JP2010513611A - 縮合したセレノフェンを含むポリマー - Google Patents
縮合したセレノフェンを含むポリマー Download PDFInfo
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- JP2010513611A JP2010513611A JP2009541821A JP2009541821A JP2010513611A JP 2010513611 A JP2010513611 A JP 2010513611A JP 2009541821 A JP2009541821 A JP 2009541821A JP 2009541821 A JP2009541821 A JP 2009541821A JP 2010513611 A JP2010513611 A JP 2010513611A
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- polymer
- diyl
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- 229920000642 polymer Polymers 0.000 title claims abstract description 119
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 title abstract description 5
- 239000000463 material Substances 0.000 claims abstract description 46
- 230000003287 optical effect Effects 0.000 claims abstract description 11
- -1 selenophene-2,5-diyl Chemical group 0.000 claims description 83
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 25
- 239000010408 film Substances 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 229920002959 polymer blend Polymers 0.000 claims description 15
- 238000009472 formulation Methods 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 239000000758 substrate Substances 0.000 claims description 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 125000006850 spacer group Chemical group 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 239000003990 capacitor Substances 0.000 claims description 4
- 230000005669 field effect Effects 0.000 claims description 4
- 238000013086 organic photovoltaic Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 3
- 108091028043 Nucleic acid sequence Proteins 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- 238000000018 DNA microarray Methods 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 239000007772 electrode material Substances 0.000 claims description 2
- 238000005401 electroluminescence Methods 0.000 claims description 2
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- 125000000217 alkyl group Chemical group 0.000 description 18
- 238000000034 method Methods 0.000 description 18
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- 150000001875 compounds Chemical class 0.000 description 13
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- FPDOSPSUXAVNKK-UHFFFAOYSA-N selenopheno[3,2-b]thiophene Chemical compound [se]1C=CC2=C1C=CS2 FPDOSPSUXAVNKK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- QKDYDXJISKWZQE-UHFFFAOYSA-N selenopheno[3,2-b]selenophene Chemical compound [se]1C=CC2=C1C=C[se]2 QKDYDXJISKWZQE-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002800 charge carrier Substances 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 7
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- 239000011541 reaction mixture Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- 0 CC(C)(*)**(*1)=C(*)C(**2)=C1C(CC*)=C2C(C)(C)* Chemical compound CC(C)(*)**(*1)=C(*)C(**2)=C1C(CC*)=C2C(C)(C)* 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 238000007641 inkjet printing Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 230000006870 function Effects 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229920000620 organic polymer Polymers 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000011669 selenium Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 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
- 238000001228 spectrum Methods 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 125000004001 thioalkyl group Chemical group 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 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 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- LNRNPOWVKSXUJF-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)selenopheno[3,2-b]thiophen-5-yl]-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C(S1)=CC2=C1C=C(B1OC(C)(C)C(C)(C)O1)[se]2 LNRNPOWVKSXUJF-UHFFFAOYSA-N 0.000 description 2
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
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- 239000003446 ligand Substances 0.000 description 2
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- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 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 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- 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
- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
- H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
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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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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K99/00—Subject matter not provided for in other groups of this subclass
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1458—Heterocyclic containing sulfur as the only heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1491—Heterocyclic containing other combinations of heteroatoms
