DETAILED ACTION
Applicant’s reply, filed 3 September 2025 to the requirement for restriction mailed 3 July 2025 (Examiner M. N. Huang), has been fully considered. As per Applicant’s election of Group I in combination with Applicant’s filed claim amendments claims 1-2, 11-13, 15, 21-22, 25, 28, 38, 44 and 59-66 are pending under examination wherein: claims 38, 44 and 59 have been amended, claims 1-2, 11-13, 15, 21-22, 25 and 28 are in the forms originally/previously presented, claims 60-66 are new, and claims 3-10, 14, 16-20, 23-24, 26-27, 29-37, 39-43 and 45-58 have been cancelled by this and/or preliminary amendment(s).
Election/Restrictions
Applicant’s election without traverse of Group I in the reply filed on 3 September 2025 is acknowledged. The Examiner agrees with Applicant’s assessment that claim 59 properly groups with the method(s) of independent claim 1. No claims stand withdrawn by this election in view of the filed claim amendments.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-2, 11-13, 21-22, 25, 28, 38, 44, 59-64 and 66 are rejected under 35 U.S.C. 103 as being unpatentable over Vespa et al. (Eur. J. Org. Chem., 2018, 4592-4599) in view of Langhals et al. (US 6,491,749).
Regarding claims 1 and 22, Vespa teaches N-annulated perylene diimide dimers having pyrrolic N-H bonds (abstract; Fig1; 3) and teaches such can be reacted with nitrogen containing bases in organic solvents and films formed therefrom via solvent removal (pg4595-4596). Vespa further teaches forming devices including organic field effect transistors and organic solar cells (pg4596).
Vespa teaches the organic solvent is trichloromethane (p4594-4596) and does not specifically teach water and/or C1-C6 alcohol. However, Langhals teaches when treating an N-annulated perylene bisiimide having an N-H bond of formula (XII) with a base material a plurality of solvents are suitable including protic solvents such as alcohols, including ethanol, etc., or chlorinated solvents such as trichloromethane. Langhals and Vespa are analogous art and are combinable because they are concerned with the same field of endeavor, namely N-annulated perylene bisiimide solutions for base treatment and modification. In view of the recognition by Langhals that trichloromethane and protic alcohols are equivalent and interchangeable in base reactions to obtain pyrrolo-derivatives, it would have been obvious to one of ordinary skill in the art to substitute the trichloromethane of Vespa with a protic alcohol, such as ethanol, of Langhals and thereby arrive at the present invention. Case law holds that the mere substitution of an equivalent (something equal in value or meaning, as taught by analogous prior art) is not an act of invention; where equivalency is known to the prior art, the substitution of one equivalent for another is not patentable (See In re Ruff 118 USPQ 343 (CCPA 1958; MPEP 2144.06).
Regarding claims 2, 11 and 38, Vespa in view of Langhals renders obvious the method as set forth above. The dimers of Vespa read on the instant claim as dimers are compounds of Formula I. Alternatively, Langhals teaches non-dimer structures of identical structure and it would have been obvious to substitute the dimers of Vespa with the non-dimer structures of Langhals with a reasonable expectation of success given the basic structure and the chemistry of the identical pyrrole N-H groups is the same.
Regarding claims 12-13, Vespa in view of Langhals renders obvious the method as set forth above. While Vespa does not specifically state that the base reacted PDI compounds result in solvent-resistant films (claim 12) where the film is resistant to solvents of water, C1-C6 alcohol, chlorinated alkanes, hydrocarbons, aromatic hydrocarbons or amides (claim 13), Vespa does teach that the compound 3 did not dissolve well in common processing solvents (pg4596). Further it is held that a chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present (see In re Spada, 911 F.2d 705, 15 USPQ2d 1655, (Fed. Cir. 1990); see also In re Best, 562 F.2d 1252, 195 USPQ 430, (CCPA 1977). “Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established.”; MPEP 2112.01)).
