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 Rejection of the previous action not repeated below are withdrawn in view of the arguments and amendments of the applicant. Responses to the arguments and amendment of the applicant are presented after the first rejection they are directed to.
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 1-4,10,13,14 and 21-22 are rejected under 35 U.S.C. 103 as being unpatentable over Urakawa et al. 20230099775, in view of Shiota et al. 20160046551 and Ogihara et al. 20140193757.
Urakawa et al. 20230099775 in example 5 teaches 19 parts of monomer A-2, 80 parts TiO2, thermal initiator and solvent. Example 6 teaches 29 parts monomer A-2 , 70 parts TiO2, thermal initiator and solvent as evidenced in table 1. These are coated upon a substrate, heated at 120 degrees C for 2 minutes to form a cured film [0207]
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(see page)
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These monomers are bounded by formulae a1 and a2
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wherein, in the formula (a1), W.sup.1 and W.sup.2 each independently represent a group represented by the following formula (a2): wherein, in the formula (a2), a ring Z represents an aromatic hydrocarbon ring, X represents a single bond or a group represented by —S—, R.sup.1 represents a single bond, an alkylene group having 1 or more and 4 or less carbon atoms, or an alkyleneoxy group having 1 or more and 4 or less carbon atoms, and when R.sup.1 is an alkyleneoxy group, the oxygen atom in the alkyleneoxy group is bonded with a ring Z, R.sup.2 represents a monovalent hydrocarbon group, a hydroxy group, a group represented by —OR.sup.4a, a group represented by —SR.sup.4b, an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxy group, an amino group, a carbamoyl group, a group represented by —NHR.sup.4c, a group represented by —N(R.sup.4d).sub.2, a sulfo group, or a group in which at least a part of hydrogen atoms bonded to the carbon atom included in a monovalent hydrocarbon group, a group represented by —OR.sup.4a, a group represented by —SR.sup.4b, an acyl group, an alkoxycarbonyl group, a group represented by —NHR.sup.4c, or a group represented by —N(R.sup.4d).sub.2 is/are substituted with a monovalent hydrocarbon group, a hydroxy group, a group represented by —OR.sup.4a, a group represented by —SR.sup.4b, an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxyl group, an amino group, a carbamoyl group, a group represented by —NHR.sup.4c, a group represented by —N(R.sup.4d).sub.2, a mesyloxy group, or a sulfo group, R.sup.4a to R.sup.4d independently represent a monovalent hydrocarbon group, m represents an integer of 0 or more, R.sup.3 represents a hydrogen atom, a vinyl group, a thiiran-2-ylmethyl group, a glycidyl group, or a (meth)acryloyl group, both W.sup.1 and W.sup.2 do not have a hydrogen atom as R.sup.3, a ring Y.sup.1 and a ring Y.sup.2 represent the same or different aromatic hydrocarbon ring, R represents a single bond, an optionally substituted methylene group, an ethylene group which is optionally substituent and includes a heteroatom between two carbon atoms, a group represented by —O—, a group represented by —NH—, or a group represented by —S—, R.sup.3a and R.sup.3b independently represent a cyano group, a halogen atom, or a monovalent hydrocarbon group, and n1 and n2 independently represent an integer of 0 or more and 4 or less [0021]. The polymerizable compounds can be sued in amounts of 3-95 wt%, most preferably 5-29 wt% [0096] Useful metal oxide particles including titania, zirconia, barium titanate and ceria with sizes in the 20-100 nm range in amounts of 50-90% by mass [0097-0108]. Initiators including photoacid generating diphenyliodonioum and triphenylsulfonium salts are disclosed [0109-0181]. Useful solvents are disclosed and can be used in mixture of two or more [0188-0190]. The curable composition can optionally contain additives such as surfactants, thermal polymerization inhibitors, defoamers, silane coupling agents, resins (thermoplastic resins, alkali-soluble resins, etc.), inorganic fillers other than the metal oxide microparticles (B), organic fillers, and the like. It is possible to use, as any additives, conventionally known additives. Examples of the surfactant include anionic, cationic, and nonionic compounds, examples of the thermal polymerization inhibitor include hydroquinone, hydroquinone monoethyl ether, and the like, and examples of the defoamer include silicone-based compounds, fluorine-based compounds, and the like [0187].
Shiota et al 20160046551 teaches vinyl group containing fluorene compounds bounded by formulae 1, 2 and 4.
