WO2010048936A2 - Doppelkomplex-salze als absorber in osc/opv-vorrichtungen - Google Patents
Doppelkomplex-salze als absorber in osc/opv-vorrichtungen Download PDFInfo
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- WO2010048936A2 WO2010048936A2 PCT/DE2009/001505 DE2009001505W WO2010048936A2 WO 2010048936 A2 WO2010048936 A2 WO 2010048936A2 DE 2009001505 W DE2009001505 W DE 2009001505W WO 2010048936 A2 WO2010048936 A2 WO 2010048936A2
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- Prior art keywords
- formula
- complex
- oligomer
- metal
- double
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 65
- 239000006096 absorbing agent Substances 0.000 title description 9
- 229910052751 metal Inorganic materials 0.000 claims abstract description 59
- 239000002184 metal Substances 0.000 claims abstract description 49
- 230000005693 optoelectronics Effects 0.000 claims abstract description 28
- 239000003446 ligand Substances 0.000 claims description 83
- 238000010521 absorption reaction Methods 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000000962 organic group Chemical group 0.000 claims description 21
- 230000007935 neutral effect Effects 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 150000004696 coordination complex Chemical class 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 230000003595 spectral effect Effects 0.000 claims description 14
- 230000003993 interaction Effects 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 229910000071 diazene Inorganic materials 0.000 claims description 11
- -1 hydrocarbon radical Chemical class 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 150000002527 isonitriles Chemical class 0.000 claims description 9
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 7
- 125000000129 anionic group Chemical group 0.000 claims description 7
- 238000009792 diffusion process Methods 0.000 claims description 7
- 150000002825 nitriles Chemical class 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 7
- ICIXQGGQPKFQRL-UHFFFAOYSA-N al7182 Chemical compound COC1=CC=CC(N2S(C=3SC(=CC=3CC2)S(N)(=O)=O)(=O)=O)=C1 ICIXQGGQPKFQRL-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 238000010276 construction Methods 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 150000002500 ions Chemical class 0.000 claims description 3
- 238000005530 etching Methods 0.000 claims description 2
- 238000007740 vapor deposition Methods 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 9
- 229930195733 hydrocarbon Natural products 0.000 claims 9
- 210000004027 cell Anatomy 0.000 claims 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 5
- 229910052737 gold Inorganic materials 0.000 claims 3
- 229910052741 iridium Inorganic materials 0.000 claims 3
- 229910052703 rhodium Inorganic materials 0.000 claims 3
- 230000005855 radiation Effects 0.000 claims 2
- YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 claims 1
- MHSLDASSAFCCDO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylpyrazol-3-yl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound CN1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MHSLDASSAFCCDO-UHFFFAOYSA-N 0.000 claims 1
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
- 101100463133 Caenorhabditis elegans pdl-1 gene Proteins 0.000 claims 1
- 210000003850 cellular structure Anatomy 0.000 claims 1
- 229940125846 compound 25 Drugs 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 229940127573 compound 38 Drugs 0.000 claims 1
- 229940125844 compound 46 Drugs 0.000 claims 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 claims 1
- 229920001296 polysiloxane Polymers 0.000 claims 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 142
- 239000010410 layer Substances 0.000 description 52
- 230000009102 absorption Effects 0.000 description 41
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 29
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 28
- 239000000463 material Substances 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 17
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 15
- 239000000975 dye Substances 0.000 description 10
- 239000011159 matrix material Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 0 CCCCCCCC1N*(C)(*)*2C1(C)CCCCC2 Chemical compound CCCCCCCC1N*(C)(*)*2C1(C)CCCCC2 0.000 description 8
- 230000031700 light absorption Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002800 charge carrier Substances 0.000 description 6
- 230000037230 mobility Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VHJFWJXYEWHCGD-UHFFFAOYSA-N 4-nonyl-2-(4-nonylpyridin-2-yl)pyridine Chemical group CCCCCCCCCC1=CC=NC(C=2N=CC=C(CCCCCCCCC)C=2)=C1 VHJFWJXYEWHCGD-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 239000001301 oxygen Substances 0.000 description 5
- 150000003009 phosphonic acids Chemical class 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 4
- 239000004020 conductor Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 3
- 238000010494 dissociation reaction Methods 0.000 description 3
- 230000005593 dissociations Effects 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
