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 Rejection of the previous action not repeated below are withdrawn in view of the arguments and amendment of the applicant. Responses to the arguments of the applicant are presented after the first rejection to which they are directed.
The amendment filed 07/06/2026 is objected to under 35 U.S.C. 132(a) because it introduces new matter into the disclosure. 35 U.S.C. 132(a) states that no amendment shall introduce new matter into the disclosure of the invention. The added material which is not supported by the original disclosure is as follows:
The text added in [0366] excluding Rl1-Rl3 not all being hydrogen at the same time and replacing “optionally having a heteroatom” with 6 lines of added text is not supported by the specification as filed.
Applicant is required to cancel the new matter in the reply to this Office Action.
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1-22 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
The language “may contain a hydroxy group, an alkoxy group, a thioalkoxy group, a fluorine-containing alkyl group, a fluorine-containing alkoxy group, a fluorine-containing thioalkoxy group, a cyano group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a carbonyl group, an ether bond, an ester bond, a sulfonic acid ester bond, a carbonate bond, a lactone ring, a sultone ring, a carboxylic anhydride, a haloalkyl group” appears in [0082] as possibilities for RL1-RL3, not RL4.
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.
Claim 1-6,8-10,12, and 15-22 are rejected under 35 U.S.C. 103 as being unpatentable over Hirano et al. JP 2008249890.
Hirano et al. JP 2008249890 (machine translation attached, cited by applicant) exemplifies repeating units
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[0054-0057]. Resist polymers A-1 to A-4, A11 to A-14,A-31, A-32, A-36 and A-37 are illustrated at [0117-0124].
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Resist compositions are disclosed in table 2 and resists 3,5,16,17,21 and 22 use resist polymers reproduced above in combination with PAGS B-16, B-82,B-87,B-80 and B-79 and P-8, P-1,P-40 and P-74, amines D-1 and surfactant W-3, W-1, and W-2
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D-1: Dicyclohexylmethylamine D-2: 2,4,6-triphenylimidazole D-3: Tetra- (n-butyl) ammonium hydroxide
W-1: Fluorosurfactant, PF6320 (manufactured by OMNOVA)
W-2: Fluorine / silicone surfactant, MegaFac R08 (manufactured by Dainippon Ink & Chemicals, Inc.)
W-3: Silicon-based surfactant, siloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.) [0318-0323]
These are coated upon s silicon wafer, dried/pre-baked, exposed using an electron beam, post baked at 100 degrees C for 90 seconds, developed in TMAH and rinsed with water [0327]
The repeating units are embraced by formula 1,
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where L represents a hydrogen atom, an alkyl group, a cycloalkyl group or an aralkyl group.
Z .sup.1 represents a group containing a group having at least one benzene ring and having at least absorption at 248 nm. Z .sup.1 and L may be bonded to each other to form a 5- or 6-membered ring. Ra and Rb are each independently a hydrogen atom, alkyl group, hydroxyl group, alkoxy group, halogen atom, cyano group, nitro group, acyl group, acyloxy group, cycloalkyl group, aryl group, carboxyl group, alkyloxycarbonyl group Represents an alkylcarbonyloxy group or an aralkyl group. Z represents a non-acid-decomposable group. k is an integer of 0 to 4, n is an integer of 1 to 4, and 1 ≦ k + n ≦ 5. The alkyl group as L may have a substituent and may be linear or branched. As a linear alkyl group, Preferably it is C1-C30, More preferably, it is 1-20, For example, a methyl group, an ethyl group, n-propyl group, n-butyl group, sec-butyl group, t-butyl Group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decanyl group and the like. As a branched alkyl group, Preferably it is C3-C30, More preferably, it is 3-20, for example, i-propyl group, i-butyl group, t-butyl group, i-pentyl group, t-pentyl group, Examples include i-hexyl group, t-hexyl group, i-heptyl group, t-heptyl group, i-octyl group, t-octyl group, i-nonyl group, t-decanoyl group and the like. The cycloalkyl group as L preferably has 6 to 15 carbon atoms, such as a cyclohexyl group and an adamantyl group. Examples of the group represented by Z .sup.1 include an arylcarbonyl group, a condensed ring aryl group, a condensed ring arylcarbonyl group, an alkyl group having an arylcarbonyl group, an alkyl group having a condensed aryl group, and an alkyl group having a condensed arylcarbonyl group. Etc. The aryl group is not particularly limited, but generally includes those having 6 to 14 carbon atoms such as a phenyl group, a xylyl group, a toluyl group, a cumenyl group, a naphthyl group, an anthracenyl group, and the above-mentioned alkyl groups and cycloalkyl groups. And may have a substituent such as an alkoxy group [0028-0058].
Other useful repeating units disclosed include (pages 31-32
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Carboxylic acid generating photoacid generators (quenchers, which generate weak acids) are disclosed at [0200-0212]. Useful photoacid generators are disclosed. The alkyl group, cycloalkyl group and aryl group in the aliphatic sulfonate anion and aromatic sulfonate anion may have a substituent. Examples of the substituent of the alkyl group, cycloalkyl group, and aryl group in the aliphatic sulfonate anion and aromatic sulfonate anion include, for example, a nitro group, a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom), carboxyl group , Hydroxyl group, amino group, cyano group, alkoxy group (preferably having 1 to 15 carbon atoms), cycloalkyl group (preferably having 3 to 15 carbon atoms), aryl group (preferably having 6 to 14 carbon atoms), alkoxycarbonyl group ( Preferably 2 to 7 carbon atoms, acyl group (preferably 2 to 12 carbon atoms), alkoxycarbonyloxy group (preferably 2 to 7 carbon atoms), alkylthio group (preferably 1 to 15 carbon atoms), alkylsulfonyl group (Preferably having 1 to 15 carbon atoms), alkyliminosulfonyl group (preferably having 2 to 15 carbon atoms), aryl Ruoxysulfonyl group (preferably having 6 to 20 carbon atoms), alkylaryloxysulfonyl group (preferably having 7 to 20 carbon atoms), cycloalkylaryloxysulfonyl group (preferably having 10 to 20 carbon atoms), alkyloxyalkyloxy group (Preferably having 5 to 20 carbon atoms), a cycloalkylalkyloxyalkyloxy group (preferably having 8 to 20 carbon atoms), and the like. About the aryl group and ring structure which each group has, an alkyl group (preferably C1-C15) can further be mentioned as a substituent. A compound that generates sulfonic acid upon irradiation with actinic rays or radiation, which is preferable as an acid generator (also referred to as a sulfonic acid generator), is