Ex Parte BEERS et al

Patent Trials and Appeals Board

Mar 13, 2019

13762612 - (D) (P.T.A.B. Mar. 13, 2019)

UNITED STA TES p A TENT AND TRADEMARK OFFICE
APPLICATION NO. FILING DATE
13/762,612 02/08/2013
111687 7590
Duane Morris LLP (UDC)
30 South 17th Street
Philadelphia, PA 19103
03/14/2019
FIRST NAMED INVENTOR
Scott BEERS
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
ATTORNEY DOCKET NO. CONFIRMATION NO.
F7059-00501 4639
EXAMINER
Y AMNITZKY, MARIE ROSE
ART UNIT PAPER NUMBER
1786
MAIL DATE DELIVERY MODE
03/14/2019 PAPER
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.
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte SCOTT BEERS, CHUANJUN (SEAN) XIA,
SUMAN LA YEK, and HARVEY WENDT
Appeal2018-005417
Application 13/762,612
Technology Center 1700
Before LINDA M. GAUDETTE, JAMES C. HOUSEL, and
JANEE. INGLESE, Administrative Patent Judges.
INGLESE, Administrative Patent Judge.
DECISION ON APPEAL
Appellant1 requests our review under 35 U.S.C. § 134(a) of the
Examiner's decision to finally reject claims 1, 2, 4, 6-15, 18-20, and 23-34.
We have jurisdiction over this appeal under 35 U.S.C. § 6(b).
We AFFIRM.
STATEMENT OF THE CASE
Appellant's invention is generally directed to compounds used as
yellow/green emitters in an organic layer of organic light emitting diodes.
1 Appellant is the applicant, Universal Display Corporation, which,
according to the Appeal Brief, is the real party in interest. Appeal Brief filed
October 19, 2017 ("App. Br."), 2.
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Application 13/762,612
Spec. ,r 2. Independent claims 1 and 19 illustrate the subject matter on
appeal and are reproduced below:
1. A compound having a structure selected from the group
consisting of:
L.
wherein R3, R 4 and R5 each represent mono, di, tri, tetra
substitutions or no substitution;
wherein R 8 represents mono, di, tri substitutions or no
substitution;
3-n,
wherein R 1 is selected from the group consisting of alkyl,
cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, alkenyl,
cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl,
carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl,
sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein R21 R22 R23 R3 R4 R6 R7 and R8 are each
' ' ' ' ' ' independently selected from the group consisting of hydrogen,
deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl,
alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl,
heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl,
carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl,
sulfonyl, phosphino, and combinations thereof;
wherein each R5 is independently selected from the group
consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl,
heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl,
cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic
acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl,
phosphino, and combinations thereof; and
wherein n is 1 or 2.
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Application 13/762,612
19. A first device comprising a first organic light emitting
device, said first organic light emitting device comprising:
an anode;
a cathode; and
an organic layer, disposed between the anode and the
cathode, comprising a compound having a structure selected
from the group consisting of:
wherein R3, R 4 and R5 each represent mono, di, tri, tetra
substitutions or no substitution;
wherein R 8 represents mono, di, tri substitutions or no
substitution;
wherein R 1 is selected from the group consisting of alkyl,
cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, alkenyl,
cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl,
carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl,
sulfinyl, sulfonyl, phosphino, and combinations thereof; and
wherein R21 R22 R23 R3 R4 R6 R7 and R8 are each
' ' ' ' ' ' independently selected from the group consisting of hydrogen,
deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl,
alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl,
heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl,
carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl,
sulfonyl, phosphino, and combinations thereof;
wherein each R5 is independently selected from the group
consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl,
heteroalkyl, alkoxy, aryloxy, amino, silyl, alkenyl,
cycloalkenyl, heteroalkenyl, alkynyl, acyl, carbonyl, carboxylic
acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl,
phosphino, and combinations thereof; and
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Application 13/762,612
wherein n is 1 or 2.
Response to Notice of Non-Compliant Appeal Brief filed January 12,
2018, 15, 22 ( Claims Appendix).
The Examiner sets forth the following rejections in the Final Office
Action entered February 14, 2017 ("Final Act."), and maintains these
rejections in the Examiner's Answer entered March 3, 2018 ("Ans."):
I. Claims 1, 2, 4, 6-15, 19, 20, and 23-34 under 35 U.S.C. § 112,
second paragraph as being indefinite for failing to particularly point out and
distinctly claim the subject matter that the inventors regard as the invention;
II. Claims 1, 2, 4, 6-15, 18-20, and 23-34 under 35 U.S.C. §
103(a) as unpatentable over Xia et al. (US 2010/0141127 Al, published June
10, 2010); and
III. Claims 1, 2, 4, 6-15, 18-20, and 23-34 on the ground of
nonstatutory double patenting as unpatentable over claims 1-23 of U.S.
Patent No. 8,367,223 B2.
