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

Figure 3. Change in dissolved ozone concentration over time.

Figure 1. Schematic of the microbubble generation system.
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
Figure 2. Size distribution of microbubbles generated by the system. 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
(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 Figure 4. Thickness of the photoresist that was removed by the ozone
ozone microbubble measurement using the null adjustment and microbubble treatment.
that in the same ozonized water after the ozone microbubbles
had completely dissolved. Figure 3 shows a comparison of the thickness from the original value. The negative value at 30 s
dissolved ozone concentration over time for the microbubble might be attributed to swelling of the photoresist layer due to
generation system and that obtained under normal bubbling. action of the ozone microbubbles, and during this initial stage,
The supply of ozone by the microbubble generation system it was also found that the surface changed from hydrophobic to
resulted in a concentration of dissolved ozone approximately hydrophilic. After this initial stage, there is an almost linear
2.5 times higher than that obtained by normal bubbling. The decrease in the thickness of the photoresist over time.
dissolved ozone concentration of the microbubble solution was Relation of Photoresist Removal to Ozone Gas
also found to linearly increase when the ozone concentration of Concentration. When applying ozonized water in semi-
the source gas supplied to the water was increased. conductor cleaning, an important factor to consider is how the
12579 dx.doi.org/10.1021/jp301746g | J. Phys. Chem. C 2012, 116, 12578−12583
The Journal of Physical Chemistry C Article

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 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 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 Figure 7. Photoresist removal rates for ozonized water with or without
Ozonized Water and Ozone Microbubble Solution. To microbubbles.
evaluate the effect of microbubbles on photoresist removal in
more detail, further tests were conducted to compare the photoresist removal rate obtained for ozonized water with or
removal rates obtained using ozonized water and an ozone without microbubbles. It can be seen that the presence of
microbubble solution. A six-inch silicon wafer coated with microbubbles in the ozonized water enhances the removal rate
unexposed g-line positive photoresist (OFPR820-23CP, by more than 30% in comparison to the ozonized water
TOKYO OHKA KOGYO Co., Inc.) was diced into test pieces without microbubbles.
of 30 mm × 30 mm. The thickness of the unexposed Removal of High-Dose Ion-Implanted Photoresist by
photoresist on the wafer was approximately 1.20 μm. Because Ozone Microbubble Water. The previous tests demon-
the photoresist includes sulfur as an ingredient, removal of the strated enhancement in the photoresist removal rate by
photoresist could be evaluated by measuring the amount of treatment with ozone microbubbles. However, in terms of
sulfur present in the photoresist layer without being affected by practical application in semiconductor manufacturing, it would
unexpected swelling or shrinking of the layer caused by the also be useful to remove photoresists damaged during
ozone microbubbles. manufacturing processes. One of the most challenging targets
The tests were conducted by pouring ozonized water, with or for the industry in terms of cleaning is the treatment of high-
without microbubbles, onto the diced wafers. In both cases, the dose ion-implanted photoresists. Cleaning such photoresists is a
water flow rate was approximately 2 L/min, and the considerable challenge due to an amorphous carbon-like
temperature was controlled at approximately 22 °C by a damage layer (crust) caused by ion-implantation at doses
cooling system. The sulfur content of the photoresist layer on higher than 5E14/cm2, and conventionally a two-step process is
the silicon wafer was measured by energy dispersive X-ray used for photoresist removal: low-pressure plasma ashing in a
spectroscopy (EDX-800HS, SHIMADZU Co. Inc.). The test single-wafer tool followed by SPM-based wet removal in a
was continued until the sulfur content reached 0%, indicating batch immersion tool. For advanced semiconductor fabrication
complete removal of the photoresist. processes, single-wafer tools are preferable as they prevent
Figure 6 shows the thickness of the photoresist evaluated as cross-contamination. Therefore, we then conducted tests on
the change in sulfur content of the wafer during application of a implementation of the ozone microbubble generation system to
microbubble solution with a dissolved ozone concentration of a conventional single-wafer spin cleaning tool, as shown in
8.7 mg/L. The photoresist thickness decreased almost linearly Figure 8.
12580 dx.doi.org/10.1021/jp301746g | J. Phys. Chem. C 2012, 116, 12578−12583
The Journal of Physical Chemistry C Article

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
Figure 8. Schematic of the single-wafer spin cleaning tool and addition of ozone for the test. The microbubble generation
microbubble generation system. system was used for the ozone microbubble solution, while the
glass-bonded diffuser was used for the ozonized water without
Eight-inch silicon wafers, spin-coated with a 0.129 μm i-line microbubbles. The electrical conductivity of the waters was
positive photoresist (TDMR AR87LB-18G, TOKYO OHKA approximately 1.0 μS/cm, and the dissolved ozone concen-
KOGYO Co. Inc.) and patterned by an exposure tool, were tration was approximately 8 mg/L in both cases. DMPO was
used as the test samples after phosphorus-ion implantation at a mixed with the samples to a concentration of approximately 40
dose of 1E15/cm2. The ion energy was 60 keV. mM under gentle stirring, and ESR spectra were measured at
The tests were conducted by pouring the ozone microbubble room temperature using an ESR spectrometer (ESRX-10SA-v4,
solution onto the wafers, which were rotating at a spin rate of KEYCOM Co., Ltd.). The hyperfine splitting constant was
200 rpm. Ultrapure water was used with an electrical resistance calibrated using Mn2+ as an external standard. Figure 10 shows
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.
Figure 10. ESR spectrum of ozone microbubbles showing DMPO−
OH. The four peaks in the midsection (marked by circles) are signals
photographs of the wafer at 0, 5, and 10 min after the start of
of the DMPO−OH adduct, and the two peaks at each end are signals
treatment, which show that the high-dose ion-implanted of Mn2+ (external reference).
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 the ESR spectrum of the ozone microbubble solution, which
of dissolved ozone without microbubbles (also with a contains four lines (hyperfine splitting constants of AN = AH =
concentration of 60 mg/L) did not remove any of the 14.9 G), consistent with the spectra of DMPO−OH, indicating
photoresist crust. Figure 9 indicates another important factor to the formation of hydroxyl radicals (·OH).29−31 In the absence
take into account when considering removal of the photoresist of microbubbles, we did not observe any spectral indications of
by the ozone microbubble solution. Because the lateral hydroxyl radicals.
movement of the spinning wafer increases away from the This finding is significant, particularly in relation to removal
central axis, the movement of the ozone microbubbles relative of the high-dose ion-implanted photoresist, because hydroxyl
to the photoresist on the wafer also increases toward the outer radicals have a much higher standard redox potential (2.80 V)
edge of the wafer. The rapid relative movement of the water than ozone (2.07 V), and exhibit immediate and nonselective
generates a turbulent flow beneath the surface. In fact, the reactivity with the majority of organic compounds. In terms of
observed trend of photoresist removal from the edge to the mechanism, the previous work has demonstrated that interfacial
center may indicate that turbulent flow plays a significant role ions accumulated at the gas−water interface might play a role in
in removal of the photoresist. However, at present we do not the generation of free radicals during collapse of the
microbubbles.