a compound that generates sulfonic acid upon irradiation with actinic rays or radiation such as KrF excimer laser light, electron beam, EUV, etc. Examples of such compounds are diazonium salts, phosphonium salts, sulfonium salts, iodonium salts, imide sulfonates, oxime sulfonates, diazodisulfones, disulfones, and o-nitrobenzyl sulfonates. [0131-0199] In the present invention, surfactants can be used, which are preferable from the viewpoints of film forming properties, pattern adhesion, development defect reduction, and the like. Specific examples of the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, polyoxyethylene Polyoxyethylene alkyl allyl ethers such as nonylphenol ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate Sorbitan fatty acid esters such as rate, polyoxyethylene sorbitan monolaurate, polyoxyethylene Sorbitan mono palmitate - door, Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, F-top EF301, EF303, EF352 (Shin-Akita Kasei) (Made by Co., Ltd.), MegaFuck F171, F173 (Dainippon Ink Chemical Co., Ltd.), Florad FC430, FC431 (Sumitomo 3M), Asahi Guard AG710, Surflon S-382, SC101, SC102 , SC103, SC104, SC105, SC106 (manufactured by Asahi Glass Co., Ltd.), Troysol S-366 (manufactured by Troy Chemical Co., Ltd.) and the like, or silicon-based surfactants, organosiloxane polymer KP341 Shin-Etsu Chemical Co., Ltd.) and acrylic or methacrylic acid-based (co) polymer Polyflow No. 75, no. 95 (manufactured by Kyoeisha Yushi Chemical Co., Ltd.). The compounding amount of these surfactants is usually 2 parts by mass or less, preferably 1 part by mass or less per 100 parts by mass of the solid content in the composition of the present invention. These surfactants may be added alone or in some combination. The surfactant is any one of fluorine and / or silicon surfactants (fluorine surfactants and silicon surfactants, surfactants containing both fluorine atoms and silicon atoms), or It is preferable to contain 2 or more types. As these surfactants, for example, JP-A-62-36663, JP-A-61-226746, JP-A-61-226745, JP-A-62-170950, JP-A-63-34540 No. 7, JP-A-7-230165, JP-A-8-62834, JP-A-9-54432, JP-A-9-5988, JP-A 2002-277862, US Pat. No. 5,405,720. , No. 5,360,692, No. 5,529,881, No. 5,296,330, No. 5,543,098, No. 5,576,143, No. 5,294,511, No. 5,824,451. The following commercially available surfactants can also be used as they are. Examples of commercially available surfactants that can be used include F-top EF301, EF303 (manufactured by Shin-Akita Kasei Co., Ltd.), Florard FC430, 431 (manufactured by Sumitomo 3M Co., Ltd.), MegaFuck F171, F173, F176, F189, R08 (Dainippon Ink Chemical Co., Ltd.), Surflon S-382, SC101, 102, 103, 104, 105, 106 (Asahi Glass Co., Ltd.), Troisol S-366 (Troy Chemical Co., Ltd.), etc. Fluorine type surfactant or silicon type surfactant can be mentioned. Polysiloxane polymer KP-341 (manufactured by Shin-Etsu Chemical Co., Ltd.) can also be used as a silicon-based surfactant. In addition to the known surfactants described above, surfactants are derived from fluoroaliphatic compounds produced by the telomerization method (also referred to as the telomer method) or the oligomerization method (also referred to as the oligomer method). A surfactant using a polymer having a fluoroaliphatic group can be used. The fluoroaliphatic compound can be synthesized by the method described in JP-A-2002-90991. As the polymer having a fluoroaliphatic group, a copolymer of a monomer having a fluoroaliphatic group and (poly (oxyalkylene)) acrylate and / or (poly (oxyalkylene)) methacrylate is preferable and distributed irregularly. Or may be block copolymerized. Examples of the poly (oxyalkylene) group include a poly (oxyethylene) group, a poly (oxypropylene) group, a poly (oxybutylene) group, and the like, and a poly (oxyethylene, oxypropylene, and oxyethylene group). A unit having different chain lengths in the same chain length, such as a block linked body) or a poly (block linked body of oxyethylene and oxypropylene) group, may be used. Furthermore, a copolymer of a monomer having a fluoroaliphatic group and (poly (oxyalkylene)) acrylate (or methacrylate) is not only a binary copolymer but also a monomer having two or more different fluoroaliphatic groups, Further, it may be a ternary or higher copolymer obtained by simultaneously copolymerizing two or more different (poly (oxyalkylene)) acrylates (or methacrylates). Examples of commercially available surfactants include Megafac F178, F-470, F-473, F-475, F-476, and F-472 (Dainippon Ink Chemical Co., Ltd.). Further, a copolymer of an acrylate (or methacrylate) having a C .sub.6 F .sub.13 group and (poly (oxyalkylene)) acrylate (or methacrylate), an acrylate (or methacrylate) having a C .sub.6 F .sub.13 group and (poly (oxy) A copolymer of (ethylene)) acrylate (or methacrylate) and (poly (oxypropylene)) acrylate (or methacrylate), an acrylate (or methacrylate) having a C .sub.8 F .sub.17 group and (poly (Oxyalkylene)) acrylate (or methacrylate) copolymer, acrylate (or methacrylate), (poly (oxyethylene)) acrylate (or methacrylate) and (poly (oxypropylene)) acrylate having C .sub.8 F .sub.17 groups ( Or a copolymer with methacrylate). The amount of the surfactant used is preferably 0.0001 to 2% by mass, more preferably 0.001 to 1% by mass, based on the total amount of the positive resist composition (excluding the solvent) [0288-0295]. Other components The positive resist composition of the present invention may further contain a dye, a photobase generator and the like, if necessary [0296-0298]. In the manufacture of precision integrated circuit elements, the pattern forming process on the resist film is carried out on the substrate (eg, silicon / silicon dioxide coated substrate, glass substrate, ITO substrate, quartz / chromium oxide coated substrate, etc.). A resist pattern is formed by applying a resist composition, forming a resist film, and then irradiating actinic rays or radiation such as KrF excimer laser light, electron beam, EUV light, etc., heating, developing, rinsing and drying [0304]. In the manufacture of precision integrated circuit elements, the pattern forming process on the resist film is carried out on the substrate (eg, silicon / silicon dioxide coated substrate, glass substrate, ITO substrate, quartz / chromium oxide coated substrate, etc.). A resist pattern is formed by applying a resist composition, forming a resist film, and then irradiating actinic rays or radiation such as KrF excimer laser light, electron beam, EUV light, etc., heating, developing, rinsing and drying. Can be formed [0304]
Hirano et al. JP 2008249890 does not exemplify polymers where at least one of RL1-RL3 is a hydrocarbyl group The reference also does not exemplify polymers with the full range of repeating units recited in claim 6 or repeating units of claim 1 with halogen or hydrocarbyl moieties other than acetate and methyl carbonyl.
