JP4754826B2 - テルピリジン系の基を有するエレクトロルミネセント金属超分子 - Google Patents
テルピリジン系の基を有するエレクトロルミネセント金属超分子 Download PDFInfo
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- JP4754826B2 JP4754826B2 JP2004549023A JP2004549023A JP4754826B2 JP 4754826 B2 JP4754826 B2 JP 4754826B2 JP 2004549023 A JP2004549023 A JP 2004549023A JP 2004549023 A JP2004549023 A JP 2004549023A JP 4754826 B2 JP4754826 B2 JP 4754826B2
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- polymer
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- terpyridine
- emission
- nmr
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- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical group N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 title description 17
- 229910052751 metal Inorganic materials 0.000 title description 9
- 239000002184 metal Substances 0.000 title description 9
- 229920000642 polymer Polymers 0.000 claims description 52
- -1 hexafluorophosphate ions Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 21
- 239000000178 monomer Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- 238000005424 photoluminescence Methods 0.000 description 12
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000005266 casting Methods 0.000 description 8
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 6
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000000295 emission spectrum Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 229920002521 macromolecule Polymers 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000000103 photoluminescence spectrum Methods 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- DRGAZIDRYFYHIJ-UHFFFAOYSA-N 2,2':6',2''-terpyridine Chemical compound N1=CC=CC=C1C1=CC=CC(C=2N=CC=CC=2)=N1 DRGAZIDRYFYHIJ-UHFFFAOYSA-N 0.000 description 3
- 0 CC1C=C2C=*(C)C3(C4C3C*3)C3C(CC3)C4C3C(C)C12 Chemical compound CC1C=C2C=*(C)C3(C4C3C*3)C3C(CC3)C4C3C(C)C12 0.000 description 3
- 229920000265 Polyparaphenylene Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- 229920000736 dendritic polymer Polymers 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229920002098 polyfluorene Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000005525 hole transport Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001432 poly(L-lactide) Polymers 0.000 description 2
- 229920000962 poly(amidoamine) Polymers 0.000 description 2
- 229920000052 poly(p-xylylene) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229920000123 polythiophene Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 2
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- SHAHPWSYJFYMRX-GDLCADMTSA-N (2S)-2-(4-{[(1R,2S)-2-hydroxycyclopentyl]methyl}phenyl)propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C[C@@H]1[C@@H](O)CCC1 SHAHPWSYJFYMRX-GDLCADMTSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- MVGFLLZPRCSFIY-UHFFFAOYSA-N 4-(2,6-dipyridin-2-ylpyridin-4-yl)phenol Chemical compound Oc1ccc(cc1)-c1cc(nc(c1)-c1ccccn1)-c1ccccn1 MVGFLLZPRCSFIY-UHFFFAOYSA-N 0.000 description 1
- BOPPHKMZOYPASP-UHFFFAOYSA-N 4-(4-bromophenyl)-2,6-dipyridin-2-ylpyridine Chemical compound C1=CC(Br)=CC=C1C1=CC(C=2N=CC=CC=2)=NC(C=2N=CC=CC=2)=C1 BOPPHKMZOYPASP-UHFFFAOYSA-N 0.000 description 1
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
- UVZMNGNFERVGRC-UHFFFAOYSA-N 4-cyclohexylbutanoic acid Chemical compound OC(=O)CCCC1CCCCC1 UVZMNGNFERVGRC-UHFFFAOYSA-N 0.000 description 1
