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Journal of Materials Chemistry CMaterials for optical, magnetic and electronic deviceswww.rsc.org/MaterialsC

ISSN 2050-7526

PAPERNguyên T. K. Thanh, Xiaodi Su et al.Fine-tuning of gold nanorod dimensions and plasmonic properties using the Hofmeister eff ects

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Volume 4 Number 1 7 January 2016 Pages 1–224

Journal of Materials Chemistry CMaterials for optical, magnetic and electronic devices

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Baryshnikov, P. Y. Stakhira, S. Pedersen, M. Pittelkow, A. Lazauskas, D. Y. Volyniuk, J. V. Grazulevicius, B.

Minaev and H. Ågren, J. Mater. Chem. C, 2017, DOI: 10.1039/C7TC00655A.

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Accepted 00th January 20xx

DOI: 10.1039/x0xx00000x

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New WOLEDs based on π-extended azatrioxa[8]circulenes

K. B. Ivaniuk,a G. V. Baryshnikov

b,c,*, P. Y. Stakhira

a, S. K. Pedersen,

d M. Pittelkow

d, A. Lazauskas

e,

D. Volyniuke, J. V. Grazulevicius

e, B. F. Minaev

b,c and H. Ågren

b

New stable WOLEDs based on π-extended azatrioxa[8]circulenes

have been fabricated. Combining the own blue emission of the

azatrioxa[8]circulenes with the yellow-green emission of the

“m-MTDATA:azatrioxa[8]circulene” exciplex a broad visible

region, from 400 to 700 nm, is covered. The so constructed

WOLEDs exhibit luminance exceeding 23700 cd m-2

and an

external quantum efficiency reaching 3%.

Azatrioxa[8]circulenes1,2 (ATOCs) are polyaromatic heterocyclic

compounds containing a planar cyclooctatetraene core (COT)

enclosed within a condensed ribbon of four benzene, three

furane and one pyrrole rings (Figure 1). The first ATOC

compounds were synthesized by Pittelkow and co-workers in

20131 by treating a suitably functionalised 3,6-

dihydroxycarbazole with 1,4-benzoquinones or 1,4-

naphthoquinone. Recently, several new representatives of

unsymmetrical ATOCs were additionally synthesized by the

Pittelkow group.2 It was shown that the synthetic pathway for

the ATOCs is very sensitive to the electronic nature of

substituents in the first 1,4-benzoquinone moiety (there

should be an electron donating substituent like the t-Bu group,

otherwise the diazadioxa[8]circulene3 is the main product).

However, such substituted ATOCs demonstrate a quite low

florescence quantum yield (φfl.) (with values less than 0.31,1-3

Fig. 1) which is not suitable for their utilization as emitters in

OLEDs. Importantly, extending the ATOC π-conjugation by two

naphthalene moieties that originate from the initial 1,4-

naphthoquinone synthetic reagent provides significant

increase of φfl up to 0.911,2 (Fig. 1, compounds 1 and 2).

Therefore, such π-extended ATOCs could be promising

fluorescent emitters for the OLEDs taking into additional

account also their extremely high thermo- and electro-

stability. Complementary theoretical justification for the

π-extended ATOCs as being suitable candidates for blue OLEDs

has been recently published by Baryshnikov et.al.4 These

authors have used the specially parameterized semiempirical

INDO approximation together with the ab initio CASPT2 (XMC-

QDPT2) method to show that for a number of ATOCs

molecules the fluorescence process strongly dominates over

the non-radiative deactivation channels providing φfl. values

up to 0.99.4

In the present study we have implemented for the first time

ATOC molecules 1 and 2 into real prototypes of

electroluminescent light-emitting devices. Particularly, we

have fabricated single-layer OLEDs with the following rather

simplified structure (the layers thickness (nm) in parentheses):

device A: ITO/1(100)/Ca(5)/Al(200)

device B: ITO/2(100)/Ca(5)/Al(200).

