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 .
Status of the Claims
Claims 22 – 37, 39, 41 – 42, 44 and newly added claims 46 – 49 are pending.
Claims 22 – 37, 39, 41 – 42 and 46 – 49 are rejected.
Claim 44 is withdrawn.
Response to Applicant’s Remarks
Applicant’s remarks filed on April 28, 2026 and May 4, 2026 have been fully considered.
The objections to claims 22, 32 and 34 are withdrawn in view of amendments to recite proper Markush group language.
Regarding the improper Markush Grouping of alternatives rejection of claims 22 – 37, 39 and 41 – 42 (claims 38 and 40 are cancelled), Applicant’s remarks have been considered and addressed below:
On page 1, 5th paragraph – page 2, 1st paragraph, Applicant state that the claims are drawn to a common core structure,
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. Applicant note that the Office Action relies in part on Ex Parte
Hozumi, 3 USPQ2d 1059 (BPAI 1984) and state that the board reversed an improper Markush rejection because the claims covered an “extremely broad” class of compounds with diverse substituent definitions, but “the breadth represented by the… variables [do] not derogate from the unity of invention”. Similarly, Applicant argue the claimed compounds (i) exhibit a common utility, and (ii) share a substantial structural feature (aza-indolo[3,2,1-jk]carbazoles) essential to the common utility (useful as fluorescent materials in OLEDs).
However, it is noted that Applicant has not established how only the structure of aza-indolo[3,2,1-jk]carbazoles is considered a substantial structural feature in relation to the common utility in view of the variables R, Ra, Rb, Rc , Rd and Re. Each of the variables encompasses structures of the formulae (I-1) to (I-30) in claim 28, the moieties having the structures of the formulae (Cy-1) to (Cy-10) in claim 29, formulae (RA-1) to (RA-13) in claim 30, as well as the alternatives for “aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms”. The presence of one or different permutations of each of the formula would alter the physical and chemical properties such that they would not be expected to have the necessary common use. Therefore, Applicant’s remarks are not persuasive and the rejection is maintained. The rejection has only been amended to address the claims pending in the application
The rejection under 35 USC §102(a)(2) of claims 22 – 23 and 28 as being anticipated by Jin et al. CN107686484 A (publ. February 13, 2018), evidenced by English translation of CN107686484 A is withdrawn in view of amendments:
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Examination: Applicant’s amendments necessitate extending the search. The search has been further extended to include the scope, wherein at least one of R, Ra, Rb, or Rd is not H.
Improper Markush Group Rejection (Maintained)
Claims 22 – 37, 39, 41 – 42, 44 and 46 – 49 are rejected on the 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). A Markush grouping is proper if the alternatives defined by the Markush group (i.e., alternatives from which a selection is to be made in the context of a combination or process, or alternative chemical compounds as a whole) share a “single structural similarity” and a common use. A Markush grouping meets these requirements in two situations. First, a Markush grouping is proper if the alternatives are all members of the same recognized physical or chemical class or the same art-recognized class, and are disclosed in the specification or known in the art to be functionally equivalent and have a common use. Second, where a Markush grouping describes alternative chemical compounds, whether by words or chemical formulas, and the alternatives do not belong to a recognized class as set forth above, the members of the Markush grouping may be considered to share a “single structural similarity” and common use where the alternatives share both a substantial structural feature and a common use that flows from the substantial structural feature. See MPEP § 2117.
The Markush grouping of the compound of Formula (II) is improper because the alternatives defined by the Markush grouping do not share both a single structural similarity and a common use for the following reasons:
Claim 22 is directed to a compound comprising at least one structure of the formula (I):
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, wherein (for example):
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The structures associated with each of the variables above in the formula (I) do not share a substantial feature to each other.
For example, in claim 28, the compound of formula (I) is selected from one structure of the formulae (I-1) to (I-30). Further, in atleast two R, Ra, Rb, Rc , Rd and Re, the following moieties having the structures of the formulae (Cy-1) to (Cy-10) as presented below (according to claim 29):
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Further, in atleast two R, Ra, Rb, Rc , Rd and Re, the following moieties having the structures of the formulae (RA-1) to (RA-13) as presented below (according to claim 30):
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The compounds of formula (I) as claimed in claim 22 do not belong to the same art-recognized class or chemical class of compounds because there is no common core structure shared among all of the compounds that would enable them to be categorized the same. For example, in atleast two R, Ra, Rb, Rc , Rd and Re, the alternatives for “aromatic or heteroaromatic ring system which has 5 to 60 aromatic ring atoms” groups can be classified as phenylenes (e.g., CPC class C07C17), thiophenes (e.g., CPC C07D333 and C07D495), pyrrole (e.g., CPC C07D207 and C07D487), or as selenophenes (e.g., CPC C07D345 and C07D517). Further, the alternatives for “phenyl” and “5-6 membered heteroaryl” groups can also be classified in different CPC classes as noted above. Besides the condensed ring systems comprising five rings, there is no shared structure amongst all of the alternatives as claimed by the variables R, Ra, Rb, Rc , Rd and Re in the structures of formulae (I) (claim 22), (Cy-1) to (Cy-10) (claim 29) and (RA-1) to (RA-13) as presented below (claim 30). The compounds do not belong to the same recognized physical or chemical class or to the same art-recognized class and each compound would possess different physical and chemical properties in view of the functional and cyclic groups such that they would not be expected to have the necessary common use. Thus, the compounds of the Markush grouping cannot be considered to share a “single structural similarity” that is essential from which a common use flows.