- RTECKDZOLWRAGK-UHFFFAOYSA-N 4-phenyl-2,6-dipyridin-2-ylpyridine Chemical compound C1=CC=CC=C1C1=CC(C=2N=CC=CC=2)=NC(C=2N=CC=CC=2)=C1 RTECKDZOLWRAGK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920000292 Polyquinoline Polymers 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- CSSQMJPRBJZJTN-UHFFFAOYSA-N [Ru+2].N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 Chemical compound [Ru+2].N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 CSSQMJPRBJZJTN-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229920000109 alkoxy-substituted poly(p-phenylene vinylene) Polymers 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000005529 alkyleneoxy group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229920001795 coordination polymer Polymers 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- MYRTYDVEIRVNKP-UHFFFAOYSA-N divinylbenzene Substances C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 125000004407 fluoroaryl group Chemical group 0.000 description 1
- BTZNPZMHENLISZ-UHFFFAOYSA-M fluoromethanesulfonate Chemical compound [O-]S(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-M 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005553 heteroaryloxy group Chemical group 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910001092 metal group alloy Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 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
- 239000002245 particle Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 238000001338 self-assembly Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
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- 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
- H10K85/30—Coordination compounds
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- 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
- C07D213/02—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 having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/22—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 having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic System
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic System without C-Metal linkages
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- 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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
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- 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
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- 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
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Description
本発明は、高度に蛍光性の金属超分子に関し、これは、超分子の部分の変動を介して、強力で異なる色発光を示し、エレクトロルミネセンスに対して、効率的な発光高分子およびデバイスの設計への新たな視野を供する。
有機および高分子発光デバイス(OLEDおよびPLED)を特徴とする製品は、1999年に、および2002年に、初めて市場へと売り出された。単純な構造、層の厚みの薄さ、軽量、広視野角、低い作動電圧、および広範な領域のディスプレイを生産する可能性といった、LCD技術を超える多くの利点に惹かれ、100を超える製造者らが、OLEDおよびPLED開発に関与している。
本発明の主な目的は、金属超分子システムおよびその使用、例えばエレクトロルミネセント(EL)デバイスを調製することである。
である。
(a)透明正孔注入陽極層;
(b)透明正孔輸送層;
(c)超分子を含む活性発光層;および、
(d)電子注入陰極層
を含む高分子発光ダイオード(PLED)を実施することであり、ここに、透明正孔注入陽極層は高仕事関数金属または金属合金の群から選択され;透明正孔輸送層は、ポリ(アニリン)(PANI)またはポリ(3,4-エチレンジオキシチオフェン)/(ポリ(スチレンスルホネート)(PEDOT/PSS)の群から選択され;活性発光層は、本発明において開示される金属超分子の群から選択され;ならびに電子注入陰極層は低仕事関数を有する金属の群から選択される。
本発明は、一般的に、合成、スペクトル特性、光ルミネセンス、超分子のエレクトロルミネセンスおよび高分子発光デバイス(PLED)におけるそれらの適用に関する。本発明において、2組の超分子が設計されている。1つの組において、スペーサーユニットR'は、超分子の主鎖に沿った弾性オキシメチレン結合(-OCH2-)に基づく。第2の組において、スペーサーは、超分子の強固な骨格に沿った、複合フェニレン誘導体に基づく。
モデル化合物5aの合成-酢酸亜鉛二水和物(1mmol)および4'-フェニル-2,2':6',2''−テルピリジン(1mmol)を、3時間、窒素雰囲気下で、10mLのN-メチルピロリジノン(NMP)において、100℃で加熱した。濾過後、過剰なヘキサフルオロリン酸カリウム(KPF6)を濾液に添加した。沈殿物をメタノールで洗浄し、固体をエタノールおよびCH3CNの混合物で再結晶化した。収率: 86 %. FABMS: m/e 685; C42H30N6Zn m/e 684.1を必要とする. 1H NMR (DMSO, δ, ppm): 9.38 (1H, s), 9.12 (4H, d, J = 8.0 Hz), 8.41 (4H, d, J = 7.1 Hz), 8.27 (4H, t, J = 7.5 Hz), 7.94 (4H, d, J = 4.2 Hz), 7.5 (6H, m), 7.48 (4H, t, J = 6.1 Hz). 13C NMR (DMSO, δ, ppm): 155.1, 149.4, 147.7, 141.2, 135.7, 131.1, 129.8, 129.4, 128.1, 127.6, 123.5, 121.1.
