JP6177929B2 - 有機半導体材料 - Google Patents
有機半導体材料 Download PDFInfo
- Publication number
- JP6177929B2 JP6177929B2 JP2015542395A JP2015542395A JP6177929B2 JP 6177929 B2 JP6177929 B2 JP 6177929B2 JP 2015542395 A JP2015542395 A JP 2015542395A JP 2015542395 A JP2015542395 A JP 2015542395A JP 6177929 B2 JP6177929 B2 JP 6177929B2
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- linear
- compound
- branched
- branched alkyl
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- 239000004065 semiconductor Substances 0.000 title claims description 35
- 239000000463 material Substances 0.000 title claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 102
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- 239000010410 layer Substances 0.000 description 32
- 125000003118 aryl group Chemical group 0.000 description 21
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 20
- 239000010408 film Substances 0.000 description 15
- 125000001072 heteroaryl group Chemical group 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- 125000003367 polycyclic group Chemical group 0.000 description 13
- -1 aromatic tetracarboxylic anhydrides Chemical class 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 125000002950 monocyclic group Chemical group 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 238000005259 measurement Methods 0.000 description 11
- 230000005693 optoelectronics Effects 0.000 description 11
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 11
- 239000004926 polymethyl methacrylate Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 125000005277 alkyl imino group Chemical group 0.000 description 8
- 125000004404 heteroalkyl group Chemical group 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 230000032258 transport Effects 0.000 description 8
- 238000002441 X-ray diffraction Methods 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 238000010586 diagram Methods 0.000 description 7
- 229930192474 thiophene Natural products 0.000 description 7
- 238000002061 vacuum sublimation Methods 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 125000005431 alkyl carboxamide group Chemical group 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 125000002843 carboxylic acid group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000000295 emission spectrum Methods 0.000 description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 125000002560 nitrile group Chemical group 0.000 description 6
- 238000012856 packing Methods 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 230000005669 field effect Effects 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000004642 Polyimide Substances 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 229920001721 polyimide Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910005965 SO 2 Inorganic materials 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- 238000002484 cyclic voltammetry Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 230000002427 irreversible effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AKAIWNDBVZJOAJ-UHFFFAOYSA-N 1,4-dithiine Chemical group S1C=CSC=C1 AKAIWNDBVZJOAJ-UHFFFAOYSA-N 0.000 description 2
