CA2549309A1 - Use of metal complexes as n-dopants for organic semiconductors and production thereof including their ligands - Google Patents
Use of metal complexes as n-dopants for organic semiconductors and production thereof including their ligands Download PDFInfo
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- CA2549309A1 CA2549309A1 CA002549309A CA2549309A CA2549309A1 CA 2549309 A1 CA2549309 A1 CA 2549309A1 CA 002549309 A CA002549309 A CA 002549309A CA 2549309 A CA2549309 A CA 2549309A CA 2549309 A1 CA2549309 A1 CA 2549309A1
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- atom
- metal
- ligand
- alkyl
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- 239000003446 ligand Substances 0.000 title claims abstract description 235
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 125
- 239000002184 metal Substances 0.000 title claims abstract description 125
- 239000002019 doping agent Substances 0.000 title claims abstract description 73
- 239000004065 semiconductor Substances 0.000 title claims abstract description 31
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 125000004429 atom Chemical group 0.000 claims abstract description 289
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 239000011159 matrix material Substances 0.000 claims abstract description 67
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 65
- 150000004696 coordination complex Chemical class 0.000 claims abstract description 59
- 229910052718 tin Inorganic materials 0.000 claims abstract description 48
- 150000003624 transition metals Chemical group 0.000 claims abstract description 40
- 238000000034 method Methods 0.000 claims abstract description 37
- -1 germylene Chemical group 0.000 claims abstract description 36
- 230000007935 neutral effect Effects 0.000 claims abstract description 28
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052745 lead Inorganic materials 0.000 claims abstract description 16
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims description 115
- 229910052717 sulfur Inorganic materials 0.000 claims description 87
- 229910052698 phosphorus Inorganic materials 0.000 claims description 83
- 229910052710 silicon Inorganic materials 0.000 claims description 60
- 125000005842 heteroatom Chemical group 0.000 claims description 59
- 229910052757 nitrogen Inorganic materials 0.000 claims description 56
- 239000000306 component Substances 0.000 claims description 52
- 229910052732 germanium Inorganic materials 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001072 heteroaryl group Chemical group 0.000 claims description 47
- 229910052760 oxygen Inorganic materials 0.000 claims description 43
- 125000004122 cyclic group Chemical group 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 229910052785 arsenic Inorganic materials 0.000 claims description 36
- 229920006395 saturated elastomer Polymers 0.000 claims description 36
- 229910052742 iron Inorganic materials 0.000 claims description 35
- 229910052759 nickel Inorganic materials 0.000 claims description 35
- 229910052804 chromium Inorganic materials 0.000 claims description 34
- 229910052725 zinc Inorganic materials 0.000 claims description 34
- 230000008569 process Effects 0.000 claims description 31
- 229910052711 selenium Inorganic materials 0.000 claims description 30
- 229910052748 manganese Inorganic materials 0.000 claims description 29
- 229910052787 antimony Inorganic materials 0.000 claims description 28
- 229910052802 copper Inorganic materials 0.000 claims description 28
- 229910052750 molybdenum Inorganic materials 0.000 claims description 28
- 229910052714 tellurium Inorganic materials 0.000 claims description 25
- 229910052723 transition metal Inorganic materials 0.000 claims description 25
- 229910052721 tungsten Inorganic materials 0.000 claims description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims description 19
- 230000027455 binding Effects 0.000 claims description 19
- 238000009739 binding Methods 0.000 claims description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910003472 fullerene Inorganic materials 0.000 claims description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 10
