DETAILED ACTION
Claims 1-4, 6-17, 19, 21-33, and 35-43 are pending. Claims 1, 2, 9-12, 14, 17, 19, 24-27, 29, 31, 32, 38-41, and 43 have been amended, and claims 5, 18, 20, and 34 have been canceled.
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 .
Claim Rejections - 35 USC § 103
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 1-4, 6-14, 17, 19, 21-33, and 35-43 are rejected under 35 U.S.C. 103 as being unpatentable over Ogura et al. (JP2019206689). Translation previously provided.
Ogura et al. teaches a polymer composition in Example 29, Polymer B 100g, B-4 10g, C-3 3g, D-1 10g and 2-nitroso-1-naphtho 0.05g were dissolved together in a mixture of solvents consisting of and ethyl lactate 20g and NMP 80g [0217] wherein for Polymer B, a reaction was carried out in the same manner as in Production Example 1 described above, except that 2-hydroxyethyl methacrylate (HEMA) 131.5g was used instead of ethanol 46. 2g in Production Example 1 [0166] in which Production Example 1 includes 155.1g of 4,4′-oxydiphthalic dianhydride (ODPA) was placed in a separable flask having a room temperature volume, and 46.5g of ethanol and 400ml of γ-butyrolactone were added thereto, followed by stirring at 2l, and 81.5g of pyridine was added thereto with stirring to obtain a reactive mixture. After completion of heat generation by the reaction, the mixture was allowed to cool to room temperature and left to stand for 16 hours. Next, under ice cooling, 206.3g of dicyclohexylcarbodiimide (DCC) dissolved in 180ml of γ-butyrolactone was added to the mixture over 40 minutes with stirring, and then a suspension of 93.0g of 4,4′-diaminodiphenyl ether (DADPE) in 350ml of γ-butyrolactone was added over 60 minutes with stirring. After further stirring at ambient temperature for 2 hours, ethyl alcohol 30ml was added and stirred for 1 hour, and then γ-butyrolactone 400ml was added. The precipitate formed in the reaction mixture was removed by filtration to obtain a reaction solution. The resulting solution was added to a 3l of ethanol to form a sediment comprising a crude polymer. The produced crude polymer was separated by filtration and dissolved in 1.5l of tetrahydrofuran to obtain a crude polymer. The resulting crude polymer was added dropwise to water in a 28l to precipitate the polymer, and the resulting precipitates were collected by filtration and dried in vacuo to obtain a powdery polymer (polymer A) [0163-0165] (claims 1, 17, and 31). Polymer B is equivalent to a polyimide precursor of instant claims 1, 17, and 31, specifically having a structural unit represented by formula (1) of instant claims 2, 19, and 32 when X1 is a tetravalent organic group, Y1 is a divalent organic group, n1 is an integer of 2 to 150, and R1 and R2 are represented by formula (2) when m1 is 2, R3 is an organic group of 1 carbon atom, and R4 and R5 are hydrogen atoms having an absorbance Xp of 0.020 based on resin A-3 on pages 61-69 of the instant specification. Compound B-4 is prepared in Synthesis Example 2 in which in a 1L separable flask equipped with a stirrer, a dropping funnel, and a thermometer, a hydroxy compound represented by the following formula (b4) [0184]:
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[0184] 30g (0.0707 mol) of 4,4′-(1-(2-(4-hydroxyphenyl) - 2-propyl)phenyl)ethylidene) bisphenol (trade name: Tris-PA, manufactured by Honshu Chemical Industry Co., Ltd.) represented by the following formula: 1,2-naphthoquinone diazido-5-suphonate chloride 47.49g (0.177 mol) in an amount corresponding to 83.3 mol% of the OH groups was dissolved with stirring in an acetone 300g, and then the flask was adjusted to 30 °C in a thermostatic bath. Next, 17.9g of triethyl amine was dissolved in 18g of acetone, and the solution was charged into a dropping funnel and then added dropwise to the flask over 30 minutes. After completion of the dropwise addition, stirring was continued for 30 minutes, then hydrochloric acid was added dropwise, and stirring was further performed for 30 minutes to complete the reaction. The reaction was then filtered to remove triethylamine hydrochloride. Pure 1640g and 30g hydrochloride were mixed and stirred in a 3L