JP6161089B2 - ナフタレンジイミド−ビニレン−オリゴチオフェン−ビニレンポリマーに基づく半導体材料 - Google Patents
ナフタレンジイミド−ビニレン−オリゴチオフェン−ビニレンポリマーに基づく半導体材料 Download PDFInfo
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- JP6161089B2 JP6161089B2 JP2015548815A JP2015548815A JP6161089B2 JP 6161089 B2 JP6161089 B2 JP 6161089B2 JP 2015548815 A JP2015548815 A JP 2015548815A JP 2015548815 A JP2015548815 A JP 2015548815A JP 6161089 B2 JP6161089 B2 JP 6161089B2
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- 229920000642 polymer Polymers 0.000 title claims description 45
- 239000004065 semiconductor Substances 0.000 title claims description 29
- 239000000463 material Substances 0.000 title claims description 25
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 230000005669 field effect Effects 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000013086 organic photovoltaic Methods 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims 1
- -1 C 2 -C 30 -alkynyl Chemical group 0.000 description 99
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- HPJFXFRNEJHDFR-UHFFFAOYSA-N 22291-04-9 Chemical compound C1=CC(C(N(CCN(C)C)C2=O)=O)=C3C2=CC=C2C(=O)N(CCN(C)C)C(=O)C1=C32 HPJFXFRNEJHDFR-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 11
- 0 CCCCCCCCC(C)CN(C(c(c1c2c(C(N3CC(C)*)=O)c(CC4(*)C(C)C)c4c11)cc(-c4ccc(-c5cc(CC6(*)C(C)C)c6[s]5)[s]4)c2C3=O)=O)C1=O Chemical compound CCCCCCCCC(C)CN(C(c(c1c2c(C(N3CC(C)*)=O)c(CC4(*)C(C)C)c4c11)cc(-c4ccc(-c5cc(CC6(*)C(C)C)c6[s]5)[s]4)c2C3=O)=O)C1=O 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 239000010931 gold Substances 0.000 description 8
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229920000620 organic polymer Polymers 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- LZPWAYBEOJRFAX-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2$l^{2}-dioxaborolane Chemical compound CC1(C)O[B]OC1(C)C LZPWAYBEOJRFAX-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002800 charge carrier Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 3
- OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003989 dielectric material Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- 125000003846 1,2-diazepinyl group Chemical group 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- RFMSIVGKBOVYMW-UHFFFAOYSA-N 2,5-diethynylthiophene Chemical compound C#CC1=CC=C(C#C)S1 RFMSIVGKBOVYMW-UHFFFAOYSA-N 0.000 description 2
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 2
