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Planar Organic Semiconductor-Materials for Flexible OLEDs

Planar Organic Semiconductor-Materials for Flexible OLEDs

Johannes Fröhlich (ORCID: 0000-0003-0840-2314)
  • Grant DOI 10.55776/I2589
  • Funding program Principal Investigator Projects International
  • Status ended
  • Start March 1, 2016
  • End October 31, 2019
  • Funding amount € 301,392
  • Project website

Bilaterale Ausschreibung: China

Disciplines

Chemistry (100%)

Keywords

    Functional Organic Materials, Solution Processing, OLED, Host Materials, Indolocarbazole

Abstract Final report

Organic light emitting diodes (OLEDs) have raised significant attention both in science and industry because of potential display and lighting applications. Benefiting from favorable features such as homogenous large-area emission, lightweight and ultra-thin applications, OLEDs are expected to become a competitive candidate in the future lighting market. In addition, unique characteristics such as flexibility in OLEDs allow for new concepts for the design of lighting products. To realize practical lighting application, the efficacy and stability of the flexible OLEDs require further improvement. Thus, the combined scientific efforts of researchers on both material synthesis and device fabrication are the prerequisite for successful research on these topics. Within this project, two teams from China and Austria will jointly develop novel materials for high performance flexible OLEDs. The research team led by Prof. Johannes Fröhlich at the Institute of Applied Synthetic Chemistry (Vienna University of Technology) will develop organic materials with desirable material characteristics with regard to stability and charge transport properties for OLEDs by designing rigid planarized molecular frameworks. The research team led by Prof. Dongge Ma in the Changchun Institute of Applied Chemistry (Chinese Academy of Sciences) will focus on developing high performance flexible OLEDs by combining both material and device engineering. As a result, the major goal of this project is to understand the relationships between material characteristics, device architectures and device performances. Hence, the intense collaboration of the material scientists in the Prof. Fröhlich group and the device engineers in the Prof. Ma group will trigger a valuable feedback loop in order to improve the OLED technology and, thus, to impact future lightning developments.

In recent years growing interest occurred in utilizing organic light emitting diodes (OLEDs) for display application, but increasingly also for solid state lighting, due to energy efficiency and the possibility of thin and flexible large area devices. Additionally, the possibility to process organic materials from solution using for example printing methods, can enable low production costs. The study of structure property relationships and their control is important for the development of new materials. This, together with advanced device engineering are important factors to generate improved devices. Lately, in my research group indolo[3,2,1-jk]carbazole (ICz) as new building block for organic electronics was introduced. ICz is a versatile building block having both weak electron donating and accepting properties, and materials utilizing it usually exhibit high triplet energies and good thermal stability, both beneficial for application in OLEDs. Within this project ICz should be used as molecular platform enabling to tune material properties with various modifications of the scaffold. In the first part of this project, sulfur and nitrogen atoms were introduced into the ICz scaffold allowing to increase electron donating or accepting strength, depending on the type of heteroatom used. A synthetic approach was developed for the selective incorporation of heteroatoms to specific positions within the scaffold. The photophysical and electrochemical properties can be fine-tuned by variation of the positions and the amount of the heteroatoms. Additionally, the nitrogen atoms introduced have large impact on the alignment in the crystalline state, which is a crucial factor for functional organic materials. The applicability of the nitrogen incorporated derivatives was investigated in a set of molecules which were utilized as emitters in OLEDs. The emission of these materials was tuned over a wide range by building block variation, proofing the possibility of property fine-tuning using these novel building blocks. Materials utilizing the ICz motif usually exhibit rather low solubilities. Therefore, in addition to the modification using heteroatoms, the attachment of alkyl chains was investigated. This significantly improved the solubility of the materials, rendering the applicability of ICz based materials for solution processing techniques. Using the alkylated ICz building blocks, materials were developed which were successfully employed in OLEDs processed from solution. Besides the improved processability also the stability of the materials was increased by the alkylation. Finally, we were able to show that the substitution pattern of the ICz motif has large impact on the interactions within thin films. It was possible to develop new materials which allowed the fabrication of OLED devices with increased performance compared to previously reported ones using similar materials.

Research institution(s)
  • Technische Universität Wien - 100%
International project participants
  • Dongge Ma, South China University of Technology - China

