COMMUNICATION
DOI: 10.1002/adma.200700208
Photoswitches and Phototransistors from Organic
Single-Crystalline Sub-micro/nanometer Ribbons**
By Qingxin Tang, Liqiang Li, Yabin Song, Yaling Liu, Hongxiang Li,* Wei Xu, Yunqi Liu,
Wenping Hu,* and Daoben Zhu*
Photoelectronic devices of organic semiconductors are of
great interest recently because organic semiconductors have
many fundamental advantages over their inorganic counter-
parts.[1] For example, their low cost is ideal for large-area
applications and their mechanical flexibility makes them natu-
rally compatible with plastic substrates for lightweight and
foldable products. The most attractive prospect, however, is
their incorporation of functionality by molecular design.
Phototransistors have much higher sensitivity and lower
noise than photodiodes and use these advantages to combine
light detection and signal magnification properties that realize
greater functionality in a single device.[2] This is an important
aspect of optoelectronic integration. Since the first concept of
a phototransistor was proposed by William Shockley in 1951,
inorganic phototransistors have been quickly developed and
used in a variety of applications. However, few reports in the
literature have addressed phototransistors made of organic
semiconductors,[2c,3] especially organic single crystals.[3c]
Organic single crystals have important merits in the study
of intrinsic properties and for the fabrication of high-quality
devices and circuits.[4] Here, we used an organic semiconduc-
tor, copper hexadecafluorophthalocyanine (F16CuPc), as the
candidate to introduce single-crystalline photoswitches and
phototransistors of organic semiconductors. F16CuPc was
selected not only because of its remarkable air-stable, n-type
– Au
[*] Dr. H. Li, Prof. W. Hu, Prof. D. Zhu, Q. Tang, L. Li, Y. Song, Y. Liu,
Dr. W. Xu, Prof. Y. Liu
Beijing National Laboratory for Molecular Sciences
Key Laboratory of Organic Solids, Institute of Chemistry
Chinese Academy of Sciences
Beijing 100080 (P.R. China )
E-mail: huwp@iccas.ac.cn; lhx@iccas.ac.cn; zhudb@iccas.ac.cn
Q. Tang, L. Li, Y. Song, Y. Liu
Graduate School of Chinese Academy of Sciences
Beijing 100039 (P.R. China)
[**] W.H. is grateful to Prof. Zhigang Shuai (Institute of Chemistry, Chi-
nese Academy of Sciences), Prof. Jean-Luc Brédas (Georgia Insti-
tute of Technology), and Dr. Vitaly Podzorov (Rutgers University)
for profound discussions. The authors acknowledge financial sup-
port from the National Natural Science Foundation of China
(20421101, 20404013, 20402015, 20571079, 20527001, 20472089),
the Ministry of Science and Technology of China (2006CB806200,
2006CB932100), and the Chinese Academy of Sciences. Supporting
Information is available online from Wiley InterScience or from the
author.
2624 © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
properties but also because of its high thermal and chemical
stability.[5] Bao et al. first paid attention to this compound in
1998.[5a] Recently, Dosch and Barrena and co-workers care-
fully investigated its structure and self-organization properties
on a solid surface.[5b–f] In addition, we synthesized single-crys-
talline sub-micro/nanoribbons of the compound by a physical
vapor transport technique and studied its field-effect perfor-
mance; we demonstrated its high field-effect mobility and on/
off ratio in transistors based on an individual ribbon.[6] How-
ever, the optical properties of this air-stable, n-type material,
are still unclear. In this Communication, we study these prop-
erties by using devices made of single-crystalline sub-micro/
nanometer ribbons of F16CuPc.
Single-crystalline sub-micro/nanometer ribbons of F16CuPc
were synthesized and transferred or in-situ patterned onto Si/
SiO2 (300 nm) substrates, as previously described.[6,7] Devices
based on an individual sub-micro/nanometer ribbon were fab-
ricated by the “multiple-times gold-wire mask moving” tech-
nique[6,7] based on the asymmetrical drain/source electrode
(Au/Ag) configuration shown in Figure 1—because such a
configuration was beneficial for injection, transport, and col-
lection. The ribbon thickness in the devices was measured
carefully by atomic force microscopy.
Ag
A B Vapor
Au
SiO2
2.5 µm
n++Si
C Au Ag D
SiO2
n++Si 5 µm
Figure 1. A) An individual sub-micrometer ribbon on a SiO2 surface
350 nm in width and 260 nm in thickness. B) Au gap electrodes were
fabricated by thermal evaporation with a micrometer-sized Au wire as the
mask; by slightly moving the Au-wire mask, Au–Ag gap electrodes were
deposited by thermal evaporation (C). D) A scanning electron microsco-
py (SEM) image of a device based on an individual F16CuPc single-crystal
sub-micrometer ribbon.
Adv. Mater. 2007, 19, 2624–2628
 COMMUNICATION
Without a gate connection, the single-crystal devices of 5
F16CuPc performed as photoswitches, as shown in Figure 2. A VG= 0 V 4.46

