Ex Parte Oka et al

Patent Trial and Appeal Board

Nov 14, 2013

11919105 (P.T.A.B. Nov. 14, 2013)

UNITED STATES PATENT AND TRADEMARK OFFICE
________________

BEFORE
THE PATENT TRIAL AND APPEAL BOARD
________________

Ex parte HIDETAKA OKA,1
Ramachandra V. Joshi, Junichi Tanabe, Sanjoy Lahiri,
Dhaval Vashi, and Preetam Ghogale
________________

Appeal 2012-008627
Application 11/919,105
Technology Center 1700
________________

Before PETER F. KRATZ, MARK NAGUMO, and
KAREN M. HASTINGS, Administrative Patent Judges.

NAGUMO, Administrative Patent Judge.

DECISION ON APPEAL
Hidetaka Oka, Ramachandra V. Joshi, Junichi Tanabe, Sanjoy Lahiri,
Dhaval Vashi, and Preetam Ghogale (“Ciba”) timely appeal under 35 U.S.C.

1 The real party in interest is listed as Ciba Specialty Chemicals Corp.
(“Ciba”) (Appeal Brief, filed 19 January 2012 (“Br.”), 3.)
Appeal 2012-008627
Application 11/919,105

2

§ 134(a) from the Final Rejection2 of claims 5-10 and 12-17. We have
jurisdiction. 35 U.S.C. § 6. We affirm-in-part.
OPINION
A. Introduction3
The subject matter on appeal relates to 1,3,5-substituted 1,2,4-triazole
compounds said to be useful as luminescent compounds in
electroluminescent devices such as full-color display devices. (Spec. 1,
ll. 3-7.) According to the 105 Specification, devices using the claimed
compounds have surprisingly high durability, energy efficiency, and
luminance. (Id. at 3, ll. 1-3.) Examples of preferred compounds A, C, and B
are shown in the Specification at pages 18-23, 24-26, and 28, respectively.
The general structure of the claimed compounds is shown on the following
page.

2 Office action mailed 24 May 2011 (“Final Rejection”; cited as “FR”).
3 Application 11/919,105, Electroluminescent device, filed 23 October 2007
as the national stage of PCT/EP2006/061670, filed 19 April 2006, claiming
the benefit of EPO applications filed 28 April 2005 and 30 August 2005.
We refer to the “105 Specification,” which we cite as “Spec.”
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Application 11/919,105

3

Representative Claim 5 reads:
A compound of the formula:
(A1)
(Claims App., Br. 24-33; the 40 structural formulas A-2 through A-29
and C-1 through C-12 (all are 1,3,5-substituted 1,2,4-triazoles) have been
omitted.)
Representative Claim 6 reads, in parts most relevant to this Opinion:
A compound of the formula
(I),
wherein
X, Y and W are independently of each other
C1-C24alkyl; C1-C24alkyl, which is substituted by E and/or
interrupted by D;
C2-C18alkenyl, C2-Cl8alkenyl, which is substituted by E,
C3-C8cycloalkyl, C3-C8cycloalkyl, which is substituted
by G,
aryl, aryl, which is substituted by G,
heteroaryl, or heteroaryl, which is substituted by G,
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Application 11/919,105

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R201 is hydrogen, C1-C24alkyl,
* * * * *
D is
-CO-, -COO-, -OCOO-, -S-, -SO-, -SO2-, -O-, -NR5-, . . . ;
E is halogen,
C6-C14aryl, which may be substituted by -OR201, -SR202
and/or -NR203R204;
-OR5’, -SR5’, -NR5R6, . . . , or C1-C18alkyl,
G is E, or C1-C18alkyl,
wherein R5 and R6 are independently of each other
H, C6-C18aryl;
C6-C18aryl which is substituted by C1-C18alkyl, or
C1-C18alkoxy;
C1-C18alkyl or C1-C18alkyl which is interrupted by -O-;
or
R5 and R6 together form a five or six membered ring,
in particular ,
R5’ is R5, except hydrogen,
* * * * *
with the proviso that the following compounds are excluded:
* * * [twelve structures] * *
and wherein at least one of X, Y and W are independently of
each other a group of the formula -W1-(W2)b-W3, wherein
b is 0, or, 1,
App
App

(Cla
num

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lication 11
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08627
/919,105
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Br. 33-40;
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* * * * *

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d
Appeal 2012-008627
Application 11/919,105

