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 .
Election/Restrictions
Applicant’s election without traverse of group I, claims 1-19 drawn to a hole transport polymer, in the reply filed on 9/29/2025 is acknowledged.
Claims 20-26 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to nonelected inventions, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 9/29/2025.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-19 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 1 recites “wettable monomers” in line 2. The term “wettable” is a relative term which renders the claim indefinite. The term “wettable” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention.
Claims 2-19 are rejected on the same ground as claim 1.
For the purpose of this office action, the term “wettable monomers” are construed as monomer with functional group(s) that can act as bonding.
Claims 4 and 5recites the limitation “the aromatic amine moiety” in line 1. There is insufficient antecedent basis for the limitation in the claims. It is unclear if “the aromatic amine moiety” is the same as or different from “polycyclic aromatic moiety” or “aromatic amine”.
Claims 6-7 are rejected on the same ground as claim 4-5.
Claim Rejections - 35 USC § 102
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.
Claim(s) 1, 2, 4-7, 10-16 and 19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Luizys et al. (“Branched Methoxydiphenylamine-Substituted Carbazole Derivatives for Efficient Perovskite Solar Cells: Bigger Is Not Always Better”).
Regarding claim 1, Luizys et al. discloses a hole transport polymer, comprising about 0.5 mol% to about 50 mol% of one or more wettable monomers comprising a polycyclic aromatic moiety (see the carbazole with alkoxy group in figs. 1-2, schemes 1-2) and a second monomer comprising an aromatic amine (see Ar in figs. 1-2 and schemes 1-2). There are 2 Ar groups on each carbazole ring. As such, there must be 1/3 carbazole in each polymer, or 33 mol% of polycyclic aromatic moiety, or within the claimed range of about 0.5 mol% to about 50mol%.
Regarding claim 2, Luizys et al. discloses a hole transport polymer as in claim 1 above, and teaches one or more wettable monomers comprise at least one oligooxy group and an alkyl side chain comprising four or fewer carbon atoms (see the alkoxy attachment on the carbazoles in figs. 1-2 and schemes 1-2).
Regarding claim 4, Luizys et al. discloses a hole transport polymer as in claim 1 above, wherein the aromatic amine moiety comprises a carbazole monomer (see figs. 1-2 and schemes 1-2).
Regarding claim 5, Luizys et al. discloses a hole transport polymer as in claim 4 above, and teaches the aromatic amine moiety comprises an oligooxy group and an amine group (see figs. 1-2 and schemes 1-2).
Regarding claim 6, Luizys et al. discloses a hole transport polymer as in claim 4 above, and teaches the choice of carbazole. Therefore, the reference is deemed to be anticipatory to the instant claim, since the instant claim is directed to the other choice, or fluorene monomer.
Regarding claim 7, Luizys et al. discloses a hole transport polymer as in claim 4 above, and teaches the carbazole monomer is selected from the group comprising dibromocarbazole (see schemes 1-2).
Regarding claim 10, Luizys et al. discloses a hole transport polymer as in claim 1 above, and teaches the aromatic amine is a derivative of aniline (see Ar group in figs. 1-2 and schemes 1-2).
Regarding claim 11, Luizys et al. discloses a hole transport polymer as in claim 1 above, and teaches including one or more second aromatic amine moieties of carbazoles (see figs. 1-2 and schemes 1-2).
Regarding claim 12, Luizys et al. discloses a hole transport polymer as in claim 1 above, and teaches the polymer having a decomposition temperature of greater than about 350 °C (see Tdec in Table 1).
Regarding claim 13, Luizys et al. discloses a hole transport polymer as in claim 12 above, and teaches the decomposition temperature is greater than about 390 °C (see Tdec in Table 1).
Regarding claim 14, Luizys et al. discloses a hole transport polymer as in claim 1 above, and teaches the polymer having a glass transition temperature greater than about 100°C (See Tg in Table 1).
Regarding claim 15, Luizys et al. discloses a hole transport polymer as in claim 1 above, and teaches the polymer having a highest occupied molecular orbital energy of about -5.4 eV to about -4.9 eV (see Ip in Table 1).
Regarding claim 16, Luizys et al. discloses a hole transport polymer as in claim 1 above, and teaches the polymer having a lowest unoccupied molecular orbital energy of about -2.5 eV to about -2.0 eV (see Eea in Table 1).
Regarding claim 19, Luizys et al. discloses a hole transport polymer as in claim 1 above, the reference is deemed to be anticipatory for the instant claim since the instant claim is directed to product-by-process. Regardless how the hole transport polymer is synthesized by a Buchwald-Hartwig cross coupling reaction or an Ullmann reaction or by other methods/reactions, in the end the hole transport polymer is still a hole transport polymer.
Claim(s) 1-5, 7, 10-16 and 18-19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Peng et al. (“Ether-soluble hole-transporting polymers based on triphenylamine/phenolthiazine moieties with shallow HOMO levels”).
Regarding claim 1, Peng et al. discloses a hole transport polymer PTPA-F and PTPA-Cz (see scheme 1) comprising 50% mole (or half of the polymer) of wettable monomers comprising a polycyclic aromatic moiety (see the carbazole moiety of PTPA-Cz or fluorene moiety of PTPA-F) and a second monomer comprising an aromatic amine (see triphenylamine moiety in PTPA-Cz and PTPA-F).
