JP5789298B2 - 半導性ポリマー - Google Patents
半導性ポリマー Download PDFInfo
- Publication number
- JP5789298B2 JP5789298B2 JP2013517060A JP2013517060A JP5789298B2 JP 5789298 B2 JP5789298 B2 JP 5789298B2 JP 2013517060 A JP2013517060 A JP 2013517060A JP 2013517060 A JP2013517060 A JP 2013517060A JP 5789298 B2 JP5789298 B2 JP 5789298B2
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- JP
- Japan
- Prior art keywords
- diyl
- atoms
- polymer
- formula
- thiophene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 229920000642 polymer Polymers 0.000 title claims description 108
- -1 1,4-phenylene, thiophene-2,5-diyl Chemical group 0.000 claims description 170
- 239000010410 layer Substances 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 74
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 239000000463 material Substances 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000002904 solvent Substances 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 26
- 238000009472 formulation Methods 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 238000013086 organic photovoltaic Methods 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 239000010408 film Substances 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 11
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 230000003287 optical effect Effects 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 238000005859 coupling reaction Methods 0.000 claims description 8
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000006413 ring segment Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 239000010409 thin film Substances 0.000 claims description 6
- 230000000903 blocking effect Effects 0.000 claims description 5
- 239000003990 capacitor Substances 0.000 claims description 5
- 125000006850 spacer group Chemical group 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- 108091028043 Nucleic acid sequence Proteins 0.000 claims description 4
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical compound C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 claims description 3
- 238000000018 DNA microarray Methods 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 238000005801 aryl-aryl coupling reaction Methods 0.000 claims description 3
- 239000007772 electrode material Substances 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 239000012528 membrane Substances 0.000 claims description 3
