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of the applicant has been read and given careful consideration Rejection of the previous action not repeated below are withdrawn. Responses to the arguments are presented after the first rejection they are directed to.
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 1,2,4,5,7,9-11 and 13 are rejected under 35 U.S.C. 102(a)(1) as being fully anticipated by Hatakeyama et al. 20190113843.
Hatakeyama et al. 20190113843 exemplifies sulfonium salt 3, which has the structure (page 93).
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Example 3 combines polymer 1, PAG 2 a sulfonium salt 3 and solvents (see table 1) on page 98).
These are bounded by formulae 3-3 and 3-4). The other examples are similar using sulfonium or iodonium salts which generated non-fluorinated sulfonic acids. These compositions are coated on a silicon wafer substrate, dried, exposure using an electron beam, post baked and developed using TMAH to yield a positive tone resist image. Other anions disclosed include:
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(page 81)
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(page 76) (
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(page 71)
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(page 63)
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Herein R.sup.1 is a hydroxyl group, carboxyl group, C.sub.1-C.sub.6 alkyl group, C.sub.1-C.sub.6 alkoxy group, C.sub.2-C.sub.6 acyloxy group, fluorine, chlorine, amino, —NR.sup.8—C(═O)—R.sup.9, or —NR.sup.8—C(═O)—O—R.sup.9, wherein R.sup.8 is hydrogen or a C.sub.1-C.sub.6 alkyl group, and R.sup.9 is a C.sub.1-C.sub.6 alkyl group, C.sub.2-C.sub.8 alkenyl group or C.sub.7-C.sub.20 aralkyl group. Examples of the alkyl group which may be straight, branched or cyclic include methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclobutyl, n-pentyl, cyclopentyl, n-hexyl and cyclohexyl. Examples of the alkyl moiety in the alkoxy and acyloxy groups are as exemplified just above for the alkyl group. Examples of the alkenyl group which may be straight, branched or cyclic include vinyl, 1-propenyl and 2-propenyl. Examples of the aralkyl group include benzyl and phenethyl. Preferably, R.sup.1 is fluorine, chlorine, hydroxyl, amino, C.sub.1-C.sub.3 alkyl, C.sub.1-C.sub.3 alkoxy, C.sub.2-C.sub.4 acyloxy or —NR.sup.8—C(═O)—R.sup.9.] R.sup.2 is a C.sub.2-C.sub.12 alkylene group or C.sub.6-C.sub.10 arylene group. In the alkylene group, at least one (one or more or even all) hydrogen may be substituted by a halogen other than fluorine. In the arylene group, at least one (one or more or even all) hydrogen may be substituted by a C.sub.1-C.sub.10 alkyl, C.sub.1-C.sub.10 alkoxy, halogen or hydroxyl moiety. Examples of the alkyl and alkoxy groups are as exemplified above. Examples of the alkylene group which may be straight, branched or cyclic include ethylene, propane-1,2-diyl, propane-1,3-diyl, propane-2,3-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-1,4-diyl, cyclohexane-1,4-diyl, adamantane-1,3-diyl, norbornane-2,3-diyl, and norbornane-2,5-diyl. Examples of the arylene group include 1,2-phenylene, 1,3-phenylene, 1,4-phenylene, 1,3-naphthylene, 1,4-naphthylene, 1,5-naphthylene, 1,6-naphthylene, 1,7-naphthylene, 1,8-naphthylene, 2,6-naphthylene, and 2,7-naphthylene. Preferably R.sup.2 is a C.sub.2-C.sub.12 alkylene group. R.sup.3, R.sup.4 and R.sup.5 are each independently fluorine, chlorine, bromine, iodine or a C.sub.1-C.sub.20 monovalent hydrocarbon group which may contain a heteroatom. Any two of R.sup.3, R.sup.4 and R.sup.5 may bond together to form a ring with the sulfur atom to which they are attached. The monovalent hydrocarbon group may be straight, branched or cyclic and examples thereof include C.sub.1-C.sub.20 alkyl groups, C.sub.2-C.sub.20 alkenyl groups, C.sub.6-C.sub.20 aryl groups, and C.sub.7-C.sub.20 aralkyl groups. Also included are substituted forms of the foregoing in which at least one (one or more or even all) hydrogen is substituted by hydroxyl, carboxyl, halogen, oxo, cyano, amide, nitro, sultone, sulfone moiety or sulfonium salt-containing moiety, or in which at least one carbon is substituted by an ether bond, ester bond, carbonyl moiety, carbonate moiety or sulfonic acid ester bond. R.sup.6 and R.sup.7 are each independently trifluoromethyl or a C.sub.1-C.sub.20 monovalent hydrocarbon group which may contain a heteroatom. The monovalent hydrocarbon group may be straight, branched or cyclic. Preferred examples thereof include C.sub.6-C.sub.10 aryl groups, C.sub.2-C.sub.6 alkenyl groups, and C.sub.2-C.sub.6 alkynyl groups, in which at least one (one or more or even all) hydrogen may be substituted by halogen, trifluoromethyl, C.sub.1-C.sub.10 alkyl, C.sub.1-C.sub.10 alkoxy, hydroxyl, carboxyl, C.sub.2-C.sub.10 alkoxycarbonyl, nitro or cyano moiety. X.sup.1 is a single bond or a (p+1)-valent C.sub.1-C.sub.20 linking group which may contain an ether bond, carbonyl, ester bond, amide bond, sultone, lactam, carbonate, halogen, hydroxyl or carboxyl moiety. X.sup.2 is an ether bond or —NR.sup.10—, wherein R.sup.10 is hydrogen or C.sub.1-C.sub.4 alkyl. The subscript m is an integer of 1 to 5, n is an integer of 0 to 3, m+n is 1 to 5, and p is an integer of 1 to 3 [0053-0060].