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- 238000005063 solubilization Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- WPUSEOSICYGUEW-UHFFFAOYSA-N 4-[4-(4-methoxy-n-(4-methoxyphenyl)anilino)phenyl]-n,n-bis(4-methoxyphenyl)aniline Chemical compound C1=CC(OC)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(OC)=CC=1)C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 WPUSEOSICYGUEW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910021607 Silver chloride Inorganic materials 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 150000003057 platinum Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000007704 wet chemistry method Methods 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 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
- DKAXSGWOJGVZGP-UHFFFAOYSA-N 3h-dithiole-3-carboxylic acid Chemical compound OC(=O)C1SSC=C1 DKAXSGWOJGVZGP-UHFFFAOYSA-N 0.000 description 1
- NBPGPQJFYXNFKN-UHFFFAOYSA-N 4-methyl-2-(4-methylpyridin-2-yl)pyridine Chemical group CC1=CC=NC(C=2N=CC=C(C)C=2)=C1 NBPGPQJFYXNFKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000000695 excitation spectrum Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000013086 organic photovoltaic Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
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- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000002468 redox effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y10/00—Nanotechnology for information processing, storage or transmission, e.g. quantum computing or single electron logic
-
- 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
- C07F15/0086—Platinum compounds
- C07F15/0093—Platinum compounds without a metal-carbon linkage
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- 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
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
-
- 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
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
-
- 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
- H10K85/371—Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
-
- 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
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- 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
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- Double complex salts as absorbers in OSC / OPV devices Double complex salts as absorbers in OSC / OPV devices
- the present invention relates to double-complex salts in opto-electronic components and, in particular, oligomers formed from charged metal complexes for use in OSCs or OPVs.
- OPV organic photo voltaic
- OSCs organic solar cells
- An important aim of the invention is the efficient conversion of solar energy into electrical energy.
- the associated requirements for the device structure are in many ways similar to those for the construction of an OLED.
- OSCs organic solar cells
- the same dye materials can be used for OLEDs and OSCs if their absorptions reach far enough into the red or IR spectral region.
- OSCs There are three different types of OSCs:
- OSCs 1 in which the organic layers consist of so-called “small molecules” (SM solar cells are produced by vacuum deposition).
- OSCs in which the organic layers consist inter alia of polymers (polymer solar cells are produced by spin-coating or ink-jet printing.) 3) "Dye-Sensitized Solar Cells", which have a highly porous OO 2 electron conduction layer (these are prepared by sintering O 2 O and covered with the dye.) (Principle realized in the so-called Grätzel cell). ,
- OSC OSCs can also be distinguished according to their operating principle.
- separation of the electric charge occurs, followed by migration of the resulting hole and electron to the respective electrodes (see FIG. 1).
- the separation of the charge carriers is realized in different ways.
- the dye molecule on the surface of the electrode acts as a photosensitizer.
- electron transfer from the excited dye molecule to the electrode occurs.
- the oxidized dye molecule is subsequently reduced again by redox-active substances present in the electrolyte.
- the charge carriers are separated at an interface between different layers of the device.
- the exciton either directly at the interface between the hole and electron conduction layer arise (heterojunction solar cell), or an additional photoactive layer is introduced (p-i-n solar cell).
- the exciton inside this photoactive layer is generated by absorption of the photon and then travels towards the hole or electron conducting layer where charge separation occurs at the interface by a heterogeneous electron / hole transfer.
- the photoactive layer may also be realized in the form of a "bulk heterojunction" which is a mixture of hole and electron conductor material.
- OSCs are: i) a relatively simple manufacturing process (eg, no large ultra-pure crystals need to be grown), H) comparatively low production temperatures,
- an organic solar cell is very similar to that of an OLED, as shown in FIG. 1.
- a cell is fabricated in a sandwich geometry, with one electrode being a transparent semiconductor layer, mostly made of indium tin oxide (ITO).
- ITO indium tin oxide
- One or more organic layers are applied to this electrode: hole-line layer, light-absorption layer, electron-line layer, and the final metal electrode.
- the invention is based on the use of the oligomers formed from double complex salts in opto-electronic components, in particular in OSCs.