- 239000005518 polymer electrolyte Substances 0.000 claims description 3
- DQZRQIOYWRRDMJ-UHFFFAOYSA-N 1,4-dithiophen-2-ylpyrrolo[3,4-c]pyrrole-3,6-dione Chemical compound C=1C=CSC=1C1=NC(=O)C2=C1C(=O)N=C2C1=CC=CS1 DQZRQIOYWRRDMJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052770 Uranium Inorganic materials 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 125000001543 furan-2,5-diyl group Chemical group O1C(=CC=C1*)* 0.000 claims description 2
- 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 claims description 2
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 239000011229 interlayer Substances 0.000 claims 2
- 230000005611 electricity Effects 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 19
- 239000004065 semiconductor Substances 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 11
- 229920002959 polymer blend Polymers 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- 239000000306 component Substances 0.000 description 9
- 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 9
- 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 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000002800 charge carrier Substances 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 0 OC(*c(cc1)ccc1NC(C(c(cc1)ccc1Br)O)=O)c(cc1)ccc1Br Chemical compound OC(*c(cc1)ccc1NC(C(c(cc1)ccc1Br)O)=O)c(cc1)ccc1Br 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000002877 alkyl aryl group Chemical group 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000007641 inkjet printing Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class 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 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 125000005605 benzo group Chemical group 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 6
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000012212 insulator Substances 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 4
- BHZBRPQOYFDTAB-UHFFFAOYSA-N 2-(4-bromophenyl)-2-hydroxyacetic acid Chemical compound OC(=O)C(O)C1=CC=C(Br)C=C1 BHZBRPQOYFDTAB-UHFFFAOYSA-N 0.000 description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- MCEWYIDBDVPMES-UHFFFAOYSA-N [60]pcbm Chemical compound C123C(C4=C5C6=C7C8=C9C%10=C%11C%12=C%13C%14=C%15C%16=C%17C%18=C(C=%19C=%20C%18=C%18C%16=C%13C%13=C%11C9=C9C7=C(C=%20C9=C%13%18)C(C7=%19)=C96)C6=C%11C%17=C%15C%13=C%15C%14=C%12C%12=C%10C%10=C85)=C9C7=C6C2=C%11C%13=C2C%15=C%12C%10=C4C23C1(CCCC(=O)OC)C1=CC=CC=C1 MCEWYIDBDVPMES-UHFFFAOYSA-N 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- 230000001965 increasing effect Effects 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
