JP2013119625A - 半導体組成物 - Google Patents
半導体組成物 Download PDFInfo
- Publication number
- JP2013119625A JP2013119625A JP2012251908A JP2012251908A JP2013119625A JP 2013119625 A JP2013119625 A JP 2013119625A JP 2012251908 A JP2012251908 A JP 2012251908A JP 2012251908 A JP2012251908 A JP 2012251908A JP 2013119625 A JP2013119625 A JP 2013119625A
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- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- heteroaryl
- aryl
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 55
- 239000000203 mixture Substances 0.000 title claims abstract description 32
- 239000002904 solvent Substances 0.000 claims abstract description 59
- -1 aromatic halogenated hydrocarbon Chemical class 0.000 claims abstract description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 22
- 125000005843 halogen group Chemical group 0.000 claims abstract description 17
- 229920000642 polymer Polymers 0.000 claims description 48
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000003107 substituted aryl group Chemical group 0.000 claims description 22
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 20
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims description 10
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 abstract description 15
- 230000005669 field effect Effects 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 230000037230 mobility Effects 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 150000002431 hydrogen Chemical class 0.000 description 15
- 239000000178 monomer Substances 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 229910052814 silicon oxide Inorganic materials 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 0 CC*(C)c1cc(*)c(-c2cc(*)c(C(N(*)C3=*)=C4C3=C(c3c(*)cc(-c5c(*)cc(C(C)(C)CC)[o]5)[s]3)N(*)C4=*)[s]2)[o]1 Chemical compound CC*(C)c1cc(*)c(-c2cc(*)c(C(N(*)C3=*)=C4C3=C(c3c(*)cc(-c5c(*)cc(C(C)(C)CC)[o]5)[s]3)N(*)C4=*)[s]2)[o]1 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000944 Soxhlet extraction Methods 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical group N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical group CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 3
- QVLAWKAXOMEXPM-UHFFFAOYSA-N 1,1,1,2-tetrachloroethane Chemical compound ClCC(Cl)(Cl)Cl QVLAWKAXOMEXPM-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-ZDOIIHCHSA-N 1,1,2,2-tetrachloroethane Chemical group Cl[13CH](Cl)[13CH](Cl)Cl QPFMBZIOSGYJDE-ZDOIIHCHSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical group C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- YPLYFEUBZLLLIY-UHFFFAOYSA-N dipropan-2-yl butanedioate Chemical compound CC(C)OC(=O)CCC(=O)OC(C)C YPLYFEUBZLLLIY-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical group C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- BNIXVQGCZULYKV-UHFFFAOYSA-N pentachloroethane Chemical compound ClC(Cl)C(Cl)(Cl)Cl BNIXVQGCZULYKV-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000007650 screen-printing Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- CUPOOAWTRIURFT-UHFFFAOYSA-N thiophene-2-carbonitrile Chemical compound N#CC1=CC=CS1 CUPOOAWTRIURFT-UHFFFAOYSA-N 0.000 description 2
