CN103649096B - 有机半导体 - Google Patents
有机半导体 Download PDFInfo
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- CN103649096B CN103649096B CN201280034825.4A CN201280034825A CN103649096B CN 103649096 B CN103649096 B CN 103649096B CN 201280034825 A CN201280034825 A CN 201280034825A CN 103649096 B CN103649096 B CN 103649096B
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 38
- 229920000642 polymer Polymers 0.000 claims abstract description 210
- 239000000203 mixture Substances 0.000 claims abstract description 150
- 238000013086 organic photovoltaic Methods 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 125000004432 carbon atom Chemical group C* 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000002904 solvent Substances 0.000 claims description 48
- 239000000463 material Substances 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 30
- 230000003252 repetitive effect Effects 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 16
- 239000010408 film Substances 0.000 claims description 15
- 230000005540 biological transmission Effects 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 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 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 229910003472 fullerene Inorganic materials 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 8
- 239000010409 thin film Substances 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 230000005611 electricity Effects 0.000 claims description 6
- 238000003682 fluorination reaction Methods 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 230000008859 change Effects 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000004020 conductor Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 108091028043 Nucleic acid sequence Proteins 0.000 claims description 3
- 239000003990 capacitor Substances 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 229920005604 random copolymer Polymers 0.000 claims description 3
- 239000011469 building brick Substances 0.000 claims description 2
- 239000007772 electrode material Substances 0.000 claims description 2
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract description 78
- 125000005605 benzo group Chemical group 0.000 abstract description 8
- 239000002244 precipitate Substances 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 5
- -1 heteroaryl oxygen Chemical compound 0.000 description 120
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 115
- 239000010410 layer Substances 0.000 description 71
- 239000007787 solid Substances 0.000 description 65
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- 239000000178 monomer Substances 0.000 description 58
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 49
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- 239000002585 base Substances 0.000 description 40
- 229930192474 thiophene Natural products 0.000 description 37
- 238000000034 method Methods 0.000 description 35
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 31
- 239000000460 chlorine Substances 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 239000003208 petroleum Substances 0.000 description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 17
- 238000000576 coating method Methods 0.000 description 17
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 16
- 239000011248 coating agent Substances 0.000 description 16
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical class COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 15
- 229920001577 copolymer Polymers 0.000 description 15
- 238000000605 extraction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000007639 printing Methods 0.000 description 14
- 238000000746 purification Methods 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 13
- 239000000758 substrate Substances 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
- 125000001118 alkylidene group Chemical group 0.000 description 11
- 238000007334 copolymerization reaction Methods 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 11
- 150000002367 halogens Chemical class 0.000 description 11
- 238000003808 methanol extraction Methods 0.000 description 11
- 238000001226 reprecipitation Methods 0.000 description 11
- 235000012239 silicon dioxide Nutrition 0.000 description 11
- 229910052717 sulfur Inorganic materials 0.000 description 11
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 239000000306 component Substances 0.000 description 10
- 229920001519 homopolymer Polymers 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical class ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 238000005804 alkylation reaction Methods 0.000 description 8
- 229920000547 conjugated polymer Polymers 0.000 description 8
