Rapid room temperature synthesis of red iridium(<scp>iii</scp>) complexes containing a four-membered Ir–S–C–S chelating ring for highly efficient OLEDs with EQE over 30%

Lu, Guangzhao; Su, Ning; Yang, Honghui; Zhu, Qi; Zhang, Wenwei; Zheng, You‐Xuan; Zhou, Liang; Zuo, Jing‐Lin; Chen, Zhao‐Xu; Zhang, Hongjie

doi:10.1039/c8sc05605f

Cited by 56 publications

(21 citation statements)

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“…[ 25 ] In the aspect of ionic complex, the tetrahalide manganese(II) complex can be prepared quantitatively by mixing organic halogen salt and MnX 2 (X = Cl, Br, I) in a stoichiometric ratio in CH 2 Cl 2 , alcohol, water, or acids at room temperature; [ 22,44 ] the AMnX 3 ‐type coordination polymers could also be obtained conveniently by evaporation of the aqueous solution with stoichiometric amounts of organic salt or free base, MnX 2 , and excess of HX at room temperature. [ 35a,36 ] Compared with the noble metal‐based phosphorescent complex, [ 10–12 ] the synthesis of phosphorescent manganese(II) complex is much easier, and the target complex can be obtained in a high yield.…”

Section: Molecular Design Strategies Of Phosphorescent Manganese(ii) mentioning

confidence: 99%

“…[1][2][3][4][5][6][7][8] Quite different from the traditional fluorescent materials with the light emission from the singlet states, PTMCs are triplet emitters. [9][10][11][12][13][14] Since Forrest and coworkers successfully realized the first phosphorescent organic should be well noted that many phosphorescent manganese(II) complexes also exhibit ferroelectric properties. [35a,36] In this progress report, we mainly focus on the luminescent properties and related photofunctional applications of various phosphorescent manganese(II) complexes.…”

Section: Introductionmentioning

confidence: 99%

“…[ 1–8 ] Quite different from the traditional fluorescent materials with the light emission from the singlet states, PTMCs are triplet emitters. [ 9–14 ] Since Forrest and co‐workers successfully realized the first phosphorescent organic light‐emitting device (OLED) in 1998, [ 1 ] phosphorescent transition‐metal complexes, especially for noble metal‐based ones (e.g., iridium(III), platinum(II), etc.) as triplet emitters toward highly efficient organic electroluminescence, have aroused extensive attention.…”

Section: Introductionmentioning

confidence: 99%

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Phosphorescent Manganese(II) Complexes and Their Emerging Applications

Tao

Liu

Wong

2020

Advanced Optical Materials

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light-emitting device (OLED) in 1998, [1] phosphorescent transition-metal complexes, especially for noble metal-based ones (e.g., iridium(III), platinum(II), etc.) as triplet emitters toward highly efficient organic electroluminescence, have aroused extensive attention. [15-21] Owing to strong spin-orbit coupling effect, these complexes may use both singlet and triplet excitons to greatly enhance the efficiency of OLED, breaking the upper limit of the conventional fluorescent device efficiency. Due to their unique properties of excited states, they also have extended their applications in other fields, for instance, catalysis, organic solar cells, organic memory devices, biological sensing and imaging, photodynamic therapy, information recording, and security protection, etc. [22-27] Although extensive works have been done to the design and preparation of phosphorescent materials based on noble metals, these noble metals usually have some disadvantages (such as high cost and low abundance in nature), thereby limiting their practical applications. The relatively abundant and cheap PTMCs of low toxicity have drawn considerable interests very recently. [4,23,24,28-31] Many kinds of non-noble metal-based PTMCs such as copper(I), tungsten(VI), and manganese(II) complexes have emerged rapidly. [4,23-25,28-31] Phosphorescent manganese(II) complexes show great potentials in many applications, due to their features including highly efficient phosphorescence, flexible design in molecular structure, ease of synthesis, and rich physical properties (e.g., triboluminescence, stimuli-responsivity, etc.). [24,25a,32-36] Compared with the noble metals, manganese element with an atomic number of 25 has abundant reserves, is environmentally friendly and inexpensive. Moreover, it has richer valence and coordination mode, which has been widely used in the fields of catalysis, ferroelectric, and magnetic materials. [37-39] Among the various valence states of manganese ion, the divalent manganese ion having a 3d 5 electron configuration has a 4 T 1 − 6 A 1 radiative transition closely related to the crystal field strength. The crystal field strength in the metal complex highly depends on the chemical structure of the ligand and the coordination number. These features make the manganese(II) complexes having rich photophysical properties. By regulating the ligand structure, the organic counterion and the coordination number of the manganese(II) complex, the green, yellow, orange, red, or even near-infrared phosphorescence can be achieved. [23-25,36,40] It Phosphorescent manganese(II) complexes are emerging as a new generation of phosphorescent materials showing great potentials in many applications, owing to their unique features including highly efficient phosphorescence, diverse structural/molecular design, and ease of synthesis, structural diversity, rich physical properties (e.g., triboluminescence, stimuli-responsivity, etc.), high abundance, and low cost. The research on phosphorescent manganese(II) complexes is just in its infancy...

