TWI418571B - 可溶性聚噻吩衍生物 - Google Patents
可溶性聚噻吩衍生物 Download PDFInfo
- Publication number
- TWI418571B TWI418571B TW098116138A TW98116138A TWI418571B TW I418571 B TWI418571 B TW I418571B TW 098116138 A TW098116138 A TW 098116138A TW 98116138 A TW98116138 A TW 98116138A TW I418571 B TWI418571 B TW I418571B
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- TW
- Taiwan
- Prior art keywords
- soluble polythiophene
- polythiophene derivative
- mmol
- organic
- formula
- Prior art date
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- 229920000123 polythiophene Polymers 0.000 title claims description 21
- 229920005603 alternating copolymer Polymers 0.000 claims description 5
- 229920005604 random copolymer Polymers 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000010410 layer Substances 0.000 description 16
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 229930192474 thiophene Natural products 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 3
- 229920000547 conjugated polymer Polymers 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- 229920000144 PEDOT:PSS Polymers 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- -1 poly Poly(styrene-sulfonate) Polymers 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 150000003577 thiophenes Chemical class 0.000 description 2
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- WAQFYSJKIRRXLP-UHFFFAOYSA-N 2,4-dibromothiophene Chemical compound BrC1=CSC(Br)=C1 WAQFYSJKIRRXLP-UHFFFAOYSA-N 0.000 description 1
- QZVHYFUVMQIGGM-UHFFFAOYSA-N 2-Hexylthiophene Chemical compound CCCCCCC1=CC=CS1 QZVHYFUVMQIGGM-UHFFFAOYSA-N 0.000 description 1
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical group C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical group CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 210000003850 cellular structure Anatomy 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- RWXCVESEMJNNMF-UHFFFAOYSA-N oxadiazolo[5,4-b]pyridine Chemical compound C1=CN=C2ON=NC2=C1 RWXCVESEMJNNMF-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010248 power generation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Chemical group C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical compound C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- TULWUZJYDBGXMY-UHFFFAOYSA-N tellurophene Chemical compound [Te]1C=CC=C1 TULWUZJYDBGXMY-UHFFFAOYSA-N 0.000 description 1
- QKTRRACPJVYJNU-UHFFFAOYSA-N thiadiazolo[5,4-b]pyridine Chemical compound C1=CN=C2SN=NC2=C1 QKTRRACPJVYJNU-UHFFFAOYSA-N 0.000 description 1
- DTDZVQXOCHUQLZ-UHFFFAOYSA-N thiadiazolo[5,4-f]quinoxaline Chemical compound C1=CC2=NC=CN=C2C2=C1N=NS2 DTDZVQXOCHUQLZ-UHFFFAOYSA-N 0.000 description 1
- YJSKZIATOGOJEB-UHFFFAOYSA-N thieno[2,3-b]pyrazine Chemical compound C1=CN=C2SC=CC2=N1 YJSKZIATOGOJEB-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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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
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/145—Side-chains containing sulfur
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/148—Side-chains having aromatic units
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/149—Side-chains having heteroaromatic units
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/15—Side-groups conjugated side-chains
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
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Description
本發明係有關於一種具備共平面基團之可溶性聚噻吩衍生物，以及該可溶性噻吩衍生物於光電元件之應用。
高分子半導體材料(polymeric semiconductor material)因具有半導體與光電特性，可應用於許多光電元件上，如有機薄膜電晶體(organic thin-film transistor,OTFT)、有機太陽能電池(organic solar cell)、有機發光二極體(organic light emitting diode,OLED)與光感測器上。再加上材料本身具有高分子的特性，可藉由溶液塗佈技術製成光電元件的主動層薄膜，形成質輕、價格便宜、製程方便以及大面積化的可撓式光電元件。目前高分子半導體材料發展之主流以共軛高分子(conjugated polymer)為主，即主鏈以共軛型態相連。一般共軛高分子應用於光電元件上的主要缺點為載子遷移率(carrier mobility)較低，且吸光範圍較窄(400nm~650nm)所以侷限了元件的使用。因此有許多研究團隊相繼投入共軛高分子材料的合成，研發具有高載子遷移及更廣波域吸收的材料，進一步提升光電元件的效能。
在有機太陽能電池的應用上，其主動層材料也必需是高遷移率的電子與電洞傳輸材料，否則因為光激或電激生成之電荷會經由複合而消散，而降低有機太陽能電池的光電轉換效率(power conversion efficiency)。而於光吸收的部分，如能有效的增加材料的太陽光譜吸收能力，配合材料高載子遷移速度的話將有機會使有機太陽能電池效率有突破性發展。其發電原理，主要結合一電子予體(donor)與電子受體(acceptor)材料，以異質接面的技術，發展有機太陽能電池，配合發展各種高分子當電子予體材料，結合碳60當電子受體材料，例如：聚(3-己烷基噻吩)(P3HT)摻混苯基-碳61-丁酸甲酯(PCBM)，其光電轉換效率提升至3.5%。
上述提及的聚(3-己烷基噻吩)(P3HT)、聚(9,9-二辛基芴基-雙噻吩)(F8T2)及環戊二噻吩衍生物(PCPDTBT)的高分子是由噻吩衍生物聚合而成，其主鏈皆以噻吩類共軛環狀分子為主，故在高分子長鏈分子互相吸引下，幫助分子間的π-π作用力，進而提升材料的載子遷移率。在2006年Yongfang Li團隊，合成一側鏈共軛共平面噻吩聚合物，文獻中提到共軛的側鏈團基，有助於幫助增加材料廣波域吸收，且具備不錯的光電轉換效率。(詳細文獻請參見J. H. Hou,Z. A. Tan,Y. Yan,Y. J. He,C. H. Yang,Y. F. Li,Synthesis and photovoltaic properties of two-dimensional conjugated polythiophenes with bi(thienylenevinylene)side chains,J. Am. Chem. Soc
. 128(2006
)4911.
