Synthesis, characterization of the phenylquinoline-based on iridium(III) complexes for solution processable phosphorescent organic light-emitting diodes

Organic Electronics

Volumn 14, Issue 9, 2013, Pages 2114-2123

  Park, Juhyeon ^a   Park, Jin Su ^a   Park, Young Geun ^b   Lee, Jin Yong ^b   Kang, Jae Wook ^c   Liu, Jun ^d   Dai, Liming ^d   Jin, Sung Ho ^a  

^a Pusan National University   (South Korea)

^b Sungkyunkwan University   (South Korea)

^c Chonbuk National University   (South Korea)

^d Case Western Reserve University   (United States)

Author keywords

Iridium complex; Organic light emitting diodes; Phosphorescent; Picolinic acid N oxide; Solution processable

Indexed keywords

DIODES; LIGANDS; LUMINANCE; ORGANIC LIGHT EMITTING DIODES (OLED); PHOSPHORESCENCE; PYRIDINE; SYNTHESIS (CHEMICAL);

ELECTRO-LUMINESCENT; EXTERNAL QUANTUM EFFICIENCY; HOMO-LUMO ENERGY GAP; IRIDIUM COMPLEX; PHOSPHORESCENT; PHOSPHORESCENT ORGANIC LIGHT EMITTING DIODES; PICOLINIC ACID N-OXIDE; SOLUTION PROCESSABLE;

IRIDIUM COMPOUNDS;

EID: 84878493953     PISSN: 15661199     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.orgel.2013.05.013     Document Type: Article

References (36)