- ONIHPYYWNBVMID-UHFFFAOYSA-N diethyl benzene-1,4-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(C(=O)OCC)C=C1 ONIHPYYWNBVMID-UHFFFAOYSA-N 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000011877 solvent mixture Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 8
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 125000004122 cyclic group Chemical group 0.000 description 7
- 238000000151 deposition Methods 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 238000007641 inkjet printing Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 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 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- QFNFDUFAPXVTAW-UHFFFAOYSA-M [OH-].[K+].[PH2](=O)O Chemical compound [OH-].[K+].[PH2](=O)O QFNFDUFAPXVTAW-UHFFFAOYSA-M 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 6
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 125000002769 thiazolinyl group Chemical group 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 150000001721 carbon Chemical class 0.000 description 5
- 229920001940 conductive polymer Polymers 0.000 description 5
- 238000007306 functionalization reaction Methods 0.000 description 5
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 5
- 238000009413 insulation Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 238000004528 spin coating Methods 0.000 description 5
- 125000003107 substituted aryl group Chemical group 0.000 description 5
- 229910052714 tellurium Inorganic materials 0.000 description 5
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- 0 CCC(c1*2c(SC(C3C)C(C)(C)C)c3[s]1)=C(C=C(CC1=C(*)*)c3c1c([s]c(C(C)(C)C)c1)c1[s]3)C2=C(C)* Chemical compound CCC(c1*2c(SC(C3C)C(C)(C)C)c3[s]1)=C(C=C(CC1=C(*)*)c3c1c([s]c(C(C)(C)C)c1)c1[s]3)C2=C(C)* 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- 229910052785 arsenic Inorganic materials 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 229920001400 block copolymer Polymers 0.000 description 4
- 239000004327 boric acid Substances 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 238000007872 degassing Methods 0.000 description 4
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 229920002313 fluoropolymer Polymers 0.000 description 4
- 239000004811 fluoropolymer Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- 125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 4
- 125000001424 substituent group Chemical class 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- SYUVAXDZVWPKSI-UHFFFAOYSA-N tributyl(phenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=C1 SYUVAXDZVWPKSI-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical class ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 3
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 3
- ROIMNSWDOJCBFR-UHFFFAOYSA-N 2-iodothiophene Chemical compound IC1=CC=CS1 ROIMNSWDOJCBFR-UHFFFAOYSA-N 0.000 description 3
- ZVGCGHVMJAECEG-UHFFFAOYSA-N Chinol Natural products COC1=C(O)C(C)=C(C)C(O)=C1OC ZVGCGHVMJAECEG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- 241001597008 Nomeidae Species 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 229910006069 SO3H Inorganic materials 0.000 description 3
- 238000006619 Stille reaction Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
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- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 150000001555 benzenes Chemical class 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 230000031709 bromination Effects 0.000 description 3
- 238000005893 bromination reaction Methods 0.000 description 3
- 230000005587 bubbling Effects 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- 230000021615 conjugation Effects 0.000 description 3
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 3
- 238000003618 dip coating Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 150000002924 oxiranes Chemical class 0.000 description 3
- 238000000059 patterning Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 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
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
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- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
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- QKWILNTYPDJSME-UHFFFAOYSA-N pyrrolo[3,4-c]pyrrole-3,6-dione Chemical class C1=NC(=O)C2=C1C(=O)N=C2 QKWILNTYPDJSME-UHFFFAOYSA-N 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 125000004151 quinonyl group Chemical group 0.000 description 1
- 238000006479 redox reaction Methods 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
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- 229910052701 rubidium Inorganic materials 0.000 description 1
