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.
Response to Amendment
Applicant’s Amendments filed 12/29/2025 have been entered and are being considered. Claim 1 has been amended to change the scope of the claim. Claims 1-22 have been amended for clarity.
Response to Arguments
Applicant’s Amendments and arguments based thereon have rendered the Objections and rejections raised over 35 USC 112(b) moot. These are each withdrawn.
Regarding Applicant’s Amendment to claim 1 changing the scope of the claim to where at least one of R1/2/3 is a -O-R10, -O-CO-O-R10, or -O-L1-CO-O-R10 group, the Examiner submits that this limitation is still met by the instant references and the prior rejection furnished in the previous office action.
As was set forth in the prior office action, the group R3 corresponds to the claimed R1 as described in the body of the action below, where R3 in the reference may be a group hydroxy group, C1-C20 alkoxy, or C2-C20 alkoxycarbonyl group, where the C1-C20 alkyl group in the alkoxy or alkoxycarbonyl group corresponds to an acid labile group R10. Claim 1 did not and still does not further delimit “an acid-labile group”. Claim 6 does further delimit the metes and bounds of the acid labile group, and claim 6 was rejected as set forth in the prior office action.
The group R10 is an acid-labile group by nature of being attached to the ring system by an oxo or acyloxo/oxycarbonyl group (-O-R10, *-CO-O-R10). Hatakeyama teaches both of these attachment groups when it describes R3 as an alkoxy group or an alkoxycarbonyl group wherein the “alk” refers to the alkyl group that then corresponds to claimed variable R10. These alkoxy or alkoxycarbonyl groups are acid-cleavable.
Pointing to specific examples of compounds that do not meet the claim limitations is not persuasive when the basis for the rejection is not grounded in those examples. Patent publications are prior art for all they contain and the rejection made in the prior office action was made on the basis of the general formula where taught examples may be considered instructive but not the sole teaching.
In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). The rejection over 35 USC 103 made is predicated on the ability of a person having ordinary skill in the art to arrive at the claimed invention through the combination of Hatakeyama and Ichikawa to arrive at an improved composition as set forth in the rejection.
Regarding Applicant’s assertions of unexpected superior results, the Examiner reminds Applicant that the standards for unexpected superior results are that the results be of both statistical and practical significance, and must be commensurate with the scope of the claims. The Examiner readily agrees that the assertions are of practical significance – LER is a processing parameter that is important to the performance of patterned resists. Applicant’s data appears statistically significant with an 8% improvement over the comparative example. However, the examples presented as evidence of unexpected results represent a very small set of embodiments in a very broadly defined genus of potential compounds and are thus not commensurate with the scope of the claims. There is a very large number of compounds that are encompassed by the claim language that are not represented among the examples presented as evidence of unexpected results, and the Examiner is unable to say that each and every one of those unrepresented compounds would show the same property improvements that applicant presents herein.
After further search and consideration, the 35 USC 103 rejections of claims 1-22 are maintained.
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) 1-22 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al (US 20200089112 A1) and Ichikawa et al (US 20110014566 A1).
Regarding Claims 1-12, Hatakeyama teaches a resist composition comprising a base polymer and a sulfonium salt quencher (Abstract).
The sulfonium salt of the quencher is described from [0045]-[0064].
PNG
media_image1.png
136
490
media_image1.png
Greyscale
R1 and R2 are each a single bond o C1-C20 divalent aliphatic hydrocarbon that may have an ether/ester/hydroxyl moeity, where the moiety may be straight, branched, or cyclic
L1 is an ester bond, ether bond, or amide bond. L2 and L3 are each independently a single bond, ester bond, ether bond, or amide bond
R3 is a hydroxyl, carboxyl, nitro, fluoro, chloro, bromo, amino, C1-C20 alkyl, C1-C20 alkoxy, C2-C20 acyloxy, C2-C20 alkoxycarbonyl to C1-C4 alkylsulfonyloxy group which may be substituted with halogen, amino, or hydroxyl, or an -NR3d-C(=O)-R3B or -NR3A-C(=O)-O-R3B, where R3A is H or C1-C6 alkyl that may have halogens, C1-C10 alkoxy, C2-C10 acyl or acyloxy, R3B is a C1-C6 alkyl, C2-C16 alkenyl or C6-C12 aryl, which may contain a halogen, C1-C10 alkoxy, C2-C10 acyl or acyloxy moeity.
