Berny, Stephane et al.

Patent Trials and Appeals Board

Sep 9, 2019

14399009 - (D) (P.T.A.B. Sep. 9, 2019)

UNITED STATES PATENT AND TRADEMARK OFFICE
UNITED STATES DEPARTMENT OF COMMERCE
United States Patent and Trademark Office
Address: COMMISSIONER FOR PATENTS
P.O. Box 1450
Alexandria, Virginia 22313-1450
www.uspto.gov
APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO.
14/399,009 11/05/2014 Stephane Berny MERCK-4247 1064
23599 7590 09/09/2019
MILLEN, WHITE, ZELANO & BRANIGAN, P.C.
2200 CLARENDON BLVD.
SUITE 1400
ARLINGTON, VA 22201
EXAMINER
HAVLIN, ROBERT H
ART UNIT PAPER NUMBER
1639
NOTIFICATION DATE DELIVERY MODE
09/09/2019 ELECTRONIC
Please find below and/or attached an Office communication concerning this application or proceeding.
The time period for reply, if any, is set in the attached communication.
Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the
following e-mail address(es):
docketing@mwzb.com
PTOL-90A (Rev. 04/07)

UNITED STATES PATENT AND TRADEMARK OFFICE
____________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
____________

Ex parte STEPHANE BERNY, AMY PHILLIPS, PRITI TIWANA,
TOBY CULL, MIGUEL CARRASCO-OROZCO, and NICOLAS BLOUIN
____________

Appeal 2019-003260
Application 14/399,009
Technology Center 1600
____________

Before JEFFREY N. FREDMAN, DEBORAH KATZ, and JOHN G. NEW,
Administrative Patent Judges.

FREDMAN, Administrative Patent Judge.

DECISION ON APPEAL

This is an appeal1,2 under 35 U.S.C. § 134(a) involving claims to
formulations for use in an electron transport layer (“ETL”) in an organic
photovoltaic (“OPV”) device. The Examiner rejected the claims as obvious.
We have jurisdiction under 35 U.S.C. § 6(b). We AFFIRM.

1 Appellants identify the Real Party in Interest as Merck Patent GmbH (see
App. Br. 1).
2 We have considered and herein refer to the Specification of Nov. 5, 2014
(“Spec.”); Final Office Action of Mar. 13, 2018 (“Final Act.”); Appeal Brief
of Oct. 29, 2018 (“App. Br.”); Examiner’s Answer of Jan. 28, 2019
(“Ans.”); and Reply Brief of Mar. 20, 2019 (“Reply Br.”).
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Statement of the Case
Background
OPVs may include interfacial materials enclosed between the
photoactive film and one of the electrodes to improve the performance and
lifetime of the devices (Spec. 1:12–18). ETLs are an example of an
interfacial layer having electron transport properties (Spec. 1:30–32). ETLs
may be incorporated into the regular structure of an OPV device (Spec. 4:1–
8). The regular structure of an OPV device may include, in order of
deposition, a transparent electrode (anode), a hole transport layer, e.g.,
PEDOT:PSS, a photoactive layer, e.g., a bulk heterojunction (“BHJ”), an
ETL, and an electrode (cathode) (id.).
The prior art describes numerous materials used as ETLs in OPVs,
including alkaline earth metals, metal oxides, semiconductors, dipole
materials, polymer electrolytes, cationic or anionic polymers, and
zwitterionic compounds (see id. at 4:10–8:26). However, these materials
suffer from various drawbacks (id. 6:6–8). Therefore, the Specification
asserts a need for “ETL materials which enable efficient charge transport
from the photoactive layer to the cathode and lead to higher cell efficiencies,
compared to materials from the prior art” (id. 6:13–16).
The Claims
Claims 1–4, 6, 7, 10, 24–26, 28, and 32 are on appeal. Independent
claim 1 is representative and reads as follows:
1. An organic electronic device, which is or comprises an
organic photovoltaic device (OPV), which device comprises:
two electrodes, a photoactive layer and an electron transport
layer (ETL) between the photoactive layer and an electrode,
which organic photovoltaic device is a bulk heterojunction
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(BHJ) OPV device or inverted BHJ OPV device and comprises
a bulk heterojunction,
wherein the electron transport layer comprises or is made
from a formulation comprising an organic salt, wherein the
organic salt comp1ises a first ionic entity and a second
counterionic entity, wherein:
the first and second entities are small molecules,
the first entity is an organic entity, comprising
- a charged organic core comprising a single charged
moiety or a plurality of charged moieties wherein the charged
organic core comprises at least one moiety selected from the
group consisting of: dialkylpyrrolidinium, mono or
dialkylpyridinium, trialkylsulfonium, carbazolium, indolium,
piperidinium, morpholinium, pyrimidinium, pyridazinium,
pyrazinium, pyrazolium, pyrrolinium, oxazolium, triazolium,
triazinium, guanidinium, uranium, sulfonium, and
phosphonium, and
- optionally one or more substituents attached to the
charged organic core, at least one of said substituents
comprising a charged moiety having a charge that is opposite in
sign to, or of the same sign as, the charged moieties of the
charged organic core,
- the second entity is an organic, inorganic or
organometallic entity, and
- the net charge of the first entity is opposite in sign to the
net charge of the second entity;
and wherein the photoactive layer comprises a p-type
semiconductor and an n-type semiconductor where the p-type
semiconductor is a conjugated organic polymer or copolymer.