DISCUSSION
Upon consideration of the evidence relied upon in this appeal and
each of Appellant's contentions, we reverse the Examiner's rejection of
claims 1, 2, 4, 6-15, 18-20, and 23-34 under 35 U.S.C. § 103(a) (Rejection
II) for the reasons set forth in the Appeal Brief and below. We summarily
affirm the Examiner's rejection of claims 1, 2, 4, 6-15, 19, 20, and 23-34
under 35 U.S.C. § 112, second paragraph (Rejection I), and rejection of
claims 1, 2, 4, 6-15, 18-20, and 23-34 for nonstatutory double patenting
(Rejection III), because Appellant does not contest these rejections.
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Application 13/762,612
Rejection II
Independent claims 1 and 19 both recite, in part, a compound having a
structure selected from the group consisting of:
L.
The Examiner finds that Xia discloses compounds "within the scope
of the present claims" having the formula:
LI
3-n
L2
where the R2 substituent on L 1 (ligand 1) can be a substituted or
unsubstituted aryl group, among other possibilities. Final Act. 4--5 ( citing
Xia ,r 16). The Examiner finds that Xia discloses several specific
compounds that differ only from the compounds recited in claims 1 and 19
by "not hav[ing] an optionally substituted phenyl group corresponding to the
present phenyl group to which R21-R23 are attached." Final Act. 4--5 (citing
compounds 2-5 and 7-9 disclosed in Xia). The Examiner determines that
"[ s ]ubstituted and unsubstituted phenyl groups would have been prima facie
5
l
I
.J 3-n.
Appeal2018-005417
Application 13/762,612
obvious to one of ordinary skill in the art at the time of the invention for an
aryl or substituted aryl." Final Act. 5. The Examiner concludes that
"[a]bsent a showing of unexpected results commensurate in scope with the
claims, it would have been an obvious modification to one of ordinary skill
in the art at the time of the invention to make and use various compounds
within the scope of Xia's disclosure having a substituted or unsubstituted
phenyl group substituted on the phenylbenzimidazole ligand at the position
of R2 in Xia's heteroleptic compound formula." Id.
On this appeal record, however, the Examiner does not provide a
sufficient factual basis to support the Examiner's conclusion of obviousness,
for reasons expressed by Appellant (App. Br. 4--12; Reply Br. 6-8) and
discussed below.
Xia discloses heteroleptic compounds that contain a phenylpyridine
ligand (L2) and a phenylbenzimidazole ligand (LI) and are useful as
emissive dopants in organic light emitting devices, due to the compounds'
emission of green light. ,r,r 3, 7, 16, and 19. As Appellant correctly points
out (App. Br. 5---6), although Xia discloses that the R2 substituent on the
phenylbenzimidazole ligand (L 1) of the compounds can be aryl or
substituted aryl, Xia discloses that "conjugation between the phenyl and the
benzimidazole portions of LI will likely result in a reduced LUMO [lowest
unoccupied molecular orbital] level and a loss of the saturated green
emission. Thus, the substituents (e.g., R1 and R2) are not fused as to form
an extended conjugated system." ,r 46 ( emphasis added). Xia goes on to
explain that branched alkyl and twisted aryl substituents-which are not
phenyl groups-have a non-planar conformation that contributes to
beneficial properties exhibited by Xia's compounds, such as better color, a
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Application 13/762,612
lower sublimation temperature, and less likelihood of lowering the triplet
energy of the compounds. ,r,r 47--48.
Appellant, with support from the Declaration of Bin Ma filed
December 2, 2016 ("the Ma Declaration"), explains that one of ordinary skill
in the art would have understood that in the compounds disclosed in Xia
"there is conjugation from the phenyl ring of a phenyl-benzimidazole ligand
all the way to the benzo ring of the benzimidazole," and bonding a phenyl
group to the benzo ring of the phenyl-benzimidazole ligand (as Xia's R2
substituent) would extend the conjugation of the ligand and lower its triplet
energy, which the skilled artisan would have expected to cause a shift in the
color of the compounds' emission. App. Br. 5---6; Ma Declaration ,r 5.
Appellant argues that the compounds recited in claims 1 and 19 exhibit
unexpected emissive properties in view of Xia's disclosures discussed above
indicating that, to prevent loss of saturated green emission, the R2 substituent
on Xia's compounds should not extend conjugation. App. Br. 6-8.
Specifically, relying on data presented in the Specification, and portions of
the Declaration of Chuanjun Xia filed June 1, 2016 ("the Xia Declaration")
and the Ma Declaration, Appellant argues that the claimed compounds-
having a substituted or unsubstituted phenyl substituent on the benzo ring of
the benzimidazole moiety----do not exhibit a red shift, which Xia suggests
would occur due to the phenyl substituent extending the conjugation of the
phenyl-benzimidazole ligand. App. Br. 6-8 (citing Spec. ,r,r 97-101, 157-
160, Table 3; Ma Declaration ,r 5; Xia Declaration ,r 3).
