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 .
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 1-13 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, 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 expecation of forming a useful photoacid generator.
With respect to claims 1-10 and 12-13, 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 expecation of forming a useful photoresist and resist pattern.;
With respect to claims 1-13, 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 ot the substrate and using the resulting photoacid generator in place of PAG-10 in the cited example with a reasonable expecation 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.
Claims 1-13 are rejected under 35 U.S.C. 103 as being unpatentable over Chuanwen et al. 20220107559.
Chuanwen 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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Chuanwen 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, 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 expecation of forming a useful photoacid generator.
With respect to claims 1-10 and 12-13, 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 expecation of forming a useful photoresist and resist pattern.;
With respect to claims 1-13, 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 ot the substrate and using the resulting photoacid generator in place of PAG-12 or PAG18 in the cited example with a reasonable expecation 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 Chuanwen et al. 20220107559 or to use other linkages between the phenyl moieties taught in Chuanwen et al. 20220107559 with a reasonable expectation of forming a useful photoacid generator, photoresist and resist pattern.
Claims 1-13 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, 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 expecation of forming a useful photoacid generator.
With respect to claims 1-13, 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 expecation 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.
Claims 1-13 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. 20230107121, Chuanwen et al. 20220107559 or Hatakeyama et al. 20180039173, in view of Adachi et al 20120270152.
Adachi et al 20120270152 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, Chuanwen 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, where an acid labile substituent is added to the iodine substituted phenyl ring with a reasonable expectation of improving the CU uniformity based upon the disclosure of Adachi et al 20120270152 with respect to example 11 and comparative example 1.
Claims 1-13 are rejected under 35 U.S.C. 103 as being unpatentable over Fukushima 20240176236, in view of Hatakeyama et al. 20180039173.
Fukushima 20240176236 (note filing date and foreign priority date) exemplifies PAG-6 (page 181)
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which is used in example 2-6 in combination with polymer P-1 , quencher Q-1 and solvents
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and a surfactant. PAG-6 is also used in examples 2-19 and 2-29 The resists are filtered ([0313] , table 1-2). The resists are coated onto a silicon wafer over a hardmask dried, exposed using EUV, post baked and developed in TMAH to yield a positive resist pattern [0324-0329]. Photoacid PAG 6 is bounded by formula (I)
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, wherein n1 is 0 or 1, n2 is an integer of 1 to 3, n3 is an integer of 1 to 4, n4 is an integer of 0 to 4, meeting n2+n3+n4 s 5 in case of n1=0 and n2+n3+n4≤7 in case of n1=1, n5 is an integer of 0 to 4, R.sup.AL forms an acid labile group with the adjoining oxygen atom. I and —O—R.sup.AL are attached to adjoining carbon atoms, R.sup.1 is a C.sub.1-C.sub.20 hydrocarbyl group which may contain a heteroatom, L.sup.A and L.sup.B are each independently a single bond, ether bond, ester bond, sulfonic ester bond, carbonate bond or carbamate bond, [0036] X.sup.L is a single bond or a C.sub.1-C.sub.40 hydrocarbylene group which may contain a heteroatom, Q.sup.1 and Q.sup.2 are each independently hydrogen, fluorine or a C.sub.1-C.sub.6 fluorinated saturated hydrocarbyl group, Q.sup.3 and Q.sup.4 are each independently fluorine or a C.sub.1-C.sub.6 fluorinated saturated hydrocarbyl group, and Z.sup.+ is an onium cation In one preferred embodiment, R.sup.AL is a group having the formula (AL-1) or (AL-2).
