Prosecution Insights
Last updated: April 19, 2026
Application No. 18/189,081

ORGANIC COMPOUND AND ELECTROCHROMIC ELEMENT

Final Rejection §103
Filed
Mar 23, 2023
Examiner
CHIEN, LUCY P
Art Unit
2871
Tech Center
2800 — Semiconductors & Electrical Systems
Assignee
Canon Kabushiki Kaisha
OA Round
3 (Final)
83%
Grant Probability
Favorable
4-5
OA Rounds
2y 9m
To Grant
88%
With Interview

Examiner Intelligence

Grants 83% — above average
83%
Career Allow Rate
745 granted / 898 resolved
+15.0% vs TC avg
Moderate +5% lift
Without
With
+5.2%
Interview Lift
resolved cases with interview
Typical timeline
2y 9m
Avg Prosecution
34 currently pending
Career history
932
Total Applications
across all art units

Statute-Specific Performance

§103
55.9%
+15.9% vs TC avg
§102
38.7%
-1.3% vs TC avg
§112
1.3%
-38.7% vs TC avg
Black line = Tech Center average estimate • Based on career data from 898 resolved cases

Office Action

§103
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 . Response to Arguments Response to Arguments Applicant's arguments filed 2/4/2026 have been fully considered but they are not persuasive. Applicant’s arguments that R3,R5-R10 are alkyl, that is incorrect. R3, R5-R10 *can be* H. They can be other moieties also. But when R3, R5-R10 are H, R4 is F, R1 and R2 are Alkyl, that matches the compound recited in the claims. Therefore, the rejection is maintained. 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. Claim(s) 1-10 is/are rejected under 35 U.S.C. 103 as being unpatentable over (JP2018508034A) Regarding Claim 1, (JP2018508034A) discloses (Also pasted below) wherein, PNG media_image1.png 138 270 media_image1.png Greyscale in formula (1), X1 and X2 are each independently selected from the group consisting of a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and a substituted or unsubstituted aralkyl group; and A1- and A2- each independently represent a monovalent anion. In the reference, you can find what compounds are for these: R1,R2 = Alkyl R4 = F X = Anion so can be PF6- (“…n one aspect, an electrochromic device comprising a non-dimerized electrochromic compound represented by formula (I) is provided.In Formula I, R 1 and R 2 are each alkyl, siloxyalkyl, hydroxyalkyl, alkenyl, or aralkyl, and R 4 , R 6 , R 8 , and R 10 are H, OR 20 , F, Cl, respectively. , Br, I, CN, NO 2 , alkyl, or aryl, and R 3 , R 5 , R 7 , and R 9 are H, OH, F, Cl, Br, I, CN, NO 2 , alkyl, respectively. Or aryl, R 20 is H or alkyl, and X is an anion. However, formula (I) indicates that R 3 and R 5 , or R 7 and R 9 , or R 3 , R 5 , R 7 , and R 9 are each secondary alkyl, tertiary alkyl, or aryl. Condition. In one aspect, an electrochromic device comprising a non-dimerized electrochromic compound represented by formula (III) is provided. In formula (III), R 1 and R 2 are each alkyl, siloxyalkyl, hydroxyalkyl, alkenyl, or aralkyl, and R 4 , R 6 , R 8 , R 10 are each H, OR 20 , F, Cl, Br, I, CN, NO 2 , alkyl, or aryl, and R 3 , R 5 , R 7 , and R 9 are each H, OH, F, Cl, Br, I, CN, NO 2 , Alkyl or aryl, R 19 is (CH 2 ) n ′ , or arylene, R 20 is H or alkyl, n ′ is 1 to 12, and X is an anion, wherein R 3 and R 5 , or R 7 and R 9 are each secondary alkyl, tertiary alkyl, or aryl…”) It would have been obvious to one of ordinary skill in the art that you would pick and choose the compounds for R1,R2,R4, from a given list. PNG media_image2.png 268 552 media_image2.png Greyscale Regarding Claim 2, (JP2018508034A) discloses (Also pasted above) wherein, in formula (1), X1 and X2 have an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 14 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. (“… As