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 12/11/2025 has been entered and is being considered. Claims 1 and 5 have been amended. Claim 21 has been added. No new matter has been added with these amendments.
Response to Arguments
Applicant’s Amendments and arguments based thereon have changed the scope of the claims and as such the prior rejections made over 35 USC 103 are considered moot. These rejections are withdrawn.
However, after further search and consideration, the Examiner makes a new grounds of rejection over 35 USC 102(a)(1) and (a)(2), and further in view of 35 USC 103, as set forth in the office action below. Applicant’s amendment necessitated the new grounds of rejection.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form 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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1, 3, 6, and 8-11 is/are rejected under 35 U.S.C. 102(a)(1) and (a)(2) as being anticipated by Kobayashi et al (US 20060160023 A1).
Regarding Claim 1, 3, 6, and 8-11, Kobayashi discloses a high resolution resist material comprising an acid generator and a base resin. Kobayashi ascribes high sensitivity and small line-edge roughness to the composition comprising the novel acid generator and base resin.
The base resin is described from [0026]-[0055], and may include components such as polyhydroxystyrene, polymethacrylic acid, or other components such as those mentioned in the cited paragraphs.
The acid generator is generally described at Formula (1) and [0020]-[025], and separately a second embodiment at [0056]-[0084].
Solvents, surfactants, quenchers, and other additives are discussed from [0085]-[0129].
In the Experimental Examples 3 and 30, PAG 3 is used:
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Polymers 1 and 21 are used in these examples:
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The resins each bear acid-labile subunits, and as such the polarity of the resin increased by acid-induced decomposition (claim 6)
The examples 3 and 30 are dissolved in PGMEA solvent (claim 8), and formed into a resist film (claim 9).
The salt PAG 3 meets the limitations of the claim where:
Cation
Lx is -O- (claim 3)
Rx11-Rx16 are each H, and subscripts m and n are each 2
Arx is an aryl group, specifically phenyl
Anion (AN5)
Ar is a phenyl group
Subscript n is 1
D is a sulfonic ester linkage
B is a toluene group
Example 3 was coated onto a silicon substrate having an antireflective coating thereatop, and prebaked at 110 degrees Celsius for one minute so as to form a resist film, then exposed to ArF radiation and baked. After baking, development was performed using an aqueous TMAH solution.
Example 30 was treated approximately the same way as Example 3, except exposed to KrF radiation (claim 10)
Regarding Claim 11, the method of the claim recites only the pattern forming method of claim 10 as a positive limitation. “for manufacturing an electronic device” in the preamble is considered “intended use”. As the method of claim 10 has been anticipated, claim 11 is also anticipated.
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 1-4, 6-13, and 15-20 are rejected under 35 U.S.C. 103 as being unpatentable over Kobayashi et al (US 20060160023 A1).
Regarding Claims 1-4, 6-13, and 15-20, Kobayashi discloses a high resolution resist material comprising an acid generator and a base resin. Kobayashi ascribes high sensitivity and small line-edge roughness to the composition comprising the novel acid generator and base resin.
The acid generator is generally described at Formula (1), 0015] and [0020]-[025], and separately a second embodiment at [0056]-[0084].
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Where:
X- is a nonnucleophilic counterion having 1-20 carbon atoms, such as an arylsulfonate like benzene sulfonate or alkylsulfonate such as butanesulfonate
R1 and R2 are a hydrogen or linear/branched/cyclic C1-C8 alkyl group,
Y represents a single bond or a bond to N/O/C1-C4 alkylene linkage
R3 represents a linear/branched/cyclic C1-C8 alkyl or a C6-C16 aryl group that may be substituted by a C1-C4 alkyl, F, CN, NO2, or fluorinated alkyl/alkoxy/aryl group or other group present in [0015].
The above formula meets the limitations of the instant claimed for where the cation:
Claimed n and m are each 2
Claimed Rx11 and Rx12 are H
Claimed L is -O- (claims 4 and 13)
Claimed Rx13-Rx16 may each independently be H or a hydrocarbon C1-C8 alkyl group, wherein the claim limitations of claim 4 are met when one of such is C1-C8 alkyl
Claimed Arx corresponds to reference R3, where R3 is a C6-C16 aryl group that may be substituted with fluorine or a fluorinated hydrocarbon group (claim 2) or another group
The anion
Benzenesulfonate meets the limitations of the claim for AN5
Ar is phenyl
Subscript n is 0
Butanesulfonate meets the limitations of the claim for anion (d1-2)
Z2c is a C4 hydrocarbon (butane)
The base resin is described from [0026]-[0055], and may include components such as polyhydroxystyrene, polymethacrylic acid, or other components such as those mentioned in the cited paragraphs. The base resin comprises subunits that bear acid-labile groups thereupon so as to increase the solubility of the resin in alkali after exposure and acid generation. Copolymers comprising monomer subunits of acrylic or methacrylic acid and derivatives thereof are explicitly described in [0026] (claim 6, 7, 15, 16)
Solvents, surfactants, quenchers, and other additives are discussed from [0085]-[0129] (claim 8, 17), where ideal solvents include but are not limited to PGMEA.
