WO2013014207A1 - Komplexverbindungen mit einem mehrzähnigen, asymmetrischen liganden und ihre verwendung im opto-elektronischen bereich - Google Patents
Komplexverbindungen mit einem mehrzähnigen, asymmetrischen liganden und ihre verwendung im opto-elektronischen bereich Download PDFInfo
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- WO2013014207A1 WO2013014207A1 PCT/EP2012/064631 EP2012064631W WO2013014207A1 WO 2013014207 A1 WO2013014207 A1 WO 2013014207A1 EP 2012064631 W EP2012064631 W EP 2012064631W WO 2013014207 A1 WO2013014207 A1 WO 2013014207A1
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- donor
- metal complex
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- 239000003446 ligand Substances 0.000 title claims abstract description 53
- 150000001875 compounds Chemical class 0.000 title description 12
- 230000005693 optoelectronics Effects 0.000 title description 5
- -1 metal complex compound Chemical class 0.000 claims abstract description 42
- 229910052751 metal Inorganic materials 0.000 claims abstract description 23
- 125000003368 amide group Chemical group 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims description 14
- 150000004696 coordination complex Chemical class 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 229910052802 copper Inorganic materials 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 239000012634 fragment Substances 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000006096 absorbing agent Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052737 gold Inorganic materials 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 229910052741 iridium Inorganic materials 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
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- 239000001257 hydrogen Substances 0.000 claims description 4
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- FVHYOVFCJQRHGS-UHFFFAOYSA-N n,n'-diethylethane-1,2-diimine Chemical compound CCN=CC=NCC FVHYOVFCJQRHGS-UHFFFAOYSA-N 0.000 description 1
- YRHYXWGIOLWSEI-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diimine Chemical compound CN=CC=NC YRHYXWGIOLWSEI-UHFFFAOYSA-N 0.000 description 1
- HLGUAVMAMZECCK-UHFFFAOYSA-N n-(2-methylphenyl)-1-pyridin-2-ylethanimine Chemical compound C=1C=CC=NC=1C(C)=NC1=CC=CC=C1C HLGUAVMAMZECCK-UHFFFAOYSA-N 0.000 description 1
- DABHMSHNJTUDIQ-UHFFFAOYSA-N n-ethyl-1-pyridin-2-ylethanimine Chemical compound CCN=C(C)C1=CC=CC=N1 DABHMSHNJTUDIQ-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- LTJMAOIYDHFJAF-UHFFFAOYSA-N n-phenyl-1-pyridin-2-ylethanimine Chemical compound C=1C=CC=NC=1C(C)=NC1=CC=CC=C1 LTJMAOIYDHFJAF-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RCIBIGQXGCBBCT-UHFFFAOYSA-N phenyl isocyanide Chemical compound [C-]#[N+]C1=CC=CC=C1 RCIBIGQXGCBBCT-UHFFFAOYSA-N 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical group C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003346 selenoethers Chemical class 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical class [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
- PFXVKGGZWQQTSE-UHFFFAOYSA-N sulfuryl dicyanide Chemical compound N#CS(=O)(=O)C#N PFXVKGGZWQQTSE-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- FAGLEPBREOXSAC-UHFFFAOYSA-N tert-butyl isocyanide Chemical compound CC(C)(C)[N+]#[C-] FAGLEPBREOXSAC-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- HVYVMSPIJIWUNA-UHFFFAOYSA-N triphenylstibine Chemical compound C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 HVYVMSPIJIWUNA-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
- H10K85/371—Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
-
- 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
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
- H10K30/50—Photovoltaic [PV] devices
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- 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
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Definitions
- amides e.g. Dimethylamide, diethylamide and morpholide
- carboxylates e.g. Acetate, trifluoroacetate, propionate and benzoate
- anionic, nitrogen-containing heterocycles e.g. Pyrrolid, imidazolide, pyrazolide, aliphatic and aromatic phosphides or aliphatic or aromatic selenides.
