Article

pubs.acs.org/JPCC

Effect of Microbubbles on Ozonized Water for Photoresist Removal

Masayoshi Takahashi,*,† Hiroaki Ishikawa,‡ Toshiyuki Asano,‡ and Hideo Horibe§
†
National Institute of Advanced Industrial Science and Technology (AIST), 16-1 Onogawa, Tsukuba, Ibaraki 305-8569, Japan
‡
Industrial Technology Institute of Ibaraki Prefecture, 3781-1 Nagaoka, Ibaraki, Higashi-Ibaraki, Ibaraki 311-3195, Japan
§
Kanazawa Institute of Technology, 3-1 Yatsukaho, Hakusan, Ishikawa 924-0838, Japan

ABSTRACT: In this paper, we describe the use of ozone

microbubbles in photoresist removal from silicon wafers.
Ozonized water has attracted much attention as an environ-
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mental friendly cleaning method in semiconductor manufac-

turing. However, it would be desirable to enhance the
oxidative ability of ozonized water for practical application.
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The existence of microbubbles in ozonized water has been

shown to significantly enhance the photoresist removal rate due to an elevated dissolved ozone concentration (approximately 2.5
times that of ordinary ozone bubbling) and a direct effect of the microbubbles (removal rate is approximately 1.3 times faster
than water with the same concentration of dissolved ozone without microbubbles). Additionally, the ozone microbubble solution
was able to effectively remove a high-dose ion-implanted photoresist, which is extremely resistant to removal by ozonized water
and other wet chemicals because of its amorphous carbon-like layer, or “crust”. Electron spin resonance experiments were also
performed without the influence of serious metal contamination and indicated the presence of hydroxyl radicals, which are
thought to be formed by interaction of ozone with hydroxide ions adsorbed at the gas−water interface upon collapse of the
microbubbles. The hydroxyl radicals play an important role in photoresist removal by the ozone microbubble treatment.

■ INTRODUCTION
Microbubbles are tiny bubbles with diameters of less than 50
μm. When generated in water, the bubbles decrease in size and
eventually disappear under water because of their long
stagnation and excellent gas dissolution ability.1 The collapse
of these bubbles in water has been shown to lead to the
generation of activated oxidizers such as hydroxyl radicals. This
is thought to arise from the extinction of the gas−water
interface, which might trigger dispersion of the elevated
chemical potential accumulated at the interface as adsorbed
ions.2−4 Similarly, when microbubbles of ozone are generated
in water, the dispersion of the chemical potential arising from
the extinction of the gas−water interface leads to the
decomposition of ozone and the generation of large quantities
of hydroxyl radicals, which may provide a new type of advanced
oxidation process (AOP).5 Such properties suggest the use of
microbubbles as a new method of wastewater treatment.
In the production of semiconductor devices, surface
contamination of the silicon wafers causes serious problems.
As a result, large amounts of chemicals, such as H2SO4, H2O2,
HCl, NH4OH, and amine solvents, are required in wet cleaning
processes.6,7 For safety and environmental reasons, the use of
ozonized water is attracting attention as a viable method for
removing organic contaminants, which have been convention-
ally removed by a high-temperature sulfuric acid−hydrogen
peroxide mixture (SPM).8−17 In terms of applications to
semiconductor manufacturing, ozonized water cleaning systems
are strongly desired as they provide enhanced removal rates for
organic contaminants. In addition, the challenge to the
amorphous carbon-like damage layer created by ion-implant
doses greater than 5E14/cm2 is significantly important to
introduce the ozone cleaning method in the semiconductor
manufacturing processes.18−25
In this paper, we investigate the effects of microbubbles on
ozonized water for the removal of photoresists. A comparison is
made between treatments with and without microbubbles. We
also discuss the physicochemical mechanism of ozone micro-
bubbles in enhancing the removal rate, taking into account the
electron spin resonance (ESR) results, and describe the
treatment of a high-dose ion-implanted photoresist.
Ozone Microbubble Generation System Used in
Silicon Wafer Cleaning. Figure 1 shows a schematic of the
microbubble generation system used in the experiments. For
practical application in semiconductor manufacturing, all parts
of the system in contact with water are made of metal-free
Teflon materials. A bellows cylinder pump (ΣP-15C, Sigma
Technology Inc.) realizes low pulsation discharge intakes of
water and gas through its intake line, and discharges them
through a dissolution tank in which the gas is effectively
dissolved in water under a pressure of approximately 0.4 MPa.
The water containing the dissolved gas is then released by a
dispersing nozzle (Shigen-kaihatu Co., Inc.), and the resulting
pressure decreased to ambient conditions causes supersatura-
tion of the dissolved gas. Bubble nuclei generated by turbulent
flow at the nozzle grow rapidly into microbubbles under the
supersaturated condition. Figure 2 shows the bubble size
distribution of generated microbubbles in distilled water
measured by a particle-counting spectrometer for liquids
Received: February 22, 2012
Revised: May 11, 2012
Published: May 16, 2012