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Herein R.sup.2, R.sup.3 and R.sup.4 are each independently a C.sub.1-C.sub.12 hydrocarbyl group in which some —CH.sub.2— may be replaced by —O— or —S—, with the proviso that when the hydrocarbyl group contains an aromatic ring, some or all of the hydrogen atoms on the aromatic ring may be substituted by halogen, cyano, nitro, optionally halogenated C.sub.1-C.sub.4 alkyl moiety or optionally halogenated C.sub.1-C.sub.4 alkoxy moiety, and R.sup.2 and R.sup.3 may bond together to form a ring with the carbon atom to which they are attached, some —CH.sub.2— in the ring may be replaced by —O— or —S—. [0042] R.sup.5 and R.sup.6 are each independently hydrogen or a C.sub.1-C.sub.10 hydrocarbyl group, R.sup.7 is a C.sub.1-C.sub.20 hydrocarbyl group in which some —CH.sub.2— may be replaced by —O— or —S—, and R.sup.6 and R.sup.7 may bond together to form a C.sub.3-C.sub.20 heterocyclic group with the carbon atom and L.sup.C to which they are attached, some —CH.sub.2— in the heterocyclic group may be replaced by —O— or —S—, [0043] L.sup.C is —O— or —S—, [0044] m1 is 0 or 1, m2 is 0 or 1, and [0045] * designates a point of attachment to the adjoining —O—. [0030-0045]. In formula (1), X.sup.L is a single bond or a C.sub.1-C.sub.40 hydrocarbylene group which may contain a heteroatom. The hydrocarbylene group may be straight, branched or cyclic and examples thereof include alkanediyl and cyclic saturated hydrocarbylene groups. Suitable heteroatoms include oxygen, nitrogen and sulfur [0106] The C.sub.1-C.sub.30 hydrocarbylene group R.sup.203 may be saturated or unsaturated and straight, branched or cyclic. Examples thereof include C.sub.1-C.sub.30 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, dodecane-1,12-diyl, tridecane-1,13-diyl, tetradecane-1,14-diyl, pentadecane-1,15-diyl, hexadecane-1,16-diyl and heptadecane-1,17-diyl groups; C.sub.3-C.sub.30 cyclic saturated hydrocarbylene groups such as cyclopentanediyl, cyclohexanediyl, norbornanediyl and adamantanediyl groups; and arylene groups such as phenylene, methylphenylene, ethylphenylene, n-propylphenylene, isopropylphenylene, n-butylphenylene, isobutylphenylene, sec-butylphenylene, tert-butylphenylene, naphthylene, methylnaphthylene, ethylnaphthylene, n-propylnaphthylene, isopropylnaphthalene, n-butylnaphthylene, isobutylnaphthylene, sec-butylnaphthylene and tert-butylnaphthylene groups. In these hydrocarbylene groups, some or all hydrogen atoms may be substituted by a moiety containing a heteroatom such as oxygen, sulfur, nitrogen or halogen, or some constituent —CH.sub.2— may be replaced by a moiety containing a heteroatom such as oxygen, sulfur or nitrogen, so that the group may contain a hydroxy, cyano, fluorine, chlorine, bromine, iodine, carbonyl, ether bond, ester bond, sulfonic ester bond, carbonate bond, lactone ring, sultone ring, carboxylic anhydride (—C(═O)—O—C(═O)—) or haloalkyl moiety. Of the heteroatoms, oxygen is preferred [0255]. Other PAG anions disclosed include
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(pages 18-37)
Useful lactones disclosed include
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(pages 73-84)
Fukushima 20240176236 does not exemplify the photoacid generator as the exemplified PAG includes a lactone for XL , rather than a phenyl group.
With respect to claims 1-5,7-8, it would have been obvious to modify PAG-6
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by replacing the lactone used for XL in formula (I) with a phenyl group as this is a hydrocarbylene groups within the meaning as evidenced at [0255] of Fukushima 20240176236 and the disclosed equivalence within the exemplified compounds of Hatakeyama et al. 20180039173 with a reasonable expectation of forming a useful photoacid generator.
With respect to claims 1-8, it would have been obvious to modify PAG-6
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by replacing the lactone used for XL in formula (I) with a phenyl group as this is a hydrocarbylene groups within the meaning as evidenced at [0255] of Fukushima 20240176236 and the disclosed equivalence within the exemplified compounds of Hatakeyama et al. 20180039173 and replacing the isopropyl cyclopentane with other leaving groups bounded by AL1 or AL2 with a reasonable expectation of forming a useful photoacid generator.
With respect to claims 1-10 and 12-13, it would have been obvious to modify PAG-6
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by replacing the lactone used for XL in formula (I) with a phenyl group as this is a hydrocarbylene groups within the meaning as evidenced at [0255] of Fukushima 20240176236 and the disclosed equivalence within the exemplified compounds of Hatakeyama et al. 20180039173 and replacing the isopropyl cyclopentane with other leaving groups bounded by AL1 or AL2 and to use the resulting PAGs in the example in place of PAG6
with a reasonable expectation of forming a useful photoresist and photoresist pattern.
With respect to claims 1-10 and 12-13, it would have been obvious to modify PAG-6
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by replacing the lactone used for XL in formula (I) with a phenyl group as this is a hydrocarbylene groups within the meaning as evidenced at [0255] of Fukushima 20240176236 and the disclosed equivalence within the exemplified compounds of Hatakeyama et al. 20180039173 and replacing the isopropyl cyclopentane with other leaving groups bounded by AL1 or AL2, to modify the polymer by adding a lactone ring based upon the disclosure at (pages 73-84) and to use the resulting PAGs in the example in place of PAG6
with a reasonable expectation of forming a useful photoresist and photoresist 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.
Claims 1-13 are rejected under 35 U.S.C. 103 as being unpatentable over Fukushima et al. 20240103364, in view of Hatakeyama et al. 20180039173.
