TWI445731B - 共軛共聚物 - Google Patents
共軛共聚物 Download PDFInfo
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- TWI445731B TWI445731B TW097144526A TW97144526A TWI445731B TW I445731 B TWI445731 B TW I445731B TW 097144526 A TW097144526 A TW 097144526A TW 97144526 A TW97144526 A TW 97144526A TW I445731 B TWI445731 B TW I445731B
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- 229920001577 copolymer Polymers 0.000 title claims description 36
- -1 n-octyl Chemical group 0.000 claims description 93
- 229920000642 polymer Polymers 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
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- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
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- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 238000013086 organic photovoltaic Methods 0.000 claims description 7
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- 125000003003 spiro group Chemical group 0.000 claims description 7
- 229910052787 antimony Inorganic materials 0.000 claims description 6
- 230000005669 field effect Effects 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 5
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- 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 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-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
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- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
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- 239000002346 layers by function Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 150000008379 phenol ethers Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001596 poly (chlorostyrenes) Polymers 0.000 description 1
- 229920000314 poly p-methyl styrene Polymers 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 229920003251 poly(α-methylstyrene) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920002776 polycyclohexyl methacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical class O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical group C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 239000002094 self assembled monolayer Substances 0.000 description 1
- 239000013545 self-assembled monolayer Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- WWGXHTXOZKVJDN-UHFFFAOYSA-M sodium;n,n-diethylcarbamodithioate;trihydrate Chemical compound O.O.O.[Na+].CCN(CC)C([S-])=S WWGXHTXOZKVJDN-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- IUMOPUXDPFMEMV-UHFFFAOYSA-L strontium;2,3-dihydroxybutanedioate Chemical compound [Sr+2].[O-]C(=O)C(O)C(O)C([O-])=O IUMOPUXDPFMEMV-UHFFFAOYSA-L 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- APBDREXAUGXCCV-UHFFFAOYSA-L tetraethylazanium;carbonate Chemical compound [O-]C([O-])=O.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC APBDREXAUGXCCV-UHFFFAOYSA-L 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N trimethylmethane Natural products CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- 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
- 238000007740 vapor deposition Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- 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
