Hole-Transporting Side-Chain Polymer Bearing a Thermally Crosslinkable Bicyclo[4.2.0]octa-1,3,5-trien-3-yl Group for High-Performing Thermally Activated Delayed Fluorescence OLED

Cheol Hun Jeong, Mallesham Godumala, Jiwon Yoon, Suna Choi, Yong Woo Kim, Dae Hyuk Choi, Min Ju Cho, Dong Hoon Choi

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A new side-chain polymer (X-TPACz) bearing hole-transporting pendant groups accompanying a thermally crosslinkable entity was synthesized using N-([1,1′-biphenyl]-4-yl)-N-(4-(9-(4-vinylbenzyl)-9H-carbazol-3-yl)phenyl)bicyclo[4.2.0]octa-1(6),2,4-trien-3-amine (6) via addition polymerization. The X-TPACz could be spontaneously crosslinked without using any further reagents and showed a good film-forming property upon low-temperature thermal treatment. The thermal curing temperature for the X-TPACz film was optimized to be 180 °C based on a differential scanning calorimetry thermogram. Moreover, the thermal degradation temperature of X-TPACz measured to be over 467 °C using thermogravimetric analysis demonstrated that it shows excellent thermal stability. In particular, X-TPACz exhibits the highest occupied molecular orbital (HOMO) energy level to be -5.26 eV, which is beneficial for facile hole injection and transportation. Consequently, the thermally activated delayed fluorescence organic light-emitting diodes fabricated using X-TPACz as the hole-transporting material showed state-of-the-art performances with a low turn-on voltage (V on ) of only 2.7 V and a high external quantum efficiency (EQE) of 19.18% with a high current efficiency (CE) of 66.88 cd/A and a high power efficiency (PE) of 60.03 lm/W, which are highly superior to those of the familiar poly(9-vinylcarbazole) (PVK)-based devices (V on = 3.9 V, EQE of 17.42%, with CE of 58.33 cd/A and PE of 33.32 lm/W). The extremely low turn-on voltage and high EQE were found to be due to the higher-lying highest occupied molecular orbital energy level (E HOMO = -5.23 eV) and better hole-transporting property of X-TPACz than those of PVK.

Original languageEnglish
Pages (from-to)17602-17609
Number of pages8
JournalACS Applied Materials and Interfaces
Volume11
Issue number19
DOIs
Publication statusPublished - 2019 May 15

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Bearings (structural)
Trientine
Organic light emitting diodes (OLED)
Molecular orbitals
Quantum efficiency
Polymers
Fluorescence
Electron energy levels
Low temperature properties
Electric potential
Amines
Curing
Thermogravimetric analysis
Differential scanning calorimetry
Pyrolysis
Thermodynamic stability
Heat treatment
Polymerization
Temperature

Keywords

  • hole-transport material
  • organic light-emitting diode
  • solution process
  • thermal crosslinking
  • thermally activated delayed fluorescence

ASJC Scopus subject areas

  • Materials Science(all)

Cite this

Hole-Transporting Side-Chain Polymer Bearing a Thermally Crosslinkable Bicyclo[4.2.0]octa-1,3,5-trien-3-yl Group for High-Performing Thermally Activated Delayed Fluorescence OLED. / Jeong, Cheol Hun; Godumala, Mallesham; Yoon, Jiwon; Choi, Suna; Kim, Yong Woo; Choi, Dae Hyuk; Cho, Min Ju; Choi, Dong Hoon.

In: ACS Applied Materials and Interfaces, Vol. 11, No. 19, 15.05.2019, p. 17602-17609.

Research output: Contribution to journalArticle

Jeong, Cheol Hun ; Godumala, Mallesham ; Yoon, Jiwon ; Choi, Suna ; Kim, Yong Woo ; Choi, Dae Hyuk ; Cho, Min Ju ; Choi, Dong Hoon. / Hole-Transporting Side-Chain Polymer Bearing a Thermally Crosslinkable Bicyclo[4.2.0]octa-1,3,5-trien-3-yl Group for High-Performing Thermally Activated Delayed Fluorescence OLED. In: ACS Applied Materials and Interfaces. 2019 ; Vol. 11, No. 19. pp. 17602-17609.
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abstract = "A new side-chain polymer (X-TPACz) bearing hole-transporting pendant groups accompanying a thermally crosslinkable entity was synthesized using N-([1,1′-biphenyl]-4-yl)-N-(4-(9-(4-vinylbenzyl)-9H-carbazol-3-yl)phenyl)bicyclo[4.2.0]octa-1(6),2,4-trien-3-amine (6) via addition polymerization. The X-TPACz could be spontaneously crosslinked without using any further reagents and showed a good film-forming property upon low-temperature thermal treatment. The thermal curing temperature for the X-TPACz film was optimized to be 180 °C based on a differential scanning calorimetry thermogram. Moreover, the thermal degradation temperature of X-TPACz measured to be over 467 °C using thermogravimetric analysis demonstrated that it shows excellent thermal stability. In particular, X-TPACz exhibits the highest occupied molecular orbital (HOMO) energy level to be -5.26 eV, which is beneficial for facile hole injection and transportation. Consequently, the thermally activated delayed fluorescence organic light-emitting diodes fabricated using X-TPACz as the hole-transporting material showed state-of-the-art performances with a low turn-on voltage (V on ) of only 2.7 V and a high external quantum efficiency (EQE) of 19.18{\%} with a high current efficiency (CE) of 66.88 cd/A and a high power efficiency (PE) of 60.03 lm/W, which are highly superior to those of the familiar poly(9-vinylcarbazole) (PVK)-based devices (V on = 3.9 V, EQE of 17.42{\%}, with CE of 58.33 cd/A and PE of 33.32 lm/W). The extremely low turn-on voltage and high EQE were found to be due to the higher-lying highest occupied molecular orbital energy level (E HOMO = -5.23 eV) and better hole-transporting property of X-TPACz than those of PVK.",
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author = "Jeong, {Cheol Hun} and Mallesham Godumala and Jiwon Yoon and Suna Choi and Kim, {Yong Woo} and Choi, {Dae Hyuk} and Cho, {Min Ju} and Choi, {Dong Hoon}",
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T1 - Hole-Transporting Side-Chain Polymer Bearing a Thermally Crosslinkable Bicyclo[4.2.0]octa-1,3,5-trien-3-yl Group for High-Performing Thermally Activated Delayed Fluorescence OLED

