Ex Parte Park et al

Patent Trial and Appeal Board

Mar 31, 2017

13349141 (P.T.A.B. Mar. 31, 2017)

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.
13/349,141 01/12/2012 Jeong-il Park 15639-000019/US/CPA 3578
30593 7590 04/04/2017
HARNESS, DICKEY & PIERCE, P.L.C.
P.O. BOX 8910
RESTON, VA 20195
EXAMINER
SOLOLA, TAOFIQ A
ART UNIT PAPER NUMBER
1625
NOTIFICATION DATE DELIVERY MODE
04/04/2017 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):
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PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte JEONG-IL PARK, BANG LIN LEE, and
JONG WON CHUNG1
Appeal 2015-002393
Application 13/349,141
Technology Center 1600
Before JOHN G. NEW, RICHARD J. SMITH, and TAWEN CHANG,
Administrative Patent Judges.
NEW, Administrative Patent Judge.
DECISION ON APPEAL
appellants state the real party-in-interest is Samsung Electronics Co., Ltd.
App. Br. 2.
Appeal 2015-002393
Application 13/349,141
SUMMARY
Appellants file this appeal under 35 U.S.C. § 134(a) from the
Examiner’s Final Rejection of claims 1, 6—10, and 12—19 as unpatentable
under U.S.C. § 103(a) as being obvious over the combination of Masakatsu
(JP 2009-027117, February 5, 2009) (“Masakatsu”), G. Wehr, Polymere
Bis(oxazolo )pyrene: Synthesen und Charakterisierung von Poly (2,8-
oxazolo[2’,3': 7,8]pyreno[4,5-d]oxazoldiyl-l,4-phenylen)en und einigen
dazugehorigen Modellverbindungen, 177 Die Makromolekulare Chemie,
351—57 (1976) (“Wehr”), and F.D. King, Bioisosteres; Conformational
Restriction, and Prodrugs — Case History: An Example of a Conformational
Restriction Approach, in Medicinal Chemistry: Principle and Practice,
206-09 (Frank D. King (ed.), 1996) (“King”).2’3
We have jurisdiction under 35 U.S.C. § 6(b).
We AFFIRM.
NATURE OF THE CFAIMED INVENTION
Appellants’ invention is directed to an organic semiconductor
compound which may be polymerized and used in transistors and electronic
devices. The organic semiconductor compound includes a base structure of
four fused benzene rings with functional groups R1 to R3 connected to a first
2 Claims 2—5, 11, and 20 are canceled. App. Br. 26, 30, 34.
3 The Examiner also rejected claims 1, 3—10, and 12—20 as unpatentable
under 35 U.S.C. § 112, first paragraph, as lacking adequate written
descriptive support. See Final Act. 2. The Examiner further rejected claim
20 (later canceled) as unpatentable under 35 U.S.C. § 102(b) as being
anticipated by Masakatsu. See Final Act. 6. These rejections have been
withdrawn by the Examiner and we do not reach them. See Ans. 5.
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Appeal 2015-002393
Application 13/349,141
benzene ring and with functional groups R4 to R6 connected to a second
benzene ring. Abstract.
