JP4960576B2 - コアシェル構造を有する有機化合物、その製造方法、その使用およびその化合物を含む電子部品 - Google Patents
コアシェル構造を有する有機化合物、その製造方法、その使用およびその化合物を含む電子部品 Download PDFInfo
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- JP4960576B2 JP4960576B2 JP2003320228A JP2003320228A JP4960576B2 JP 4960576 B2 JP4960576 B2 JP 4960576B2 JP 2003320228 A JP2003320228 A JP 2003320228A JP 2003320228 A JP2003320228 A JP 2003320228A JP 4960576 B2 JP4960576 B2 JP 4960576B2
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- 150000001875 compounds Chemical class 0.000 title claims description 84
- 238000000034 method Methods 0.000 title claims description 30
- 239000011258 core-shell material Substances 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 6
- 150000002894 organic compounds Chemical class 0.000 title description 8
- 239000004065 semiconductor Substances 0.000 claims description 38
- 238000004519 manufacturing process Methods 0.000 claims description 19
- -1 n-decyl Chemical group 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 125000000524 functional group Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- 230000005669 field effect Effects 0.000 claims description 6
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical group C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000005859 coupling reaction Methods 0.000 claims description 3
- 229920000570 polyether Polymers 0.000 claims description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 238000005577 Kumada cross-coupling reaction Methods 0.000 claims description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical group CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims description 2
- CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical group CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 claims description 2
- LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical group C[Sn](C)C LYRCQNDYYRPFMF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 229920000642 polymer Polymers 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 239000012071 phase Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
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- 239000012043 crude product Substances 0.000 description 4
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- 150000002431 hydrogen Chemical class 0.000 description 4
- 229920000587 hyperbranched polymer Polymers 0.000 description 4
- 238000010653 organometallic reaction Methods 0.000 description 4
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 4
- 229920002098 polyfluorene Polymers 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
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- 229910052710 silicon Inorganic materials 0.000 description 4
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- 239000010409 thin film Substances 0.000 description 4
- 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 3
- FRYRJNHMRVINIZ-UHFFFAOYSA-N B1CCOO1 Chemical compound B1CCOO1 FRYRJNHMRVINIZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 229910001623 magnesium bromide Inorganic materials 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000005442 molecular electronic Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen 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
- 239000002244 precipitate Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SZQQTWLBYAKIOT-UHFFFAOYSA-N (3,5-dibromophenyl)-trimethylsilane Chemical compound C[Si](C)(C)C1=CC(Br)=CC(Br)=C1 SZQQTWLBYAKIOT-UHFFFAOYSA-N 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 238000012679 convergent method Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000000412 dendrimer Substances 0.000 description 2
- 125000005266 diarylamine group Chemical group 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000012678 divergent method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 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 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- KUJYDIFFRDAYDH-UHFFFAOYSA-N 2-thiophen-2-yl-5-[5-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophene Chemical compound C1=CSC(C=2SC(=CC=2)C=2SC(=CC=2)C=2SC(=CC=2)C=2SC(=CC=2)C=2SC=CC=2)=C1 KUJYDIFFRDAYDH-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C)(*)c1ccc(C(C)(C)*)[s]1 Chemical compound CC(C)(*)c1ccc(C(C)(C)*)[s]1 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 239000002322 conducting polymer Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
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- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
