Use of pyrimidine and pyrazine bridges as a design strategy to improve the performance of thermally activated delayed fluorescence organic light emitting diodes

Paloma Lays dos Santos; Dongyang Chen; Rajamalli Pachai Gounder; Tomas Matulaitis; David Bradford Cordes; Alexandra Martha Zoya Slawin; Denis Jacquemin; Eli Zysman-Colman; Ifor David William Samuel

doi:10.1021/acsami.9b16952

Use of pyrimidine and pyrazine bridges as a design strategy to improve the performance of thermally activated delayed fluorescence organic light emitting diodes

Paloma Lays dos Santos, Dongyang Chen, Rajamalli Pachai Gounder, Tomas Matulaitis, David Bradford Cordes, Alexandra Martha Zoya Slawin, Denis Jacquemin, Eli Zysman-Colman, Ifor David William Samuel

Research output: Contribution to journal › Article › peer-review

Abstract

We present a study of two isomeric thermally activated delayed fluorescence (TADF) emitters 9,9'- (sulfonylbis(pyrimidine-5,2-diyl))bis(3,6-di-tert-butyl-9H-carbazole) (pDTCz-DPmS) and 9,9'- (sulfonylbis(pyrazine-5,2-diyl))bis(3,6-di-tert-butyl-9H-carbazole) (pDTCz-DPzS). The use of pyrimidine and pyrazine as bridging units between the electron donor and acceptor moieties is found to be advantageous compared to the phenyl- (pDTCz-DPS) and pyridine-based analogues (pDTCz-3DPyS and pDTCz-2DPyS). Conformational modulation of the donor groups as a function of the bridge results in high photoluminescence quantum yields (Φ_PL > 68%) and small energy gaps between singlet and triplet excited states (ΔE_ST < 160 meV). OLEDs using pDTCz-DPmS and pDTCz-DPzS as emitters exhibit blue and green electroluminescence, respectively, with higher maximum external quantum efficiencies (EQE_max of 14% and 18%, respectively) and reduced efficiency roll-off as compared to the reference devices using pDTCz-DPS, pDTCz-3DPyS, and pDTCz-2DPyS as the emitters. Our results provide a more complete understanding on the impact of the bridge structure in D-A-D TADF systems on the optoelectronic properties of the emitter, and how the balance between color purity and EQE in the devices can be controlled, advancing the design strategies for TADF emitters.

Original language	English
Pages (from-to)	45171-45179
Journal	ACS Applied Materials & Interfaces
Volume	11
Issue number	48
Early online date	7 Nov 2019
DOIs	https://doi.org/10.1021/acsami.9b16952
Publication status	Published - 4 Dec 2019

Keywords

TADF
Organic light emitting diodes
Pyrimidine
Pyrazine
Blue OLED
Intramolecular hydrogen bond

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10.1021/acsami.9b16952

Revised Manuscript
Copyright © 2019 American Chemical Society. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1021/acsami.9b16952
Accepted author manuscript, 1.1 MB

Chemistry EPSRC-JSPS: EPSRC-JSPS Core-to-Core Grant Application
Zysman-Colman, E. (PI)
1/08/18 → 31/01/24
Project: Standard
TADF Emitters for OLEDs - Eli Zysman: TADF Emitters for OLEDs
Zysman-Colman, E. (PI)
EPSRC
1/03/17 → 31/03/21
Project: Standard
DENTADFE: DENTADFE
Zysman-Colman, E. (PI)
European Commission
1/03/17 → 28/02/19
Project: Fellowship

The use of Pyrimidine and Pyrazine Bridges as a Design Strategy to Improve the Performance of Thermally Activated Delayed Fluorescence Organic Light Emitting Diodes (dataset)
dos Santos, P. L. (Creator), Chen, D. (Creator), Rajamalli, P. (Creator), Matulaitis, T. (Creator), Cordes, D. B. (Creator), Slawin, A. M. Z. (Creator), Jacquemin, D. (Creator), Zysman-Colman, E. (Creator) & Samuel, I. D. W. (Creator), University of St Andrews, 2019
DOI: 10.17630/c5c98330-f798-40ca-a721-9015b91b2b9b
Dataset

File

Cite this

dos Santos, P. L., Chen, D., Pachai Gounder, R., Matulaitis, T., Cordes, D. B., Slawin, A. M. Z., Jacquemin, D., Zysman-Colman, E., & Samuel, I. D. W. (2019). Use of pyrimidine and pyrazine bridges as a design strategy to improve the performance of thermally activated delayed fluorescence organic light emitting diodes. ACS Applied Materials & Interfaces, 11(48), 45171-45179. https://doi.org/10.1021/acsami.9b16952