used herein, an “alkyl” group is from 1 to about 20 carbon atoms, and typically 1 to 12 carbon atoms, or in some embodiments 1 to 8 carbon atoms…”) Regarding Claim 3, (JP2018508034A) discloses (Also pasted above) wherein, in formula (1), X1 and X2 have a n-heptyl group, a phenyl group, or a benzyl group. (“… As used herein, an “aryl” or “aromatic” group is a cyclic aromatic hydrocarbon that does not contain heteroatoms. Aryl groups include monocyclic, bicyclic, and polycyclic ring systems. Thus, aryl groups include, but are not limited to, phenyl, azulenyl, heptaenyl, biphenylenyl, indacenyl, fluorenyl, phenanthrenyl, triphenylenyl, pyrenyl, naphthacenyl, chrysenyl, biphenyl…”) Regarding Claim 4, (JP2018508034A) discloses (Also pasted above) wherein, in formula (1), X1 and X2 have the same structure. Regarding Claim 5, (JP2018508034A) discloses (Also pasted above) wherein, in formula (1), A1- and A2- are each independently selected from the group consisting of PF6-. (“…X is an anion that can be, but is not limited to, halide, borate, fluoroborate, tetraarylborate, hexafluorometal or metalloid, sulfate, sulfonate, sulfonamide, carboxylate, perchlorate, tetrachloroferrate, and the like. Exemplary X groups include, but are not limited to: F − , Cl − , Br − , I − , BF 4 − , PF 6 –…”) Regarding Claim 6, (JP2018508034A) discloses (Also pasted above) wherein, in formula (1), A1- and A2- are each independently selected from the group consisting of PF6- and BF4-.(“…X is an anion that can be, but is not limited to, halide, borate, fluoroborate, tetraarylborate, hexafluorometal or metalloid, sulfate, sulfonate, sulfonamide, carboxylate, perchlorate, tetrachloroferrate, and the like. Exemplary X groups include, but are not limited to: F − , Cl − , Br − , I − , BF 4 − , PF 6 –…”) Regarding Claim 7, (JP2018508034A) discloses (Also pasted above) wherein, in formula (1), A1- and A2- represent the same anion. (“…In one aspect, an electrochromic device comprising a non-dimerized electrochromic compound represented by formula (I) is provided.In Formula I, R 1 and R 2 are each alkyl, siloxyalkyl, hydroxyalkyl, alkenyl, or aralkyl, and R 4 , R 6 , R 8 , and R 10 are H, OR 20 , F, Cl, respectively. , Br, I, CN, NO 2 , alkyl, or aryl, and R 3 , R 5 , R 7 , and R 9 are H, OH, F, Cl, Br, I, CN, NO 2 , alkyl, respectively. Or aryl, R 20 is H or alkyl, and X is an anion. However, formula (I) indicates that R 3 and R 5 , or R 7 and R 9 , or R 3 , R 5 , R 7 , and R 9 are each secondary alkyl, tertiary alkyl, or aryl. Condition…”) Regarding Claim 8, (JP2018508034A) discloses (Also pasted above) wherein, in formula (1), X1 and X2 have an ionic group, an adsorptive group, or an acid ester group (“…X is an anion that can be, but is not limited to, halide, borate, fluoroborate, tetraarylborate, hexafluorometal or metalloid, sulfate, sulfonate, sulfonamide, carboxylate, perchlorate, tetrachloroferrate, and the like. Exemplary X groups include, but are not limited to: F − , Cl − , Br − , I − , BF 4 − , PF 6 − , SbF 6 − , AsF 6 − , ClO 4 − , SO 3 CF 3 − , N (CN) 2 − , N (CF 3 SO 2) 2 -, C (CF 3 SO 2) 3 -, N (SO 2 C 2 F 5) 2 -, - Al (OC (CF 3) 3) 4 or, - BAr 4, wherein, Ar is An aryl or fluorinated aryl group. In one embodiment, X - is - BAr is 4, Ar is pentafluorophenyl group. In some embodiments, X is tetrafluoroborate or a bis (trifluoromethylsulfonyl) imide anion. Where indicated for any compound herein, the plurality of Xs may be a mixture of two or more such anions...”) Regarding Claim 9, (JP2018508034A) discloses (Also pasted above) wherein, in formula (1), the ionic group, the adsorptive group, or the acid ester group