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- 125000001424 substituent group Chemical group 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KZPJVVSJJZPJSE-UHFFFAOYSA-N 3,7-bis(4-bromophenyl)-1,5-dihydropyrrolo[2,3-f]indole-2,6-dione Chemical compound C1=CC(Br)=CC=C1C(C(N1)=O)=C2C1=CC1=C(C=3C=CC(Br)=CC=3)C(=O)NC1=C2 KZPJVVSJJZPJSE-UHFFFAOYSA-N 0.000 description 3
- ANEUZWSLUNWJJI-UHFFFAOYSA-N 7-(2,2-dibromoethenyl)pentadecane Chemical compound CCCCCCCCC(C=C(Br)Br)CCCCCC ANEUZWSLUNWJJI-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000000944 Soxhlet extraction Methods 0.000 description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 229910052785 arsenic Inorganic materials 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000003618 dip coating Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
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- 230000005525 hole transport Effects 0.000 description 3
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- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
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- 229920006301 statistical copolymer Polymers 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 229910052714 tellurium Inorganic materials 0.000 description 3
- 125000004001 thioalkyl group Chemical group 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- GXEVGKKATYYGRS-UHFFFAOYSA-N 1,4-bis(3-hexylundec-1-ynyl)-2,5-dimethoxybenzene Chemical compound CCCCCCCCC(CCCCCC)C#CC1=CC(OC)=C(C#CC(CCCCCC)CCCCCCCC)C=C1OC GXEVGKKATYYGRS-UHFFFAOYSA-N 0.000 description 2
- AEXSEYIASUPTFC-UHFFFAOYSA-N 1,4-bis(3-hexylundecyl)-2,5-dimethoxybenzene Chemical compound CCCCCCCCC(CCCCCC)CCC1=CC(OC)=C(CCC(CCCCCC)CCCCCCCC)C=C1OC AEXSEYIASUPTFC-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- VZHJIJZEOCBKRA-UHFFFAOYSA-N 1-chloro-3-fluorobenzene Chemical compound FC1=CC=CC(Cl)=C1 VZHJIJZEOCBKRA-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- OXQOBQJCDNLAPO-UHFFFAOYSA-N 2,3-Dimethylpyrazine Chemical compound CC1=NC=CN=C1C OXQOBQJCDNLAPO-UHFFFAOYSA-N 0.000 description 2
