Rohm and Haas Electronic Materials LLCDownload PDFPatent Trials and Appeals BoardOct 27, 20212021003642 (P.T.A.B. Oct. 27, 2021) 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. 14/027,400 09/16/2013 James W. THACKERAY 58726-104001US(73526- US) 8571 14324 7590 10/27/2021 Mintz Levin/Rohm&Haas/Dow Mintz Levin One Financial Center Boston, MA 02111 EXAMINER CEPLUCH, ALYSSA L ART UNIT PAPER NUMBER 1772 NOTIFICATION DATE DELIVERY MODE 10/27/2021 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): IPDocketingBos@mintz.com IPFileroomBos@mintz.com mintzdocketing@cpaglobal.com PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE ____________ BEFORE THE PATENT TRIAL AND APPEAL BOARD ____________ Ex parte JAMES W. THACKERAY, JIN WUK SUNG, PAUL J. LaBEAUME, and VIPUL JAIN ____________ Appeal 2021-003642 Application 14/027,400 Technology Center 1700 ____________ Before MICHAEL P. COLAIANNI, GEORGE C. BEST, and CHRISTOPHER C. KENNEDY, Administrative Patent Judges. BEST, Administrative Patent Judge. DECISION ON APPEAL Pursuant to 35 U.S.C. § 134(a), Appellant1 appeals from the Examiner’s decision to reject claims 1, 2, 5, 7–10, 24, and 26–282 of Application 14/027,400. Final Act. (January 22, 2020). We have jurisdiction under 35 U.S.C. § 6. 1 “Appellant” refers to “applicant” as defined in 37 C.F.R. § 1.42. Appellant identifies Rohm & Haas Electronic Materials LLC as the real party in interest. Appeal Br. 1. 2 Appellant has cancelled claims 23 and 25. Amendment After Final Action Under 37 C.F.R. § 1.116 (filed April 22, 2020; entered May 12, 2020). Appeal 2021-003642 Application 14/027,400 2 A video hearing was held on October 4, 2021. A hearing transcript has been added to the ’400 Application’s prosecution history. For the reasons set forth below, we affirm. I. BACKGROUND The ’400 Application describes photoresist compositions comprising two or more distinct acid generating compounds, particularly (a) a polymer- bonded acid generator and (b) an acid generator that is not bonded to the polymer and comprises one or more acid-labile groups. Spec. 1. In particular, the Specification states that preferred polymer bound and non- polymer bound acid generator compounds include thioxanthones having the structure depicted in Formula (IB): Wherein: Z is a counter anion; R is a non-hydrogen substituent; each T and each T′ are the same or different non-hydrogen substituent; each L and each L′ are the same or different acid-labile group, with T, L, T′, and L′ non-hydrogen groups may be taken together to form a ring; m and m′ are each independently 0, 1, 2, 3, or 4; and Appeal 2021-003642 Application 14/027,400 3 n and n′ are each independently 0, 1, 2, 3, or 4. Id. at 4. The Specification further states that embodiments where one or both of m and m′ are 0 are particularly preferred. Id. Claim 1 is representative of the ’400 Application’s claims and is reproduced below from the Appeal Brief’s Claims Appendix. 1. A photoresist composition comprising: (a) a polymer comprising an acid generator bonded thereto; and (b) an acid generator compound that is not bonded to the polymer and that comprises a thioxanthone moiety and one or more acid-labile groups, wherein the (a) bonded acid generator comprises i) a thioxanthone moiety and ii) an acid-labile group. Appeal Br. 11. II. REJECTION On appeal, the Examiner maintains3 the following rejection: Claims 1, 2, 5, 7–10, 24, and 26–28 are rejected under 35 U.S.C. § 103(a) as unpatentable over the combination of Tsuchimura ’075,4 Tsuchimura ’149,5 and Tsubaki.6 Final Act. 6. 3 Because claim 23 has been canceled, the rejection of claim 23 under 35 U.S.C. § 112, ¶ 4, Final Act. 5, is moot. 4 JP 2012-048075, published March 8, 2012. We cite the machine translation that is of record. 5 US 2010/0248149 A1, published September 30, 2010. 6 WO 2013/047091 A1, published April 4, 2013. Appeal 2021-003642 Application 14/027,400 4 III. DISCUSSION A. Claim 1 In rejecting claim 1, the Examiner found that Tsuchimura ’075 describes a photoresist composition comprising a resin having a cation, an anion and an acid generator compound bound to the polymer. Final Act. 6 (citing Tsuchimura ’075 ¶¶ 29, 31, 322). The Examiner found that Tsuchimura ’075’s polymer comprises a cation monomer having general formula A3: Id. at 6–7 (citing Tsuchimura ’075 ¶¶ 38, 51); see also Tsuchimura ’075 ¶¶ 16–17. The Examiner further found that Tsuchimura ’075 teaches that, in formula A3, Z may be a carbonyl group. Id. at 7 (citing Tsuchimura ’075 ¶ 48). When Z is a carbonyl group, Tsuchimura ’075’s polymer comprises a sulfonium cation within a thioxanthone moiety. Id. The Examiner found that Tsuchimura ’075 does not describe the polymer-bonded acid generator A3 as comprising an acid-labile group. Final Act. 7. The Examiner also found that Tsuchimura ’149 describes the photoresist