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In formulae (3-3) and (3-4), R.sup.411 is each independently a hydroxyl, C.sub.1-C.sub.20 alkyl or alkoxy group, C.sub.2-C.sub.20 acyl or acyloxy group, fluorine, chlorine, bromine, amino, or alkoxycarbonyl-substituted amino group. R.sup.412 is each independently a single bond or C.sub.1-C.sub.4 alkylene group. R.sup.413 is a single bond or C.sub.1-C.sub.20 divalent linking group when u=1, or a C.sub.1-C.sub.20 tri- or tetravalent linking group when u=2 or 3, the linking group optionally containing an oxygen, sulfur or nitrogen atom. Rf.sup.21 to Rf.sup.24 are each independently hydrogen, fluorine or trifluoromethyl, at least one of Rf.sup.21 to Rf.sup.24 being fluorine or trifluoromethyl. Rf.sup.21 and Rf.sup.22, taken together, may form a carbonyl group. R.sup.414, R.sup.415, R.sup.416, R.sup.417 and R.sup.418 are each independently a C.sub.1-C.sub.20 monovalent hydrocarbon group which may contain a heteroatom. Any two ofR.sup.414, R.sup.415 and R.sup.416 may bond together to form a ring with the sulfur atom to which they are attached. The monovalent hydrocarbon group may be straight, branched or cyclic, and examples thereof are as exemplified above for R.sup.3 to R.sup.5 in formulae (A-1) and (A-2). The subscript u is an integer of 1 to 3, v is an integer of 1 to 5, and w is an integer of 0 to 3. The foregoing alkyl, alkoxy, acyl, acyloxy and alkenyl groups may be straight, branched or cyclic. The cation in the sulfonium salt having formula (3-1) or (3-3) is as exemplified above for the cation in the sulfonium salt of formula (A-1). The cation in the iodonium salt having formula (3-2) or (3-4) is as exemplified above for the cation in the iodonium salt of formula (A-2) [0130-0135]. The divalent hydrocarbon groups may be straight, branched or cyclic, and examples thereof include linear or branched alkane diyl groups such as methylene, ethylene, 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, heptadecane-1,17-diyl; saturated cyclic divalent hydrocarbon groups such as cyclopentanediyl, cyclohexanediyl, norbornanediyl, and adamantanediyl; and unsaturated cyclic divalent hydrocarbon groups such as phenylene and naphthylene. Also included are the foregoing groups in which at least one hydrogen atom is substituted by an alkyl group such as methyl, ethyl, propyl, n-butyl or t-butyl, or in which at least one hydrogen atom is substituted by a moiety containing a heteroatom such as oxygen, sulfur, nitrogen or halogen, or in which at least one carbon atom is substituted by a moiety containing a heteroatom such as oxygen, sulfur or nitrogen, so that the group may contain a hydroxyl, cyano, carbonyl, ether bond, ester bond, sulfonic acid ester bond, carbonate, lactone ring, sultone ring, carboxylic acid anhydride or haloalkyl moiety. Suitable heteroatoms include oxygen, nitrogen, sulfur and halogen, with oxygen being preferred [0130-0135]. Useful acid labile groups are bounded by
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In formulae (AL-1) and (AL-2), R.sup.L1 and R.sup.L2 are each independently a C.sub.1-C.sub.40 monovalent hydrocarbon group which may contain a heteroatom such as oxygen, sulfur, nitrogen or fluorine. The monovalent hydrocarbon groups may be straight, branched or cyclic, with alkyl groups of 1 to 40 carbon atoms, especially 1 to 20 carbon atoms being preferred. In formula (AL-1), “a” is an integer of 0 to 10, especially 1 to 5. In formula (AL-2), R.sup.L3 and R.sup.L4 are each independently hydrogen or a C.sub.1-C.sub.20 monovalent hydrocarbon group which may contain a heteroatom such as oxygen, sulfur, nitrogen or fluorine. The monovalent hydrocarbon groups may be straight, branched or cyclic, with C.sub.1-C.sub.20 alkyl groups being preferred. Any two of R.sup.L2, R.sup.L3 and R.sup.L4 may