Online citations, reference lists, and bibliographies.

TADFMaterial Design : Photophysical Background And Case Studies Focusing On Cu ( I ) And Ag ( I ) Complexesa

H. Yersin, Rafał Czerwieniec, M. Z. Shafikov, Alfiya F Suleymanova
Published 2018 ·
Cite This
Download PDF
Analyze on Scholarcy
Share
Basic research of photophysical and chemical properties of organo-transition metal compounds was strongly activated by their potential commercial use. This became particularly apparent for classes of compounds that may be applied as emitters in organic light-emitting diodes (OLEDs) [1–19] or in light emitting electrochemical cells (LEEC) [7, 20–28]. These scientific investigations led to a much deeper understanding of the photophysical principles and of the compound’s properties resulting in the development of an enormous number of new materials in part with drastically improved properties for OLED applications [4, 9, 29–52]. Improvements were also stimulated in the fields of related functional materials based on metal complexes for sensing of oxygen or temperature [53–59] or for photocatalysis [60–66]. For luminescent materials to be applied in OLEDs, it is essential that all excitons generated in the emission layer are harvested and converted into photons. Since the statistic ratio of the formed excitons is 1 singlet to 3 triplets [67, 68], special mechanisms that allow to harvest all of them are required, as the two types of excitons show different relaxation properties [67]. Already about 20 years ago, it was discovered that third-row transition metal complexes, especially those with Ir(III), Pt(II), or Os(II) metal centers, are well suited for such harvesting processes, since the metal centers can induce efficient spin–orbit coupling (SOC) [69–77] between the lowest triplet state T1 and higher-lying singlet states Sn (with n > 1) [1, 9, 11, 12, 67, 69–89]. As a consequence, fast intersystem crossing (ISC) to the lowest triplet state of several tens of femtosecond [88, 90] can occur, and relatively high radiative phosphorescent rates from the T1 state to the electronic
This paper references
10.1021/ic5012204
Luminescent dinuclear Cu(I) complexes containing rigid tetraphosphine ligands.
Claudia Bizzarri (2014)
10.1021/ic1009253
Iridium metal complexes containing N-heterocyclic carbene ligands for blue-light-emitting electrochemical cells.
C. Yang (2010)
10.1021/ja2026568
Systematic investigation of the metal-structure-photophysics relationship of emissive d10-complexes of group 11 elements: the prospect of application in organic light emitting devices.
Chien-Wei Hsu (2011)
10.1002/adma.201405897
Bridging the efficiency gap: fully bridged dinuclear Cu(I)-complexes for singlet harvesting in high-efficiency OLEDs.
Daniel Volz (2015)
10.1002/JSID.654
Design strategies for materials showing thermally activated delayed fluorescence and beyond: Towards the fourth‐generation OLED mechanism
Hartmut Yersin (2018)
Energy transfer and harvesting in [Ru 1− x Os x (bpy) 3](PF 6) 2 and {Λ-[Ru(bpy) 3]Δ-[Os(bpy) 3]}(PF 6) 4
Hartmut Yersin (2002)
10.1021/ja00857a013
Charge-transfer exited states of ruthenium(II) complexes. I. Quantum yield and decay measurements
G. Hager (1975)
10.1021/ACS.JPCC.5B03530
On Predicting the Excited State Properties of Thermally Activated Delayed Fluorescence Emitters
T. Penfold (2015)
10.1002/chin.199739314
Low-Lying Electronic States of (Rh(bpy)3)3+, (Pt(bpy)2)2+, and (Ru(bpy) 3)2+. A Comparative Study Based on Highly Resolved and Time-Resolved Spectra
Hartmut Yersin (1997)
Komplexe mit kleinen
H. Yersin (1988)
TADF for singlet
H. Yersin (2014)
10.1002/chem.201301449
Aryl radical formation by copper(I) photocatalyzed reduction of diaryliodonium salts: NMR evidence for a Cu(II)/Cu(I) mechanism.