■
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 DISCUSSION
in collapsing of the microbubbles. Generation of free radicals is one of the most important
Determination of Hydroxyl Radical Generation by features of microbubble treatment methods in applications such
ESR Measurement. The above experiments demonstrate that as disinfection and water treatment. The present work has
12581 dx.doi.org/10.1021/jp301746g | J. Phys. Chem. C 2012, 116, 12578−12583
The Journal of Physical Chemistry C Article

revealed that microbubbles are very effective in photoresist cations, that is, protons in this case, and generates an electrical
removal because of the generation of hydroxyl radicals and an double layer as shown in Figure 11. Because the interior gases
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 Figure 11. Generation of hydroxyl radicals at the gas−water interface
consequently attracted to the gas−water interface, of ozone microbubbles.
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 of the microbubbles are effectively dissolved into the
near the interface, resulting in a rapid increase in the surrounding water through the interface region, ozone
absolute value of the ζ potential. The drastic environ- molecules encounter accumulated hydroxide ions at the
mental change caused by the extinction of the gas−water interface. This is almost the same situation for ozone as
interface triggers radical generation via dispersion of the being dissolved in a high pH aqueous solution, and the radical
elevated chemical potential that has accumulated around chain that produces hydroxyl radicals is stimulated by the
chemical reaction between ozone and hydroxide ions.

■
the interface.
(4) Low pH conditions are thought to be unfavorable for the
generation of hydroxyl radicals in the case of a dissolved CONCLUSION
ozone solution, but in the case of an ozone microbubble Ozonized water has attracted much attention as an environ-
solution, a significant amount of hydroxyl radicals are mentally friendly cleaning method in semiconductor manu-
generated under strongly acidic conditions. facturing, but its oxidative ability must be enhanced for practical
From a mechanistic point of view, it is important to clarify application. Ozone microbubbles generated from a metal-free
the relationship between radical generation and the ions microbubble generator were investigated in the removal of
accumulated at the gas−water interface. As described, two types photoresists from silicon wafers. It was found that the existence
of ions exist at the interface of the collapsing microbubble: of microbubbles in ozonized water significantly enhances the
adsorbed ions and those electrically attracted as counterions. photoresist removal rate due to the elevated dissolved ozone
The counterions are mainly electrolytes in typical cases. For concentration and the collapse of the microbubbles. Moreover,
microbubble solutions in deionized water, the adsorbed ions are the ozone microbubble solution was able to effectively remove
mainly hydroxide ions while the counterions are protons a high-dose ion-implanted photoresist that is extremely
(hydronium ions).32 Li et al. revealed that copper significantly resistant to removal by ozonized water and other wet chemicals.
catalyzes the generation of hydroxyl radicals from microbubbles ESR experiments revealed that the hydroxide ions adsorbed at
under strongly acidic conditions.4 Iron ions have also been the gas−water interface of the collapsing microbubbles may
found to play an important role in catalytic reaction in the well- initiate the transformation of ozone into hydroxyl radicals,
known Fenton reaction, although hydrogen peroxide is used which play an important role in photoresist removal by the
ozone microbubble treatment.

■
here as an oxidizer instead of ozone.33,34 While there is
insufficient data to discuss the mechanism in detail, it might be AUTHOR INFORMATION
considered that the positively charged metallic ions are
attracted to the microbubble interface, thus playing an Corresponding Author
important catalytic role in the generation of hydroxyl radicals. *E-mail: m.taka@aist.go.jp.
Meanwhile, the present study suggests that hydroxide ions Notes
The authors declare no competing financial interest.

■
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 ACKNOWLEDGMENTS
generated by the dissociation of water molecules. In a This study was partly supported by the Japan Science and
microbubble solution, these ions tend to be adsorbed at the Technology Agency (JST) and the Ministry of Economy, Trade
gas−water interface, with OH− tending to be more effectively and Industry (METI). The authors also acknowledge
adsorbed at the interface than H+, giving rise to a negative Hitachinaka Techno Center, Inc., Renesas Electronics Corpo-
charge at the interface under a wide range of pH conditions. ration, Hitachi, Ltd., Toshiba Mitsubishi-Electric Industrial
The negatively charged gas−water interfaces then attracts Systems Corporation, and Seto Engineering Co., Ltd. for a wide
12582 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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