- H01B1/124—Intrinsically conductive polymers
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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
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- 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
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- H10K85/151—Copolymers
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- H10K2102/10—Transparent electrodes, e.g. using graphene
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- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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Description
本發明係關於含有茚並茀和三芳基胺單元之共軛共聚物,和關於其用於有機電子裝置之用途。
最近幾年,已發展有機半導體(OSC)材料,以為了產生更多樣化、更低成本之電子裝置。發現此等材料在寬廣範圍的裝置或設備內的應用,包括,例如,有機場效電晶體(OFET)、有機發光二極體(OLED)、光偵測器、光伏打(PV)電池、感測器、記憶元件和邏輯電路等。有機半導體材料典型地以薄層(例如,小於1微米厚)存在於電子裝置中。
OFET裝置的效能主要係基於半導體材料的電荷載子移動率(charge carrier mobility)和電流開/關比,因此理想的半導體於關狀態、與高電荷載子移動率(>1×10-3
cm2
V-1
s-1
)組合時應具有低傳導性。此外,重要的是,半導體材料對氧化作用而言是相當安定的,即,其具有高游離電位,當氧化作用造成減低裝置效能。半導體材料的另外要求為良好的可加工性,特別是薄層和所欲之圖案的大量生產,和有機半導體層的高安定性、膜均勻度和完整性。
於先前技藝中,已建議各種材料作為OFET中的有機半導體,包括小分子(像例如稠五苯),和聚合物(像例如聚己基噻吩)。然而,迄今所研究的材料和裝置仍具有數種缺點,且其性質,特別是可加工性、電荷載子移動率、開/關比和安定性,仍留有進一步改善之空間。
本發明的一個目標是提供用於電子裝置之新的有機半導體材料,其於電子裝置中具有有利的性質,特別是良好的可加工性、高電荷載子移動率、高開/關比、高氧化安定性和長壽命。另一目標是擴大專家利用半導體材料的範圍(pool)。本發明的其它目標,專家由下面詳細說明立即明白。
已發現,這些目標可藉由提供如本發明所主張之半導體材料而達成。這些材料係基於聚合物,該聚合包括下面化學式之一或多種順式-或反式-茚並茀或其衍生物單元
(其中R1-4
表示芳香族或脂族烴基,且2個相鄰基團R1,2
或R3,4
亦可形成螺基團),且另外包括一或多種三芳基胺部分。特別地,已發現此等聚合物適於作為電子裝置(像電晶體)中的半導體材料,和作為聚合物發光二極體(PLED)中的電荷傳輸層或中間層,其具有良好的可加工性且同時顯示高電荷載子移動率和高氧化安定性。
WO 2004/041901描述含有芳基取代的茚並茀和另外單元(像三芳基胺或雜芳基部分)之聚合物,和其於OLED或OFET裝置之用途,但並未揭示如本發明所主張之裝置。WO 2005/024971揭示含有作為電子阻隔層之交聯緩衝層之OLED裝置,和另外揭示含有50%的茚並茀和50%的三芳基胺單元之聚合物,但並未揭示如本發明所主張之聚合物。
三芳基胺具有良好的電洞傳輸能力。然而,其於許多有機溶劑中只具有中等溶解度,其負面地影響其在膜形成加工的可加工性且導致具有中等均勻度的膜。另一方面,茚並茀溶於慣用的有機溶劑且因此顯示良好的可加工性,能形成具有高均勻度的膜。然而,大部分已報導其高效率的電子傳輸和發光部分。因此出人意外地,本發明之聚合物,其中茚並茀單元與電洞傳輸部分(像三芳基胺)組合,顯示高電荷載子移動率,且能製備電子裝置,像具有高開/關比之電晶體。
本發明係關於共軛共聚物,其包括>50莫耳%的一或多種相同或不同之式I單元
和>0莫耳%且<50莫耳%的一或多種相同或不同之式II單元
其中A和A'中之一者為單鍵且另一者為CR1
R2
,B和B'中之一者為單鍵且另一者為CR3
R4
,R1-4
彼此獨立地為相同或不同基團,該等基團係選自H、鹵素、-CN、-NC、-NCO、-NCS、-OCN、-SCN、-C(=O)NR0
R00
、-C(=O)X、-C(=O)R0
、-NH2
、-NR0
R00
、-SH、-SR0
、-SO3
H、-SO2
R0
、-OH、-NO2
、-CF3
、-SF5
、隨意地經取代之矽基、或具有1至40個C原子之二價碳基或烴基,該二價碳基或烴基隨意地經取代且隨意地包括一或多個雜原子,X 為鹵素,R0
和R00
彼此獨立地為H或隨意地包括一或多個雜原子之隨意地經取代的二價碳基或烴基,Ar 為單鍵或表示單核或多核芳基或雜芳基,m 為之整數,Y 為N、P、P=O、PF2
、P=S、As、As=O、As=S、Sb、Sb=O或Sb=S,Ar1
其可為相同或不同,若於不同的重複單元中獨立地表示單鍵或隨意地經取代的單核或多核芳基,Ar2
其可為相同或不同,若於不同的重複單元中獨立地表示隨意地經取代的單核或多核芳基,Ar3
其可為相同或不同,若於不同的重複單元中獨立地表示隨意地經取代的單核或多核芳基,其可隨意地經連接不同的式III鏈殘基的橋基取代,及k 為1、2或3,且其中隨意地,基團R1
和R2
和/或基團R3
和R4
一起與相鄰的茀部分形成螺基團。
本發明進一步關於如上面和下面所述之共聚物的用途,其係用於如上面和下面所述之有機電子裝置。
本發明係關於有機電子裝置,其包括含有如上面和下面所述之共軛共聚物之半導體層。
有機電子裝置,包括但不限於,有機場效電晶體(OFET)、薄膜電晶體(TFT)、積體電路(IC)、射頻識別(RFID)標籤、光偵測器、感測器、邏輯電路、記憶元件、電容器、有機光伏打(OPV)電池、電荷注入層、電荷傳輸層或聚合物發光二極體(PLED)中的中間層、肖特基二極體(Schottky diode)、平面化層、抗靜電膜、聚合物電解質膜(PEM)、傳導基板或圖案、光導體、電子照像元件或有機發光二極體(OLED)。
術語"聚合物"一般意指相對高分子質量的分子,其結構實質上包括實際上或概念上衍生自相對低分子質量的分子的單元的倍數重複(PAC,1996,68,2291)。術語"寡聚物"一般意指相對中等分子質量的分子,其結構實質上包括實際上或概念上衍生自具有相對更低分子質量的分子的單元的少倍數重複(PAC,1996,68,2291)。於依據本發明的較佳觀念中,聚合物意指具有>1,較佳地>10重複單元之化合物,而寡聚物意指具有>1且<20,較佳地重複單元。
