TWI602798B - Composition for the production of organic transistors, and use of the solvent or solvent composition for the production of organic transistors - Google Patents
Composition for the production of organic transistors, and use of the solvent or solvent composition for the production of organic transistors Download PDFInfo
- Publication number
- TWI602798B TWI602798B TW102145490A TW102145490A TWI602798B TW I602798 B TWI602798 B TW I602798B TW 102145490 A TW102145490 A TW 102145490A TW 102145490 A TW102145490 A TW 102145490A TW I602798 B TWI602798 B TW I602798B
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- TW
- Taiwan
- Prior art keywords
- ether
- group
- solvent
- acetate
- composition
- Prior art date
Links
- 239000002904 solvent Substances 0.000 title claims description 114
- 239000000203 mixture Substances 0.000 title claims description 65
- 238000004519 manufacturing process Methods 0.000 title claims description 21
- 239000004065 semiconductor Substances 0.000 claims description 56
- 239000000463 material Substances 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229910052799 carbon Chemical group 0.000 claims description 15
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- JXYRIQRQKAUQIY-UHFFFAOYSA-N acetic acid;oxolane Chemical compound CC(O)=O.C1CCOC1 JXYRIQRQKAUQIY-UHFFFAOYSA-N 0.000 claims description 8
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- RZXAHVCTRLTLNA-UHFFFAOYSA-N 2-(2-methoxypropoxy)-1-propoxypropane Chemical compound CCCOCC(C)OCC(C)OC RZXAHVCTRLTLNA-UHFFFAOYSA-N 0.000 claims description 7
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- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 claims description 6
- STXQJDVOMPXMMW-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)butane Chemical compound CCCCOC(C)COC STXQJDVOMPXMMW-UHFFFAOYSA-N 0.000 claims description 6
- LIYRYVJXMPWPAS-UHFFFAOYSA-N 1-methoxy-2-propoxypropane Chemical compound CCCOC(C)COC LIYRYVJXMPWPAS-UHFFFAOYSA-N 0.000 claims description 6
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- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 6
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 5
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- DRLRGHZJOQGQEC-UHFFFAOYSA-N 2-(2-methoxypropoxy)propyl acetate Chemical compound COC(C)COC(C)COC(C)=O DRLRGHZJOQGQEC-UHFFFAOYSA-N 0.000 claims description 4
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 claims description 4
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- 150000001721 carbon Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