bond together to form a ring with the carbon atom or carbon and oxygen atoms to which they are attached. The ring contains 3 to 20 carbon atoms, preferably 4 to 16 carbon atoms, and is typically alicyclic. In formula (AL-3), R.sup.L5, R.sup.L6 and R.sup.L7 are each independently a C.sub.1-C.sub.20 monovalent hydrocarbon group which may contain a heteroatom such as oxygen, sulfur, nitrogen or fluorine. The monovalent hydrocarbon groups may be straight, branched or cyclic, with C.sub.1-C.sub.20 alkyl groups being preferred. Any two of R.sup.L5, R.sup.L6 and R.sup.L7 may bond together to form a ring with the carbon atom to which they are attached. The ring contains 3 to 20 carbon atoms, preferably 4 to 16 carbon atoms and is typically alicyclic. The base polymer may further comprise recurring units (b) having a phenolic hydroxyl group as an adhesive group. Examples of suitable monomers from which recurring units (b) are derived are given below, but not limited thereto. Herein R.sup.A is as defined above [0072-0076]. . Exemplary surfactants are described in JP-A 2008-111103, paragraphs [0165]-[0166]. Inclusion of a surfactant may improve or control the coating characteristics of the resist composition. The surfactant may be used alone or in admixture. The surfactant is preferably added in an amount of 0.0001 to 10 parts by weight per 100 parts by weight of the base polymer [0148]. To the resist composition, a polymeric additive (or water repellency improver) may also be added for improving the water repellency on surface of a resist film as spin coated. The water repellency improver may be used in the topcoatless immersion lithography. Suitable water repellency improvers include polymers having a fluoroalkyl group and polymers having a specific structure with a 1,1,1,3,3,3-hexafluoro-2-propanol residue and are described in JP-A 2007-297590 and JP-A 2008-111103, for example. The water repellency improver to be added to the resist composition should be soluble in the organic solvent as the developer. The water repellency improver of specific structure with a 1,1,1,3,3,3-hexafluoro-2-propanol residue is well soluble in the developer. A polymer having an amino group or amine salt copolymerized as recurring units may serve as the water repellent additive and is effective for preventing evaporation of acid during PEB, thus preventing any hole pattern opening failure after development. An appropriate amount of the water repellency improver is 0 to 20 parts, preferably 0.5 to 10 parts by weight per 100 parts by weight of the base polymer [0156].
The cited resist composition meets the claim limitations of the claims rejected under this heading. With respect to claims 4 and 13, these claims do not require that the onium salt contain a heterocyclic structure, merely that when it doe, it is a pyrrolidone or piperidine structure. In this embodiment, n is equal to 1 and L2 is a methylene (C1) group.
The 1.132 declaration of Ryuichi NEMOTO is noted here, but is not pursuasive as the rejection is a 102 rejection. This is a new rejection which the arguments of the applicant do not address.
Claims 1,2,4,5,7-11 and 13 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. 20190113843.
With respect to claims 1,2,4,5,7-11 and 13, it would have been obvious to modify the cited example by adding a fluorinated polymer are disclosed at [0156] with a reasonable expectation of preventing evaporation of acid during PEB and preventing any hole pattern opening failure after development which are disclosed advantages.
With respect to claims 1,2,4,5,7,9-11 and 13, it would have been obvious to modify the cited example by replacing at least a portion of the methylcyclopentyl acid labile group with another acid labile groups bounded by the disclosure based upon the disclosure of equivalence at [0072-0076].
