Detailed Action
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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. 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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 01/20/2026 has been entered.
Response to Amendment
Applicant’s Amendment filed 01/20/2026 has been entered and is being considered. Claims 1 and 16 have been amended. Claim 7 has been amended for clarity. Claim 8 has been made independent. No new matter has been added with these amendments.
Response to Arguments
Applicant’s Amendments and arguments based thereon have been considered, and are persuasive or not persuasive as discussed below.
Regarding claims 2-4, the 35 USC 103 rejections are maintained as the arguments/amendments are not considered persuasive. While the Examiner appreciates the time and effort put into preparing the Declaration traversing the rejection, allegations of superior unexpected results must be of both practical and statistical significance and also be commensurate with the scope of the claims.
The Examiner takes no issue with the variable being pointed to – CDU is an important and well-known parameter for optimization and reflects the quality of a finished work product – the results are of practical significance. However, the statistical significance of the examples pointed to in the rejection not entirely clear – the closest prior art, Hatakeyama, also makes CDU a central parameter in the disclosure. At Table 1, Using Polymer 1, a range of CDUs from 2..3-2.9 are achieved – indicating that at least as a point of comparison the compositions of Hatakeyama can be seen to perform at least as well as the inventive compositions pointed to in the Declaration. While the relationship between Applicant’s own internal examples pointed to show a clear relationship of improvement against each other, the ultimate concern is that these examples are to be compared against the closest prior art. The Examiner is open to being convinced otherwise on this evaluation – if Applicant can provide further data and/or rationale as to explain/distinguish between the prior art and their invention and any chemical effects that may confound this particular type of analysis , then the Examiner is perfectly willing to consider these. The Examiner is very aware that chemistry in theory or legal analysis does not always translate perfectly to chemistry as per the benchtop.
However, on the matter of scope of the claims – applicant’s Declaration is restricted to a small subset of examples wherein the X01-L01 structure is an ether linkage or ester linkage and uses this example to provide support by teaching away from the ester linkage. The claim language does encompass other embodiments such as where carbonyl, thiol, and sulfonyl groups are used in place of -CH2- linkages. Further, the Examiner posits that the current claim language does still encompass ester linkages. The claim language at issue reads “L10 represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms with may have a substituent, and a -CH2- included in the hydrocarbon group may be replaced by -O-, -S,-, -SO2-, or -CO-“. The claim language uses “including/having” language (interpreted as “comprising”) and does not explicitly rule out embodiments where multiple -CH2- linkages are replaced with any of the aforementioned groups and/or where these linkages are replaced sequentially – where two sequential -CH2- linkages that have been replaced with -CO- and -O- constitute an ester group. If applicant wishes to exclude ester linkages entirely from the consideration of prior art, amending this claim language herein and elsewhere in the claims would likely be fruitful.
Regarding claim 1 and dependents therefrom, the above arguments substantially are generally applied to the allegations of unexpected results, particularly where the scope of the claims is not commensurate with the narrow scope of examples pointed to. Hatakeyama presents halogens broadly as substituents in both general formulas and in examples, and a person having ordinary skill in the art would consider the substitution of one halogen for another obvious as a matter of chemical similarity.
Regarding Claim 8, the amendments to the claim have significantly changed the scope of the claim and as such new search and consideration require a new grounds of rejection as made in the body of this action.
The amendments to claim 16 have rendered the prior rejection moot and as such the 35 USC 103 rejection thereon is withdrawn. After further consideration of the prior art however, a new rejection is furnished as the subject matter of the amended claim is present in the art used in the prior rejection. This new grounds of rejection is necessitated by Applicant’s amendment.
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.
Claim(s) 1, 5-7 and 9-20 are rejected under 35 U.S.C. 103 as being unpatentable over Nishimura et al (US 20180113382 A1, published 04/26/2018) and Hatakeyama (US 20210149300 A1, published 05/22/2021).
Regarding Claim 1 and 5-7, Nishimura discloses a salt, acid generator, resin, resist composition made therefrom, and a method for producing a resist pattern using the resist composition and components thereof.
Nishimura does not specifically disclose a single experimental embodiment that encompasses the limitations of the claim.
These limitations are met by the general disclosure of the reference.
