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 .
The response of the applicant has been read and given careful consideration. Rejection not repeated below are withdrawn in view of the amendment and arguments of the applicant (the rejection of based in part upon Fukushima 20240176236 or Fukushima 20240176236 are withdrawn. Responses to the arguments of the applicant are presented after the first rejection they are directed to.
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
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.
Claims 1-14 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. 20230107121.
Hatakeyama et al. 20230107121 exemplifies PAG-10
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Which in example 19 is combined with polymer 1, quencher Q-7, a surfactant and solvents ([0213], table 1). This resist is coated upon a silicon wafer, with a hardcoat, dried, exposed, post baked and developed ion TMAH to form a positive resist pattern [0220-0223]
Other disclosed PAG anions include
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(Pages 64-134). These PAGs are bounded by formulae
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n the formulae (2-1) and (2-2), “p” represents an integer satisfying 1≤p≤3. “q” and “r” represent integers satisfying 1≤q5, 0≤r≤3, and 1≤q+r≤5. L.sup.11 represents a single bond, or a linear, branched, or cyclic saturated hydrocarbylene group having 1 to 6 carbon atoms and optionally containing an ether bond or an ester bond. L.sup.12 represents a single bond or a divalent linking group having 1 to 20 carbon atoms when “p” is 1, or represents a trivalent or tetravalent linking group having 1 to 20 carbon atoms when “p” is 2 or 3, the linking groups optionally containing an oxygen atom, a sulfur atom, a nitrogen atom, a chlorine atom, a bromine atom, or an iodine atom. R.sup.401 represents a hydroxy group, a carboxyl group, a fluorine atom, a chlorine atom, a bromine atom, an amino group, —NR.sup.401A—C(═O)—R.sup.401B, or —NR.sup.401A—C(═O)—O—R.sup.401B, or a saturated hydrocarbyl group having 1 to 20 carbon atoms, a saturated hydrocarbyloxy group having 1 to 20 carbon atoms, a saturated hydrocarbyloxycarbonyl group having 2 to 10 carbon atoms, a saturated hydrocarbylcarbonyloxy group having 2 to 20 carbon atoms, a saturated hydrocarbylsulfonyloxy group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms each of which optionally contains an ether bond. R.sup.401A represents a hydrogen atom or a saturated hydrocarbyl group having 1 to 6 carbon atoms, and optionally contains a halogen atom, a hydroxy group, an alkoxy group having 1 to 6 carbon atoms, a saturated hydrocarbylcarbonyl group having 2 to 6 carbon atoms, or a saturated hydrocarbylcarbonyloxy group having 2 to 6 carbon atoms. R.sup.401B represents an aliphatic hydrocarbyl group having 1 to 16 carbon atoms or an aryl group having 6 to 12 carbon atoms, and optionally contains a halogen atom, a hydroxy group, a saturated hydrocarbyloxy group having 1 to 6 carbon atoms, a saturated hydrocarbylcarbonyl group having 2 to 6 carbon atoms, or a saturated hydrocarbylcarbonyloxy group having 2 to 6 carbon atoms; the aliphatic hydrocarbyl group is saturated or unsaturated, and linear, branched, or cyclic; and the saturated hydrocarbyl group, saturated hydrocarbyloxy group, saturated hydrocarbyloxycarbonyl group, saturated hydrocarbylcarbonyl groups, saturated hydrocarbylcarbonyloxy groups, and saturated hydrocarbylsulfonyloxy group are linear, branched, or cyclic. When “p” and/or “r” are 2 or more, R.sup.401's are identical to or different from one another. Rf.sup.11 to Rf.sup.14 each independently represent a hydrogen atom, a fluorine atom, or a trifluoromethyl group, at least one of Rf.sup.11 to Rf.sup.14 is a fluorine atom or a trifluoromethyl group, and Rf.sup.11 and Rf.sup.12 optionally bond with each other to form a carbonyl group. R.sup.402, R.sup.403, R.sup.404, R.sup.405 and R.sup.906 each independently represent a hydrocarbyl group having 1 to 20 carbon atoms and optionally containing a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a heteroatom; the hydrocarbyl group is saturated or unsaturated, and linear, branched, or cyclic; and the groups as R.sup.402, R.sup.403, R.sup.404, R.sup.405, and R.sup.406 have some or all of hydrogen atoms optionally substituted with a hydroxy group, a carboxyl group, a halogen atom, a cyano