With respect to claims 1-6 and 8, it would have been obvious to one skilled in the art to modify the polymer A-13 or A-2 by replacing the C1 methyl in the acetal group with a C2-19 alkyl group based upon the disclosed at disclosed that L can be a linear or branched C1-30 alkyl at [0030] with a reasonable expectation of forming a useful resist polymer.
With respect to claims 1-6 and 8, it would have been obvious to one skilled in the art to modify the polymer A-13 or A-2 by replacing the C1 methyl in the acetal group with a C2-19 alkyl group based upon the disclosed at disclosed that L can be a linear or branched C1-30 alkyl at [0030] and the terminal phenyl ring is substituted with an ether (-O-),, alkoxy or thioalkoxy groups rather than an ester group based upon the disclosure at [0033-0034] with a reasonable expectation of forming a useful resist polymer.
With respect to claims 1-6,8-10,12, and 15-20, it would have been obvious to one skilled in the art to modify the resist composition of example 10 by using a polymer similar to polymer A-13 where the the C1 methyl in the acetal group is replaced with a C2-19 alkyl group based upon the disclosed at disclosed that L can be a linear or branched C1-30 alkyl at [0030] with a reasonable expectation of forming a useful resist composition.
With respect to claims 1-6,8-10,12, and 15-20, it would have been obvious to one skilled in the art to modify the resist composition of example 10 by using a polymer similar to polymer A-13 where the C1 methyl in the acetal group is replaced with a C2-19 alkyl group based upon the disclosed at disclosed that L can be a linear or branched C1-30 alkyl at [0030] and the terminal phenyl ring is substituted with an ether (-O-),, alkoxy or thioalkoxy groups rather than an ester group based upon the disclosure at [0033-0034] with a reasonable expectation of forming a useful resist composition.
In addition to the basis above, it would have been obvious to one skilled in the art to modify the exemplified polymers of Hirano et al. JP 2008249890, resists using them or polymers/resists rendered obvious by Hirano et al. JP 2008249890 by adding a other repeating units disclosed such as those disclosed on pages 31 and 32 of Hirano et al. JP 2008249890 with a reasonable expectation of forming as useful resist based upon the disclosure of these as useful repeating units, by using other exposures, such as excimer lasers, EUV with a reasonable expectation of forming a useful pattern based upon the disclosure of these as actinic light at [0304] and/or by using other disclosed substrates such as a chromium oxide coated quartz substrate
With respect to claims 15 and 16, the examiner holds that the dissolution rate of the unexposed resist is less than 10 nm/min for at least one alkaline developer composition. With respect to claim 17, the examiner holds that the dissolution rate of the exposed resist is more than 50 nm/min for at least one alkaline developer composition.
In the response of 7/6/2026, the applicant argues that the claims do not disclosed/exemplify a polymer having a repeating unit bounded by the added claim language. The examiner points to
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, where the RL1-RL3 are hydrogen, and n1 is 1, and RL4 is an ester, which also includes a -O- bond and L can be C2-19 alkyl which is within the C1-30 range disclosed at [0030].
Claims 1-6,8-10,12 and 15-20 are rejected under 35 U.S.C. 103 as being unpatentable over Mizutani JP 2005274878.
Mizutani JP 2005274878 (machine translation attached) exemplifies resist polymers (P-4 and P-5) on page 23.
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The inventive examples (see table 1) combine polymers with photoacid generators, amines (basic compounds/quenchers) and surfactants [0190-0194]. A resist film was obtained in the same manner as in Example 1 using the resist compositions in Examples 1 and 2 and Comparative Examples 1 and 2. However, the resist film thickness was 0.15 μm. The obtained resist film was subjected to surface exposure using EUV light (wavelength 13 nm) while changing the exposure amount by 0.5 mJ in the range of 0 to 5.0 mJ, and further baked at 110 ° C. for 90 seconds. Thereafter, using a 2.38 mass% tetramethylammonium hydroxide (TMAH) aqueous solution, the dissolution rate at each exposure amount was measured to determine the sensitivity [0195]. The polymers are bounded by A1, A2,X1 and X2, where
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Z represents a hydroxyl group, a halogen atom, a cyano group, a nitro group, an acyl group or an acyloxy group. A .sub.1 represents a group containing a cyclic carbon structure and decomposing by the action of an acid m and n each independently represent 0-4. And in x1 and x2 R .sub.1 and R .sub.2 each independently represents a hydrogen atom or an alkyl group (preferably having 1 to 4 carbon atoms). R .sub.3 and R .sub.4 each independently represents a hydrogen atom, an alkyl group or a cycloalkyl group. m represents an integer of 0 to 20. W represents a divalent linking group. Y represents —O—, —OCO—, —COO—, —NHCO—, —CONH—, —S—, —SO .sub.2 —, or —SO .sub.3 —. Z .sub.a represents a group having a cycloalkyl group or a group having an aryl group [0011-0015]. Examples of the aryl group of the Z .sub.a in the general formula (X1), preferably 6 to 30 carbon atoms, more preferably from 6 to 20 carbon atoms, e.g., phenyl, 4-methylphenyl, 3-methylphenyl group 2-methylphenyl group, 4-ethylphenyl group, 3-ethylphenyl group, 2-ethylphenyl group, 4-n-propylphenyl group, 3-n-propylphenyl group, 2-n-propylphenyl group, 4 -I-propylphenyl group, 3-i-propylphenyl group, 2-i-propylphenyl group, 4-cyclopropylphenyl group, 3-cyclopropylphenyl group, 2-cyclopropylphenyl group, 4-n-butylphenyl Group, 3-n-butylphenyl group, 2-n-butylphenyl group, 4-i-butylphenyl group, 3-i-butylphenyl group, 2-i- Tilphenyl group, 4-t-butylphenyl group, 3-t-butylphenyl