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wherein W.sup.1 and W.sup.2 each independently represent a group represented by the following general formula (2), a group represented by the following general formula (4), a hydroxyl group, or a (meth)acryloyloxy group, provided that W.sup.1 and W.sup.2 do not simultaneously represent a hydroxyl group or the group represented by the following general formula (4); R.sup.3a and R.sup.3b each independently represent a cyano group, a halogen atom, or a monovalent hydrocarbon group; and n1 and n2 each independently represent an integer of 0 to 4,
wherein a ring Z represents an aromatic hydrocarbon ring; X represents a single bond or a group represented by —S—; R.sup.1 represents a single bond or an alkylene group having 1 to 4 carbon atoms; R.sup.2 represents a monovalent hydrocarbon group, a hydroxyl group, a group represented by —OR.sup.4a, a group represented by —SR.sup.4b, an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxyl group, an amino group, a carbamoyl group, a group represented by —NHR.sup.4c, a group represented by —N(R.sup.4d).sub.2, a (meth)acryloyloxy group, a sulfo group, or a group formed by substituting at least a part of hydrogen atoms bonded to carbon atoms contained in a monovalent hydrocarbon group, a group represented by —OR.sup.4a, a group represented by —SR.sup.4b, an acyl group, an alkoxycarbonyl group, a group represented by —NHR.sup.4c, or a group represented by —N(R.sup.4d).sub.2 with a monovalent hydrocarbon group, a hydroxyl group, a group represented by —OR.sup.4a, a group represented by —SR.sup.4b, an acyl group, an alkoxycarbonyl group, a halogen atom, a nitro group, a cyano group, a mercapto group, a carboxyl group, an amino group, a carbamoyl group, a group represented by —NHR.sup.4c, a group represented by —N(R.sup.4d).sub.2, a (meth)acryloyloxy group, a mesyloxy group, or a sulfo group; R.sup.4a to R.sup.4d each independently represent a monovalent hydrocarbon group; and m is an integer of 0 or more
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[0006].
Exemplified compounds include
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[0030,0106].
The negative-type photosensitive resin composition may contain various additives as required. Examples of the additives include a sensitizer, a curing accelerator, a filler, an adhesion accelerator, an antioxidant, an ultraviolet ray absorber, a flocculation inhibitor, thermal polymerization inhibitor, an anti-foaming agent, a surfactant, and the like [0102].
Ogihara et al. 20140193757 teaches phenol (B-III)
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[0159-0160]. Synthetic examples teach zirconium, titanium, hafnium and/or aluminum oxide dispersions [0148-0154]. Underlayer sol 15 includes oxide dispersion 4 parts A-1, 0.4 parts phenol B-III and PGMEA. Underlayer sol 19 includes oxide dispersion 4 parts A-1, 0.4 parts phenol B-III, a silicon polymer C-III, thermal acid generator (triphenyl sulfonium maleate and PGMEA (table 2). These were spin coated on a wafer, heated to 350 degrees C for 1 minute to form thin films. [0166-0167]. A wafer coated with a carbon film was spin coated with the underlayer compositions, a carbon thin film was then coated followed by a silicon film and resist, which was dried, a top coat applied,, exposed using an ArF immersion exposure apparatus, post baked as 100 degrees C for 60 seconds and developed in TMAH [0168-0170]. The etch characteristics were then evaluated [0171-0182]. Negative development of a wafer/carbon layer/ underlayer/resist laminate was evaluated as well as the etch characteristics of the resulting pattern [0183-0190]. Useful compounds include (page 14)
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Component A can be oxides of aluminum, gallium, yttrium, titanium, zirconium, hafnium, bismuth, tin, vanadium, and tantalum [0070-0092]. The composition for forming a metal oxide-containing film of the present invention may further contain a photoacid generator. As the photoacid generator, the materials specifically described at the paragraphs [0160] to [0179] of Japanese Patent Laid-Open Publication No. 2009-126940 can be used. The composition for forming a metal oxide-containing film of the present invention may further contain a thermal acid generator. As the thermal acid generator, the materials specifically described at the paragraphs [0061] to [0085] of Japanese Patent Laid-Open Publication No. 2007-199653 can be used. As mentioned above, when the photoacid generator or the thermal acid generator is added to the composition for forming a metal oxide-containing film of the present invention, in addition to the above-mentioned characteristics, resolution of the pattern can be further improved. The composition for forming a metal oxide-containing film of the present invention may further contain a crosslinking accelerator, if necessary. Such a crosslinking accelerator may be exemplified by the compound shown by the following general formula (1) or (2)
K.sub.aH.sub.bX (1)
wherein K represents lithium, sodium, potassium, rubidium or cesium, X represents a hydroxyl group, or a monovalent or divalent or more of an organic acid group having 1 to 30 carbon atoms, "a" is an integer of 1 or more, "b" is 0 or an integer of 1 or more, and "a+b" is a valence number of the hydroxyl group or the organic acid group.