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- 150000002148 esters Chemical class 0.000 claims description 3
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- 238000000034 method Methods 0.000 description 21
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
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- HGERSUQOJQWENV-UHFFFAOYSA-N 1-pentan-2-yloxypropan-2-ol Chemical compound CCCC(C)OCC(C)O HGERSUQOJQWENV-UHFFFAOYSA-N 0.000 description 1
- JOERQAIRIDZWHX-UHFFFAOYSA-N 1-propoxy-2-(2-propoxypropoxy)propane Chemical compound CCCOCC(C)OCC(C)OCCC JOERQAIRIDZWHX-UHFFFAOYSA-N 0.000 description 1
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 1
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- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 description 1
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- IPSOQTFPIWIGJT-UHFFFAOYSA-N acetic acid;1-propoxypropane Chemical compound CC(O)=O.CCCOCCC IPSOQTFPIWIGJT-UHFFFAOYSA-N 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 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
- GSCLMSFRWBPUSK-UHFFFAOYSA-N beta-Butyrolactone Chemical compound CC1CC(=O)O1 GSCLMSFRWBPUSK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000012461 cellulose resin Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- UBPGILLNMDGSDS-UHFFFAOYSA-N diethylene glycol diacetate Chemical compound CC(=O)OCCOCCOC(C)=O UBPGILLNMDGSDS-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- UYAAVKFHBMJOJZ-UHFFFAOYSA-N diimidazo[1,3-b:1',3'-e]pyrazine-5,10-dione Chemical compound O=C1C2=CN=CN2C(=O)C2=CN=CN12 UYAAVKFHBMJOJZ-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- CNEKKZXYBHKSDC-UHFFFAOYSA-N ethyl acetate;propane-1,2-diol Chemical compound CC(O)CO.CCOC(C)=O CNEKKZXYBHKSDC-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- 125000002463 lignoceryl 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])C([H])([H])C([H])([H])[H] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
- H01B1/20—Conductive material dispersed in non-conductive organic material
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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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- 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]
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Dispersion Chemistry (AREA)
- Materials Engineering (AREA)
- Thin Film Transistor (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Description
本發明關於對有機半導體材料的溶解性優異之有機電晶體製造用溶劑或溶劑組成物、及含該有機電晶體製造用溶劑或溶劑組成物與有機半導體材料之有機電晶體製造用組成物。本案主張於2012年12月12日在日本申請之特願2012-271139號之優先權，在此援用其內容。