Alexandre Baralle (2013)
10.1117/12.731225
Spin-orbit coupling routes and OLED performance: studies of blue-light emitting Ir(III) and Pt(II) complexes
Andreas F. Rausch (2007)
10.1002/CHIN.201431226
Bright Coppertunities: Multinuclear CuI Complexes with N—P Ligands and Their Applications
Manuela Wallesch (2014)
10.1002/chem.201504392
Red Phosphorescent Bis-Cyclometalated Iridium Complexes with Fluorine-, Phenyl-, and Fluorophenyl-Substituted 2-Arylquinoline Ligands.
Jwajin Kim (2016)
10.1021/ACS.CHEMMATER.5B03245
Light-Emitting Electrochemical Cells and Solution-Processed Organic Light-Emitting Diodes Using Small Molecule Organic Thermally Activated Delayed Fluorescence Emitters
Michael Y. Wong (2015)
10.1021/jacs.6b13311
Highly Stable Red-Light-Emitting Electrochemical Cells.
Cathrin D. Ertl (2017)
10.1039/c5cc04326c
Copper(I) complexes as alternatives to iridium(III) complexes for highly efficient oxygen sensing.
Santiago Medina-Rodríguez (2015)
10.1021/ACS.INORGCHEM.6B00068
Highly Efficient Thermally Activated Delayed Fluorescence in Dinuclear Ag(I) Complexes with a Bis-Bidentate Tetraphosphane Bridging Ligand.
Jin Chen (2016)
10.1039/c4cp03843f
The substituent effect on the MLCT excited state dynamics of Cu(I) complexes studied by femtosecond time-resolved absorption and observation of coherent nuclear wavepacket motion.
Linqiang Hua (2015)
10.1002/anie.201205915
Photocatalytic water reduction with copper-based photosensitizers: a noble-metal-free system.
Shu-Ping Luo (2013)
10.1196/annals.1430.044
Thermally activated delayed fluorescence in fullerenes.
Carlos Baleizão (2008)
10.1039/c6cc06729h
Lessons learned in tuning the optoelectronic properties of phosphorescent iridium(iii) complexes.
Adam F Henwood (2017)
10.1021/CM5006086
Simple and High Efficiency Phosphorescence Organic Light-Emitting Diodes with Codeposited Copper(I) Emitter
Zhongyuan Liu (2014)
10.1021/j100001a035
Time-resolved vibrational structures of the triplet sublevel emission of Pd(2-thpy)2
Jürgen Schmidt (1995)
10.1016/J.JLUMIN.2016.08.004
Highly efficient blue–green neutral dinuclear copper(I) halide complexes containing bidentate phosphine ligands
X. Hong (2016)
10.1063/1.1733823
Electronic Excitation Transfer and Relaxation
G. W. Robinson (1963)
10.1002/ADFM.201101907
Triplet exciton confinement in green organic light-emitting diodes containing luminescent charge-transfer Cu(I) complexes
Qisheng Zhang (2012)
3ππ* state of rhodium complexes with 1,10-phenanthroline
S. Kimachi (1997)
Copper(I) complexes for opto-electronic devices
H. 52 Yersin (2011)
10.1021/j100818a043
TRIPLET-SINGLET EMISSION IN FLUID SOLUTION
C. Parker (1962)
10.1002/EJOC.201600247
Bis-Sulfone- and Bis-Sulfoxide-Spirobifluorenes: Polar Acceptor Hosts with Tunable Solubilities for Blue-Phosphorescent Light-Emitting Devices
Cathrin D. Ertl (2016)
10.1039/C2JM33291D
Auto-catalysed crosslinking for next-generation OLED-design
D. Volz (2012)
Optical oxygen sensors with copper(I) complexes
R. Czerwieniec (2013)
10.1039/c5dt03065j
A new class of deep-blue emitting Cu(I) compounds--effects of counter ions on the emission behavior.
Timo Gneuß (2015)
10.1039/c4dt02631d
A new class of luminescent Cu(I) complexes with tripodal ligands – TADF emitters for the yellow to red color range.