- 150000003577 thiophenes Chemical class 0.000 description 2
- CCRMAATUKBYMPA-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C.C[Sn](C)C CCRMAATUKBYMPA-UHFFFAOYSA-N 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- 229910052727 yttrium Inorganic materials 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical group N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 1
- HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical group C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- UMZCLZPXPCNKML-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole Chemical group C1=NC2=NCSC2=N1 UMZCLZPXPCNKML-UHFFFAOYSA-N 0.000 description 1
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical compound C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
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Classifications
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- 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
- C08G61/124—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 nitrogen atom in the ring
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- 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
- C08G61/125—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 oxygen atom in the ring
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- 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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- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
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- 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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- 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
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Abstract
【解決手段】この半導体組成物は、ジケトピロロピロール−チオフェンコポリマーと、少なくとも2個の炭素原子および少なくとも3個のハロゲン原子を含む非芳香族ハロゲン化炭化水素溶媒とを含む。好ましくは、非芳香族ハロゲン化炭化水素溶媒は、少なくとも2個の炭素原子と、少なくとも3個のハロゲン原子とを含む。
【選択図】なし
Description
Y1およびY2は、独立してSまたはOであり;aは、少なくとも1であり;(p+q)の合計は少なくとも1であり;Mは、共役部分であり;bは、0〜約20であり;nは、2〜約5,000であり;
それぞれのAr1単位およびAr2単位は、独立して、以下のものからなる群から選択され、
Y1およびY2は、独立してSまたはOであり;
それぞれのX1およびX2は、独立して、S、Se、OまたはNR”であり、各R”は、独立して、水素、アリールまたはアルキルであってもよく;
それぞれのZ1およびZ2は、独立して、アルキル、置換アルキル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、ハロゲン、アルコキシ、アルキルチオ、トリアルキルシリル、−CNまたは−NO2であり;
Mは、共役部分であり;
aは、少なくとも1であり;bは、0〜約20であり;(c+d)の合計は、少なくとも1であり;eおよびfは、独立して、0〜2であり;nは、2〜約5,000である。
Y1およびY2は、SまたはOであり;
各Z’は、独立して、水素、アルキル、置換アルキル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、ハロゲン、アルコキシ、アルキルチオ、トリアルキルシリル、−CNまたは−NO2であり;cおよびdは、独立して、1、2、3または4である。