Regarding claims 2-3, Peng et al. discloses a hole transport polymer as in claim 1 above, and teaches the one or more wettable monomers comprises at least one oligooxy group and an alkyl side chain comprising four or few carbon atoms such as methoxyethoxy(ethyl) group (see the group being circle below):
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Regarding claim 4, Peng et al. discloses a hole transport polymer as in claim 1 above, and teaches the aromatic amine moiety comprises fluorene monomer (see PTPA-F in Scheme 1) or carbazole monomer (see PTPA-Cz in Scheme 1).
Regarding claim 5, Peng et al. discloses a hole transport polymer as in claim 1 above, and teaches the aromatic amine moiety comprises oligooxy group (see Scheme 1).
Regarding claim 7, Peng et al. discloses a hole transport polymer as in claim 1 above. The reference is deemed to be anticipatory for the instant claim
Regarding claim 10, Peng et al. discloses a hole transport polymer as in claim 1 above, and teaches the aromatic amine is triphenylamine which comprises an aniline (see scheme 1).
Regarding claims 12 and 13, Peng et al. discloses a hole transport polymer as in claim 1 above, and teaches a decomposition temperature greater than 350oC or 390oC (see Table 1).
Regarding claim 14, Peng et al. discloses a hole transport polymer as in claim 1 above, and teaches the glass transition temperature greater than 100oC (see Tg of PTPA-Cz in Table 1).
Regarding claim 15, Peng et al. discloses a hole transport polymer as in claim 1 above, and discloses the highest occupied molecular orbital energy of -5.12eV and -5.08eV (see Table 1), which are right within the claimed range of about -5.4eV to -4.9eV.
Regarding claim 16, Peng et al. discloses a hole transport polymer as in claim 1 above, and discloses the lowest unoccupied molecular of -2.17 eV and -2.1eV (see Table 1), which are right within the claimed range of about -2.5eV to about -2.0eV.
Regarding claim 18, Peng et al. discloses a hole transport polymer as in claim 1 above, and teaches the second monomer to be triphenylamineamine that is hydrophobic (or hydrophobic monomers having hydrophobic side chains, see scheme 1).
Regarding claim 19, Peng et al. discloses a hole transport polymer as in claim 1 above, the reference is deemed to be anticipatory for the instant claim since the instant claim is directed to product-by-process. Regardless how the hole transport polymer is synthesized by a Buchwald-Hartwig cross coupling reaction or an Ullmann reaction or by other methods/reactions, in the end the hole transport polymer is still a hole transport polymer.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 6, 8-9 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Peng et al. as applied to claims 1 and 4 above, in view of Huang et al. (“Novel Electroluminescent Conjugated Polyelectrolytes Based on Polyfluorene”).
Regarding claims 6 and 8, Peng et al discloses a hole transport polymer as in claim 4 above, wherein Peng et al. uses two monomers. Peng et al. does not disclose further comprising one or more second aromatic amine moieties selected from a group comprising carbazoles, derivatives of carbazoles, fluorenes, derivatives of fluorenes, and combination thereof as claimed in claim 11. Peng et al. also do not teach including a fluorene monomer selected from the group comprising dimethylfluorene, dihexylfluorene, dimethylaminopropylfluorene, and dibromofluorene as claimed in claim 6; the one or more wettable monomers comprises at least one wettable dialkylfluorene monomer and a second wettable fluorene monomer having a side chain comprising at least one an amide group, a phosphine group, an oligoalkyl group, a halogen, and an amine group as claimed in claim 8, or the second wettable fluorene monomer is a dimethylaminopropylfluorene monomer as claimed in claim 9.
Huang et al. teaches adding dimethylaminopropylfluorene monomer to a polymer would tune the optical properties of the polymer (see Scheme 1, Table 1).
It would have been obvious to one skilled in the art at the time of the invention was made to modify the hole transport polymer of Peng et al. by adding dimethylaminopropylfluorene monomer to tune the optical properties as taught by Huang et al. In such modification, the additional dimethylaminopropylfluorene corresponds to the fluorene monomer as claimed in claim 6, the one or more second aromatic amine moieties as claimed as claim 11, a second wettable fluorene comprising dimethylaminoprypylfluorene as claimed in claims 8-9.
Claim(s) 17 is rejected under 35 U.S.C. 103 as being unpatentable over Peng et al. as applied to claim 1 above, in view of Lunt et al. (US 2020/0303667).
Regarding claim 17, Peng et al. discloses a hole transport polymer as claimed in claim 1 above, wherein Peng et al. discloses all the structural limitations of the claimed hole transport polymer and uses hydrophobic monomers.
Peng et al. does not explicitly disclose the property/characteristic of water contact angle of greater than about 80 degrees.
Lunt et al. teaches adjusting and tuning an organic layer to have water angle of greater than about 80 degrees to increase the lifetimes of the layer/device ([0061], [0066-0070]).
It would have been obvious to one skilled in the art before the effective filing date of the claimed invention to have adjusted and tuned the hole transport polymer to have water contact angle greater than about 80 degrees to increase lifetimes of the layer/device as taught by Lunt et al.
Conclusion
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THANH-TRUC TRINH
Primary Examiner
Art Unit 1726
/THANH TRUC TRINH/Primary Examiner, Art Unit 1726