術語"重複單元"意指組成重複單元(CRU),其為最小的組成單元,其重複作用組成規則巨分子、規則寡聚物分子、規則嵌段或規則鏈(PAC,1996,68,2291)。
術語"脫離基"意指從參與特定反應的分子的殘基或主要部分之原子脫離的原子或基團(有電荷或無電荷)(亦參見PAC,1994,66,1134)。
術語"經共軛的"意指主要地含有具有sp2
-混成(或隨意地亦為sp-混成)之C原子之化合物,其亦可被雜原子置換。於最簡單的案例中,此為,例如,具有交替C-C單鍵和雙(或三)鍵之分子,但亦包括具有像1,3-伸苯基之單元的化合物。"主要地"意指具有天然(自發地)存在缺點(其可導致共軛中斷)之化合物仍被視為經共軛的化合物(“Mainly" means in this connection that a compound with naturally(spontaneously)occurring defects,which may lead to interruption of the conjugation,is still regarded as a conjugated compound.)。
除非另有所指否則,所給予的分子量視為數量平均分子量Mn
,其係藉由凝膠滲透層析術(GPC)對照聚苯乙烯標準而測量的。聚合程度(n)意指聚合作用的數量平均程度,以n=Mn
/MU
表示,其中MU
為單一重複單元的分子量。
術語"二價碳基",如上面和下面所使用,表示任何單價或多價有機基團部分,該有機基團部分包括至少一個碳原子,或者無任何非碳原子(像,例如,-C≡C-),或隨意地與至少一個非碳原子(例如N、O、S、P、Si、Se、As、Te或Ge)組合(例如,羰基等等)。術語"烴基"表示額外地含有一或多個H原子和隨意地含有一或多個雜原子(像,例如,N、O、S、P、Si、Se、As、Te或Ge)之二價碳基。
含有3或更多個C原子鏈的二價碳基或烴基亦可為線性、支鏈和/或包括螺和/或稠合環之環狀。
較佳的二價碳基和烴基包括烷基、烷氧基、烷基羰基、烷氧基羰基、烷基羰基氧基和烷氧基羰基氧基,其各自隨意地經取代且具有1至40,較佳地1至25,非常佳地1至18個C原子,和具有6至40,較佳地6至25個C原子之隨意地經取代的芳基或芳氧基,和烷基芳基氧基、芳基羰基、芳基氧基羰基、芳基羰基氧基和芳基氧基羰基氧基,其各自隨意地經取代且具有6至40,較佳地7至40個C原子。
二價碳基或烴基可為飽和或不飽和的非環狀基團、或飽和或不飽和的環狀基團。不飽和的非環狀或環狀基團為較佳的,特別是芳基、烯基和炔基(特別是乙炔基)。當C1
-C40
二價碳基或烴基為非環狀,該基團可為線性或支鏈。C1
-C40
二價碳基或烴基包括,例如:C1
-C40
烷基、C2
-C40
烯基、C2
-C40
炔基、C3
-C40
烯丙基、C4
-C40
烷二烯基(alkyldienyl)、C4
-C40
多烯基、C6
-C18
芳基、C2
-C18
雜芳基、C6
-C40
烷基芳基、C6
-C40
芳基烷基、C4
-C40
環烷基、C4
-C40
環烯基等等。前面基團中較佳者分別為C1
-C20
烷基、C2
-C20
烯基、C2
-C20
炔基、C3
-C20
烯丙基、C4
-C20
烷二烯基、C6
-C12
芳基、C2
-C12
雜芳基和C4
-C20
多烯基。亦包括具有碳原子之基團和具有雜原子之基團的組合,像,例如,炔基,較佳地乙炔基,其經矽基取代,較佳地三烷基矽基。
另外較佳的二價碳基和烴基包括具有1至40,較佳地1至25個C-原子之直鏈、支鏈或環狀烷基,其為未經取代、經F、Cl、Br、I或CN單-或多取代,和其中一或多個非相鄰CH2
基團隨意地,於每一案例中,彼此獨立地,經-O-、-S-、-NH-、-NR0
-、-SiR0
R00
-、-CO-、-COO-、-OCO-、-O-CO-O-、-S-CO-、-CO-S-、-SO2
-、-CO-NR0
-、-NR0
-CO-、-NR0
-CO-NR00
-、-CY1
=CY2
-或-C≡C-置換,使得O和/或S原子彼此不直接連接,其中Y1
和Y2
彼此獨立地為H、F、Cl或CN,且R0
和R00
彼此獨立地為H或具有1至20個C原子之隨意地經取代的脂族或芳香族烴。
R0
和R00
較佳地選自H、具有1至12個C原子之直鏈或支鏈烷基、或具有6至12個C原子之芳基。
-CY1
=CY2
-較佳地為-CH=CH-、-CF=CF-或-CH=C(CN)-。
鹵素為F、Cl、Br或I。
較佳的烷基包括但不限於,甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、2-甲基丁基、正戊基、第二戊基、環戊基、正己基、環己基、2-乙基己基、正庚基、環庚基、正辛基、環辛基、十二基、十四基、十六基、三氟甲基、全氟-正丁基、2,2,2-三氟乙基、全氟辛基、全氟己基等等。
較佳的烯基包括但不限於,乙烯基、丙烯基、丁烯基、戊烯基、環戊烯基、己烯基、環己烯基、庚烯基、環庚烯基、辛烯基、環辛烯基等等。
較佳的炔基包括但不限於,乙炔基、丙炔基、丁炔基、戊炔基、己炔基、辛炔基等等。
較佳的烷氧基包括但不限於,甲氧基、乙氧基、2-甲氧基乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第二丁氧基、第三丁氧基、2-甲基丁氧基、正戊氧基、正己氧基、正庚氧基、正辛氧基等等。
較佳的胺基包括但不限於,二甲基胺基、甲基胺基、甲基苯基胺基、苯基胺基等等。
芳基可為單核,即,具有只有1個芳香族環(像,例如,苯基或伸苯基)、或多核,即,具有2或更多個芳香族環,其可為稠合(像,例如,萘基或伸萘基)、個別共價地連接(像,例如,聯苯基)、和/或稠合和個別連接的芳香族環兩者的組合。較佳地,芳基為芳香族基團,該芳香族基團實質上整個基團實質上為共軛的。
芳基和雜芳基較佳地表示具有至多25個C原子之單-、雙-或三環芳香族或雜芳香族基團,其亦可包括縮合環和隨意地經取代。
較佳的芳基包括但不限於,苯、聯伸二苯、聯伸三苯、[1,1':3',1"]聯三苯基-2'-伸基、伸萘基、蒽、伸聯萘基(binaphthylene)、菲、芘、二氫芘、、苝、四、稠五苯、苯並芘、茀、茚、茚並茀、螺聯茀等等。
較佳的雜芳基包括但不限於,5-員環如吡咯、吡唑、咪唑、1,2,3-三唑、1,2,4-三唑、四唑、呋喃、噻吩、硒吩、唑、異唑、1,2-噻唑、1,3-噻唑、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑,6-員環如吡啶、嗒、嘧啶、吡、1,3,5-三、1,2,4-三、1,2,3-三、1,2,4,5-四、1,2,3,4-四、1,2,3,5-四,和稠合系統如咔唑、吲哚、異吲哚、吲、吲唑、苯並咪唑、苯並三唑、嘌呤、萘並咪唑、啡並咪唑、吡啶並咪唑、吡並咪唑、喹啉並咪唑、苯並唑、萘並唑、蒽並唑、啡並唑、異唑、苯並噻唑、苯並呋喃、異苯並呋喃、二苯並呋喃、喹啉、異喹啉、喋啶、苯並-5,6-喹啉、苯並-6,7-喹啉、苯並-7,8-喹啉、苯並異喹啉、吖啶、啡噻、啡、苯並嗒、苯並嘧啶、喹啉、啡、啶、氮咔唑(azacarbazole)、苯並咔啉、啡啶、啡啉、噻吩並[2,3b]噻吩、噻吩並[3,2b]噻吩、二噻吩並噻吩、二噻吩並吡啶、異苯並噻吩、二苯並噻吩、苯並噻二唑並噻吩、或其組合。雜芳基可經烷基、烷氧基、硫烷基、氟、氟烷基或另外的芳基或雜芳基取代基取代。
