JP2013530135A - 四配位パラジウム錯体の合成およびその発光素子におけるその適用 - Google Patents
四配位パラジウム錯体の合成およびその発光素子におけるその適用 Download PDFInfo
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- JP2013530135A JP2013530135A JP2013508082A JP2013508082A JP2013530135A JP 2013530135 A JP2013530135 A JP 2013530135A JP 2013508082 A JP2013508082 A JP 2013508082A JP 2013508082 A JP2013508082 A JP 2013508082A JP 2013530135 A JP2013530135 A JP 2013530135A
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- alkyl
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- hydrogen
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title description 47
- 229910052763 palladium Inorganic materials 0.000 title description 14
- 230000015572 biosynthetic process Effects 0.000 title description 5
- 238000003786 synthesis reaction Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 239000000463 material Substances 0.000 claims description 25
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 150000003573 thiols Chemical group 0.000 claims 6
- 238000013086 organic photovoltaic Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 12
- 150000002940 palladium Chemical class 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 35
- 239000003446 ligand Substances 0.000 description 31
- 125000003118 aryl group Chemical group 0.000 description 24
- -1 3- (pyridin-2-yl) phenoxy Chemical group 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 125000004429 atom Chemical group 0.000 description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 description 8
- 238000005859 coupling reaction Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 125000002524 organometallic group Chemical group 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 0 C*(C(c1ccc2-c3ccccc3*(C=C3)=C(**4ccccc4)*3c2c1)=CC1Cc2c3c(Oc4c5cccc4)ccc2)=C1*35*1ccccc1 Chemical compound C*(C(c1ccc2-c3ccccc3*(C=C3)=C(**4ccccc4)*3c2c1)=CC1Cc2c3c(Oc4c5cccc4)ccc2)=C1*35*1ccccc1 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 3
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 3
- FSPDNMWLDGIQLE-UHFFFAOYSA-N 3-pyridin-2-yloxyphenol Chemical compound OC1=CC=CC(OC=2N=CC=CC=2)=C1 FSPDNMWLDGIQLE-UHFFFAOYSA-N 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000000103 photoluminescence spectrum Methods 0.000 description 3
- 238000006862 quantum yield reaction Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 2
- XGSPYABSHRHUIN-UHFFFAOYSA-N 2-[3-(3-bromophenoxy)phenoxy]pyridine Chemical compound BrC1=CC=CC(OC=2C=C(OC=3N=CC=CC=3)C=CC=2)=C1 XGSPYABSHRHUIN-UHFFFAOYSA-N 0.000 description 2
- OSFJZWLZCXXZFK-UHFFFAOYSA-N 2-[3-(3-pyridin-2-yloxyphenoxy)phenyl]pyridine Chemical compound C=1C=CC(C=2N=CC=CC=2)=CC=1OC(C=1)=CC=CC=1OC1=CC=CC=N1 OSFJZWLZCXXZFK-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-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
- 239000006096 absorbing agent Substances 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical group NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 230000031700 light absorption Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 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 2