- the invention for use in opto-electronic construction elements, in particular in OSCs therefore relates to an oligomer comprising at least one, in particular at least two positively charged metal complexes and at least one, in particular at least two negatively charged metal complexes, wherein the metal complexes
- M1 and M2 independently represent a metal center selected from Ir (I), Rh (I), Pt (II), Pd (II), Au (III) and L1, L2, L3 and L4 and L5, L6 , L7 and L8 each represent a neutral or charged ligand, wherein two or more of the ligands L1, L2, L3 and L4 as well as L5, L6, L7 and L8 may also be linked together and n is 1 or 2.
- the ligands L1 - L8 must be chosen so that the specified and required total charge of the complex is maintained.
- the invention relates to the use of oligomers of differently charged metal complexes in optoelectronic components, preferably in OSCs, lasers, diodes or transistors.
- the electronic component is selected from OSCs 1 organic diode, organic transistor or organic laser.
- the optoelectronic component is preferably not an OLED (organic light emitting device).
- Oligomers preferably comprise at least 3, more preferably at least 4, more preferably at least 5, even more preferably at least 10, and most preferably at least 20 metal complexes.
- oligomers Preferably, oligomers have at most 200, in particular at most 100 metal complexes. By increasing the number of metal complexes in the oligomers, it is often possible to shift absorption further into the red spectral range in the case of absorber materials. Preference is given to trimers and tetramers of the metal complexes.
- the common structural feature of all the complexes used in the double complex salts is that the central ions M are square-planar coordinated four-fold, where the coordinations may be symmetric or asymmetric, with asymmetric arrangements being preferred.
- This invention relates to the use of a class of compounds in which an extremely intense absorption can arise only through a pronounced metal-metal interaction between planar, oppositely charged metal complexes.
- the transitions leading to absorption are thus based on metal-metal interactions of the individual complexes in the oligomer in this class of compounds. This is a huge difference to previous systems where light absorption is based on isolated, neutral molecules.
- Pt (II) complexes and structurally related second- and third-generation complexes of transition metals with a d 8 electron configuration show a tendency to form metal-metal interactions and form trimers, tetramers, .... or in general oligomers or columnar structures (the terms columnar structures, stacking arrangement, oligomers and aggregates are used synonymously here).
- Pd (II), Ir (I), Rh (I), and limited Au (III ) show a tendency to form metal-metal interactions and form trimers, tetramers, .... or in general oligomers or columnar structures (the terms columnar structures, stacking arrangement, oligomers and aggregates are used synonymously here).
- compounds show intense absorptions resulting from states that arise from metal-metal interactions.
- the invention is based on the use of differently charged metal complexes, ie, double-complex salts, which form trimers, tetramers, etc., or generally oligomers, in opto-electronic devices, which are preferably hermetically sealed to the outside.
- the permeability of the housing is particularly preferred for water vapor ⁇ 10 " ⁇ g * m '2 * d " 1 and particularly preferably for oxygen ⁇ 10 "6 cm 3 * m " 2 * d "1 * bar ' 1 , so that no gas exchange with the environment.
- the inventively used oligomers are metal complexes of
- K 2 [L5l_6L7L8M2f
- the metal centers M1 and M2 of the metal complexes are independently selected from Ir (I), Rh (I), Pt (II), Pd (II) or Au (III), preferably Pt (II) and Pd (II).
- M1 M2 or M1 ⁇ M2. Any combinations are possible, the charges of the individual complex building blocks must add up to zero.
- L1, L2, L3 and L4 and L5, L6, L7 and L8 are each independently a neutral or charged ligand, especially a monodentate or multidentate ligand.
- NL denotes neutral monodentate ligands
- AL denotes anionic monodentate ligands (for a more detailed definition of ligands see below).
- the ligands Ll 1 L2, L3 and L4 in the general formula [L1 L2L3L4M1] n + are not necessarily identical to the ligands also designated L1 to L4 of another general formula [L1 L2L3L4M1] n + . Since, according to the invention, the states leading to the absorption essentially result from MM interactions, the ligands themselves do not have to have any chromophoric .pi. Systems.
- oligomers to be used according to the invention are explained in more detail below. Preference is given to using oligomers / columnar structures which have comparatively small M-M distances in order to ensure the high absorptions, which are important for OSCs, as far as the red or the near IR spectral range. Also preferred are oligomers / columnar structures with medium and larger M-M distances, with which high absorptions z. B. in the green or blue spectral range.