group, a nitro group, a mercapto group, a sultone group, a sultone group, or a sulfonium salt-containing group, and have some of carbon atoms optionally substituted with an ether bond, an ester bond, a carbonyl group, an amide bond, a carbonate group, or a sulfonic acid ester bond. R.sup.402 and R.sup.403 are optionally bonded to each other to form a ring together with a sulfur atom bonded thereto In the formulae (2-1) and (2-2), “p” is an integer of 1≤p≤3. “q” and “r” are integers satisfying 1≤q≤5, 0≤r≤3, and 1≤q+r≤.Math.5. Preferably, “q” is an integer of 1≤q≤3, and “r” is an integer of 0≤r≤2. L.sup.11 is a single bond, or a linear, branched, or cyclic saturated hydrocarbylene group having 1 to 6 carbon atoms optionally containing an ether bond or an ester bond. L.sup.12 is a single bond or a divalent linking group having 1 to 20 carbon atoms when “p” is 1, or a trivalent or tetravalent linking group having 1 to 20 carbon atoms when “p” is 2 or 3. The linking groups may contain an oxygen atom, a sulfur atom, a nitrogen atom, a chlorine atom, a bromine atom, or an iodine atom. R.sup.401 is a hydroxy group, a carboxyl group, a fluorine atom, a chlorine atom, a bromine atom, an amino group, —NR.sup.401A—C(═O)—R.sup.401B, or —NR.sup.401A—C(═O)—O—R.sup.401B. Alternatively, R.sup.401 is a saturated hydrocarbyl group having 1 to 20 carbon atoms, a saturated hydrocarbyloxy group having 1 to 20 carbon atoms, a saturated hydrocarbyloxycarbonyl group having 2 to 10 carbon atoms, a saturated hydrocarbylcarbonyloxy group having 2 to 20 carbon atoms, a saturated hydrocarbylsulfonyloxy group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms, and each of these groups may contain an ether bond. R.sup.401A is a hydrogen atom or a saturated hydrocarbyl group having 1 to 6 carbon atoms, and may contain a halogen atom, a hydroxy group, an alkoxy group having 1 to 6 carbon atoms, a saturated hydrocarbylcarbonyl group having 2 to 6 carbon atoms, or a saturated hydrocarbylcarbonyloxy group having 2 to 6 carbon atoms. R.sup.401B is an aliphatic hydrocarbyl group having 1 to 16 carbon atoms or an aryl group having 6 to 12 carbon atoms, and may contain a halogen atom, a hydroxy group, a saturated hydrocarbyloxy group having 1 to 6 carbon atoms, a saturated hydrocarbylcarbonyl group having 2 to 6 carbon atoms, or a saturated hydrocarbylcarbonyloxy group having 2 to 6 carbon atoms. The aliphatic hydrocarbyl group may be saturated or unsaturated, and may be linear, branched, or cyclic. The saturated hydrocarbyl group, saturated hydrocarbyloxy group, saturated hydrocarbyloxycarbonyl group, saturated hydrocarbylcarbonyl groups, saturated hydrocarbylcarbonyloxy groups, and saturated hydrocarbylsulfonyloxy group may be linear, branched, or cyclic. When “p” and/or “r” are 2 or more, R.sup.401's may be identical to or different from one another. Rf.sup.11 to Rf.sup.14 are each independently a hydrogen atom, a fluorine atom, or a trifluoromethyl group, but at least one of Rf.sup.11 to Rf.sup.14 is a fluorine atom or a trifluoromethyl group. Rf.sup.11 and Rf.sup.12 may bond with each other to form a carbonyl group. R.sup.402, R.sup.403, R.sup.404, R.sup.405, and R.sup.406 are each independently a hydrocarbyl group having 1 to 20 carbon atoms, and may contain a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a heteroatom. The hydrocarbyl group may be saturated or unsaturated, and may be linear, branched, or cyclic. The groups as R.sup.402, R.sup.403, R.sup.404, R.sup.405, and R.sup.406 may have some or all of hydrogen atoms substituted with a hydroxy group, a carboxyl group, a halogen atom, a cyano group, a nitro group, a mercapto group, a sultone group, a sulfone group, or a sulfonium salt-containing group, and may have some of carbon atoms substituted with an ether bond, an ester bond, a carbonyl group, an amide bond, a carbonate group, or a sulfonic acid ester bond. Alternatively, R.sup.402 and R.sup.403 may bond to each other to form a ring together with a sulfur atom bonded thereto. Specific examples of R.sup.402, R.sup.403, R.sup.404, R.sup.405, and R.sup.406 include those described above for R.sup.101 to R.sup.105 [0148-0154]. Useful lactones are disclosed as adhesive increasing units [0105]
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Hatakeyama et al. 20230107121 does not exemplify the compounds having the OR5 group (O-5a) recited in the instant claims.