Regarding claims 21 and 25, Vespa in view of Langhals renders obvious the method as set forth above. Vespa further teaches 0-20 equivalents (Fig6) and 10% v/v of volatile organic base (Fig7). Further, it is noted that generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indication such concentration or temperature is critical (MPEP 2144.05 IIA; see In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955); see also Peterson, 315 F.3d at 1330, 65 USPQ2d at 1382; see also Smith v. Nichols, 88 U.S. 112, 118-19 (1874) (a change in form, proportions, or degree "will not sustain a patent"); In re Williams, 36 F.2d 436, 438 (CCPA 1929) ("It is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions."); see also KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 416 (2007)).
Regarding claim 28, Vespa in view of Langhals renders obvious the method as set forth above. Vespa further teaches spin-coating (pg4596).
Regarding claim 44, Vespa in view of Langhals renders obvious the method as set forth above. Vespa further teaches thin films (Fig5) made from spin coating solutions. While Vespa does not specifically teach the thickness of the film, such is generally held to be a result of the rate of spin coating and is result effective. It is further noted that changes in size/proportion are found to be prima facie obvious and do not render the instant claims patentable (see MPEP 2144.04; see In re Rose, 220 F.2d 459, 105 USQP 237 (CCPA 1955); see In re Rinehart, 531 F.2d 1048, 189 USPQ 143 (CCPA 1976)).
Regarding claims 59-61, Vespa in view of Langhals renders obvious the method as set forth in claims 1 above incorporated here by reference. Vespa further teaches forming devices including organic field effect transistors, where the film is an electron transport layer, and organic solar cells, by spin-coating and solvent removal (pg4596).
Regarding claims 62-64, Vespa in view of Langhals renders obvious the method as set forth in claim 59 above. The dimers of Vespa read on the instant claim as dimers are compounds of Formula I. Alternatively, Langhals teaches non-dimer structures of identical structure and it would have been obvious to substitute the dimers of Vespa with the non-dimer structures of Langhals with a reasonable expectation of success given the basic structure and the chemistry of the identical pyrrole N-H groups is the same.
Regarding claim 66, Vespa in view of Langhals renders obvious the method as set forth in claim 59 above. Vespa further teaches 0-20 equivalents (Fig6) and 10% v/v of volatile organic base (Fig7). Further, it is noted that generally, differences in concentration will not support the patentability of subject matter encompassed by the prior art unless there is evidence indication such concentration or temperature is critical (MPEP 2144.05 IIA; see In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955); see also Peterson, 315 F.3d at 1330, 65 USPQ2d at 1382; see also Smith v. Nichols, 88 U.S. 112, 118-19 (1874) (a change in form, proportions, or degree "will not sustain a patent"); In re Williams, 36 F.2d 436, 438 (CCPA 1929) ("It is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions."); see also KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 416 (2007)).
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-2, 11-13, 15, 21-22, 25, 28, 38, 44 and 59-66 provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-4, 8, 10, 31-34, 36 and 39-47 of copending Application No. 18/683,908 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of both the instant and copending applications are directed to substantially similar methods (and/or in the case of the copending application a device/film resulting from the method(s) of the instant application) and devices comprising a layer film comprising substantially the same N-annulated perylene diimide (PDI) compound having at least one pyrrole N-H bond in combination with similar equivalents of a base (instant carbonate base; copending Cs2CO3) cast from solutions of substantially similar solvents.
Where the copending claims fail to recite the concentration of the PDI (instant claim 25) and/or the thickness (instant claim 44) of the film: i) it is noted that differences in concentration generally do not support patentability of subject matter (MPEP 2144.05); and ii) it is noted that changes in size/proportion are generally found to be prima facie obvious (see MPEP 2144.04). Where the copending claim fails to state solvent resistance properties: it is generally held a chemical composition and its properties are inseparable (MPEP 2112.01).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JANE L STANLEY whose telephone number is (571)270-3870. The examiner can normally be reached M-F 7:30 AM to 3:30 PM.
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/JANE L STANLEY/ Primary Examiner, Art Unit 1767