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 .
Status of the Claims
Claims 1-8 are pending.
Priority
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55. Instant application is a U.S. National Stage Entry of PCT/JP2022/014732, filed 03/25/2022. PCT/JP2022/014732 claims priority of foreign application JP2021-057864, filed 03/30/2021. Therefore, the effective filing date is 03/30/2021.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 10/30/2025, 10/21/2025, 07/07/2025, and 10/24/2023 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
The information disclosure statement filed 08/29/2025 fails to comply with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609 because references CN 105720210 A and CN 107438597 A do not have English translations provided. It has been placed in the application file, but the information referred to in these references only has not been considered as to the merits. Applicant is advised that the date of any re-submission of any item of information contained in this information disclosure statement or the submission of any missing element(s) will be the date of submission for purposes of determining compliance with the requirements based on the time of filing the statement, including all certification requirements for statements under 37 CFR 1.97(e). See MPEP § 609.05(a).
Objections – Specification
The disclosure is objected to because of the following informalities:
Compound A – 53, shown below, on page 18 of the specification appears to be missing a bond. The examiner believes a bond should be between the two phenyl groups so that compound A – 53 reads on instant Formula (1).
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Appropriate correction is required.
Objections – Drawings
37 C.F.R. 1.84:
(p) Numbers, letters, and reference characters.
(1) Reference characters (numerals are preferred), sheet numbers, and view numbers must be plain and legible, and must not be used in association with brackets or inverted commas, or enclosed within outlines, e.g., encircled. They must be oriented in the same direction as the view so as to avoid having to rotate the sheet. Reference characters should be arranged to follow the profile of the object depicted.
The drawings are objected to because the sheet number and view are not oriented in the same directed. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Claim Objections
Claim 8 is objected to because of the following informalities:
Claim 8 reads “A photoelectric conversion element using the hole transport material…” (emphasis added). To avoid the recitation of a use, without setting forth any steps involved in the process, the claim should instead read “A photoelectric conversion element comprising the hole transport material…”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
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 1-8 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for compounds of Formula (1) where R1 is a linear or branched C1-C5 alkyl group optionally substituted with phenyl, C3-7 cycloalkyl, C1-3 alkyl, C2-6 alkenyl, or C2-6 alkynyl, and where R2 to R9 are C1-10 alkyl, C2-10 alkenyl, C2-10 alkynyl, or
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, optionally substituted with one or more C1-3 alkoxy groups, does not reasonably provide enablement for compounds of Formula (1). The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make the invention commensurate in scope with these claims.
To be enabling, the specification of the patent application must teach those skilled in the art how to make and use the full scope of the claimed invention without undue experimentation. In re Wright, 999 F.2d 1557, 1561 (Fd. Cir. 1993). Explaining what is meant by "undue experimentation," the Federal Circuit has stated that:
The test is not merely quantitative, since a considerable amount of experimentation is permissible, if it is merely routine, or if the specification in question provides a reasonable amount of guidance with respect to the direction in which experimentation should proceed to enable the determination of how to practice a desired embodiment of the claimed invention. PPG v. Guardian, 75 F.3d 1558, 1564 (Fed. Cir. 1996). As pointed out by the court in In re Angstadt, 537 F.2d 498 at 504 (CCPA 1976), the key word is "undue", not "experimentation".
The factors that may be considered in determining whether a disclosure would require undue experimentation are set forth In re Wands, 8 USPQ2d 1400 (CAFC 1988) at 1404 wherein, citing Ex parte Forman, 230 USPQ 546 (Bd. Apls. 1986) at 547 the court recited eight factors:
1- the quantity of experimentation necessary,
2- the amount of direction or guidance provided,
3- the presence or absence of working examples,
4- the nature of the invention,
5- the state of the prior art,
6- the relative skill of those in the art,
7- the predictability of the art, and
8- the breadth of the claims
These factors are always applied against the background understanding that scope of enablement varies inversely with the degree of unpredictability involved. In re Fisher, 57 CCPA 1099, 1108, 427 F.2d 833, 839, 166 USPQ 18, 24 (1970). Keeping that in mind, the Wands factors are relevant to the instant fact situation for the following reasons:
The nature of the invention
The nature of the invention relates to compounds of formula (1) in claim 1. Such compounds are taught to be useful in hole transport materials. This invention is also directed to hole transport materials and photoelectric conversion elements comprising said compounds.
