Greenish yellow organic light emitting devices based on novel iridium complexes containing 2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole

Liangliang Han; Dongyu Zhang; Yuanhang Zhou; Ying Yang; Han Young Woo; Fali Bai; Renqiang Yang

doi:10.1016/j.dyepig.2013.08.011

Greenish yellow organic light emitting devices based on novel iridium complexes containing 2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole

Liangliang Han, Dongyu Zhang, Yuanhang Zhou, Ying Yang, Han Young Woo, Fali Bai, Renqiang Yang

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

2-Cyclohexenyl-1-phenyl-1H-benzo[d]imidazole (Hcyclopbi) and its heterocyclometalated iridium complexes bis[2-cyclohexenyl-1-phenyl-1H-benzo[d] imidazole](acetylacetonate)iridium(III) [(cyclopbi)₂Iracac] and bis[2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole][2-(3-(trifluoromethyl) -1H-pyrazol-5-yl)pyridinate]iridium(III) [(cyclopbi)₂IrCF ₃] were firstly designed and synthesized. Owing to the strong electron withdrawing ability of 2-(3-(trifluoromethyl)-1H-pyrazol) compared to that of acetylacetonate, blue shifted phosphorescence 542 nm was obtained for (cyclopbi)₂IrCF₃ compared to that of (cyclopbi) ₂Iracac 545 nm with photoluminescence quantum yields (φ) 0.22 and 0.25, respectively, as well the highest occupied molecular orbit (HOMO) energy level was estimated to be -5.10 eV for (cyclopbi)₂IrCF₃, 0.19 eV lower than that of -4.91 eV for (cyclopbi)₂Iracac. When (cyclopbi)₂Iracac was doped into 4,4′-bis(9H-carbazol-9-yl) biphenyl (CBP) as the emitting layer, high efficiency organic light emitting devices (OLEDs) were obtained with maximum current efficiency (η_c) 22.3 cd/A at 3.1 mA/cm² and maximum brightness 16,300 cd/m² at 171.6 mA/cm², which were comparable to those of bis(2-phenylpyridine)(acetylacetonate)iridium(III) [(ppy) ₂Iracac] with the same device structure. This results indicate that (cyclopbi)₂Iracac and (cyclopbi)₂IrCF₃ are potential phosphorescent dyes used for OLEDs.

Original language	English
Pages (from-to)	1010-1015
Number of pages	6
Journal	Dyes and Pigments
Volume	99
Issue number	3
DOIs	https://doi.org/10.1016/j.dyepig.2013.08.011
Publication status	Published - 2013
Externally published	Yes

Bibliographical note

Funding Information:
This work was supported by Outstanding Young Scientists Research Award Fund of Shandong Province ( BS2010NJ021 ), Shandong Provincial Natural Science Foundation ( ZR2011BZ007 ), Qingdao Municipal Science and Technology Program (11-2-4-22-hz), and State Key Laboratory of Luminescent Materials and Devices (South China University of Technology) . We thank Dr. Xiao Li and Haijun Chi for the NMR analysis in University of Science and Technology Liaoning.

Keywords

2-Cyclohexenyl-1-phenyl-1H-benzo[d]imidazole
Electroluminescence
Greenish yellow phosphorescence
Heterocyclometalated iridium complexes
Organic light emitting devices
Photoluminescence

ASJC Scopus subject areas

Chemical Engineering(all)
Process Chemistry and Technology

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10.1016/j.dyepig.2013.08.011