Fukushima et al. 20240103364 (note filing date and foreign priority date) exemplifies PAG-6 (page 228)
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which is combined with polymer P-1 and quencher Q-1 , solvents and surfactants and filtered.. [0323 and table 1). PAG- 6 is also used in examples 2-16, 2-29 (tables 1 and 2). Thr resists are coated on a silicon wafer having a hardmask, dried, exposed using EUV, post baked and developed in TMAH to yield a positive resist pattern [0334-0347]. PAG 6 is bounded by formula (I)
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Herein n1 is 0 or 1, n2 is an integer of 1 to 3, n3 is an integer of 1 to 4, n4 is an integer of 0 to 4, meeting n2+n3+n4≤5 in case of n1=0 and n2+n3+n4≤7 in case of n1=1, n5 is an integer of 0 to 4, R.sup.AL forms an acid labile group with the adjoining oxygen atom. R.sup.F is fluorine, a C.sub.1-C.sub.6 fluorinated saturated hydrocarbyl group, C.sub.1-C.sub.6 fluorinated saturated hydrocarbyloxy group, or C.sub.1-C.sub.6 fluorinated saturated hydrocarbylthio group, a plurality of R.sup.F may be identical or different in case of n3≥2, R.sup.F and —O—R.sup.AL are attached to adjoining carbon atoms, R.sup.1 is a C.sub.1-C.sub.20 hydrocarbyl group which may contain a heteroatom, L.sup.A and L.sup.B are each independently a single bond, ether bond, ester bond, sulfonic ester bond, carbonate bond or carbamate bond, X.sup.L is a single bond or a C.sub.1-C.sub.40 hydrocarbylene group which may contain a heteroatom, Q.sup.1 and Q.sup.2 are each independently hydrogen, fluorine or a C.sub.1-C.sub.6 fluorinated saturated hydrocarbyl group,Q.sup.3 and Q.sup.4 are each independently fluorine or a C.sub.1-C.sub.6 fluorinated saturated hydrocarbyl group, and [0035] Z.sup.+ is an onium cation.
In one preferred embodiment, R.sup.AL is a group having the formula (AL-1) or (AL-2).
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Herein R.sup.2, R.sup.3 and R.sup.4 are each independently a C.sub.1-C.sub.12 hydrocarbyl group in which some —CH.sub.2— may be replaced by —O— or —S—, with the proviso that when the hydrocarbyl group contains an aromatic ring, some or all of the hydrogen atoms on the aromatic ring may be substituted by halogen, cyano, nitro, optionally halogenated C.sub.1-C.sub.4 alkyl moiety or optionally halogenated C.sub.1-C.sub.4 alkoxy moiety, and R.sup.2 and R.sup.3 may bond together to form a ring with the carbon atom to which they are attached, some —CH.sub.2— in the ring may be replaced by —O— or —S—, R.sup.5 and R.sup.6 are each independently hydrogen or a C.sub.1-C.sub.10 hydrocarbyl group, R.sup.7 is a C.sub.1-C.sub.20 hydrocarbyl group in which some —CH.sub.2— may be replaced by —O— or —S—, and R.sup.6 and R.sup.7 may bond together to form a C.sub.3-C.sub.20 heterocyclic group with the carbon atom and L.sup.C to which they are attached, some —CH.sub.2— in the heterocyclic group may be replaced by —O— or —S—, L.sup.C is —O— or —S—, [0040] m1 is 0 or 1, m2 is 0 or 1, designates a point of attachment to the adjoining —O—. [0025-0041] In formula (1), X.sup.L is a single bond or a C.sub.1-C.sub.40 hydrocarbylene group which may contain a heteroatom. The hydrocarbylene group may be straight, branched or cyclic and examples thereof include alkanediyl and cyclic saturated hydrocarbylene groups. Suitable heteroatoms include oxygen, nitrogen and sulfur [0119]. The C.sub.1-C.sub.30 hydrocarbylene group R.sup.203 may be saturated or unsaturated and straight, branched or cyclic. Examples thereof include C.sub.1-C.sub.30 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, dodecane-1,12-diyl, tridecane-1,13-diyl, tetradecane-1,14-diyl, pentadecane-1,15-diyl, hexadecane-1,16-diyl, and heptadecane-1,17-diyl; C.sub.3-C.sub.30 cyclic saturated hydrocarbylene groups such as cyclopentanediyl, cyclohexanediyl, norbornanediyl and adamantanediyl: and arylene groups such as phenylene, methylphenylene, ethylphenylene, n-propyiphenylene, isopropylphenylene, n-butylphenylene, isobutylphenylene, sec-butylphenylene, tert-butylphenylene, naphthylene, methylnaphthylene, ethylnaphthylene, n-propyinaphthylene, isopropyinaphthylene, n-butyinaphthylene, isobutylnaphthylene, sec-butylnaphthylene, and tert-butylnaplithylene. In these hydrocarbylene groups, some or all of the hydrogen atoms may be substituted by a moiety containing a heteroatom such as oxygen, sulfur, nitrogen or halogen, or some constituent —CH.sub.2— may be replaced by a moiety containing a heteroatom such as oxygen, sulfur or nitrogen, so that the group may contain a hydroxy, cyano, fluorine, chlorine, bromine, iodine, carbonyl, ether bond, ester bond, sulfonic ester bond, carbonate bond, lactone ring, sultone ring, carboxylic anhydride (—C(═O)—O—C(═O)—) or haloalkyl moiety. Of the heteroatoms, oxygen is preferred [0266]. Examples of PAG anions include
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(Pages 19-84).
