Utilization of Multi-Heterodonors in Thermally Activated Delayed Fluorescence Molecules and Their High Performance Bluish-Green Organic Light-Emitting Diodes

Umamahesh Balijapalli; Masaki Tanaka; Morgan Auffray; Chin-Yiu Chan; Yi-Ting Lee; Youichi Tsuchiya; Hajime Nakanotani; Chihaya Adachi

doi:10.1021/acsami.9b20020

Utilization of Multi-Heterodonors in Thermally Activated Delayed Fluorescence Molecules and Their High Performance Bluish-Green Organic Light-Emitting Diodes

Umamahesh Balijapalli, Masaki Tanaka, Morgan Auffray, Chin-Yiu Chan, Yi-Ting Lee, Youichi Tsuchiya, Hajime Nakanotani, Chihaya Adachi^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

32 Citations (Scopus)

Abstract

We report a series of pentacarbazolyl-benzonitrile derivatives such as 2,4,6-tri(9H-carbazol-9-yl)-3,5-bis(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)benzonitrile (mPyBN), 3,5-bis(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,4,6-tri(9H-carbazol-9-yl)benzonitrile (pCF3BN), 2,4,6-tri(9H-carbazol-9-yl)-3-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)-5-(3,6-diphenyl-9H-carbazol-9-yl)benzonitrile (PyPhBN), 3-(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,4,6-tri(9H-carbazol-9-yl)-5-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)benzonitrile (PyCF3BN), and 3-(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,6-di(9H-carbazol-9-yl)-5-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)-4-(9H-pyrido[3,4-b]indol-9-yl)benzonitrile (CbPyCF3BN) in which some of the carbazoles are substituted with modified 3,5-diphenyl carbazoles, exhibiting thermally activated delayed fluorescence (TADF) properties. These emitters comprised two, three, and four different types of donors, capable of bluish-green emission of around 480 nm with relatively high photoluminescence quantum yields over 90% in solution. Emitters, namely, PyPhBN, PyCF3BN, and CbPyCF3BN, composed of three and four different types of donors endowed a rather short delayed lifetime (τ_d) of 4.25, 5.01, and 3.65 μs in their film state, respectively. Bluish-green organic light-emitting diodes based on PyPhBN, PyCF3BN, and CbPyCF3BN exhibit a high external quantum efficiency of 20.6, 19.5, and 19.6%, respectively, with unsurpassed efficiency roll-off behavior. These results indicate that the TADF properties of multidonor type molecules can be manipulated by controlling the types and number of electron donor units. © 2020 American Chemical Society

Original language	English
Pages (from-to)	9498-9506
Number of pages	9
Journal	ACS Applied Materials and Interfaces
Volume	12
Issue number	8
Online published	5 Feb 2020
DOIs	https://doi.org/10.1021/acsami.9b20020
Publication status	Published - 26 Feb 2020
Externally published	Yes

Funding

This work was supported financially by the Program for Building Regional Innovation Ecosystems of the Ministry of Education, Culture, Sports, Science and Technology, Japan the Japan Science and Technology Agency, ERATO, Adachi Molecular Exciton Engineering Project, under JST ERATO grant no. JPMJER1305, and the Japan Society for the Promotion of Science KAKENHI (grant nos. JP17J04907 JP17H01232, JP18H02047, and JP18H03902), Japan and Kyulux Inc.

Research Keywords

bluish-green emission
delay lifetime
multidonor
OLED
pentacarbazole
roll-off behavior
TADF

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10.1021/acsami.9b20020

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Balijapalli, U., Tanaka, M., Auffray, M., Chan, C.-Y., Lee, Y.-T., Tsuchiya, Y., Nakanotani, H., & Adachi, C. (2020). Utilization of Multi-Heterodonors in Thermally Activated Delayed Fluorescence Molecules and Their High Performance Bluish-Green Organic Light-Emitting Diodes. ACS Applied Materials and Interfaces, 12(8), 9498-9506. https://doi.org/10.1021/acsami.9b20020