較佳的芳基烷基包括但不限於,2-甲苯基、3-甲苯基、4-甲苯基、2,6-二甲基苯基、2,6-二乙基苯基、2,6-二-異丙基苯基、2,6-二-第三丁基苯基、o-第三丁基苯基、m-第三丁基苯基、p-第三丁基苯基、4-苯氧基苯基、4-氟苯基、3-羰基甲氧基苯基、4-羰基甲氧基苯基等等。
較佳的烷基芳基包括但不限於,苯甲基、乙基苯基、2-苯氧基乙基、丙基苯基、二苯基甲基、三苯基甲基或萘基甲基(naphthalinylmethyl)。
較佳的芳基氧基包括但不限於,苯氧基、萘氧基、4-苯基苯氧基、4-甲基苯氧基、聯苯基氧基、蒽基氧基、菲基氧基等等。
芳基、雜芳基、二價碳基和烴基隨意地包括一或多個取代基,較佳地選自矽基、磺酸基、磺醯基、甲醯基、胺基、亞胺基、氮基(nitrilo)、巰基、氰基、硝基、鹵素、C1-12
烷基、C6-12
芳基、C1-12
烷氧基、羥基和/或其組合。隨意的取代基可包括前述基團中的相同基團和/或複數個基團(較佳地2個)的所有化學上可能組合(例如,胺基和磺醯基,若彼此直接連接,則表示胺磺醯基)。
較佳的取代基包括但不限於,F、Cl、Br、I、-CN、-NO2
、-NCO、-NCS、-OCN、-SCN、-C(=O)NR0
R00
、-C(=O)X0
、-C(=O)R0
、-NR0
R00
、隨意地經取代的矽基、具有6至40(較佳地6至20個)C原子之芳基、具有2至40(較佳地2至20個)C原子之雜芳基、和具有1至20(較佳地1至12個)C原子之直鏈或支鏈烷基、烷氧基、烷基羰基、烷氧基-羰基、烷基羰基氧基或烷氧基羰基氧基,其中一或多個H原子隨意地經F或Cl置換,其中R0
和R00
為如上所定義者,和X0
為鹵素。
特別地,較佳的取代基係選自烷基、烷氧基、烯基、氧烷基、硫烷基、氟烷基和氟烷氧基,係如針對下面較佳基團R1,2
所定義者。
若R1-4
中之一者為烷基或烷氧基,即,其中終端CH2
基團被-O-置換,此可為直鏈或支鏈。較佳者為具有2至8個碳原子之直鏈且據此較佳地為乙基、丙基、丁基、戊基、己基、庚基、辛基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、庚氧基、或辛氧基,此外例如,甲基、壬基、癸基、十一基、十二基、十三基、十四基、十五基、壬氧基、癸氧基、十一氧基、十二氧基、十三氧基、或十四氧基。特別地,較佳者為正己基和正十二基。
若R1-4
中之一者為烷基,其中一或多個CH2
基團經-CH=CH-置換,此可為直鏈或支鏈。較佳者為具有2至12個C-原子之直鏈且據此較佳地為乙烯基,丙-1-或丙-2-烯基,丁-1-、2-或丁-3-烯基,戊-1-、2-、3-或戊-4-烯基,己-1-、2-、3-、4-或己-5-烯基,庚-1-、2-、3-、4-、5-或庚-6-烯基,辛-1-、2-、3-、4-、5-、6-或辛-7-烯基,壬-1-、2-、3-、4-、5-、6-、7-或壬-8-烯基,癸-1-、2-、3-、4-、5-、6-、7-、8-或癸-9-烯基,十一-1-、2-、3-、4-、5-、6-、7-、8-、9-或十一-10-烯基,十二-1-、2-、3-、4-、5-、6-、7-、8-、-9、-10或十二-11-烯基。烯基可包括具有E-或Z-構形或其混合物之C=C-鍵。
若R1-4
中之一者為氧烷基,即,當1個CH2
基團被-O-置換,較佳地為例如,直鏈2-氧丙基(=甲氧基甲基),2-(=乙氧基甲基)或3-氧丁基(=2-甲氧基乙基),2-、3-、或4-氧戊基,2-、3-、4-、或5-氧己基,2-、3-、4-、5-、或6-氧庚基,2-、3-、4-、5-、6-或7-氧辛基,2-、3-、4-、5-、6-、7-或8-氧壬基,或2-、3-、4-、5-、6-、7-、8-或9-氧癸基。
若R1-4
中之一者為硫烷基,即,當1個CH2
基團被-S-置換,較佳地為直鏈硫甲基(-SCH3
)、1-硫乙基(-SCH2
CH3
)、1-硫丙基(=-SCH2
CH2
CH3
)、1-(硫丁基)、1-(硫戊基)、1-(硫己基)、1-(硫庚基)、1-(硫辛基)、1-(硫壬基)、1-(硫癸基)、1-(硫十一基)或1-(硫十二基),其中較佳地,相鄰至sp2
混成乙烯基碳原子之CH2
基團被置換。
若R1-4
中之一者為氟烷基或氟烷氧基,較佳者為直鏈基團(O)Ci
F2i+1
,其中i為從1至15之整數,特別是CF3
、C2
F5
、C3
F7
、C4
F9
、C5
F11
、C6
F13
、C7
F15
或C8
F17
,非常佳地C6
F13
、或相對應的氟烷氧基。
若基團R1
和R2
和/或基團R3
和R4
一起與茀基團形成螺基團,較佳者為螺聯茀。
式I的較佳單元為該等,其中
- Ar為單鍵或隨意地經取代的單核或多核芳基,非常佳地為單鍵,
- Ar係選自隨意地經取代的茚並茀、隨意地經取代的螺聯茀、隨意地經取代的9,10-二氫菲或隨意地經取代的菲,
- m為<10,非常佳地為1、2、3、4或5,最佳地為1,
- A'為CR1
R2
,B為CR3
R4
,Ar為單鍵,和m較佳地為1,
- A'為CR1
R2
,B'為CR3
R4
,Ar為單鍵,和m較佳地為1,
- R1-4
表示隨意地經取代的二價碳基或烴基,非常佳地為隨意地經取代的烷基、芳基或雜芳基。
於式I單元(其中m>1)中,於每一茚並茀基團中的B和B'的意義彼此獨立地選自茚並茀基團。因此,式I單元可專門地由稠合的順式-茚並茀基團所組成,或可專門地由稠合的反式-茚並茀基團所組成,或可包括稠合的順式-和反式-茚並茀基團的交替或隨意順序。
式I單元較佳地選自下面亞化學式:
其中R1-4
為如式I中所定義者,R和R5-8
彼此獨立地具有於式I中針對R1
所給予的定義中之一者,r為0、1、2、3或4,t為0、1或2,且u為0、1、2或3。
式I的特佳單元係選自下面亞化學式:
其中L為H、鹵素或具有1至12個C原子之隨意地經氟化、線性或支鏈烷基或烷氧基,且較佳地為H、F、甲基、異丙基、第三丁基、正戊氧基、或三氟甲基,且L'為具有1至12個C原子之隨意地經氟化、線性或支鏈烷基或烷氧基,且較佳地為正辛基或正辛氧基。
Ar1
和Ar2
於式II中較佳地選自1,4-伸苯基,其中1、2或3個CH基團隨意地被N置換,和其隨意地經一或多個如上定義的基團R1
取代。另外,較佳者為式II單元,其中Ar1
為單鍵。
Ar1-3
於式II中較佳地選自苯基,其中1、2或3個CH基團隨意地被N置換,和其隨意地經一或多個如上定義的基團R1
取代。
k於式II中非常佳地為1。
Y於式II中非常佳地為N。
式II單元較佳地選自下面亞化學式:
其中R和r為如上面所定義者,且s為0、1、2、3、4或5。
式II的特佳單元係選自下面亞化學式:
其中L和L'為如上面所定義者,L較佳地為異丙基、第三丁基或三氟甲基,和L'較佳地為正辛基或正辛氧基。
較佳地,共聚物係由一或多種(較佳地一、二或三種,最佳地一種)類型的式I單元,和一或多種(較佳地一、二或三種,最佳地為一種)類型的式II單元。
式I單元於共聚物中的比例的上限較佳地為99莫耳%,更佳地90%。式I單元於共聚物中的比例的下限較佳地為55莫耳%,更佳地65莫耳%,最佳地75莫耳%。
式II單元於共聚物中的比例的上限較佳地為45莫耳%,更佳地35莫耳%,最佳地25莫耳%。式II單元於共聚物中的比例的下限較佳地為1莫耳%,最佳地10莫耳%。
除了式I和II的單元之外,如上面和下面所述,共聚物亦可包括一或多種(較佳地一種)額外類型的單元,較佳地選自具有電洞或電子傳輸性質之單元。