In order to improve the lighting characteristics of these OLEDs

and to extend their electroluminescence spectra over the

visible range we have inserted ATOCs 1 and 2 between

exciplex-forming layers of star-shaped 4,4′,4′′-tris[phenyl(m-

tolyl)amino]triphenylamine (m-MTDATA)5-7 from one side and

electron-transporting layers of 2,2′,2"-(1,3,5-benzinetriyl)-

tris(1-phenyl-1-H-benzimidazole) (TPBi)8 from the other side

(for the chemical structures of m-MTDATA and TPBi see Figure

S1 in ESI). We have additionally used an inorganic CuI layer as a

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View Article OnlineDOI: 10.1039/C7TC00655A


COMMUNICATION J. Mat. Chem. C

2 | J. Name., 2012, 00, 1-3 This journal is © The Royal Society of Chemistry 20xx



hole-transporting material.9 The final scheme of the improved

devices looks as follows (Figures S2, S3):

Device C:

ITO/CuI(8)/m-MTDATA(10)/1(50)/ TPBi(10)/Ca(5)/Al(200)

Device D:

ITO/CuI(8)/m-MTDATA(10)/2(50)/TPBi(10)/Ca(5)/Al(200).

All the OLEDs (devices A–D) were fabricated as reported

earlier.10-13,‡

The theoretical interpretation of the electronic spectra of the

compounds 1 and 2 was performed by the time dependent

(TD)14 density functional theory (DFT) method using the

specially exchange-parameterized B3LYP15,16 functional

(aXHF=0.14, aX

Slater=0.86) and 6-31G(d)17 basis set within the

polarizable continuum model (PCM)18 for account of the

solvent effect (dichloromethane in our case). All the

calculations have been carried out using the Gaussian 0919

program package.

As can be seen in Figure 2 the profiles of the experimental

absorption spectra (measured in CH2Cl2 solutions) are very

similar for the ATOCs 1 and 2. Our TDDFT simulations (Tables

S1, S2 for spectral assignment, Figures S4, S5 for MOs)

reproduce well the experimentally observed spectra excluding

the 0-1 and 0-2 vibronic satellites for the S0–S1 transition in the

region of 360-400 nm (Figure 2). These bands can not be

reproduced by the regular TDDFT calculations but their

vibronic origin was recently identified by the TDDFT method

with the Franck–Condon and Herzberg–Teller approaches

including Duschinsky effect.20 The most vibronically active

modes were determined as the asymmetrical stretching

vibrations of the inner octatetraene core. A clear visible

vibronic progression of the S1–S0 transition is also observed in

the emission spectra of ATOCs 1 and 2 measured for the solid

films samples and dichloromethane solutions (Figure 3). It is

noteworthy that the fluorescence spectra of the solid films are

clearly broadened in the long-wavelength region for both

circulenes (Figure 3, 470-590 nm). That is probably caused by

the excimer emission of the π-stacked dimers as detected by

the single crystal X-ray crystallography measurements (Figure

S6). It can be seen from Figure 3 that the fluorescence spectra

of the N-benzyl substituted compound 2 (measured for the

CH2Cl2 solution and for the solid phase) are the same

concerning the peak positions while the solid film fluorescence

spectrum of N-propyl substituted compound 1 is 10 nm red-

shifted for the most intense 0-1 vibronic band comparing with

its solution spectrum. Such a substituent effect can be

explained by the fact that the molecules of N-propyl

substituted ATOC 1 are more close-packed in the condensed

phase comparing with the more voluminous N-benzyl

substituted ATOC 2 molecules. At the same time, the Pr and Bn

substituents do not affect the EL spectra of the simplest single-

layered devices A and B (Figure 4). The technical

characteristics of these devices are quite pure (Figures S7 and

S8): the high current densities provide the very low values of

the external quantum efficiencies (EQE); the brightness values

are also extremely small (only 1900 Cd/m2 at 15 V). Such low

efficiency is probably caused by the poor charge carrier

mobility within the active layer. Varying the thickness of the

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emissive layer does not provide any significant improvement

of the device performance. Thus we have assumed that such

poor device efficiency could be attributed to the limitations of

the ATOCs as it has been shown previously for the related

tetraoxa[8]circulenes.21 However the main drawback of the

devices A and B is that the blue emission colour from the 0-0,

0-1 and 0-2 bands (410-480 nm) is contaminated by the long-

wavelength electromer-type emission in the region of 550-700

nm (Figure 4). The resulting colour of devices A and B is light-

purple that does not satisfy the requirements for the color

chromaticity of the commercial OLEDs.22 In order to improve

the lighting characteristics of the devices A and B we have

fabricated multilayered OLEDs using the CuI and TPBi materials

as the hole- and electron-transporting layers, respectively. We

have additionally used the commercial m-MTDATA interlayer

as the exciplex-forming material (Figures S2, S3). Here, we

should note, that the thin films of both ATOC 1 and 2 have very

low roughness values which are acceptable for structuring

OLEDs. The topography of ATOC 2 (Figure 6a) shows a

homogeneous surface with morphological features having a

mean height of 1.19 nm and a root mean square roughness (Rq)

