JP2011524908A - 溶液処理可能な有機半導体 - Google Patents
溶液処理可能な有機半導体 Download PDFInfo
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- JP2011524908A JP2011524908A JP2011514647A JP2011514647A JP2011524908A JP 2011524908 A JP2011524908 A JP 2011524908A JP 2011514647 A JP2011514647 A JP 2011514647A JP 2011514647 A JP2011514647 A JP 2011514647A JP 2011524908 A JP2011524908 A JP 2011524908A
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- Prior art keywords
- semiconductor
- layer
- alkyl
- formula
- alkenyl
- Prior art date
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 198
- 239000000203 mixture Substances 0.000 claims abstract description 82
- 150000003384 small molecules Chemical class 0.000 claims abstract description 40
- -1 silylethynyl groups Chemical group 0.000 claims abstract description 35
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 229920000642 polymer Polymers 0.000 claims description 42
- 239000010409 thin film Substances 0.000 claims description 37
- 239000003960 organic solvent Substances 0.000 claims description 35
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 13
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 3
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 3
- 239000011118 polyvinyl acetate Substances 0.000 claims description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
- 229920002981 polyvinylidene fluoride Polymers 0.000 claims description 3
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 2
- 239000004373 Pullulan Substances 0.000 claims description 2
- 229920001218 Pullulan Polymers 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 229920003251 poly(α-methylstyrene) Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- 235000019423 pullulan Nutrition 0.000 claims description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 claims 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 229920000915 polyvinyl chloride Polymers 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 36
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract description 6
- 125000005577 anthracene group Chemical group 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 130
- 125000004432 carbon atom Chemical group C* 0.000 description 50
- 239000000758 substrate Substances 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 125000004122 cyclic group Chemical group 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 239000002335 surface treatment layer Substances 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000011247 coating layer Substances 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 229920001940 conductive polymer Polymers 0.000 description 5
- 150000003254 radicals Chemical group 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 238000003491 array Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- OCKPCBLVNKHBMX-UHFFFAOYSA-N butylbenzene Chemical compound CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 4
- 125000002837 carbocyclic group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000002390 rotary evaporation Methods 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- SKRWFPLZQAAQSU-UHFFFAOYSA-N stibanylidynetin;hydrate Chemical compound O.[Sn].[Sb] SKRWFPLZQAAQSU-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- JUFYHUWBLXKCJM-UHFFFAOYSA-N 2,6-dibromoanthracene-9,10-dione Chemical compound BrC1=CC=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 JUFYHUWBLXKCJM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZLWDQLLYCNFCNH-UHFFFAOYSA-N 2-[2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-10-[2-tri(propan-2-yl)silylethynyl]anthracen-9-yl]ethynyl-tri(propan-2-yl)silane Chemical compound C1=C2C(C#C[Si](C(C)C)(C(C)C)C(C)C)=C3C=CC(B4OC(C)(C)C(C)(C)O4)=CC3=C(C#C[Si](C(C)C)(C(C)C)C(C)C)C2=CC=C1B1OC(C)(C)C(C)(C)O1 ZLWDQLLYCNFCNH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 230000032683 aging Effects 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 3
- 239000003989 dielectric material Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
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- AYFJBMBVXWNYLT-UHFFFAOYSA-N 2-bromo-6-methoxynaphthalene Chemical compound C1=C(Br)C=CC2=CC(OC)=CC=C21 AYFJBMBVXWNYLT-UHFFFAOYSA-N 0.000 description 2
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- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 2
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
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- 238000000206 photolithography Methods 0.000 description 2
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- 239000002356 single layer Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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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
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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]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/464—Lateral top-gate IGFETs comprising only a single gate
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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]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Thin Film Transistor (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7400208P | 2008-06-19 | 2008-06-19 | |
| US61/074,002 | 2008-06-19 | ||