本發明提供一種可溶性聚噻吩衍生物，具有下列結構：
其中R為氫、烷基、羥基、醛基、酯基、鹵素、氰基(-CN)、亞硝酸基(-NO2
)、胺基、或取代或未取代之芳香基；Ar為取代或未取代之芳香烴基、取代或未取代之雜芳香烴基、或上述之組合；m介於2～100之間；n介於0～100之間；以及p介於1～10之間。
本發明提供一種可溶性聚噻吩衍生物如式1。
由實驗數據可知，本發明之交替共聚物的結構相對比較整齊，分子間的π-π作用力較強，所以材料的載子遷移率較高。另一方面，本發明之無規共聚物的結構相對比較散亂，溶解度較高，有利於光電元件的製程。但不論採用何種共聚物，均具有共軛側鏈噻吩之單體的重要特性：熱穩定性佳，高載子遷移率、低HOMO值、高開路電壓、及高光電轉換效率。
本發明之可溶性聚噻吩衍生物應用於有機薄膜電晶體裝置，並以該衍生物作為主動層材料。有關有機薄膜電晶體裝置詳細結構與製作方式例如可參見美國專利號6107117。
本發明之可溶性聚噻吩衍生物應用於有機發光二極體裝置，以該衍生物作為主動層材料。有關有機發光二極體裝置詳細結構與製作方式例如可參見美國專利號6488555。
本發明之可溶性聚噻吩衍生物應用於有機太陽能電池裝置，以該衍生物作為主動層材料。有關有機太陽能電池裝置詳細結構與製作方式例如可參見美國專利號6852920。
上述有機太陽能電池之主動層包含本發明之可溶性聚噻吩衍生物與一電子受體材料(acceptor)，例如為苯基-碳 61-丁酸甲酯(PC61
BM)或苯基-碳 71-丁酸甲酯(PC71
BM)，於一實施例中，其中該可溶性聚噻吩衍生物與電子受體材料混合比例約為1：3時，其光電轉換效率最佳。
為了讓本發明之上述和其他目的、特徵、和優點能更明顯易懂，下文特舉數實施例配合所附圖示，作詳細說明如下：
【實施例】
實施例1(合成具共軛側鏈噻吩之單體)
如式5所示，取2-己基噻吩(7.00g，41.6mmol)溶於無水THF後降溫至-78℃，於氮氣下慢慢滴入正丁基鋰(2.5M,18.4mL,46.0mmol)後於-78℃下反應1小時。接著一次加入氯化三甲基錫(10g，50mmol)，緩慢回溫至室溫後反應12小時。最後將Na2
CO3
飽和水溶液加入上述反應後之混合物，以正己烷萃取有機層並以無水硫酸鎂除水。以迴旋濃縮儀抽除有機層之有機溶劑後，以蒸餾法得產物(8.9g，產率65%)，其NMR氫譜如下：1
H NMR(CDCl3
,500MHz)6.98(d,1H),2.80(t,2H),1.68(m,2H),1.33(m,4H),0.84(t,3H),0.32(s,9H).
如式6所示，取式5之產物(10.00g,30.2mmol)、2-溴噻吩(4.92g,30.2mmol)、及Pd(PPh3
)4
(0.69g,0.6mmol)溶於DMF(20mL)及甲苯(80mL)之混合溶液中。將上述混合溶液通入氮氣十分鐘後，於氮氣下加熱至120℃後反應24小時，再降至室溫。將水加入上述反應後之混合物，以正己烷萃取有機層並以無水硫酸鎂除水。以迴旋濃縮儀抽除有機層之有機溶劑後，以減壓蒸餾法得產物(3.9g，產率52%)，其NMR氫譜如下：1
H NMR(CDCl3
,500MHz)7.16(d,1H),7.09(d,1H),6.97(d,1H),6.67(d,1H),2.77(t,2H),1.68(t,2H),1.33(m,6H),0.88(t,3H).
如式7所示，取式6之產物(10g,40mmol)溶於無水THF後，降溫至-78℃，於氮氣下慢慢滴入正丁基鋰(2.5M,17.6mL,44.0mmol)後於-78℃下反應1小時。接著一次加入氯化三甲基錫(9.6g，48mmol)，緩慢回溫至室溫後反應12小時。最後將Na2
CO3
飽和水溶液加入上述反應後之混合物，以正己烷萃取有機層並以無水硫酸鎂除水。以迴旋濃縮儀抽除有機層之有機溶劑後，以蒸餾法得產物(7.9g，產率48%)，其NMR氫譜如下：1
H NMR(CDCl3
,500MHz)7.20(d,1H),7.06(d,1H),6.96(m,2H),6.66(d,1H),2.76(t,2H),1.68(t,2H),1.33(m,2H),0.88(t,3H).
如式8所示，取2,4-二溴噻吩(21.5g,89.0mmol)溶於無水***(100mL)後，於氮氣下慢慢滴入-78℃之正丁基鋰(2.5M,42mL,98mmol)的無水***(200mL)溶液，並攪拌反應15分鐘。接著一次加入CuCl2
(14.4g，107mmol)後緩慢回溫至室溫並攪拌隔夜。過濾上述反應後之懸浮液，將濾液加水進行萃取，並以無水硫酸鎂乾燥分離之有機層。以迴旋濃縮儀抽除有機層之有機溶劑後,以***再結晶純化的方式得到產物(6.05g，產率42%)，其NMR氫譜如下：1
H NMR(CDCl3
,500MHz)7.15(d,J
=1,2Hz,2H),7.08(d,J
=1.2Hz,2H).
如式9所示,取式8之產物(1.0g,3.0mmol)、式7之產物(3.2g,7.5mmol)、及Pd(PPh3
)4
(0.07g,0.06mmol)溶於DMF(10mL)及甲苯(40mL)之混合溶液中。將上述混合溶液通入氮氣十分鐘後,於氮氣下加熱至120℃後反應24小時，再降至室溫。將水加入上述反應後之混合物，以50℃之氯仿萃取有機層並以無水硫酸鎂除水。以迴旋濃縮儀抽除有機層之有機溶劑後，以減壓蒸餾法得黃色粉狀產物(1.4g，產率68%)，其NMR氫譜如下：1
H NMR(CD2
Cl2
,500MHz)7.28(s,2H),7.15(s,2H),6.99(d,2H),6.90(d,2H),6.86(d,2H),6.86(d,2H),2.64(t,4H),1.52(quint,4H),1.18(m,12H),0.74(t,6H).
如式10所示，取式9之產物(3.0g,4.5mmol)溶於氯仿(30mL)及冰醋酸(10mL)之溶液後，於暗態及0℃加入NBS(1.61g,9.00mmol)，接著緩慢升溫至室溫後攪拌12小時。最後將水加入上述反應後之混合物，以50℃之氯仿萃取有機層並以無水硫酸鎂除水。以迴旋濃縮儀抽除有機層之有機溶劑後，以管柱層析法(沖提液為70℃之甲苯)得產物(2.85g，產率77%)，其NMR氫譜如下：1
H NMR(CDCl3
,500MHz)7.34(d,2H),7.13(s,2H),7.05(d,2H),7.01(d,2H),6.67(d,2H),2.78(t,4H),1.65(quint,4H),1.37(m,8H),0.87(t,6H)；其NMR碳譜如下：13
C NMR(CDCl3
,125MHz)145.6,138.15,136.02,134.81,134.26,134,127.01,124.90,124.44,123.66,122.98,106.91,31.55,30.20,29.71,28.74,22.57,14.04.
如式11所示，取式9之產物(0.82g,1mmol)溶於無水THF後降溫至-78℃，於氮氣下慢慢滴入正丁基鋰(2.5M,0.88mL,2.2mmol)後於-78℃下反應1小時。接著一次加入氯化三甲基錫(0.48g，2.4mmol)，緩慢回溫至室溫後反應12小時。最後將Na2
CO3
飽和水溶液加入上述反應後之混合物，以正己烷萃取有機層並以無水硫酸鎂除水。以迴旋濃縮儀抽除有機層之有機溶劑後，以蒸餾法得產物(0.62g，產率62%)，其NMR氫譜如下：1
H NMR(CDCl3
,500MHz)7.42(s,2H),7.04(d,2H),6.99(d,2H),6.94(d,2H),6.70(d,2H),2.80(t,4H),1.70(quint,4H),1.39(m,8H),0.91(t,6H),0.38(s,18H)。
實施例2聚噻吩衍生物(交替共聚物)
如式2和式3所示，取式10之產物(0.49g,0.6mmol)或其他二溴化物、含硫之雜芳香烴基二錫化物如表1(0.6mmol)、Pd2
(dba)3
(11g,2mol%)、及三(鄰甲苯基)膦(29.2mg,16mol%)溶於氯苯(10mL)中，通入氮氣以去除溶液中殘存氧氣，接著以微波加熱器加熱上述混合物30分鐘。接著將反應後之溶液倒入甲醇(1L)中，形成黑色沉澱。以索氏萃取器(Soxhlet extractor)及甲醇、丙酮、及己烷清洗上述黑色沉澱，並以氯仿萃取溶解的部份。濃縮萃取物並以甲醇再沉澱，可得深紅色產物P1(0.31g，產率68%)。
實施例3聚噻吩衍生物(無規共聚物)
如式4所示，取式10之產物(0.25g,0.3mmol)、含硫之雜芳香烴基二溴化物(0.3mmol)及含硫之雜芳香烴基二錫化物如表2(0.6mmol)、Pd2
(dba)3
(11g,2mol%)、及三(鄰甲苯基)膦(29.2mg,16mol%)溶於氯苯(20mL)中，通入氮氣以去除溶液中殘存氧氣，接著以微波加熱器加熱上述混合物30分鐘。接著將反應後之溶液倒入甲醇(1L)中，形成黑色沉澱。以索氏萃取器(Soxhlet extractor)及甲醇、丙酮、及己烷清洗上述黑色沉澱，並以氯仿萃取溶解的部份。濃縮萃取物並以甲醇再沉澱，可得紅色產物P8。
實施例4有機太陽能電池元件
本實施例製備如第1圖所示之有機太陽能電池裝置10，其包括一氧化銦錫(ITO)陽極11；一電洞傳輸層12，材料為聚3,4-乙基二氧噻吩：聚對苯乙烯磺酸Poly(3,4-ethylenedioxythiophene)：poly(styrene-sulfonate)(PEDOT:PSS)，形成於陽極之上；一主動層13，包含本發明之可溶性聚噻吩衍生物，形成於電洞傳輸層之上；以及一陰極14為鈣(Ca)/鋁(Al)。
上述之主動層由本發明之聚合物與苯基-碳-丁酸甲酯([6,6]-phenyl-C-butyric acid methyl ester,PCBM)以1:3的比例摻混而組成，其中PCBM中的碳可以是碳61或是碳71的衍生物。效率的量測是在AM 1.5的太陽光照度下測量。
製備的步驟如下：
1.於實驗前一天配置主動層溶液(Polymer/PCBM=1:3,10mg/mL)，攪拌一晚。
2.氧化銦錫(ITO)玻璃分別用丙酮及異丙醇以超音波震盪清洗15分鐘，以氮氣吹乾後，置於加熱板烘烤5分鐘。
3.將氧化銦錫(ITO)玻璃置於氧氣電漿下5分鐘。
4.以3000rpm/30sec旋轉塗佈聚3,4-乙基二氧塞吩：聚對苯乙烯磺酸(PEDOT:PSS,Baytron P-VP AI4083)，之後放置手套箱以150℃加熱烤一小時。
5.在手套箱中以1000rpm/60sec旋轉塗佈主動層(Polymer/PCBM=1:3,w/w)。
6.將ITO玻璃置於140℃加熱板上退火20分鐘，靜置冷卻。
7.放至光罩上，蒸鍍鈣/鋁電極。
8.最後封裝整個元件、進行I-V量測。
表3為本發明實施例2之交替共聚物及實施例3之無規共聚物應用於有機太陽能電池中的光電轉換效率、短路電流、開路電壓與填充因子。
雖然本發明已以數個較佳實施例揭露如上，然其並非用以限定本發明，任何熟習此技藝者，在不脫離本發明之精神和範圍內，當可作任意之更動與潤飾，因此本發明之保護範圍當視後附之申請專利範圍所界定者為準。
10．．．有機太陽能電池
11．．．陽極
12．．．電洞傳輸層
13．．．主動層
14．．．陰極
第1圖係本發明一實施例中，有機太陽能電池的裝置圖。
10．．．有機太陽能電池
11．．．陽極
12．．．電洞傳輸層
13．．．主動層
14．．．陰極
Claims (6)
- 一種可溶性聚噻吩衍生物，具有下列結構：
- 如申請專利範圍第1項所述之可溶性聚噻吩衍生物，其中該可溶性聚噻吩衍生物分子量介於1,000~100,000之間。
- 如申請專利範圍第1項所述之可溶性聚噻吩衍生物，係一無規共聚物。
- 如申請專利範圍第1項所述之可溶性聚噻吩衍生物，係一交替共聚物。
- 如申請專利範圍第1項所述之可溶性聚噻吩衍生物，係使用於光電元件上。
- 如申請專利範圍第5項所述之可溶性聚噻吩衍生物，其中該光電元件為有機薄膜電晶體、有機發光二極體或有機太陽能電池。
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| TW098116138A TWI418571B (zh) | 2009-05-15 | 2009-05-15 | 可溶性聚噻吩衍生物 |
| US12/492,740 US7999062B2 (en) | 2009-05-15 | 2009-06-26 | Soluble polythiophene derivative |
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| TW098116138A TWI418571B (zh) | 2009-05-15 | 2009-05-15 | 可溶性聚噻吩衍生物 |
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| TW201040208A TW201040208A (en) | 2010-11-16 |