- OOFFPJPKXRNVDN-UHFFFAOYSA-N 2-ethynyl-5-(5-ethynylthiophen-2-yl)thiophene Chemical compound S1C(C#C)=CC=C1C1=CC=C(C#C)S1 OOFFPJPKXRNVDN-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 238000000944 Soxhlet extraction Methods 0.000 description 2
- YLEIFZAVNWDOBM-ZTNXSLBXSA-N ac1l9hc7 Chemical compound C([C@H]12)C[C@@H](C([C@@H](O)CC3)(C)C)[C@@]43C[C@@]14CC[C@@]1(C)[C@@]2(C)C[C@@H]2O[C@]3(O)[C@H](O)C(C)(C)O[C@@H]3[C@@H](C)[C@H]12 YLEIFZAVNWDOBM-ZTNXSLBXSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004097 arachidonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002785 azepinyl group Chemical group 0.000 description 2
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 2
- 125000005070 decynyl 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])C#C* 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 125000005980 hexynyl group Chemical group 0.000 description 2
- 125000005644 linolenyl group Chemical group 0.000 description 2
- 125000005645 linoleyl group Chemical group 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 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 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 2
- 125000005071 nonynyl group Chemical group C(#CCCCCCCC)* 0.000 description 2
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 2
- 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 2
- 125000001117 oleyl 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])/C([H])=C([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])[H] 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052715 tantalum Inorganic materials 0.000 description 2
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 2
- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 description 1
- 125000005330 8 membered heterocyclic group Chemical group 0.000 description 1
- 206010063836 Atrioventricular septal defect Diseases 0.000 description 1
- JVPSGMLEYUYPLU-UHFFFAOYSA-N CC(C)c1cc([s]c2c3[s]c(C(C)C)c2)c3[s]1 Chemical compound CC(C)c1cc([s]c2c3[s]c(C(C)C)c2)c3[s]1 JVPSGMLEYUYPLU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000003725 azepanyl group Chemical group 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001211 electron capture detection Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
- 125000005969 isothiazolinyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 125000003971 isoxazolinyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 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
