JP5946273B2 - 有機半導体化合物および、これを含むトランジスタと電子素子 - Google Patents
有機半導体化合物および、これを含むトランジスタと電子素子 Download PDFInfo
- Publication number
- JP5946273B2 JP5946273B2 JP2011290399A JP2011290399A JP5946273B2 JP 5946273 B2 JP5946273 B2 JP 5946273B2 JP 2011290399 A JP2011290399 A JP 2011290399A JP 2011290399 A JP2011290399 A JP 2011290399A JP 5946273 B2 JP5946273 B2 JP 5946273B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- unsubstituted
- general formula
- organic semiconductor
- 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.)
- Active
Links
- 239000004065 semiconductor Substances 0.000 title claims description 77
- 150000001875 compounds Chemical class 0.000 title claims description 51
- 229920000642 polymer Polymers 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 16
- 238000009413 insulation Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000010410 layer Substances 0.000 description 37
- -1 trizolyl group Chemical group 0.000 description 32
- 125000001072 heteroaryl group Chemical group 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
- 239000010409 thin film Substances 0.000 description 16
- 150000002431 hydrogen Chemical class 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 13
- 125000000753 cycloalkyl group Chemical group 0.000 description 12
- 125000000524 functional group Chemical group 0.000 description 11
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004642 Polyimide Substances 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 229920001721 polyimide Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 239000004417 polycarbonate Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 3
- 229920000144 PEDOT:PSS Polymers 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229910021417 amorphous silicon Inorganic materials 0.000 description 3
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- DVRXLNPMPZGGED-UHFFFAOYSA-N (5-bromo-4-hexylthiophen-2-yl)-trimethylstannane Chemical compound CCCCCCC=1C=C([Sn](C)(C)C)SC=1Br DVRXLNPMPZGGED-UHFFFAOYSA-N 0.000 description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- ATRJNSFQBYKFSM-UHFFFAOYSA-N 2,3-dibromothiophene Chemical compound BrC=1C=CSC=1Br ATRJNSFQBYKFSM-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OLDXRTOEUPVZKB-UHFFFAOYSA-N B1CCCC1 Chemical group B1CCCC1 OLDXRTOEUPVZKB-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 238000000944 Soxhlet extraction Methods 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 229910052454 barium strontium titanate Inorganic materials 0.000 description 2
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 2
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
- 239000002041 carbon nanotube Substances 0.000 description 2
- 229910021393 carbon nanotube Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229910003472 fullerene Inorganic materials 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004366 heterocycloalkenyl group Chemical group 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 2
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 239000011112 polyethylene naphthalate Substances 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 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 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
- QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 1
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 1