With respect to claims 1,2,4,5,7,9-11,13,15 and 17, it would have been obvious to modify the cited example by replacing the ethylene R2 with a C3-C12 alkylene moiety as taught at [0053-0055] with a reasonable expectation of forming a useful resist composition based upon the disclosed equivalence of C2-C12 alkylene chains.
With respect to claims 10,11 13 and 16, it would have been obvious to one skilled in the art to form a sulfonium or iodonium salt using the exemplified anion
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with a reasonable expectation of forming a useful photoacid generator. The examiner notes that the L2 embraces substituted alkylene groups, such as the 2,2,2-triflluoroethyl group. Claim 11 is met for n=1
With respect to claims 10,11,13 and 16, it would have been obvious to one skilled in the art to form a sulfonium or iodonium salt using the exemplified anion
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with a reasonable expectation of forming a useful photoacid generator. The examiner notes that the L2 embraces substituted alkylene groups, such as the 2,2,2-triflluoroethyl group. Claim 11 is met for n=1
With respect to claims 10,11,13 and 16-17, it would have been obvious to one skilled in the art to form sulfonium or iodonium salt using an anion similar to the exemplified anions
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or
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where a C1-C20 alkylene linkage is added as taught in for R411 in formulae 3-3 and 3-4 between the other oxygen and the fluorinated groups with a reasonable expectation of forming a useful photoacid generator. Claims 11 and 17 are met when it is a methylene linkage, Claim 17 is met when a C2-C20 linkage is used (1 or 2 of the alkylene linkages in addition to the -CH(CF3)CF2- linkages for n=3 or n=4)
With respect to claims 1,2,4-7,9-11 13,14 and 16, it would have been obvious to one skilled in the art to form a sulfonium or iodonium salt using the exemplified anion
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or
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with a reasonable expectation of forming a useful photoacid generator and to add at least some of the resulting PAG to the resist of the examples which include compounds generating non-fluorinated sulfonic acids (weak acids) with a reasonable expectation of forming a useful resist.
With respect to claims 1,2,4-7,9-11 and 13-16, it would have been obvious to one skilled in the art to form sulfonium or iodonium salt using an anion similar to the exemplified anions
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or
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where a C1-C20 alkylene linkage is added as taught in for R411 in formulae 3-3 and 3-4 between the other oxygen and the fluorinated groups and to add at least some of the resulting PAG to the resist of the examples which include compounds generating non-fluorinated sulfonic acids (weak acids/quencher) with a reasonable expectation of forming a useful resist.
With respect to claims 1,2,4-7,9-11 and 13-16, it would have been obvious to one skilled in the art to form sulfonium or iodonium salt using an anion similar to the exemplified anions
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or
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where a C1-C20 alkylene linkage is added as taught in for R411 in formulae 3-3 and 3-4 between the other oxygen and the fluorinated groups, to add at least some of the resulting PAG to the resists of the examples which include compounds generating non-fluorinated sulfonic acids (weak acids) and adding a fluorinated polymer are disclosed at [0156] with a reasonable expectation of preventing evaporation of acid during PEB and preventing any hole pattern opening failure after development which are disclosed advantages with a reasonable expectation of forming a useful resist. Further it would have been obvious to one skilled in the art to replace at least a portion of the methylcyclopentyl acid labile group with another acid labile groups bounded by the disclosure based upon the disclosure of equivalence at [0072-0076].
The 1.132 declaration of Ryuichi NEMOTO is noted here, but is not pursuasive as the sulfonium salt is bounded by the claims and not one where the carboxyl group is reversed relative to the formula recited in the claims. In terms of the unexpected results, those replied upon by the applicant are realized in the photoresist and are not found in the photoacid generator alone. There is also a question regarding the amount of the polymer, and photoacid generator which must be present for the argued benefits to be realized. This is a new rejection which the arguments of the applicant do not address.
Claims 1,2,4,5,7-11 and 13 are rejected under 35 U.S.C. 102(a)(1) as being fully anticipated by Hatakeyama et al. 20180267402
Hatakeyama et al. 20180267402 exemplifies sulfonium salt 3 having the structure (page 63)
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Which is combined with polymer 1, PAG 1, water repellant polymer 1 and solvents (table 1, page 67).
These are bounded by formulae A-1 and A-2)
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.