- 229910052796 boron Inorganic materials 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 229910052782 aluminium Inorganic materials 0.000 claims description 8
- 150000007942 carboxylates Chemical class 0.000 claims description 8
- 239000000758 substrate Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 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 claims description 5
- 229910052733 gallium Inorganic materials 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 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 claims description 4
- 230000005669 field effect Effects 0.000 claims description 4
- 150000002460 imidazoles Chemical class 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 150000003233 pyrroles Chemical class 0.000 claims description 4
- 238000000859 sublimation Methods 0.000 claims description 4
- 230000008022 sublimation Effects 0.000 claims description 4
- 239000010953 base metal Substances 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000002916 oxazoles Chemical class 0.000 claims description 3
- 150000003217 pyrazoles Chemical class 0.000 claims description 3
- 150000003557 thiazoles Chemical class 0.000 claims description 3
- 150000003577 thiophenes Chemical class 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052792 caesium Inorganic materials 0.000 claims description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 2
- 238000002425 crystallisation Methods 0.000 claims description 2
- 150000004292 cyclic ethers Chemical class 0.000 claims description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 150000001983 dialkylethers Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229920000570 polyether Polymers 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 30
- 229940076134 benzene Drugs 0.000 claims 3
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 1
- 239000011368 organic material Substances 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- 230000009467 reduction Effects 0.000 abstract description 7
- 239000010410 layer Substances 0.000 description 65
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 35
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 29
- 210000000080 chela (arthropods) Anatomy 0.000 description 27
- 239000011701 zinc Substances 0.000 description 27
- 239000010949 copper Substances 0.000 description 21
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 19
- 125000000753 cycloalkyl group Chemical group 0.000 description 18
- 125000006193 alkinyl group Chemical group 0.000 description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 description 16
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 150000001721 carbon Chemical group 0.000 description 10
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 10
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 10
- 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 10
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 9
- WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 8
- 229940125758 compound 15 Drugs 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- 229910052727 yttrium Inorganic materials 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 239000002800 charge carrier Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 6
- 150000004032 porphyrins Chemical class 0.000 description 6
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 6
- 238000001308 synthesis method Methods 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical class N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 description 5
- VCZBRPRKZKPDQD-UHFFFAOYSA-N 1,5,6,7-tetrahydroimidazo[1,2-a]pyrimidine Chemical compound C1CCN=C2NC=CN21 VCZBRPRKZKPDQD-UHFFFAOYSA-N 0.000 description 4
- JAQPBKRMYZOTHW-UHFFFAOYSA-N 2,4-dimethyl-2,3,4,6,7,8-hexahydro-1h-pyrimido[1,2-a]pyrimidine Chemical compound C1CCN=C2NC(C)CC(C)N21 JAQPBKRMYZOTHW-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- ILZSSCVGGYJLOG-UHFFFAOYSA-N cobaltocene Chemical compound [Co+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 ILZSSCVGGYJLOG-UHFFFAOYSA-N 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 239000003792 electrolyte Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000006413 ring segment Chemical group 0.000 description 4