Useful lactones disclosed include
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(pages 122-130)
Fukushima et al. 20240103364 does not exemplify the photoacid generator as the exemplified PAG includes a lactone for XL , rather than a phenyl group.
With respect to claims 1-5,7-8, it would have been obvious to modify PAG-6 (page 228)
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by replacing the lactone used for XL in formula (I) with a phenyl group as this is a hydrocarbylene groups within the meaning as evidenced at [0255] of Fukushima 20240176236 and the disclosed equivalence within the exemplified compounds of Hatakeyama et al. 20180039173 with a reasonable expectation of forming a useful photoacid generator.
With respect to claims 1-8, it would have been obvious to modify PAG-6 (page 228)
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by replacing the lactone used for XL in formula (I) with a phenyl group as this is a hydrocarbylene groups within the meaning as evidenced at [0255] of Fukushima 20240176236 and the disclosed equivalence within the exemplified compounds of Hatakeyama et al. 20180039173 and replacing the isopropyl cyclopentane with other leaving groups bounded by AL1 or AL2 with a reasonable expectation of forming a useful photoacid generator.
With respect to claims 1-10 and 12-13, it would have been obvious to modify PAG-6 (page 228)
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by replacing the lactone used for XL in formula (I) with a phenyl group as this is a hydrocarbylene groups within the meaning as evidenced at [0255] of Fukushima 20240176236 and the disclosed equivalence within the exemplified compounds of Hatakeyama et al. 20180039173 and replacing the isopropyl cyclopentane with other leaving groups bounded by AL1 or AL2 and to use the resulting PAGs in the example in place of PAG6 with a reasonable expectation of forming a useful photoresist and photoresist pattern.
With respect to claims 1-10 and 12-13, it would have been obvious to modify PAG-6 (page 228)
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by replacing the lactone used for XL in formula (I) with a phenyl group as this is a hydrocarbylene groups within the meaning as evidenced at [0255] of Fukushima 20240176236 and the disclosed equivalence within the exemplified compounds of Hatakeyama et al. 20180039173 and replacing the isopropyl cyclopentane with other leaving groups bounded by AL1 or AL2, to modify the polymer by adding a lactone ring based upon the disclosure at (pages 121--130) and to use the resulting PAGs in the example in place of PAG6 with a reasonable expectation of forming a useful photoresist and photoresist 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.
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Fukushima et al. 20240126168 exemplifies the onium salt monomers
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192
81
media_image82.png
Greyscale
PNG
media_image83.png
196
87
media_image83.png
Greyscale
PNG
media_image84.png
197
74
media_image84.png
Greyscale
PNG
media_image85.png
194
88
media_image85.png
Greyscale
PNG
media_image86.png
235
89
media_image86.png
Greyscale
PNG
media_image87.png
229
67
media_image87.png
Greyscale
PNG
media_image88.png
228
125
media_image88.png
Greyscale
PNG
media_image89.png
227
124
media_image89.png
Greyscale
PNG
media_image90.png
224
67
media_image90.png
Greyscale
PNG
media_image91.png
194
131
media_image91.png
Greyscale
PNG
media_image92.png
196
70
media_image92.png
Greyscale
PNG
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248
230
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Greyscale
(page 8-74)
Other PAG anions disclosed include
PNG
media_image94.png
133
187
media_image94.png
Greyscale
PNG
media_image95.png
98
134
media_image95.png
Greyscale
PNG
media_image96.png
91
205
media_image96.png
Greyscale
PNG
media_image97.png
121
133
media_image97.png
Greyscale
PNG
media_image98.png
137
117
media_image98.png
Greyscale
PNG
media_image99.png
184
185
media_image99.png
Greyscale
PNG
media_image100.png
203
113
media_image100.png
Greyscale
(pages 155-186).
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 June 4, 2026
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