Detailed Action
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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Response to Amendment
Applicant’s Amendment filed 03/03/2026 has been entered and is being considered. Claims 1, 4-6, and 11 have been amended. Claim 3 has been canceled. No new matter is added with these claim amendments.
Response to Arguments
Regarding the Amendments made and the arguments set forth therefrom – the Amendments have changed the scope of the claims to encompass a different set of possible embodiments and as such the grounds of rejection set forth in the prior office action are moot. These rejections are withdrawn.
However, after further search and consideration, the Examiner makes a new grounds of rejection over 35 USC 103 over the same references as in the prior office action. Applicant’s assertions that Kamemoto does not in any way teach a polyimide subunit are not persuasive, as they are not representative of the reference as a whole. Patents and corresponding applications are prior art for All they contain. A polyimide precursor is treated to imidize the polyamic acid subunits and the reference Kamemoto teaches such treatment – arguments couched in the language “a polyimide precursor” that ignore the rest of the disclosure of the reference are not persuasive. The entire reference is directed to a polyimide precursor that is heated to force imide ring closure in the precursor, where at [0030] 5-50% of the polymer may be subjected to ring closure from heat treatment. In regards to the experimental examples - Kamemoto describes a thermal heating process at evaluation procedure (2) described as applied to the example compositions ([0062]) that the composition(s) is applied to a silicon wafer, baked on a hotplate at 120 degrees Celsius for 3 minutes, then heat-treated in an oven at 170 degrees for 30 minutes and then 300 degrees for an hour.
Applicant’s assertion of unexpected results and data supporting such is appreciated but not persuasive because while the data appear to show a concrete relationship, the data is directed to a narrow subset of embodiments of the subunits claimed. Unexpected results must be commensurate in scope with the claims (See MPEP 716.02(d)) -the experimental data pointed to appears to be predicated on embodiments having three subunits ODPA, P6FDA, and BPDA being present, while the scope of the claims allows for any number of subunits to be present having structures with moeities not covered by the claims. The Examiner is unable to determine if these results would be indicated for instances where, for instance, the phenyl rings of ODPA were instead anthracene rings, or where claimed X1 and X2 were decyl groups. If applicant wishes to amend the claims to better align their scope with that of the data asserted to show unexpected superior results, they may do so at their leisure.
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.
Claim(s) 1-5, 7-10, 14, and 16 is/are rejected under 35 U.S.C. 103 as obvious over Kamemoto et al (JP 2011202059 A).
Regarding Claims 1-7, 7-10, 14, 16-17, and 19, Kamemoto discloses a positive type photosensitive resin composition that is suitable for a surface protective film, an interlayer insulating film, or other films produced for use in semiconductor or electronic device components ([0001), wherein the film comprises a resin dissolved in an organic solvent to be coated upon a substrate. The composition of the resin has a polyimide structure described generally from [0013]-[0036], wherein other resin components are described from [0037]-[0051], such as a quinonediazide compound, solvent, a phenolic compound, and a surfactant.
Kamemoto does not explicitly disclose, in an experimental embodiment, a characterized polymer embodiment comprising both polyamic acid and polyimide units. Kamemoto describes a thermal heating process at evaluation procedure (2) described as applied to the example compositions ([0062]) that the composition(s) is applied to a silicon wafer, baked on a hotplate at 120 degrees Celsius for 3 minutes, then heat-treated in an oven at 170 degrees for 30 minutes and then 300 degrees for an hour. Kamemoto does not state a particular % imidization of the amic acid subunits by ring closure regarding this procedure and as such while it should be clear to the average person in the field of endeavor that this imidization occurs – technically the imide embodiment(s) is not explicitly disclosed.
This limitation is met by the general disclosure of the reference – Kamamoto does disclose in general disclosure that the polyimide precursors of the reference are heated and imidized to a degree of between 5% and 50% at [0030]. As such the polymer must comprise at least some (5-50% of present structural units) polyimide units as a function of the heating step performed.
The resin of the reference have a general formula conforming to the structure (1) at [014]-[0028], which is ring closed to form a polyimide having excellent heat resistance and solvent resistance. The structural unit (1) comprises 50% or more units of the structural units of the resin.:
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Wherein R1 is a tetravalent organic group having 2 or more carbons, and R2 is a divalent group having 2 or more carbon atoms. The structural unit (1) comprises 50% or more units of the structural units of the resin. 10-50% of R1s in the units are represented by a structure conforming to formula (2) and 10-100% of R2 are represented by a group conforming to formula (3):
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Where p and q are each 0-1, and p+q may be 0 but is preferably greater than 0. When R1 comprises a structure (2) in an amount ranging from 10 ro 50%, solubility in solvents is improved. When R2 comprises the structure (3) in 10-100%, the photosensitivity is improved.