Herein R.sup.1 is a hydroxyl group, carboxyl group, C.sub.1-C.sub.6 straight, branched or cyclic alkyl or alkoxy group, C.sub.2-C.sub.6 straight, branched or cyclic acyloxy group, fluorine, chlorine, bromine, amino, —NR.sup.8—C(═O)—R.sup.9, or —NR.sup.8—C(═O)—O—R.sup.9, wherein R.sup.8 is hydrogen or a C.sub.1-C.sub.6 straight, branched or cyclic alkyl group, R.sup.9 is a C.sub.1-C.sub.6 straight, branched or cyclic alkyl group or C.sub.2-C.sub.8 straight, branched or cyclic alkenyl group. R.sup.2 is a C.sub.2-C.sub.12 straight, branched or cyclic alkylene group or C.sub.6-C.sub.10 arylene group. At least one hydrogen (one or more or even all hydrogen atoms) in the alkylene group may be substituted by a halogen other than fluorine, and at least one hydrogen (one or more or even all hydrogen atoms) in the arylene group may be substituted by a C.sub.1-C.sub.10 straight, branched or cyclic alkyl or alkoxy moiety, halogen other than fluorine, or hydroxyl moiety. R.sup.3, R.sup.4 and R.sup.5 are each independently fluorine, chlorine, bromine, iodine, 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 aryloxoalkyl group. At least one hydrogen (one or more or even all hydrogen atoms) in these groups may be substituted by a hydroxyl, carboxyl, halogen, oxo, cyano, amide, nitro, sultone, sulfone or sulfonium salt-containing moiety, or at least one carbon in these groups may be substituted by an ether, ester, carbonyl, carbonate or sulfonate moiety. R.sup.3 and R.sup.4 may bond together to form a ring with the sulfur atom to which they are attached. R.sup.6 and R.sup.7 are each independently trifluoromethyl, a C.sub.6-C.sub.10 aryl group, C.sub.2-C.sub.6 straight, branched or cyclic alkenyl group, or C.sub.2-C.sub.6 straight, branched or cyclic alkynyl group. At least one hydrogen (one or more or even all hydrogen atoms) in these groups may be substituted by a halogen, trifluoromethyl, C.sub.1-C.sub.10 straight, branched or cyclic alkyl or alkoxy, hydroxyl, carboxyl, C.sub.2-C.sub.10 straight, branched or cyclic alkoxycarbonyl, nitro or cyano moiety. X.sup.1 is a single bond, or a (p+1)-valent C.sub.1-C.sub.20 linking group which may contain an ether, carbonyl, ester, amide, sultone, lactam, carbonate, halogen, hydroxyl or carboxyl moiety. X.sup.2 is an ether group or —NR.sup.10—, wherein R.sup.10 is hydrogen or C.sub.1-C.sub.4 straight or branched alkyl group, 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 [0054-0055].
Useful acid labile groups are bounded by
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[0066].
The cited resist composition meets the claim limitations of the claims rejected under this heading. With respect to claims 4 and 13, these claims do not require that the onium salt contain a heterocyclic structure, merely that when it does, the heterocycle has a pyrrolidone or piperidine structure.
Claims 1,2,4-11 and 13 are rejected under 35 U.S.C. 102(a)(1)as being fully anticipated by Hatakeyama et al. 20170369616.
Hatakeyama et al. 20170369616 exemplifies PAG 3 (page 68).
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which in resist 1-3 is combined with polymer 1 (page 72), quencher 1 (weak photoacid), a water repellant (fluorinated) polymer 1 and solvents. (table 1, page 75). This is coated, dried, exposed using ArF, post baked and developed in TMAH to yields a positive tone image [0120].
Claims 1,2,4-11,13,14 and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Fujiwara et al. 20190324367
Fujiwara et al. 20190324367 exemplifies the following photoacid generators (pages 16, 21 and 22)
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,
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where RFA is hydrogen or trifluoromethyl [0066].