モデル化合物5bの合成-収率: 80 %. FABMS: m/e 885; C54H54N6O2Zn m/e 884.4を必要とする. 1H NMR (CDCl3, δ, ppm): 9.33 (4H, s), 9.14 (4H, d, J = 8.0 Hz), 8.44 (4H, d, J = 8.5 Hz), 8.27 (4H, t, J = 7.6 Hz), 7.93 (4H, d, J = 4.7 Hz), 7.48 (4H, dd, J = 12.6 Hz, J = 5.6 Hz), 7.29 (4H, d, J = 8.7 Hz), 4.17 (4H, t, J = 6.6 Hz), 1.81 (8H, m), 1.48 (4H, m), 0.92 (6H, t, J = 6.8 Hz). 13C NMR (CDCl3, δ, ppm): 161.9, 155.1, 149.8, 148.3, 141.7, 130.3, 128.1, 127.7, 123.9, 120.4, 115.8, 68.4, 31.5, 29.1, 25.7, 22.6, 14.4.
単量体6aの合成-100mLのDMSO中のKOH(2.5mmol)の懸濁液に、4'-(4-ヒドロキシフェニル)-2,2':6',2''−テルピリジン(2.05mmol)を、その混合物へと添加した。90℃にて1時間撹拌後、1,8-ジブロモクタン(1.0mmol)およびKI(触媒量)を添加した。得られた混合物を、24時間撹拌した。懸濁液を室温まで冷却し、500mLの水に注いだ。沈殿物を濾過した。得られた固体を、エタノールおよびアセトンの混合物から再結晶化した。収率: 72 %. FABMS: m/e 761; C50H44N6O2 m/e 760.9を必要とする. 1H NMR (CDCl3, δ, ppm): 8.71 (8H, m), 8.66 (6H, d, J = 8.0 Hz), 7.86 (8H, m), 7.34 (4H, dt, J = 4.8 Hz, J = 1.0 Hz), 7.02 (4H, d, J = 8.8 Hz), 4.04 (4H, t, J = 6.5 Hz), 1.83 (4H, m), 1.50 (8H, m). 13C NMR (CDCl3, δ, ppm): 156.4, 155.8, 149.8, 149.1, 136.8, 130.5, 128.5, 123.7, 121.3, 118.2, 118.1, 114.9, 68.1, 29.3, 29.2, 26.3.
単量体6bの合成-収率: 60 %. FABMS: m/e 898; C58H40N8O3 m/e 897.0を必要とする. 1H NMR (CDCl3, δ, ppm): 8.72 (8H, m), 8.66 (4H, d, J = 8.0 Hz), 8.19 (4H, d, J = 8.3 Hz), 7.89 (8H, m), 7.65 (4HHcfsasad, d, J = 8.2 Hz), 7.34 (4H, m), 7.13 (4H, d, J = 1.9 Hz), 5.24 (4H, s). 13C NMR (CDCl3, δ, ppm): 166.1, 161.1, 158.1, 157.6, 151.4, 150.8, 142.5, 138.6, 135.9, 133.2, 130.4, 129.6, 129.0, 125.5, 125.3, 123.1, 120.1, 117.0, 100.6, 71.2.
単量体6cの合成-収率: 58 %. FABMS: m/e 753; C52H36N6O2 m/e 752.9を必要とする. 1H NMR (CDCl3, δ, ppm): 8.70 (8H, m), 8.65 (4H, d, J = 8.0 Hz), 7.87 (8H, m), 7.59 (1H, s), 7.46 (3H, s), 7.33 (4H, m), 7.12 (4H, d, J = 8.0 Hz), 5.18 (4H, s). 13C NMR (CDCl3, δ, ppm): 156.4, 155.8, 149.1, 136.8, 131.1, 129.0, 128.6, 127.1, 126.5, 123.7, 121.3, 118.3, 115.3, 69.9.
