WO2011088916A1 - Phosphoreszente metallkomplexverbindung, verfahren zur herstellung und lichtemittierendes bauelement - Google Patents
Phosphoreszente metallkomplexverbindung, verfahren zur herstellung und lichtemittierendes bauelement Download PDFInfo
- Publication number
- WO2011088916A1 WO2011088916A1 PCT/EP2010/067653 EP2010067653W WO2011088916A1 WO 2011088916 A1 WO2011088916 A1 WO 2011088916A1 EP 2010067653 W EP2010067653 W EP 2010067653W WO 2011088916 A1 WO2011088916 A1 WO 2011088916A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound according
- alkyl
- ligand
- central atom
- triazole
- Prior art date
Links
- -1 metal complex compound Chemical class 0.000 title claims description 54
- 238000000034 method Methods 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 239000003446 ligand Substances 0.000 claims description 30
- 150000003852 triazoles Chemical group 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 18
- 150000003254 radicals Chemical class 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052741 iridium Inorganic materials 0.000 claims description 15
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 13
- 239000011159 matrix material Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000006850 spacer group Chemical group 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 229910052693 Europium Inorganic materials 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000000177 1,2,3-triazoles Chemical class 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 150000002739 metals Chemical class 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 150000000178 1,2,4-triazoles Chemical class 0.000 claims description 2
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 2
- 229910052779 Neodymium Inorganic materials 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 229910052753 mercury Inorganic materials 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- 229920000131 polyvinylidene Polymers 0.000 claims description 2
- 125000002577 pseudohalo group Chemical group 0.000 claims description 2
- 229910052702 rhenium Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- ZPFAVCIQZKRBGF-UHFFFAOYSA-N 1,3,2-dioxathiolane 2,2-dioxide Chemical group O=S1(=O)OCCO1 ZPFAVCIQZKRBGF-UHFFFAOYSA-N 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 238000004440 column chromatography Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 14
- 230000007935 neutral effect Effects 0.000 abstract description 5
- 238000005516 engineering process Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 25
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 125000001424 substituent group Chemical group 0.000 description 13
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 230000005684 electric field Effects 0.000 description 4
- 238000000295 emission spectrum Methods 0.000 description 4
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 4
- 239000002608 ionic liquid Substances 0.000 description 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 3
- LOIBXBUXWRVJCF-UHFFFAOYSA-N 4-(4-aminophenyl)-3-phenylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=CC=C1 LOIBXBUXWRVJCF-UHFFFAOYSA-N 0.000 description 3
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001556 benzimidazoles Chemical class 0.000 description 3
- 238000005538 encapsulation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- BOPVDKBKABSTCC-UHFFFAOYSA-N CC1(C)c2ccccc2-c2cccc(c12)-c1ccccc1 Chemical compound CC1(C)c2ccccc2-c2cccc(c12)-c1ccccc1 BOPVDKBKABSTCC-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 150000007960 acetonitrile Chemical class 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- MRKVYAQCIIPPFP-UHFFFAOYSA-N c1ccc(cc1)-c1cccc2-c3ccccc3C(c12)(c1ccccc1)c1ccccc1 Chemical compound c1ccc(cc1)-c1cccc2-c3ccccc3C(c12)(c1ccccc1)c1ccccc1 MRKVYAQCIIPPFP-UHFFFAOYSA-N 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 238000010657 cyclometalation reaction Methods 0.000 description 2
- 150000002170 ethers Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 239000012212 insulator Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002503 iridium Chemical class 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 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
