DE60307333T2 - Polythiophene und damit hergestellte Vorrichtungen - Google Patents
Polythiophene und damit hergestellte Vorrichtungen Download PDFInfo
- Publication number
- DE60307333T2 DE60307333T2 DE60307333T DE60307333T DE60307333T2 DE 60307333 T2 DE60307333 T2 DE 60307333T2 DE 60307333 T DE60307333 T DE 60307333T DE 60307333 T DE60307333 T DE 60307333T DE 60307333 T2 DE60307333 T2 DE 60307333T2
- Authority
- DE
- Germany
- Prior art keywords
- polythiophene
- polythiophenes
- bis
- devices
- layer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 229920000123 polythiophene Polymers 0.000 title claims description 100
- -1 oligoarylene Chemical group 0.000 claims description 22
- 125000000732 arylene group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 125000005556 thienylene group Chemical group 0.000 claims description 10
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 9
- 125000005567 fluorenylene group Chemical group 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
- 229920000570 polyether Polymers 0.000 claims description 8
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000005560 phenanthrenylene group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 45
- 239000004065 semiconductor Substances 0.000 description 29
- 239000010409 thin film Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
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- 239000000203 mixture Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- 238000004528 spin coating Methods 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
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- 229910052710 silicon Inorganic materials 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 229930192474 thiophene Natural products 0.000 description 7
- 239000011701 zinc Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 230000001590 oxidative effect Effects 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
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 5
- YNZKCHBXBASBJT-UHFFFAOYSA-N 3,4-dioctyl-2,5-dithiophen-2-ylthiophene Chemical compound CCCCCCCCC=1C(CCCCCCCC)=C(C=2SC=CC=2)SC=1C1=CC=CS1 YNZKCHBXBASBJT-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
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- 239000000976 ink Substances 0.000 description 5
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- 239000000725 suspension Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- BNXJIUWYGDXAOL-UHFFFAOYSA-N 2,5-bis(5-bromothiophen-2-yl)-3,4-dioctylthiophene Chemical compound CCCCCCCCC=1C(CCCCCCCC)=C(C=2SC(Br)=CC=2)SC=1C1=CC=C(Br)S1 BNXJIUWYGDXAOL-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 239000011521 glass Substances 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
- 125000005549 heteroarylene group Chemical group 0.000 description 4
- 238000004377 microelectronic Methods 0.000 description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052814 silicon oxide Inorganic materials 0.000 description 4
- UBKCMQCDHVYUAF-UHFFFAOYSA-N (2,2-dichloro-3-diphenylphosphanylpropyl)-diphenylphosphane Chemical compound ClC(CP(C1=CC=CC=C1)C1=CC=CC=C1)(CP(C1=CC=CC=C1)C1=CC=CC=C1)Cl UBKCMQCDHVYUAF-UHFFFAOYSA-N 0.000 description 3
- HTYVENFRAWYMAH-UHFFFAOYSA-N 2,5-dibromo-3,4-dioctylthiophene Chemical compound CCCCCCCCC1=C(Br)SC(Br)=C1CCCCCCCC HTYVENFRAWYMAH-UHFFFAOYSA-N 0.000 description 3
- WAOUDPOLPWAIGN-UHFFFAOYSA-N 3,4-dioctylthiophene Chemical compound CCCCCCCCC1=CSC=C1CCCCCCCC WAOUDPOLPWAIGN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-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
- 239000004642 Polyimide Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 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 3
- 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 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 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 3
- 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 3
- 239000003446 ligand Substances 0.000 description 3
- 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 3
- 125000002347 octyl 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])[H] 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
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- 229920000728 polyester Polymers 0.000 description 3
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- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
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- 239000007772 electrode material Substances 0.000 description 2