Cite this

@article{dcbea0d5aa584d85a0f9c8fb1d8330e5,

title = "Greenish yellow organic light emitting devices based on novel iridium complexes containing 2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole",

abstract = "2-Cyclohexenyl-1-phenyl-1H-benzo[d]imidazole (Hcyclopbi) and its heterocyclometalated iridium complexes bis[2-cyclohexenyl-1-phenyl-1H-benzo[d] imidazole](acetylacetonate)iridium(III) [(cyclopbi)2Iracac] and bis[2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole][2-(3-(trifluoromethyl) -1H-pyrazol-5-yl)pyridinate]iridium(III) [(cyclopbi)2IrCF 3] were firstly designed and synthesized. Owing to the strong electron withdrawing ability of 2-(3-(trifluoromethyl)-1H-pyrazol) compared to that of acetylacetonate, blue shifted phosphorescence 542 nm was obtained for (cyclopbi)2IrCF3 compared to that of (cyclopbi) 2Iracac 545 nm with photoluminescence quantum yields (φ) 0.22 and 0.25, respectively, as well the highest occupied molecular orbit (HOMO) energy level was estimated to be -5.10 eV for (cyclopbi)2IrCF3, 0.19 eV lower than that of -4.91 eV for (cyclopbi)2Iracac. When (cyclopbi)2Iracac was doped into 4,4′-bis(9H-carbazol-9-yl) biphenyl (CBP) as the emitting layer, high efficiency organic light emitting devices (OLEDs) were obtained with maximum current efficiency (ηc) 22.3 cd/A at 3.1 mA/cm2 and maximum brightness 16,300 cd/m2 at 171.6 mA/cm2, which were comparable to those of bis(2-phenylpyridine)(acetylacetonate)iridium(III) [(ppy) 2Iracac] with the same device structure. This results indicate that (cyclopbi)2Iracac and (cyclopbi)2IrCF3 are potential phosphorescent dyes used for OLEDs.",

keywords = "2-Cyclohexenyl-1-phenyl-1H-benzo[d]imidazole, Electroluminescence, Greenish yellow phosphorescence, Heterocyclometalated iridium complexes, Organic light emitting devices, Photoluminescence",

author = "Liangliang Han and Dongyu Zhang and Yuanhang Zhou and Ying Yang and Woo, {Han Young} and Fali Bai and Renqiang Yang",

note = "Funding Information: This work was supported by Outstanding Young Scientists Research Award Fund of Shandong Province ( BS2010NJ021 ), Shandong Provincial Natural Science Foundation ( ZR2011BZ007 ), Qingdao Municipal Science and Technology Program (11-2-4-22-hz), and State Key Laboratory of Luminescent Materials and Devices (South China University of Technology) . We thank Dr. Xiao Li and Haijun Chi for the NMR analysis in University of Science and Technology Liaoning. ",

year = "2013",

doi = "10.1016/j.dyepig.2013.08.011",

language = "English",

volume = "99",

pages = "1010--1015",

journal = "Dyes and Pigments",

issn = "0143-7208",

publisher = "Elsevier BV",

number = "3",

}

TY - JOUR

T1 - Greenish yellow organic light emitting devices based on novel iridium complexes containing 2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole

AU - Han, Liangliang

AU - Zhang, Dongyu

AU - Zhou, Yuanhang

AU - Yang, Ying

AU - Woo, Han Young

AU - Bai, Fali

AU - Yang, Renqiang

N1 - Funding Information: This work was supported by Outstanding Young Scientists Research Award Fund of Shandong Province ( BS2010NJ021 ), Shandong Provincial Natural Science Foundation ( ZR2011BZ007 ), Qingdao Municipal Science and Technology Program (11-2-4-22-hz), and State Key Laboratory of Luminescent Materials and Devices (South China University of Technology) . We thank Dr. Xiao Li and Haijun Chi for the NMR analysis in University of Science and Technology Liaoning.