単量体6dの合成-収率: 62 %. FABMS: m/e 753; C52H36N6O2 m/e 752.9を必要とする
単量体6eの合成-収率: 52 %. FABMS: m/e 1094; C70H72N6O6 m/e 1093.4を必要とする. 1H NMR (CDCl3, δ, ppm): 8.75 (4H, s), 8.73 (4H, d, J = 4.7 Hz), 8.68 (4H, d, J = 8.0 Hz), 8.00 (4H, d, J = 8.6 Hz), 7.88 (4H, dt, J = 7.6 Hz, J = 1.7 Hz), 7.62 (2H, s), 7.38 (8H, m), 1.53 (14H, m), 1.22 (24H, m). 13C NMR (CDCl3, δ, ppm): 156.1, 152.4, 149.2, 136.9, 128.5, 123.8, 122.2, 121.4, 118.8, 70.1, 31.9, 29.6, 29.3, 26.0.
単量体6fの合成-4'-(4-ブロモフェニル)-2,2':6',2''−テルピリジン(2.05mmol)、2,5-ジドデシルオキシベンゼン-1,4-二ボロン酸(1mmol)、および[Pd(PPh3)4](1mol-%)を、25mLトルエンおよび25mL水性1M Na2CO3の多相系において、24時間還流した。撹拌後、100mLの水を添加し、得られた混合物をCHCl3(3x100mL)で抽出した。有機層をNa2SO4で乾燥させ、真空下で除去した。固体を、エタノールおよびクロロホルム(9:1; v/v)の混合物から再結晶化した。収率: 80 %. FABMS: m/e 1062; C72H80N6O2 m/e 1061.4を必要とする. 1H NMR (CDCl3, δ, ppm): 8.83 (4H, s), 8.73 (4H, m), 8.69 (4H, d, J = 8.0 Hz), 8.01 (4H, d, J = 8.3 Hz), 7.90 (4H, dt, J = 7.7 Hz, J = 1.1 Hz), 7.79 (4H, d, J = 8.6 Hz), 7.36 (4H, m), 7.09 (2H, s), 1.72 (4H, m), 1.17 (40H, m), 0.83 (6H, m). 13C NMR (CDCl3, δ, ppm): 156.4, 156.0, 150.5, 150.0, 149.2, 139.3, 136.8, 130.1, 116.9, 123.8, 121.4, 118.8, 116.3, 69.9, 31.9, 29.7, 29.6, 29.4, 29.3, 26.1, 22.7, 14.1.
単量体6gの合成-収率: 70 %. FABMS: m/e 954; C66H44N6O2 m/e 953.1を必要とする. 1H NMR (CDCl3, δ, ppm): 8.83 (4H, s), 8.77 (4H, dd, J = 1.7 Hz, J = 0.9 Hz), 8.69 (4H, m), 8.00 (4H, d, J = 8.4 Hz), 7.90 (4H, dt, J = 7.7 Hz, J = 1.8 Hz), 7.77 (4H, d, J = 8.4 Hz), 7.35 (4H, m), 5.10 (4H, s). 13C NMR (CDCl3, δ, ppm): 156.4, 156.0, 150.3, 149.2, 136.8, 130.1, 128.5, 127.8, 127.2, 127.0, 123.8, 121.4, 118.8, 117.3, 71.8.
単量体6hの合成-収率: 73 %. FABMS: m/e 1006; C71H68N6 m/e 1005.4を必要とする. 1H NMR (DMSO, δ, ppm): 8.83 (4H, s), 8.76 (4H, m), 8.68 (4H, m), 8.05 (4H, m), 7.90 (4H, dt, J = 7.8 Hz, J = 1.8 Hz), 7.83 (6H, d, J = 8.2 Hz), 7.70 (4H, m), 7.38 (4H, m), 2.11 (4H, m), 1.11 (18H, m), 0.80 (8H, m). 13C NMR (DMSO, δ, ppm): 156.4, 156.1, 151.9, 149.8, 149.2, 142.4, 140.4, 139.4, 137.2, 136.9, 127.7, 127.7, 126.1, 123.8, 121.5, 121.4, 120.2, 118.7, 55.4, 40.4, 31.8, 30.0, 29.2, 23.9, 22.6, 14.0.
