DE60308534T2 - Dendritisches polymer und element für elektronisches bauteil, bei dem das polymer verwendet wird - Google Patents
Dendritisches polymer und element für elektronisches bauteil, bei dem das polymer verwendet wird Download PDFInfo
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- DE60308534T2 DE60308534T2 DE2003608534 DE60308534T DE60308534T2 DE 60308534 T2 DE60308534 T2 DE 60308534T2 DE 2003608534 DE2003608534 DE 2003608534 DE 60308534 T DE60308534 T DE 60308534T DE 60308534 T2 DE60308534 T2 DE 60308534T2
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- dendritic polymer
- dendritic
- polymer according
- substituent
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- 229920000642 polymer Polymers 0.000 title claims description 45
- 239000000412 dendrimer Substances 0.000 claims description 159
- 229920000736 dendritic polymer Polymers 0.000 claims description 155
- 238000006243 chemical reaction Methods 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000962 organic group Chemical group 0.000 claims description 14
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 9
- 239000002019 doping agent Substances 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 150000001491 aromatic compounds Chemical class 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000001334 alicyclic compounds Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 5
- 230000005284 excitation Effects 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 4
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- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
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- 230000005611 electricity Effects 0.000 claims description 3
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- 239000000126 substance Substances 0.000 claims description 3
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- 239000000203 mixture Substances 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
- 150000001875 compounds Chemical class 0.000 description 36
- 230000015572 biosynthetic process Effects 0.000 description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 34
- 239000000047 product Substances 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
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- 235000011152 sodium sulphate Nutrition 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000010409 thin film Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
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- 229910052740 iodine Inorganic materials 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 6
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 5
- BJRLIJAXUVPMJP-UHFFFAOYSA-N 2-(3,5-dibromophenyl)-5-thiophen-2-ylthiophene Chemical compound BrC1=CC(Br)=CC(C=2SC(=CC=2)C=2SC=CC=2)=C1 BJRLIJAXUVPMJP-UHFFFAOYSA-N 0.000 description 5
- LWALQZXAZDVFDT-UHFFFAOYSA-N 3-n-benzo[a]anthracen-1-ylbenzene-1,3-diamine Chemical compound NC1=CC=CC(NC=2C3=C4C=C5C=CC=CC5=CC4=CC=C3C=CC=2)=C1 LWALQZXAZDVFDT-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 229920001940 conductive polymer Polymers 0.000 description 5
- 229920000547 conjugated polymer Polymers 0.000 description 5
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
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- 239000011734 sodium Substances 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 150000001642 boronic acid derivatives Chemical class 0.000 description 4
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- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 4
- 230000002165 photosensitisation Effects 0.000 description 4
- 239000003504 photosensitizing agent Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
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- 239000007858 starting material Substances 0.000 description 4
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 4
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- OEERIBPGRSLGEK-UHFFFAOYSA-N carbon dioxide;methanol Chemical compound OC.O=C=O OEERIBPGRSLGEK-UHFFFAOYSA-N 0.000 description 3