- 125000000740 n-pentyl group Chemical group [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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003551 oxepanyl group Chemical group 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 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 1
- 238000000059 patterning Methods 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000005458 thianyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001583 thiepanyl group Chemical group 0.000 description 1
- 125000003777 thiepinyl group Chemical group 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Description
有機半導体材料は、有機光起電素子(OPVs)、有機電界効果トランジスタ(OFET)、有機発光ダイオード(OLED)、及び有機エレクトロクロミック素子(ECD)などの電子機器に使用され得る。
R1及びR2は互いに独立してC1〜C30−アルキル、C2〜C30−アルケニル、C2〜C30−アルキニル、フェニル又は5〜8員の複素環系であり、その際、
C1〜C30−アルキル、C2〜C30−アルケニル又はC2〜C30−アルキニル基はそれぞれ、ハロゲン、−CN、−NO2、−OH、−NH2、−NH(C1〜20−アルキル)、−N(C1〜20−アルキル)2、−NH−C(O)−(C1〜20−アルキル)、−S(O)2OH、−CHO、−C(O)−C1〜20−アルキル、−C(O)OH、−C(O)−OC1〜20−アルキル、−C(O)NH2、−CO(O)NH−C1〜20−アルキル、−C(O)N(C1〜20アルキル)2、−O−C1〜20−アルキル、−O−C(O)−C1〜20−アルキル、−SiH3、SiH2(C1〜20−アルキル)、SiH(C1〜20−アルキル)2、Si(C1〜20−アルキル)3、C4〜8−シクロアルキル、フェニル、及び5〜8員の複素環系、及びフェニルからなる群から独立して選択される1〜10個の置換基で置換されてよく、且つ
フェニル及び5〜8員の複素環系は1〜5個のC1〜16−アルキル基で置換されてよく、
oは1、2又は3であり且つ
nは2〜10000の整数である)
の単位を含むポリマーである。
その際、C6〜30−アルキル、C6〜30−アルケニル又はC6〜30−アルキニル基は、それぞれ、ハロゲン、−CN、−NO2、−OH、−NH2、−NH(C1〜20−アルキル)、−N(C1〜20アルキル)2、−NH−C(O)−(C1〜20−アルキル)、−S(O)2OH、−CHO、−C(O)−C1〜20−アルキル、−C(O)OH、−C(O)−OC1〜20−アルキル、−C(O)NH2、−CO(O)NH−C1〜20−アルキル、−C(O)N(C1〜20アルキル)2、−O−C1〜20−アルキル、及びN−O−C(O)−C1〜20−アルキルからなる群から独立して選択される1〜10個の置換基で置換されてよく、且つ
フェニルは1個又は2個のC1〜16−アルキル基で置換されてよい。
その際、C6〜30−アルキル、C6〜30−アルケニル又はC6〜30−アルキニル基は、それぞれ、ハロゲン、−CN、−NO2、−NH(C1〜20−アルキル)、−N(C1〜20−アルキル)2、−NH−C(O)−(C1〜20−アルキル)、−C(O)−C1〜20−アルキル、−C(O)−OC1〜20−アルキル、−C(O)NH2、−CO(O)NH−C1〜20−アルキル、−C(O)N(C1〜20−アルキル)2、−O−C1〜20−アルキル、及びN−O−C(O)−C1〜20−アルキルからなる群から独立して選択される1〜10個の置換基で置換されてよい。
R1及びR2が、互いに独立してC6〜30−アルキル、C6〜30−アルケニル、C6〜30−アルキニル、又はフェニルであり、
その際、C6〜30−アルキル、C6〜30−アルケニル又はC6〜30−アルキニル基が、それぞれ、ハロゲン、−CN、−NO2、−OH、−NH2、−NH(C1〜20−アルキル)、−N(C1〜20−アルキル)2、−NH−C(O)−(C1〜20−アルキル)、−S(O)2OH、−CHO、−C(O)−C1〜20−アルキル、−C(O)OH、−C(O)−OC1〜20−アルキル、−C(O)NH2、−CO(O)NH−C1〜20−アルキル、−C(O)N(C1〜20−アルキル)2、−O−C1〜20−アルキル、及びN−O−C(O)−C1〜20−アルキルからなる群から独立して選択される1〜10個の置換基で置換されてよく、且つフェニルが1個又は2個のC1〜C16−アルキル基で置換されてよく、
oが1、2又は3であり、且つ
nが5〜1000の整数である、ポリマーである。
R1及びR2が、互いに独立してC6〜30−アルキル、C6〜30−アルケニル又はC6〜30−アルキニルであり、
その際、C6〜30−アルキル、C6〜30−アルケニル又はC6〜30−アルキニル基が、それぞれ、ハロゲン、−CN、−NO2、−NH(C1〜20−アルキル)、−N(C1〜20アルキル)2、−NH−C(O)−(C1〜20−アルキル)、−C(O)−C1〜20−アルキル、−C(O)−OC1〜20−アルキル、−C(O)NH2、−CO(O)NH−C1〜20−アルキル、−C(O)N(C1〜20−アルキル)2、−O−C1〜20−アルキル、及びN−O−C(O)−C1〜20−アルキルからなる群から独立して選択される1〜10個の置換基で置換されてよく、