- 238000004009 13C{1H}-NMR spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- HWSOCIIMMAKNCR-UHFFFAOYSA-N 2,6-dichloro-4-n,8-n-dioctylpyrimido[5,4-d]pyrimidine-4,8-diamine Chemical compound N1=C(Cl)N=C2C(NCCCCCCCC)=NC(Cl)=NC2=C1NCCCCCCCC HWSOCIIMMAKNCR-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- QZVHYFUVMQIGGM-UHFFFAOYSA-N 2-Hexylthiophene Chemical compound CCCCCCC1=CC=CS1 QZVHYFUVMQIGGM-UHFFFAOYSA-N 0.000 description 1
- XQJNXCHDODCAJF-UHFFFAOYSA-N 2-bromo-3-hexylthiophene Chemical compound CCCCCCC=1C=CSC=1Br XQJNXCHDODCAJF-UHFFFAOYSA-N 0.000 description 1
- FSEJXNVEILKEQU-UHFFFAOYSA-N 3,4-dibromo-2-thiophen-2-ylthiophene Chemical compound BrC1=CSC(C=2SC=CC=2)=C1Br FSEJXNVEILKEQU-UHFFFAOYSA-N 0.000 description 1
- JEDHEMYZURJGRQ-UHFFFAOYSA-N 3-hexylthiophene Chemical compound CCCCCCC=1C=CSC=1 JEDHEMYZURJGRQ-UHFFFAOYSA-N 0.000 description 1
- JQXJBXVWVPVTOO-UHFFFAOYSA-L 4-diphenylphosphanylbutyl(diphenyl)phosphane;palladium(2+);dichloride Chemical compound Cl[Pd]Cl.C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 JQXJBXVWVPVTOO-UHFFFAOYSA-L 0.000 description 1
- LDFNJUPAWDJLNK-UHFFFAOYSA-N 5,8-dibromo-2,3-bis(3-dodecoxyphenyl)pyrido[3,4-b]pyrazine Chemical compound CCCCCCCCCCCCOC1=CC=CC(C=2C(=NC3=C(Br)N=CC(Br)=C3N=2)C=2C=C(OCCCCCCCCCCCC)C=CC=2)=C1 LDFNJUPAWDJLNK-UHFFFAOYSA-N 0.000 description 1
- MZFPAWGWFDGCHP-UHFFFAOYSA-N 5-diphenylphosphanylpentyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 MZFPAWGWFDGCHP-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 229910017109 AlON Inorganic materials 0.000 description 1
- VNBQVRSIKWVFLI-UHFFFAOYSA-N BrC=1SC(=CC1CCCCCC)[Sn](C)(C)C.BrC=1SC(=CC1CCCCCC)[Sn](C)(C)C Chemical compound BrC=1SC(=CC1CCCCCC)[Sn](C)(C)C.BrC=1SC(=CC1CCCCCC)[Sn](C)(C)C VNBQVRSIKWVFLI-UHFFFAOYSA-N 0.000 description 1
- QQTKVVPIMSHYSW-UHFFFAOYSA-N C(CCCCCCCCCCC)OC=1C=C(C=CC1)C=1N=C2C(=NC1C1=CC(=CC=C1)OCCCCCCCCCCCC)C(=NC=C2Br)Br.C(CCCCCCCCCCC)OC=2C=C(C=CC2)C=2N=C1C(=NC2C2=CC(=CC=C2)OCCCCCCCCCCCC)C(=NC=C1Br)Br Chemical compound C(CCCCCCCCCCC)OC=1C=C(C=CC1)C=1N=C2C(=NC1C1=CC(=CC=C1)OCCCCCCCCCCCC)C(=NC=C2Br)Br.C(CCCCCCCCCCC)OC=2C=C(C=CC2)C=2N=C1C(=NC2C2=CC(=CC=C2)OCCCCCCCCCCCC)C(=NC=C1Br)Br QQTKVVPIMSHYSW-UHFFFAOYSA-N 0.000 description 1
- 125000003184 C60 fullerene group Chemical group 0.000 description 1
- QCPBQOCHJRMVNW-UHFFFAOYSA-N C[Sn](C=1SC(=CC1)[Sn](C)(C)C)(C)C.C[Sn](C=1SC(=CC1)[Sn](C)(C)C)(C)C Chemical compound C[Sn](C=1SC(=CC1)[Sn](C)(C)C)(C)C.C[Sn](C=1SC(=CC1)[Sn](C)(C)C)(C)C QCPBQOCHJRMVNW-UHFFFAOYSA-N 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- COCWWTNKIGVXHM-UHFFFAOYSA-N ClC=1N=C(C2=C(N1)C(=NC(=N2)Cl)NCCCCCCCC)NCCCCCCCC.ClC=2N=C(C1=C(N2)C(=NC(=N1)Cl)NCCCCCCCC)NCCCCCCCC Chemical compound ClC=1N=C(C2=C(N1)C(=NC(=N2)Cl)NCCCCCCCC)NCCCCCCCC.ClC=2N=C(C1=C(N2)C(=NC(=N1)Cl)NCCCCCCCC)NCCCCCCCC COCWWTNKIGVXHM-UHFFFAOYSA-N 0.000 description 1
- 229910000846 In alloy Inorganic materials 0.000 description 1
- 229910000799 K alloy Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical compound CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
- 229910020684 PbZr Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910002367 SrTiO Inorganic materials 0.000 description 1
- 229910004168 TaNb Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- 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 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 229920000109 alkoxy-substituted poly(p-phenylene vinylene) Polymers 0.000 description 1
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005229 chemical vapour deposition Methods 0.000 description 1
- KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- VBXJWRFADSRGDI-UHFFFAOYSA-L dichloronickel propane Chemical compound CCC.Cl[Ni]Cl VBXJWRFADSRGDI-UHFFFAOYSA-L 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000007606 doctor blade method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- ZULTVNRFZRQYKL-UHFFFAOYSA-M fluorotin Chemical compound [Sn]F ZULTVNRFZRQYKL-UHFFFAOYSA-M 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 229910021389 graphene Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910052752 metalloid Inorganic materials 0.000 description 1
- 150000002738 metalloids Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- LRYYUQJFQWSHNC-UHFFFAOYSA-N phenyl(4-phenylphosphanylbutyl)phosphane Chemical compound C=1C=CC=CC=1PCCCCPC1=CC=CC=C1 LRYYUQJFQWSHNC-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000012994 photoredox catalyst Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000264 poly(3',7'-dimethyloctyloxy phenylene vinylene) Polymers 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920000052 poly(p-xylylene) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000307 polymer substrate Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- CRUIOQJBPNKOJG-UHFFFAOYSA-N thieno[3,2-e][1]benzothiole Chemical compound C1=C2SC=CC2=C2C=CSC2=C1 CRUIOQJBPNKOJG-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 1
- KKRPPVXJVZKJON-UHFFFAOYSA-N trimethyl-(5-trimethylstannylthiophen-2-yl)stannane Chemical compound C[Sn](C)(C)C1=CC=C([Sn](C)(C)C)S1 KKRPPVXJVZKJON-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical class 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
-
- 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
-
- 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
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
-
- 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
-
- 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
- H10K85/151—Copolymers
-
- 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
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
- H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/12—Copolymers
- C08G2261/124—Copolymers alternating
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/324—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain condensed
- C08G2261/3241—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 nitrogen atoms as the only heteroatom, e.g. carbazole
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- 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
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/40—Polymerisation processes
- C08G2261/41—Organometallic coupling reactions
- C08G2261/414—Stille reactions
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/91—Photovoltaic applications
-
- 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
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/92—TFT applications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nanotechnology (AREA)
- Physics & Mathematics (AREA)
- Mathematical Physics (AREA)
- Theoretical Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Thin Film Transistor (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Photovoltaic Devices (AREA)
Description
本発明の他の実施形態に係る目的は、前記有機半導体化合物を含むトランジスタを提供することにある。
本発明のさらに他の実施形態に係る目的は、前記有機半導体化合物を含む電子素子を提供することにある。
R1およびR2は、それぞれ独立して、水素、ハロゲン、置換若しくは無置換のC1〜C20の直鎖又は分岐鎖のアルキル基、置換若しくは無置換のC3〜C20のシクロアルキル基、置換若しくは無置換の直鎖又は分岐鎖のC1〜C20のアルコキシ基、置換若しくは無置換のC3〜C20のシクロアルキロキシ基、置換若しくは無置換のC6〜C30のアリール基、置換若しくは無置換のC6〜C30のアリーロキシ基、置換若しくは無置換のC2〜C30のヘテロアリール基およびこれらの組み合わせよりなる群から選ばれ、あるいは、選択的に、1又は隣接しない2以上のCH2基が、−O−、−S−、−S(O)2−、−CO−、−OCO−、−C(O)O−、−CR51=CR52−、−C≡C−又はSiR53R54−(ここで、R51〜R54は、それぞれ独立して、水素、置換若しくは無置換のC1〜C15の直鎖又は分岐鎖のアルキル基、置換若しくは無置換のC3〜C15のシクロアルキル基、置換若しくは無置換のC1〜C15のアルコキシ基、置換若しくは無置換のC6〜C15のアリール基、置換若しくは無置換のC2〜C15のヘテロアリール基およびこれらの組み合わせよりなる群から選ばれる)で置換されたC1〜C20のアルキル基、C1〜C20のアルコキシ基またはC3〜C20のシクロアルキル基であり、但し、R1は水素ではなく、