group, 2-t-butylphenyl group, 4-cyclobutylphenyl group, 3-cyclobutylphenyl group, 2-cyclobutylphenyl group, 4- Cyclopentylphenyl group, 4-cyclohexylphenyl group, 4-cycloheptenylphenyl group, 4-cyclooctanylphenyl group, 2-cyclopentylphenyl group, 2-cyclohexylphenyl group, 2-cycloheptenylphenyl group, 2-cycloocta Nylphenyl, 3-cyclopentylphenyl, 3-cyclohexylphenyl, 3-cycloheptenylphenyl, 3-cyclooctanylphenyl, 4-cyclopentyloxyphenyl, 4-cyclohexyloxyphenyl, 4-cyclohept Tenyloxyphenyl group Crooctanyloxyphenyl group, 2-cyclopentyloxyphenyl group, 2-cyclohexyloxyphenyl group, 2-cycloheptenyloxyphenyl group, 2-cyclooctanyloxyphenyl group, 3-cyclopentyloxyphenyl group, 3-cyclohexyloxy Phenyl group, 3-cycloheptenyloxyphenyl group, 3-cyclooctanyloxyphenyl group, 4-n-pentylphenyl group, 4-n-hexylphenyl group, 4-n-heptenylphenyl group, 4-n- Octanylphenyl group, 2-n-pentylphenyl group, 2-n-hexylphenyl group, 2-n-heptenylphenyl group, 2-n-octanylphenyl group, 3-n-pentylphenyl group, 3-n -Hexylphenyl group, 3-n-heptenylphenyl group, 3-n-octanyl group Nyl group, 2,6-di-isopropylphenyl group, 2,3-di-isopropylphenyl group, 2,4-di-isopropylphenyl group, 3,4-di-isopropylphenyl group, 3,6-di-t -Butylphenyl group, 2,3-di-t-butylphenyl group, 2,4-di-t-butylphenyl group, 3,4-di-t-butylphenyl group, 2,6-di-n-butyl Phenyl group, 2,3-di-n-butylphenyl group, 2,4-di-n-butylphenyl group, 3,4-di-n-butylphenyl group, 2,6-di-i-butylphenyl group 2,3-di-i-butylphenyl group, 2,4-di-i-butylphenyl group, 3,4-di-i-butylphenyl group, 2,6-di-t-amylphenyl group, 2 , 3-di-t-amylphenyl group, 2,4-di-t-amylphenyl group, 3 4-di-t-amylphenyl group, 2,6-di-i-amylphenyl group, 2,3-di-i-amylphenyl group, 2,4-di-i-amylphenyl group, 3,4- Di-i-amylphenyl group, 2,6-di-n-pentylphenyl group, 2,3-di-n-pentylphenyl group, 2,4-di-n-pentylphenyl group, 3,4-di- n-pentylphenyl group, 4-adamantylphenyl group, 2-adamantylphenyl group, 4-isoboronylphenyl group, 3-isoboronylphenyl group, 2-isobornylphenyl group, 4-cyclopentyloxyphenyl group, 4 -Cyclohexyloxyphenyl group, 4-cycloheptenyloxyphenyl group, 4-cyclooctanyloxyphenyl group, 2-cyclopentyloxyphenyl group, 2-cyclohexyloxyphenyl group, 2-cycloheptenyloxyphenyl group, 2-cyclooctanyloxyphenyl group, 3-cyclopentyloxyphenyl group, 3-cyclohexyloxyphenyl group, 3-cycloheptenyloxyphenyl group, 3-cyclooctenyloxyphenyl group, 4-n-pentyloxyphenyl group, 4-n-hexyloxyphenyl group, 4-n-heptenyloxyphenyl group, 4-n-octanyloxyphenyl group, 2-n-pentyloxyphenyl group, 2 -N-hexyloxyphenyl group, 2-n-heptenyloxyphenyl group, 2-n-octanyloxyphenyl group, 3-n-pentyloxyphenyl group, 3-n-hexyloxyphenyl group, 3-n- Heptenyloxyphenyl group, 3-n-octanyloxyphenyl group, 2,6-di-isopropyl Pyroxyphenyl group, 2,3-di-isopropyloxyphenyl group, 2,4-di-isopropyloxyphenyl group, 3,4-di-isopropyloxyphenyl group, 2,6-di-t-butyloxyphenyl group 2,3-di-t-butyloxyphenyl group, 2,4-di-t-butyloxyphenyl group, 3,4-di-t-butyloxyphenyl group, 2,6-di-n-butyloxy Phenyl group, 2,3-di-n-butyloxyphenyl group, 2,4-di-n-butyloxyphenyl group, 3,4-di-n-butyloxyphenyl group, 2,6-di-i- Butyloxyphenyl group, 2,3-di-i-butyloxyphenyl group, 2,4-di-i-butyloxyphenyl group, 3,4-di-i-butyloxyphenyl group, 2,6-di- t-Amyloxyphenyl 2,3-di-t-amyloxyphenyl group, 2,4-di-t-amyloxyphenyl group, 3,4-di-t-amyloxyphenyl group, 2,6-di-i-amyloxy Phenyl group, 2,3-di-i-amyloxyphenyl group, 2,4-di-i-amyloxyphenyl group, 3,4-di-i-amyloxyphenyl group, 2,6-di-n- Pentyloxyphenyl group, 2,3-di-n-pentyloxyphenyl group, 2,4-di-n-pentyloxyphenyl group, 3,4-di-n-pentyloxyphenyl group, 4-adamantyloxyphenyl group , 3-adamantyloxyphenyl group, 2-adamantyloxyphenyl group, 4-isoboronyloxyphenyl group, 3-isoboronyloxyphenyl group, 2-isoboronyloxyphenyl group, etc. These may be further substituted as long as they are within the above range, and are not limited to substituents other than the above examples [0025] Further, the further substituents that the above group may have include a hydroxyl group, a halogen atom (fluorine, chlorine, bromine, iodine), a nitro group, a cyano group, the above alkyl group, a methoxy group, an ethoxy group, Hydroxyethoxy group, propoxy group, hydroxypropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, alkoxy group such as t-butoxy group, alkoxycarbonyl group such as methoxycarbonyl group, ethoxycarbonyl group, benzyl group, phenethyl Group, aralkyl group such as cumyl group, aralkyloxy group, formyl group, acetyl group, butyryl group, benzoyl group, cyanamyl group, acyl group such as valeryl group, acyloxy group such as butyryloxy group, the above alkenyl group, vinyloxy group, Such as propenyloxy group, allyloxy group, butenyloxy group, etc. Rukeniruokishi group, said aryl group, an aryloxy group such as phenoxy group, and an aryloxycarbonyl group such as benzoyloxy group [0032]. In the manufacture of precision integrated circuit elements, the pattern forming process on the resist film is carried out by applying the positive resist composition of the present invention on a substrate (eg, a transparent substrate such as a silicon / silicon dioxide covering, a glass substrate, an ITO substrate) [0177].
Mizutani JP 2005274878 does not exemplify polymers include the full range of repeating of claim 1 where at least one of RL1-RL3 is a hydrocarbyl group, the terminal phenyl groups is with halogen or hydrocarbyl moieties other than phenyl or adamantyl or exemplify the use of polymers P-4 or P-5 in resist compositions or processes using resists
With respect to claims 1-6 and 8, it would have been obvious to one skilled in the art to modify polymer P5 by replacing the methyl group of the acetal moiety with a ethyl, propyl, isopropyl , butyl, i-butyl or t-butyl moiety based upon the teaching that R .sub.1 and R .sub.2 each independently represents a hydrogen atom or an alkyl group (preferably having 1 to 4 carbon atoms) [0011-0015] with a reasonable expectation of forming a useful resist polymer based upon the equivalence.
