JP7162129B2 - 有機半導体としてのインダセノ誘導体 - Google Patents
有機半導体としてのインダセノ誘導体 Download PDFInfo
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- JP7162129B2 JP7162129B2 JP2021520921A JP2021520921A JP7162129B2 JP 7162129 B2 JP7162129 B2 JP 7162129B2 JP 2021520921 A JP2021520921 A JP 2021520921A JP 2021520921 A JP2021520921 A JP 2021520921A JP 7162129 B2 JP7162129 B2 JP 7162129B2
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- 239000004065 semiconductor Substances 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 113
- 229910052799 carbon Inorganic materials 0.000 claims description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 50
- 150000002367 halogens Chemical class 0.000 claims description 50
- 125000001424 substituent group Chemical group 0.000 claims description 40
- 229920000642 polymer Polymers 0.000 claims description 38
- 125000005549 heteroarylene group Chemical group 0.000 claims description 37
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 23
- 229910052711 selenium Inorganic materials 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 16
- 229910052710 silicon Inorganic materials 0.000 claims description 16
- 230000005669 field effect Effects 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 229910018557 Si O Inorganic materials 0.000 claims description 6
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 claims description 6
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims description 4
- -1 n-hexyl (n- hexyl) Chemical group 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
- 239000000203 mixture Substances 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000000034 method Methods 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 125000006574 non-aromatic ring group Chemical group 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000010931 gold Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000013086 organic photovoltaic Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 229910052714 tellurium Inorganic materials 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 7
- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 229910052732 germanium Inorganic materials 0.000 description 5
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000003989 dielectric material Substances 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 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
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 3
- VUDZSIYXZUYWSC-DBRKOABJSA-N (4r)-1-[(2r,4r,5r)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one Chemical compound FC1(F)[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)N[C@H](O)CC1 VUDZSIYXZUYWSC-DBRKOABJSA-N 0.000 description 3
- IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 3
- HPKJGHVHQWJOOT-ZJOUEHCJSA-N N-[(2S)-3-cyclohexyl-1-oxo-1-({(2S)-1-oxo-3-[(3S)-2-oxopyrrolidin-3-yl]propan-2-yl}amino)propan-2-yl]-1H-indole-2-carboxamide Chemical compound C1C(CCCC1)C[C@H](NC(=O)C=1NC2=CC=CC=C2C=1)C(=O)N[C@@H](C[C@H]1C(=O)NCC1)C=O HPKJGHVHQWJOOT-ZJOUEHCJSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000002800 charge carrier Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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 2
