DETAILED ACTION
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 .
Continued Examination Under 37 CFR 1.114
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 01/28/2026 has been entered.
This office action is in response to the amendment filed 01/28/2026, which amends claims 21, 36, 38, 47.
Election/Restrictions
In a requirement for election of species dated 12/27/2024, Applicant was required to choose from
Species I: A compound selected from formula I
Species II: A compound selected from formula II
Wherein if Species I (formula I) is elected, a second election must be made between:
Subspecies Ia: a+b+c = 3
Subspecies Ib: a+b+c < 3
Wherein if Species II (formula II) is elected, a second election must be made between:
Subspecies IIa: d+e+f+g = 4
Subspecies IIb: d+e+f+g < 4
Additionally, regardless of whether Species I or Species II is elected, Applicant should specify:
Option 1: All Y characters are oxygen atoms
Option 2: All Y characters are sulfur atoms
Option 3: All Y characters are nitrogen atoms
Option 4: at least one Y character is not oxygen, sulfur, or nitrogen.
In light of Applicant’s amendments to the claims, as well as the number of subspecies which have already been examined, the requirement for election of species between Species I and II, as well as all subspecies Ia, Ib, IIa, and IIb, as well as all of Options 1-4 , as set forth in the Office action mailed on 12/27/2024, has been reconsidered pursuant to MPEP § 821.04(a).
The requirement for election of species set forth on 12/27/2024 is hereby withdrawn and all species/claims rejoined.
Specifically, claims 26, 27, 31, 41, 42, and 47, directed to a previously non-elected species, are no longer withdrawn from consideration.
In light of the withdrawal of the requirement for election of species, the allowability of claim 35 is also withdrawn as one or more of the rejoined species meet the requirements of the claim.
In view of the above noted withdrawal of the restriction requirement, applicant is advised that if any claim presented in a divisional application is anticipated by, or includes all the limitations of, a claim that is allowable in the present application, such claim may be subject to provisional statutory and/or nonstatutory double patenting rejections over the claims of the instant application.
Once a restriction requirement is withdrawn, the provisions of 35 U.S.C. 121 are no longer applicable. See In re Ziegler, 443 F.2d 1211, 1215, 170 USPQ 129, 131-32 (CCPA 1971). See also MPEP § 804.01.
Claims 21, 25-27, 31, and 34-47 are examined herein.
Response to Amendment
In the response filed 01/28/2026, the claims were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the claims, the objection to claims 26, 27, 31, 33, 41, 42, and 44 is withdrawn by the Office.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 112(a) of claims 21, 25, 34, 36-40, 43, and 45-47 for failing to comply with the written description requirement, 35 U.S.C. 112(b) of claim 47 as failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention, the rejection under 35 U.S.C. 112(d) of claim 47 as being of improper dependent form, and the rejection under 35 U.S.C. 102 of claims 21, 25, 28, 31, and 45 as being anticipated by Nagata et al. (Nagata, Y.; Kato, S.; Miyake, Y.; Shinokubo, H., 2017, Synthesis of Tetraaza[8]circulenes from Tetrathia[8]circulenes through an SNAr-Based Process, Org. Lett. 2718-2721), are withdrawn by the Office.
Response to Arguments
Applicant’s arguments have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Claim Objections
Claims 25 and 31, and claims 26 and 27 are objected to under 37 CFR 1.75 as being a substantial duplicate of each other. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m).
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
Claims 21 and 44 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Lee et al. (US 2018/0108844 A1).
The applied reference has a common Assignee with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2).
This rejection might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C.102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B); or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement. See generally MPEP § 717.02.
With respect to claim 21, Lee discloses Compound D7 (page 17), which is pictured below.
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This compound meets the requirements of condition (v) of Formula II of the claim when d+e+f+g<4, Y1 is CRR’, two R5 are joined to form a ring, and R1-R4 and R6-R7 are not present or are hydrogen atoms, and R and R’ are both a carbazole group when (X9 through X16 are each carbon and Z is nitrogen).
With respect to claim 44, Lee teaches the compound of claim 21, and the compound is of Formula II and d+e+f+g<4.
Claims 21, 25-28, 31, 34, 36, and 44 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Kim et al. (US 2018/0105534 A1).
With respect to claim 21, Kim discloses compound 2 (page 3), which is pictured below.