R1 may also comprise a structural unit corresponding to formula (4) in an amount ranging from 20% to 90%. R2 may be comprised of a structural component conforming to formula (5). R3 may be a hydrogen or a C1-C20 organic group, and each R3 may independently be H or C1-C20 organic group.
At [0030], the reference states that between 5 and 50% of structural units may be subjected to imide closure as a function of heating.
The experimental examples of the reference describe the use of 6 varieties of diamine and carboxylic acid anhydrides in [0068] that are used in the synthetic examples of [0069]-[0094] and Tables 1 and 2.
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Additionally, a hydroxyamino compound (a) was also synthesized as per the synthetic example 1:
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A quinone diazide compound (b) is also included as created in the synthetic example 2 ([0072]-[0073]):
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At [0076] the compositions of Table 1 are cured and evaluated as described in the specification at [0060]-[0067], forming cured films (bodies) (claims 14 and 16- claim 16 recites a property of the cured body of claim 14. As claim 14 is considered obvious, it must bear any properties ascribed to it and as such claim 16 is also obvious.).
Resin A in Table 1 comprises BSAA, BPDA, BAHF, 4,4’-DAE, and SiDA monomer constituents, where the component monomers are dissolved into a solution together and heated to react for an hour, then combined with quinone diazide (b) in a gamma-butyrolactone solvent (claim 10) as described in [0074]-[0075]. This embodiment reads upon the claimed chemical formulas 1 and 2 for where:
Regarding Chemical Formula 1
BAHF and BPDA react to form a structure having 2 hydroxyl groups and 2 carboxylic acid groups (a, b, c, and each = 1, a+b=2 (claim 2))
R1 (BAHF) is a C15 group
R2 (BPDA) is a C12 group
X1 and X2 are H
Regarding Chemical formula 2
BAHF and BSAA (and/or 4’,4-DAE) react to form a structure having 2 hydroxyl groups and 2 carboxylic acid groups
R3 (BAHF) is a C15 group
R4 (BSAA) is a C26 group and/or may be (4,4’-DAE) a C12 organic group
BSAA conforms to General Formula 1 where X3 and X4 are hydrogen, subscript a and b are each 1, and R5 and R6 are each C1 groups (methyl) (claim 7 and claim 8)
4,4’-DAE conforms to General Formula 1 where C3 and C4 are hydrogen, subscripts a and b are each 0. (claim 7 and 8)
X1 and X2 are H
Resins B-O each comprise the subunits mentioned above and read upon the claimed formulas for the reasons above.
In the evaluation procedure (2) described as applied to the example compositions ([0062]) that the composition(s) is applied to a silicon wafer, baked on a hotplate at 120 degrees Celsius for 3 minutes, then heat-treated in an oven at 170 degrees for 30 minutes and then 300 degrees for an hour. This process will imidize the polyimide precursor, wherein the carboxylic acid anhydride monomer(s) (BSAA monomer and BPDA monomer) present in examples 3 and 4 (Resins C and D) will form an imide ring arriving at structures meeting the limitations of the claim. When there remain unimidized structures (such as during the 170 degree cure), all 3 claimed structural units (Chemical Formula 1, Chemical Formula 2, and Imidized units) are present. Example 3 (Resin C) comprises the BSAA monomer in 0.05 mols, the 4,4’-DAE monomer in 0.025 mols, and BPDA in 0.05 moles. Dividing these two monomers’ molar abundance (which conform to General Formula 1 as discussed above) by the total number of moles yields a 42 mol% abundance of monomers that conform to General Formula 1. Repeating this calculation for Example 4 (Resin D) yields 65 mol% abundance.
Kamemoto ascribes improved heat resistance and solvent resistance to the polyimide resultant from treatment.
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention from the general disclosure of the reference, using the known materials and procedures discussed therein to arrive at a polyimide having improved heat and solvent resistance.
Regarding Claim 5, Kamemoto discloses a positive type photosensitive resin composition that is suitable for a surface protective film, an interlayer insulating film, or other films produced for use in semiconductor or electronic device components ([0001), wherein the film comprises a resin dissolved in an organic solvent to be coated upon a substrate. The composition of the resin has a polyimide structure described generally from [0013]-[0036], wherein other resin components are described from [0037]-[0051], such as a quinonediazide compound, solvent, a phenolic compound, and a surfactant.