@article{79d5716230904a0b8666d574e889b6c2,

title = "Use of pyrimidine and pyrazine bridges as a design strategy to improve the performance of thermally activated delayed fluorescence organic light emitting diodes",

abstract = "We present a study of two isomeric thermally activated delayed fluorescence (TADF) emitters 9,9'- (sulfonylbis(pyrimidine-5,2-diyl))bis(3,6-di-tert-butyl-9H-carbazole) (pDTCz-DPmS) and 9,9'- (sulfonylbis(pyrazine-5,2-diyl))bis(3,6-di-tert-butyl-9H-carbazole) (pDTCz-DPzS). The use of pyrimidine and pyrazine as bridging units between the electron donor and acceptor moieties is found to be advantageous compared to the phenyl- (pDTCz-DPS) and pyridine-based analogues (pDTCz-3DPyS and pDTCz-2DPyS). Conformational modulation of the donor groups as a function of the bridge results in high photoluminescence quantum yields (ΦPL > 68%) and small energy gaps between singlet and triplet excited states (ΔEST < 160 meV). OLEDs using pDTCz-DPmS and pDTCz-DPzS as emitters exhibit blue and green electroluminescence, respectively, with higher maximum external quantum efficiencies (EQEmax of 14% and 18%, respectively) and reduced efficiency roll-off as compared to the reference devices using pDTCz-DPS, pDTCz-3DPyS, and pDTCz-2DPyS as the emitters. Our results provide a more complete understanding on the impact of the bridge structure in D-A-D TADF systems on the optoelectronic properties of the emitter, and how the balance between color purity and EQE in the devices can be controlled, advancing the design strategies for TADF emitters.",

keywords = "TADF, Organic light emitting diodes, Pyrimidine, Pyrazine, Blue OLED, Intramolecular hydrogen bond",

author = "{dos Santos}, {Paloma Lays} and Dongyang Chen and {Pachai Gounder}, Rajamalli and Tomas Matulaitis and Cordes, {David Bradford} and Slawin, {Alexandra Martha Zoya} and Denis Jacquemin and Eli Zysman-Colman and Samuel, {Ifor David William}",

note = "Authors are grateful to the Engineering and Physical Sciences Research Council (EPSRC) for support from grants EP/P010482/1 and EP/R035164/1. P. Rajamalli acknowledges support from a Marie Sk{\l}odowska-Curie Individual Fellowship (MCIF; No. 749557). Dongyang Chen thanks the China Scholarship Council (grant numbers 201603780001).",

year = "2019",

month = dec,

day = "4",

doi = "10.1021/acsami.9b16952",

language = "English",

volume = "11",

pages = "45171--45179",

journal = "ACS Applied Materials & Interfaces",

issn = "1944-8244",

publisher = "American Chemical Society (ACS)",

number = "48",

}

dos Santos, PL, Chen, D, Pachai Gounder, R, Matulaitis, T, Cordes, DB , Slawin, AMZ, Jacquemin, D, Zysman-Colman, E & Samuel, IDW 2019, 'Use of pyrimidine and pyrazine bridges as a design strategy to improve the performance of thermally activated delayed fluorescence organic light emitting diodes', ACS Applied Materials & Interfaces, vol. 11, no. 48, pp. 45171-45179. https://doi.org/10.1021/acsami.9b16952

Use of pyrimidine and pyrazine bridges as a design strategy to improve the performance of thermally activated delayed fluorescence organic light emitting diodes. / dos Santos, Paloma Lays; Chen, Dongyang; Pachai Gounder, Rajamalli et al.
In: ACS Applied Materials & Interfaces, Vol. 11, No. 48, 04.12.2019, p. 45171-45179.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Use of pyrimidine and pyrazine bridges as a design strategy to improve the performance of thermally activated delayed fluorescence organic light emitting diodes

AU - dos Santos, Paloma Lays

AU - Chen, Dongyang

AU - Pachai Gounder, Rajamalli

AU - Matulaitis, Tomas

AU - Cordes, David Bradford

AU - Slawin, Alexandra Martha Zoya

AU - Jacquemin, Denis

AU - Zysman-Colman, Eli

AU - Samuel, Ifor David William

N1 - Authors are grateful to the Engineering and Physical Sciences Research Council (EPSRC) for support from grants EP/P010482/1 and EP/R035164/1. P. Rajamalli acknowledges support from a Marie Skłodowska-Curie Individual Fellowship (MCIF; No. 749557). Dongyang Chen thanks the China Scholarship Council (grant numbers 201603780001).