- RWRXDIMAXLSQMK-UHFFFAOYSA-N 3h-1,2,3-benzodithiazole Chemical compound C1=CC=C2NSSC2=C1 RWRXDIMAXLSQMK-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- PHXQIAWFIIMOKG-UHFFFAOYSA-N NClO Chemical compound NClO PHXQIAWFIIMOKG-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001454 anthracenes Chemical class 0.000 description 2
- 238000006254 arylation reaction Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000000089 atomic force micrograph Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000006880 cross-coupling reaction Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000002950 deficient Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical class N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 2
- 229910000071 diazene Inorganic materials 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 2
- HKNRNTYTYUWGLN-UHFFFAOYSA-N dithieno[3,2-a:2',3'-d]thiophene Chemical compound C1=CSC2=C1SC1=C2C=CS1 HKNRNTYTYUWGLN-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000000879 optical micrograph Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- WPPDXAHGCGPUPK-UHFFFAOYSA-N red 2 Chemical compound C1=CC=CC=C1C(C1=CC=CC=C11)=C(C=2C=3C4=CC=C5C6=CC=C7C8=C(C=9C=CC=CC=9)C9=CC=CC=C9C(C=9C=CC=CC=9)=C8C8=CC=C(C6=C87)C(C=35)=CC=2)C4=C1C1=CC=CC=C1 WPPDXAHGCGPUPK-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000000527 sonication Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- OSEFDTSYKYIFNC-UHFFFAOYSA-N thieno[2,3-c]pyrrole-4,6-dione Chemical class S1C=CC2=C1C(=O)NC2=O OSEFDTSYKYIFNC-UHFFFAOYSA-N 0.000 description 2
- VJYJJHQEVLEOFL-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2 VJYJJHQEVLEOFL-UHFFFAOYSA-N 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- VXBHLQIFGXDFDS-UHFFFAOYSA-N tributyl-(5-thiophen-2-ylthiophen-2-yl)stannane Chemical compound S1C([Sn](CCCC)(CCCC)CCCC)=CC=C1C1=CC=CS1 VXBHLQIFGXDFDS-UHFFFAOYSA-N 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- 238000001075 voltammogram Methods 0.000 description 2
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 description 1
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 1
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- KXSFECAJUBPPFE-UHFFFAOYSA-N 2,2':5',2''-terthiophene Chemical compound C1=CSC(C=2SC(=CC=2)C=2SC=CC=2)=C1 KXSFECAJUBPPFE-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- ODFFQGIOBCTXHR-UHFFFAOYSA-N 2-[5-[5-[5-(1,3-dioxolan-2-yl)thiophen-2-yl]thiophen-2-yl]thiophen-2-yl]-5-hexylthieno[2,3-c]pyrrole-4,6-dione Chemical compound O1C(OCC1)C1=CC=C(S1)C1=CC=C(S1)C=1SC(=CC1)C1=CC2=C(C(N(C2=O)CCCCCC)=O)S1 ODFFQGIOBCTXHR-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- FHPFDCRNWLVVHD-UHFFFAOYSA-N 2-thiophen-2-yl-1,3-dioxolane Chemical compound O1CCOC1C1=CC=CS1 FHPFDCRNWLVVHD-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- BCLYNNCSKHBRLD-UHFFFAOYSA-N 5-butyl-2-(5-thiophen-2-ylthiophen-2-yl)thieno[2,3-c]pyrrole-4,6-dione Chemical compound S1C=2C(=O)N(CCCC)C(=O)C=2C=C1C(S1)=CC=C1C1=CC=CS1 BCLYNNCSKHBRLD-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005082 alkoxyalkenyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- CJXGPJZUDUOZDX-UHFFFAOYSA-N fluoromethanone Chemical group F[C]=O CJXGPJZUDUOZDX-UHFFFAOYSA-N 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 229910003472 fullerene Inorganic materials 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000005020 hydroxyalkenyl group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000005016 hydroxyalkynyl group Chemical group 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 238000005040 ion trap Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical compound C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical compound C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 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
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000010079 rubber tapping Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical class O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- FIDKFEIEZJGDBE-UHFFFAOYSA-N thieno[2,3-c]furan-4,6-dione Chemical compound S1C=CC2=C1C(=O)OC2=O FIDKFEIEZJGDBE-UHFFFAOYSA-N 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- WFFUXODEBRWZNO-UHFFFAOYSA-N tributyl-(5-hexylthiophen-2-yl)stannane Chemical compound CCCCCCC1=CC=C([Sn](CCCC)(CCCC)CCCC)S1 WFFUXODEBRWZNO-UHFFFAOYSA-N 0.000 description 1
- LPAWLMVOUBWAHW-UHFFFAOYSA-N tributyl-[5-(1,3-dioxolan-2-yl)thiophen-2-yl]stannane Chemical compound S1C([Sn](CCCC)(CCCC)CCCC)=CC=C1C1OCCO1 LPAWLMVOUBWAHW-UHFFFAOYSA-N 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
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
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
- C07D495/12—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 three hetero rings
- C07D495/14—Ortho-condensed systems
-
- 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
- C07D495/22—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 four or more hetero rings
-
- 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
- C09B57/00—Other synthetic dyes of known constitution
-
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- 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
- C09B69/008—Dyes containing a substituent, which contains a silicium atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- 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]
- H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/30—Organic light-emitting transistors
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- Spectroscopy & Molecular Physics (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thin Film Transistor (AREA)
Description
R1、R2は互いに独立して、水素、C1〜C40直鎖状または分岐状アルキル基、C2〜C40直鎖状または分岐状アルケニル基、C2〜C40直鎖状または分岐状アルキニル基、C1〜C40直鎖状または分岐状ヘテロアルキル基、C2〜C40直鎖状または分岐状ヘテロアルケニル基、C2〜C40直鎖状または分岐状ヘテロアルキニル基、C3〜C40直鎖状または分岐状シクロアルキル基、C2〜C40直鎖状または分岐状ヘテロシクロアルキル基、C2〜C40直鎖状または分岐状アルキルカルボン酸基、C2〜C40直鎖状または分岐状アルキルカルボキサミド基、C2〜C40直鎖状または分岐状アルキルイミノ基、C1〜C40直鎖状または分岐状アルキルスルホン酸基、C1〜C40直鎖状または分岐状アルキルニトリル基からなる群において選択され、
Ar、Ar’、Ar”は互いに独立して、単環式アリール基、置換単環式アリール基、多環式アリール基、置換多環式アリール基、単環式ヘテロアリール基、置換単環式ヘテロアリール基、多環式ヘテロアリール基、置換多環式ヘテロアリール基、ならびに二量体、三量体および四量体としてのそれらの組合せからなる群において選択され、
