Prosecution Insights
Last updated: April 19, 2026
Application No. 18/277,366

RESIN, COMPOSITION, RESIST PATTERN FORMATION METHOD, CIRCUIT PATTERN FORMATION METHOD AND METHOD FOR PURIFYING RESIN

Non-Final OA §102§103
Filed
Aug 15, 2023
Examiner
EOFF, ANCA
Art Unit
1722
Tech Center
1700 — Chemical & Materials Engineering
Assignee
Mitsubishi Gas Chemical Company Inc.
OA Round
1 (Non-Final)
80%
Grant Probability
Favorable
1-2
OA Rounds
2y 10m
To Grant
91%
With Interview

Examiner Intelligence

Grants 80% — above average
80%
Career Allow Rate
982 granted / 1230 resolved
+14.8% vs TC avg
Moderate +11% lift
Without
With
+11.3%
Interview Lift
resolved cases with interview
Typical timeline
2y 10m
Avg Prosecution
48 currently pending
Career history
1278
Total Applications
across all art units

Statute-Specific Performance

§101
0.2%
-39.8% vs TC avg
§103
47.1%
+7.1% vs TC avg
§102
20.0%
-20.0% vs TC avg
§112
20.0%
-20.0% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1230 resolved cases

Office Action

§102 §103
DETAILED ACTION The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Claims 1-26 are pending. The foreign priority document No.2021-022454 filed on February 16, 2021 in Japan has been received and it is acknowledged. Claim Rejections - 35 USC § 102 The following is a quotation of the appropriate paragraph of 35 U.S.C. 102 that form s 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. Claim s 1-8, 10-14, 16-22, and 24-26 are rejected under 35 U.S.C. 102 (a)(1) as being anticipated by Makinoshima et al. (US 2017/0073288). With regard to claim s 1 , 3, and 4 , Makinoshima et al. teach a resin having a structure of formula (2): . wherein R 1 is a 2n-valent group having 1 to 30 carbon atoms, each of R 2 to R 5 is a linear, branched or cyclic alkyl group having 1-10 carbon atoms, an aryl group having 2 to 10 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a thiol group or a hydroxyl group, each of m 2 and m 3 is independently an integer of 0 to 8, each of m 4 and m 5 is an integer of 0 to 9, n is an integer of 1 to 4, each of p 2 to p 5 is independently an integer of 0 to 2 (par.0031-0032 , par.0097 ). This resin is derived from a compound of formula (1): ,wherein R 1 is a 2n-valent group having 1 to 30 carbon atoms, each of R 2 to R 5 is a linear, branched or cyclic alkyl group having 1-10 carbon atoms, an aryl group having 2 to 10 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, a thiol group or a hydroxyl group, each of m 2 and m 3 is independently an integer of 0 to 8, each of m 4 and m 5 is an integer of 0 to 9, n is an integer of 1 to 4, each of p 2 to p 5 is independently an integer of 0 to 2 (par.0021-0022 , par.0097 ). A specific example of the compound of formula (1) is (BiF-1): (par.0209), and this compound produces a resin (BiFP- 2)( par.0227). The resin (BiFP-2) is a resin comprising a unit of formula (1) in claim s 1 , 3, and 4 , wherein n=1, R 1 is a divalent linking group with 13 carbon atoms, A is a single bond, p 2 -p 5 =0, m 4 =0, m 5 =0, m 2 -m 5 = 1, R 2 -R 5 are hydroxyl groups. The resin (BiFP-2) is also a resin comprising a unit of formula (1’) in claims 1, 3, and 4, wherein n 0 =1, R 1 ’ is a divalent linking group with 13 carbon atoms, A is a single bond, p 2 -p 5 =0, m 4 =0, m 5 =0, m 2 -m 5 =1, R 2 -R 5 are hydroxyl groups. With regard to claim 2, the resin (BiFP-2) is a resin comprising a unit of formula (2), wherein R 1 ’ is a divalent linking group with 13 carbon atoms, A is a single bond, p 2 -p 5 =0, m 4 =0, m 5 =0, m 2 -m 5 =1, R 2 -R 5 are hydroxyl groups. With regard to claim 5, the resin (BiFP-2) is a resin comprising a unit of formula (2a), wherein n A =1, R 1 A is a divalent linking group with 13 carbon atoms, R 4A and R 5A are hydroxyl groups, m 2A =0 , m 3A =0, m 4A =1, and m 5A =1. With regard to claim 6, the resin (BiFP-2) is a resin comprising a unit of formula (2b), wherein R 1 A’ is a divalent linking group with 13 carbon atoms, R 4A and R 5A are hydroxyl groups, m 2A =0, m 3A =0, m 4A =1, and m 5A 1. With regard to claim 7, the resin (BiFP-2) is a resin comprising a unit of formula (3b), wherein n 0 =1. With regard to claim 8, Makinoshima et al. teach that the resin may be a copolymer of