Timo Gneuß (2015)
Design of organic TADF molecules. The role
H. Yersin (2017)
Excited states in organic chemistry
J. Barltrop (1975)
10.1016/J.CPLETT.2008.11.086
Photophysical properties of Re(pbt)(CO)4 studied by high resolution spectroscopy
Rafał Czerwieniec (2009)
10.1016/J.ORGEL.2016.02.016
Highly phosphorescent platinum(II) complexes based on rigid unsymmetric tetradentate ligands
Xiao-qing Zhang (2016)
10.1002/9783527621309.CH1
Triplet emitters for organic light emitting diodes: basic properties
Hartmut Yersin (2008)
Photophysical characterizations of OLED relevant Cu(I) complexes exhibiting thermally activated delayed fluorescence (TADF)
Markus J. Leitl (2015)
10.1021/ic0608086
Photophysical properties of highly luminescent copper(I) halide complexes chelated with 1,2-bis(diphenylphosphino)benzene.
A. Tsuboyama (2007)
10.1063/1.1733610
Spin—Orbit Coupling and the Radiationless Processes in Nitrogen Heterocyclics
Mostafa A. El-Sayed (1963)
10.1021/ja103112m
Oxygen gas sensing by luminescence quenching in crystals of Cu(xantphos)(phen)+ complexes.
Conor S. Smith (2010)
10.1021/acs.inorgchem.6b01602
Synthesis, Properties, and Light-Emitting Electrochemical Cell (LEEC) Device Fabrication of Cationic Ir(III) Complexes Bearing Electron-Withdrawing Groups on the Cyclometallating Ligands
A. K. Pal (2016)
Molecular construction kit
U. Lemmer (2013)
10.1021/ja503220w
Brightly luminescent Pt(II) pincer complexes with a sterically demanding carboranyl-phenylpyridine ligand: a new material class for diverse optoelectronic applications.
A. M. Prokhorov (2014)
10.1021/acs.inorgchem.5b02444
Homoleptic Tris-Cyclometalated Iridium Complexes with Substituted o-Carboranes: Green Phosphorescent Emitters for Highly Efficient Solution-Processed Organic Light-Emitting Diodes.
Yunhan Kim (2016)
10.1038/NPHOTON.2016.230
Near-infrared organic light-emitting diodes with very high external quantum efficiency and radiance
Kiet Tuong Ly (2017)
10.1021/CM4018375
Heteroleptic, Dinuclear Copper(I) Complexes for Application in Organic Light-Emitting Diodes
Daniel M Zink (2013)
10.1126/sciadv.1500889
Direct observation of intersystem crossing in a thermally activated delayed fluorescence copper complex in the solid state
Larissa Bergmann (2016)
10.1063/1.1727152
Transients of Volume‐Controlled Current and of Recombination Radiation in Anthracene
Wolfgang Helfrich (1966)
10.1016/J.ORGEL.2016.11.037
Sustainable phosphorescence based on solution-processable and vacuum-sublimable cationic ruthenium(II) complexes achieved by counter-ion control
Dongxin Ma (2017)
10.1063/1.1680504
Symmetry assignments of the lowest CT excited states of ruthenium (II) complexes via a proposed electronic coupling model
R. Harrigan (1973)
10.1039/c4dt02853h
Application of three-coordinate copper(I) complexes with halide ligands in organic light-emitting diodes that exhibit delayed fluorescence.
Masahisa Osawa (2015)
10.1595/147106708X332215
Highly Efficient OLEDs with Phosphorescent Materials
Robert J. Potter (2008)
10.1007/BFb0119209
Spectroscopy of the spin sublevels of transition metal complexes
Tohru Azumi (1997)
10.1021/j100145a010
Effect of the ligand-field strength on the radiative properties of the ligand-localized 3.pi..pi.* state of rhodium complexes with 1,10-phenanthroline: proposed role of dd states
Hisayuki Miki (1993)
10.1016/S0009-2614(03)01142-4
Emission of Ir(ppy)3. Temperature dependence, decay dynamics, and magnetic field properties
W. Finkenzeller (2003)
10.1021/ic900203x
Luminescent mononuclear Ag(I)-bis(diphosphine) complexes: correlation between the photophysics and the structures of mononuclear Ag(I)-bis(diphosphine) complexes.
Kenji Matsumoto (2010)
10.1002/anie.201501880
Trifluoromethylchlorosulfonylation of alkenes: evidence for an inner-sphere mechanism by a copper phenanthroline photoredox catalyst.
Dattatraya B. Bagal (2015)
10.1002/chem.201405356
Long-lived excited states of zwitterionic copper(I) complexes for photoinduced cross-dehydrogenative coupling reactions.