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- 238000006731 degradation reaction Methods 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000000608 laser ablation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 125000006610 n-decyloxy group Chemical group 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000006609 n-nonyloxy group Chemical group 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 229920003257 polycarbosilane Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
Classifications
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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
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/20—Polysulfones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
-
- 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
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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
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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
- H10K85/40—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
- H10K85/791—Starburst compounds
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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
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1416—Condensed systems
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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
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
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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
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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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
- C09K2211/1458—Heterocyclic containing sulfur as the only heteroatom
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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]
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- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
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- 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
- H10K85/115—Polyfluorene; Derivatives thereof
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- H—ELECTRICITY
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- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Thin Film Transistor (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Developing Agents For Electrophotography (AREA)
- Bipolar Transistors (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Description
ポリフルオレンおよびフルオレンコポリマー、たとえば、ポリ(9,9−ジオクチルフルオレン−コ−ビチオフェン)(I)
Lは線状の共役オリゴマー鎖であり、
Rは直鎖または分枝鎖のC2〜C20−アルキル基、モノ不飽和またはポリ不飽和のC2〜C20−アルケニル基、C2〜C20−アルコキシ基、C2〜C20−アルアルキル基またはC2〜C20オリゴエーテル基またはC2〜C20−ポリエーテル基であり、
nは3以上、好ましくは6以上の整数である]のコア−シェル−構造を有する。
R4は同一かまたは異なって、それぞれ水素であるか、あるいは直鎖または分枝鎖のC1〜C20−アルキル基またはC1〜C20−アルコキシ基であってもよく、好ましくは水素またはC6〜C12−アルキル基であり、かつ、
R5は水素またはメチル基またはエチル基であり、好ましくは水素である]の2〜10個、特に好ましくは2〜7個の単位から成る鎖である。
例1:(線状の共役オリゴマー鎖および末端鎖を有する中間体)
例2
(シラン−官能性モノ樹状構造中間体の製造)
例7:(本発明による化合物の製造)
Claims (14)
- 多官能性単位から成るコアと、それぞれ末端結合位でフレキシブルな非共役鎖を有している線状の共役オリゴマー鎖のシェルとを含むコア−シェル構造を含み、その際、コア−シェル構造は、式(Z)
Lは式(VI−a)又は(VI−b)
Rは直鎖または分枝鎖のC2〜C20−アルキル基、モノ不飽和のC2〜C20−アルケニル基、C2〜C20−アルコキシ基、C2〜C20−アルアルキル基またはC 2 〜C20−ポリエーテル基であり、
nは3以上の整数である]の構造であることを特徴とする、化合物。 - 線状の共役オリゴマー鎖が、2〜7個の単位の鎖長を有する鎖である、請求項1記載の化合物。
- 線状の共役オリゴマー鎖が、それぞれ末端結合位で、同一かまたは異なる分枝又は非分枝のC 2 〜C 20 −アルキル又はC 2 〜C 20 −アルコキシ基によりキャップされている、請求項1又は2記載の化合物。
- アルキル基又はアルコキシ基が、非分枝のC2〜C20−アルキル又はC2〜C20−アルコキシ基である、請求項3に記載の化合物。
- アルキル基がn−ヘキシル、n−デシル又はn−ドデシル基である、請求項3又は4に記載の化合物。
- 半導体である、請求項1から5までのいずれか1項に記載の化合物。
- ハロゲン基、オルガノ錫基、オルガノ珪素基およびオルガノ硼素基からなる群から選択される官能基が、樹状コア、線状の共役オリゴマー鎖およびフレキシブルな非共役鎖中に挿入され、その後これらはオルガノ金属反応によって互いに結合される、請求項1から6までのいずれか1項に記載の化合物を製造する方法。
- ハロゲンが、塩素、臭素又はヨウ素であり、オルガノ錫基が、トリメチル錫基又はトリエチル錫基であり、オルガノ珪素基が、トリメチルシラン基又はトリエチルシラン基であり、オルガノ硼素基が、ホウ素酸から選択される、請求項7記載の化合物を製造する方法。
- 2個のブロモ基がグリニャード化合物を介してパラジウム触媒を用いて結合する、Kumadaカップリングを用いて製造する、請求項7に記載の化合物を製造する方法。
- 硼素含有基が、塩基性条件下で、パラジウム触媒を用いてブロモ基と結合する、Suzukiカップリングを用いて製造する、請求項7に記載の化合物を製造する方法。
- 電子部品中の半導体としての、請求項1から6までのいずれか1項に記載の化合物の使用。
- 電界効果トランジスタ、発光部品、有機ルミネセンスダイオード、光電池、レーザー及びセンサー中の半導体としての、請求項11に記載の化合物の使用。
- 溶液からの塗布される層の形での、請求項11又は12に記載の化合物の使用。
- 半導体として、請求項1から6までのいずれか1項に記載の化合物を含む電子部品。
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DE10242715.1 | 2002-09-13 | ||
DE10242715 | 2002-09-13 | ||
DE10305945A DE10305945A1 (de) | 2002-09-13 | 2003-02-12 | Organische Verbindungen mit Kern-Schale-Struktur |
DE10305945.8 | 2003-02-12 |
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JP2004149514A JP2004149514A (ja) | 2004-05-27 |