具有電子傳輸性質之額外單元較佳地選自下面化學式:
其中R和R'為如上面所定義者,且較佳地為H、烷基、芳基、全氟烷基、硫烷基、氰基、烷氧基、雜芳基、烷基芳基或芳基烷基。
R較佳地為H、苯基或具有1、2、3、4、5或6個C原子之烷基。R'較佳地為正辛基或正辛氧基。
本發明共聚物包括統計(statistical)或雜亂共聚物、交替共聚物和嵌段共聚物、及其組合。
特別佳者為雜亂和嵌段共聚物,其包括,非常佳地係由,>50莫耳%的一或多種式I單元和>0莫耳%且<50莫耳%的一或多種式II單元,所組成。
最佳者為共聚物,其專門地由>50莫耳%的一種類型的式I單元和>0莫耳%且<50莫耳%的一種類型的式II單元所組成。
共聚物較佳地選自下面化學式:
其中U1
為式I單元或其較佳亞化學式,U2
為式II單元或其較佳亞化學式,x 為>0.5且<1,y 為>0且<0.5,x+y 為1。
式1的較佳聚合物係選自下面亞化學式:
其中R1-4
、R、R'、r、s、x和y為如上面所定義者。
於本發明聚合物中,重複單元的總數量n較佳地為,非常佳地為,且較佳地為至多2,000,非常佳地為至多5,000,最佳地為至多10,000。
本發明聚合物可藉由任何適當的方法製備。例如,其可藉由芳基-芳基偶合反應,例如山本(Yamamoto)偶合、鈴木(Suzuki)偶合、Stille偶合、園頭(Sonogashira)偶合或Heck偶合而適當地製備。鈴木偶合和山本偶合為特佳的。
被聚合以形成本發明聚合物的重複單元的單體可依據專家已知且已揭示於文獻中的適當方法製備。製備式I之茚並茀單體的適當且較佳的方法被描述,例如,於WO 2004/041901 A1和 WO 2006/015862 A1。製備式II之三芳基胺單體的適當且較佳的方法被描述,例如,於WO 99/54385 A1。
較佳地,聚合物係從含有上述式I-IX基團中之一者之單體予以製備,該聚合物被連接至2個可聚合的基團P。據此,例如,可使用選自下面化學式之茚並茀和三芳基胺單體:
其中P1
和P2
彼此獨立地為可聚合的或反應性基團,且A、A'、B、B'、Ar、Y、Ar1-3
、R、R1-4
、k、m、r和s為如上面所定義者。其它共單體可據此被建立。
較佳地,基團P1,2
彼此獨立地選自Cl、Br、I、O-甲苯磺酸酯、O-三氟甲磺酸酯、O-甲磺酸酯、O-九氟丁磺酸酯、-SiMe2
F、-SiMeF2
、-O-SO2
Z、-B(OZ1
)2
、-CZ2
=C(Z2
)2
、-C≡CH和-Sn(Z3
)3
,其中Z和Z1-3
係選自烷基和芳基,其各自隨意地經取代的,且2個基團Z1
亦可形成環狀基團。
本發明的另一方面為製備聚合物之方法,其係藉由在聚合反應中,使一或多種基於式I單元之單體與一或多種基於式II單元之單體偶合,和隨意地與一或多種另外的單元(例如選自式III-IX)偶合。
聚合的較佳方法為該等導致C-C偶合或C-N偶合者,如鈴木聚合作用,如被描述於例如WO 00/53656,山本聚合作用,如被描述於例如山本等人,Progress in Polymer Science 1993,17,1153-1205或於WO 2004/022626 A1,和Stille偶合。例如,當藉由山本聚合作用合成線性聚合物,較佳地使用如上述之具有2個反應性鹵化物基團P1,2
之單體。當藉由鈴木聚合作用合成線性聚合物,較佳地使用如上述之單體,其中至少一個反應性基團P1,2
為硼酸或硼酸衍生物基團。
可使用鈴木聚合作用製備統計、交替和嵌段、雜亂共聚物。特別地,統計或嵌段共聚物可從上面單體製備,其中反應性基團P1
和P2
中之一者為鹵素,且其它反應性基團為硼酸或硼酸衍生物基團。統計、交替和嵌段共聚物的合成被詳細描述例如於WO 03/048225 A2或WO 2005/014688 A2。
鈴木聚合作用使用Pd(0)錯合物或Pd(II)鹽。較佳的Pd(0)錯合物為該等帶有至少一個膦配位基者,例如Pd(Ph3
P)4
。另一較佳的膦配位基為三(鄰-甲苯基)膦,即,Pd(o-Tol)4
。較佳的Pd(II)鹽類包括乙酸鈀,即,Pd(OAc)2
。鈴木聚合作用係在鹼(例如,碳酸鈉、磷酸鉀)或有機鹼(例如,碳酸四乙銨)存在下進行。山本聚合作用使用Ni(0)錯合物,例如,雙(1,5-環辛二烯基)鎳(0)。
作為如上述之鹵素的替代者,可使用式-O-SO2
Z之脫離基,其中Z為如上述者。此等脫離基的特定實例為甲苯磺酸酯、甲磺酸酯和三氟甲磺酸酯。
有機電子裝置為,例如,有機場效電晶體(OFET)、薄膜電晶體(TFT)、積體電路(IC)、射頻識別(RFID)標籤、光偵測器、感測器、邏輯電路、記憶元件、電容器、有機光伏打(OPV)電池、電荷注入層、電荷傳輸層、肖特基二極體(Schottky diode)、平面化層、抗靜電膜、聚合物電解質膜(PEM)、傳導基板或圖案、光導體、電子照像元件或有機發光二極體(OLED)。
本發明之OFET裝置較佳地包括:
-隨意地基板,
-閘極電極,
-介電絕緣層,
-半導體層,
-源極電極,
-汲極電極。
其中半導體層包括一或多種如上面和下面所述之共聚物。
閘極電極、源極電極和汲極電極及絕緣層和半導體層於OFET裝置中可以任何順序配置,但先決條件是,源極電極和汲極電極藉由絕緣層而與閘極電極分開,閘極電極和半導體層兩者接觸絕緣層,及源極電極和汲極電極兩者接觸半導體層。
較佳地,電子裝置為OFET,該OFET包括介電絕緣層、與介電層的一個表面接觸之閘極電極、與正面遠離閘極電極之介電層的表面接觸之半導體層、及與正面遠離介電層之半導體層的表面接觸之汲極電極和源極電極。
OFET較佳地為頂部閘極裝置或底部閘極裝置。
OFET裝置的適當結構和製造方法為熟習該項技術者已知且被描述於文獻中,例如於WO 03/052841。
有機半導體層較佳地少於30微米厚度。典型地,半導體層至多1微米(=1μm)厚度,雖然若需要其可更厚。對各種電子裝置應用而言,厚度亦可少於1微米。關於在OFET之用途,層厚度典型地為500nm或更小,關於在OLED之用途,典型地為100nm或更小。層的確切厚度將取決於,例如,使用該層的電子裝置的要求。
一般地,本發明電子裝置中功能層的厚度範圍可從1nm(於單層的案例中)至10μm,較佳地從1nm至1μm,更佳地從1nm至500nm。
有機半導體層可藉由任何適當的方法沈積。液態塗覆是比真空沈積技術為更想要的。溶液沈積方法為特佳的。較佳的沈積技術包括但不限於,浸塗、旋轉塗佈、噴墨列印、凸版印刷、網板印刷、刮刀塗佈、滾筒印刷、反轉輥印刷、平版微影印刷(offset lithography printing)、柔性凸版印刷(flexographic printing)、網頁列印(web printing)、噴霧塗佈、刷塗或移印。噴墨列印為特佳的。
有機半導體層較佳地由含有共聚物和一或多種有機溶劑之調合物,非常佳地溶液或分散液,沈積。
適當且較佳的有機溶劑的實例包括但不限於,二氯甲烷、三氯甲烷、單氯苯、鄰-二氯苯、四氫呋喃、苯甲醚、味啉、甲苯、鄰-二甲苯、間-二甲苯、對-二甲苯、1,4-二、丙酮、甲基乙基酮、1,2-二氯乙烷、1,1,1-三氯乙烷、1,1,2,2-四氯乙烷、乙酸乙酯、乙酸正丁酯、二甲基甲醯胺、二甲基乙醯胺、二甲基亞碸、萘滿、十氫萘、二氫茚和/或其混合物。
共聚物於調合物中的總濃度較佳地為0.1至10重量%,更佳地0.5至5重量%。