beaker, and the filtered solution was added dropwise to the mixture with stirring to obtain a precipitate. The precipitate was washed with water, filtered, and then dried at 40 °C under reduced pressure for 48 hours to obtain photosensitive diazonaphthoquinone (B-4) [0184] which is equivalent to an exposure ray absorber of instant claims 1, 17, and 31, specifically having a 1,2-naphthoquinonediazide structure of instant claims 7, 22, and 36, more specifically a 1,2-napthoquinone diazide-5-sulfonic acid ester of a hydroxy compound represented by formula (6) of instant claims 11, 12, 26, 27, 40, and 41, even more specifically formula (11) of instant claims 14, 29, and 43 when r20 are 0 having an esterification rate of 83.3% (claims 13, 28, and 42) and having an absorbance Xt of 0.021 based on exposure ray absorber B-1 on pages 61-69 of the instant specification. Compound C-3 is (1,2-octanedion-1-[4-(phenylthio)phenyl]-2-(O-benzoyloxime)) (trade name: IRGACURE-OXE-01, manufactured by BASF) [0187] which is equivalent to an oxime ester photopolymerization initiator represented by general formula (5) of instant claims 1, 17, and 31 when R16-R18 are monovalent organic groups and having an absorbance Xr of 0.009 based on photopolymerization initiator C-2 on pages 68-70 of the instant specification. D-1 is tetraethylene glycol dimethacrylate [0187] which is equivalent to a photopolymerizable compound of instant claims 8, 23, and 37. Ogura et al. also teaches the resin composition was spin-coated and dried on a 6-inch silicon wafer so that the film thickness after curing was about 8 μm, and then heated at 200 °C for 2 hours under a nitrogen atmosphere using a temperature-programmed curing furnace (VF-2000 type, manufactured by Koyo Lindberg Co., Ltd.) to obtain a cured film. The obtained polyimide coating film was cut into 3mm wide strips using a dicing saw (DAD3350 type, manufactured by DISCO Corporation), and the cured film was peeled off from the silicon wafers using 46% hydrofluoric acid to obtain 10 polyimide tapes [0161] and in addition, in a case where the resin composition is a photosensitive resin composition, after the step of applying the resin composition onto a substrate to form a resin film on the substrate, the resin film may be exposed to an ultraviolet light source or the like directly or through a photomask or a reticle having a pattern using an exposure device such as a contact aligner, a mirror projection, or a stepper [0155]. The thickness of the film before curing is assumed to be about 10 µm (claims 1, 3, 17, 30, and 31). The amount of compound B-4 (exposure ray absorber) does not satisfy the formula 0.7 ≤ (Xp + Xt x α + Xr x β) x D ≤ 2.2 when D is 10.
However, Ogura et al. teaches the blending amount of the compound (B) having an aromatic sulfonic acid ester structure in the resin composition is 1 part by mass to 50 parts by mass, preferably 3 parts by mas to 30 parts by mass, and more preferably 5 parts by mass to 10 parts by mass, with respect to 100 parts by mass of the resin (A) [0108]. Ogura et al. also teaches the present invention will be specifically described with reference to Examples, but the present invention is not limited thereto [0158] and an object the present invention is to provide a resin composition that adheres to copper after a curing step and provides a cured film that does not form a step with an exposed copper surface after polishing [0009]. When the amount of compound B-4 in Example 29 is reduced to 5 parts by mass, the resin composition of Ogura et al. satisfies the formula (Xp + Xt x α + Xr x β) x D = 1.52 when D is 10.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of claimed invention to modify the teachings of Ogura et al. to include additional compositions implementing different amounts, e.g. 5 parts by mass of the compound B-4, and arrive at the instant claims through routine optimization with a reasonable expectation of success regarding adhesion.
With regard to claims 4 and 33, Ogura et al. teaches in Example 29 a precured (prebaked) film thickness of about 10 μm.
Ogura et al. does not teach when the prebaked film thickness (actual or assumed) is 1 μm ≤ D’ < 7 μm.