composition comprising a polymer and an acid generator. Final Act. 7. The Examiner further found that Tsuchimura ’149’s polymer Appeal 2021-003642 Application 14/027,400 5 comprises a sulfonium ion in which the sulfur is part of a thioxanthone moiety. Id. (citing Tsuchimura ’149 ¶¶ 59, 72). The Examiner found that Tsuchimura ’149 describes the thioxanthone moiety as including an acid- decomposable group. Id. at 7–8 (citing Tsuchimura ’149 ¶ 11). Based on these findings, the Examiner concluded that it would have been obvious to a person having ordinary skill in the art to incorporate Tsuchimura ’149’s acid-labile group into the polymer-bonded cation of Tsuchimura ’075 because the use of an acid-labile group is said to increase the sensitivity and resolution of the photoresist and provide a resist film with a small number of development defects. Final Act. 8 (citing Tsuchimura ’149 ¶¶ 57, 331). The Examiner found that the combination of Tsuchimura ’075 and Tsuchimura ’149 does not specifically teach that the non-polymer bound acid generator comprises an acid-labile group. Final Act. 8. The Examiner found that Tsubaki describes a photoresist composition comprising a polymer and an acid generator compound. Final Act. 8. Tsubaki’s acid generator compound can be a sulfonium ion wherein the sulfur is part of a thioxanthone moiety. Id. at 8–9 (citing Tsubaki 111–112). Tsubaki also describes its acid generating compound as including an acid- labile group. Id. at 9. The Examiner further found that Tsubaki describes the use of an acid generator including an acid-labile group creates a photoresist composition with higher sensitivity that created a well-informed extremely fine pattern when exposed to extreme ultraviolet light. Id. at 9–10. Based on these findings, the Examiner concluded that it would been obvious to a person having ordinary skill in the art to combine Tsubaki’s non-polymer bonded acid generator compound with the photoresist Appeal 2021-003642 Application 14/027,400 6 composition suggested by the combination of Tsuchimura ’075 and Tsuchimura ’149. Final Act. 10. Appellant argues that the rejection of claim 1 should be reversed for any of four reasons. We address each of these arguments separately. First, Appellant argues that the Examiner has not provided any evidence that the proposed substitution of Tsuchimura ’149’s acid-labile group into the Tsuchimura ’075 structure is feasible. Appeal Br. 4. This argument is not persuasive. We begin by noting that the apparent level of ordinary skill in the art of chemical synthesis for photoresist formulations is high. We make this finding after review of Appellant’s Specification and the prior art. See, e.g., Ex parte Jud, Appeal No. 2006-1061, 2006 WL 4080053 (BPAI Jan. 29, 2006) (informative) (inferring level of skill in the art from the specification); see also Okajima v. Bourdeau, 261 F.3d 1350, 1355 (Fed. Cir. 2001) (indicating that the prior art can reflect the level of skill in the art). At the hearing, Appellant’s counsel agreed that the level of ordinary skill in this art is high. Tr. 8–10. Moreover, Tsuchimura ’149 describes a thioxanthone-containing moiety that includes acid-labile groups. Tsuchimura ’149 ¶¶ 18, 59. In particular, Tsuchimura ’149 describes a photoresist composition containing a cation moiety with the structure shown below. Appeal 2021-003642 Application 14/027,400 7 As Tsuchimura ’149 explains, in this structure, Z1 represents the acid decomposable group, while L represents a single bond or a divalent linking group. Id. Tsuchimura ’149 specifically teaches that it is preferable that L be a carbonyl group. Id. ¶ 72. When L is a carbonyl group, Tsuchimura ’149’s structure depicts a thioxanthone. For the purpose of rejections pursuant to § 102 and § 103, prior art references are presumptively enabled. In re Antor Media Corp., 689 F.3d 1282, 1287–88 (Fed. Cir. 2012). This presumption, however, may be rebutted by an applicant. In re Morsa, 713 F.3d 104, 110 (Fed. Cir. 2013) (“The presumption in Antor is a procedural one—designed to put the burden on the applicant in the first instance to challenge the cited prior art . . . . Once an applicant makes a non-frivolous argument that cited prior art is not enabling, however, the examiner must address that challenge.”). In this case, (1) the level of ordinary skill in the art is high, (2) Tsuchimura ’149 describes a thioxanthone-containing moiety with an acid labile group, and (3) Appellant has not presented any evidence in support of its argument that the incorporation of acid-labile groups in a thioxanthone moiety is not feasible. See Appeal Br. 3–5. We, therefore, are Appeal 2021-003642 Application 14/027,400 8 not persuaded that incorporation of an acid-labile group in Tsuchimura ’075’s cation containing monomer would not have been feasible, or that it