The resist composition is used in a patterning process to form a patterned resist film as described in [0130], where the composition is applied to a substrate, baked to remove solvent, exposed to radiation, post-baked, and developed to form the pattern (claims 9, 10, 18, 19).
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention from the general disclosure of the reference, which discloses substantially similar and identical chemical compounds to the claimed invention and therefore discloses compounds expected to perform similarly, to arrive at a chemical resist composition and salt therein displaying improved sensitivity and resolution.
Regarding Claim 11 and 20, the method of the claim recites only the pattern forming method of claim 10/19 as a positive limitation. “for manufacturing an electronic device” in the preamble is considered “intended use”. As the method of claim 10 and 19 has been rendered, claim 11 and 20 are also obvious as described above regarding claim 10 and 19.
Claim 14 is rejected under 35 U.S.C. 103 as being unpatentable over Kobayashi et al (US 20060160023 A1) as applied to claim 1 above, and further in view of Tango et al (WO2020158467 A1, published 08/06/2020 - US 20210286263 A1 used lieu of translation) .
Regarding Claim 14, Kobayashi discloses the limitations of the claim as discussed regarding claims 1 and 2 above.
Kobayashi however fails to teach a compound that conforms to the limitations of claim 14.
This limitation is met by Tango.
Tango discloses a radiation-sensitive composition, a method of pattern forming, a resultant patterned resist film, and a method or manufacturing an electronic device (Background).
Tango discloses composition having a base resin having a polarity that increases by the action of an acid, as well as additional resins that may be fluorinated and increase by the action of acid and/or alkali ([0021]-[0035]) as well as a solvent ([0036]-[0037]). Additionally included in the composition is a photoacid generator that is selected from the group of compounds (I) through (III), where more than one of such compound may be present ([0067]-[0068]).
The compound (I) is described from [0639]-[0727], where the compound conforms to formula (Ia):
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Where M11+, A11- corresponds to a structural unit X and A12-, M12+ correspond to a structural unit Y. Upon exposure the compound generates an acid represented by H-A11-L11-A12-H, where the cations are displaced by the protons H, forming a first moeity HA11 and a second moeity HA12, where the two moieties are acids having structures different from each other. L11 here represents a divalent linking group. The acid dissociation constant (a2) of the acidic group A12-H is larger than the corresponding acid dissociation constant (a1) of the acidic group H-A11.
Examples of the anionic group corresponding to A11 and A12- are depicted and described from [0658]-[0682], and cationic examples corresponding to M11+ and M12+ are depicted and described from [0683]-[0727] and at compounds B-1 to B-18 and B-22 described in the experimental examples ([1054]).
This photoacid generator maps onto the claimed compound (I) and condition I described in claim 14, where the cations and anions corresponding to groups Y and X are differently labeled but still correspond to the claimed limitations
Also discussed is the compound (III), which is described from [0776]-[0796] as a compound having two or more structural moieties X and a structural site Z, where Z is a moeity that is capable of neutralizing acid. Z is an organic group capable of interacting electrostatically with a proton through a functional group or an electron pair – such as nitrogen-bearing moieties described from [0781]-[0783]. The compound (III) preferably corresponds to a formula (IIIa):
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Where, M31+ corresponds to a cation, M31- corresponds to an acidic moeity that becomes HA31 upon irradiation, L3 and L4 are linking groups, and R2X is a monovalent organic group.
This photoacid generator maps onto the claimed compound (II) described in claim 5 and 14, where the cations and anions, and nonionic site corresponding to groups Z and X are differently labeled but still correspond to the claimed limitations.
In [0074], when the composition described comprises a compound corresponding to the photoacid generator of at least (I)-(III), the performance of a pattern is improved by suppressing aggregation in the composition.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention before the time of filing in view of the disclosures of Kobayashi and Tango, incorporating the salt (1) and/or (III) disclosed by Tango into the composition of Kobayashi to arrive at a resist composition having improved pattern performance brought on by the reduction of aggregation.
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Kobayashi et al (US 20060160023 A1) and Tango et al (WO2020158467 A1, published 08/06/2020 - US 20210286263 A1 used lieu of translation) .