- Ki square-planar, singly positively charged complex
- K 2 square-planar, singly negatively charged complex
- Ki [L1 L2L3L4M1 (I)] +
- the ligands of the second formula are marked with a dash and are therefore designated as L1 ', L2', L3 1 or L4 '. These ligands may be ligands other than the non-struck ligands to achieve charge balance. In principle, the ligands L1 'to L8' can have the meanings given for the ligands L1 to L8.
- K 2 [L 5 L 6 L 7 L 8 M 2 (I)] - [L5 ' L6 ' L7 ' L8 ' M2 (II)] -
- Ki square-planar, double-positively charged complex
- K 2 square-planar, double negatively charged complex
- K 1 [L1 L2L3L4M1 (II) J i2 +
- MI MI
- M2 (II) Pt (II)
- Examples of the component K 1 [L1L2L3L4Pt (H)] 2+ :
- Examples of cationic complexes which can be used are ⁇ -diimine complexes such as 74-78, carbene complexes such as 83-84, Pinzer complexes such as 85-103 and generally square-planar platinum complexes (104) with neutral ligands NL1-NL4 ,
- diimine ligands R1 to R20, NU to NL4 and AL1 to AL4 are as defined herein (see Chapter: Definition of Ligands and Residues).
- carbene ligands R1 to R20, NL1 to NL4 and AL1 to AL4 are as defined herein (see Chapter: Definition of Ligands and Residues).
- 135-141 exemplifies a series of complex anions of the general form (133) and (134):
- Double complex salts consisting of differently charged complexes with different central metals
- the Pd complex stack acts like a matrix interacting with the doped Pt complex. Due to this principle, the absorption maxima shift and the emissions change.
- the doping can be carried out on columnar structures, which are composed of singly or doubly charged complexes (Kt, K 2 ).
- Doped columnar structures are preferably suitable for use in optoelectronic components, such as lasers, diodes or transistors.
- Doped columnar structures are particularly suitable for achieving a blue emission.
- a shift or influence on the emission wavelength towards blue wavelengths is often desired, especially in laser applications.
- K- I square-planar, singly positively charged Pd complex
- K 2 square-planar, singly negatively charged Pd complex
- Di square-planar, singly positively charged Pt complex
- D 2 square-planar, simply negatively charged Pt complex
- Ki square-planar, doubly positively charged Pd complex
- K 2 square-planar, doubly negatively charged Pd complex
- Di square-planar, doubly positively charged Pt complex
- D 2 square-planar, doubly negatively charged Pt -Complex
- the complex used for the doping is in the oligomer matrix preferably in a molar ratio of at most 1: 3, preferably at most 1: 10, preferably at most 1: 50 and in particular at most 1: 100, based on the oligomer matrix-forming complexes, in front.
- the complex used for the doping is preferably present in the oligomer matrix in a molar ratio of at least 1: 100,000, preferably at least 1: 10,000, more preferably at least 1: 1,000, based on the oligomer matrix-forming complexes.
- the illustrated concept of doping columnar structures can be used primarily to control the absorption and emission wavelengths and is therefore of great importance for OSC applications.
- This inventive concept is particularly characterized by the fact that due to the defined charge of the doped complexes, D1 or D2, in the inventive construction principle no -D1-D1 or -D2-D2 neighbor arrangements can occur.
- double-complex salts with different metal centers in stoichiometric composition may also occur.
- a further component is doped.
- Such structures can be used for all opto-electronic components mentioned herein, preferably for OSCs.
- Ki square planar, single positive (negatively) charged complex
- K 2 square planar, single negative (positive) charged complex
- Ki [L1L2L3L4M1 (I)] +
- MI (II) / M2 (II) Pt (II), Pd (II)
- Ki square-planar, two-fold positive (negatively charged) complex
- K 2 square-planar, two-fold negative (positive) charged complex
- Ki [L1L2L3L4M1 (H) I 2+
- L1-L4 and L5-L8 are each independently a neutral or charged ligand, especially a monodentate or multidentate ligand.
- the ligands L1 - L8 must be chosen so that the respective required total charge of the complex is maintained.
