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of the applicant has been read and given careful consideration Rejection of the previous action not repeated below are withdrawn.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 1,2,4-11,13,14 and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Fujiwara et al. 20180275516.
Fujiwara et al. 20180275516 exemplifies the anion
PNG
media_image1.png
75
166
media_image1.png
Greyscale
on page 24, where A can be hydrogen or trifluoromethyl and the anion
PNG
media_image2.png
137
163
media_image2.png
Greyscale
on page 30, structure
PNG
media_image3.png
119
145
media_image3.png
Greyscale
are shown on page 23.These are bounded by the formula (3)
PNG
media_image4.png
128
397
media_image4.png
Greyscale
, where wherein, R.sup.10 represents a linear, a branched, or a cyclic monovalent hydrocarbon group having 1 to 40 carbon atoms optionally containing a heteroatom; “L” represents a single bond or a divalent linking group; each of X.sup.f1 and X.sup.f2 independently represents a hydrogen atom, a fluorine atom, or an alkyl group substituted by one or more fluorine atoms; and “k” represents an integer of 0 to 4. Each of X.sup.f1 and X.sup.f2 in the general formula (3) independently represents a hydrogen atom or a fluorine atom, or an alkyl group substituted by one or more fluorine atoms, preferably a hydrogen atom, a fluorine atom, or a trifluoromethyl group. “L” in each of the general formulae (3), (4a), and (4b) represents a single bond or a divalent linking group, preferably a single bond, an ether bond, an ester bond, a sulfonic ester bond, an amide bond, a carbonate bond, and a carbamate bond, particularly preferably a single bond, an ether bond, and an ester bond. R.sup.10 in each of the general formulae (3) and (4a) to (4c) represents a linear, a branched, or a cyclic monovalent hydrocarbon group having 1 to 40 carbon atoms optionally containing a heteroatom. Illustrative example of the monovalent hydrocarbon group includes groups as shown in the examples of the R.sup.1 to R.sup.3, and in such groups, part of hydrogen atoms may be substituted by a substituent such as an alkyl group, an alkoxy group, an alkylcarbonyloxy group, and an alkyloxycarbonyl group. Illustrative example of the monovalent hydrocarbon group also includes a monovalent hydrocarbon group having a steroid skeleton and a monovalent hydrocarbon group having a dehydrocholic acid structure whose part of a steroid skeleton is modified with a substituent. R.sup.10 preferably has a ring structure as a partial structure. The acid diffusion of an anion is controlled by a ring structure to improve lithography performance [0072-0078]. The anions of formula 3 are part of the salt of formula (2)
PNG
media_image5.png
189
370
media_image5.png
Greyscale
, wherein, each of R.sup.1, R.sup.2, and R.sup.3 independently represents any of a hydrogen atom, a partial structure represented by the general formula (1), a linear, a branched, or a cyclic monovalent hydrocarbon group having 1 to 20 carbon atoms optionally containing a heteroatom, or direct binding with an adjacent benzene ring; each of “p1”, “q1”, and “r1” independently represents an integer of 0 to 5, and when “p1”, “q1”, or “r1” represents 2 or more, a plurality of R.sup.1s, R.sup.2s, or R.sup.3s corresponding thereto may be the same or different, when p1+q1+r1 represents 2 or more, a plurality of R.sup.1s, R.sup.2s, or R.sup.3s may be bonded to form a ring together with a carbon atom on a benzene ring bonded thereto, and R.sup.1 and R.sup.2, R.sup.1 and R.sup.3, or R.sup.2 and R.sup.3 may be bonded to form a ring together with two benzene rings bonded thereto and a sulfur atom in the formula, one or more of R.sup.1, R.sup.2, and R.sup.3 represent a partial structure represented by the general formula (1); “*” in the general formula (1) represents a bond with a benzene ring; and Z.sup.− represents a monovalent anion. The sulfonium groups can include
PNG
media_image6.png
218
216
media_image6.png
Greyscale
PNG
media_image7.png
299
220
media_image7.png
Greyscale
PNG
media_image8.png
158
149
media_image8.png
Greyscale
PNG
media_image9.png
171
139
media_image9.png
Greyscale
[0066-0072]. The resist polymers, such as (P-1)of the examples include acid labile moieties
PNG
media_image10.png
117
235
media_image10.png
Greyscale
, a sulfonium salt, a quenchers and surfactant dissolved in a solvent.[0279-0301]. The resists are coated of a silcion wafer including a OSC layer, dried, exposed, post baked and developed [0302]. The full range of the [0126-0135]. The quencher is discussed at composition of the resist polymer can be an amine or a generated weak acid [0158-0174]. The use of sulfonium, iodonium sulfonyldiazo methane, N-sulfonyl oxydicarboxy imide, O-arylsulfonyl oxime, and O-alkylsulfonyl oxime compounds as photoacid generators, including a preference for diphenyliodonium salts when an iodonium salts is used is disclosed [0139].