has a carboxyl group, a sulfonic acid group, a phosphonic acid group, a trialkoxysilyl group, a carboxylic acid ester group, a sulfonic acid ester group, a phosphonic acid ester group, a pyridinium group, or a quinolinium group. (“…X is an anion that can be, but is not limited to, halide, borate, fluoroborate, tetraarylborate, hexafluorometal or metalloid, sulfate, sulfonate, sulfonamide, carboxylate, perchlorate, tetrachloroferrate, and the like. Exemplary X groups include, but are not limited to: F − , Cl − , Br − , I − , BF 4 − , PF 6 − , SbF 6 − , AsF 6 − , ClO 4 − , SO 3 CF 3 − , N (CN) 2 − , N (CF 3 SO 2) 2 -, C (CF 3 SO 2) 3 -, N (SO 2 C 2 F 5) 2 -, - Al (OC (CF 3) 3) 4 or, - BAr 4, wherein, Ar is An aryl or fluorinated aryl group. In one embodiment, X - is - BAr is 4, Ar is pentafluorophenyl group. In some embodiments, X is tetrafluoroborate or a bis (trifluoromethylsulfonyl) imide anion. Where indicated for any compound herein, the plurality of Xs may be a mixture of two or more such anions...”) Regarding Claim 10, (JP2018508034A) discloses (Also pasted above) wherein, in formula (1), X1 and X2 have a phosphonic acid group, a carboxylic acid ester group, a phosphonic acid ester group, or a pyridinium group. (“…X is an anion that can be, but is not limited to, halide, borate, fluoroborate, tetraarylborate, hexafluorometal or metalloid, sulfate, sulfonate, sulfonamide, carboxylate, perchlorate, tetrachloroferrate, and the like. Exemplary X groups include, but are not limited to: F − , Cl − , Br − , I − , BF 4 − , PF 6 − , SbF 6 − , AsF 6 − , ClO 4 − , SO 3 CF 3 − , N (CN) 2 − , N (CF 3 SO 2) 2 -, C (CF 3 SO 2) 3 -, N (SO 2 C 2 F 5) 2 -, - Al (OC (CF 3) 3) 4 or, - BAr 4, wherein, Ar is An aryl or fluorinated aryl group. In one embodiment, X - is - BAr is 4, Ar is pentafluorophenyl group. In some embodiments, X is tetrafluoroborate or a bis (trifluoromethylsulfonyl) imide anion. Where indicated for any compound herein, the plurality of Xs may be a mixture of two or more such anions...”) Claim(s) 11-18,21,22 is/are rejected under 35 U.S.C. 103 as being unpatentable over (JP2018508034A) in view of Yashiro Tohru et al (CN 102666778A) Regarding Claim 11, (JP2018508034A) discloses everything as disclosed above. (JP2018508034A) does not disclose a pair of electrodes; and an electrochromic layer [0024] disposed between the pair of electrodes, wherein the electrochromic layer contains the organic compound according to Claim 1 Yashiro Tohru et al discloses a pair of electrodes; and an electrochromic layer [0024] disposed between the pair of electrodes, wherein the electrochromic layer contains the organic compound according to Claim 1. It would have been obvious to one of ordinary skill in the art to modify (JP2018508034A) to include the organic compounds in Yashiro Tohru et al’s electrochromic layer motivated by the desire to provide a color display with a sharp light absorption spectrum characteristic [0027]. Regarding Claim 12, In addition to (JP2018508034A) and Yashiro Tohru et al, Yashiro Tohru et al discloses wherein the electrochromic layer [0129] contains the organic compound and a second organic compound. Regarding Claim 13, In addition to (JP2018508034A) and Yashiro Tohru et al, Yashiro Tohru et al discloses wherein the second organic compound is selected from the group consisting of a phenazine-based compound, a metallocene-based compound, a phenylenediamine-based compound, and a pyrazoline-based compound.[0182] Regarding Claim 14, In addition to (JP2018508034A) and Yashiro Tohru et al, Yashiro Tohru et al discloses wherein the electrochromic layer further contains an electrolyte.