単量体6iの合成-ジビニルベンゼン(1mmol)、4'-(4-ブロモフェニル)-2,2':6',2''−テルピリジン(2mmol)、酢酸パラジウム(II)(5mol-%)、およびトリ-o-トリフォスフィン(0.4当量)を、窒素雰囲気下で、50mLフラスコに添加した。無水DMFをシリンジを介して添加し、溶液を全ての固体が溶解するまで撹拌した。トリ-n-ブチルアミン(1mL)を添加し、溶液を、5日間、100℃にて撹拌した。溶液をメタノールに注いだ。固体をエタノールおよびクロロホルム(8:2; v/v)の混合物から再結晶化した。 収率: 77 %. FABMS: m/e 745; C52H36N6 m/e 744.9を必要とする.
高分子7hの合成-50mLのN-メチルピロリジノン(NMP)溶液中の単量体6h(0.1mmol)に、5mL NMP中の酢酸亜鉛二水和物(0.1mmol)を105℃にて滴下した。N2下で24時間撹拌後、過剰なヘキサフルオロリン酸カリウム(KPF6)を熱い溶液に添加した。得られた溶液をメタノールに注ぐと、固体が沈殿した。精製を、DMACおよびメタノールを用いる反復沈殿によって実施した。得られた高分子を、24時間、80℃にて真空下で乾燥させ、黄色固体として収集した。収率: 80%.
b 精製後の収率
c 20℃/分での加熱速度を有するTGAによって決定された分解温度
表1.高分子7aないし7iおよびモデル化合物5aおよび5bの物理的性質
b DMAC (N, N-ジメチルアセトアミド)における1x10-5 g dm-3での濃度
c フィルムの厚みは〜38-70nmであった。
d フィルムの厚みは〜0.5-2μmであった。
e ピークはショルダーとして現れる。
f 吸光係数(εmax)は103xmol-1dm3cm-1の単位で表される。
表2. DMACにおけるおよび薄いフィルムとしての高分子7aないし7i、およびDMACにおけるモデル化合物5aおよび5bの光物理的性質
図7は、高分子7aの代表的なUV-vis吸収スペクトルを示す。DMAC溶液において、λmax 287nm(amax=73900g-1dm3cm-1)での強い吸収バンドおよび約λmax 328ないし342nm(amax=36500ないし28800g-1dm3cm-1)でのショルダーが観察される。光学バンドギャップ(吸収エッジ)は、3.19eVである。溶液におけるおよび薄いフィルムとしての高分子7aのPLスペクトルもまた示される。青色PL発光は、DMACにおいておよびキャスティングフィルムとしての両方で、λmax 450および448nmで観察される。
溶液におけるおよび薄いフィルムとしての高分子7cのPL発光スペクトルを図8に示す。DMACにおいて、λmax 457nmで特徴のない発光バンドを有する強い青色発光が観察される。スピンコートされたおよびキャスティングフィルムとしての高分子の最大発光は、それぞれ溶液中のものと比較して、376cm-1シフトする。
スピンコートされたフィルムとしての高分子7a、7f、7g、および7iのPLスペクトルを図9に表す。主鎖における異なる結合を組合せることによって、あるいは側基置換を介して、超分子のPL発光色を調整することができる。これらの高分子の発光色は、青色(高分子7a)、緑色(高分子7f)、緑色(高分子7g)、および黄色(高分子7i)であり、これらは、それぞれ、λmax 450、546、530、および567nmのPL発光ピークを有する。
スピンコートされたおよびキャスティングフィルムとしてのDMACにおける高分子7hの正規化されたPLスペクトルを、図10に示す。白色発光が、434nmの最大発光および518nm辺りのショルダーで、DMACにおいて、高分子7hから観察されている。対照的に、4350cm-1の大きなストークシフトを有するスピンコートされたおよびキャスティングフィルムとしての7hの構造のない黄色発光スペクトルが、それぞれ示される。
b HOMOレベルを、LUMOエネルギーレベルおよびバンドギャップの間のエネルギー差から予測した。
c バンドギャップを、最低エネルギーピークのテイルを推定することによって、DMACにおける吸収スペクトルから予測した。
表3.超分子およびモデル化合物のHOMO-LUMOエネルギーレベルおよびバンドギャップ
これらの超分子の相対的なHOMOおよびLUMOレベルを、還元電位および光学バンドギャップによって予測することができる。電気的性質を表3に要約する。図11は、超分子のHOMO-LUMOレベルおよびバンドギャップを、図式的に説明する。骨格に沿ってオキシメチレン結合を有する超分子のHOMO-LUMOレベルの間のエネルギーギャップは非常に似ており、これは7aに対して3.19eVないし7dに対して3.26eVである。これらの高分子は、DMAC溶液において、および薄いフィルムとして、それぞれ、強い青色発光を示す。高分子7f、7gおよび7hは、-3.61ないし-3.67eVのLUMOエネルギーレベルおよび-6.56ないし-6.59eVのHOMOエネルギーレベルを有する同様の電気エネルギーレベルを呈し、薄いフィルムとして、強い緑色PL発光を示す。高分子7hは、2.64eVの最も狭いバンドギャップを有する。薄いフィルムとしての高分子の明るい黄色発光を得る。