- WUHLVXDDBHWHLQ-UHFFFAOYSA-N pentazole Chemical compound N=1N=NNN=1 WUHLVXDDBHWHLQ-UHFFFAOYSA-N 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- HOFHXPAKHZZSTF-UHFFFAOYSA-N N1=C(C=CC=C1)C=1C=C(OC=2C=C(OC=3C=NC=CC3)C=CC2)C=CC1 Chemical compound N1=C(C=CC=C1)C=1C=C(OC=2C=C(OC=3C=NC=CC3)C=CC2)C=CC1 HOFHXPAKHZZSTF-UHFFFAOYSA-N 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])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
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- MTFJSAGADRTKCI-VMPITWQZSA-N chembl77510 Chemical compound O\N=C\C1=CC=CC=N1 MTFJSAGADRTKCI-VMPITWQZSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 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
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 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
- 239000000382 optic material Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- IUZNODGZDISGCS-UHFFFAOYSA-N tripropyl(pyridin-2-yl)stannane Chemical compound CCC[Sn](CCC)(CCC)C1=CC=CC=N1 IUZNODGZDISGCS-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
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Abstract
【選択図】図1
Description
光学的および電気光学材料に専念した研究におけるかなりの進歩にもかかわらず、有機または有機金属材料を含む多くの現在の素子はまだ最適化されていない。光学的および電子光学素子において現在使用されている多くの材料は、低い加工能力、非効率的な放射または吸収、および、とりわけ、理想には不十分な安定性を含む、いくつかの欠点を有する。
[式中、(R1)2および(R2)2中のR1およびR2はそれぞれ独立して、水素、場合によって置換されたC1〜C4アルキル、ハロゲン、ヒドロキシル、アミノ、ニトロ、またはチオールを表し;
R3は、メチル、エチル、プロピル、またはブチルを表し、
Y1aは、O、S、R4aが場合によって置換されたC1〜C4アルキルを表すNR4a;
(R4b)2中の各R4bが独立して、場合によって置換されたC1〜C4アルキルを表すSi(R4b)2;または、(R4c)2中の各R4cが水素、もしくは場合によって置換されたC1〜C4アルキルを表すC(R4c)2を表し;
nは整数0または1であり;
Y1bは、存在する場合、O、S、R5aが場合によって置換されたC1〜C4アルキルを表すNR5a;(R5b)2中の各R5bが独立して、場合によって置換されたC1〜C4アルキルを表すSi(R5b)2;または、(R5c)2中の各R5cが、水素、もしくは場合によって置換されたC1〜C4アルキルを表すC(R5c)2を表し;
Y2a、Y2b、Y2c、およびY2dのそれぞれは独立して、N、NR6a、またはCR6bを表し、ここで、R6aおよびR6bのそれぞれは独立して、水素、場合によって置換されたC1〜C4アルキル、ハロゲン、ヒドロキシル、アミノ、ニトロ、またはチオールを表し;
Y3a、Y3b、Y3c、Y3d、Y3e、Y4a、Y4b、Y4c、およびY4dのそれぞれは独立して、N、O、S、R6aおよびR6bのそれぞれが独立して、水素、もしくは場合によって置換されたC1〜C4アルキルを表すNR6a、CR6b;または、ZがCもしくはSiであり、(R6c)2中のR6cがそれぞれ独立して、水素、もしくは場合によって置換されたC1〜C4アルキルを表すZ(R6c)2を表し;
ここで、mは整数1または2であり;
ここで、点線の開いた円
は、それが関係する環の部分的なまたは完全な不飽和を示し;
ただし、mが1であり、Y2aおよびY2dのそれぞれがCHであり、Y2bおよびY2cのそれぞれがNである場合、Y4a、Y4b、Y3a、またはY3dの少なくとも1つは、Nではなく;かつ
ただし、nが0であり、mが2であり、Y2aおよびY2dのそれぞれがCHであり、Y2bおよびY2cのそれぞれがNである場合、Y3bまたはY3cの少なくとも1つはNではない。]
は、それが関係する環の部分的なまたは完全な不飽和を示す。
スキーム2
Claims (8)
- 下式によって表される化合物。
R3は、メチル、エチル、プロピル、またはブチルを表し;
Y1aは、O、S、R4aが場合によって置換されたC1〜C4アルキルを表すNR4a;
(R4b)2中の各R4bが独立して、場合によって置換されたC1〜C4アルキルを表すSi(R4b)2;または、(R4c)2中の各R4cが水素、もしくは場合によって置換されたC1〜C4アルキルを表すC(R4c)2を表し;
nは整数0または1であり;
Y1bは、存在する場合、O、S、R5aが場合によって置換されたC1〜C4アルキルを表すNR5a;(R5b)2中の各R5bが独立して、場合によって置換されたC1〜C4アルキルを表すSi(R5b)2;または、(R5c)2中の各R5cが、水素、もしくは場合によって置換されたC1〜C4アルキルを表すC(R5c)2を表し;
Y2a、Y2b、Y2c、およびY2dのそれぞれは独立して、N、NR6a、またはCR6bを表し、ここで、R6aおよびR6bのそれぞれは独立して、水素、場合によって置換されたC1〜C4アルキル、ハロゲン、ヒドロキシル、アミノ、ニトロ、またはチオールを表し;
Y3a、Y3b、Y3c、Y3d、Y3e、Y4a、Y4b、Y4c、およびY4dのそれぞれは独立して、N、O、S、R6aおよびR6bのそれぞれが独立して、水素、もしくは場合によって置換されたC1〜C4アルキルを表すNR6a、CR6b;または、ZがCもしくはSiであり、(R6c)2中のR6cがそれぞれ独立して、水素、もしくは場合によって置換されたC1〜C4アルキルを表すZ(R6c)2を表し;