Xは、それぞれ独立して、−CR3=N−、−N=N−、−CR4=CR5−、−O−、−S−、−Se−および−NR6−よりなる群から選ばれ、
Yは、−CR7=CR8−、−O−、−S−、−Se−および−NR9−よりなる群から選ばれ、
前記R3〜R9は、それぞれ独立して、水素、ハロゲン、置換若しくは無置換のC1〜C20の直鎖又は分岐鎖のアルキル基、置換若しくは無置換のC3〜C20のシクロアルキル基、置換若しくは無置換の直鎖又は分岐鎖のC1〜C20のアルコキシ基、置換若しくは無置換のC3〜C20のシクロアルキロキシ基、置換若しくは無置換のC6〜C30のアリール基、置換若しくは無置換のC6〜C30のアリーロキシ基、置換若しくは無置換のC2〜C30のヘテロアリール基およびこれらの組み合わせよりなる群から選ばれ、あるいは、選択的に、1又は隣接しない2以上のCH2基が、−O−、−S−、−S(O)2−、−CO−、−OCO−、−C(O)O−、−CR51=CR52−、−C≡C−又は−SiR53R54−(ここで、R51〜R54は、それぞれ独立して、水素、置換若しくは無置換のC1〜C15の直鎖又は分岐鎖のアルキル基、置換若しくは無置換のC3〜C15のシクロアルキル基、置換若しくは無置換のC1〜C15のアルコキシ基、置換若しくは無置換のC6〜C15のアリール基、置換若しくは無置換のC2〜C15のヘテロアリール基およびこれらの組み合わせよりなる群から選ばれる)で置換されたC1〜C20のアルキル基、C1〜C20のアルコキシ基またはC3〜C20のシクロアルキル基であり、又は
Xが−CR4=CR5−である場合に、隣り合うR4およびR5は互いに連結されて融合環(fused ring)を形成してもよく、又は
Yが−CR7=CR8−である場合に、隣り合うR7およびR8は互いに連結されて融合環を形成してもよく、
Zは、置換若しくは無置換のC1〜C40のアリーレン基、置換若しくは無置換のC4〜C14のヘテロ芳香族環基(heteroaromatic ring group)又はヘテロ芳香族環基を含む置換若しくは無置換のC6〜C30の縮合多環基であり、
pおよびqは、それぞれの構造単位のモル比を示し、p/(p+q)は、0.5〜0.95である。
上記の一般式4のそれぞれの環に存在する水素は、置換若しくは無置換のC1〜C15の直鎖又は分岐鎖のアルキル基、置換若しくは無置換のC3〜C15のシクロアルキル基、置換若しくは無置換のC1〜C15のアルコキシ基、置換若しくは無置換のC6〜C15のアリール基、置換若しくは無置換のC2〜C15のヘテロアリール基およびこれらの組み合わせよりなる群から選ばれる置換基で置換されていてもよい。
R1、R2、X、Y、Z、pおよびqは、一般式1の定義と同じ意味を有し、
Z’は、上記の一般式4から選ばれる少なくとも一つの官能基であり、Z’はZとは異なり、
rは、r/(p+q+r)が0.2以下の範囲にあるように存在してもよく、好ましくは、0.05〜0.15の範囲にあってもよい。
R1およびR2は、それぞれ独立して、水素、ハロゲン、置換若しくは無置換のC1〜C20の直鎖又は分岐鎖のアルキル基、置換若しくは無置換のC3〜C20のシクロアルキル基、置換若しくは無置換の直鎖又は分岐鎖のC1〜C20のアルコキシ基、置換若しくは無置換のC3〜C20のシクロアルキロキシ基、置換若しくは無置換のC6〜C30のアリール基、置換若しくは無置換のC6〜C30のアリーロキシ基、置換若しくは無置換のC2〜C30のヘテロアリール基およびこれらの組み合わせよりなる群から選ばれ、あるいは、選択的に、1又は隣接しない2以上のCH2基が、−O−、−S−、−S(O)2−、−CO−、−OCO−、−C(O)O−、−CR51=CR52−、−C≡C−又は−SiR53R54−(ここで、R51〜R54は、それぞれ独立して、水素、置換若しくは無置換のC1〜C15の直鎖又は分岐鎖のアルキル基、置換若しくは無置換のC3〜C15のシクロアルキル基、置換若しくは無置換のC1〜C15のアルコキシ基、置換若しくは無置換のC6〜C15のアリール基、置換若しくは無置換のC2〜C15のヘテロアリール基およびこれらの組み合わせよりなる群から選ばれる)で置換されたC1〜C20のアルキル基、C1〜C20のアルコキシ基またはC3〜C20のシクロアルキル基であり、但し、R1は水素ではない。
前記R3〜R9は、それぞれ独立して、水素、ハロゲン(例えば、フルオロ基)、置換若しくは無置換のC1〜C20の直鎖又は分岐鎖のアルキル基(例えば、フルオロアルキル基)、置換若しくは無置換のC3〜C20のシクロアルキル基、置換若しくは無置換の直鎖又は分岐鎖のC1〜C20のアルコキシ基、置換若しくは無置換のC3〜C20のシクロアルキロキシ基、置換若しくは無置換のC6〜C30のアリール基、置換若しくは無置換のC6〜C30のアリーロキシ基、置換若しくは無置換のC2〜C30のヘテロアリール基およびこれらの組み合わせよりなる群から選ばれ、あるいは、選択的に、1又は隣接しない2以上のCH2基が、−O−、−S−、−S(O)2−、−CO−、−OCO−、−C(O)O−、−CR51=CR52−、−C≡C−又はSiR53R54−(ここで、R51〜R54は、それぞれ独立して、水素、置換若しくは無置換のC1〜C15の直鎖又は分岐鎖のアルキル基、置換若しくは無置換のC3〜C15のシクロアルキル基、置換若しくは無置換のC1〜C15のアルコキシ基、置換若しくは無置換のC6〜C15のアリール基、置換若しくは無置換のC2〜C15のヘテロアリール基およびこれらの組み合わせよりなる群から選ばれる)で置換されたC1〜C20のアルキル基、C1〜C20のアルコキシ基またはC3〜C20のシクロアルキル基であり、又はXが−CR4=CR5−である場合に、隣り合うR4およびR5は互いに連結されて融合環を形成してもよく、Yは、−CR7=CR8−である場合に、隣り合うR7およびR8は互いに連結されて融合環を形成してもよい。
Z’は、一般式4から選ばれる少なくとも一つの官能基であり、Z’はZとは異なり、
rは、r/(p+q+r)が約0.2以下の範囲にあるように存在してもよく、好ましくは、0.05〜0.2又は0.05〜0.15の範囲にあってもよい。
前記有機半導体化合物は、p型有機半導体化合物であってもよい。
[反応式1]
A1〜A6は、それぞれ独立して、−Br、−I、−Clなどのハロゲン、トリアルキルスズ官能基およびボロラン官能基(borolane group)よりなる群から選ばれる反応性基(reactive group)であるが、これに限定されるものではなく、
前記トリアルキルスズ官能基は、下記の一般式9で表され、前記ボロラン官能基は、下記の一般式10又は11で表され得る。
[化12−1]
Pd(L1)x
[化12−2]
Pd(L2)4−yCly
[化12−3]
Ni(L3)x
[化12−4]
Ni(L4)3−yCly
前記反応式1の反応は、窒素雰囲気下、80〜120℃で6〜48時間行われる。
図3を参照すれば、有機太陽電池30は、基板31の上にアノード(anode)32が位置する。
[実施例]
[合成例1、単量体の合成]
2,3−ジ(3−ドデシロキシフェニル)−5,8−ジブロモピリド[3,4−b]ピラジン(2,3−di(3−dodecyloxylphenyl)−5,8−dibromopyrido[3,4−b]pyrazine)は、Macromolecules 1999, 32, 1375−1382、Bang−Lin Lee and Takakazu Yamamotoを参照して合成する。
1H NMR (CDCl3, ppm): δ(ppm): 8.76 (s, 1H), 7.59−7.73 (m, Ph), 7.59−7.73 (m, Ph), 3.86 (t, 4H), 1.71 (m, 4H), 1.35 (m, 36H, (CH2)9), 0.88 (t, 6H, CH3).