With respect to claims 1-8 and 14, it would have been obvious to modify PAG-10
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by replacing the nitro substituent with either a halogen or hydrogen based upon the teaching of the reference including the exemplification of compounds
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and
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and adding an acid labile group such as a t-butoxy, ketal or carbonate acid labile group to the iodine substituted phenyl ring based upon the teachings of the reference including the exemplification of compounds
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with a reasonable expectation of forming a useful photoacid generator.
With respect to claims 1-10 and 12-14, it would have been obvious to modify PAG-10
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by replacing the nitro substituent with either a halogen or hydrogen based upon the teaching including the exemplification of compounds
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and
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and adding an acid labile group such as a t-butoxy, ketal or carbonate acid labile group to the iodine substituted phenyl ring based upon the teachings of the reference including the exemplification of compounds
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and using the resulting photoacid generator in place of PAG-10 in the cited example with a reasonable expectation of forming a useful photoresist and resist pattern.
With respect to claims 1-14, it would have been obvious to modify PAG-10
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by replacing the nitro substituent with either a halogen or hydrogen based upon the teaching including the exemplification of compounds
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and
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and adding an acid labile group such as a t-butoxy, ketal or carbonate acid labile group to the iodine substituted phenyl ring based upon the teachings of the reference including the exemplification of compounds
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, adding a lactone such as
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to the resist polymer as taught at [0105] to increase the adhesion to the substrate and using the resulting photoacid generator in place of PAG-10 in the cited example with a reasonable expectation of forming a useful photoresist and resist pattern.
In addition to the basis above, it would have been obvious to substitute the replacement phenyl ring as taught in Hatakeyama et al. 20230107121 or to use other linkages between the phenyl moieties taught in Hatakeyama et al. 20230107121 with a reasonable expectation of forming a useful photoacid generator, photoresist and resist pattern.
In the response of 8/10/2026, the applicant argues that the specification demonstrates that the salts of formula (I) provide superior results. Specifically pointing to the line edge roughness. The examiner notes the results and points out that the inventive examples of the instant specification are evidencing improved LER in photoresist compositions including the photoacid generator in specific amounts together with a photoresist resin/polymer containing acid labile groups, while claims 1-8 and 14 only require the salt. None of the claims are commensurate in scope with the showing. The specification describes the inventive resists as having 1 to 45 parts by mass of the inventive photoacid generating salt based upon 100 parts of the polymer in the prepub of the instant specification at [0494]. The showing is not commensurate in scope with the coverage sought. The breadth of Hatakeyama et al. 20230107121 does not negate the teachings of specific anions.
Claims 1-14 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. 20220107559.
Hatakeyama et al. 20220107559 exemplifies PAG 12 and PAG 18
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Which are combined with polymer 3 or polymer 5, quencher, surfactant and solvent to form a resist composition.
