Journal of Chemical Sciences

, 131:94 | Cite as

Synthesis of acridone-naphthylamine derivative and its thermally-activated delayed fluorescence studies for application in OLEDs

  • SANGITA BOSEEmail author
  • NEERAJ AGARWALEmail author
Regular Article


Acridone (acceptor) and naphthylamine (donor) based Donor-Acceptor-Donor (D-A-D) compound (1) was synthesised, characterised and its thermally-activated delayed fluorescence (TADF) properties were studied in detail. Compound 1 is fluorescent and emits in the green region (550 nm). The energy gap between the ground and the lowest excited singlet (S1) state is estimated to be 2.55 eV. The energy gap between the CT singlet and triplet states (∆EST) was found to be ~0.3 eV. Small ∆ES1-T1 is one of the important criteria for TADF to take place in a molecule and thus detailed photophysics has been studied. Transient lifetime measurements showed an increase in the fluorescence lifetime (τ) on purging with N2, as compared with that in air-saturated solution, indicating the involvement of the triplet state in emission. Emission at 550 nm was also observed with a delay of 100 µs which corresponded to the delayed fluorescence in 1. The lifetime of TADF was found to be 176 µs. Applications of TADF materials in organic light-emitting devices (OLEDs) has gotten attention as TADF materials utilise the triplet excitons which helps in increasing internal quantum efficiency of device. Air-saturated based on 1 were fabricated and their intensity was found to be nearly as high as 17,000 Cd/m2 at 25 mA/cm2 which was comparable to many of the known TADF emitters.

Graphic abstract

Acridone-amine derivatives was synthesized and its photophysical properties were carried out to establish TADF. It was also used in fabrication of OLEDs.


Acridone thermally activated delayed fluorescence organic light-emitting devices 



We thank Swati Dixit for her assistance in cyclic voltammetric studies. We thank Tata Institute of Fundamental Research, Mumbai for NMR and MALDI-TOF. We also thank the Radiation and Photochemistry Division, Bhabha Atomic Research Centre for TCSPC. NA and SB thank the Department of Science and Technology for partial financial support (EMR/2017/000805).

Supplementary material

12039_2019_1667_MOESM1_ESM.pdf (978 kb)
Supplementary material 1 (PDF 978 kb)