| PCT/US2009/041904 WO2009154877A1 (en) | 2008-06-19 | 2009-04-28 | Solution processable organic semiconductors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011524908A true JP2011524908A (ja) | 2011-09-08 |
| JP2011524908A5 JP2011524908A5 (enExample) | 2012-06-14 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011514647A Pending JP2011524908A (ja) | 2008-06-19 | 2009-04-28 | 溶液処理可能な有機半導体 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20110079775A1 (enExample) |
| EP (1) | EP2318420A1 (enExample) |
| JP (1) | JP2011524908A (enExample) |
| CN (1) | CN102119164A (enExample) |
| WO (1) | WO2009154877A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101926017B (zh) * | 2007-12-17 | 2013-09-25 | 3M创新有限公司 | 基于蒽的可溶液加工的有机半导体 |
| EP2304821B1 (en) * | 2008-06-11 | 2012-06-27 | 3M Innovative Properties Company | Mixed solvent systems for deposition of organic semiconductors |
| KR20100075100A (ko) * | 2008-12-24 | 2010-07-02 | 서울대학교산학협력단 | 잉크젯 프린팅 방법을 이용한 유기 전계효과 트랜지스터의 활성 채널층 형성방법 및 이를 이용한 유기 전계효과 트랜지스터 |
| WO2012112893A1 (en) * | 2011-02-19 | 2012-08-23 | United Arab Emirates University | Semiconducting polymer |
| WO2012123058A1 (en) * | 2011-03-11 | 2012-09-20 | Merck Patent Gmbh | Dinaphtho[2,3-a:2',3'-h]phenazines and their use as organic semiconductors |
| CN102637825B (zh) * | 2012-04-24 | 2015-03-04 | 中国科学院苏州纳米技术与纳米仿生研究所 | 一种有机薄膜晶体管的制备方法 |
| CN107628924A (zh) * | 2017-09-25 | 2018-01-26 | 中国科学院化学研究所 | 一种蒽类衍生物及其制备方法与应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006050496A1 (en) * | 2004-11-02 | 2006-05-11 | E.I. Dupont De Nemours And Company | Substituted anthracenes and electronic devices containing the substituted anthracenes |
| JP2007088115A (ja) * | 2005-09-21 | 2007-04-05 | Konica Minolta Holdings Inc | 有機半導体材料，有機半導体膜，有機半導体デバイス及び有機薄膜トランジスタ |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6433359B1 (en) * | 2001-09-06 | 2002-08-13 | 3M Innovative Properties Company | Surface modifying layers for organic thin film transistors |
| US6998068B2 (en) * | 2003-08-15 | 2006-02-14 | 3M Innovative Properties Company | Acene-thiophene semiconductors |
| US6617609B2 (en) * | 2001-11-05 | 2003-09-09 | 3M Innovative Properties Company | Organic thin film transistor with siloxane polymer interface |
| US6946676B2 (en) * | 2001-11-05 | 2005-09-20 | 3M Innovative Properties Company | Organic thin film transistor with polymeric interface |
| US20030227014A1 (en) * | 2002-06-11 | 2003-12-11 | Xerox Corporation. | Process for forming semiconductor layer of micro-and nano-electronic devices |
| EP1682605B1 (en) * | 2003-10-28 | 2012-06-20 | Basf Se | Novel diketopyrrolopyrrole polymers |
| JP5089986B2 (ja) * | 2003-11-28 | 2012-12-05 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 有機半導体層およびその改善 |
| WO2006003842A1 (ja) * | 2004-07-02 | 2006-01-12 | Chisso Corporation | 発光材料およびこれを用いた有機電界発光素子 |
| KR101068372B1 (ko) * | 2005-07-05 | 2011-09-28 | 히다치 가세고교 가부시끼가이샤 | 감광성 접착제, 및 이것을 이용하여 얻어지는 접착 필름, 접착 시트, 접착제층 부착 반도체 웨이퍼, 반도체장치 및 전자부품 |
| KR101215758B1 (ko) * | 2006-01-17 | 2012-12-26 | 삼성전자주식회사 | Ｎｐｎ-타입의 저분자 방향족 고리 화합물, 이를 이용한유기 반도체 및 전자 소자 |
| US7667230B2 (en) * | 2006-03-31 | 2010-02-23 | 3M Innovative Properties Company | Electronic devices containing acene-thiophene copolymers |
| US7495251B2 (en) * | 2006-04-21 | 2009-02-24 | 3M Innovative Properties Company | Electronic devices containing acene-thiophene copolymers with silylethynyl groups |
| KR101059408B1 (ko) * | 2006-08-03 | 2011-08-29 | 아사히 가세이 일렉트로닉스 가부시끼가이샤 | 감광성 수지 조성물 및 적층체 |
| EP2132213B1 (en) * | 2007-03-07 | 2013-05-15 | University of Kentucky Research Foundation | Silylethynylated heteroacenes and electronic devices made therewith |
| WO2008120839A1 (en) * | 2007-03-30 | 2008-10-09 | Gyeongsang National University Industrial And Academic Collaboration Foundation | Novel organic semiconductor compound, and organic thin film transistor using the same |
| EP2134725B1 (en) * | 2007-04-19 | 2012-07-04 | Merck Patent GmbH | Process for preparing substituted pentacenes |
| CN101679150B (zh) * | 2007-05-17 | 2013-05-15 | Lg化学株式会社 | 蒽衍生物和使用该蒽衍生物的有机电子器件 |
| KR101554751B1 (ko) * | 2007-06-01 | 2015-09-22 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 녹색 발광 재료 |
| CN101926017B (zh) * | 2007-12-17 | 2013-09-25 | 3M创新有限公司 | 基于蒽的可溶液加工的有机半导体 |
-
2009
- 2009-04-28 CN CN2009801310799A patent/CN102119164A/zh active Pending
- 2009-04-28 WO PCT/US2009/041904 patent/WO2009154877A1/en not_active Ceased
- 2009-04-28 JP JP2011514647A patent/JP2011524908A/ja active Pending
- 2009-04-28 EP EP09767189A patent/EP2318420A1/en not_active Withdrawn
- 2009-04-28 US US12/994,898 patent/US20110079775A1/en not_active Abandoned
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006050496A1 (en) * | 2004-11-02 | 2006-05-11 | E.I. Dupont De Nemours And Company | Substituted anthracenes and electronic devices containing the substituted anthracenes |
| JP2007088115A (ja) * | 2005-09-21 | 2007-04-05 | Konica Minolta Holdings Inc | 有機半導体材料，有機半導体膜，有機半導体デバイス及び有機薄膜トランジスタ |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2318420A1 (en) | 2011-05-11 |
| WO2009154877A1 (en) | 2009-12-23 |
| CN102119164A (zh) | 2011-07-06 |
| US20110079775A1 (en) | 2011-04-07 |
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