Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
DETAILED ACTION
1. Claims 1-2, 5-7 are pending in the current application.
2. This application is a CON of 16/481,179 now US 11,708,385 07/26/2019 which is a 371 of PCT/US18/15506 01/26/2018 which claims benefit of 62/451,574 01/27/2017.
Request for Continued Examination
3. A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on July 3, 2025 has been entered.
Restriction/Election Maintained
4. Applicant’s election of group I and the species, the compound in claim 3, in the reply filed on August 26, 2024 was previously acknowledged. The election was made without traverse. According to applicants’ representative claims 1-3 read on the elected species. The elected species of claim 3 has been canceled. As detailed in the following rejections, the elected species and the generic claim was not found patentable. The search and examination was continued until prior art was found that anticipated or rendered obvious a non-elected species that falls within the scope of the generic Markush claim reading on the elected species. As per MPEP 803.02 II. C. “[T]he examiner must continue to search the species of the claim unless the claim has been found to be unpatentable over prior art.” The examiner “need not continue to search the claim if the claim is rejected over prior art”. [ibid. D.]
Claim Rejections/Objections Withdrawn
5. The rejection of claim 2 under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends is withdrawn based upon the amendments.
Claim Rejections/Objections Maintained/ New Grounds of Rejection
6. The rejection of claim 1-2 on the judicially-created basis that it contains an improper Markush grouping of alternatives is maintained. Applicant's arguments filed November 26, 2025 have been fully considered but they are not persuasive. The specification discloses no compounds that have the property of fluorescent emitter beyond those in canceled claims 3 and 4. No disclosed compounds read on the instant claims. The disclosed species compounds were in canceled claims 3 and 4 and are homogenous and have other features that are not claimed. In this case the claims are so expansive that a common utility cannot be expected. All of the compounds, have a very specific structure absent from the instant claims.
The rejection of claims 1-2 rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement is maintained. Applicant's arguments filed November 26, 2025 have been fully considered but they are not persuasive. According to the arguments, “support is found on pages 53-69”. There are only certain subgeneric descriptions and no genus of claim 1 formula II having this ring forming feature. These subgenera are already in claim 2. None of the compounds in the subgenera have a “substituted” ring and every example in the subgeneric structures there is an unsubstituted ring.
The rejection of claim(s) 1-2 under 35 U.S.C. 103 as being unpatentable over Li US 20160359125 A1 in view of Chen “Nitrogen heterocycle-containing materials for highly efficient phosphorescent OLEDs with low operating voltage” J. Mater. Chem. C, 2014, 2, 9565 is maintained. Applicant's arguments filed November 26, 2025 have been fully considered but they are not persuasive. According to the arguments Chen does not teach “a single example in which a N-heterocyclic unit is part of a fused ring system”, but is drawn only to non-fused congeners. According to the arguments Chen is a teaching away. Presumably this argument applies only to V1a, V1b, V1c, V1d, V1e, V1f, V2a V2b, V2c, V2d, V2e, V2f, V3a V3b, V3c, V3d, V3e, V3f, since these are the Vs part of a fused ring system since V4a V4b, V4c, V5a V5b, V5c, V5d, and V5e are not fused. In response to applicant's argument that the references fail to show certain features of the invention, it is noted that the features upon which applicant relies are not recited in the rejected claim(s). Even if the claims were so limited the argument is unpersuasive, nitrogen atom doping is well-known in both fused and non-fused compounds, Bunz "Large N-Heteroacenes: New Tricks for Very Old Dogs?" Angew. Chem. Int. Ed. 2013, 52, 3810 - 3821; explains on page 3810,
The substitution of CH units through nitrogen atoms to generate pyridine or pyrazine rings comes to mind. The resulting N-heteroacenes should display attractive properties, complementary to those of the “normal” acenes. The last five years have witnessed significant activity in the synthesis and property evaluation of larger N-hetero-acenes. Several overviews have already been written,[4] but the area has expanded such that a new overview of this exciting and emerging topic is timely. It is important to look at issues that encompass synthetic approaches, structures, physical and optical properties, as well as applications of N-heteroacenes in organic electronic devices. Here we present developments since 2010.
Bunz reviews a number of examples. See also Richards "Putting the 'N' in ACENE: Pyrazinacenes and their structural relatives" Org. Biomol. Chem., 2011, 9, 5005; Miao "Ten Years of N-Heteropentacenes as Semiconductors for Organic Thin-Film Transistors" Adv. Mater. 2014, 26, 5541-5549.
The rejection of claims 1-2 on the ground of nonstatutory double patenting as being unpatentable over claims 1-11, 13 of U.S. Patent No. 11,472,827 in view of Chen “Nitrogen heterocycle-containing materials for highly efficient phosphorescent OLEDs with low operating voltage” J. Mater. Chem. C, 2014, 2, 9565 is maintained. Applicant's arguments filed November 26, 2025 have been fully considered but they are not persuasive.
