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 Amendment filed 11/25/2025 has been considered and is entered. Claims 10-12 are added. No new matter is added with these amendments.
Response to Arguments
Applicant’s filing of a Terminal Disclaimer regarding the Non-statutory Double Patenting rejection over copending US Patent Application 18095235 has been accepted. The Non-statutory Double Patenting rejection is withdrawn.
Applicant’s arguments regarding the 35 USC 103 rejections over Aqad, and separately over Aqad in view of LaBeaume are not persuasive. These rejections are maintained.
Applicant argues that the cited compounds are structurally different than the claims. The Examiner agrees; however the rejections were not made solely in view of those cited structures. The Examiner respectfully reminds Applicant that the rejection made was not one of anticipation, but obviousness, and the obviousness rejection was made in view of the entire reference and general teachings thereof. The rejection over Aqad was made in view of the cited structures as a structurally similar embodiment, and the general teachings of the art clearly shows that such groups are interchangeable, and a person of ordinary art could immediately envision an embodiment where both R3 and R4 are, for instance, methyl groups. A person of ordinary skill in the art would find it obvious to use such an embodiment with recognition that the chemical similarity between such structures would render both embodiments similar in performance and compatibility (See MPEP 2144.09). Patents are valid art for all they contain, including teachings of functional groups not explicitly present in a given chemical structure.
Similarly, the rejection over Aqad and LaBeaume is also grounded in the obviousness of structural similarity and taught functional groups that are art-recognized alternatives.
Applicant’s arguments fail to address the obviousness rejections proffered and as such these rejections are maintained. The Examiner suggests that arguments and/or statistically relevant and significant data establishing that the compounds reflected in the claims would behave in a manner superior to the structurally similar and suggested compounds of Aqad and/or LaBeaume would help to advance prosecution.
In view of Applicant’s Amendments to add new claims 10-12, a new grounds of rejection is made – these new grounds are necessitated by these amendments.
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) 1-12 are rejected under 35 U.S.C. 103 as being unpatentable over Aqad (US 20220214614 A1).
Regarding Claims 1 -10 and 12 , Aqad discloses photoacid generators (PAGs) having a moiety of formula (1) (abstract), wherein the generator is used in photoresist compositions for forming patterned resists in electronic devices.
Aqad does not disclose a specific experimental embodiment meeting the limitations of the claims. These limitations are met by the general disclosure of the reference
The PAGs of Aqad are generally disclosed from [0018]-[0031], where the PAG may be a polymer or a discrete monocationic-anionic salt ([0026]-[0028]), where the polymer may be a polyanion or a polycation and the corresponding cation/anion electrostatically associated therewith.
The general formula (1) is preferably embodied by a formula (2-1) as follows:
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Where Ar1 is a substituted or unsubstituted C6-C40 aryl or heteroaryl group, R1 is an alkyl, branched alkyl, cycloalkyl, aryl, or heteroaryl group as described in [0019], Y is a single bond or divalent group as described in [0019], Ar2 represents an arylene group that may or may not be substituted and bear 6-40 carbons thereupon, X is S or I, R2 independently represents a linear/branched/cyclic alkyl group, aryl group, heteroaryl group, or other group as defined in [0021].
Exemplary cations are depicted in [0022]:
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248
568
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210
160
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The above cations meet the limitations of the claimed formula (I) for where:
R8 is a phenyl group (C6 hydrocarbyl group) and s=2
Subscript q=0, subscript p=1
R1 is an ether bond (claim 10)
R2 is a C1 methylene linkage (C1 alkanediyl group) (claim 10)
R5 is a fluorine or iodine, and subscript m=1 (claim 3)
Subscript n=0
R3 or R4 is a methyl, ethyl, or phenyl group
The reference does not explicitly show an instance where both R3 and R4 are a hydrocarbyl group of a particular embodiment. However – the art clearly shows that such groups are interchangeable, and a person of ordinary art could immediately envision an embodiment where both R3 and R4 are, for instance, methyl groups. A person of ordinary skill in the art would find it obvious to use such an embodiment with recognition that the chemical similarity between such structures would render both embodiments similar in performance and compatibility (See MPEP 2144.09).
Exemplary anions (in monomer form) for use in a polymeric anion are shown in [0028]:
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216
44
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180
546
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170
96
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The above anions meet the limitations of claim 2’s claimed formulas (a1) and (a2) where:
X1 is an ester bond
X2 is a methyladamantyl group bonded to a carboxyl group (-X21-C(=O)-), or a single bond (clam 12)
X3 is a methylene or ethylene, or a single bond (claim 12)
Rf1-Rf4 are fluorines, or Rf1 and Rf2 are hydrogens and Rf3 and Rf4 are fluorines
X4 is a fluorinated phenylene ring
The polymerized PAG may be present with other monomer units that are not PAGs, and the PAG-bearing polymer may or may not be present alone or in admixture with other non-PAG polymers ([0033]-[0034]). Example monomers are depicted from [0035]-[0046], and exemplary polymers are depicted from [0047]-[0048].