oが1、2又は3であり且つ
nが5〜500の整数である、ポリマーである。
R1及びR2が、互いに独立してC6〜30−アルキルであり、
その際、C6〜30−アルキルが、それぞれ、ハロゲン、−CN、−NO2、−NH(C1〜20−アルキル)、−N(C1〜20アルキル)2、−NH−C(O)−(C1〜20−アルキル)、−C(O)−C1〜20−アルキル、−C(O)−OC1〜20−アルキル、−C(O)NH2、−CO(O)NH−C1〜20−アルキル、−C(O)N(C1〜20−アルキル)2、−O−C1〜20−アルキル、及びN−O−C(O)−C1〜20−アルキルからなる群から独立して選択される1〜10個の置換基で置換されてよく、
oが1又は2であり且つ
nが10〜100の整数である、ポリマーである。
R1及びR2は互いに独立してC1〜C30−アルキル、C2〜C30−アルケニル又はC2〜C30−アルキニル、フェニル又は5〜8員の複素環系であり、
その際、C1〜C30−アルキル、C2〜C30−アルケニル又はC2〜C30−アルキニル基は、それぞれ、ハロゲン、−CN、−NO2、−OH、−NH2、−NH(C1〜20−アルキル)、−N(C1〜20−アルキル)2、−NH−C(O)−(C1〜20−アルキル)、−S(O)2OH、−CHO、−C(O)−C1〜20−アルキル、−C(O)OH、−C(O)−OC1〜20−アルキル、−C(O)NH2、−CO(O)NH−C1〜20−アルキル、−C(O)N(C1〜20−アルキル)2、−O−C1〜20−アルキル、−O−C(O)−C1〜20−アルキル、−SiH3、SiH2(C1〜20−アルキル)、SiH(C1〜20−アルキル)2、Si(C1〜20−アルキル)3、C4〜8−シクロアルキル、フェニル及び5〜8員の複素環系からなる群から独立して選択される1〜10個の置換基で置換されてよく、且つ
フェニル又は5〜8員の複素環系は1〜5個のC1〜16−アルキル基で置換されてよく、且つ
oは1、2又は3であり、
nは2〜10000の整数である)
の単位を含むポリマーの製造方法であって、
以下の式
R1及びR2は互いに独立してC1〜C30−アルキル、C2〜C30−アルケニル、C2〜C30−アルキニル、フェニル又は5〜8員の複素環系であり、
その際、C1〜C30−アルキル、C2〜C30−アルケニル又はC2〜C30−アルキニル基は、それぞれ、ハロゲン、−CN、−NO2、−OH、−NH2、−NH(C1〜20−アルキル)、−N(C1〜20−アルキル)2、−NH−C(O)−(C1〜20−アルキル)、−S(O)2OH、−CHO、−C(O)−C1〜20−アルキル、−C(O)OH、−C(O)−OC1〜20−アルキル、−C(O)NH2、−CO(O)NH−C1〜20−アルキル、−C(O)N(C1〜20アルキル)2、−O−C1〜20−アルキル、−O−C(O)−C1〜20−アルキル、−SiH3、SiH2(C1〜20−アルキル)、SiH(C1〜20−アルキル)2、Si(C1〜20−アルキル)3、C4〜8−シクロアルキル、フェニル、及び5〜8員の複素環系からなる群から独立して選択される1〜10個の置換基で置換されてよく、且つ
フェニル又は5〜8員の複素環系は1〜5個のC1〜16−アルキル基で置換されてよく、且つ
Xはトリフラート又はハロゲン、好ましくは、Br−である)
の化合物と、
以下の式
R3及びR4は互いに独立してH又はC1〜C10−アルキルであるか、又はR3及びR4は、それらに結合する−O−B−O−単位と一緒に環、好ましくは、1個又は2個のC1〜C6−アルキル、好ましくは、メチルで置換され得る5員環を形成し、
Mはアルカリ金属、アルカリ土類金属又はAlであり、
mは1、2又は3であり、
oは1、2又は3である)
の化合物とを反応させる工程を含む前記方法である。
の化合物と、
(R3O)−B−(OR4)(6)(式中、
R3及びR4は互いに独立してH又はC1〜C10−アルキルであるか、又はR3及びR4は、それらを連結する−O−B−O−単位と一緒に環、好ましくは、1個又は2個のC1〜C6−アルキル、好ましくは、メチルで置換され得る5員環を形成する)
とを反応させることによって製造され得る。
ソース電極及びドレイン電極は、適切なソース/ドレイン材料、例えば、Agを適した基板、例えば、PET上にリソグラフィでパターン形成することにより形成され得る。ソース/ドレイン電極は、次いで、溶媒処理によって、例えば、本発明の半導体材料の、好適な溶媒、例えば、テトラリン又はトルエンの溶液をスピンコーティングすることによって、半導体層で被覆され得る。半導体層は、誘電材料、例えば、ポリスチレンを、半導体層上にスピンコーティングすることによって誘電体層で被覆され得る。ゲート電極は、例えば、好適なソース/ドレイン材料、例えば、金(Au)の蒸着によって誘電体層上に堆積され得る。
5,5’−ジエチニル−2,2’−ビチオフェン(4a)(2.2g、10ミリモル)、ピナコールボラン(6a)(2.7g、21ミリモル)及びZrCp2HCl(シュワルツ試薬)(260mg、1ミリモル)の混合物を管内に密封し、65℃で48時間撹拌する。その後、混合物をシリカゲルパッドに通し、溶離液としてヘキサンと酢酸エチル(ヘキサン:酢酸エチル=10:1)を用いて逆相カラムで更に精製すると、白色固体(2.1g、49%)として化合物3aが得られる。1H NMR(400MHz,CDCl3)δ7.39(d,2H,J=18Hz),7.07(d,2H,J=3.6Hz),7.97(d,2H,J=3.6Hz),5.97(d,2H,J=18Hz),1.50(s,24H).