SY (2)
wherein S represents a sulfonium, an iodonium or an ammonium, and Y represents a non-nucleophilic counter-ion. Incidentally, the above crosslinking accelerator may be used a single kind alone or two or more kinds in combination. To the composition for forming a metal oxide-containing film of the present invention may be further added a surfactant, if necessary. As such a surfactant, the materials specifically described at the paragraph [0129] of Japanese Patent Laid-Open Publication No. 2009-126940 can be used [0124- 0132]. The resist upper layer film is not particularly limited, and may be exemplified by, for example, a chemical amplification type photoresist film. Also, in the patterning process of the present invention, a middle layer film may be formed between the resist upper layer film and the metal oxide-containing film, if necessary[0139].
With respect to claims 1-4,10,13,14 and 21-22 , it would have been obvious to one skilled in the art to modify examples 5 or 6 of Urakawa et al. 20230099775 by replacing the bis(vinyloxynaphthyl)fluorene with 9-hydroxynaphthyl-9-allyloxynaphthyl)fluorene [aka 9-hydroxynaphthyl-9-vinylmethyloxynaphthyl)fluorene] based upon the disclosure of the monomer
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in Urakawa et al. 20230099775 and Shiota et al 20160046551 and the disclosed equivalence or vinyl and allyl (vinylmethyl) in Shiota et al 20160046551 with a reasonable expectation of forming a useful metal oxide particle containing composition based upon the teachings in Ogihara et al. 20140193757 that bis(allyloxynaphthyl)fluorene is a useful monomer on page 14. Further it would have been obvious to use the resulting composition as in the examples with a reasonable expectation forming a cured film. (the proportion of hydrogen would be 0.5 in claim 9)
In addition to the basis above, it would have been obvious to modify the compositions rendered obvious above by adding a surfactant or resin (blend polymer) or a solvent mixture including high and low boiling solvents based upon the disclosure in Urakawa et al. 20230099775 at [0187],0188-0190].
In addition to the basis above, it would have been obvious to modify the compositions rendered obvious above by replacing a portion of the titania with zirconia or ceria based and/or changing the amounts of the oxide particles within the disclosed range upon the disclosure at [0097-0108] with a reasonable expectation of forming a useful curable composition and cured film
In the response of 7/13/2026, the applicant argues that the prior art does not describe the excellence in flowability and etch resistance, noting that the flowability contributes the filling, planarizing, film forming, and outgassing properties. The applicant also argues that the specification at [0031] in particular ascribes these properties to the recited ratio of the hydroxy group to the combination of the hydroxy and crosslinking groups being within the range of 0.2 to 0.8. The applicant states that this is evidenced by the examples at [0217,0214,0236,0257]. There does not seem to be any difference in performance between examples using UDL-1 and UDL-2 or the examples using UDL-4 and UDL-6 in tables 5, 6, 7,10, or 14 to support this assertion. The ratio of monomer to inorganic particle in Urakawa et al. 20230099775 is within the range and the comparative data does not represent a comparison which is equal to pr preferable to a direct comparison with the prior art (example 5 and 6 of Urakawa et al. 20230099775). The rejection stands.
Claims 1-4,10,13,14 and 21-23 are rejected under 35 U.S.C. 103 as being unpatentable over Urakawa et al. 20230099775, in view of Shiota et al. 20160046551 and Ogihara et al. 20140193757, further in view of (Hatakeyama et al. 20170199457, Daiseuke et al. 20170184968, Hatakeyama et al. JP 2007199653 and/or Kanao et all. 20120252218)
Hatakeyama et al. 20170199457 exemplifies
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These are used in underlayers UDL-1, UDL-4, UDL-7-11 with solvents and a surfactant [0148-0149]. A silicon dioxide hardcoat layer is formed by coating a silicon containing polymer with an acid generator [0150]. The underlayer composition were coated on a silicon wafer and baked at 200 degrees C for 60 seconds and then at 350 and 450 degrees C [0152]. The coating of the underlayer, the silicon oxide films and the resist is taught at [0152-0158]. This was then exposed, post baked, developed in TMAH and the layers etched [0161-0173]. The under layer can be baked in the atmosphere (air) or an inert gas such as nitrogen, helium or argon. [0089].
