Molecular Design on Highly Efficient White Electroluminescence

from a Single-Polymer System with Simultaneous Blue, Green, and

Red Emission**

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DOI: 10.1002/adma.200601580

By Jun Liu, Zhiyuan Xie, Yanxiang Cheng, Yanhou Geng, Lixiang Wang,* Xiabin Jing, and
Fosong Wang
White polymer light-emitting diodes (WPLEDs) have received great attention because of their potential use in fullcolor displays in combination with color filters and as a backlight for liquid-crystal displays.[123] In order to get white emission, the general strategy is to use a blend as the emissive
layer, such as a polymerpolymer blend,[16] polymersmallmolecule blend,[710] or polymerorganometallic-complex
blend.[1115] In order to enhance the efficiency of WPLEDs
based on this strategy, a multilayer device configuration,[13]
triplet utilization,[1115] and interface engineering[6] have been
used. Although very high efficiency has been achieved, these
blend systems suffer from bias-dependent electroluminescence (EL) spectra and intrinsic phase separation.
Our solution to achieving white EL is to develop singlepolymer systems with different emission components based
on the control of energy transfer and charge trapping between
the chromophores in the designed polymers.[1922] For example, we succeeded in realizing highly efficient white electroluminescence with simultaneous blue and orange emission from
a single polymer, in which a small amount of orange-lightemissive 1,8-naphthalimide derivatives or 2,1,3-benzothiadiazole derivatives were incorporated into the main chain of a
blue-light-emitting polyfluorene.[1921] This approach has also
been used to design a single-polymer system with simultaneous light emission of all three primary colors (blue, green,
and red) by incorporating a red-light-emitting unit in the main
chain and attaching a green emissive unit to the side chain of
a blue-light-emitting polymer host. However, its current efficiency is as low as 1.59 cd A1, which is not sufficient for potential display applications.[22] Very recently, Cao and co-

[*] Prof. L. X. Wang, J. Liu, Prof. Z. Y. Xie, Dr. Y. X. Cheng,

Prof. Y. H. Geng, Prof. X. B. Jing, Prof. F. S. Wang
State Key Laboratory of Polymer Physics and Chemistry
Changchun Institute of Applied Chemistry
and Graduate School of the Chinese Academy of Sciences
Chinese Academy of Sciences
Changchun 130022 (P.R. China)
E-mail: lixiang@ciac.jl.cn
[**] This work was supported by the National Natural Science Foundation of China (Nos. 20574067 and 50633040) and the 973 Project
(No. 2002CB613402). The authors thank Dr. Matthew P. Aldred for
fruitful discussion. Supporting Information is available online from
Wiley InterScience or from the authors.

Adv. Mater. 2007, 19, 531535

workers reported white electroluminescent single polymers

with both singlet and triplet emission. A high luminance efficiency of 4.7 cd A1 with International Commission on Illumination (CIE) coordinates of (0.38, 0.35) was achieved.[23]
In our previous work, we proposed a new approach to designing highly efficient blue and green electroluminescent
polymers using the dopant/host strategy by grafting small
amounts of blue or green fluorescent dye (dopant) to the side
chain of the polymer host to form an intramolecular dopant/
host system, resulting in a significant improvement in both EL
efficiency and color stability.[24,25] For example, the singlelayer device based on the blue-light-emitting polymer with
poly(fluorene-co-benzene) as the host and 4-dimethylamino1,8-naphthalimide as the dopant in the side chain exhibited a
maximum luminance efficiency of 6.85 cd A1 and external
quantum efficiency of 3.54 %, about 46 times that of the
corresponding polyfluorene homopolymer.[24] Therefore, the
dopant/host strategy is suitable for developing highly efficient
electroluminescent polymers with the potential to display the
full-color spectrum.
In this Communication, we introduce the dopant/host strategy to the molecular design on white electroluminescence
from a single-polymer system with simultaneous blue-, green-,
and red-light emission, to improve the electroluminescent
efficiency, and to investigate the influence of the attachment
of the dopants to the host on the electroluminescent performance. Two kinds of attachment of dopants (green- and redlight-emitting dopants) to the blue-light-emitting polymer
host (polyfluorene backbone) were involved in the molecular
design. One was with the green- and red-light-emitting dopants both in the side chain of the blue-light-emitting polymer
host. The other was with the green-light-emitting dopant in
the side chain and the red-light-emitting dopant in the main
chain of the blue-light-emitting polymer host for the control
study. The former design has the advantage of forming an intramolecular dopant/host system without affecting the electronic properties of the polymer backbone (host), which is
suitable for the individual emission of each emissive species
and is expected to lead to remarkable improvement in luminous efficiency, as reported in our previous publications.[24,25]
By adjusting the content of green- and red-light-emitting dopants, we controlled the partial energy transfer from the blue
species to the green species and from the blue species to the
red species, and prevented energy transfer from the green spe-

