Yellowish-orange and red emitting quinoline-based iridium(III) complexes: Synthesis, thermal, optical and electrochemical properties and OLED application
Source abstract
Abstract
Two novel heteroleptic iridium(III) acetylacetonate (acac) complexes K3a and K3b were synthesised from cyclometallating ligands of 2-(4′-formylphenyl)quinoline 11a and 2-(5′-formylphenyl)quinoline 11b. Complexes K3a and K3b were fully characterised by NMR spectroscopy, mass spectrometry and FT-IR. Differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA) indicate that both complexes were amorphous solids, stable up to 303 °C and 313 °C, respectively. Complexes K3a and K3b showed strong, high-energy absorption bands (<400 nm) due to ligand-centred (1LC) transitions and weaker, low-energy absorption bands (400−600 nm) arising from a mixture of metal-to-ligand charge transfer (1MLCT/3MLCT) and ligand-centred (3LC) transitions. In degassed dichloromethane solutions, complexes K3a and K3b gave yellowish-orange and red phosphorescent emissions at 579 nm and 630 nm, with quantum efficiencies of 99.3 % and 79.3 %, respectively. At positive potential, complexes K3a and K3b exhibited a one-electron reversible oxidation (Eox1/2) peak at 0.69 V and a quasi-reversible oxidation (Eox1/2) peak at 0.60 V, respectively, which were assigned to the Ir(III)/Ir(IV) couple. At negative potentials, complexes K3a and K3b exhibited a one-electron irreversible reduction peak at -1.79 V and -1.94 V, respectively. Phosphorescent organic light-emitting diodes (PhOLEDs) were fabricated with a device configuration of ITO/PEDOT:PSS/EML/TPBi/LiF/Al, in which K3a and K3b gave yellowish-orange and red electroluminescence (EL) at 572 nm and 628 nm, respectively. Complex K3a gave the highest luminance of 2773 cd/m2, current efficiency of 3.3 cd/A, external quantum efficiency of 1.2 % and maximum power efficiency of 1.05 lm/W with a turn-on voltage of 5.0 V (Device A).
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Research context
OpenAlex topics: Organic Light-Emitting Diodes Research · Conducting polymers and applications · Organic Electronics and Photovoltaics
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (75)
Show source-provided references
1. Room-temperature combinatorial screening of cyclometallated iridium(III) complexes for a step towards molecular control of colour purity10.1039/c0dt01697g ↗
2. Blue-emitting iridium complexes with substituted 1,2,4-triazole ligands: synthesis, photophysics, and devices10.1021/ic701110p ↗
3. Iridium(III) 2-Phenylbenzimidazole complexes: synthesis, structure, optical properties, and applications in dye-sensitized solar cells10.1002/ejic.201501068 ↗
4. Photophysical and electrochemical properties of heteroleptic tris-cyclometalated iridium(III) complexes10.1021/ic050324u ↗
5. Solution-processible multi-component cyclometalated iridium phosphors for high-efficiency orange-emitting OLEDs and their potential use as white light sources10.1002/adfm.200601205 ↗
6. Synthesis and characterization of phosphorescent cyclometalated iridium complexes10.1021/ic0008969 ↗
7. Synthesis and characterization of facial and meridional tris-cyclometalated iridium(III) complexes10.1021/ja034537z ↗
8. Novel design of iridium phosphors with pyridinylphosphinate ligands for high-efficiency blue organic light-emitting diodes10.1038/srep38478 ↗
9. Phosphorescent iridium(III) complexes: toward high phosphorescence quantum efficiency through ligand control10.1039/B812281D ↗
10. Synthesis, separation, and circularly polarized luminescence studies of enantiomers of iridium(III) luminophores10.1021/ic701747j ↗
11. A comprehensive survey of cationic iridium(III) complexes bearing nontraditional ligand chelation motifs10.1002/ejic.201300171 ↗
12. Influence of substituents on the energy and nature of the lowest excited states of heteroleptic phosphorescent Ir(III) complexes: a joint theoretical and experimental study10.1021/ja0711011 ↗
13. Highly efficient, conventional and flexible deep-red phosphorescent OLEDs using ambipolar thiophene/selenophene-phenylquinoline ligand-based Ir(III) complexes10.1016/j.dyepig.2016.08.060 ↗
14. A facile color-tuning strategy for constructing a library of Ir(III) complexes with fine-tuned phosphorescence from bluish green to red using a synergetic substituent effect of -OCH3 and -CN at only the C-ring of CN ligand10.1039/C6TC00153J ↗
15. Synthesis and photophysical properties of bis-cyclometallated Iridium(III)-Styryl complexes and their saturated analogues10.1002/ejic.200700042 ↗