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- WUOIAOOSKMHJOV-UHFFFAOYSA-N ethyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CC)C1=CC=CC=C1 WUOIAOOSKMHJOV-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
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- 238000003818 flash chromatography Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000005232 molecular self-assembly Methods 0.000 description 2
- 125000001421 myristyl 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])[H] 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 125000002958 pentadecyl 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])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
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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 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- 229910021523 barium zirconate Inorganic materials 0.000 description 1
- DQBAOWPVHRWLJC-UHFFFAOYSA-N barium(2+);dioxido(oxo)zirconium Chemical compound [Ba+2].[O-][Zr]([O-])=O DQBAOWPVHRWLJC-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
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- 238000011068 loading method Methods 0.000 description 1
- IOOQQIVFCFWSIU-UHFFFAOYSA-M magnesium;octane;bromide Chemical compound [Mg+2].[Br-].CCCCCCC[CH2-] IOOQQIVFCFWSIU-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- NFBAXHOPROOJAW-UHFFFAOYSA-N phenindione Chemical class O=C1C2=CC=CC=C2C(=O)C1C1=CC=CC=C1 NFBAXHOPROOJAW-UHFFFAOYSA-N 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000807 solvent casting Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- 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
-
- 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
-
- 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
-
- 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
- H10K85/151—Copolymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Thin Film Transistor (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/042,359 US6777529B2 (en) | 2002-01-11 | 2002-01-11 | Polythiophenes and devices thereof |
| US42359 | 2002-01-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60307333D1 DE60307333D1 (de) | 2006-09-21 |
| DE60307333T2 true DE60307333T2 (de) | 2006-12-14 |
Family
ID=21921464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60307333T Expired - Lifetime DE60307333T2 (de) | 2002-01-11 | 2003-01-10 | Polythiophene und damit hergestellte Vorrichtungen |
Country Status (4)
| Country | Link |
|---|---|
| US (2) | US6777529B2 (enExample) |
| EP (1) | EP1329477B1 (enExample) |
| JP (1) | JP2003231739A (enExample) |
| DE (1) | DE60307333T2 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1456892A1 (en) * | 2001-11-30 | 2004-09-15 | Acreo AB | Electrochemical device |
| US6770904B2 (en) * | 2002-01-11 | 2004-08-03 | Xerox Corporation | Polythiophenes and electronic devices generated therefrom |
| US7141644B2 (en) * | 2002-01-11 | 2006-11-28 | Xerox Corporation | Polthiophenes and devices thereof |
| US6777529B2 (en) * | 2002-01-11 | 2004-08-17 | Xerox Corporation | Polythiophenes and devices thereof |
| TWI297553B (enExample) * | 2002-08-28 | 2008-06-01 | Ind Tech Res Inst | |
| KR100524552B1 (ko) * | 2002-09-28 | 2005-10-28 | 삼성전자주식회사 | 유기 게이트 절연막 및 이를 이용한 유기박막 트랜지스터 |
| US6803262B2 (en) * | 2002-10-17 | 2004-10-12 | Xerox Corporation | Process using self-organizable polymer |
| US7973313B2 (en) * | 2003-02-24 | 2011-07-05 | Semiconductor Energy Laboratory Co., Ltd. | Thin film integrated circuit device, IC label, container comprising the thin film integrated circuit, manufacturing method of the thin film integrated circuit device, manufacturing method of the container, and management method of product having the container |
| US7169883B2 (en) * | 2003-08-22 | 2007-01-30 | Xerox Corporation | Polymers |
| WO2005053001A2 (en) * | 2003-11-25 | 2005-06-09 | Northwestern University | Method and system for electronic detection of mechanical perturbations using bimos readouts |
| US7759924B2 (en) * | 2003-11-25 | 2010-07-20 | Northwestern University | Cascaded MOSFET embedded multi-input microcantilever |
| US7767998B2 (en) * | 2003-12-04 | 2010-08-03 | Alcatel-Lucent Usa Inc. | OFETs with active channels formed of densified layers |
| US7768405B2 (en) * | 2003-12-12 | 2010-08-03 | Semiconductor Energy Laboratory Co., Ltd | Semiconductor device and manufacturing method thereof |
| KR101137797B1 (ko) * | 2003-12-15 | 2012-04-20 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 박막 집적회로장치의 제조방법, 비접촉형 박막집적회로장치 및 그 제조 방법, 비접촉형 박막 집적회로장치를 가지는 아이디 태그 및 동전 |