© 2012 American Chemical Society 12578 dx.doi.org/10.1021/jp301746g | J. Phys. Chem. C 2012, 116, 12578−12583
The Journal of Physical Chemistry C
Figure 1. Schematic of the microbubble generation system.
Figure 2. Size distribution of microbubbles generated by the system.
(LiQuilaz-E20; Particle Measuring Systems Inc.) using a light-
obscuration method. The microbubble solution, milky in
appearance, exhibits two peaks: a sharp peak around 15 μm
in diameter and a broader peak around 40 μm.
The change in concentration of dissolved ozone was
compared between a glass-bonded diffuser and the microbubble
generation system. In both cases, approximately 50 g/m3 of
ozone gas was fed at a flow rate of 1 L/min to 5 L of distilled
water in a glass container. The dissolved ozone concentration
was measured by an ultraviolet ozone analyzer (PL-620A, Ebara
Jitsugyo Co., Ltd.). Because the light-obscuration caused by the
presence of microbubbles introduced errors in the analysis of
the ozone concentration, we accounted for the effect of
microbubbles on the analysis by performing a null adjustment
for solutions in which air microbubbles were generated by the
system. As a result, it was found that there was no significant
difference between the indicated ozone concentration in the
ozone microbubble measurement using the null adjustment and
that in the same ozonized water after the ozone microbubbles
had completely dissolved. Figure 3 shows a comparison of the
dissolved ozone concentration over time for the microbubble
generation system and that obtained under normal bubbling.
The supply of ozone by the microbubble generation system
resulted in a concentration of dissolved ozone approximately
2.5 times higher than that obtained by normal bubbling. The
dissolved ozone concentration of the microbubble solution was
also found to linearly increase when the ozone concentration of
the source gas supplied to the water was increased.
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Figure 3. Change in dissolved ozone concentration over time.
Photoresist Removal by Ozone Microbubbles. The
performance of the ozone microbubble solution in photoresist
removal was investigated by measuring the change in thickness
of the photoresist residue. A 6 in. silicon wafer coated with
unexposed high-contrast i-line positive photoresist (THMR-
iP3300, TOKYO OHKA KOGYO Co. Inc.) was diced into test
pieces of 30 mm × 30 mm. The tests were conducted by
pouring the microbubble solution onto the diced wafers, as
shown in Figure 1. In this test, the flow rate of the microbubble
solution was approximately 8 L/min, which was sufficient to
cover the entire surface of the diced wafer, ensuring uniform
removal of the photoresist. The average thickness of nine
distinct measurement points on the wafer was obtained from
measurements taken every 30 s for 2 min using a thin film
analyzer (F20, Filmetrics Inc.). The dissolved ozone concen-
tration was approximately 15 mg/L, and the water temperature
was approximately 30 °C throughout the test.
Figure 4 shows the thickness of the photoresist that was
removed during the treatment as indicated by the difference in
Figure 4. Thickness of the photoresist that was removed by the ozone
microbubble treatment.
thickness from the original value. The negative value at 30 s
might be attributed to swelling of the photoresist layer due to
action of the ozone microbubbles, and during this initial stage,
it was also found that the surface changed from hydrophobic to
hydrophilic. After this initial stage, there is an almost linear
decrease in the thickness of the photoresist over time.
Relation of Photoresist Removal to Ozone Gas
Concentration. When applying ozonized water in semi-
conductor cleaning, an important factor to consider is how the
dx.doi.org/10.1021/jp301746g | J. Phys. Chem. C 2012, 116, 12578−12583
The Journal of Physical Chemistry C
rate of photoresist removal could be increased. A determining
factor in this process has been shown to be the ozone
concentration. Thus, we investigated the effect of ozone
concentration of the source gas supplied for microbubble
generation on the rate of photoresist removal. The tests were
conducted under the same conditions as shown in Figure 1
with the exception that the ozone gas concentration was varied
from 30 to 150 g/m3. The removal rate of photoresist was
evaluated by measuring the thickness of the photoresist over
time by the thin film analyzer. The results of the average
removal rate during the initial 3 min are shown in Figure 5 as a
Figure 5. Effect of ozone gas concentration on photoresist removal
rate.
function of ozone gas concentration. It can be seen that that
there is a linear relationship between the ozone gas
concentration and the photoresist removal rate. In terms of
the photoresist removal rate, the increase in ozone gas