would have been beyond the level of ordinary skill in the art. Second, Appellant argues that the Examiner did not identify a reason to substitute an acid-labile group from Tsuchimura ’149 into the Tsuchimura ’075 structure. Appeal Br. 4. We are not persuaded by this argument. As the Examiner found, Tsuchimura ’149 describes the incorporation of an acid-labile group as improving the sensitivity and resolution of the resist and as providing a resist film that has a small number of development defects. Tsuchimura ’149 ¶¶ 57, 331. Based upon this description, a person having ordinary skill in the art would have had a reason to combine Tsuchimura ’075 and Tsuchimura ’149 in the manner set forth in the Final Action. Third, Appellant argues that the combination of Tsuchimura ’075 and Tsuchimura ’149 does not teach that the non-polymer bound acid generator compound comprises an acid-labile group. Appeal Br. 4. Appellant recognizes that the Examiner relies upon Tsubaki’s teaching the non- polymer bound acid generator compound. Id. Appellant, however, argues that (1) there is no evidence that the cited generic formula would be acid decomposable, and (2) there is no showing that the proposed substitution would be operable. Id. We are not persuaded by these arguments. The Examiner found that Tsubaki describes the non-polymer bound acid generator compound. Final Act. 8. In particular, Tsubaki describes the acid generator compound having the following structure and comprising a Appeal 2021-003642 Application 14/027,400 9 site capable of decomposing by action of an acid. Id. at 8–9 (citing Tsubaki 111–12). In this structure, Q1 is a divalent linking group or a single bond, and B1 is an acid-labile group. Id. at 9 (citing Tsubaki 112). The Examiner further found that Tsubaki describes structures in which one R1d is a hydrogen atom and the other two R1d groups bond to each other to form a ring. Id. Tsubaki specifically states that the two R1d moieties may form a divalent linking group having four or fewer carbon atoms. Tsubaki 112. Tsubaki further identifies a carbonyl group as a specific divalent linking group that may be present in the acid generating compound. Id. (“The divalent linking group is preferably a linking group having 4 or less carbon atoms and, for example, a methylene group, an ethylene group, an ether bond, a carbonyl group and an ester group are exemplified.”). Tsubaki, therefore, specifically identifies acid generator compounds containing a thioxanthone moiety. Tsubaki, therefore, specifically describes a non-polymer bound acid generator compound that includes acid labile groups. As discussed above, Tsubaki is presumed to be enabled. Antor Media, 689 F.3d at 1287–88. Appellant has not presented any evidence to rebut this presumption. See Appeal 2021-003642 Application 14/027,400 10 Appeal Br. 3–4. Moreover, as discussed above, the level of ordinary skill in this art is high. We, therefore, are not persuaded that Tsubaki fails to describe an operable thioxanthone moiety containing an acid decomposable group. Fourth, Appellant argues that the rejection should be reversed because Tsubaki does not exemplify a compound with an acid-labile group. Appeal Br. 4. At the hearing, Appellant further explained its position, arguing that the Examiner had failed to establish a prima facie case of unpatentability because Tsubaki describes a broad genus of acid generator compounds without exemplifying the particular subgenus encompassed by claim 15. Appellant asserted that its position was supported by In re Jones, 958 F.2d 347 (Fed. Cir. 1992).7 Tr. 5, 12–13. We are not persuaded by this argument. Appellant correctly argues that a prior art description of a broad genus does not make every member of that genus prima facie obvious. See Jones, 958 F.2d at 350; In re Baird, 16 F.3d 380, 382 (Fed. Cir. 1994). In Jones, the claim at issue encompassed a single ammonium salt of the herbicide dicamba. Jones, 958 F.2d at 348. The prior art reference 7 When asked why Jones was not cited in either the Appeal Brief or the Reply Brief, Appellant’s counsel argued that the Reply Brief’s citation of In re Grabiak, 769 F.2d 729 (Fed. Cir. 1985), meant that Appellant was entitled to rely on an entire line of cases that included Jones. Tr. 14. Grabiak, however, was cited for a different proposition in a section of the Reply Brief that did not address Tsubaki’s disclosure. Reply Br. 1–2 (“The secondary citation of Tsuchimura ‘149 which ‘075.reports [sic] distinct materials cannot be relied upon for importing an isolating [sic] feature into Tsuchimura ‘075. See In re Grabiak . . . .”). Nonetheless, we shall address Appellant’s untimely argument. Appeal 2021-003642 Application 14/027,400 11 described a genus consisting of any amine salt of dicamba. Id. at 349. Amine salts identified in the prior art