The reference discloses a salt (I) represented by the formula (1) as presented in [0054], wherein the formula’s limitations are delimited in [0054]-[0084], and specific examples of the anion are disclosed in [0085]. Specific examples are reproduced below – it should be noted these examples are some of many and should not be taken as the sum total of the teachings of the reference relevant to the claims:
PNG
media_image1.png
102
350
media_image1.png
Greyscale
PNG
media_image2.png
154
354
media_image2.png
Greyscale
Anion Ia-13 meets the limitations of the claimed anion for where, in the claim:
Q1 and Q2 are fluorines
Lb1 is a C4 hydrocarbyl group wherein two of the CH2 linkages have been substituted with a successive -O- and -CO- group
Yb1 is an adamantyl group (alicyclic hydrocarbon having 10 atoms) (Claim 5)
X10 represents a -CO-O- group (Claims 6 and 7, where X10 is the claims’ X1-1 group)
L10 represents a C9 hydrocarbon group having 2 separate replacements of -CH2- groups for -O- linkages
Regarding the cation, the cation may be a triphenylsulfonium cation of the salt provided as described from [0086] to [0122], where the cation is a sulfonium that may conform to formula (b2-4).
Nishimura does not disclose a cation that conforms to the limitations of claim 1.
This limitation is met by Hatakeyama.
Hatakeyama discloses a resist composition comprising a base polymer and an acid generator having a sulfonium or iodonium cation and corresponding fluorosulfonic acid anion (abstract).
The acid generator of Hatakeyama is disclosed from [0041]-[0057], where exemplary cations include the following:
PNG
media_image3.png
9
346
media_image3.png
Greyscale
PNG
media_image3.png
9
346
media_image3.png
Greyscale
The above cations meet the limitations of the claim for where, as claimed:
Subscripts m2 and m3 are 0, m1 is 1, m4 is 1/2/5 , m7 is 0, m8 is 0 and m9 is 0
A1 is a C2 hydrocarbon group that has had its -CH2- linkages replaced with sequential -O- and -CO- linkages
R4 is a Fluorine or CF3 group in these instances, which is not Iodine as required by the claim:
However – in describing the sulfonium cation at [0043]-[0050], the sulfonium bearing R3-R5 groups thereupon may bear a C1-C20 hydrocarbyl group that contains at least one heteroatom, where hydrogens may be substituted by at least one halogen. In the examples provided, a variety of halogen substituents, including both F and I, are present on the substituents of the sulfonium cation.
The genus of halogen is (practically speaking) 4 members – Br, Cl, I, and F. A person having ordinary skill in the field would consider the substitution of a general halogen for another halogen with the expectation that such substitution would not substantially change the performance of the compound.
Hatakeyama ascribed improved patterning performance, such as improved line width resolution, to the sulfonium salts disclosed (Abstract).
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by adding a photoacid generator having one of the cations above to the composition of Nishimura to improve patterning performance - such salts will be in admixture with those of Nishimura’s disclosure and through ion exchange would arrive at the claimed invention.
Regarding Claims 9-11, 15, and 18-19, Nishimura and Hatakeyama disclose the limitations of the claim as discussed above regarding claim 1, but do not teach an experimental example of a resin comprising a structural unit meeting the limitations of claim 1.
These limitations are met by the general disclosure of Nishimura, where in [0149] the resin contained in the resist composition of the reference is a resin having a structural unit derived from the salt (I), also described as structural unit (I), where the resin is also referred to as resin (A). The resin may also comprise further structural units such as units comprising an acid labile group ([0152]). The resist composition (see [0498]) further comprises an acid generator that comprises the salt(I) singly or in admixture with a second acid generator (B), where (B) may be a known acid generator in the art.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the filing from the general disclosure of Nishimura, which teaches substantially similar resin and its inclusion in a photoresist, to arrive at a photoresist pattern having excellent resolution.
Regarding Claim 12, Nishimura and Hatakeyama the limitations of the claim as discussed above regarding claim 11, but do not teach an experimental example of a resin comprising a structural unit meeting the limitations of claim 11.
This limitation is met by the general disclosure of Nishimura.