電晶體係被廣泛運用作為構成顯示器、電腦機器的重要半導體電子裝置，先前多晶矽、非晶矽等無機物係作為半導體材料使用。然而，在採用此種無機物之薄膜電晶體的製造中，真空製程或高溫製程為必要者，而有高製造成本之問題。又，由於含高溫製程，所以對可使用的基板有限制，例如現今係主要使用玻璃基板等。然而，玻璃基板雖耐熱性高，但對於衝擊弱、難以輕量化、缺乏柔軟性，因此難以形成可撓性電晶體。
於是，近年來大量進行關於利用有機半導體材料之有機電子裝置的研究開發。有機半導體材料能夠以印刷法、旋轉塗布法等濕式製程之簡便方法輕易地形成薄膜，與利用習知之無機半導體材料的電晶體相比，具有可使製造製程溫度低溫化之優點。藉此，一般耐熱
性低的塑膠基板之使用變為可能，可實現顯示器等電子裝置之輕量化、低成本化，同時能夠期待利用塑膠基板的可能性之用途等多樣的展開。
作為有機半導體材料，已知藉由使用例如二萘[2,3-b：2’,3’-f]噻吩并[3,2-b]噻吩等之低分子的半導體材料，以顯現高半導體裝置性能(非專利文獻1)。然而，以二萘[2,3-b：2’,3’-f]噻吩并[3,2-b]噻吩為代表的未經取代的并苯(acene)系化合物多半因πt共軛系統導致的強分子間相互作用而缺乏對溶劑之溶解性(專利文獻1)。因此，無法調整高濃度溶解有機半導體材料之有機電晶體製造用組成物，以印刷法形成的有機半導體係晶粒變小，若不施加高電壓則無法通電，進而有施加高電壓時絕緣膜剝落等問題。
作為解決上述問題之方法，專利文獻2、3中記載使用附有用以對并苯系化合物賦予溶解性之脫離基的化合物作為有機半導體材料，使用氯仿或二氯苯等鹵化物作為溶劑。然而，與不附有脫離基的并苯系化合物相比，前述具有脫離基的并苯系化合物大多有在溶解時的加熱中不安定、及電荷移動度低之問題。
又，非專利文獻2中記載使用附有烷基取代基以對并苯系化合物賦予溶解性之化合物作為有機半導體材料，使用對前述有機半導體材料具有高溶解性之鹵化物作為溶劑。然而，鹵化物恐有生態毒性之虞，有作業安全上的問題。
又，專利文獻4記載使用未經取代的并苯系化
合物之分散液以形成薄膜。然而，難以防止分散液中所含之未經取代的并苯系化合物的凝集以維持其分散性，因未經取代的并苯系化合物係不規則地凝集而有電荷移動度降低之問題。
[專利文獻1]日本特開2009-302264號公報
[專利文獻2]日本特開2011-148743號公報
[專利文獻3]日本特開2012-041327號公報
[專利文獻4]日本特開2011-003852號公報
[非專利文獻1]J. Am. Chem. Soc., 2005, 127 (14), p 614-618
[非專利文獻2]J. Am. Chem. Soc., 2007, 129 (14), p 15732-15733
因此，本發明之目的為提供一種對有機半導體材料的溶解性優異、可形成結晶性高之有機電晶體的有機電晶體製造用溶劑或溶劑組成物。
本發明之其他目的為提供包含前述有機電晶體製造用溶劑或溶劑組成物之有機電晶體製造用組成物。
本發明人等為解決上述課題而進行鑽研探討，結果發現若使用特定溶劑或溶劑組成物，則即使在較低溫下亦可實現高有機半導體材料溶解性，在與玻璃基板相比耐熱性較低的塑膠基板上也可利用印刷法形成有機電晶體。又，發現若將含有前述溶劑或溶劑組成物的有機電晶體製造用組成物塗布在基板上時，有機半導體材料係利用自組織化作用而進行結晶化。進一步發現：視需要將通常用於電子材料用途的溶劑混合於前述溶劑或溶劑組成物時，能夠進一步提升塗布性、乾燥性。本發明係根據此等發現而完成者。
亦即，本發明為提供一種有機電晶體製造用溶劑或溶劑組成物，其係有機半導體材料溶解用的溶劑或溶劑組成物，其包含下述式(A)所示之溶劑A。
作為前述溶劑A，較佳為包含選自乙二醇二甲醚、二乙二醇二甲醚、乙二醇單乙醚乙酸酯、乙二醇
單丙醚乙酸酯、乙二醇單丁醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單丁醚乙酸酯、丙二醇二甲醚、丙二醇甲基乙醚、丙二醇甲基丙醚、丙二醇甲基丁醚、二丙二醇二甲醚、二丙二醇甲基乙醚、二丙二醇甲基丙醚、二丙二醇甲基丁醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、二丙二醇單甲醚乙酸酯、二丙二醇單乙醚乙酸酯、3-甲氧基丁醇乙酸酯、乙酸四氫呋喃酯、及環己醇乙酸酯中之至少1種。
作為前述有機半導體材料，較佳為選自下述式(1)所示之化合物(1)、及具有1種或2種以上之下述式(2-a)~(2-d)所示之重複單位的化合物(2)中之至少一種化合物：
本發明又提供含有機半導體材料與前述有機電晶體製造用溶劑或溶劑組成物之有機電晶體製造用組成物。
作為前述有機半導體材料，較佳為選自下述式(1)所示之化合物(1)、及具有1種或2種以上之下述式(2-a)~(2-d)所示之重複單位的化合物(2)中之至少一種化合物：
亦即，本發明係關於以下者。
(1)一種有機電晶體製造用溶劑或溶劑組成物，其係有機半導體材料溶解用的溶劑或溶劑組成物；其包含前述式(A)所示之溶劑A。
(2)如(1)所記載之有機電晶體製造用溶劑或溶劑組成物，其中溶劑A包含選自乙二醇二甲醚、二乙二醇二甲醚、乙二醇單乙醚乙酸酯、乙二醇單丙醚乙酸酯、乙二醇單丁醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單丁醚乙酸酯、丙二醇二甲醚、丙二醇甲基乙醚、丙二醇甲基丙醚、丙二醇甲基丁醚、二丙二醇二甲醚、二丙二醇甲基乙醚、二丙二醇甲基丙醚、二丙二醇甲基丁醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、二丙二醇
單甲醚乙酸酯、二丙二醇單乙醚乙酸酯、3-甲氧基丁醇乙酸酯、乙酸四氫呋喃酯、及環己醇乙酸酯中之至少1種。
(3)如(1)或(2)所記載之有機電晶體製造用溶劑或溶劑組成物，其中有機半導體材料係選自前述式(1)所示之化合物(1)、及具有1種或2種以上之前述式(2-a)~(2-d)所示之重複單位的化合物(2)中之至少1種化合物。