In order to overcome this rejection, Applicant may set forth each alternative (or grouping of patentably indistinct alternatives) within an improper Markush grouping in a series of independent or dependent claims and/or present convincing arguments that the group members recited in the alternative within a single claim in fact share a single structural similarity as well as a common use. For example, the following is a proper Markush group of structure of formula (I):
X is N,
R and one Rd form a condensed ring system consisting of seven rings,
The other Rd is H,
Both Rbs are each H,
Both Ras together form a C5 (cyclopentyl) ring system, each ring system is independently substituted with four C1 (methyl) alkyl groups.
Both Rcs together form a C5 (cyclopentyl) ring system, each ring system is independently substituted with four C1 (methyl) alkyl groups.
The following is a proper Markush group of structure of formula (I-31):
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, wherein:
m is 3, each Re is combined with each other to form a condensed ring system consisting of six rings,
Rd is H,
Both Rbs are each H,
Both Ras together form a C5 (cyclopentyl) ring system, each ring system is independently substituted with four C1 (methyl) alkyl groups.
Both Rcs together form a C5 (cyclopentyl) ring system, each ring system is independently substituted with four C1 (methyl) alkyl groups.
or a single grouping of patentably indistinct species such that the variables R, Ra, Rb, Rc , Rd and Re are conserved across all species of formula (I).
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.
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.
Claims 22 – 23 and 28 are rejected under 35 U.S.C. 103 as being unpatentable over Jin et al. CN107686484 A (publ. February 13, 2018), evidenced by English translation of CN107686484 A, https://worldwide.espacenet.com/publicationDetails/biblio?CC=CN&NR= 107686484A&KC=A&FT=D&ND=3&date=20180213&DB=EPODOC&locale=en_EP, Retrieved on January 24, 2026.
Determining the scope and contents of the prior art
Jin et al. teach compound 87. See, e.g., paragraph [0029], page 33, and claim 6. Compound 87 is presented below:
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.
Compound 87 reads on the compound comprising at least one structure of the formula (I) (claims 22 – 23):
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, wherein
X is CRb,
Each R, Ra, Rb and Rd is H,
One Rc is H, and the other is C1 (CH2) alkyl group, further wherein, the CH2 group is replaced with a substituted heteroaromatic ring.
Compound 87 reads on the compound comprising at least one structure of the formula (I-1) (claim 28):
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, wherein:
Each Ra, Rb, Rd and Re is H,
One Rc is H, and the other is C1 (CH2) alkyl group, further wherein, the CH2 group is replaced with a substituted heteroaromatic ring.
Ascertaining the differences between the prior art and the claims at issue
With respect to compound of formula (I) and formula (I-1), Jin et al. does not explicitly teach the compound, wherein the hydrogen atom on one of the α-carbon positions (R, Ra, Rb and Rd) of the aza-indolo[3,2,1-jk]carbazole is replaced with C1 alkyl (methyl group).
Rationale for a prima facie case of obviousness
Compound 87 and the compound in the instant claims, wherein hydrogen on one of the α-carbon positions (R, Ra, Rb and Rd) of the aza-indolo[3,2,1-jk]carbazole is replaced with C1 alkyl, are considered structural analogs because hydrogen and methyl are deemed obvious variants absent unexpected or unobvious results. In re Wood, Whittaker, Stirling, and Ohta, 582 F.2d 638, 199 U.S.P.Q 137 (C.C.P.A. 1978). According to MPEP §2141(III), one of the rationales in the KSR decision states “(G) Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention”. KSR, 550 U.S. at 418, 82 USPQ2d at 1396. A person having ordinary skill in the art would have been motivated to make structural analogs of compound 87 because said compound is identified in Jin as a lead compound. The PHOSITA would have had a reasonable expectation that the structural analogs of compound 87, wherein C1 alkyl is present on one of the α-carbon positions (R, Ra, Rb and Rd) of the aza-indolo[3,2,1-jk]carbazole instead of a hydrogen atom, would be useful as fluorescent materials OLEDs successfully because similar properties would have been expected from such structurally similar compounds.
The prior art would render the present claims prima facie obvious as presented below:
Claims 22 – 23, directed to a compound comprising at least one structure of the formula (I):
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, wherein
X is CRb,
One of R, Ra, Rb and Rd is C1 alkyl, and the rest is H,
One Rc is H, and the other is C1 (CH2) alkyl group, further wherein, the CH2 group is replaced with a substituted heteroaromatic ring.
Claim 28, directed to the compound comprising at least one structure of the formula (I-1):
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, wherein:
One of R, Ra, Rb and Rd is C1 alkyl, and the rest is H,
One Rc is H, and the other is C1 (CH2) alkyl group, further wherein, the CH2 group is replaced with a substituted heteroaromatic ring.
Conclusion
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 Sagar Patel whose telephone number is (571)272-1317. The examiner can normally be reached Monday - Friday: 9am to 5pm EST.
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/Sagar Patel/Examiner, Art Unit 1626
/KAMAL A SAEED/Primary Examiner, Art Unit 1626
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