Fujiwara et al. 20180275516 does not exemplify a photoacid generator bounded by the claims where the cation is bounded by formulae X-1 to X-6, or resists including such a photoacid generator.
With respect to claims 10,11,13,14,16,17 and 20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by pairing the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen with a sulfonium cation bounded by the teachings of formula (2) which specifically refer to the anions of formula (3) with a reasonable expectation of forming a useful photoacid generator.
With respect to claims 10,11,13,14,16,17 and 20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by forming an anion similar to the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen where the piperidine ring of the anion (illustrated) is replaced with a pyrrolidone structure, based upon their equivalence in the anions
PNG
media_image3.png
119
145
media_image3.png
Greyscale
and pairing the resulting anion with a sulfonium cation bounded by the teachings of formula (2) which specifically refer to the anions of formula (3) with a reasonable expectation of forming a useful photoacid generator.
With respect to claims 10,11,13,14,16,17 and 20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by forming an anion similar to the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen where the fluorine atoms are replaced with fluoroalkyl groups and/or k is 2-4 in the formula (3) and pairing the resulting anion with a sulfonium cation bounded by the teachings of formula (2) which specifically refer to the anions of formula (3) with a reasonable expectation of forming a useful photoacid generator.
With respect to claims 10,11,13,14,16,17 and 20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by forming an anion similar to the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen where the fluorine atoms are replaced with fluoroalkyl groups and/or k is 2-4 in the formula (3) and pairing the resulting anion with a iodonium cation based upon the equivalence of these cations in photoacid generators at [0139] with a reasonable expectation of forming a useful photoacid generator.
With respect to claims 1,2,4-5,7,8,10,11 and 13-20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by pairing the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen with a sulfonium cation bounded by the teachings of formula (2) which specifically refer to the anions of formula (3) and using it is a photoresist composition such as those of the examples which contain a resist polymer with an acid labile group bounded by formula (2) of instant claim 7, a quencher and a fluorinated surfactant with a reasonable expectation of forming a useful photoresist. The polymeric fluorinated surfactant addresses the limitation of claim 8.
With respect to claims 1,2,4-5,7,8,10,11 and 13-20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by forming an anion similar to the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen where the piperidine ring of the anion (illustrated) is replaced with a pyrrolidone structure, based upon their equivalence in the anions
PNG
media_image3.png
119
145
media_image3.png
Greyscale
and pairing the resulting anion with a sulfonium cation bounded by the teachings of formula (2) which specifically refer to the anions of formula (3) and using it is a photoresist composition such as those of the examples which contain a resist polymer with an acid labile group bounded by formula (2) of instant claim 7, a quencher and a fluorinated surfactant with a reasonable expectation of forming a useful photoresist. The polymeric fluorinated surfactant addresses the limitation of claim 8.
With respect to claims 1,2,4-5,7,8,10,11 and 13-20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by forming an anion similar to the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen where the fluorine atoms are replaced with fluoroalkyl groups and/or k is 2-4 in the formula (3) and pairing the resulting anion with a sulfonium cation bounded by the teachings of formula (2) which specifically refer to the anions of formula (3) and using it is a photoresist composition such as those of the examples which contain a resist polymer with an acid labile group bounded by formula (2) of instant claim 7, a quencher and a fluorinated surfactant with a reasonable expectation of forming a useful photoresist. The polymeric fluorinated surfactant addresses the limitation of claim 8.