R3は、水素、ハロゲン、C1〜C20直鎖状または分岐状アルキル基、C2〜C20直鎖状または分岐状アルケニル基、C2〜C20直鎖状または分岐状アルキニル基、C1〜C20直鎖状または分岐状ヘテロアルキル基、C2〜C20直鎖状または分岐状ヘテロアルケニル基、C2〜C20直鎖状または分岐状ヘテロアルキニル基、C3〜C20直鎖状または分岐状シクロアルキル基、C2〜C20ヘテロシクロアルキル基、C2〜C20直鎖状または分岐状アルキルカルボン酸基、C2〜C20直鎖状または分岐状アルキルカルボキサミド基、C2〜C20直鎖状または分岐状アルキルイミノ基、C1〜C20直鎖状または分岐状アルキルスルホン酸基、C1〜C20直鎖状または分岐状アルキルニトリル基からなる群において選択され、
n、rは互いに独立して、1〜50の間の整数であり、
pは、0〜5の間の整数であり、さらに
Tは、化合物の末端単位であり、C1〜C40直鎖状または分岐状アルキル基、C2〜C40直鎖状または分岐状アルケニル基、C2〜C40直鎖状または分岐状アルキニル基、C1〜C40直鎖状または分岐状ヘテロアルキル基、C2〜C40直鎖状または分岐状ヘテロアルケニル基、C2〜C40直鎖状または分岐状ヘテロアルキニル基、C3〜C40直鎖状または分岐状シクロアルキル基、C2〜C40ヘテロシクロアルキル基、C2〜C40直鎖状または分岐状アルキルカルボン酸基、C2〜C40直鎖状または分岐状アルキルカルボキサミド基、C2〜C40直鎖状または分岐状アルキルイミノ基、C1〜C40直鎖状または分岐状アルキルスルホン酸基、C1〜C40直鎖状または分岐状アルキルニトリル基、単環式アリール基、置換単環式アリール基、多環式アリール基、置換多環式アリール基、単環式ヘテロアリール基、置換単環式ヘテロアリール基、多環式ヘテロアリール基、置換多環式ヘテロアリール基、ベンジル基、及び置換ベンジル基、ならびに二量体、三量体および四量体としてのそれらの組合せからなる群において選択され、
pの値が0の場合にはTはAr’とは異なり、pの値が1〜5の場合にはTはA”とは異なる]
からなる群において選択される式を有し、式A
R5は、単環式アリール基及び置換単環式アリール基からなる群において選択される]
の化合物を除き、また式B
の化合物を除く、化合物が提供される。
- 「ヘテロアルキル基」とは、例えば、ハロゲノアルキル基、ヒドロキシアルキル基、アルコキシアルキル基を含むよう意図されており、
- 「ヘテロアルケニル基」とは、例えば、ハロゲノアルケニル基、ヒドロキシアルケニル基、アルコキシアルケニル基を含むよう意図されており、
-「ヘテロアルキニル基」は、例えば、ハロゲノアルキニル基、ヒドロキシアルキニル基、アルコキシアルキニル基を含むよう意図される。
n及びrの値は、好ましくは、2〜50の間、より好ましくは2〜30の間、さらにより好ましくは2〜10の間に含まれる。
Dは、C、S、O、Se原子、およびSO、SO2、R14-P=O、P-(R14)、BR14、N-R15、Si(R15)2基からなる群において選択され、
B、Cは互いに独立して、C、N原子からなる群において選択され、
Eは、C(R15)2、S、OおよびNR15基からなる群において選択され、
R8、R9、R10、R11、R12およびR13は、互いに独立して、水素、ハロゲン、C1〜C20直鎖状または分岐状アルキル基、C2〜C20直鎖状または分岐状アルケニル基、C2〜C20直鎖状または分岐状アルキニル基、C1〜C20直鎖状または分岐状ヘテロアルキル基、C2〜C20直鎖状または分岐状ヘテロアルケニル基、C2〜C20直鎖状または分岐状ヘテロアルキニル基、C3〜C20シクロアルキル基、C2〜C20直鎖状または分岐状ヘテロシクロアルキル基、C2〜C20直鎖状または分岐状アルキルカルボン酸基、C2〜C20直鎖状または分岐状アルキルカルボキサミド基、C2〜C20直鎖状または分岐状アルキルイミノ基、C1〜C20直鎖状または分岐状アルキルスルホン酸基、C1〜C20直鎖状または分岐状アルキルニトリル基、C5〜C40アリール基、C1〜C40ヘテロアリール基、C6〜C40アルキルアリール基からなる群において選択され、
R14、R15は、互いに独立して、水素、C1〜C20直鎖状または分岐状アルキル基、C2〜C20直鎖状または分岐状アルケニル基、C2〜C20直鎖状または分岐状アルキニル基、C1〜C20直鎖状または分岐状ヘテロアルキル基、C2〜C20直鎖状または分岐状ヘテロアルケニル基、C2〜C20直鎖状または分岐状ヘテロアルキニル基、C3〜C20直鎖状または分岐状シクロアルキル基、C2〜C20直鎖状または分岐状ヘテロシクロアルキル基、C2〜C20直鎖状または分岐状アルキルカルボン酸基、C2〜C20直鎖状または分岐状アルキルカルボキサミド基、C2〜C20直鎖状または分岐状アルキルイミノ基、C1〜C20直鎖状または分岐状アルキルスルホン酸基、C1〜C20直鎖状または分岐状アルキルニトリル基、C5〜C40アリール基、C1〜C40ヘテロアリール基、C6〜C40アルキルアリール基からなる群において選択される。
における場合のように、以上に示される(a)〜(r)基などの別のアリール単位に連結した、チオフェン、チアゾール、フラン、ベンゾジチアゾール、チエノチオフェン、またはフェニル単位を含む、二量体であってよい。
におけるものなどの多環式またはオリゴアリール単位にα結合している、チオフェン単位を含む二量体とすることができる。
Yは、CおよびNからなる群において選択され、
からなる群において選択される。
N2雰囲気下、化合物1(82mg、0.28mmol)およびその場で調製した触媒Pd(AsPh3)4(8mol%、Pd2dba3 11mgおよびAsPh3 27mg)の還流トルエン溶液(8ml)に、トルエン(0.5ml)中の5-(トリブチルスタニル)-2,2’-ビチオフェン、2(135mg、0.3mmol)を滴下して加えた。この溶液を6時間還流し、次に、この溶媒を真空下で除去し、粗生成物を、pet. eth./DCM/AcOEt = 90:5:5である溶液を溶離剤として用いてシリカゲルのフラッシュクロマトグラフィーで精製した。化合物3を橙色粉末として単離し(83mg、収率79%)、更なる精製なしに以下の工程に用いた。MS (70 eV, EI): m/z 373 (M. +1). 1H NMR (CDCl3, TMS/ppm)δ: 7.29 (s, 1 H), 7.28 (dd, 3J=5,2 Hz, 4J=1,2 1H), 7.23 (m, 2H), 7.12 (d, 3J=3,6 Hz 1H), 7.05 (dd, 3J=5,2 Hz, 3J=4.8 1H), 3.60 (t, 2H), 1.63 (m, 2H), 1.36 (m, 2H), 0.95 (t, 3H). 13C NMR (CDCl3, TMS/ppm): 163.9, 162.8, 149.9, 145.2, 139.3, 137.1, 136.1, 133.6, 128.1, 126.7,125.5, 124.7,124.5, 116.3, 38.3, 30.8, 20.0, 13.6.