- the ligands designated in a metal-complex combination with L1 to L8 and LT to L8 ' are not necessarily identical to the ligands named in another combination also with L1 to L8 and L1 ' to L8 ' .
- the NL1-NL4 ligands are neutral ligands, eg, carbonyl CO, nitriles NCR 1 , isonitrile CNR "(R 'and R” are defined as R1-R20), or oxazoles.
- R 'and R are defined as R1-R20
- nitriles or isonitriles which are substituted by a large organic group R 'or R "(R' and R" defined as R1-R20).
- the ligands AL1-AL4 are anionic ligands, such as cyanide CN ⁇ chloride bromide CF 1 Br "iodide T 1 RS", RO ⁇ ⁇ SCN OCN "aryl groups, alkenyl groups, alkynyl groups or borates.
- carbene ligand specifically means:
- Cyclometalating ligands as used herein, are bidentate, simply negatively charged ligands
- Units A and B can be made up of five or six rings exist, as well as be open-chain.
- R (X) organic radical defined as R1-R20
- N 1 E can be either NR, O or S.
- the unit B may consist of a five- or six-ring, but also be open-chain.
- R1-R20 are organic groups which may be the same or different.
- the organic groups may in particular be selected from: hydrogen, halogen or groups which are bonded via oxygen (-OR), nitrogen (-NR 2) or silicon (-SiR 3 ), as well as alkyl, aryl, heteroaryl and alkenyl Groups or substituted alkyl, aryl, heteroaryl and alkenyl groups having substituents such as halogens, alkyl groups and other well-known donor and acceptor groups.
- the organic groups R1 -R20 can also lead to fused ring systems.
- the groups R1-R20 preferably contain 1 to 30 C atoms, more preferably 1 to 20 C atoms.
- long chain - and branched - alkyl chains (Ci- C 3 0) and short chain polyether [for example, polymers (-OCH 2 CH 2 O-) n, n ⁇ 500].
- the alkyl chains can also be modified with polar groups, for example with alcohols, aldehydes, amines, carboxylic acids, ethers, phosphoric esters, phosphonic acids, which allow a further increase in the solubility.
- the radical R is organic groups (analogous to the definition of R 1 -R 2 O).
- the organic groups may in particular be selected from hydrogen, halogen or groups which are bonded via oxygen (-OR), nitrogen ( -NR2) or silicon (-SiR3), as well as alkyl, aryl, heteroaryl and alkenyl groups or substituted alkyl, aryl, heteroaryl and alkenyl groups having substituents such as halogens, alkyl groups and other generally known Donor and acceptor groups.
- the organic groups can also lead to annelated ring systems.
- long-chain - also branched - alkyl chains C1-C30
- short-chain polyethers eg polymers (-OCH 2 CH 2 O-) n, n ⁇ 500].
- the alkyl chains can also be modified with polar groups, for example with alcohols, aldehydes, amines, carboxylic acids, ethers, phosphoric esters, phosphonic acids, which allow a further increase in the solubility.
- the organic groups may in particular be selected from: hydrogen, Halogen or groups which are bonded via oxygen (-OR), nitrogen (-NR 2 ) or silicon (-SiR 3 ), and also alkyl, aryl, heteroaryl and alkenyl groups or substituted alkyl, aryl, Heteroaryl and alkenyl groups having substituents such as halogens, alkyl groups and other well-known donor and acceptor groups.
- the organic groups can also lead to annelated ring systems.
- long-chain - also branched - alkyl chains C 1 -C 30
- short-chain polyether eg polymers (- OCH 2 CH 2 O-) n , n ⁇ 500].
- the alkyl chains can also be modified with polar groups, for example with alcohols, aldehydes, amines, carboxylic acids, ethers, phosphoric esters, phosphonic acids, which allow a further increase in the solubility.
- R (X) herein represents organic groups (analogous to the definition of R1-R20) which may be the same or different. X is a running digit and is used to number the rest R (eg R (1), R (2), ).
- the organic groups may in particular be selected from: hydrogen, halogen or groups which are bonded via oxygen (-OR), nitrogen (-NR 2 ) or silicon (-SiRs), as well as alkyl, aryl, heteroaryl and alkenyl Groups or substituted alkyl, aryl, heteroaryl and alkenyl groups having substituents such as halogens, alkyl groups and other well-known donor and acceptor groups.
