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
Claims 1-15 are pending in the instant application.
Election/Restrictions
Applicant’s election without traverse of Group I,
PNG
media_image1.png
316
556
media_image1.png
Greyscale
and the species of Compound 1-1 (disclosed on page 52 and in Table 1 on page 110 of the instant specification),
PNG
media_image2.png
210
344
media_image2.png
Greyscale
,
in the reply filed on November 12, 2025 is acknowledged. The requirement is still deemed proper and is therefore made FINAL.
The compounds of elected Group I are being examined according to MPEP §803.02. The claims have been examined to the extent that they are readable on the elected the species of Compound 1-1. Prior art was found on the elected species. The subject matter of the search and examination thus far, inclusive of the elected species of Compound 1-1, is as follows:
a heterocyclic compound represented by instant Chemical Formula 1,
PNG
media_image3.png
322
390
media_image3.png
Greyscale
,
wherein
at least one of R1, R5, R6 or R8 represents
PNG
media_image4.png
182
202
media_image4.png
Greyscale
; and
all other variables are as defined in independent claim 1.
Claims 1-3, 5, and 6 are embraced by the above identified search and examination. Subject matter not embraced by the elected embodiment is withdrawn from further consideration. Note, MPEP § 803.02.
Claims 4 and 7-15 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected inventions, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on
November 12, 2025.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The Examiner has considered the Information Disclosure Statement filed on March 31, 2023. The submission is in compliance with the provisions of
37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Specification
The disclosure is objected to because of the following informalities: some of the chemical structures and/or the numbering of the chemical structures on pages 52-75 and 89-96 of the instant specification are not completely legible.
Appropriate correction is required.
Claim Objections
Claim 6 is objected to because of the following informalities:
some of the compounds claimed or the compound numbers in claim 6 are not completely legible; and
an “or” should be added before the last compound claimed in claim 6 for proper Markush language format.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 2 is rejected 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.
Claim 2 fails to further limit claim 1 because claim 2 is of the same scope as claim 1. All of the possible permutations of the attachment of the
PNG
media_image5.png
166
194
media_image5.png
Greyscale
moiety to the
PNG
media_image6.png
170
238
media_image6.png
Greyscale
moiety in [Chemical Formula 1] as shown in claim 1 are found in claim 2.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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 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 1-3 and 5 are rejected under
35 U.S.C. 102(a)(1) as being anticipated by Nishimura et al. {US 2012/0138915}.
Nishimura et al. disclose on page 245, for instance, Compound (I-138),
PNG
media_image7.png
388
452
media_image7.png
Greyscale
{a heterocyclic compound represented by instant [Chemical Formula 1] or instant [Chemical Formula 6],
PNG
media_image3.png
322
390
media_image3.png
Greyscale
or
PNG
media_image8.png
328
388
media_image8.png
Greyscale
,
wherein
X = O;
Ar1 = hydrogen;
Ar2 = hydrogen;
Ar3 = hydrogen;
Ar4 = hydrogen;
Ar5 = hydrogen;
R1 = hydrogen;
R2 = hydrogen;
R3 = unsubstituted C12 heteroaryl group (i.e., carbazoyl, a -N-Het);
R4 = hydrogen;
R5 = hydrogen;
R6 = Chemical Formula B or Chemical Formula B-5,
PNG
media_image4.png
182
202
media_image4.png
Greyscale
or
PNG
media_image9.png
172
216
media_image9.png
Greyscale
,
where
R10 and R40 = hydrogen,
R11 and R41 = hydrogen,
R12 and R42 = hydrogen,
R13 and R43 = hydrogen,
R21 and R44 = hydrogen,
R22 and R45 = hydrogen,
R23 and R46 = hydrogen, and
R24 and R47 = hydrogen;
R7 = hydrogen;
R8 = hydrogen;
R9 = hydrogen; and
a = one},
and Compound (I-139),
PNG
media_image10.png
412
458
media_image10.png
Greyscale
{a heterocyclic compound represented by instant [Chemical Formula 1] or instant [Chemical Formula 6],
PNG
media_image3.png
322
390
media_image3.png
Greyscale
or
PNG
media_image8.png
328
388
media_image8.png
Greyscale
,
wherein
X = S;
Ar1 = hydrogen;
Ar2 = hydrogen;
Ar3 = hydrogen;
Ar4 = hydrogen;
Ar5 = hydrogen;
R1 = hydrogen;
R2 = hydrogen;
R3 = unsubstituted C12 heteroaryl (i.e., carbazoyl, a -N-Het);
R4 = hydrogen;
R5 = hydrogen;
R6 = Chemical Formula B or Chemical Formula B-5,
PNG
media_image4.png
182
202
media_image4.png
Greyscale
or
PNG
media_image9.png
172
216
media_image9.png
Greyscale
,
where
R10 and R40 = hydrogen,
R11 and R41 = hydrogen,
R12 and R42 = hydrogen,
R13 and R43 = hydrogen,
R21 and R44 = hydrogen,
R22 and R45 = hydrogen,
R23 and R46 = hydrogen, and
R24 and R47 = hydrogen;
R7 = hydrogen;
R8 = hydrogen;
R9 = hydrogen; and
a = one}.
Therefore, Nishimura et al. anticipate the instantly claimed invention.
