Material and device properties of highly birefringent nematic glasses and polymer

networks for organic electroluminescence

K. L. Woon
A. E. A. Contoret
S. R. Farrar
A. Liedtke
M. ONeill
P. Vlachos
M. P. Aldred
S. M. Kelly
Abstract Light-emitting nematic liquid crystals are promising materials for organic light-emitting
devices because their orientational anisotropy allows polarized electroluminescence and improved
carrier transport. Two classes of nematics, i.e., room-temperature glasses and crosslinked polymer
networks are discussed. The latter class has an additional advantage in that photolithography can be
used to pixelate a full-color display. We show that the order parameter and birefringence of a new
light-emitting nematic liquid crystal with an extended aromatic core both have values greater than
0.9. The performance of green light-emitting devices incorporating liquid crystals of different conju-
gation lengths is discussed. Efficacies up to 11.1 cd/A at 1160 cd/m
2
at an operating voltage of 7 V
were obtained. A spatially graded, color organic light-emitting device obtained by overlapping pixels
of blue-, green-, and red-emitting liquid crystals were demonstrated. Some regions of the red pixel
were only partially photopolymerized in order to obtain different hues in the overlapping region with
green. We also show that the photolithographic process has micron-scale resolution.
Keywords Organic EL, birefringence, nematic, polymer networks.
1 Introduction
The polymerization of small liquid-crystalline molecules
with a polymerizable group attached to the end of two ali-
phatic chains, the so-called reactive mesogens, is a well-
known technique to develop thermally stable, anisotropic
optical films used as compensation films for liquid-crystal
displays (LCDs) or for optical security products.
1,2
Such
reactive mesogens are deposited by solution processing to
form a thin film. This is subsequently converted to a liquid-
crystal (LC) polymer network by heating or photolithogra-
phy. Recently, we have applied this technology to organic
light-emitting diodes (OLEDs) by developing a new range
of light-emitting reactive mesogens. The chemical structure
of the aromatic core of the LC, which forms the light-emit-
ting chromophore, can be tailored for hole or electron injec-
tion and transport as well as for different colored emission.
A significant advantage of this novel solution-based approach
to OLEDs is that mutlilayer devices are easily made, even
using the same solvent for the deposition of each layer, since
crosslinking renders the underlying layers insoluble. Differ-
ent colored pixels can also be formed using standard
photolithographic techniques,
3
and the materials are also
compatible with the more recently developed ink-jet print-
ing techniques. These advantages also apply to crosslinkable
main-chain polymers, which have also beendevelopedrecently.
4
However, the latter materials do not benefit from the self-
assembling properties of liquid crystals. The delocalized
electrons of extended nematic LCs ensures a high degree of
electronic wave-function overlap.
5,6
This results in rela-
tively high mobility values. The external quantum efficiency
of OLEDs, limited by total internal reflection, is improved
when the rod-like emitters are aligned in the plane com-
pared with an isotropic orientation.
7
Uniform alignment of
the LCs gives linearly polarized emission. Applications include
backlights for LCDs, portable displays suitable for bright
daylight, and three-dimensional displays.
810
In 2000, we
first demonstrated blue-green polarized electrolumines-
cence (EL) using an emitting reactive mesogen uniformly
aligned using photoalignment techniques.
9,11
Reactive
mesogens have since been used by other groups in OLEDs
and organic field-effect transistors.
12,13
More recently, we
have developed a wide range of light-emitting nematic
materials,
1418
studied their physical properties,
5,19
demon-
strated a red, green, and blue pixellated prototype display,
3
synthesized a carrier-transporting photo-aligning polymer,
and shown the three-dimensional potential of the photoalign-
ment technique.
20
In this paper, we report the anisotropic
properties of new extended nematic LCs and their OLED
device characteristics. Both reactive mesogens and non-poly-
merizable light-emitting nematic liquid crystals
21,22
are dis-
cussed. We also show how photolithography can be used to
obtain a new type of color-graded OLED and comment on
the resolution capability of the photolithographic process.
2 Experimental description
Tables 1 and 2 show the chemical structure of the nematic
liquid crystals used in this work. Compounds 1 and 37 are
reactive mesogens and compounds 2 and 8 have nonpolym-
erizable (octyloxy) aliphatic terminal groups. The synthesis
of the compounds 14, and 6 has been discussed pre-
viously.
14,16,18
The synthesis of 5, 7, and 8 will be reported
K. L. Woon, A. E. A. Contoret, S. R. Farrar, A. Liedtke, and M. ONeill are with the Department of Physics, University of Hull.