Y1およびY2は、SまたはOであり;
それぞれのZ’およびR’は、独立して、水素、アルキル、置換アルキル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、ハロゲン、アルコキシ、アルキルチオ、トリアルキルシリル、−CNまたは−NO2であり;cおよびdは、独立して、1または2である。
Y1およびY2は、独立してSまたはOであり;
R3およびR4は、独立して、水素、アルキル、置換アルキル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、ハロゲン、アルコキシ、アルキルチオ、トリアルキルシリル、−CNまたは−NO2であり;
Mは共役部分であり;
aは、少なくとも1であり;bは0〜約20であり;nは、2〜約5,000である。
Y1およびY2は、独立してSまたはOであり;
aは、少なくとも1であり;hは、0または1であり;(h+j+k)の合計は、少なくとも1であり;bは0〜約20であり;nは、2〜約5,000であり;
それぞれのAr1単位およびAr2単位は、独立して、以下からなる群から選択され、
Ar3は、以下のもの
Mは、Ar1およびAr2の可能な選択肢のいずれかではない共役部分である。
Y1およびY2は、独立して、SまたはOであり;
それぞれのZ’、R’、R3、R4、R5およびR6は、独立して、水素、アルキル、置換アルキル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、ハロゲン、アルコキシ、アルキルチオ、トリアルキルシリル、−CNまたは−NO2である。
以下のスキーム1に概要を説明するように、ポリ(2,5−ジオクタデシル−3,6−ビス(チエニル−5−イル)−ジケトピロロピロールを合成した。このコポリマーは、式(I)、式(II)、式(2)(Y1=Y2=O、R1=R2=C18H37、R3=R4=H)に含まれる。
スキーム1.ポリマー4の合成
60mLのt−アミルアルコールにナトリウム(3.45グラム、0.15mol)を加え、少量の塩化鉄(III)(50mg)を加えた。この混合物を、ナトリウムが消失するまで95〜102℃で1時間激しく撹拌した。この溶液を85℃まで冷却した。得られた溶液に、10.9グラム(0.1mol)の2−チオフェンカルボニトリルを加えた。次いで、8.3グラム(0.04mol)のコハク酸ジイソプロピルをt−アミルアルコール5mLに加えたものを85℃で1時間かけて滴下した。加え終わったら、混合物をこの温度で2時間維持した。次いで、反応混合物を50℃まで冷却し、メタノール50mLで希釈し、次いで、氷酢酸約15mLでゆっくりと中和し、短時間環流させ、反応混合物を濾過した。残渣を熱メタノールおよび水で数回洗浄した後、得られた溶液を50℃、減圧下で乾燥させた。青みがかった赤色の固体(11グラム、収率92%)を得た(化合物(1))。この固体をNMRで分析し、結果は以下のとおりである:1H NMR(DMSO−D6):11.23(s、2H)、8.20(d、J=3.7Hz、2H)、7.95(d、J=4.9、2H)、7.29(dd、J1=3.7Hz、J2=4.9Hz、2H)。
化合物(1)(1.5グラム、5mmol)、2.31グラム(16.7mmol)のK2CO3、12mgの18−クラウン−6、1−ブロモオクタデカン(5.57グラム、16.7mmol)をジメチルホルムアミド(DMF)75mL中で混合し、混合物を120℃で一晩加熱した。室温まで冷却した後、溶液を濾過し、固体を水で数回洗浄した。加熱することによって固体をクロロホルムに溶解し、濾過した。濾液を室温まで冷却し、赤色沈殿が生成した。固体を濾過し、減圧下で乾燥させた(化合物(2))。収率3.01g(74.7%)。1H NMR(CDCl3):8.93(dd、J1=3.9Hz、J2=1.1Hz、2H)、7.64(dd、J1=5.0Hz、J2=1.1Hz、2H)、7.28(dd、J1=5.0Hz、J2=3.9Hz、2H)、4.07(t、J=7.8Hz、4H)、1.74(m、4H)、1.20−1.50(m、60H)、0.88(t、J=6.6Hz、6H)。融点:124℃。
化合物(2)(4.416グラム、3mmol)および30mLのクロロホルムを、撹拌棒、凝縮器、滴下漏斗を取り付けた100mLの3ッ口フラスコに加えた。次いで、0.96グラム(6mmol)のBr2を20mLのクロロホルムに加えたものを室温でこのフラスコに加えた。混合物を室温で10分間撹拌し、次いで、60℃まで加温し、さらに1時間撹拌した。次いで、反応混合物を室温まで冷却し、濾過した。この赤色固体をNa2SO3溶液、水で洗浄し、最後にメタノールで広範囲に洗浄した。次いで、加熱することによって固体をクロロホルムに溶解し、室温まで冷却した。濾過した後、暗紫色固体を得て、これを減圧下で乾燥させた。収率:1.78グラム(61.6%)。1H NMR(CDCl3):8.69(d、J=4.2Hz、2H)、7.24(d、J=4.2Hz、2H)、3.98(t、J=7.7Hz、4H)、1.71(m、4H)、1.20−1.50(m、60H)、0.88(t、J=6.6Hz、6H)。融点:161℃。
100mLフラスコに、ヘキサメチルジスズ(0.344グラム、1.05mmol)、テトラキス(トリフェニルホスフィン)パラジウム(0)、Pd(PPh3)4(58mg、0.05mmol)、ヨウ化銅(I)(3.8mg、0.02mmol)、化合物(3)(0.9631g、1mmol)、THF(30mL)および1−メチル−2−ピロリジノン(NMP)(15mL)を加えた。反応混合物を加熱して48時間環流させ、次いで、室温まで冷却し、アセトン200mLを撹拌したものに加えた。固体を濾別し、メタノールで洗浄し、乾燥させた。次いで、固体を、ヘプタンを用いたソックスレー抽出によって48時間かけてさらに精製し、次いで、クロロベンゼンに溶解した。溶媒を除去すると、暗青色固体が得られた(0.50グラム、62.5%)(化合物(4))。
式(A)のジケトピロロピロール−チオフェンコポリマー(以下、ポリマーAと称する)を合成した。
本実施例では、1,1,2,2−テトラクロロエタンを溶媒として使用した。12mgのポリマーAを、熱を加え、振盪しつつ、2グラムの1,1,2,2−テトラクロロエタン溶媒に溶解し、暗青色溶液を作成した。この溶液(0.6重量%のポリマーA)は、室温で数日間、沈殿せずに安定である。