concentration has the same effect in the microbubble treatment
as that in the ordinary ozone treatment.
Comparison of Photoresist Removal Rate between
Ozonized Water and Ozone Microbubble Solution. To
evaluate the effect of microbubbles on photoresist removal in
more detail, further tests were conducted to compare the
removal rates obtained using ozonized water and an ozone
microbubble solution. A six-inch silicon wafer coated with
unexposed g-line positive photoresist (OFPR820-23CP,
TOKYO OHKA KOGYO Co., Inc.) was diced into test pieces
of 30 mm × 30 mm. The thickness of the unexposed
photoresist on the wafer was approximately 1.20 μm. Because
the photoresist includes sulfur as an ingredient, removal of the
photoresist could be evaluated by measuring the amount of
sulfur present in the photoresist layer without being affected by
unexpected swelling or shrinking of the layer caused by the
ozone microbubbles.
The tests were conducted by pouring ozonized water, with or
without microbubbles, onto the diced wafers. In both cases, the
water flow rate was approximately 2 L/min, and the
temperature was controlled at approximately 22 °C by a
cooling system. The sulfur content of the photoresist layer on
the silicon wafer was measured by energy dispersive X-ray
spectroscopy (EDX-800HS, SHIMADZU Co. Inc.). The test
was continued until the sulfur content reached 0%, indicating
complete removal of the photoresist.
Figure 6 shows the thickness of the photoresist evaluated as
the change in sulfur content of the wafer during application of a
microbubble solution with a dissolved ozone concentration of
8.7 mg/L. The photoresist thickness decreased almost linearly
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Figure 6. Change in photoresist thickness by the ozone microbubble
treatment.
over time, and the photoresist was completely removed by 9.6
min. Because the thickness of the photoresist was 1.20 μm, the
average photoresist removal rate was calculated to be 0.125
μm/min in this case. Figure 7 shows a comparison of the
Figure 7. Photoresist removal rates for ozonized water with or without
microbubbles.
photoresist removal rate obtained for ozonized water with or
without microbubbles. It can be seen that the presence of
microbubbles in the ozonized water enhances the removal rate
by more than 30% in comparison to the ozonized water
without microbubbles.
Removal of High-Dose Ion-Implanted Photoresist by
Ozone Microbubble Water. The previous tests demon-
strated enhancement in the photoresist removal rate by
treatment with ozone microbubbles. However, in terms of
practical application in semiconductor manufacturing, it would
also be useful to remove photoresists damaged during
manufacturing processes. One of the most challenging targets
for the industry in terms of cleaning is the treatment of high-
dose ion-implanted photoresists. Cleaning such photoresists is a
considerable challenge due to an amorphous carbon-like
damage layer (crust) caused by ion-implantation at doses
higher than 5E14/cm2, and conventionally a two-step process is
used for photoresist removal: low-pressure plasma ashing in a
single-wafer tool followed by SPM-based wet removal in a
batch immersion tool. For advanced semiconductor fabrication
processes, single-wafer tools are preferable as they prevent
cross-contamination. Therefore, we then conducted tests on
implementation of the ozone microbubble generation system to
a conventional single-wafer spin cleaning tool, as shown in
Figure 8.
dx.doi.org/10.1021/jp301746g | J. Phys. Chem. C 2012, 116, 12578−12583
The Journal of Physical Chemistry C
Figure 8. Schematic of the single-wafer spin cleaning tool and
microbubble generation system.
Eight-inch silicon wafers, spin-coated with a 0.129 μm i-line
positive photoresist (TDMR AR87LB-18G, TOKYO OHKA
KOGYO Co. Inc.) and patterned by an exposure tool, were
used as the test samples after phosphorus-ion implantation at a
dose of 1E15/cm2. The ion energy was 60 keV.
The tests were conducted by pouring the ozone microbubble
solution onto the wafers, which were rotating at a spin rate of
200 rpm. Ultrapure water was used with an electrical resistance
of approximately 17 MΩ/cm. The dissolved ozone concen-
tration was approximately 60 mg/L, and the water temperature
was approximately 22 °C throughout the test. Figure 9 shows
Figure 9. Removal of high-dose ion-implanted photoresist by ozone
microbubbles.
photographs of the wafer at 0, 5, and 10 min after the start of
treatment, which show that the high-dose ion-implanted
photoresist was being removed from the outer edge to the
center of the wafer. We also conducted the same test for an
ozone solution without microbubbles. Significantly, the solution
of dissolved ozone without microbubbles (also with a
concentration of 60 mg/L) did not remove any of the