New grounds of rejection are set forth below.
Claim Interpretation
7. The claims in this application are given their broadest reasonable interpretation using the plain meaning of the claim language in light of the specification as it would be understood by one of ordinary skill in the art. The following claim limitations are in a new proviso in claim 1:
“only one of V1b, V1c and V1d is N;
only one of V2d and V2e is N;
only one of V3a and V3d is N;
only one of V4a, V4b, and V4c is N; and
only one or two of V5b, V5c, and V5d is N;”
This sets a limit on the number of nitrogen atoms in the various V#x containing rings but does not require that any of the variables be a nitrogen atom. An alternative interpretation would be that each set has one nitrogen or one to two of V5b, V5c, and V5d however this is not seen and if this were true then none of the substructures in claim 2 would lack antecedent basis and claim 2 would be deficient under 112 (d) as failing to further limit the claim from which it depends as those compounds would lie outside of the scope of claim 1.
Rejection under the judicially created doctrine of improper Markush grouping
8. Claim 1-2 rejected on the judicially-created basis that it contains an improper Markush grouping of alternatives. See In re Harnisch, 631 F.2d 716, 721-22 (CCPA 1980) and Ex parte Hozumi, 3 USPQ2d 1059, 1060 (Bd. Pat. App. & Int. 1984). The improper Markush grouping includes species of the claimed invention that do not share both a substantial structural feature and a common use that flows from the substantial structural feature. The members of the improper Markush grouping do not share a substantial feature and/or a common use that flows from the substantial structural feature for the following reasons: The claim 1 is drawn to a Markush of Formula (II) contains nested variables for Vs, Rs and Xs, forming or not forming various rings. A Markush claim contains an ‘‘improper Markush grouping’’ if: (1) The species of the Markush group do not share a ‘‘single structural similarity,’’ or (2) the species do not share a common use. The compounds of Formula (II) do not share a “single structural similarity” since there is no common core due to the variable permutations of the variables. They do not belong to the same recognized physical or chemical class or to the same art-recognized class. This structure is insubstantial to the disclosure of the compounds in the specification. According to the specification the compounds are fluorescent emitters. The structure of the molecule governs its ability to fluoresce.
The specification discloses no compounds that have the property of fluorescent emitter beyond those in canceled claims 3 and 4. No disclosed compounds read on the instant claims. The disclosed species compounds were in canceled claims 3 and 4 and are homogenous and have other features that are not claimed. In this case the claims are so expansive that a common utility cannot be expected. All of the compounds, have a very specific structure absent from the instant claims.
In response to this rejection, Applicant should either amend the claim(s) to recite only individual species or grouping of species that share a substantial structural feature as well as a common use that flows from the substantial structural feature, or present a sufficient showing that the species recited in the alternative of the claims(s) in fact share a substantial structural feature as well as a common use that flows from the substantial structural feature. This is a rejection on the merits and may be appealed to the Board of Patent Appeals and Interferences in accordance with 35 U.S.C. §134 and 37 CFR 41.31(a)(1) (emphasis provided).
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
9. Claims 1-2 rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention. This is a rejection for new matter. The new proviso in claim 1 is unsupported:
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R7 and R8 were not previously described as forming a ring. Claim 2 also adds this ring forming provision. While some subgeneric descriptions have this ring, they are specific embodiments. There is no support for the at least one of language regarding X1/X2 in claim 1. There is no mention of any substitution of this ring in the specification.
The claim also adds an additional proviso,
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which is also new matter.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
10. Claim(s) 1 is/are rejected under 35 U.S.C. 102(a) (1) as being anticipated by Li US 20160359125 A1. Page 82 has the compound of claim 2, which is the elected species1:
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M is defined as Pd or Pt. This is the first compound on page 48 of claim 2.
Page 79 column 2 has the following compound which is a compound of claim 1 Formula II where X1 is CR7R8 and they join to form a ring.
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This compound reads on claim 1 where M is Pd or Pt, V1a is N, V1b, V1c, V1d, V1e, V1f, V2a V2b, V2c, V2d, V2e, V2f, V3a V3b, V3c, V3d, V3e, V3f, V4a V4b, V4c, V5a V5b, V5c, V5d, and V5e are C, X is O, X1 is CR7R8 and R7/R8 join to form a ring as shown in the claim, X2 is a bond, and Y1 is N. The prior compound is the same vis-à-vis the same definitions except the definitions of X1 and X2 are swapped.
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.