With respect to claims 1-6 and 8, it would have been obvious to one skilled in the art to modify polymer P5 by replacing the methyl group of the acetal moiety with a ethyl, propyl, isopropyl , butyl, i-butyl or t-butyl moiety based upon the teaching that R .sub.1 and R .sub.2 each independently represents a hydrogen atom or an alkyl group (preferably having 1 to 4 carbon atoms) [0011-0015] replacing the adamantyl group with an alkoxy, alkyl, halogen groups based upon the teachings at [0025,0032] with a reasonable expectation of forming as useful resist polymer based upon the disclosed equivalence with unsubstituted and other substituted phenyl groups.
With respect to claims 1-6,8-10,12 and 15-17, it would have been obvious to one skilled in the art to modify polymer P5 by replacing the methyl group of the acetal moiety with a ethyl, propyl, isopropyl , butyl, i-butyl or t-butyl moiety based upon the teaching that R .sub.1 and R .sub.2 each independently represents a hydrogen atom or an alkyl group (preferably having 1 to 4 carbon atoms) [0011-0015] replacing the adamantyl group with an alkoxy, alkyl, halogen groups based upon the teachings at [0025,0032] and to forma resist composition by adding photoacid generators, solvents and amine/quenchers to the resultant polymers with a reasonable expectation of forming a useful resist.
With respect to claims 1-6,8-10,12 and 15-20, it would have been obvious to one skilled in the art to modify polymer P5 by replacing the methyl group of the acetal moiety with a ethyl, propyl, isopropyl , butyl, i-butyl or t-butyl moiety based upon the teaching that R .sub.1 and R .sub.2 each independently represents a hydrogen atom or an alkyl group (preferably having 1 to 4 carbon atoms) [0011-0015] replacing the adamantyl group with an alkoxy, alkyl, halogen groups based upon the teachings at [0025,0032] and to forma resist composition by adding photoacid generators, solvents and amine/quenchers to the resultant polymers and to use them in the exemplified lithographic processes with a reasonable expectation of forming a useful resist composition and pattern.
In addition to the basis above, it would have been obvious to modify the processes exemplified using the compositions of the examples or rendered obvious as discussed above by using other exposures, such as electron beam with a reasonable expectation of forming a useful pattern based upon the disclosure of these as actinic light throughout (see abstract and title)
With respect to claims 15 and 16, the examiner holds that the dissolution rate of the unexposed resist is less than 10 nm/min for at least one alkaline developer composition. With respect to claim 17, the examiner holds that the dissolution rate of the exposed resist is more than 50 nm/min for at least one alkaline developer composition.
In the response of 7/6/2026, the applicant argues that the claims do not disclosed/exemplify a polymer having a repeating unit bounded by the added claim language. The examiner points to
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, the disclose that the acetal can include a C2-24 alkyl groups and the disclosed substituents for Q the terminal phenyl ring.
Claims 1-10,12 and 15-22 are rejected under 35 U.S.C. 103 as being unpatentable over Inasaki et al. 20120202141.
Inasaki et al. 20120202141 on page 7 exemplifies polymer repeating units
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, which are bounded by formulae (I) and (4)
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In the general formula (1), Ac is a group leaving by the action of an acid, and --OAc represents an acetal group which decomposes by the action of an acid to generate an alkali-soluble group (a phenolic hydroxyl group). It is preferable that Ac be, specifically, a group represented by general formula (4). In the general formula (4), R.sup.41 represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group or an aralkyl group,
M.sup.41 represents a single bond or a divalent linking group, and Q represents an alkyl group, an alicyclic group which may contain a heteroatom, or an aromatic ring group which may contain a heteroatom. In addition, at least two of R.sup.41, M.sup.41 and Q may bind together to form a ring. It is preferable that this ring be a 5- or 6-membered ring. The examples of alkyl group as R.sup.41 include an alkyl group having a carbon number of 1 to 8. The preferred examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, a hexyl group and an octyl group. The alkyl group as R.sup.41 may have a substituent, and the examples thereof include a cyano group, a halogen atom, a hydroxyl group, an alkoxy group, a carboxyl group and an alkoxycarbonyl group. The examples of the cycloalkyl group as R.sup.41 include a cycloalkyl group having a carbon number of 3 to 15. The preferred examples thereof include a cyclohexyl group, a norbornyl group and an adamantyl group. The examples of the aryl group of R.sup.41 include an aryl group having a carbon number of 6 to 15. The preferred examples thereof include a phenyl group, a tolyl group, naphthyl group and anthryl group. The examples of the aralkyl group of R.sup.41 include an aralkyl group having a carbon number of 6 to 20. Preferably, the examples thereof include a benzyl group and a phenethyl group. As R.sup.41, particularly preferred are a hydrogen atom, a methyl group, a phenyl group and a benzyl group The alicyclic group and the aromatic ring group as Q may have a substituent, and the examples thereof include an alkyl group, a cycloalkyl group, a cyano group, a halogen atom, a hydroxyl group, an alkoxy group, a carboxyl group and an alkoxycarbonyl group [0030-0057]. Other repeating useful repeating units disclosed include those with pendant photoacid generators bounded by
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, where X is a onium such as sulfonium or iodonium disclosed at [0060-0095]. Other useful repeating units are those which control the solubility in the developing solution include hydroxystyrene and hydroxy substituted vinylnaphthalenes disclosed at [0096-0105]. Lactone containing repeating units are disclosed at [0106-0111]. The use of indene repeating units is disclosed at [0112] and acenaphthanene is exemplified as (M-8) on page 45. Useful polymeric/pendant photoacid generators are disclosed at [0060-0095]. Useful photoacid generators are disclosed [0123-0126]. Basic compounds are disclosed at [0127-0132]. Surfactants are disclosed at [0133-0135], dyes, plasticizers, photodecomposible bases, photobases and the like are disclosed [0136]. The substrate can be a silicon wafer (semiconductor substrate) or a substrate having a MoSi, Cr, TaSi, oxides of these or the like (photomask substrates) [0140-0148]. In the examples, the resist polymers such as
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are combined with a basic compound/quencher, surfactant, solvent (and in example 28 an additional photoacid generator, PAG2) coated on a glass substrate, dried, exposed using an electron beam, post baked and developed in TMAH [0172-0196]. Disclosed PAGs include
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Exposure includes exposure to a mercury lamp, far ultraviolet rays typified by an excimer laser, X-rays, EUV light, particles beams and the like [0022].