of 0.11 nm. The surface of ATOC 2 has more valleys with a

skewness (Rsk) value of -0.02 and exhibits a leptokurtoic

distribution of the morphological features with a kurtosis (Rku)

value of 4.15 indicating relatively many high peaks and low

valleys. In contrast to ATOC 2, the ATOC 1 surface (Figure 6b)

was found to be rougher with randomly oriented surface

mounds having a mean height of 0.81 and an Rq value of 0.16

nm. The surface of ATOC 1 exhibits a relatively different

symmetry and leptokurtoic distribution of the morphological

features with Rsk and Rku values of -0.31 and 3.64, respectively.

As can be seen from the Figure 5 the separate m-MTDATA and

ATOCs 1, 2 materials demonstrate a similar fluorescence pattern

in the blue spectral region except for the long-wavelength

excimer-type emission of ATOC 1. In contrast, the spin-coated

m-MTDATA:1(or 2) equimolar solid films exhibit an intense

broad exciplex-type PL emission with a strong maximum

around 550 nm (Figure 5, red and green curves). The short-

wavelength emission bands at about 480 nm can be assigned

as the own red-shifted fluorescence of ATOCs 1 and 2. The

same slightly shifted exciplex emission (520 nm) has also been

observed in the EL spectrum of Device C mixed with the

vibronically-resolved fluorescence of compound 1 in the region

of 420-500 nm. Device D (based on ATOC 2) is characterized by

a similar shape of EL spectrum, but the intensity of the 0-0 and

0-1 bands of ATOC 2 (Figure 4, green line) is two times weaker

compared with the Device C. It is probably caused by the more

effective exciplex formation between the ATOC 2 and m-

MTDATA rather than between ATOC 1 and m-MTDATA due to

the N-substituent effect. The lighting characteristics of the


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fabricated devices are summarized in Table 1 and are also

presented in Figures 7-9. The CIE chromaticity coordinates (x,

y) of the devices C and D were found to be (0.27, 0.33) and

(0.28, 0.36), corresponding to white emission colour in

accordance with CIE1931 standard (Table 1, Figure 7, Figure S9).

Table 1. EL Characteristics of the Fabricated Devices A-D.

Device

Von, at 10

Cd/m2

Brightness at 15 V, Cd/m2

Current efficiency,

Cd/A

EQE, %

CIE 1931, (x, y)

at 100/1000 Cd/m2

A 6.8 1900 0.61/1.0 0.3/0.4 (0.23,0.24)

B 6.6 1900 1.49/2.5 0.6/1.0 (0.27,0.26) C 5.4 12 800 3.2/6.4 1.5/3.0 (0.27,0.33)

D 4.2 23 700 1.5/4.2 0.6/1.8 (0.28,0.36)

The exciplex-based OLEDs C and D demonstrate a stable

luminance performance in the vide range of current density

regimes. For instance, the OLED D shows a high brightness of

23700 Cd/m2 at 15V (Table 1) and the current efficiency of

4.2 Cd/A (at 1000 Cd/m2); this value is almost independent on

the current density in the range from 30 to 200 (500) mA/cm2

(Fig. S9 b), which suggests the possible usage of such OLED

structures in display technologies. We note that the current

and power efficiencies as well as external quantum efficiency

for the studied devices C and D can be improved by additional

device passivation, more careful selection of the transporting

layers and also by varying the layer thickness. We also note

that the brightness of the devices C and D is quite high

comparing with similar exciplex-based WOLEDs containing

purely organic fluorescent exciplex-forming materials23-25,

which refers to the particular property of the m-

MTDATA/ATOC interface. Therefore it is our conviction that

the ATOC compounds are truly promising candidates for

exciplex-based organic light emitting devices.

