Prosecution Insights
Last updated: April 18, 2026
Application No. 17/490,923

IODINE-CONTAINING ACID CLEAVABLE COMPOUNDS, POLYMERS DERIVED THEREFROM, AND PHOTORESIST COMPOSITIONS

Non-Final OA §103
Filed
Sep 30, 2021
Examiner
MALLOY, ANNA E
Art Unit
1737
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Rohm And Haas Electronic Materials LLC
OA Round
5 (Non-Final)
45%
Grant Probability
Moderate
5-6
OA Rounds
3y 7m
To Grant
41%
With Interview

Examiner Intelligence

Grants 45% of resolved cases
45%
Career Allow Rate
218 granted / 481 resolved
-19.7% vs TC avg
Minimal -4% lift
Without
With
+-4.1%
Interview Lift
resolved cases with interview
Typical timeline
3y 7m
Avg Prosecution
52 currently pending
Career history
533
Total Applications
across all art units

Statute-Specific Performance

§101
0.6%
-39.4% vs TC avg
§103
47.5%
+7.5% vs TC avg
§102
17.2%
-22.8% vs TC avg
§112
22.2%
-17.8% vs TC avg
Black line = Tech Center average estimate • Based on career data from 481 resolved cases

Office Action

§103
DETAILED ACTION Claims 1, 2, 5, 6, 9-11, 16, 19, and 24-27 are pending. Claims 1, 2, 5, 6, and 9 have been amended, claims 3, 4, 7, 8, 12-15, 17, 18, and 20-23 have been canceled, and claims 24-27 have been added. 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 was filed in this application after a decision by the Patent Trial and Appeal Board, but before the filing of a Notice of Appeal to the Court of Appeals for the Federal Circuit or the commencement of a civil action. 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examination under 37 CFR 1.114 and the fee set forth in 37 CFR 1.17(e) has been timely paid, the appeal has been withdrawn pursuant to 37 CFR 1.114 and prosecution in this application has been reopened pursuant to 37 CFR 1.114. Applicant’s submission filed on March 13, 2026 has been entered. 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 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 1, 2, 5, 6, 9-11, 16, 19, and 24-27 are rejected under 35 U.S.C. 103 as being unpatentable over Kita et al. (JP2021130808) as evidenced by Aqad et al. (U.S. 10,495,968). Translation previously provided. Kita et al. teaches a resin comprising a structural unit denoted by formula (I) and a structural unit denoted by formula (III) [0009] in which a specific example of formula (I) includes the following formula (I-21): PNG media_image1.png 257 182 media_image1.png Greyscale [0026] which is equivalent to a second repeating unit comprising a tertiary alkyl ester group of instant claims 1, 26, and 27; and a specific example of formula (III) includes the following formula (III-30): PNG media_image2.png 181 144 media_image2.png Greyscale [0040] which is structurally similar to a compound and polymer comprising a repeating unit derived from said compound of formula (1) of instant claims 1, 2, 5, 6, 12, 15, 16, 19, 24, and 25 when X is an unsubstituted C2 alkenyl which does not have an acid-labile group, L1 is a single bond, k is 1, Ar1 is C6 aryl, m is 1, L2 is -C(O)OC(X1X2)- where X1 and X2 are hydrogen, and R1 is represented by Formula (2) when R2 is an unsubstituted C2 alkyl and R3 and R4 are unsubstituted alkyl which form a ring via a single bond which is unsubstituted, except that n is 0 and therefore missing iodine. However, Kita et al. teaches formula (III) can be defined as the following: PNG media_image3.png 118 324 media_image3.png Greyscale [0034] wherein R11 expresses a hydrogen atom or a methyl group, R12, R13, and R14 are independently alkyl groups of the carbon numbers 1-8, alkenyl group of the carbon numbers 2-8, alicyclic hydrocarbon group of the carbon numbers 3-20, aromatic hydrocarbon group of the carbon numbers 6-18, or these, or R12 and R13 combined to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with a carbon atom to which they are bonded, X11 can be a single bond, X12 can be *-CO-O-L12- where L12 can be an alkanediyl group of 1 carbon number and * expresses the joint hand of Ar11, Ar11 expresses the aromatic hydrocarbon group of the carbon numbers 6-20 which may have a substituent [0034] and as an aromatic hydrocarbon group in Ar11, a phenylene group is mentioned. The basis illustrated as a substituent which Ar1 and Ar2 may have as a substituent which Ar11 may have, and the same basis are mentioned [0037] and as a substituent of an aromatic hydrocarbon group, they can be a halogen atom, [0011] and examples of the halogen atom include an iodine atom [0011]. Furthermore, as evidenced by Aqad et al., the iodine atom has remarkably higher absorption cross-section at EUV. Iodine-containing resins and corresponding resist compositions with improved photoresist sensitivity at EUV. The sensitivity improvement was achieved by incorporating iodine atoms onto the resist resin, while extending chain of the iodine-containing monomers improved their incorporation in the resin [col 5 lines 57-65]. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the specific teachings of Kita et al. to include additional structural units which include an iodine substituent through routine experimentation of selecting suitable variables for the sought invention in order to improve sensitivity. Kita et al. also taches the content of structural unit (III) in resin (A) is 3-80 mol % is preferable to the whole structure unit of (A) [0042] which overlaps the instantly claimed range of 0.1 to 10 mol% (claim 6). In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976). Kita et al. further teaches the resin (A) may be a polymer containing one or more structural units other than a structural unit (I) and a structural unit (III). Structural units (I) and structural units (III) other than structural units (I), structural units (hereinafter referred to as "structural units (a1)") having acid-labile groups other than structural units (I) and structural units (III), structural units other than structural units having an acid-labile group (hereinafter referred to as "structural units (a4)"), structural units having no acid-labile groups other than structural units (I) (hereinafter referred to as "structural units (s)"), A structural unit having a non-desorbed hydrocarbon group (hereinafter referred to as a "structural unit (a 5)"), etc. may be cited. Here, the acid-labile group has a leaving group, and the leaving group is desorbed by contact with an acid to mean a group forming a hydrophilic group (e.g. a hydroxy group or a carboxy group) [0043] wherein