Inasaki et al. 20120202141 does not exemplify polymers including repeating units
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where the terminal phenyl moiety is substituted with an alkyl group, a cycloalkyl group, a halogen atom, an alkoxy group (contains -O-) or an alkoxycarbonyl group (ester), resist composition including these repeating units (as liquid compositions or as films on substrates) or lithographic processes using the resists with these repeating units.
With respect to claims 1-2, and 8, it would have been obvious to one skilled in the art to form polymers by replacing at least a portion of the acetal groups with repeating units
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or
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with similar acetal containing repeating units which are substituted with an alkyl group, a cycloalkyl group, a halogen atom, an alkoxy group (contains -O-) or an alkoxycarbonyl group (ester) based upon the disclosure at [0030-0057].
With respect to claims 1-8, it would have been obvious to one skilled in the art to form resist copolymers similar to those of the examples by replacing at least a portion of the polymers with repeating units
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or
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with similar acetal containing repeating units which are substituted with an alkyl group, a cycloalkyl group, a halogen atom, an alkoxy group (contains -O-) or an alkoxycarbonyl group (ester) based upon the disclosure at [0030-0057] and adding other repeating units disclosed as useful such as sulfonium or iodonium disclosed at [0060-0095], hydroxystyrene and hydroxy substituted vinylnaphthalenes disclosed at [0096-0105], Lactone containing repeating units are disclosed at [0106-0111], indene repeating units is disclosed at [0112] and/or acenaphthanene is exemplified as (M-8) on page 45 with a reasonable expectation of forming as useful resist polymer.
With respect to claims 1-10,12, and 15-17, it would have been obvious to one skilled in the art to form resist copolymers similar to those of the examples by replacing at least a portion of the polymers with repeating units
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or
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with similar acetal containing repeating units which are substituted with an alkyl group, a cycloalkyl group, a halogen atom, an alkoxy group (contains -O-) or an alkoxycarbonyl group (ester) based upon the disclosure at [0030-0057] and adding other repeating units disclosed as useful such as sulfonium or iodonium disclosed at [0060-0095], hydroxystyrene and hydroxy substituted vinylnaphthalenes disclosed at [0096-0105], Lactone containing repeating units are disclosed at [0106-0111], indene repeating units is disclosed at [0112] and/or acenaphthanene is exemplified as (M-8) on page 45 with a reasonable expectation of forming as useful resist polymer and combine them with a basic compound/quencher, surfactant, solvent and photoacid generator as in the examples with a reasonable expectation of forming a useful resist composition based upon their disclosed equivalence.
With respect to claims 1-10,12 and 15-20 it would have been obvious to one skilled in the art to form resist copolymers similar to those of the examples by replacing at least a portion of the polymers with repeating units or with similar acetal containing repeating units which are substituted with an alkyl group, a cycloalkyl group, a halogen atom, an alkoxy group (contains -O-) or an alkoxycarbonyl group (ester) based upon the disclosure at [0030-0057] and adding other repeating units disclosed as useful such as sulfonium or iodonium disclosed at [0060-0095], hydroxystyrene and hydroxy substituted vinylnaphthalenes disclosed at [0096-0105], Lactone containing repeating units are disclosed at [0106-0111], indene repeating units is disclosed at [0112] and/or acenaphthanene is exemplified as (M-8) on page 45 with a reasonable expectation of forming as useful resist polymer and combine them with a basic compound/quencher, surfactant, solvent and photoacid generator as in the examples and exposing them using the exposure source of the examples or another disclosed at [0022] with a reasonable expectatiuon of forming a useful resist pattern.
With respect to claims 1-10,12 and 15-17 and 22, it would have been obvious to one skilled in the art to form resist copolymers similar to those of the examples by replacing at least a portion of the polymers with repeating units or with similar acetal containing repeating units which are substituted with an alkyl group, a cycloalkyl group, a halogen atom, an alkoxy group (contains -O-) or an alkoxycarbonyl group (ester) based upon the disclosure at [0030-0057] and adding other repeating units disclosed as useful such as sulfonium or iodonium disclosed at [0060-0095], hydroxystyrene and hydroxy substituted vinylnaphthalenes disclosed at [0096-0105], Lactone containing repeating units are disclosed at [0106-0111], indene repeating units is disclosed at [0112] and/or acenaphthanene is exemplified as (M-8) on page 45 with a reasonable expectation of forming as useful resist polymer and combine them with a basic compound/quencher, surfactant, solvent and photoacid generator as in the examples and coat them on a photomask substrate such as those taught at [0140-0148] with a reasonable expectation of forming a useful resist pattern.
With respect to claims 1-10,12 and 15-22, it would have been obvious to one skilled in the art to form resist copolymers similar to those of the examples by replacing at least a portion of the polymers with repeating units or with similar acetal containing repeating units which are substituted with an alkyl group, a cycloalkyl group, a halogen atom, an alkoxy group (contains -O-) or an alkoxycarbonyl group (ester) based upon the disclosure at [0030-0057] and adding other repeating units disclosed as useful such as sulfonium or iodonium disclosed at [0060-0095], hydroxystyrene and hydroxy substituted vinylnaphthalenes disclosed at [0096-0105], Lactone containing repeating units are disclosed at [0106-0111], indene repeating units is disclosed at [0112] and/or acenaphthanene is exemplified as (M-8) on page 45 with a reasonable expectation of forming as useful resist polymer and combine them with a basic compound/quencher, surfactant, solvent and photoacid generator as in the examples and coat them on a photomask substrate such as those taught at [0140-0148], exposing them using the exposure source of the examples or another disclosed at [0022] with a reasonable expectation of forming with a reasonable expectation of forming a useful resist pattern.
With respect to claims 15 and 16, the examiner holds that the dissolution rate of the unexposed resist is less than 10 nm/min for at least one alkaline developer composition. With respect to claim 17, the examiner holds that the dissolution rate of the exposed resist is more than 50 nm/min for at least one alkaline developer composition.
In the response of 7/6/2026, the applicant argues that the claims do not disclosed/exemplify a polymer having a repeating unit bounded by the added claim language. The examiner points to repeating units
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or
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and the disclosed substituents for the terminal phenyl ring.
Claim 1-6,8-12, and 15-22 are rejected under 35 U.S.C. 103 as being unpatentable over Hirano et al. JP 2008249890, in view of Hatakeyama et al. 20190113843.
