Prosecution Insights
Last updated: April 19, 2026
Application No. 19/169,745

FUNCTIONALIZED AROMATIC PHOSPHONIC ACIDS FOR DISPLAY AND SOLAR CELL APPLICATIONS

Non-Final OA §102§103
Filed
Apr 03, 2025
Examiner
KANG, TAE-SIK
Art Unit
1728
Tech Center
1700 — Chemical & Materials Engineering
Assignee
The University of North Carolina at Chapel Hill
OA Round
1 (Non-Final)
58%
Grant Probability
Moderate
1-2
OA Rounds
2y 9m
To Grant
85%
With Interview

Examiner Intelligence

Grants 58% of resolved cases
58%
Career Allow Rate
314 granted / 546 resolved
-7.5% vs TC avg
Strong +28% interview lift
Without
With
+27.5%
Interview Lift
resolved cases with interview
Typical timeline
2y 9m
Avg Prosecution
33 currently pending
Career history
579
Total Applications
across all art units

Statute-Specific Performance

§101
0.4%
-39.6% vs TC avg
§103
44.8%
+4.8% vs TC avg
§102
18.9%
-21.1% vs TC avg
§112
32.1%
-7.9% vs TC avg
Black line = Tech Center average estimate • Based on career data from 546 resolved cases