(4)一種有機電晶體製造用組成物，其包含有機半導體材料、與如(1)或(2)所記載之有機電晶體製造用溶劑或溶劑組成物。
(5)如(4)所記載之有機電晶體製造用組成物，其中有機半導體材料係選自前述式(1)所示之化合物(1)、及具有1種或2種前述式(2-a)~(2-d)所示之重複單位之化合物(2)中之至少1種化合物。
本發明之有機電晶體製造用溶劑或溶劑組成物即使在較低溫下，仍具有高有機半導體材料溶解性。因此，在耐熱性較玻璃基板低但對於衝擊強、輕量且可撓性的塑膠基板等上，亦可直接形成有機電晶體；並且，能夠形成對於衝擊強、輕量且可撓的顯示器或電腦機器。又，能夠以印刷法、旋轉塗布法等濕式製程之簡便方法輕易地製造有機電晶體，可大幅削減成本。
於是，若在基板上塗布本發明之有機電晶體製造用組成物時，有機半導體材料係藉由自組織化作用而結晶化，可得具有高結晶性之有機電晶體。
[有機電晶體製造用溶劑或溶劑組成物]
本發明之有機電晶體製造用溶劑或溶劑組成物為有機半導體材料溶解用的溶劑或溶劑組成物；其特徵為包含上述式(A)所示之溶劑A。
(溶劑A)
本發明之溶劑A為上述式(A)所示。式(A)中、R1為C1-4烷基、C1-4醯基、C5-6環烷環、C5-6環烯環、C6-12芳基、或此等結合2個以上而成的基。R2、R3、R4、R5係相同或相異，為氫原子、C1-4烷基、或C1-4醯基。R6為C1-4烷基、或C1-4醯基。R1與R3亦可相互結合而與相鄰的氧原子及碳原子一起形成環。n為1或2、m為0~2之整數。
作為R1~R6中的C1-4(=碳數1~4)烷基，例如可舉出甲基、乙基、丙基、丁基等。
作為R1~R6中的C1-4(=碳數1~4)醯基，例如可舉出乙醯基、丙醯基、丁醯基等。
作為R1中的C5-6(=碳數5~6)環烷環，例如可舉出環戊烷環、環己烷環等，作為C5-6(碳數5~6)環烯環，例如可舉出環戊烯環、環己烯環等。
作為R1中的C6-12(=碳數6~12)芳基，例如可舉出苯基、萘基等。
作為R1與R3相互結合而與相鄰的氧原子及碳原子一起形成的環，例如可舉出四氫呋喃環等的含有氧原子作為雜原子的5~7員雜環式化合物等。
作為本發明之溶劑A，例如可舉出乙二醇二甲醚、乙二醇二乙醚、乙二醇二丙醚、乙二醇二丁醚、乙二醇甲基乙醚、乙二醇甲基丙醚、乙二醇甲基丁醚、乙二醇乙基丙醚、乙二醇乙基丁醚、乙二醇丙基丁醚、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇二丙醚、二乙二醇二丁醚、二乙二醇甲基乙醚、二乙二醇甲基丙醚、二乙二醇甲基丁醚、二乙二醇乙基丙醚、二乙二醇乙基丁醚、二乙二醇丙基丁醚、乙二醇單甲醚乙酸酯、乙二醇單乙醚乙酸酯、乙二醇單丙醚乙酸酯、乙二醇單丁醚乙酸酯、二乙二醇單甲醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單丙醚乙酸酯、二乙二醇單丁醚乙酸酯、丙二醇二甲醚、丙二醇二乙醚、丙二醇二丙醚、丙二醇二丁醚、丙二醇甲基乙醚、丙二醇甲基丙醚、丙二醇甲基丁醚、丙二醇乙基丙醚、丙二醇乙基丁醚、丙二醇丙基丁醚、二丙二醇二甲醚、二丙二醇二乙醚、二丙二醇二丙醚、二丙二醇二丁醚、二丙二醇甲基乙醚、二丙二醇甲基丙醚、二丙二醇甲基丁醚、二丙二醇乙基丙醚、二丙二醇乙基丁醚、二丙二醇丙基丁醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、丙二醇單丙醚乙酸酯、丙二醇單丁醚乙酸酯、二丙二醇單甲醚乙酸酯、二丙二醇單乙醚乙酸酯、二丙二醇單丙醚乙酸酯、二丙二醇單丁醚乙酸酯、3-甲氧基丁醇乙酸酯、乙酸四氫呋喃酯、乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸異丙酯、乙酸丁酯、環己醇乙酸酯、乙二醇二乙酸酯、二乙二醇二乙酸酯、丙二醇二乙酸酯、二丙二醇二乙酸酯、1,3-
丁二醇二乙酸酯等。此等係可1種單獨使用或組合2種以上使用。
於本發明，以對有機半導體材料的溶解性優異方面而言，其中以選自乙二醇二甲醚、二乙二醇二甲醚、乙二醇單乙醚乙酸酯、乙二醇單丙醚乙酸酯、乙二醇單丁醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單丁醚乙酸酯、丙二醇二甲醚、丙二醇甲基乙醚、丙二醇甲基丙醚、丙二醇甲基丁醚、二丙二醇二甲醚、二丙二醇甲基乙醚、二丙二醇甲基丙醚、二丙二醇甲基丁醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、二丙二醇單甲醚乙酸酯、二丙二醇單乙醚乙酸酯、3-甲氧基丁醇乙酸酯、乙酸四氫呋喃酯、及環己醇乙酸酯中之至少1種化合物為較佳。
有機電晶體製造用溶劑或溶劑組成物中(100重量%)的溶劑A之含量(含有2種以上的情況為其總量)以50重量%以上(例如50~100重量%)為較佳，70重量%以上(例如70~100重量%)為特佳。溶劑A的含量低於上述範圍時，則有有機半導體材料的溶解性降低的傾向。
(溶劑B)
本發明之有機電晶體製造用溶劑或溶劑組成物除上述溶劑A以外，亦可併用一般用於電子材料用途的溶劑，即與上述溶劑A相溶之溶劑(=溶劑B)。
作為溶劑B，例如可舉出(單,二,三)伸烷基二醇單烷基醚、C3-6醇、C3-6烷二醇、C3-6烷二醇單烷基醚、C3-6烷二醇烷基醚乙酸酯、C4-6烷二醇二乙酸酯、丙三
醇三乙酸酯、羥基羧酸酯、羥基羧酸二酯、烷氧基羧酸酯、環狀酮、內酯、環狀醚、醯胺類、吡啶類、芳香族烴、芳香族乙酸酯、芳香族醚、胺類等。此等係可1種單獨使用或組合2種以上使用。
作為前述(單,二,三)伸烷基二醇單烷基醚，例如可舉出乙二醇單甲醚、乙二醇單乙醚、乙二醇正丙醚、乙二醇正丁醚、二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇正丙醚、二乙二醇正丁醚、丙二醇單甲醚、丙二醇單乙醚、丙二醇正丙醚、丙二醇正丁醚、二丙二醇單甲醚、二丙二醇單乙醚、二丙二醇正丙醚、二丙二醇正丁醚、三丙二醇單甲醚、三丙二醇正丁醚等。