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920000301 poly(3-hexylthiophene-2,5-diyl) polymer Polymers 0.000 description 2
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 2
- AZEPJCYDCKVUJI-UHFFFAOYSA-N 1'-phenyl-9,9'-spirobi[fluorene] Chemical compound c1ccc(cc1)-c1cccc2-c3ccccc3C3(c4ccccc4-c4ccccc34)c12 AZEPJCYDCKVUJI-UHFFFAOYSA-N 0.000 description 1
- DOYSIZKQWJYULQ-UHFFFAOYSA-N 1,1,2,2,2-pentafluoro-n-(1,1,2,2,2-pentafluoroethylsulfonyl)ethanesulfonamide Chemical compound FC(F)(F)C(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)C(F)(F)F DOYSIZKQWJYULQ-UHFFFAOYSA-N 0.000 description 1
- VECGWISURDHBJL-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate;tetrabutylazanium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F VECGWISURDHBJL-UHFFFAOYSA-M 0.000 description 1
- MUOQTHSUZGSHGW-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate;tetrabutylazanium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC.[O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F MUOQTHSUZGSHGW-UHFFFAOYSA-M 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical class N1=C(N=CN=C1)* 0.000 description 1
- PUHVBRXUKOGSBC-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;methanesulfonate Chemical compound CS([O-])(=O)=O.CCCC[N+]=1C=CN(C)C=1 PUHVBRXUKOGSBC-UHFFFAOYSA-M 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical class C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 1
- KSSABTOENVKMLW-UHFFFAOYSA-N 2-N,2-N,2-N',2-N'-tetrakis(4-phenylphenyl)-9,9'-spirobi[fluorene]-2,2'-diamine Chemical compound C1=CC=CC=C1C1=CC=C(N(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=C3C4(C5=CC(=CC=C5C5=CC=CC=C54)N(C=4C=CC(=CC=4)C=4C=CC=CC=4)C=4C=CC(=CC=4)C=4C=CC=CC=4)C4=CC=CC=C4C3=CC=2)C=C1 KSSABTOENVKMLW-UHFFFAOYSA-N 0.000 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- BXSXNLBKCNVUGA-UHFFFAOYSA-N 2-n,2-n,2-n',2-n'-tetrakis(4-methoxyphenyl)-9,9'-spirobi[fluorene]-2,2'-diamine Chemical compound C1=CC(OC)=CC=C1N(C=1C=C2C3(C4=CC(=CC=C4C4=CC=CC=C43)N(C=3C=CC(OC)=CC=3)C=3C=CC(OC)=CC=3)C3=CC=CC=C3C2=CC=1)C1=CC=C(OC)C=C1 BXSXNLBKCNVUGA-UHFFFAOYSA-N 0.000 description 1
- MTUBTKOZCCGPSU-UHFFFAOYSA-N 2-n-naphthalen-1-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1 MTUBTKOZCCGPSU-UHFFFAOYSA-N 0.000 description 1
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 1
- QKYZQKJXAKNEPA-UHFFFAOYSA-N 3-hydroxy-5-methyl-1-phenylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1N(O)C(=O)C=2C(C)=CSC=2N1C1=CC=CC=C1 QKYZQKJXAKNEPA-UHFFFAOYSA-N 0.000 description 1
- TYOVSFHFYHSADG-UHFFFAOYSA-N 4,8-dichloro-2-methylquinoline Chemical compound C1=CC=C(Cl)C2=NC(C)=CC(Cl)=C21 TYOVSFHFYHSADG-UHFFFAOYSA-N 0.000 description 1
- PWFFDTZNRAEFIY-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1C1=CC(N)=CC=C1C1=CC=C(N)C=C1 PWFFDTZNRAEFIY-UHFFFAOYSA-N 0.000 description 1
- QQVZARAXLWAUOB-UHFFFAOYSA-N 4-(4-aminophenyl)-5,5-dimethyl-6-phenylcyclohexa-1,3-dien-1-amine Chemical compound CC1(C)C(C=2C=CC=CC=2)C(N)=CC=C1C1=CC=C(N)C=C1 QQVZARAXLWAUOB-UHFFFAOYSA-N 0.000 description 1
- RYUDABJFYDZBRR-UHFFFAOYSA-N 4-(4-anilinophenyl)-3-(4-butylphenyl)-n-phenylaniline Chemical compound C1=CC(CCCC)=CC=C1C1=CC(NC=2C=CC=CC=2)=CC=C1C(C=C1)=CC=C1NC1=CC=CC=C1 RYUDABJFYDZBRR-UHFFFAOYSA-N 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
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
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- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Chemical group 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 101000606537 Homo sapiens Receptor-type tyrosine-protein phosphatase delta Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920000144 PEDOT:PSS Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 102100039666 Receptor-type tyrosine-protein phosphatase delta Human genes 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- LWCLHBMVBRXXPV-UHFFFAOYSA-M [O-]C(=O)C1=CC=CC=N1.FC1=CC(F)=CC=C1C1=CC=CN=C1[Ir+]C1=NC=CC=C1C1=CC=C(F)C=C1F Chemical class [O-]C(=O)C1=CC=CC=N1.FC1=CC(F)=CC=C1C1=CC=CN=C1[Ir+]C1=NC=CC=C1C1=CC=C(F)C=C1F LWCLHBMVBRXXPV-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- INDFXCHYORWHLQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butyl-3-methylimidazol-3-ium Chemical compound CCCCN1C=C[N+](C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F INDFXCHYORWHLQ-UHFFFAOYSA-N 0.000 description 1