as “typical” were structurally dissimilar to the claimed salt. Id. at 349–50. Based on these facts, the Federal Circuit rejected a rule that “regardless of how broad, a disclosure of a chemical genus renders obvious any species that happens to fall within it.” Id. at 350 (discussing Merck & Co. v. Biocraft Labs., Inc., 874 F.2d 804, 806–09 (Fed. Cir. 1989). Baird concerned a similar fact pattern. In Baird, the claim at issue was directed to a flash fusible binder resin comprising a polyester made from bisphenol A and one of three dicarboxylic acids. Baird, 16 F.3d at 381. The Federal Circuit determined that this very narrow subgenus was not prima facie obvious over a reference that describes a genus estimated to include polyesters made from combinations of more than 100 million species of diphenols and a large number of dicarboxylic acids. Id. at 381–82. The Federal Circuit concluded that “[a] disclosure of millions of compounds does not render obvious a claim to three compounds, particularly when that disclosure indicates a preference leading away from the claimed compounds.” Id. at 383. Although Appellant is correct that mere disclosure of a species as part of a large genus does not automatically render that species obvious, Appellant’s broader interpretation of Jones (and, by extension, Baird) is incorrect. Appellant’s argument implies that it believes that a claim directed to a species is per se patentable over prior art describing a genus encompassing a large number of species, including the claimed species, unless the claimed species is exemplified in the prior art. See Appeal Br. 4. The predecessor to this Board has expressly rejected a similar proposition in a case that is, for us, binding precedent. See Ex parte Fu, Appeal 2021-003642 Application 14/027,400 12 Appeal No. 2008-0601, 2008 WL 867826 (BPAI March 31, 2008) (precedential). In that case, the Board distinguished Baird and then stated: We expressly reject the notion that a claim reciting a species is per se patentable when the prior art discloses a genus encompassing a broad but finite number of known options which include the claimed species. . . . That is not to say, however, that an applicant would never be entitled to a patent in a situation as here. For example, KSR [Int’l Co. v. Teleflex Inc., 550 U.S. 398 (2007)] and Graham, as well as a myriad of precedents of our reviewing court, teach that secondary considerations such as unexpected results may confer patentability. Also, for example, patentability may be shown if the prior art teaches away from the species within the genus. But here, Appellants did not rely on any such persuasive evidence in support of nonobviousness. Id. at *8. Indeed, it has long been the law that “a reference is not limited to the disclosure of specific working examples.” In re Mills, 470 F.2d 649, 651 (CCPA 1972). Moreover, disclosure of particular examples does not constitute a teaching away from the remainder of a broader disclosure. In re Susi, 440 F.2d 442, 446 n.3 (CCPA 1971). Instead, “all of the relevant teachings of the cited references must be considered in determining what they fairly teach to one having ordinary skill in the art.” In re Mercier, 515 F.2d 1161, 1165 (CCPA 1975). As a result of cases such as Jones, Baird, and Fu, we may not use per se rules to determine whether claim 15’s subject matter is prima facie obvious. Cf. In re Ochiai, 71 F.3d 1565, 1572 (Fed. Cir. 1995) (“[R]eliance on per se rules of obviousness is legally incorrect and must cease.”). Instead, we consider the particular facts concerning claim 15’s scope and the Graham factors. In Graham v. John Deere Co., 383 U.S. 1, 17–18 (1966), the Supreme Court identified four factual determinations forming the background against Appeal 2021-003642 Application 14/027,400 13 which the obviousness or nonobviousness of the subject matter is determined. These four factors are (1) the scope and content of the prior art, (2) the differences between the prior art and the claims at issue, (3) the level of ordinary skill in the art, and (4) objective evidence of nonobviousness such as commercial success or long felt but unsolved needs. Id. We address each of these factors in turn. First, as discussed above, Tsubaki describes a broad genus of acid generating compounds. See Tsubaki 111–12. Appellant does not dispute the Examiner’s finding that Tsubaki’s broad genus includes thioxanthones having at least one acid-labile group. Second, the difference between the combined disclosures of Tsuchimura ’075, Tsuchimura ’149, and Tsubaki and claim 1’s subject matter is the breadth of the genus each describes. With respect to the non- polymer bound acid generator compound, Tsubaki describes an extremely broad genus, while claim 1 encompasses a narrower genus comprising “a thioxanthone moiety and one or more acid-labile