- the organic groups can also lead to annelated ring systems.
- the alkyl chains can also be modified with polar groups, for example with alcohols, aldehydes, amines, carboxylic acids, ethers, phosphoric esters, phosphonic acids, which allow a further increase in the solubility.
- Alkyl groups as described herein mean especially C1 -C30, Cr C preferably 2 o-alkyl, particularly preferably C 1 -C 1 0 alkyl radicals may also form a cycle.
- Alkenyl and alkynyl radicals preferably have 1 to 30, in particular 2 to 20, carbon atoms, more preferably 2 to 8.
- Aryl groups are preferably systems having 5 to 30, in particular 5 to 10, ring atoms, preferably 1 to 4 heteroatoms selected from O, N, P
- ligand units A and / or B of the ⁇ -diimine ligands, carbene ligands and cyclometalating ligands may also be bridged with NL and / or AL.
- double-complex salts which can preferably be used as absorbers in OSCs (OPVs).
- OCVs OSCs
- the absorptions of the materials reach into the near IR range.
- CNR denotes common isonitrile ligands
- the oligomers described in Table 1 are outstandingly suitable for use in opto-electronic components, especially in OSCs.
- OSCs In the fabrication of OSCs, all of the oligomers or columnar structures described herein can be used.
- the particular desired absorption wavelength can optionally be selectively changed.
- double-complex salts, combinations, dopants which are preferably used in opto-electronic devices, such as lasers, diodes or transistors.
- CNR denotes common isonitrile ligands
- Platinum-double complex salts of the general form [L1 L2L3L4Pt] 2+ [Pt (AL1) 4 ] 2 " are generally insoluble
- the ligands L1-L4 are neutral
- L1-L4 may also be interconnected, ie, multidentate They form complexes that contain, for example, either a) a bidentate and two monodentate ligands, b) two bidentate ligands, c) a tridentate and a monodentate ligand, or d) a tetradentate ligand Ligands to ⁇ -diimines, such as 2,2'-bipyridine or 1, 10-phenanthroline, and AL1 is a cyanide, chloride, bromide or iodide ion. Because of their outstanding photophysical properties, this invention provides this double complex Salts are good candidates for optoelectronic applications (OSCs).
- OSCs optoelectronic applications
- Glass or any other suitable solid or flexible transparent material may be used as the substrate.
- ITO indium tin oxide
- ETL electron transport layer
- the solubilisable oligomers / columnar structures described herein are preferably from 5% by weight to 100% by weight (particularly preferably from 30 to 100%) and may be e.g. dissolved in organic solvents and then applied (Method A).
- the oligomers / columnar structures in the case of insufficient solubility
- the stated process C can also be used .
- a suitable electron or hole-conducting substance or a mixture of the two
- Some examples of the n- and p-type materials can be found in FIGS. 4A and 4B.
- HTL hole transport layer
- MeO-TPD ⁇ /, ⁇ /, ⁇ / ', ⁇ /' - tetrakis- (4-methoxyphenyl) -benzidine.
- the HTL matrix material can also be doped with a p-dopant, eg MeO-TPD + F 4 -TCNQ (tetrafluoro-tetracyanoquinodimethane)
- the conductive metal layer is evaporated.
- Au represents an example. Other metals can also be used.
- Fig. 3 shows an embodiment
- a further aspect of the invention is an optoelectronic device, in particular a light absorbing device comprising (i) an anode, (ii) a cathode and (iii) an absorption layer arranged between and in direct or indirect contact with the anode or cathode comprising at least one oligomer as defined herein.
- the optoelectronic devices according to the invention are preferably produced by wet chemistry.
- insoluble double-complex salt [Pt (bpy) 2 ] [Pt (CN) 4 ] is intended to illustrate the concept of solubilization of metal-metal double complex salts.
- the solution is placed in the freezer overnight, with a beige solid precipitating.
- the precipitate is filtered off with suction and washed with ethanol and ether, and then dried.
- the solid is dissolved in dichloromethane and precipitated with ether.
- the fine, pale green precipitate is filtered off and dried in a desiccator.
- Fig. 5 shows the optical excitation spectrum and the emission spectrum of this new substance.