作為前述C3-6醇，例如可舉出正丙醇、異丙醇、正丁醇、二級丁醇、三級丁醇、正戊醇、正己醇、2-己醇等。
作為前述C3-6烷二醇，例如可舉出1,3-丁二醇、1,4-丁二醇、1,6-己二醇等。
作為前述C3-6烷二醇單烷基醚，例如可舉出3-甲氧基丁醇等。
作為前述C3-6烷二醇烷基醚乙酸酯，例如可舉出乙酸3-甲氧基丁酯等。
作為前述C4-6烷二醇二乙酸酯，例如可舉出1,4-丁二醇二乙酸酯、1,6-己二醇二乙酸酯等。
作為前述羥基羧酸酯，例如可舉出乳酸甲酯、乳酸乙酯等。
作為前述羥基羧酸二酯，例如可舉出乙酸乳
酸甲酯、乙酸乳酸乙酯等。
作為前述烷氧基羧酸酯，例如可舉出甲氧基丙酸甲酯、乙氧基丙酸乙酯等。
作為前述環狀酮，例如可舉出環戊酮、環己酮、4-側氧異佛酮等。
作為前述內酯類，例如可舉出β-丁內酯、γ-丁內酯、ε-己內酯、δ-戊內酯、γ-戊內酯、α-乙醯基-γ-丁內酯等。
作為前述環狀醚，例如可舉出四氫呋喃、四氫呋喃基醇等。
作為前述醯胺類，例如可舉出二甲基甲醯胺等。
作為前述吡啶類，例如可舉出吡啶、甲基吡啶等。
作為前述芳香族烴，例如可舉出甲苯、四氫萘等。
作為前述芳香族乙酸酯，例如可舉出醋酸苯酯等。
作為前述芳香族醚，例如可舉出苯甲醚等。
作為前述胺類，例如可舉出二乙基胺、三乙基胺等。
在本發明，藉由併用上述溶劑A與溶劑B，而可含有高濃度有機半導體材料，且形成塗布性、乾燥性等優異之有機電晶體製造用組成物。
為更提升塗布性，併用1種或2種以上之選自
前述(單,二,三)伸烷基二醇單烷基醚、及烷氧基羧酸酯之溶劑為有效。
為更提升乾燥性，併用1種或2種以上之選自環狀酮、環狀醚、芳香族烴、芳香族乙酸酯、及芳香族醚之溶劑為有效。
併用溶劑A與溶劑B的情況下，其混合比(前者/後者(重量比))為例如95/5~50/50，較佳為95/5~70/30。相較於溶劑A，溶劑B的比例增多時，會有有機半導體材料的溶解性降低之傾向。又，組合使用2種以上之溶劑作為溶劑A時，為其合計量。關於溶劑B亦相同。
由於本發明之有機電晶體製造用溶劑或溶劑組成物含有溶劑A，因此即使較低溫仍具有高有機半導體材料溶解性。例如，在100℃下，相對於有機電晶體製造用溶劑或溶劑組成物100重量份而言，前述式(1)所示之化合物的溶解度為例如0.05重量份以上，較佳為0.06重量份以上，特佳為0.07重量份以上。溶解度的上限為例如0.5重量份，較佳為0.4重量份，特佳為0.3重量份。
(有機半導體材料)
本發明之有機電晶體製造用溶劑或溶劑組成物為有機半導體材料溶解用的溶劑或溶劑組成物。關於前述有機半導體材料係無特別限定，但在本發明中較佳為選自前述式(1)所示之化合物(1)、及具有1種或2種以上之式(2-a)~(2-d)所示重複單位的化合物(2)中之至少1種化合物。此等係可1種單獨使用或組合2種以上使用。
前述式(1)中，Ar為從環式化合物去除2個氫
原子的基，前述環式化合物為式(A-1)~式(A-5)中任一者所示之化合物。R’、R”係相同或相異，表示氫原子、亦可有取代基之C1-18烷基、亦可有取代基之苯基、亦可有取代基之萘基、或亦可有取代基之苯硫基。
作為前述C1-18(=碳數1~18)烷基，例如可舉出甲基、乙基、丙基、丁基、戊基、己基、辛基、乙基己基、癸基、十二烷基、肉豆蔻基、己基癸基、辛基癸基等之直鏈狀或分枝鏈狀烷基。作為C1-18烷基亦可具有的取代基，例如可舉出苯基、萘基等之碳數6~10的芳基。作為苯基、萘基、苯硫基亦可具有的取代基，例如可舉出甲基、乙基、正丙基、異丙基、正丁基、二級丁基、三級丁基等之碳數1~12的直鏈狀或分枝鏈狀的烷基。
作為式(1)所示之化合物(1)，其中，由可得晶粒大之有機電晶體方面而言，以下述式(1-1)所示之化合物為較佳。
前述式(2-b)中、R表示亦可有取代基之C1-24烷基、亦可有取代基之苯基、亦可有取代基之萘基、或亦可有取代基之苯硫基。
作為前述C1-24(=碳數1~24)烷基，例如可舉出甲基、乙基、丙基、丁基、戊基、己基、辛基、乙基己基、癸基、十二烷基、肉豆蔻基、己基癸基、辛基癸基、二十烷基、二十四烷基等之直鏈狀或分枝鏈狀的烷
基。
作為R中的C1-24烷基、苯基、萘基、及苯硫基亦可具有的取代基，可舉出與上述R’、R”同樣的例子。
關於前述化合物(2)中的重複單位數(聚合度)，較佳為例如2~5000左右。又，具有2種以上重複單位的情況，各重複單位係可無規鍵結，亦可規則地鍵結。
作為化合物(2)，其中，就可得晶粒大的有機電晶體方面而言，以具有下述式(2-1)~(2-3)所示之重複單位之化合物為較佳。式中，k、l、m表示括弧內所示之重複單位的數目，為2~5000之整數。
[有機電晶體製造用組成物]
本發明之有機電晶體製造用組成物之特徵為包含上述有機半導體材料與上述有機電晶體製造用溶劑或溶劑組成物。
本發明之有機電晶體製造用組成物係可藉由如下方式調製：例如混合上述有機半導體材料與上述有機電晶體製造用溶劑或溶劑組成物，在氮氣環境下、遮光條件下、以70~150℃左右的溫度加熱0.1~10小時左右。
本發明之有機電晶體製造用組成物(100重量%)中的有機半導體材料(尤其是前述式(1)所示之化合物)的含量(含有2種以上時為其總量)為例如0.05重量%以上，較佳為0.06重量%以上，特佳為0.07重量%以上。上限為例如0.5重量%，較佳為0.4重量%，特佳為0.3重量%。
本發明之有機電晶體製造用組成物(100重量%)中有機電晶體製造用溶劑或溶劑組成物的含量(含有2種以上時為其總量)為例如99.99重量%以下。其下限為例如92.00重量%，較佳為95.00重量%，特佳為95.50重量%，上限較佳為99.98重量%，特佳為99.96重量%。
亦即，就可促進因有機半導體材料之自組織化作用所致之結晶化方面來看，本發明之有機電晶體製造用組成物中所含的有機電晶體製造用溶劑或溶劑組成物量(含有2種以上時為其總量)相對於本發明之有機電晶體製造用組成物中所含的有機半導體材料量(尤其是前述式(1)所示之化合物的量、含有2種以上時為其總量)而言，較佳為例如200倍(重量)以上，更佳為250倍(重量)