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(page 28)
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(page 27). These are bounded by the formula 1A’,
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In formula (1A′), R.sup.d is hydrogen or trifluoromethyl, preferably trifluoromethyl. R.sup.e is a C.sub.1-C.sub.38 monovalent hydrocarbon group which may contain a heteroatom. The heteroatom is preferably selected from oxygen, nitrogen, sulfur and halogen, with oxygen being more preferred. The monovalent hydrocarbon group is preferably of 6 to 30 carbon atoms because a high resolution is achievable in forming fine size patterns. The monovalent hydrocarbon group may be straight, branched or cyclic. Examples include straight or branched alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, cyclopentyl, hexyl, heptyl, 2-ethylhexyl, nonyl, undecyl, tridecyl, pentadecyl, heptadecyl, and icosanyl; monovalent saturated alicyclic hydrocarbon groups such as cyclohexyl, 1-adamantyl, 2-adamantyl, 1-adamantylmethyl, norbornyl, norbornylmethyl, tricyclodecanyl, tetracyclododecanyl, tetracyclododecanylmethyl, and dicyclohexylmethyl; monovalent unsaturated aliphatic hydrocarbon groups such as allyl and 3-cyclohexenyl; and aralkyl groups such as benzyl and diphenylmethyl. Suitable heteroatom-containing monovalent hydrocarbon groups include tetrahydrofuryl, methoxymethyl, ethoxymethyl, methylthiomethyl, acetamidomethyl, trifluoroethyl, (2-methoxyethoxy)methyl, acetoxymethyl, 2-carboxy-1-cyclohexyl, 2-oxopropyl, 4-oxo-1-adamantyl, and 3-oxocyclohexyl. In the foregoing groups, one or more hydrogen atoms may be substituted by a substituent containing a heteroatom such as oxygen, sulfur, nitrogen or halogen, or one or more carbon atoms may be substituted by a substituent containing a heteroatom such as oxygen, sulfur or nitrogen, so that the group may contain a hydroxyl radical, cyano radical, carbonyl radical, ether bond, ester bond, sulfonic acid ester bond, carbonate bond, lactone ring, sultone ring, carboxylic anhydride or haloalkyl radical [0056-0057].
The disclosed cation has the structure
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In formula (1a), X.sup.a and X.sup.b are each independently a C.sub.1-C.sub.30 divalent hydrocarbon group which may contain a heteroatom [0040-0053]. In the examples a resist polymer is combined with the photoacid generator, a quencher (weak photoacid) , a surfactant (fluoropolymer F-1, [0275])an alkali soluble surfactant and solvents. (see table 1, page 93). These are coated upon a silicon wafer, dried, exposed using an ArF laser exposure device, post baked and developed in TMAH to yield a positive image [0279].
With respect to claims 10,11, and 16, it would have been obvious to one skilled in the art to combine the anions exemplified
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with the disclosed cations with a reasonable expectation of forming useful photoacid generators.
With respect to claims 1,2,5-11, 14 and 16, it would have been obvious to one skilled in the art to combine the anions exemplified
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or
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and to add these to the compositions of the examples with a reasonable expectation of forming useful photoresist. Further, it would have been obvious to use them in the processes disclosed with a reasonable expectation of forming a useful resist pattern.
With respect to claims 10,11,13 and 16, it would have been obvious to one skilled in the art to modify the anions
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or
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by replacing the nitrogen containing piperidine ring other exemplified nitrogen containing rings, such as pyrimidine and combining the resulting anion with the disclosed cations with a reasonable expectation of forming useful photoacid generators.
With respect to claims 1,2,4-11,13,14 and 16, it would have been obvious to one skilled in the art to modify the anions
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by replacing the nitrogen containing piperidine ring other exemplified nitrogen containing rings, such as pyrimidine and combining the resulting anion with the disclosed cations and to add these to the compositions of the examples with a reasonable expectation of forming useful photoresist. Further, it would have been obvious to use them in the processes disclosed with a reasonable expectation of forming a useful resist pattern.
With respect to claims 1,2,4-11,13,14 and 16, it would have been obvious to one skilled in the art to modify the anions
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by replacing the nitrogen containing piperidine ring other exemplified nitrogen containing rings, such as a pyrrolidone ring (which is the exemplified pyrrole ring with a carbonyl on the ring) and combining the resulting anion with the disclosed cations and to add these to the compositions of the examples with a reasonable expectation of forming useful photoresist. Further, it would have been obvious to use them in the processes disclosed with a reasonable expectation of forming a useful resist pattern.
Claims 1,2,4-11, and 13-17 are rejected under 35 U.S.C. 103 as being unpatentable over Fujiwara et al. 20190324367, in view of Hatakeyama et al. 20190113843.
In addition to the basis above, it would have been obvious to modify the photoacids rendered obvious by Fujiwara et al. 20190324367 and the resists using them by adding a C.sub.1-C.sub.12 alkyl group between the fluoroalkyl group and the oxygen based upon the teaching for R.sup.411 in formulae (3-3) and (3-4) of Hatakeyama et al. with a reasonable expectation of forming a useful photoacid generator and resist including it.
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.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mark F Huff can be reached at 571-272-1385. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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MARTIN J. ANGEBRANNDT
Primary Examiner
Art Unit 1737
/MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 March 31, 2026
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