New Class of Organic Hole-Transporting Materials Based on Xanthene Derivatives for Organic Electronic Applications

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Martins, Jefferson S. ; Bartolomeu, Aloisio A. ; dos Santos, Willian Henrique ; da Silva Filho, Luiz Carlos ; de Oliveira, Eliezer Fernando ; Lavarda, Francisco Carlos ; Cuin, Alexandre ; Legnani, Cristiano ; Maciel, Indhira O. ; Fragneaud, Benjamin ; Quirino, Welber G.

• Document type: Journal article
• Source: Journal of Physical Chemistry C; v. 121, n. 24, p. 12999-13007, JUN 22 2017.
• Web of Science Citations: 6

Abstract

In this work, we investigate the influence of three novel 14-aril-14H-dibenzo{[}a,j]xanthene derivatives (XDs) modified with different functional groups as very promising hole-transporting materials for organic optoelectronic devices. Optical, electronic, and structural properties were analyzed by UVvis absorption spectrum, cyclic voltammetry, and powder X-ray powder diffraction (XRPD). We investigated the influence of these XD as hole-transporting layers (HTL) on the performance of a simple stack bilayer OLED built with commercial aluminum tris(8-hydroxyquinoline) Alq(3) acting as an electron-transporting and emissive layer (EML). As a proof-of-principle the XD devices were compared to reference devices fabricated with one of the most common hole-transporting materials, the N,N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-2,2'-dimethylbenzidine (alpha-NPD). The structure of the devices was ITO/HTL (50 nm)/Alq(3) (50 nm)/Al (120 nm) without encapsulation. Under the same conditions, the devices using XD as HTL exhibited high performance and significant durability when compared to the reference ones. These results are also supported by a theoretical study using density functional theory (DFT) showing that this set of XD presents a higher hole mobility than alpha-NPD. Thus, we demonstrated that this class of molecules are very promising when used as hole-transport material in organic electronic devices. (AU)

• FAPESP's process: 13/08697-0 - Studies about the use niobium pentachloride in multicomponent reactions toward the synthesis of dye-sensitizers with potential application in photoelectrochemical devices of Grätzel
• Grantee: Luiz Carlos da Silva Filho
• Support Opportunities: Regular Research Grants
• FAPESP's process: 14/20410-1 - Electronic structure of organic materials for applications in the active layer of solar cells
• Grantee: Francisco Carlos Lavarda
• Support Opportunities: Regular Research Grants
• FAPESP's process: 16/01599-1 - Studies about the use of NbCl5 in multicomponent reactions for the synthesis of organic dyes
• Grantee: Luiz Carlos da Silva Filho
• Support Opportunities: Regular Research Grants
• FAPESP's process: 12/21983-0 - ELECTRONIC STRUCTURE OF ORGANIC MATERIALS FOR APPLICATIONS IN SOLAR CELLS' ACTIVE LAYERS
• Grantee: Eliezer Fernando de Oliveira
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 12/23821-7 - Synthesis of 14-Aryl-14H-dibenzo[a,j]xanthenes and 4-Aryl-3,4-dihydro-benzo[f]coumarins promoted by niobium pentachloride, with potential application in the preparation of dyes-sensitizers for use in Grätzel devices.
• Grantee: Aloisio de Andrade Bartolomeu
• Support Opportunities: Scholarships in Brazil - Master