化合物2a(300mg、0.31ミリモル)、化合物3a(180mg、0.38ミリモル)、N−フェニルピロール−P(tert−ブチル)2(18mg、0.06ミリモル)、Pd(OAc)2(3mg、0.02ミリモル)及びLiOH(96mg、2.29ミリモル)をシュレンク管に加える。反応容器を排気し、N2で3回再充填する。次に、無水THF(13ml)を添加し、N2下にて70℃で加熱する。20分後、1滴の2−ブロモチオフェンを添加し、1時間撹拌する。1滴の2−チオフェンボロン酸を添加し、反応混合物を更に1時間70℃で撹拌する。反応混合物を、1時間にわたりMeOH(900ml)を撹拌する大きなビーカー内に沈殿させた後に濾過し、残留物を、抽出物が無色になるまで一晩アセトン(250ml)によるソックスレー抽出にかける。残留物を、真空下で乾燥させ、最少量の熱いクロロベンゼン中に溶解し、1時間にわたりMeOH(900ml)を撹拌するビーカー内に沈殿させた後に濾過し、残留物を真空下で一晩乾燥させると、ポリマー1a(310mg、97%)が得られる。1H NMR(400MHz,DCE,r.t.)δ9.06(brs,2H),8.74(d,2H,15.6Hz),7.64(d,2H,15.6Hz),7.27〜7.03(m,4H),4.25(br,4H),2.40(br,2H),1.49〜1.17(m,64H),1.01〜0.90(brs,12H).
Mn:3.44×104,PDI:2.06.
2,5−ジエチニルチオフェン(4b)(1.4g、10ミリモル)、ピナコールボラン(6a)(2.8g、21ミリモル)及びZrCp2HCl(シュワルツ試薬)(260mg、1ミリモル)の混合物を管内に密閉し、65℃で70時間撹拌する。その後、混合物をシリカゲルパッドに通し、溶離液(ヘキサン:酢酸エチル=15:1)としてヘキサンと酢酸エチルを用いる逆相カラムで更に精製すると、白色固体(1.55g、40%)として化合物3bが得られる。1H NMR(400MHz,CDCl3)δ7.38(d,2H,J=18Hz),6.95(s,2H),5.91(d,2H,J=18Hz),1.50(s,24H)。
化合物2a(450mg、0.46ミリモル)、化合物3b(177mg、0.46ミリモル)、N−フェニルピロール−P(t−ブチル)2(21mg、0.07ミリモル)、Pd(OAc)2(4mg、0.02ミリモル)及び水酸化リチウム(115mg、2.74ミリモル)をシュレンク管に加える。反応容器を排気し、N2で3回再充填する。次に、無水THF(11ml)を添加し、N2下にて70℃で加熱する。22時間後、1滴の2−ブロモチオフェンを添加し、1時間撹拌する。1滴の2−チオフェンボロン酸を添加し、反応混合物を更に4時間70℃で撹拌する。反応混合物を、1時間にわたりMeOH(900ml)を撹拌する大きなビーカー内に沈殿させた後に濾過し、残留物を、抽出物が無色になるまで一晩アセトン(250ml)によるソックスレー抽出にかける。残留物を、真空下で乾燥させ、最少量の熱いクロロベンゼン中に溶解し、1時間にわたりMeOH(900ml)を撹拌するビーカー内に沈殿させた後に濾過し、残留物を真空下で一晩乾燥させると、ポリマー1b(330mg、73%)が得られる。1H NMR(400MHz,DCE,r.t),δ9.06(brs,2H),8.70(d,2H,15.6Hz),7.58(d,2H,15.6Hz),7.52〜7.40(m,2H),4.29(br,4H),2.14(br,2H),1.50〜1.34(m,64H),1.01〜0.90(brs,12H).Mn:2.85×104,PDI:2.25.