(2,6−ジクロロ−4,8−ビス(N−オクチルアミノ)ピリミド[5,4−d]ピリミジン(2,6−dichloro−4,8−bis(N−octylamino)pyrimido[5,4−d]pyrimidine)は、Macromolecules 2002, 35, 2993−2999、Takakazu Yamamoto and Bang−Lin Leeを参照して合成する。
1H NMR (CDCl3): δ(ppm): 6.86 (t, 2H, J = 5.37 Hz, NH), 3.57 (q, 4H, J = 6.25 Hz, N−CH2), 1.68 (m, 4H, CH2), 1.36 (m, 20H, (CH2)5), 0.88 (t, 6H, CH3). 13C{1H} NMR (CDCl3): δ(ppm): 159.38 (4,8−C), 156.52 (2,6−C), 131.66 (4a, 8a−C), 41.20 (C1 of octyl group), 31.77 (C2), 29.18 (C3), 29.16 (C4), 28.99 (C5), 26.84 (C6), 22.64 (C7), 14.05 (C8).
2−ブロモ−3−ヘキシル−5−トリメチルスタンニルチオフェン(2−bromo−3−hexyl−5−trimethylstannylthiophene)は、下記のようにして合成する。
[反応式2]
1H NMR (300MHz, CDCl3) δ(ppm): 0.34 (9H, CH3), 0.88 (3H, CH3), 1.31 (broad, 2nH, −(CH2)n−), 1.56 (m, 2H, −CH2−), 2.55 (t, 2H, Thiophene−CH2−), 6.84 (s, Thiophene−H).
2,5−ビス(トリメチルスタンニル)チオフェン(下記の反応式3中、m=1の場合)と、2,5−ビス(トリメチルスタンニル)ビチオフェン(2,5−bis(trimethylstannyl)bithiophene)(下記の反応式3中、m=2の場合)は、J. Org. Chem., 1984, 49, 5250の合成方法を参照して合成する。
[反応式3]
窒素雰囲気下で−50℃まで下げたジブロモチオフェン3.0g(12.4mmol)のテトラヒドロフラン(THF、50mL)溶液に、n−ブチルリチウム(1.63M n−BuLi in Hexane)18.4mL(30mmol)を入れ、同温度で30分間反応させた後、トリメチルスタンニルクロリド(以下、Me3SnClと称する、5g、25mmol)を入れて−50℃で4〜5時間反応させる。次いで、水およびエーテルで分液して得た有機層を乾燥剤で乾燥させた後に溶媒を除去する。そして、エーテルを用いた2回の再結晶化により白色の結晶3.1gを得る(収率:60%)。
1H−NMR (300 MHz, CDCl3) δ (ppm): 0.38 (CH3, 18H), 7.38 (2H, Thiophene−H).
2,5−ビス(トリメチルスタンニル)ビチオフェン(2,5−bis(trimethylstannyl)bithiophene)(上記の反応式3中、m=2の場合)は、下記のように合成する。
ジブロモチオフェンに代えて、ジブロモビチオフェンを用いる以外は、前記合成例1−4の方法と同様にして、2,5−ビス(トリメチルスタンニル)ビチオフェン(2,5−bis(trimethylstannyl)bithiophene)を合成する。
1H NMR (300MHz, CDCl3) δ(ppm): 0.38 (CH3, 18H), 7.08 (d, 2H, Thiophene−H), 7.27 (d, 2H, Thiophene−H).
1H NMR (300MHz, CDCl3) δ(ppm): 0.86−1.83 (alkyl−CH2), 2.60 (Th−CH2, Head−to−Head), 2.80 (Th−CH2, Head−to−Tail), 3.92 (b, −O−CH2−), 6.76 − 7.60(Th−H, Ph−H), 7.78 (b, Th−H), 8.52 (b, Th−H), 9.13 (s, pyrido[3,4−b]pyrazine−H).
