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CC BY-NC-ND 4.0 · Organic Materials 2020; 02(01): 011-019
DOI: 10.1055/s-0039-3402513
Original Article
The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/). (2020) The Author(s).

Fluorine-Substituted Phenanthro[9,10-d]imidazole Derivatives with Optimized Charge-Transfer Characteristics for Efficient Deep-Blue Emitters

Zhiqiang Li 
a   State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
,
Ning Xie
a   State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
,
Yincai Xu
a   State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
,
Chenglong Li 
a   State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
,
Xiaoyue Mu 
a   State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
,
Yue Wang 
a   State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
› Author Affiliations Funding Information This work was supported by the National Natural Science Foundation of China (21935005 and 51803069) and Program for JLU Science and Technology Innovative Research Team (2019TD-33).
Further Information

Publication History

Received: 15 October 2019

Accepted after revision: 19 November 2019

Publication Date:
23 January 2020 (online)

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Abstract

The development of high-efficiency deep-blue emitters is of great importance for full-color organic light-emitting diodes (OLEDs). In this contribution, three difluorine-substituted phenanthro[9,10-d]imidazole derivatives with optimized charge-transfer character and deep-blue emission have been developed. It is demonstrated that the fluorine substitution can facilitate the “state mixing” of singlet and triplet excitons, which increases the utilization of triplet excitons. The fluorine substitution also brings more intermolecular interactions which have influence on the molecular packing pattern of the solid states, ultimately impacting their carrier mobilities. Through fine-tuning of molecular structures, 4'-(1-(3,5-difluorophenyl)-1H-phenanthro[9,10-d]imidazol-2-yl)-N,N-diphenyl-[1,1'-biphenyl]-4-amine (2FPPIDPA) realized a high exciton utilization ratio with Commission Internationale de L'Eclairage (CIE) coordinates of (0.156, 0.046), and 4'-(1-(3,5-difluorophenyl)-1H-phenanthro[9,10-d]imidazol-2-yl)-N,N-diphenyl-[1,1'-biphenyl]-4-amine (2FPPIDPA) achieved an external quantum efficiency of 8.47% with CIE coordinates of (0.152, 0.083) in multilayer OLEDs. Due to their good hole-transport abilities, double-layer OLEDs without the hole-transport layer showed performances comparable or even superior to the multilayer ones.

Key words

organic light-emitting diodes - blue emitters - phenanthro[9 - 10-d]imidazole - charge-transfer state - fluorine substituents

Supporting Information

Supporting information for this article is available online at: https://doi.org/10.1055/s-0039-3402513.


Supporting Information

Primary Data

    Crystal files of 2FPPImTPA, 2FPPIDPA, and 2FPPITPA are provided in CCDC 1939337, 1939338, and 1939339, respectively. Primary data for this article are available online at: https://doi.org/10.1055/s-0039-3402513 and can be cited using the following DOI: 10.5281/zenodo.4610547.

  • Primary Data
 

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