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This compound meets the requirements of condition (v) of instant Formula II when g and e are 1, Y1 and Y3 are oxygen, and d and f are 0 so that Y2 and Y4 are not present, R4 is amino and hydrogen, R5 is aryl and hydrogen, R6 is amino and hydrogen, and R7 is hydrogen and a naphthyl group (X9 through X16 are CH).
With respect to claims 25/31, Kim teaches the compound of claim 21, and Y1 and Y3 are oxygen, as discussed above.
With respect to claim 26/27, Kim teaches the compound of claim 21, and two of d, e, f, and g are 0.
With respect to claim 28, Kim teaches the compound of claim 21, and the compound has the structure of the last embodiment of the claim.
With respect to claim 34, Kim teaches the compound of claim 21, and R7 is naphthyl (Z1 through Z8 are CH), as discussed above.
With respect to claim 36, Kim teaches an organic light emitting device comprising an anode, a cathode, and an organic layer between the electrodes, and the organic layer comprises an emission layer (EML) and the EML comprises Compound 2 (paragraphs 0163-0164), which is pictured below.
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This compound meets the requirements of condition (v) of instant Formula II when g and e are 1, Y1 and Y3 are oxygen, and d and f are 0 so that Y2 and Y4 are not present, R4 is amino and hydrogen, R5 is aryl and hydrogen, R6 is amino and hydrogen, and R7 is hydrogen and a naphthyl group (X9 through X16 are CH).
With respect to claim 44, Kim teaches the compound of claim 21, and d+e+f+g<4, as discussed above.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
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.
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.
Claims 21, 25, 28, 31, 34-35, 40, and 43 are rejected under 35 U.S.C. 103 as being unpatentable over Hirao et al. (US 2006/0142370 A1).
With respect to claim 21, Hirao discloses Compound (89) (paragraph 0087), which is pictured below.
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This compound is derived from Hirao formula (1) (paragraph 0008), which is pictured below.
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Hirao also teaches that X1 through X3, can be the divalent groups pictured below (paragraph 0011).
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Hirao also teaches that any of A1 to A6 can be a hydrogen atom or aromatic hydrocarbon (paragraph 0009) such as cyclic substituents pictured in paragraph [0079], including formula (14), which is pictured below.
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Such modifications produce a compound that meets the requirements of condition (ii) of instant Formula 1 when a+b+c=3 and Y1 through Y3 are sulfur, and R1 is a naphthyl group (X9 through X16 CR), X3 through X8 are carbon atoms and R2 and R3 are hydrogen atoms.
Hirao includes each element claimed, with the only difference between the claimed invention and Hirao being a lack of the aforementioned combination being explicitly stated. Absent a showing of unexpected results, it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to select any known substituent from each of the finite lists of possible combinations to arrive at the compound of the instant claim since the combination of elements would have yielded the predictable result of a compound which can be used as a synthesis raw material for fullerenes and heterofullerenes (paragraph 0007), commensurate in scope with the claimed invention. See Section 2143 of the MPEP, rationales (A) and (E).
With respect to claims 25/31, Hirao teaches the compound of claim 21, and Y1 through Y3 are each sulfur, as discussed above.
With respect to claim 28, Hirao teaches the compound of claim 21, and the compound is selected as the first embodiment of the claim, as pictured above.
With respect to claim 34, Hirao teaches the compound of claim 21, and R1 is a naphthyl group (Z1 through Z8 are CH), as discussed above.
With respect to claim 35, Hirao teaches the compound of claim 21, and the compound is instant Compound 13A or 14A.
With respect to claim 40, Hirao teaches the compound of claim 21, and Hirao also teaches a solution of hexahydrosumanene in toluene (paragraph 0105).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to creation a formulation comprising the compound of claim 21 in toluene in order to use it in a synthesis process, as taught by Hirao.
With respect to claim 43, Hirao teaches the compound of claim 21, and the compound is of Formula I, wherein a+b+c=3 and none of Y1 through Y3 are oxygen, as discussed above.
Claims 36-39 are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al. (US 2018/0108844 A1).
With respect to claim 36, Lee teaches and OLED comprising an anode, a cathode, an organic layer between the electrodes, and the organic layer comprises a compound of Formula I (paragraph 0097), such as Compound D7 (page 17), which is pictured below.
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This compound meets the requirements of condition (v) of Formula II of the claim when d+e+f+g<4, Y1 is CRR’, two R5 are joined to form a ring, and R1-R4 and R6-R7 are not present or are hydrogen atoms, and R and R’ are both a carbazole group when (X9 through X16 are each carbon and Z is nitrogen).