- NOFBAVDIGCEKOQ-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;1-butyl-3-methylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC(C)=C1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F NOFBAVDIGCEKOQ-UHFFFAOYSA-N 0.000 description 1
- CFAPFDTWIGBCQK-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide;tetrabutylazanium Chemical compound FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.CCCC[N+](CCCC)(CCCC)CCCC CFAPFDTWIGBCQK-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- QQHZPQUHCAKSOL-UHFFFAOYSA-N butyl nitrate Chemical compound CCCCO[N+]([O-])=O QQHZPQUHCAKSOL-UHFFFAOYSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 125000003790 chinazolinyl group Chemical group 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000007647 flexography Methods 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
- 125000000524 functional group Chemical group 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 238000007646 gravure printing Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- RHYDJSYLYBUSEY-UHFFFAOYSA-N imidazol-1-yloxyboronic acid Chemical compound OB(O)On1ccnc1 RHYDJSYLYBUSEY-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 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
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 239000010416 ion conductor Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000003854 isothiazoles Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- XHYYGJAYKIYARQ-UHFFFAOYSA-M methanesulfonate;tetrabutylazanium Chemical compound CS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC XHYYGJAYKIYARQ-UHFFFAOYSA-M 0.000 description 1
- DSQCNXSPLHDLED-UHFFFAOYSA-M methanesulfonate;tetrabutylphosphanium Chemical compound CS([O-])(=O)=O.CCCC[P+](CCCC)(CCCC)CCCC DSQCNXSPLHDLED-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 1
- 150000002979 perylenes Chemical class 0.000 description 1
- 150000005053 phenanthridines Chemical class 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- LYKXFSYCKWNWEZ-UHFFFAOYSA-N pyrazino[2,3-f][1,10]phenanthroline-2,3-dicarbonitrile Chemical compound N1=CC=CC2=C(N=C(C(C#N)=N3)C#N)C3=C(C=CC=N3)C3=C21 LYKXFSYCKWNWEZ-UHFFFAOYSA-N 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical class OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000007764 slot die coating Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Chemical group 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical class [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- WGYONVRJGWHMKV-UHFFFAOYSA-M tetrabutylazanium;benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.CCCC[N+](CCCC)(CCCC)CCCC WGYONVRJGWHMKV-UHFFFAOYSA-M 0.000 description 1
- YNJQKNVVBBIPBA-UHFFFAOYSA-M tetrabutylazanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CCCC[N+](CCCC)(CCCC)CCCC YNJQKNVVBBIPBA-UHFFFAOYSA-M 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- AEXDMFVPDVVSQJ-UHFFFAOYSA-N trifluoro(trifluoromethylsulfonyl)methane Chemical compound FC(F)(F)S(=O)(=O)C(F)(F)F AEXDMFVPDVVSQJ-UHFFFAOYSA-N 0.000 description 1
- UFMOMJZZKFLOSJ-UHFFFAOYSA-M trifluoromethanesulfonate;1,2,3-trimethylimidazol-1-ium Chemical compound CC=1N(C)C=C[N+]=1C.[O-]S(=O)(=O)C(F)(F)F UFMOMJZZKFLOSJ-UHFFFAOYSA-M 0.000 description 1
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 1
- KNXVOGGZOFOROK-UHFFFAOYSA-N trimagnesium;dioxido(oxo)silane;hydroxy-oxido-oxosilane Chemical compound [Mg+2].[Mg+2].[Mg+2].O[Si]([O-])=O.O[Si]([O-])=O.[O-][Si]([O-])=O.[O-][Si]([O-])=O KNXVOGGZOFOROK-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- 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
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen 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
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/135—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising mobile ions
Definitions
- Phosphorescent metal complex compound Phosphorescent metal complex compound, method of preparation and light emitting device
- the invention relates to a phosphorescent Metallkomplexver ⁇ bond, processes for preparing it and a radiation-emitting component, in particular an organic light-emitting electrochemical cell (organic light emitting electrochemical cell OLEEC).