PY - 2013

Y1 - 2013

N2 - 2-Cyclohexenyl-1-phenyl-1H-benzo[d]imidazole (Hcyclopbi) and its heterocyclometalated iridium complexes bis[2-cyclohexenyl-1-phenyl-1H-benzo[d] imidazole](acetylacetonate)iridium(III) [(cyclopbi)2Iracac] and bis[2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole][2-(3-(trifluoromethyl) -1H-pyrazol-5-yl)pyridinate]iridium(III) [(cyclopbi)2IrCF 3] were firstly designed and synthesized. Owing to the strong electron withdrawing ability of 2-(3-(trifluoromethyl)-1H-pyrazol) compared to that of acetylacetonate, blue shifted phosphorescence 542 nm was obtained for (cyclopbi)2IrCF3 compared to that of (cyclopbi) 2Iracac 545 nm with photoluminescence quantum yields (φ) 0.22 and 0.25, respectively, as well the highest occupied molecular orbit (HOMO) energy level was estimated to be -5.10 eV for (cyclopbi)2IrCF3, 0.19 eV lower than that of -4.91 eV for (cyclopbi)2Iracac. When (cyclopbi)2Iracac was doped into 4,4′-bis(9H-carbazol-9-yl) biphenyl (CBP) as the emitting layer, high efficiency organic light emitting devices (OLEDs) were obtained with maximum current efficiency (ηc) 22.3 cd/A at 3.1 mA/cm2 and maximum brightness 16,300 cd/m2 at 171.6 mA/cm2, which were comparable to those of bis(2-phenylpyridine)(acetylacetonate)iridium(III) [(ppy) 2Iracac] with the same device structure. This results indicate that (cyclopbi)2Iracac and (cyclopbi)2IrCF3 are potential phosphorescent dyes used for OLEDs.

AB - 2-Cyclohexenyl-1-phenyl-1H-benzo[d]imidazole (Hcyclopbi) and its heterocyclometalated iridium complexes bis[2-cyclohexenyl-1-phenyl-1H-benzo[d] imidazole](acetylacetonate)iridium(III) [(cyclopbi)2Iracac] and bis[2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole][2-(3-(trifluoromethyl) -1H-pyrazol-5-yl)pyridinate]iridium(III) [(cyclopbi)2IrCF 3] were firstly designed and synthesized. Owing to the strong electron withdrawing ability of 2-(3-(trifluoromethyl)-1H-pyrazol) compared to that of acetylacetonate, blue shifted phosphorescence 542 nm was obtained for (cyclopbi)2IrCF3 compared to that of (cyclopbi) 2Iracac 545 nm with photoluminescence quantum yields (φ) 0.22 and 0.25, respectively, as well the highest occupied molecular orbit (HOMO) energy level was estimated to be -5.10 eV for (cyclopbi)2IrCF3, 0.19 eV lower than that of -4.91 eV for (cyclopbi)2Iracac. When (cyclopbi)2Iracac was doped into 4,4′-bis(9H-carbazol-9-yl) biphenyl (CBP) as the emitting layer, high efficiency organic light emitting devices (OLEDs) were obtained with maximum current efficiency (ηc) 22.3 cd/A at 3.1 mA/cm2 and maximum brightness 16,300 cd/m2 at 171.6 mA/cm2, which were comparable to those of bis(2-phenylpyridine)(acetylacetonate)iridium(III) [(ppy) 2Iracac] with the same device structure. This results indicate that (cyclopbi)2Iracac and (cyclopbi)2IrCF3 are potential phosphorescent dyes used for OLEDs.

KW - 2-Cyclohexenyl-1-phenyl-1H-benzo[d]imidazole

KW - Electroluminescence

KW - Greenish yellow phosphorescence

KW - Heterocyclometalated iridium complexes

KW - Organic light emitting devices

KW - Photoluminescence

UR - http://www.scopus.com/inward/record.url?scp=84883533180&partnerID=8YFLogxK

U2 - 10.1016/j.dyepig.2013.08.011

DO - 10.1016/j.dyepig.2013.08.011

M3 - Article

AN - SCOPUS:84883533180

SN - 0143-7208

VL - 99

SP - 1010

EP - 1015

JO - Dyes and Pigments

JF - Dyes and Pigments

IS - 3

ER -

Greenish yellow organic light emitting devices based on novel iridium complexes containing 2-cyclohexenyl-1-phenyl-1H-benzo[d]imidazole

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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