• Bulletin of the Korean Chemical Society
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• v.35 no.8
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• pp.2410-2414
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• 2014

A kinetic study is reported on nucleophilic substitution reactions of Y-substituted-phenyl picolinates (7a-7h) with a series of cyclic secondary amines in 80 mol % $H_2O$/20 mol % DMSO at $25.0{\pm}0.1^{\circ}C$. Comparison of the kinetic results with those reported previously for the corresponding reactions of Y-substituted-phenyl benzoates (1a-1f) reveals that 7a-7h are significantly more reactive than 1a-1f. The Br${\o}$nsted-type plot for the aminolysis of 4-nitrophenyl picolinate (7a) is linear with ${\beta}_{nuc}=0.78$, which is typical for reactions proceeding through a stepwise mechanism with expulsion of the leaving group being the rate-determining step. The Br${\o}$nsted-type plots for the piperidinolysis of 7a-7h and 1a-1f are also linear with ${\beta}_{lg}=-1.04$ and -1.39, respectively, indicating that the more reactive 7a-7h are less selective than the less reactive 1a-1f to the leaving-group basicity. One might suggest that the enhanced reactivity of 7a-7h is due to the inductive effect exerted by the electronegative N atom in the picolinyl moiety, while the decreased selectivity of the more reactive substrates is in accord with the reactivity-selectivity principle. However, the nature of intermediate (e.g., a stabilized cyclic intermediate through the intramolecular H-bonding interaction for the reactions of 7a-7h, which is structurally not possible for the reactions of 1a-1f) is also responsible for the enhanced reactivity with a decreased selectivity.

• Transactions on Electrical and Electronic Materials
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• v.12 no.2
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• pp.84-87
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• 2011

We fabricated phosphorescent organic light-emitting devices with a 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC) host layer. Two kinds of devices, one of ITO/TAPC/TAPC:FIrpic/TAZ/LiF/Al (device A) and one of ITO/TAPC:FIrpic/TAPC/TAZ/LiF/Al (device B), were prepared to investigate electrical and optical properties. Iridium(III) bis[(4,6-difluorophenyl)-pyridinato-N,$C^{2'}$]picolinate (FIrpic) and 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (TAZ) were used as a blue phosphorescent guest material and an electron transport layer, respectively. The TAPC layer in device B strongly contributes to whitish emission, higher driving voltage, and lower current efficiency characteristics compared with device A. The mechanisms of these electrical and optical characteristics of the devices were investigated.

• Journal of Information Display
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• v.12 no.4
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• pp.219-222
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• 2011

Iridium-(III)-bis[(4,6-di-fluorophenyl)-pyridinate-N,$C^2$' ]picolinate-based blue phosphorescent organic light-emitting diodes with different electron transport materials were fabricated. Each electron transport material had different electron mobilities and triplet energies. The device with 1,3,5-tri(m-pyrid-3-yl-phenyl)benzene had the highest external quantum efficiency (20.1%) and luminous current efficiency (33.1 cd/A) due to its high electron mobility and triplet energy. The operational stability of each device was also compared with that of the others. The device with 2,2',2"(1,3,5-benzenetriyl)tris-(1-phenyl-1H-benzimidazole) was found to have a longer lifetime than the other devices.

• Transactions on Electrical and Electronic Materials
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• v.12 no.2
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• pp.80-83
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• 2011

We have fabricated phosphorescent white organic light-emitting devices (WOLEDs) with a spin-coated poly(Nvinylcarbazole) [PVK] host layer. Iridium(III) bis[(4,6-difluorophenyl)-pyridinato-N,$C^{2'}$]picolinate (FIrpic), tris(2-phenylpyridine)iridium(III) [$Ir(ppy)_3$], and tris(2-phenyl-1-quinoline)iridium(III) [$Ir(phq)_3$], were used as the blue, green, and red guest materials, respectively. The PVK was mixed with FIrpic, $Ir(ppy)_3$, and $Ir(phq)_3$ molecules in a chlorobenzene solution and spin-coated in order to prepare the emission layer; 3-(4-biphenylyl)-4-phenyl-5-(4-tertbutylphenyl)-1,2,4-triazole (TAZ) was used as an electron transport material. The resultant device structure was ITO/PVK:FIrpic:$Ir(ppy)_3:Ir(phq)_3$/TAZ/LiF/Al. The electroluminescence, efficiency, and electrical conduction characteristics of the WOLEDs based on the doped PVK host layer were investigated. The maximum current efficiency of the three wavelength WOLED with the doped PVK host was 19.2 cd/A.

• Journal of the Korean Chemical Society
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• v.55 no.3
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• pp.354-363
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• 2011

Quantum-chemistry study was explored to investigate the electronic structures, absorption and phosphorescence mechanism, as well as electroluminescence (EL) properties of three red-emitting Ir(III) complexes, $(fpmqx)_2Ir$(L) {fpmqx=2-(4-fluorophenyl)-3-methyl-quinoxaline; L=triazolylpyridine (trz) (1); L=picolinate (pic) (2) and L=acetylacetonate (acac) (3)}. The calculated results show that the HOMO distribution for 1 is mainly localized on trz moiety due to its stronger ${\pi}$-electron acceptor ability, and HOMO for 2 and 3 is the combination of Ir d- and phenyl ring ${\pi}$-orbital. The higher phosphorescence yields and differences among 1-3 are investigated in this paper. In addition, the reasons of higher EL efficiency of 2 than 1 and 3 have been rationalized.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.27 no.4
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• pp.232-237
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• 2014

We have fabricated white organic light-emitting diodes (OLEDs) by co-doping of red and blue phosphorescent guest emitters into the single host layer. Tris(2-phenyl-1-quinoline) iridium(III) [$Ir(phq)_3$] and iridium(III)bis[(4,6-di-fluorophenyl)-pyridinato-$N,C^{2^{\prime}}$]picolinate (FIrpic) were used as red and blue dopants, respectively. The effects of dopant concentration on the emission, carrier conduction and external quantum efficiency characteristics of the devices were investigated. The emissions on the guest emitters were attributed to the energy transfer to the guest emitters and direct excitation by trapping of the carriers on the guest molecules. The white OLED with 5% FIrpic and 2% $Ir(phq)_3$ exhibited a maximum external quantum efficiency of 19.9% and a maximum current efficiency of 45.2 cd/A.