- LJIOTBMDLVHTBO-CUYJMHBOSA-N (2s)-2-amino-n-[(1r,2r)-1-cyano-2-[4-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]phenyl]cyclopropyl]butanamide Chemical compound CC[C@H](N)C(=O)N[C@]1(C#N)C[C@@H]1C1=CC=C(C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)C=C1 LJIOTBMDLVHTBO-CUYJMHBOSA-N 0.000 description 2
- IXULCOYQSDIBFO-UHFFFAOYSA-N (3-bromothiophen-2-yl)methanol Chemical compound OCC=1SC=CC=1Br IXULCOYQSDIBFO-UHFFFAOYSA-N 0.000 description 2
- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 2
- BCZHCWCOQDRYGS-UHFFFAOYSA-N 3-bromothiophene-2-carbaldehyde Chemical compound BrC=1C=CSC=1C=O BCZHCWCOQDRYGS-UHFFFAOYSA-N 0.000 description 2
- WCDLCPLAAKUJNY-UHFFFAOYSA-N 4-[4-[3-(1h-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidin-6-yl]phenyl]morpholine Chemical compound C1COCCN1C1=CC=C(C2=CN3N=CC(=C3N=C2)C2=CNN=C2)C=C1 WCDLCPLAAKUJNY-UHFFFAOYSA-N 0.000 description 2
- MITGKKFYIJJQGL-UHFFFAOYSA-N 9-(4-chlorobenzoyl)-6-methylsulfonyl-2,3-dihydro-1H-carbazol-4-one Chemical compound ClC1=CC=C(C(=O)N2C3=CC=C(C=C3C=3C(CCCC2=3)=O)S(=O)(=O)C)C=C1 MITGKKFYIJJQGL-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- KQIADDMXRMTWHZ-UHFFFAOYSA-N chloro-tri(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)C(C)C KQIADDMXRMTWHZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000004811 fluoropolymer Substances 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 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
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 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
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- 239000002094 self assembled monolayer Substances 0.000 description 2
- 239000013545 self-assembled monolayer Substances 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052721 tungsten Inorganic materials 0.000 description 2
- AFINAILKDBCXMX-PBHICJAKSA-N (2s,3r)-2-amino-3-hydroxy-n-(4-octylphenyl)butanamide Chemical compound CCCCCCCCC1=CC=C(NC(=O)[C@@H](N)[C@@H](C)O)C=C1 AFINAILKDBCXMX-PBHICJAKSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- IBXMKLPFLZYRQZ-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 IBXMKLPFLZYRQZ-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- UVAMFBJPMUMURT-UHFFFAOYSA-N 2,3,4,5,6-pentafluorobenzenethiol Chemical compound FC1=C(F)C(F)=C(S)C(F)=C1F UVAMFBJPMUMURT-UHFFFAOYSA-N 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- FEOWHLLJXAECMU-UHFFFAOYSA-N 4,7-dibromo-2,1,3-benzothiadiazole Chemical compound BrC1=CC=C(Br)C2=NSN=C12 FEOWHLLJXAECMU-UHFFFAOYSA-N 0.000 description 1
- 206010063836 Atrioventricular septal defect Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 239000007983 Tris buffer Substances 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