photoresist crust. Figure 9 indicates another important factor to
take into account when considering removal of the photoresist
by the ozone microbubble solution. Because the lateral
movement of the spinning wafer increases away from the
central axis, the movement of the ozone microbubbles relative
to the photoresist on the wafer also increases toward the outer
edge of the wafer. The rapid relative movement of the water
generates a turbulent flow beneath the surface. In fact, the
observed trend of photoresist removal from the edge to the
center may indicate that turbulent flow plays a significant role
in removal of the photoresist. However, at present we do not
have sufficient information to clarify the mechanism, and can
only state that it may be a result of accelerated mass transfer of
ozone to the surface of the wafer, or an effect of turbulent flow
in collapsing of the microbubbles.
Determination of Hydroxyl Radical Generation by
ESR Measurement. The above experiments demonstrate that
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the existence of microbubbles in ozonized water enhanced the
photoresist removal rate for a backed photoresist and could
effectively remove a high-dosed ion-implant photoresist. To
clarify the mechanism by which the ozone microbubble
solution acts on the photoresist, we performed ESR measure-
ments by the spin-trap method. 5,5-Dimethyl-1-pyrroline-N-
oxide (DMPO) was used as the spin-trap reagent because it has
been widely used to identify oxygen-centered radicals such as
superoxide and the hydroxyl radical.26−31
Ozonized water with or without microbubbles was tested by
the ESR spin-trap method. Distilled water was used after the
addition of ozone for the test. The microbubble generation
system was used for the ozone microbubble solution, while the
glass-bonded diffuser was used for the ozonized water without
microbubbles. The electrical conductivity of the waters was
approximately 1.0 μS/cm, and the dissolved ozone concen-
tration was approximately 8 mg/L in both cases. DMPO was
mixed with the samples to a concentration of approximately 40
mM under gentle stirring, and ESR spectra were measured at
room temperature using an ESR spectrometer (ESRX-10SA-v4,
KEYCOM Co., Ltd.). The hyperfine splitting constant was
calibrated using Mn2+ as an external standard. Figure 10 shows
Figure 10. ESR spectrum of ozone microbubbles showing DMPO−
OH. The four peaks in the midsection (marked by circles) are signals
of the DMPO−OH adduct, and the two peaks at each end are signals
of Mn2+ (external reference).
the ESR spectrum of the ozone microbubble solution, which
contains four lines (hyperfine splitting constants of AN = AH =
14.9 G), consistent with the spectra of DMPO−OH, indicating
the formation of hydroxyl radicals (·OH).29−31 In the absence
of microbubbles, we did not observe any spectral indications of
hydroxyl radicals.
This finding is significant, particularly in relation to removal
of the high-dose ion-implanted photoresist, because hydroxyl
radicals have a much higher standard redox potential (2.80 V)
than ozone (2.07 V), and exhibit immediate and nonselective
reactivity with the majority of organic compounds. In terms of
mechanism, the previous work has demonstrated that interfacial
ions accumulated at the gas−water interface might play a role in
the generation of free radicals during collapse of the
microbubbles.
■
DISCUSSION
Generation of free radicals is one of the most important
features of microbubble treatment methods in applications such
as disinfection and water treatment. The present work has
dx.doi.org/10.1021/jp301746g | J. Phys. Chem. C 2012, 116, 12578−12583
The Journal of Physical Chemistry C
revealed that microbubbles are very effective in photoresist
removal because of the generation of hydroxyl radicals and an
elevated concentration of dissolved ozone. Furthermore, the
newly developed, metal-free microbubble generation system
can produce microbubbles without serious contamination,
enabling us to investigate the mechanism of transformation of
ozone into hydroxyl radicals.
Our experimental research into radical generation by
collapsing microbubbles has revealed the following re-
sults:1−5,32
(1) The microbubbles decrease in size at an increasing rate
and eventually disappear because of dissolution of the
interior gas into solution.
(2) ζ potential measurements reveal that the microbubbles
are electrically charged owing to the adsorption of H+
and OH− ions at the gas−water interface. The pH level
of the water significantly affects the ζ potential of the
microbubble, and the interface is negatively charged over
a wide range of pH conditions. Counter ions are
consequently attracted to the gas−water interface,
resulting in the formation of an electrical double layer.
(3) In the collapse process, the increasing rate of shrinking of
the gas−water interface leads to the accumulation of ions