Power (mW/cm )
2
By switching the light source on/off, the devices were capable 4
3.04
of switching on/off reversibly and fast. The response and

ISD(nA)
3
1.98
2
400 1.12
0.37
Current (pA)

1
300 Dark
200
0
0 2 4 6 8 10
100
VSD(V)
-8
0 10
0 200 400 600 B
Time (s) 10
-9 Dark
Light
Figure 2. Photoresponse of single-crystalline devices of F16CuPc, which

can be switched on/off quickly by light irradiation. Conditions: under
6 mW cm–2 of white-light irradiation, a conductive channel length of
∼ 13 lm and width of ∼ 500 nm, with voltage between electrodes kept
constant at 10.0 V.
recovery velocities (for the 80 % of devices that responded
and recovered) were estimated to be near 100 Hz and 50 Hz,
respectively. The devices also exhibited high reproducibility
and retention ability. After several tens of cycles and nearly
1 h of continuous work, no degradation was observed (see
Supporting Information, Figure S1). In fact, we have tried
hundred of cycles on a single device in a single run and its per-
formance was almost identical. For most devices, the perfor-
mance did not change until the Ag electrode was oxidized.
With a gate connection, it is interesting to note that, under
light irradiation, our single-crystal transistors exhibited strong
photodependence, working as phototransistors. This is differ-
ent from inorganic phototransistors, in that in our organic
phototransistors the light entered the transistors from the
semiconductor side instead of from the back gate (see Sup-
porting Information, Figure S2). Approximately 60 photo-
transistors of sub-micro- and nanometer F16CuPc ribbons
were investigated, the “output” characteristics of one such
device being shown in Figure 3A, where ISD (source–drain
current) as a function of the VSD (source–drain voltage) under
different power density of illumination (gate voltage,
VG = 0 V) is plotted. The transistor was controlled by the inci-
dent light, and its output characteristics were very similar to
those of organic field-effect transistors. This suggests that the
light could substitute VG as an independent variable to con-
trol the output of the transistor, indicating a new way to rea-
lize light detection and signal magnification in a single organic
device for future low-cost, ultrahigh-density organic photo-
electric integration. The corresponding “transfer” characteris-
tics of the phototransistor in the dark (solid circles) and under
illumination (closed circles, 1.12 mW cm–2) are shown in Fig-
ure 3B. An obvious increase of ISD was observed under illumi-
nation because of the contribution of the photocurrent. At
VG = –6.0 V, the transistor was charge-depleted in the dark; in
this case only the photocurrent contributed to the measured
ISD.[3c] The maximum on/off ratio of the phototransistor was
ISD(A)
-10
10
10
-11
4
Ion/Ioff=4.5x10
-12
10
-13
10
-15 -10 -5 0 5 10
VG(V)
Figure 3. A) The “output” characteristics of a F16CuPc phototransistor,
using light irradiation to substitute the effect of VG. The light density
changed from 0 to 4.46 mW cm–2 with a fixed VG = 0 V. The channel
length of the device was around 10 lm with a width of 350 nm. B) The
“transfer” characteristics of a single-crystal F16CuPc phototransistor
measured in the dark (solid circles) and under illumination (open circles,
1.12 mW cm–2), at VSD = 10 V with a channel length of 10 lm with a
width of 350 nm.
calculated to be 4.5 × 104 (at VG = –6.0 V). Actually, among
the 60 investigated devices, the on/off ratio ranged from ap-
proximately 102–105, around 10 % of devices having an on/off
ratio between 104–105, 80 % devices with an on/off ratio be-
tween 102–103, and 10 % devices with an on/off ratio below
102. The large range of the on/off ratio of our devices is proba-
bly because the on/off ratio depends on many parameters,
such as the length and width of the conductive channel as well
as the thickness of the single-crystal ribbons. It should be
noted that the single-crystalline transistor of F16CuPc was a
normal on-behaving device, probably because of the random
doping for this n-type material.
As we know, phototransistors are based on photo-generated
free carriers, such as electrons or holes. Hence, there are two
possible working mechanisms for the F16CuPc single-crystal-
line phototransistors. One is similar to that of organic photo-
voltaic devices. The absorbed light of the single crystals gener-
ates huge excitons, then the excitons dissociate into free
electrons and holes. After that, the free electrons and holes
diffuse in the single crystals and finally are collected at the an-
ode and cathode electrodes. The devices efficiency depends
on the light absorbance, exciton dissociation, electron and
hole diffusion, and electrode collection. However, unfortu-
nately no photovoltage was observed for either end of the
organic single-crystalline devices of F16CuPc (see Fig. 1), de-