The comparison showing and discussion on pages 175-182 of the instant specification has been considered. However, the showing is not persuasive. To establish unexpected, beneficial and superior results of the instant claimed compounds over the closest prior art compounds, Applicant should compare by testing a sufficient number of exemplified structurally closest prior art compounds with the compounds of the instant claimed invention. Therefore, the following rejection applies.
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 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 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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
Claims 1-3, 5, and 6 are rejected under
35 U.S.C. 103 as being unpatentable over Seo et al. {KR 2020-069247 A}. A machine generated English translation of the KR document has been provided with this Office Action and will be referred to hereinafter.
Determination of the scope and content of the prior art (MPEP §2141.01)
Applicant claims heterocyclic compounds represented by instant [Chemical Formula 1],
PNG
media_image3.png
322
390
media_image3.png
Greyscale
,
wherein
X can represent O or S;
Ar1 to Ar5 can each represent hydrogen;
R1 to R9 can each represent hydrogen or a
substituted or unsubstituted C2 to C60
heteroaryl; and
a can represent 0 to 2;
with the proviso:
that at least one of R1, R5, R6 and R8
represents [Chemical Formula B],
PNG
media_image11.png
170
204
media_image11.png
Greyscale
,
where R10-R13 and R21-R24 can each
represent hydrogen; and
that one of R1 to R8 represents -N-Het (i.e., a
nitrogen containing heteroaryl).
Seo et al. teach compounds of Formulae [1-2], [1-3], [1-4], [1-5], [1-6] and [1-7] on pages 2-3 of the provided English translation,
PNG
media_image12.png
254
652
media_image12.png
Greyscale
PNG
media_image13.png
348
654
media_image13.png
Greyscale
,
PNG
media_image14.png
324
656
media_image14.png
Greyscale
,
PNG
media_image15.png
260
650
media_image15.png
Greyscale
,
PNG
media_image16.png
374
588
media_image16.png
Greyscale
,
PNG
media_image17.png
354
646
media_image17.png
Greyscale
.
The compounds taught by Seo et al. are structurally similar to the instant claimed compounds. See the compounds disclosed on pages 8-11 of the original KR document of Seo et al.
Ascertainment of the difference between the prior art and the claimed invention (MPEP §2141.02)
The difference between the compounds of Seo et al. and the compounds instantly claimed is that of positional isomerism. See where the carbazolyl ring,
PNG
media_image18.png
90
56
media_image18.png
Greyscale
, in the compounds of Seo et al. {i.e.,
PNG
media_image19.png
254
793
media_image19.png
Greyscale
} is attached to the instant R2 or R7 position of the compounds of instant Chemical Formula 1 instead of the R1, R5, R6 or R8 position as required in the proviso of instant claim 1. Additionally, compare the structural similarities between the elected species of Compound 1-1 claimed in instant claim 6,
PNG
media_image20.png
224
296
media_image20.png
Greyscale
,
and the 3rd compound disclosed on page 8 in Seo et al. (the original KR document),
PNG
media_image21.png
178
228
media_image21.png
Greyscale
.
Finding of prima facie obviousness--rational and motivation
(MPEP §2142-2143)
Position isomers are a basic form of close “structural isomers.” MPEP 2144.09(II), first paragraph, states the following:
II. HOMOLOGY AND ISOMERISM ARE FACTS WHICH MUST BE CONSIDERED WITH ALL OTHER RELEVANT FACTS IN DETERMINING OBVIOUSNESS
Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious); Aventis Pharma Deutschland v. Lupin Ltd., 499 F.3d 1293, 84 USPQ2d 1197 (Fed. Cir. 2007) (5(S) stereoisomer of ramipril obvious over prior art mixture of stereoisomers of ramipril.).
It is well established that position isomers are prima facie structurally obvious even in the absence of a teaching to modify. The isomer is expected to be preparable by the same method and to have generally the same properties. This expectation is then deemed the motivation for preparing the positional isomers.
A person of ordinary skill in the art would have been motivated to prepare positional isomers of the compounds taught in Seo et al. to arrive at the instant claimed compounds with the expectation of obtaining additional beneficial compounds which would be useful in organic light emitting devices. The instant claimed invention would have been suggested to one skilled in the art and therefore, the instant claimed invention would have been obvious to one skilled in the art.
The elected species of Compound 1-1 is not allowable in view of the teachings in Seo et al.
Reminder to Applicant
As a reminder, Applicant should specifically point out the support in the original disclosure {i.e., page number(s) and line number(s)} for any new claims or amended claims and for any amendments made to the disclosure. Making generic statements such as “all amendments are fully supported in the originally filed disclosure or the originally filed claims” without specifying page numbers and originally filed claim numbers are insufficient. See MPEP §714.02 and MPEP §2163.06(I).
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to:
Laura L. Stockton
(571) 272-0710.
The examiner can normally be reached on Monday-Friday from 8:30 am to 6 pm, Eastern Standard Time.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s acting supervisor,
James Alstrum-Acevedo can be reached on 571/272-5548. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/LAURA L STOCKTON/ Primary Examiner, Art Unit 1626 Work Group 1620
Technology Center 1600
December 10, 2025Book XXVIII, page 269
Prosecution Insights