CN103975454B - 用于有机半导体器件的二酮基吡咯并吡咯聚合物 - Google Patents
用于有机半导体器件的二酮基吡咯并吡咯聚合物 Download PDFInfo
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- CN103975454B CN103975454B CN201280059932.2A CN201280059932A CN103975454B CN 103975454 B CN103975454 B CN 103975454B CN 201280059932 A CN201280059932 A CN 201280059932A CN 103975454 B CN103975454 B CN 103975454B
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- 229920000642 polymer Polymers 0.000 title claims abstract description 128
- 239000004065 semiconductor Substances 0.000 title claims abstract description 67
- 230000005669 field effect Effects 0.000 claims abstract description 15
- 238000013086 organic photovoltaic Methods 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 239000000463 material Substances 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 43
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 41
- 229910052760 oxygen Inorganic materials 0.000 claims description 41
- 239000001301 oxygen Substances 0.000 claims description 41
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 150000002367 halogens Chemical class 0.000 claims description 38
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- SKOWZLGOFVSKLB-UHFFFAOYSA-N hypodiboric acid Chemical compound OB(O)B(O)O SKOWZLGOFVSKLB-UHFFFAOYSA-N 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 9
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 2
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- 239000002585 base Substances 0.000 description 68
- -1 alcohol radical boron ester Chemical class 0.000 description 57
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 35
- 239000000243 solution Substances 0.000 description 34
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 16
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- 239000010931 gold Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- 239000003513 alkali Substances 0.000 description 13
- 238000000151 deposition Methods 0.000 description 13
- 229910052737 gold Inorganic materials 0.000 description 13
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229910052796 boron Inorganic materials 0.000 description 9
- 230000008021 deposition Effects 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 0 CCC*C(CC)CN Chemical compound CCC*C(CC)CN 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 238000007641 inkjet printing Methods 0.000 description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
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- 230000000052 comparative effect Effects 0.000 description 6
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000002322 conducting polymer Substances 0.000 description 5
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- 238000001035 drying Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- RZJRJXONCZWCBN-UHFFFAOYSA-N octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 5
- 238000000059 patterning Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910002666 PdCl2 Inorganic materials 0.000 description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
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- 125000002511 behenyl 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])([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([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000008859 change Effects 0.000 description 4
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- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 4
- 238000003618 dip coating Methods 0.000 description 4
- 125000003438 dodecyl 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([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
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- YKPJEYXZEBLYCI-UHFFFAOYSA-N pyrrolo[3,4-c]pyrrole Chemical class C1=NC=C2C=NC=C21 YKPJEYXZEBLYCI-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- MSIUQOWNDKIKSG-UHFFFAOYSA-N Cc1cc([s]c(C)c2)c2[s]1 Chemical compound Cc1cc([s]c(C)c2)c2[s]1 MSIUQOWNDKIKSG-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
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- 229910019142 PO4 Inorganic materials 0.000 description 3
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000001204 arachidyl 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])([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([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 125000000755 henicosyl 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])([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([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002463 lignoceryl 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])([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([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 125000002960 margaryl 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])([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 3
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- 125000001421 myristyl 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])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 125000000913 palmityl 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])([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 3
- 125000002958 pentadecyl 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])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
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- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
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- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 229910000077 silane Inorganic materials 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
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- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- KGYLMXMMQNTWEM-UHFFFAOYSA-J tetrachloropalladium Chemical compound Cl[Pd](Cl)(Cl)Cl KGYLMXMMQNTWEM-UHFFFAOYSA-J 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
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- WHLUQAYNVOGZST-UHFFFAOYSA-N tifenamil Chemical group C=1C=CC=CC=1C(C(=O)SCCN(CC)CC)C1=CC=CC=C1 WHLUQAYNVOGZST-UHFFFAOYSA-N 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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- XLOMVQKBTHCTTD-UHFFFAOYSA-N zinc oxide Inorganic materials [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 229940043798 zincon Drugs 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
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- 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
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- 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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- C08K5/45—Heterocyclic compounds having sulfur in the ring
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Abstract
本发明涉及聚合物(I)或(II)及其作为有机器件,尤其是有机光伏器件(太阳能电池)和光电二极管,或含有二极管和/或有机场效应晶体管的器件中的有机半导体的用途。本发明的聚合物具有在有机溶剂中的优异溶解度和优异成膜性质。此外,当将本发明的聚合物用于有机场效应晶体管、有机光伏器件(太阳能电池)和光电二极管中时,可观察到高能量转化效率、优异场效应迁移率、良好开/关电流比和/或优异稳定性。
Description
本发明涉及聚合物 及其作为有机器件,尤其是有机光伏器件(太阳能电池)和光电二极管,或含有二极管和/或有机场效应晶体管的器件中的有机半导体的用途。本发明的聚合物具有在有机溶剂中的优异溶解度和优异成膜性质。此外,当将本发明的聚合物用于有机场效应晶体管、有机光伏器件(太阳能电池)和光电二极管中时,可观察到高能量转化效率、优异场效应迁移率、良好开/关电流比和/或优异稳定性。
US6451459描述基于二酮基吡咯并吡咯的聚合物和共聚物及其在EL器件中的用途,该聚合物和共聚物包含以下单元
其中x选自0.005至1的范围,优选为0.01至1,和y为0.995至0,优选0.99至0,且其中x+y=1,和
其中Ar1和Ar2彼此独立地表示
和m、n为1至10的数,和
R1和R2彼此独立地表示H、C1-C18烷基、-C(O)O-C1-C18烷基、C1-C12全氟烷基、未经取代的C6-C12芳基、或经C1-C12烷基、C1-C12烷氧基或卤素取代1-3次的C6-C12芳基、C1-C12烷基-C6-C12芳基或C6-C12芳基-C1-C12烷基,
R3和R4优选表示氢、C1-C12烷基、C1-C12烷氧基、未经取代的C6-C12芳基或经C1-C12烷基、C1-C12烷氧基或卤素取代1-3次的C6-C12芳基或C1-C12全氟烷基,和R5优选表示C1-C12烷基、C1-C12烷氧基、未经取代的C6-C12芳基或经C1-C12烷基、C1-C12烷氧基或卤素取代1-3次的C6-C12芳基或C1-C12全氟烷基。
WO05/049695公开基于二酮基吡咯并吡咯(DPP)的聚合物及其在PLED、有机集成电路(O-IC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机太阳能电池(O-SC)或有机激光电二极管中的用途,但未公开式I的具体基于DPP的聚合物。
优选聚合物包含式的重复单元和式的重复单元,其中R1和R2彼此独立地为可经一个或多个氧原子间隔的C1-C25烷基,尤其是C4-C12烷基,和Ar1和Ar2彼此独立地为下式的基团:
其中-Ar3-为下式的基团: 其中R6为氢、C1-C18烷基或C1-C18烷氧基,和R32为甲基、Cl或OMe,和R8为H、C1-C18烷基或经E取代和/或经D间隔的C1-C18烷基,尤其是经-O-间隔的C1-C18烷基。
WO08/000664描述包含下式的(重复)单元的聚合物
在一个优选实施方案中,WO08/000664涉及式的聚合物,其中A如上所定义和-COM1-选自下式的重复单元:
其中R7和R7'为…,R44和R41为氢、C1-C18烷基或C1-C18烷氧基,和R45为H、C1-C18烷基或经E取代和/或经D间隔的C1-C18烷基,尤其是经-O-间隔的C1-C18烷基,其中D和E为…,和-COM2-为式 的基团,其中
R116和R117彼此独立地为H、可任选经O间隔的C1-C18烷基或可任选经O间隔的C1-C18烷氧基,
R119和R120彼此独立地为H、可任选经O间隔的C1-C18烷基,或
R119和R120一起形成式=CR100R101的基团,其中
R100和R101彼此独立地为H、C1-C18烷基,或
R119和R120一起形成可任选经C1-C18烷基取代的五或六员环。
Y.Zhu等,Macromolecules40(2007)6981-6989描述五种新的可溶性共轭聚合物,其通过Suzuki缩聚反应制备。聚合物由1,4-二酮基-2,5-二己基-3,6-双(4-溴苯基)吡咯并[3,4-c]吡咯(1a)、1,4-二酮基-2,5-二(2-乙基己基)-3,6-双(4-溴苯基)吡咯并[3,4-c]吡咯(1b)或1,4-二酮基-2,5-二己基-3,6-双(4-(4,4,5,5-四甲基-1,3,2-二氧杂硼杂戊环-2-基)苯基)吡咯并[3,4-c]吡咯(1c),和3,6-双(4,4,5,5-四甲基-1,3,2-二氧杂硼杂戊环-2-基)-9-乙基己基咔唑(2)、4,4'-二溴三苯基胺(3)、4,4'-双(4,4,5,5-四甲基-1,3,2-二氧杂硼杂戊环-2-基)三苯基胺(4)、2,7-双(4,4,5,5-四甲基-1,3,2-二氧杂硼杂戊环-2-基)-9,9-二己基芴(5)、9,10-蒽双频哪醇基硼酯(9,10-anthracenebispinacolatoboronester)(6)和4,7-二溴-2,1,3-苯并噻二唑(7)制备。这些聚合物呈现亮红色。聚合物溶液高度发荧光,最大光发射为552-600nm。
K.Zhang等,Makcromolecules41(2008)7287-7295描述主链含有2,3,5,6-四芳基化吡咯并[3,4-c]吡咯-1,4-二酮单元的聚合物P-1-P-3的合成和特性性质。P-1由2,5-双(4-叔丁基苯基)-3,6-双(4'-溴苯基)吡咯并[3,4-c]吡咯-1,4-二酮(DPP1)和9,9-二正己基芴-2,7'-双频哪醇基硼酯3制备,P-2由2,5-双(4'-溴苯基)-3,6-双(4-叔丁基苯基)-吡咯并[3,4-c]吡咯-1,4-二酮(DPP2)和3制备,和P-3由DPP1、3和2,5-双(正己氧基苯)-1,4-双频哪醇基硼酯4,经由Pd催化Suzuki偶联制备。这些聚合物的分子量为约8000-10000Da。
A.Kuehne等,Tetrahedron Letters49(2008)4722-4724公开通过Suzuki偶联的以下聚合物的合成
乙烯基醚官能团允许发光聚合物活性掺入至标准乙烯醚和缩水甘油醚光致抗蚀剂材料中。
EP2034537A2涉及包含半导体层的薄膜晶体管器件,该半导体层包含含由以下式表示的化学结构的化合物:
其中各X独立地选自S、Se、O和NR",各R"独立地选自氢、任选经取代烃和含杂原子基团,各Z独立地为任选经取代烃、含杂原子基团和卤素中的一种,d为至少1的数,e为0至2的数;a表示至少1的数;b表示0至20的数;和n表示至少1的数。
EP2075274A1公开含有高度共平面重复单元的可溶性聚噻吩衍生物。TPT(噻吩-亚苯基-噻吩)单元的共平面特性改进分子内共轭和分子间π-π相互作用的程度。
WO2010/049321公开包含下式的一个或多个(重复)单元的聚合物及其作为有机器件中的有机半导体的用途
其中
Ar1、Ar1'、Ar3和Ar3'彼此独立地为式的基团,Ar2为下式的基团:
X1和X2中的一个为N且另一个为CH。
在WO2010/049321的实施例4中,描述以下聚合物的制备:
WO2010/049323涉及包含式的一个或多个(重复)单元和选自式的重复单元的至少一种(重复)单元的聚合物;和式III或IV的聚合物及其作为有机器件中,尤其是有机光伏器件(太阳能电池)和光电二极管中的有机半导体的用途。
在一个优选实施方案中,这些聚合物包含式的重复单元,其中A为下式的基团
R1和R2为C8-C35烷基,
R3为C1-C18烷基,
B为式的基团,
R15为C4-C18烷基,
D为式的基团,和
x=0.995至0.005,y=0.005至0.995,尤其是x=0.4至0.9,y=0.6至0.1,且其中x+y=1。
在另一优选实施方案中,这些聚合物包含式的重复单元,其中A为下式的基团:
R1和R2为C8-C35烷基,R3为C4-C18烷基,和
B为式Va、IIb、IIc、IId、IIe、IIf、IIg、IIh或IIi的基团,或式Ia、Ib、Ic、Id、Ie、If或Ig的基团,条件为B不同于A,
R1"和R2"为C8-C35烷基,
X1和X2中的一个为N且另一个为CH,
D为式的基团,和
x=0.995至0.005,y=0.005至0.995,且其中x+y=1。
本发明的聚合物不同于WO2010/049323中明确公开的聚合物(例如(x=0.05至0.8和y=0.95至0.2)),其中Ar1和Ar2表示未经取代的(杂)亚芳基和/或D表示未经取代的(杂)亚芳基。
WO2010/108873涉及包含下式的一个或多个(重复)单元的聚合物
其中Ar1和Ar1'彼此独立地为稠和(芳族)杂环体系,含有至少一个噻吩环,这些噻吩环可任选经一个或多个基团取代(参见WO2010/135723)。
WO2010/115767包含下式的重复单元
其中Ar1'为稠和(芳族)杂环体系,含有至少一个噻唑环,其可任选经一个或多个基团取代,
WO2010/136352涉及一种制备具有高分子量和高区域规则度的共轭聚合物的方法,和可通过此方法获得的新聚合物。特别优选共聚物的实例显示在WO2010/136352的第21页上:
根据本发明的式(I)的聚合物不同于WO2010/136352的第21页上所公开的聚合物,其中D不可为式的基团。
WO2011/144566涉及包含式的一个或多个(重复)单元的聚合物或式 的聚合物,及其作为有机器件,尤其是有机光伏器件(太阳能电池)和光电二极管,或含有二极管和/或有机场效应晶体管的器件中的有机半导体的用途。
在一个优选实施方案中,WO2011/144566涉及包含式的重复单元的聚合物,其中
x=0.995至0.005,y=0.005至0.995,尤其是x=0.2至0.8,y=0.8至0.2,且其中x+y=1;
A为式IVa、IVc、IVe、IVg、IVh、IVi或IVj的基团,
R1和R2为C1-C35烷基,尤其是C8-C35烷基,
R104为C1-C25烷基,尤其是C4-C25烷基,其可任选经一个或多个氧或硫原子间隔,
B和D彼此独立地为式Va、Vb、Vc,尤其是Ve、Vf、Vh、Vi、Vj、Vk、Vl、Vm、Vn、Vo、Vp、Vq、Vr、Vs、Vu、Vv、Vw、Vx,尤其是Vy、Vz或Va'的基团。
在另一优选实施方案中,WO2011/144566涉及包含式的重复单元的聚合物,其中
r=0.985至0.005,s=0.005至0.985,t=0.005至0.985,u=0.005至0.985,且其中r+s+t+u=1,
A为式IVa、IVc、IVe、IVg、IVh、IVi或IVj的基团,
R1和R2为C1-C35烷基,尤其是C8-C35烷基,
R104为C1-C25烷基,尤其是C4-C25烷基,其可任选经一个或多个氧或硫原子间隔,
B、D和E彼此独立地为式Va、Vb、Vc,尤其是Ve、Vf、Vh、Vi、Vj、Vk、Vl、Vm、Vn、Vo、Vp、Vq、Vr、Vs、Vu、Vv、Vw、Vx,尤其是Vy、Vz或Va'的基团。
本发明的聚合物不同于WO2011/144566的优选聚合物,其中B、D和E不为DPP重复单元。
此外,WO2011/144566公开聚合物,例如,其不包含在本发明的式I的聚合物(两个不同DPP重复单元,不含重复单元E),也不包含在本发明的式II的聚合物(不含重复单元E)。
本发明的一个目的为降低或克服现有技术的OSC层的缺点,提供改进的电子器件,提供改进的OSC材料和组件以用于这些器件且提供其制造方法。该器件应显示出改进的稳定性、高度的膜均一性和高OSC层完整性,这些材料应具有高电荷迁移率和良好可加工性,且该方法应允许简易和具时间和成本效益的器件制造,尤其是在大规模下。专家参考以下详细说明应立刻理解本发明的其他目的。
因此,本发明的目的为提供当用于有机场效应晶体管、有机光伏器件(太阳能电池)和光电二极管中时显示出高能量转化效率、优异场效应迁移率、良好开/关电流比和/或优异稳定性的聚合物。
该目的已通过下式的聚合物实现
其中
x=0.51至0.99,y=0.49至0.01,尤其是x=0.70至0.99,y=0.30至0.01,非常特别是x=0.80至0.99和y=0.20至0.01;且其中x+y=1,
r+s=0.50至0.99,t+u=0.50至0.01,且其中r+s+t+u=1,
A为式的基团,其中
R1和R2可相同或不同和选自氢、C1-C38烷基、C2-C36链烯基、C3-C36炔基,其各自可任选经-O-、-S-或COO间隔一次或多次;C7-C100芳烷基,其可经C1-C8烷基、C1-C8烷氧基、CF3和/或F取代1-5次;和可任选经C1-C25烷基、C1-C8烷氧基、卤素或氰基取代一次或多次的苯基;
Ar1和Ar2彼此独立地为下式的基团:
B为式III的基团,其不同于A,
D具有Ar1的含义,或为式的基团;
R204和R205彼此独立地为H、CN、COOR206或C1-C6烷基;
R206为C1-C18烷基;
E为下式的基团:
其不同于D,其中
k为1,
l为0或1,
v为0或1,
z为0或1,
a为1至5,尤其是1至3的整数,
Ar4、Ar5、Ar6和Ar7彼此独立地为下式的基团:
其中X5和X6中的一个为N且另一个为CR14,
Ar20为亚芳基,或亚杂芳基,其各自可任选经取代,
R12和R12'彼此独立地为氢、卤素、C1-C25烷基,尤其是C4-C25烷基,其可任选经一个或多个氧或硫原子间隔;C1-C25烷氧基、C7-C25芳烷基或
R13为C1-C8烷基或三(C1-C8烷基)甲硅烷基,
R14、R14'、R15、R15'、R17和R17'彼此独立地为H或C1-C25烷基,其可任选经一个或多个氧原子间隔;
R18和R18'彼此独立地为氢、卤素、C1-C25烷基,其可任选经一个或多个氧或硫原子间隔;C7-C25芳烷基或C1-C25烷氧基;
R19为氢、C7-C25芳烷基、C6-C18芳基;经C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或可任选经一个或多个氧或硫原子间隔的C1-C25烷基;R20和R20'彼此独立地为氢、C7-C25芳烷基、C1-C25烷基,其可任选经一个或多个氧或硫原子间隔,
X7为-O-、-S-、-NR115-、-Si(R117)(R117')-、-C(R120)(R120')-、-C(=O)-、
X8为-O-或-NR115-;
R100和R100'彼此独立地为H、F、C1-C18烷基、经O间隔的C1-C18烷基、C1-C18烷氧基、经O间隔的C1-C18烷氧基、C1-C18全氟烷基、可任选经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基、可任选经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C2-C20杂芳基;
R101和R101'彼此独立地为H、F、C1-C18烷基、经O间隔的C1-C18烷基、C1-C18烷氧基、经O间隔的C1-C18烷氧基、C1-C18全氟烷基、可任选经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基、可任选经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C2-C20杂芳基;
R102和R102'彼此独立地为H、卤素、可任选经一个或多个氧或硫原子间隔的C1-C25烷基;C7-C25芳烷基或C1-C25烷氧基;
R103和R103'彼此独立地为氢、卤素、可任选经一个或多个氧或硫原子间隔的C1-C25烷基;可任选经C1-C8烷基和/或C1-C8烷芳基取代1-3次的C6-C24芳基;C7-C25芳烷基、CN或C1-C25烷氧基;或
R103和R103'一起形成环,
R115和R115'彼此独立地为氢、C6-C18芳基;经C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;可任选经一个或多个氧或硫原子间隔的C1-C25烷基;或C7-C25芳烷基,
R116为氢、C7-C25芳烷基、C6-C18芳基;经C1-C18烷基、C1-C18全氟烷基或C1-C18烷氧基取代的C6-C18芳基;C1-C25烷基;通过-O-或-S-间隔的C1-C25烷基;或-COOR119;R119为C1-C38烷基;
R117和R117'彼此独立地为C1-C35烷基、C7-C25芳烷基或可任选经C1-C8烷基和/或C1-C8烷氧基取代1-3次的苯基,
R120和R120'彼此独立地为氢、可任选经一个或多个氧或硫原子间隔的C1-C38烷基;或C7-C25芳烷基,
R121为H、可任选经一个或多个氧或硫原子间隔的C1-C18烷基、C1-C18全氟烷基、可任选经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基;可任选经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C2-C20杂芳基;或CN。
优选地,R12和R12'彼此独立地为氢、卤素、C1-C25烷基,尤其是C4-C25烷基,其可任选经一个或多个氧或硫原子间隔;C1-C25烷氧基、C7-C25芳烷基或
优选地,R13为C1-C8烷基或三(C1-C8烷基)甲硅烷基,
优选地,R15和R15'彼此独立地为H或可任选经一个或多个氧原子间隔的C1-C25烷基,
优选地,R18和R18'彼此独立地为氢、卤素、C1-C25烷基,尤其是C4-C25烷基,其可任选经一个或多个氧或硫原子间隔;C7-C25芳烷基或C1-C25烷氧基。
优选地,R20和R20'彼此独立地为氢、C7-C25芳烷基、C1-C25烷基,尤其是C4-C25烷基,其可任选经一个或多个氧或硫原子间隔。
优选地,R100、R100'、R102和R102'为氢。优选地,R120和R120'为C1-C38烷基。
R1和R2可不同,但优选相同。优选地,R1和R2为C1-C38烷基,优选C4-C24烷基,更优选C8-C24烷基,例如,正十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、2-乙基己基、2-丁基己基、2-丁基辛基、2-己基癸基、2-辛基十二烷基、2-癸基十四烷基、十七烷基、十八烷基、二十烷基、二十一烷基、二十二烷基或二十四烷基。C1-C38烷基、C4-C24烷基和C8-C24烷基可为线性或支化的,但优选为支化的。
有利地,基团R1和R2可由式表示,其中m1=n1+2和m1+n1≤24。手性侧链如R1和R2可为纯手性或外消旋的,其可影响化合物的形态。
优选x=0.70至0.99和y=0.30至0.01,最优选x=0.80至0.99和y=0.20至0.01。x和y表示用于制造相应式(I)聚合物中的各重复单元的量。
r+s=0.50至0.99,t+u=0.50至0.01,尤其是r+s=0.80至0.99,t+u=0.20至0.01。r、s、t和u表示用于制造相应式(II)聚合物中的各重复单元的量。
在一个优选实施方案中,Ar1和Ar2彼此独立地为式 的基团。
A优选为式的基团,其中R1和R2彼此独立地为C1-C38烷基。式IIIb的基团比式IIIa的基团更优选。
D优选为式的基团。
E优选为下式的基团:
其中R100、R100'、R102、R102'、R120和R120'如上所定义,
Ar20为可任选经取代的亚芳基、或亚杂芳基,
R12和R12'彼此独立地为氢、卤素、C1-C25烷基,尤其是C4-C25烷基,其可任选经一个或多个氧或硫原子间隔;C1-C25烷氧基、C7-C25芳烷基,或
R13为C1-C8烷基,或三(C1-C8烷基)甲硅烷基,
R15和R15'彼此独立地为H或可任选经一个或多个氧原子间隔的C1-C25烷基,
R18和R18'彼此独立地为氢、卤素、C1-C25烷基,尤其是C4-C25烷基,其可任选经一个或多个氧或硫原子间隔;C7-C25芳烷基或C1-C25烷氧基;和
R20和R20'彼此独立地为C7-C25芳烷基、C1-C25烷基,尤其是C4-C25烷基,其可任选经一个或多个氧或硫原子间隔。
亚芳基的实例为下式的基团: R18和R18'彼此独立地为氢、卤素、C1-C25烷基,尤其是C4-C25烷基,其可任选经一个或多个氧或硫原子间隔;C7-C25芳烷基或C1-C25烷氧基。
亚杂芳基的实例为下式的基团: R114和R114'彼此独立地为氢或C1-C18烷基,和R116为H或C1-C25烷基。
在一个优选实施方案中,本发明涉及包含式的重复单元的聚合物,其中
x=0.70至0.99,y=0.30至0.01,尤其是x=0.80至0.99,y=0.20至0.01,且其中x+y=1,
A为式的基团,其中R1为C1-C38烷基,尤其是C8-C38烷基,
D为式的基团,
E为下式的基团: 其中
R12和R12'彼此独立地为氢、卤素、可任选经一个或多个氧或硫原子间隔的C1-C25烷基、C1-C25烷氧基、C7-C25芳烷基或
R13为C1-C8烷基或三(C1-C8烷基)甲硅烷基,和
R120和R120'彼此独立地为氢或可任选经一个或多个氧或硫原子间隔的C1-C38烷基。
式(IIIa')的基团比式(IIIb')的基团较不优选。
在另一优选实施方案中,本发明涉及包含式的重复单元的聚合物,其中r+s=0.70至0.99,t+u=0.30至0.01,尤其是r+s=0.80至0.99,t+u=0.20至0.01,且其中r+s+t+u=1,
A为式的基团,
B为式的基团,
其不同于A,其中
R1为C1-C38烷基,尤其是C8-C38烷基,
D为式的基团,
E为下式的基团: 其中
R12和R12'彼此独立地为氢、卤素、可经一个或多个氧或硫原子间隔的C1-C25烷基、C1-C25烷氧基、C7-C25芳烷基或
R13为C1-C8烷基或三(C1-C8烷基)甲硅烷基,和
R120和R120'彼此独立地为氢或可任选地经一个或多个氧或硫原子间隔的C1-C38烷基。
式(IIIa')的基团比式(IIIb')的基团较不优选。
在该实施方案中,A可为式的基团,其中R1为线性C2-C24烷基,尤其是线性C8-C24烷基,
B为式的基团,其中
R2为支化C2-C24烷基,尤其是支化C8-C24烷基;或
A为式的基团,和
B为式的基团,其中
R1和R2不同且为线性或支化C2-C24烷基。
优选聚合物的实例显示如下:
其中x=0.70至0.99,y=0.30至0.01,尤其是x=0.80至0.99,y=0.20至0.01,且其中x+y=1,和R1为C2-C24烷基。C2-C24烷基优选为支化C2-C24烷基,例如,2-己基癸基、2-辛基十二烷基或2-癸基十四烷基。
式I或II的聚合物可通过例如Suzuki反应获得。芳族硼酸盐与卤化物(尤其是溴化物)的缩合反应,常称为“Suzuki反应”,允许存在各种有机官能团,如N.Miyaura和A.Suzuki在Chemical Reviews,第95卷,第457-2483(1995)页中所报道。
为了制备对应式I的聚合物,使对应式X11′-A-X11′的二卤化物与对应式X11-D-X11和X11-E-X11的二硼酸或二硼酸盐反应;或使对应式X11-A-X11的二硼酸或二硼酸盐与对应式X11′-D-X11′和X11′-E-X11′的二卤化物反应,其中X11'在每次出现时独立地为Cl、Br或I,和X11在每次出现时独立地为-B(OH)2、-B(OY1)2、其中Y1在每次出现时独立地为C1-C10烷基和Y2在每次出现时独立地为C2-C10亚烷基,如-CY3Y4-CY5Y6-、或-CY7Y8-CY9Y10-CY11Y12-,其中Y3、Y4、Y5、Y6、Y7、Y8、Y9、Y10、Y11和Y12彼此独立地为氢或C1-C10烷基,尤其是-C(CH3)2C(CH3)2-、-CH2C(CH3)2CH2-、或-C(CH3)2CH2C(CH3)2-,且Y13和Y14彼此独立地为氢或C1-C10烷基,反应在溶剂中和在催化剂存在下进行,例如在Pd和三苯基膦的催化作用下进行。为了制备对应式II的聚合物,使对应式X11′-A-X11′和X11′-B-X11′的二卤化物与对应式X11-D-X11和X11-E-X11的二硼酸或二硼酸盐反应;或使对应式X11-A-X11和X11-B-X11的二硼酸或二硼酸盐与对应式X11′-D-X11′和X11′-E-X11′的二卤化物反应;其中r、s、t、u、v、x和y、X11、X11'、A、B、D和E如上所定义。
优选催化剂为2-环己基膦基-2',6'-二烷氧基联苯基/乙酸钯(II)、三烷基盐/钯(0)衍生物和三烷基膦/钯(0)衍生物。尤其优选催化剂为2-二环己基膦基-2',6'-二甲氧基联苯基(sPhos)/乙酸钯(II)和四氟硼酸三叔丁基((t-Bu)3P*HBF4)/三(二亚苄基丙酮)二钯(0)(Pd2(dba)3)和三叔丁基膦(t-Bu)3P/三(二亚苄基丙酮)二钯(0)(Pd2(dba)3)。该反应通常在约0℃至180℃下于芳族烃溶剂(如甲苯,二甲苯)中进行。其他溶剂,如二甲基甲酰胺、二烷、二甲氧基乙烷和四氢呋喃也可单独或与芳族烃混合使用。将碱水溶液,优选碳酸钠或碳酸氢钠、磷酸钾、碳酸钾或碳酸氢钾用作硼酸、硼酸盐的活化剂且用作HBr净化剂。聚合反应可进行0.2-100小时。有机碱(例如氢氧化四烷基铵)和相转移催化剂(例如,TBAB)可提高硼的活性(参见例如Leadbeater&Marco;Angew.Chem.Int.Ed.Eng.42(2003)1407及其中所引的文献)。反应条件的其他变化示于T.I.Wallow和B.M.Novak,J.Org.Chem.59(1994)5034-5037;和M.Remmers、M.Schulze和G.Wegner,Macromol.RapidCommun.17(1996)239-252中。分子量的控制可通过使用过量二溴化物、二硼酸或二硼酸盐或链终止剂实现。
特别优选的方法描述于WO2010/136352中。根据WO2010/136352中所描述的方法,聚合在以下物质存在下实施
a)催化剂/配体体系,包含钯催化剂和具体有机膦或化合物,
b)碱,
c)溶剂或溶剂混合物。优选有机膦选自下式的三取代膦
1)R305和R306一起形成环 2)R303和R304一起形成环
优选催化剂的实例包括以下化合物:
乙酰丙酮钯(II)、二亚苄基丙酮钯(0)配合物、丙酸钯(II),
Pd2(dba)3:[三(二亚苄基丙酮)二钯(0)],
Pd(dba)2:[双(二亚苄基丙酮)钯(0)],
Pd(PR3)2,其中PR3为式VI的三取代膦,
Pd(OAc)2:[乙酸钯(II)]、氯化钯(II)、溴化钯(II)、四氯钯酸(II)锂,
PdCl2(PR3)2;其中PR3为式VI的三取代膦;钯(0)二烯丙醚配合物、硝酸钯(II),
PdCl2(PhCN)2:[二氯双(苄腈)钯(II)],
PdCl2(CH3CN):[二氯双(乙腈)钯(II)],和
PdCl2(COD):[二氯(1,5-环辛二烯)钯(II)]。
尤其优选为PdCl2、Pd2(dba)3、Pd(dba)2、Pd(OAc)2或Pd(PR3)2。最优选为Pd2(dba)3和Pd(OAc)2。
钯催化剂以催化量存在于反应混合物中。术语“催化量”是指明显低于一当量(杂)芳族化合物的量,优选基于所使用的(杂)芳族化合物的当量数为0.001-5摩尔%,最优选0.001-1摩尔%。
反应混合物中膦或盐的量优选基于所使用的(杂)芳族化合物的当量数为0.001-10摩尔%,最优选0.01-5摩尔%。Pd:膦的优选比为1:4。
该碱可选自所有水性和非水性碱且可为无机或有机的。反应混合物优选存在至少1.5当量该碱/硼官能团。合适碱为,例如,碱金属和碱土金属的氢氧化物、羧酸盐、碳酸盐、氟化物和磷酸盐,如钠和钾的氢氧化物、乙酸盐、碳酸盐、氟化物和磷酸盐,或金属醇化物。也可使用碱混合物。碱优选为锂盐,例如,锂的烷醇盐(例如,甲醇锂和乙醇锂)、锂的氢氧化物、羧酸盐、碳酸盐、氟化物和/或磷酸盐。
当前最优选碱为水性LiOHxH2O(LiOH的单水合物)和(无水)LiOH。
该反应通常在约0℃至180℃,优选20-160℃,更优选40-140℃,最优选40-120℃下进行。聚合反应可进行0.1小时,尤其是0.2-100小时。
在本发明的一个优选实施方案中,溶剂为THF,碱为LiOH*H2O且反应在THF回流温度(约65℃)下进行。
该溶剂例如选自甲苯、二甲苯、苯甲醚、THF、2-甲基四氢呋喃、二烷、氯苯、氟苯或包含一种或多种溶剂的溶剂混合物,例如THF/甲苯和任选水。最优选为THF或THF/水。
有利地,该聚合在以下物质存在下实施
a)乙酸钯(II)或Pd2(dba)3、(三(二亚苄基丙酮)二钯(0))和有机膦A-1至A-13,
b)LiOH或LiOHxH2O;和
c)THF,和任选水。若使用LiOH的单水合物,则不需要添加水。
优选地,该聚合反应在不存在氧的惰性条件下进行。将氮气和更优选氩气用作惰性气体。
WO2010/136352中描述的方法适合大规模应用,可轻易实现和以高产率、高纯度和高选择性将原料转化为各聚合物。若需要,可将单官能芳基卤化物或芳基硼酸盐用作这些反应的链终止剂,形成端芳基。
可通过控制Suzuki反应中单体进料的顺序和组成来控制所获得的共聚物中单体单元的顺序。
本发明聚合物的其他制备方法更详细地在下文中对式I聚合物说明。式II的聚合物可利用对制备式I聚合物所描述的方法制备。
本发明的聚合物也可通过Stille偶联合成(参见例如Babudri等,J.Mater.Chem.,2004,14,11-34;J.K.Stille,Angew.Chemie Int.Ed.Engl.1986,25,508)。
为了制备对应式I的聚合物,使式X11′-A-X11′的二卤化物与式X21-D-X21和X21-E-X21的化合物反应;或使式X11′-D-X11′和X11′-E-X11′的二卤化物与式X21-A-X21的化合物反应,其中X21为基团-SnR207R208R209和X11'如上所定义,反应在0℃至200℃的温度下在惰性溶剂中在含钯催化剂存在下进行,其中R207、R208和R209相同或不同且为H或C1-C6烷基,其中两个基团任选地形成共同环且该基团任选地支化或未支化。此处必须确保所用所有单体的总体中有机锡官能团与卤素官能团的比率高度平衡。此外,可以证实,在反应结束时通过使用单官能试剂进行封端来去除任何过量的反应性基团为有利的。为进行该方法,优选地将锡化合物和卤素化合物引入一种或多种惰性有机溶剂中,且在0-200℃,优选30-170℃的温度下搅拌1-200小时,优选5-150小时。可通过本领域熟练技术人员所已知且适用于各种聚合物的方法来纯化粗产物,例如重复进行的再沉淀或甚至通过透析来纯化。
用于所描述方法的合适有机溶剂为例如醚,例如二乙醚、二甲氧基乙烷、二乙二醇二甲醚、四氢呋喃、二烷、二氧杂环戊烷、二异丙醚和叔丁基甲醚;烃,例如己烷、异己烷、庚烷、环己烷、苯、甲苯和二甲苯;醇,例如甲醇、乙醇、1-丙醇、2-丙醇、乙二醇、1-丁醇、2-丁醇和叔丁醇;酮,例如丙酮、乙基甲基酮和异丁基甲基酮;酰胺,例如二甲基甲酰胺(DMF)、二甲基乙酰胺和N-甲基吡咯烷酮;腈,例如乙腈、丙腈和丁腈;及其混合物。
钯和膦组分应类似于对Suzuki反应所描述进行选择。
或者,本发明的聚合物也可通过Negishi反应合成,使用锌试剂A-(ZnX22)2,其中X22为卤素和卤化物;和D-(X23)2和E-(X23)2,其中X23为卤素或三氟甲磺酸根,或使用D-(X22)2、E-(X22)2和A-(ZnX23)2。参考例如E.Negishi等,Heterocycles18(1982)117-22。
或者,本发明的聚合物也可通过Hiyama反应合成,使用有机硅试剂A-(SiR210R211R212)2,其中R210、R211和R212相同或不同且为卤素或C1-C6烷基,和D-(X23)2和E-(X23)2,其中X23为卤素或三氟甲磺酸根,或使用A-(X23)2、D-(SiR210R211R212)2和E-(SiR210R211R212)2。参考例如T.Hiyama等,Pure Appl.Chem.66(1994)1471-1478和T.Hiyama等,Synlett(1991)845-853。
卤素为氟、氯、溴和碘,尤其是氟。
若可能,C1-C25烷基(C1-C18烷基)通常为线性或支化的。实例为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、1,1,3,3-四甲基戊基、正己基、1-甲基己基、1,1,3,3,5,5-六甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基、正壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、二十烷基、二十一烷基、二十二烷基、二十四烷基或二十五烷基。C1-C8烷基通常为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、2-戊基、3-戊基、2,2-二甲基丙基、正己基、正庚基、正辛基、1,1,3,3-四甲基丁基和2-乙基己基。C1-C4烷基通常为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基。卤代烷基为其中一个或大于一个氢原子经卤素原子代替的烷基。实例为C1-C4全氟烷基,其可经支化或未支化,例如,-CF3、-CF2CF3、-CF2CF2CF3、-CF(CF3)2、-(CF2)3CF3、和-C(CF3)3。
C1-C25烷氧基(C1-C18烷氧基)为直链或支化烷氧基,例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、叔丁氧基、戊氧基、异戊氧基或叔戊氧基、庚氧基、辛氧基、异辛氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十四烷氧基、十五烷氧基、十六烷氧基、十七烷氧基和十八烷氧基。
C1-C8烷氧基的实例为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基、正戊氧基、2-戊氧基、3-戊氧基、2,2-二甲基丙氧基、正己氧基、正庚氧基、正辛氧基、1,1,3,3-四甲基丁氧基和2-乙基己氧基,优选C1-C4烷氧基,如通常为甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、仲丁氧基、异丁氧基、叔丁氧基。术语“烷硫基”意指与烷氧基相同的基团,不同的是醚链接的氧原子经硫原子代替。
C2-C38链烯基为直链或支化烯基且可未经取代或经取代。实例为烯丙基、甲基烯丙基、异丙烯基、2-丁烯基、3-丁烯基、异丁烯基、正戊-2,4-二烯基、3-甲基丁-2-烯基、正辛-2-烯基、正十二烷-2-烯基、异十二烷烯基、正十二烷-2-烯基或正十八烷-4-烯基。
C2-38炔基为直链或支化且可未经取代或经取代。实例为乙炔基、1-丙炔-3-基、1-丁炔-4-基、1-戊炔-5-基、2-甲基-3-丁炔-2-基、1,4-戊二炔-3-基、1,3-戊二炔-5-基、1-己炔-6-基、顺式-3-甲基2-戊烯-4-炔-1-基、反式-3-甲基2-戊烯-4-炔-1-基、1,3-己二炔-5-基、1-辛炔-8-基、1-壬炔-9-基、1-癸炔-10-基或1-二十四炔-24-基。
C7-C100芳烷基通常为C7-C25芳烷基。芳烷基可经C1-C8烷基、C1-C8烷氧基、CF3和/或F取代1-5次。实例为苄基、2-苄基-2-丙基、β-苯基乙基、α,α-二甲基苄基、ω-苯基丁基、ω,ω-二甲基-ω-苯基丁基、ω-苯基十二烷基、ω-苯基十八烷基、ω-苯基二十烷基或ω-苯基二十二烷基,优选C7-C18芳烷基,如苄基、2-苄基-2-丙基、β-苯基乙基、α,α-二甲基苄基、ω-苯基丁基、ω,ω-二甲基-ω-苯基丁基、ω-苯基十二烷基或ω-苯基十八烷基,特别优选C7-C12芳烷基,如苄基、2-苄基-2-丙基、β-苯基乙基、α,α-二甲基苄基、ω-苯基丁基、或ω,ω-二甲基-ω-苯基丁基,其中脂族烃基和芳族烃基均可未经取代或经取代。优选实例为苄基、2-苯基乙基、3-苯基丙基、萘基乙基、萘基甲基和异丙苯基。
亚芳基通常为C6-C24亚芳基,其任选可经取代。实例为亚苯基、4-甲基亚苯基、4-甲氧基亚苯基、亚萘基,尤其是1-亚萘基或2-亚萘基、亚芘基、2-或9-亚芴基、亚菲基或亚蒽基,其可未经取代或经一个或多个C1-C18烷基取代。
可任选经G取代的C2-C30亚杂芳基A4、A5和A6表示具有五至七个环原子的环或稠和环体系,其中杂原子可为氮、氧或硫,且通常为具有五至30个具有至少六个共轭电子的原子的杂环基团,如亚噻吩基、亚噻吩并噻吩基、亚苯并噻吩基、亚二苯并噻吩基、亚噻蒽基、亚呋喃基、亚糠基、2H-亚吡喃基、亚苯并呋喃基、亚异苯并呋喃基、亚二苯并呋喃基、亚苯氧基噻吩基、亚吡咯基、亚咪唑基、亚吡唑基、亚吡啶基、亚联吡啶基、亚三嗪基、亚嘧啶基、亚吡嗪基、亚哒嗪基、亚中氮茚基、亚异氮茚基、亚吲哚基、亚吲唑基、亚嘌呤基、亚喹嗪基、亚喹啉基、亚异喹啉基、2,3-亚二氮杂萘基、1,5-亚二氮杂萘基、亚喹喔啉基、亚喹唑啉基、亚肉啉基、亚蝶啶基、亚咔唑基、亚咔啉基、亚苯并三唑基、亚苯并唑基、亚菲啶基、亚吖啶基、亚嘧啶基、亚菲咯啉基、亚吩嗪基、亚异噻唑基、亚吩噻嗪基、亚异唑基、亚呋咱基、亚咔唑基或亚吩嗪基,其可未经取代或经一个或多个C1-C18烷基取代。
上述基团的可能取代基为C1-C8烷基、羟基、巯基、C1-C8烷氧基、C1-C8烷硫基、卤素、C1-C8卤代烷基、氰基、硝基或甲硅烷基,尤其是C1-C8烷基、C1-C8烷氧基、C1-C8烷硫基、卤素、C1-C8卤代烷基或氰基。
经一个或多个O间隔的C1-C25烷基为例如(CH2CH2O)1-9-Rx,其中Rx为H或C1-C10烷基;CH2-CH(ORy')-CH2-O-Ry,其中Ry为C1-C18烷基,和Ry'涵盖与Ry相同的含义或为H。经一个或多个S间隔的C1-C25烷基为例如(CH2CH2S)1-9-Rx,其中Rx为H或C1-C10烷基;CH2-CH(SRy')-CH2-S-Ry,其中Ry为C1-C18烷基,和Ry'涵盖与Ry相同的含义或为H。
若取代基如R101在基团中出现大于一次,则其在每次出现时可不同。
本发明的聚合物可用作半导体器件中的半导体层。因此,本发明也涉及包含本发明的聚合物的半导体器件或有机半导体材料、层或组件。该半导体器件尤其是有机光伏(PV)器件(太阳能电池)、光电二极管或有机场效应晶体管。
含有本发明聚合物的混合物形成包含本发明聚合物(通常5-99.9999重量%,尤其是20-85重量%)和至少其他材料的半导体层。该其他材料可为但不限于具有不同分子量的同一本发明聚合物的一部分、另一本发明聚合物、半导体聚合物、聚合粘合剂、有机小分子、碳纳米管、富勒烯衍生物、无机颗粒(量子点、量子棒、量子三脚架、TiO2、ZnO等)、导电颗粒(Au、Ag等)、绝缘材料,类似于对栅极介电材料所描述的那些(PET、PS等)。如上所述,半导体层也可由本发明的一种或多种聚合物与聚合粘合剂的混合物组成。本发明聚合物与聚合粘合剂之比可在5至95的百分比内变化。优选,该聚合粘合剂为半结晶聚合物,如聚苯乙烯(PS)、高密度聚乙烯(HDPE)、聚丙烯(PP)和聚甲基丙烯酸甲酯(PMMA)。通过该技术,可避免电学性能降低(参见WO2008/001123A1)。
因此,本发明也涉及有机半导体材料、层或组件,其包含
(a)本发明的聚合物,和
(b)任选其他材料。
在一个优选实施方案中,该其他材料为小分子。此类小分子描述于例如WO2010/108873、WO09/047104、US6,690,029、WO2007082584(包括但不限于化合物(I1)、(I2)、(I3)、(I4)、(I5)、(I6)、(I7)、(I8)和(I9))、WO2008107089(包括但不限于化合物A1、A2、B1、B2、C1和C2)和WO2009047104中。
小分子优选为下式的化合物
其中
A1和A2彼此独立地为下式的基团
a'为1或2;b为0或1;c为0或1;
R1'和R2'可相同或不同且选自氢、C1-C38烷基、C2-C38链烯基、C3-C38炔基,其各自可任选经-O-、-S-或COO间隔一次或多次;可经C1-C8烷基、C1-C8烷氧基、CF3和/或F取代1-5次的C7-C100芳烷基;和可任选经C1-C25烷基、C1-C8烷氧基、卤素或氰基取代一次或多次的苯基;
A3、A4和A5彼此独立地为下式的二价基团
R214和R214'彼此独立地为氢、卤素、C1-C25卤代烷基,尤其是CF3、氰基、可任选经一个或多个氧或硫原子间隔的C1-C25烷基;C7-C25芳烷基或C1-C25烷氧基;
R3为氢、卤素、氰基、C1-C25烷基、其中R22至R25和R29至R33彼此独立地表示H、卤素、氰基或C1-C25烷基,和R26为H、卤素、氰基、苯基或C1-C25烷基。
式VI的化合物以基于式I或II的DPP聚合物与式VI的化合物的量为0.1-99.9%,尤其是5-95重量%的量使用。
A3、A4和A5彼此独立地为式的二价基团。
A3优选为式的基团(虚线表示与DPP基础单元的键)。更优选,A3为式的基团。最优选,A3为式的基团。A3和A4优选为式的基团。更优选,A3和A4为式的基团。
R3优选为氢、氰基、
式VI的化合物优选为下式的化合物
其中
a'为1或2;b为0或1;c为0或1;
R1'和R2'相同或不同且为C1-C38烷基,
A3、A4和A5彼此独立地为式的二价基团,
R3为氢、氰基、式VI的化合物的实例显示如下:
其中R1'和R2'相同且为C1-C38烷基。
R1'和R2'为C1-C38烷基,优选C4-C24烷基,更优选C8-C24烷基,例如,正十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、2-乙基己基、2-丁基己基、2-丁基辛基、2-己基癸基、2-癸基十四烷基、十七烷基、十八烷基、二十烷基、二十一烷基、二十二烷基或二十四烷基。C1-C38烷基、C4-C24烷基和C8-C24烷基可为线性或支化的,但优选为支化的。优选R1'和R2'具有相同含义。有利地,基团R1'和R2'可由式表示,其中m1=n1+2且m1+n1≤24。手性侧链如R1'和R2'可为纯手性或外消旋的,其可影响化合物的形态。
式(VI)的化合物及其合成例如描述于WO2009/047104和WO2012/041849中。
当前最优选的式VI的化合物为下式的化合物
该衍生物特别利于掺杂DPP聚合物,键合至源极/漏极电极,并提供在常见溶剂中的良好稳定性。
本发明聚合物可单独或组合用作半导体器件的有机半导体层。可通过任一有用方式来提供层,例如,蒸气沉积(用于分子量相对较低的材料)和印刷技术。本发明化合物可充分地溶于有机溶剂中且可进行溶液沉积和图案化(例如,通过旋涂、浸涂、喷墨印刷、凹版印刷、柔性印刷、胶版印刷、丝网印刷、微接触(波)印刷、滴注或分区浇注或其他已知技术来进行)。
本发明聚合物可用于包含多个OTFT的集成电路以及各种电子制品中。该制品包括例如射频识别(RFID)标签、用于挠性显示器(例如,用于个人计算机、移动电话或手持式器件)的背板、智能卡、存储器件、传感器(例如光传感器、图像传感器、生物传感器、化学传感器、机械传感器或温度传感器),尤其是光电二极管或安全器件等。由于其两极性,该材料也可用于有机发光晶体管(OLET)中。
本发明另一方面为包含一种或多种本发明聚合物的有机半导体材料、层或组件。另一方面为本发明聚合物或材料在有机光伏(PV)器件(太阳能电池)、光电二极管或有机场效应晶体管(OFET)中的用途。另一方面为包含本发明聚合物或材料的有机光伏(PV)器件(太阳能电池)、光电二极管或有机场效应晶体管(OFET)。
本发明聚合物通常以薄有机层或膜形式用作有机半导体,优选小于30微米厚。通常,本发明的半导体层至多为1微米(=1μm)厚,然而若需要,可更厚。对于各种电子器件应用而言,厚度也可小于约1微米。例如,就用于OFET中而言,层厚度通常可为100nm或更小。层的准确厚度取决于例如使用该层的电子器件的要求。
例如,OFET中漏极电极与源电极之间的活性半导体通道可包含本发明的层。
本发明OFET器件优选包含:
-源极电极,
-漏极电极,
-栅极电极,
-半导体层,
-一个或多个栅极绝缘体层,和
-任选地基材,其中该半导体层包含本发明的聚合物,或本发明的有机半导体材料、层或组件。
OFET器件中的栅极电极、源极电极和漏极电极以及绝缘和半导体层可以任何顺序排列,条件为源极电极和漏极电极通过绝缘层与栅极电极分开,栅极电极和半导体层均接触绝缘层,且源极电极和漏极电极均接触半导体层。
优选地,OFET包含具有第一侧和第二侧的绝缘体、位于该绝缘体第一侧上的栅极电极、位于该绝缘体第二侧上且包含本发明聚合物的层以及位于该聚合物层上的漏极电极和源极电极。
OFET器件可为顶栅极器件或底栅极器件。
OFET器件的合适结构和制造方法已为本领域熟练技术人员所熟知且阐述于文献例如WO03/052841中。
通常,本发明的半导体层至多为1微米(=1μm)厚,然而若需要,可更厚。对于各种电子器件应用而言,厚度也可小于约1微米。例如,就用于OFET中而言,层厚度通常可为100nm或更小。层的准确厚度取决于例如使用该层的电子器件的要求。
绝缘层(介电层)通常可为无机材料膜或有机聚合膜。适合作为栅极介电层的无机材料的说明性实例包括氧化硅、氮化硅、氧化铝、钛酸钡、钛酸钡锆等。用于栅极介电层的有机聚合物的说明性实例包括聚酯、聚碳酸酯、聚(乙烯基苯酚)、聚酰亚胺、聚苯乙烯、聚(甲基丙烯酸酯)、聚(丙烯酸酯)、环氧树脂、如WO07/113107中所描述的光敏光致抗蚀剂等。在示例性实施方案中,热生长氧化硅(SiO2)可用作该介电层。
该介电层的厚度为例如约10纳米至约2000纳米,取决于所使用的介电材料的介电常数。介电层的典型厚度为约100纳米至约500纳米。介电层可具有例如小于约10-12S/cm的导电率。
该栅极绝缘层可包含例如氟聚合物,例如市售Cytop或Cytop(获自Asahi Glass)。优选,栅极绝缘层通过例如旋涂、刮涂、绕线棒涂覆、喷涂或浸涂或其他已知方法由包含绝缘体材料和具有一个或多个氟原子的一种或多种溶剂(氟溶剂),优选全氟溶剂的配制剂沉积。合适全氟溶剂为例如(购自Acros,目录号12380)。其他合适氟聚合物和氟溶剂在现有技术中已知,例如全氟聚合物Teflon 1600或2400(获自DuPont),或(获自Cytonix)或全氟溶剂FC(Acros,No.12377)。
为了利用式I或II的DPP聚合物形成有机活性层,可将包括氯仿或氯苯的组合物用于该有机活性层。在用于有机活性层的组合物中使用的溶剂的实例可包括氯仿、氯苯、二氯苯、三氯苯、甲苯、二甲苯、甲基萘、均三甲苯、茚满、四氢化萘、十氢化萘或其混合物。形成该有机活性层的方法的实例包括但不限于丝网印刷、印刷、旋涂、狭模涂覆(slot-diecoating)、浸涂或喷墨。
若介电材料由溶液沉积至有机半导体上,则其不应导致有机半导体溶解。类似地,若将有机半导体由溶液沉积于介电材料上,则该介电材料不应被溶解。避免此类溶解的技术包括:使用正交溶剂(orthogonal solvent),即使用用于沉积最上层但不溶解下层和使下层交联的溶剂。该绝缘层的厚度优选小于2微米,更优选小于500nm。
在包含于本发明的OFET中的栅极电极和源极/漏极电极中,可使用常见金属,其具体实例包括但不限于铂(Pt)、钯(Pd)、金(Au)、银(Ag)、铜(Cu)、铝(Al)、镍(Ni)。也可使用合金和氧化物,如三氧化钼和氧化铟锡(ITO)。优选,栅极、源极和漏极电极中的至少一个的材料选自Cu、Ag、Au或其合金。源极和漏极电极可通过热蒸发沉积且使用本领域已知的标准光刻和剥离技术图案化。
基材可为刚性或挠性的。刚性基材可选自玻璃或硅且挠性基材可包括薄玻璃或塑料,如聚(对苯二甲酸乙二醇酯)(PET)、聚萘二甲酸乙二醇酯(PEN)、聚碳酸酯、聚碳酸酯、聚乙烯醇、聚丙烯酸酯、聚酰亚胺、聚降冰片烯和聚醚砜(PES)。
或者,导电聚合物可沉积作为源极和漏极电极。此类导电聚合物的一个实例为聚(亚乙基二氧噻吩)(PEDOT),然而本领域已知其他导电聚合物。此类导电聚合物可由溶液使用例如旋涂或喷墨印刷技术及其他溶液沉积技术沉积。
为了制造简易,源极和漏极电极优选由相同材料形成。然而,应理解源极和漏极电极可由不同材料形成以使电荷注入和提取分别最优化。
源极和漏极电极的常见厚度为例如约40纳米至约1微米,更具体厚度为约100纳米至约400纳米。
在源极与漏极电极之间所界定的通道的长度可至多为500微米,但优选该长度小于200微米,更优选小于100微米,最优选小于20微米。
在器件结构中可包含其他层。例如,可将自组装单层(SAM)沉积于栅极、源极或漏极电极、基材、绝缘层和有机半导体材料上以提高结晶度、降低接触电阻、修复表面特性和提高需要处的粘合。用于此类单层的示例性材料包括具有长链烷基的氯-或烷氧基-硅烷,例如十八烷基三氯硅烷。
制造该有机薄膜晶体管的方法可包括:沉积源极和漏极电极;将半导体层形成于该源极和漏极电极上,该半导体层包含DPP聚合物和在该源极与漏极电极之间的通道区域中的受体化合物。该有机半导体材料优选由溶液沉积。优选溶液沉积技术包括旋涂和喷墨印刷。其他溶液沉积技术包括浸涂、辊印刷和丝网印刷。
底栅极OFET器件可利用如下说明的方法形成。
1.栅极沉积和图案化(例如,ITO涂覆基材的图案化)。
2.介电材料沉积和图案化(例如,可交联、可光图案化介电材料)。
3.源极-漏极材料沉积和图案化(例如,银,光刻)。
4.源极-漏极表面处理。可通过将基材浸入自组装材料溶液中,或通过旋涂稀释溶液来施加表面处理基团。可通过清洗移除过量(未连接)材料。
5.沉积有机半导体材料(例如,通过喷墨印刷)。
此技术也与顶栅极器件相容。在此情况下,首先沉积和图案化源极-漏极层。随后对该源极-漏极层施加表面处理,然后为有机半导体材料、栅极介电材料和栅极沉积。
OFET具有宽范围应用。一种应用为驱动有机器件(设备),优选有机光学器件中的像素。此类光学器件的实例包括光响应器件,特别是光探测器,和光发射器件,特别是有机发光器件。高迁移率OTFT特别适合作为用于主动矩阵有机发光器件,例如显示器应用中使用的背板。
本发明的聚合物可用于有机光伏(PV)器件(太阳能电池)中。因此,本发明提供包含本发明聚合物的PV器件。具有此结构的器件也具有整流性质,故也可称为光电二极管。光响应器件可用作由光产电的太阳能电池和测量或侦测光的光探测器。
PV器件依照此顺序包含:
(a)阴极(电极),
(b)任选过渡层,如碱金属卤化物,尤其是氟化锂,
(c)光活性层,
(d)任选平滑层,
(e)阳极(电极),
(f)基材。
光活性层包含本发明的聚合物。优选,光活性层由作为电子供体的本发明的共轭聚合物和作为电子受体的受体材料,类似于富勒烯,尤其是官能化富勒烯PCBM制成。
对于异质结太阳能电池而言,活性层优选包含重量比率为1:1-1:3的本发明聚合物与富勒烯的混合物,该富勒烯为例如[60]PCBM(=6,6-苯基-C61-丁酸甲酯)或[70]PCBM。可用于本发明中的富勒烯具有宽范围的大小(碳原子数/分子)。本文所用的术语富勒烯包括纯碳的各种笼状分子,包括Buckminster富勒烯(C60)和相关“球形”富勒烯以及碳纳米管。富勒烯可选自本领域中所已知的那些,例如C20-C1000。优选地,富勒烯选自C60-C96。最优选地,富勒烯为C60或C70,例如[60]PCBM或[70]PCBM。还容许使用经化学改性的富勒烯,条件为经改性富勒烯保持受体型和电子迁移率特性。受体材料还可为选自如下的材料:任一半导体聚合物(例如,本发明聚合物,条件为聚合物保持受体型和电子迁移率特性)、有机小分子、碳纳米管、无机颗粒(量子点、量子棒、量子三脚架、TiO2、ZnO等)。
光活性层由本发明聚合物(作为电子供体)和富勒烯,尤其是官能化富勒烯PCBM(作为电子受体)构成。将该两种组分与溶剂混合并通过例如以下方法以溶液形式施加至平滑层上:旋涂法、浇注法、Langmuir-Blodgett(“LB”)法、喷墨印刷法和滴涂法。还可使用刮擦辊或印刷方法来使用该光活性层涂覆较大表面。优选使用分散剂如氯苯来代替通常所用的甲苯作为溶剂。在这些方法中,从操作容易性和成本角度考虑,尤其优选真空沉积法、旋涂法、喷墨印刷法和浇注法。
在使用旋涂法、浇注法和喷墨印刷法形成层的情形下,可使用通过将组合物溶解或分散于合适有机溶剂如苯、甲苯、二甲苯、四氢呋喃、甲基四氢呋喃、N,N-二甲基甲酰胺、丙酮、乙腈、苯甲醚、二氯甲烷、二甲亚砜、氯苯、1,2-二氯苯及其混合物中制得的浓度为0.01-90重量%的溶液和/或分散体来实施涂覆。
光伏(PV)器件还可由多结点太阳能电池构成,该多结点太阳能电池在彼此的顶部经加工以吸收更多太阳光谱。该结构描述于例如例如App.Phys.Let.90,143512(2007),Adv.Funct.Mater.16,1897-1903(2006)和WO2004/112161中。
所谓的“串级太阳能电池”按以下顺序包含:
(a)阴极(电极),
(b)任选的过渡层,例如碱金属卤化物,尤其是氟化锂,
(c)光活性层,
(d)任选的平滑层,
(e)中间电极(例如Au、Al、ZnO、TiO2等)
(f)任选的用于匹配能级的额外电极,
(g)任选的过渡层,例如碱金属卤化物,尤其是氟化锂,
(h)光活性层,
(i)任选的平滑层,
(j)阳极(电极),
(k)基材。
还可在纤维上加工PV器件,例如如US20070079867和US20060013549中所述。
由于具有优异的自组织性能,包含本发明聚合物的材料或膜还可单独或与其他材料一起用于LCD或OLED器件中或作为对准层用于LCD或OLED器件中,例如如US2003/0021913中所述。
所包括的下列实施例仅用于阐释本发明而并不限制权利要求书的范畴。除非另有说明,否则所有份数和百分比均以重量计。
重均分子量(Mw)和多分散性(Mw/Mn=PD)通过高温凝胶渗透色谱法(HT-GPC)测得[设备:GPC PL220,来自Polymer实验室(Church Stretton,UK;现为Varian),其由折射率(RI)产生反应,色谱条件:柱:3“PLgel Olexis”柱,来自Polymer实验室(Church Stretton,UK);平均粒度为13μm(尺寸为300×8mm I.D.)流动相:1,2,4-三氯苯,通过真空蒸馏纯化且通过丁羟基甲苯(BHT,200mg/l)稳定,色谱温度:150℃;流动相流量:1ml/min;溶质浓度:约1mg/ml;注射体积:200μl;检测:RI,分子量校准程序:使用一组由Polymer实验室(ChurchStretton,UK)获得的10份聚苯乙烯校准标样来实施相对校准,该聚苯乙烯的分子量范围跨度为1,930,000-5,050Da,即,PS1,930,000、PS1,460,000、PS1,075,000、PS560,000、PS330,000、PS96,000、PS52,000、PS30,300、PS10,100、PS5,050Da。使用多项式校准来计算分子量。
下文实施例给出的所有聚合物结构均为经由所述聚合程序获得的聚合物产物的理想化代表。若两种以上组分彼此共聚,则聚合物中的顺序取决于聚合条件可为交替或无规的。
实施例
实施例1
a)聚合物制备:
在氩气下,将4.021g(1当量)二溴化合物[1000623-98-2]、1.204g(0.8当量)二硼酸酯[175361-81-6]、0.368g(0.2当量)二硼酸酯[239075-02-6]、0.0395g乙酸钯(II)和0.202g膦配体[672937-61-0]溶于在反应器中回流的脱气四氢呋喃中。随后添加1.13g LiOH单水合物[1310-66-3]并将反应混合物再回流2小时。随后将反应混合物倾于甲醇上,过滤且通过甲醇清洗。随后通过索格利特(Soxhlet)萃取来分级滤饼,首先使用正庚烷,随后使用环己烷且最后使用四氢呋喃。使用丙酮将产物由四氢呋喃级分中沉淀出来,过滤并通过丙酮清洗。随后将产物溶于氯仿中并与5%NaCN水溶液一起回流过夜。分离各相,通过水清洗氯仿溶液三次并随后使用甲醇将产物由氯仿溶液中沉淀出来以得到式P-1的聚合物(x:y=80:20)。通过高温GPC表征该聚合物且分子量为54700,Mw/Mn比为2。
b)溶液制备:
随后通过将0.75%聚合物P-1溶于甲苯中制备溶液(Sol-1)。在40℃下搅拌2小时后,通过0.45微米过滤器(micron filter)过滤Sol-1。
c)有机场效应晶体管(OFET;顶栅极底接触)的制备
c1)基材制备
通过30nm厚金层涂覆挠性聚对苯二甲酸乙二醇酯(PET)箔(MitsubishiHostaphan GN)。通过光刻在金层上制造叉指电极(interdigited electrode)。通道宽度L为10微米且其长度W为10000微米,获得1000的W/L比。随后通过丙酮和异丙醇小心清洁基材以移除用于制造电极的任何残留痕量光致抗蚀剂。
c2)有机半导体层
将半导体溶液Sol-1旋涂于经清洁的挠性基材上。随后在加热板上,在90℃下在空气中干燥膜30秒。旋涂条件(1500rpm,持续15秒)使得干燥后的半导体膜的厚度为50+/-5nm(通过Dektak6M(获自Veeco)测量厚度)。
c3)介电层
介电材料溶液为4%聚甲基丙烯酸甲酯(PMMA)950K的乙酸丁酯/乳酸乙酯(60/40)溶液(1004084,购自Allresist)。通过旋涂(rpm=1800,持续30秒)将介电材料溶液施用于干半导体层,获得500nm+/-10nm的厚度(干燥后)。将介电层在90℃下在空气中干燥2分钟。介电膜的电容为5.8±0.2nF/cm2。
c4)栅极
栅极电极通过在介电材料上热蒸发50nm金制成。蒸发在高真空(<10-5托)下进行。
c5)OFET测量
OFET的饱和转移曲线通过Keithley2612A数字源表(source meter)测量。在-15V的栅极电压下所观察到的饱和空穴迁移率(42个OFET的平均值)为0.11+/-0.004cm2/sec*V(漏极电压设定为-20V)且亚阈值变化(subthresold swing)为1V/dec。
聚合物P-1具有在有机溶剂中的优异溶解度和优异成膜性质。应用实施例1的OFET(其中半导体层由聚合物P-1组成)显示出优异可加工性(可再现性)、空穴迁移率和亚阈值变化。
实施例2至5和对照实施例1至4
a)聚合物制备:
聚合物P-2至P-9如对实施例1a)中的聚合物P-1所述制备,不同的是二硼酸酯[175361-81-6]与二硼酸酯[239075-02-6]之比经相应改变。
b)溶液制备
随后通过将0.75%各聚合物溶于甲苯中来制备溶液。在40℃下搅拌2小时后,通过0.45微米过滤器过滤溶液,由此获得半导体溶液。
c)有机场效应晶体管(OFET;顶栅极底接触)的制备
c1)基材制备
通过30nm厚金层涂覆聚对苯二甲酸乙二醇酯(PET)挠性箔(MitsubishiHostaphan GN)。通过光刻在金层上制造叉指电极。通道宽度L为10微米及其长度W为10000微米,获得1000的W/L比。随后通过丙酮和异丙醇小心清洁基材以移除用于制造电极的任何残留痕量光致抗蚀剂。
c2)有机半导体层
将半导体溶液旋涂于经清洁的挠性基材上。随后将膜在加热板上在90℃下在空气中干燥30秒。旋涂条件使得干燥后的半导体膜的厚度为50+/-5nm(通过Dektak6M(获自Veeco)测量厚度)。
c3)介电层
介电材料溶液为4%PMMA950K(1004084,购自Allresist)的乙酸丁酯/乳酸乙酯(60/40)溶液。通过旋涂(rpm=1800,持续30秒)将介电材料溶液施用于干半导体层,获得500nm+/-10nm的厚度(干燥后)。将介电层在90℃下在空气中干燥2分钟。介电膜的电容为5.8±0.1nF/cm2。
c4)栅极
栅极电极通过在介电材料上热蒸发50nm金制成。蒸发在高真空(<10-5托)下进行。
c5)OFET测量
在实施例2至5和对照实施例1至4中所获得的OFET饱和转移曲线通过Keithley2612A数字源表测量。所观察到的空穴迁移率为使用漏极电压=-20V在-15V栅极电压下由饱和转移曲线计算出的42个OFET的平均值。在实施例2至5和对照实施例1至4中通过将聚合物P-2至P-9用作半导体所获得的OFET的空穴迁移率和聚合物P-2至P-9的x、Mw、Mn和Mw/Mn示于下表中:
1)(x+y=1)
2)Mw=重均分子量,Mn=数均分子量
对照实施例2和3中所获得的OFET的迁移率(其中将聚合物P-7(x=0.60)、P-8(x=0.40)和P-9(x=0)用作半导体)低于实施例2至5中所获得的OFET的迁移率(其中将x=0.70至0.99的聚合物用作半导体)。在对照实施例1中所获得的OFET的迁移率的标准偏差(其中将聚合物P-6(x=1)用作半导体)高于在实施例2至5中所获得的OFET的迁移率的标准偏差(其中将x=0.70至0.99的聚合物用作半导体)(较高再现性)。x=0.8(y=0.2)时的值对应最优平衡,在最高的迁移率下达到最小标准偏差(最高再现性)。
实施例6
a)基材制备:
通过30nm厚金层涂覆聚对苯二甲酸乙二醇酯(PET)挠性箔(MitsubishiHostaphan GN)。通过光刻在金层上制造叉指电极。通道宽度L为10微米且其长度W为10000微米,获得1000的W/L比。随后通过丙酮和异丙醇小心清洁基材以移除用于制造电极的任何残留痕量光致抗蚀剂材料。
b)溶液制备:
溶液A:将0.75%聚合物(P-10,Mw:60700;x=0.80,y=0.20)在4小时内在80℃下溶于甲苯中。
溶液B:将0.75%化合物在2小时内在50℃下溶于甲苯与氯仿(95:5)的混合物中。将5重量%溶液B与95重量%溶液A混合(=半导体溶液)。
c)OFET制备(顶栅极底接触)
c1)有机半导体层
将半导体溶液在空气(洁净室(clean room))中刮涂于经清洁的挠性基材上。随后在加热板上在90℃下在空气中将该膜干燥30秒。该刮涂条件使得该半导体膜在干燥后的厚度为60±5nm(厚度通过Dektak6M(获自Veeco)测量)。
c2)介电层
介电材料溶液为Cytop溶液(AGC CE(Asahi Glass Chemical),CYTOPCT-809M)。通过旋涂(rpm=1800,持续30秒)将介电材料溶液施用于干半导体层上,获得500nm±10nm的厚度(干燥后)。将介电层在90℃下在空气中干燥2分钟。介电膜的电容为3.8±0.02nF/cm2。
c3)栅极
栅极电极通过在介电材料上热蒸发50nm金制成。蒸发在高真空(<10-5托)下进行。
d)OFET测量
OFET的饱和转移曲线通过Keithley2612A数字源表测量。在-15V的栅极电压下所观察到的空穴迁移率(使用漏极电压=-20V由饱和转移曲线计算出的42个OFET的平均值)为0.75±0.03cm2/sec*V且亚阈值变化为小于0.6V/DEC。亚阈值变化(越低越好)为在介电/半导体界面处的陷阱能级的浓度的指示。在最佳情况下,在室温下,其可为60mV/dec。
对照实施例5
重复实施例7,不同的是以聚合物P-10代替聚合物P-10与化合物A-1形成半导体层,获得0.5±0.05cm2/秒*V的迁移率和小于0.7V/DEC的亚阈值变化。
Claims (17)
1.一种下式的聚合物
其中
x=0.70至0.99,y=0.30至0.01,且其中x+y=1,
A为式的基团,其中
R1和R2可相同或不同且选自氢、C1-C38烷基、C2-C38链烯基、C3-C38炔基,其各自可任选经-O-、-S-或COO间隔一次或多次;可经C1-C8烷基、C1-C8烷氧基、CF3和/或F取代1-5次的C7-C100芳烷基;和可任选经C1-C25烷基、C1-C8烷氧基、卤素或氰基取代一次或多次的苯基;
Ar1和Ar2彼此独立地为下式的基团:
D为式的基团;
E为下式的基团:
其中
Ar20为可任选经取代的亚芳基或可任选经取代的亚杂芳基,
R12和R12'彼此独立地为氢、卤素、可任选经一个或多个氧或硫原子间隔的C1-C25烷基;C1-C25烷氧基、C7-C25芳烷基,或
R13为C1-C8烷基,或三(C1-C8烷基)甲硅烷基,
R15和R15'彼此独立地为H或可任选经一个或多个氧原子间隔的C1-C25烷基,
R18和R18'彼此独立地为氢、卤素、可任选经一个或多个氧或硫原子间隔的C1-C25烷基、C7-C25芳烷基或C1-C25烷氧基;和
R20和R20'彼此独立地为氢、C7-C25芳烷基、可任选经一个或多个氧或硫原子间隔的C1-C25烷基,
R100和R100'彼此独立地为H、F、C1-C18烷基、经O间隔的C1-C18烷基、C1-C18烷氧基、经O间隔的C1-C18烷氧基、C1-C18全氟烷基、可任选经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C6-C24芳基、可任选经C1-C8烷基和/或C1-C8烷氧基取代1-3次的C2-C20杂芳基;
R102和R102'彼此独立地为H、卤素、可任选经一个或多个氧或硫原子间隔的C1-C25烷基;C7-C25芳烷基或C1-C25烷氧基;
R120和R120'彼此独立地为氢、可任选经一个或多个氧或硫原子间隔的C1-C38烷基;或C7-C25芳烷基。
2.根据权利要求1的聚合物,其中R1和R2可相同或不同且选自C1-C38烷基。
3.根据权利要求1的聚合物,其中A为式 的基团,其中R1和R2彼此独立地为C1-C38烷基。
4.根据权利要求2的聚合物,其中A为式 的基团,其中R1和R2彼此独立地为C1-C38烷基。
5.根据权利要求1的聚合物,其包含式的重复单元,其中
x=0.70至0.99,y=0.30至0.01,且其中x+y=1,
A为式的基团,其中R1为C1-C38烷基,
D为式的基团,
E为下式的基团: 其中
R12和R12'彼此独立地为氢、卤素、可任选经一个或多个氧或硫原子间隔的C1-C25烷基、C1-C25烷氧基、C7-C25芳烷基,或
R13为C1-C8烷基或三(C1-C8烷基)甲硅烷基,和
R120和R120'彼此独立地为氢或可任选经一个或多个氧或硫原子间隔的C1-C38烷基。
6.根据权利要求5的聚合物,其中x=0.80至0.99,y=0.20至0.01。
7.根据权利要求5的聚合物,其中R1为C8-C38烷基。
8.根据权利要求5的聚合物,其中A为式的基团,其中R1如权利要求5中所定义。
9.根据权利要求1的聚合物,其为下式的聚合物
其中x=0.70至0.99,y=0.30至0.01,且其中x+y=1,
R1为C2-C24烷基。
10.一种有机半导体材料、层或组件,包含
(a)根据权利要求1-9中任一项的聚合物,和
(b)任选地至少其他材料。
11.根据权利要求10的有机半导体材料、层或组件,其中该其他材料为下式的化合物
其中
A1和A2彼此独立地为下式的基团
a'为1或2;b为0或1;c为0或1;
R1'和R2'可相同或不同且选自氢、C1-C38烷基、C2-C38链烯基、C3-C38炔基,其各自可任选经-O-、-S-或COO间隔一次或多次;可经C1-C8烷基、C1-C8烷氧基、CF3和/或F取代1-5次的C7-C100芳烷基;和可任选经C1-C25烷基、C1-C8烷氧基、卤素或氰基取代一次或多次的苯基;
A3、A4和A5彼此独立地为下式的二价基团
R214和R214'彼此独立地为氢、卤素、C1-C25卤代烷基、氰基、可任选经一个或多个氧或硫原子间隔的C1-C25烷基、C7-C25芳烷基或C1-C25烷氧基;R3为氢、卤素、氰基、C1-C25烷基、其中R22至R25和R29至R33彼此独立地表示H、卤素、氰基或C1-C25烷基,和R26为H、卤素、氰基、苯基或C1-C25烷基。
12.根据权利要求11的有机半导体材料、层或组件,其中所述C1-C25卤代烷基为CF3。
13.一种半导体器件,包含根据权利要求1-9中任一项的聚合物,或根据权利要求10-12中任一项的有机半导体材料、层或组件。
14.根据权利要求13的半导体器件,其为有机光伏器件、光电二极管或有机场效应晶体管。
15.一种制备有机半导体器件的方法,该方法包括将根据权利要求1-9中任一项的聚合物在有机溶剂中的溶液和/或分散体施用至合适基材并移除该溶剂。
16.根据权利要求1-9中任一项的聚合物或根据权利要求10-12中任一项的有机半导体材料、层或组件在光伏器件、光电二极管或有机场效应晶体管中的用途。
17.一种制备式的聚合物的方法,包括使对应于式X11′-A-X11′的二卤化物与对应于式X11-D-X11和X11-E-X11的二硼酸或二硼酸酯在溶剂中和在催化剂存在下反应;或
包括使对应于式X11-A-X11的二硼酸或二硼酸酯与对应于式X11′-D-X11′和X11′-E-X11′的二卤化物在溶剂中和在催化剂存在下反应;
其中x和y、A、D和E如权利要求1中所定义,
X11'在每次出现时独立地为Cl、Br或I,
X11在每次出现时独立地为-B(OH)2、-B(OY1)2、其中Y1在每次出现时独立地为C1-C10烷基和Y2在每次出现时独立地为C2-C10亚烷基,和Y13和Y14彼此独立地为氢或C1-C10烷基。
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EP2834284B1 (en) | 2012-04-02 | 2017-05-10 | Basf Se | Phenanthro[9,10-b]furan polymers and small molecules for electronic applications |
CN104334610A (zh) | 2012-04-04 | 2015-02-04 | 巴斯夫欧洲公司 | 二酮基吡咯并吡咯聚合物和小分子 |
KR102173448B1 (ko) | 2013-05-06 | 2020-11-04 | 주식회사 클랩 | 유기 전자 응용품 내의 유전체로서의 가용성 시클릭 이미드 함유 중합체 |
US9786409B2 (en) | 2013-06-27 | 2017-10-10 | Basf Se | Metathesis polymers as dielectrics |
WO2015009768A1 (en) | 2013-07-15 | 2015-01-22 | Polyera Corporation | Photopatternable materials and related electronic devices and methods |
KR102409794B1 (ko) | 2014-09-25 | 2022-06-17 | 주식회사 클랩 | 광-가교성 유전체로서의 에테르계 중합체 |
US9580556B2 (en) | 2015-01-29 | 2017-02-28 | Corning Incorporated | DPP with branched alkyl-chain or (and) fused thiophene with branched alkyl-chain and the related designing strategy to increase the molecular weight of their semi-conducting copolymers |
CN105891267B (zh) * | 2015-04-27 | 2018-08-28 | 济南大学 | 一种基于一氨基苯基取代卟啉纳米材料的二氧化氮气敏传感器 |
JP6442057B2 (ja) * | 2015-07-07 | 2018-12-19 | 富士フイルム株式会社 | 有機半導体素子、化合物、有機半導体組成物、並びに、有機半導体膜及びその製造方法 |
EP3464415B1 (en) * | 2016-05-25 | 2020-08-19 | Basf Se | Semiconductors |
WO2018060015A1 (en) | 2016-09-27 | 2018-04-05 | Basf Se | Star-shaped styrene polymers with enhanced glass transition temperature |
CN109715717B (zh) | 2016-09-27 | 2022-09-20 | 巴斯夫欧洲公司 | 具有经增强的可交联性的星形及三嵌段聚合物 |
US11296290B2 (en) | 2018-03-07 | 2022-04-05 | Clap Co., Ltd. | Patterning method for preparing top-gate, bottom-contact organic field effect transistors |
WO2019170719A1 (en) | 2018-03-08 | 2019-09-12 | Basf Se | Organic field effect transistor comprising semiconducting single-walled carbon nanotubes and organic semiconducting material |
JP2021530577A (ja) | 2018-06-26 | 2021-11-11 | クラップ カンパニー リミテッドClap Co., Ltd. | 誘電体としてのビニルエーテル系高分子 |
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---|---|---|---|---|
CN102203160A (zh) * | 2008-10-31 | 2011-09-28 | 巴斯夫欧洲公司 | 用于有机半导体器件的二酮吡咯并吡咯聚合物 |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
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TWI290164B (en) | 1999-08-26 | 2007-11-21 | Ciba Sc Holding Ag | DPP-containing conjugated polymers and electroluminescent devices |
US20030021913A1 (en) | 2001-07-03 | 2003-01-30 | O'neill Mary | Liquid crystal alignment layer |
US6690029B1 (en) | 2001-08-24 | 2004-02-10 | University Of Kentucky Research Foundation | Substituted pentacenes and electronic devices made with substituted pentacenes |
WO2003052841A1 (en) | 2001-12-19 | 2003-06-26 | Avecia Limited | Organic field effect transistor with an organic dielectric |
DE10326547A1 (de) | 2003-06-12 | 2005-01-05 | Siemens Ag | Tandemsolarzelle mit einer gemeinsamen organischen Elektrode |
WO2005049695A1 (en) | 2003-10-28 | 2005-06-02 | Ciba Specialty Chemicals Holding Inc. | Novel diketopyrrolopyrrole polymers |
US7194173B2 (en) | 2004-07-16 | 2007-03-20 | The Trustees Of Princeton University | Organic devices having a fiber structure |
US20070079867A1 (en) | 2005-10-12 | 2007-04-12 | Kethinni Chittibabu | Photovoltaic fibers |
JP2009524226A (ja) | 2006-01-21 | 2009-06-25 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 有機半導体配合物を備える電子短チャネル装置 |
JP5015231B2 (ja) | 2006-03-30 | 2012-08-29 | チバ ホールディング インコーポレーテッド | 電子ペーパーディスプレイ装置に用いるカラーフィルター用感光性レジスト組成物 |
GB0612929D0 (en) | 2006-06-29 | 2006-08-09 | Univ Cambridge Tech | High-performance organic field-effect transistors based on dilute, crystalline-crystalline polymer blends and block copolymers |
WO2008000664A1 (en) | 2006-06-30 | 2008-01-03 | Ciba Holding Inc. | Diketopyrrolopyrrole polymers as organic semiconductors |
EP2132213B1 (en) | 2007-03-07 | 2013-05-15 | University of Kentucky Research Foundation | Silylethynylated heteroacenes and electronic devices made therewith |
US7910684B2 (en) | 2007-09-06 | 2011-03-22 | Xerox Corporation | Diketopyrrolopyrrole-based derivatives for thin film transistors |
US8404864B2 (en) | 2007-10-09 | 2013-03-26 | Basf Se | Pyrrolopyrrole derivatives, their manufacture and use |
ES2345739T3 (es) | 2007-12-27 | 2010-09-30 | Industrial Technology Research Institute | Derivados de politiofeno solubles. |
WO2010049321A1 (en) * | 2008-10-31 | 2010-05-06 | Basf Se | Diketopyrrolopyrrole polymers for use in organic field effect transistors |
BRPI1013566A2 (pt) | 2009-03-23 | 2016-04-12 | Basf Se | polímero, composto, material, camada ou componente orgânicos semi condutores, dispositivo semicondutor, processos para a preparação de um dispositivo semicondutor orgânico, de um composto, e de um polímero, e, uso do polímero, do composto e/ou do material, camada ou componente orgânicos semi condutores |
BRPI1014578A2 (pt) | 2009-04-08 | 2015-08-25 | Basf Se | Composto, material, camada ou componente semicondutor orgânico, dispositivo, semicondutor, e, uso de um composto. |
CN102439059B (zh) | 2009-05-21 | 2014-06-11 | 破立纪元有限公司 | 共轭聚合物及其在光电子器件中的用途 |
JP5623512B2 (ja) * | 2009-05-27 | 2014-11-12 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | (複素環式)芳香族化合物の重合方法 |
WO2011144566A2 (en) | 2010-05-19 | 2011-11-24 | Basf Se | Diketopyrrolopyrrole polymers for use in organic semiconductor devices |
KR20130094773A (ko) * | 2010-06-24 | 2013-08-26 | 바스프 에스이 | 온/오프 전류비가 개선되고 임계 이동이 제어가능한 유기 전계 효과 트랜지스터 |
EP2621927B1 (en) | 2010-09-29 | 2020-02-12 | Basf Se | Semiconductors based on diketopyrrolopyrroles |
US9362508B2 (en) | 2011-06-22 | 2016-06-07 | Basf Se | Diketopyrrolopyrrole oligomers for use in organic semiconductor devices |
-
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