Adv. Mater. 2007, 19, 2624–2628 © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.advmat.de 2625
COMMUNICATION
spite a large photocurrent being observed. Another possible
mechanism is that our F16CuPc single-crystalline ribbons
worked as a photoconductor. When incident light falls on the
surface of the photoconductor, carriers are generated and
result in an increase of conductivity (r = nel, where r is the
conductivity, n is the number of carriers, l is the mobility of
F16CuPc, and e is the electronic charge). The results of
Figure 2 demonstrate that F16CuPc has very high sensitivity
to irradiation by light. Hence, it is highly possible that our
F16CuPc single-crystalline ribbons work as photoconductors.
As is known, photoswitches and phototransistors are both
based on photo-generated free carriers. Hence, the efficiency
of the devices is closely related to the light absorbed by the
materials. The absorption spectrum of F16CuPc is shown in
Figure 4. From the long wavelength edge, the bandgap of
F16CuPc is estimated to be around 1.4–1.5 eV, which agrees
well with the reference value.[5g] The narrower energy gap in-
dicates that the devices of F16CuPc are easily excited by light.
Absorbance (a.u.)
Current (pA)
4
3
2
300 600 900
Wavelength(nm)
Figure 4. Absorbance spectrum of F16CuPc and the wavelength depen-
dence of F16CuPc sub-micro/nanometer-sized ribbon devices. The ribbon
of the device shown was ∼ 14 lm long and 200 nm wide. The power of
the incident light at every wavelength was fixed at 10 lW cm–2.
When light with photon energy equal to or higher than the
bandgap energy of F16CuPc is absorbed, a number of charge
carriers are generated. Hence, light could play a role as an
additional terminal that optically controls the device opera-
tion, alongside the three conventional terminals, source, drain,
and gate electrodes.[2c] Moreover, it is also found that F16CuPc
has a wider absorbance range in both B- and Q-bands than
many other phthalocyanines, such as copper phthalocya-
nine.[8–9] The B-bands of phthalocyanines are known to be
mainly associated with the transition from the second highest
occupied molecular orbital (HOMO) to the lowest unoccu-
pied molecular orbital (LUMO), and Q-bands are assigned to
the transition from HOMO to LUMO.[8–9] The wide absorp-
tion range of F16CuPc suggests that the transition from
HOMO to LUMO, or from the second HOMO to LUMO, of
F16CuPc easily occurs, indicating that F16CuPc is easily ex-
cited by light, that is, the material is a good photoconductor.
This agrees well with our above assumption.
The photoresponse characteristics to wavelength of the de-
vices were investigated by using a series of filters with wave-
2626 www.advmat.de © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
lengths at 408, 445, 494, 525, 553, 595, 624, 651, 705, 736, 755,
and 785 nm (the power of the incident light at every wave-
length was fixed at 10 lW cm–2). The results are shown in Fig-
ure 4, and from these it is obvious that the photosensitivity of
the devices is in accord with the absorbance of F16CuPc, indi-
cating that the performance of the photodevices is strongly
dependent on the wavelength of the incident light, that is, on
the absorption of the organic single-crystalline ribbons. The
good agreement of the photosensitivity and absorption spec-
tra of our devices suggest its potential use in light-controlled
devices.
Comparing the switch ratios of the photoswitches with
those of the phototransistors, the maximum on/off ratio of the
latter was nearly two–three orders of magnitude higher than
that of the former. This is probably due to the gate applied
bias of the transistors providing an efficient way for the disso-
ciation of the photo-generated excitons, and is beneficial for
the formation of the conducting channel of the transistors. Ac-
cording to the Beer–Lambert law, the light absorbed in an or-
ganic material decreases exponentially with the thickness of
the organic layer. Hence, it is highly possible that the intensity
of the incident light on the crystal/SiO2 is very weak after it
has traveled through the single-crystal layer (ca. 260 nm
thick).[3a] Without a gate bias, the two ends of the device are
actually surface-activated photoswitches (Fig. 5A), in which
the exciton dissociation is inefficient because of the recombi-
nation caused by the disorder and dissipation. Based on a
series of device results, it was empirically found when the
thickness of the ribbons was larger than 80 nm, the switch
ratio of the photoswitches increased linearly with the width of
the ribbons (Fig. 5B) (the length of the conducting channel
was kept constant, ca. 12 lm) regardless of the large thickness
variation of the ribbons (the thickness of the ribbons was
changed from 80 to 450 nm). This confirmed the surface-acti-
vated process of the photoswitches in this case. It agreed
υ
hυ 100
Switch Ratio
A
B
Au 50
Ag
F16CuPc
0
SiO2
400 800
n++Si Width (nm)
υ
hυ 3000
Switch Ratio
C D
2000
Au Ag 1000
0
SiO2
0 600 1200 1800
n++Si Width (nm)
Figure 5. A) Working model of the F16CuPc single-crystal photoswitches.
B) Switch-ratio dependence of the photoswitches on the ribbon width.
C) Working model of the F16CuPc single-crystal phototransistors.
D) Switch-ratio dependence of the phototransistors on the ribbon width.
Adv. Mater. 2007, 19, 2624–2628
 COMMUNICATION
well with our assumed device model in Figure 5A. It should
A B
be mentioned when the thickness of the ribbons was lower
than 80 nm, no such empirical rule was found between the
υ

