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.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 05/26/2023 is being considered by the examiner.
Response to Amendment
Applicant’s Amendment filed 03/16/2026 has been considered and is being entered. Claims 3, 10, and 16 have been canceled. Claims 1, 8, 14, and 19 have been amended.
Response to Arguments
Applicant’s Amendments and arguments based therefrom have placed the scope of the claims outside that of the prior art used in furnishing the 35 USC 102 and separate 35 USC 103 rejections set forth in the prior office action. All rejections set forth in the prior Nonfinal Rejection are withdrawn.
However, After further search and consideration, the examiner makes a new grounds of rejection as set forth in the body of the office action below. Applicant’s Amendments 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) 1-2, 4, 6-7, 14, and 18 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Shibayama et al (US 20210181635 A1, published 06/17/2021)
Regarding Claim 1, 2, 4, 6-7, 14, and 18, Shibayama discloses a method for producing a semiconductor device comprising a silicon-containing resist underlayer composition, and the aforementioned resist underlayer composition. The resist underlayer composition comprises a hydrolysis condensate prepared through the hydrolysis of a silane conforming to a formula (1):
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294
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Wherein –
R1 is an organic group having a primary amino group, a secondary amino group, or a tertiary amino group and is bonded to a silicon atom via a S-C bond
R2 is an alkyl, aryl, haloalkyl, haloaryl, alkoxy aryl group, alkenyl group, or other group recited in [0013]
R3 is an alkoxy group, acyl oxy group, or halogen group
Subscript a is 1, b may be 0-2, and the sum of a and b is 1-3.
Additional silanes conforming to formulas (2) and (3) as set forth at [0018] may also be present.
Exemplary organic groups that may be present on the silane as R1 and R2 are discussed from [0050]-[0070], with examples of compounds conforming to formula 1 presented at [0071]
Hydrolysable silanes conforming to formulas (2) and (3) are discussed and presented at [0075]-[0082].
Exemplary hydrolysis condensates (polymers) are presented at [0083] – these embodiments are used in the experimental examples disclosed by the reference.
In the experimental examples, polymers A-1 (Synthesis example 1 at [0160]) and A-13 (Synthesis example A-14, [0173]) feature the following monomer subunits, one subunit having an unsaturated isocyanurate group, another having a dimethylammonium nitrate group in addition to other monomers:
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152
102
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196
182
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Polymer A-14 (Synthesis example 15, [0174]) features the following subunits
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216
372
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Polymer A-15 (Synthesis example 16, [0175) features the following subunits
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274
326
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Polymer A-16 features the following subunits
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380
314
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In the above embodiments, each of the aforementioned polymers meet the limitations of the claims 1 and 14 for where:
The embodiments are polymers
The embodiments bear a salt comprising
A cationic component
An anionic component
At least one (the cationic) component is bonded covalently by a linker/group to the polymer
The polymer of the resist composition comprises a crosslinker (the isocyanurate monomer) that is covalently bound (claim 2) to the polymer (claim 4)
The polymer contains a cation component that is a protonated tertiary amine (A-1, A-13, and A-16), an imidazolium (A-15), and/or a quaternary ammonium (A-14) (claim 6)
The polymer contains a crosslinker having a vinyl group (the vinyl-substituted isocyanurate) (claim 7)
The salt(s) of the composition comprise a carbon-carbon bond, a carbon-hydrogen bond, and/or a cation component that is a protonated tertiary amine (A-1, A-13, and A-16), an imidazolium (A-15), and/or a quaternary ammonium (A-14) (claim 18)
The polymers above are dissolved with an acid and solvent as per Table 1 (See [0183]-[0186]) to form compositions which are then coated onto a substrate and heated to dry into films. As the compositions comprise all the limitations of the claims 1 and 14 and dependents therefrom, they function as ion-conductors – see MPEP 2112.01.I and .II.
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) 5, 8-9, 11-13, 15, and 17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Shibayama et al ( US 20210181635 A1, published 06/17/2021) .