前記実施例1で用いられた2,5−ビス(トリメチルスタンニル)ビチオフェンスタンニルに代えて、0.15g(0.2mmol)の2,6−ジトリメチルチン−4,8−ジエチルヘキシロキシ−ベンゾジチオフェンを用いる以外は、前記実施例1の方法と同様にして、6−1(2)で表される濃い紺色の高分子を合成する(収率=52%、数平均分子量=32、000、高温GPC、ポリスチレン標準品)。
1H NMR (300MHz, CDCl3) δ(ppm) : 0.84−1.73 (alkyl−CH2), 2.60 (Th−CH2, Head−to−Head), 2.80 (Th−CH2, Head−to−Tail), 3.90 (b, −O−CH2−), 4.24 (b, −O−CH2−), 6.90 − 7.64(Th−H, Ph−H), 7.84 (b, Th−H), 8.55 (b, Th−H), 9.13 (s, pyrido[3,4−b]pyrazine−H).
前記実施例1で用いられた2,5−ビス(トリメチルスタンニル)ビチオフェンの代わりに、0.15g(0.2mmol)の2,6−ジトリメチルチン−4,8−ジエチルヘキシロキシ−ベンゾジチオフェンを用いる以外は、前記実施例1の方法と同様にして、一般式6−1(1)で表される濃い紺色の高分子を合成する(収率=42%、数平均分子量=28、000、高温GPC、ポリスチレン標準品)。
1H NMR (300MHz, CDCl3) δ(ppm): 0.92−1.67 (alkyl−CH2), 2.60 (Th−CH2, Head−to−Head), 2.80 (Th−CH2, Head−to−Tail), 4.21 (b, −O−CH2−),6.90 − 7.98 (Aromatic −H)
1H NMR (300 MHz, CDCl3) δ (ppm): 0.92 (−CH3), 1.10−1.72 (alkyl−CH2), 2.60 (Th−CH2, Head−to−Head), 2.81 (Th−CH2, Head−to−Tail), 3.94 (b, −O−CH2−, −N−CH2−), 6.95−7.43 (Th−H, Ph−H), 7.80 (b, Th−H), 8.53 (b, Th−H), 9.13 (s, pyrido[3,4−b]pyrazine−H).
まず、洗浄されたガラス基板に、ゲート電極としてのクロムをスパッターリング法で1000Åの厚さで蒸着した後、ゲート絶縁膜としてのSiO2をCVD法で1000Åの厚さで蒸着する。その上に、ソース−ドレイン電極としてのAuをスパッターリング法で1200Åの厚さで蒸着する。基板は、有機半導体材料を蒸着する前に、イソプロピルアルコールを用いて10分間洗浄しかつ乾燥させて使用する。前記実施例1〜実施例4の有機半導体高分子をクロロホルムに10mMの濃度で希釈させたオクタデシルトリクロロシラン溶液に30秒間浸漬し、アセトンで洗浄して乾燥させた後に、前記実施例1〜実施例4で合成された有機半導体高分子をそれぞれクロロベンゼンに1.0重量%の濃度で溶解させてスピンコート法で塗布し、窒素雰囲気下、150℃で1時間ベークを行うことで有機薄膜トランジスタ(OTFT)素子を製作する。
前記実施例1〜実施例4で合成された有機半導体高分子をそれぞれPCBM(fullerene derivative[6,6]−phenyl−C61−butyric acid methylester)と1:1の重量比でクロロベンゼン溶媒の存在下で混合して、10mg/mLの濃度の溶液を製造する。ITOの表面を洗浄した後、PEDOT:PSS(Baytron P TP AI 4083、Bayer AG)を40nmの厚さでスピンコートした後、120℃で60分間ベークを行う。このようにして形成されたPEDOT:PSS層の上に前記溶液をそれぞれスピンコートして100nmの厚さの光活性層を形成し、1X10−6mbarの真空下でLiF(0.6nm)/Al(150nm)を熱蒸着してカソードを形成して有機太陽電池を製造する。
前記数式1に従い計算された実施例2による6−1(2)で表される有機半導体高分子とPCBMとの混合物(重量比=1:1)を含む有機太陽電池の効率は、2.85%であった。
12、22 基板、
16、26 絶縁層
18、28 活性層
14、24 ゲート電極
17a、27a ソース電極
17b、27b ドレイン電極
30 有機太陽電池
31 基板
32 アノード
33 正孔輸送層
34 光活性層
35 カソード
Claims (6)
- 請求項1に記載の有機半導体化合物を含むことを特徴とするトランジスタ。
- 前記トランジスタは、基板の上に位置するゲート電極と、相対向するように位置してチャンネル領域を限定するソース電極およびドレイン電極と、前記ソース電極およびドレイン電極とゲート電極を電気的に絶縁させる絶縁層と、前記チャンネル領域に形成された活性層と、を備え、
前記活性層は、有機半導体高分子を含むものであることを特徴とする請求項2に記載のトランジスタ。 - 請求項1に記載の有機半導体化合物を含むことを特徴とする電子素子。
- 前記電子素子は、有機太陽電池であることを特徴とする請求項4に記載の電子素子。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2011-0000692 | 2011-01-04 | ||
KR1020110000692A KR102011872B1 (ko) | 2011-01-04 | 2011-01-04 | 낮은 밴드 갭을 갖는 유기 반도체 화합물 및 이를 포함하는 트랜지스터와 전자 소자 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2012140624A JP2012140624A (ja) | 2012-07-26 |
JP5946273B2 true JP5946273B2 (ja) | 2016-07-06 |
Family
ID=45401015
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011290399A Active JP5946273B2 (ja) | 2011-01-04 | 2011-12-29 | 有機半導体化合物および、これを含むトランジスタと電子素子 |
Country Status (5)
Country | Link |
---|---|
US (1) | US9379329B2 (ja) |
EP (1) | EP2472625B1 (ja) |
JP (1) | JP5946273B2 (ja) |
KR (1) | KR102011872B1 (ja) |
CN (1) | CN102585173B (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2935427B1 (en) | 2012-12-18 | 2018-12-26 | Merck Patent GmbH | Polymer comprising a thiadiazol group, the production of such polymer and its use in organic electronic devices |
TW201501340A (zh) * | 2013-06-27 | 2015-01-01 | Inst Nuclear Energy Res Atomic Energy Council | 製備大面積有機太陽能電池之方法 |
US9876184B2 (en) * | 2013-08-28 | 2018-01-23 | Taiwan Semiconductor Manufacturing Company, Ltd. | Organic photosensitive device with an electron-blocking and hole-transport layer |