the structural unit (s) is derived from a monomer having no acid-labile group (hereinafter referred to as "monomer (s)"). The monomer that guides the structural unit (s) can use a monomer that does not have an acid-labile group known in the field of resist. The structural unit (s) preferably has a hydroxy group or a lactone ring. When a resin having a hydroxy group and having no acid-labile group (hereinafter referred to as "structural unit (a2)") and/or a lactone ring and having no acid-labile group (hereinafter referred to as "structural unit (a3)") is used in the resist composition of the present invention, it is possible to improve the resolution of the resist pattern and the adhesion with the substrate [0073] wherein structural unit (a3) is a structural unit denoted by the formula (a3-1), the formula (a3-2), the formula (a3-3), or a formula (a3-4) preferably [0088] which are the following: PNG media_image4.png 215 707 media_image4.png Greyscale [0088] wherein La4, La5, and La6 express independently the basis denoted by -O- or *-O-(CH2)k3-CO-O- (k3 expresses the integer of either 1-7.), respectively among [type (a3-1), a formula (a3-2), a formula (a3-3), and a formula (a3-4). La7 expresses -O-, *-O-La8-O-, *-O-La8-CO-O-, *-O-La8-CO-O-La9-CO-O-, or *-O-La8-O-CO-La9-O-. La8 and La9 express the alkanediyl group of the carbon numbers 1-6 independently, respectively. * Express at least combination with a carbonyl group. Ra18, Ra19, and Ra20 express a hydrogen atom or a methyl group independently, respectively. Ra24 expresses the alkyl group, hydrogen atom, or halogen atom of the carbon numbers 1-6 which may have a halogen atom. Xa3 expresses -CH2- or an oxygen atom. Ra21 expresses the aliphatic hydrocarbon group of the carbon numbers 1-4. Ra22, Ra23, and Ra25 express a carboxy group, a cyano group, or the aliphatic hydrocarbon group of the carbon numbers 1-4 independently, respectively. P1 expresses the integer of either 0-5. Q1 expresses the integer of either 0-3. R1 expresses the integer of either 0-3. W1 expresses the integer of either 0-8. When p1, q1, r1, and/or w1 are two or more, a plurality of Ra21, Ra22, Ra23, and/or Ra25 may be each other the same, or they may differ [0088] which are equivalent to a third repeating unit comprising a polar group pendant to a backbone of the polymer which is a lactone of instant claim 1. Kita et al. further teaches the resin which consists of structural unit (I), structural unit (III), and a structural unit (s) [0162] which meets the “consisting of” claim language of instant claim 1. Kita et al. also teaches as for the resist composition of the present invention, it is preferable resin (A) and to contain a publicly known acid generator (it may be called the following "acid generator (B)") in the resist field. The resist composition of the present invention may contain resin other than resin (A) further. As for the resist composition of the present invention, it is preferable to contain quenchers (it may be called the following "quencher (C)"), such as a salt which generates acid whose acidity is weaker than acid generated from an acid generator, and it is preferable to contain a solvent (it may be called the following "solvent (E)") [0165] (claims 9 and 10). Kita et al. further teaches a manufacturing method of the resist pattern of the present invention: (1) The process of applying the resist composition of the present invention on a substrate, (2) The process of drying the constituent after application and forming a constituent layer, (3) The process exposed in a constituent layer, (4) the process of heating the constituent layer after exposure and (5) Include the process of developing the constituent layer after heating [0232] (claim 11). Kita et al. also teaches the present invention makes it problem to provide the resin in which CD homogeneity (CDU) forms a good resist pattern rather than the resist pattern formed with the resist composition which contains the (prior art) resin [0005]. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the specific teachings of Kita et al. to include additional resist compositions comprising a resin having the above defined structural units and arrive at the instant claims through routine experimentation of combining equally suitable components for the sought invention in order to achieve optimum CDU and pattern formed. Response to Arguments Applicant's arguments filed March 13, 2026 have been fully considered but they are not persuasive. Applicant argues Kita discloses polymers having a structural unit denoted by formula (I) and formula (III). Kita does not disclose, teach, or suggest a polymer as recited by amended claim 1 that consists of the requisite repeating units. Aqad cannot remedy the noted deficiency of Kita. Further, there would have been no guidance in the disclosure of Kita t derive the subject matter of amended claim 1, Kita teaches a multitude of other repeating units may be present in the polymer but provides no direction to select a combination as claimed. The Examiner respectfully disagrees. Kita teaches in paragraph [0162] several variations of the inventive polymer comprising different repeating units. Specifically, Kita teaches “the resin which consists of structural unit (I), structural unit (III), and a structural unit (s)” [0162] in which specific examples of formula (I) correspond to the instantly claimed second repeating unit having an acid labile group (i.e. formula I-21) [0026], formula (III) corresponds to the instantly claimed first repeating unit of formula (1) [0034] and [0040], and specific examples of (s) include lactone rings [0088] which corresponds to the instantly claimed third repeating unit having a polar group selected from a lactone group. Therefore, the instant claims are still obvious over the entire disclosure of Kita as evidenced by Aqad. Conclusion The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. JP2020070435 and U.S. 2013/0084438. Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANNA E MALLOY whose telephone number is (571)270-5849. The examiner can normally be reached 8:00-4:30 EST M-F. 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, Mark Huff can be reached at 571-272-1385. 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. /Anna Malloy/Examiner, Art Unit 1737 /MARK F. HUFF/Supervisory Patent Examiner, Art Unit 1737
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Prosecution Timeline