- SJUBABADVCIUHZ-UHFFFAOYSA-N 2,5-bis(3-hexylundecyl)benzene-1,4-diol Chemical compound CCCCCCCCC(CCCCCC)CCC1=CC(O)=C(CCC(CCCCCC)CCCCCCCC)C=C1O SJUBABADVCIUHZ-UHFFFAOYSA-N 0.000 description 2
- ARWUWADTKZCNIL-UHFFFAOYSA-N 2-(4-bromophenyl)-n-[4-[[2-(4-bromophenyl)-2-hydroxyacetyl]amino]phenyl]-2-hydroxyacetamide Chemical compound C=1C=C(Br)C=CC=1C(O)C(=O)NC(C=C1)=CC=C1NC(=O)C(O)C1=CC=C(Br)C=C1 ARWUWADTKZCNIL-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- GRBBBAWAAORSRN-UHFFFAOYSA-N 3,7-bis(4-bromophenyl)-1,3,5,7-tetrahydropyrrolo[2,3-f]indole-2,6-dione Chemical compound C1=CC(Br)=CC=C1C1C2=CC(NC(=O)C3C=4C=CC(Br)=CC=4)=C3C=C2NC1=O GRBBBAWAAORSRN-UHFFFAOYSA-N 0.000 description 2
- KKMXTOBNHTWSFC-UHFFFAOYSA-N 3,7-bis(4-bromophenyl)-1,5-dioctylpyrrolo[2,3-f]indole-2,6-dione Chemical compound C=12C=C3N(CCCCCCCC)C(=O)C(C=4C=CC(Br)=CC=4)=C3C=C2N(CCCCCCCC)C(=O)C=1C1=CC=C(Br)C=C1 KKMXTOBNHTWSFC-UHFFFAOYSA-N 0.000 description 2
- NXYWAVNCOBWTSB-UHFFFAOYSA-N 3,7-bis(4-bromophenyl)-4,8-dioctylfuro[2,3-f][1]benzofuran-2,6-dione Chemical compound C=12C(CCCCCCCC)=C3OC(=O)C(C=4C=CC(Br)=CC=4)=C3C(CCCCCCCC)=C2OC(=O)C=1C1=CC=C(Br)C=C1 NXYWAVNCOBWTSB-UHFFFAOYSA-N 0.000 description 2
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
- XXGCSAZSECYLMB-UHFFFAOYSA-N 7-ethynylpentadecane Chemical compound CCCCCCCCC(C#C)CCCCCC XXGCSAZSECYLMB-UHFFFAOYSA-N 0.000 description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 2
- 229910020366 ClO 4 Inorganic materials 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- APBDREXAUGXCCV-UHFFFAOYSA-L tetraethylazanium;carbonate Chemical compound [O-]C([O-])=O.CC[N+](CC)(CC)CC.CC[N+](CC)(CC)CC APBDREXAUGXCCV-UHFFFAOYSA-L 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical compound FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Description
本発明は、ベンゾジフラン、ベンゾジピロールまたはベンゾジチオフェンに基づいた繰り返し単位を含む新規なポリマー、それらの調製のためのモノマーおよび方法、有機電子(OE)デバイスにおける、特に有機光起電(OPV)装置における半導体としてのそれらの使用、ならびにこれらのポリマーを含むOEおよびOPVデバイスに関する。
近年、電子的適用のための半導性ポリマーの使用において高まりつつある関心があった。重要な1つの特定の分野は、有機光起電(OPV)である。ポリマーは、デバイスを溶液加工手法、例えば回転成形、浸漬コーティングまたはインクジェット印刷によって製造することを可能にするので、OPVにおいて用途が見出されている。溶液加工を、無機薄膜デバイスを作製するために使用される蒸発手法と比較して安価に、かつ大規模で行うことができる。現在、ポリマーに基づいた光起電デバイスは、7%までの効率を達成している。
Spは、スペーサー基または単結合であり、
X0は、ハロゲンである、
で表される1つまたは2つ以上の同一であるかまたは異なる繰り返し単位を含む共役ポリマーに関する。
−[(Ar1−U−Ar2)x−(Ar3)y]n− II
式中、
Uは、各出現において同一に、または異なって、本明細書中に記載した式Iで表される単位であり、