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The Rejections
A. The Examiner rejected claims 1–4, 6, 10, 24–26, 28, and 32 under 35
U.S.C. § 103(a) as unpatentable over Pho3 and Raffaelle4 (Final Act. 10–14).
B. The Examiner rejected claims 1–4, 7, 10, 24–26, 28, and 32 under 35
U.S.C. § 103(a) as being unpatentable over Pho and Jayaweera5 (Final Act.
14–17).
A and B. Obviousness
Because both of the obviousness rejections share similar issues as to
the teachings of Pho in combination with Raffaelle or Jayaweera, we
consider them together.
The Examiner finds Pho teaches solar cells including two electrodes
(Al/ITO), a photoactive layer (BHJ p-type/n-type semiconductor), an ETL
between the photoactive layer and an electrode (Al), and a PEDOT:PSS hole
transport layer (see Final Act. 10–11). The Examiner finds Pho teaches the
ETL layer includes a dye which is a small molecule organic salt, including
first and second ionic entities (see id.). The Examiner acknowledges that
Pho does not teach the claimed organic salt or small molecule dye (Final
Act. 11).
The Examiner finds Raffaelle teaches “dye sensitized organic bulk
heterojunction solar cells [] with two electrodes (Al/ ITO), a photoactive
layer (P3HT:PCBM ; p-type:n-type semiconductor), and a PEDOT:PSS hole

3 Pho, T. V. et al., Quinacridone-Based Electron Transport Layers for
Enhanced Performance in Bulk-Heterojunction Solar Cells, 21 ADV. FUNCT.
MATER. 4338–4341 (2011).
4 Raffaelle, R. P. et al., Dye-sensitized bulk heterojunction polymer solar
cells, 33RD IEEE PHOTOVOLTAIC SPECIALISTS CONFERENCE, 1–6 (2008).
5 Jayaweera, P. V. V. et al., Dye-sensitized near-infrared room-temperature
photovoltaic photon detectors, 85 APPL. PHYS. LETT. 5754–5756 (2004).
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transport layer” (Final Act. 11). The Examiner finds Raffaelle teaches the
photoactive layer includes dye 815 which “comprises a charged organic core
of indolium (first entity) and iodine (second entity)” (id.).
The Examiner finds that one of ordinary skill in the art would have
been motivated to improve Pho’s dye sensitized solar cell (“DSSC”),
“because Pho concludes that the process would be applicable generally: ‘the
simple application of a solution-deposited, small molecule ETL can improve
the [power conversion efficiency (‘PCE’)] of OPVs, obviating the need for
post-deposition treatments such as cross-linking’” (Final Act. 12). The
Examiner finds “[o]ne of ordinary skill in the art would have a reasonable
expectation of success in applying the teaching of the small molecule of
[Raffaelle] to Pho to because the devices share substantial structural
similarities . . . and because they both utilize small molecule absorbers to
enhance efficiency” (id.).
The Examiner finds “Jayaweera teaches the dye sensitization of
photovoltaics including solar cells using commercially available dyes such
as IR 820 (anionic) - IR 1040 (cationic) (Table I)” (Final Act. 15). The
Examiner finds “[o]ne of ordinary skill in the art would have a reasonable
expectation of success in applying the teaching of the small molecule of
Jayaweera to Pho to because the devices share substantial structural
similarities such as described in Jayaweera’s Fig. 1 and because they both
utilize small molecule absorbers to enhance efficiency” (Final Act. 16).
The issues with respect to these rejections are:
(i) Does a preponderance of evidence of record support the
Examiner’s conclusion that the prior art renders the claims obvious?
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(ii) If so, have Appellants presented evidence of secondary
considerations, that when weighed with the evidence of obviousness, is
sufficient to support a conclusion of non-obviousness?
Findings of Fact (“FF”)
1. Pho teaches the addition of an ETL between the active layer and the
cathode of an OPV can facilitate electron transport to the cathode (Pho
4338).
2. Pho teaches “the use of an ETL complicates the solution processing of
multilayered OPV devices, as solvents of orthogonal polarity for each
successive layer are needed to prevent removal of the underlying layers,
thereby necessitating the development of ETL materials that are
water/alcohol-soluble” (Pho 4338).
3. Pho teaches “water/alcohol-soluble small molecules for ETLs are a
simpler, more attractive alternative to their polymeric and inorganic
counterparts” (Pho 4338).
4. Pho teaches:
[W]ater-soluble small molecules based on the commercially
available pigment quinacridone has been shown to significantly
reduce the electron injection barrier in organic light emitting
diodes (“OLEDs”). Given the apparent advantages in OLEDs,
we evaluated the applicability of the easily accessible
quinacridone material . . . as an ETL in OPVs.