Daiseuke et al. 20170184968 teaches compounds (pages 33-38)
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These are used in underlayer compositions UDL-1, UDL-4, UDL-5, UDL-10 to UDL-12 which also include surfactants and solvents (table 5). These are coated upon silicon substrates and their filling of specific substrate topography measured by coating them and baking at 250 or 450 degrees C for 60 seconds. [0144--0147]. An example teaches each of the underlayer compositions by coating them on a silicon wafer heating at 450 degrees C for 60 seconds, forming a SiON hardmask by CVD, coating an Ar layer and then a resist which is dried at 100 degrees C for 60 seconds, and then a topcoat. This is exposed using an ArF immersion exposure apparatus, post baked, at 100 degrees C for 60 seconds and then developed in TMAH, the resist was used to pattern the dry etch of the Ar coating and the hardmask. The hardmask was then used to control the etch of the underlayer [0150-0161,0162-0164]. In the underlayer composition components are described at [0182-0164], including other compounds/polymers to improve spin coating, filling properties, and etch resistance (high carbon density additives) [0087], acid generators and crosslinking agents [0188-0189], surfactants [0190], quenchers [0191] and other additives ( plasticizers) [0192-0194]. The atmosphere during baking may be any atmosphere that has an oxygen concentration of 0.1% to 21%; the atmosphere may be air or a mixed gas of an oxygen gas and an inert gas such as N.sub.2, Ar, and He. The baking temperature and other conditions may be the same as above. When the baking is performed in such oxygen atmosphere, an organic film sufficiently cured can be formed [0100]. The substrate to be processed preferably has steps or a structure with a height of 30 nm or more [0039]
Hatakeyama et al. JP 2007199653 (machine translation attached) exemplifies the additive
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on page 46. Underlayer 9 combines this with polymer 1, a crosslinking agents (CR1), a thermal acid generator (AG) and PGMEA (table 1, page 48). Additives include blending polymers, crosslinkers, thermal acid generator, basic compounds and solvents [0054-0092].
Kanao et all. 20120252218 exemplifies
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These were used in underlayer compositions 1,2,4-10,12-15,17,18 and 20 in combination with a solvent mixture (PGMEA/cyclohexane). Underlayer compositions 17,18,20 added a thermal acid generator and a crosslinker.(table 5). The coating of the underlayer, a silicon middle layer, a resist layer, topcoat and the exposure and development of the resist are disclosed. The etch characteristic were also evaluated [0203-0211]. The fill characteristics were evaluated [0212]. Additives to the underlayer including solvents, surfactants, basic compounds, crosslinkers, acid generators and the like are disclosed [0100-0111]. Although the bake atmosphere may be air, it is sometimes preferred to introduce an inert gas such as N.sub.2, Ar or He into the atmosphere for reducing the oxygen content for the purpose of preventing the resist bottom layer from oxidation. Where it is necessary to control the oxygen concentration for preventing oxidation, the oxygen concentration is preferably up to 1,000 ppm, more preferably up to 100 ppm. It is preferred to prevent the resist bottom layer from oxidation during bake because oxidation can cause an increase of absorption or a drop of etch resistance. On the other hand, bake in air or oxygen-rich gas is sometimes preferable when molecular crosslinking by oxidative coupling is intended [0115].
The combination of Urakawa et al. 20230099775, Shiota et al. 20160046551 and Ogihara et al. 20140193757 does not teach the fully breadth of compounds.