| KR101169820B1 (ko) * | 2004-03-17 | 2012-07-30 | 다우 글로벌 테크놀로지스 엘엘씨 | 펜타티에닐-플루오렌 공중합체 |
| US20050211973A1 (en) * | 2004-03-23 | 2005-09-29 | Kiyotaka Mori | Stressed organic semiconductor |
| US7102017B2 (en) * | 2004-06-10 | 2006-09-05 | Xerox Corporation | Processes to prepare small molecular thiophene compounds |
| US7294850B2 (en) * | 2004-06-10 | 2007-11-13 | Xerox Corporation | Device with small molecular thiophene compound having divalent linkage |
| WO2006011643A1 (ja) * | 2004-07-30 | 2006-02-02 | Sumitomo Chemical Company, Limited | 高分子化合物、高分子薄膜およびそれを用いた高分子薄膜素子 |
| KR20070102661A (ko) * | 2004-09-24 | 2007-10-19 | 플렉스트로닉스, 인크 | 광기전 전지에서의 헤테로 원자를 갖는 위치 규칙적폴리(3-치환 티오펜) |
| GB0428403D0 (en) * | 2004-12-24 | 2005-02-02 | Cambridge Display Tech Ltd | Optical devices and their manufacture |
| US7619242B2 (en) * | 2005-02-25 | 2009-11-17 | Xerox Corporation | Celluloses and devices thereof |
| EP1864300A4 (en) * | 2005-03-16 | 2009-12-02 | Plextronics Inc | COPOLYMERS OF SOLUBLE POLY (THIOPHENES) WITH IMPROVED ELECTRONIC PERFORMANCE |
| US8089062B2 (en) * | 2005-03-23 | 2012-01-03 | Xerox Corporation | Wax encapsulated electronic devices |
| GB2424759A (en) * | 2005-04-01 | 2006-10-04 | Seiko Epson Corp | Inkjet deposition of polythiophene semiconductor material dissolved in halogenated aromatic solvents |
| KR20080043772A (ko) * | 2005-08-01 | 2008-05-19 | 플렉스트로닉스, 인크 | 전도성 중합체의 잠재성 도핑 |
| TWI261361B (en) * | 2005-08-31 | 2006-09-01 | Ind Tech Res Inst | Organic thin-film transistor structure and method for fabricating the same is provided |
| US20070278453A1 (en) * | 2006-06-02 | 2007-12-06 | Steffen Zahn | Electrically conductive polymers and method of making electrically conductive polymers |
| KR101206659B1 (ko) | 2006-09-21 | 2012-11-30 | 삼성전자주식회사 | 올리고머 화합물을 포함하는 유기반도체 조성물, 이를포함하는 유기 반도체층 형성용 조성물, 이를 이용한유기반도체 박막 및 유기 전자소자 |
| US20100084000A1 (en) * | 2006-09-26 | 2010-04-08 | Sumitomo Chemical Company, Limited | Organic photoelectric conversion device and polymer useful for producing the same |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2703359B1 (fr) * | 1993-03-31 | 1995-06-23 | Cis Bio Int | Copolymère nucléotide(s)/polymère conducteur électronique ; son procédé de préparation et son utilisation . |
| US5619357A (en) | 1995-06-06 | 1997-04-08 | International Business Machines Corporation | Flat panel display containing black matrix polymer |
| US6242561B1 (en) * | 1996-03-06 | 2001-06-05 | Basf Aktiengesellschaft | Substituted polythiophenes, processes for their preparation their use |
| US5969376A (en) | 1996-08-23 | 1999-10-19 | Lucent Technologies Inc. | Organic thin film transistor having a phthalocyanine semiconductor layer |
| US6107117A (en) | 1996-12-20 | 2000-08-22 | Lucent Technologies Inc. | Method of making an organic thin film transistor |
| US5777070A (en) | 1997-10-23 | 1998-07-07 | The Dow Chemical Company | Process for preparing conjugated polymers |
| JP2001261796A (ja) * | 2000-03-14 | 2001-09-26 | Japan Science & Technology Corp | アルコキシポリチオフェンとアルコキシチオフェン |
| GB0028867D0 (en) * | 2000-11-28 | 2001-01-10 | Avecia Ltd | Field effect translators,methods for the manufacture thereof and materials therefor |
| EP1279690A1 (en) * | 2001-07-25 | 2003-01-29 | MERCK PATENT GmbH | Mono-oligo- and poly-3-substituted-4-fluorothiophenes and their use as charge transport materials |
| EP1279689B1 (en) | 2001-07-25 | 2008-10-01 | MERCK PATENT GmbH | Mono-, Oligo and Poly-3-(1,1-difluoroalkyl)thiophenes and their use as charge transport materials |
| US6777529B2 (en) * | 2002-01-11 | 2004-08-17 | Xerox Corporation | Polythiophenes and devices thereof |
| US7141644B2 (en) * | 2002-01-11 | 2006-11-28 | Xerox Corporation | Polthiophenes and devices thereof |
-
2002
- 2002-01-11 US US10/042,359 patent/US6777529B2/en not_active Expired - Lifetime
-
2003
- 2003-01-10 JP JP2003004779A patent/JP2003231739A/ja active Pending
- 2003-01-10 EP EP03000429A patent/EP1329477B1/en not_active Expired - Lifetime
- 2003-01-10 DE DE60307333T patent/DE60307333T2/de not_active Expired - Lifetime
-
2004
- 2004-06-23 US US10/874,929 patent/US6992167B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20030144466A1 (en) | 2003-07-31 |
| US6992167B2 (en) | 2006-01-31 |
| EP1329477B1 (en) | 2006-08-09 |
| EP1329477A1 (en) | 2003-07-23 |
| US20040236070A1 (en) | 2004-11-25 |
| US6777529B2 (en) | 2004-08-17 |
| JP2003231739A (ja) | 2003-08-19 |
| DE60307333D1 (de) | 2006-09-21 |
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| 8364 | No opposition during term of opposition |