Claim 1 is representative of the claims on appeal and recites:
1. An organic semiconductor compound having a
structure represented by the following Chemical Formula 2:
[Chemical Formula 2]
wherein, in the above Chemical Formula 2,
R1 to R6 are each independently one of (i) hydrogen, a
halogen, a substituted Cl to C20 linear alkyl group, a substituted
Cl to C20 branched alkyl group, an unsubstituted Cl to C20
linear alkyl group, an unsubstituted Cl to C20 branched alkyl
group, a substituted or unsubstituted C3 to C20 cycloalkyl group,
a substituted or unsubstituted Cl to C20 alkoxy group, a
substituted or unsubstituted C3 to C20 cycloalkyloxy group, a
substituted or unsubstituted C6 to C30 aryl group, a substituted
or unsubstituted C6 to C30 aryloxy group, a substituted or
unsubstituted heteroaryl group, a heteroaromatic ring wherein
the heteroatom is at least one electron withdrawing imine
nitrogen atom, a heteroaromatic ring wherein the heteroatom is
at least one sulfur atom, NR51R52, C(0)0R53, C(0)NR54R55, and
(ii) structured so two adjacent substituents of R1 to R6 are linked
to each other to provide one of a thiophenyl ring group fused with
REPRESENTATIVE CLAIM
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Application 13/349,141
a pyrene moiety and a thiazolyl ring group fused with a pyrene
moiety,
wherein R51 to R55 are each independently one of
hydrogen, a substituted Cl to C20 linear alkyl group, a
substituted Cl to C20 branched alkyl group, an unsubstituted Cl
to C20 linear alkyl group, an unsubstituted Cl to C20 branched
alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl
group, a substituted or unsubstituted C6 to C30 aryl group, and a
substituted or unsubstituted heteroaryl group,
R7 and R8 are each independently one of hydrogen, a
halogen, a substituted Cl to C20 linear alkyl group, a substituted
Cl to C20 branched alkyl group, an unsubstituted Cl to C20
linear alkyl group, an unsubstituted Cl to C20 branched alkyl
group, a substituted or unsubstituted C3 to C20 cycloalkyl group,
a substituted or unsubstituted Cl to C20 alkoxy group, a
substituted or unsubstituted C3 to C20 cycloalkyloxy group, a
substituted or unsubstituted C6 to C30 aryl group, a substituted
or unsubstituted C6 to C30 aryloxy group, a substituted or
unsubstituted heteroaryl group, a heteroaromatic ring wherein
the heteroatom is at least one electron withdrawing imine
nitrogen atom, a heteroaromatic ring wherein the heteroatom is
at least one sulfur atom, NR51R52, C(0)0R53, and C(0)NR54R55,
wherein the heteroaromatic ring wherein the heteroatom is
at least one electron withdrawing imine nitrogen atom bonded to
a functional group is one of the groups represented by the
following Chemical Formula 3:
[Chemical Formula 3]
4
Appeal 2015-002393
Application 13/349,141
€ ,stO C 2 i?S' 0 0 0 H'
V
;3-»} (3-43
/T\
N==\
% 1
<. N
M
c ^
H »
v y
(W) (3-43 CM®
N N
Ss
r ^ A*ff
4.
N N$ tj
/ \ M
\J
M
\J v/
(J-U) ts~w (HS 5: A US (3-453
"J
n fa
/ \
% f
V. /)-'
N
7
&%n C3“1£
wherein, in the above Chemical Formula 3,
Y is one of hydrogen, a Cl to C20 linear or branched alkyl
group, a C3 to C20 cycloalkyl group, a C6 to C30 aryl group, a
Cl to Cl6 linear or branched alkoxy group, and a C3 to Cl6
cycloalkoxyalkyl group,
wherein the heteroaromatic ring wherein the heteroatom is
at least one sulfur atom is one of the groups represented by the
following Chemical Formula 4:
[Chemical Formula 3]
f\
V
*4-1 >
S
f\_J l.x A- \V V
<4-43
ICJ
S'
(4-K)
03
S- '-S
V Y
*4-5>
wherein, in the above Chemical Formula 4,
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Appeal 2015-002393
Application 13/349,141
Y is one of hydrogen, a Cl to C20 linear or branched alkyl
group, a C3 to C20 cycloalkyl group, a C6 to C30 aryl group, a
Cl to Cl6 linear or branched alkoxy group, and a C3 to Cl6
cycloalkoxyalkyl group.
App. Br. 23—26.
ISSUES AND ANALYSES
We agree with, and adopt, the Examiner’s findings of fact and
conclusion that the claims are obvious over the combined cited prior art and
adopt the Examiner’s rationale. We address the arguments raised on appeal
by Appellants below.
Issue 1
Appellants argue the Examiner erred by failing to provide sufficient
reasoning as to why a person of ordinary skill in the art would have selected
one of Masakatsu’s and/or Wehr’s compounds as a lead compound. App.
Br. 16.
Analysis
Appellants argue that Masakatsu discloses 80 compounds, from which
the Examiner has selected but two. App. Br. 16. According to Appellants,
compounds 1—20 of Masakatsu do not have two sulfur atoms in the same
positions as compounds 21 and 22 of Masakatsu, and Appellants contend the
Examiner focuses only on these two compounds of Masakatsu without
providing an explanation why. Id. Appellants also argue the Examiner fails
to provide sufficient reasoning to explain why either of compounds 2 or 3 of
Wehr would have been chosen as a lead compound, but rather focuses on a
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Application 13/349,141
perceived structural similarity between the compounds in Masakatsu, Wehr,
the organic semiconductor compound of claim 1, and the organic
semiconductor polymer of claim 10. Id.