Signal out
hυ

Signal out
switch ratio and the width of the ribbons. Moreover, the

Input

Input
switch ratio of the photoswitches was found to be in propor-
tion to the width of the ribbons when their length and thick- υ
hυ
ness were both kept constant. In addition, considering that
the back Si gate of our photoswitches was floating and it had Optoisolator Optical Switch
a large volume (the volume of the heavily doped Si substrate C D
was large and had many bulk electrons), the application of a
υ
hυ υ
hυ
source potential VSD would probably polarize the gate (or
change its net charge), resulting in a “pseudo-gating” effect in
al

In
the ISD(VSD) characteristics. Therefore, in our experiments, gn R

pu
i
S ut Vo
the back Si of all devices was set to zero by grounding before

every measurement.
With an applied gate bias, the switch ratio of the same
device was greatly increased compared with that of its corre-
sponding photoswitch. It is highly likely that the dissociated
electrons from the photo-generated excitons were attracted to
the F16CuPc crystal/SiO2 interface to form the conductive
channel between the source and drain electrodes (Fig. 5C),
which provided an efficient way for the dissociation of exci-
tons into free electrons and holes, and increased the charge
density in the conductive channel. Correspondingly, our
device results suggest that the switch ratio of the phototransis-
tors increases nonlinearly with the width of the ribbons, as
shown in Figure 5D, although the length of the conducting
channels of the devices were kept constant (ca. 12 lm)—the
selected transistors had similar mobilities of ca. 0.05–
0.10 cm2 V–1 s–1 to guarantee the similar quality of the devices.
These nonlinear characteristics are different from that of the
photoswitches, indicating that the phototransistors are not sur-
face-activated devices in this case and the contribution from
exciton dissociation and the formation of a conductive chan-
nel by gate bias could not be neglected.
Based on the high sensitivity and large on/off ratio of the
F16CuPc single-crystalline phototransistors, a series of devices
with potential applications could be fabricated. For example,
considering the strong absorbance of F16CuPc in the UV-vis
and near-IR spectra range, low-cost, visible and near-IR
photodetectors could be fabricated, such as optoisolators,
highly sensitive optical switches, and retro-sensors (Fig. 6A–
C, respectively). Moreover, the phototransistors are also
applicable in some circuits (Fig. 6D–F). Finally, it should be
mentioned that the single-crystalline phototransistors of
F16CuPc exhibit an almost identical performance in vacuum
and in air, indicating little influence of oxygen and water on
F16CuPc, that is, the excellent air stability of F16CuPc.
In summary, here we studied photoswitches and phototran-
sistors of organic single crystals, for the first time, by using
sub-micro/nanometer ribbons of a remarkable air-stable,
n-type organic semiconductor, F16CuPc. From this study,
we have demonstrated: 1) High-quality photoswitches of
F16CuPc single crystals could be fabricated, which were capa-
ble of both reversible and fast switching. 2) Single-crystal
field-effect phototransistors of F16CuPc individual sub-micro/
t
o
Retro Sensor Vo “high” with light
E F
υ
Vo hυ R R Load
υ
hυ
Vo “low” with light A load circuit
Figure 6. Demonstration of the potential application of F16CuPc single-