With respect to claims 1,2,4-5,7,8,10,11 and 13-20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by forming an anion similar to the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen where the fluorine atoms are replaced with fluoroalkyl groups and/or k is 2-4 in the formula (3) and pairing the resulting anion with a iodonium cation based upon the equivalence of these cations in photoacid generators at [0139] and using it is a photoresist composition such as those of the examples which contain a resist polymer with an acid labile group bounded by formula (2) of instant claim 7, a quencher and a fluorinated surfactant with a reasonable expectation of forming a useful photoresist. The polymeric fluorinated surfactant addresses the limitation of claim 8.
With respect to claims 1,2,4-5,7-11 and 13-20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by pairing the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen with a sulfonium cation bounded by the teachings of formula (2) which specifically refer to the anions of formula (3), using it is a photoresist composition such as those of the examples which contain a resist polymer with an acid labile group bounded by formula (2) of instant claim 7, a quencher and a fluorinated surfactant, coating, drying, exposing, and developing the resist with a reasonable expectation of forming a useful photoresist pattern. The polymeric fluorinated surfactant addresses the limitation of claim 8.
With respect to claims 1,2,4-5,7-11 and 13-20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by forming an anion similar to the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen where the piperidine ring of the anion (illustrated) is replaced with a pyrrolidone structure, based upon their equivalence in the anions
PNG
media_image3.png
119
145
media_image3.png
Greyscale
and pairing the resulting anion with a sulfonium cation bounded by the teachings of formula (2) which specifically refer to the anions of formula (3) using it is a photoresist composition such as those of the examples which contain a resist polymer with an acid labile group bounded by formula (2) of instant claim 7, a quencher and a fluorinated surfactant, coating, drying, exposing, and developing the resist with a reasonable expectation of forming a useful photoresist pattern. The polymeric fluorinated surfactant addresses the limitation of claim 8.
With respect to claims 1,2,4-5,7-11 and 13-20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by forming an anion similar to the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen where the fluorine atoms are replaced with fluoroalkyl groups and/or k is 2-4 in the formula (3) and pairing the resulting anion with a sulfonium cation bounded by the teachings of formula (2) which specifically refer to the anions of formula (3) using it is a photoresist composition such as those of the examples which contain a resist polymer with an acid labile group bounded by formula (2) of instant claim 7, a quencher and a fluorinated surfactant, coating, drying, exposing, and developing the resist with a reasonable expectation of forming a useful photoresist pattern. The polymeric fluorinated surfactant addresses the limitation of claim 8.
With respect to claims 1,2,4-5,7-11 and 13-20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by forming an anion similar to the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen where the fluorine atoms are replaced with fluoroalkyl groups and/or k is 2-4 in the formula (3) and pairing the resulting anion with a iodonium cation based upon the equivalence of these cations in photoacid generators at [0139] using it is a photoresist composition such as those of the examples which contain a resist polymer with an acid labile group bounded by formula (2) of instant claim 7, a quencher and a fluorinated surfactant, coating, drying, exposing, and developing the resist with a reasonable expectation of forming a useful photoresist pattern. The polymeric fluorinated surfactant addresses the limitation of claim 8.
With respect to claims 1,2,4-11 and 13-20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by pairing the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen with a sulfonium cation bounded by the teachings of formula (2) which specifically refer to the anions of formula (3), using it is a photoresist composition similar to those of the examples which contain a resist polymer with an acid labile group bounded by formula (2) of instant claim 7 and a fluorinated surfactant, but where the quencher in a photosensitive quencher such as those disclosed at [0160-169,173] and a fluorinated surfactant, coating, drying, exposing, and developing the resist with a reasonable expectation of forming a useful photoresist pattern. The polymeric fluorinated surfactant addresses the limitation of claim 8.
