示すことが確認された。
以上、本発明を好ましい実施例を挙げて説明したが、本発明は前記実施例に限定されるものではない。
12:ソース電極
13:ドレイン電極
14:ゲート電極
15:有機半導体薄膜
16:基板
Claims (11)
- n型有機半導体素子として使用可能な有機半導体薄膜用材料であって、80℃〜250℃の温度領域に相転移温度を有し、かつ、下記一般構造式(1)で表される、加熱することで液晶状態へ相転移し、分解温度以下でサーモトロピック液晶相を有するナフタレンテトラカルボキシジイミド誘導体を含むことを特徴とする有機半導体薄膜用材料。
(但し、式中、R1、R2は、それぞれ独立に、炭素数が11、13、15又は17の奇数の炭素数の、分岐または非分岐のアルキル基であり、さらにN、O、S、Pのヘテロ原子を含んでいてもよい。X1、X2、X3、X4は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基から選ばれる。) - 前記一般構造式(1)で表される誘導体が、下記構造式(1)で表わされるN,N'−ジウンデシル−1,4,5,8−ナフタレンテトラカルボキシジイミド、下記構造式(2)で表わされるN,N'−ジトリデシル−1,4,5,8−ナフタレンテトラカルボキシジイミド、下記構造式(3)で表わされるN,N'−ジペンタデシル−1,4,5,8−ナフタレンテトラカルボキシジイミド、下記構造式(4)で表わされるN,N'−ジヘプタデシル−1,4,5,8−ナフタレンテトラカルボキシジイミド、或いは、下記構造式(5)で表わされるN,N'−ビス(3−(n−ドデシルオキシ)−n−プロピル)−1,4,5,8−ナフタレンテトラカルボキシジイミドのいずれかである請求項1に記載の有機半導体薄膜用材料。
- 前記一般構造式(1)で表される誘導体が、下記構造式(1)で表わされるN,N'−ジウンデシル−1,4,5,8−ナフタレンテトラカルボキシジイミド、下記構造式(2)で表わされるN,N'−ジトリデシル−1,4,5,8−ナフタレンテトラカルボキシジイミド、或いは、下記構造式(3)で表わされるN,N'−ジペンタデシル−1,4,5,8−ナフタレンテトラカルボキシジイミドのいずれかである請求項1に記載の有機半導体薄膜用材料。
- 80℃〜250℃の温度領域に相転移温度を有し、かつ、下記一般構造式(1)で表される、加熱することで液晶状態へ相転移してサーモトロピック液晶性を示すナフタレンテトラカルボキシジイミド誘導体を含む有機半導体薄膜用材料を用い、該材料を、有機溶媒に溶解又は/及び分散させた状態で基板上に塗工し、乾燥後、形成した塗工膜を80℃〜350℃の温度で加熱処理して該塗工膜を加熱し、さらに冷えた後の塗工膜の膜厚を10nm〜10μmとすることを特徴とする有機半導体薄膜の形成方法。
(但し、式中、R1、R2は、それぞれ独立に、炭素数が10〜22の分岐または非分岐のアルキル基であり、さらにN、O、S、Pのヘテロ原子を含んでいてもよい。X 1 、X 2 、X 3 、X 4 は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基から選ばれる。) - 前記分岐または非分岐のアルキル基の炭素数が、11、13、15又は17の奇数の炭素数である請求項4に記載の有機半導体薄膜の形成方法。
- 前記一般構造式(1)で表される誘導体が、下記構造式(1)で表わされるN,N'−ジウンデシル−1,4,5,8−ナフタレンテトラカルボキシジイミド、下記構造式(2)で表わされるN,N'−ジトリデシル−1,4,5,8−ナフタレンテトラカルボキシジイミド、下記構造式(3)で表わされるN,N'−ジペンタデシル−1,4,5,8−ナフタレンテトラカルボキシジイミド、下記構造式(4)で表わされるN,N'−ジヘプタデシル−1,4,5,8−ナフタレンテトラカルボキシジイミド、或いは、下記構造式(5)で表わされるN,N'−ビス(3−(n−ドデシルオキシ)−n−プロピル)−1,4,5,8−ナフタレンテトラカルボキシジイミドのいずれかである請求項4に記載の有機半導体薄膜の形成方法。
- 前記塗工膜を80℃〜250℃の温度に加熱する請求項4〜6のいずれか1項に記載の有機半導体薄膜の形成方法。
- 前記加熱処理を、10-5〜50,000Paの減圧雰囲気下において行う請求項4〜7のいずれか1項に記載の有機半導体薄膜の形成方法。
- 前記加熱処理を、不活性ガス雰囲気下において行う請求項4〜8のいずれか1項に記載の有機半導体薄膜の形成方法。
- 基板上に、ゲート電極、ゲート絶縁層、有機半導体薄膜ならびにソース電極およびドレイン電極が少なくとも形成されている有機薄膜トランジスタにおいて、上記有機半導体薄膜が、請求項1〜3のいずれか1項に記載の有機半導体薄膜用材料で形成されたものであることを特徴とする有機薄膜トランジスタ。
- そのキャリア移動度が0.01cm2/Vs以上である請求項10に記載の有機薄膜トランジスタ。
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