• Journal of the Korean Institute of Electrical and Electronic Material Engineers
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• v.27 no.6
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• pp.377-382
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• 2014

We have investigated the effects of spacer layer inserted between blue and red doped emission layers on the emission and efficiency characteristics of phosphorescent OLEDs. N,N'-di-carbazolyl-3,5-benzene (mCP) was used as a host layer. Iridium(III)bis[(4,6-di-fluorophenyl)- pyridinato-N,$C^2$']picolinate (FIrpic) and tris(1-phenyl-isoquinolinato-$C^2$,N)iridium(III) [Ir(piq)3] were used as blue and red dopants, respectively. The emission layer structure was mCP (1-x) nm/mCP:$Ir(piq)_3$ (5 nm, 10%)/mCP (x nm)/mCP:FIrpic (5 nm, 10%). The thickness of mCP spacer layer was varied from 0 to 15 nm. The emission from $Ir(piq)_3$ and the efficiency of the device were dominated by energy transfer from mCP host and FIrpic molecules, and by diffusion of mCP host triplet excitons.

• Journal of the Korean Applied Science and Technology
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• v.24 no.1
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• pp.74-78
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• 2007

A new blue phosphorescent material for organic light emitting diodes (OLEDs), Iridium(III)bis[2-(4-fIuoro-3-benzonitrile)-pyridinato-N,C2'] picolinate (Firpic-CN), was synthesized and studied. We compared characteristics of Firpic-CN and Bis(3,5-Difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl) iridium III (FIrpic) which has been used for blue dopant materials frequently. The devices structure were indium tin oxide (ITO) (1000 ${\AA}$)/N,N'-diphenyl-N,N'-(2-napthyl)-(1,1'-phenyl)-4,4'-diamine (NPB) (500 ${\AA}$)/4,4'-N,N'-dicarbazole-biphyenyl (CBP) : FIrpic and FIrpic-CN (X wt%)/4,7-diphenyl-1,10-phenanthroline (BPhen) (300 ${\AA}$)/lithum quinolate (Liq) (20 ${\AA}$)/Al (1000 ${\AA}$). 15 wt% FIrpic-CN doped device exhibits a luminance of $1450\;cd/m^2$ at 12.4 V, luminous efficiency of 1.31 cd/A at $3.58mA/cm^2$, and Commission Internationale d'Eclairage $(CIE_{x,y})$ coordinates of (0.15, 0.12) at 12 V which shows a very deep blue emission. We also measured lifetime of devices and was presented definite difference between devices of FIrpic and FIrpic-CN. Device with FIrpic-CN as a dopant presented lower longevity due to chemical effect of CN ligand.

• Korean Journal of Materials Research
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• v.26 no.3
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• pp.117-122
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• 2016

White organic light-emitting diodes with a structure of indium-tin-oxide [ITO]/N,N-diphenyl-N,N-bis-[4-(phenylm-tolvlamino)-phenyl]-biphenyl-4,4-diamine [DNTPD]/[2,3-f:2, 2-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile [HATCN]/1,1-bis(di-4-poly-aminophenyl) cyclo -hexane [TAPC]/emission layers doped with three color dopants/4,7-diphenyl-1,10-phenanthroline [Bphen]/$Cs_2CO_3$/Al were fabricated and evaluated. In the emission layer [EML], N,N-dicarbazolyl-3,5-benzene [mCP] was used as a single host and bis(2-phenyl quinolinato)-acetylacetonate iridium(III) [Ir(pq)2acac]/fac-tris(2-phenylpyridinato) iridium(III) $[Ir(ppy)_3]$/iridium(III) bis[(4,6-di-fluoropheny)-pyridinato-N,C2] picolinate [FIrpic] were used as red/green/blue dopants, respectively. The fabricated devices were divided into five types (D1, D2, D3, D4, D5) according to the structure of the emission layer. The electroluminescence spectra showed three peak emissions at the wavelengths of blue (472~473 nm), green (495~500 nm), and red (589~595 nm). Among the fabricated devices, the device of D1 doped in a mixed fashion with a single emission layer showed the highest values of luminance and quantum efficiency at the given voltage. However, the emission color of D1 was not pure white but orange, with Commission Internationale de L'Eclairage [CIE] coordinates of (x = 0.41~0.45, y = 0.41) depending on the applied voltages. On the other hand, device D5, with a double emission layer of $mCP:[Ir(pq)_2acac(3%)+Ir(ppy)_3(0.5%)]$/mCP:[FIrpic(10%)], showed a nearly pure white color with CIE coordinates of (x = 0.34~0.35, y = 0.35~0.37) under applied voltage in the range of 6~10 V. The luminance and quantum efficiency of D5 were $17,160cd/m^2$ and 3.8% at 10 V, respectively.