Exemplary monomers include those depicted below:
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362
356
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310
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Where the above monomers read upon the claimed formula (b1) of Claim 5 where:
RA is a hydrogen or methyl group (see [0041])
Y1 is a single bond or phenyl group
R11 is an acid-labile group
The reference discloses a chemically amplified resist composition, describing a resist that describes acid-labile groups being cleaved during a post-exposure bake process after exposure generates acid from the PAG (claim 6).
The composition of the reference comprises the above PAG and a solvent (claim 4), as well as optional components such as surfactants (claim 7 – see [0066]-[0067]).
The composition of the reference is used in a pattern forming process, wherein the resist is coated onto a substrate and baked to form a film thereupon, then patternwise exposed to radiation such as from a ArF/EB/EUV source (claim 9), and developed using a developer (claim 8) – See [0074]-[0081].
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to filing date from the disclosure of Aqad, which discloses substantially chemically similar embodiments and substantially similar processing methods/parameters, to arrive at a composition and resist having good CDU and minimized patterning defects.
Regarding claim 11, Aqad and Labeaume disclose the limitations of claim 1 as discussed above.
Aqad and Labeaume do not disclose experimental embodiments having structures that would read upon the limitations of the claim where R1 and R2 as depicted in claim 1 are each a single bond.
This limitation is met by the general disclosure of Aqad.
The PAGs of Aqad are generally disclosed from [0018]-[0031], where the PAG may be a polymer or a discrete monocationic-anionic salt ([0026]-[0028]), where the polymer may be a polyanion or a polycation and the corresponding cation/anion electrostatically associated therewith.
The general formula (1) is preferably embodied by a formula (2-1) as follows:
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344
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Where Ar1 is a substituted or unsubstituted C6-C40 aryl or heteroaryl group, R1 is an alkyl, branched alkyl, cycloalkyl, aryl, or heteroaryl group as described in [0019], Y is a single bond or divalent group as described in [0019], Ar2 represents an arylene group that may or may not be substituted and bear 6-40 carbons thereupon, X is S or I, R2 independently represents a linear/branched/cyclic alkyl group, aryl group, heteroaryl group, or other group as defined in [0021].
As discussed above regarding claim 1, Aqad and Labeaume disclose various embodiments that, taken with their general disclosures read upon the claim limitations. Aqad presents the formula above where Y is a single bond or a divalent group – the art recognizes these as alternatives to each other. As such, a person of ordinary skill in the art would find it obvious to consider embodiments of taught compounds where, instead of a divalent group, there is a single bond between the aryl group and the *-(C=O)-O-** group of Aqad. As these art art-recognized alternatives, these substitutions would be expected to perform similarly.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to filing date from the disclosure of Aqad and LaBeaume, which disclose substantially chemically similar embodiments and exemplary art-recognized functional groups thereupon, and also disclose substantially similar processing methods/parameters to arrive at a composition and resist having good CDU and minimized patterning defects.
Claim(s) 1-12 are rejected under 35 U.S.C. 103 as being unpatentable over Aqad (US 20220214614 A1) and LaBeaume (US 20150093709 A1).
Regarding Claims 1 -10 and 12 , Aqad discloses photoacid generators (PAGs) having a moiety of formula (1) (abstract), wherein the generator is used in photoresist compositions for forming patterned resists in electronic devices.
Aqad does not disclose a specific experimental embodiment meeting the limitations of the claims. These limitations are met by the general disclosure of the reference
The PAGs of Aqad are generally disclosed from [0018]-[0031], where the PAG may be a polymer or a discrete monocationic-anionic salt ([0026]-[0028]), where the polymer may be a polyanion or a polycation and the corresponding cation/anion electrostatically associated therewith.
The general formula (1) is preferably embodied by a formula (2-1) as follows:
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120
344
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Where Ar1 is a substituted or unsubstituted C6-C40 aryl or heteroaryl group, R1 is an alkyl, branched alkyl, cycloalkyl, aryl, or heteroaryl group as described in [0019], Y is a single bond or divalent group as described in [0019], Ar2 represents an arylene group that may or may not be substituted and bear 6-40 carbons thereupon, X is S or I, R2 independently represents a linear/branched/cyclic alkyl group, aryl group, heteroaryl group, or other group as defined in [0021].
Exemplary cations are depicted in [0022]:
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248
568
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210
160
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The above cations meet the limitations of the claimed formula (I) for where:
R8 is a phenyl group (C6 hydrocarbyl group) and s=2
Subscript q=0, subscript p=1
R1 is an ether bond
R2 is a C1 methylene linkage (C1 alkanediyl group)
R5 is a fluorine or iodine, and subscript m=1 (claim 3)
Subscript n=0
R3 or R4 is a methyl, ethyl, or phenyl group
The reference does not explicitly show an instance where both R3 and R4 are a hydrocarbyl group of a particular embodiment.