@article{60829dd43e544e878d902f2cd6c22d0c,

title = "Utilization of Multi-Heterodonors in Thermally Activated Delayed Fluorescence Molecules and Their High Performance Bluish-Green Organic Light-Emitting Diodes",

abstract = "We report a series of pentacarbazolyl-benzonitrile derivatives such as 2,4,6-tri(9H-carbazol-9-yl)-3,5-bis(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)benzonitrile (mPyBN), 3,5-bis(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,4,6-tri(9H-carbazol-9-yl)benzonitrile (pCF3BN), 2,4,6-tri(9H-carbazol-9-yl)-3-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)-5-(3,6-diphenyl-9H-carbazol-9-yl)benzonitrile (PyPhBN), 3-(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,4,6-tri(9H-carbazol-9-yl)-5-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)benzonitrile (PyCF3BN), and 3-(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,6-di(9H-carbazol-9-yl)-5-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)-4-(9H-pyrido[3,4-b]indol-9-yl)benzonitrile (CbPyCF3BN) in which some of the carbazoles are substituted with modified 3,5-diphenyl carbazoles, exhibiting thermally activated delayed fluorescence (TADF) properties. These emitters comprised two, three, and four different types of donors, capable of bluish-green emission of around 480 nm with relatively high photoluminescence quantum yields over 90% in solution. Emitters, namely, PyPhBN, PyCF3BN, and CbPyCF3BN, composed of three and four different types of donors endowed a rather short delayed lifetime (τd) of 4.25, 5.01, and 3.65 μs in their film state, respectively. Bluish-green organic light-emitting diodes based on PyPhBN, PyCF3BN, and CbPyCF3BN exhibit a high external quantum efficiency of 20.6, 19.5, and 19.6%, respectively, with unsurpassed efficiency roll-off behavior. These results indicate that the TADF properties of multidonor type molecules can be manipulated by controlling the types and number of electron donor units. {\textcopyright} 2020 American Chemical Society",

keywords = "bluish-green emission, delay lifetime, multidonor, OLED, pentacarbazole, roll-off behavior, TADF",

author = "Umamahesh Balijapalli and Masaki Tanaka and Morgan Auffray and Chin-Yiu Chan and Yi-Ting Lee and Youichi Tsuchiya and Hajime Nakanotani and Chihaya Adachi",

year = "2020",

month = feb,

day = "26",

doi = "10.1021/acsami.9b20020",

language = "English",

volume = "12",

pages = "9498--9506",

journal = "ACS Applied Materials and Interfaces",

issn = "1944-8244",

publisher = "American Chemical Society",

number = "8",

}

Balijapalli, U, Tanaka, M, Auffray, M, Chan, C-Y, Lee, Y-T, Tsuchiya, Y, Nakanotani, H & Adachi, C 2020, 'Utilization of Multi-Heterodonors in Thermally Activated Delayed Fluorescence Molecules and Their High Performance Bluish-Green Organic Light-Emitting Diodes', ACS Applied Materials and Interfaces, vol. 12, no. 8, pp. 9498-9506. https://doi.org/10.1021/acsami.9b20020

Utilization of Multi-Heterodonors in Thermally Activated Delayed Fluorescence Molecules and Their High Performance Bluish-Green Organic Light-Emitting Diodes. / Balijapalli, Umamahesh; Tanaka, Masaki; Auffray, Morgan et al.
In: ACS Applied Materials and Interfaces, Vol. 12, No. 8, 26.02.2020, p. 9498-9506.

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

TY - JOUR

T1 - Utilization of Multi-Heterodonors in Thermally Activated Delayed Fluorescence Molecules and Their High Performance Bluish-Green Organic Light-Emitting Diodes