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[0188], table 2 and 3). These coated, dried, exposure using EUV, post baked and developed in TMAH [0193-0196]. These PAGs are bounded by formula I-3
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, where
p is an integer of 1 to 3; q is an integer of 1 to 5, r is an integer of 0 to 3, and 1≤q+r≤5. In formula (1-3), L.sup.1 is a single bond, ether bond, ester bond, amide bond, imide bond, or a C.sub.1-C.sub.6 saturated hydrocarbylene group in which any constituent —CH.sub.2— may be replaced by an ether bond or ester bond. Notably, the constituent —CH.sub.2— may be positioned at the end of the saturated hydrocarbylene group. The C.sub.1-C.sub.6 saturated hydrocarbylene group L may be straight, branched or cyclic. Examples thereof include C.sub.1-C.sub.6 alkanediyl groups such as methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl; C.sub.3-C.sub.6 cyclic saturated hydrocarbylene groups such as cyclopropanediyl, cyclobutanediyl, cyclopentanediyl, and cyclohexanediyl; and combinations thereof. In formula (1-3), L.sup.2 is a single bond or a C.sub.1-C.sub.20 hydrocarbylene group which may contain a heteroatom in case of p=1; and a C.sub.1-C.sub.20 (p+1)-valent hydrocarbon group which may contain a heteroatom in case of p=2 or 3. The C.sub.1-C.sub.20 hydrocarbylene group L.sup.2 may be saturated or unsaturated and straight, branched or cyclic. Examples thereof include C.sub.1-C.sub.20 alkanediyl groups such as methanediyl, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, and dodecane-1,12-diyl; C.sub.3-C.sub.20 cyclic saturated hydrocarbylene groups such as cyclopentanediyl, cyclohexanediyl, norbornanediyl and adamantanediyl; C.sub.2-C.sub.20 unsaturated aliphatic hydrocarbylene groups such as vinylene and propene-1,3-diyl; C.sub.6-C.sub.20 arylene groups such as phenylene and naphthylene; and combinations thereof. The C.sub.1-C.sub.20 (p+1)-valent hydrocarbon group L.sup.2 may be saturated or unsaturated and straight, branched or cyclic. Examples thereof include groups obtained by removing one or two hydrogen atoms from the above-described examples of the C.sub.1-C.sub.20 hydrocarbylene group. In formula (1-3), L.sup.3 is a single bond, ether bond or ester bond. In formula (1-3), R.sup.3 is a hydroxy group, carboxy group, fluorine, chlorine, bromine or amino group, or a C.sub.1-C.sub.20 hydrocarbyl group, C.sub.1-C.sub.20 hydrocarbyloxy group, C.sub.2-C.sub.20 hydrocarbylcarbonyl group, C.sub.2-C.sub.20 hydrocarbyloxycarbonyl group, C.sub.2-C.sub.20 hydrocarbylcarbonyloxy group or C.sub.1-C.sub.20 hydrocarbylsulfonyloxy group, which may contain fluorine, chlorine, bromine, hydroxy, amino or ether bond, or —N(R.sup.3A)(R.sup.3B), —N(R.sup.3C)—C(═O)—R.sup.3D or —N(R.sup.3C)—C(═O)O—R.sup.3D. R.sup.3A and R.sup.3B are each independently hydrogen or a C.sub.1-C.sub.6 saturated hydrocarbyl group. R.sup.3C is hydrogen or a C.sub.1-C.sub.6 saturated hydrocarbyl group in which some or all of the hydrogen atoms may be substituted by halogen, hydroxy, C.sub.1-C.sub.6 saturated hydrocarbyloxy, C.sub.2-C.sub.6 saturated hydrocarbylcarbonyl or C.sub.2-C.sub.6 saturated hydrocarbylcarbonyloxy moiety. R.sup.3D is a C.sub.1-C.sub.16 aliphatic hydrocarbyl group, C.sub.6-C.sub.12 aryl group or C.sub.7-C.sub.15 aralkyl group, in which some or all of the hydrogen atoms may be substituted by halogen, hydroxy, C.sub.1-C.sub.6 saturated hydrocarbyloxy, C.sub.2-C.sub.6 saturated hydrocarbylcarbonyl or C.sub.2-C.sub.6 saturated hydrocarbylcarbonyloxy moiety. When p and/or r is 2 or more, groups R.sup.3 may be the same or different. The C.sub.1-C.sub.20 hydrocarbyl group, and hydrocarbyl moiety in the C.sub.1-C.sub.20 hydrocarbyloxy group, C.sub.2-C.sub.20 hydrocarbylcarbonyl group, C.sub.2-C.sub.20 hydrocarbyloxycarbonyl group, C.sub.2-C.sub.20 hydrocarbylcarbonyloxy group or C.sub.1-C.sub.20 hydrocarbylsulfonyloxy group, represented by R.sup.3, may be saturated or unsaturated and straight, branched or cyclic. Examples thereof include C.sub.1-C.sub.20 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, heptadecyl, octadecyl, nonadecyl and icosyl; C.sub.3-C.sub.20 cyclic saturated hydrocarbyl groups such as cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, 4-methylcyclohexyl, cyclohexylmethyl, norbornyl, adamantyl; C.sub.2-C.sub.20 alkenyl groups such as vinyl, propenyl, butenyl and hexenyl; C.sub.2-C.sub.20 cyclic unsaturated aliphatic hydrocarbyl