[0077] Regarding Claim 15, In addition to (JP2018508034A) and Yashiro Tohru et al, Yashiro Tohru et al discloses wherein the electrochromic layer further contains a thickener.[0225] Regarding Claim 16, In addition to (JP2018508034A) and Yashiro Tohru et al, Yashiro Tohru et al discloses wherein the thickener is polymethyl methacrylate, polyethylene oxide, or polypropylene oxide.[0225] Regarding Claim 17, In addition to (JP2018508034A) and Yashiro Tohru et al, Yashiro Tohru et al discloses the electrochromic element according to Claim 11; and an active element connected to the electrochromic element [0129]. Regarding Claim 18, In addition to (JP2018508034A) and Yashiro Tohru et al, Yashiro Tohru et al discloses wherein the active element drives the electrochromic element to adjust an amount of light passing through the electrochromic element [0129]. Regarding Claim 21, In addition to (JP2018508034A) and Yashiro Tohru et al, Yashiro Tohru et al discloses a pair of substrates; the electrochromic element [0129] according to Claim 11 disposed between the pair of substrates; and an active element connected to the electrochromic element. Regarding Claim 22, In addition to (JP2018508034A) and Yashiro Tohru et al, Yashiro Tohru et al discloses An electrochromic mirror comprising: a pair of substrates; the electrochromic element [0129] according to Claim 11 disposed between the pair of substrates (11,12); an active element [0230]connected to the electrochromic element; and a reflective member. 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. Claim(s) 19,20, is/are rejected under 35 U.S.C. 103 as being unpatentable over (JP2018508034A) and of Yashiro Tohru et al (CN102666778A) in view of Kubo et al (US 20200233277) Regarding Claim 19, (JP2018508034A) and Yashiro Tohru et al discloses everything as disclosed above. (JP2018508034A) and Yashiro Tohru et al does not disclose the optical filter according to Claim 17; and an image pickup optical system having a plurality of lenses. Kubo et al discloses the optical filter (101) according to Claim 17; and an image pickup optical system having a plurality of lenses.[0121] It would have been obvious to one of ordinary skill in the art to modify (JP2018508034A) and Yashiro Tohru et al to include Kubo et al’s lenses motivated by the desire to adjust the amount of light that passes through or has passed through the image pickup optical system [0121]. Regarding Claim 20, In addition to (JP2018508034A) and Yashiro Tohru et al and Kubo et al, Kubo et al discloses and an image pickup element configured to receive light that has passed through the optical filter.[0121] Conclusion THIS ACTION IS MADE FINAL. 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 LUCY P CHIEN whose telephone number is (571)272-8579. The examiner can normally be reached 9AM-5PM PST Monday, Tuesday, and Wednesday. 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 supervisor, Michael Caley can be reached at 571-272-2286. 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. /LUCY P CHIEN/Primary Examiner, Art Unit 2871
Read full office action

Prosecution Timeline

Mar 23, 2023
Application Filed
Jul 25, 2025
Non-Final Rejection — §103
Oct 08, 2025
Response Filed
Nov 06, 2025
Non-Final Rejection — §103
Feb 04, 2026
Response Filed
Feb 25, 2026
Final Rejection — §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

4-5
Expected OA Rounds
83%
Grant Probability
88%
With Interview (+5.2%)
2y 9m
Median Time to Grant
High
PTA Risk
Based on 898 resolved cases by this examiner. Grant probability derived from career allow rate.

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