Ar1、Ar2、Ar3は、各出現において同一に、または異なって、および互いに独立して、任意に置換されているアリールまたはヘテロアリールであり、
Y1およびY2は、互いに独立してH、F、ClまたはCNであり、
yは、各出現において同一に、または異なって0、1または2であり、
nは、>1の整数である、
から選択される。
本発明はさらに、本発明の1種または2種以上のポリマーならびに、好ましくは半導性、電荷輸送、正孔/電子輸送、正孔/電子遮断、電気伝導性、光伝導性または発光特性を有する化合物およびポリマーから選択される1種または2種以上の付加的な化合物またはポリマーを含む、混合物またはブレンドに関する。
本発明はさらに、本発明のポリマー、混合物、ブレンドおよび調合物の、電荷輸送、半導性、電気伝導性、光伝導性または発光材料としての、光学的、電気光学的、電子的、エレクトロルミネセントまたは光ルミネセント部品またはデバイスにおける使用に関する。
本発明はさらに、本発明の1種または2種以上のポリマー、ポリマーブレンド、調合物、部品または材料を含む、光学的、電気光学的または電子部品またはデバイスに関する。
本発明のモノマーおよびポリマーは、合成するのが容易であり、いくつかの有利な特性、例えば低いバンドギャップ、高い電荷担体可動性、有機溶媒への高い可溶性、デバイス製造プロセスのための良好な加工性、高い酸化安定性および電子デバイスにおける長い寿命を示す。
i)式Iで表される繰り返し単位は、それ自体ポリマーの主鎖内に含まれる中心のベンゼン環に融合した2つの5員環を含む。核のあらかじめ確立されたキノン型(quinoidal)バンド構造によって、得られたポリマーのキノン型バンド構造が増大し、したがってポリマーのバンドギャップが低下し、それにより材料の集光能力が改善される。
ハロゲンは、F、Cl、BrまたはI、好ましくはF、ClまたはBrである。
Y1およびY2は、互いに独立してH、F、ClまたはCNである。
R2−[(Ar1−U−Ar2)x−(Ar3)y]n−R3 IIa
式中、U、Ar1〜3、n、xおよびyは、式IおよびIIの意味を有し、ならびに
から選択される。
R2−U−R3 Ia
式中、Uは、式I、I1またはI2で表されるかまたは本明細書中に記載したその好ましい従属式もしくは好ましい意味から選択された単位であり、R2およびR3は、式IIaにおいて示した意味を有する、
で表されるモノマーに関する。
− xは1であり、yは0であり、それによって繰り返し単位[Ar1−U−Ar2]を形成する、
− xは1であり、yは1であり、それによって繰り返し単位[Ar1−U−Ar2−Ar3]を形成する、
− Mwは、少なくとも5,000、好ましくは少なくとも8,000、極めて好ましくは少なくとも10,000、および好ましくは300,000まで、極めて好ましくは100,000までである、
− Rは、Hである、
− Rは、Hとは異なる、
− Rは、アリール、ヘテロアリール、アリールオキシまたはヘテロアリールオキシであり、その各々は、任意にアルキル化またはアルコキシル化されており、4〜30個の環原子を有する、
− Rxは、1〜30個のC原子を有するアルキルである、
− R2およびR3は、H、ハロゲン、−CH2Cl、−CHO、−CH=CH2、−SiR’R’’R’’’、−SnR’R’’R’’’、−BR’R’’、−B(OR’)(OR’’)、−B(OH)2、P−Sp、C1〜C20アルキル、C1〜C20アルコキシ、C2〜C20アルケニル、C1〜C20フルオロアルキルおよび任意に置換されているアリールまたはヘテロアリールから選択される、
− R1は、Hである、
− Rは、P−Sp−である。
R2−chain−R3
式中、「chain」は、上記の式II1−から選択されたポリマー鎖であり、R2およびR3は、式IIaにおいて示したR2およびR3の意味の1つまたは本明細書中に示したR2およびR3の好ましい意味の1つを有する、
から選択される。
好ましくは、ポリマーを、式Iaで表されるモノマーまたは本明細書中に記載したその好ましい態様から調製する。
R2−Ar3−R3
式中、Ar3、R2およびR3は、上に定義した通りである、
で表されるものである。
− 一方が透明である、低い仕事関数の電極(11)(例えば金属、例えばアルミニウム)および高い仕事関数の電極(12)(例えばITO)、
− 一方が透明である、低い仕事関数の電極(21)(例えば金属、例えば金)および高い仕事関数の電極(22)(例えばITO)、
− 正孔についての抵抗接点を提供するための、活性層(23)に面する高い仕事関数の電極(22)の側の任意のコーティング(25)(例えばTiOxの)。
− ソース電極、
− ドレイン電極、
− ゲート電極、
− 半導性層、
− 1つまたは2つ以上のゲート絶縁体層、
− 任意に基板。
ここで半導体層は、好ましくは、本明細書中に記載したポリマー、ポリマーブレンドまたは調合物を含む。
本明細書の記載および特許請求の範囲の全体にわたって、「含む(comprise)」および「含有する(contain)」の語ならびに例えば当該後の変化形、例えば「含む(comprising)」および「含む(comprises)」は、「含むがこれらには限定されない」を意味し、他の構成成分を除外することを意図しない(および除外しない)。
本発明をここで、以下の例への参照によってより詳細に記載し、それは例示的であるに過ぎず、本発明の範囲を限定しない。