Appellants argue further that King is related to medicinal chemistry,
specifically the use of bioisosteric replacement to modify “a target lead
compound and then convert that compound into a potential development
candidate for eventual marketing as a drug.” App. Br. 16. Appellants assert
that the Examiner does not show why a person of ordinary skill in the art of
medicinal chemistry (i.e., the field of King’s teachings) would have selected
one of the organic semiconductor compounds in Masakatsu and/or the
compounds in Wehr as a lead compound in drug development. Id.
The Examiner responds that Masakatsu teaches compounds which are
useful as semiconductors in transistors, and in electronic devices. Final Act.
7 (citing Masakatsu 8—26). The Examiner finds Wehr teaches compounds
1—3, and polymers thereof, that are also useful as semiconductors in
transistors. Id. (citing Wehr 352—53). The Examiner finds the difference
between the instant invention and those taught by Masakatsu and Wehr is
that Appellants’ claimed compounds replace a hydrogen with an alkyl as
substituents on the rings and replace a carbon atom with a nitrogen atom
(Masakatsu compounds) or substitute a sulfur atom (Wehr compounds) for
the oxygen in the pentene rings. Id.
The Examiner finds that it was well-known in the contemporary art
that nitrogen, oxygen, and sulfur are isosteric equivalents, and replacing the
isostere with another is well-known in semiconductor chemistry. Ans. 7.
The Examiner therefore concludes it would have been obvious for a person
of ordinary skill in the art to substitute one for another at the time the
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Appeal 2015-002393
Application 13/349,141
invention was made, and with a reasonable expectation of success. Id. The
Examiner finds Appellants performed the modification taught by King to
obtain compounds with the same expected chemical properties as those
taught by Masakatsu and Wehr. Id.
Appellants reply that the Federal Circuit has held that, when deciding
whether “a new chemical compound would have been prima facie obvious
over particular prior art compounds,” courts have considered (1) “whether a
chemist of ordinary skill would have selected the asserted prior art
compounds as lead compounds, or starting points, for further development
efforts”; and (2) “whether the prior art would have supplied one of ordinary
skill in the art with a reason or motivation to modify a lead compound to
make the claimed compound with a reasonable expectation of success.”
Reply Br. 3 (quoting Otsuka Pharm. Co., Ltd. v. Sandoz, Inc., 678 F.3d
1280, 1291-92 (Fed. Cir. 2012), cert, den’d, 133 S. Ct. 940 (2013).
Appellants contend the Examiner has failed to articulate sufficient reasoning
as to why a person of ordinary skill would select the compounds cited by the
Examiner as lead compounds. See App. Br. 16.
We are not persuaded by Appellants’ arguments, which begin from a
false premise. The Examiner did not merely, as Appellants suggest, pluck
one compound out of the 80 taught by Masakatsu and arbitrarily designate it
as a lead compound. Rather it is the central core structure of compounds
21—52 taught by Masakatsu, as exemplified by compound 21, upon which
the Examiner relies. Compound 21 of Masakatsu is reproduced below:
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Appeal 2015-002393
Application 13/349,141
Compound 21 of Masakatsu
This basic core structure is shared by almost half of the compounds taught
by Masakatsu, with the various additional groups added at points around the
core, which remains, however, unmodified in all of these embodiments.
This core is identical to that of Chemical Formula 2 in claim 1, as
reproduced supra, and Chemical Formula 6 in claim 10, with the exception
of the nitrogen substitution on the pentene rings in the latter. Similarly,
Wehr teaches, in two of three embodiments, a similar core structure. Figure
2 of Wehr is reproduced below:
Figure 2 of Wehr
In this instance, the sole difference between the core structure of Wehr
and that of the claims is the substitution of sulfur atoms (at the locations
taught by Masakatsu) for the oxygen atoms taught by examples 2 and 3 of
Wehr. Furthermore, the Examiner finds, and Appellants do not contest, that
both references teach these core structures are useful as semiconductor
elements in electronic circuits.
King teaches, as a matter of general principle, that: “[ijsosteres are
substituents or groups which have the same size or volume.” King 207.
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Application 13/349,141
King also teaches that: “[b]ioisosteres ... are substituents or groups that do
not necessarily have the same size or volume, but have a similarity in
chemical or physical properties which produce broadly similar biological
properties.” Id. King further teaches oxygen, sulfur, and methyl and amino
groups are “ [cjlassical isosteres which may function as bioisosteres’ '' when
acting as ring equivalents. King 208, Table 1.