KR102168174B1 (ko) | 2014-03-19 | 2020-10-20 | 삼성전자주식회사 | 니켈 화합물 및 이를 이용한 박막 형성 방법 |
Family Cites Families (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5946551A (en) | 1997-03-25 | 1999-08-31 | Dimitrakopoulos; Christos Dimitrios | Fabrication of thin film effect transistor comprising an organic semiconductor and chemical solution deposited metal oxide gate dielectric |
US6215130B1 (en) | 1998-08-20 | 2001-04-10 | Lucent Technologies Inc. | Thin film transistors |
WO2002059121A1 (en) | 2001-01-24 | 2002-08-01 | Cambridge Display Technology Limited | Monomer for use in preparation of a polymer to be used in optical devices |
KR101007787B1 (ko) | 2003-12-08 | 2011-01-14 | 삼성전자주식회사 | 퀴녹살린환을 주쇄에 포함하는 유기박막 트랜지스터용유기반도체 고분자 |
WO2006036756A2 (en) | 2004-09-24 | 2006-04-06 | Plextronics, Inc. | Heteroatomic regioregular poly(3-substitutedthiophenes) in photovoltaic cells |
KR101224708B1 (ko) | 2004-10-19 | 2013-01-21 | 삼성전자주식회사 | (올리고티오펜-아릴렌) 유도체 및 이를 이용한유기박막트랜지스터 |
KR20070112799A (ko) | 2005-03-16 | 2007-11-27 | 플렉스트로닉스, 인크 | 개선된 전자 성능을 갖는 가용성 폴리(티오펜)의 공중합체 |
KR101314931B1 (ko) | 2006-10-30 | 2013-10-04 | 삼성전자주식회사 | 유기 고분자 반도체, 이의 제조방법 및 이를 이용한 양극성 유기 박막 트랜지스터 |
JP2008208289A (ja) | 2007-02-28 | 2008-09-11 | Sumitomo Chemical Co Ltd | 芳香族重合体およびそれを用いた有機光電変換素子 |
US20080262183A1 (en) | 2007-04-17 | 2008-10-23 | Lutz Uwe Lehmann | Dithienopyrrole-containing copolymers |
KR101548764B1 (ko) | 2008-04-11 | 2015-08-31 | 도레이 카부시키가이샤 | 전자 공여성 유기 재료, 광 기전력 소자용 재료 및 광 기전력 소자 |
CN102027612B (zh) * | 2008-05-12 | 2013-11-13 | 东丽株式会社 | 碳纳米管复合体、有机半导体复合材料和场效应晶体管 |
US8367798B2 (en) | 2008-09-29 | 2013-02-05 | The Regents Of The University Of California | Active materials for photoelectric devices and devices that use the materials |
JP5655267B2 (ja) | 2008-11-10 | 2015-01-21 | 東レ株式会社 | キノキサリン化合物、これを用いた電子供与性有機材料、光起電力素子用材料および光起電力素子 |
JP5533646B2 (ja) | 2009-01-20 | 2014-06-25 | 東レ株式会社 | 光起電力素子用材料および光起電力素子 |
CN102439059B (zh) | 2009-05-21 | 2014-06-11 | 破立纪元有限公司 | 共轭聚合物及其在光电子器件中的用途 |
WO2010138566A2 (en) | 2009-05-26 | 2010-12-02 | University Of Florida Research Foundation, Inc. | Green soluble conjugated polymers with high charge carrier mobilities |
KR101648072B1 (ko) * | 2009-07-03 | 2016-08-12 | 삼성전자 주식회사 | 유기 반도체 고분자 및 이를 포함하는 트랜지스터 |
WO2011138885A1 (ja) | 2010-05-06 | 2011-11-10 | 住友化学株式会社 | 高分子化合物及びそれを用いた有機光電変換素子 |
-
2011
- 2011-01-04 KR KR1020110000692A patent/KR102011872B1/ko active IP Right Grant
- 2011-08-17 US US13/211,810 patent/US9379329B2/en active Active
- 2011-12-29 JP JP2011290399A patent/JP5946273B2/ja active Active
-
2012
- 2012-01-03 EP EP12150078.9A patent/EP2472625B1/en active Active
- 2012-01-04 CN CN201210001157.7A patent/CN102585173B/zh active Active
Also Published As
Publication number | Publication date |
---|---|
EP2472625B1 (en) | 2020-04-01 |
CN102585173B (zh) | 2016-11-02 |
KR102011872B1 (ko) | 2019-08-19 |
KR20120079423A (ko) | 2012-07-12 |
CN102585173A (zh) | 2012-07-18 |
US20120168727A1 (en) | 2012-07-05 |
JP2012140624A (ja) | 2012-07-26 |
EP2472625A1 (en) | 2012-07-04 |
US9379329B2 (en) | 2016-06-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5311936B2 (ja) | ジケトピロロピロール系ポリマーおよびその形成方法 | |
Tsai et al. | New two-dimensional thiophene− acceptor conjugated copolymers for field effect transistor and photovoltaic cell applications | |