Bin Wang (2015)
10.1007/s41061-016-0040-4
Light-Emitting Electrochemical Cells: A Review on Recent Progress
Shi Tang (2016)
Organische Moleküle für Direktes Singulett-Harvesting mit kurzer Emissionsabklingzeit zur Verwendung in opto-elektronischen Vorrichtungen
H. Yersin (2017)
10.1002/asia.200700298
Exceptionally long-lived luminescence emitted from Tb(III) ion caged in an Ag(I)-Tb(III)-thiacalix[4]arene supramolecular complex in water.
Nobuhiko Iki (2008)
10.1039/c6cc90240e
Correction: A strongly greenish-blue-emitting Cu4Cl4 cluster with an efficient spin-orbit coupling (SOC): fast phosphorescence versus thermally activated delayed fluorescence.
Xu-Lin Chen (2016)
10.1016/S0010-8545(00)00326-X
Triplets in metal-organic compounds. Chemical tunability of relaxation dynamics
H. Yersin (2000)
10.1038/25954
Highly efficient phosphorescent emission from organic electroluminescent devices
Marc A Baldo (1998)
77–113. Cambridge: Woodhead Publishing
ed. A. Buckley (2017)
TADF Material Design
G. J. Hedley (2008)
10.1021/ic034412v
Structure-dependent photophysical properties of singlet and triplet metal-to-ligand charge transfer states in copper(I) bis(diimine) compounds.
Z. A. Siddique (2003)
10.1021/ja202965y
Highly efficient green organic light-emitting diodes containing luminescent three-coordinate copper(I) complexes.
M. Hashimoto (2011)
10.1016/J.CCR.2011.01.042
The triplet state of organo-transition metal compounds. Triplet harvesting and singlet harvesting for efficient OLEDs
H. Yersin (2011)
10.1039/C2TC00263A
Highly efficient green organic light-emitting diodes containing luminescent tetrahedral copper(I) complexes
Satoshi Igawa (2013)
10.1021/acs.jpclett.7b03160
Dinuclear Ag(I) Complex Designed for Highly Efficient Thermally Activated Delayed Fluorescence.
Marsel Z Shafikov (2018)
10.1021/acs.jpca.5b03842
Theoretical Rationalization of the Emission Properties of Prototypical Cu(I)-Phenanthroline Complexes.
G. Capano (2015)
10.1007/3418_2009_6
Organometallic Pt(II) and Ir(III) Triplet Emitters for OLED Applications and the Role of Spin–Orbit Coupling: A Study Based on High-Resolution Optical Spectroscopy
Andreas F. Rausch (2010)
Patent DE 102017101432.2
H. 182 Yersin (2017)
10.1021/ja2107788
Harvesting highly electronically excited energy to triplet manifolds: state-dependent intersystem crossing rate in Os(II) and Ag(I) complexes.
Cheng-Chih Hsu (2012)
10.1002/ADOM.201700197
Highly Efficient Organic Light-Emitting Diode Using A Low Refractive Index Electron Transport Layer
Amin Salehi (2017)
10.1021/JP503437B
Efficient “Warm-White” OLEDs Based on the Phosphorescent bis-Cyclometalated iridium(III) Complex
Vladyslav Cherpak (2014)
10.1039/c3cp53806k
Principles of phosphorescent organic light emitting devices.
Boris F. Minaev (2014)
plexes that bind to DNA
M. W. Mara (2015)
10.1002/CHIN.201615275
Highly Phosphorescent Platinum(II) Emitters: Photophysics, Materials and Biological Applications
Kuntai Li (2016)
10.1002/anie.201412199
Efficient Cu-catalyzed atom transfer radical addition reactions of fluoroalkylsulfonyl chlorides with electron-deficient alkenes induced by visible light.
Xiao-jun Tang (2015)
10.1021/ar500353h
Ultrafast excited-state dynamics of copper(I) complexes.
Munetaka Iwamura (2015)
10.1021/ja0294663
MLCT state structure and dynamics of a copper(I) diimine complex characterized by pump-probe X-ray and laser spectroscopies and DFT calculations.
L. Chen (2003)
10.1063/1.4891680
Extracting the emitter orientation in organic light-emitting diodes from external quantum efficiency measurements
Tobias D. Schmidt (2014)
10.1021/ja108645x
Coherent nuclear dynamics in ultrafast photoinduced structural change of bis(diimine)copper(I) complex.