JP4960576B2 true JP4960576B2 (ja) | 2012-06-27 |
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US (1) | US7078724B2 (ja) |
EP (1) | EP1398341B1 (ja) |
JP (1) | JP4960576B2 (ja) |
KR (1) | KR101061310B1 (ja) |
CN (1) | CN100564374C (ja) |
AT (1) | ATE393186T1 (ja) |
CA (1) | CA2440307A1 (ja) |
DE (1) | DE50309671D1 (ja) |
IL (1) | IL157840A (ja) |
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CN100372142C (zh) * | 2001-09-05 | 2008-02-27 | 夏普株式会社 | 高分子结构体及具有它的功能元件、和晶体管及显示装置 |
DE102004014621A1 (de) | 2004-03-25 | 2005-10-13 | H.C. Starck Gmbh | Organische Verbindungen mit Kern-Schale-Struktur |
GB0602347D0 (en) * | 2006-02-06 | 2006-03-15 | Isis Innovation | Image sensor |
CN1974709B (zh) * | 2006-06-30 | 2010-05-12 | 华南理工大学 | 含极性基团电磷光共轭聚合物及其应用 |
JP2008053659A (ja) * | 2006-08-28 | 2008-03-06 | Olympus Corp | 高品位分子性結晶製造方法及び有機半導体デバイス |
DE102006043039A1 (de) * | 2006-09-14 | 2008-03-27 | H.C. Starck Gmbh | Halbleiterschichten bildende Mischungen von organischen Verbindungen |
JP5035958B2 (ja) * | 2006-11-24 | 2012-09-26 | 住友化学株式会社 | 分岐型化合物、これを用いた有機薄膜及び有機薄膜素子 |
US20080251919A1 (en) * | 2007-04-12 | 2008-10-16 | Chien-Hsueh Shih | Ultra-low resistance interconnect |
US9520563B2 (en) * | 2007-11-21 | 2016-12-13 | The Board Of Trustees Of The Leland Stanford Junior University | Patterning of organic semiconductor materials |
CN101952345A (zh) * | 2008-02-13 | 2011-01-19 | 国立大学法人大阪大学 | 聚合物、使用它的有机薄膜以及有机薄膜元件 |
DE102008014158A1 (de) | 2008-03-14 | 2009-09-17 | H.C. Starck Gmbh | Neue makromolekulare Verbindungen aufweisend eine Kern-Schale-Struktur zur Verwendung als Halbleiter |
DE102014211239A1 (de) * | 2014-06-12 | 2015-12-17 | Benecke-Kaliko Ag | Folie mit integrierter Sensorik |
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US4507466A (en) | 1983-01-07 | 1985-03-26 | The Dow Chemical Corporation | Dense star polymers having core, core branches, terminal groups |
US4631337A (en) | 1983-01-07 | 1986-12-23 | The Dow Chemical Company | Hydrolytically-stable dense star polyamine |
JPS60120722A (ja) * | 1983-12-02 | 1985-06-28 | Matsushita Electric Ind Co Ltd | 導電体 |
JPS63162687A (ja) * | 1986-12-25 | 1988-07-06 | Agency Of Ind Science & Technol | チオフエン系化合物及びその製造方法 |
US5070183A (en) | 1987-12-07 | 1991-12-03 | E. I. Du Pont De Nemours And Company | Hyperbranched polyarylene |
US5145930A (en) | 1987-12-07 | 1992-09-08 | E. I. Du Pont De Nemours And Company | Preparation of hyperbranched polyarylenes |
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US5183862A (en) | 1990-06-22 | 1993-02-02 | E. I. Du Pont De Nemours And Company | Hyperbranched polyesters |
US5264543A (en) | 1991-10-30 | 1993-11-23 | E. I. Du Pont De Nemours And Company | Hyperbranched aramid |
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US5225522A (en) | 1992-07-13 | 1993-07-06 | Eastman Kodak Company | Multiply-branched aliphatic-aromatic polyesters and method for preparing multiply-branched aliphatic-aromatic polyesters |
JPH1048678A (ja) * | 1996-03-06 | 1998-02-20 | Basf Ag | 非線形光学材料 |
US6025462A (en) * | 1997-03-06 | 2000-02-15 | Eic Laboratories, Inc. | Reflective and conductive star polymers |
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JP3693224B2 (ja) * | 1999-05-17 | 2005-09-07 | 富士写真フイルム株式会社 | 有機エレクトロルミネッセンス素子 |
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JP4729776B2 (ja) * | 2000-08-04 | 2011-07-20 | 東レ株式会社 | 発光素子 |
DE60125202T2 (de) | 2000-09-26 | 2007-11-08 | Cambridge Display Technology Ltd. | Polymere und ihre verwendungen |
US6384172B1 (en) | 2001-01-02 | 2002-05-07 | Michigan Molecular Institute | Hyperbranched polycarbosilanes, polycarbosiloxanes, polycarbosilazenes and copolymers thereof |
JP4103493B2 (ja) * | 2002-08-13 | 2008-06-18 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子および表示装置 |
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- 2003-09-03 EP EP03019574A patent/EP1398341B1/de not_active Expired - Lifetime
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IL157840A (en) | 2007-03-08 |
EP1398341A2 (de) | 2004-03-17 |
DE50309671D1 (de) | 2008-06-05 |
KR20040027325A (ko) | 2004-04-01 |
KR101061310B1 (ko) | 2011-08-31 |
ATE393186T1 (de) | 2008-05-15 |
CA2440307A1 (en) | 2004-03-13 |
US7078724B2 (en) | 2006-07-18 |
US20040132959A1 (en) | 2004-07-08 |
EP1398341A3 (de) | 2004-03-24 |
CN100564374C (zh) | 2009-12-02 |
EP1398341B1 (de) | 2008-04-23 |
IL157840A0 (en) | 2004-03-28 |
JP2004149514A (ja) | 2004-05-27 |
CN1495179A (zh) | 2004-05-12 |
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