適當的混合和老化之後,評定溶液為下面種類中之一者:完全溶液、邊界溶液(borderline solution)或不溶。繪製外形線(contour line)以畫出區分為溶解度和不溶性之溶解度參數-氫結合限制。落在溶解度面積內之'完全'溶劑可選自文獻值,例如被公開於"Crowley、J.D.、Teague、G.S. Jr and Lowe、J.W. Jr.、Journal of Paint Technology、38、No 496、296(1966)"。溶劑摻合物亦可被使用且可被鑑定為如"Solvents,W.H.Ellis,Federation of Societies for Coatings Technology、p9-10,1986"中所述者。此一程序亦可導致將溶解本發明兩種聚合物之'非'溶劑的摻合物,雖然想要在摻合物中有至少一種真溶劑。
溶液較佳地藉由噴墨列印或微分配(microdispensing)而被施用至預先製造的裝置基板。較佳地,使用工業上壓電式列印頭,例如但不限於,Aprion、Hitachi-Koki、InkJet Technology、On Target Technology、Picojet、Spectra、Trident、Xaar所供應者。可使用另外的準工業頭(semi-industrial heads),例如,Brother、Epson、Konica、Seiko Instruments Toshiba TEC所製造者,或單一噴嘴微分配器,例如,Microdrop and Microfab所製造者。
用於噴墨列印或微分配之適當溶劑必須滿足上述之要求且必須對所選擇之列印頭不具有任何不利的作用。此外,溶劑應具有>100℃(較佳地>140℃且更佳地>150℃)之沸點,以防止溶液在列印頭內部變乾所引起的操作問題。除上述溶劑之外,適當的溶劑包括經取代和未經取代的二甲苯衍生物、二-C1
-2
-烷基甲醯胺、經取代和未經取代的苯甲醚和其它酚-醚衍生物、經取代的雜環(例如,經取代的吡啶、吡、嘧啶、吡咯啶酮)、經取代和未經取代的N
,N
-二-C1
-2
-烷基苯胺和其它氟化或氯化的芳香族。
用於藉由噴墨列印而沈積本發明共聚物之較佳溶劑包括苯衍生物,其具有經一或多個取代基取代的苯環,其中於一或多個取代基中,碳原子的總數目為至少3個。例如,苯衍生物可經丙基或3個甲基取代,不論在哪一情況中,總共有至少3個碳原子。此一溶劑能使欲形成之噴墨流體含有溶劑與聚合物,該溶劑減少或預防在噴塗期間噴嘴阻塞和成分分離。溶劑可包括選自下面實例者:十二基苯、1-甲基-4-第三丁基苯、烯醇、薴烯、異荰、1,4(8)-對二烯(terpinolene)、對異丙甲苯、二乙基苯。溶劑可為溶劑混合物,該混合物為二或多種溶劑之組合,每一溶劑較佳地具有>100℃(更佳地>140℃)之沸點。此溶劑亦在沈積層中增加膜形成和減少層中的缺陷。
噴墨流體(其為溶劑、黏合劑和半導體化合物之混合物)在20℃的黏度較佳地為1-100mPa‧s,更佳地為1-50mPa‧s和最佳地為1-30mPa‧s。
有機半導體調合物可額外地包括一或多種另外成分,像例如,表面活性化合物、潤滑劑、潤濕劑、分散劑、疏水劑、黏合劑、流動改善劑、消泡劑、除氣劑、可為反應性或無反應性之稀釋劑、助劑、著色劑、染料或顏料、敏化劑、安定劑、奈米顆粒或抑制劑。
於本發明的另一較佳具體例中,用於其沈積作用之有機半導體層或調合物包括一或多種有機黏合劑以調整其流變性質,如例如WO 2005/055248 A1中所述。
電子裝置的其它組件,像基板、介電層和電極,可選自標準材料和可藉由標準方法而予以製造和應用至裝置。這些組件和層的適當材料和製造方法為此項技術者所周知且被描述於文獻。
沈積方法包括液體塗覆和蒸汽或真空沈積。較佳的沈積技術包括但不限於,浸塗、旋轉塗佈、噴墨列印、凸版印刷、網板印染、刮刀塗佈、滾筒印刷、反轉輥印刷、平版微影印刷、柔性凸版印刷、網頁列印、噴霧塗佈、刷塗或移印。噴墨列印是特佳的,其可製備高解析層和裝置。
可使用各種基板以製備有機電子裝置,例如,玻璃或塑膠,塑膠材料為較佳的,實例包括酸醇樹脂、烯丙基酯、苯並環丁烯、丁二烯-苯乙烯、纖維素、纖維素乙酸酯、環氧化物、環氧聚合物、乙烯-氯三氟乙烯、乙烯-四氟乙烯、玻璃纖維強化的塑膠、氟碳聚合物、六氟丙烯亞乙烯-氟化物共聚物、高密度聚乙烯、聚對二甲苯基、聚醯胺、聚醯亞胺、聚芳醯胺、聚二甲基矽氧烷、聚醚碸、聚乙烯、聚萘二酸乙二醇酯、聚對苯二甲酸乙二醇酯、聚酮、聚甲基丙烯酸甲酯、聚丙烯、聚苯乙烯、聚碸、聚四氟乙烯、聚胺基甲酸酯、聚氯乙烯、矽氧橡膠、聚矽氧。較佳的基板材料為聚對苯二甲酸乙二醇酯、聚醯亞胺、和聚萘二酸乙二醇酯。基板可為任何塑膠材料、金屬或塗覆上述材料之玻璃。基板應較佳地為均質,以保證良好的圖案清晰。基板亦可藉由擠壓、拉伸、摩擦或藉由光化學技術而被均勻地預先配向(pre-aligned),以引起有機半導體的定向,以增加載子移動率。
電極可藉由液體塗覆,例如,噴霧-、浸泡-、網狀-或旋轉-塗覆,或藉由真空沈積或蒸汽沈積方法,予以沈積。適當的電極材料和沈積方法為熟習該領域者所周知的。適當的電極材料,包括但不限於,無機材料或有機材料、或兩者之複合物。
適當電極材料的實例包括聚苯胺、聚吡咯、PEDOT或經摻雜的共軛聚合物、石墨的另外分散液或糊、或金屬粒子如Au、Ag、Cu、Al、Ni或其混合物,及經噴濺塗覆或經蒸鍍的金屬,像例如Cu、Cr、Pt/Pd等等,和半導體,像例如ITO。有機金屬前驅物亦可被使用且從液相沈積(Organometallic precursors may also be used deposited from a liquid phase)。
用於絕緣層之介電材料可為無機或有機,或兩者的複合物。較佳的是,絕緣體為可環境加工(ambient processing)之溶液塗覆,且亦可藉由各種真空沈積技術予以沈積。當絕緣體被圖案化,其可表現中間層絕緣體的功能或作為OFET的閘極絕緣體。較佳的沈積技術,包括但不限於,浸塗、旋轉塗佈、噴墨列印、凸版印刷、網板印染、刮刀塗佈、滾筒印刷、反轉輥印刷、平版微影印刷、柔性凸版印刷、網頁列印、噴霧塗佈、刷塗或移印。噴墨列印為特佳的,其可製備高解析層和裝置。隨意地,介電材料可被交聯或固化,以達到較好的抗溶劑性和/或結構整體性,和/或能圖案化(光微影)。較佳的閘極絕緣體為對OSC提供低介電常數界面者。
適當且較佳的有機介電材料包括但不限於,氟化的對-二甲苯、氟聚芳基醚、氟化的聚醯亞胺聚苯乙烯、聚(α-甲基苯乙烯)、聚(α-乙烯萘)、聚(乙烯基甲苯)、聚乙烯、順式-聚丁二烯、聚丙烯、聚異戊二烯、聚(4-甲基-1-戊烯)、聚(4-甲基苯乙烯)、聚(氯三氟乙烯)、聚(2-甲基-1,3-丁二烯)、聚(對-茬)、聚(α-α-α'-α'四氟-對-茬)、聚[1,1-(2-甲基丙烷)雙(4-苯基)碳酸酯]、聚(環己基甲基丙烯酸酯)、聚(氯苯乙烯)、聚(2,6-二甲基-1,4-伸苯基醚)、聚異丁烯、聚(乙烯基環己烷)、聚(乙烯基桂皮酸酯)、聚(4-乙烯基聯苯基)、聚(1,3-丁二烯)、聚苯烯。另外的較佳者為共聚物,包括規則、雜亂或嵌段共聚物,像聚(乙烯/四氟乙烯)、聚(乙烯/氯三氟-乙烯)、氟化乙烯/丙烯共聚物、聚苯乙烯-co-α-甲基苯乙烯、乙烯/丙烯酸乙酯共聚物、聚(苯乙烯/10%丁二烯)、聚(苯乙烯/15%丁二烯)、聚(苯乙烯/2,4-二甲基苯乙烯)。另外的較佳者為購自Topas系列(Ticona)之聚合物、聚環烯烴像購自Avatrel系列(Promerus LLC)者、和高度可溶解的全氟聚合物像購自Cytop系列(Asahi Glass)或Teflon AF系列(DuPont)者。