ここで、mは整数1または2であり;
ここで、点線の開いた円
は、それが関係する環の部分的なまたは完全な不飽和を示し;
ただし、mが1であり、Y2aおよびY2dのそれぞれがCHであり、Y2bおよびY2cのそれぞれがNである場合、Y4a、Y4b、Y3a、またはY3dの少なくとも1つは、Nではなく;かつ
ただし、nが0であり、mが2であり、Y2aおよびY2dのそれぞれがCHであり、Y2bおよびY2cのそれぞれがNである場合、Y3bまたはY3cの少なくとも1つはNではない。] - 放射材料として、下式:
[式中、(R1)2および(R2)2中のR1およびR2はそれぞれ独立して、水素、場合によって置換されたC1〜C4アルキル、ハロゲン、ヒドロキシル、アミノ、ニトロ、またはチオールを表し;
R3は、メチル、エチル、プロピル、またはブチルを表し;
Y1aは、O、S、R4aが場合によって置換されたC1〜C4アルキルを表すNR4a;
(R4b)2中の各R4bが独立して、場合によって置換されたC1〜C4アルキルを表すSi(R4b)2;または、(R4c)2中の各R4cが水素、もしくは場合によって置換されたC1〜C4アルキルを表すC(R4c)2を表し;
nは整数0または1であり;
Y1bは、存在する場合、O、S、R5aが場合によって置換されたC1〜C4アルキルを表すNR5a;(R5b)2中の各R5bが独立して、場合によって置換されたC1〜C4アルキルを表すSi(R5b)2;または、(R5c)2中の各R5cが、水素、もしくは場合によって置換されたC1〜C4アルキルを表すC(R5c)2を表し;
Y2a、Y2b、Y2c、およびY2dのそれぞれは独立して、N、NR6a、またはCR6bを表し、ここで、R6aおよびR6bのそれぞれは独立して、水素、場合によって置換されたC1〜C4アルキル、ハロゲン、ヒドロキシル、アミノ、ニトロ、またはチオールを表し;
Y3a、Y3b、Y3c、Y3d、Y3e、Y4a、Y4b、Y4c、およびY4dのそれぞれは独立して、N、O、S、R6aおよびR6bのそれぞれが独立して、水素、もしくは場合によって置換されたC1〜C4アルキルを表すNR6a、CR6b;または、ZがCもしくはSiであり、(R6c)2中のR6cがそれぞれ独立して、水素、もしくは場合によって置換されたC1〜C4アルキルを表すZ(R6c)2を表し;
ここで、mは整数1または2であり;
ここで、点線の開いた円
は、それが関係する環の部分的なまたは完全な不飽和を示し;
ただし、mが1であり、Y2aおよびY2dのそれぞれがCHであり、Y2bおよびY2cのそれぞれがNである場合、Y4a、Y4b、Y3a、またはY3dの少なくとも1つは、Nではなく;かつ
ただし、nが0であり、mが2であり、Y2aおよびY2dのそれぞれがCHであり、Y2bおよびY2cのそれぞれがNである場合、Y3bまたはY3cの少なくとも1つはNではない。] - ドナーまたはアクセプター材料として、下式:
[式中、(R1)2および(R2)2中のR1およびR2はそれぞれ独立して、水素、場合によって置換されたC1〜C4アルキル、ハロゲン、ヒドロキシル、アミノ、ニトロ、またはチオールを表し;
R3は、メチル、エチル、プロピル、またはブチルを表し;
Y1aは、O、S、R4aが場合によって置換されたC1〜C4アルキルを表すNR4a;
(R4b)2中の各R4bが独立して、場合によって置換されたC1〜C4アルキルを表すSi(R4b)2;または、(R4c)2中の各R4cが水素、もしくは場合によって置換されたC1〜C4アルキルを表すC(R4c)2を表し;
nは整数0または1であり;
Y1bは、存在する場合、O、S、R5aが場合によって置換されたC1〜C4アルキルを表すNR5a;(R5b)2中の各R5bが独立して、場合によって置換されたC1〜C4アルキルを表すSi(R5b)2;または、(R5c)2中の各R5cが、水素、もしくは場合によって置換されたC1〜C4アルキルを表すC(R5c)2を表し;
Y2a、Y2b、Y2c、およびY2dのそれぞれは独立して、N、NR6a、またはCR6bを表し、ここで、R6aおよびR6bのそれぞれは独立して、水素、場合によって置換されたC1〜C4アルキル、ハロゲン、ヒドロキシル、アミノ、ニトロ、またはチオールを表し;
Y3a、Y3b、Y3c、Y3d、Y3e、Y4a、Y4b、Y4c、およびY4dのそれぞれは独立して、N、O、S、R6aおよびR6bのそれぞれが独立して、水素、もしくは場合によって置換されたC1〜C4アルキルを表すNR6a、CR6b;または、ZがCもしくはSiであり、(R6c)2中のR6cがそれぞれ独立して、水素、もしくは場合によって置換されたC1〜C4アルキルを表すZ(R6c)2を表し;
ここで、mは整数1または2であり;
ここで、点線の開いた円
は、それが関係する環の部分的なまたは完全な不飽和を示し;
ただし、mが1であり、Y2aおよびY2dのそれぞれがCHであり、Y2bおよびY2cのそれぞれがNである場合、Y4a、Y4b、Y3a、またはY3dの少なくとも1つは、Nではなく;かつ
ただし、nが0であり、mが2であり、Y2aおよびY2dのそれぞれがCHであり、Y2bおよびY2cのそれぞれがNである場合、Y3bまたはY3cの少なくとも1つはNではない。]
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- 2011-05-02 KR KR1020127031530A patent/KR20130067276A/ko not_active Application Discontinuation
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US20130203996A1 (en) | 2013-08-08 |
DE112011101526T5 (de) | 2013-05-16 |
US20140114072A1 (en) | 2014-04-24 |
US20190312217A1 (en) | 2019-10-10 |
CN102971396B (zh) | 2016-06-22 |
WO2011137429A3 (en) | 2012-04-05 |
CN102971396A (zh) | 2013-03-13 |
US9382273B2 (en) | 2016-07-05 |
US20170005278A1 (en) | 2017-01-05 |
KR20130067276A (ko) | 2013-06-21 |
US20180130960A1 (en) | 2018-05-10 |
US10263197B2 (en) | 2019-04-16 |
US10727422B2 (en) | 2020-07-28 |
WO2011137429A2 (en) | 2011-11-03 |
US9755163B2 (en) | 2017-09-05 |
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