- 239000008346 aqueous phase Substances 0.000 description 1
- 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 1
- 239000012267 brine Substances 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000012043 crude product Substances 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
- 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 1
- 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 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LMBWSYZSUOEYSN-UHFFFAOYSA-N diethyldithiocarbamic acid Chemical compound CCN(CC)C(S)=S LMBWSYZSUOEYSN-UHFFFAOYSA-N 0.000 description 1
- 229950004394 ditiocarb Drugs 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
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 125000005644 linolenyl group Chemical group 0.000 description 1
- 125000005645 linoleyl group Chemical group 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 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 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
- 125000005071 nonynyl group Chemical group C(#CCCCCCCC)* 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 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 1
- 239000003921 oil Substances 0.000 description 1
- 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 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 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
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical group CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 0.000 description 1
- COHOGNZHAUOXPA-UHFFFAOYSA-N trimethyl(phenyl)stannane Chemical compound C[Sn](C)(C)C1=CC=CC=C1 COHOGNZHAUOXPA-UHFFFAOYSA-N 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 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
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Description
Claims (14)
- 1つ以上の化学式1Aの単位、化学式1Bの単位、化学式1Cの単位、化学式1Dの単位、化学式1Eの単位、化学式1’Aの単位、化学式1’Bの単位、化学式1’Cの単位又は化学式1’Dの単位を含む、化合物。
Xは、それぞれの場合にO、S、Se又はTeであり、
Qは、それぞれの場合にC、Si又はGeであり、
R1は、それぞれの場合にH、C1-50-アルキル(C1-50-alkyl)、-[CH2]O-[O-SiRaRa]p-OSiRaRaRa、-[CH2]O-[RaRaSi-O]p-SiRaRaRa、-[CRbRb]q-CRbRbRb、C2-50-アルケニル、C2-50-アルキニル、C5-8-シクロアルキル、C6-14-アリール及び5~14角形のヘテロアリールからなる群から選ばれ、
ここで、
oは、0~10の整数であり、
pは、1~40の整数であり、
Raは、それぞれの場合にC1-10-アルキル、C2-10-アルケニル又はC2-10-アルキニルであり、
qは、1~50の整数であり、
Rbは、それぞれの場合にH又はハロゲンであり、ただし、-[CRbRb]q-CRbRbRbにおいてすべてのRbがHであるものではなく、
C1-50-アルキル、C2-50-アルケニル及びC2-50-アルキニルは、ORc、OC(O)-Rc、C(O)-ORc、C(O)-Rc、NRcRc、NRc-C(O)Rc、C(O)-NRcRc、N[C(O)Rc][C(O)Rc]、SRc、CN、-SiRcRcRc及びNO2からなる群から独立して選ばれた1つ~4つの置換基で置換されてもよく、
C5-8-シクロアルキルは、C1-10-アルキル、C2-10-アルケニル、C2-10-アルキニル、ORc、OC(O)-Rc、C(O)-ORc、C(O)-Rc、NRcRc、NRc-C(O)Rc、C(O)-NRcRc、N[C(O)Rc][C(O)Rc]、SRc、ハロゲン、CN、-SiRcRcRc及びNO2からなる群から独立して選ばれた1つ又は2つの置換基で置換されてもよく、C5-8-シクロアルキルの1つのCH2基は、O、S、OC(O)、CO、NRc又はNRc-COに置き換えられ、
C6-14-アリール及び5~14角形のヘテロアリールは、C1-10-アルキル、C2-10-アルケニル、C2-10-アルキニル、ORc、OC(O)-Rc、C(O)-ORc、C(O)-Rc、NRcRc、NRc-C(O)Rc、C(O)-NRcRc、N[C(O)Rc][C(O)Rc]、SRc、ハロゲン、CN及びNO2からなる群から独立して選ばれた1つ~3つの置換基で置換されてもよく、
ここで、
Rcは、それぞれの場合にH、C1-20-アルキル、C2-10-アルケニル又はC2-10-アルキニルであり、