關於特定的裝置,其可較佳地使用具有高介電常數之介電材料。此類型的適當且較佳的有機介電材料,包括但不限於,例如,聚乙烯醇、聚乙烯酚、聚甲基丙烯酸甲酯、氰基乙基化的多醣如氰基乙基聚三葡萄糖、高介電常數之氟聚合物如聚二氟亞乙烯、聚胺基甲酸酯聚合物和聚(氯乙烯/乙酸乙烯酯)聚合物。此類型的適當且較佳的無機介電材料,包括但不限於,例如,TiO2
、Ta2
O5
、SrTiO3
、Bi4
Ti3
O12
、BaMgF4
、酒石酸鋇鋯或酒石酸鋇鍶的複合物。
於本發明的較佳具體例中,絕緣層包括或由具有低介電常數(較佳地具有從1.1至低於3.0之相對介電常數)之有機介電材料所組成,如例如描述於WO 03/052841。用於此具體例之適當且較佳的材料,包括但不限於,聚丙烯、聚異丁烯、聚(4-甲基-1-戊烯)、聚異戊二烯、聚(乙烯基環己烷)、或含有這些材料中之至少一者的單體單元的共聚物、聚環烯烴像購自Avatrel系列者、和氟聚合物,特別是購自Cytop或TeflonAF系列者。
較佳地,絕緣層包括氟聚合物,像例如,購買的Cytop 809M或Cytop 107M(來自Asahi Glass)。較佳地,閘極絕緣層,例如,藉由旋轉塗佈、刮刀塗佈、塗佈棒塗佈、噴霧或浸塗、或其它已知方法,從含有絕緣材料和一或多種具有一或多個氟原子之溶劑(氟溶劑)(較佳地為全氟溶劑)之調合物沈積。適當的全氟溶劑為,例如,FC75(購自Acros,目錄號碼12380)。其它適當的氟聚合物和氟溶劑為先前技藝所周知的,像例如,全氟聚合物Teflon AF1600或2400(購自DuPont)或Fluoropel(購自Cytonix)或全氟溶劑FC 43(Acros,No. 12377)。
另外的較佳者為含有本發明之場效電晶體之積體電路。
另外的較佳者為含有一或多種如上面或下面所述之共聚合物之光伏打電池。
本發明之OPV裝置較佳地包括:
-低功函數電極(例如,鋁),
-高功函數電極(例如,ITO),其中一者為透明,
-由電洞傳輸材料和電子傳輸材料所組成的雙層;雙層可以2個不同的層存在、或經摻合的混合物(參見,例如,Coakley、K. M. and McGehee、M. D.Chem. Mater. 2004、 16
、4533),
-隨意的傳導聚合物層(例如,PEDOT:PSS)以減輕高功函數電極的功函數,以提供電洞的歐姆接觸,
-在高功函數電極上的隨意塗層(例如,LiF),以提供電子的歐姆接觸。
於摻合物中的電洞傳輸材料為上面和下面所述之共聚物中之一者。電子傳輸材料可為無機材料,例如,氧化鋅或硒化鎘,或有機材料,例如,富勒烯(fullerene)衍生物(例如,PCBM、[(6,6)-苯基C61-丁酸甲酯]或聚合物(參見,例如,Coakley、K. M. and McGehee、M. D.Chem. Mater
. 2004
、16
、4533))。若雙層為摻合物,隨意的退火步驟可能是需要的以最佳化裝置性能。
除非內容清楚指明否則,如文中所使用,文中術語的複數形式被理解為包括單數形式,反之亦然。
遍及本說明書的發明說明和申請專利範圍,用語"包括"和"包含"和該用語的變體,例如"含有(comprising)(comprises)"意指“包括但不限於",且不打算(和不)排除其它成分。
將理解的是,本發明的前面具體例的變體可被達成,同時仍落在本發明的範圍內。除非另有說明否則,本說明書所述之每一特徵可被用於相同、等同或類似目的之替代特徵置換。因此,除非另有說明否則,所揭示的每一特徵僅為一般系列的等同或類似特徵的一個實例。
本說明書所揭示之所有特徵可以任何組合方式予以組合,除了至少一些此等特徵和/或步驟彼此獨有之組合。特別地,本發明的較佳特徵應用至本發明的所有方面,且可以任何組合方式使用。同樣地,於非必要的組合中所述之特徵可個別地使用(不以組合方式)。
將理解的是,許多上述之特徵(特定的較佳具體例)因其自身條件而被發明的,而非僅作為本發明的部分具體例。除了或替代任何本發明所主張者之外,可對這些特徵請求獨立保護。
下面實例用於說明本發明而非限制本發明。於前面和下面中,除非另有說明否則,所有溫度係以攝氏(Celsius)表示,且所有百分比皆以重量表示。
在N2
下,將N
,N
-雙[4-(4,4,5,5-四甲基-1,3,2-二氧硼(dioxaborolan)-2-基)苯基]-N
-(4-第二-丁基苯基)胺(2.70g、4.88mmol)、2,8-雙(4,4,5,5-四甲基-1,3,2-二氧硼-2-基)-6,6'12,12'-四辛基-6,12-二氫茚並-[1,2b
]茀(3.11g、3.25mmol)、2,8-二溴-6,6'12,12'-四辛基-6,12-二氫茚並-[1,2b
]茀(7.00g、8.13mmol)、磷酸鉀單水合物(8.24g、35.78mmol)和硼酸甲苯酯(9.9mg、0.061mmol)加到配有機械攪拌器和迴流冷凝器之1000cm3
RBF中。經除氣(N2
)的甲苯(81cm3
)、經除氣的1,4-二 (81cm3
)和經除氣的HPLC水(81cm3
)加到上述溶液中。接著混濁混合物被除氣(攪拌、通氣N2
)1小時。同時,預熱油浴至105℃,和製備觸媒的儲液[要求4.5倍量:乙酸鈀(II)(32.9mg、0.147mmol)和三(o
-甲苯基)膦(267.3mg、0.878mmol)於經除氣的1,4-二 (15.8cm3
)中,其於密封的玻璃瓶中除氣50分鐘]。反應混合物被除氣之後,除氣玻璃試管用1,4-二 (6cm3
)和甲苯(6cm3
)清洗,接著將燒瓶置入在105℃預熱的油浴中且10分鐘之後,加入觸媒溶液(3.5cm3
)。接著於黑暗中激烈攪拌反應混合物2小時。加入硼酸甲苯酯(31.3mg、0.193mmol),接著加入另外的觸媒溶液(3.5cm3
),且混合物在105℃受熱1小時。冷卻至65℃之後,加入二乙二硫胺甲酸鈉三水合物(81cm3
,10重量%)和甲苯(81cm3
),且混合物在65℃攪拌2小時。冷卻至23℃隔夜之後,將反應混合物倒到分液漏斗中,加入甲苯(200cm3
)。有機層用水清洗(3×500cm3
),有機層被分離且被沈降至甲醇中。聚合物被過濾收集且在真空下乾燥。聚合物溶於甲苯(200cm3
)和透過矽藻土墊與熱甲苯過濾。聚合物溶液從攪拌的甲醇(1200cm3
)沈澱,且聚合物被過濾收集、用甲醇清洗和在真空下乾燥,產生為淡黃色固體之產物(7.71g、80%)。GPC(PhCl在60℃):Mn
=99,000g mol-1
;Mw
=208,100g mol-1
。
製備場效電晶體,如下:在玻璃基板上,圖案化的Au源極電極和汲極電極藉由遮罩(shadow masking)而被提供。五氟苯-硫酚的自組裝單層(self assembling monolayer)(電子注入層)被旋轉塗佈在Au電極且用IPA清洗。半導體調合物係藉由將實例1之產物以1重量%濃度溶於三甲苯中而製備。半導體溶液接著在室溫於空氣中以500rpm持續3秒,接著2000rpm持續30秒而旋轉塗佈在基板上,和蒸發溶劑。接著將絕緣材料(Cytop809M,購自Asahi Glass)旋轉塗佈在半導體上,得到厚度近乎1μm,和蒸發溶劑。金閘極接觸(gold gate contact)藉由蒸發透過遮罩而在裝置隧道面積上確定界線。