However, Ogura et al. teaches the resin composition of the present invention is applied onto a substrate, and then dried as necessary to form a resin layer. As the coating method, for example, a coating method using a spin coater, a bar coater, a blade coater, a curtain coater, a screen printing machine, or the like, a spray coating method using a spray coater, or the like can be used [0051] such that different coating methods allow for different thicknesses of the resultant film.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the specific teachings of Ogura et al. to include other film thicknesses such as 5 μm and arrive at the instant claims through routine experimentation with a reasonable expectation of success and still satisfy the formula (Xp + Xt x α + Xr x β) x D = 0.76 when D is 5.
With regard to claims 6, 21, and 35, Ogura et al. teaches in the resin composition of the present invention, a nitrogen-containing heterocyclic compound such as an azole compound or a purine derivative can be optionally blended in order to suppress discoloration on copper [0135]. Ogura et al. also teaches the present invention will be specifically described with reference to Examples, but the present invention is not limited thereto [0158].
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the specific teachings of Ogura et al. to additionally include a rust inhibitor and arrive at the instant claims through routine experimentation of combining equally suitable components for the sought invention in order to suppress discoloration on a copper substrate.
With regard to claims 9, 10, 24, 25, 38, and 39, Ogura et al. teaches a resin composition comprising, as essential components, (A) 100 parts by mass of a resin and (B) 1 to 50 parts by mass of a compound having an aromatic sulfonic acid ester structure [0014] in which the resin may be a polyimide precursor which is prepared by an appropriate dehydrating condensing agent such as dicyclocarbodiimide, 1-carboethoxy-2-ethoxy-1,2-dihydroquinoline, 1,1-carbonyldioxy-di-1,2,3-benzotriazole, or N,N′-disuccinimidyl carbonate is added to and mixed with the acid / ester compound under ice cooling to convert the acid / ester compound into a polyanhydride, and then a diamine containing a divalent organic group Y1, which is suitably used in the present invention, is separately dissolved or dispersed in a solvent and added dropwise to the polyanhydride to perform amide polycondensation, thereby obtaining a desired polyimide precursor [0030] wherein examples of diamines include 4,4′-diaminodiphenyl ether [0031] used in Polymer B, as well as 2,2′-dimethyl-4,4’-diaminobiphenyl [0032] which is equivalent to Y1 in formula (1) which is represented by formula (3) of instant claims 9, 24, and 38, specifically formula (4) of instant claims 10, 25, and 39 when R14 and R25 are methyl. When 2,2′-dimethyl-4,4’-diaminobiphenyl is substituted for 4,4′-diaminodiphenyl ether in Polymer B of Example 29, along with the reduced amount of the compound B-4, it continues to satisfy the claimed formula (Xp + Xt x α + Xr x β) x D = 0.8 and 1.6 when D is 5 or 10 respectively (claims 1, 17, and 31). Ogura et al. also teaches the present invention will be specifically described with reference to Examples, but the present invention is not limited thereto [0158]. Ogura et al. further teaches an object of the present invention is to provide a resin composition that adheres to copper after a curing step and provides a cured film that does not form a step with an exposed copper surface after polishing, a method for producing a cured film using the resin composition, and a semiconductor device [0009].
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the specific teachings of Ogura et al. to include additional polymers such as that defined above and arrive at the instant claims through routine experimentation of substituting equally suitable components for the sought invention with a reasonable expectation of success regarding adhesion.
Claims 15 and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Ogura et al. (JP2019206689) as applied to claim 1 above, and further in view of Yorisue et al. (U.S. 2019/0113845).
With regard to claims 15 and 16, Ogura et al. teaches the above composition is applied, baked, and exposed to obtain a resin film. Ogura et al. also teaches the present invention also provides a semiconductor device obtained by the above-described method for producing a cured film of the present invention. The present invention also provides a semiconductor device including a substrate which is a semiconductor element, and a cured film of a resin formed on the substrate by the above-described method for producing a cured film. In addition, the present invention can also be applied to a method for manufacturing a semiconductor device in which a semiconductor element is used as a base material and the above-described method for manufacturing a cured film is included as a part of the process. The semiconductor device of the present invention can be produced by forming the cured film formed by the method for producing a cured film as a surface protective film, an interlayer insulating film, an insulating film for rewiring, a protective film for a flip chip device, a protective film of a semiconductor device having a bump structure, or the like, and combining the cured film with a known method for producing a semiconductor device [0157].