Regarding Claim 5, 15, and 17, Shibayama discloses the limitations of the claims as described above regarding claims 1 and 14.
Shibayama does not disclose a second polymer in an experimental embodiment of the compositions or resultant products.
This limitation is met by the general disclosure of Shibayama.
The resist underlayer composition comprises a hydrolysis condensate prepared through the hydrolysis of a silane conforming to a formula (1):
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Wherein –
R1 is an organic group having a primary amino group, a secondary amino group, or a tertiary amino group and is bonded to a silicon atom via a S-C bond
R2 is an alkyl, aryl, haloalkyl, haloaryl, alkoxy aryl group, alkenyl group, or other group recited in [0013]
R3 is an alkoxy group, acyloxy group, or halogen group
Subscript a is 1, b may be 0-2, and the sum of a and b is 1-3.
Additional silanes conforming to formulas (2) and (3) as set forth at [0018] may also be present.
Exemplary organic groups that may be present on the silane as R1 and R2 are discussed from [0050]-[0070], with examples of compounds conforming to formula 1 presented at [0071].
Hydrolysable silanes conforming to formulas (2) and (3) are discussed and presented at [0075]-[0082].
Exemplary hydrolysis condensates (polymers) are presented at [0083] – these embodiments are used in the experimental examples disclosed by the reference. These condensates are prepared from acid hydrolysis, such as in the presence of nitric, sulfuric, acetic, and other acids as described at [0090]. In the Experimental results, the polymers A-1 and A-13 through A-16 as referred to above regarding the rejections of claims 1, 14 and dependent claims therefrom are synthesized using nitric acid to generate a nitrate salt with a nitrogenous basic group attached to the siloxane subunit of the polymer – the cationic component being bound to the polymer by a covalent linker and the nitrate anion electrostatically associated with the cation. These polymers additionally comprise a vinyl-substituted isocyanurate moeity that will crosslink in the presence of light (claim 9, where the crosslinker is covalently bonded to the polymer)
Additional components that may be included include bisphenol S derivatives ([0093]), curing catalysts such as those presented from [0096]-[0116], organic acids, photoacid generators ([0123]-[0129]), surfactants, rheology modifiers, and solvents ([0130]-[0134]). Surfactants that may be added include polymeric surfactants such as polyoxyethylene lauryl ethers and polyoxyethylene-polyoxypropylene bock copolymers (claim 5, claim 15 – where the second polymer comprises a non-siloxane). A surfactant suppresses the formation of pinholes and striations formed during application of the composition to a substrate for processing ([0130]).
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, incorporating the polymeric surfactant as taught by the reference in order to suppress the formation of unwanted defects such as pinholes and striations during deposition onto a substrate.
Regarding Claim 8, 9, and 11-13, Shibayama discloses a method for producing a semiconductor device comprising a silicon-containing resist underlayer composition, and the aforementioned resist underlayer composition.
Shibayama however does not explicitly disclose the method steps as required by claim 8 and the dependents in an experimental embodiment.
These limitations are met by the general disclosure of the reference.
The resist underlayer composition comprises a hydrolysis condensate prepared through the hydrolysis of a silane conforming to a formula (1):
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294
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Wherein –
R1 is an organic group having a primary amino group, a secondary amino group, or a tertiary amino group and is bonded to a silicon atom via a S-C bond
R2 is an alkyl, aryl, haloalkyl, haloaryl, alkoxy aryl group, alkenyl group, or other group recited in [0013]
R3 is an alkoxy group, acyloxy group, or halogen group
Subscript a is 1, b may be 0-2, and the sum of a and b is 1-3.
Additional silanes conforming to formulas (2) and (3) as set forth at [0018] may also be present.
Exemplary organic groups that may be present on the silane as R1 and R2 are discussed from [0050]-[0070], with examples of compounds conforming to formula 1 presented at [0071].
Hydrolysable silanes conforming to formulas (2) and (3) are discussed and presented at [0075]-[0082].