洗剤溶液、脱イオン水、エタノール、およびアセトン中で順次に洗浄した20Ω/∀のシート耐性を有する酸化スズインジウム(ITO)ガラス上で、デバイスAを調製した。湿潤洗浄プロセスは次のように示される:
柔らかいティッシュおよびアセトンでITOガラスを洗浄して、粘着するガラス粒子を除去する
10分間、50℃にて、ガラス洗剤によって脱イオン水中で超音波洗浄する
脱イオン水で、完全に濯ぐ
5分間、50℃にて、エタノール中で超音波洗浄する
脱イオン水で、完全に濯ぐ
5分間、40℃にて、アセトン中で超音波洗浄する
湿潤洗浄プロセスの後、ITOガラスを、130℃にて、24時間、乾燥させ、10分間、UVオゾンクリーナー中で処理して、微量の有機物質を除去する。ポリ(3,4-エチレンジオキシチオフェン)/(ポリ(スチレンスルホネート)(PEDOT/PSS)および高分子7aを、標準的な回転塗布様式によって、ITO上に堆積させた。PEDOT/PSSの層の厚みは30ないし100nmであった。高分子7aの層の厚みは、30ないし70nmであった。カルシウム(30nm)およびアルミニウム(120nm)電極の堆積を、高真空状態(6x10-6Torr)において実施した。典型的な成長速度は、2Å/sであった。デバイスのEL性能を、カプセル充填なしで、空気雰囲気下で検査した。
10Vのバイアス電圧の高分子7aのELスペクトルは、図13において、450nmにて発光ピークを示した。それはスピンコートされたおよびキャスティングフィルムとしてのその対応するPL発光と似ていることが分かった。また、デバイスAの電流密度−電圧−輝度特徴曲線を図14に示す。青色光EL強度は、バイアス電圧を増加させるに従い増加した。ターンオン電圧は、約6Vであった。デバイスの最大効率は、0.8cd/Aであった。1698cd/m2 の最大輝度は、13Vの駆動電圧にて得た。デバイスAのEL色は青色である(CIE座標: x=0.15, y=0.21)。
この実施例は、ITO/PEDOT/PSS/高分子7h/Ca(30Å)/Al(120Å)の配置を有する黄色光PLEDの調製を説明する。デバイスBを、デバイスAと同様に作った。
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US10/290,120 US7811675B2 (en) | 2002-11-06 | 2002-11-06 | Electroluminescent metallo-supramolecules with terpyridine-based groups |
US10/290,120 | 2002-11-06 | ||
PCT/CN2003/000891 WO2004041913A1 (en) | 2002-11-06 | 2003-10-23 | Electroluminescent metallo-supramolecules with terpyridine-based groups |
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US8147986B2 (en) * | 2005-09-30 | 2012-04-03 | Fujifilm Corporation | Organic electroluminescent device |
JP4959270B2 (ja) * | 2005-09-30 | 2012-06-20 | 富士フイルム株式会社 | 有機電界発光素子 |
JP5062711B2 (ja) * | 2005-10-24 | 2012-10-31 | 独立行政法人物質・材料研究機構 | ターピリジン型モノマー、ビスターピリジン型モノマー、および、その製造方法 |
JP5062712B2 (ja) * | 2005-10-24 | 2012-10-31 | 独立行政法人物質・材料研究機構 | 高分子材料、その製造方法およびエレクトロクロミック素子 |
WO2008024950A1 (en) * | 2006-08-25 | 2008-02-28 | The University Of Akron | Methods for producing materials with photo- and electroluminescence properties and systems using such materials |
JP5013366B2 (ja) * | 2006-12-28 | 2012-08-29 | 独立行政法人物質・材料研究機構 | ビス(ターピリジン)化合物の合成方法 |