- the light absorption strength of a material at a given wavelength ⁇ is given by the Lambert-Beer law:
- the ⁇ ( ⁇ ) values for most known materials in the visible or in the near IR are only 10 3 - 10 4 ] mol "1 cm '1 , which means that the extinction coefficients are too low!
- the MM distances in the oligomers / columnar structures and the average chain lengths of these oligomers / columnar structures can be varied almost as desired.
- the layers of the absorption bands can be selectively controlled over a wide range, and it is possible to produce new oligomers / columnar structures whose absorption can be adjusted over the entire spectral range (visible spectral range to the near infrared range).
- These high absorptions z. B. to the red or in the near IR range can be realized with small MM intervals in the oligomers / columnar structures of the double complex salts.
- the absorber material can be optimally adapted to the solar spectrum.
- Such oligomers / columnar structures are especially well suited for use in the OSCs mentioned here and are not yet to be found in this form in the prior art.
- the oligomers / columnar structures of the double-complex salts can be used, which are composed of monomers which are described above.
- the double-complex salts are chemically and photochemically particularly stable and are therefore particularly suitable for use as absorbers in OSCs (OPVs).
- oligomer / columnar structure double complex salts to be used according to the invention in optoelectronic devices have very good charge carrier mobilities. Due to the M-M interactions, the HOMO and LUMO are electronically delocalized over many molecules (building blocks of the oligomers / columnar structures). This also leads to a significant improvement in hole and electron mobility. As a result, the absorber layer does not require additional components to enhance mobility, i. the sometimes restrictive matrix requirements for good carrier mobility can be eliminated with the use of these double-complex salts in many applications. This makes it possible to achieve a large increase in efficiency and a cheaper production of OSCs (OPVs).
- OSCs OSCs
- the salts are readily soluble, but still retain the favorable optical properties.
- preferably long-chain - also branched - alkyl chains (C1-C30) and short-chain polyether [eg polymers (-OCH 2 CH 2 O-) n, n ⁇ 500]. be used.
- the alkyl chains can also be modified with polar groups, for example with alcohols, aldehydes, amines, carboxylic acids, ethers, phosphoric esters, phosphonic acids, which allow a further increase in the solubility.
- colloidal dispersions of the oligomers / columnar structures can be mixed in / mixed in a suitable polymer.
- concentration of the oligomers in the polymer is 2 to 10 wt .-% or 10 to 90 wt .-%.
- the pure oligomers / columnar structures i.e., without polymer
- the oligomer strands / columnar structures can be reduced in size prior to incorporation into the polymer by ultrasonic processing in the liquid phase. This is done by introducing the first component and adding the second, third, ... component in the ultrasonic bath.
- the double complex salts are then introduced into the polymer after filtering by micro / nanofilters. This also applies to the application as a 100% emitter layer.
- the novel diffusion method proposed here for the first time is suitable for the production of the emission layers.
- one of the generally soluble components of the double complex salts is introduced into the optically relevant polymer layer.
- the second component is then applied to this layer.
- the second component migrates to the first component where it forms the insoluble oligomer.
- the process is stopped when the desired double complex salt concentration is reached.
- the oligomers / columnar structures in one of the forms discussed above are used in the preparation of the OSCs, then the oligomer strands in the absorption layer are present in disordered relation to one another. If light strikes this layer, part of it is absorbed by one oligomer strand, the other part is reflected by it and strikes neighboring strands. There again a part is absorbed and reflected. Until the incident light has passed through the absorption layer, this process of absorption and reflection occurs many times, resulting in improved absorption efficiencies compared to conventional OSCs. In the case of OSCs which correspond to the state of the art, the incident light is often already reflected on the surface of the absorption layer and can thus no longer be used.
- the electronic properties of the complex salts of the oligomers described herein are anisotropic.
- isotropic properties of the optoelectronic component result again parallel to the surface.
- an absorber layer is obtained, which in addition to the increased absorption also has a high charge carrier mobility in a defined direction.
- the increase in absorption is achieved in comparison to the random orientation of the columnar structures in that these layers can be oriented optimally to the irradiation direction of the light (see FIG. 6A, which is a schematic of a component with columnar structures aligned perpendicular to the substrate surface).
