Synthesis of an aromatic amine derivative with novel double spirobifluorene core and its application as a hole transport material

Cho, Yongjoo; Kim, Oh Young; Lee, Jun Yeob

doi:10.1016/j.orgel.2011.11.028

Cited by 25 publications

(8 citation statements)

References 30 publications

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“…The electron transport type material, DSPPO1, adopted a double spirobifluorene core structure to acquire high thermal stability and high triplet energy as mentioned in our previous work [19][20][21]. The double spirobifluorene core derived hole transport material was modified with a diphenylamine moiety in order to increase hole transport property due to strong electron donating property of the diphenylamine moiety [19][20][21]. Comparing the hole transport material with the diphenylamine moiety, DSPPO1 was introduced into a diphenylphosphine oxide group for good electron transport properties due to enhanced electron-withdrawing property compared to the diphenylamine group.…”

Section: Resultsmentioning

confidence: 99%

“…Our group reported hole transport materials with a double spirobifluorene core structure. The spiro(cyclopenta[def]fluorene-1,5,9 ,9 -bifluorene) with the double spirobifluorene core exhibited good charge transport property, good thermal stability and high triplet energy compared to the spirobifluorene core structure [19][20][21]. However, there was any research on the electron transport material based on the double spirobifluorene core structure, yet.…”

Section: Introductionmentioning

confidence: 99%

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A phosphine oxide-substituted double spirobifluorene compound with high thermal stability

Cho

Lee

2015

Journal of Information Display

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A high thermal stability spirobifluorene core derivative with a substituted diphenylphosphine oxide moiety was synthesized as a new electron transport material (spiro(cyclopenta[def]fluorene-1,5,9 9-bifluorene)-2 ,2diylbis(diphenylphosphineoxide) [DSPPO1]) for phosphorescent organic light-emitting diodes (PHOLEDs). The glass transition temperature of DSPPO1 was observed at 156°C and was higher than that of common electron transport materials. The triplet energy of DSPPO1 was 2.77 eV and DSPPO1 was appropriate as an electron transport material for PHOLEDs. The highest occupied molecular orbital and lowest unoccupied molecular orbital of DSPPO1 were − 6.51 and − 2.70 eV, respectively. The energy level of DSPPO1 was suitable for hole blocking and electron injection as an electron transport material for PHOLEDs.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

A phosphine oxide-substituted double spirobifluorene compound with high thermal stability

Cho

Lee

2015

Journal of Information Display

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“…Having synthesized the dibromoketone for P4 , we decide to investigate polymers containing a highly novel bis-spirocyclic system. Triple-decker spirocyclic systems have been reported previously but to the best of our knowledge they have never been incorporated into conjugated polymers [ 41 ]. The intermediate dibromo-compound was synthesized via addition of 2-lithiobiphenyl to 2,7-dibromofluoerenone to give the carbinol, which was cyclized with concentrated HCl in acetic acid in an overall yield of 83% ( Figure 10 ) in a similar fashion to that reported by Cho et al [ 41 ].…”

Section: Discussionmentioning

confidence: 99%

Energetic Tuning in Spirocyclic Conjugated Polymers

Bronstein¹,

King²

2016

Polymers

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Precise control of the energy levels in a conjugated polymer is the key to allowing their exploitation in optoelectronic devices. The introduction of spirocycles into conjugated polymers has traditionally been used to enhance their solid state microstructure. Here we present a highly novel method of energetic tuning through the use of electronically active spirocyclic systems. By modifying the size and oxidation state of a heteroatom in an orthogonal spirocycle we demonstrate energetic fine tuning in both the absorption and emission of a conjugated polymer. Furthermore, the synthesis of highly novel triplet-decker spirocyclic conjugated polymers is presented. This new method of energetic manipulation in a conjugated polymer paves the way for future application targeted synthesis of polymers with electronically active spirocycles.

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“…The author revealed that the higher triplet energy can prevent the triplet exciton which come from the emission material. NPB, which showed a lower triplet energy (2.3 eV) than the green dopant Ir(ppy) 3 (2.4 eV), led to a drop in device efficiency [41].…”

Section: Electrochemical and Photophysical Propertiesmentioning

confidence: 99%

Acridine-Triphenylamine Based Hole-Transporting and Hole-Injecting Material for Highly Efficient Phosphorescent-Based Organic Light Emitting Diodes

et al. 2018

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Featured Application: We have idenfied our synthesized TPA-1A material can apply as hole injecting and hole transporting material for PhOLEDs applications.Abstract: In this study, triphenylamine-based hole-transporting material 4-(9,9-diphenylacridin-10(9H)-yl)-N-(4-(9,9-diphenylacridin-10(9H)-yl) phenyl)-N-phenylaniline (TPA-1A) was designed and synthesized by using single-step Buchwald-Hartwig coupling reaction with higher yield percentage of 76%. Our synthesized TPA-1A showed excellent thermal stability, with a higher glass transition temperature of 176 • C and decomposition temperature of 474 • C at 5% weight reduction. TPA-1A based green phosphorescent organic light emitting diodes (PhOLED) device was fabricated to investigate the device properties and compare it with the similar reference N,N -Di(1-naphthyl)-N,N -diphenyl-(1,1 -biphenyl)-4,4 -diamine (NPB)based device. The TPA-1A-based PhOLED demonstrated an excellent current and power efficiency of 49.13 cd/A and 27.56 lm/W, respectively. Moreover, TPA-1A demonstrated better hole injection efficiencies as well. The overall efficiencies were better than the reference NPB-based device.

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Synthesis of an aromatic amine derivative with novel double spirobifluorene core and its application as a hole transport material

Cited by 25 publications

References 30 publications

A phosphine oxide-substituted double spirobifluorene compound with high thermal stability

A phosphine oxide-substituted double spirobifluorene compound with high thermal stability

Energetic Tuning in Spirocyclic Conjugated Polymers

Acridine-Triphenylamine Based Hole-Transporting and Hole-Injecting Material for Highly Efficient Phosphorescent-Based Organic Light Emitting Diodes

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