以上，特佳為333倍(重量)以上。上限為例如2000倍(重量)，較佳為1667倍(重量)，特佳為1429倍(重量)。
本發明之有機電晶體製造用組成物除上述有機半導體材料與上述有機電晶體製造用溶劑或溶劑組成物以外，視需要可適當摻合一般的有機電晶體製造用組成物所含的其他成分(例如，環氧樹脂、丙烯酸樹脂、纖維素樹脂、及丁醛樹脂等之樹脂的原料)。
本發明之有機電晶體製造用組成物即使在較低溫下，仍可高濃度地溶解有機半導體材料。因此，在耐熱性較玻璃基板低但對於衝擊強、輕量且可撓的塑膠基板亦可直接形成有機電晶體；並且，能夠形成對於衝擊強、輕量且可撓之顯示器或電腦機器。又，本發明之有機電晶體製造用組成物由於含有本發明之有機電晶體製造用溶劑或溶劑組成物，所以塗布在基板上時，有機半導體材料藉由自組織化作用而結晶化，可得具有高結晶性之有機電晶體。進而能夠以印刷法、旋轉塗布法等之濕式製程之簡便方法容易地形成有機電晶體，可大幅削減成本。
以下藉由實施例更具體地說明本發明，但本發明係不因此等實施例而限定。
實施例1
使用二萘[2,3-b：2’,3’-f]噻吩并[3,2-b]噻吩(DNTT：式(1-1)所示之化合物)(和光純藥工業(股)製)作為有機半導體材料，使用乙酸四氫呋喃酯(THFFA：DAICEL(股)
製)作為有機電晶體製造用溶劑。
在20℃環境下，在有機電晶體製造用溶劑中將有機半導體材料分散成使其濃度為0.08重量%~0.15重量%。然後，在氮氣環境、遮光條件下，以100℃加熱6小時左右，獲得有機電晶體製造用組成物。以目視確認所得的有機電晶體製造用組成物中之不溶物，依照下述基準評估有機半導體材料之溶解性。
評估基準
無法確認不溶物之情形：○(溶解)
確認到不溶物之情形：×(不溶解)
實施例2~9、比較例1
除了使用表1所示之有機電晶體製造用溶劑以外，與實施例1同樣地進行，而調製有機電晶體製造用組成物，並評估有機半導體材料的溶解性。
THFFA：乙酸四氫呋喃酯(DAICEL(股)製)
EDGAC：二乙二醇單乙醚乙酸酯(DAICEL(股)製)
DPMA：二丙二醇單甲醚乙酸酯(DAICEL(股)製)
PMNP：丙二醇甲基正丙醚(DAICEL(股)製)
PMNB：丙二醇甲基正丁醚(DAICEL(股)製)
DMM：二丙二醇二甲醚(DAICEL(股)製)
DPMNP：二丙二醇甲基正丙醚(DAICEL(股)製)
DPMNB：二丙二醇甲基正丁醚(DAICEL(股)製)
MBA：3-甲氧基丁醇乙酸酯(DAICEL(股)製)
o-DCB：1,2-二氯苯(東京化成工業(股)製)
實施例10
使用聚(3-己基噻吩-2,5-二基)(立體規則，regioregular)(P3HT：式(2-1)所示之化合物)作為有機半導體材料，使用環己醇乙酸酯作為有機電晶體製造用溶劑。
在20℃環境下，將有機半導體材料分散在有機電晶體製造用溶劑中，使其濃度成為0.50重量%。然後，在氮氣環境、遮光條件下，以100℃加熱約6小時左右，獲得有機電晶體製造用組成物。
於所得有機電晶體製造用組成物無法確認到不溶物。
由上述實施例1~9可知：相比於迄今所使用的1,2-二氯苯(o-DCB)，本發明之有機電晶體製造用溶劑係對有機半導體材料(式(1)所示之化合物，尤其是二萘[2,3-b：2’,3’-f]噻吩并[3,2-b]噻吩：DNTT)的溶解性優異。
由上述實施例10可知：本發明之有機電晶體製造用溶劑即使對聚(3-己基噻吩-2,5-二基)(立體規則)(P3HT：式(2-1)所示之化合物)仍具有優異之溶解性。
又，1,2-二氯苯(o-DCB)因為具有毒性而難以處理，但本發明之有機電晶體製造用溶劑其處理性亦為優異。
本發明之有機電晶體製造用溶劑或溶劑組成物即使在較低溫下仍具有高有機半導體材料溶解性。因此，在耐熱性較玻璃基板低但對於衝擊強、輕量且可撓的塑膠基板等上，亦可直接形成有機電晶體；並且，能夠形成對於衝擊強、輕量且可撓的顯示器或電腦機器。又，能以印刷法、旋轉塗布法等之濕式製程的簡便方法容易地製造有機電晶體，可大幅削減成本。
而且，本發明之有機電晶體製造用組成物塗布在基板上時，有機半導體材料係藉由自組織化作用而結晶化，可得具有高結晶性之有機電晶體。
Claims (3)
- 一種有機電晶體製造用組成物，其係用於製造有機電晶體之組成物，其包含下述式(A)所示之溶劑A、
- 如請求項1之有機電晶體製造用組成物，其中溶劑A包含選自乙二醇二甲醚、二乙二醇二甲醚、乙二醇單乙醚乙酸酯、乙二醇單丙醚乙酸酯、乙二醇單丁醚乙酸酯、二乙二醇單乙醚乙酸酯、二乙二醇單丁醚乙酸酯、丙二醇二甲醚、丙二醇甲基乙醚、丙二醇甲基丙醚、丙二醇甲基丁醚、二丙二醇二甲醚、二丙二醇甲基乙醚、二丙二醇甲基丙醚、二丙二醇甲基丁醚、丙二醇單甲醚乙酸酯、丙二醇單乙醚乙酸酯、二丙二醇單甲醚乙酸酯、二丙二醇單乙醚乙酸酯、3-甲氧基丁醇 乙酸酯、乙酸四氫呋喃酯、及環己醇乙酸酯中之至少1種。
- 一種溶劑或溶劑組成物在有機電晶體製造中用於溶解有機半導體材料之用途，其中該溶劑或溶劑組成物包含選自下列中之至少一種溶劑：二乙二醇單丁醚乙酸酯、丙二醇二甲醚、丙二醇甲基乙醚、丙二醇甲基丙醚、丙二醇甲基丁醚、二丙二醇甲基乙醚、二丙二醇甲基丙醚、二丙二醇甲基丁醚、二丙二醇單甲醚乙酸酯、二丙二醇單乙醚乙酸酯、3-甲氧基丁醇乙酸酯、乙酸四氫呋喃酯、及環己醇乙酸酯。
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1976084A (zh) * | 2005-11-29 | 2007-06-06 | Lg.菲利浦Lcd株式会社 | 有机半导体薄膜晶体管及其制造方法 |
| JP2008124085A (ja) * | 2006-11-08 | 2008-05-29 | Canon Inc | 有機薄膜トランジスタ |
| JP2011195566A (ja) * | 2010-02-25 | 2011-10-06 | Adeka Corp | 新規ビベンゾ［ｂ］フラン化合物、並びに該化合物を含有してなる有機半導体材料及び有機半導体素子 |