Although we acknowledge Appellants’ contention that King is
primarily directed to medicinal chemistry, we agree with the Examiner that
King teaches that isosteric substitution was broadly known in the organic
chemistry arts. Moreover, King teaches not only that oxygen and sulfur are
ring equivalents known to be “classical isosteres,” which we interpret to
mean that they are broadly well-known in the art of organic chemical
substitution as having “the same size or volume,” but also that these classical
isosteres “have a similarity in chemical or physical properties,” because they
may function as bioisosteres. Id. at 207. We agree with the Examiner that a
person of ordinary skill would find it obvious to substitute sulfur atoms for
oxygen atoms, as taught by the core structures of Wehr, positioned in the
same location as taught by Masakatsu, and have a reasonable expectation
that such a substitution would also successfully function as a semiconductor.
Moreover, in In re Dillon, 919 F.2d 688 (Fed. Cir. 1990), the Federal
Circuit noted:
In brief, the cases establish that if an examiner considers that he
has found prior art close enough to the claimed invention to give
one skilled in the relevant chemical art the motivation to make
close relatives (homologs, analogs, isomers, etc.) of the prior art
compound(s), then there arises what has been called a
presumption of obviousness or aprima facie case of obviousness.
In re Henze, 181 F.2d 196, 37 C.C.P.A. 1009, 85 USPQ 261,
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Application 13/349,141
(C.C.P.A. 1950); In re Hass, 141 F.2d 122, 127, 130,31 C.C.P.A.
895, 60 USPQ 544, 548, 552 (C.C.P.A. 1944). The burden then
shifts to the applicant, who then can present arguments and/or
data to show that what appears to be obvious, is not in fact that,
when the invention is looked at as a whole. In re Papesch, 315
F.2d 381, 50 C.C.P.A. 1084137 USPQ 43 (C.C.P.A. 1963). The
cases of Hass and Henze established the rule that, unless an
applicant showed that the prior art compound lacked the property
or advantage asserted for the claimed compound, the
presumption of unpatentability was not overcome.
919 F.2d at 696; see also In re Shetty, 566 F.2d 81, 85-86 (C.C.P.A. 1977)
(concluding that “the difference of a mere methylene group between the
compound of the claim and the prior art compounds” is clearly obvious); In
re Bowers, 359 F.2d 886, 887 (C.C.P.A. 1966) (Bowers’ claimed steroid
compounds differed from the claimed compounds in commonly assigned
“patents by the presence in the steroid structure of a 2-methyl group instead
of a hydrogen atom”).
The Examiner has found that the compounds of Wehr teach a core
structure identical to that of Appellants’ claims, with the exception of the
substitution of sulfur atoms for Wehr’s oxygen atoms, at the locations taught
by Masakatsu, and that King teaches that such a substitution is a “classical
isoster[ic]” substitution. Appellants make no argument that their claimed
compounds are fundamentally different in properties or advantages than the
organic semiconductors taught by Masakatsu and Wehr. Having thus failed
to meet their burden under the Dillon analysis, we affirm the Examiner’s
findings and conclusion.
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Issue 2
Appellants argue the Examiner erred by failing to demonstrate that
Appellants’ claimed modification of the teachings of the combined cited
prior art would have provided a person of skill in the art with a reasonable
expectation of success. App. Br. 17.
Analysis
Appellants argue that the modification of Masakatsu and/or Wehr
does not have a rationale underpinning to support a prima facie case of
obviousness because King does not teach thiophene, oxazole, and thiazole
are bioisosteric equivalents, let alone equivalents. App. Br. 17. Appellants’
illustrations of thiophene, oxazole, and thiazole, as taught, respectively, by
Masakatsu, Wehr and Appellants’ claimed compounds, are provided below:
Thiophene
Masakatsu.
Omaote “Wehr Thiassote - see claims 1 and
10 of present application.
0 Q
Appellants’ illustrations of thiophene, oxazole. and thiazole compounds
Appellants contend Table 1 of King does not teach that thiophene,
oxazole, and thiazole are ring equivalents. App. Br. 17. Furthermore, argue
Appellants, unlike the thiazole structure shown above, none of the examples
of ring equivalents in Table 1 of King include more than 1 heteroatom
(i.e., any atom that is not carbon or hydrogen). Id.
Appellants argue further that King does not teach bioisosteres are
necessarily equivalent, and that one must consider the predictability of the
technology.