Exemplary hydrolysis condensates (polymers) are presented at [0083] – these embodiments are used in the experimental examples disclosed by the reference. These condensates are prepared from acid hydrolysis, such as in the presence of nitric, sulfuric, acetic, and other acids as described at [0090]. In the Experimental results, the polymers A-1 and A-13 through A-16 as referred to above regarding the rejections of claims 1, 14 and dependent claims therefrom are synthesized using nitric acid to generate a nitrate salt with a nitrogenous basic group attached to the siloxane subunit of the polymer – the cationic component being bound to the polymer by a covalent linker and the nitrate anion electrostatically associated with the cation. These polymers additionally comprise a vinyl-substituted isocyanurate moeity that will crosslink in the presence of light (claim 9, where the crosslinker is covalently bonded to the polymer)
Additional components that may be included include bisphenol S derivatives ([0093]), curing catalysts such as those presented from [0096]-[0116], organic acids, photoacid generators ([0123]-[0129]), surfactants, rheology modifiers, and solvents ([0130]-[0134]). Surfactants that may be added include polymeric surfactants such as polyoxyethylene lauryl ethers and polyoxyethylene-polyoxypropylene bock copolymers.
The composition(s) is/are processed according to the lithographic process outlined from [0135], wherein the compositions are coated onto a substrate (claim 12, where the mixture is coated onto the substrate) and baked. In an embodiment, a photoresist layer may be deposited thereatop, baked, exposed to radiation, and developed ([00137]-[0157]). The photoresist layer may be positive or negative – development may remove exposed regions or unexposed regions depending on the nature of the resist. The composition(s) may absorb light from the photolithographic process even from underneath a conventional/EUV photoresist layer, instituting reactions in the patterned regions from exposure. After development of the photoresist layer, the underlayer composition is etched using the patterned photoresist layer as a mask – removal of the underlayer composition may result in removal of the exposed underlayer or unexposed underlayer regions depending on the removal of respective exposed or unexposed photoresist during development (claim 11, where at least partial removal of the mixture that has not been crosslinked is performed). The etching step is performed using a halogenated gas in order to more quickly remove the etched portions of the composition.
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date in view of the disclosure of the reference, arriving at an ion conductor obtained by the processes described – these processes are known lithographic techniques such as deposition, exposure, development, and etching, and the application of these known techniques to a known composition as disclosed by the prior art would necessarily yield predictable results.
Claim(s) 19 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Shibayama et al ( US 20210181635 A1, published 06/17/2021) and Fukuzaki et al (US 2021/0080829 A1).
Shibayama discloses a method for producing a semiconductor device comprising a silicon-containing resist underlayer composition, and the aforementioned resist underlayer composition.
Shibayama however does not explicitly disclose the method steps as required by claim 8 and the dependents in an experimental embodiment.
These limitations are met by the general disclosure of the reference.
The resist underlayer composition comprises a hydrolysis condensate prepared through the hydrolysis of a silane conforming to a formula (1):
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24
294
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Wherein –
R1 is an organic group having a primary amino group, a secondary amino group, or a tertiary amino group and is bonded to a silicon atom via a S-C bond
R2 is an alkyl, aryl, haloalkyl, haloaryl, alkoxy aryl group, alkenyl group, or other group recited in [0013]
R3 is an alkoxy group, acyloxy group, or halogen group
Subscript a is 1, b may be 0-2, and the sum of a and b is 1-3.
Additional silanes conforming to formulas (2) and (3) as set forth at [0018] may also be present.
Exemplary organic groups that may be present on the silane as R1 and R2 are discussed from [0050]-[0070], with examples of compounds conforming to formula 1 presented at [0071]. Exemplary species include triethoxysilylpropylsuccinic anhydride, glyxidoxypropyltrimethoxysilane, and silanes having epoxycyclohexyl groups.
Hydrolysable silanes conforming to formulas (2) and (3) are discussed and presented at [0075]-[0082]. Exemplary species include methyltriethoxysilane, phenyltriethoxysilane, and tetraethoxysilane.