2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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cies to the red species, therefore realizing individual emission

from blue-, green-, and red-light-emitting species (Fig. 1).
As a result, white electroluminescence with simultaneous
blue (maximum wavelength, kmax = 436 nm/460 nm), green
(kmax = 496 nm), and red emission (kmax = 570 nm) with the
CIE coordinates (0.31, 0.32) was observed. Great improvement in the EL efficiency was observed for the polymer based
on the side-chain methodology. A single-layer device of the
polymer exhibited luminous efficiency as high as 7.3 cd A1
and power efficiency up to 4.17 lm W1. To the best of our
knowledge, this is the most efficient white electroluminescent
single polymer with three emission species.
The chemical structures of the polymers WRGB-P1 and
WRGB-P2, are shown in Figure 1. Polyfluorene was selected

Figure 1. The chemical structures of the polymers and model compounds.

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as the blue-light-emitting conjugated polymer host.[26,27] 4-Diphenylamino-1,8-naphthalimide (DPAN) (model compound

GMC, photoluminescence (PL) quantum efficiency
UPL = 0.91) was chosen as the green-light-emitting dopant unit
and was attached to the side chain of the blue-light-emitting
host.[25] The 4-(5-(4-(diphenylamino)-phenyl)-thienyl-2-)-7-(4methoxybenzene)-2,1,3-benzothiadiazole
unit
(MB-BTThTPA) (model compound RMC, UPL = 0.51) was selected as
the red-light-emitting species, which was attached to the side
chain of polyfluorene in WRGB-P1 and was incorporated into
the main chain of polyfluorene in WRGB-P2. The contents of
the red- and green-light-emitting species were tuned between
0.01 mol % and 0.05 mol %. The best white EL spectrum was
obtained from the polymer containing 0.02 mol % greenlight-emitting dopant and 0.02 mol %
red-light-emitting dopant. All the polymers were synthesized using the Suzuki
reaction with corresponding comonomers and feed ratios. All the polymers
are soluble in common organic solvents,
such as toluene, dichloromethane, and
tetrahydrofuran (THF). All three polymers exhibit good thermal stability with
a glass-transition temperature (Tg) of
65 C and thermal-degradation temperature (Td) above 430 C. Polyfluorene
containing only 0.3 mol % of the redlight-emitting MB-BT-ThTPA unit on
the side chain or main chain with complete energy transfer were also synthesized.
To investigate the EL properties of the
polymers, single-layer devices (device
configuration: ITO / poly(3,4-ethylenedioxythiophene):poly(styrene
sulfonic
acid) (PEDOT:PSS) (40 nm) / polymer (90 nm) / Ca (10 nm) / Al (100 nm))
were fabricated with the polymers as
emissive layers. As shown in Figure 2,
the EL spectra of WRGB-P1 and
WRGB-P2 both exhibit simultaneous
blue (kmax = 433 nm/460 nm), green
(kmax = 496 nm), and red (kmax = 570 nm)
emission bands with comparable intensity. By comparing the EL spectra of
WRGB-P1 and WRGB-P2 with the EL
spectra of polyfluorene containing only
0.02 mol % DPAN (green-light-emitting
unit) or only 0.02 mol % MB-BT-ThTPA
(red-light-emitting unit) (not shown), we
attribute the blue, green, and red emission in the EL spectra of WRGB-P1 and
WRGB-P2 to the individual emission
from polyfluorene, DPAN, and MBBT-ThTPA, respectively.[22] The strong
green/red emission from the DPAN/MB-