  1. 1.
    Sasabe H and Kido J 2011 Multifunctional Materials in High-Performance OLEDs: Challenges for Solid-State Lighting Chem. Mater. 23 621Google Scholar
  2. 2.
    Ali F, Nayak P K, Periasamy N and Agarwal N 2017 Synthesis, photophysical, electrochemical and electroluminescence studies of red emitting phosphorescent Ir(III) heteroleptic complexes J. Chem. Sci. 129 1391CrossRefGoogle Scholar
  3. 3.
    Bhui P, Siddiqui Q T, Muneer M, Agarwal N and Bose S 2018 Deep blue organic light-emitting diodes of 1,8-diaryl anthracene J. Chem. Sci. 130 167CrossRefGoogle Scholar
  4. 4.
    Forrest S R 2004 The path to ubiquitous and low-cost organic electronic appliances on plastic Nature 428 911CrossRefGoogle Scholar
  5. 5.
    Nayak P K, Agarwal N, Ali F, Patankar M, Periasamy N and Narasimhan K L 2010 Blue and white light electroluminescence in a multilayer OLED using a new aluminium complex J. Chem. Sci. 122 847CrossRefGoogle Scholar
  6. 6.
    Siddiqui Q T, Bhui P, Muneer M, Chandrakumar K R S, Bose S and Agarwal N 2018 Nanoassembly of Dipolar Imidazoanthraquinone Derivatives Leading to Enhanced Hole Mobility J. Phys. Chem. C 122 25804CrossRefGoogle Scholar
  7. 7.
    Xu R-P, Li Y-Q and Tanga J-X 2016 Recent advances in flexible organic light-emitting diodes J. Mater. Chem. C 4 9116CrossRefGoogle Scholar
  8. 8.
    Yang Z, Mao Z, Xie Z, Zhang Y, Liu S, Zhao J, Xu J, Chi Z and Aldred M P 2017 Recent advances in organic thermally activated delayed fluorescence materials Chem. Soc. Rev. 46 915CrossRefGoogle Scholar
  9. 9.
    Forrest S R, Baldo M A, O’Brien D F, You Y, Shoustikov A, Sibley S and Thompson M E 1998 Highly Efficient Phosphorescent Emission from Organic Electroluminescent Devices Nature 395 151CrossRefGoogle Scholar
  10. 10.
    Méhes G, Nomura H, Zhang Q, Nakagawa T and Adachi C 2012 Enhanced Electroluminescence Efficiency in a Spiro-acridine Derivative through Thermally Activated Delayed Fluorescence Angew. Chem. Int. Ed. 51 11311CrossRefGoogle Scholar
  11. 11.
    Nasu K, Nakagawa T, Nomura H, Lin C-J, Cheng C-H, Tseng M-R, Yasuda T and Adachi C 2013 A Highly Luminescent Spiro-Anthracenone-Based Organic Light-Emitting Diode Exhibiting Thermally Activated Delayed Fluorescence Chem. Commun. 49 10385Google Scholar
  12. 12.
    Reineke S 2014 Organic Light-Emitting Diodes: Phosphorescence meets its Match Nat. Photonics 8 269CrossRefGoogle Scholar
  13. 13.
    Adachi C, Baldo M A, Thompson M E and Forrest S R 2001 Nearly 100% internal phosphorescence efficiency in an organic light-emitting device J. Appl. Phys. 90 5048CrossRefGoogle Scholar
  14. 14.
    Cui L-S, Liu Y, Liu X-Y, Jiang Z-Q and Liao L-S 2015 Design and Synthesis of Pyrimidine-Based Iridium(III) Complexes with Horizontal Orientation for Orange and White Phosphorescent OLEDs ACS Appl. Mater. Interfaces 7 11007CrossRefGoogle Scholar
  15. 15.
    Kaji H, Suzuki H, Fukushima T, Shizu K, Suzuki K, Kubo S, Komino T, Oiwa H, Suzuki F, Wakamiya A, Murata Y and Adachi C 2015 Purely Organic Electroluminescent Material Realizing 100% Conversion from Electricity to Light Nat. Commun. 6 8476Google Scholar
  16. 16.
    Siddiqui Q T, Awasthi A A, Bhui P, Muneer M, Chandrakumar K R S, Bose S and Agarwal N 2019 Thermally Activated Delayed Fluorescence (Green) in Undoped Film and Exciplex Emission (Blue) in Acridone–Carbazole Derivatives for OLEDs J. Phys. Chem. C 123 1003CrossRefGoogle Scholar
  17. 17.
    Uoyama H, Goushi K, Shizu K, Nomura H and Adachi C 2012 Highly Efficient Organic Light-Emitting Diodes from Delayed Fluorescence Nature 492 234CrossRefGoogle Scholar
  18. 18.
    Wong M Y and Zysman-Colman E 2017 Purely Organic Thermally Activated Delayed Fluorescence Materials for Organic Light-Emitting Diodes Adv. Mater. 29 1605444Google Scholar
  19. 19.
    Zhao J, Chen X, Yang Z, Chi Z, Yang Z, Zhang Y, Xu J, Chi Z and Aldreda M P 2018 Highly-efficient fully non-doped white organic light-emitting diodes consisting entirely of thermally activated delayed fluorescence emitters J. Mater. Chem. C 6 3226CrossRefGoogle Scholar