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- VXWZPLQTNYSOCY-UHFFFAOYSA-N 2,3,4,10-tetrahydropyrimido[1,2-a]benzimidazole Chemical compound N1C2=CC=CC=C2N2C1=NCCC2 VXWZPLQTNYSOCY-UHFFFAOYSA-N 0.000 description 3
- NMFGZMLSEVQWDG-UHFFFAOYSA-N 2,4-dimethyl-3,4-dihydro-2h-pyrimido[1,2-a]pyrimidine Chemical compound C1=CC=NC2=NC(C)CC(C)N21 NMFGZMLSEVQWDG-UHFFFAOYSA-N 0.000 description 3
- ZCRYXUJJFHGSRU-UHFFFAOYSA-N 4,6-dimethyl-1,4,5,6-tetrahydropyrimidin-2-amine Chemical compound CC1CC(C)N=C(N)N1 ZCRYXUJJFHGSRU-UHFFFAOYSA-N 0.000 description 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003574 free electron Substances 0.000 description 3
- INSWZAQOISIYDT-UHFFFAOYSA-N imidazo[1,2-a]pyrimidine Chemical compound C1=CC=NC2=NC=CN21 INSWZAQOISIYDT-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 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 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000004892 pyridazines Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- HOHWYQSDLRTVDK-UHFFFAOYSA-N pyrimido[1,2-a]benzimidazole Chemical compound N1=CC=CN2C3=CC=CC=C3N=C21 HOHWYQSDLRTVDK-UHFFFAOYSA-N 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
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- 125000006850 spacer group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical compound S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 238000009834 vaporization Methods 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
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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
-
- 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/30—Doping active layers, e.g. electron transporting layers
-
- H—ELECTRICITY
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004010954.0 | 2004-03-03 | ||
| DE102004010954A DE102004010954A1 (de) | 2004-03-03 | 2004-03-03 | Verwendung eines Metallkomplexes als n-Dotand für ein organisches halbleitendes Matrixmaterial, organisches Halbleitermaterial und elektronisches Bauteil |
| PCT/DE2005/000372 WO2005086251A2 (de) | 2004-03-03 | 2005-03-03 | Verwendung von metallkomplexen als n-dotanden für organische halbleiter und die darstellung derselbigen inkl. ihrer liganden |
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| CA2549309A1 true CA2549309A1 (en) | 2005-09-15 |
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| Application Number | Title | Priority Date | Filing Date |
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| CA002549309A Abandoned CA2549309A1 (en) | 2004-03-03 | 2005-03-03 | Use of metal complexes as n-dopants for organic semiconductors and production thereof including their ligands |
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| Country | Link |
|---|---|
| US (1) | US8258501B2 (Direct) |
| EP (3) | EP1672714A3 (Direct) |
| JP (1) | JP4847947B2 (Direct) |
| KR (1) | KR100867028B1 (Direct) |
| CN (2) | CN101580519A (Direct) |
| CA (1) | CA2549309A1 (Direct) |
| DE (3) | DE102004010954A1 (Direct) |
| IN (1) | IN2006MU00293A (Direct) |
| WO (1) | WO2005086251A2 (Direct) |
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| EP2786435B1 (en) | 2011-11-30 | 2019-07-17 | Novaled GmbH | Compounds |
| CN104115296B (zh) | 2011-11-30 | 2016-09-14 | 诺瓦尔德股份有限公司 | 有机电子器件 |
| JP6204371B2 (ja) | 2011-11-30 | 2017-09-27 | ノヴァレッド ゲーエムベーハー | 有機電子装置 |
| JP6139552B2 (ja) | 2011-12-06 | 2017-05-31 | ノヴァレッド ゲーエムベーハー | 有機発光素子およびその製造方法 |
| EP2793280B1 (en) * | 2011-12-12 | 2017-03-29 | Nippon Steel & Sumikin Chemical Co., Ltd. | Organic electroluminescent element material and organic electroluminescent element using same |
| DE102012100642B4 (de) | 2012-01-26 | 2015-09-10 | Novaled Ag | Anordnung mit mehreren organischen Halbleiterbauelementen und Verfahren zum Herstellen sowie Verwendung der Anordnung |
| DE102012103448B4 (de) | 2012-04-19 | 2018-01-04 | Heliatek Gmbh | Verfahren zur Optimierung von in Reihe geschalteten, photoaktiven Bauelementen auf gekrümmten Oberflächen |