| WO2011151460A1 (en) * | 2010-06-04 | 2011-12-08 | Plastic Logic Limited | Production of electronic switching devices |
| TW201247676A (en) * | 2011-02-25 | 2012-12-01 | Univ Hiroshima | Method for producing dianthra [2,3-b:2',3'-f] thieno [3,2-b] thiophen and application thereof |
Family Cites Families (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6166172A (en) * | 1999-02-10 | 2000-12-26 | Carnegie Mellon University | Method of forming poly-(3-substituted) thiophenes |
| JP2003211070A (ja) * | 2002-01-21 | 2003-07-29 | Toshiba Corp | 塗膜の形成方法、半導体装置の製造方法および塗布液 |
| US6656763B1 (en) * | 2003-03-10 | 2003-12-02 | Advanced Micro Devices, Inc. | Spin on polymers for organic memory devices |
| DE102004007777A1 (de) * | 2004-02-18 | 2005-09-08 | Covion Organic Semiconductors Gmbh | Lösungen organischer Halbleiter |
| DE102004023276A1 (de) * | 2004-05-11 | 2005-12-01 | Covion Organic Semiconductors Gmbh | Lösungen organischer Halbleiter |
| US7371906B2 (en) * | 2004-08-24 | 2008-05-13 | Eastman Kodak Company | Process for photo-oxidative stability improvements |
| WO2006132128A1 (ja) * | 2005-06-06 | 2006-12-14 | Sharp Kabushiki Kaisha | 正孔注入輸送層用塗液、正孔注入輸送層の製造方法、有機エレクトロルミネセンス素子、及び、その製造方法 |
| GB2441701B (en) * | 2005-06-24 | 2009-01-14 | Konica Minolta Holdings Inc | Method for forming organic semiconductor film, organic semiconductor film, and organic thin film transistor |
| US7960717B2 (en) * | 2005-12-29 | 2011-06-14 | E.I. Du Pont De Nemours And Company | Electronic device and process for forming same |
| KR101215758B1 (ko) * | 2006-01-17 | 2012-12-26 | 삼성전자주식회사 | Ｎｐｎ-타입의 저분자 방향족 고리 화합물, 이를 이용한유기 반도체 및 전자 소자 |
| KR101304697B1 (ko) * | 2006-06-07 | 2013-09-06 | 삼성전자주식회사 | 적층 유도 화합물을 사용한 유기 반도체 소재, 이를포함하는 조성물, 이를 이용한 유기 반도체 박막 및 유기전자 소자 |
| KR20080100982A (ko) * | 2007-05-15 | 2008-11-21 | 삼성전자주식회사 | 헤테로아센 화합물, 이를 포함하는 유기 박막 및 상기박막을 포함하는 전자 소자 |
| US7932128B2 (en) * | 2007-06-29 | 2011-04-26 | International Business Machines Corporation | Polymeric material, method of forming the polymeric material, and method of forming a thin film using the polymeric material |
| KR101475520B1 (ko) * | 2008-01-14 | 2014-12-23 | 삼성전자주식회사 | 잉크젯 프린트용 양자점 잉크 조성물 및 그를 이용한전자소자 |
| US8598569B2 (en) * | 2008-04-30 | 2013-12-03 | International Business Machines Corporation | Pentacene-carbon nanotube composite, method of forming the composite, and semiconductor device including the composite |
| JP5314814B2 (ja) | 2008-06-13 | 2013-10-16 | ウシオケミックス株式会社 | チエノチオフェン骨格を特徴とする有機半導体材料 |
| JP2010028105A (ja) * | 2008-06-20 | 2010-02-04 | Semiconductor Energy Lab Co Ltd | 記憶素子及び記憶素子の作製方法 |