AU - Balijapalli, Umamahesh

AU - Tanaka, Masaki

AU - Auffray, Morgan

AU - Chan, Chin-Yiu

AU - Lee, Yi-Ting

AU - Tsuchiya, Youichi

AU - Nakanotani, Hajime

AU - Adachi, Chihaya

PY - 2020/2/26

Y1 - 2020/2/26

N2 - We report a series of pentacarbazolyl-benzonitrile derivatives such as 2,4,6-tri(9H-carbazol-9-yl)-3,5-bis(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)benzonitrile (mPyBN), 3,5-bis(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,4,6-tri(9H-carbazol-9-yl)benzonitrile (pCF3BN), 2,4,6-tri(9H-carbazol-9-yl)-3-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)-5-(3,6-diphenyl-9H-carbazol-9-yl)benzonitrile (PyPhBN), 3-(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,4,6-tri(9H-carbazol-9-yl)-5-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)benzonitrile (PyCF3BN), and 3-(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,6-di(9H-carbazol-9-yl)-5-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)-4-(9H-pyrido[3,4-b]indol-9-yl)benzonitrile (CbPyCF3BN) in which some of the carbazoles are substituted with modified 3,5-diphenyl carbazoles, exhibiting thermally activated delayed fluorescence (TADF) properties. These emitters comprised two, three, and four different types of donors, capable of bluish-green emission of around 480 nm with relatively high photoluminescence quantum yields over 90% in solution. Emitters, namely, PyPhBN, PyCF3BN, and CbPyCF3BN, composed of three and four different types of donors endowed a rather short delayed lifetime (τd) of 4.25, 5.01, and 3.65 μs in their film state, respectively. Bluish-green organic light-emitting diodes based on PyPhBN, PyCF3BN, and CbPyCF3BN exhibit a high external quantum efficiency of 20.6, 19.5, and 19.6%, respectively, with unsurpassed efficiency roll-off behavior. These results indicate that the TADF properties of multidonor type molecules can be manipulated by controlling the types and number of electron donor units. © 2020 American Chemical Society

AB - We report a series of pentacarbazolyl-benzonitrile derivatives such as 2,4,6-tri(9H-carbazol-9-yl)-3,5-bis(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)benzonitrile (mPyBN), 3,5-bis(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,4,6-tri(9H-carbazol-9-yl)benzonitrile (pCF3BN), 2,4,6-tri(9H-carbazol-9-yl)-3-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)-5-(3,6-diphenyl-9H-carbazol-9-yl)benzonitrile (PyPhBN), 3-(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,4,6-tri(9H-carbazol-9-yl)-5-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)benzonitrile (PyCF3BN), and 3-(3,6-bis(4-(trifluoromethyl)phenyl)-9H-carbazol-9-yl)-2,6-di(9H-carbazol-9-yl)-5-(3,6-di(pyridin-3-yl)-9H-carbazol-9-yl)-4-(9H-pyrido[3,4-b]indol-9-yl)benzonitrile (CbPyCF3BN) in which some of the carbazoles are substituted with modified 3,5-diphenyl carbazoles, exhibiting thermally activated delayed fluorescence (TADF) properties. These emitters comprised two, three, and four different types of donors, capable of bluish-green emission of around 480 nm with relatively high photoluminescence quantum yields over 90% in solution. Emitters, namely, PyPhBN, PyCF3BN, and CbPyCF3BN, composed of three and four different types of donors endowed a rather short delayed lifetime (τd) of 4.25, 5.01, and 3.65 μs in their film state, respectively. Bluish-green organic light-emitting diodes based on PyPhBN, PyCF3BN, and CbPyCF3BN exhibit a high external quantum efficiency of 20.6, 19.5, and 19.6%, respectively, with unsurpassed efficiency roll-off behavior. These results indicate that the TADF properties of multidonor type molecules can be manipulated by controlling the types and number of electron donor units. © 2020 American Chemical Society

KW - bluish-green emission

KW - delay lifetime

KW - multidonor

KW - OLED

KW - pentacarbazole

KW - roll-off behavior

KW - TADF

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UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-85081165746&origin=recordpage

U2 - 10.1021/acsami.9b20020

DO - 10.1021/acsami.9b20020

M3 - RGC 21 - Publication in refereed journal

C2 - 32020791

AN - SCOPUS:85081165746

SN - 1944-8244

VL - 12

SP - 9498

EP - 9506

JO - ACS Applied Materials and Interfaces

JF - ACS Applied Materials and Interfaces

IS - 8

ER -

Utilization of Multi-Heterodonors in Thermally Activated Delayed Fluorescence Molecules and Their High Performance Bluish-Green Organic Light-Emitting Diodes

Abstract

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Research Keywords

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