groups such as cyclohexenyl and norbornenyl; C.sub.2-C.sub.20 alkynyl groups such as ethynyl, propynyl and butynyl; C.sub.6-C.sub.20 aryl groups such as phenyl, methylphenyl, ethylphenyl, n-propylphenyl, isopropylphenyl, n-butylphenyl, isobutylphenyl, sec-butylphenyl, tert-butylphenyl, naphthyl, methylnaphthyl, ethylnaphthyl, n-propylnaphthyl, isopropylnaphthyl, n-butylnaphthyl, isobutylnaphthyl, sec-butylnaphthyl, tert-butylnaphthyl; C.sub.7-C.sub.20 aralkyl groups such as benzyl and phenethyl; and combinations thereof. The C.sub.1-C.sub.6 saturated hydrocarbyl groups represented by R.sup.3A, R.sup.3B and R.sup.3C may be straight, branched or cyclic. Examples thereof include C.sub.1-C.sub.6 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl and n-hexyl; and C.sub.3-C.sub.6 cyclic saturated hydrocarbyl groups such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Examples of the saturated hydrocarbyl moiety in the C.sub.1-C.sub.6 saturated hydrocarbyloxy group represented by R.sup.3C are as exemplified above for the saturated hydrocarbyl group. Examples of the saturated hydrocarbyl moiety in the C.sub.2-C.sub.6 saturated hydrocarbylcarbonyl group and C.sub.2-C.sub.6 saturated hydrocarbylcarbonyloxy group represented by R.sup.3C are as exemplified above for the C.sub.1-C.sub.6 saturated hydrocarbyl group, but of 1 to 5 carbon atoms. The aliphatic hydrocarbyl group represented by R.sup.3D may be saturated or unsaturated and straight, branched or cyclic. Examples thereof include C.sub.1-C.sub.16 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, tridecyl, tetradecyl, and pentadecyl; C.sub.3-C.sub.16 cyclic saturated hydrocarbyl groups such as cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, 4-methylcyclohexyl, cyclohexylmethyl, norbornyl, adamantyl; C.sub.2-C.sub.16 alkenyl groups such as vinyl, propenyl, butenyl and hexenyl; C.sub.2-C.sub.16 alkynyl groups such as ethynyl, propynyl and butynyl; C.sub.3-C.sub.16 cyclic unsaturated aliphatic hydrocarbyl groups such as cyclohexenyl and norbornenyl; and combinations thereof. Examples of the C.sub.6-C.sub.12 aryl group R.sup.3D include phenyl and naphthyl. Examples of the C.sub.7-C.sub.15 aralkyl group R.sup.3D include benzyl and phenethyl. Of the groups represented by R.sup.3D, examples of the hydrocarbyl moiety in the C.sub.1-C.sub.6 saturated hydrocarbyloxy group are as exemplified above for the C.sub.1-C.sub.6 saturated hydrocarbyl group represented by R.sup.3A, R.sup.3B and R.sup.3C; examples of the hydrocarbyl moiety in the C.sub.2-C.sub.6 saturated hydrocarbylcarbonyl group or C.sub.2-C.sub.6 saturated hydrocarbylcarbonyloxy group are as exemplified above for the C.sub.1-C.sub.6 saturated hydrocarbyl group, but of 1 to 5 carbon atoms. In formula (1-3), Rf.sup.1 to Rf.sup.4 are each independently hydrogen, fluorine or trifluoromethyl, at least one thereof being fluorine or trifluoromethyl. Also Rf.sup.1 and Rf.sup.2, taken together, may form a carbonyl group. The total number of fluorine atoms in Rf.sup.1 to Rf.sup.4 is preferably at least 2, more preferably at least 3 [0055-0066]. Examples include
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(pages 8-62). Useful lactones are disclosed on pages 97-101)
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Hatakeyama et al. 20220107559 does not exemplify the compounds having the OR5 group (O-5a) recited in the instant claims.
With respect to claims 1-8 and 14, it would have been obvious to modify PAG-12 or PAG 18
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by adding an acid labile group such as a t-butoxy, ketal or carbonate acid labile group to the iodine substituted phenyl ring based upon the teachings of the reference including the exemplification of compounds
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with a reasonable expectation of forming a useful photoacid generator.
With respect to claims 1-10 and 12-14, it would have been obvious to modify PAG-12 or PAG 18
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by adding an acid labile group such as a t-butoxy, ketal or carbonate acid labile group to the iodine substituted phenyl ring based upon the teachings of the reference including the exemplification of compounds
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and using the resulting photoacid generator in place of PAG-12 or PAG18 in the cited example with a reasonable expectation of forming a useful photoresist and resist pattern.