P. Vlachos, M. P. Aldred, and S. M. Kelly are with the Department of Chemistry, University of Hull, Cottingham Rd., Hull, U.K. HU6 7RX;
e-mail: s.m.kelly@hull.ac.uk.
Copyright 2006 Society for Information Display 1071-0922/06/1406-0557$1.00
Journal of the SID 14/6, 2006 557
elsewhere. An interference method was used to measure
the birefringence n and extraordinary refractive index n
e
of LCs 1 and 2.
23
Two kinds of cells were used, both consist-
ing of glass substrates coated with rubbed polyimide align-
ment layers to provide uniaxial homogeneous alignment. A
wedge cell was employed to find n
e
at 589 nm by reflection
of light from a sodium lamp, using a travelling microscope.
Then n
e
() was obtained from the interference spectrum
obtained by reflecting white light from both interfaces of a
second cell with parallel faces. The same cell was used as
a retardation plate to find n(), assuming the ordinary
refractive index of the LCs is nondispersive. This assump-
tion is only valid for highly elongated LCs having a high
degree of orientational order. The films for dichroic absor-
bance and PL measurements were spun-cast from chloro-
form and aligned on rubbed polystyrene sulphonate/
polyethylene dioxythiophene (PSS/PEDOT) (Baytron P VP
CH 8000, Bayer) on a glass substrate by heating to 220C.
They were then cooled at 1C/minute to 10C above the
glass-transition temperature and then quenched to room
temperature. The PSS/PEDOT was rubbed uniaxially fol-
lowing annealing at 120C for 30 minutes. Polarized absor-
bance spectra were recorded using a Unicam 5625 UV
spectrophotometer and a Coherent sheet UV polarizer (Pola-
coat 105UV). On excitation with a GaN laser at 405-nm, PL
was detected normally from the substrate using a fiber cou-
pled to an Ocean Optics spectrometer. A Glan-Thompson
Polarizer was used to detect the polarization ratio.
OLEDs were fabricated on a glass substrate (25 45
1 mm) covered with an ITO transparent anode and PSS/PE-
DOT (thickness 45 nm), deposited by spin-coating. The
PSS/PEDOT layer was baked at 165C for 5 minutes in
order to cure the layer and remove volatile components.
Thin films of the light-emitting materials as specified below
were prepared by spin-coating from a 11.5 wt.% solution
in chloroform followed by baking at 50C. The films of 4, 6,
and 7 were crosslinked by UV irradiation using a HeCd laser
at 325 nm of fluence 500 J/cm
2
to render the materials com-
pletely insoluble. A hole-blocking layer (6 nm) of commer-
cially available (H. W. Sands) 3-(4-biphenylyl)-4-phenyl-
5-tert-butylphenyl-1,2,4-triazole (TAZ) was deposited on
top of the crosslinked emission layer by vapor deposition
using a vacuum of 10
6
mbar or better. 1,3,5-tris(2-N-phenyl-
benzimidazolyl)benzene (TPBI) was used as a hole-blocking
layer for 8, which is not photopolymerizable, but has a
nematic glass phase at room temperature. Layers of lithium
fluoride (1 nm) and aluminium (80 nm) were sequentially
deposited in the same chamber as a combined cathode. All
OLED processing was carried out in a glove box. EL was
measured using a Labview-controlled Agilent E3631A DC
power supply with a Minolta LS100 luminance meter and
Avaspec2048 fibre spectrometer. The PL quantum efficien-
cies were used using an integrating sphere.
24
The graded-color OLED was prepared using materi-
als 35.Compound 5 is a crystal at room temperature so that
the red-emitting layer consisted of a blend of 20% by weight
of 5 in 4. Solutions of 3 and 4 in chloroform were used to
form the blue- and green-light-emitting layers, respectively.
The individual layers of the device were processed similarly
to the red, green, and blue pixelated OLED discussed else-
where.
3
In this case, however, the pixels had an overlapping
region as discussed in detail below. The preparation of the
device involved the spatial variation of the irradiation condi-
tion for photopolymerization. This was done by focusing the
beam from the HeCd laser to a spot of 1 mm
2
and translat-
ing it across the sample. The total irradiation dose was var-
ied according to the translation speed.
3 Results and discussion
3.1 Liquid-crystal transition temperatures
Table 3 shows the liquid-crystal transition temperatures of
compounds 18. All compounds form nematic glasses on
quenching from the nematic phase. Compounds 2 and 68
are nematic LCs with no discernible melting point. The exact
transition temperatures for 7 and 8 cannot be determined
exactly due to polymerization and/or thermal decomposi-
tion during DSC and optical microscopy measurements.