2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Adv. Mater. 2007, 19, 531535

BT-ThTPA unit results from the partial energy transfer and

charge trapping from polyfluorene to the DPAN/MB-BTThTPA unit, as favored by the overlap of the absorption spectra
of GMC/RMC and emission spectra of PF (Fig. 3a; structure of
PF shown in Fig. 1) as well as the positions of the lowest unoccupied molecular orbital (LUMO) / highest occupied molecular orbital (HOMO) energy levels of PF and GMC/RMC
(Fig. 3b).[28] The CIE coordinates of the EL spectra of WRGBP1 and WRGB-P2 were (0.31, 0.32) and (0.30, 0.31), respectively, which are located close to the (0.33, 0.33) of standard
white-light emission. The EL spectra shapes of WRGB-P1 and
WRGB-P2 were stable when the bias was increased from 5 V
to 10 V (Fig. 2). The EL spectra at 5 V exhibited larger contri-

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Figure 2. EL spectra of WRGB-P1 (a) and WRGB-P2 (b).

butions from the green-light-emitting DPAN unit and red-lightemitting MB-BT-ThTPA unit than those in the EL spectra at
610 V. This is because of the more serious charge trapping by
the DPAN unit and MB-BT-ThTPA unit at low driving voltage.
The EL performance data of all the devices are listed in
Table 1. Impressive EL performance was observed for
WRGB-P1. The WRGB-P1 device exhibited a turn-on voltage of 4.0 V, luminance efficiency of 7.30 cd A1, power efficiency of 4.17 lm W1 and a maximum brightness of
12 710 cd m2. The current-densityvoltage and brightness
voltage curves of the device with WRGB-P1 as the emissive
layer are shown in Figure 4. These efficiencies are more than
four times those given in our previous publication.[22] The
WRGB-P1 device also exhibited moderate thermal stability.
Thermal-annealing of the device at 60 C for 2 h in nitrogen
atmosphere did not lead to a decrease of its EL efficiencies.
Figure 5 compares the luminous efficiencies of the WRGBP1 and WRGB-P2 devices. The luminous efficiency obtained
from WRGB-P1 was about two times that observed for
WRGB-P2. The higher EL efficiency of WRGB-P1 demonstrated the effectiveness of the molecular design and the improvement in the attachment methodology, in which both the
red-light-emitting dopant and the green-light-emitting dopant
were attached to the side chain of the blue-light-emitting
polymer host instead of to the main chain. To support this, we
investigated the EL properties of the polymers that incorporated only 0.3 mol % of the red-light-emitting MB-BT-ThTPA
unit in the main chain or the side chain. Complete energy
transfer is observed and emission comes dominantly from the
MB-BT-ThTPA unit. As listed in Table 1, the side-chain-type
polymer P1-30 (see Fig. 1) exhibited slightly higher EL effi-

Table 1. EL performance of the devices of the polymers (device configuration: ITO/PEDOT/polymer/Ca/Al).

Polymer

WRGB-P1
WRGB-P2
P1-30
P2-30

Figure 3. a) The absorption spectra of GMC and RMC and the emission
spectra of PF. b) The energy levels of PF, GMC, and RMC.

Adv. Mater. 2007, 19, 531535

Turn-on
voltage [V]

Luminous
efficiency
[cd A1]

Power
efficiency
[lm W1]

Maximum
brightness
[cd m2]

CIE
coordinates
(x,y)

4.0
4.0
5.5
6.0

7.30
3.80
5.08
4.14

4.17
1.99
1.92
1.46

12 710
12 870
9 615
8 427

(0.31, 0.32)
(0.30, 0.31)
(0.51, 0.43)
(0.51, 0.45)

Figure 4. Current-densityvoltage and brightnessvoltage curves of the

WRGB-P1 device.