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- 239000013049 sediment Substances 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- OEIMLTQPLAGXMX-UHFFFAOYSA-I tantalum(v) chloride Chemical compound Cl[Ta](Cl)(Cl)(Cl)Cl OEIMLTQPLAGXMX-UHFFFAOYSA-I 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 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
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- RBNWAMSGVWEHFP-UHFFFAOYSA-N trans-p-Menthane-1,8-diol Chemical compound CC(C)(O)C1CCC(C)(O)CC1 RBNWAMSGVWEHFP-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- GQHWSLKNULCZGI-UHFFFAOYSA-N trifluoromethoxybenzene Chemical compound FC(F)(F)OC1=CC=CC=C1 GQHWSLKNULCZGI-UHFFFAOYSA-N 0.000 description 1
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000005491 wire drawing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
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- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3243—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed containing one or more sulfur atoms as the only heteroatom, e.g. benzothiophene
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- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
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Abstract
Description
Claims (14)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP11005901.1 | 2011-07-19 | ||
EP11005901 | 2011-07-19 | ||
PCT/EP2012/002625 WO2013010614A2 (en) | 2011-07-19 | 2012-06-21 | Organic semiconductors |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103649096A CN103649096A (zh) | 2014-03-19 |
CN103649096B true CN103649096B (zh) | 2016-12-07 |
Family
ID=46397141
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN201280034825.4A Active CN103649096B (zh) | 2011-07-19 | 2012-06-21 | 有机半导体 |
Country Status (10)
Country | Link |
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US (1) | US9761805B2 (zh) |
EP (1) | EP2734528B1 (zh) |
JP (1) | JP6101263B2 (zh) |
KR (1) | KR101935077B1 (zh) |
CN (1) | CN103649096B (zh) |
BR (1) | BR112014001176A2 (zh) |
GB (1) | GB2507023A (zh) |
RU (1) | RU2014105870A (zh) |
TW (1) | TWI565786B (zh) |
WO (1) | WO2013010614A2 (zh) |
Families Citing this family (32)
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GB2472413B (en) * | 2009-08-05 | 2014-04-23 | Cambridge Display Tech Ltd | Organic semiconductors |
US9520565B2 (en) * | 2011-06-28 | 2016-12-13 | Merck Patent Gmbh | Indaceno derivatives as organic semiconductors |
GB2516207A (en) * | 2012-04-25 | 2015-01-14 | Merck Patent Gmbh | Conjugated polymers |
JP6465801B2 (ja) * | 2012-10-05 | 2019-02-06 | メルク パテント ゲーエムベーハー | 有機半導体 |
GB2530954A (en) * | 2013-06-21 | 2016-04-06 | Merck Patent Gmbh | Conjugated polymers |
US9876182B2 (en) | 2013-07-26 | 2018-01-23 | University Of Oregon | Thieno-containing compounds and processes and uses thereof |
WO2015025981A1 (ja) | 2013-08-23 | 2015-02-26 | 住友化学株式会社 | 高分子化合物およびそれを用いた有機半導体素子 |
WO2015058827A1 (en) * | 2013-10-22 | 2015-04-30 | Merck Patent Gmbh | Conjugated polymers |
EP3074451B1 (en) * | 2013-11-28 | 2017-12-27 | Merck Patent GmbH | Novel polycyclic polymer comprising thiophene units, a method of producing and uses of such polymer |
KR102173046B1 (ko) * | 2013-12-06 | 2020-11-03 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
JP6607864B2 (ja) * | 2014-04-10 | 2019-11-20 | メルク パテント ゲーエムベーハー | 有機半導体化合物 |
CN106661209A (zh) * | 2014-07-23 | 2017-05-10 | 住友化学株式会社 | 高分子化合物和使用该高分子化合物的有机半导体元件 |
JP6898224B2 (ja) * | 2014-07-29 | 2021-07-07 | 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Merck Patent Gesellschaft mit beschraenkter Haftung | テトラ−ヘテロアリールインダセノジチオフェン系多環式ポリマーおよびそれらの使用 |
CN105315298B (zh) * | 2014-08-04 | 2017-10-10 | 中国科学院化学研究所 | 基于七并稠环单元的a‑d‑a共轭分子及其制备方法和应用 |
CN104557972B (zh) * | 2015-01-20 | 2017-02-22 | 武汉理工大学 | 双(噻吩并[3,2‑b]噻吩)并芴单体、共轭聚合物及其应用 |
CN106905344B (zh) * | 2015-12-23 | 2018-11-30 | 北京大学 | 基于七并稠环单元的共轭大分子及其制备方法和在太阳能电池中的应用 |
CN108603012A (zh) | 2016-01-29 | 2018-09-28 | 住友化学株式会社 | 组合物及使用其的有机薄膜晶体管 |
WO2018007479A1 (en) * | 2016-07-08 | 2018-01-11 | Merck Patent Gmbh | Organic semiconducting compounds |
CN106543201B (zh) * | 2016-11-01 | 2020-05-19 | 西安近代化学研究所 | 一种基于取代茚并噻吩稠环单元的a-d-a型共轭分子及其制备方法 |
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US9761805B2 (en) | 2017-09-12 |
CN103649096A (zh) | 2014-03-19 |
KR101935077B1 (ko) | 2019-01-03 |
US20140158949A1 (en) | 2014-06-12 |
JP2014529349A (ja) | 2014-11-06 |
WO2013010614A3 (en) | 2013-06-20 |
RU2014105870A (ru) | 2015-08-27 |
TWI565786B (zh) | 2017-01-11 |
WO2013010614A2 (en) | 2013-01-24 |
JP6101263B2 (ja) | 2017-03-22 |
TW201309779A (zh) | 2013-03-01 |
EP2734528B1 (en) | 2017-03-29 |
BR112014001176A2 (pt) | 2017-01-10 |
KR20140063608A (ko) | 2014-05-27 |
GB2507023A (en) | 2014-04-16 |
EP2734528A2 (en) | 2014-05-28 |
GB201402509D0 (en) | 2014-04-02 |
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