PY - 2019/12/4

Y1 - 2019/12/4

N2 - We present a study of two isomeric thermally activated delayed fluorescence (TADF) emitters 9,9'- (sulfonylbis(pyrimidine-5,2-diyl))bis(3,6-di-tert-butyl-9H-carbazole) (pDTCz-DPmS) and 9,9'- (sulfonylbis(pyrazine-5,2-diyl))bis(3,6-di-tert-butyl-9H-carbazole) (pDTCz-DPzS). The use of pyrimidine and pyrazine as bridging units between the electron donor and acceptor moieties is found to be advantageous compared to the phenyl- (pDTCz-DPS) and pyridine-based analogues (pDTCz-3DPyS and pDTCz-2DPyS). Conformational modulation of the donor groups as a function of the bridge results in high photoluminescence quantum yields (ΦPL > 68%) and small energy gaps between singlet and triplet excited states (ΔEST < 160 meV). OLEDs using pDTCz-DPmS and pDTCz-DPzS as emitters exhibit blue and green electroluminescence, respectively, with higher maximum external quantum efficiencies (EQEmax of 14% and 18%, respectively) and reduced efficiency roll-off as compared to the reference devices using pDTCz-DPS, pDTCz-3DPyS, and pDTCz-2DPyS as the emitters. Our results provide a more complete understanding on the impact of the bridge structure in D-A-D TADF systems on the optoelectronic properties of the emitter, and how the balance between color purity and EQE in the devices can be controlled, advancing the design strategies for TADF emitters.

AB - We present a study of two isomeric thermally activated delayed fluorescence (TADF) emitters 9,9'- (sulfonylbis(pyrimidine-5,2-diyl))bis(3,6-di-tert-butyl-9H-carbazole) (pDTCz-DPmS) and 9,9'- (sulfonylbis(pyrazine-5,2-diyl))bis(3,6-di-tert-butyl-9H-carbazole) (pDTCz-DPzS). The use of pyrimidine and pyrazine as bridging units between the electron donor and acceptor moieties is found to be advantageous compared to the phenyl- (pDTCz-DPS) and pyridine-based analogues (pDTCz-3DPyS and pDTCz-2DPyS). Conformational modulation of the donor groups as a function of the bridge results in high photoluminescence quantum yields (ΦPL > 68%) and small energy gaps between singlet and triplet excited states (ΔEST < 160 meV). OLEDs using pDTCz-DPmS and pDTCz-DPzS as emitters exhibit blue and green electroluminescence, respectively, with higher maximum external quantum efficiencies (EQEmax of 14% and 18%, respectively) and reduced efficiency roll-off as compared to the reference devices using pDTCz-DPS, pDTCz-3DPyS, and pDTCz-2DPyS as the emitters. Our results provide a more complete understanding on the impact of the bridge structure in D-A-D TADF systems on the optoelectronic properties of the emitter, and how the balance between color purity and EQE in the devices can be controlled, advancing the design strategies for TADF emitters.

KW - TADF

KW - Organic light emitting diodes

KW - Pyrimidine

KW - Pyrazine

KW - Blue OLED

KW - Intramolecular hydrogen bond

U2 - 10.1021/acsami.9b16952

DO - 10.1021/acsami.9b16952

M3 - Article

SN - 1944-8244

VL - 11

SP - 45171

EP - 45179

JO - ACS Applied Materials & Interfaces

JF - ACS Applied Materials & Interfaces

IS - 48

ER -

Use of pyrimidine and pyrazine bridges as a design strategy to improve the performance of thermally activated delayed fluorescence organic light emitting diodes

Abstract

Keywords

Access to Document

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Projects

Chemistry EPSRC-JSPS: EPSRC-JSPS Core-to-Core Grant Application

TADF Emitters for OLEDs - Eli Zysman: TADF Emitters for OLEDs

DENTADFE: DENTADFE

Datasets

The use of Pyrimidine and Pyrazine Bridges as a Design Strategy to Improve the Performance of Thermally Activated Delayed Fluorescence Organic Light Emitting Diodes (dataset)

Cite this