2−(4−ブロモ−フェニル)−N−{4−[2−(4−ブロモ−フェニル)−2−ヒドロキシ−アセチルアミノ]−フェニル}−2−ヒドロキシ−アセトアミド(1.1)
3,7−ビス−(4−ブロモ−フェニル)−1,5−ビス−(2−ヘキシル−デシル)−1H,5H−ピロロ[2,3−f]インドール−2,6−ジオン(2.1)
3,7−ビス−(4−ブロモ−フェニル)−4,8−ジオクチル−ベンゾ[1,2−b;4,5−b’]ジフラン−2,6−ジオン(3.1)
7−(2,2−ジブロモ−ビニル)−ペンタデカン(4.1)
Claims (19)
- 式I:
Xは、O、SまたはNRxであり、
Rは、各出現において同一に、または異なって、H、F、Cl、Br、I、CNまたは1〜35個のC原子を有する直鎖状、分枝状もしくは環状アルキルであり、ここで1個または2個以上の隣接していないC原子は、任意に−O−、−S−、−CO−、−CO−O−、−O−CO−、−O−CO−O−、−CR0=CR00−または−C≡C−によって置き換えられており、およびここで1個または2個以上のH原子は、任意にF、Cl、Br、IまたはCNによって置き換えられており、あるいは非置換であるかまたは1つもしくは2つ以上の非芳香族基R1によって置換されている4〜30個の環原子を有するアリール、ヘテロアリール、アリールオキシ、ヘテロアリールオキシ、アリールカルボニル、ヘテロアリールカルボニル、アリールカルボニルオキシ、ヘテロアリールカルボニルオキシ、アリールオキシカルボニルまたはヘテロアリールオキシカルボニルを示し、
Rxは、各出現において同一に、または異なって、1〜30個のC原子を有する直鎖状、分枝状または環状アルキルであり、ここで1個または2個以上の隣接していないC原子は、任意に−O−、−S−、−CO−、−CO−O−、−O−CO−、O−CO−O−、−CR0=CR00−または−C≡C−によって置き換えられており、およびここで1個または2個以上のH原子は、任意にF、Cl、Br、IまたはCNによって置き換えられており、
R0およびR00は、互いに独立してHまたは任意に1個もしくは2個以上のヘテロ原子を含む、任意に置換されたカルビルもしくはヒドロカルビルであり、
R1は、各出現において同一に、または異なってH、ハロゲン、−CN、−NC、−NCO、−NCS、−OCN、−SCN、−C(=O)NR0R00、−C(=O)X0、−C(=O)R0、−NH2、−NR0R00、−SH、−SR0、−SO3H、−SO2R0、−OH、−NO2、−CF3、−SF5、任意に置換されており、任意に1個もしくは2個以上のヘテロ原子を含む、任意に置換された1〜40個のC原子を有するシリル、カルビルもしくはヒドロカルビル、またはP−Sp−であり、
Pは、重合性であるかまたは架橋可能な基であり、
Spは、スペーサー基または単結合であり、
X0は、ハロゲンである、
で表される1つまたは2つ以上の同一であるかまたは異なる繰り返し単位を含む、ポリマー。 - 請求項1において定義した式Iで表される単位を含み、かつ/または、任意に置換されているアリールおよびヘテロアリール単位から選択された1つもしくは2つ以上の単位を含む1つまたは2つ以上の繰り返し単位を含み、ここでポリマー中の繰り返し単位の少なくとも1つが、請求項1において定義した式Iで表される少なくとも1つの単位を含む、ポリマー。
- 式II
−[(Ar1−U−Ar2)x−(Ar3)y]n− II
式中、
Uは、各出現において同一に、または異なって、請求項1において定義した式Iで表される単位であり、
Ar1、Ar2、Ar3は、各出現において同一に、または異なって、および互いに独立して、任意に置換されているアリールまたはヘテロアリールであり、
xは、各出現において同一に、または異なって0、1または2であり、ここで少なくとも1つの繰り返し単位において、すなわち少なくとも1つの単位−[(Ar1−U−Ar2)x−(Ar3)y]−において、xは1であり、
yは、各出現において同一に、または異なって0、1または2であり、
nは、>1の整数である、
から選択される、請求項1または2に記載のポリマー。 - 式IIa
R2−[(Ar1−U−Ar2)x−(Ar3)y]n−R3 IIa
式中、U、Ar1〜3、n、xおよびyは、請求項2の意味を有し、ならびに
R2およびR3は、互いに独立して請求項1におけるR1の意味の1つを有するか、またはH、−CH2Cl、−CHO、−CH=CH2、−SiR’R’’R’’’、−SnR’R’’R’’’、−BR’R’’、−B(OR’)(OR’’)、−B(OH)2もしくはP−Spを示し、ここでPおよびSpは、上に定義した通りであり、R’、R’’およびR’’’は、互いに独立して請求項1におけるR0の意味の1つを有し、R’、R’’およびR’’’の2つはまた、それらが結合しているヘテロ原子と一緒に環を形成してもよい、
から選択される、請求項1〜3のいずれか一項に記載のポリマー。 - 式IIまたはIIa中のアリールもしくはヘテロアリール単位、または単位Ar1およびAr2が、互いに独立して1,4−フェニレン、チオフェン−2,5−ジイル、チアゾール−2,5−ジイル、セレノフェン−2,5−ジイル、フラン−2,5−ジイル、チエノ[3,2−b]チオフェン−2,5−ジイル、チエノ[2,3−b]チオフェン−2,5−ジイル、セレノフェノ[3,2−b]セレノフェン−2,5−ジイル、セレノフェノ[2,3−b]セレノフェン−2,5−ジイル、セレノフェノ[3,2−b]チオフェン−2,5−ジイルおよびセレノフェノ[2,3−b]チオフェン−2,5−ジイルからなる群から選択され、それらのすべてが、非置換であるかまたは請求項1において定義したRもしくはR1で単置換もしくは多置換されている、請求項2〜4のいずれか一項に記載のポリマー。