Kamemoto does not explicitly disclose, in an experimental embodiment, a characterized polymer embodiment comprising both polyamic acid and polyimide units. Kamemoto describes a thermal heating process at evaluation procedure (2) described as applied to the example compositions ([0062]) that the composition(s) is applied to a silicon wafer, baked on a hotplate at 120 degrees Celsius for 3 minutes, then heat-treated in an oven at 170 degrees for 30 minutes and then 300 degrees for an hour. Kamemoto does not state a particular % imidization of the amic acid subunits by ring closure regarding this procedure and as such while it should be clear to the average person in the field of endeavor that this imidization occurs – technically the imide embodiment(s) is not explicitly disclosed.
This limitation is met by the general disclosure of the reference – Kamamoto does disclose in general disclosure that the polyimide precursors of the reference are heated and imidized to a degree of between 5% and 50% at [0030]. As such the polymer must comprise at least some (5-50% of present structural units) polyimide units as a function of the heating step performed.
The resin of the reference have a general formula conforming to the structure (1) at [014]-[0028], which is ring closed to form a polyimide having excellent heat resistance and solvent resistance. Example 3 (Resin C) comprises the BSAA monomer in 0.05 mols, the 4,4’-DAE monomer in 0.025 mols, and BPDA in 0.05 moles. Dividing these two monomers’ molar abundance (which conform to General Formula 1 as discussed above) by the total number of moles yields a 42 mol% abundance of monomers that conform to General Formula 1. Repeating this calculation for Example 4 (Resin D) yields 65 mol% abundance.
Kamemoto ascribes improved heat resistance and solvent resistance to the polyimide resultant from treatment.
A person having ordinary skill in the art would have found it obvious to arrive at the claimed invention from the general disclosure of the reference, using the known materials and procedures discussed therein to arrive at a polyimide having improved heat and solvent resistance.
Regarding Claim 9, Kamemoto discloses a positive type photosensitive resin composition that is suitable for a surface protective film, an interlayer insulating film, or other films produced for use in semiconductor or electronic device components ([0001), wherein the film comprises a resin dissolved in an organic solvent to be coated upon a substrate. The composition of the resin has a polyimide structure described generally from [0013]-[0036], wherein other resin components are described from [0037]-[0051], such as a quinonediazide compound, solvent, a phenolic compound, and a surfactant.
Kamemoto does not explicitly disclose, in an experimental embodiment, a characterized polymer embodiment comprising both polyamic acid and polyimide units. Kamemoto describes a thermal heating process at evaluation procedure (2) described as applied to the example compositions ([0062]) that the composition(s) is applied to a silicon wafer, baked on a hotplate at 120 degrees Celsius for 3 minutes, then heat-treated in an oven at 170 degrees for 30 minutes and then 300 degrees for an hour. Kamemoto does not state a particular % imidization of the amic acid subunits by ring closure regarding this procedure and as such while it should be clear to the average person in the field of endeavor that this imidization occurs – technically the imide embodiment(s) is not explicitly disclosed.
This limitation is met by the general disclosure of the reference – Kamamoto does disclose in general disclosure that the polyimide precursors of the reference are heated and imidized to a degree of between 5% and 50% at [0030]. As such the polymer must comprise at least some (5-50% of present structural units) polyimide units as a function of the heating step performed.
The resin of the reference have a general formula conforming to the structure (1) at [014]-[0028], which is ring closed to form a polyimide having excellent heat resistance and solvent resistance.
The quinone diazide compound (b) is obtained by reacting a naphthoquinone diazide sulfonyl chloride compound with a phenolic compound TrisP-PA as described in [0072]-[0073]:
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’
This compound TrisP-PA meets the limitations of claim 9 at formula (a) where all aryl-bound R groups are H, R9 and R10 are methyl, and X3 is methyl
Regarding Claim 6, the reference Kamemoto discloses the limitations of the claim as discussed above regarding claim 1. However, Kamemoto fails to disclose a composition that comprises the resin, quinone diazide, solvent, and the thermal crosslinking agent of claim 6
This limitation is met by the general disclosure of the reference, which discloses that there may be a thermal crosslinker that may be an alkoxymethyl compound present in 10-30 parts by weight per 100 parts of resin. The solvent may be present in 100 to 1500 parts by weight of solvent relative to 100 parts by weight of resin (See [0045]-[0046]). The reference asserts that the inclusion of the crosslinker will improve the resultant mechanical properties of films produced.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention at the time of filing from the general disclosure of the reference, incorporating the thermal crosslinking compound of Kamemoto into a taught composition so as to improve the mechanical properties of films produced using the composition.
Regarding Claims 17 and 19, the reference discloses all of the limitations of the claims as discussed above regarding claims 1 and 14. The reference does not disclose an experimental embodiment of the devices discussed.