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Application 13/349,141
We are not persuaded. We acknowledge Appellants’ argument that
King does not teach that thiophene, oxazole, and thiazole rings are
bioisosteric equivalents. However, as we have related supra, King does
teach that oxygen and sulfur are classic isosteric ring equivalent
substitutions and that a person of ordinary skill in the prior art would find it
obvious to substitute the sulfur of the thiophene taught by Masakatsu for the
oxygen in the oxazole taught by Wehr to arrive at Appellants’ claimed
thiazole.
Furthermore, the Examiner need not demonstrate that a person of
ordinary skill would have more than a reasonable expectation of success in
combining the teachings of Masakatsu and Wehr, in view of the teachings of
King. See In reLongi, 759 F.2d 887, 897 (Fed. Cir. 1985) (“Only a
reasonable expectation of success, not absolute predictability, is necessary
for a conclusion of obviousness”). We agree with the Examiner that,
because Masakatsu and Wehr teach that their compounds act as organic
semiconductors, and given their structural similarity, a person of ordinary
skill in the art would find it reasonable to expect Appellants’ claimed
compounds to have similar properties. Appellants adduce no evidence to the
contrary, nor do they adduce any evidence with respect to the alleged
unpredictability of the art. We consequently agree again with the
Examiner’s findings and conclusions.
Issue 3
Appellants next argue that the Examiner erred because King provides
no pertinent reason to a person of ordinary skill in the art in the field of
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Application 13/349,141
organic semiconductor compounds to modify the compounds in Masakatsu
orWehr. App. Br. 19.
Analysis
Appellants contend that, because King does not suggest bioisosteric
replacement could improve characteristics such as mobility (“p”), Ln/Ioff, and
the threshold Vth of an organic field effect transistor (“OFET”) — the
parameters Appellants allege would have been of interest to persons of
ordinary skill in the art of organic semiconductor compounds — a person of
ordinary skill in the art would not be guided by King to make the
substitutions necessary to arrive at Appellants’ claimed compounds. App.
Br. 19—20 (citing the Declaration of co-inventor Dr. Jeong-il Park 18—19).
We are not persuaded for the reasons we have explained supra. King
teaches that sulfur and oxygen are classical isosteric ring substituents, and
likely to have similar functional properties. Both Masakatsu and Wehr teach
their components act as organic semiconductors. We find, for the reasons
we have explained, that a person of ordinary skill in the art of organic
semiconductor synthesis, would find it obvious to make the substitutions in
the teachings of the prior art to arrive at Appellants’ claimed compounds.
Issue 4
Appellants argue that the Examiner erred because King is not
analogous art that can be properly used in an obviousness rejection with
Masakatsu and Wehr. App. Br. 20.
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Analysis
Appellants advance another variation on their arguments supra, viz.,
that King relates to a different field (i.e., medicinal chemistry) than the
organic semiconductor compound field of Masakatsu, Wehr, or Appellants’
claimed compounds. App. Br. 21.
Appellants also argue that, because King does not mention how
replacing carbon with nitrogen or oxygen with sulfur in a ring of an organic
compound affects p, Ion/Ioff, and Vth of an OFET, King is not reasonably
pertinent to the issues that would concern one of ordinary skill in the art of
organic semiconductor compounds and organic semiconductor polymers.
App. Br. 21.
We find Appellants’ argument no more persuasive than its
predecessors. We acknowledge Appellants’ point that King is related to the
field of medicinal chemistry and not to that of organic semiconductor
chemistry. However, as we have discussed supra, King teaches generally
that sulfur and oxygen are classical ring substituent isosteres, likely to have
similar physical characteristics, and that Wehr and Masakatsu together teach
that compounds with nitrogen and sulfur substitutions at the locations
claimed in Appellants’ compounds have organic semiconductor qualities.
We therefore conclude that the teachings of King are reasonably pertinent to
the issues that would concern one of ordinary skill in the art of organic
semiconductor compounds and organic semiconductor polymers, viz., the
substitution of isomeric sulfur atoms for oxygen atoms at locations known in
the prior art to exist in essentially the same core structure claimed by
Appellants and having organic semiconductor properties. See In re Bigio,
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Application 13/349,141
381 F.3d 1320, 1325 (Fed. Cir. 2004). We consequently affirm the
Examiner’s rejection of the claims.
DECISION
The Examiner’s rejection of claims 1, 6—10, and 12—19 as
unpatentable under 35 U.S.C. § 103(a) is affirmed.
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a)(1). See 37 C.F.R.
§ 1.136(a)(l)(iv).
AFFIRMED
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