The resin of Nishimura is described from [0149]-[0496], wherein acid labile group-bearing structural units include those described by formula (1) in [0156], formulas (a1-0)- (a1-2) in [0180]-[0208], (a1-4) in [0228]-[0249], among others. Specific examples have been selected from the disclosure for clarity (presented in monomer form or in a chain structure):
PNG
media_image4.png
216
334
media_image4.png
Greyscale
The above meets the limitations of claimed (a1-0) for where:
Ra01 is methyl
La01 is an oxygen -O- linkage
Ra02 and Ra03 are each methyl (C1 alkyl group)
Ra04 is a cyclohexyl group (C6 alicyclic hydrocarbon)
PNG
media_image5.png
180
342
media_image5.png
Greyscale
The above meets the limitations of claimed (a1-1) for where:
Ra4 is methyl
La1 is oxygen -O- linkage
Ra6 is an ethyl group (C2 alkyl)
Subscript m1 is 0
PNG
media_image6.png
152
368
media_image6.png
Greyscale
The above meets the limitations of claimed (a1-2) for where:
Ra5 is methyl
La2 is oxygen
Ra7 is an isopropyl group (C3 alkyl)
Subscripts n1 and n1’ are each 0
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention from the general disclosure of the reference, which teaches subunits that are substantially chemically similar to those claimed – a person of ordinary skill in the art would expect chemically similar compounds to behave similarly, allowing the production of a resist to be used in a high resolution patterning process.
Regarding Claim 13 and 17, Nishimura and Hatakeyama disclose the limitations of the claim as discussed above regarding claim 11 and 1 respectively, but do not teach an experimental example of a resin comprising a structural unit meeting the limitations of claim 11 and 1.
The resin of Nishimura is described from [0149]-[0496], wherein acid labile group-bearing structural units include those described by formula (1) in [0156], formulas (a1-0)- (a1-2) in [0180]-[0208], (a2-0) in [0272]-[0290], among others. Specific examples have been selected from the disclosure for clarity:
PNG
media_image7.png
150
330
media_image7.png
Greyscale
The above reads upon the claimed formula (a2-A) for where:
Ra50 represents a methyl group
Aa50 is a single bond
Subscript mb is 0
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the filing from the general disclosure of Nishimura, which teaches substantially similar salt and its inclusion in a photoresist, to arrive at a photoresist pattern having excellent resolution.
Regarding Claim 14, Nishimura and Hatakeyama disclose the limitations of the claim as discussed above regarding claim 11, but do not teach an experimental example of a resin comprising a structural unit meeting the limitations of the claim.
This limitation is met by the general disclosure of the reference, where the discussion of the resist composition includes presentation of a quencher, where the quencher is a nitrogenous base or a compound that generates an acid lower in acidity than the primary acid generators ([0629]-[00652], such as an onium carboxylate salt.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the filing from the general disclosure of Nishimura, which teaches substantially similar components and their inclusion in a photoresist, to arrive at a photoresist pattern having excellent resolution.
Regarding Claim 16, Nishimura and Hatakeyama the limitations of the claim as discussed above regarding claim 1, but do not teach an experimental example of a resin comprising a structural unit meeting the limitations of claim 1 and as such do not teach an experimental example of claim 16.
These limitations are met by the general disclosure of the reference.
The resin of Nishimura is described from [0149]-[0496], wherein acid labile group-bearing structural units include those described by formula (1) in [0156], formulas (a1-0)- (a1-2) in [0180]-[0208], (a1-4) in [0228]-[0249], and (a3) at [0305]-[0342], among others.
Unit (a3-4) bears the general formula below and is exemplified by compounds disclosed at [0339]:
PNG
media_image8.png
208
332
media_image8.png
Greyscale
.where:
Ra24 is H, halogen, or C1-C6 alkyl or haloalkyl
La7 is a single bond, La8-O, La8-CO-O, La8-CO-O-La9-CO-O, or La8-O-CO-La9-O
La8 and La9 each independently represent a C1-C8 alkanediyl group
Ra25, in each instance, is independently a carboxy group, cyano group, or C1-C4 aliphatic hydrocarbon
Subscript w1 is an integer of 0-8
These structural identifiers are identical in their corresponding structures and also in name (for instance claimed Ra24 is also reference Ra24, claimed La7 is also reference La7) and as such the formula a3-4 above is considered to read on the instant claim as given in the claimed formula.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention from the general disclosure of the reference, which teaches subunits that are substantially chemically similar to those claimed – a person of ordinary skill in the art would expect chemically similar compounds to behave similarly, allowing the production of a resist to be used in a high resolution patterning process.