Both compounds 3 and 4 are nematic reactive mesogens,
TABLE 1 Chemical structures of compounds 14, 6, and 7.
TABLE 2 Chemical structures of the compounds 5 and 8 with the
symmetrical general formula R
1
AR
2
.
558 Woon et al. / Highly birefringent nematic glass
which exhibit a metastable supercooled nematic phase for
room-temperature processing over long periods. Com-
pound 5 is a nematic liquid crystal, which is a crystalline
solid at room temperature and therefore must be used in a
guest-host configuration to obtain a room-temperature nematic
phase.
3.2 Anisotropic properties of extended liquid
crystals
One of the potentially exciting applications of linearly polar-
ized OLEDs is a low-cost near-to-eye three-dimensional
display. The alignment direction of the liquid-crystalline
emitter, and consequently the polarization direction of the
emitted light, can be spatially patterned, when photoalign-
ment techniques are employed.
9,10
Illumination of a pho-
toalignment film with polarized light generates a surface
anisotropy in the alignment layer. Whenthe LCfilmis deposited
on top, the directors orient along the easy axis of the align-
ment layer, on annealing in the nematic phase. Hence, each
pixel can be subdivided into two subpixels having orthogo-
nal polarization directions of emission simply by irradiating
the adjacent subpixels of the photoalignment film with
orthogonally polarized light. The two sets of subpixels are
separately addressed to create two separate images with
orthogonal polarization. A three-dimensional effect is cre-
ated when viewed through glasses having orthogonally
polarized lenses; each eye sees a different image. Very high
polarization ratios are required to avoid crosstalk between
the images. R
EL(PL)
gives the ratio of the measured intensity
of polarized light parallel and perpendicular to the align-
ment direction for EL [photoluminescence (PL)]. The
dichroic ratio D is the ratio of the absorbance of polarised
light parallel and perpendicular to the alignment direction.
An R
EL
value of 13 was found from a photoaligned and
crosslinked reactive mesogen with eight aromatic rings.
3
According to the Onsager theory, the order parameter of
nematics increases with molecular length,
25
and Culligan et
al. obtained a peak R
EL
value of 31 using an oligofluorene
with 24 aromatic rings aligned on a rubbed PSS/PEDOT
substrate.
22
Using a similar approach, we synthesised extended
nematic LCs to increase the anisotropy. n and n
e
of LCs 1
and 2 with six and 14 aromatic rings, respectively, are plot-
ted as a function of wavelength in Fig. 1. The highly disper-
sive nature of n
e
() results from the * absorption reso-
nances, which peak at 395 and 452 nm for compounds 1 and
2, respectively. The dipole moments of the transitions lie
along the long axes of the molecules so that n
e
rather than
n
o
is affected by absorption. The measurements were made
in thick homogeneously aligned cells so that the short wave-
length limit of the data in Fig. 1 is determined by material
absorbance. A maximum n value of 0.7 and 1.1 is obtained
for the six- and 14-ring compounds respectively, confirming
the expected increase with molecular length. As Fig. 1 illus-
trates, the birefringence values of 2 are extremely high, with
a maximum value equal to 0.4n
e
. Hence, extremely large
anisotropy is also expected in absorption and emission. Fig-
ure 2(a) shows the dichroic absorption spectrum of 2 at
room temperature. D has a maximum value of 35, which
corresponds to an order parameter of 0.92. Figure 2(b)
shows the PL spectrum of 2 aligned on rubbed PSS/PE-
DOT. The maximum value of R
PL
is 30. These extremely
high values of the order parameter and R for a nematic
rather then a smectic phase are equivalent to the highest
obtained for LC polymers and oligofluorenes on rubbed
substrates,
25,22
showing the potential of the extended ne-
matics approach. As discussed in the experimental section,
the films were aligned on the rubbed PSS/PEDOT by heat-
ing to 220C and rapid cooling to room temperature. Similar
order parameters were also obtained using a low-tempera-
ture annealing method.
26
The film was spin-cast from
xylene, a high-boiling-point aromatic solvent, which acts as
a plasticizer and thus can be aligned by annealing for 30
minutes at the relatively low temperature of 70C. We are
currently preparing polarized EL devices from compound 2
and from an aligned polymer network based on its photopo-
lymerizable homologue 6.
FIGURE 1 n
e
and n of compounds 1 and 2 as a function of wave-
length.