Office Action

§102 §103
DETAILED ACTION Examiner’s Notes The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . Election/Restrictions Applicant’s election without traverse of Group I, Species A1, and Species B1 (claims 1, 3-8) in the reply on 03/02/2026 is acknowledged. Claims 2 and 9-30 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to nonelected Group, there being no allowable generic or linking claim. Claim Objections Claims 1 and 3-8 are objected to because of the following informality: Claim 1 is objected to because of the informality in the recitation “R1” in line 5. Examiner suggests changing the recitation to “R1”. All claims which depend on clam 1 are objected by virtue of dependency. Appropriate correction is required. Claim 1 is objected to because of the informality in the recitation “R2” in line 7. Examiner suggests changing the recitation to “R2”. All claims which depend on clam 1 are objected by virtue of dependency. Appropriate correction is required. Claim 3 is objected to because of the informality in the recitation “R1” in line 1. Examiner suggests changing the recitation to “R1”. Appropriate correction is required. Claim 3 is objected to because of the informality in the recitation “R2” in line 1. Examiner suggests changing the recitation to “R2”. Appropriate correction is required. Claim 6 is 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. 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. (a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention. Claims 1, 4-5, and 8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by HE (CN 117603266 A, see English Machine Translation). Regarding claim 1, HE teaches a chemical compound represented by any one of the structural formulas (see the compound represented by the following compound formula (I), see [0085]-[0092]) comprising: PNG media_image1.png 122 474 media_image1.png Greyscale PNG media_image2.png 94 402 media_image2.png Greyscale PNG media_image3.png 88 406 media_image3.png Greyscale wherein R1 or R is an alkyl group containing at least 1 and no more than 8 carbon atoms or a group of the form -CH2CH2(OCH2CH2)nOCH3, where n is an integer equal to at least 0 and no more than 5, and R2 is ethyl or vinyl (see PNG media_image4.png 112 228 media_image4.png Greyscale , PNG media_image5.png 176 152 media_image5.png Greyscale , see [0087]). Regarding claim 4, Applicant is directed above for a full discussion as applied to claim 1. HE teaches a perovskite film (see the perovskite film with the transparent conductive layer and the hole transport layer, see Fig. 1), comprising: a transparent conducting oxide (TCO) substrate layer (see the transparent conductive layer 2); a perovskite layer (see the perovskite absorber layer 4); and a hole transport layer (see the hole transport layer 3) comprising at least one chemical compound according to claim 1 ([0103] The hole transport layer 3 is formed from any of the hole transport materials mentioned above, such as the compound shown in formula (I); see the compound formula (I) in the rejection of claim 1), disposed between and linking the TCO substrate and the perovskite layer (see Fig. 1). Regarding claim 5, Applicant is directed above for a full discussion as applied to claim 4. HE teaches wherein the at least one compound comprises (2- (9-ethyl-9H-carbazol-3-yl)ethyl)phosphonic acid, (E)-(2-(9-ethyl-9H-carbazol-3- yl)vinyl)phosphonic acid, (E)-(2-(9-ethyl-carbazol-2-yl)vinyl)phosphonic acid, (2-(9-ethyl- carbazol-2-yl)ethyl)phosphonic acid (EtCz2EPA), or a combination thereof (see (2-(9-ethyl-9H-carbazol-3-yl)ethyl)phosphonic acid (see PNG media_image4.png 112 228 media_image4.png Greyscale ), see the rejection of claim 1). Regarding claim 8, Applicant is directed above for a full discussion as applied to claim 4. HE teaches a solar cell (see the perovskite solar cell in Fig. 1), comprising the perovskite film of claim 4 (see the rejection of claim 4). 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 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. Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over HE (CN 117603266 A, see English Machine Translation) as applied claim 1 above, further in view of BRAID (Conjugated Phosphonic Acid Modified Zinc Oxide Electron Transport Layers for Improved Performance in Organic Solar Cells). Regarding claim 3, Applicant is directed above for a full discussion as applied to claim 1. HE teaches R1 is ethyl, R2 is ethyl, and the chemical compound is (2-(9-ethyl-9H-carbazol-3-yl)ethyl)phosphonic acid (see PNG media_image4.png 112 228 media_image4.png Greyscale ), but does not explicitly disclose the claimed “vinyl” in the phosphonic acid substituent ( PNG media_image6.png 80 102 media_image6.png Greyscale ). However, BRAID disclose an improved performance in organic solar cell, wherein the conjugated phosphonic acid ( PNG media_image7.png 78 90 media_image7.png Greyscale , which is (E) type) modified solar cells shows higher power conversion efficiency than the nonconjugated phosphonic acid ( PNG media_image8.png 74 88 media_image8.png Greyscale ) modified devices (see Abstract, Fig. 1, Conclusions), wherein the conjugated linkage led not only to an improvement in work function, but also to increased open circuit voltage, short circuit current, and power conversion efficiency (PCE) of devices compared to the nonconjugated modifier (see P19230). It would have been obvious to one of the ordinary skill in the art before the effective filing date of the claimed invention to have substituted the nonconjugated phosphonic acid ( PNG media_image6.png 80 102 media_image6.png Greyscale ) in HE with the conjugated phosphonic acid ( PNG media_image7.png 78 90 media_image7.png Greyscale , which is (E) type) as taught by BRAID, because the conjugated phosphonic acid ( PNG media_image7.png 78 90 media_image7.png Greyscale , which is (E) type) led not only to an improvement in work function, but also to increased open circuit voltage, short circuit current, and power conversion efficiency (PCE) of solar cell devices compared to the phosphonic acid ( PNG media_image6.png 80 102 media_image6.png Greyscale ), and because the selection of a known material based on its suitability for its intended use supports a prima facie obviousness determination (MPEP 2144). Therefore, modified HE teaches R1 is ethyl, R2 is vinyl, and the chemical compound is (E)-(2-(9-ethyl-9H-carbazol-3-yl)vinyl)phosphonic acid (see the discussion above). Claim 7 is rejected under 35 U.S.C. 103 as being unpatentable over HE (CN 117603266 A, see English Machine Translation) as applied claim 4 above. Regarding claim 7, Applicant is directed above for a full discussion as applied to claim 4. HE teaches a total thickness of between about 500 nm and about 1500 nm ([0101] the thickness of the hole transport layer is 20-200 nm, [0106] The thickness of the transparent conductive layer 2 can be 50-500 nm, [0107] The thickness of the perovskite absorber layer 4 can be 200-1000 nm; Based on the disclosure, the total thickness is calculated as to be 270-1700 nm; Given the teachings above, it would have been obvious to have selected thickness within the disclosed range. In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. See In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990) (see MPEP § 2144.05, I.).). Contact Information Any inquiry concerning this communication or earlier communications from the examiner should be directed to TAE-SIK KANG whose telephone number is 571-272-3190. The examiner can normally be reached on 9:00am – 5:00pm. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Matthew T. Martin can be reached on 571-270-7871. 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. /TAE-SIK KANG/ Primary Examiner, Art Unit 1728
Read full office action

Prosecution Timeline

Apr 03, 2025
Application Filed
Mar 21, 2026
Non-Final Rejection — §102, §103 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
58%
Grant Probability
85%
With Interview (+27.5%)
2y 9m
Median Time to Grant
Low
PTA Risk
Based on 546 resolved cases by this examiner. Grant probability derived from career allow rate.

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