- a radiation-emitting component in particular an organic light-emitting electrochemical cell (organic light emitting electrochemical cell OLEEC).
- the OLEECs are characterized by a much simpler structure, since usually only one organic active Layer is required, which is preferably also still mass production suitable for wet-chemical methods can be applied.
- OLEDs organic light emitting diodes
- a so-called multi-layer structure is, in particular in the using so-called small molecules up ⁇ built OLEDs realized because, in addition to the light emitting layer also efficiency-enhancing layers, such as hole and / or electron injection layers Blocker layers between the electrodes for better transfer of the charge carriers are arranged.
- efficiency-enhancing layers such as hole and / or electron injection layers
- Blocker layers between the electrodes for better transfer of the charge carriers are arranged.
- highly reactive materials are thereby turned ⁇ is because the materials are characterized by low beit Austrittsar-. Therefore, hermetic encapsulation is essential in OLEDs.
- organic electroluminescent elements have at least one organic layer located between two electrodes. As voltage is applied to the electrodes, electrons from the cathode are injected into the lowest unoccupied molecular orbitals of the organic light emitting layer and migrate toward the anode.
- holes from the anode are injected into the uppermost occupied molecular orbitals of the organic layer and migrate accordingly to the cathode.
- the FAEL ⁇ len where itinerant hole and migrating electron within the organic light emitting layer to make a light-emitting material, an exciton is formed, which decomposes with emission of light. Allow the light to at all emerge from the electroluminescent element, at least one electrode must be transparent, in most FAEL ⁇ len which is an electrode made of indium tin oxide, which is used as Ano ⁇ de.
- the ITO layer is usually deposited on a glass slide.
- Solution of the problem and object of the invention is therefore ei ⁇ ne charged zyklometallographe metal complex compound, which emits under tension in the visible range, characterized in that the metal complex compound of an aromatic structural element of a directly bound which ligands at least one of a positive charge carrying to the central atom, Imidazolinium unit bound via a spacer.
- Structural Formula I shows a generalized scheme of the known metal complex emitter materials. Representative of all emitting systems (see above) are iridium complexes with the coordination number 6 mapped. Be under ⁇ emmesichtung the coordination number 4, for example platinum, europium mostly 8, Os 6, the considerations for other Sys ⁇ tems apply. The carbon- ⁇ bond is shown here as a solid line, the coordinate bond of the bidentate ligand ge ⁇ dashed. The structural formula I shows these ratios Ver ⁇ highly schematic.
- A is in principle one of the known aromatics bound to the central atom containing ligands, in particular a substituted or unsubstituted aromatic or heteroaromatic, which is capable of said binding ratios. All aromatics can be independently varied as shown by the structures cited or depicted herein.
- the solid bond to Koh ⁇ lenstoff or nitrogen is formed by a CH or NH precursor by elimination of hydrogen (cyclometallation).
- the dashed line indicates either a carbene carbon or a nitrogen or phosphorus coordinating through a lone pair of electrons.
- e instead of an alkyl chain, it is also possible to use a polyethylene glycol, polyethylene diamine, polyester, polyurethane, polyvinylidene phenylene chain,
- transition metal ⁇ le such as, but not limited to, called Eu, Nd, Gd, Re, Os, Pt, Au, Hg and Ru, Rh, Pd, Ag be used in addition to Ir as the central atom.
- the other ligands L can be formed independently of one another analogously to the imidazolinium-substituted ligands "Ax-spacer-imidazole” according to the invention or are selected from the classical cyclometallizing ligands, as described, for example, in WO2005097942A1, WO2006013738A1, US Pat.
- the central atom for example, 2-phenylpyridine, or 2-phenylimidazole and related struc ⁇ acids, such as, for example, benzimidazoles or phenanthridines.
- the OLEECs basically work with only one active organic layer, which is additionally produced by mass production methods such as simple coating methods, for example spin coating, knife coating, dipping, slot die coating or printing methods such as screen printing, flexography, gravure printing, Inkjet printing can be applied.
- mass production methods such as simple coating methods, for example spin coating, knife coating, dipping, slot die coating or printing methods such as screen printing, flexography, gravure printing, Inkjet printing can be applied.
- the typical layer thickness is 10 to 200 nm, but can also assume other values, for example up to 1000 nm. Since in OLEECs the electric field drops primarily over the electrodes and not over the light-emitting layer, layer thicknesses above 100 nm can still provide good components.