a compound formula (1) with a copolymerizable phenol or copolymerizable monomer other than phenols (par.0114-0115) . With regard to claim 10, the resin (BiFP-2) is a resin comprising a block unit of formula (4), wherein k is a positive integer, n=1, R 1 is a divalent linking group with 13 carbon atoms, A is a single bond, p 2 -p 5 =0, m 4 =0, m 5 =0, m 2 -m 5 =1, R 2 -R 5 are hydroxyl groups , and L is a divalent group derived from biphenylaldehyde (divalent group with 13 carbon atoms). With regard to claim 11, the resin (BiFP-2) is a resin comprising a block unit of formula (5), wherein k is a positive integer, n=1, R 1 ’ is a divalent linking group with 13 carbon atoms, A is a single bond, p 2 -p 5 =0, m 4 =0, m 5 =0, m 2 -m 5 =1, R 2 -R 5 are hydroxyl groups , and L is a divalent group derived from biphenylaldehyde (divalent group with 13 carbon atoms). With regard to claim 12, the resin (BiFP-2) is a resin comprising a block unit of formula (5a), wherein k is a positive integer, n A =1, R 1 A is a divalent linking group with 13 carbon atoms, R 4A and R 5A are hydroxyl groups, m 2A =0, m 3A =0, m 4A =1, m 5A =1 , and L is a divalent group derived from biphenylaldehyde (divalent group with 13 carbon atoms). With regard to claim 13, the resin (BiFP-2) is a resin comprising a block unit of formula (5b), wherein k is a positive integer, R 1 A’ is a divalent linking group with 13 carbon atoms, R 4A and R 5A are hydroxyl groups, m 2A =0, m 3A =0, m 4A =1, m 5A =1 , and L is a divalent group derived from biphenylaldehyde (divalent group with 13 carbon atoms). With regard to claim 14, Makinoshima et al. teach that the resin may be a copolymer of a compound formula (1) with a copolymerizable phenol or copolymerizable monomer other than phenols (par.0114-0115). With regard to claims 16 and 17, Makinoshima et al. teach a material comprising the resin and an organic solvent (par.0035). With regard to claims 18 and 19, Makinoshima et al. teach that the material further comprises an acid generator and a crosslinking agent (par.0036-0037). The examiner would like to note that the limitations of claims 20-22 are directed to an intended use of the material. Therefore, these limitations do not add any patentable weight to the claims. The material of Makinoshima et al. anticipates the material in claims 20-22 of the instant application. With regard to claim 24, Makinoshima et al. teach a resist pattern forming method comprising: -forming an underlayer on a substrate by using the material for forming an underlayer film; -forming a photoresist layer on the underlayer film; -irradiating a predetermined region of the photoresist layer with radiation, followed by development with an alkali (par.0039-0042). With regard to claim 25, Makinoshima et al. teach a circuit pattern forming method comprising: -forming an underlayer film on a substrate by using the material for forming an underlayer film; -forming an intermediate film on the underlayer; -forming a photoresist layer on the intermediate film; -irradiating a predetermined region of the photoresist layer with radiation, followed by development with an alkali to form a resist pattern; -etching the intermediate layer using the resist pattern as etching mask, etching the underlayer film with an obtained intermediate layer film pattern as an etching mask, and etching the substrate with an obtained underlayer film pattern as etching mask to form a pattern on the substrate (par.0043-0048). With regard to claim 26, Makinoshima et al. teach a method of purifying the resin, the method comprising a step of bring ing a solution comprising an organic solvent immiscible with water and the resin into contact with an acid aqueous solution for extraction (par.0049-0050). Claim s 1-6, 8, 10-16, 16-23, 25, and 26 are rejected under 35 U.S.C. 102 (a)(1) as being anticipated by Makinoshima et al. (WO 2020/0158931, with citations from the English language equivalent US 2022/0144738). With regard to claims 1, 3, and 4 , Makinoshima et al. teach a resin comprising a structure of formula (2-1): (par.0077), which is derived from a compound of formula (1): (par.0074, par.0032). Makinoshima et al. specifically teach a resin derived from BiP-1 and