- 式IIまたはIIa中のアリールもしくはヘテロアリール単位、または単位Ar3が、各出現において同一に、または異なって、1,4−フェニレン、チオフェン−2,5−ジイル、セレノフェン−2,5−ジイル、チエノ[3,2−b]チオフェン−2,5−ジイル、チエノ[2,3−b]チオフェン−2,5−ジイル、セレノフェノ[3,2−b]セレノフェン−2,5−ジイル、セレノフェノ[2,3−b]セレノフェン−2,5−ジイル、セレノフェノ[3,2−b]チオフェン−2,5−ジイル、セレノフェノ[2,3−b]チオフェン−2,5−ジイル、ベンゾ[1,2−b:4,5−b’]ジチオフェン−2,6−ジイル、2,2−ジチオフェン、2,2−ジセレノフェン、ジチエノ[3,2−b:2’,3’−d]シロール−5,5−ジイル、4H−シクロペンタ[2,1−b:3,4−b’]ジチオフェン−2,6−ジイル、カルバゾール−2,7−ジイル、フルオレン−2,7−ジイル、インダセノ[1,2−b:5,6−b’]ジチオフェン−2,7−ジイル、ベンゾ[1’’,2’’:4,5;4’’,5’’:4’,5’]ビス(シロロ[3,2−b:3’,2’−b’]チオフェン)−2,7−ジイル、フェナントロ[1,10,9,8−c,d,e,f,g]カルバゾール−2,7−ジイル、ベンゾ[2,1,3]チアジアゾール−4,7−ジイル、ベンゾ[2,1,3]セレナジアゾール−4,7−ジイル、ベンゾ[2,1,3]オキサジアゾール−4,7−ジイル、2H−ベンゾトリアゾール−4,7−ジイル、3,4−ジフルオロチオフェン−2,5−ジイル、チエノ[3,4−b]ピラジン−2,5−ジイル、キノキサリン−5,8−ジイル、チエノ[3,4−b]チオフェン−4,6−ジイル、チエノ[3,4−b]チオフェン−6,4−ジイル、3,6−ジ−チエン−2−イル−ピロロ[3,4−c]ピロール−1,4−ジオンおよび[1,3]チアゾロ[5,4−d][1,3]チアゾール−2,5−ジイルからなる群から選択され、それらのすべてが、非置換であるかまたは請求項1において定義したRもしくはR1で単置換もしくは多置換されている、請求項2〜5のいずれか一項に記載のポリマー。
- Rが、1〜30個のC原子を有する第一アルキルまたはアルコキシ、3〜30個のC原子を有する第二アルキルまたはアルコキシ、4〜30個のC原子を有する第三アルキルまたはアルコキシから選択され、ここですべてのこれらの基中で、1個または2個以上のH原子が、任意にFによって置き換えられているか、あるいはRが、任意にアルキル化またはアルコキシル化され、4〜30個の環原子を有するアリール、アリールオキシ、ヘテロアリールまたはヘテロアリールオキシから選択される、請求項1〜6のいずれか一項に記載のポリマー。
- 混合物またはブレンドであって、請求項1〜7のいずれか一項に記載の1種または2種以上のポリマーおよび半導性、電荷輸送、正孔/電子輸送、正孔/電子遮断、電気伝導性、光伝導性または発光特性を有する1種または2種以上の化合物またはポリマーを含む、前記混合物またはブレンド。
- 請求項1〜8のいずれか一項に記載の1種または2種以上のポリマー、混合物またはブレンド、および好ましくは有機溶媒から選択された1種または2種以上の溶媒を含む、調合物。
- 請求項1〜9のいずれか一項に記載のポリマー、混合物、ブレンドまたは調合物の、光学的、電気光学的、電子的、エレクトロルミネセントまたは光ルミネセント部品における電荷輸送、半導性、電気伝導性、光伝導性または発光材料としての使用。
- 請求項1〜9のいずれか一項に記載のポリマー、混合物、ブレンドまたは調合物の、光学的、電気光学的、電子的、エレクトロルミネセントまたは光ルミネセントデバイスにおける電荷輸送、半導性、電気伝導性、光伝導性または発光材料としての使用。
- 請求項1〜9のいずれか一項に記載の1種または2種以上のポリマー、混合物、ブレンドまたは調合物を含む、光学的、電気光学的または電子的部品。
- 有機電界効果トランジスタ(OFET)、薄膜トランジスタ(TFT)、集積回路(IC)、論理回路、キャパシタ、電波認識(RFID)タグ、デバイスまたは部品、有機発光ダイオード(OLED)、有機発光トランジスタ(OLET)、フラットパネルディスプレイ、ディスプレイのバックライト、有機光起電デバイス(OPV)、太陽電池、レーザーダイオード、光伝導体、光検出器、電子写真装置、電子写真記録装置、有機記憶装置、センサーデバイス、電荷注入層、電荷輸送層またはポリマー発光ダイオード(PLED)中の中間層、ショットキーダイオード、平坦化層、帯電防止フィルム、ポリマー電解膜(PEM)、伝導性基板、伝導性パターン、電池における電極材料、整列層、バイオセンサー、バイオチップ、セキュリティマーキング、セキュリティーデバイス、ならびにDNA配列を検出し、識別するための部品またはデバイスからなる群から選択される、請求項12に記載の部品。
- OFETまたはバルクヘテロ接合OPVデバイスである、請求項12または13に記載の部品。
- 請求項1〜9のいずれか一項に記載の1種または2種以上のポリマー、混合物、ブレンドまたは調合物を含む、光学的、電気光学的または電子的デバイス。