crystalline phototransistors in A) optoisolators: the optoisolator is simi-
lar to a transformer in that the output is electronically isolated from the
input; B) highly sensitive optical switches: an object is detected when it
enters the gap of the optical switch and blocks the light path between the
emitter and detector; C) retro sensors: the retro sensor detects the pres-
ence of an object by generating light and then looking for its reflectance
off of the object to be sensed; D–E) basic circuits; and F) a circuit with
greater voltage-switching capability.
nanoribbons exhibited strong photodependence, that is, inci-
dent light can act as an independent variable to control the
output current of the single-crystalline transistors. 3) The
maximum on/off ratio of the phototransistor was 4.5 × 104 (at
VG = –6.0 V), which was probably due to the gate applied bias
providing an efficient way for the dissociation of the photo-
generated excitons, and which was beneficial for the forma-
tion of a conducting channel in the phototransistors. 4) The
high light sensitivity and large on/off ratio of the phototransis-
tors suggest their potential application in optoisolators, opti-
cal switches, retro sensors and circuits. Thus, a new way to rea-
lize light detection and signal magnification in a single organic
device is opened up, indicating a future for this material in
low-cost, ultrahigh density organic photoelectric integration.
Experimental
F16CuPc nanoribbons were synthesized by a physical vapor trans-
port process, as previous described.[6,7] The photoswitches and photo-
transistors were fabricated on a Si/SiO2 (300 nm) substrate based on
the coplanar geometry of electrodes. The nanoribbins were first trans-
ferred to a Si/SiO2 substrate, and then the Au and Ag were deposited
by thermal evaporation on an individual ribbon as drain and source
electrodes, respectively, by the “multiple-times, gold-wire mask mov-

Adv. Mater. 2007, 19, 2624–2628 © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.advmat.de 2627
COMMUNICATION
ing” technique. For the fabrication of a F16CuPc device with a Au–Ag
asymmetrical electrode configuration, the mask of the micrometer-
sized gold wire needed to be moved once by our Micromanipula-
tor 6150 probe station (which could control the movement of the gold
wire mask accurately within 5 lm); the device yield factor was ∼ 70 %
with the length of the conducting channel ranging from ca. 7 to
15 lm. In our experience, this method is useful for basic research on
devices from such sub-micro- or nanometer scaled ribbons. The mor-
phology of the devices was examined using a field-emission scanning
electron microscope (Hitachi S-4300). The thickness of the F16CuPc
ribbons was measured by atomic force microscopy (Nanoscopy IIIa,
USA). To study the effect of light on the electrical properties of the
devices, a white-light iodine–tungsten lamp with a power density rang-
ing from 0.37 to 5.76 mW cm–2 was employed as the illumination
source. Current–voltage (I–V) characteristics of devices were re-
corded with a Keithley 4200 SCS and a Micromanipulator 6150 probe
station in a clean and shielded box at room temperature in air, as well
as a Lakeshore XTPP6 low-temperature vacuum probe station.
Received: January 24, 2007
Revised: April 10, 2007
Published online: August 15, 2007
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