Lee teaches that the fused tetraphenylene compounds of the invention may be used a charge transporters, hosts, or emitters in OLED devices (abstract).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use Compound D7 in the organic layer of an OLED device, as the compounds are useful as charge transporters, hosts, or emitters in OLED devices, as taught by Lee.
With respect to claim 37, Lee teaches the OLED of claim 36, and Lee also teaches that the organic layer may comprise an emitter material (paragraph 0119), and examples of the emitter material include the compound pictured below (page 226), which meets the requirements of the instant claim.
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With respect to claim 38, Lee teaches a consumer product (flat panel display, paragraph 0031), comprising an OLED comprising an anode, a cathode, an organic layer between the electrodes, and the organic layer comprises a compound of Formula I (paragraph 0097), such as Compound D7 (page 17), which is pictured below.
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This compound meets the requirements of condition (v) of Formula II of the claim when d+e+f+g<4, Y1 is CRR’, two R5 are joined to form a ring, and R1-R4 and R6-R7 are not present or are hydrogen atoms, and R and R’ are both a carbazole group when (X9 through X16 are each carbon and Z is nitrogen).
Lee teaches that the fused tetraphenylene compounds of the invention may be used a charge transporters, hosts, or emitters in OLED devices (abstract).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use Compound D7 in the organic layer of an OLED device in a consumer product such as a flat panel display, as the compounds are useful as charge transporters, hosts, or emitters in OLED devices, as taught by Lee.
With respect to claim 39, Lee teaches the consumer product of claim 38, and the consumer product is a flat panel display, as discussed above.
Claims 40 and 46-47 are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al. (US 2018/0108844 A1), as applied above.
With respect to claim 40, Lee teaches the compound of claim 21, and Lee also teaches a formulation comprising the compound (paragraph 0099).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound in a formulation, as taught by Lee.
With respect to claims 46 and 47, Lee teaches the compound of claim 21, and Lee also teaches that the compound may be partially or fully deuterated (paragraph 0128).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to partially or fully deuterate Compound D7, as taught by Lee.
Allowable Subject Matter
Claims 41-42, and 45 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
With respect to dependent claim 41, the claim requires a compound of independent claim 21, wherein the compound has a structure of Formula I, wherein Y1 to Y3 are each a nitrogen atom, and a+b+c<3.
A search of the prior art did not identify the claimed invention.
The closest identified prior art is Hirao et al. (US 2006/0142370 A1).
With respect to dependent claim 41, Hirao discloses a compound of formula (1) (paragraph 0008), which is pictured below.
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Hirao teaches that X1 through X3, can be the divalent groups pictured below (paragraph 0011).
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However, Hirao does not teach that any of X1 through X3 can be absent.
Additionally, there existed no teaching nor motivation to remove one of X1 through X3 in the broader prior art as of the effective filing date of the claimed invention.
With respect to dependent claim 42, the claim requires a compound of independent claim 21, wherein the compound has a structure of Formula I, and a+b+c=2.
A search of the prior art did not identify the claimed invention.
The closest identified prior art is Hirao et al. (US 2006/0142370 A1).
With respect to dependent claim 41, Hirao discloses a compound of formula (1) (paragraph 0008), which is pictured below.
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Hirao teaches that X1 through X3, can be the divalent groups pictured below (paragraph 0011).
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However, Hirao does not teach that any of X1 through X3 can be absent.
Additionally, there existed no teaching nor motivation to remove one of X1 through X3 in the broader prior art as of the effective filing date of the claimed invention.
With respect to dependent claim 45, the claim requires a compound of independent claim 21, wherein the compound has a structure of Formula II, wherein d+e+f+g = 4, and at least one of Y1 through Y4 is not an oxygen atom.
A search of the prior art did not identify the claimed invention.
The closest identified prior art is Tamano et al. (JP 2000/077186 A, using the previously provided translation for references).
With respect to dependent claim 45, Tamano discloses a compound of formula (1) (paragraph 0008), which is pictured below.
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However, Tamano does not teach nor fairly suggest that any of the oxygen atoms can be replaced by another element.
Additionally, there existed no teaching nor motivation to change the oxygen atom in the broader prior art as of the effective filing date of the claimed invention.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer Boyd can be reached at 571-272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/RACHEL SIMBANA/Examiner, Art Unit 1786