With respect to claims 1-14, it would have been obvious to modify PAG-12 or PAG 18
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by adding an acid labile group such as a t-butoxy, ketal or carbonate acid labile group to the iodine substituted phenyl ring based upon the teachings of the reference including the exemplification of compounds
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, adding a lactone such as
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to the resist polymer as taught at pages 97-101 to increase the adhesion to the substrate and using the resulting photoacid generator in place of PAG-12 or PAG18 in the cited example with a reasonable expectation of forming a useful photoresist and resist pattern.
In addition to the basis above, it would have been obvious to substitute the replacement phenyl ring as taught in Hatakeyama et al. 20220107559 or to use other linkages between the phenyl moieties taught in Hatakeyama et al. 20220107559 with a reasonable expectation of forming a useful photoacid generator, photoresist and resist pattern.
In the response of 8/10/2026, the applicant argues that the specification demonstrates that the salts of formula (I) provide superior results. Specifically pointing to the line edge roughness. The examiner notes the results and points out that the inventive examples of the instant specification are evidencing improved LER in photoresist compositions including the photoacid generator in specific amounts together with a photoresist resin/polymer containing acid labile groups, while claims 1-8 and 14 only require the salt. None of the claims are commensurate in scope with the showing. The specification describes the inventive resists as having 1 to 45 parts by mass of the inventive photoacid generating salt based upon 100 parts of the polymer in the prepub of the instant specification at [0494]. The showing is not commensurate in scope with the coverage sought. The breadth of Hatakeyama et al. 20220107559 does not negate the teachings of specific anions having acid labile groups and iodine on the same phenyl ring.
Claims 1-14 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. 20180039173.
Hatakeyama et al. 20180039173 exemplifies PAG 7 and PAG 18
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Which are combined with polymers 1 or polymer 3, as well as a quenchers, surfactant and solvents.
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The PAGs are bounded by formulae
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Herein R.sup.1 is each independently a hydroxyl, C.sub.1-C.sub.20 straight, branched or cyclic alkyl or alkoxy group, C.sub.2-C.sub.20 straight, branched or cyclic acyl or acyloxy group, fluorine, chlorine, bromine, amino, or alkoxycarbonyl-substituted amino group. R.sup.2 is each independently a single bond or C.sub.1-C.sub.4 alkylene group. R.sup.3 is a single bond or C.sub.1-C.sub.20 divalent linking group when p=1, or a C.sub.1-C.sub.20 tri- or tetravalent linking group when p=2 or 3, the linking group optionally containing an oxygen, sulfur or nitrogen atom. Rf.sup.1 to Rf.sup.4 are each independently hydrogen, fluorine or trifluoromethyl, at least one of Rf.sup.1 to Rf.sup.4 being fluorine or trifluoromethyl, or Rf.sup.1 and Rf.sup.2, taken together, may form a carbonyl group. R.sup.4, R.sup.5, R.sup.6, R.sup.7 and R.sup.8 are each independently a C.sub.1-C.sub.12 straight, branched or cyclic alkyl group, C.sub.2-C.sub.12 straight, branched or cyclic alkenyl group, C.sub.6-C.sub.20 aryl group or C.sub.7-C.sub.12 aralkyl or aryloxyalkyl group, in which at least one hydrogen may be substituted by a hydroxyl, carboxyl, halogen, cyano, oxo, amide, nitro, sultone, sulfone, or sulfonium salt-containing moiety, or in which an ether, ester, carbonyl, carbonate or sulfonic acid ester moiety may intervene in a carbon-carbon bond, or R.sup.4 and R.sup.5 may bond together to form a ring with the sulfur atom to which they are attached, m is an integer of 1 to 5, n is an integer of 0 to 3, and p is an integer of 1 to 3 [0010,0038-]
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Hatakeyama et al. 20180039173 does not exemplify the compounds having the OR5 group (O-5a) recited in the instant claims.
With respect to claims 1-8 and 14, it would have been obvious to modify PAG 7 or PAG 18
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by adding an acid labile group such as a t-butoxy, ketal or carbonate acid labile group to the iodine substituted phenyl ring based upon the teachings of the reference including the exemplification of compounds
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with a reasonable expectation of forming a useful photoacid generator.