benzaldehyde, wherein BiP-1 is represented by the formula: (par.0460, Example A1 in Table 1, par.0462). The compound BiP-1 is a compound (1) (see par.0298). Therefore, the resin in Example A1 is a resin comprising a constituent unit of formula (1) in claims 1, 3, and 4, wherein n = 1, R 1 is a divalent linking group with 7 carbon atoms, m 2 -m 5 =2, one group R 2 -R 5 is hydroxy, one group R 2 -R 5 is a linear alkyl group with 1 carbon atom, p 2 -p 5 =0, and A is a single bond. With regard to claim 2, the resin in Example A1 is a resin comprising a constituent unit of formula (2), wherein R 1 ’ is a divalent linking group with 7 carbon atoms, m 2 -m 5 =2, one group R 2 -R 5 is hydroxy, one group R 2 -R 5 is a linear alkyl group with 1 carbon atom, p 2 -p 5 =0, and A is a single bond. With regard to claim 5, the resin in Example A1 is a resin comprising a constituent unit of formula (2a), wherein R 1A is a divalent linking group with 7 carbon atoms, m 2A = 1,m 5A =1, R 2A and R 5A are linear alkyl groups with 1 carbon atom, m 4A =2, m 5A =2, one group R 4A and one group R 5A are hydroxyl groups, one group R 4A and one group R 5A are linear alkyl groups with 1 carbon atom. With regard to claim 6, the resin in Example A1 is a resin comprising a constituent unit of formula (2a), wherein R 1A ’ is a divalent linking group with 7 carbon atoms, m 2A = 1,m 5A =1, R 2A and R 5A are linear alkyl groups with 1 carbon atom, m 4A =2, m 5A =2, one group R 4A and one group R 5A are hydroxyl groups, one group R 4A and one group R 5A are linear alkyl groups with 1 carbon atom. With regard to claim 8, Makinoshima et al. teach that the resin may be a copolymer of a compound formula (1) with a copolymerizable phenol or copolymerizable monomer other than phenols (par.0344-0345). With regard to claim 10, the resin in Example A1 is a resin comprising a block unit of formula (4), wherein k is a positive integer, n=1, R 1 is a divalent linking group with 7 carbon atoms, m 2 -m 5 =2, one group R 2 -R 5 is hydroxy, one group R 2 -R 5 is a linear alkyl group with 1 carbon atom, p 2 -p 5 =0, A is a single bond, L is a divalent linking bond with 7 carbon atoms (divalent linking bond derived from benzaldehyde). With regard to claim 11, the resin in Example A1 is a resin comprising a block unit of formula (5), wherein k is a positive integer, R 1 ’ is a divalent linking group with 7 carbon atoms, m 2 -m 5 =2, one group R 2 -R 5 is hydroxy, one group R 2 -R 5 is a linear alkyl group with 1 carbon atom, p 2 -p 5 =0, A is a single bond, L is a divalent linking bond with 7 carbon atoms (divalent linking bond derived from benzaldehyde). With regard to claim 12, the resin in Example A1 is a resin comprising a block unit of formula (5 a ), wherein k is a positive integer, n A =1, R 1 A is a divalent linking group with 7 carbon atoms, m 2A =1,m 5A =1, R 2A and R 5A are linear alkyl groups with 1 carbon atom, m 4A =2, m 5A =2, one group R 4A and one group R 5A are hydroxyl groups, one group R 4A and one group R 5A are linear alkyl groups with 1 carbon atom, L is a divalent linking bond with 7 carbon atoms (divalent linking bond derived from benzaldehyde). With regard to claim 13, the resin in Example A1 is a resin comprising a block unit of formula (5b), wherein k is a positive integer, R 1 A’ is a divalent linking group with 7 carbon atoms, m 2A =1,m 5A =1, R 2A and R 5A are linear alkyl groups with 1 carbon atom, m 4A =2, m 5A =2, one group R 4A and one group R 5A are hydroxyl groups, one group R 4A and one group R 5A are linear alkyl groups with 1 carbon atom, L is a divalent linking bond with 7 carbon atoms (divalent linking bond derived from benzaldehyde). With regard to claim 14, Makinoshima et al. teach that the resin may be a copolymer of a compound formula (1) with a copolymerizable phenol or copolymerizable monomer other than phenols (par.0344-0345). With regard to claims 16 and 17, Makinoshima et al. teach a composition comprising the resin and a solvent (par.0079-0080). With regard to claims 18 and 19, Makinoshima et al. teach that the composition comprises an acid generating agent and a crosslinking agent (par.0081-0082). The examiner would like to note that the limitations of