2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

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WRGB-P1
WRGB-P2

Figure 5. The dependence of the luminous efficiencies of WRGB-P1 and

WRGB-P2 devices on the current density.

ciencies than the main-chain-type counterpart P2-30 (see

Fig. 1). We also fabricated a control device with the blend PF,
0.02 mol % GMC, and 0.02 mol % RMC, which exhibited a
luminous efficiency of 4.7 cd A1 (not shown). The EL efficiency of the blend was lower than that of WRGB-P1 but
higher than that of WRGB-P2. The detailed reason for the
different EL efficiencies of main-chain-type polymer and
side-chain-type polymer is not clear yet because the concentrations of green- and red-light-emitting dopant units are too
low to give signals in common characterization methods.
Moreover, the interchain and intrachain energy transfer and
charge trapping between the chromophores in the white polymers are believed to differ from the energy transfer and
charge trapping between small molecules.[29] Mllen and coworkers[30] have reported that when a green chromophore
(perylene) and a red chromophore (perylene diimide) are simultaneously incorporated into the main chain of a bluelight-emitting conjugated polymer (polyfluorene), the resulting polymer exhibits very low PL quantum efficiency. Therefore, we speculate that the relatively low efficiency of
WRGB-P2 is caused by the through-conjugation interaction
of the excitons of the three emission species, which decreases
the radiative decay rate of the excitons. In addition, the incorporation of chromophores into the main chain of the polymer
host will change the electronic properties of the polymer
backbone, preventing the polymer backbone from functioning
well as a host. This may be another reason for the low efficiency of WRGB-P2.
In conclusion, by introducing the strategy of a dopant/host
system to the molecular design of white-light-emitting polymers, we have developed a highly efficient white electroluminescent polymer, in which both green- and red-light-emitting
dopant units are covalently attached to the side chain of a
blue-light-emitting host polymer with alkyl spacers. Singlelayer devices of the resulting polymers emitted white light
with simultaneous blue, green, and red emission. We also
demonstrated that the EL efficiencies of white polymers
based on three emission species could be enhanced by attaching both the dopants to the side chain of the blue-light-emitting conjugated polymer host instead of incorporating one or

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both dopants into the main chain of the blue-light-emitting

host. A resultant turn-on voltage of 4.0 V, luminous efficiency
of 7.30 cd A1, power efficiency of 4.17 lm W1, maximum
brightness of 12 710 cd m2 and CIE coordinates (0.31, 0.32)
were demonstrated. This performance, which is achieved by
molecular design, is among the best reported for single-layer
WPLEDs. Further investigation of white-light-emitting polymers with three dopants (blue-, green-, and red-light-emitting
dopants) attached to the side chain of a conjugated polymer
host is in progress in our laboratory.