Regarding Claim 20, Nishimura and Hatakeyama disclose the limitations of the claim as discussed above regarding claim 11, but do not disclose an experimental procedure using the composition of claim 11 to form a patterned resist.
This limitation is met by the general disclosure of the reference.
Nishimura teaches a method for producing a resist pattern in [0656]-[0676], wherein the resist pattern is formed by 1) applying the resist composition to the substrate, 2) drying the applied composition to form a layer, 3)exposing the composition layer, 4) heating the exposed composition layer, and 5) developing the heated composition layer.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention from the general disclosure of Nishimura, such disclosure amounting to a known product (a taught resist composition) used in a known process (a taught patterning method) to achieve a predictable result - a patterned resist having high resolution.
Claims 2-4 are rejected under 35 U.S.C. 103 as being unpatentable over Nishimura et al (US 20180113382 A1, published 04/26/2018), and Hatakeyama et al (US 20210149300 A1).
Regarding Claims 2-4, Nishimura discloses a salt, acid generator, resin, resist composition made therefrom, and a method for producing a resist pattern using the resist composition and components thereof.
Nishimura does not specifically disclose a single experimental embodiment that encompasses the limitations of the claim.
These limitations are met by the general disclosure of the reference.
The reference discloses a salt (I) represented by the formula (1) as presented in [0054], wherein the formula’s limitations are delimited in [0054]-[0084], and specific examples of the anion are disclosed in [0085]. Specific examples are reproduced below – it should be noted these examples are some of many and should not be taken as the sum total of the teachings of the reference relevant to the claims:
PNG
media_image1.png
102
350
media_image1.png
Greyscale
PNG
media_image2.png
154
354
media_image2.png
Greyscale
Anion Ia-13 meets the limitations of the claimed anion for where, in the claim:
Q1 and Q2 are fluorines
Lb1 is a C4 hydrocarbyl group wherein two of the CH2 linkages have been substituted with a successive -O- and -CO- group
Yb1 is an adamantyl group (alicyclic hydrocarbon having 10 atoms) (Claim 5)
X10 represents a -CO-O- group (Claims 6 and 7, where X10 is the claims’ X1-1 group)
L10 represents a C9 hydrocarbon group having 2 separate replacements of -CH2- groups for -O- linkages
Regarding the cation, the cation may be a triphenylsulfonium cation of the salt provided as described from [0086] to [0122], where the cation is a sulfonium that may conform to formula (b2-4).
Nishimura does not disclose a cation that conforms to the limitations of claim 1.
This limitation is met by Hatakeyama.
Hatakeyama discloses a resist composition comprising a base polymer and an acid generator having a sulfonium or iodonium cation and corresponding fluorosulfonic acid anion (abstract).
The acid generator of Hatakeyama is disclosed from [0041]-[0057], where exemplary cations include the following:
PNG
media_image3.png
9
346
media_image3.png
Greyscale
PNG
media_image3.png
9
346
media_image3.png
Greyscale
The above cations meet the limitations of the claim for where, as claimed:
Subscripts m2 and m3 are 0, m1 is 1, m4 is 1/2/5 , m7 is 0, m8 is 0 and m9 is 0
A1 is a C2 hydrocarbon group that has had its -CH2- linkages replaced with sequential -O- and -CO- linkages
R4 is a F atom or a C1 fluoroalkyl group (CF3)
The above cations do not disclose an embodiment corresponding to the claim where A1 is X01-L01 where X01 is a -O-, CO-, S, or SO2- and L01 is a C1-C18 hydrocarbon group.
This limitation is met by Hatakeyama’s general disclosure, which recites that the sulfonium acid generator conforms to formula (A-2), where the sulfonium R groups R3-R5 are each C1-C20 hydrocarbyl groups that may contain a heteroatom and may contain a halogen, haloalkyl, O, N, S, ether, carbonyl, ester, sulfonate ester, or other linkage/substitution mentioned in [0049]. The hydrocarbyl groups are further delimited to include alkyl, aryl, aralkyl, and alkenyl groups – and/or mixtures thereof.
