Ex Parte Kramer

Patent Trial and Appeal Board

Mar 27, 2017

13529541 (P.T.A.B. Mar. 27, 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.
13/529,541 06/21/2012 John W. Kramer 71018-US-NP 1043
(RHA0043U S 2)
14268 7590 03/29/2017
The Dow Chemical Company/Cantor Colburn LLP
20 Church Street
22nd Floor
Hartford, CT 06103-3207
EXAMINER
HAMILTON, CYNTHIA
ART UNIT PAPER NUMBER
1722
NOTIFICATION DATE DELIVERY MODE
03/29/2017 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):
ffuimpc@dow.com
u sptopatentmail @ C antorColburn .com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte JOHN W. KRAMER
Appeal 2016-002760
Application 13/529,5411
Technology Center 1700
Before LINDA M. GAUDETTE, CHRISTOPHER L. OGDEN, and
BRIAN D. RANGE, Administrative Patent Judges.
RANGE, Administrative Patent Judge.
DECISION ON APPEAL
SUMMARY
Appellant appeals under 35 U.S.C. § 134(a) from the Examiner’
decision rejecting claims 1—9. We have jurisdiction. 35 U.S.C. § 6(b)
We AFFIRM.
1 According to the Appellant, the real party in interest is DOW Global
Technologies LLC. Appeal Br. 2.
Appeal 2016-002760
Application 13/529,541
STATEMENT OF THE CASE2
Appellant describe the invention as relating to photoresist polymers
with improved linewidth roughness. Spec. Tflf 2—5. Claim 1, reproduced
below with some spacing added for readability and emphases added as to
certain recitations at issue, is illustrative of the claimed subject matter:
1. A polymer, comprising the polymerized product of
monomers comprising:
an acid-deprotectable monomer having the formula (I), a base-
soluble monomer having the formula (II), a lactone-containing
monomer of the formula (III), and a photo acid-generating
monomer of the formula (IV):
wherein each Ra is independently H, F, Ci-io alkyl, or C
1_10 fluoroalkyl,
Rb is independently Ci 20 alkyl, Ci 30 cycloalkyl, CV, 20
aryl, or C7-20 aralkyl, and each Rb is separate or at least
one Rb is bonded to an adjacent Rb to form a cyclic
structure,
Qi is an ester-containing or non-ester containing Ci 20
alkyl, C3-20 cycloalkyl, Ce 20 aryl, or C7-20 aralkyl,
W is a base-reactive group comprising -C(=0)-0H;
-C(CF3)2OH; -NH-SO2Y1 where Y1 is F or Ci^
2 In this decision, we refer to the Final Office Action mailed January 15,
2015 (“Final Act.”), the Appeal Brief filed June 8, 2015 (“Appeal Br.”), the
Examiner’s Answer mailed November 5, 2015 (“Ans.”), and the Reply Brief
filed January 4, 2016 (“Reply Br.”).
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Appeal 2016-002760
Application 13/529,541
perfluoroalkyl; an aromatic -OH; or an adduct of any of
the foregoing with a vinyl ether,
a is an integer of 1 to 3,
L is a monocyclic, polycyclic, or fused polycyclic C^-20
lactone-containing group,
Q2 is ester-containing or non-ester containing and
fluorinated or non-fluorinated and is Ci 20 alkyl, C3-20
cycloalkyl, CV, 20 aryl, or C7-20 aralkyl group,
A is ester-containing or non ester-containing and
fluorinated or non-fluorinated, and is C1-20 alkyl, C3-20
cycloalkyl, C6-20 aryl, or C7-20 aralkyl,
Z is an anionic moiety comprising sulfonate, an anion
of a sulfonamide, or an anion of a sulfonimide,
G has formula (V):
wherein X is S or I,
each Rc is halogenated or non-halogenated and is
independently a Ci 30 alkyl group; a polycyclic or
monocyclic C3 30 cycloalkyl group; a polycyclic or
monocyclic C4 30 aryl group, wherein when X is S,
one of the Rc groups is optionally attached to one
adjacent Rc group by a single bond, and
z is 2 or 3, provided that when Xis I, z is 2, or
when X is S, z is 3;
wherein in formula (IX):
Z is a y valent C1-20 organic group, x is 0 or 1,
(V)
a chain transfer agent of formula (IX);
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Application 13/529,541
Rd is a substituted or unsubstituted C1-20 alkyl, (A 20 cycloalkyl,
Cr, 20 aryl, or C7-20 aralkyl; and
optionally, an initiator.
Appeal Br. 17—18 (Claims App’x).
REFERENCES
The Examiner relies upon the prior art below in rejecting the claims
on appeal:
Lee et al. US 2005/0032997 Al Feb. 10, 2005
(hereinafter “Lee”)
Kaneko et al. US 2010/0104974 Al Apr. 29, 2010
(hereinafter “Kaneko”)
Le et al. WO 98/01478 Jan. 15, 1998
(hereinafter “Le”)
Benoit et al. WO 2005/00924 Al Jan. 6, 2005
(hereinafter “Benoit”)
Sato et al. EP 1 630 607 A2 Aug. 26, 2005
(hereinafter “Sato”)
Masubuchi et al. WO 2010/044372 Apr. 22, 2010
(hereinafter “Masubuchi”)
Appellant cites the Handbook of Raft Polymerization, (Christopher
Bamer-Kowollik ed., WILEY-VCH Verlag GmbH & Co., 2008) (hereinafter
“Bamer-Kowollik”) as evidence supporting Appellant’s position.
REJECTION
On appeal, the Examiner maintains the rejection of claims 1—9 under
35 U.S.C. § 103 as unpatentable over Masubuchi (as translated in
Masubuchi et al., US 2011/0177453 Al, July 21, 20113) in view ofLe
further in view of Benoit, Sato, Lee, and Kaneko. Final Act. 2.
3 Appellant does not object to the Examiner’s reliance on the U.S.
Masubuchi publication for an English translation. We likewise cite to the
U.S. Masubuchi publication.
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Application 13/529,541
ANALYSIS
We review the appealed rejections for error based upon the issues
identified by Appellant and in light of the arguments and evidence produced
thereon. Cf. Ex parte Frye, 94 USPQ2d 1072, 1075 (BPAI 2010)
(precedential) (cited with approval in In re Jung, 637 F.3d 1356, 1365 (Fed.
Cir. 2011) (“it has long been the Board’s practice to require an applicant to
identify the alleged error in the examiner’s rejections”)). After considering
the evidence presented in this Appeal and each of Appellant’s contentions,
we are not persuaded that Appellant identifies reversible error. Thus, we
affirm the Examiner’s rejections for the reasons expressed in the Final Office
Action and the Answer. We add the following primarily for emphasis.
Appellant does not separately argue claims 2—9. We therefore limit
our discussion to claim 1. Claims 2—9 stand or fall with that claim. 37
C.F.R. §41.37(c)(l)(iv) (2013).
The Examiner finds that Masubuchi teaches polymers for use as a
photo resist resin having high resolution, broad depth of focus tolerance,
small line edge roughness, and high sensitivity. Final Act. 2—3 (providing
citations to Masubuchi). The Examiner finds that Masubuchi teaches a
polymer comprising four monomers within the scope of the four polymers
recited by claim 1. Id. at 3—5 (citing Masubuchi Table 1 located at 1277).
The Examiner also finds that Masubuchi teaches that an organic solvent (in
particular, 2-butanone) may be used in conjunction with a sulfonate
monomer (in particular, PAG-1). Ans. 7. The Examiner finds that
Masubuchi teaches that the process to form its product can be “any common
polymerization process” but also finds that Masubuchi does not specifically
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Application 13/529,541
disclose the polymerization method of claim 1 (i.e., use of the recited chain
transfer agent). Final Act. 5.
The Examiner finds that Le, Lee, Benoit, and Kanecto all teach
polymerization processes making use of a chain transfer agent akin to claim
1 as being beneficial. Id. at 5—6 (providing citations to Le, Lee, Benoit, and
Kanecto). For example, the Examiner finds that Le teaches chain transfer
agents “inclusive of those used by applicants” and teaches that its
polymerization technique “is good for controlling molecular weight and
reducing polydispersity.” Id. at 5 (citing Le). The Examiner establishes that
this control is beneficial by citing Sato as teaching that control of
polydispersity yields resins with less deterioration in resolution and less
roughness of walls on the resist pattern. Id. at 6 (providing citations to
Sato). Similarly, the Examiner finds that Lee, Benoit, and Kanecto teach the
use of chain transfer agents with benefits of controlling polydispersity (Lee
and Kanecto), allowing thinner layers (Benoit), and better resolution with
smoother side walls (Kanecto). Id. (providing citations to Lee, Benoit and
Kanecto). The Examiner thus concludes that Le, Benoit, Sato, Lee, and
Kenko make Appellant’s invention an obvious improvement of the
compositions and polymers of Masubuchi. Id. A preponderance of the
evidence supports the Examiner’s findings and conclusion.
Appellant does not persuasively dispute the findings of fact above.
Rather, Appellant argues that a person of skill would not have had a
reasonable expectation of success in combining the recited monomers with
the chain transfer agent of formula IX. Appeal Br. 12. Appellant supports
this argument by explaining that chain-transfer agents are used in RAFT
(reversible addition-fragmentation chain-transfer) polymerization and by
explaining that Bamer-Kowollik teaches that only water-based RAFT agents
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Application 13/529,541
(i.e., agents different from the chain transfer agent of claim 1) may be used
in conjunction with sulfonate-containing monitors (such as monomer IV of
claim 1). Appeal Br. 12 (citing Bamer-Kowollik 249). Appellant further
explains that a water-based solvent is not practical for monomers (I) to (III)
of claim 1. Thus, according to Appellant, a person of skill in the art would
not have had a reasonable expectation of success in combining monomers (I)
to (IV) while making use of a chain transfer agent of formula (IX). Appeal
Br. 12—13, 15. Appellant further emphasizes that none of the references
(individually) teach such a combination:
[Ajmong numerous references, the Examiner fails to point out a single
example of RAFT polymerization between a monomer bearing a
hydrophilic group and a hydrophobic monomer in non-aqueous
solvent to support her assertion of obviousness.