6

occasional inconsistent use of commas and semicolons as separators in the
various definitions.
Second, claims 5 and 6, the only independent claims, have no
common members. For example, none of compounds A-1 through A-29 and
C-1 through C-12 contain X, Y, or W comprising the required
formula -W1-(W2)b-W3. In particular, none of these compounds contains an
amine, W3, linked to an aryl group, W1, through an amine nitrogen.
Third, claim 5 is a pure “Markush” claim, that is, it specifies 41
distinct, specific compounds. In contrast, claim 6 is generic to a very large
number of compounds.
Fourth, in the X, Y, and W substituents defined in claim 6, only the
alkyl groups may be “interrupted” by divalent moieties D. The alkenyl,
cycloalkyl, aryl, and heteroaryl groups may only be substituted by the
monovalent moieties E or G.
Fifth, the final definition of W3, in which -NR70R71 forms a five or six
membered heterocycle, brings certain “dimer” compounds containing two
1,2,4-triazole moieties (see, e.g., compound D-5 Spec. 12) within the scope
of claim 6.4, 5

4 Dimer compounds D-1 through D-4, and D-6 through D-8 (Spec. 11-13)
appear to be excluded by the definition of W1 and W2. These compounds
appear to be encompassed by the formula (II) (id. at 3, l. 6).
5 The substituents R18 and R19 of the C-9 carbon of the fluorenyl group
defining W1 and W2 (supra, second compound from the left) do not appear
to be defined. We trust that this irregularity will be addressed, due concern
being taken to ensure antecedent basis in the originally filed Specification, in
the event of further prosecution.
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The Examiner maintains the following grounds of rejection (the
independent claims are shown in bold font):6
A. Claim 5 stands rejected under 35 U.S.C. § 103(a) in view of
Takahashi.7
A1. Claims 6, 7, 16, and 17 stand rejected under
35 U.S.C. § 103(a) in view of Takahashi and Tang.8
B. Claims 5, 6, 7, 16, and 17 stand rejected under
35 U.S.C. § 103(a) in view of Kohama.9
B1. Claims 8-10, 14, and 15 stand rejected under
35 U.S.C. § 103(a) in view of the combined teachings of
Kohama and Adachi.10
B2. Claims 12 and 13 stand rejected under 35 U.S.C. § 103(a) in
view of the combined teachings of Kohama, Adachi,
and Ma.11

6 Examiner’s Answer mailed 17 February 2012 (“Ans.”).
7 Akira Takahashi et al., Negative type resist composition for electron beam
or x-ray, JP 2003-005356 (2003) (JPO machine translation).
8 Ching W. Tang et al., Electroluminescent device with modified thin film
luminescent zone, U.S. Patent 4,769,292 (1988).
9 Toru Kohama et al., Luminescent device, JP 2000-100570 (2000)
(JPO machine translation).
10 Chihaya Adachi et al., Double doped-layer, phosphorescent organic light
emitting devices, U.S. Patent Application Publication 2002/0180347 Al
(2002).
11 Bin Ma et al., Organic light emitting materials and devices, U.S.
Patent 6,916,554 B2 (2005).
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B. Discussion
Findings of fact throughout this Opinion are supported by a
preponderance of the evidence of record.
Initially, we find that Ciba argues for the separate patentability of
claims 5 and 6 only. (Br. 14, 1st full para.) The remaining claims therefore
stand or fall with claim 6, from which they depend. (Id.)
Claim 5
The difficulty with the appealed rejections of claim 5 is the absence of
a demonstration that any particular compound of the 41 compounds recited
in the claim would have been obvious in view of particular disclosures in
Takahashi or in Kohama.
As Ciba argues (Br. 19, last para.), the 1,2,4-triazole compounds
described by Kohama will form complexes with a metal atom. In Kohama’s
words, “at least one of the R1-the R3 of general formula (1) has
unsubstituted a hydroxyl group and a sulfhydryl group required to form a
metal complex, no substituting [or], 1 substituted amino group, or a carboxyl
group.” (Kohama 7 [0015], last sentence; see also the compounds of
formula (11) at page 10, and the compounds of formula (12) at page 11.)
In other words, Kohama requires an unsubstituted hydroxyl (OH), sulfhydryl
(-SH), amino (-NH2), or “1 substituted amino” (NHR) group at
the 2-position of the phenyl group attached to the 1,2,4-triazole ring to form
stable complexes with a metal. None of the compounds covered by claim 5
have such a group on the aryl groups bonded to the 1,2,4-triazole ring. The
Examiner has not explained how or why a person having ordinary skill in the
art would have removed a feature taught by Kohama to be critical to the
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Application 11/919,105