JP5013365B2 (ja) * | 2006-12-28 | 2012-08-29 | 独立行政法人物質・材料研究機構 | スペーサー導入型ビス(ターピリジン)化合物の合成方法 |
JP5092140B2 (ja) * | 2006-12-28 | 2012-12-05 | 独立行政法人物質・材料研究機構 | 非対称型ビス(ターピリジン)化合物の合成方法 |
TWI477564B (zh) * | 2008-07-28 | 2015-03-21 | Sharp Kk | A polymer pigment material, a color conversion film thereof, and a multi-color light emitting organic EL device |
US20120070378A1 (en) * | 2008-12-16 | 2012-03-22 | The University Of Akron | Lanthanide ion complexes and imaging method |
WO2011065530A1 (ja) * | 2009-11-30 | 2011-06-03 | 昭和電工株式会社 | 有機発光素子 |
JP5747247B2 (ja) * | 2011-03-10 | 2015-07-08 | 国立研究開発法人物質・材料研究機構 | 有機/蛍光性金属ハイブリッドポリマー及びその配位子 |
CN102277155B (zh) * | 2011-06-28 | 2014-10-15 | 中国科学院福建物质结构研究所 | 一种有机白光发射材料l-cooh的制备和用途 |
CN102584686B (zh) * | 2012-01-11 | 2014-02-12 | 淮海工学院 | 一种水溶性三联吡啶荧光化合物及其制备方法 |
JP5376547B2 (ja) * | 2012-04-25 | 2013-12-25 | 独立行政法人物質・材料研究機構 | ターピリジン型モノマー、および、その製造方法 |
CN103336042B (zh) * | 2013-06-26 | 2015-05-13 | 新余学院 | 一种电化学检测铜离子的三联吡啶衍生物修饰电极及其制备方法 |
CN103374132B (zh) * | 2013-07-12 | 2015-04-08 | 中科院广州化学有限公司 | 一种金属离子直接诱导的荧光超分子凝胶的制备及应用 |
US10334685B2 (en) * | 2014-11-14 | 2019-06-25 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Carbon dot light emitting diodes |
US10961259B2 (en) * | 2014-12-02 | 2021-03-30 | Massachusetts Institute Of Technology | Multistimuli-responsive white luminescent materials including metal elements |
WO2016109542A1 (en) * | 2014-12-30 | 2016-07-07 | Momentive Performance Materials Inc. | Luminescent silicone coatings |
US10208069B2 (en) * | 2015-02-02 | 2019-02-19 | The University Of Akron | Precise three-dimensional supramacromolecule interconversions |
CN105111458B (zh) * | 2015-09-14 | 2018-07-10 | 安徽大学 | 一种卤化锌三联吡啶配位聚合物多功能材料及其制备方法 |
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CN112279871A (zh) * | 2020-09-24 | 2021-01-29 | 桂林理工大学 | 一系列基于三联吡啶类配体的六氟乙酰丙酮铕配合物的制备、结构及荧光 |
CN112250881B (zh) * | 2020-10-23 | 2022-06-14 | 南京林业大学 | 一类烷基链桥连的三联吡啶铁配位聚合物电致变色材料 |
CN113801147B (zh) * | 2021-10-26 | 2022-06-14 | 南京邮电大学 | 一类基于腙的Zn(II)配合物光致变色材料及其制备与应用 |
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US7811675B2 (en) | 2010-10-12 |
CN100516119C (zh) | 2009-07-22 |
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