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- 125000000623 heterocyclic group Chemical group 0.000 description 3
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- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 description 2
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
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- 101150096839 Fcmr gene Proteins 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
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- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 2
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 2
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- 235000019270 ammonium chloride Nutrition 0.000 description 2
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- UVBXZOISXNZBLY-UHFFFAOYSA-L palladium(2+);triphenylphosphane;diacetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O.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 UVBXZOISXNZBLY-UHFFFAOYSA-L 0.000 description 1
- JGBZTJWQMWZVNX-UHFFFAOYSA-N palladium;tricyclohexylphosphane Chemical compound [Pd].C1CCCCC1P(C1CCCCC1)C1CCCCC1.C1CCCCC1P(C1CCCCC1)C1CCCCC1 JGBZTJWQMWZVNX-UHFFFAOYSA-N 0.000 description 1
- 150000002964 pentacenes Chemical class 0.000 description 1
- GUVXZFRDPCKWEM-UHFFFAOYSA-N pentalene Chemical compound C1=CC2=CC=CC2=C1 GUVXZFRDPCKWEM-UHFFFAOYSA-N 0.000 description 1
- JQQSUOJIMKJQHS-UHFFFAOYSA-N pentaphene Chemical compound C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C=CC3=CC2=C1 JQQSUOJIMKJQHS-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- GJSGGHOYGKMUPT-UHFFFAOYSA-N phenoxathiine Chemical compound C1=CC=C2OC3=CC=CC=C3SC2=C1 GJSGGHOYGKMUPT-UHFFFAOYSA-N 0.000 description 1
- 230000001443 photoexcitation Effects 0.000 description 1
- 238000005268 plasma chemical vapour deposition Methods 0.000 description 1
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 description 1
- 229920000414 polyfuran Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- NTUROZDXWLPVHB-UHFFFAOYSA-M sodium;3-diphenylphosphanylbenzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NTUROZDXWLPVHB-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 238000002366 time-of-flight method Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 1
- PGXOVVAJURGPLL-UHFFFAOYSA-N trinaphthylene Chemical group C1=CC=C2C=C3C4=CC5=CC=CC=C5C=C4C4=CC5=CC=CC=C5C=C4C3=CC2=C1 PGXOVVAJURGPLL-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- CMLWFCUAXGSMBB-UHFFFAOYSA-N tris(2,6-dimethoxyphenyl)phosphane Chemical compound COC1=CC=CC(OC)=C1P(C=1C(=CC=CC=1OC)OC)C1=C(OC)C=CC=C1OC CMLWFCUAXGSMBB-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- LFNXCUNDYSYVJY-UHFFFAOYSA-N tris(3-methylphenyl)phosphane Chemical compound CC1=CC=CC(P(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 LFNXCUNDYSYVJY-UHFFFAOYSA-N 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 238000005019 vapor deposition process Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
-
- 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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/002—Dendritic macromolecules
- C08G83/003—Dendrimers
-
- 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
-
- 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
- H01B1/122—Ionic conductors
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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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
- H10K85/791—Starburst compounds
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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 a potential-jump barrier or a surface barrier
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
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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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| JP2002210210 | 2002-07-18 | ||
| JP2002210210 | 2002-07-18 | ||
| PCT/JP2003/008899 WO2004009680A2 (en) | 2002-07-18 | 2003-07-14 | Dendritic polymer and electronic device element employing the polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60308534D1 DE60308534D1 (de) | 2006-11-02 |
| DE60308534T2 true DE60308534T2 (de) | 2007-09-13 |
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| DE2003608534 Expired - Lifetime DE60308534T2 (de) | 2002-07-18 | 2003-07-14 | Dendritisches polymer und element für elektronisches bauteil, bei dem das polymer verwendet wird |
| DE2003605942 Expired - Lifetime DE60305942T2 (de) | 2002-07-18 | 2003-07-14 | Dendrimer und element für elektronisches bauteil, bei dem das dendrimer verwendet wird |
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| DE2003605942 Expired - Lifetime DE60305942T2 (de) | 2002-07-18 | 2003-07-14 | Dendrimer und element für elektronisches bauteil, bei dem das dendrimer verwendet wird |
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| WO2003023876A1 (fr) * | 2001-09-05 | 2003-03-20 | Sharp Kabushiki Kaisha | Structure polymere, element fonctionnel comportant une telle structure ; transistor et ecran presentant cette structure |
| US6998068B2 (en) * | 2003-08-15 | 2006-02-14 | 3M Innovative Properties Company | Acene-thiophene semiconductors |
| KR100544145B1 (ko) * | 2004-05-24 | 2006-01-23 | 삼성에스디아이 주식회사 | 박막 트랜지스터 및 이를 구비한 평판표시장치 |
| US7714320B2 (en) * | 2005-10-25 | 2010-05-11 | Alcatel-Lucent Usa Inc. | Branched phenylene-terminated thiophene oligomers |
| US8138075B1 (en) | 2006-02-06 | 2012-03-20 | Eberlein Dietmar C | Systems and methods for the manufacture of flat panel devices |
| US7608679B2 (en) * | 2006-03-31 | 2009-10-27 | 3M Innovative Properties Company | Acene-thiophene copolymers |
| 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 |
| US7666968B2 (en) * | 2006-04-21 | 2010-02-23 | 3M Innovative Properties Company | Acene-thiophene copolymers with silethynly groups |
| US7547757B2 (en) * | 2006-08-01 | 2009-06-16 | Headwaters Technology Innovation, Llc | Methods for manufacturing aryl-aryl coupled polymers |
| KR101249117B1 (ko) * | 2006-11-13 | 2013-03-29 | 삼성전자주식회사 | 메탈로센 덴드리머, 이를 이용한 유기 메모리 소자 및 그의제조방법 |
| GB0720553D0 (en) * | 2007-10-19 | 2007-11-28 | Isis Innovation | Branched materials for photovoltaic devices |
| WO2009064661A1 (en) | 2007-11-15 | 2009-05-22 | Nitto Denko Corporation | Light emitting devices and compositions |
| EP2243796A4 (en) * | 2008-02-13 | 2012-04-25 | Univ Osaka | POLYMER, ORGANIC THIN LAYER AND ORGANIC THIN LAYER |
| JP2009215279A (ja) * | 2008-02-13 | 2009-09-24 | Osaka Univ | 分岐型化合物、これを用いた有機薄膜及び有機薄膜素子 |
| KR20100129760A (ko) * | 2008-03-12 | 2010-12-09 | 스미또모 가가꾸 가부시키가이샤 | 유기 광전 변환 소자 |
| WO2009136626A1 (ja) * | 2008-05-07 | 2009-11-12 | 国立大学法人九州大学 | エレクトロクロミック材料 |
| WO2009142763A1 (en) * | 2008-05-23 | 2009-11-26 | Swaminathan Ramesh | Hybrid photovoltaic cell module |
| JP5581607B2 (ja) * | 2008-06-05 | 2014-09-03 | 住友化学株式会社 | 高分子化合物及びそれを用いた有機トランジスタ |
| US20110062424A1 (en) * | 2009-09-11 | 2011-03-17 | Nitto Denko Corporation | Polymer compositions comprising additive block copolymers |
| US8247151B2 (en) * | 2009-10-19 | 2012-08-21 | Hewlett-Packard Development Company, L.P. | Liquid toner, electrophoretic ink, and methods of making and use |
| WO2011149500A1 (en) | 2010-01-07 | 2011-12-01 | Nitto Denko Corporation | Emissive compounds for organic light-emitting diodes |
| DE102011117422A1 (de) * | 2011-10-28 | 2013-05-02 | Merck Patent Gmbh | Hyperverzweigte Polymere, Verfahren zu deren Herstellung sowie deren Verwendung in elektronischen Vorrichtungen |
| TW201329063A (zh) | 2012-01-02 | 2013-07-16 | Ind Tech Res Inst | 聯噻吩衍生物及包含此衍生物之半導體元件 |
| US20150118494A1 (en) | 2012-05-09 | 2015-04-30 | Sun Chemical Corporation | Surface modified pigment particles, method of preparation & application thereof |
| JP2015098471A (ja) * | 2013-11-18 | 2015-05-28 | 東洋合成工業株式会社 | 化学種発生向上試剤 |
| US9470625B1 (en) | 2015-05-28 | 2016-10-18 | National Chung Cheng University | Method of examining purity of dendrimers |
| CN110105333A (zh) * | 2019-04-29 | 2019-08-09 | 武汉华星光电半导体显示技术有限公司 | 电致发光材料、电致发光材料的制备方法及发光器件 |
| US11339246B2 (en) * | 2020-03-03 | 2022-05-24 | Lg Energy Solution, Ltd. | Preparation method of polymer |
| CN115521470B (zh) * | 2022-08-29 | 2023-10-31 | 中国人民解放军国防科技大学 | N-氯代锆-卟啉mof、n-氯代锆-卟啉mof/聚合物复合材料及制备方法 |
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| GB8429111D0 (en) * | 1984-11-17 | 1984-12-27 | British Petroleum Co Plc | Conductive polymers |
| JPS6376378A (ja) | 1986-09-18 | 1988-04-06 | Mitsubishi Electric Corp | 電界効果型トランジスタ |
| GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
| JP3006718B2 (ja) | 1990-09-25 | 2000-02-07 | 科学技術振興事業団 | オリゴチオフェンを用いた電子素子 |
| JP2774868B2 (ja) * | 1990-10-19 | 1998-07-09 | 日本石油株式会社 | 重合体の製造方法および有機磁性体 |
| FR2677986B1 (fr) * | 1991-06-18 | 1994-05-20 | Thomson Csf | Procede d'obtention de polymeres de type polyparaphenylene vinylene ou de type polyparathienylene vinylene. |
| JPH05110069A (ja) | 1991-10-14 | 1993-04-30 | Mitsubishi Electric Corp | 電界効果トランジスタの製造方法 |
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| JP3534445B2 (ja) * | 1993-09-09 | 2004-06-07 | 隆一 山本 | ポリチオフェンを用いたｅｌ素子 |
| US5556706A (en) | 1993-10-06 | 1996-09-17 | Matsushita Electric Industrial Co., Ltd. | Conductive layered product and method of manufacturing the same |
| JP3246189B2 (ja) * | 1994-06-28 | 2002-01-15 | 株式会社日立製作所 | 半導体表示装置 |
| JP3074277B2 (ja) * | 1995-08-29 | 2000-08-07 | 工業技術院長 | 多分岐重合体及びその製造方法 |
| US6025462A (en) * | 1997-03-06 | 2000-02-15 | Eic Laboratories, Inc. | Reflective and conductive star polymers |
| JP3972405B2 (ja) | 1997-05-09 | 2007-09-05 | 東ソー株式会社 | ３級アリールアミン類の製造方法 |
| DE69824439T2 (de) * | 1997-10-23 | 2005-06-16 | Isis Innovation Ltd., Summertown | Lichtemittierende dendrimere |
| JP3846760B2 (ja) | 1997-12-17 | 2006-11-15 | 昭和電工株式会社 | 固体電解コンデンサ及びその製造方法 |
| JP2000336171A (ja) | 1999-05-26 | 2000-12-05 | Mitsubishi Chemicals Corp | ホール伝導性を有する超分岐高分子 |
| TW484341B (en) | 1999-08-03 | 2002-04-21 | Sumitomo Chemical Co | Polymeric fluorescent substance and polymer light emitting device |
-
2003
- 2003-07-14 WO PCT/JP2003/008898 patent/WO2004009679A2/en active IP Right Grant
- 2003-07-14 CN CNB038171775A patent/CN100379796C/zh not_active Expired - Fee Related
- 2003-07-14 CN CNB038171759A patent/CN1298768C/zh not_active Expired - Fee Related
- 2003-07-14 EP EP20030765288 patent/EP1543066B1/en not_active Expired - Lifetime
- 2003-07-14 EP EP20030765289 patent/EP1539864B1/en not_active Expired - Lifetime
- 2003-07-14 US US10/521,846 patent/US7687598B2/en not_active Expired - Fee Related
- 2003-07-14 US US10/521,843 patent/US7585933B2/en not_active Expired - Fee Related
- 2003-07-14 DE DE2003608534 patent/DE60308534T2/de not_active Expired - Lifetime
- 2003-07-14 KR KR1020057000941A patent/KR100643589B1/ko not_active IP Right Cessation
- 2003-07-14 WO PCT/JP2003/008899 patent/WO2004009680A2/en active IP Right Grant
- 2003-07-14 DE DE2003605942 patent/DE60305942T2/de not_active Expired - Lifetime
- 2003-07-14 KR KR1020057000921A patent/KR100625016B1/ko not_active IP Right Cessation
- 2003-07-17 TW TW92119519A patent/TWI319767B/zh not_active IP Right Cessation
- 2003-07-17 TW TW92119521A patent/TWI323736B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2004009680A3 (en) | 2004-04-22 |
| EP1539864B1 (en) | 2006-09-20 |
| DE60305942T2 (de) | 2007-01-18 |
| TW200403271A (en) | 2004-03-01 |
| CN100379796C (zh) | 2008-04-09 |
| KR100625016B1 (ko) | 2006-09-18 |
| KR20050036958A (ko) | 2005-04-20 |
| EP1543066A2 (en) | 2005-06-22 |
| CN1671773A (zh) | 2005-09-21 |
| TWI323736B (en) | 2010-04-21 |
| TWI319767B (en) | 2010-01-21 |
| WO2004009679A2 (en) | 2004-01-29 |
| WO2004009679A3 (en) | 2004-04-22 |
| DE60308534D1 (de) | 2006-11-02 |
| CN1774464A (zh) | 2006-05-17 |
| US7687598B2 (en) | 2010-03-30 |
| US20060009614A1 (en) | 2006-01-12 |
| TW200408658A (en) | 2004-06-01 |
| CN1298768C (zh) | 2007-02-07 |
| KR20050036957A (ko) | 2005-04-20 |
| DE60305942D1 (de) | 2006-07-20 |
| US20060102890A1 (en) | 2006-05-18 |
| EP1539864A2 (en) | 2005-06-15 |
| EP1543066B1 (en) | 2006-06-07 |
| US7585933B2 (en) | 2009-09-08 |
| WO2004009680A2 (en) | 2004-01-29 |
| KR100643589B1 (ko) | 2006-11-10 |
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Owner name: SHARP K.K., OSAKA, JP |