工程(a)で得られた化合物3(90mg、0.24mmol)を、ジクロロメタンと酢酸溶液との1:1混合物8mlに溶解させた。NBS (50 mg、0.28 mmol)を加え、反応混合物を室温で一晩、暗所にて攪拌した。かくして得られた黄色溶液を、その後10mlの水で希釈し、ジクロロメタンで抽出し、10%のNaHCO3、次いで水で洗浄した。有機相を無水硫酸ナトリウムで乾燥させ、蒸発させ、粗生成物を、pet. eth./AcOEt = 94:6〜80:20を溶離剤として用いてシリカゲルのフラッシュクロマトグラフィーで精製した。化合物4を橙色粉末として単離した(収率97%)。M.p. 153°C, MS (70 eV, EI): m/z 451,453 (M. +1). 1H NMR (CDCl3, TMS/ppm)δ: 7.29 (s, 1H), 7.21 (d, 3J=4.0Hz, 1H), 7.05 (d, 3J=3.6 Hz, 1H), 7.00 (d, 3J=4.0 Hz, 1H), 6.96 (d, 3J=4.0 Hz, 1H), 3.60 (t, 2H), 1.62 (m, 2H), 1.36 (m, 2H), 0.95 (t, 3H). 13C NMR (CDCl3, TMS/ppm) 163.9, 162.7, 149.5, 145.2, 138.1, 137.6, 137.4, 134.0, 130.9, 126.7, 124.8, 124.7, 116.7, 112.3, 38.3, 30.8, 20.0, 13.6.
N2雰囲気下、工程(b)で得られた化合物4(0.22mmol)及びPd(AsPh3)4(8mol%、その場で調製)の還流トルエン溶液(12ml)に、3mlのトルエンで希釈した化合物5(0.26mmol)を滴下して加えた。この溶液を8時間還流し、次に、この溶媒を真空下で除去し、粗生成物を、pet. eth./酢酸エチル= 95:5〜0:100を溶離剤として用いてシリカゲルのフラッシュクロマトグラフィーで精製し、次いで結晶化させた。
化合物6を橙色粉末として得た(収率68%)。M.p. 178° (K→LC), 260°; MS (70 eV, EI): m/z 539 (M. +1). 1H NMR (CDCl3, TMS/ppm): 7.28 (s, 1H), 7.22 (d, 3J=3.6 Hz 1H), 7.10 (d, 3J =3.6 Hz 1H), 7.09 (d, 3J =4.0 Hz, 1H), 7.01 (d, 3J =4.0 Hz, 1H), 7.00 (d, 3J =3.6 Hz, 1H), 7.69 (d, 3J =3.6 Hz, 1H), 3.60 (t, 2H), 2.80 (t, 2H), 1.66 (m, 4H), 1.35 (m, 8H), 0.92 (m, 6H). 13C NMR (CDCl3, TMS/ppm): 163.9, 162.8, 149.9, 146.2, 145.3, 139.2, 138.2, 137.0, 134.0, 133.3, 126.7, 125.2, 124.9, 124.2, 123.8, 123.7,116.2, 38.3, 31.5, 30.9, 30.2, 28.7, 22.6, 20.0, 14.1, 13.6. Anal. Calcd for C28H29NO2S4 (539.80): C, 62.30; H, 5.42. Found: C, 62.24; H, 5.49.