(Pho 4338).
5. Pho teaches a OPV structure as shown in Figure 1(c), reproduced
below:
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Figure 1(c) shows a device architecture including an electrode
(Al), a small molecule ETL between the electrode and a BHJ
photoactive layer, a PEDOT:PSS hole transport layer, and a
second electrode (ITO).

(Pho 4339).

6. Pho teaches “[t]o avoid perturbation of the active layer, the
quinacridone-based ETL (Na+QHSO3-) was deposited from methanol” (Pho
4339).
7. Pho teaches “[t]he addition of the ETL to the PCDTBT:PC71BM
devices resulted in a significant increase in the [fill factor (‘FF’)],
contributing to an overall improvement in the [power conversion efficiency
(‘PCE’)] from 4.3% to 5.2%” (Pho 4339).
8. Pho teaches “[t]he use of ETL enhanced the FF of the devices and had
a negligible impact on the Voc and Jsc.” (Pho 4339).
9. Pho teaches “[w]hile the use of conjugated polyelectrolyte-based
ETLs has been correlated primarily to an increase in Voc we observed little-
to-no change in the Voc with the addition of our small molecule Na+QHSO3−
-based ETL. . . . Nonetheless, the promising improvements with the FF and
PCE warrant further investigation” (Pho 4341).
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10. Pho teaches “the simple addition of a solution-deposited small
molecule ETL can improve the PCE of OPVs” (Pho 4341).
11. Raffaelle teaches “[e]mpirical simulations show that molecular dyes
absorbing between 800–900 nm in a properly structured device can
theoretically increase the device photocurrent sufficient to reach a power
conversion efficiency of 16% in a bulk heterojunction polymer solar cell”
(Raffaelle 1).
12. Raffaelle teaches “[t]he incorporation of these dyes into a PCBM-
P3HT device structure has shown an enhancement in the spectral response at
1.5 eV” (Raffaelle 1).
13. Raffaelle teaches “[t]he theoretical prospect of using [near-infrared
(‘NIR’)] dyes to enhance the photocurrent has been calculated using [a]
semi-empirical model . . . The limiting Jsc with a PCBM[70]-MEH-PPV
composite is calculated to be 28.5 mA/cm2 for a 775 nm indolylidene dye
and 26.8 mA/cm2 for a 815 nm indolylidene dye” (Raffaelle 3).
14. Raffaelle teaches indolium Dyes 775 and Dye 815 in Figure 8,
reproduced below:

Dye 775
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Dye 815
Figure 8 shows indolium-containing small molecule dyes.
(Raffaelle 4).
15. Raffaelle teaches:
Empirical modeling has been performed on PCBM-Polymer
bulk heterojunction using parameters from current-voltage and
spectral response measurements. The maximum efficiency for
these systems is calculated to be between 6 and 9%, under 1 sun
illumination. The prospect of enhancing the device spectral
response into the near-infrared (NIR) through the use of soluble
dyes has been calculated to equal 14–17% for an optimized
polymer device