- 有機電界効果トランジスタ(OFET)、薄膜トランジスタ(TFT)、集積回路(IC)、論理回路、キャパシタ、電波認識(RFID)タグ、デバイスまたは部品、有機発光ダイオード(OLED)、有機発光トランジスタ(OLET)、フラットパネルディスプレイ、ディスプレイのバックライト、有機光起電デバイス(OPV)、太陽電池、レーザーダイオード、光伝導体、光検出器、電子写真装置、電子写真記録装置、有機記憶装置、センサーデバイス、電荷注入層、電荷輸送層またはポリマー発光ダイオード(PLED)中の中間層、ショットキーダイオード、平坦化層、帯電防止フィルム、ポリマー電解膜(PEM)、伝導性基板、伝導性パターン、電池における電極材料、整列層、バイオセンサー、バイオチップ、セキュリティマーキング、セキュリティーデバイス、ならびにDNA配列を検出し、識別するための部品またはデバイスからなる群から選択される、請求項15に記載のデバイス。
- OFETまたはバルクヘテロ接合OPVデバイスである、請求項15または16に記載のデバイス。
- 式Ia
R2−U−R3 Ia
式中、Uは式I1またはI2
Rは、請求項1または7で定義されたとおりであり、R x は請求項1で定義されたとおりであり、
R 2 およびR 3 は、互いに独立してCl、Br、I、O−トシレート、O−トリフレート、O−メシレート、O−ノナフレート、−SiMe 2 F、−SiMeF 2 、−O−SO 2 Z 1 、−B(OZ 2 ) 2 、−CZ 3 =C(Z 3 ) 2 、−C≡CHおよび−Sn(Z 4 ) 3 からなる群から選択されるモノマーであり、ここでZ 1〜4 は、各々が任意に置換されていてもよいアルキルおよびアリールからなる群から選択され、2つの基Z 2 はまた、環式基を形成してもよい、
で表されるモノマー。 - 請求項1〜7のいずれか一項に記載のポリマーを調製する方法であって、
式Ia
R 2 −U−R 3 Ia
式中、Uは、請求項1または7において定義した式Iで表される単位であり、R 2 およびR 3 は、請求項4において示した意味を有する、
で表される1種または2種以上のモノマーを互いに、および/または式
R2−Ar3−R3
式中、R2、R3およびAr3は、請求項4または6において定義した通りである、
で表される1種または2種以上のモノマーと、アリール−アリールカップリング反応においてカップリングさせることによる、前記方法。
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2011
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- 2011-06-14 KR KR1020137003288A patent/KR101792901B1/ko active IP Right Grant
- 2011-06-14 SG SG2012096558A patent/SG186874A1/en unknown
- 2011-06-14 RU RU2013105371/04A patent/RU2013105371A/ru not_active Application Discontinuation
- 2011-06-14 DE DE112011102301T patent/DE112011102301T5/de active Pending
- 2011-06-14 JP JP2013517060A patent/JP5789298B2/ja active Active
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Publication number | Publication date |
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GB2494607A (en) | 2013-03-13 |
CN103025788A (zh) | 2013-04-03 |
HK1183679A1 (zh) | 2014-01-03 |
GB2494607B (en) | 2018-05-02 |
CN103025788B (zh) | 2015-08-12 |
TW201209071A (en) | 2012-03-01 |
SG186874A1 (en) | 2013-02-28 |
EP2591038B1 (en) | 2014-11-05 |
TWI508992B (zh) | 2015-11-21 |
US20130175481A1 (en) | 2013-07-11 |
GB201300592D0 (en) | 2013-02-27 |
EP2591038A1 (en) | 2013-05-15 |
DE112011102301T5 (de) | 2013-05-16 |
WO2012003918A1 (en) | 2012-01-12 |
US9287504B2 (en) | 2016-03-15 |
JP2013531106A (ja) | 2013-08-01 |
KR101792901B1 (ko) | 2017-11-02 |
RU2013105371A (ru) | 2014-08-20 |
KR20130100978A (ko) | 2013-09-12 |
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