Hatakeyama et al. 20190113843 teaches sulfonium salts having the formulae
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With
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exemplified on page 28. These can be used with resist having acetal acid generative groups
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, where 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 [0062-0068]. Useful phenolic repeating units which control the dissolution is disclosed [0069] Useful hydroxy or lactone containing repeating unit are disclosed at [0070-0071. Useful fused rings containing repeating units including indene and acenaphthylene are disclosed at [0072-0073]. Useful photoacid repeating units with the structures
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,
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and
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are disclosed [0074-0082]. Other acid generators are disclosed [0090-0114]. Useful quenchers are disclosed [0115-0118]. The addition of surfactants is disclosed [0126-0128]. The addition of water repellant polymers, particularly those having a hexafl;uoro-2-propanol moiety is disclosed and those disclosed in JP 2007297590[0133-0134]. For example, the positive resist composition is first applied onto a substrate on which an integrated circuit is to be formed (e.g., Si, SiO.sub.2, SiN, SiON, TiN, WSi, BPSG, SOG, or organic antireflective coating) or a substrate on which a mask circuit is to be formed (e.g., Cr, CrO, CrON, MoSi.sub.2, or SiO.sub.2) by a suitable coating technique such as spin coating, roll coating, flow coating, dipping, spraying or doctor coating. The coating is prebaked on a hotplate at a temperature of 60 to 150° C. for 10 seconds to 30 minutes, preferably at 80 to 120° C. for 30 seconds to 20 minutes. The resulting resist film is generally 0.01 to 2.0 μm thick [0159].
Hirano et al. JP 2008249890 does not teach a PAG bounded by the formula of claim 11.
It would have been obvious to one skilled in the art to modify the compositions rendered obvious by the teachings of Hirano et al. JP 2008249890 by adding other photoacid generators known in the art, such as those taught by Hatakeyama et al. 20190113843 with a reasonable expectation of forming useful resists and resist patterns based upon the disclosed utility with acetal containing resists. Further it would have been obvious to use the resulting resists on other substrates such as the photomask substrates disclosed by Hatakeyama et al. 20190113843 at [0159].
Claim 1-6 and 8-22 are rejected under 35 U.S.C. 103 as being unpatentable over Hirano et al. JP 2008249890, in view of Hatakeyama et al. 20190113843, further in view of Kaneko et al. JP 2007297590 and/or Masunaga et al. 20180039175
Kaneko et al. JP 2007297590 (machine translation attached) exemplifies polymers
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On pages 62—67. The addition of a hydroxy containing repeating unit is disclosed [0052-0053].
Masunaga et al. 20180039175 teaches fluorinated polymers using the repeating units
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at [118-0132]. Exemplified fluorinated polymers include
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(pages 44 and 45)
In addition to the basis above, it would have been obvious one skilled int art to modify the resists rendered obvious by the combination of Hirano et al. JP 2008249890 and Hatakeyama et al. 20190113843 by adding a fluorinated polymer such as those disclosed by Kaneko et al. JP 2007297590 and/or Kaneko et al. JP 2007297590 to improve the water repellency which allows water to be used as the immersion fluid for high NA exposures.
Claim 1-6,8-12 and 15--22 are rejected under 35 U.S.C. 103 as being unpatentable over Mizutani JP 2005274878, in view of Hatakeyama et al. 20190113843
It would have been obvious to one skilled in the art to modify the teachings of Mizutani JP 2005274878 by adding other photoacid generators known in the art, such as those taught by Hatakeyama et al. 201901267402 with a reasonable expectation of forming useful resists and resist patterns based upon the disclosed utility with acetal containing resists. Further it would have been obvious to use the resulting resists on other substrates such as the photomask substrates disclosed by Hatakeyama et al. 20190113843 at [0159].
Claim 1-6 and 8-22 are rejected under 35 U.S.C. 103 as being unpatentable over Mizutani JP 2005274878, in view of Hatakeyama et al. 20190113843, further in view of Kaneko et al. JP 2007297590 and/or Masunaga et al. 20180039175
In addition to the basis above, it would have been obvious one skilled in the art to modify the resists rendered obvious by the combination of Mizutani JP 2005274878 and Hatakeyama et al. 20190113843 by adding a fluorinated polymer such as those disclosed by Kaneko et al. JP 2007297590 and/or Masunaga et al. 20180039175 to improve the water repellency which allows water to be used as the immersion fluid for high NA exposures.
Claim 1-12 and 15-22 are rejected under 35 U.S.C. 103 as being unpatentable over Inasaki et al. 20120202141, in view of Hatakeyama et al. 20190113843
It would have been obvious to one skilled in the art to modify the teachings of Inasaki et al. 20120202141 by adding other photoacid generators known in the art, such as those taught by Hatakeyama et al. 201901267402 with a reasonable expectation of forming useful resists and resist patterns based upon the disclosed utility with acetal containing resists. Further it would have been obvious to use the resulting resists on other substrates such as the photomask substrates disclosed by Hatakeyama et al. 20190113843 at [0159].
Claim 1-22 are rejected under 35 U.S.C. 103 as being unpatentable over Inasaki et al. 20120202141, in view of Hatakeyama et al. 20190113843, further in view of Kaneko et al. JP 2007297590 and/or Masunaga et al. 20180039175
In addition to the basis above, it would have been obvious one skilled int art to modify the resists rendered obvious by the combination of Inasaki et al. 20120202141and Hatakeyama et al. 20190113843 by adding a fluorinated polymer such as those disclosed by Kaneko et al. JP 2007297590 and/or Masunaga et al. 20180039175 to improve the water repellency which allows water to be used as the immersion fluid for high NA exposures.
Claims 1,2,8-10,12 and 15-20 are rejected under 35 U.S.C. 103 as being unpatentable over Kanna et al. JP 2004086020.