With respect to claims 1-14, it would have been obvious to modify PAG 7 or PAG 18
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by adding an acid labile group such as a t-butoxy, ketal or carbonate acid labile group to the iodine substituted phenyl ring based upon the teachings of the reference including the exemplification of compounds
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and using the resulting photoacid generator in place of PAG-12 or PAG18 in the cited example with a reasonable expectation of forming a useful photoresist and resist pattern.
In addition to the basis above, it would have been obvious to substitute the replacement phenyl ring as taught in Hatakeyama et al. 20180039173 or to use other linkages between the phenyl moieties taught in Hatakeyama et al. 20180039173 with a reasonable expectation of forming a useful photoacid generator, photoresist and resist pattern.
In the response of 8/10/2026, the applicant argues that the specification demonstrates that the salts of formula (I) provide superior results. Specifically pointing to the line edge roughness. The examiner notes the results and points out that the inventive examples of the instant specification are evidencing improved LER in photoresist compositions including the photoacid generator in specific amounts together with a photoresist resin/polymer containing acid labile groups, while claims 1-8 and 14 only require the salt. None of the claims are commensurate in scope with the showing. The specification describes the inventive resists as having 1 to 45 parts by mass of the inventive photoacid generating salt based upon 100 parts of the polymer in the prepub of the instant specification at [0494]. The showing is not commensurate in scope with the coverage sought. The breadth of Hatakeyama et al. 20180039173 does not negate the teachings of specific anions having acid labile groups and iodine on the same phenyl ring.
Claims 1-14 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. 20230107121, Hatakeyama et al. 20220107559 or Hatakeyama et al. 20180039173, in view of Ichikawa et al. 20120270153.
Ichikawa et al. 20120270153 teaches inventive PAG I6 having the structure (page 45)
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and PAG B-1 (page 52)
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These are used in the resists of example 11 and comparative example 1 (see table 5). These were coated upon silicon wafers, dried, exposed using KrF, post baked and developed in TMAH. The CD uniformity of the example 11 was 1.69 and that of comparative example 1 was 2.28, which is much higher and higher than any of the inventive examples (see table 6) [0173-0177].
Neither Hatakeyama et al. 20230107121, Hatakeyama et al. 20220107559 nor Hatakeyama et al. 20180039173 describe the effect of the addition of the acid labile groups to the anion of the photoacid generator.
In addition to the basis above, it would have been obvious to make the modifications described above to the embodiments rendered obvious by Hatakeyama et al. 20230107121, Hatakeyama et al. 20220107559 or Hatakeyama et al. 20180039173, where an acid labile substituent is added to the iodine substituted phenyl ring with a reasonable expectation of improving the CDU uniformity based upon the disclosure of Ichikawa et al. 20120270153 with respect to example 11 and comparative example 1.
In the response of 8/10/2026, the applicant argues that the comparison in Ichikawa et al. 20120270153 also includes a difference in the resin used and a ethyl (sic methyl, -CH2-) linking group, rather than a direct bond and the point of attachment is a tertiary carbon , rather than a quaternary carbon. The examiner responds that the differences in the anion structure do not significantly affect the acidity of the photoacid anion as the methyladamantyl and adamamantyl moieties are predominantly cycloalkyl moieties with similar carbon contents (C10 vs C11). The resin X1 is fluorinated, so it acts as a surfactant. None of these differences would explain the size the CDU difference between the example 11 and comparative example 1. The examiner is not suggesting that the magnitude of the improvement in CDU uniformity observed in Ichikawa et al. 20120270153 would be expected to be observed when adding an acid labile substituent is added to the iodine substituted phenyl ring to the photoacid generators/salts of Hatakeyama et al. 20230107121, Hatakeyama et al. 20220107559 or Hatakeyama et al. 20180039173, but is asserting that one of ordinary skill in the art would expect improvement in the CDU. The examiner notes that the acid induced cleavage of the ketal yields an oxygen/hydroxy group, which has a similar polarity to the comparative PAG B2 [0170], which yielded a CDU of 1.91 when used in the resist. It is clear that the polar group generated by cleavage of the acid labile moiety on the PAG anion significantly affects the CDU.
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 Martin J Angebranndt whose telephone number is (571)272-1378. The examiner can normally be reached 7-3:30 pm EST.
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, Ching-Yu (Coris) Fung can be reached at 571-270-5713. 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.
MARTIN J. ANGEBRANNDT
Primary Examiner
Art Unit 1737
/MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 September 8, 2026
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