| JPWO2010032796A1 (ja) * | 2008-09-19 | 2012-02-16 | 日産化学工業株式会社 | サイドウォール形成用組成物 |
| WO2010098372A1 (ja) * | 2009-02-27 | 2010-09-02 | 国立大学法人広島大学 | 電界効果トランジスタ |
| KR101763669B1 (ko) * | 2009-03-31 | 2017-08-01 | 디아이씨 가부시끼가이샤 | 유기 반도체 잉크 조성물 및 이를 사용한 유기 반도체 패턴 형성 방법 |
| JP2011003852A (ja) | 2009-06-22 | 2011-01-06 | Asahi Kasei Corp | 硫黄原子を含有する縮合多環芳香族化合物のシート状結晶が基板上に積層された有機半導体薄膜、及びその製法 |
| JP2011148743A (ja) | 2010-01-22 | 2011-08-04 | Teijin Ltd | 縮合多環芳香族化合物の精製及び製造方法 |
| KR101604513B1 (ko) * | 2009-08-28 | 2016-03-17 | 데이진 가부시키가이샤 | 신규한 부가 화합물, 축합 다고리 방향족 화합물의 정제 및 제조 방법, 유기 반도체막 형성용 용액, 및 신규한 α-디케톤 화합물 |
| JP5664897B2 (ja) | 2009-09-11 | 2015-02-04 | 株式会社リコー | ベンゼン環を有するπ電子共役系化合物を含有する膜状体の製法、及び該π電子共役系化合物の製法。 |
| JP2011195568A (ja) * | 2010-02-23 | 2011-10-06 | Asahi Kasei Corp | 多糖類と細胞接着ペプチドを含む多糖類ゲル組成物 |
| JP2012092187A (ja) * | 2010-10-26 | 2012-05-17 | Daicel Corp | 印刷用溶剤組成物 |
-
2013
- 2013-12-02 DE DE112013005942.8T patent/DE112013005942T5/de not_active Ceased
- 2013-12-02 JP JP2014551987A patent/JP6228129B2/ja not_active Expired - Fee Related
- 2013-12-02 CN CN201380064733.5A patent/CN104854719B/zh active Active
- 2013-12-02 US US14/651,312 patent/US20150333269A1/en not_active Abandoned
- 2013-12-02 WO PCT/JP2013/082369 patent/WO2014091960A1/ja active Application Filing
- 2013-12-02 KR KR1020157014848A patent/KR102118354B1/ko active IP Right Grant
- 2013-12-11 TW TW102145490A patent/TWI602798B/zh not_active IP Right Cessation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1976084A (zh) * | 2005-11-29 | 2007-06-06 | Lg.菲利浦Lcd株式会社 | 有机半导体薄膜晶体管及其制造方法 |
| JP2008124085A (ja) * | 2006-11-08 | 2008-05-29 | Canon Inc | 有機薄膜トランジスタ |
| JP2011195566A (ja) * | 2010-02-25 | 2011-10-06 | Adeka Corp | 新規ビベンゾ［ｂ］フラン化合物、並びに該化合物を含有してなる有機半導体材料及び有機半導体素子 |
| WO2011151460A1 (en) * | 2010-06-04 | 2011-12-08 | Plastic Logic Limited | Production of electronic switching devices |
| TW201247676A (en) * | 2011-02-25 | 2012-12-01 | Univ Hiroshima | Method for producing dianthra [2,3-b:2',3'-f] thieno [3,2-b] thiophen and application thereof |
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|---|---|
| CN104854719A (zh) | 2015-08-19 |
| KR20150095647A (ko) | 2015-08-21 |
| JP6228129B2 (ja) | 2017-11-08 |
| CN104854719B (zh) | 2018-11-13 |
| US20150333269A1 (en) | 2015-11-19 |
| DE112013005942T5 (de) | 2015-09-24 |
| WO2014091960A1 (ja) | 2014-06-19 |
| KR102118354B1 (ko) | 2020-06-03 |
| TW201434797A (zh) | 2014-09-16 |
| JPWO2014091960A1 (ja) | 2017-01-05 |
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