Experimental
The synthesis of the monomers and the model compounds are provided in the Supporting Information.
General Procedure of Suzuki Polymerization: To a mixture of 2,7-dibromo-9,9-dioctylfluorene (1) (quantities given below), 2,7-bis(trimethylene boronate)-9,9-dioctylfluorene (2), and Pd(PPh3)4 (0.0115 g,
0.01 mmol) under argon was added a drop of Aliquat 336, 2M aqueous
potassium carbonate (2.5 mL), and degassed toluene (5 mL). Solutions of 2,7-dibromo-9-hexyl-9-(6-(4-diphenylamino-1,8-naphthalimide-9-)hexyl)fluorene (monomer G), 2,7-dibromo-9-hexyl-9-(6-(4(7-(5-(4-(di(4-bromophenyl)amino)phenyl)thienyl-2-yl)-2,1,3-benzothiadiazole-4-yl)phenyloxy)hexyl)fluorene (monomer R-P) or 4-(4methoxyphenyl)-7-(5-(4-(di(4-bromophenyl)amino)phenyl)thienyl2-yl)-2,1-3-benzothiadiazole (monomer R-M) were also added. The
mixture was stirred at 90 C for 48 h and then poured into methanol.
The precipitate was collected by using filtration, dried, and then dissolved in dichloromethane. The solution was washed with water and
dried over anhydrous Na2SO4. After most of the solvent had been removed, the residue was poured into stirred methanol to give a fiberlike
solid. The polymer was further purified by extracting with acetone for
24 h. The reprecipitation procedure in dichloromethane/methanol was
then repeated several times. The final product, a light orange-colored
fiber, was obtained after drying in a vacuum with a yield of 4560 %.
PF: 1 (0.2742 g, 0.5000 mmol) and 2 (0.2792 g, 0.5000 mmol) were
used in the polymerization. Gel-permeation chromatography (GPC):
Mn = 2.47 104, polydispersity index (PDI) = 2.09 (polystyrene as standard).
WRGB-P1: 1 (0.2739 g, 0.4996 mmol), 2 (0.2792 g, 0.5000 mmol),
monomer G (0.40 mL 5 104 M solution in toluene, 2 104 mmol),
and monomer R-P (0.40 mL 5 104 M solution in toluene,
2 104 mmol) were used in the polymerization. GPC: Mn = 2.30 104,
PDI = 1.92.
WRGB-P2: 1 (0.2739 g, 0.4996 mmol), 2 (0.2792 g, 0.5000 mmol),
monomer G (0.40 mL 5 104 M solution in toluene, 2 104 mmol),
and monomer R-M (0.40 mL 5 104 M solution in toluene,
2 104 mmol) were used in the polymerization. GPC: Mn = 2.48 104,
PDI = 1.98.
P1-30: 1 (0.2725 g, 0.497 mmol), 2 (0.2792 g, 0.5000 mmol), and
monomer R-P (3.2 mg, 3 103 mmol) were used in the polymerization. GPC: Mn = 2.39 104, PDI = 1.99.
P2-30: 1 (0.2725 g, 0.497 mmol), 2 (0.2792 g, 0.5000 mmol), and
monomer R-M (2.2 mg, 3 103 mmol) were used in the polymerization. GPC: Mn = 2.63 104, PDI = 1.96.
All these polymers showed similar 1H NMR spectra and elemental
analysis results. For example, PF: 1H NMR (300 MHz, CDCl3) d
(parts per million; ppm): 7.87 (d, 2H), 7.72 (br, 4H), 2.10 (br, 4H),
1.14 (br, 24H), 0.81 (t, 6H). Analysis calculated: C 89.69, H 10.31.
Found: C 89.08, H 10.02. The contents of green- and red-light-emitting dopant units in these polymers were too low to be detected using
1
H NMR and elemental analysis. According to our previous publication [25], we assumed that the actual contents of DPAN and MB-BTThTPA units in all the polymers are the same as the feed ratio of the
corresponding monomers.

2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Adv. Mater. 2007, 19, 531535

Received: July 14, 2006

Revised: September 28, 2006
Published online: January 24, 2007

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Device Fabrication: The indium tin oxide (ITO) glass plates were
degreased in an ultrasonic solvent bath and then dried in a heating
chamber at 120 C. The poly(styrene sulfonic acid)-doped poly(ethylenedioxythiophene) was spin-coated on the treated ITO at 3000 rpm
for 60 s and then baked for 15 min at 120 C to give an approximate
thickness of 40 nm. The polymer layer (ca. 90 nm) was then spin-coated onto the PEDOT/ITO-coated glass substrate in fresh toluene
solution (15 mg mL1) at ambient atmosphere, followed by thermalannealing in a vacuum at 80 C for 1 h. Finally, a thin layer of calcium (10 nm) followed by a layer of aluminum (100 nm) was deposited in a vacuum thermal evaporator through a shadow mask at a
pressure of 5 103 Pa. The active area of the diodes was 10 mm2.

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