R2は、それぞれの場合にH、C1-30-アルキル、C2-30-アルケニル、C2-30-アルキニル又はハロゲンであり、
nは、0、1、2、3又は4であり、
mは、0、1、2、3又は4であり、
L1及びL2は、互いに独立して、それぞれの場合に、C6-26-アリレン、5~20角形のヘテロアリレン、
C6-26-アリレン及び5~20角形のヘテロアリレンは、それぞれの場合にC1-30-アルキル、C2-30-アルケニル、C2-30-アルキニル及びハロゲンからなる群から選ばれた1つ~4つの置換基Rdで置換されてもよく、
Yは、それぞれの場合にO、S、Se、又はTeであり、
R3は、それぞれの場合にH、C1-30-アルキル、C2-30-アルケニル、C2-30-アルキニル又はハロゲンである。 - 前記化合物は、ポリマーである、請求項1に記載の化合物。
- Xは、O、S又はSeである、請求項1または2に記載の化合物。
- Qは、C又はSiである、請求項1~3のいずれか一項に記載の化合物。
- R1は、それぞれの場合にH、C1-50-アルキル、-[CH2]O-[RaRaSi-O]p-SiRaRaRa、-[CRbRb]q-CRbRbRb、C2-50-アルケニル及びC2-50-アルキニルからなる群から選ばれてもよく、
ここで、
oは、1~10の整数であり、
pは、1~40の整数であり、
Raは、それぞれの場合にC1-10-アルキル、C2-10-アルケニル又はC2-10-アルキニルであり、
qは、1~50の整数であり、
Rbは、それぞれの場合にH又はハロゲンであり、ただし、-[CRbRb]q-CRbRbRbにおいてすべてのRbがHであるものではなく、
C1-50-アルキル、C2-50-アルケニル及びC2-50-アルキニルは、ORc、OC(O)-Rc、C(O)-ORc、C(O)-Rc、NRcRc、NRc-C(O)Rc、C(O)-NRcRc、N[C(O)Rc][C(O)Rc]、SRc、CN、及びNO2からなる群から独立して選ばれた1つ~4つの置換基で置換されてもよく、
ここで、
Rcは、それぞれの場合にH、C1-20-アルキル、C2-10-アルケニル又はC2-20-アルキニルである、請求項1~4のいずれか一項に記載の化合物。 - R1は、それぞれの場合にC1-50-アルキルである、請求項1~4のいずれか一項に記載の化合物。
- R2は、それぞれの場合にH、C1-30-アルキル又はハロゲンである、請求項1~6のいずれか一項に記載の化合物。
- mは、0、1又は2である、請求項1~7のいずれか一項に記載の化合物。
- nは、0である、請求項1~8のいずれか一項に記載の化合物。
- L1及びL2は、互いに独立して、それぞれの場合に、C6-26-アリレン、5~20角形のヘテロアリレン及び
C6-26-アリレン及び5~20角形のヘテロアリレンは、それぞれの場合にC1-30-アルキル、C2-30-アルケニル、C2-30-アルキニル及びハロゲンからなる群から選ばれた1つ~4つの置換基Rdで置換されてもよく、
ここで、1つ~4つの置換基Rdで任意に置換されたC6-26-アリレンは、
R101は、それぞれの場合にH又はC1-30-アルキルであり、
ここで、1つ~4つの置換基Rdで任意に置換された5~20角形のヘテロアリレンは、
R103は、それぞれの場合にH、C1-30-アルキル、C2-30-アルケニル、C2-30-アルキニル又はハロゲンであり、
R102は、それぞれの場合にH又はC1-30-アルキルである、請求項1~9のいずれか一項に記載の化合物。 - 化学式3Aの化合物、化学式3Bの化合物、化学式3Cの化合物、化学式3Dの化合物、化学式3Eの化合物、化学式3’Aの化合物、化学式3’Bの化合物、化学式3’Cの化合物又は化学式3’Dの化合物である、化合物。
Xは、それぞれの場合にO、S、Se又はTeであり、
Qは、それぞれの場合にC、Si又はGeであり、
R1は、それぞれの場合にH、C1-50-アルキル(C1-50-alkyl)、-[CH2]O-[O-SiRaRa]p-OSiRaRaRa、-[CH2]O-[RaRaSi-O]p-SiRaRaRa、-[CRbRb]q-CRbRbRb、C2-50-アルケニル、C2-50-アルキニル、C5-8-シクロアルキル、C6-14-アリール及び5~14角形のヘテロアリールからなる群から選ばれ、
ここで、
oは、0~10の整数であり、
pは、1~40の整数であり、
Raは、それぞれの場合にC1-10-アルキル、C2-10-アルケニル又はC2-10-アルキニルであり、
qは、1~50の整数であり、
Rbは、それぞれの場合にH又はハロゲンであり、ただし、-[CRbRb]q-CRbRbRbにおいてすべてのRbがHであるものではなく、
C1-50-アルキル、C2-50-アルケニル及びC2-50-アルキニルは、ORc、OC(O)-Rc、C(O)-ORc、C(O)-Rc、NRcRc、NRc-C(O)Rc、C(O)-NRcRc、N[C(O)Rc][C(O)Rc]、SRc、CN、-SiRcRcRc及びNO2からなる群から独立して選ばれた1つ~4つの置換基で置換されてもよく、
C5-8-シクロアルキルは、C1-10-アルキル、C2-10-アルケニル、C2-10-アルキニル、ORc、OC(O)-Rc、C(O)-ORc、C(O)-Rc、NRcRc、NRc-C(O)Rc、C(O)-NRcRc、N[C(O)Rc][C(O)Rc]、SRc、ハロゲン、CN、-SiRcRcRc及びNO2からなる群から独立して選ばれた1つ又は2つの置換基で置換されてもよく、C5-8-シクロアルキルの1つのCH2基は、O、S、OC(O)、CO、NRc又はNRc-COに置き換えられ、
C6-14-アリール及び5~14角形のヘテロアリールは、C1-10-アルキル、C2-10-アルケニル、C2-10-アルキニル、ORc、OC(O)-Rc、C(O)-ORc、C(O)-Rc、NRcRc、NRc-C(O)Rc、C(O)-NRcRc、N[C(O)Rc][C(O)Rc]、SRc、ハロゲン、CN及びNO2からなる群から独立して選ばれた1つ~3つの置換基で置換されてもよく、
ここで、
Rcは、それぞれの場合にH、C1-20-アルキル、C2-10-アルケニル又はC2-10-アルキニルであり、
R2は、それぞれの場合にH、C1-30-アルキル、C2-30-アルケニル、C2-30-アルキニル又はハロゲンであり、
Yは、それぞれの場合にO、S、Se、又はTeであり、
R3は、それぞれの場合にH、C1-30-アルキル、C2-30-アルケニル、C2-30-アルキニル又はハロゲンである。 - 請求項1~請求項10のいずれか一項に記載の化合物を含む電子装置。
- 前記電子装置は、有機電界効果トランジスタである、請求項12に記載の電子装置。
- 前記化合物は、半導体物質である、請求項1に記載の化合物。
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