This limitation is met by Labeaume, which discloses acid generators having a carbocyclic aryl or heteroaromatic group substituted with acetate moieties (abstract), wherein the acid generators may be sulfonium salts such as those depicted below:
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98
302
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98
302
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Wherein the above cations meet the limitations of the claim where
R8 is a phenyl group (C6 hydrocarbyl group) and s=2, and the two phenyl groups may be bound together with a bond
Subscript q=0, subscript p=1
R1 is an ether bond
R2 is a C1 methylene linkage (C1 alkanediyl group) (claim 10)
Subscript m=0
Subscript n=0
R3 and R4 may be methyl groups, or may be a methyl group and a trifluoropropyl group
Ar is a phenyl group
A person of ordinary skill in the art would recognize these sulfonium cations and the functional groups thereupon as art-directed alternatives to each other, and would find it obvious to select functional groups from Aqad and LaBeaume with the expectations that such substitutions (such as using two methyl groups on the R3/R4 positions of Aqad’s generators, or using an I/F on the terminal phenyl group of LaBeaume ) would result in substantially similarly behaving cations for acid generation.
Exemplary anions (in monomer form) for use in a polymeric anion are shown in [0028]:
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216
44
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180
546
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170
96
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The above anions meet the limitations of claim 2’s claimed formulas (a1) and (a2) where:
X1 is an ester bond
X2 is a methyladamantyl group bonded to a carboxyl group (-X21-C(=O)-), or a single bond (clam 12)
X3 is a methylene or ethylene, or a single bond (claim 12)
Rf1-Rf4 are fluorines, or Rf1 and Rf2 are hydrogens and Rf3 and Rf4 are fluorines
X4 is a fluorinated phenylene ring
The polymerized PAG may be present with other monomer units that are not PAGs, and the PAG-bearing polymer may or may not be present alone or in admixture with other non-PAG polymers ([0033]-[0034]). Example monomers are depicted from [0035]-[0046], and exemplary polymers are depicted from [0047]-[0048].
Exemplary monomers include those depicted below:
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362
356
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242
310
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Where the above monomers read upon the claimed formula (b1) of Claim 5 where:
RA is a hydrogen or methyl group (see [0041])
Y1 is a single bond or phenyl group
R11 is an acid-labile group
The reference discloses a chemically amplified resist composition, describing a resist that describes acid-labile groups being cleaved during a post-exposure bake process after exposure generates acid from the PAG (claim 6).
The composition of the reference comprises the above PAG and a solvent (claim 4), as well as optional components such as surfactants (claim 7 – see [0066]-[0067]).
The composition of the reference is used in a pattern forming process, wherein the resist is coated onto a substrate and baked to form a film thereupon, then patternwise exposed to radiation such as from a ArF/EB/EUV source (claim 9), and developed using a developer (claim 8) – See [0074]-[0081].
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to filing date from the disclosure of Aqad and LaBeaume, which disclose substantially chemically similar embodiments and exemplary art-recognized functional groups thereupon, and also disclose substantially similar processing methods/parameters to arrive at a composition and resist having good CDU and minimized patterning defects.
Regarding claim 11, Aqad and Labeaume disclose the limitations of claim 1 as discussed above.
Aqad and Labeaume do not disclose experimental embodiments having structures that would read upon the limitations of the claim where R1 and R2 as depicted in claim 1 are each a single bond.
This limitation is met by the general disclosure of Aqad.
The PAGs of Aqad are generally disclosed from [0018]-[0031], where the PAG may be a polymer or a discrete monocationic-anionic salt ([0026]-[0028]), where the polymer may be a polyanion or a polycation and the corresponding cation/anion electrostatically associated therewith.
The general formula (1) is preferably embodied by a formula (2-1) as follows:
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120
344
media_image1.png
Greyscale
Where Ar1 is a substituted or unsubstituted C6-C40 aryl or heteroaryl group, R1 is an alkyl, branched alkyl, cycloalkyl, aryl, or heteroaryl group as described in [0019], Y is a single bond or divalent group as described in [0019], Ar2 represents an arylene group that may or may not be substituted and bear 6-40 carbons thereupon, X is S or I, R2 independently represents a linear/branched/cyclic alkyl group, aryl group, heteroaryl group, or other group as defined in [0021].
As discussed above regarding claim 1, Aqad and Labeaume disclose various embodiments that, taken with their general disclosures read upon the claim limitations. Aqad presents the formula above where Y is a single bond or a divalent group – the art recognizes these as alternatives to each other. As such, a person of ordinary skill in the art would find it obvious to consider embodiments of taught compounds where, instead of a divalent group, there is a single bond between the aryl group and the *-(C=O)-O-** group of Aqad. As these art art-recognized alternatives, these substitutions would be expected to perform similarly.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to filing date from the disclosure of Aqad and LaBeaume, which disclose substantially chemically similar embodiments and exemplary art-recognized functional groups thereupon, and also disclose substantially similar processing methods/parameters to arrive at a composition and resist having good CDU and minimized patterning defects.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
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/A.P.T./Examiner, Art Unit 1737
/JONATHAN JOHNSON/Supervisory Patent Examiner, Art Unit 1734
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