claims 20-22 are directed to an intended use of the material. Therefore, these limitations do not add any patentable weight to the claims. The composition of Makinoshima et al. anticipates the material in claims 20-22 of the instant application. With regard to claim 23, Makinoshima et al. teach a pattern forming method comprising the steps of: -forming a photoresist film on a substrate using the composition including the resin; -irradiating a predetermined region of the photoresist film and developing to form a pattern (par.0090-0092). With regard to claim 25, Makinoshima et al. teach a circuit pattern forming method comprising: -forming an underlayer film on a substrate using the composition including the resin; -forming an intermediate film on the underlayer; -forming a photoresist layer on the intermediate film; -irradiating a predetermined region of the photoresist layer with radiation, followed by development with an alkali to form a resist pattern; -etching the intermediate layer using the resist pattern as etching mask, etching the underlayer film with an obtained intermediate layer film pattern as an etching mask, and etching the substrate with an obtained underlayer film pattern as etching mask to form a pattern on the substrate (par.00 93-100 ). With regard to claim 26, Makinoshima et al. teach a method of purifying the resin, the method comprising a step of bring ing a solution comprising the resin and an organic solvent that does not inadvertently mix with water into contact with an acid aqueous solution for extraction (par.0 101-0102 ). 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. Claim s 9 and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Makinoshima et al. (WO 2020/0158931, with citations from the English language equivalent US 2022/0144738). With regard to claim 9 , Makinoshima et al. teach the resins of claim 1 and 10 (see paragraph 6 above), but fail to teach that the resin comprises one of the claimed constituent unit . However, Makinoshima et al. teach that fluorenone may be used for a condensation reaction with a compound of formula (1) in order to obtain a resin (par.0 335, par.0337 ). A compound of formula (1) may be : (par.0298). Therefore, it would have been obvious to one of ordinary skill in the art before the filing date of the claimed invention to obtain a resin by condensing a compound of formula (BiP-1) and fluorenone. A resin obtain by condensation of with fluorenone comprises a constituent unit of formula (U1) wherein Ar U1 and Ar U2 are phenyl rings, R U1 and R U2 are hydrogen atoms . Conclusion The prior art made of record and not relied upon is considered pertinent to applicant's disclosure: Makinoshima et al. (US 2020/0361843) teach a resin comprising a structure of formula (2): wherein A is a group containing a heteroatom, R 1 is a 2n-valent group having 1 to 30 carbon atoms, R 2 -R 5 may be hydroxyl groups, m 2 and m 3 are integers from 0 to 9, m 4 and m 5 are integers from 0 to 9, n is integer from 1 to 4, p 2 -p 5 are integers from 1 to 2, wherein L is a single bind or a linking group (par.0030-0032, par.0038) , Any inquiry concerning this communication or earlier communications from the examiner should be directed to FILLIN "Examiner name" \* MERGEFORMAT ANCA EOFF whose telephone number is FILLIN "Phone number" \* MERGEFORMAT (571)272-9810 . The examiner can normally be reached FILLIN "Work Schedule?" \* MERGEFORMAT Mon-Fri 10am-6:30pm . 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, FILLIN "SPE Name?" \* MERGEFORMAT Niki Bakhtiari can be reached at FILLIN "SPE Phone?" \* MERGEFORMAT (571)272-3433 . 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. /ANCA EOFF/ Primary Examiner, Art Unit 1722
Read full office action

Prosecution Timeline

Aug 15, 2023
Application Filed
Feb 26, 2026
Non-Final Rejection — §102, §103 (current)

Precedent Cases

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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
80%
Grant Probability
91%
With Interview (+11.3%)
2y 10m
Median Time to Grant
Low
PTA Risk
Based on 1230 resolved cases by this examiner. Grant probability derived from career allow rate.

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