11. Claim(s) 1-2 is/are rejected under 35 U.S.C. 103 as being unpatentable over Li US 20160359125 A1 in view of Chen “Nitrogen heterocycle-containing materials for highly efficient phosphorescent OLEDs with low operating voltage” J. Mater. Chem. C, 2014, 2, 9565.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
Li teaches the complexes of the instant claims sans proviso “wherein at least one of V1b-V1f, V2a-V2f, V3a-V3f, V4a-V4c, and V5a-V5e is N” . Page 82 has the compound of claim 2, which is the elected species2:
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M is defined as Pd or Pt. This is the first compound on page 48 of claim 2.
Page 79 column 2 has the following compound which is a compound of claim 1 Formula II where X1 is CR7R8 and they join to form a ring.
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The generic structure on page 353 Formula A1 corresponds to that of claim 1:
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The L1 rings can be any heteroaryl.
The incorporation of additional nitrogen atoms into polycyclic aromatic scaffolds has been demonstrated to effectively modify the photophysical and electrochemical properties of the parent material. Chen explains the effects of adding nitrogens to these materials, on page 9567 column 2, under heading “2. Fundamentals of PHOLEDs”:
Aryl-N-heterocyclic units are generally considered to be electron-deficient in nature. As shown in Fig. 2, the typical six membered aryl cycles such as benzene, pyridine, pyrimidine, and triazine can achieve lower-lying LUMO and HOMO energy levels by introducing one or more nitrogen atoms into the cycle; the more added nitrogen atoms, the lower lying the LUMO and HOMO energy levels are.
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Thus, the incorporation of these N-heterocyclic units into one molecule generally lowers its LUMO and HOMO energy levels, imparting good electron injection and hole-blocking abilities. In addition, electrons generally transport well in the organic semiconductors that contain them, resulting in relatively high electron mobility. These characteristics clearly make N-heterocyclic groups widely applicable for the construction of ETMs for OLEDs. Moreover, due to their electron-deficient nature, these N-heterocyclic fragments can also be used as the acceptor units to build bipolar transport materials combined with the donor units, which are preferable as host materials for phosphors. Thereby, N-heterocyclic compounds have significant potential for the development of high-performance host and electron transport materials. Based on these high-performance materials, PHOLEDs with high efficiencies as well as low driving voltages close or equal to the theoretical limits are anticipated.
2. Ascertaining the differences between the prior art and the claims at issue.
The compounds discussed in Li have a phenyl ring while the claimed compounds have a pyridine or additional nitrogen containing ring, where one of the carbons has been replaced with a nitrogen atom. These compounds include but are not limited to those in claim 2:
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3. Resolving the level of ordinary skill in the pertinent art. Rationales, motivational statements (MPEP 2142-2143).
The artisan of ordinary skill would be motivated to make the pyridine analogs of the prior art compounds of Li because they are expected to work better. The nitrogen atom is a classical isostere of CH. Pyridine is a chemical approximations of the aromatic benzene ring. One of ordinary skill would be motivated to make the compounds of the invention because he or she would expect the compounds to “achieve lower-lying LUMO and HOMO energy levels by introducing one or more nitrogen atoms into the cycle; the more added nitrogen atoms, the lower lying the LUMO and HOMO energy levels are.” As explained by Chen “[T]he incorporation of these N-heterocyclic units into one molecule generally lowers its LUMO and HOMO energy levels, imparting good electron injection and hole-blocking abilities. In addition, electrons generally transport well in the organic semiconductors that contain them, resulting in relatively high electron mobility.”
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 claims at issue 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); and 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 a nonstatutory double patenting ground provided the reference application or patent either is shown to be commonly owned with this application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The USPTO internet Web site contains terminal disclaimer forms which may be used. Please visit http://www.uspto.gov/forms/. The filing date of the application will determine what form 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 http://www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
12. Claims 1-2 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-11, 13 of U.S. Patent No. 11,472,827 in view of Chen “Nitrogen heterocycle-containing materials for highly efficient phosphorescent OLEDs with low operating voltage” J. Mater. Chem. C, 2014, 2, 9565. Although the claims at issue are not identical, they are not patentably distinct from each other because the compound of instant claim 1 and 2 are the compounds of the patent claims. Species of claim 1 Formula II include compounds on column 636:
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Column 641-642:
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Col. 645:
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For the same reasons as set forth in the 103 rejection over Li in view of Chen, the claims are obviousness type double patenting.
Conclusion
13. Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID K O'DELL whose telephone number is (571)272-9071. The examiner can normally be reached on Monday - Friday 9:30 - 7:00 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks can be reached on 571-270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/DAVID K O'DELL/ Primary Examiner, Art Unit 1621
1 The claims no longer read on the elected species or any disclosed species in the specification.
2 The claims no longer read on the elected species or any disclosed species in the specification.