この比較例では、クロロホルムを溶媒として使用した。この機器を、上に記載したのと同様の手順を用いて加工した。
この比較例では、クロロベンゼンを溶媒として使用した。この機器を、上に記載したのと同様の手順を用いて加工した。
この比較例では、1,2−ジクロロベンゼンを溶媒として使用した。この機器を、上に記載したのと同様の手順を用いて加工した。
この比較例では、クロロトルエンを溶媒として使用した。このポリマーは、濃度0.3重量%、高温であっても、この溶媒に完全に溶解させることはできなかった。
表2には、上の実施例とその結果をまとめている。
式(B)のジケトピロロピロール−チオフェンコポリマー(以下、ポリマーBと称する)を、ポリマーAと同様の様式で合成した。
Claims (4)
- 組成物であって、
少なくとも2個の炭素原子および少なくとも3個のハロゲン原子を含む非芳香族ハロゲン化炭化水素溶媒と、
式(I)のポリマーとを含み、
Y1およびY2は、独立してSまたはOであり;
aは、少なくとも1であり;
(p+q)の合計は少なくとも1であり;
Mは、共役部分であり;
bは、0〜約20であり;
nは、2〜約5,000であり;
それぞれのAr1単位およびAr2単位は、独立して、以下のものからなる群から選択され、
- 半導体組成物であって、
1,1,2,2−テトラクロロエタンと、
式(1−A)、(18)、(19)、(20)、(22)、(21−A)からなる群から選択されるポリマーとを含み、
Y1およびY2は、独立してSまたはOであり;
R3、R4、R5およびR6は、独立して、水素、アルキル、置換アルキル、アリール、置換アリール、ヘテロアリール、置換ヘテロアリール、ハロゲン、アルコキシ、アルキルチオ、トリアルキルシリル、−CNまたは−NO2である、半導体組成物。 - 電子機器であって、半導体層を含み、この半導体層が、
少なくとも2個の炭素原子および少なくとも3個のハロゲン原子を含む非芳香族ハロゲン化炭化水素溶媒と、
式(I)のポリマーとを含む半導体組成物から作られ、
Y1およびY2は、独立してSまたはOであり;
aは、少なくとも1であり;
(p+q)の合計は少なくとも1であり;
Mは、共役部分であり;
bは、0〜約20であり;
nは、2〜約5,000であり;
それぞれのAr1単位およびAr2単位は、独立して、以下のものからなる群から選択され、
半導体層の平均移動度が、上のポリマーと、1個または2個の塩素原子を含む異なる炭化水素溶媒とを含む半導体組成物から作られる半導体層の平均移動度より少なくとも100%大きい、電子機器。 - 少なくとも2個の炭素原子および少なくとも3個のハロゲン原子を含む非芳香族ハロゲン化炭化水素溶媒と、
場合により置換されたジケトピロロピロール/ジチオケトピロロピロール部分および場合により置換されたチオフェン部分を含むコポリマーとを含む、組成物。
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WO2015147459A1 (ko) * | 2014-03-24 | 2015-10-01 | 경상대학교산학협력단 | 비대칭 다이케토피롤로피롤 중합체 및 이를 함유하는 유기 전자 소자 |
WO2016076213A1 (ja) * | 2014-11-13 | 2016-05-19 | 住友化学株式会社 | インク組成物およびそれを用いて製造した光電変換素子 |
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US9214258B2 (en) * | 2012-12-06 | 2015-12-15 | Xerox Corporation | Semiconductor composites comprising carbon nanotubes and diketopyrrolopyrrole-thiophene based copolymers |
US9399698B2 (en) | 2014-01-31 | 2016-07-26 | Xerox Corporation | Processes for purifying diketopyrrolopyrrole copolymers |
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Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000506914A (ja) * | 1996-03-06 | 2000-06-06 | ビーエーエスエフ アクチェンゲゼルシャフト | 置換ポリチオフェン、その製造及びその用途 |
JP2004197023A (ja) * | 2002-12-20 | 2004-07-15 | Dainippon Ink & Chem Inc | 発光材料及びこれを含有する有機エレクトロルミネッセンス素子 |
JP2008031337A (ja) * | 2006-07-31 | 2008-02-14 | Sumitomo Chemical Co Ltd | 高分子発光素子及び有機トランジスタ並びにそれらに有用な組成物 |
WO2011131280A1 (en) * | 2010-04-19 | 2011-10-27 | Merck Patent Gmbh | Polymers of benzodithiophene and their use as organic semiconductors |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
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ES2387304T3 (es) | 2003-10-28 | 2012-09-20 | Basf Se | Nuevos polímeros de dicetopirrolopirrol |
CA2655076A1 (en) * | 2006-06-30 | 2008-01-03 | Ciba Holding Inc. | Diketopyrrolopyrrole polymers as organic semiconductors |
US7932344B2 (en) | 2007-09-06 | 2011-04-26 | Xerox Corporation | Diketopyrrolopyrrole-based polymers |