Kanna et al. JP 2004086020 (machine translation attached), exemplifies the repeating unit A-13
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, which are bounded by formulae VI and V,
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R in the general formulas (I), (II) and (VI).sub.1, R.sub.5, R.sub.17aAnd R.sub.17May be the same or different and each represents a hydrogen atom, a halogen atom, a cyano group or an alkyl group. R.sub.2, R.sub.3, R.sub.6And R.sub.7May be the same or different and each represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, an acyl group, an acyloxy group, an alkenyl group, an aryl group or an aralkyl group. R.sub.50~ R.sub.55May be the same or different and each represents a hydrogen atom, a fluorine atom or an alkyl group. However, R.sub.50~ R.sub.55Of these, at least one represents a fluorine atom or an alkyl group in which at least one hydrogen atom is substituted with a fluorine atom. R.sub.4Represents a group of the following general formula (IV) or (V). R.sub.18Is -C (R.sub.18d) (R.sub.18e) (R.sub.18f) Or -C (R.sub.18d) (R.sub.18e) (OR.sub.18g). R.sub.18d~ R.sub.18gMay be the same or different and each represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an aralkyl group or an aryl group. R.sub.18d, R.sub.18e, R.sub.18f2 of R or R.sub.18d, R.sub.18e, R.sub.18gTwo of these may combine to form a ring. In general formula (V), R.sub.14And R.sub.15May be the same or different and each represents a hydrogen atom or an alkyl group. R.sub.16Represents an alkyl group, a cycloalkyl group, an aralkyl group or an aryl group. R.sub.14~ R.sub.16May be combined to form a ring. As the aryl group, for example, an aryl group having 6 to 15 carbon atoms, specifically. Preferable examples include phenyl group, tolyl group, dimethylphenyl group, 2,4,6-trimethylphenyl group, naphthyl group, anthryl group, 9,10-dimethoxyanthryl group and the like. As the aralkyl group, for example, an aralkyl group having 7 to 12 carbon atoms, Physically, a benzyl group, a phenethyl group, a naphthylmethyl group, etc. can be mentioned preferably. The alkyl group, cycloalkyl group, alkoxy group, acyl group, acyloxy group, alkynyl group, alkenyl group, aryl group, aralkyl group, alkoxycarbonyl group, alkylene group, cycloalkylene group, alkenylene group, arylene group, etc. are substituents. You may have. Substituents substituted with these groups include those having active hydrogen such as amino groups, amide groups, ureido groups, urethane groups, hydroxyl groups, carboxyl groups, halogen atoms (fluorine atoms, chlorine atoms, bromine atoms, Iodine atom), alkoxy group (methoxy group, ethoxy group, propoxy group, butoxy group, etc.), thioether group, acyl group (acetyl group, propanoyl group, benzoyl group, etc.), acyloxy group (acetoxy group, propanoyloxy group, benzoyl) Oxy group etc.), alkoxycarbonyl group (methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group etc.), alkyl group (methyl group, ethyl group, propyl group, butyl group), cycloalkyl group (cyclohexyl group), aryl group ( Phenyl group), cyano group, nitro group and the like [0015-0054]. Useful photoacid generators generating fluorinated sulfonic acids are disclosed [0117-0126]. Useful photoacid generators generating non-fluorinated sulfonic acids [0125-0131] carboxylic acids (quenchers) are disclosed [0132-0161]. Surfactant are disclosed [0162-0165]. In the manufacture of precision integrated circuit elements, the pattern forming process on the resist film is carried out by applying the positive resist composition of the present invention on a substrate (eg, a transparent substrate such as a silicon / silicon dioxide covering, a glass substrate, an ITO substrate). A good resist pattern can be formed by applying an object, then irradiating with an actinic ray or radiation drawing apparatus, heating, developing, rinsing and drying [0177]. In the example composition the polymer is combined with a photoacid generator, basic compound, surfactant and solvent. These are coated onto a silicon wafer, dried, exposed using an F2 excimer laser, post baked and developed in TMAH [0201-0210]. That is, known light (400 to 200 nm ultraviolet light, far-off light used for photoinitiators of photocationic polymerization, photoinitiators of photoradical polymerization, photodecolorants of dyes, photochromic agents, micro-resist, etc. UV, particularly preferably g-line, h-line, i-line, KrF excimer laser beam), ArF excimer laser beam, F.sub.2A compound that generates an acid by an excimer laser beam, an electron beam, an X-ray, a molecular beam, or an ion beam and a mixture thereof can be appropriately selected and used [0111].
Kanna et al. JP 2004086020 does not exemplify polymers similar to
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where the acertal includes a C2 or larger alkyl groups or the terminal phenyl is substituted by hydrocarbyl or halogen.
With respect to claims 1,2 and 8, it would have been obvious to one skilled in the art to for a polymer using a repeating unit similar to
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where the methyl group in the acetal is replaced with a C2 or larger alkyl group based upon the language at [0035] and [0028] and to substitute the terminal phenyl group with halogen atoms (fluorine atoms, chlorine atoms, bromine atoms, Iodine atom), alkoxy group (methoxy group, ethoxy group, propoxy group, butoxy group, etc.), thioether group, acyl group (acetyl group, propanoyl group, acyloxy group (acetoxy group, propanoyloxy group, benzoyl) Oxy group etc.), alkoxycarbonyl group (methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group etc.), alkyl group (methyl group, ethyl group, propyl group, butyl group), cycloalkyl group (cyclohexyl group) or fluoroalkyl [0015-0054] with a reasonable expectation of forming a useful resist polymer.
With respect to claims 1,2,8-10,12 and 15-17, it would have been obvious to one skilled in the art to for a polymer using a repeating unit similar to
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where the methyl group in the acetal is replaced with a C2 or larger alkyl group based upon the language at [0035] and [0028] and to substitute the terminal phenyl group with halogen atoms (fluorine atoms, chlorine atoms, bromine atoms, Iodine atom), alkoxy group (methoxy group, ethoxy group, propoxy group, butoxy group, etc.), thioether group, acyl group (acetyl group, propanoyl group, acyloxy group (acetoxy group, propanoyloxy group, benzoyl) Oxy group etc.), alkoxycarbonyl group (methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group etc.), alkyl group (methyl group, ethyl group, propyl group, butyl group), cycloalkyl group (cyclohexyl group) or fluoroalkyl [0015-0054] and to add a photoacid generator, solvent, quencher and surfactant as taught in the cited portions with a reasonable expectation of forming a useful positive resist.
With respect to claims 1,2,8-10,12 and 15-20, it would have been obvious to one skilled in the art to for a polymer using a repeating unit similar to
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where the methyl group in the acetal is replaced with a C2 or larger alkyl group based upon the language at [0035] and [0028] and to substitute the terminal phenyl group with halogen atoms (fluorine atoms, chlorine atoms, bromine atoms, Iodine atom), alkoxy group (methoxy group, ethoxy group, propoxy group, butoxy group, etc.), thioether group, acyl group (acetyl group, propanoyl group, acyloxy group (acetoxy group, propanoyloxy group, benzoyl) Oxy group etc.), alkoxycarbonyl group (methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group etc.), alkyl group (methyl group, ethyl group, propyl group, butyl group), cycloalkyl group (cyclohexyl group) or fluoroalkyl [0015-0054] and to add a photoacid generator, solvent, quencher and surfactant as taught in the cited portions and using them with the disclosure exposure and development processes with a reasonable expectation of forming a useful resist pattern.
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.
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MARTIN J. ANGEBRANNDT
Primary Examiner
Art Unit 1737
/MARTIN J ANGEBRANNDT/Primary Examiner, Art Unit 1737 July 30, 2026
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