US8871884B2 (en) | Copolymer semiconductors comprising thiazolothiazole or benzobisthiazole, or benzobisoxazole electron acceptor subunits, and electron donor subunits, and their uses in transistors and solar cells | |
Cheng et al. | Carbazole-based ladder-type heptacylic arene with aliphatic side chains leading to enhanced efficiency of organic photovoltaics | |
TWI511997B (zh) | 共軛聚合物及其於光電子裝置的用途 | |
Kim et al. | Incorporation of pyrene units to improve hole mobility in conjugated polymers for organic solar cells | |
Gu et al. | Synthesis and photovoltaic properties of copolymers based on benzo [1, 2-b: 4, 5-b′] dithiophene and thiophene with different conjugated side groups | |
EP2034537A2 (en) | Diketopyrrolopyrrole-based derivatives for thin film transistors | |
JP2014512100A (ja) | 電気光学デバイスの活性物質および電気光学デバイス | |
Hou et al. | Synthesis and photovoltaic properties of the copolymers of 2-methoxy-5-(2′-ethylhexyloxy)-1, 4-phenylene vinylene and 2, 5-thienylene-vinylene | |
Shi et al. | Bichalcogenophene imide-based homopolymers: chalcogen-atom effects on the optoelectronic property and device performance in organic thin-film transistors | |
Kim et al. | Introduction of perylene units for enhanced interchain interaction in conjugated polymers for organic photovoltaic devices | |
EP2270064B1 (en) | Organic semiconductor polymer, transistor including an organic semiconductor polymer and methods of fabricating the same | |
JP5946273B2 (ja) | 有機半導体化合物および、これを含むトランジスタと電子素子 | |
Gunawardhana et al. | Thieno [3, 2-b] pyrrole and Benzo [c][1, 2, 5] thiadiazole Donor–Acceptor Semiconductors for Organic Field-Effect Transistors | |
Lee et al. | Synthesis of random copolymers based on 3-hexylthiophene and quinoxaline derivative: Influence between the intramolecular charge transfer (ICT) effect and π-conjugation length for their photovoltaic properties | |
US20150194608A1 (en) | Building block for low bandgap conjugated polymers | |
KR101553806B1 (ko) | 포스핀 옥사이드기를 포함하는 유기 반도체 화합물 및 이를 이용한 유기태양전지 | |
US8933441B2 (en) | Organic electronic device | |
Bagde et al. | Diketopyrrolopyrrole-based narrow band gap donors for efficient solution-processed organic solar cells | |
KR101947020B1 (ko) | 낮은 밴드 갭을 갖는 유기 반도체 화합물 및 이를 포함하는 트랜지스터와 전자 소자 | |
KR101535066B1 (ko) | 두 개의 적층형 유기 태양전지 소자용 유기 반도체 화합물, 및 이를 포함하는 유기전자소자 | |
Wang et al. | Synthesis and photovoltaic properties of organic small molecules containing triphenylamine and benzothiadiazole moieties with different terminal groups | |
KR101935466B1 (ko) | 유기 전자 소자 | |
KR20080069813A (ko) | 티아졸 함유 유기반도체 고분자, 이의 제조방법 및 이를이용한 유기박막트랜지스터 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20140528 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20150130 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150224 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20150428 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20150721 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20151016 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20151215 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20160412 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20160420 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20160524 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20160531 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5946273 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |