Ex Parte KramerDownload PDFPatent Trial and Appeal BoardMar 27, 201713529541 (P.T.A.B. Mar. 27, 2017) Copy Citation 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.”). 2 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); 3 Appeal 2016-002760 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. 4 Appeal 2016-002760 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 5 Appeal 2016-002760 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 6 Appeal 2016-002760 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 7 Appeal 2016-002760 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 8 Appeal 2016-002760 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, 9 Appeal 2016-002760 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 10 Copy with citationCopy as parenthetical citation