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Derivatives of Cyanonaphthyl-Substituted Phenanthroimidazole as Blue Emitters for Nondoped Organic Light-Emitting Diodes.

ABSTRACT: New multifunctional blue-emissive materials with superior thermal properties, viz., 4,4'-bis(1-(4-naphthyl)-1H-phenanthro[9,10-d]imidazol-2-yl)binaphthyl (NPIBN), 4,4'-bis(1-(4-cyanonaphthyl)-1H-phenanthro[9,10-d]imidazol-2-yl)biphenyl (CNPIBP), and 4,4'-bis(1-(4-cyanonaphthyl)-1H-phenanthro[9,10-d]imidazol-2-yl)binaphthyl (CNPIBN) have been synthesized. The said molecules show high photoluminescence quantum yield (?_s/f: NPIBN-0.75/0.68, CNPIBP-0.85/0.76, and CNPIBN-0.90/0.88). The fabricated nondoped/doped device with CNPIBN/4,4'-bis(carbazol-9-yl)biphenyl: CNPIBN display maximum efficiencies (?_ex 4.96/5.4%; ?_c 7.46/7.56 cd A^-1; ?_p 6.85/6.91 lm W^-1) at low turn-on voltage (3.5/3.8 V). Nondoped devices based on D-?-A architecture, 4-(2-(5-(9H-carbazol-9-yl)thiophen-2-yl)-1H-phenanthro[9,10-d]imidazol-1-yl)naphthalene-1-carbonitrile exhibit maximum efficiencies (?_ex 2.32%; ?_c 4.00 cd A^-1; ?_p 3.42 lm W^-1) compared to 4-(2-(5-(4-(diphenylamino)phenyl)thiophen-2-yl)-1H-phenanthro[9,10-d]imidazol-1-yl)naphthalene-1-carbonitrile (?_ex 2.01%; ?_c 3.89 cd A^-1; ?_p 3.15 lm W^-1).

SUBMITTER: Jayabharathi J

PROVIDER: S-EPMC6649183 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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Derivatives of Cyanonaphthyl-Substituted Phenanthroimidazole as Blue Emitters for Nondoped Organic Light-Emitting Diodes.

Jayabharathi Jayaraman J Nethaji Pavadai P Thanikachalam Venugopal V Ramya Ramaiyan R

ACS omega 20190301 3

New multifunctional blue-emissive materials with superior thermal properties, viz., 4,4'-bis(1-(4-naphthyl)-1H-phenanthro[9,10-d]imidazol-2-yl)binaphthyl (NPIBN), 4,4'-bis(1-(4-cyanonaphthyl)-1H-phenanthro[9,10-d]imidazol-2-yl)biphenyl (CNPIBP), and 4,4'-bis(1-(4-cyanonaphthyl)-1H-phenanthro[9,10-d]imidazol-2-yl)binaphthyl (CNPIBN) have been synthesized. The said molecules show high photoluminescence quantum yield (Φs/f: NPIBN-0.75/0.68, CNPIB ...[more]

PMID: 31459647

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Project description:Aggregation-induced emission (AIE) is an extraordinary photochemical phenomenon described by Tang's group in 2001, where the aggregation of some organic molecules enhances their light emission by limiting intramolecular activity in the aggregate state. This phenomenon offers new opportunities for researchers due to its potential applications in optoelectronics, energy, and biophysics. Tetraphenylethylenes (TPEs) are reliable AIE luminogens with a wide range of successful applications in material chemistry. To expand the library of AIE-active TPEs, both a series of TPE analogues, in which the phenyl rotor has been replaced by the indole ring, and indole-substituted TPE derivatives were designed and synthesized through vinyl-aryl and aryl-aryl bond formations using the Suzuki coupling reaction. Efficient synthetic routes that delivered indole-modified and indole-substituted TPEs have been developed, and almost all heterocyclic TPE analogues have demonstrated AIE behavior. Furthermore, to test whether the indole ring can be diversified, two title compounds were converted to a series of bis(indolyl)methane (BIM), and these BIM-TPE materials showed typical AIE properties. Interestingly, two compounds indicated a solvent vapor fuming reversible switch between bright blue emission and greenish-yellow emission. Upon fuming with dichloromethane, their fluorescence spectra showed 8 and 32 nm red-shift and could return to the original state after fuming with hexane. Furthermore, we have explored the effects of replacing the phenyl ring in TPE with indole together with the substitution of TPE with indole ring(s) on the performance of organic light-emitting diode (OLED) device applications. In addition, density functional theory calculations; the optical, electrochemical, light emission, electroluminescence characteristics; and admittance spectroscopic analysis of OLED devices of four representative TPEs have been investigated in detail. As a result, the indole-TPEs are potential blue emitters with AIE features for conventional OLEDs, which is a significant color in displays and lighting.

Dataset Information

Derivatives of Cyanonaphthyl-Substituted Phenanthroimidazole as Blue Emitters for Nondoped Organic Light-Emitting Diodes.

Publications

Derivatives of Cyanonaphthyl-Substituted Phenanthroimidazole as Blue Emitters for Nondoped Organic Light-Emitting Diodes.

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