半導体材料としてポリマー1a、1bをそれぞれ含むトップゲートボトムコンタクト型の電界効果トランジスタの製法
ポリマー1aをトルエン(5mg/ml)に溶解し、リソグラフィでパターン形成された銀(Ag)コンタクト(W/L=1000、L=10μm)を有するPET基板上に1500rpmで1分間スピンコートした後に、110℃のホットプレート上で2分間乾燥させる。
Claims (11)
- 以下の式
R1及びR2は互いに独立してC6〜30−アルキルであり、
その際、C6〜30−アルキルが、それぞれ、ハロゲン、−CN、−NO2、−NH(C1〜20−アルキル)、−N(C1〜20アルキル)2、−NH−C(O)−(C1〜20−アルキル)、−C(O)−C1〜20−アルキル、−C(O)−OC1〜20−アルキル、−C(O)NH2、−CO(O)NH−C1〜20−アルキル、−C(O)N(C1〜20−アルキル)2、及び−O−C1〜20−アルキルからなる群から独立して選択される1〜10個の置換基で置換されてよく、
oは1、2又は3であり且つ
nは5〜1000の整数である)
の単位を含むポリマー。 - R1及びR2が、互いに独立してC10〜30−アルキルである、請求項1に記載のポリマー。
- oが1又は2である、請求項1又は2に記載のポリマー。
- nが5〜500の整数である、請求項1から3までのいずれか1項に記載のポリマー。
- nが10〜100の整数である、請求項1から4までのいずれか1項に記載のポリマー。
- 請求項1に記載のポリマーの製造方法であって、以下の式
R1及びR2は互いに独立してC6〜30−アルキルであり、
その際、C6〜30−アルキルが、それぞれ、ハロゲン、−CN、−NO2、−NH(C1〜20−アルキル)、−N(C1〜20アルキル)2、−NH−C(O)−(C1〜20−アルキル)、−C(O)−C1〜20−アルキル、−C(O)−OC1〜20−アルキル、−C(O)NH2、−CO(O)NH−C1〜20−アルキル、−C(O)N(C1〜20−アルキル)2及び−O−C1〜20−アルキルからなる群から独立して選択される1〜10個の置換基で置換されてよく、且つ
Xはトリフラート又はハロゲンである)
の化合物と、
以下の式
R3及びR4は互いに独立してH又はC1〜C10−アルキルであるか、又はR3及びR4は、それらを連結する−O−B−O−単位と一緒に環を形成し、
Mはアルカリ金属及びアルカリ土類金属又はAlであり、
mは1、2又は3であり、
oは1、2又は3である)
の化合物とを反応させる工程を含む、前記方法。 - 半導体材料として請求項1に記載のポリマーを含む電子デバイス。
- 電子デバイスが有機電界効果トランジスタである、請求項8に記載の電子デバイス。
- 電子デバイスが有機光起電素子である、請求項8に記載の電子デバイス。
- 請求項1から6までのいずれか1項に記載のポリマーの半導体材料としての使用。
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US8883873B2 (en) | 2009-05-18 | 2014-11-11 | Agfa Graphics Nv | Polymerizable polymeric photoinitiators and radiation curable compositions |
CN102906892B (zh) * | 2010-03-25 | 2016-03-16 | 破立纪元有限公司 | 共轭聚合物及采用该聚合物的器件 |
IT1400116B1 (it) | 2010-05-21 | 2013-05-17 | Eni Spa | Composizione fotoattiva ad elevata mobilita' delle lacune elettroniche. |
US8633258B2 (en) | 2010-06-30 | 2014-01-21 | Dsm Ip Assets B.V. | D1492 liquid BAPO photoinitiator and its use in radiation curable compositions |
CN102344551B (zh) * | 2010-07-30 | 2013-04-03 | 海洋王照明科技股份有限公司 | 含萘四羧酸二酰亚胺单元有机半导体材料及其制备方法和应用 |
CN102344553B (zh) * | 2010-08-03 | 2014-02-19 | 海洋王照明科技股份有限公司 | 一类萘四羧酸二酰亚胺有机半导体材料及其制备方法和应用 |
CN102924509A (zh) | 2011-08-09 | 2013-02-13 | 陈婷 | 双膦酰膦酸酯化合物 |
CN103044662A (zh) * | 2011-10-11 | 2013-04-17 | 中国科学院化学研究所 | 芳酰亚胺共轭聚合物、其制备方法及其在有机光电子器件中的应用 |
CN103044660A (zh) * | 2011-10-11 | 2013-04-17 | 中国科学院化学研究所 | 芳酰亚胺共轭聚合物、其制备方法及其在有机光电子器件中的应用 |
US10005879B2 (en) * | 2012-02-03 | 2018-06-26 | Basf Se | Method for producing an organic semiconductor device |
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CN105051087A (zh) | 2015-11-11 |
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EP2935393A4 (en) | 2016-06-01 |
EP2935393A1 (en) | 2015-10-28 |
WO2014097079A1 (en) | 2014-06-26 |
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