- the reactive electrodes such as barium, calcium, lithium fluoride, cesium fluoride, magnesium, etc., must not be used for OLEECs, but air-stable metals such as gold, palladium, platinum, aluminum, magnesium, silver,
- the active layer is a mixture of a conductor for ions and electrons and an emitting species.
- Ionic transition metal complexes iTMC
- a typical representative is the ruthenium tris-bipyridine hexafluorophosphate [Ru (bpy) 3 described by Q. Pei, G. Yu, C. Zhang, Y. Yang, AJ Heeger in Science, Vol. 269, 1086-1088, 1995 ] 2+ (PF 6 ⁇ ) 2 ⁇
- the classical iridium ethers show at least one phenylpyridine ligand:
- cyclometallized iridium based emitters are:
- the phenylpyridine ligand is bound to the central atom in the sense of a cyclometalation, whereby a direct metal-carbon bond is formed.
- Fluorination of the phenylpyridine ligand shifts the emission in the spectrum towards blue.
- fluorinated species are the bis (2, 4-difluorophenyl-2-pyridyl) iridium (III) picolinates (FIrPic) or bis (2,4-difluorophenylpyridinato) tetrakis (1-pyrazolyl) borates iridium III (FIr6).
- the known ligands L may have another carbene functionality that serves as a source of deep blue emission.
- these ligands L are in the publications WO200519373, EP1692244B1 or WO
- ligands L are known in the publica ⁇ fentlichungen EP1904508A2, W02007004113A2, W02007004113R4A3, said ligands L are also shown in the context of charged metal complexes, which have at least one phenylpyridine ligand with appropriate donor groups such as dimethylamino. These compounds show an increased LUMO level of the complex, with acceptor groups such as 2,4-difluoro being introduced into the phenyl ring to the level of the HOMO orbital. It is shown that by varying the ligands and their substituents, the emission color can vary throughout the visible spectrum.
- Iridiumcarbenkomplexe be ⁇ known. Moreover emitting systems are of course not limited to Iridium, rather, neutral Emit ⁇ ter with lanthanides, especially europium and other heavy metals such as osmium, are formed.
- R independently H vonvent-, branched alkyl, unbranched alkyl radicals, fused alkyl ring-shaped radicals, completely or partially substituted straight ⁇ chain, branched, fused and / or cyclic alkyl ⁇ radicals, alkoxy groups, amines, amides, esters, carbonates, aroma ⁇ th, completely or partially substituted aromatics, hetero- roaromaten, condensed aromatics, completely or partially substituted fused aromatic, heterocyclic, completeness dig or partially substituted heterocycles, fused heterocycles, halogens, pseudohalogens.
- All substituents Ri, R2, R + can be independently selected from each other from the abovementioned radicals, are preferably Ci to C2 0, condensed example decahydronaph- tyl-, adamantyl, cyclic, cyclohexyl, or fully or partially substituted alkyl radical , preferably C ⁇ 1 > to C ⁇ b> 2.
- the chains or groups may carry different end groups, for example charged end groups such as SO x ⁇ 'NR + and so forth .
- alkyl radicals may in turn carry groups such as ethers, ethoxy, methoxy, etc. ester, amide, carbonate, etc. or halogens, preferably fluorine.
- R should not be on alkyl ⁇ be limited, but may also include well-substituted or un- substituted aromatic systems, such crizspielswei ⁇ se phenyl, biphenyl, naphthyl, phenanthryl, benzyl, and so on.
- Table 1 A list of the most important representatives can be seen in the following Table 1.
- Table 1 shows a selection of substituted or unsubstitu ⁇ FOURTH heterocycles which are suitable as radicals R. For simplicity, only the basic unit is shown. The binding to the ligands can be done at any bondable site of the body.
- R + introduces the positive charge on the nitrogen atom and is preferably a substituted or unsubstituted aliphatic radical such as a methyl, ethyl or a general straight-chain or branched, condensed
- the data needed for Kompensati ⁇ on the positive charge of anions are selected from fluoride, chloride, bromide, iodide, sulfate, phosphate, carbonate, trifluoromethanesulfonate, trifluoroacetate, tosylate,
- Bis (trifluoromethylsulfone) imide tetraphenylborate, B 9 C2H 11 2 ; Hexafluorophosphate, tetrafluoroborate, hexafluoroantimonate, tetrapyrazolato borate.