R4 is a hydroxyl, carboxyl, nitro, cyano, fluorine, bromine, chlorine, iodine, hydroxyl, amino, or ether
Examples of alkyl group, alkoxy groups, acyl groups, acyloxy groups, alkoxycarbonyl groups, alkenyl groups, and aryl groups are given in[0051-[0057]
R5 is a C1-C20 monovalent hydrocarbon group which may contain a heteroatom. The monovalent hydrocarbon group may be straight, branched or cyclic, and examples thereof include C1 -C20 alkyl groups, C2-C20 alkenyl groups, C2-C24 alkynyl groups, C6-C20 aryl groups, C7 -C20 aralkyl groups, and combinations thereof. In these groups, some or all hydrogen may be substituted by hydroxyl moiety, carboxyl moiety, halogen, cyano moiety, amino moiety, nitro moiety, sultone ring-containing moiety, sulfone moiety or sulfonium salt-containing moiety, or an ether bond, ester bond, carbonyl moiety, sulfide bond, sulfonyl moiety or amide moiety may intervene in a carbon-carbon bond.
When subscript r=1, two R5 may be bonded together to form a ring with the sulfur atom, where the ring includes a structure such as those below:
PNG
media_image2.png
99
302
media_image2.png
Greyscale
PNG
media_image2.png
99
302
media_image2.png
Greyscale
PNG
media_image3.png
108
174
media_image3.png
Greyscale
The salt cation has an X- anion, where X- is a carboxylic acid, amic acid anion, non-fluorinated sulfonic acid anion, or halide anion.
Subscript m is 1-5, n is an integer of 0-3, p is 0 or 1, q is an integer of 0-4, and r is an integer of 1-3
The cation of Hatakeyama reads upon the claimed cation of claim 1 for where:
X4 is a single bond, methylene group, -S-, -O-, -CO-, -SO-, or -SO2- ( where reference’s r is 1, and the two R5 are phenyl)
R1 is a hydroxy group, C1-C20 alkoxy, or C2-C20 alkoxycarbonyl group, where the C1-C20 alkyl group in the alkoxy or alkoxycarbonyl group corresponds to an acid labile group R10
Regarding claim 6, the disclosure discloses that alkyl groups (such as those on an alkoxy group or alkoxycarbonyl group) may be straight, branched, or cyclic, such as t-butyl and neopentyl, which meet the limitations of claim 6 for where the acid-labile group (1a) bears Raa1 and Raa3 as methyl groups and Raa2 is a methyl or ethyl group (see reference [0049]-[0057])
R4 is an iodine atom, and subscript m4 is 0-4
A1 is a C1-C20 hydrocarbon group that has an ester or ether bond therein (wherein a methylene group is replaced by -O- or a successive substitution of -CO- and -O-) ( for example - in the reference – R1, L2, and L3 are each a single bond, L1 is an ester bond or ether bond, R2 is a C1-C20 divalent aliphatic hydrocarbon group – other configurations exist but are not described here for brevity)
Regarding claim 2 and claim 3, this reads upon the claim limitation for where A1 is -X01-L01- where X01 is a -O- and L01 is a hydrocarbon having 1-18 carbons having -CO- substitution or optionally not having such -CO- substitution
For when the hydrocarbon have 1-6 carbon atoms, claim 4 is met
Regarding claim 5, Hatakeyama’s cation may bear a variety of substituents across the organic groups attached to the sulfur of the sulfonium cation – a person of ordinary skill in the art would find it obvious to arrive at an embodiment where r=3 and two of the aryl groups therein directly attached to the sulfur ring are bonded – such chemical structure would be similar to the non-conjoined species and likely to behave in a way similar to such – therefore an embodiment where each of R1-R3 are independently a hydroxy group or OR10 moeity.
Hatakeyama does not present a carboxylic acid anion that meets the limitations of the claim. This limitation is met by Ichikawa, which discloses a salt having the general formula :
PNG
media_image4.png
224
360
media_image4.png
Greyscale
Where further description of the anion is given from [0014]-[0022], including drawn-out examples:
PNG
media_image5.png
398
370
media_image5.png
Greyscale
Where the anions above read on the claimed anion for where:
Rbb1 is H or methyl
X10 is a -CO-O group (claims 10 and 11 – X10-1)
L10 is a single bond (claim 12)
X0 is a chain hydrocarbon group (methylene linkage) or an alicyclic hydrocarbon group (adamantyl – C10, cyclohexyl – C6) group (claim 7, 8, and 9)
Cations corresponding to the anion above are described and depicted from [0023]-[0046], where the cation is a sulfonium or iodonium, preferably a sulfonium.
The reference Ichikawa ascribes good line-edge roughness in photoresist patterns that contain the salt described.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed intention by substituting the carboxylic acid anion of Hatakeyama for that of Ichikawa to arrive at a composition exhibiting improved line edge roughness in a resultant photoresist.
