A triphenylamine substituted quinacridone derivative for solution processed organic light emitting diodes

M. Pilz da Cunha, T.T. Do, S.D. Yambem, H.D. Pham, S. Chang, S. Manzhos, R. Katoh, P. Sonar

Research output: Contribution to journalArticleAcademicpeer-review

5 Citations (Scopus)

Abstract

We report on a novel quinacridone derivative design, namely, 2,9-bis(4-(bis(4-methoxyphenyl)amino)phenyl)-5,12-bis(2-ethylhexyl)-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione (TPA-QA-TPA) for possible use as a solution processable emissive layer in organic light emitting diodes (OLEDs). TPA-QA-TPA contains branched alkyl chains for enhanced solubility and methoxytriphenylamine moieties (TPA) as end capping groups. The end capping groups not only extend the molecular conjugation leading to a red shifted emission, but have a propeller shaped conformation. The propeller design hinders the intermolecular π-π stacking, hindering aggregation and hence suppressing concentration quenching of the fluorophores in the solid state. The new molecular design shows good thermal stability, with a decomposition temperature of 390 °C and a melting temperature of 295 °C. The absorption and emission maxima for TPA-QA-TPA compound are 552 and 622 nm respectively. Using TPA-QA-TPA as a dopant in tris(8-hydroxyquinolinato)aluminum (Alq3), organic light emitting diodes were realized in a simple device structure.

LanguageEnglish
Pages56-63
Number of pages8
JournalMaterials Chemistry and Physics
Volume206
DOIs
StatePublished - 15 Feb 2018

Fingerprint

Organic light emitting diodes (OLED)
propellers
light emitting diodes
Propellers
Derivatives
Acridines
Fluorophores
Dione
Aluminum
conjugation
Melting point
Conformations
Quenching
Thermodynamic stability
thermal stability
Agglomeration
solubility
Solubility
quenching
Doping (additives)

Keywords

  • Fluorescence
  • Organic light emitting diode
  • Quinacridone
  • Solution process
  • Triphenylamine

Cite this

Pilz da Cunha, M. ; Do, T.T. ; Yambem, S.D. ; Pham, H.D. ; Chang, S. ; Manzhos, S. ; Katoh, R. ; Sonar, P./ A triphenylamine substituted quinacridone derivative for solution processed organic light emitting diodes. In: Materials Chemistry and Physics. 2018 ; Vol. 206. pp. 56-63
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A triphenylamine substituted quinacridone derivative for solution processed organic light emitting diodes. / Pilz da Cunha, M.; Do, T.T.; Yambem, S.D.; Pham, H.D.; Chang, S.; Manzhos, S.; Katoh, R.; Sonar, P.

In: Materials Chemistry and Physics, Vol. 206, 15.02.2018, p. 56-63.

Research output: Contribution to journalArticleAcademicpeer-review

TY - JOUR

T1 - A triphenylamine substituted quinacridone derivative for solution processed organic light emitting diodes

AU - Pilz da Cunha,M.

AU - Do,T.T.

AU - Yambem,S.D.

AU - Pham,H.D.

AU - Chang,S.

AU - Manzhos,S.

AU - Katoh,R.

AU - Sonar,P.

PY - 2018/2/15

Y1 - 2018/2/15

N2 - We report on a novel quinacridone derivative design, namely, 2,9-bis(4-(bis(4-methoxyphenyl)amino)phenyl)-5,12-bis(2-ethylhexyl)-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione (TPA-QA-TPA) for possible use as a solution processable emissive layer in organic light emitting diodes (OLEDs). TPA-QA-TPA contains branched alkyl chains for enhanced solubility and methoxytriphenylamine moieties (TPA) as end capping groups. The end capping groups not only extend the molecular conjugation leading to a red shifted emission, but have a propeller shaped conformation. The propeller design hinders the intermolecular π-π stacking, hindering aggregation and hence suppressing concentration quenching of the fluorophores in the solid state. The new molecular design shows good thermal stability, with a decomposition temperature of 390 °C and a melting temperature of 295 °C. The absorption and emission maxima for TPA-QA-TPA compound are 552 and 622 nm respectively. Using TPA-QA-TPA as a dopant in tris(8-hydroxyquinolinato)aluminum (Alq3), organic light emitting diodes were realized in a simple device structure.

AB - We report on a novel quinacridone derivative design, namely, 2,9-bis(4-(bis(4-methoxyphenyl)amino)phenyl)-5,12-bis(2-ethylhexyl)-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione (TPA-QA-TPA) for possible use as a solution processable emissive layer in organic light emitting diodes (OLEDs). TPA-QA-TPA contains branched alkyl chains for enhanced solubility and methoxytriphenylamine moieties (TPA) as end capping groups. The end capping groups not only extend the molecular conjugation leading to a red shifted emission, but have a propeller shaped conformation. The propeller design hinders the intermolecular π-π stacking, hindering aggregation and hence suppressing concentration quenching of the fluorophores in the solid state. The new molecular design shows good thermal stability, with a decomposition temperature of 390 °C and a melting temperature of 295 °C. The absorption and emission maxima for TPA-QA-TPA compound are 552 and 622 nm respectively. Using TPA-QA-TPA as a dopant in tris(8-hydroxyquinolinato)aluminum (Alq3), organic light emitting diodes were realized in a simple device structure.

KW - Fluorescence

KW - Organic light emitting diode

KW - Quinacridone

KW - Solution process

KW - Triphenylamine

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