Diarylamino functionalized pyrene derivatives for use in blue OLEDs and complex formation

Wen Li Jia, Theresa McCormick, Qin De Liu, Hiroshi Fukutani, Michael Motala, Rui Yao Wang, Ye Tao*, Suning Wang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

102 Citations (Scopus)

Abstract

Three new 2,2′-dipyridylamino functionalized pyrene derivatives, 1-pyrenyl-2,2′-dipyridylamine (1), 4-(1-pyrenyl)phenyl-2,2′- dipyridylamine (2), and 4-[4′-(1-pyrenyl)biphenyl]-2,2′- dipyridylamine (3) have been synthesized and fully characterized. For comparison of electronic properties, a diphenylamino functionalized molecule 4-[4′-(1-pyrenyl)biphenyl]diphenylamine (4) has also been synthesized. Compounds 1-4 are bright blue emitters in solution and in the solid state with λmax at ∼420-460 nm and a high emission efficiency in solution. All four compounds form amorphous glasses with Tg values of 66 °C, 79 °C, °165 °C, and 98 °C, respectively. The electronic properties of the four compounds were examined by spectroscopic methods, cyclic voltammetry and Gaussian 98 molecular orbital calculations. The utilities of this class of molecules in OLEDs have been demonstrated by EL devices of compounds 3 and 4, which showed that 3 can function as a bright blue emitter and an electron transport material in a double-layer device while 4 can function as a bright blue emitter and a hole transport molecule in a triple-layer device. The dipyridylamino functional group in molecules 1-3 are capable of chelating to metal ions such as Zn(II) as demonstrated by the synthesis and structure of the complex [2-(Zn(O2CCF3) 2]2 (5). The binding of Zn(II) ions to the dipyridyl group causes a reduction of the emission efficiency of the ligand 2.

Original languageEnglish
Pages (from-to)3344-3350
Number of pages7
JournalJournal of Materials Chemistry
Volume14
Issue number22
DOIs
Publication statusPublished - 21 Nov 2004
Externally publishedYes

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