near the interface, resulting in a rapid increase in the
absolute value of the ζ potential. The drastic environ-
mental change caused by the extinction of the gas−water
interface triggers radical generation via dispersion of the
elevated chemical potential that has accumulated around
the interface.
(4) Low pH conditions are thought to be unfavorable for the
generation of hydroxyl radicals in the case of a dissolved
ozone solution, but in the case of an ozone microbubble
solution, a significant amount of hydroxyl radicals are
generated under strongly acidic conditions.
From a mechanistic point of view, it is important to clarify
the relationship between radical generation and the ions
accumulated at the gas−water interface. As described, two types
of ions exist at the interface of the collapsing microbubble:
adsorbed ions and those electrically attracted as counterions.
The counterions are mainly electrolytes in typical cases. For
microbubble solutions in deionized water, the adsorbed ions are
mainly hydroxide ions while the counterions are protons
(hydronium ions).32 Li et al. revealed that copper significantly
catalyzes the generation of hydroxyl radicals from microbubbles
under strongly acidic conditions.4 Iron ions have also been
found to play an important role in catalytic reaction in the well-
known Fenton reaction, although hydrogen peroxide is used
here as an oxidizer instead of ozone.33,34 While there is
insufficient data to discuss the mechanism in detail, it might be
considered that the positively charged metallic ions are
attracted to the microbubble interface, thus playing an
important catalytic role in the generation of hydroxyl radicals.
Meanwhile, the present study suggests that hydroxide ions
adsorbed at the gas−water interface may also have a catalytic
role in the chain reaction of ozone decomposition.
In pure water, H+ and OH− exclusively exit as ions, which are
generated by the dissociation of water molecules. In a
microbubble solution, these ions tend to be adsorbed at the
gas−water interface, with OH− tending to be more effectively
adsorbed at the interface than H+, giving rise to a negative
charge at the interface under a wide range of pH conditions.
The negatively charged gas−water interfaces then attracts
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cations, that is, protons in this case, and generates an electrical
double layer as shown in Figure 11. Because the interior gases
Figure 11. Generation of hydroxyl radicals at the gas−water interface
of ozone microbubbles.
of the microbubbles are effectively dissolved into the
surrounding water through the interface region, ozone
molecules encounter accumulated hydroxide ions at the
interface. This is almost the same situation for ozone as
being dissolved in a high pH aqueous solution, and the radical
chain that produces hydroxyl radicals is stimulated by the
chemical reaction between ozone and hydroxide ions.
■
CONCLUSION
Ozonized water has attracted much attention as an environ-
mentally friendly cleaning method in semiconductor manu-
facturing, but its oxidative ability must be enhanced for practical
application. Ozone microbubbles generated from a metal-free
microbubble generator were investigated in the removal of
photoresists from silicon wafers. It was found that the existence
of microbubbles in ozonized water significantly enhances the
photoresist removal rate due to the elevated dissolved ozone
concentration and the collapse of the microbubbles. Moreover,
the ozone microbubble solution was able to effectively remove
a high-dose ion-implanted photoresist that is extremely
resistant to removal by ozonized water and other wet chemicals.
ESR experiments revealed that the hydroxide ions adsorbed at
the gas−water interface of the collapsing microbubbles may
initiate the transformation of ozone into hydroxyl radicals,
which play an important role in photoresist removal by the
ozone microbubble treatment.
■
AUTHOR INFORMATION
Corresponding Author
*E-mail: m.taka@aist.go.jp.
Notes
The authors declare no competing financial interest.
■
ACKNOWLEDGMENTS
This study was partly supported by the Japan Science and
Technology Agency (JST) and the Ministry of Economy, Trade
and Industry (METI). The authors also acknowledge
Hitachinaka Techno Center, Inc., Renesas Electronics Corpo-
ration, Hitachi, Ltd., Toshiba Mitsubishi-Electric Industrial
Systems Corporation, and Seto Engineering Co., Ltd. for a wide
dx.doi.org/10.1021/jp301746g | J. Phys. Chem. C 2012, 116, 12578−12583
The Journal of Physical Chemistry C Article

variety of technical support. We are also very grateful to T. (34) Burbano, A. A.; Dionysiou, D. D.; Suidan, M. T.; Richardson, T.
Nishimoto for assisting in experimental work. L. Water Res. 2005, 39, 107−118.

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