Landscapes
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- High Energy & Nuclear Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Photovoltaic Devices (AREA)
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12738475.8A EP2737556A1 (de) | 2011-07-26 | 2012-07-25 | Komplexverbindungen mit einem mehrzähnigen, asymmetrischen liganden und ihre verwendung im opto-elektronischen bereich |
JP2014522088A JP2014532290A (ja) | 2011-07-26 | 2012-07-25 | 非対称多座配位子を有する錯体化合物およびオプトエレクトロニクス分野におけるその使用 |
US14/234,710 US20140176022A1 (en) | 2011-07-26 | 2012-07-25 | Complex compounds having a polydentate, asymmetrical ligand and the use thereof in the opto-electronic field |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102011079846.3 | 2011-07-26 | ||
DE102011079846.3A DE102011079846B4 (de) | 2011-07-26 | 2011-07-26 | Komplexverbindungen mit einem mehrzähnigen, asymmetrischen Liganden und ihre Verwendung im opto-elektronischen Bereich |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2013014207A1 true WO2013014207A1 (de) | 2013-01-31 |
Family
ID=46579043
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2012/064631 WO2013014207A1 (de) | 2011-07-26 | 2012-07-25 | Komplexverbindungen mit einem mehrzähnigen, asymmetrischen liganden und ihre verwendung im opto-elektronischen bereich |
Country Status (5)
Country | Link |
---|---|
US (1) | US20140176022A1 (de) |
EP (1) | EP2737556A1 (de) |
JP (1) | JP2014532290A (de) |
DE (1) | DE102011079846B4 (de) |
WO (1) | WO2013014207A1 (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10517849B2 (en) | 2016-10-26 | 2019-12-31 | Constellation Pharmaceuticals, Inc. | LSD1 inhibitors and medical uses thereof |
US10526287B2 (en) | 2015-04-23 | 2020-01-07 | Constellation Pharmaceuticals, Inc. | LSD1 inhibitors and uses thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6963005B2 (en) * | 2002-08-15 | 2005-11-08 | E. I. Du Pont De Nemours And Company | Compounds comprising phosphorus-containing metal complexes |
US20070111026A1 (en) * | 2005-11-15 | 2007-05-17 | Deaton Joseph C | Oled devices with dinuclear copper compounds |
WO2010006681A1 (de) | 2008-07-17 | 2010-01-21 | Merck Patent Gmbh | Komplexe zur verwendung in opto-elektronischen bauteilen |
-
2011
- 2011-07-26 DE DE102011079846.3A patent/DE102011079846B4/de not_active Expired - Fee Related
-
2012
- 2012-07-25 EP EP12738475.8A patent/EP2737556A1/de not_active Withdrawn
- 2012-07-25 JP JP2014522088A patent/JP2014532290A/ja active Pending
- 2012-07-25 WO PCT/EP2012/064631 patent/WO2013014207A1/de active Application Filing
- 2012-07-25 US US14/234,710 patent/US20140176022A1/en not_active Abandoned
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6963005B2 (en) * | 2002-08-15 | 2005-11-08 | E. I. Du Pont De Nemours And Company | Compounds comprising phosphorus-containing metal complexes |
US20070111026A1 (en) * | 2005-11-15 | 2007-05-17 | Deaton Joseph C | Oled devices with dinuclear copper compounds |
WO2010006681A1 (de) | 2008-07-17 | 2010-01-21 | Merck Patent Gmbh | Komplexe zur verwendung in opto-elektronischen bauteilen |
Non-Patent Citations (2)
Title |
---|
HARKINS S B ET AL: "A Highly Emissive Cu2N2 Diamond Core Complex Supported by a [PNP]- Ligand", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, ACS PUBLICATIONS, US, vol. 127, 27 January 2005 (2005-01-27), pages 2030 - 2031, XP002425033, ISSN: 0002-7863, DOI: 10.1021/JA043092R * |
JOSEPH C. DEATON ET AL: "E-Type Delayed Fluorescence of a Phosphine-Supported Cu 2 ([mu]-NAr 2 ) 2 Diamond Core: Harvesting Singlet and Triplet Excitons in OLEDs ||", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 132, no. 27, 17 June 2010 (2010-06-17), pages 9499 - 9508, XP055031756, ISSN: 0002-7863, DOI: 10.1021/ja1004575 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10526287B2 (en) | 2015-04-23 | 2020-01-07 | Constellation Pharmaceuticals, Inc. | LSD1 inhibitors and uses thereof |
US10517849B2 (en) | 2016-10-26 | 2019-12-31 | Constellation Pharmaceuticals, Inc. | LSD1 inhibitors and medical uses thereof |
US11013718B2 (en) | 2016-10-26 | 2021-05-25 | Constellation Pharmaceuticals, Inc. | LSD1 inhibitors and medical uses thereof |
US11547695B2 (en) | 2016-10-26 | 2023-01-10 | Constellation Pharmaceuticals, Inc. | LSD1 inhibitors and medical uses thereof |
Also Published As
Publication number | Publication date |
---|---|
EP2737556A1 (de) | 2014-06-04 |
DE102011079846A1 (de) | 2013-01-31 |
JP2014532290A (ja) | 2014-12-04 |
US20140176022A1 (en) | 2014-06-26 |
DE102011079846B4 (de) | 2014-02-06 |
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