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Section: Molecular Design Strategies Of Phosphorescent Manganese(ii) mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Phosphorescent Manganese(II) Complexes and Their Emerging Applications

Tao

Liu

Wong

2020

Advanced Optical Materials

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“…Besides, the sulfur atom is able to stabilize metal ions in unusual oxidation states [ 13 , 14 , 15 ]. Therefore, it has a great advantage over the costly traditional way of refluxing the [(C^N) 2 Ir(μ-Cl)] 2 chloride-bridged dimers with cyclometalated or ancillary ligands at high temperature for a long time [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

“…In our former study, we prepared some red Ir(III) complexes using 4-(4-(trifluoromethyl)phenyl)quinazoline (4tfmpq) as the cyclometalated ligand. Diisopropylamine, diphenylamine, carbazole and their derivatives substituted dithiocarbamates as ancillary ligands at room temperature within 10 min, and the device performances were improved greatly [ 16 , 21 , 22 ]. Furthermore, from our investigation we found that the Ir-S-C-S structures were only valuable for the red Ir(III) complexes with excellent device performance.…”

Section: Introductionmentioning

confidence: 99%

Simple Synthesis of Red Iridium(III) Complexes with Sulfur-Contained Four-Membered Ancillary Ligands for OLEDs

Mao

Shen

et al. 2021

Molecules

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Phosphorescent iridium(III) complexes have been widely researched for the fabrication of efficient organic light-emitting diodes (OLEDs). In this work, three red Ir(III) complexes named Ir-1, Ir-2, and Ir-3, with Ir-S-C-S four-membered framework rings, were synthesized efficiently at room temperature within 5 min using sulfur-containing ancillary ligands with electron-donating groups of 9,10-dihydro-9,9-dimethylacridine, phenoxazine, and phenothiazine, respectively. Due to the same main ligand of 4-(4-(trifluoromethyl)phenyl)quinazoline, all Ir(III) complexes showed similar photoluminescence emissions at 622, 619, and 622 nm with phosphorescence quantum yields of 35.4%, 50.4%, and 52.8%, respectively. OLEDs employing these complexes as emitters with the structure of ITO (indium tin oxide)/HAT-CN (dipyra-zino[2,3-f,2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile, 5 nm)/TAPC (4,4′-cyclohexylidenebis[N,N-bis-(4-methylphenyl)aniline], 40 nm)/TCTA (4,4″,4″-tris(carbazol-9-yl)triphenylamine, 10 nm)/Ir(III) complex (10 wt%): 2,6DCzPPy (2,6-bis-(3-(carbazol-9-yl)phenyl)pyridine, 10 nm)/TmPyPB (1,3,5-tri(mpyrid-3-yl-phenyl)benzene, 50 nm)/LiF (1 nm)/Al (100 nm) achieved good performance. In particular, the device based on complex Ir-3 with the phenothiazine unit showed the best performance with a maximum brightness of 22480 cd m−2, a maximum current efficiency of 23.71 cd A−1, and a maximum external quantum efficiency of 18.1%. The research results suggest the Ir(III) complexes with a four-membered ring Ir–S–C–S backbone provide ideas for the rapid preparation of Ir(III) complexes for OLEDs.