16. Inter-ligand energy transfer and related emission change in the cyclometalated heteroleptic iridium complex: facile and efficient color tuning over the whole visible range by the ancillary ligand structure10.1021/ja052880t ↗
17. Cyclometalated iridium(III) chelates—a new exceptional class of the electrochemiluminescent luminophores10.1007/s00216-016-9615-8 ↗
18. Facile synthesis and characterization of iridium(III) complexes containing an N-ethylcarbazole-thiazole main ligand using a tandem reaction for solution processed phosphorescent organic light-emitting diodes10.1039/c3tc00323j ↗
19. Cyclometalated iridium(III) complexes with 5-acetyl-2-phenypyridine derived ligands for red phosphorescent OLEDs10.1016/j.synthmet.2011.03.030 ↗
20. Yellow/orange emissive heavy-metal complexes as phosphors in monochromatic and white organic light-emitting devices10.1039/C4CS00110A ↗
21. High-efficiency red electrophosphorescence devices10.1063/1.1355007 ↗
22. Highly phosphorescent bis-cyclometalated iridium complexes: synthesis, photophysical characterization, and use in organic light emitting diodes10.1021/ja003693s ↗
23. Homoleptic cyclometalated iridium complexes with highly efficient red phosphorescence and application to organic light-emitting diode10.1021/ja034732d ↗
24. New deep-red heteroleptic iridium complex with 3-hexylthiophene for solution-processed organic light-emitting diodes emitting saturated red and high CRI white colors10.1016/j.orgel.2015.02.016 ↗
25. Solution-processible red iridium dendrimers based on oligocarbazole host dendrons: synthesis, properties, and their applications in organic light-emitting diodes10.1002/adfm.200800259 ↗
26. Highly efficient solution-processed red organic light-emitting diodes with long-side-chained triplet emitter10.1016/j.synthmet.2010.11.013 ↗
27. Improved luminance and external quantum efficiency of red and white organic light-emitting diodes with iridium(III) complexes with phenyl-substituted 2-phenylpyridine as a second cyclometalated ligand10.1039/C5TC02728D ↗
28. Efficient red-emitting cyclometalated iridium(III) complex and applications of organic light-emitting diode10.1016/j.ica.2009.08.002 ↗
29. A novel deep-red-emitting iridium complex with single-peaked narrow emission band Synthesis, photophysical properties, and electroluminescence performances10.1016/j.jlumin.2010.09.032 ↗
30. Red to near-infrared organometallic phosphorescent dyes for OLED applications10.1016/j.jorganchem.2013.09.035 ↗
31. Highly efficient iridium(III) complexes with diphenylquinoline ligands for organic light-emitting diodes: synthesis and effect of fluorinated substitutes on electrochemistry, photophysics and electroluminescence10.1016/j.jorganchem.2006.07.008 ↗
32. Tuning the emission and morphology of cyclometalated iridium complexes and their applications to organic light-emitting diodes10.1039/b415754k ↗
33. Highly efficient red electrophosphorescent devices based on iridium isoquinoline complexes: remarkable external quantum efficiency over a wide range of current10.1002/adma.200304630 ↗
34. High color rendering index in phosphorescent white organic light-emitting diodes using a yellowish-green dopant with broad light emission10.1016/j.orgel.2013.03.014 ↗
35. Efficient red-emitting cyclometalated iridium(III) complexes containing lepidine-based ligands10.1021/ic050385s ↗
36. Optimization of the synthesis of quinoline-based neutral cyclometalated iridium complexes via microwave irradiation: design of light harvesting and emitting complexes using bulky quinolines10.1039/C9QO00870E ↗
37. Highly efficient phosphorescent bis-cyclometalated iridium complexes based on quinoline ligands10.1016/j.synthmet.2005.08.034 ↗
38. Synthesis and characterization red emitting iridium (III) complex with 2-(4-cynophenyl)-4 phenyl quinoline for PhOLEDs10.1016/j.matpr.2018.06.581 ↗
39. Color tuning of iridium complexes – part I: substituted phenylisoquinoline-based iridium complexes as the triplet emitter10.1016/j.ica.2005.10.003 ↗
40. New luminescent cyclometalated iridium(III) complexes containing fluorinated phenylisoquinoline-based ligands: synthesis, structures, photophysical properties and DFT calculations10.1016/j.cclet.2015.12.007 ↗
41. Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties10.3762/bjoc.16.93 ↗
42. Wide tuning of emission color of iridium (III) complexes from green to deep red via dicyanovinyl substituent effect on 2-phenylpyridine ligands10.1016/j.orgel.2013.05.001 ↗
43. Formylated chloro-bridged iridium(iii) dimers as OLED materials: opening up new possibilities10.1039/C4DT03127J ↗
44. Benzo[a]carbazole-Based donor-pi-Acceptor type organic dyes for highly efficient dye-sensitized solar cells10.1021/am508400a ↗