Conclusions

We conclude that the azatrioxa[8]circulenes (ATOCs) studied in

this work represent novel highly-stable and low-cost blue

organic fluorophores that show intense exciplex-type emission

at the organic-organic interface with an exciplex-forming star-

shaped m-MTDATA counterpart. This finding is very useful for

application in OLEDs. Particularly, combining the own blue

electroluminescence of the ATOCs with the exciplex emission

at m-MTDATA:1(or 2) interface makes it possible to cover the

whole visible region and to achieve finally white emission

colour. Actually, these are the first exciplex-based bright

WOLEDs based on hetero[8]circulene species.§ This class of

materials complements and extends the manifold of stable

emissive materials for WOLED applications.26 The extremely

high stability and the low cost of azatrioxa[8]circulenes could

be useful as well as crucial factors for their commercial

utilization in real WOLED-type light sources.

Acknowledgements

The calculations were performed with the computational

resources provided by the Swedish National Infrastructure for

Computing (SNIC) at the Parallel Computer Center (PDC)

through the project “Multiphysics Modeling of Molecular

Materials” SNIC 020/11-23. This research was supported by

the Ministry of Education and Science of Ukraine (project

number 0115U000637), FP7/2007-2013 project AmbiPOD

(grant agreement No 612670), Carl Tryggers foundation (Grant

No. CTS 16:536)

Notes and references

*Email - [email protected]

‡ Devices A–D were fabricated by means of vacuum deposition

of organic semiconductor layers and metal electrodes onto

pre-cleaned ITO coated glass substrate under vacuum of

10−5 Torr. Calcium (Ca) layer topped with aluminum (Al) layer


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J. Mat. Chem. C COMMUNICATION




were used as the cathode. The active area of the obtained

device was 6 mm2.

The current density-voltage and luminance-voltage

dependences were recorded with a semiconductor parameter

analyzer (HP 4145A) using it in the air without passivation

immediately after fabrication of the device. The measurement

of brightness was performed using a calibrated photodiode.

The electroluminescence spectra were recorded with an Ocean

Optics USB2000 spectrometer. Photoluminescence (PL)

spectra and PL decay curves were recorded with the Edinburgh

Instruments FLS980 spectrometer at room temperature using

a low repetition rate μF920H Xenon Flash lamp as the

excitation source.

The PL measurements were performed for the layer prepared

by thermo vacuum deposition and for the layer of the

molecular mixture m-MTDATA:AOC 1(or 2) prepared by casting

the THF solution of the mixture consisting of 50% of m-

MTDATA and 50% of AOC 1 (or 2) onto clean quartz substrate.

Surface morphology of vacuum deposited films of ATOCs 1 and

2 was investigated using atomic force microscopy (AFM). AFM

experiments were carried out in air at room temperature using

a NanoWizardIII atomic force microscope (JPK Instruments),

while data was analyzed using SurfaceXplorer and JPKSPM

Data Processing software. The AFM images were collected

using a V-shaped silicon cantilever (spring constant of 3 N/m,

tip curvature radius of 10.0 nm and the cone angle of 20º)

operating in a contact mode.

§ The first attempt to fabricate the OLEDs based on

hetero[8]circulene representatives was made in 2010 by

Pittelkow et.al.21 They have used the series of unsymmetrical

π-extended tetraoxa[8]circulenes as the emissive species

doped into the (4,4’-N,N’-dicarbazole)biphenyl (CBP) host

matrix. The additional hole- and electron-transporting layers

have been also used, but the final OLEDs have demonstrated

quite poor lighting performance (brightness no more than 817

Cd/A at 12 V, Von more than 7 V, current efficiency no more

than 1.7 Cd/A). Depending on the chemical structure of the

tetraoxa[8]circulenes the resulting emission colour of

performed OLEDs has changed in the range from light-blue to

green. In summary of Ref.21 the authors have concluded that

tetraoxa[8]circulenes are the promising materials for the

development of blue OLEDs. “The very high chemical stability

and the intriguing optical and electrochemical properties of

the tetraoxa[8]circulenes gives rise to optimism with regards

to their use in optical devices.”21 This conclusion is also true

regarding AOCs emitters accounting that in the present work

we have significantly improved the lighting characteristics of

the circulene-based OLEDs comparing with Ref.21. 1 C. B. Nielsen, T. Brock-Nannestad, P. Hammershøj, T. K.

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Journal of Mas Chemterl ia y trCis - Københavns Universitet · Royal Society of Chemistry peer...

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