TABLE 3 Transition temperatures (C) for compounds 18.
Journal of the SID 14/6, 2006 559
3.3 OLEDs incorporating extended liquid
crystals
We have previously reported blue, green, and red EL from
compounds 35.
3
The green-emitting device produced using
4 showed an efficacy of 1.2 cd/A at a luminance of 100
cd/m
2
. We now investigate whether extended nematics pro-
vide improved performance. Table 4 shows the device char-
acteristics of green OLEDs fabricated using compounds 4
and 68. The data shown is typical of the set of best devices
made from the different materials. The reactive mesogen 4
has eight aromatic rings whereas the mesogens 6 and 7 each
have 14. As shown in Table 4, the only difference between
the latter compounds is the replacement of four thiophene
rings by two fused dithiophene groups to improve the color
purity of the green emission. As Table 4 shows, the efficacy
of the crosslinked devices improves with increased conjuga-
tion length. Devices made from 6 and 7 have comparable
values, which are more than four times greater than that
from 4. All three polymerizable materials have the same
value of ionization potential value, very similar band ener-
gies, and small differences in solid-state PL quantum effi-
ciencies, which are 27% for 4 and 33% for both 6 and 7. The
OLED incorporating 4 draws a much larger current than
the others so that the different efficacies are tentatively
attributed to differences in charge transport or charge trap-
ping at chromophore sites. The nematic glass 8 has 18 aro-
matic rings and has a green/yellow emission. It has the
highest efficacy of all the devices, confirming that longer
chromophores improve OLED performance. Figure 3
shows the currentvoltage and luminance of an OLED incor-
porating 8. The efficacy peaks at a luminance of 1160 cd/m
2
at 7 V.
3.4 Resolution of photolithographic process
Afull-color high-information-content flat-panel OLEDrequires
micron-sized pixels. We investigate the spatial resolution of
photopatterning by irradiating a thin film of monomer 3
with light from a HeCd laser of wavelength 325 nm and a
fluence of 150 J/cm
2
through a shadow mask in close contact
with the thin film. The irradiation conditions were chosen
to give a completely insoluble film. The sample was then
washed in chloroform to remove the soluble material. Fig-
ure 4(a) shows a transmission electron micrograph of the
washed film. The darker regions have been irradiated with
ultraviolet light and are insoluble. The lighter regions show
the substrate remaining when the unirradiated film is
removed. The two closest perpendicular stripes are sepa-
FIGURE 2 (a) Dichroic absorbance spectrum of 2 aligned on a rubbed
PSS/PEDOT substrate. (b) PL spectrum from 2 aligned on a rubbed
PSS/PEDOT substrate. I
||
and I

represent the polarized PL intensity

parallel and perpendicular to the director, respectively.
FIGURE 3 Currentvoltage and luminancevoltage characteristics of
OLED incorporating 8.
TABLE 4 Device characteristics of single-pixel OLEDs using com-
pounds 4 and 68.
560 Woon et al. / Highly birefringent nematic glass
rated by 20 m and are clearly resolved. Indeed, micron-
scale resolution is possible with the photolithographic proc-
ess, as shown by exposing a second thin film of 3 through a
phase mask of 1-m period in soft contact with the film. The
phase mask produces a spatially modulated irradiance pat-
tern with the same period as the phase mask; the exact spa-
tial distribution of the irradiance depends on the relative
intensity of the different diffraction orders of the grating.
27
The sample was then washed in chloroform to remove the
soluble material. Figure 4(b) shows the surface profile of
the washed film measured by atomic force microscopy. A
surface-relief grating is formed with a period equal to that
of the phase mask. The non-crosslinked material in the
minimally exposed regions is completely removed while the
fully crosslinked material in the maximally exposed regions
is completely retained. A grating thickness of 85 nm is ob-
tained.
3.5 Color-graded OLED
The photolithographic process can also give a new type of
color-graded image using partial photopolymerization. Fig-
ure 5 shows a photograph of an operating single-pixel mul-
ticolor OLED, prepared by the sequential deposition of the
red, green, and blue materials 35. The EL spectra and
characteristics of single-pixel devices fabricated using the
materials are given elsewhere.
3
The red material was depos-
ited first, irradiated through a mask and washed to remove
the unirradiated material. The green and blue materials
were then processed similarly with the crosslinked green
region partially overlapping the insoluble red film and the
crosslinked blue partially overlapping the green. This results in
blue-green and green-red emission because there is some
EL from both layers in the overlapping regions. A closer
look at Fig. 5 shows that the overlapping green-red region
has two distinct zones giving yellow and orange EL. This
arises because the red material in the overlapping region is
not uniformly thick because the irradiation conditions were
spatially varied to give nonuniform and incomplete polym-
erization resulting in partial removal of the film on washing.