| DE102012104118B4 (de) | 2012-05-10 | 2021-12-02 | Heliatek Gmbh | Lochtransportmaterialien für optoelektronische Bauelemente |
| DE102012104247B4 (de) | 2012-05-16 | 2017-07-20 | Heliatek Gmbh | Halbleitendes organisches Material für optoelektronische Bauelemente |
| WO2013179220A2 (de) | 2012-05-30 | 2013-12-05 | Heliatek Gmbh | Solarmodul zur anordnung auf formteilen |
| DE102012209523A1 (de) | 2012-06-06 | 2013-12-12 | Osram Opto Semiconductors Gmbh | Hauptgruppenmetallkomplexe als p-Dotanden für organische elektronische Matrixmaterialien |
| DE102012209520A1 (de) | 2012-06-06 | 2013-12-12 | Osram Opto Semiconductors Gmbh | Metallkomplexe als p-Dotanden für organische elektronische Matrixmaterialien |
| EP2859587B1 (de) | 2012-06-11 | 2017-08-09 | Heliatek GmbH | Filtersystem für photoaktive bauelemente |
| DE102012105022A1 (de) | 2012-06-11 | 2013-12-12 | Heliatek Gmbh | Fahrzeug mit flexiblen organischen Photovoltaik-Modulen |
| DE102012105810B4 (de) | 2012-07-02 | 2020-12-24 | Heliatek Gmbh | Transparente Elektrode für optoelektronische Bauelemente |
| DE102012105812A1 (de) | 2012-07-02 | 2014-01-02 | Heliatek Gmbh | Elektrodenanordnung für optoelektronische Bauelemente |
| DE102012105809B4 (de) | 2012-07-02 | 2017-12-07 | Heliatek Gmbh | Organisches optoelektronisches Bauelement mit transparenter Gegenelektrode und transparenter Elektrodenvorrichtung |
| ES2762410T3 (es) | 2012-07-02 | 2020-05-25 | Heliatek Gmbh | Electrodo transparente para componentes optoelectrónicos |
| JP2014053383A (ja) * | 2012-09-05 | 2014-03-20 | Konica Minolta Inc | タンデム型の有機光電変換素子およびこれを用いた太陽電池 |
| DE102012217587A1 (de) * | 2012-09-27 | 2014-03-27 | Siemens Aktiengesellschaft | Salze des Cyclopentadiens als n-Dotierstoffe für die organische Elektronik |
| EP2811000B1 (en) | 2013-06-06 | 2017-12-13 | Novaled GmbH | Organic electronic device |
| DE102013212018A1 (de) * | 2013-06-25 | 2015-01-08 | Evonik Industries Ag | Metalloxid-Prekursoren, sie enthaltende Beschichtungszusammensetzungen, und ihre Verwendung |
| EP2840622B1 (en) | 2013-08-19 | 2019-02-13 | Novaled GmbH | Electronic or optoelectronic device comprising an anchored thin molecular layer, process for its preparation and compound used therein |
| DE102013013876A1 (de) | 2013-08-20 | 2015-03-12 | Merck Patent Gmbh | Metallkomplexe |
| CN103483365B (zh) * | 2013-09-03 | 2016-04-27 | 太仓碧奇新材料研发有限公司 | 一种并三噻吩硼烷晶体管材料及其制备方法 |
| DE102013110693B4 (de) | 2013-09-27 | 2024-04-25 | Heliatek Gmbh | Photoaktives, organisches Material für optoelektronische Bauelemente |
| US10374170B2 (en) | 2013-12-06 | 2019-08-06 | Merck Patent Gmbh | Substituted oxepines |
| KR102388354B1 (ko) | 2013-12-19 | 2022-04-19 | 메르크 파텐트 게엠베하 | 헤테로시클릭 스피로 화합물 |
| ES2673573T3 (es) | 2013-12-23 | 2018-06-22 | Novaled Gmbh | Material semiconductor con dopaje N que comprende una matriz de óxido de fosfina y un metal dopante |
| DE102014202718A1 (de) | 2014-02-14 | 2015-08-20 | Evonik Degussa Gmbh | Beschichtungszusammensetzung, Verfahren zu ihrer Herstellung und ihre Verwendung |
| EP2924753B1 (en) | 2014-03-25 | 2017-04-19 | Novaled GmbH | Polychromatic light emitting devices and versatile hole transporting matrix for them |
| EP2933852B2 (en) | 2014-04-17 | 2023-09-06 | Novaled GmbH | Phosphorescent OLED and hole transporting materials for phosphorescent OLEDs |
| EP2963010B1 (en) | 2014-07-04 | 2018-02-21 | Novaled GmbH | Electronic device and compound |
| EP3172775B1 (de) | 2014-07-21 | 2022-04-20 | Merck Patent GmbH | Materialien für elektronische vorrichtungen |
| JP6695863B2 (ja) | 2014-09-05 | 2020-05-20 | メルク パテント ゲーエムベーハー | 調合物と電子素子 |
| DE102014114224A1 (de) | 2014-09-30 | 2016-03-31 | Osram Oled Gmbh | Organisches elektronisches Bauteil, Verwendung eines Zinkkomplexes als p-Dotierungsmittel für organische elektronische Matrixmaterialien |
| EP3002801B1 (en) | 2014-09-30 | 2018-07-18 | Novaled GmbH | Organic electronic device |
| WO2016107663A1 (de) | 2014-12-30 | 2016-07-07 | Merck Patent Gmbh | Formulierungen und elektronische vorrichtungen |