Reply Br. 5.
As explained above, the Examiner and Appellant present conflicting
prior art evidence. The Examiner finds that Masubuchi teaches that an
organic solvent may be used with a sulfonate monomer (Ans. 7) while
Appellant argues that Bamer-Kowollik teaches that sulfonate monomers
must be polymerized in an aqueous solvent (at least for RAFT
polymerization) (Appeal Br. 12). “When prior art contains apparently
conflicting references, the Board must weigh each reference for its power to
suggest solutions to an artisan of ordinary skill” and, in so doing, “consider
the degree to which one reference might accurately discredit another.” In re
Young, 927 F.2d 588, 591 (Fed. Cir. 1991).
Here, a preponderance of the evidence weighs against Appellant’s
position. As a threshold matter, and as explained above, the Examiner
generally identifies substantial evidence supporting the Examiner’s
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Application 13/529,541
obviousness conclusion. A person of skill in the art desiring to make the
polymer taught by Masubuchi via “any common polymerization process”
(Masubuchi 1179) would reasonably have chosen to make use of a chain
transfer agent-based process as taught by Le, Lee, Benoit, and/or Kaneko
because of the many advantages of such a process as taught by those
references. The Examiner’s obviousness conclusion is well founded because
making use of a chain transfer agent to control the polymer of Masubuchi is
no more than a predictable use of a prior art element according to established
function. KSRInt’l Co. v. Teleflex Inc., 550 U.S. 398 (2007).
With respect to the tension between the teachings of Masubuchi and
Bamer-Kowollik, a preponderance of the evidence supports the Examiner’s
finding that Masubuchi teaches that an organic solvent (in particular, 2-
butanone) may be used in conjunction with a sulfonate monomer (in
particular, PAG-1). Ans. 7; Masubuchi || 273, 274. Thus, Masubuchi
supports the Examiner’s finding that the sulfonate monomers of Masubuchi
“are not as limited in solubility as set forth by [Ajppellants and that workers
of ordinary skill in the resist arts would have so recognized this in view of
Masubuchi et al.” Ans. 7. While Bamer-Kowollik (published in 2008)
indicates that the hydrophilic nature of sulfonate monomers discourages an
organic solvent, Masubuchi (published in 2010) teaches that an organic
solvent will work with its sulfonate monomers. Meanwhile, Appellants
identify no evidence suggesting that the addition of a chain transfer agent
affects whether or not use of an organic solvent is appropriate.
On balance and weighing the entirety of each reference alongside each
other, the evidence supports the Examiner’s determination that a person of
ordinary skill would have had reasonable expectation of success in using
organic solvents with Masubuchi’s monomers combined with a chain
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Application 13/529,541
transfer agent. Ans. 7, 9; see Para-Ordnance Mfg., Inc. v. SGS Imps. Int’l,
Inc., 73 F.3d 1085, 1090 (Fed. Cir. 1995) (holding that teachings of a
reference that arguably teaches away from a claimed feature must be
weighed alongside teachings of cited reference that teaches propriety of
employing feature). The preponderance of the evidence supports the
Examiner’s finding that Bamer-Kowollik would not have dissuaded a person
of skill from seeking to polymerize the monomers of Masubuchi while
adding a chain transfer agent. Id. at 7.
Moreover, the Examiner correctly concludes that claim 1 does not
expressly recite RAFT polymerization as a limitation. Ans. 4. Rather, claim
1 requires a polymerization product resulting from the four recited
monomers and the recited chain transfer agent. Id. Appellant does not
present evidence (or argument) that the utility of the chain transfer agents of
Le, Lee, Benoit and/or Kanecto is limited to RAFT polymerizations. Indeed,
it appears that only the Lee reference explicitly refers to RAFT. Thus, the
evidence in the present record is unclear as to whether Bamer-Kowollik’s
caution against using an organic solvent in combination with a sulfonate
monomer for a RAFT reaction would apply in the context of using the chain
transfer agents of Le, Lee, Benoit, and/or Kaneko in conjunction with the
sulfonate monomer of Masubuchi. Ans. 8. Alternatively, even if claim 1
were necessarily directed to a product of a RAFT reaction (due to the
recitation of the chain transfer agent), a person of skill in the art would
recognize that Masubuchi teaches its sulfonate monomers have soluability in
an organic solvent (2-butanone) and, given this recognition, would also have
expectation of success given Bamer-Kowollik’s teaching that some of the
most beneficial features of RAFT include “versatility of monomer choice,
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Application 13/529,541
functional group tolerance and general experimental conditions under which
it can be successfully executed.” Ans. 6 (citing Bamer-Kowollik 248).
Because Appellant’s argument does not identify reversible error, we
sustain the Examiner’s rejection.
DECISION
We affirm the Examiner’s rejection of claims 1-9.
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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