AU - Jeong, Cheol Hun

AU - Godumala, Mallesham

AU - Yoon, Jiwon

AU - Choi, Suna

AU - Kim, Yong Woo

AU - Choi, Dae Hyuk

AU - Cho, Min Ju

AU - Choi, Dong Hoon

PY - 2019/5/15

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N2 - A new side-chain polymer (X-TPACz) bearing hole-transporting pendant groups accompanying a thermally crosslinkable entity was synthesized using N-([1,1′-biphenyl]-4-yl)-N-(4-(9-(4-vinylbenzyl)-9H-carbazol-3-yl)phenyl)bicyclo[4.2.0]octa-1(6),2,4-trien-3-amine (6) via addition polymerization. The X-TPACz could be spontaneously crosslinked without using any further reagents and showed a good film-forming property upon low-temperature thermal treatment. The thermal curing temperature for the X-TPACz film was optimized to be 180 °C based on a differential scanning calorimetry thermogram. Moreover, the thermal degradation temperature of X-TPACz measured to be over 467 °C using thermogravimetric analysis demonstrated that it shows excellent thermal stability. In particular, X-TPACz exhibits the highest occupied molecular orbital (HOMO) energy level to be -5.26 eV, which is beneficial for facile hole injection and transportation. Consequently, the thermally activated delayed fluorescence organic light-emitting diodes fabricated using X-TPACz as the hole-transporting material showed state-of-the-art performances with a low turn-on voltage (V on ) of only 2.7 V and a high external quantum efficiency (EQE) of 19.18% with a high current efficiency (CE) of 66.88 cd/A and a high power efficiency (PE) of 60.03 lm/W, which are highly superior to those of the familiar poly(9-vinylcarbazole) (PVK)-based devices (V on = 3.9 V, EQE of 17.42%, with CE of 58.33 cd/A and PE of 33.32 lm/W). The extremely low turn-on voltage and high EQE were found to be due to the higher-lying highest occupied molecular orbital energy level (E HOMO = -5.23 eV) and better hole-transporting property of X-TPACz than those of PVK.

AB - A new side-chain polymer (X-TPACz) bearing hole-transporting pendant groups accompanying a thermally crosslinkable entity was synthesized using N-([1,1′-biphenyl]-4-yl)-N-(4-(9-(4-vinylbenzyl)-9H-carbazol-3-yl)phenyl)bicyclo[4.2.0]octa-1(6),2,4-trien-3-amine (6) via addition polymerization. The X-TPACz could be spontaneously crosslinked without using any further reagents and showed a good film-forming property upon low-temperature thermal treatment. The thermal curing temperature for the X-TPACz film was optimized to be 180 °C based on a differential scanning calorimetry thermogram. Moreover, the thermal degradation temperature of X-TPACz measured to be over 467 °C using thermogravimetric analysis demonstrated that it shows excellent thermal stability. In particular, X-TPACz exhibits the highest occupied molecular orbital (HOMO) energy level to be -5.26 eV, which is beneficial for facile hole injection and transportation. Consequently, the thermally activated delayed fluorescence organic light-emitting diodes fabricated using X-TPACz as the hole-transporting material showed state-of-the-art performances with a low turn-on voltage (V on ) of only 2.7 V and a high external quantum efficiency (EQE) of 19.18% with a high current efficiency (CE) of 66.88 cd/A and a high power efficiency (PE) of 60.03 lm/W, which are highly superior to those of the familiar poly(9-vinylcarbazole) (PVK)-based devices (V on = 3.9 V, EQE of 17.42%, with CE of 58.33 cd/A and PE of 33.32 lm/W). The extremely low turn-on voltage and high EQE were found to be due to the higher-lying highest occupied molecular orbital energy level (E HOMO = -5.23 eV) and better hole-transporting property of X-TPACz than those of PVK.

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KW - thermally activated delayed fluorescence

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