有機薄膜トランジスタを、ボトムゲートトップ接触構成で作製した。ITO基板を、2回の音波照射周期(1回目はアセトン中、次に2-イソプロパノール中で、各10分間)により清浄した。次に、厚さ450nmのPMMA誘電体層を、上記の清浄なITO基板の上部でスピンコーティングによって成長させた。比誘電率εは、100Hzにおいて3.6であった。次に、このPMMA層をグローブボックス中、120℃(すなわち、PMMAのガラス転移温度よりも約10℃高い)で15時間、不活性雰囲気下で熱的にアニーリングした。(CPMMA=7.08nF/cm2)。
[式1]μ=L/(W*C)A^2
(式中、Aは印加電位に対するドレイン電流の平方根を直線にあてはめた場合の角度係数であり、Lはチャネル長であり、Wはチャネル幅であり、Cはトランジスタの誘電キャパシタンスである)
を使用して、軌跡曲線から算出した。
実施例2のトランジスタの構造を有する有機発光トランジスタを作製し、すなわち、次いで同様の操作を行った。
工程(d):2-(5”-(ペルフルオロヘキシル)-2,2’:5’,2”-ターチオフェン-5-イル)-5-ブチル-5H-チエノ[3,2-c]ピロール-4,6-ジオン、8の合成
N2雰囲気下、Pd(AsPh3)4(8mol%、その場で調製)及び化合物4(0.237mmol)の還流トルエン溶液(8ml)に、0.5mlのトルエン中に希釈した化合物7(0.26mmol)を滴下して加えた。この溶液を8時間還流し、次に、この溶媒を真空下で除去した。粗生成物を、DCMを溶離剤とし、シリカゲルのフラッシュクロマトグラフィーで精製し、次いでトルエンから結晶化させた。
X線データを、入射放射線としてMo-Kα (λ= 0.71073Å)を備えたBruker SMART Apex II CCD面積検出器回折計を用いて収集した。構造を、SIR 97を用いて解析し、SHELXL97を用い、Fo 2に対する完全行列最小二乗法によって精密化した。
有機薄膜トランジスタを、ボトムゲートトップ接触構成で作製した。ITO基板を、まずはアセトン中、次いで2-イソプロパノール中で、各10分間に亘る、2回の音波照射周期によって清浄化した。次に、厚さ450nmのPMMA誘電体層を、上記の清浄なITO基板の上部でスピンコーティングによって堆積させた。比誘電率εは、100Hzにおいて3.6であった。次に、このPMMA層をグローブボックス中、120℃(すなわち、PMMAのガラス転移温度よりも約10℃高い)で15時間、不活性雰囲気下で熱的にアニーリングした。(CPMMA=7.08nF/cm2)。
有機発光トランジスタを、実施例3に記載のように作製した。
図12(a)は、化合物8で形成された半導体層を備えて得られたOLETデバイスの概略図を示す。
9mlのフルオロベンゼン中のチオフェン-2-カルボアルデヒド(1g、0.0089mol)、エチレングリコール(1.3g、0.02mol)、p-TsOH(0.022g)の混合物を、H2O分離の下、還流温度で5時間に亘って撹拌した。55℃(0.1mmHg)での蒸留により、1.06gの19をオイルとして得た(収率76%)。
1H NMR (CDCl3, TMS/ppm) δ 7.33 (m, 1H), 7.17 (m, 1H), 7.04 (d, 3J = 4.0 Hz, 2H), 6.00 (dd, 3J = 3.6 Hz, 3J = 3.2 Hz, 1H), 6.12 (s, 1H), 4.14 (m, 2H), 4.02 (m, 2H).