Munetaka Iwamura (2011)
10.1002/9783527654949.CH13
Organometallic Emitters for OLEDs: Triplet Harvesting, Singlet Harvesting, Case Structures, and Trends
H. Yersin (2013)
10.1021/CM4024309
Rational Design of Strongly Blue-Emitting Cuprous Complexes with Thermally Activated Delayed Fluorescence and Application in Solution-Processed OLEDs
Xu-Lin Chen (2013)
3ππ* state of cyclometalated ruthenium(II) complexes
S. Obara (2006)
10.1021/ja900921p
Capturing and analyzing the excited-state structure of a Cu(I) phenanthroline complex by time-resolved diffraction and theoretical calculations.
Ivan I. Vorontsov (2009)
10.1016/j.ica.2005.06.083
Optical properties of Ag(tripod)X with tripod = 1,1,1-tris(diphenyl-phosphinomethyl)ethane and X− = Cl− and I−: Intraligand and ligand-to-ligand charge transfer
H. Kunkely (2006)
10.1002/cphc.201402585
Substitution-controlled excited state processes in heteroleptic copper(I) photosensitizers used in hydrogen evolving systems.
Stefanie Tschierlei (2014)
10.1002/EJIC.201301349
Homoleptic Copper(I), Silver(I), and Gold(I) Bisphosphine Complexes
Adrien Kaeser (2014)
10.1021/ic401213p
Design of a long-lifetime, earth-abundant, aqueous compatible Cu(I) photosensitizer using cooperative steric effects.
Catherine E McCusker (2013)
10.1002/chin.199830320
Photoprocesses of Copper Complexes That Bind to DNA.
David R McMillin (1998)
10.1039/b508541a
Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy.
F. Weigend (2005)
10.1063/1.1840685
Radiationless Transitions in Polyatomic Molecules. I. Calculation of Franck—Condon Factors
W. Siebrand (1967)
10.1039/c4cc02037e
Control of emission colour with N-heterocyclic carbene (NHC) ligands in phosphorescent three-coordinate Cu(I) complexes.
Valentina A. Krylova (2014)
10.1021/MA502384Y
Photocatalyzed Cu-Based ATRP Involving an Oxidative Quenching Mechanism under Visible Light
Qizhi Yang (2015)
10.1117/12.921372
Singlet harvesting with brightly emitting Cu(I) and metal-free organic compounds
H. Yersin (2012)
10.1007/s41061-016-0036-0
Luminescent Iridium Complexes Used in Light-Emitting Electrochemical Cells (LEECs)
A. F. Henwood (2016)
10.1039/c3cp50838b
Probing the excited state dynamics of a new family of Cu(I)-complexes with an enhanced light absorption capacity: excitation-wavelength dependent population of states through branching.
Panagiotis Al. Papanikolaou (2013)
complexes and singlet harvesting
R. Czerwieniec (2015)
10.1002/adma.200502365
Highly Luminescent CuI Complexes for Light-Emitting Electrochemical Cells†
N. Armaroli (2006)
10.5860/choice.29-4528
Quanta: A Handbook of Concepts
P. Atkins (1974)
10.1021/ic100872w
The triplet state of fac-Ir(ppy)3.
Thomas Hofbeck (2010)
10.1021/ja067271f
Ultrafast structural rearrangements in the MLCT excited state for copper(I) bis-phenanthrolines in solution.
G. Shaw (2006)
10.1039/c3cc42280a
Outstanding luminescence from neutral copper(I) complexes with pyridyl-tetrazolate and phosphine ligands.
Larissa Bergmann (2013)
Singulett-Harvesting mit löslichen Kupfer(I)-Komplexen für opto-elektronische Vorrichtungen
H. 51 Yersin (2010)
10.1021/ja1004575
E-type delayed fluorescence of a phosphine-supported Cu2(mu-NAr2)2 diamond core: harvesting singlet and triplet excitons in OLEDs.
Joseph C. Deaton (2010)
10.1016/0022-2860(72)85053-1
Molecular spectroscopy of the triplet state
Sean P. McGlynn (1969)
10.1021/ja003693s
Highly phosphorescent bis-cyclometalated iridium complexes: synthesis, photophysical characterization, and use in organic light emitting diodes.