US7910684B2 (en) | 2007-09-06 | 2011-03-22 | Xerox Corporation | Diketopyrrolopyrrole-based derivatives for thin film transistors |
US7928181B2 (en) | 2008-08-18 | 2011-04-19 | Xerox Corporation | Semiconducting polymers |
US8624232B2 (en) | 2009-08-28 | 2014-01-07 | Prashant Sonar | Ambipolar polymeric semiconductor materials and organic electronic devices |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2000506914A (ja) * | 1996-03-06 | 2000-06-06 | ビーエーエスエフ アクチェンゲゼルシャフト | 置換ポリチオフェン、その製造及びその用途 |
JP2004197023A (ja) * | 2002-12-20 | 2004-07-15 | Dainippon Ink & Chem Inc | 発光材料及びこれを含有する有機エレクトロルミネッセンス素子 |
JP2008031337A (ja) * | 2006-07-31 | 2008-02-14 | Sumitomo Chemical Co Ltd | 高分子発光素子及び有機トランジスタ並びにそれらに有用な組成物 |
WO2011131280A1 (en) * | 2010-04-19 | 2011-10-27 | Merck Patent Gmbh | Polymers of benzodithiophene and their use as organic semiconductors |
Non-Patent Citations (5)
Title |
---|
JPN6016001970; Li, Yuning et al: 'A High Mobility P-Type DPP-Thieno[3,2-b]thiophene Copolymer for Organic Thin-Film Transistors' Advanced Materials 22(43), 2010, p4862-4866 * |
JPN6016001972; Min, Jie et al: 'Low bandgap copolymer of 1,4-diketopyrrolo[3,4-c]pyrrole and thieno[3,2-b]thiophene - synthesis and' Synthetic Metals 161(17-18), 2011, p1832-1837 * |
JPN6016001974; Zhang, Xinran et al: 'Molecular Packing of High-Mobility Diketo Pyrrolo-Pyrrole Polymer Semiconductors with Branched Alkyl' Journal of the American Chemical Society 133(38), 2011, p15073-15084 * |
JPN6016017575; Li, Yuning et al: 'Annealing-free high-mobility diketopyrrolopyrrole-quaterthiophene Copolymer for Solution-Processed O' Journal of the American Chemical Society 133(7), 2011, p2198-2204 * |
JPN6016017577; Ha, Jae Seung et al: '2,5-Bis(2-octyldodecyl)pyrrolo[3,4-c]pyrrole-1,4-(2H,5H)-dione-Based Donor-Acceptor Alternating Copo' Journal of the American Chemical Society 133(27), 2011, p10364-10367 * |
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Publication number | Priority date | Publication date | Assignee | Title |
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WO2015147459A1 (ko) * | 2014-03-24 | 2015-10-01 | 경상대학교산학협력단 | 비대칭 다이케토피롤로피롤 중합체 및 이를 함유하는 유기 전자 소자 |
KR20150110127A (ko) * | 2014-03-24 | 2015-10-02 | 경상대학교산학협력단 | 비대칭 다이케토피롤로피롤 중합체 및 이를 함유하는 유기 전자 소자 |
KR101600031B1 (ko) * | 2014-03-24 | 2016-03-07 | 경상대학교산학협력단 | 비대칭 다이케토피롤로피롤 중합체 및 이를 함유하는 유기 전자 소자 |
WO2016076213A1 (ja) * | 2014-11-13 | 2016-05-19 | 住友化学株式会社 | インク組成物およびそれを用いて製造した光電変換素子 |
JPWO2016076213A1 (ja) * | 2014-11-13 | 2017-06-29 | 住友化学株式会社 | インク組成物およびそれを用いて製造した光電変換素子 |
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US20130140494A1 (en) | 2013-06-06 |
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CA2797308A1 (en) | 2013-06-06 |
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