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Electroluminescent Light Sources (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06026786 | 2006-12-22 | ||
| PCT/EP2007/010704 WO2008077465A2 (en) | 2006-12-22 | 2007-12-08 | Polymers comprising fused selenophene |
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| JP2010513611A true JP2010513611A (ja) | 2010-04-30 |
| JP2010513611A5 JP2010513611A5 (enExample) | 2013-11-21 |
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| EP (1) | EP2121797B1 (enExample) |
| JP (1) | JP2010513611A (enExample) |
| KR (1) | KR20090104054A (enExample) |
| CN (1) | CN101563389B (enExample) |
| AT (1) | ATE554122T1 (enExample) |
| TW (1) | TWI445730B (enExample) |
| WO (1) | WO2008077465A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090140219A1 (en) * | 2007-07-13 | 2009-06-04 | Air Products And Chemicals, Inc. | Selenium Containing Electrically Conductive Polymers and Method of Making Electrically Conductive Polymers |
| US7982055B2 (en) | 2007-07-13 | 2011-07-19 | Konarka Technologies, Inc. | Heterocyclic fused selenophene monomers |
| US8148548B2 (en) * | 2007-07-13 | 2012-04-03 | Konarka Technologies, Inc. | Heterocyclic fused selenophene monomers |
| US7981323B2 (en) * | 2007-07-13 | 2011-07-19 | Konarka Technologies, Inc. | Selenium containing electrically conductive copolymers |
| EP2814861B1 (en) * | 2012-02-16 | 2017-03-08 | Merck Patent GmbH | Organic semiconducting polymers |
| CN104395372B (zh) * | 2012-07-02 | 2017-04-05 | 默克专利股份有限公司 | 共轭聚合物 |
| ITMI20122052A1 (it) * | 2012-11-30 | 2014-05-31 | Eni Spa | Procedimento per la preparazione di composti benzoditiofenici |
| JP5556917B2 (ja) * | 2013-02-12 | 2014-07-23 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| JP6370909B2 (ja) | 2013-09-05 | 2018-08-08 | チュビタック （ターキー ビリムセル ヴィ テクノロジク アラスティルマ クルム）Ｔｕｂｉｔａｋ （Ｔｕｒｋｉｙｅ Ｂｉｌｉｍｓｅｌ Ｖｅ Ｔｅｋｎｏｌｏｊｉｋ Ａｒａｓｔｉｒｍａ Ｋｕｒｕｍｕ） | 白色発光ダイオード用のポリ（チエノチオフェニルボラン）類及びポリ（ジチエノチオフェニルボラン）類 |
| CN107210366B (zh) * | 2014-11-06 | 2020-05-19 | 浦项工科大学校产学协力团 | 包含激子缓冲层的钙钛矿发光器件以及制造其的方法 |
| GB201502113D0 (en) | 2015-02-09 | 2015-03-25 | Cambridge Display Tech Ltd | Solution for a semiconducting layer of an organic electronic device |
| TR201712311T1 (tr) | 2015-02-20 | 2018-03-21 | Tuerkiye Bilimsel Ve Teknolojik Arastirma Kurumu Tuebitak | Organik Temelli Işık Yayan Diyotlar İçin Tiyenotiyofen Bor (Elektron Verici-Alıcı) Temelli Malzemeler |
| KR102349852B1 (ko) | 2015-02-20 | 2022-01-10 | 티유비아이티에이케이 | 유기발광 다이오드용 티에노티오펜/다이티에노티오펜 - 트라이페닐아민/테트라페닐에틸렌 유도체 |
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| JPH08245636A (ja) * | 1995-03-06 | 1996-09-24 | Fuji Electric Co Ltd | セレノロセレノフェンオリゴマおよびその製造方法 |
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| CN101693722A (zh) * | 2004-06-09 | 2010-04-14 | 默克专利股份有限公司 | 可聚合的噻吩并[3,2-b]噻吩 |
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2007
- 2007-12-08 US US12/520,306 patent/US8529794B2/en not_active Expired - Fee Related
- 2007-12-08 CN CN2007800469703A patent/CN101563389B/zh not_active Expired - Fee Related
- 2007-12-08 KR KR1020097015271A patent/KR20090104054A/ko not_active Abandoned
- 2007-12-08 JP JP2009541821A patent/JP2010513611A/ja not_active Ceased
- 2007-12-08 WO PCT/EP2007/010704 patent/WO2008077465A2/en not_active Ceased
- 2007-12-08 AT AT07856480T patent/ATE554122T1/de active
- 2007-12-08 EP EP07856480A patent/EP2121797B1/en not_active Not-in-force
- 2007-12-19 TW TW096148753A patent/TWI445730B/zh not_active IP Right Cessation
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| US4663001A (en) * | 1984-06-15 | 1987-05-05 | Solvay & Cie. (Societe Anonyme) | Electroconductive polymers derived from heterocycles polycyclic monomers and process for their manufacture |
| JPH08245636A (ja) * | 1995-03-06 | 1996-09-24 | Fuji Electric Co Ltd | セレノロセレノフェンオリゴマおよびその製造方法 |
| WO2005026144A1 (ja) * | 2003-09-12 | 2005-03-24 | Sumitomo Chemical Company, Limited | デンドリマー化合物及びそれを用いた有機発光素子 |
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| JP2006089413A (ja) * | 2004-09-24 | 2006-04-06 | Japan Science & Technology Agency | 新規な有機半導体化合物、その製造方法およびそれを用いた有機半導体デバイス |
| JP2006176705A (ja) * | 2004-12-24 | 2006-07-06 | Sumitomo Chemical Co Ltd | 高分子化合物およびそれを用いた高分子発光素子 |
| JP2007051289A (ja) * | 2005-08-16 | 2007-03-01 | Merck Patent Gmbh | チオフェンまたはセレノフェン化合物の重合方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| HK1137770A1 (en) | 2010-08-06 |
| WO2008077465A2 (en) | 2008-07-03 |
| TWI445730B (zh) | 2014-07-21 |
| KR20090104054A (ko) | 2009-10-05 |
| CN101563389B (zh) | 2013-07-17 |
| ATE554122T1 (de) | 2012-05-15 |
| CN101563389A (zh) | 2009-10-21 |
| US20090278093A1 (en) | 2009-11-12 |
| WO2008077465A3 (en) | 2008-08-28 |
| EP2121797B1 (en) | 2012-04-18 |
| TW200842140A (en) | 2008-11-01 |
| US8529794B2 (en) | 2013-09-10 |
| EP2121797A2 (en) | 2009-11-25 |
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