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success of the disclosed invention. We therefore reverse the rejection of
claim 5 in view of Kohama.
Although Ciba has not identified a similar disqualifying requirement
in Takahashi, as Ciba argues, the Examiner has not made the case that any
particular compound covered by claim 5 would have been obvious starting
from any particular compound taught by Takahashi. As our reviewing court
has explained, the Supreme Court’s analysis in KSR12 assumes a starting
reference point or points in the prior art, the existence of a reason to make
particular modifications to achieve the claimed compound, and a reason to
narrow the prior art universe to a finite number of identified, predictable
solutions. Eisai Co. Ltd. v. Dr. Reddy’s Labs, Ltd., 533 F.3d 1353, 1359
(Fed. Cir. 2008). The focus in § 103 on the differences between the claimed
invention and the prior art, and the insistence by the Court that factual
findings support the legal conclusion of obviousness, preclude the broad-
brush analysis applied by the Examiner to claim 5.
A Markush group of 41 members is not particularly large. The
Examiner has found that the class of 1,3,5-substituted 1,2,4-triazoles is
known to the chemical arts, and that various aryl and hetero aryl groups are
known as substituents. We do not understand Ciba to dispute these findings.
As the Federal Circuit has explained, however “[w]e decline to extract from
Merck the rule that the Solicitor appears to suggest — that regardless of how
broad, a disclosure of a chemical genus renders obvious any species that
happens to fall within it.”). In re Jones, 958 F.2d 347, 350 (Fed. Cir. 1992),
citing Merck & Co. v. Biocraft Labs., Inc., 874 F.2d 804, 806-09 (Fed.

12 KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398 (2007).
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Cir. 1989). We therefore reverse the rejection of claim 5 in view of
Takahashi.
Claim 6
Claim 6 stands differently from claim 5. First, claim 6 covers vastly
more compounds than the 41 specific compounds covered by claim 5. This
disparity is enhanced by the relatively few (five) compounds specifically
described that fall within the scope of claim 6 (Spec. 12, compound D-7, and
Spec. 28, compounds B-1 through B-4) compared to the 41 specifically
illustrated compounds A-1 through A-29 and C-1 through C-12 covered by
claim 5. Ciba has not, however, with one exception discussed infra, argued
that any particular structures would not have been obvious. Rather, Ciba has
argued, for very broad reasons, that the Examiner failed to establish a prima
facie case of obviousness.
Ciba argues that the Examiner failed to consider the size of the genus,
the alleged failure of Takahashi to expressly teach or suggest the claimed
compounds, Takahashi’s teachings of structural similarity, similar properties
or uses, or teachings to support the selection of the species or the subgenus.
(Br. 16, 1st full para.)
These arguments are not persuasive on the present facts of harmful
error as to claim 6. First, claim 6 is very, very broad. It is not unreasonable
to conclude, as did the Examiner, that an extremely broad genus (particularly
one supported by only five specific examples) may be suggested fairly by a
rather broad disclosure of similar compounds. Moreover, the Examiner
made specific findings as to structures taught by a second prior art reference,
Tang. The Examiner found that Tang teaches the equivalence of
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N-substituted carbazol groups to diaryl- and triaryl-amines corresponding to
aromatic amines taught by Takahashi (FR 3, citing Takahashi [0115]-[0123]
for substituents R11 and R12 of the 1,3,5-substituted 1,2,4-triazole of
formula (3); Takahashi paragraphs [0115]-[0117] describe various amines).
On this basis, the Examiner concluded that triazoles substituted by the
amines W3 in the manner required by claim 6 would have been obvious.
(FR 5, ll. 5-8, citing Tang, col. 37, ll. 62-68.)
Ciba’s only response to these findings is the assertion, unsupported by
citation or analysis, that all combinations of the primary and the secondary
references “fail to disclose or suggest the presently recited compounds,” and
that the secondary references “fail to cure at least the above-noted
deficiencies of Takahashi and Kohama.” (Br. 20, 2d para.) Such
unsupported arguments amount to nothing more than an invitation to the
Board to reconsider the references, de novo and without the guidance of
Ciba’s well-informed views, and arrive at a conclusion favoring Ciba.
Because our primary role is review, not de novo fact-finding and analysis,
we decline the invitation.
As for the teachings of Takahashi regarding structural similarities,
properties, and uses, the Examiner relied on such teachings relating to
Takahashi formula (3), the triazole, not on properties based on other
heterocycles such as Takahashi formulas (52) and (53), cited by Ciba.
Ciba’s arguments based on the supposed breadth of Takahashi’s teachings
do not prove harmful error in the Examiner’s rejection.
We conclude that Ciba has not proven harmful error in the prima facie
case of obviousness of claim 6 in view of Takahashi and Tang.
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As noted supra, Ciba does advance the specific argument that
Kohama requires 1,2,4-triazoles that are “characterized by having a
2-hydroxyphenyl group on the 1-site.” (Br. 19, 2d full paragraph.) Ciba
argues that “[t]he presently recited triazoles, in contrast to Kohama, do not
contain such a group.” (Id.)
This argument is persuasive as to the hydroxyphenyl group (and also
as to the sulfhydryl group) disclosed by Kohama at [0015]. Regarding
compounds covered by claim 6, the group of moieties G, which are
substituents of the cyclic (cycloalkyl, aryl, or heteroaryl) groups that can be
X, Y, and W, include all the moieties E. Moieties E include C6-C14 aryl,
which may be substituted by -OR201, where R201 can be hydrogen. Thus, for
example, a phenyl group attached to the 1,2,4-triazole ring can be substituted
by a phenol group, -C6H4(OH). However, groups X, Y, or W can be
substituted directly by an oxygen-linked group only when G is -OR5’
or -SR5’; and R5’ specifically excludes hydrogen. Thus, phenol (and the
corresponding thiol) are excluded by definition.
However, as the Examiner points out (FR 5, ll. 3-5; Ans. 7, ll. 10-12
and 14, ll. 1-3), Kohama’s list of substituents includes amines (unsubstituted
and singly-substituted). It has not escaped our notice that substituting
group E includes the moiety -NR5R6, where R5 and R6 can be, e.g., H, aryl,
or alkyl, variously substituted or interrupted. Thus, claim 6 includes
compounds having phenyl groups substituted at the 2-position by primary
(-NH2) and secondary (-NHR) amines that would also be suitable for making
Kohama’s metal complexes. Thus, although the Examiner erred harmfully
in interpreting claim 6 as including phenylhydroxyl groups, that error does
not extend to the corresponding phenyl-amine groups.
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We conclude that Ciba has not proven harmful error in the prima facie
case of obviousness of claim 6 in view of Kohama.
Ciba argues that the 105 Specification provides evidence of
unexpected results that rebut any prima facie case of obviousness.
(Br. 21-23.) These arguments are not persuasive for at least two reasons.
First, the Specification provides 12 synthetic examples
and 16 “Application Examples.” (Spec. 46-56.) All of the examples are
reported in the present tense, which, by standard practice dating back to at
least January 1981,13 indicates a “paper,” or “prophetic” example, i.e., an
example that was not actually carried out, but that is provided in the spirit of
guidance or instruction. Ten of the synthetic examples and 15 of
the 16 Application Examples relate to compounds A within the scope of
independent claim 5, and therefore are irrelevant as evidence regarding the
obviousness of compounds of claim 6. Ciba has not come forward with any
credible evidence or argument that a single example of a single bright blue
EL emission is fairly representative of the scope of compounds covered by
claim 6. Thus, even if the presumption that the use of the present tense
indicates a prophetic, rather than a real example, were rebutted by credible
testimony, the evidence of record is not commensurate with the scope of the
subject matter Ciba seeks to exclude from the American public.
Second, Ciba has not provided any data relating to the performance of
the prior art compounds. Nor has Ciba come forward with any argument,
supported by relevant evidence, regarding what a person having ordinary