groups.” Third, as discussed above, the level of ordinary skill in the pertinent art of the photoresist formulations is high. At oral argument, Appellant’s counsel agreed that a person having ordinary skill in the art would have at least a bachelor’s degree in chemistry plus several years of experience working in photoresist formulations. Tr. 9–10. Fourth, Appellant has not presented any evidence regarding the so- called secondary considerations of nonobviousness. See Appeal Br. 3–5. After due consideration of the Graham factors, we conclude that the subject matter of claim 1 would have been obvious to a person having ordinary skill in the art at the time of the invention. Appeal 2021-003642 Application 14/027,400 14 Our conclusion is consistent with the cases discussed above. In particular, Jones and Baird are readily distinguished from the facts of the case at hand. As discussed above, Baird discusses a fact pattern in which the prior art contained a description “indicate[d] a preference leading away from” the applicant’s claimed invention. Baird, 16 F.3d at 383. Similarly, Jones discusses a fact pattern in which the “typical” in embodiments of the claim genera are structurally dissimilar from the specific compound claimed in the application at issue. Jones, 956 F.2d at 350. In this case, we find that the disclosure of the prior art specifically leads toward the claimed subgenera of polymer bound and non-polymer bound acid generator compounds. The combination of references cited by the Examiner specifically identifies both the polymer bound and non- polymer bound acid generator compounds as comprising thioxanthone moiety as preferred members of the broad genera described. See Tsuchimura ’149 ¶ 72 (describing a carbonyl linking group as preferred); Tsubaki 112 (stating that a carbonyl group is “exemplified” as a preferable divalent linking group). The prior art, therefore, would have specifically pointed a person of ordinary skill in the art toward acid-labile group substituted thioxanthones as a promising category of acid generator compounds for experimentation. In view of the foregoing, we conclude that the Examiner correctly determined that the combination of Tsuchimura ’075, Tsuchimura ’149, and Tsubaki renders obvious a genus that includes the specific structures set forth in claim 1. Because Appellant does not argue or provide any evidence that the specific subgenus it wishes to claim provides unexpected results Appeal 2021-003642 Application 14/027,400 15 relative to the prior art, the Examiner correctly determined that the subject matter of claim 1 was obvious. B. Claims 2, 5, 7, 10, 24, and 26–28 Appellant identifies each of the dependent claims under a separate heading as if it wishes to present separate argument for the patentability of each of the claims. See Appeal Br. 5–9. For each of the dependent claims, Appellant first asserts that the claim is patentable for the same reasons that claim 1 is said to be patentable. See, e.g., Appeal Br. 5 (“Appellant’s dependent claim 2 incorporates all [of] the limitations of independent claim 1 and therefore is patentable for the above reasons discussed with respect to claim 1.”). For the reasons set forth above, we have determined that independent claim 1 is not patentable over the combination of references asserted by the Examiner. For each of the dependent claims, Appellant then asserts that the claim is separately patentable and then summarizes the additional limitations added by the dependent claim. See, e.g., Appeal Br. 6. The summary is followed by a one-sentence assertion that the cited documents do not teach the summarized limitations. Id. We are not persuaded by these arguments. Our rules provide that “[a] statement which merely points out what a claim recites will not be considered an argument for separate patentability of the claim.” 37 C.F.R. § 41.37(c)(1)(iv). In this case, Appellant has done little more than summarize what each of the dependent claims recites. We have reviewed the Examiner’s Final Action. In it, the Examiner made specific findings regarding how the combination of references describes or suggests the limitations for each of the dependent claims. Appellant’s argument Appeal 2021-003642 Application 14/027,400 16 neither acknowledges these findings nor specifically addresses the question of how the Examiner reversibly erred in determining that each of the dependent claims was unpatentable. For the reasons set forth above, we affirm the rejections of dependent claims 2, 5, 7–10, 24, and 26–28. IV. CONCLUSION In summary: Claim(s) Rejected 35 U.S.C. § Reference(s)/Basis Affirmed Reversed 1, 2, 5, 7–10, 24, 26–28 103(a) Tsuchimura ’075, Tsuchimura ’149, Tsubaki 1, 2, 5, 7–10, 24, 26–28 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 Copy with citationCopy as parenthetical citation