Research Output

  • 114 Citations
  • 20 Publications
  • 19 Datasets & models
  • 2 Scientific Awards
Publications
  • 2021
    Title Alkylated indolo[3,2,1-jk]carbazoles as new building blocks for solution processable organic electronics
    DOI 10.1016/j.orgel.2021.106215
    Type Journal Article
    Author Kader T
    Journal Organic Electronics
    Pages 106215
    Link Publication
  • 2020
    Title Synthesis of Nitrogen-Incorporated Indolo[3,2,1-jk]carbazole Derivatives
    Type Other
    Author Birgit Meindl
  • 2020
    Title Development of Novel Planarized Triarylamine Based Materials for OLEDs
    Type Other
    Author Thomas Kader
  • 2019
    Title Free-Energy Calculations for Bioisosteric Modifications of A3 Adenosine Receptor Antagonists
    DOI 10.3390/ijms20143499
    Type Journal Article
    Author Jandova Z
    Journal International Journal of Molecular Sciences
    Pages 3499
    Link Publication
  • 2019
    Title PET imaging of the mouse brain reveals a dynamic regulation of SERT density in a chronic stress model
    DOI 10.1038/s41398-019-0416-7
    Type Journal Article
    Author Reisinger S
    Journal Translational Psychiatry
    Pages 80
    Link Publication
  • 2019
    Title The phase transitions of 4-aminopyridine-based indolocarbazoles: twinning, local- and pseudo-symmetry
    DOI 10.1107/s2052520618017341
    Type Journal Article
    Author Kader T
    Journal Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
    Pages 97-106
    Link Publication
  • 2019
    Title Thienopyrrolocarbazoles: New Building Blocks for Functional Organic Materials
    DOI 10.26434/chemrxiv.7777343.v1
    Type Preprint
    Author Bader D
  • 2019
    Title Azaindolo[3,2,1-jk]carbazole based donor-acceptor materials as potential TADF emitters
    Type Other
    Author Nikolaus Poremba
  • 2019
    Title Azaindolo[3,2,1-jk]carbazoles: New Building Blocks for Functional Organic Materials
    DOI 10.1002/chem.201805578
    Type Journal Article
    Author Kader T
    Journal Chemistry – A European Journal
    Pages 4412-4425
    Link Publication
  • 2019
    Title Thienopyrrolo[3,2,1-jk]carbazoles: Building Blocks for Functional Organic Materials
    DOI 10.1021/acs.joc.9b02426
    Type Journal Article
    Author Bader D
    Journal The Journal of Organic Chemistry
    Pages 3865-3871
    Link Publication
  • 2018
    Title Novel annulated heterocycles based on the indolo[3,2,1-jk]carbazole scaffold
    Type Other
    Author Dorian Bader
  • 2016
    Title Synthesis of novel carboline-based annulated heterocyclic systems for organic electronics
    Type Other
    Author Thomas Kader
  • 2017
    Title Intramolekularer Charge Transfer in funktionellen organischen Materialien
    DOI 10.34726/hss.2017.43446
    Type Other
    Author Kautny P
    Link Publication
  • 2018
    Title Controlling excimer formation in indolo[3,2,1- jk ]carbazole/9 H -carbazole based host materials for RGB PhOLEDs
    DOI 10.1039/c8tc03537g
    Type Journal Article
    Author Zhao C
    Journal Journal of Materials Chemistry C
    Pages 9914-9924
    Link Publication
  • 2018
    Title A novel selenoalkenyl-isoxazole based donor–acceptor nonlinear optical material
    DOI 10.1039/c7ce01925d
    Type Journal Article
    Author Holzer B
    Journal CrystEngComm
    Pages 12-16
    Link Publication
  • 2017
    Title Thieno[3,4- c ]pyrrole-4,6-dione as novel building block for host materials for red PhOLEDs
    DOI 10.1039/c6tc05248g
    Type Journal Article
    Author Kautny P
    Journal Journal of Materials Chemistry C
    Pages 1997-2004
    Link Publication
  • 2017
    Title An unusual case of OD-allotwinning: 9,9'-(2,5-dibromo-1,4-phenylene)bis[9H-carbazole]
    DOI 10.1107/s2052520616018291
    Type Journal Article
    Author Kautny P
    Journal Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
    Pages 65-73
    Link Publication
  • 2017
    Title Indolo[3,2,1-jk]carbazole based materials for OLED applications
    Type Other
    Author Thomas Schwartz
  • 2017
    Title OD- and non-OD-polytypism of 9-(3-chloropyridin-4-yl)-9H-carbazole
    DOI 10.1515/zkri-2016-2040
    Type Journal Article
    Author Kader T
    Journal Zeitschrift für Kristallographie - Crystalline Materials
    Pages 375-384
    Link Publication
  • 2017
    Title Functional organic click-materials: application in phosphorescent organic light emitting diodes
    DOI 10.1039/c6ra28212a
    Type Journal Article
    Author Kautny P
    Journal RSC Advances
    Pages 12150-12160
    Link Publication
Datasets & models
  • 2019 Link
    Title CCDC 1864321: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc20kzdz
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1864322: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc20kzf0
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1864324: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc20kzh2
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1864325: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc20kzj3
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1864326: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc20kzk4
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1864327: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc20kzl5
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1864328: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc20kzm6
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1883688: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc21744l
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1883689: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc21745m
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1883690: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc21746n
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1883691: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc21747p
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1883692: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc21748q
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1883693: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc21749r
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1883694: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc2174bs
    Type Database/Collection of data
    Public Access
    Link Link
  • 2019 Link
    Title CCDC 1864323: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc20kzg1
    Type Database/Collection of data
    Public Access
    Link Link
  • 2018 Link
    Title CCDC 1568697: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc1pnc4v
    Type Database/Collection of data
    Public Access
    Link Link
  • 2017 Link
    Title CCDC 1517284: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc1mxvn1
    Type Database/Collection of data
    Public Access
    Link Link
  • 2017 Link
    Title CCDC 1517283: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc1mxvm0
    Type Database/Collection of data
    Public Access
    Link Link
  • 2017 Link
    Title CCDC 1504135: Experimental Crystal Structure Determination
    DOI 10.5517/ccdc.csd.cc1mh5hs
    Type Database/Collection of data
    Public Access
    Link Link
Scientific Awards
  • 2019
    Title Master thesis award - GOECH
    Type Research prize
    Level of Recognition National (any country)
  • 2016
    Title Master thesis award - GOECH
    Type Research prize
    Level of Recognition National (any country)

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