1. C.H. Chien, C.K. Chen, F.M. Hsu, C.F. Shu, P.T. Chou, C.H. Lai, Multifunctional deep-blue emitter comprising an anthracene core and terminal triphenylphosphine oxide groups, Adv. Funct. Mater. 19 (2009) 560-566.
2. X. Xing, L. Zhang, R. Liu, S. Li, B. Qu, Z. Chen, W. Sun, L. Xiao, Q. Gong, A deep-blue emitter with electron transporting property to improve charge balance for organic light-emitting device, ACS Appl. Mater. Interf. 4 (2012) 2877-2880.
3. L. Xiao, Z. Chen, B. Qu, J. Luo, S. Kong, Q. Gong, J. Kido, Recent progresses on materials for electrophosphorescent organic lightemitting devices, Adv. Mater. 23 (2011) 926-952.
4. R. Ragni, E. Plummer, K. Brunner, J.W. Hofstraat, F. Babudri, G.M. Farinola, F. Naso, L. De Cola, Blue emitting iridium complexes: synthesis, photophysics and phosphorescent devices, J. Mater. Chem. 16 (2006) 1161-1170.
5. H.J. Bolink, E. Coronado, S.G. Santamaria, M. Sessolo, N. Evans, C. Klein, E. Baranoff, K. Kalyanasundaram, M. Gräetzel, Md.K. Nazeeruddin, Highly phosphorescent perfect green emitting iridium(III) complex for application in OLEDs, Chem. Commun. (2007) 3276-3278. (Pubitemid 47197856)
6. P. Coppo, E.A. Plummer, L. De Cola, Tuning iridium(III) phenylpyridine complexes in the "almost blue" region, Chem. Commun. (2004) 1774-1775. (Pubitemid 39127876)
7. T. Sajoto, P.I. Djurovich, A.B. Tamayo, M. Yousufuddin, R. Bau, M.E. Thompson, R.J. Holmes, S.R. Forrest, Blue and near-UV phosphorescence from iridium complexes with cyclometalated pyrazolyl or n-heterocyclic carbene ligands, Inorg. Chem. 44 (2005) 7992-8003. (Pubitemid 41619101)
8. C. Yang, X. Zhang, H. You, L. Zhu, L. Chen, L. Zhu, Y, Tao, D. Ma, Z. Shuai, J. Qin, Tuning the energy level and photophysical and electroluminescent properties of heavy metal complexes by controlling the ligation of the metal with the carbon of the carbazole unit, Adv. Funct. Mater. 17 (2007) 651-661. (Pubitemid 46423480)
9. R.N. Bera, N. Cumpstey, P.L. Burn, I.D.W. Samuel, highly branched phosphorescent dendrimers for efficient solution-processed organic light-emitting diodes, Adv. Funct. Mater. 17 (2007) 1149-1152. (Pubitemid 46762602)
10. P. Wellmann, M. Hofmann, O. Zeika, A. Werner, J. Birnstock, R. Meerheim, G.F. He, K. Walzer, M. Pfeiffer, K. Leo, High-efficiency p-i- n organic light-emitting diodes with long lifetime, J. Soc. Inf. Display 13 (2005) 393-397.
11. M. Cai, T. Xiao, E. Hellerich, Y. Chen, R.J. Shinar, High-efficiency solution-processed small molecule electrophosphorescent organic light-emitting diodes, Adv. Mater. 23 (2011) 3590-3596.
12. S. Ye, Y. Liu, K. Lu, W. Wu, C. Du, Y. Liu, H. Liu, T. Wu, G. Yu, An alternative approach to constructing solution processable multifunctional materials: their structure, properties, and application in high-performance organic light-emitting diodes, Adv. Funct. Mater. 20 (2010) 3125-3135.
13. E. Ahmed, T. Earmme, S.A. Jenekhe, New solution-processable electron transport materials for highly efficient blue phosphorescent OLEDs, Adv. Funct. Mater. 21 (2011) 3889-3899.
14. Y. Yang, Y. Zhou, Q. He, C. Yang, F. Bai, Y. Li, Solution-processable redemission organic materials containing triphenylamine and benzothiodiazole units: synthesis and applications in organic lightemitting diodes, J. Phys. Chem. B. 113 (2009) 7745-7752.
15. S. Feng, L. Duan, L. Hou, J. Qiao, D. Zhang, G. Dong, L. Wang, Y.A. Qiu, A comparison study of the organic small molecular thin films prepared by solution process and vacuum deposition: roughness, hydrophilicity, absorption, photoluminescence, density, mobility, and electroluminescence, J. Phys. Chem. C. 115 (2011) 14278- 14284.
16. X.H. Yang, F.I. Wu, D. Neher, C.H. Chien, C.F. Shu, Efficient redemitting electrophosphorescent polymers, Chem. Mater. 20 (2008) 1629-1635.
17. Y.J. Pu, M. Higashidate, K.I. Nakayama, J. Kido, Solution-processable organic fluorescent dyes for multicolor emission in organic light emitting diodes, J. Mater. Chem. 18 (2008) 4183-4188.