Regarding Claim 5, Kobayashi discloses a high resolution resist material comprising an acid generator and a base resin. Kobayashi ascribes high sensitivity and small line-edge roughness to the composition comprising the novel acid generator and base resin.
The acid generator is generally described at Formula (1), 0015] and [0020]-[025], and separately a second embodiment at [0056]-[0084].
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Where:
X- is a nonnucleophilic counterion having 1-20 carbon atoms, such as an arylsulfonate like benzene sulfonate or alkylsulfonate such as butanesulfonate
R1 and R2 are a hydrogen or linear/branched/cyclic C1-C8 alkyl group,
Y represents a single bond or a bond to N/O/C1-C4 alkylene linkage
R3 represents a linear/branched/cyclic C1-C8 alkyl or a C6-C16 aryl group that may be substituted by a C1-C4 alkyl, F, CN, NO2, or fluorinated alkyl/alkoxy/aryl group or other group present in [0015].
The above formula meets the limitations of the instant claimed for where the cation:
Claimed n and m are each 2
Claimed Rx11 and Rx12 are H
Claimed L is -O-
Claimed Rx13-Rx16 may each independently be H or a hydrocarbon C1-C8 alkyl group, wherein the claim limitations of claim 4 are met when one of such is C1-C8 alkyl
Claimed Arx corresponds to reference R3, where R3 is a C6-C16 aryl group that may be substituted with fluorine or a fluorinated hydrocarbon group or another group
Kobayashi however fails to teach a compound that conforms to the limitations of claims 5 for the formula X as incorporated into compounds (I) and/or (II) as required by the claim.
This limitation is met by Tango.
Tango discloses a radiation-sensitive composition, a method of pattern forming, a resultant patterned resist film, and a method or manufacturing an electronic device (Background).
Tango discloses composition having a base resin having a polarity that increases by the action of an acid, as well as additional resins that may be fluorinated and increase by the action of acid and/or alkali ([0021]-[0035]) as well as a solvent ([0036]-[0037]). Additionally included in the composition is a photoacid generator that is selected from the group of compounds (I) through (III), where more than one of such compound may be present ([0067]-[0068]).
The compound (I) is described from [0639]-[0727], where the compound conforms to formula (Ia):
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Where M11+, A11- corresponds to a structural unit X and A12-, M12+ correspond to a structural unit Y. Upon exposure the compound generates an acid represented by H-A11-L11-A12-H, where the cations are displaced by the protons H, forming a first moeity HA11 and a second moeity HA12, where the two moieties are acids having structures different from each other. L11 here represents a divalent linking group. The acid dissociation constant (a2) of the acidic group A12-H is larger than the corresponding acid dissociation constant (a1) of the acidic group H-A11.
Examples of the anionic group corresponding to A11 and A12- are depicted and described from [0658]-[0682], and cationic examples corresponding to M11+ and M12+ are depicted and described from [0683]-[0727] and at compounds B-1 to B-18 and B-22 described in the experimental examples ([1054]).
This photoacid generator maps onto the claimed compound (I) and condition I described in claim 5, where the cations and anions corresponding to groups Y and X are differently labeled but still correspond to the claimed limitations. Exemplary instances of the compound salt include that of the sulfonyl imide – sulfonic acid dual salt B1:
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Where the anionic site A2- corresponds to claimed sulfonylimide BB-1 (claim 21)
Also discussed is the compound (III), which is described from [0776]-[0796] as a compound having two or more structural moieties X and a structural site Z, where Z is a moeity that is capable of neutralizing acid. Z is an organic group capable of interacting electrostatically with a proton through a functional group or an electron pair – such as nitrogen-bearing moieties described from [0781]-[0783]. The compound (III) preferably corresponds to a formula (IIIa):
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Where, M31+ corresponds to a cation, M31- corresponds to an acidic moeity that becomes HA31 upon irradiation, L3 and L4 are linking groups, and R2X is a monovalent organic group.
This photoacid generator maps onto the claimed compound (II) described in claim 5 and 14, where the cations and anions, and nonionic site corresponding to groups Z and X are differently labeled but still correspond to the claimed limitations.
In [0074], when the composition described comprises a compound corresponding to the photoacid generator of at least (I)-(III), the performance of a pattern is improved by suppressing aggregation in the composition.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention before the time of filing in view of the disclosures of Kobayashi and Tango, incorporating the salt anion (I) and/or (III) disclosed by Tango into the composition and cation-pairing it with Kobayashi’s cation to arrive at a resist composition having improved pattern performance brought on by the reduction of aggregation, and improved sensitivity brought on by the cation incorporated from Kobayashi.
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