| KR102038124B1 (ko) * | 2016-06-27 | 2019-10-29 | 숭실대학교산학협력단 | 유기 반도체 소자의 제조 방법 |
| EP3278377B1 (en) | 2015-03-30 | 2020-08-05 | Merck Patent GmbH | Formulation of an organic functional material comprising a siloxane solvent |
| CN111477766B (zh) | 2015-06-12 | 2023-04-07 | 默克专利有限公司 | 作为用于oled制剂的溶剂的含有非芳族环的酯 |
| EP3109919B1 (en) | 2015-06-23 | 2021-06-23 | Novaled GmbH | N-doped semiconducting material comprising polar matrix and metal dopant |
| KR102581918B1 (ko) | 2015-06-23 | 2023-09-21 | 노발레드 게엠베하 | 극성 매트릭스 및 금속 도펀트를 포함하는 n-도핑된 반도전성 물질 |
| EP3109916B1 (en) | 2015-06-23 | 2021-08-25 | Novaled GmbH | Organic light emitting device comprising polar matrix, metal dopant and silver cathode |
| US11046884B2 (en) | 2015-08-28 | 2021-06-29 | Merck Patent Gmbh | Formulation of an organic functional material comprising an epoxy group containing solvent |
| KR102721890B1 (ko) | 2015-12-10 | 2024-10-24 | 메르크 파텐트 게엠베하 | 비-방향족 사이클을 함유하는 케톤을 포함하는 제형 |
| JP6711602B2 (ja) * | 2015-12-10 | 2020-06-17 | キヤノン株式会社 | 有機発光素子 |
| US11171294B2 (en) | 2015-12-15 | 2021-11-09 | Merck Patent Gmbh | Esters containing aromatic groups as solvents for organic electronic formulations |
| CN108431143A (zh) | 2015-12-16 | 2018-08-21 | 默克专利有限公司 | 含固体溶剂的制剂 |
| WO2017102049A1 (en) | 2015-12-16 | 2017-06-22 | Merck Patent Gmbh | Formulations containing a mixture of at least two different solvents |
| KR102776731B1 (ko) | 2016-02-17 | 2025-03-05 | 메르크 파텐트 게엠베하 | 유기 기능성 재료의 제형 |
| EP3208863B1 (en) | 2016-02-22 | 2019-10-23 | Novaled GmbH | Charge transporting semi-conducting material and electronic device comprising it |
| DE102016003104A1 (de) | 2016-03-15 | 2017-09-21 | Merck Patent Gmbh | Behälter umfassend eine Formulierung enthaltend mindestens einen organischen Halbleiter |
| EP3242340B1 (en) * | 2016-05-04 | 2023-05-24 | Novaled GmbH | Solar cell |
| WO2017196076A2 (ko) * | 2016-05-10 | 2017-11-16 | 주식회사 엘지화학 | 유기 전계 발광 소자 및 이의 제조 방법 |
| DE102016208298A1 (de) * | 2016-05-13 | 2017-11-16 | Siemens Aktiengesellschaft | Organische elektronenleitende Schicht mit n-Dotierstoff |
| WO2017216129A1 (en) | 2016-06-16 | 2017-12-21 | Merck Patent Gmbh | Formulation of an organic functional material |
| WO2017216128A1 (en) | 2016-06-17 | 2017-12-21 | Merck Patent Gmbh | Formulation of an organic functional material |
| TW201815998A (zh) | 2016-06-28 | 2018-05-01 | 德商麥克專利有限公司 | 有機功能材料之調配物 |
| KR102078435B1 (ko) * | 2016-07-14 | 2020-02-17 | 주식회사 엘지화학 | 유기 전계 발광 소자 및 이의 제조 방법 |
| CN109563402B (zh) | 2016-08-04 | 2022-07-15 | 默克专利有限公司 | 有机功能材料的制剂 |
| US10573522B2 (en) | 2016-08-16 | 2020-02-25 | Lam Research Corporation | Method for preventing line bending during metal fill process |
| EP3312896B1 (en) | 2016-10-24 | 2021-03-31 | Novaled GmbH | Organic electroluminescent device comprising a redox-doped electron transport layer and an auxiliary electron transport layer |
| EP3312895B1 (en) | 2016-10-24 | 2021-07-28 | Novaled GmbH | Organic semiconducting material comprising an electrical n-dopant and an electron transport matrix and electronic device comprising the semiconducting material |
| CN109863223B (zh) | 2016-10-31 | 2023-06-20 | 默克专利有限公司 | 有机功能材料的制剂 |
| JP7013459B2 (ja) | 2016-10-31 | 2022-01-31 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
| TW201833118A (zh) | 2016-11-22 | 2018-09-16 | 德商麥克專利有限公司 | 用於電子裝置之材料 |
| US10892414B2 (en) | 2016-12-06 | 2021-01-12 | Merck Patent Gmbh | Process for making electronic device |
| JP7091337B2 (ja) | 2016-12-13 | 2022-06-27 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
| WO2018114883A1 (de) | 2016-12-22 | 2018-06-28 | Merck Patent Gmbh | Mischungen umfassend mindestens zwei organisch funktionelle verbindungen |
| TWI763772B (zh) | 2017-01-30 | 2022-05-11 | 德商麥克專利有限公司 | 電子裝置之有機元件的形成方法 |
| TWI791481B (zh) | 2017-01-30 | 2023-02-11 | 德商麥克專利有限公司 | 形成有機電致發光（ｅｌ）元件之方法 |
| EP3355378B1 (en) | 2017-01-30 | 2022-12-28 | Novaled GmbH | Electroluminescent device comprising a defined layer arrangement comprising a light emitting layer, a hole transport layer and an electron transport layer |
| EP3369729B1 (en) | 2017-03-02 | 2022-01-12 | Novaled GmbH | Fused 9-phenyl-acridine derivatives for use in an electronic device and display device |