45. Ruthenium-catalyzed meta-selective CAr—H bond formylation of arenes10.1021/acs.joc.0c00007 ↗
46. PdCl2(dppf)-catalyzed in situ coupling of 2-hydroxypyridines with aryl boronic acids mediated by PyBroP and the one-pot chemo- and regioselective construction of two distinct aryl–aryl bonds10.1039/c1cc15753a ↗
47. Heteroarylmethoxyphenylalkoxyiminoalkylcarboxylic acids as leukotriene biosynthesis inhibitors10.1021/jm9904102 ↗
48. Photophysical effects of metal-carbon sigma-bonds in ortho-metalated complexes of Ir(Iii) and Rh(Iii)10.1021/ja00334a031 ↗
49. A promising phosphorescent heteroleptic iridium complex with carbazole-functionalized substituent: synthesis, photophysical and electroluminescent performances10.1016/j.optmat.2012.09.002 ↗
50. Electroluminescent devices based on cross-linked polymer blends10.1063/1.1599625 ↗
51. Tetrathiafulvalene-oligofluorene star-shaped systems: new semiconductor materials for fluorescent moisture indicators10.1039/C9TC00845D ↗
52. Improving the performance of phosphorescent polymer light-emitting diodes using morphology-stable carbazole-based iridium complexes10.1039/b705342h ↗
53. Orange-yellow phosphorescent iridium(III) complex for solution-processed organic light-emitting diodes: structural, optical and electroluminescent properties of bis(2-phenylbenzothiazole)[2-(2-hydroxyphenyl)benzothiazole]iridium(III)10.1002/bkcs.11144 ↗
54. Study of the influences of molecular planarity and aluminum evaporation rate on the performances of electrical memory devices10.1039/C4TC00311J ↗
55. Blue emitting cationic iridium complexes containing two substituted 2-Phenylpyridine and one 2,2’ -Biimidazole for solution-processed organic light-emitting diodes (OLEDs)10.5012/bkcs.2012.33.11.3645 ↗
56. Highly efficient electrochemiluminescence from iridium(III) complexes with 2-phenylquinoline ligand10.1039/C4DT02809K ↗
57. Synthesis and electroluminescent properties of red emissive iridium(III) complexes with ester-substituted phenylquinoline ligands10.1016/j.synthmet.2012.06.016 ↗
58. Effect of solvent polarity on nonradiative processes in xanthene dyes: rhodamine B in normal alcohols10.1021/j100334a023 ↗
59. Highly efficient, solution-processed, single-layer, electrophosphorescent diodes and the effect of molecular dipole moment10.1002/adfm.201100324 ↗
60. Effect of PEDOT-PSS resistivity and work function on PLED performance10.1016/j.orgel.2013.11.029 ↗
61. Iridium(III) complexes with orthometalated quinoxaline ligands: subtle tuning of emission to the saturated red color10.1021/ic0489443 ↗
62. Structure properties of a highly luminescent yellow emitting material for OLED and its application10.1039/C2RA21951D ↗
63. Blue emitting iridium complexes: synthesis, photophysics and phosphorescent devices10.1039/b512081k ↗
64. Solution-processable phosphorescence based on iridium-cored small molecules with the trifluoromethyl group10.1016/j.optmat.2014.12.033 ↗
65. Colour tuning from green to red by substituent effects in phosphorescent tris-cyclometalated iridium(III) complexes of carbazole-based ligands: synthetic, photophysical, computational and high efficiency OLED studies10.1039/c2jm15049b ↗
66. Yellow-orange electroluminescence of novel tin complexes
67. Comprehensive study on the Electron transport layer in blue flourescent organic light-emitting diodes10.1149/2.034311jss ↗
68. Improved hole-blocking and Electron injection using a TPBI interlayer at the cathode interface of OLEDs10.1088/0256-307X/28/4/047803 ↗
69. Energy transfer and triplet exciton confinement in polymeric electrophosphorescent devices10.1002/polb.10648 ↗
70. Saturated red phosphorescent Iridium(III) complexes containing phenylquinoline ligands for efficient organic light-emitting diodes10.1016/j.dyepig.2020.108405 ↗
71. Synthesis and characterization of red-emitting iridium(III) complexes for solution-processable phosphorescent organic light-emitting diodes10.1002/adfm.200900322 ↗
72. Phosphorescence from iridium complexes doped into polymer blends10.1063/1.1635976 ↗
73. Synthesis and photophysical, electrochemical, and electrophosphorescent properties of a series of iridium(III) complexes based on quinoline derivatives and different beta-diketonate ligands10.1021/om060037d ↗
74. Iridium complexes containing 2-aryl-benzothiazole ligands: color tuning and application in high-performance organic light-emitting diodes10.1039/c3tc30586d ↗
75. Tunable emission of polymer light emitting diodes bearing green-emitting Ir(III) complexes: the structural role of 9-((6-(4-fluorophenyl)pyridin-3-yl)methyl)-9H-carbazole ligands10.1016/j.dyepig.2009.10.017 ↗