Exemplary hydrolysis condensates (polymers) are presented at [0083] – these embodiments are used in the experimental examples disclosed by the reference. These condensates are prepared from acid hydrolysis, such as in the presence of nitric, sulfuric, acetic, and other acids as described at [0090]. In the Experimental results, the polymers A-1 and A-13 through A-16 as referred to above regarding the rejections of claims 1, 14 and dependent claims therefrom are synthesized using nitric acid to generate a nitrate salt with a nitrogenous basic group attached to the siloxane subunit of the polymer – the cationic component being bound to the polymer by a covalent linker and the nitrate anion electrostatically associated with the cation. These polymers additionally comprise a vinyl-substituted isocyanurate moeity that will crosslink in the presence of light.
Additional components that may be included include bisphenol S derivatives ([0093]), curing catalysts such as those presented from [0096]-[0116], organic acids, photoacid generators ([0123]-[0129]), surfactants, rheology modifiers, and solvents ([0130]-[0134]). Surfactants that may be added include polymeric surfactants such as polyoxyethylene lauryl ethers and polyoxyethylene-polyoxypropylene bock copolymers.
The composition(s) is/are processed according to the lithographic process outlined from [0135], wherein the compositions are coated onto a substrate and baked. In an embodiment, a photoresist layer may be deposited thereatop, baked, exposed to radiation, and developed ([00137]-[0157]). The photoresist layer may be positive or negative – development may remove exposed regions or unexposed regions depending on the nature of the resist. The composition(s) may absorb light from the photolithographic process even from underneath a conventional/EUV photoresist layer, instituting reactions in the patterned regions from exposure. After development of the photoresist layer, the underlayer composition is etched using the patterned photoresist layer as a mask – removal of the underlayer composition may result in removal of the exposed underlayer or unexposed underlayer regions depending on the removal of respective exposed or unexposed photoresist during development. The etching step is performed using a halogenated gas in order to more quickly remove the etched portions of the composition.
Shibayama does not disclose or teach that the composition is incorporated into a device.
This limitation is met by Fukuzaki.
Fukuzaki discloses a negative photosensitive resin composition comprising a siloxane resin having a radically polymerizable group and a carboxyl group and/or dicarboxylic anhydride group, a reactive monomer, a radical photopolymerization initiator, silica particles, and a siloxane compound having an oxetanyl group (Abstract).
silica particles, and a siloxane compound having an oxetanyl group (Abstract).
The siloxane resin is described from [0020]-[0045] and comprises monomers such as those encapsulated by the formulas (1)-(9), where the polymeric resin is synthesized via a hydrolysis reaction and subsequent condensation.
The polymerizable monomer is described from [0046] to [0048], where exemplary monomers include polyfunctional methacrylates, but vinyl group monomers such as styrenes may be used.
The photoinitiator is described from [0049]-[0052], where exemplary initiators may be phenone initiators, phosphine oxides, or oxime esters.
A metal chelate compound (metal salt) used to promote densification of the cured film by catalyzing silanol condensation is also present in the composition, as discussed from [0070]-[0077].
In an experimental embodiment described at [0134], polymer PS-1 is synthesized by condensing methyltrimethoxysilane, phenyltrimethoxysilane, 3-trimethoxysilylpropylsuccinic acid, and gamma-acryloylpropyltrimethoxysilane in diacetone dialcohol solvent, The resultant polymer bears a crosslinkable group in both the acryloyl group side chain and in the succinic acid group.
The photoresist composition and films formed therefrom may be incorporated into devices such as smartphones. Smartphones are devices having at least one of a battery, an electronic circuit, and are electrooptic devices.
The compositions of Shibayama and Fukuzaki are both directed to silicon-containing resist compositions having reactive side groups and photopatterning applications thereof.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention prior to the effective filing date from the generally disclosed methods and materials described within by incorporating the composition and/or films made therefrom of Shibayama into the composition and/or Device(s) of Fukuzaki with the expectation that chemically similar compositions would behave similarly
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.
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.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sally Merkling can be reached at 571-272-6792. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/A.P.T./Examiner, Art Unit 1737
/SALLY A MERKLING/SPE, Art Unit 1738
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