| TWI418571B true TWI418571B (zh) | 2013-12-11 |
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| US8895693B2 (en) | 2010-06-25 | 2014-11-25 | Samsung Electronics Co., Ltd. | Electron-donating polymers and organic solar cells including the same |
| KR101853395B1 (ko) | 2011-05-23 | 2018-04-30 | 삼성전자주식회사 | 전자 공여체 고분자 및 이를 포함하는 태양 전지 |
| TWI431002B (zh) | 2011-05-30 | 2014-03-21 | Ind Tech Res Inst | 富勒烯衍生物與光電元件 |
| KR101777326B1 (ko) | 2011-10-05 | 2017-09-12 | 삼성전자주식회사 | 전자 공여체 고분자 및 이를 포함하는 유기 태양 전지 |
| CN104017181A (zh) * | 2013-02-28 | 2014-09-03 | 海洋王照明科技股份有限公司 | 含萘并二噻吩基的聚合物及其制备方法和应用 |
| CN104017175A (zh) * | 2013-02-28 | 2014-09-03 | 海洋王照明科技股份有限公司 | 含噻吩并噻吩基的聚合物及其制备方法和应用 |
| US9428603B2 (en) | 2014-03-18 | 2016-08-30 | Council Of Scientific & Industrial Research | Polymeric dispersion of thiophene copolymers and a process for preparation thereof |
| CN112661942B (zh) * | 2020-12-16 | 2023-03-21 | 华南理工大学 | 基于3-氰基噻吩的p-型共轭聚合物及其制备方法与光伏应用 |
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| US6994805B2 (en) * | 2001-10-26 | 2006-02-07 | Infineon Technologies Ag | Polythiophene polymer with high charge-carrier mobilities, method for fabricating the polymer, and semiconductor component and organic field effect transistor including the polymer |
| WO2007148914A1 (en) * | 2006-06-20 | 2007-12-27 | Lg Chem, Ltd. | Polyheterocyclic compound, organic electronic device using polyheterocyclic compound, and electronic apparatus including organic electronic device |
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| GB2332094A (en) | 1996-09-04 | 1999-06-09 | Cambridge Display Tech Ltd | Electrode deposition for organic light-emitting devices |
| US6107117A (en) | 1996-12-20 | 2000-08-22 | Lucent Technologies Inc. | Method of making an organic thin film transistor |
| US6852920B2 (en) | 2002-06-22 | 2005-02-08 | Nanosolar, Inc. | Nano-architected/assembled solar electricity cell |
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| US6994805B2 (en) * | 2001-10-26 | 2006-02-07 | Infineon Technologies Ag | Polythiophene polymer with high charge-carrier mobilities, method for fabricating the polymer, and semiconductor component and organic field effect transistor including the polymer |
| WO2007148914A1 (en) * | 2006-06-20 | 2007-12-27 | Lg Chem, Ltd. | Polyheterocyclic compound, organic electronic device using polyheterocyclic compound, and electronic apparatus including organic electronic device |
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| TW201040208A (en) | 2010-11-16 |
| US7999062B2 (en) | 2011-08-16 |
| US20100292433A1 (en) | 2010-11-18 |
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