13 See Manual of Patent Examining Procedure (“MPEP”) 608.01(p), 4th Ed.,
5th revision (January 1981), and all more recent editions and versions.
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skill in the art would have expected as a result of the novel features of the
invention.
In this regard, we find that the 105 Specification teaches that the
twelve compounds expressly excluded from claim 6 are known to the prior
art, specifically, in Swiss patent CH 542 212, JP 2003-005356,
JP2000-100570, and JP 2004-146368 (Spec. 1-2).14 Interestingly, of the
twelve expressly excluded compounds shown, only the third through the
sixth, and the ninth, are within the scope of claim 6.15 The 105 Specification
does not appear to report measurements of any properties, including
fluorescent properties, of the excluded compounds.
Claim 6 includes compounds having relatively minor substitutions, for
example, on the distal rings of the excluded compounds. Thus, Ciba has not
compared to the closest prior art, as is generally required for a convincing
showing of unexpected results.
We conclude Ciba has not proven harmful error in the rejections of
claim 6. The claims dependent on claim 6 thus fall with claim 6.
C. Order
We reverse the rejection of claim 5 under 35 U.S.C. § 103(a) in view
of Takahashi.

14 Copies of the original documents, as well as abstracts in English, were
provided in the Information Disclosure Statement filed 25 January 2008,
prior to the first Office Action.
15 The first two and the last three compounds lack a group within the scope
of W3; while the seventh and eighth compounds lack a group within the
scope of W1.
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We affirm the rejection of claims 6, 7, 16, and 17 under
35 U.S.C. § 103(a) in view of Takahashi and Tang.
We reverse the rejection of claim 5 under 35 U.S.C. § 103(a) in view
of Kohama.
We affirm the rejection of claims 6, 7, 16, and 17 under
35 U.S.C. § 103(a) in view of Kohama.
We affirm the rejection of claims 8-10, 14, and 15 under
35 U.S.C. § 103(a) in view of the combined teachings of Kohama and
Adachi
We affirm the rejection of claims 12 and 13 stand rejected under
35 U.S.C. § 103(a) in view of the combined teachings of Kohama, Adachi,
and Ma.
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-IN-PART

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