N2雰囲気下、THF15ml中の19(0.970g、0.0062mol)の無水溶液に、BuLi(ヘキサン中2.5M)(3.0ml、0.0074mol)を滴下して加えた。この混合物を2時間撹拌し、その後同じ温度でBu3SnCl(2.0g、0.0062mol)を滴下して加えた。反応を、室温で撹拌しつつ一晩放置した。溶媒を真空下で除去し、その後、粗生成物を、エチルエーテルに溶解させ、水でクエンチした。抽出後、有機相をNa2SO4で乾燥させ、溶媒を蒸発させ、化合物20を褐色オイルとして得た(2.7mg、収率98%)。
1H NMR (CDCl3, TMS/ppm) δ 7.27 (d, 3J = 3.2 Hz, 1H), 7.05 (d, 3J = 3.2 Hz, 1H), 6.15 (s, 1H), 4.15 (m, 2H), 4.01 (m, 2H), 1.55 (m, 6H), 1.31 (m, 6H), 1.08 (m, 6H), 0.89 (t, 9H).
N2雰囲気下、22(100mg、0.2mmol)およびその場で調製した触媒Pd(AsPh3)4(8mol%、すなわち4mlのトルエン中のPd2dba3 8mgおよびAsPh3 19mg)の還流トルエン溶液(3ml)に、トルエン(1ml)中の20(102mg、0.23mmol)を滴下して加えた。この溶液を12時間還流し、次に、溶媒を蒸発させ、粗生成物をペンタンにより洗浄した。得られた固体を、シリカゲル(CH2Cl2で溶離)のフラッシュクロマトグラフィーによって精製した。生成物を含むフラクションをまとめ、溶媒を蒸発させ、残渣を熱トルエンから結晶化させて橙赤色固体を得た(60mg、収率54%)。
M.p. 190 °C. EI-MS m/z 555 (M.+). λlmax (CH2Cl2), 439 nm, λlem (CH2Cl2), 604 nm.
1H NMR (CDCl3, TMS/ppm) δ 7.30 (s, 1 H), 7.24 (d, 3J = 4.0 Hz, 1H), 7.13 (d, 3J = 4.0 Hz, 1H), 7.12 (d, 3J = 4.0 Hz, 1H), 7.09 (d, 3J = 4.0 Hz, 1H), 7.07 (d, 3J = 4.0 Hz, 1H), 7.06 (d, 3J = 4.0 Hz, 1H), 6.09 (s, 1H), 4.15 (m, 2H), 4.04 (m, 2H), 3.60 (t, 2H) 1.64 (m, 2H), 1.31 (m, 6H), 0.88 (t, 3H).
13C NMR (CDCl3, TMS/ppm) δ 163.9, 162.8, 149.7, 145.2, 141.2, 138.8, 137.6, 137.2, 137.1, 135.1, 133.7, 127.0, 126.8, 125.3, 124.7, 124.5, 123.6, 116.3, 100.1, 65.3, 38.6, 31.4, 28.8, 26.5, 22.5, 14.0.
Claims (4)
- 式(IIa)
nは2であり、
Ar’はチエニル基であり、
Tは、C1〜C20直鎖状または分岐状アルキル基、及び少なくとも1つのC1〜C10 アルキル基またはハロアルキル基で置換されたチエニル基からなる群において選択され、
R1は、C1〜C40直鎖状または分岐状アルキル基からなる群において選択される]
からなる群において選択される式を有する化合物。 - 以下の化合物6及び8
- 電子デバイスにおける、有機半導体材料としての、請求項1または2に記載の化合物の使用。
- 多数の電極に接している半導体層を備えた電子デバイスであって、半導体層が、請求項1または2に記載の少なくとも1つの化合物を含む、電子デバイス。
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