JP7308489B2 - 化合物、化合物の前駆体、化合物を含む有機半導体材料、および有機半導体材料を含む有機電子デバイス - Google Patents
化合物、化合物の前駆体、化合物を含む有機半導体材料、および有機半導体材料を含む有機電子デバイス Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims description 139
- 239000004065 semiconductor Substances 0.000 title claims description 40
- 239000000463 material Substances 0.000 title claims description 36
- 239000002243 precursor Substances 0.000 title claims description 17
- 229920000642 polymer Polymers 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000001931 aliphatic group Chemical group 0.000 claims description 20
- 125000002723 alicyclic group Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229920002521 macromolecule Polymers 0.000 claims 1
- -1 n-octyl group Chemical group 0.000 description 134
- 239000002904 solvent Substances 0.000 description 54
- 239000003054 catalyst Substances 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000005859 coupling reaction Methods 0.000 description 14
- 230000008878 coupling Effects 0.000 description 13
- 238000010168 coupling process Methods 0.000 description 13
- 238000005259 measurement Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 12
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 12
- 125000005843 halogen group Chemical group 0.000 description 12
- 229910052763 palladium Inorganic materials 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- 239000003446 ligand Substances 0.000 description 11
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- 229940126062 Compound A Drugs 0.000 description 8
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 238000000137 annealing Methods 0.000 description 8
- 229910052731 fluorine Inorganic materials 0.000 description 8
- 125000001153 fluoro group Chemical group F* 0.000 description 8
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 239000003849 aromatic solvent Substances 0.000 description 6
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 6
- 229910052796 boron Inorganic materials 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 230000026030 halogenation Effects 0.000 description 6
- 238000005658 halogenation reaction Methods 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 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 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 229910052718 tin Inorganic materials 0.000 description 6
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
- KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 150000001805 chlorine compounds Chemical class 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 230000002140 halogenating effect Effects 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 4
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000006352 cycloaddition reaction Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000003963 dichloro group Chemical group Cl* 0.000 description 4
- 229940117389 dichlorobenzene Drugs 0.000 description 4
- 229940093499 ethyl acetate Drugs 0.000 description 4
- 238000004770 highest occupied molecular orbital Methods 0.000 description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 4
- 229940011051 isopropyl acetate Drugs 0.000 description 4
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 4
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 4
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 229940090181 propyl acetate Drugs 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 229940043232 butyl acetate Drugs 0.000 description 3
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 3
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 239000003759 ester based solvent Substances 0.000 description 3
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- OIXJMPDGGDWJOG-UHFFFAOYSA-N 1,1,1-trichloro-2-[chloro(2,2,2-trichloroethyl)phosphoryl]ethane Chemical compound ClC(Cl)(Cl)CP(Cl)(=O)CC(Cl)(Cl)Cl OIXJMPDGGDWJOG-UHFFFAOYSA-N 0.000 description 2
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Description
[1] 下記式(I)で表されるドナー性ユニットと、アクセプター性ユニットとを有する化合物。
[式(I)中、R1は、脂肪族炭化水素基または脂環式炭化水素基を表し、mは、0~2の整数を表す。A1は、それぞれ独立に、置換基を有していてもよい芳香族環を表し、nは、1~5の整数を表す。]
[2] 前記ドナー性ユニットを1~3と、前記アクセプター性ユニットを1~3有する[1]に記載の化合物。
[3] 前記ドナー性ユニットと、前記アクセプター性ユニットとを繰り返し単位として有する高分子である[1]または[2]に記載の化合物。
[4] 前記ドナー性ユニットと、前記アクセプター性ユニットとが交互に配置されている[3]に記載の化合物。
[5] 数平均分子量が2000以上、300000以下である[3]または[4]に記載の化合物。
[6] 前記アクセプター性ユニットが、下記式(Ac-1)~式(Ac-6)で表されるユニットである[1]~[5]のいずれかに記載の化合物。
[式(Ac-1)~式(Ac-6)中、R2は、それぞれ独立に、水素原子またはアルキル基を表す。*は、結合手を表す。]
[7] [1]に記載の化合物の前駆体であって、下記式(II)で表わされるユニットと、アクセプター性ユニットとを有する前駆体。
[式(II)中、R1、m、A1、nは、それぞれ上記と同義である。]
[8] 前記アクセプター性ユニットが、下記式(Ac-1)~式(Ac-6)で表されるユニットである[7]に記載の前駆体。
[式(Ac-1)~式(Ac-6)中、R2、*は、それぞれ上記と同義である。]
[9] [1]~[6]のいずれかに記載の化合物を含む有機半導体材料。
[10] n型有機半導体材料である[9]に記載の有機半導体材料。
[11] [9]または[10]に記載の有機半導体材料を含む有機電子デバイス。
本発明の化合物は、下記式(I)で表されるドナー性ユニットと、アクセプター性ユニットとを有する。なお、以下、「式(x)で表されるユニット」を、単に「ユニット(x)」という場合がある。また、「式(x)で表される化合物」を、単に「化合物(x)」という場合がある。
上記ドナー性ユニット(I)を含むことによって、HOMO準位を低く維持したままLUMO準位を引き下げることができ、安定性が良好になるとともに、熱安定性も向上し、さらには種々の官能基を付加することも容易になる。また、上記式(I)で表わされるユニットは、拡張π共役系でドナー性を示すため、このドナー性ユニット(I)と、アクセプター性ユニットとを有する化合物は、有機半導体材料(ドナー-アクセプター型有機半導体材料)として優れたものとなる。
R1の脂肪族炭化水素基は、直鎖状または分岐鎖状のいずれであってもよい。
R1の脂環式炭化水素基は、単環、多環のいずれであってもよい。
上記芳香族炭化水素環としては、例えば、ベンゼン環、ナフタレン環、アントラセン環、フェナントレン環等が挙げられ、これらの中でも、ベンゼン環が好ましい。
上記芳香族複素環としては、例えば、下記式で表される芳香族複素環が挙げられ、これらの中でも、チオフェン環、チアゾール環、ピリジン環、ピロール環、イミダゾール環、フラン環、オキサゾール環等が好ましい。
上記アクセプター性ユニットは、電子受容性の構造単位を意味しており、下記式(Ac-1)~式(Ac-6)で表されるユニットが好ましく、下記式(Ac-1)または式(Ac-2)で表されるユニットがより好ましく、下記式(Ac-1)で表されるユニットが更に好ましい。
ドナー性ユニット(I)と、アクセプター性ユニットの組合せとしては、以下の組合せが好ましい。
本発明には、上記化合物の前駆体も包含され、該前駆体は、下記式(II)で表わされるユニットと、アクセプター性ユニットとを有するところに特徴がある。
本発明には、上記化合物を含む有機半導体材料も含まれる。即ち、上記式(I)で表わされるドナー性ユニットは、熱的安定性が高く、電子供与性に優れており、上記式(I)で表わされるドナー性ユニットと、アクセプター性ユニットとを含む化合物は、HOMO準位を低く維持したままLUMO準位を引き下げることができ、安定性の観点からも有機半導体材料として有用である。
本発明の化合物は、例えば、下記ルート1またはルート2で製造できる。
本発明の化合物(X)は、下記式(1)で表される化合物と、下記式(5)で表される化合物とを反応させることによって製造できる。以下、化合物(1)と化合物(5)とを反応させる工程を「カップリング工程」という場合がある。
酸化工程では、下記化合物(3)と、酸化剤とを反応させることによって、化合物(2)を得ることができる。
芳香族環付加工程では、下記化合物(2)と、下記式(4)で表される化合物とを反応させることによって、芳香族環を有する化合物(2B)を製造できる。
化合物(2)、(2B)、または(2C)に、塩基の存在下、アジド化合物を反応させることによって、化合物(1)を得ることができる。
上記スルホニルハライド化合物としては、例えば、メタンスルホニルクロリド、エタンスルホニルクロリド、プロパンスルホニルクロリド、イソプロパンスルホニルクロリド、ブタンスルホニルクロリド、ペンタンスルホニルクロリド、ヘキサンスルホニルクロリド等のアルキルスルホニルクロリド化合物;ベンゼンスルホニルクロリド、2-メチルベンゼンスルホニルクロリド、3-メチルベンゼンスルホニルクロリド、4-メチルベンゼンスルホニルクロリド、2-クロロベンゼンスルホニルクロリド、3-クロロベンゼンスルホニルクロリド、4-クロロベンゼンスルホニルクロリド、2-ブロモベンゼンスルホニルクロリド、3-ブロモベンゼンスルホニルクロリド、4-ブロモベンゼンスルホニルクロリド、2-ヨードベンゼンスルホニルクロリド、3-ヨードベンゼンスルホニルクロリド、4-ヨードベンゼンスルホニルクロリド、2-フルオロベンゼンスルホニルクロリド、3-フルオロベンゼンスルホニルクロリド、4-フルオロベンゼンスルホニルクロリド、2-トリフルオロメチルベンゼンスルホニルクロリド、3-トリフルオロメチルベンゼンスルホニルクロリド、4-トリフルオロメチルベンゼンスルホニルクロリド等のアリールスルホニルクロリド化合物;塩化スルフリル等のスルホニルクロリド化合物;ノナフルオロブタンスルホン酸フルオリド、フェニルスルホン酸フルオリド等のスルホニルフルオリド化合物;等が挙げられる。これらの中でも、アリールスルホニルクロリド化合物またはスルホニルクロリド化合物が好ましく、アリールスルホニルクロリド化合物がより好ましく、4-メチルベンゼンスルホニルクロリドがさらに好ましい。
上記リン酸ハライド化合物としては、例えば、ジメチルホスホリルクロリド、ジエチルホスホリルクロリド、ジプロピルホスホリルクロリド、ジイソプロピルホスホリルクロリド、ジブチルホスホリルクロリド等のジアルキルホスホリルクロリド化合物;ビス(2,2,2-トリクロロエチル)ホスホリルクロリド等のジハロゲン化アルキルホスホリルクロリド化合物;2-クロロ-2-オキソ-1,3,2-ジオキサホスホラン;ジフェニルホスホリルクロリド、ビス(2-メチルフェニル)ホスホリルクロリド、ビス(3-メチルフェニル)ホスホリルクロリド、ビス(4-メチルフェニル)ホスホリルクロリド、ビス(3,5-ジメチルフェニル)ホスホリルクロリド、ビス(2-クロロフェニル)ホスホリルクロリド、ビス(3-クロロフェニル)ホスホリルクロリド、ビス(4-クロロフェニル)ホスホリルクロリド、ビス(3,5-ジクロロフェニル)ホスホリルクロリド等のジアリールホスホリルクロリド化合物;1,2-フェニレンホスホロクロリデート;等が挙げられる。これらの中でも、ジハロゲン化アルキルホスホリルクロリド化合物またはジアリールホスホリルクロリド化合物が好ましく、ビス(2,2,2-トリクロロエチル)ホスホリルクロリドまたはジフェニルホスホリルクロリドがより好ましい。
ハロゲン化は、種々の方法によって行うことができ、例えば、化合物(1B)または化合物(2B)を、酸の共存下、ハロゲン化試薬と接触させることによって行うことができる。
本発明の化合物(X)は、下記式(11)で表される化合物と、下記式(5)で表される化合物とを反応させて下記式(12)の化合物とし、更にN-オキサイド化合物(13)に誘導した後、塩基の存在下、アジド化合物を反応させることによって製造できる可能性がある。
300mLナスフラスコに、2,5-dibromopyridine(11.8g,50mmol)、mCPBA(18.5g、75mmol)、および無水ジクロロメタン(100mL)を入れ、室温で2日間撹拌した。反応終了後、飽和炭酸水素ナトリウム水溶液を加え、有機層をジクロロメタンで抽出し、無水硫酸ナトリウムを用いて乾燥させた。濃縮後、シリカゲルカラムクロマトグラフィー(Hexane/AcOEt=5:1)を用いて精製し、2,5-dibromopyridine N-oxide(白色固体)を6.74g得た(収率53%)。
1H-NMR(400MHz,CDCl3)δ=7.23(dd,J=2.1,8.7Hz,1H)、7.52(d,J=8.7Hz,1H)、8.50(d,J=2.1Hz,1H)。
1H-NMR(400MHz,CDCl3)δ=7.14(dd,J=4.0,5.0Hz,1H)、7.22(dd,J=4.0,5.0Hz,1H)、7.39(dd,J=1.0,4.0Hz,1H)、7.41(dd,J=1.0,5.0Hz,1H)、7.52(dd,J=1.9,8.6Hz,1H)、7.58(dd,J=1.0,5.0Hz,1H)、7.85(dd,J=1.0,4.0Hz,1H)、7.92(d,J=8.6Hz,1H)、8.61(d,J=1.9Hz,1H)。
1H-NMR(400MHz,CDCl3)δ=7.25(m,1H)、7.29(dd,J=4.0,5.0Hz,1H)、7.51(dd,J=1.0,5.0Hz,1H)、7.55(d,J=7.7Hz,1H)、7.63(dd,J=1.0,5.0Hz,1H)、7.89(d,J=7.7Hz,1H)、8.39(dd,J=1.0,4.0Hz,1H)、8.41(dd,J=1.0,4.0Hz,1H)。
1H-NMR(400MHz,CDCl3)δ=7.19(d,J=4.0Hz,1H)、7.25(m,1H)、7.47(d,J=7.8Hz,1H)、7.78(d,J=7.8Hz,1H)、8.07(d,J=4.0Hz,1H)、8.13(d,J=4.0Hz,1H)。
上記で得られたブロモ化体を用い、化合物(単量体)を製造した。即ち、2口フラスコに、上記ブロモ化体(132mg,0.3mmol)、および無水THF(20mL)を入れ、-78℃でブチルリチウム(1.6M,0.38mL)を加え1時間撹拌した。撹拌後、塩化トリブチルスズ(1M,0.18mL)を加え、室温でさらに一晩撹拌した。一晩撹拌後、水を加えて反応を停止させたのち、ジエチルエーテルを用いて抽出を行った。溶媒を濃縮し、アルミナカラムクロマトグラフィー(hexane/AcOEt=1:1)を用いて精製し、GPCをかけてDTTP-SnBu3を121mg得た(収率47%)。
上記実施例1で得られたDTTP-SnBu3を用い、高分子化合物を製造した。即ち、耐圧試験管に、上記DTTP-SnBu3(86mg,0.1mmol)、NDI-OD(78mg,0.1mmol)、Pd2(dba)3(5mg,0.005mmol)、P(furyl)3(6mg,0.02mmol)、および無水トルエン(4mL)、DMF(1mL)を入れ、80℃で12時間加熱撹拌した。反応終了後、メタノールで再沈殿を行い、得られた固体はソックスレー抽出した(メタノール,アセトン,塩化メチレン,クロロホルム)。そのうちクロロホルム抽出分の溶媒を濃縮し、目的の高分子化合物B(濃青色固体)を70mg得た。得られた高分子化合物は溶解性が高いので、分取GPCを用いて高分子量成分を回収した。回収した高分子量成分は、Mn=13700、Mw/Mn=2.05であった。
上記実施例2で用いたDTTP-SnBu3の前駆体と、NDI-ODを用い、上記実施例2と同様の条件で、DTTP-SnBu3の前駆体の高分子化合物を製造した。得られた固体は、ソックスレー抽出した(メタノール,アセトン,塩化メチレン,クロロホルム)。そのうちクロロホルム抽出分の溶媒を濃縮し、目的のDTTP-SnBu3の前駆体の高分子化合物C(青色固体)を55mg得た。得られた高分子化合物は溶解性が高いので、分取GPCを用いて高分子量成分を回収した。回収した高分子量成分は、Mn=21800、Mw/Mn=1.37であった。
上記実施例2で得られた高分子化合物B、上記実施例3で得られた高分子化合物Cについて、熱重量分析装置(島津製作所社製、「TGA-50」)を用いて熱重量分析測定を行った。測定には、アルミパンを用い、窒素雰囲気下、20℃から500℃まで測定した。その結果、重量減少開始温度は、高分子化合物Bが264℃、高分子化合物Cが387℃であった。これらの結果から、得られた高分子化合物B、Cは、200℃以上まで安定でありデバイスの作製に用いることができると考えられる。
上記実施例1で得られた化合物A、上記実施例2で得られた高分子化合物B、上記実施例3で得られた高分子化合物Cについて、クロロホルム溶液を調製し、紫外可視分光装置(島津製作所社製、「UV-310PC」)、および光路長1cmのセルを用いて紫外可視吸収スペクトル測定を行った。
上記実施例2で得られた高分子化合物B、上記実施例3で得られた高分子化合物Cについて、サイクリックボルタンメトリー測定装置(BAS社製、「CV-620C voltammetric analyzer」)を用い、溶媒がo-ジクロロベンゼンとアセトニトリルの5:1溶媒で、Bu4NPF6が0.1Mの溶液を用いて測定した。測定結果を上記表4に併せて示す。上記表4から明らかなように、高分子化合物B、Cは、低いLUMO準位を有しているため、n型半導体の材料として用いることができると考えられる。
オゾン処理したシリコン基板上を、オクタデシルトリクロロシラン(ODTS)を用いて処理した。処理後の基板表面に、上記実施例1で得られた化合物Aを、0.1mg/mLの濃度となるようにクロロホルムに溶解した溶液をドロップキャストすることで、ボトムゲート-ボトムコンタクト型のFET素子を作製し、FET測定を行った。チャンネル長さは5μmとした。次に、得られた素子を80℃で1時間アニールし、同様の方法でFET特性の評価を行った。得られた結果を表5に示す。μeは、電子移動度を示している。
Claims (7)
- 数平均分子量が2000以上、300000以下である請求項2に記載の化合物。
- 請求項1~3のいずれかに記載の化合物を含む有機半導体材料。
- n型有機半導体材料である請求項5に記載の有機半導体材料。
- 請求項5または6に記載の有機半導体材料を含む有機電子デバイス。
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