Ogura et al. does not explicitly teach a step of developing the film.
However, Yorisue et al. teaches a photosensitive resin composition has for essential components thereof a polyimide precursor (A) having a specific structure and a photosensitive component (B) [0088] and a method for producing a cured relief pattern, comprising: (1) a step for forming a resin layer on a substrate by coating the previously described photosensitive resin composition of the present invention on the substrate, (2) a step for exposing the resin layer to light, (3) a step for forming a relief pattern by developing the resin layer after exposing to light, and (4) a step for forming a cured relief pattern by heat-treating the relief pattern by irradiating with microwaves 1024] specifically, a photosensitive resin composition prepared according to the method to be subsequently described was spin-coated on Cu subjected to surface treatment using a coater developer (Model D-Spin60A, Sokudo Co., Ltd.) followed by drying to form a coating film having a thickness of 10 μm. This coating film was then irradiated at an energy level of 300 mJ/cm2 with a parallel light mask aligner (Model PLA-501FA, Canon Inc.) (i-line) using a mask having a test pattern. Next, this coating film was spray-developed with a coater developer (Model D-Spin60A, Sokudo Co., Ltd.) using cyclopentanone in the case of a negative type or using 2.38% TMAH in the case of a positive type followed by rinsing with propylene glycol methyl ether acetate in the case of a negative type or pure water in the case of a positive type to obtain a relief pattern on Cu. The wafer having the relief pattern formed on Cu was subjected to heat treatment for 2 hours at the temperature indicated in each example in a nitrogen atmosphere using a programmable curing oven (Model VF-2000, Koyo Lindberg Ltd.) to obtain a cured relief pattern composed of resin having a thickness of about 6 μm to 7 μm on Cu [1193-1194]. It should be noted that the selection of a known material based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 65 USPQ 297 (1945). See MPEP 2144.07. In the instant case, both Ogura et al. and Yorisue et al. are directed to photosensitive resin compositions and their use in semiconductor devices. Yorisue et al. also teaches additional steps in semiconductor manufacturing includes development.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the teachings of Ogura et al. to include additional steps such as development as taught by Yorisue et al. through routine experimentation of combining known steps in the semiconductor manufacturing process and arrive at the instant claims with a reasonable expectation of success. A 10 μm film obtained by the method of Yorisue et al. having the modified composition of Ogura et al. satisfies (Xp + Xt x α + Xr x β ) x D’ = 1.52 (claim 16).
Response to Arguments
Due to the amendment filed June 23, 2026 of instant claims 1, 17, and 31, the 102(a)(1) rejections over Banba and Ogura and the 103 rejections over Banba, Ogura, and Ogura further in the of Yorisue have been withdrawn. Applicants’ arguments regarding these rejections have been considered but are moot due to the amendment of instant claims 1, 17, and 31. However, Ogura is still being used as prior art because it continues to teach the claimed PI precursor resin composition. Specifically, Ogura teaches the amount of the component (B) (Applicant’s ray absorber) is more preferably 5 to 10 parts by mass per 100 parts by mass of the resin [0108]. Ogura also teaches different coating methods which allow for different thickness of the precured (prebaked) resin film [0051]. Therefore, when the amount of the component (B) is reduced and/or the thickness is reduced, the composition of Ogura continues to satisfy the instantly claimed formula.
Due to the amendment of the abstract, the objection to the specification has been withdrawn.
Due to the amendment of instant claims 2, 9-11, 14, 17, 19, 24-26, 29, 32, 38-40, and 43 and cancelation of claims 5, 20, and 34, the objections have been withdrawn.
Due to the amendment of instant claims 9, 10, 12, 14, 24, 25, 27, 29, 38, 39, 41, and 43, the 112(d) rejections have been withdrawn.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. JPH06130664.
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 ANNA E MALLOY whose telephone number is (571)270-5849. The examiner can normally be reached 6:30-3:00 EST M-F.
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/Anna Malloy/Examiner, Art Unit 1737
/KEITH WALKER/Supervisory Patent Examiner, Art Unit 1735
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