- HTL hole transport layer (FIG. Hole transport layer)
- ETL electron transport layer
- Such structures can be conveniently prepared from a dispersion of already formed columnar structures (see item A or B) by applying the dispersion to the desired substrate and uniformly aligning the complex stacks by shear (e.g., by means of a brush or spatula).
- the complex stacks can also be aligned by stretching the film in the stretch direction (shown schematically in FIG. 6B).
- Columnar structures can additionally act as a scaffold for polymeric (matrix) materials.
- polymeric (matrix) materials As a result of the presence of the complex stacks embedded in a polymer, the polymers surrounding them can be excited to partially crystallize (analogously to corresponding additives in the case of polyolefins). Due to the presence of crystalline polymeric domains, the efficiency of e.g. Charge carrier materials can be increased because the order and thus the conjugation length of the polymers increases.
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Abstract
Description
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EP09805900A EP2337828A2 (de) | 2008-10-24 | 2009-10-22 | Doppelkomplex-salze als absorber in osc/opv-vorrichtungen |
US13/125,949 US8728567B2 (en) | 2008-10-24 | 2009-10-22 | Double complex salts as absorbers in OSC/OPV devices |
CN2009801518354A CN102257099A (zh) | 2008-10-24 | 2009-10-22 | Osc/opv装置中作为吸收剂的复络合盐 |
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JP2014508817A (ja) * | 2010-12-23 | 2014-04-10 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子 |
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DE102016105205A1 (de) * | 2016-03-21 | 2017-09-21 | Osram Oled Gmbh | Optoelektronisches Bauelement und Verfahren zum Betreiben eines optoelektronischen Bauelements |
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US6160267A (en) | 1999-01-05 | 2000-12-12 | Regents Of The University Of Minnesota | Vapochromic led |
US20050211974A1 (en) * | 2004-03-26 | 2005-09-29 | Thompson Mark E | Organic photosensitive devices |
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DE102006030860A1 (de) * | 2006-07-04 | 2008-01-10 | Universität Regensburg | Oligomere von Isonitril-Metallkomplexen als Triplett-Emitter für OLED-Anwendungen |
JP2008066542A (ja) * | 2006-09-07 | 2008-03-21 | Univ Chuo | 金属錯体化合物、電子素子、デバイス、電子素子の駆動方法 |
DE102008013691A1 (de) * | 2008-03-11 | 2009-09-17 | Merck Patent Gmbh | Verwendung von Zusammensetzungen neutraler Übergangsmetallkomplexe in opto-elektronischen Bauelementen |
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2008
- 2008-10-24 DE DE102008053107.3A patent/DE102008053107B4/de not_active Expired - Fee Related
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2009
- 2009-10-22 EP EP09805900A patent/EP2337828A2/de not_active Withdrawn
- 2009-10-22 US US13/125,949 patent/US8728567B2/en active Active
- 2009-10-22 JP JP2011532497A patent/JP5490126B2/ja not_active Expired - Fee Related
- 2009-10-22 CN CN2009801518354A patent/CN102257099A/zh active Pending
- 2009-10-22 WO PCT/DE2009/001505 patent/WO2010048936A2/de active Application Filing
- 2009-10-22 KR KR1020117011384A patent/KR20110090936A/ko not_active Application Discontinuation
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2014508817A (ja) * | 2010-12-23 | 2014-04-10 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセンス素子 |
DE102011017572A1 (de) * | 2011-04-27 | 2012-10-31 | Siemens Aktiengesellschaft | Bauteil mit orientiertem organischem Halbleiter |
US9159959B2 (en) | 2011-04-27 | 2015-10-13 | Siemens Aktiengesellschaft | Component having an oriented organic semiconductor |
Also Published As
Publication number | Publication date |
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CN102257099A (zh) | 2011-11-23 |
EP2337828A2 (de) | 2011-06-29 |
JP5490126B2 (ja) | 2014-05-14 |
US20110212258A1 (en) | 2011-09-01 |
DE102008053107A1 (de) | 2010-04-29 |
DE102008053107B4 (de) | 2022-05-12 |
KR20110090936A (ko) | 2011-08-10 |
WO2010048936A3 (de) | 2010-07-29 |
US8728567B2 (en) | 2014-05-20 |
JP2012506625A (ja) | 2012-03-15 |
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