The R groups of the above cations are phenyl (C6) and phenyl-ester-phenyl (C15-C16, where some C have been substituted with O to form the ester). A person of ordinary skill in the art would have found it obvious to consider all structural motifs advanced by the reference – these structural motifs are art-recognized alternatives to one another by nature of their disclosure together. A person of ordinary skill in the art would thus consider the substitution of an ester group for an ether group and the inclusion of a C1-C6 alkylene group between the two phenylene units in one of the above structures as a chemically similar embodiment expected to behave in a manner similar to other embodiments advanced by the reference (MPEP 2144.09), meeting the claim limitation where A1 is -X01-L01- is -O-(C1-C6-alkyl).
Hatakeyama ascribes improved patterning performance, such as improved line width resolution, to the sulfonium salts disclosed (Abstract).
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by adding a photoacid generator having one of the cations above to the composition of Nishimura to improve patterning performance - such salts will be in admixture with those of Nishimura’s disclosure and through ion exchange would arrive at the claimed invention.
Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable over Ohashi (US 20100055608 A1) and Hatakeyama et al (US 20210149300 A1),
Regarding Claim 8,
Ohashi discloses a polymerizable anion-containing sulfonium salt and a resist composition comprising a polymer derived from the sulfonium salt (Abstract).
The salt of Ohashi is disclosed from [0067]-[0073 and the polymerized form is discussed from [0074]-[0081]. Examples of the anion of the salt are provided in [0071]:
PNG
media_image9.png
156
310
media_image9.png
Greyscale
The anion meets the limitations of the claims 1 and 8 for where:
Q1 and Q2 are a fluorine atom
Lb1 is a divalent C4 alkyl group where one carbon is trifluoro-substituted and two CH2 groups have been replaced with a CO-O group
Yb1 is a norbornane or cyclohexane group
L10 is a single bond
X10 is a carboxyl group
While not explicitly a formula assigned to one of X1-2 through X1-8, the chemical structure of X10 as defined here is similar to that of X1-8, where both structures bear carboxyl group functionalities and the linkages of each are cleavable by acid – a person having ordinary skill in the art would consider the additional oxygen to be obvious by way of expecting similar acid lability, as such chemical structural similarity begets similar properties.
Rbb1 is a hydrogen
The anion is paired with a sulfonium cation such as a substituted triphenylsulfonium.
Ohashi does not disclose a cation that conforms to the limitations of claim 1.
This limitation is met by Hatakeyama.
Hatakeyama discloses a resist composition comprising a base polymer and an acid generator having a sulfonium or iodonium cation and corresponding fluorosulfonic acid anion (abstract).
The acid generator of Hatakeyama is disclosed from [0041]-[0057], where exemplary cations include the following:
PNG
media_image3.png
9
346
media_image3.png
Greyscale
PNG
media_image3.png
9
346
media_image3.png
Greyscale
The above cations meet the limitations of the claim for where, as claimed:
Subscripts m2 and m3 are 0, m1 is 1, m4 is 1/2/5 , m7 is 0, m8 is 0 and m9 is 0
A1 is a C2 hydrocarbon group that has had its -CH2- linkages replaced with sequential -O- and -CO- linkages
R4 is a Fluorine or CF3 group
Hatakeyama ascribed improved patterning performance, such as improved line width resolution, to the sulfonium salts disclosed (Abstract).
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention by incorporating the salt of Ohashi into the composition of Hatakeyama. As the resist composition of Nishimura is prepared by dissolving the components into a solvent under mixing conditions, some degree of salt cation-anion exchange is likely to occur, generating the mixed salt using Hatakeyama’s cation and Ohashi’s anion. Additionally and in the alternative, a person of ordinary skill in the art would have found it obvious to exchange one anion for another to attenuate the strength of the acid released – Ohashi’s acid is likely slightly stronger as it bears additional fluoro-substitution and as such it may improve the resolution of the resist pattern.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANDREW PRESTON TRAYWICK whose telephone number is (571)272-2982. The examiner can normally be reached Monday - Friday 8-5.
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.
/A.P.T./Examiner, Art Unit 1737
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734