With respect to claims 1-4,10,13,14 and 21-23, It would have been obvious to modify underlayer coating compositions rendered obvious by the combination of Urakawa et al. 20230099775, Shiota et al. 20160046551 and Ogihara et al. 20140193757 by replacing at least a portion of the fluorene based compound/monomer including a hydroxy and allyloxy group with one of the fluorene based non-polymeric monomer/compounds taught by either ( Hatakeyama et al. 20170199457, Daiseuke et al. 20170184968, Hatakeyama et al. JP 2007199653 or Kanao et all. 20120252218) having a hydroxy and either an allyloxy or propagyl group group with a reasonable expectation of forming a useful resist underlayer based upon the prior use of these compounds in resist underlayers based upon their equivalence. Further, it would have been obvious to one skilled in the art to modify the resulting compositions by using them in known multilayer resist structures, such as the trilayer resists with the silicon intermediate layer taught by Hatakeyama et al. 20170199457, Daiseuke et al. 20170184968, Hatakeyama et al. JP 2007199653 or Kanao et all. 20120252218 based upon the use of the metal oxide underlayers is two and three layer structures in Ogihara et al. 20140193757 and Hatakeyama et al. 20170199457 (claims 16-19), to use the coating with substrates having structures which are 30 nm or greater as taught by Daiseuke et al. 20170184968 at [0039] (claim 20) and/or to use heating in air or an inert atmosphere based upon the teachings of Hatakeyama et al. 20170199457, Daiseuke et al. 20170184968, and Kanao et all. 20120252218 (claim 23).
Claims 1-4 and 10-23 are rejected under 35 U.S.C. 103 as being unpatentable over Urakawa et al. 20230099775, in view of Shiota et al. 20160046551 and Ogihara et al. 20140193757, further in view of (Hatakeyama et al. 20170199457, Kori et al. 20210269597 and/or Hatakeyama et al. 20100099044)
Hatakeyama et al. 20100099044 exemplifies polymer 1.
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which is dissolved in PGMEA in underlayer composition 1. It is also used in underlayer composition 6, where it is combined with PGMEA, crosslinking agent (CR1) and thermal acid generator (triethylammonium nonafluorobutylsulfonate, AG1). A silicon wafer is coated with SiO2, the underlayer composition, a spin on glass (silicon dioxide, SOG) layer, a resist layer, a resist topcoat. The resist is exposed using an ArF immersion exposure apparatus, post baked, developed and the layers etched [0214-0229]. Additives for the underlayer include other polymers, crosslinker, thermal acid generator, basic compound, solvents and surfactants [0096-0109]. Baking atmosphere may be an air, but in order to reduce an oxygen gas, sealing with an inert gas such as N.sub.2, Ar, and He is preferable to inhibit oxidation of a resist underlayer film. In order to inhibit the oxidation, an oxygen gas concentration needs to be controlled, preferably at 1,000 ppm or less, more preferably 100 ppm or less. If a resist underlayer film is oxidized during baking, the case may happen that an absorption is increased or an etching resistance is decreased, which is not preferable [0113].
Kori et al. 20210269597 teaches underlayers including compounds containing imide and a fluorene moieties such as 6 on page 37, P11 on page 30, P12 on page 39, P8 on page 42. Further, as the body to be processed, a substrate to be processed having a structure or a step with a height of 30 nm or more is preferably used [0187].
The combination of Urakawa et al. 20230099775, in view of Shiota et al. 20160046551 and Ogihara et al. 20140193757 does not teach the fully range of compounds recited. .
With respect to claims 1-4 and 10-23, It would have been obvious to modify underlayer coating compositions rendered obvious by the combination of Urakawa et al. 20230099775, Shiota et al. 20160046551 and Ogihara et al. 20140193757 by replacing at least a portion of the fluorene based compound/monomer including a hydroxy and allyloxy group with one of the low MW fluorene based polymeric monomer/compounds taught by Hatakeyama et al. 20170199457, Kori et al. 20210269597 and/or Hatakeyama et al. 20100099044 and having a hydroxy and allyloxy group with a reasonable expectation of forming a useful resist underlayer based upon the prior use of these compounds in resist underlayers based upon thier equivalence
Further, it would have been obvious to one skilled in the art to modify the resulting compositions by using them in known multilayer resist structures, such as the trilayer resists with the silicon intermediate layer taught by Hatakeyama et al. 20170199457, Kori et al. 20210269597 and/or Hatakeyama et al. 20100099044 based upon the use of the metal oxide underlayers is two and three layer structures in Ogihara et al. 20140193757, Kori et al. 20210269597 and/or Hatakeyama et al. 20100099044 claims 16-19), to use the coating with substrates having structures which are 30 nm or greater as taught by Kori et al. 20210269597 at [0187] (claim 20) and/or to use heating in air or an inert atmosphere based upon the teachings of Hatakeyama et al. 20170199457, Daiseuke et al. 20170184968, and Kanao et all. 20120252218 (claim 23).
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 27, 2026
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