These limitations are met by the general disclosure of the reference, where in [0059] the reference asserts utility for the composition in films and the films produced may be used in the formation of devices having insulation films formed from the composition of the disclosure.
A person of ordinary skill in the art would have found it obvious to arrive at the claimed invention at the time of filing from the disclosed use of the inventive film of the disclosure – using a known product as part of a known process (curing) to be used as part of a known product (insulating film or protective layer).
Claim(s) 11-13 and 18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kamemoto et al (JP 2011202059 A) as applied to claim 1 above, and further in view of Komuro et al (JPWO 2017217292 A).
Regarding Claim 11-13, Kamemoto discloses the limitations of the claims as discussed above regarding claim 1.
Kamemoto however does not disclose a crosslinking compound that meets the limitations of the claim 11, rather generally teaching phenolic compounds and alkoxymethyl compounds as crosslinkers.
This limitation is met by Komuro.
Komuro discloses a composition comprising a polyimide resin and a photosensitive compound described from [0010]-[0057] and [0058]-[0078 respectively, where the polyimide resin may comprise phenolic hydroxyl groups present on the main chain. Additionally comprised are solvents ([0079], polymerizable compounds ([0080]-[0085], thermal crosslinking agents ([0086]-[0090]), colorants, dyes, and pigments ([0091]-[0125], as well as dispersants.
At [0213] exemplary crosslinking agents are depicted, such as e-1:
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Compound e-1 meets the limitations of the claim 11 where R61 and R26 are methyl groups, but has an additional carbon between the aryl and methoxy group (this is a methylmethoxy group, rather than a methoxy group). However, a person of ordinary skill in the art would find it obvious to arrive at the claimed invention from the above compound due to the chemical structural similarity of the two compounds which would beget similar crosslinking behavior. This compound would also meet the limitations of claim 12 at formula (j) where R71-R76 are each methylmethoxy groups. Thermal crosslinkers, such as alkoxy compounds, are included in the composition of Kamemoto in an amount ranging from 10-30 parts by weight per 100 parts of resin (claim 13).
A person of ordinary skill in the art would find it obvious to arrive at the claimed invention from the above compound due to the chemical structural similarity of the two compounds which would beget similar crosslinking behavior (See MPEP 2144.09) when including the compound from Komuro into the composition of Kamemoto.
Regarding Claim 18, Kamemoto discloses the limitations of the claims as discussed above regarding claim 1 and 14.
Kamemoto does not disclose a bending test or a flexible display device.
These limitations are met by Komuro, whose disclosure covers flexible films formed from polyimides. Komuro discloses a composition comprising a polyimide resin and a photosensitive compound described from [0010]-[0057] and [0058]-[0078 respectively, where the polyimide resin may comprise phenolic hydroxyl groups present on the main chain. Additionally comprised are solvents ([0079], polymerizable compounds ([0080]-[0085], thermal crosslinking agents ([0086]-[0090]), colorants, dyes, and pigments ([0091]-[0125], as well as dispersants.
The composition of Komuro may be used in a display device, such as a flexible organic EL display device ([0192]), wherein the composition’s cured film is comprised therein as an insulating layer.
Claim(s) 15 is rejected under 35 U.S.C. 103 as being unpatentable over Kamemoto et al (JP 2011202059 A) as applied to claim 1 and 14 above, and further in view of Hong et al (US 20200353668 A1)
Regarding Claim 15, Kamemoto discloses the limitations of the claims as described above regarding claims 1 and 14. Kamemoto also discloses that the thickness of films made from the inventive composition may be between 0.1 to 150 microns at [0054].
Kamemoto does not disclose a bending/folding test having a curvature of 1R.
This limitation is met by Hong.
Hong discloses a polyimide film and for use in an electronic device having flexible characteristics (abstract). The polyimide film of Hong is made using BPDA (see above regarding claim 1) and 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA) in combination with bistrifluoromethyl benzidine. Both of the dianhydride monomers are monomers contemplated by Kamemoto at [0067]. The polymer was treated with silica and cast into a film, after which it was baked and framed, where the frame was put under tension to as to deform it ([0062]-[0099]. The film had a thickness of 50 microns. The film is deemed foldable at a radius of curvature (1R) at 1mm or less.
A person of ordinary skill in the art would have found it obvious to apply the testing conditions of Hong to the composition film(s) of Kamemoto, which discloses polyimide films made from similar monomers and having a range of thicknesses overlapping that of Hong. Such testing would be useful to determine the mechanical properties of the films of Kamemoto and amount to performing routine experimentation as guided by a prior art reference disclosing such experimentation.
Conclusion
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.
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/A.P.T./Examiner, Art Unit 1737
/MARK F. HUFF/Supervisory Patent Examiner, Art Unit 1737
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