(Raffaelle 6).
16. Jayaweera teaches “[i]n dye-sensitization (‘DSN’), dye molecules
anchored to a semiconductor surface inject carriers into a band leaving dye
ions of opposite charge on the semiconductor surface. . . . These attractive
features DSN have been exploited to construct solar cells using
nanocrystalline films of oxide semiconductors” (Jayaweera 5754).
17. Jayaweera teaches “[t]his investigation indicates that some of these
dyes sensitize the heterojunctions of the configuration, n-type
semiconductor/dye/p-type semiconductor” (Jayaweera 5754).
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18. Jayaweera teaches “[t]he observation of sensitized photocurrents with
IR 783, IR 820, IR 792, and IR 1040 shows that these dyes have ground and
excited level positions” that energetically permit charge transfers
(Jayaweera 5755).
19. The Examiner finds that IR 1040 is a cationic dye and IR 820 is an
anionic dye with the following structure:

IR 820 is a small molecule indolium compound forming Na+ organic salt
(Final Act. 15).
20. Jayaweera teaches “[t]he peak spectral response of these devices can
be readily adjusted by choice of the dye and tuning by structural
modifications to the dye molecule” (Jayaweera 5756).
21. Jayaweera teaches “[e]xtensive effort is under way for improvement
of the efficiencies of dye-sensitized solar cells . . . Combination of IR dyes
with visible sensitizers may also enhance the efficiencies of dye-sensitized
solar cells” (Jayaweera 5756).

Principles of Law
“The combination of familiar elements according to known methods
is likely to be obvious when it does no more than yield predictable results.”
KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398,416 (2007).
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Analysis
We adopt the Examiner’s findings of fact and conclusions of law (see
Final Act. 9–17, FFs 1–21) and agree that Pho and Raffaelle or Jayaweera
render the claims obvious. We address Appellants’ arguments below.
Appellants contend “Pho specifically requires the quinacridone dye-
based compound as the charged material for the ETL layer and contemplates
no other small molecule to replace the quinacridone dye part of the small
molecule” (App. Br. 4). Appellants contend “Pho specifically teaches that
the quinacridone dye is essential to its results and is the new aspect they had
discovered” (id.). Appellants argue “that there would be no motivation to
modify Pho to replace the quinacridone-based core material with some other
small molecule core material” and therefore, “[i]t would not have been
obvious to one of ordinary skill in the art to use one of the dyes in Raffaelle
in place of the quinacridone dye of Pho” (App. Br. 4, 5).
We find this argument unpersuasive. Pho teaches “water/alcohol-
soluble small molecules for ETLs are a simpler, more attractive alternative
to their polymeric and inorganic counterparts” (FF 3). Although Pho only
evaluates an “easily accessible quinacridone material,” Pho does not exclude
the use of other water/alcohol small molecules. Rather, Pho broadly teaches
“the simple addition of a solution-deposited small molecule ETL can
improve the PCE of OPVs” (FF 10). Because, “the question is whether there
is something in the prior art as a whole to suggest the desirability, and thus
the obviousness, of making the combination, not whether there is something
in the prior art as a whole to suggest that the combination is the most
desirable combination available,” we are not persuaded that the Examiner
erred in modifying Pho by using known materials that were used in similar
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devices in Raffaelle and Jayaweera. In re Fulton, 391 F.3d 1195, 1200 (Fed.
Cir. 2004) (citation omitted).
Appellants contend:
[T]he dyes taught in Raffaelle for a DSSC device are taught for
use in a different context and different type of device than the
quinacridone dye is used in Pho. There is no ETL layer in the
Raffaelle device and the dyes are used as a sensitizer in a
polymer layer, not an ETL layer and not an ETL layer based on
small molecule compounds. Pho makes clear that its intention
is to avoid an ETL which contains polymers . . . Thus, one of
ordinary skill in the art would not be directed to the teachings
of Raffaelle to modify Pho because Raffaelle is directed to a
device wherein the dye is used together with and sensitizes a
polymer-based layer, while Pho seeks to avoid such a polymer
ETL layer.