  20. 20.
    Grybauskaite-Kaminskiene G, Ivaniuk K, Bagdziunas G, Turyk P, Stakhira P, Baryshnikov G, Volyniuk D, Cherpak V, Minaev B, Hotra Z, Ågrencg H and Grazulevicius J V 2018 Contribution of TADF and exciplex emission for efficient “warm-white” OLEDs J. Mater. Chem. C 6 1543CrossRefGoogle Scholar
  21. 21.
    Zhang D, Duan L, Li C, Li Y, Li H, Zhang D and Qiu Y 2014 High-efficiency Fluorescent Organic Light-Emitting Devices using Sensitizing Hosts with a Small Singlet–Triplet Exchange Energy. Adv. Mater. 26 5050CrossRefGoogle Scholar
  22. 22.
    Penfold T J 2015 On Predicting the Excited-State Properties of Thermally Activated Delayed Fluorescence Emitters J. Phys. Chem. C 24 13535CrossRefGoogle Scholar
  23. 23.
    Mamada M, Inada K, Komino T, Potscavage W J J, Nakanotani H and Adachi C 2017 Highly Efficient Thermally Activated Delayed Fluorescence from an Excited-State Intramolecular Proton Transfer System ACS Cent. Sci. 3 769CrossRefGoogle Scholar
  24. 24.
    Pander P, Swist A, Motyka R, Soloducho J, Dias F B and Data P 2018 Thermally Activated Delayed Fluorescence with a Narrow Emission Spectrum and Organic Room Temperature Phosphorescence by Controlling Spin-Orbit Coupling and Phosphorescence Lifetime of Metal-free Organic Molecules J. Mater. Chem. C 6 5434CrossRefGoogle Scholar
  25. 25.
    Wang C, Zhang Z and Wang Y 2016 Quinacridone-Based π-Conjugated Electronic Materials J. Mater. Chem. C 4 9918CrossRefGoogle Scholar
  26. 26.
    Wang Y, Zhu Y, Lin X, Yang Y, Zhang B, Zhan H, Xie Z and Cheng Y 2018 Efficient Non-doped Yellow OLEDs Based on Thermally Activated Delayed Fluorescence Conjugated Polymers with an Acridine/Carbazole Donor Backbone and Triphenyltriazine Acceptor Pendant J. Mater. Chem. C 6 568CrossRefGoogle Scholar
  27. 27.
    Sharma B K, Shaikh A M, Agarwal N and Kamble R M 2016 Synthesis, photophysical and electrochemical studies of acridone-amine based donor–acceptors for hole transport materials RSC Adv. 6 17129CrossRefGoogle Scholar
  28. 28.
    Khopde S M, Priyadarsini K I, Palit D K and Mukherjee T 2000 Effect of solvent on the excited-state photophysical properties of curcumin Photochem. Photobiol. 72 625CrossRefGoogle Scholar
  29. 29.
    Lakowicz J R 2006 Principle of Fluorescence Spectroscopy 3rd edn. (New York: Springer-Verlag)CrossRefGoogle Scholar
  30. 30.
    Kappaun S, Slugovc C and List E J W 2008 Phosphorescent Organic Light-Emitting Devices: Working Principle and Iridium Based Emitter Materials Int. J. Mol. Sci. 9 1527CrossRefGoogle Scholar
  31. 31.
    Minaev B, Baryshnikov G and Agren H 2014 Principles of phosphorescent organic light emitting devices Phys. Chem. Chem. Phys. 16 1719CrossRefGoogle Scholar
  32. 32.
    Masui K, Nakanotani H and Adachi C 2013 Analysis of Exciton Annihilation in High-efficiency Sky-Blue Organic Light-Emitting Diodes with Thermally Activated Delayed Fluorescence Org. Electron. 14 2721CrossRefGoogle Scholar
  33. 33.
    Serevičius T, Nakagawa T, Kuo M-C, Cheng S-H, Wong K-T, Chang C-H, Kwong R C, Xia S and Adachi C 2013 Enhanced Electroluminescence based on Thermally Activated Delayed Fluorescence from a Carbazole–Triazine Derivative Phys. Chem. Chem. 15 15850CrossRefGoogle Scholar
  34. 34.
    Gritzner G and Kuta J 1984 Recommendations on Reporting Electrode Potentials in Nonaqueous Solvents J. Pure Appl. Chem. 56 461CrossRefGoogle Scholar

Copyright information

© Indian Academy of Sciences 2019

Authors and Affiliations

    • 1
    • 1
    • 1
    • 2
    • 3
    • 1
    • 3
    Email author
    • 1
    Email author
  1. 1.School of Chemical Sciences, UM-DAE Centre for Excellence in Basic SciencesUniversity of MumbaiMumbaiIndia
  2. 2.Department of ChemistryAligarh Muslim UniversityAligarhIndia
  3. 3.School of Physical Sciences, UM-DAE Centre for Excellence in Basic SciencesUniversity of MumbaiMumbaiIndia

Personalised recommendations