Regarding Claims 13-22, Hatakeyama and Ichikawa disclose the limitations of the claim as discussed above regarding claim 1.
Hatakeyama and Ichikawa however do not disclose explicit experimental embodiments meeting the limitations of the claim to a carboxylic acid generator comprising the carboxylate according to claim 1 or a structural unit derived therefrom.
This limitation is met by the general disclosure of Ichikawa.
Ichikawa discloses at [0049]-[0050] the polymer of the disclosure comprises a structural unit derived from the salt of the disclosure, (I-Pa) (claims 13 and 14). In [0091], the salt (I-Pa) as disclosed is also comprised in the composition as a free salt (claim 13 and 15).
Ichikawa describes the composition of the reference as having the salt (i-Pa) and a base resin. The base resin of Ichikawa may be one that comprises the salt-unit (I-Pa) and a structural unit that has an acid-labile group on its side chain ([0052]-[0083] – claim 16-18).
The base resin of Ichikawa comprises subunits having an acid-labile group conforming to formula 10 and the claimed limitations of claim 19:
PNG
media_image6.png
178
384
media_image6.png
Greyscale
The above formula is further described from [0058]-[0083], where groups that meet the limitations of the Ra1-Ra3 groups above include methyl, ethyl, propyl, among others – or when combining two of Ra1-Ra3 - 2-alkyl-2-adamantyl, 2-alkyl-2-cycloheptyl, and 2-alkyl-2-cyclohexyl, or other cyclic groups described in the cited sections.
Where specific examples of the structural unit include those recited from [0063]-[0083], such as but not limited to 2-methyl-2-adamantyl methacrylate, which reads upon the claimed formula (a1-1) for where Ra4 is a methyl group, La1 is an -O-, Ra6 is a methyl group, and m1’ is 0.
The reference’s general disclosure further meets the limitations of claim 19’s (a1-0) where Ra02-Ra04 are each a C1-C8 alkyl group, C3-C18 alicyclic hydrocarbon group, or a group bonded together; Ra01 is a hydrogen or methyl group; La01 is an O linkage.
The reference’s general disclosure also meets the limitations of the claim 19 for formula (a1-2) where Ra5 is a hydrogen or methyl group, La2 is a O linkage, Ra7 is a C1-C8 alkyl group, and subscript n1’ is an integer of 0-3, and m1’ is 0.
Further comprised in the resin may be a structural unit comprising a hydroxyl group such as p-hydroxystyrene, which reads upon the claim limitations of claim 20 for where Ra50 is H, Aa50 is a single bond, and mb is an integer of 0.
The resist composition of Ichikawa further comprises an acid generator, described from [0091]-[0114], which conforms to the general formula (I):
PNG
media_image7.png
348
368
media_image7.png
Greyscale
Where the reference’s salt reads upon the claimed salt of claim 21 for where:
-Q1 and Q2 are each independently a fluorine atom or a C1-C4 perfluoroalkyl group
- Lb1 is a saturated hydrocarbon group having 1-17 carbon atoms, where a methylene group may be replaced by an oxy or carbon group
-Y is C1-C24 hydrocarbon group that is alicyclic and may have a methylene group therein substituted with an oxy or carbonyl group.
- Z+ is an organic cation.
The reference Ichikawa ascribes good line-edge roughness in photoresist patterns that contain the salt described and to the composition at large.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed intention by incorporating the salt of Hatakeyama and Ichikawa as well as the compositional elements of Ichikawa into the composition of Hatakeyama to arrive at a composition exhibiting improved line edge roughness in a resultant photoresist .
Regarding Claim 22, Hatakeyama and Ichikawa disclose the limitations of the claim as discussed above regarding claim 15.
Hatakeyama and Ichikawa fail to disclose an explicit experimental embodiment where the composition of claim 15 is applied to a method for a resist pattern as delimited in the body of the claim.
This limitation is met by Hatakeyama, which teaches a pattern formation process involving the application of a resist composition onto a substrate, then baking to form a composition layer (resist film), then exposing the resist film to radiation such as EB, DUV, EUV, gamma-ray, or other radiation. After exposure, the resist film is heated and developed ([00127]-[0135].
A person of ordinary skill in the art would have found it obvious to apply the processing method taught by Hatakeyama to the composition of Hatakeyama and Ichikawa – such application constitutes practicing a known and art-directed process with an art-recognized material to arrive at a predictable result (a patterned resist) with a reasonable expectation that such practice would work.
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 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
Prosecution Insights