(App. Br. 5–6).
Appellants’ argument is unpersuasive. “[W]hen a patent claims a
structure already known in the prior art that is altered by the mere
substitution of one element for another known in the field, the combination
must do more than yield a predictable result.” KSR Int’l Co. v. Teleflex Inc.,
550 U.S. 398, 416 (2007). As shown by the Examiner, Pho discloses an
organic photovoltaic device with the structure recited by the claims and
suggests further investigation of small molecule organic compounds in ETLs
for OPVs (FF 9). Pho is altered by the mere substitution of one known small
molecule organic salt for another known in the field. Raffaelle teaches small
molecule indolium dyes may be used to optimize the efficiency of PCBM-
Polymer bulk heterojunction OPV devices. Although Pho and Raffaelle do
not teach identical devices, “the analysis need not seek out precise teachings
directed to the specific subject matter of the challenged claim, for a court
can take account of the inferences and creative steps that a person of
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ordinary skill in the art would employ.” KSR Int’l Co. v. Teleflex Inc., 550
U.S. 398, 418 (2007). Accordingly, we agree with the Examiner that “both
devices are solar cells and the success of Raffaelle in enhancing the spectral
response and PCE of the related device would reasonably suggest that the
dye could be used in other devices which could be improved with a
broadened spectral response such as Pho’s device” (Ans. 8).
Appellants contend “[s]imilar to Raffaelle, Jayaweera teaches the use
of a dye in a distinct context from how the dye in Jayaweera [Pho] is used.
Thus, there is no adequate reasoning on the record to support substituting a
dye taught in Jayaweera for the quinacridone dye used in Pho” (App. Br. 8).
Appellants argue “[t]here is nothing to suggest that the dyes used in
Jayaweera — which are used as sensitizers — would be successfully used in
a device such as Pho — which is not a DSSC device and does not use the
dye as a sensitizer in a polymer layer” (App. Br. 9).
Appellants’ argument is unpersuasive. Although the Pho and
Jayaweera devices are not identical, a person of ordinary skill in the art
would have inferred that the beneficial properties of the small molecule
organic salts of Jayaweera used to enhance charge transfer efficiency (FF
18) would provide similar benefits in Pho’s ETL that also requires charge
transfer (FF 1). Accordingly, we agree with the Examiner that “[o]ne of
ordinary skill in the art . . . would understand that sensitizing dyes
demonstrated as having useful absorption properties in a related device [of
Jayaweera] would likely be useful in an ETL such as taught by Pho where
the known electronic properties would be compatible to improve device
performance” (Ans. 14.)
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Appellants contend “the claimed devices provide significant
improvement in each of fill factor, short circuit current (Jsc), open circuit
voltage (Voc) and power conversion efficiency (PCE)” (App. Br. 6).
Appellants’ Specification compares the “claimed devices to devices without
an ETL (i.e., the same type of comparison Pho did)” (id.). Appellants
contend “Pho discloses that the use of its quinacridone-based ETL layer
provides a significant increase in the fill factor (FF). However, the Pho
device does not provide any improvement in short circuit current (Jsc) or
open circuit voltage (Voc)” (id.).
We are not persuaded by Appellants’ evidence. “To be particularly
probative, evidence of unexpected results must establish that there is a
difference between the results obtained and those of the closest prior art, and
that the difference would not have been expected by one of ordinary skill in
the art at the time of the invention.” Bristol-Myers Squibb Co. v. Teva
Pharms. USA, Inc., 752 F.3d 967, 977 (Fed. Cir. 2014). Appellants cite
Example 2 of the Specification, incorporating the elected indolium organic
salt (S1) into the ETL, as indicative of unexpected and superior results as
compared to Pho’s quinacridone containing ETL. However, the
combination of Pho and Raffaelle or Jayaweera teach an ETL containing an
indolium compound. Moreover, the references suggest that the optimization
of different organic salts will improve the performance of the OPV devices
(see FFs 9–11, 15, 20). Therefore, the results are not compared to those of
the closest prior art, nor would the differences have been unexpected to
those of ordinary skill in the art at the time of the invention.
Moreover, the results in the Specification are limited to a few
compounds in specific concentrations (see Spec. 39–43, 46, 47 (Tables 1–6,
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11, 12)). The results are not commensurate in scope with claim 1, which
recites numerous charged moieties without limitation to amount or
concentration (see Claim 1). Unexpected results must be “commensurate in
scope with the degree of protection sought by the claimed subject matter.”
In re Harris, 409 F.3d 1339, 1344 (Fed. Cir. 2005).
Conclusion of Law
A preponderance of the evidence of record supports the Examiner’s
conclusion that the prior art renders the claims obvious. Appellants have not
presented evidence of secondary considerations, that when weighed with the
evidence of obviousness, is sufficient to support a conclusion of non-
obviousness.

CONCLUSION
In summary:
Claim(s)
Rejected
Basis Affirmed Reversed
1–4, 6, 10, 24–26,
28, and 32
§ 103 Pho and
Raffaelle
1–4, 6, 10, 24–
26, 28, and 32

1–4, 7, 10, 24–26,
28, and 32
§ 103 Pho and
Jayaweera
1–4, 7, 10, 24–
26, 28, and 32

Overall Outcome 1–4, 6, 10, 24–
26, 28, and 32

No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a).

AFFIRMED