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Semitransparent Circularly Polarized Phosphorescent Organic Light‐Emitting Diodes with External Quantum Efficiency over 30% and Dissymmetry Factor Close to 10⁻²

et al. 2021

Adv Funct Materials

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To concurrently realize large electroluminescence dissymmetry factor and high device efficiency remains a formidable challenge in the development of circularly polarized organic light‐emitting diode (CP‐OLED). In this work, by introducing a famous chiral resource of R‐camphor, two green chiral iridium(III) isomers of Λ/Δ‐Ir‐(R‐camphor) containing dual stereogenic centers at iridium and ancillary ligand, are efficiently synthesized. Benefiting from their high phosphorescence quantum yields (≈93%) and obvious circularly polarized photoluminescence property with dissymmetry factors (|gPL|) in the 10−3 order of magnitude, the circularly polarized phosphorescent organic light‐emitting diodes using these chiral emitters show excellent performances with the maximum external quantum efficiency (EQEmax) of 30.6%, low efficiency roll‐off, and intense circularly polarized electroluminescence signal with dissymmetry factor (gEL) in the 10−4 order of magnitude. By the novel device engineering with semitransparent cathode, the resulting gEL values are significantly boosted by one order of magnitude, up to 7.70 × 10−3, which is the highest among the CP‐OLEDs with chiral iridium complexes. Noteworthy, the semitransparent devices deliver a record‐high EQEmax of 18.8% among the semitransparent OLEDs. The combination of novel chiral Ir(III) complexes and the semitransparent devices sheds light on the development of high performance CP‐OLEDs with simultaneously high efficiency and large dissymmetry factor.

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Rapid room temperature synthesis of red iridium(iii) complexes containing a four-membered Ir–S–C–S chelating ring for highly efficient OLEDs with EQE over 30%

Abstract: Three red iridium(iii) complexes with dithiocarbamate ligands were rapidly synthesized at room temperature with good yields, and their OLEDs exhibit an EQEmax of 30.54% with mild efficiency roll-off.

Cited by 56 publications

References 56 publications

Phosphorescent Manganese(II) Complexes and Their Emerging Applications

Phosphorescent Manganese(II) Complexes and Their Emerging Applications

Simple Synthesis of Red Iridium(III) Complexes with Sulfur-Contained Four-Membered Ancillary Ligands for OLEDs

Semitransparent Circularly Polarized Phosphorescent Organic Light‐Emitting Diodes with External Quantum Efficiency over 30% and Dissymmetry Factor Close to 10⁻²

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Rapid room temperature synthesis of red iridium(iii) complexes containing a four-membered Ir–S–C–S chelating ring for highly efficient OLEDs with EQE over 30%

Abstract: Three red iridium(iii) complexes with dithiocarbamate ligands were rapidly synthesized at room temperature with good yields, and their OLEDs exhibit an EQEmax of 30.54% with mild efficiency roll-off.

Cited by 56 publications

References 56 publications

Phosphorescent Manganese(II) Complexes and Their Emerging Applications

Phosphorescent Manganese(II) Complexes and Their Emerging Applications

Simple Synthesis of Red Iridium(III) Complexes with Sulfur-Contained Four-Membered Ancillary Ligands for OLEDs

Semitransparent Circularly Polarized Phosphorescent Organic Light‐Emitting Diodes with External Quantum Efficiency over 30% and Dissymmetry Factor Close to 10−2

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About

Semitransparent Circularly Polarized Phosphorescent Organic Light‐Emitting Diodes with External Quantum Efficiency over 30% and Dissymmetry Factor Close to 10⁻²