In response to Appellant's arguments, the Examiner relies on three
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Application 13/762,612
evidentiary references2-which the Examiner does not apply as prior art
references in the rejection3-that the Examiner asserts demonstrate that
"extending conjugation, per se, does not always result in a red shift," and the
position of a phenyl substituent on the pyridine ring of a phenylpyridine
ligand affects the amount of color shift. Ans. 6-7, 9 ( citing Xia 049 ,r 27 6
(Table 5), ,r 282 (Table 7); Ma col. 11, 11. 1-14, col. 12, 11. 11-38; Moore
col. 6, 11. 31--42, col. 6, 1. 59---col. 10, 1. 23). When addressing the relied-
upon disclosures in Appellant's Specification, the Examiner explicitly takes
the position that "[b ]enzimidazole and pyridine are not equivalent structures,
nor is the benzo moiety of benzimidazole equivalent to pyridine." Ans. 8.
The disclosures in Xia 049 cited by the Examiner describe the Amax
(wavelength of maximum absorption) of several unsubstituted and phenyl-
substituted phenylpyridine compounds. The relied-upon disclosures of Ma
also relate to phenylpyridine compounds, and indicate that the sign and
magnitude of the color-shifting effect of a phenyl pyridine substituent may
change depending on whether the substituent is attached to the phenyl
moiety (at any position) or is attached to the pyridyl moiety (at any
position). The disclosures in Moore cited by the Examiner describe
substitutions on 8-quinolinolato rings, and indicate that the color shifting
effect of such substituents depends on whether the substituent is electron
donating or accepting.
2 Xia et al. (US 2011/0227049 Al, published September 22, 2011) ("Xia
049"); Ma et al. (US 6,916,554 B2, issued July 12, 2005); and Moore et al.
(US 5,484,922, issued January 16, 1996).
3 Even if the Examiner had applied these references as prior art references in
the rejection of claims 1, 2, 4, 6-15, 18-20, and 23-34 under 35 U.S.C.
§ 103(a), such a rejection would nonetheless still be subject to the reversible
error discussed in this decision.
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Application 13/762,612
In view of the Examiner's position taken to refute Appellant's
evidence of non-obviousnes that "[b ]enzimidazole and pyridine are not
equivalent structures, nor is the benzo moiety of benzimidazole equivalent to
pyridine," the Examiner's reliance on disclosures in Xia 049 and Ma relating
to phenylpyridines, and reliance on disclosures in Moore relating to
quinolinolatos, which also differ structurally from benzimidazoles, to
support the Examiner's assertion of the obviousness of the Examiner's
proposed phenyl R2 substituent on the benzimidazole moiety of Xia's
compounds, is contradictory. Moreover, none of the relied-upon disclosures
in the three evidentiary references provides any teaching that would have led
one of ordinary skill in the art to utilize a phenyl group for the R2 substituent
in Xia's compounds. The Examiner does not identify any disclosure in Xia
049, Ma, or Moore that calls into question or contradicts Xia's teaching that
the R2 substituent is "not fused as to form an extended conjugated system."
Further undermining the Examiner's position, Xia 049 explicitly discloses
that "increase in conjugation also causes red shift in the emission of the
corresponding Ir complexes," resulting in a yellow emission that "is not
suitable for full color RGB display." ,r 127.
Therefore, on this appeal record, the Examiner does not provide a
sufficient factual basis to establish that one of ordinary skill in the art would
have been led to modify the compounds disclosed in Xia to produce
compounds as recited in claims 1 and 19. 4 We accordingly do not sustain
the Examiner's rejection under 35 U.S.C. § 103(a) of independent claims 1
4 Because we reverse the Examiner's rejection on this basis, we do not reach
Appellant's additional arguments directed to further asserted unexpected
results. App. Br. 10-12.
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and 19, and of claims 2, 4, 6-15, 18, 20, and 23-34, which each depend
from either claim 1 or claim 19.
Rejections I and III
We summarily sustain the Examiner's rejection of claims 1, 2, 4, 6-
15, 19, 20, and 23-34 under 35 U.S.C. § 112, second paragraph, and
rejection of claims 1, 2, 4, 6-15, 18-20, and 23-34 for nonstatutory double
patenting, because Appellant does not contest these rejections. App. Br. 4--
14; 37 C.F.R. § 4I.37(c)(l)(iv) (requiring that "arguments shall explain why
the examiner erred as to each ground of rejection ... [and that] any
arguments or authorities not included in the appeal brief will be refused
consideration by the Board"); see also Manual of Patent Examining
Procedure (MPEP) § 1205.02 (9th ed. Mar. 2014) ("If a ground of rejection
stated by the examiner is not addressed in the appellant's brief, appellant has
waived any challenge to that ground of rejection and the Board may
summarily sustain it, unless the examiner subsequently withdrew the
rejection in the examiner's answer.").
DECISION
We affirm the Examiner's rejection of claims 1, 2, 4, 6-15, 19, 20,
and 23-34 under 35 U.S.C. § 112, second paragraph, and rejection of claims
1, 2, 4, 6-15, 18-20, and 23-34 for nonstatutory double patenting. We
reverse the Examiner's rejection of claims 1, 2, 4, 6-15, 18-20, and 23-34
under 35 U.S.C. § 103(a).
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Application 13/762,612
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
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