- Figure 1 shows the structure of an OLEEC schematically.
- An OLEEC 7 is in principle simpler than the OLED constructed and in most cases by a simple introduction of an organic layer 3 between two electrodes 2 and 4 and subsequent encapsulation 5 feasible. When voltage is applied, light 6 emerges.
- the preferred active emitting layer 3 of an OLEEC consists of a matrix in which an emitting species is embedded.
- the matrix may consist of an insulator or of a material that is either an ion conductor with electrolyte properties or an inert matrix (insulator).
- the emitting species is one or more ionic trans- stion metal complexes (iTMCs), such as For example, the compounds of the present invention in polymeric matrix.
- the lower electrode layer 2 On the transparent substrate 1 is the lower electrode layer 2, for example, the anode.
- the emitter material (iTMC) constituting the active layer 3 that is the phosphorescent metal complex compound together with a matrix material in a Solvent dissolved.
- iTMC the emitter material constituting the active layer 3
- a matrix material in a Solvent dissolved.
- the soluble matrix materials used in conjunction with iTMCs are, for example, polymers, oligomers and ionic liquids.
- polymeric matrix materials are among many others: polycarbonate (PC), polymethyl methacrylate (PMMA), polyvinyl carbazole (PVK).
- PC polycarbonate
- PMMA polymethyl methacrylate
- PVK polyvinyl carbazole
- PEDOT poly (3, 4-ethylenedioxythiophene)
- any co-polymers and / or block-co-polymers also called "insulating", but may contain, for example lö ⁇ sungsverffennde units may be used.
- Examples are polysytrol, ABS, ethylene units, vinyl units etc.
- non-ionic matrix materials can also be used.
- iTMCs are used:
- the emitters described here show, for example, the chemical structure according to structure III with triazole unit.
- the invention encompasses both the 1,2,3 and the
- 1, 2, 4-triazole based systems contain up to 2 independent "classic", that is already known
- the third ligand according to the invention may for example consist of a triazole unit
- Imidazoliniumaku be formed, wherein the nitrogen 1 is bound to the iridium and in position 5 of the triazole ring has a heteroaromatic substituent which forms a coordinative bond from nitrogen to iridium
- 1,2,4-triazoles are obtained by C and N are formally out ⁇ exchanges.
- 1,2,4-triazole ⁇ * The following are some examples of the ring structure of the heteroaromatic, for example a 6-membered ring, ortho to the two adjacent nitrogens of the triazole ring. In the simplest case, it is a pyridine ring or a derivative thereof:
- X is either the radical -C-R, where R is one of the substituents below or a nitrogen atom with a lone pair of electrons.
- Phthalazine derivatives wherein Xi N and all other residues of type -CR.
- substituent "c" on the triazole are:
- Isoquinoline derivatives which are structural isomers to the isoquinoline derivatives of the derivatives mentioned above to the substituents "b" on the triazole.
- Higher condensed systems can be prepared analogously, for example pteridine, acridine, phenazine, phenanthridine and / or purine and derivatives thereof as well as compounds having additional heteroatoms such as oxygen or sulfur in the condensed ring bearing the coordinating nitrogen atom.
- ring structure of the heteroaromatic in ortho position to the two adjacent nitrogens of the triazole ring for example a 5-membered ring:
- the 6-membered ring is again a pyridine ring.
- hetero-five-membered substituted triazoles are given:
- Imidazole derivatives wherein Xi, X2 are residues of type -CR and X 3 is a residue of type NR.
- Benzimidazole derivatives wherein X5 of type NR and Xi, X 2 , X 3 , X 4 are radicals of type -CR. Further nitrogen atoms may be included in the attached benzene ring, thus forming benzimidazole analog pyridine, pyrimidine, pyrazine or pyrimidazine ring, by substitution of CR with nitrogen.
- X5 is a radical of the type NR and Xi, X3, are of the type N, and X 4 are of the type -CR. All substituents R can independently of one another H,
- the alkyl groups may be functional groups such as ethers (ethoxy, methoxy, etc.), esters, amides, carbonates etc. or halogens, preferably F.
- R is not limited to alkyl type radicals but may have substituted or unsubstituted aromatic systems such as phenyl, biphenyl, naphthyl, phenanthryl, etc., and benzyl, etc.
- This invention describes phosphorescent ionic emitters for applications in organic light emitting electrochemical cells.