| CN110446611B (zh) | 2017-03-31 | 2021-05-25 | 默克专利有限公司 | 用于有机发光二极管(oled)的印刷方法 |
| JP7200128B2 (ja) | 2017-04-10 | 2023-01-06 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
| CN110520503A (zh) | 2017-04-13 | 2019-11-29 | 默克专利有限公司 | 用于有机电子器件的组合物 |
| KR102585423B1 (ko) | 2017-04-25 | 2023-10-05 | 메르크 파텐트 게엠베하 | 전자 디바이스용 화합물 |
| JP7330898B2 (ja) | 2017-05-03 | 2023-08-22 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
| DE102017111137B4 (de) | 2017-05-22 | 2025-07-10 | Novaled Gmbh | Organische elektrolumineszente Vorrichtung |
| EP3406599B1 (en) | 2017-05-23 | 2023-02-22 | Novaled GmbH | Organic electronic device comprising an organic semiconductor layer |
| EP3407401A1 (en) | 2017-05-23 | 2018-11-28 | Novaled GmbH | Organic electronic device comprising an organic semiconductor layer and a device |
| WO2019002198A1 (en) | 2017-06-26 | 2019-01-03 | Merck Patent Gmbh | HOMOGENEOUS MIXTURES |
| KR102717279B1 (ko) | 2017-07-05 | 2024-10-15 | 메르크 파텐트 게엠베하 | 유기 전자 디바이스용 조성물 |
| KR102653984B1 (ko) | 2017-07-05 | 2024-04-02 | 메르크 파텐트 게엠베하 | 유기 전자 디바이스용 조성물 |
| CN110892543B (zh) | 2017-07-18 | 2023-07-28 | 默克专利有限公司 | 有机功能材料的制剂 |
| CN107501269B (zh) * | 2017-08-08 | 2019-06-18 | 华中科技大学 | 有机脒分子n型掺杂剂及其在半导体光电器件中的应用 |
| EP3470398B1 (en) | 2017-10-13 | 2022-05-04 | Novaled GmbH | Organic electronic device comprising an organic semiconductor layer |
| EP3470412B1 (en) | 2017-10-13 | 2020-07-22 | Novaled GmbH | Organic electronic device comprising an organic semiconductor layer |
| EP3483153A1 (en) | 2017-11-09 | 2019-05-15 | Novaled GmbH | Compounds comprising triazine group, fluorene-group and aryl group and their use in organic electronic devices |
| EP3483154A1 (en) | 2017-11-09 | 2019-05-15 | Novaled GmbH | Compounds comprising triazine, fluorene and aryl groups and their use in organic electronic devices |
| TWI785142B (zh) | 2017-11-14 | 2022-12-01 | 德商麥克專利有限公司 | 用於有機電子裝置之組成物 |
| JP7293229B2 (ja) | 2017-12-15 | 2023-06-19 | メルク パテント ゲーエムベーハー | 有機機能材料の調合物 |
| EP3503234B1 (en) * | 2017-12-20 | 2020-11-04 | Novaled GmbH | Organic electronic device comprising an inverse coordination complex and a method for preparing the same |
| EP3503241B1 (en) * | 2017-12-22 | 2022-08-24 | Novaled GmbH | Electronic device and method for preparing the same |
| EP4234539A1 (en) | 2018-02-07 | 2023-08-30 | Novaled GmbH | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
| CN111712551A (zh) | 2018-02-26 | 2020-09-25 | 默克专利有限公司 | 有机功能材料的制剂 |
| EP3533788A1 (en) | 2018-02-28 | 2019-09-04 | Novaled GmbH | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
| WO2019229011A1 (de) | 2018-05-30 | 2019-12-05 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
| EP3582280B1 (en) | 2018-06-14 | 2024-03-20 | Novaled GmbH | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
| US11603479B2 (en) | 2018-06-15 | 2023-03-14 | Merck Kgaa | Formulation of an organic functional material |
| EP3857621B1 (de) | 2018-09-24 | 2025-10-29 | Merck Patent GmbH | Verfahren zur herstellung von granulat |
| DE102018125307A1 (de) | 2018-10-12 | 2020-04-16 | Novaled Gmbh | Organische lichtemittierende Vorrichtung |
| CN112930606A (zh) | 2018-11-06 | 2021-06-08 | 默克专利有限公司 | 用于形成电子器件的有机元件的方法 |
| EP3653619A1 (en) | 2018-11-16 | 2020-05-20 | Novaled GmbH | Compound, organic electronic device comprising the same, and display device and lighting device comprising the same |
| KR20250116174A (ko) | 2018-11-19 | 2025-07-31 | 램 리써치 코포레이션 | 텅스텐을 위한 몰리브덴 템플릿들 |
| EP3667753B1 (en) | 2018-12-14 | 2025-04-23 | Novaled GmbH | Organic light emitting device and a compound for use therein |
| JP7581213B2 (ja) | 2019-01-28 | 2024-11-12 | ラム リサーチ コーポレーション | 金属膜の蒸着 |
| US20220127286A1 (en) | 2019-03-04 | 2022-04-28 | Merck Patent Gmbh | Ligands for nano-sized materials |
| WO2020185618A1 (en) | 2019-03-11 | 2020-09-17 | Lam Research Corporation | Precursors for deposition of molybdenum-containing films |
| CN111825591B (zh) * | 2019-04-22 | 2023-11-21 | 北京大学 | 三胺基甲烷衍生物作为n型掺杂剂在半导体材料中的应用 |
| KR20220053668A (ko) | 2019-09-03 | 2022-04-29 | 램 리써치 코포레이션 | 몰리브덴 증착 |