S. Lamansky (2001)
Modern Quantum Chemistry: Introduction to Advanced Electronic Structure Theory
A. Szabo (1989)
10.1007/128_2007_128
Photochemistry and Photophysics of Coordination Compounds: Copper
N. Armaroli (2007)
10.1021/cm9003678
Exceptional Oxygen Sensing Capabilities and Triplet State Properties of Ir(ppy-NPh2)3
Chris S. K. Mak (2009)
10.1117/12.2060499
Bright coppertunities: efficient OLED devices with copper(I)iodide-NHetPHOS-emitters
Manuela Wallesch (2014)
10.1039/C5RA04591F
Four highly efficient cuprous complexes and their applications in solution-processed organic light-emitting diodes
Qing Zhang (2015)
10.1007/s10854-015-3506-1
Electric-field induced nonlinear optical materials based on a bipolar copper (I) complex embedded in polymer matrices
Rafal Czerwieniec (2015)
10.1038/nature04645
Management of singlet and triplet excitons for efficient white organic light-emitting devices
Yiru Sun (2006)
10.1016/J.CCR.2008.03.013
Improving the photophysical properties of copper(I) bis(phenanthroline) complexes
Aurélie Lavie-Cambot (2008)
10.1039/c9cc03915e
Chiral iridium(iii) complexes with four-membered Ir-S-P-S chelating rings for high-performance circularly polarized OLEDs.
Zhiping Yan (2019)
10.1002/9781119007166.CH1
Archetypal Iridium(III) Compounds for Optoelectronic and Photonic Applications
Joseph C. Deaton (2017)
10.1021/ic300333c
Photoluminescence properties, molecular structures, and theoretical study of heteroleptic silver(I) complexes containing diphosphine ligands.
S. Igawa (2012)
10.1039/C4TC00410H
Efficient orange-red phosphorescent organic light-emitting diodes using an in situ synthesized copper(I) complex as the emitter
Feng Ru Wei (2014)
Chemical tunability of relaxation dynamics
H. Yersin (1997)
German Patent DE 10 2008 033563
Regensburg (2006)
10.1007/b96858
Triplet emitters for OLED applications. Mechanisms of exciton trapping and control of emission properties
H. Yersin (2004)
10.1007/s41061-016-0019-1
Copper(I) Complexes for Thermally Activated Delayed Fluorescence: From Photophysical to Device Properties
Markus J. Leitl (2016)
10.1016/J.ORGEL.2016.12.024
New platinum(II) one-armed Schiff base complexes for blue and orange PHOLEDs applications
Jie Zhang (2017)
10.1021/acs.inorgchem.5b02839
Thermally Tunable Dual Emission of the d(8)-d(8) Dimer [Pt2(μ-P2O5(BF2)2)4](4).
Thomas Hofbeck (2016)
10.1002/ADFM.201300104
Organic Light‐Emitting Diodes with 30% External Quantum Efficiency Based on a Horizontally Oriented Emitter
Sei-Yong Kim (2013)
10.1007/3-540-44474-2_3
Low-Lying Electronic States and Photophysical Properties of Organometallic Pd(II) and Pt(II) Compounds. Modern Research Trends Presented in Detailed Case Studies
H. Yersin (2001)
10.1039/DT9960004583
Silver complexes with the nido-diphosphine [7,8-(PPh2)2-7,8-C2B9H10]–
Olga Crespo (1996)
On the multiplic
T. Azumi (1966)
10.1021/ja5109672
Highly efficient luminescence of Cu(I) compounds: thermally activated delayed fluorescence combined with short-lived phosphorescence.
Thomas Hofbeck (2015)
10.1021/acs.jpca.5b00901
Transient absorption dynamics of sterically congested Cu(I) MLCT excited states.
Sofia Garakyaraghi (2015)
10.1063/1.1733166
Relationship between Absorption Intensity and Fluorescence Lifetime of Molecules
S. Strickler (1962)
10.1063/1.464304
A new mixing of Hartree–Fock and local density‐functional theories
A. D. Becke (1993)



Semantic Scholar Logo Some data provided by SemanticScholar