- the compounds are derived from known OLED emitters by providing a peripheral substituent of the ligand with an imidazolinium moiety.
- Stability criteria of OLED emitters can be transferred to OLEECs.
- Devices can be fabricated by inexpensive wet process with simultaneous use of the advantages of the low molecular weight compounds (ease of manufacture, reproducibility of the synthesis, good tearing open ⁇ nists., good solubility).
- FIG. 2 shows the emission spectrum in dichloromethane with the maximum emission "excitation” at 368 nm.
- FIG. 3 shows the emission spectrum in air-saturated acetonitrile. "aerated acetonitrile" The emission spectrum shows a maximum at 355 nm.
- Figure 4 shows the emission spectrum in butyl nitrate at 77K, with emission occurring at 370nm.
- the OLEEC component was tested on a pre-structured ITO
- a 100 nm PEDOT: PSS layer (here: AI4083 from HC Starck) and the Emit ⁇ ter substances consisting of (dfppy) 2 + PF 6 lrTrim Imidazolim-PF 6 in a molar concentration ratio of 1: 1.
- acetonitrile was used as solvent.
- Ka ⁇ method a 200 nm thick aluminum layer was deposited by thermal ⁇ cal evaporation. The component was sealed by glued-on glass cap.
- Figure 5 shows the luminance as a function of time measured at a constant voltage of 5.5 V. Referring to Figure 5, the emission over almost the entire visible spectral range extends ge ⁇ why the light appears white.
- This invention first introduces the principle that simple and known per se neutral emitter materials, as they are known for example from OLED technology, can be converted into a charged species by the introduction of a charged imidazolinium radical. This charged species can then be used in organic light-emitting electrochemical cells.
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US13/575,265 US9169434B2 (en) | 2010-01-25 | 2010-11-17 | Phosphorescent metal complex, process for production and light-emitting component |
CN201080065767.2A CN102844402B (zh) | 2010-01-25 | 2010-11-17 | 磷光性的金属络合化合物、用于制造其的方法和发光器件 |
EP10782248A EP2528988A1 (de) | 2010-01-25 | 2010-11-17 | Phosphoreszente metallkomplexverbindung, verfahren zur herstellung und lichtemittierendes bauelement |
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WO2015086400A1 (de) | 2013-12-12 | 2015-06-18 | Siemens Aktiengesellschaft | Metallionaddukte von neutralen phosphoreszenten emittern zur verwendung in lichtemittierenden organischen optoelektronischen bauteilen |
CN104093813B (zh) * | 2011-12-01 | 2017-06-06 | 联邦印刷厂有限公司 | 光电安全元件 |
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DE102010006280A1 (de) * | 2010-01-30 | 2011-08-04 | Merck Patent GmbH, 64293 | Farbkonvertierung |
DE102010023959B4 (de) | 2010-06-16 | 2013-02-21 | Osram Ag | Neue Verbindungen als Liganden für Übergangsmetallkomplexe und daraus hergestellte Materialien, sowie Verwendung dazu |
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US8784690B2 (en) | 2010-08-20 | 2014-07-22 | Rhodia Operations | Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels and foams |
US9552903B2 (en) | 2010-08-20 | 2017-01-24 | Rhodia Operations | Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels and foams |
CN104093813B (zh) * | 2011-12-01 | 2017-06-06 | 联邦印刷厂有限公司 | 光电安全元件 |
JP2015504884A (ja) * | 2011-12-27 | 2015-02-16 | メルク パテント ゲーエムベーハー | 1,2,3−トリアゾールを含む金属錯体 |
WO2015086400A1 (de) | 2013-12-12 | 2015-06-18 | Siemens Aktiengesellschaft | Metallionaddukte von neutralen phosphoreszenten emittern zur verwendung in lichtemittierenden organischen optoelektronischen bauteilen |
DE102013225682A1 (de) | 2013-12-12 | 2015-06-18 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Metallionaddukte von neutralen phosphoreszenten Emittern zur Verwendung in lichtemittierenden organischen optoelektronischen Bauteilen |
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EP2528988A1 (de) | 2012-12-05 |
US20130046096A1 (en) | 2013-02-21 |
CN102844402A (zh) | 2012-12-26 |
CN102844402B (zh) | 2016-06-22 |
DE102010005632A1 (de) | 2011-07-28 |
US9169434B2 (en) | 2015-10-27 |
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