Sep 30, 2021
Application Filed
Jun 11, 2023
Non-Final Rejection — §103
Sep 18, 2023
Response Filed
Nov 29, 2023
Final Rejection — §103
Jan 19, 2024
Response after Non-Final Action
Jan 31, 2024
Request for Continued Examination
Feb 04, 2024
Response after Non-Final Action
Feb 28, 2024
Non-Final Rejection — §103
Jun 06, 2024
Response Filed
Sep 11, 2024
Final Rejection — §103
Nov 13, 2024
Response after Non-Final Action
Dec 03, 2024
Notice of Allowance
Jan 27, 2025
Response after Non-Final Action
Feb 13, 2025
Response after Non-Final Action
Apr 01, 2025
Response after Non-Final Action
May 19, 2025
Response after Non-Final Action
May 24, 2025
Response after Non-Final Action
May 26, 2025
Response after Non-Final Action
May 27, 2025
Response after Non-Final Action
Jan 12, 2026
Response after Non-Final Action
Mar 13, 2026
Request for Continued Examination
Mar 17, 2026
Response after Non-Final Action
Mar 23, 2026
Non-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

5-6
Expected OA Rounds
45%
Grant Probability
41%
With Interview (-4.1%)
3y 7m
Median Time to Grant
High
PTA Risk
Based on 481 resolved cases by this examiner. Grant probability derived from career allow rate.

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