CN101176217B - 作为有机半导体的氮杂二萘嵌苯 - Google Patents
作为有机半导体的氮杂二萘嵌苯 Download PDFInfo
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- CN101176217B CN101176217B CN200680016379.9A CN200680016379A CN101176217B CN 101176217 B CN101176217 B CN 101176217B CN 200680016379 A CN200680016379 A CN 200680016379A CN 101176217 B CN101176217 B CN 101176217B
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- Prior art keywords
- replace
- alkyl
- replacement
- aryl
- replaces
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 49
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 13
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 9
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 150000001875 compounds Chemical group 0.000 claims description 51
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000003118 aryl group Chemical group 0.000 claims description 32
- -1 tetralyl Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000000304 alkynyl group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 239000002243 precursor Substances 0.000 claims description 21
- 230000005669 field effect Effects 0.000 claims description 17
- 150000001721 carbon Chemical group 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005493 quinolyl group Chemical group 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 150000003949 imides Chemical group 0.000 claims description 2
- 150000002596 lactones Chemical class 0.000 claims description 2
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000005561 phenanthryl group Chemical group 0.000 claims 2
- 125000001725 pyrenyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 5
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 5
- 125000004426 substituted alkynyl group Chemical group 0.000 abstract 5
- 125000003107 substituted aryl group Chemical group 0.000 abstract 5
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 abstract 1
- HDMSISRTSCLVOX-UHFFFAOYSA-N azaperylene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=NC=CC3=C1 HDMSISRTSCLVOX-UHFFFAOYSA-N 0.000 abstract 1
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- 239000010409 thin film Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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- 239000002184 metal Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 238000000059 patterning Methods 0.000 description 4
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VEMPRDIRDOOADO-UHFFFAOYSA-N 3,4-diazapentacyclo[9.7.1.12,6.015,19.010,20]icosa-1(18),2(20),3,5,7,9,11,13,15(19),16-decaene Chemical group C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=NN=CC3=C1 VEMPRDIRDOOADO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
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- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
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- 238000000206 photolithography Methods 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FQMPGJJOTKXCJR-UHFFFAOYSA-N C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12.N1C=CC=CC=C1 Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12.N1C=CC=CC=C1 FQMPGJJOTKXCJR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
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- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 2
- 229910002113 barium titanate Inorganic materials 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
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- 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 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 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 2
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- WOIHABYNKOEWFG-UHFFFAOYSA-N [Sr].[Ba] Chemical compound [Sr].[Ba] WOIHABYNKOEWFG-UHFFFAOYSA-N 0.000 description 1
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- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
- C09B5/022—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position not provided for in one of the sub groups C09B5/04 - C09B5/20
- C09B5/028—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position not provided for in one of the sub groups C09B5/04 - C09B5/20 only N-containing hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- 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]
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- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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| EP2251920A1 (en) * | 2009-05-12 | 2010-11-17 | Università Degli Studi Di Milano - Bicocca | Method of manufacturing electrical contacts on organic semiconductors |
| JP5811542B2 (ja) * | 2010-06-15 | 2015-11-11 | 株式会社リコー | ジチエノベンゾジチオフェン誘導体からなる有機半導体材料前駆体、インク、絶縁部材、電荷輸送性部材の製造方法 |
| TW201339138A (zh) * | 2012-01-20 | 2013-10-01 | Univ Southern California | 作為用於有機電子裝置之新穎ｎ－型材料之氮雜－并苯之合成 |
| JP6555667B2 (ja) * | 2016-06-27 | 2019-08-07 | 富士フイルム株式会社 | 有機薄膜トランジスタ、有機半導体膜、化合物、有機薄膜トランジスタ用組成物及び有機薄膜トランジスタの製造方法 |
| JP7086391B2 (ja) * | 2017-09-25 | 2022-06-20 | 国立研究開発法人理化学研究所 | キノイド型π共役系近赤外有機色素化合物 |
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| US7026643B2 (en) * | 2001-05-04 | 2006-04-11 | International Business Machines Corporation | Organic n-channel semiconductor device of N,N' 3,4,9,10 perylene tetracarboxylic diimide |
| US6690029B1 (en) * | 2001-08-24 | 2004-02-10 | University Of Kentucky Research Foundation | Substituted pentacenes and electronic devices made with substituted pentacenes |
| JP4132761B2 (ja) * | 2001-09-21 | 2008-08-13 | 独立行政法人科学技術振興機構 | 電荷注入制御型有機トランジスターデバイス |
| DE60212668T2 (de) * | 2001-09-27 | 2007-06-21 | 3M Innovative Properties Co., St. Paul | Halbleiter auf basis von substituiertem pentacen |
| US7125989B2 (en) * | 2001-11-26 | 2006-10-24 | International Business Machines Corporation | Hetero diels-alder adducts of pentacene as soluble precursors of pentacene |
| TWI314947B (en) * | 2002-04-24 | 2009-09-21 | Eastman Kodak Compan | Organic light emitting diode devices with improved operational stability |
| JP4486316B2 (ja) * | 2003-04-28 | 2010-06-23 | 大日本印刷株式会社 | 機能性素子の製造方法およびその製造装置 |
-
2006
- 2006-05-03 WO PCT/EP2006/062007 patent/WO2006120143A1/en not_active Ceased
- 2006-05-03 CN CN200680016379.9A patent/CN101176217B/zh not_active Expired - Fee Related
- 2006-05-03 US US11/919,605 patent/US7723521B2/en not_active Expired - Fee Related
- 2006-05-03 DE DE602006017060T patent/DE602006017060D1/de active Active
- 2006-05-03 AT AT06754974T patent/ATE482477T1/de not_active IP Right Cessation
- 2006-05-03 EP EP06754974A patent/EP1880428B1/en not_active Not-in-force
- 2006-05-03 JP JP2008510543A patent/JP5522936B2/ja not_active Expired - Fee Related
- 2006-05-11 TW TW095116755A patent/TWI404787B/zh not_active IP Right Cessation
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2012
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Also Published As
| Publication number | Publication date |
|---|---|
| JP5580848B2 (ja) | 2014-08-27 |
| EP1880428B1 (en) | 2010-09-22 |
| TW200704747A (en) | 2007-02-01 |
| US20090101890A1 (en) | 2009-04-23 |
| DE602006017060D1 (de) | 2010-11-04 |
| CN101176217A (zh) | 2008-05-07 |
| ATE482477T1 (de) | 2010-10-15 |
| JP5522936B2 (ja) | 2014-06-18 |
| WO2006120143A1 (en) | 2006-11-16 |
| JP2008541440A (ja) | 2008-11-20 |
| EP1880428A1 (en) | 2008-01-23 |
| JP2012176967A (ja) | 2012-09-13 |
| US7723521B2 (en) | 2010-05-25 |
| TWI404787B (zh) | 2013-08-11 |
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