18. S.C. Lo, G.J. Richards, J.P.I. Markham, E.B. Naamdas, S. Sharma, P.L. Burn, I.D.W. Samuel, A light-blue phosphorescent dendrimer for efficient solution-processed light-emitting diodes, Adv. Funct. Mater. 15 (2005) 1451-1458. (Pubitemid 41284824)
19. R.H. Friend, R.W. Gymer, A.B. Holmes, J.H. Burroughes, R.N. Marks, C. Taliani, D.D.C. Bradley, D.A. Dos Santos, J.L. Brédas, M. Lögdlund, W.R. Salaneck, Electroluminescence in conjugated polymers, Nature 397 (1999) 121-128. (Pubitemid 29050908)
20. T. Guo, R. Guan, J. Zou, J. Liu, L. Ying, W. Yang, H. Wu, Y. Cao, Red light-emitting hyperbranched fluorene-alt-carbazole copolymers with an iridium complex as the core, Polym. Chem. 2 (2011) 2193-2203.
21. J. Ding, J. Lü, Y. Cheng, Z. Xie, L. Wang, X. Jing, F. Wang, A divergent synthesis of very large polyphenylene dendrimers with iridium(III) cores: molecular size effect on the performance of phosphorescent organic light-emitting diodes, Adv. Funct. Mater. 18 (2008) 2754- 2762.
22. B. Liang, L. Wang, Y. Xu, H. Shi, Y. Cao, High-efficiency red phosphorescent iridium dendrimers with charge-transporting dendrons: synthesis and electroluminescent properties, Adv. Funct. Mater. 17 (2007) 3580-3589. (Pubitemid 350221712)
23. G. Zhou, W.Y. Wong, B. Yao, Z. Xie, L. Wang, Triphenylamine- Dendronized pure red iridium phosphors with superior OLED efficiency/color purity trade-offs, Angew. Chem. Int. Ed. 46 (2007) 1149-1151. (Pubitemid 46959371)
24. S.C. Lo, R.E. Harding, E. Brightman, P.L. Burn, I.D.W. Samuel, The development of phenylethylene dendrons for blue phosphorescent emitters, J. Mater. Chem. 19 (2009) 3213-3227.
25. X. Yang, D.C. Müller, D. Neher, K. Meerholz, Adv. Mater. 18 (2006) 948-954.
26. K.S. Yook, J.Y. Lee, Solution processed multilayer deep blue and white phosphorescent organic light-emitting diodes using an alcohol soluble bipolar host and phosphorescent dopant materials, J. Mater. Chem. 22 (2012) 14546-14550.
27. S.J. Lee, J.S. Park, M. Song, I.A. Shin, Y.I. Kim, J.W. Lee, J.W. Kang, Y.S. Gal, S. Kang, Y. Lee, S.H. Jung, H.S. Kim, M.Y. Chae, S.H. Jin, Synthesis and characterization of red-emitting iridium(III) complexes for solution-processable phosphorescent organic light-emitting diodes, Adv. Funct. Mater. 19 (2009) 2205-2212.
28. A.K. Agrawal, S.A. Jenekhe, Thin-film processing and optical properties of conjugated rigid-rod polyquinolines for nonlinear optical applications, Chem. Mater. 4 (1992) 95-104.
29. S.J. Lee, J.S. Park, K.J. Yoon, S.H. Jim, S.K. Kang, Y.S. Gal, S. Kang, J.Y. Lee, J.W. Kang, S.H. Lee, H.D. Park, J.J. Kim, High-efficiency deep-blue light-emitting diodes based on phenylquinoline/carbazole-based compounds, Adv. Funct. Mater. 18 (2008) 3922-3930.
30. S. Lamansky, P. Djurovich, D. Murphy, F. Abdel-Razzaq, R. Kwong, I. Tsyba, M. Bortz, B. Mui, R. Bau, M.E. Tompson, Synthesis and characterization of phosphorescent cyclometalated iridium complexes, Inorg. Chem. 40 (2001) 1704-1711. (Pubitemid 32879659)
31. H. Razafitrimo, Y. Cao, W.A. Feld, B.R. Hsieh, A layer-wise topographic study of a polymeric light-emitting diode: indium-tin oxide/poly (2, 3-diphenyl-p-phenylene vinylene)/Ag, Synth. Met. 79 (1996) 103-106. (Pubitemid 126369177)
32. C. Liu, X.C. Zou, S. Yin, W.X. Zhang, Influence of spin methods on the performance of polymer light-emitting devices, Thin Solid Films 466 (2004) 279-284.
33. H.A. Al-Attar, A.P. Monkman, Solution processed multilayer polymer light-emitting diodes based on different molecular weight host, J. Appl. Phys. 109 (2011) 074516.
34. Q.X. Tong, S.L. Lai, M.Y. Chan, K.H. Lai, J.X. Tang, H.L. Kwong, C.S. Lee, S.T. Lee, Efficient green organic light-emitting devices with a nondoped dual-functional electroluminescent material, Appl. Phys. Lett. 91 (2007) 153504.
35. M.J. Frisch et al., Gaussian 09, Revision B.01; Gaussian Inc.: Wallingford, CT, 2010.
36. M. Nonoyama, Chelating C-metallation of N-phenylpyrazole with rhodium(III) and iridium(III), J. Organomet. Chem. 86 (1975) 263- 267.