| JP2022551965A (ja) | 2019-10-15 | 2022-12-14 | ラム リサーチ コーポレーション | モリブデン充填 |
| EP3840080A1 (en) | 2019-12-17 | 2021-06-23 | Novaled GmbH | Organic electronic device and display device comprising the organic electronic device |
| WO2021213918A1 (en) | 2020-04-21 | 2021-10-28 | Merck Patent Gmbh | Formulation of an organic functional material |
| KR102914927B1 (ko) | 2020-06-23 | 2026-01-19 | 메르크 파텐트 게엠베하 | 혼합물의 제조 방법 |
| GB202017456D0 (en) * | 2020-11-04 | 2020-12-16 | Johnson Matthey Plc | Process |
| WO2022122607A1 (en) | 2020-12-08 | 2022-06-16 | Merck Patent Gmbh | An ink system and a method for inkjet printing |
| DE102021108497A1 (de) | 2021-04-06 | 2022-10-06 | Heliatek Gmbh | Dotanden für elektronische Bauelemente, deren Verwendung in elektronischen Bauelementen, sowie elektronische Bauelemente mit solchen Dotanden |
| CN117321504A (zh) * | 2021-04-23 | 2023-12-29 | 恩特格里斯公司 | 用于低曝光剂量euv辐射的高量子效率干式抗蚀剂 |
| EP4326826A1 (en) | 2021-04-23 | 2024-02-28 | Merck Patent GmbH | Formulation of an organic functional material |
| KR20240012506A (ko) | 2021-05-21 | 2024-01-29 | 메르크 파텐트 게엠베하 | 적어도 하나의 기능성 물질의 연속 정제 방법 및 적어도 하나의 기능성 물질의 연속 정제를 위한 디바이스 |
| DE102021116886A1 (de) | 2021-06-30 | 2023-01-05 | Heliatek Gmbh | Verfahren zur Herstellung mindestens einer dotierten Ladungstransportschicht eines Schichtsystems eines organischen elektronischen Bauelements |
| TW202349760A (zh) | 2021-10-05 | 2023-12-16 | 德商麥克專利有限公司 | 電子裝置之有機元件的形成方法 |
| DE102022116253A1 (de) | 2022-06-29 | 2024-01-04 | Heliatek Gmbh | Organisches elektronisches Bauelement mit einer chemischen Verbindung der allgemeinen Formel I, sowie Verwendung einer solchen chemischen Verbindung als n-Dotand in einem organischen elektronischen Bauelement |
| EP4299573A1 (en) | 2022-06-30 | 2024-01-03 | Novaled GmbH | Compound, organic semiconducting material comprising the same, organic electronic device comprising the same and a method for preparing the organic electronic device |
| EP4321511A1 (en) | 2022-08-09 | 2024-02-14 | Novaled GmbH | Compound, organic semiconducting material comprising the same, organic electronic device comprising the same and display device comprising the same |
| EP4346357A1 (en) | 2022-09-29 | 2024-04-03 | Novaled GmbH | Semiconducting material, process for preparing a layer of the semiconducting material, organic semiconducting device comprising the organic semiconducting material, display device comprising the organic semiconducting device and compound |
| EP4383988A1 (en) | 2022-12-06 | 2024-06-12 | Novaled GmbH | Organic light emitting diode, device comprising the same and compound |
| EP4383989A1 (en) | 2022-12-06 | 2024-06-12 | Novaled GmbH | Organic light emitting diode and device comprising the same |
| TW202440819A (zh) | 2022-12-16 | 2024-10-16 | 德商麥克專利有限公司 | 有機功能性材料之調配物 |
| DE102023100108A1 (de) | 2023-01-03 | 2024-07-04 | Heliatek Gmbh | Elektronisches Bauelement mit einer chemischen Verbindung der allgemeinen Formel I, II und/oder III |
| EP4418842A1 (en) | 2023-02-14 | 2024-08-21 | Novaled GmbH | Organic light emitting diode, display device comprising the same and compound |
| EP4472384B1 (en) | 2023-05-30 | 2025-11-19 | Novaled GmbH | Compound, organic light emitting diode, and display device |
| WO2025032039A1 (en) | 2023-08-07 | 2025-02-13 | Merck Patent Gmbh | Process for the preparation of an electronic device |
| EP4531522A1 (en) | 2023-09-27 | 2025-04-02 | Novaled GmbH | Organic light emitting device, display device comprising the same |
| EP4572585A1 (en) | 2023-12-12 | 2025-06-18 | Novaled GmbH | Compound and organic light emitting diode |
| WO2025132547A1 (en) | 2023-12-21 | 2025-06-26 | Merck Patent Gmbh | Mechanochemical method for deuterating organic compounds |
| DE102024111658B4 (de) | 2024-04-25 | 2026-01-08 | Novaled Gmbh | Verbindung, organisches halbleitendes Material, organische elektronische Vorrichtung und Anzeigevorrichtung |
| EP4669067A1 (en) | 2024-06-17 | 2025-12-24 | Novaled GmbH | Organic light emitting diode, and display device |