The photograph was taken at an operating voltage of 5 V.
The threshold voltage for EL varies between 3.5 and 4 V
across the device.
FIGURE 4 (a) Scanning electron micrograph of photolithographically
patterned filmof 3. The dark regions have been irradiated with ultraviolet
light and show the insoluble film. The unirradiated regions of the film
were washed away by rinsing the sample in chloroform and the substrate
appears light in the image. (b) The surface profile obtained using atomic
force microscopy of the washed polymer network film produced by
irradiation of monomer 3 through a phase mask of 1-m period. The
period of the surface profile is equal to that of the phase mask.
FIGURE 5 Photograph of graded-color single-pixel OLED operating
at 5 V. The logo represents the Humber bridge located near Hull,
England. This is one of the longest single-span bridges in the world.
Journal of the SID 14/6, 2006 561
4 Conclusions
We show that light-emitting nematic liquid crystals repre-
sent an attractive alternative material choice to the more-
standard small molecules and main-chain polymers for
OLEDs. Extended nematic LCs, with up to 14 rings in the
aromatic core, have extremely high values of birefringence.
They show order parameters as large as those of main-chain
polymers and give bright EL We also show that polym-
erizable LCs have an extra advantage in that they can be
patterned photolithographically with micron-scale resolu-
tion. They also allow a new type of graded-color OLED to
be fabricated.
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Kai L. Woon received his B.S. and Ph.D. degrees
in physics from the University of Hull in 2000 and
2004, respectively. His Ph.D. topic was circularly
polarized photoluminescence from chiral nematic
liquid crystals. As a postdoctoral researcher at
Hull, he studied the light-emission and semicon-
ducting properties of liquid crystals. He is cur-
rently a postdoctoral researcher at the University
of Oxford.
AdamE. A. Contoret was awarded his M.Eng. degree
in optoelectronics in 1997 and his Ph.D. in phys-
ics in 2001, both from the University of Hull. He
has since worked as a researcher at the University
and as a development engineer at Hewlett-
Packard. He is currently a director of Dream-
science, Ltd.
562 Woon et al. / Highly birefringent nematic glass
Simon R. Farrar received his B.S. and Ph.D. degrees
in physics from the University of Hull. He has
since worked on laser ablation of a range of mate-
rials. More recently, he has studied charge trans-
port and organic electroluminescence from novel
light-emitting liquid crystals.
Alicia Liedtke received her Diploma degree in
applied laser technology at the University of Applied
Sciences in Emden in 2004 and then pursued her
Ph.D. at the organophotonics group at the Univer-
sity of Hull.
Mary ONeill received her Ph.D. in physics from
the University of Strathclyde, Scotland. After a
postdoctoral fellowship in integrated optics at the
University of Glasgow and a short spell in indus-
try, she joined the Physics department of the Uni-
ver si t y of Hul l . She i s joi nt l eader of t he
interdisciplinary organophotonics group, which
investigates new photonic and optoelectronic
applications for liquid crystals.
Panos Vlachos completed his undergraduate de-
gree in chemistry at the University of Hull in
1999. He obtained his Ph.D. from the University
of Hull in 2003 before carrying out postdoctoral
research at Hull. He is currently studying for his
MBA at the University of Durham, U.K.
Matthew Aldred completed his undergraduate
degree in chemistry at the University of Hull in
1999. He obtained his M.Sc. from UMIST in 2000
and his Ph.D. from the University of Hull in 2004
before carrying out postdoctoral research at Hull.
He is currently a postdoctoral researcher at the
Changchun Institute of Applied Chemistry in the
Peoples Republic of China.
Steve M. Kelly began his research career in liquid
crystals in 1976 at the University of Hull with Pro-
fessors G.W. Gray, FRS, and E.P. Raynes, FRS, as
Ph.D. supervisors. He spent 15 years in liquid-
crystal industrial research at Asea Brown Boveri
with J. Nehring and T. J. Scheffer and F. Hoff-
mann-La Roche with M. Schadt before returning
to the U.K. in 1995 as an Advanced Fellow of the
EPSRC. He was appointed to the academic staff in
2000 and promoted to professor in 2004. He has
over 160 scientific publications and 75 patents.
Journal of the SID 14/6, 2006 563