With respect to claims 1,2,4-11 and 13-20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by forming an anion similar to the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen where the piperidine ring of the anion (illustrated) is replaced with a pyrrolidone structure, based upon their equivalence in the anions
PNG
media_image3.png
119
145
media_image3.png
Greyscale
and pairing the resulting anion with a sulfonium cation bounded by the teachings of formula (2) which specifically refer to the anions of formula (3) using it is a photoresist composition similar to those of the examples which contain a resist polymer with an acid labile group bounded by formula (2) of instant claim 7 and a fluorinated surfactant, but where the quencher in a photosensitive quencher such as those disclosed at [0160-169,173] and a fluorinated surfactant, coating, drying, exposing, and developing the resist with a reasonable expectation of forming a useful photoresist pattern. The polymeric fluorinated surfactant addresses the limitation of claim 8.
With respect to claims 1,2,4-11 and 13-20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by forming an anion similar to the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen where the fluorine atoms are replaced with fluoroalkyl groups and/or k is 2-4 in the formula (3) and pairing the resulting anion with a sulfonium cation bounded by the teachings of formula (2) using it is a photoresist composition similar to those of the examples which contain a resist polymer with an acid labile group bounded by formula (2) of instant claim 7 and a fluorinated surfactant, but where the quencher in a photosensitive quencher such as those disclosed at [0160-169,173] and a fluorinated surfactant, coating, drying, exposing, and developing the resist with a reasonable expectation of forming a useful photoresist pattern. The polymeric fluorinated surfactant addresses the limitation of claim 8.
With respect to claims 1,2,4-11 and 13-20, it would have been obvious to one skilled in the art to modify the teachings of Fujiwara et al. 20180275516 by forming an anion similar to the anion
PNG
media_image11.png
117
259
media_image11.png
Greyscale
which is bounded by formula (3) where A is hydrogen where the fluorine atoms are replaced with fluoroalkyl groups and/or k is 2-4 in the formula (3) using it is a photoresist composition similar to those of the examples which contain a resist polymer with an acid labile group bounded by formula (2) of instant claim 7 and a fluorinated surfactant, but where the quencher in a photosensitive quencher such as those disclosed at [0160-169,173] and a fluorinated surfactant, coating, drying, exposing, and developing the resist with a reasonable expectation of forming a useful photoresist pattern. The polymeric fluorinated surfactant addresses the limitation of claim 8.
In response to the arguments of 7/1/2026, Fujiwara et al. 20180275516 is similar to Fujiwara et al. 20190324367 (previously applied), but differs in that the cation disclosed is bounded by the language of X-1 to X-6 of the instant claims. The applicant’s argument regrading the cation directed at Fujiwara et al. 20190324367 in not applicable.
Claims 1,2,4-11, and 13-20 are rejected under 35 U.S.C. 103 as being unpatentable over Fujiwara et al. 20180275516, in view of Hatakeyama et al. 20190113843.
Hatakeyama et al. 20190113843 exemplifies sulfonium salt 3, which has the structure (page 93).
PNG
media_image12.png
111
221
media_image12.png
Greyscale
PNG
media_image13.png
159
214
media_image13.png
Greyscale
PNG
media_image14.png
117
229
media_image14.png
Greyscale
PNG
media_image15.png
159
83
media_image15.png
Greyscale
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:
PNG
media_image16.png
119
150
media_image16.png
Greyscale
(page 81)
PNG
media_image17.png
90
176
media_image17.png
Greyscale
(page 76) (
PNG
media_image18.png
81
191
media_image18.png
Greyscale
(page 71)
PNG
media_image19.png
86
168
media_image19.png
Greyscale
(page 63)
PNG
media_image20.png
145
213
media_image20.png
Greyscale
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].
PNG
media_image21.png
180
236
media_image21.png
Greyscale
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
PNG
media_image22.png
146
192
media_image22.png
Greyscale
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].
In addition to the basis above, it would have been obvious to modify the photoacids rendered obvious by Fujiwara et al. 20180275516 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.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to 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 July 31, 2026
Prosecution Insights