| DE102024121413A1 (de) | 2024-07-26 | 2026-01-29 | Novaled Gmbh | Verbindung, organisches halbleitendes Material, organische elektronische Vorrichtung und Anzeigevorrichtung |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3069926D1 (en) | 1979-07-10 | 1985-02-21 | Japan Synthetic Rubber Co Ltd | Doped polyacetylenes and their production |
| IT1175989B (it) * | 1984-04-10 | 1987-08-12 | Montedison Spa | Procedimento per la preparazione di polifenileteri |
| WO1999007028A1 (fr) | 1997-07-31 | 1999-02-11 | Ecole Polytechnique Federale De Lausanne | Dispositif electroluminescent |
| US6660410B2 (en) | 2000-03-27 | 2003-12-09 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence element |
| CN1267525C (zh) * | 2001-03-08 | 2006-08-02 | 香港大学 | 有机金属光发射材料 |
| JP4169246B2 (ja) | 2001-03-16 | 2008-10-22 | 富士フイルム株式会社 | ヘテロ環化合物及びそれを用いた発光素子 |
| US6787249B2 (en) * | 2001-03-28 | 2004-09-07 | Semiconductor Energy Laboratory Co., Ltd. | Organic light emitting element and light emitting device using the same |
| CN101694867B (zh) * | 2001-08-29 | 2014-10-22 | 普林斯顿大学理事会 | 具有含金属配合物的载流子传输层的有机发光元件 |
| US6646285B1 (en) * | 2002-04-05 | 2003-11-11 | International Business Machines Corporation | Molecular electronic device using metal-metal bonded complexes |
| AU2002323418A1 (en) * | 2002-04-08 | 2003-10-27 | The University Of Southern California | Doped organic carrier transport materials |
| GB0216154D0 (en) * | 2002-07-12 | 2002-08-21 | Elam T Ltd | Metal chelates |
| JP5166675B2 (ja) * | 2002-07-24 | 2013-03-21 | ケッデム バイオ−サイエンス リミテッド | 創薬手法 |
| EP1539773A4 (en) | 2002-08-16 | 2009-11-11 | Univ Southern California | ORGANIC, LIGHT-EMITTING MATERIALS WITH ANIONIC LIGANDS |
| US20040043140A1 (en) | 2002-08-21 | 2004-03-04 | Ramesh Jagannathan | Solid state lighting using compressed fluid coatings |
| US7029766B2 (en) * | 2003-12-05 | 2006-04-18 | Eastman Kodak Company | Organic element for electroluminescent devices |
-
2004
- 2004-03-03 DE DE102004010954A patent/DE102004010954A1/de not_active Ceased
-
2005
- 2005-03-03 US US10/585,215 patent/US8258501B2/en active Active
- 2005-03-03 DE DE502005010680T patent/DE502005010680D1/de not_active Expired - Lifetime
- 2005-03-03 EP EP06007372A patent/EP1672714A3/de not_active Withdrawn
- 2005-03-03 CN CNA2009101182646A patent/CN101580519A/zh active Pending
- 2005-03-03 JP JP2007501110A patent/JP4847947B2/ja not_active Expired - Fee Related
- 2005-03-03 CN CN200580003728.9A patent/CN1914747B/zh not_active Expired - Lifetime
- 2005-03-03 EP EP05729708A patent/EP1721347B1/de not_active Expired - Lifetime
- 2005-03-03 KR KR1020067006767A patent/KR100867028B1/ko not_active Expired - Fee Related
- 2005-03-03 WO PCT/DE2005/000372 patent/WO2005086251A2/de not_active Ceased
- 2005-03-03 DE DE502005004031T patent/DE502005004031D1/de not_active Expired - Lifetime
- 2005-03-03 EP EP06025887A patent/EP1768200B1/de not_active Expired - Lifetime
- 2005-03-03 CA CA002549309A patent/CA2549309A1/en not_active Abandoned
-
2006
- 2006-03-13 IN IN293MU2006 patent/IN2006MU00293A/en unknown
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Also Published As
| Publication number | Publication date |
|---|---|
| KR20060110269A (ko) | 2006-10-24 |
| JP4847947B2 (ja) | 2011-12-28 |
| WO2005086251A3 (de) | 2006-02-16 |
| CN1914747B (zh) | 2014-12-10 |
| CN101580519A (zh) | 2009-11-18 |
| WO2005086251A2 (de) | 2005-09-15 |
| DE502005010680D1 (de) | 2011-01-27 |
| EP1672714A2 (de) | 2006-06-21 |
| DE102004010954A1 (de) | 2005-10-06 |
| EP1672714A3 (de) | 2006-10-18 |
| KR100867028B1 (ko) | 2008-11-04 |
| US20090212280A1 (en) | 2009-08-27 |
| EP1768200A1 (de) | 2007-03-28 |
| EP1721347B1 (de) | 2010-12-15 |
| IN2006MU00293A (Direct) | 2007-06-22 |
| JP2007526640A (ja) | 2007-09-13 |
| EP1768200B1 (de) | 2008-05-07 |
| US8258501B2 (en) | 2012-09-04 |
| DE502005004031D1 (de) | 2008-06-19 |
| CN1914747A (zh) | 2007-02-14 |
| EP1721347A2 (de) | 2006-11-15 |
| HK1100266A1 (en) | 2007-09-14 |
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Legal Events
| Date | Code | Title | Description |
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| FZDC | Discontinued application reinstated | ||
| FZDE | Discontinued |
Effective date: 20180305 |