關於電測量,電晶體樣品設置在樣品支架上。使用Karl Suss PH100微型探針-頭對閘極電極、汲極電極和源極電極進行微探針連接。此等被連接至Hewlett-Packard 4155B參數分析器。汲極電壓設定為-5V,且閘極電壓於1V步驟中掃瞄,從+20至-60V和回至+20V。ISD
(源極-汲極電流)對VG
(閘極電壓)特性顯示於圖1。
場效移動率值係在線性區(Lin mob)和飽和區(Sat mob)從ISD
對VG
特性的梯度計算。所有測量係在室溫空氣中進行。結果總結如下:
Lin mob=0.011cm2
/Vs
Sat mob=0.015cm2
/Vs
圖1顯示依據實例2所製備之OFET的源極-汲極電流對閘極電壓的特性。
Claims (10)
- 一種共軛共聚物,其包括>50莫耳%的一或多種相同或不同之式I單元
- 如申請專利範圍第1項之共聚物,其中式I單元係選自下面亞化學式:
- 如申請專利範圍第2項之共聚物,其中L為H、F、甲基、異丙基、第三丁基、正戊氧基、或三氟甲基。
- 如申請專利範圍第2項之共聚物,其中L'為正辛基或正辛氧基。
- 如申請專利範圍第1項之共聚物,其中式II單元係選自下面亞化學式:
- 如申請專利範圍第1項之共聚物,其中式I單元的比例的上限為90%,且式I單元的比例的下限為55莫耳%。
- 如申請專利範圍第1項之共聚物,其中式II單元的比例的上限為45莫耳%,且式II單元的比例的下限為10莫耳%。
- 如申請專利範圍第1項之共聚物,其只由>50莫 耳%的一種類型的式I單元和>0莫耳%且<50莫耳%的一種類型的式II單元所組成。
- 一種有機電子裝置,其包括如申請專利範圍第1項之共聚物。
- 如申請專利範圍第9項之有機電子裝置,其為有機場效電晶體(OFET)、薄膜電晶體(TFT)、積體電路(IC)、射頻識別(RFID)標籤、光偵測器、感測器、邏輯電路、記憶元件、電容器、有機光伏打(OPV)電池、電荷注入層、電荷傳輸層或聚合物發光二極體(PLED)中的中間層、肖特基二極體(Schottky diode)、平面化層、抗靜電膜、聚合物電解質膜(PEM)、傳導基板或圖案、光導體、電子照像元件或有機發光二極體(OLED)。
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DE102009030848A1 (de) * | 2009-06-26 | 2011-02-03 | Merck Patent Gmbh | Polymere enthaltend Struktureinheiten, die Alkylalkoxygruppen aufweisen, Blends enthaltend diese Polymere sowie optoelektronische Vorrichtungen enthaltend diese Polymere und Blends |
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DE102010007938A1 (de) * | 2010-02-12 | 2011-10-06 | Merck Patent Gmbh | Elektrolumineszierende Polymere, Verfahren zu ihrer Herstellung sowie ihre Verwendung |
US9206352B2 (en) * | 2010-05-27 | 2015-12-08 | Merck Patent Gmbh | Formulation and method for preparation of organic electronic devices |
GB201108864D0 (en) | 2011-05-26 | 2011-07-06 | Ct For Process Innovation The Ltd | Transistors and methods of making them |
GB201108865D0 (en) * | 2011-05-26 | 2011-07-06 | Ct For Process Innovation The Ltd | Semiconductor compounds |
TW201339138A (zh) * | 2012-01-20 | 2013-10-01 | Univ Southern California | 作為用於有機電子裝置之新穎n-型材料之氮雜-并苯之合成 |
JP6078998B2 (ja) * | 2012-06-20 | 2017-02-15 | 住友化学株式会社 | 高分子化合物およびそれを用いた発光素子 |
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US7666956B2 (en) | 2003-05-30 | 2010-02-23 | Merck Patent Gmbh | Polymer |
DE10340711A1 (de) * | 2003-09-04 | 2005-04-07 | Covion Organic Semiconductors Gmbh | Elektronische Vorrichtung enthaltend organische Halbleiter |
EP1627891A1 (en) * | 2004-08-11 | 2006-02-22 | Covion Organic Semiconductors GmbH | Polymers for use in organic electroluminescent devices |
GB2453457B (en) * | 2006-05-12 | 2011-06-01 | Merck Patent Gmbh | Indenofluorene polymer based organic semiconductor materials |
KR101412956B1 (ko) * | 2006-07-25 | 2014-07-09 | 메르크 파텐트 게엠베하 | 중합체 블렌드 및 유기 발광 장치에서의 이의 용도 |
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US8586684B2 (en) | 2013-11-19 |
EP2222749A1 (en) | 2010-09-01 |
JP2011505439A (ja) | 2011-02-24 |
US20100256328A1 (en) | 2010-10-07 |
CN101868490A (zh) | 2010-10-20 |
CN101868490B (zh) | 2014-06-04 |
GB2467498A (en) | 2010-08-04 |
GB2467498B (en) | 2012-11-28 |
WO2009065479A1 (en) | 2009-05-28 |
GB201009961D0 (en) | 2010-07-21 |
KR101532458B1 (ko) | 2015-06-29 |
KR20100100897A (ko) | 2010-09-15 |
TW200942560A (en) | 2009-10-16 |
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