Predictability of the art
The compounds A-1 to A-76 synthesized in the instant specification appear novel. However, the hypothetical compounds in claim 1 would be unpredictable in terms of one skilled in the art being able to synthesize every possible compound claimed in instant claim 1. It is well established that “the scope of enablement varies inversely with the degree of unpredictability of the factors involved,” and physiological activity is generally considered to be an unpredictable factor. See In re Fisher, 427 F.2d 833, 839, 166 USPQ 18, 24 (CCPA 1970).
In terms of the law, MPEP 2107.03 states “evidence of pharmacological or other biological activity of a compound will be relevant to an asserted therapeutic use if there is a reasonable correlation between the activity in question and the asserted utility. Cross v. Iizuka, 753 F.2d 1040, 224 USPQ 739 (Fed. Cir. 1985); In re Jolles, 628 F.2d 1322, 206 USPQ 885 (CCPA 1980); Nelson v. Bowler, 626 F.2d 853, 206 USPQ 881 (CCPA 1980).” If correlation is lacking, it cannot be relied upon, Ex parte Powers, 220 USPQ 924; Rey-Bellet and Spiegelberg v. Engelhardt v. Schindler, 181 USPQ 453; Knapp v. Anderson, 177 USPQ 688. Indeed, the correlation must have been established “at the time the tests were performed”, Hoffman v. Klaus, 9 USPQ2d 1657.
Level of skill in the art
An ordinary artisan in the area of photoelectric conversion would have experience in synthesizing and screening chemical compounds for particular activities, such as an engineer or a chemist. Screening of new compounds, while complex, is routine in the art.
4. The breadth of the claims
The scope of the claims involves compounds of formula (1), shown below.
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Claim 1 is very broad in the number of variables (R1 to R9 and X) and the options of substituents for each variable. There is an infinite amount of hypothetical compounds included in claim 1.
5. The amount of direction provided, the presence or absence of working examples, and the quantity of experimentation necessary
The specification only provides the synthesis of 20 compounds, with 76 example compounds total shown in the specification. In all of the compounds synthesized, R1 is a linear or branched C1-C5 alkyl group optionally substituted with phenyl, cyclohexyl, C1-3 alkyl, C2-6 alkenyl, or C2-6 alkynyl; and R2 to R9 are C1-10 alkyl, C2-10 alkenyl,
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, or
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. Additionally, although there are no examples where R2 to R9 are alkynyl, it would be assumed that the inventors are also enabled for R2 to R9 to be C2-10 alkynyl, since these substituents are similar in size and reactivity.
Synthesis methods are not taught in the specification to provide for the aforementioned variables to include all of the possible substituents listed in the claims. It would be expected that the varying ring sizes (e.g., R1 to R9 being C6-36 aryl) and heteroatoms in the rings (e.g., R1 to R9 being 5 to 36 membered heterocyclic rings, with any heteroatoms) would change the reactivity of the compounds, and therefore may require alternate synthesis methods. It could also be possible that some combinations of compounds may not be able to be synthesized due to their instability (e.g., where R1 to R9 are all 36-membered heterocyclic groups). It would require one skilled in the art, such as a chemist, to perform thousands of reactions to determine which compounds of formula (1) can be prepared and would likely require synthesis methods other than those provided in the specification. This is undue experimentation given the limited guidance and direction provided by Applicants.
Accordingly, the instant claims do not comply with the enablement requirement of 35 U.S.C. 112(a), since to practice the claimed invention a person of ordinary skill in the art would have to engage in undue experimentation, with no assurance of success.
Claims 6-8 are rejected for being dependent upon a rejected claim and failing to further limit the structure of formula (I).
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 1-8 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.
Regarding claims 1-4, the phrase "optionally has a substituent group" renders the claims indefinite because the claims include elements not actually disclosed. The optional substituent groups are not defined in the claim, and the specification, in paragraph [0031], only provides non-limiting examples. Therefore, an indefinite number of compounds arise from the claims.
Claims 5-8 are rejected as being dependent upon a rejected claim and failing to give structure to all “optional substituents”.
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.
Claims 1, 2, and 4-7 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Oda et al. (Research upon Joint Reaction and Transjointing. (I), Bulletin of the Institute for Chemical Research, Kyoto University, 30 July 1954, Vol. 32(4), pages 159-167).
Oda et al. teaches, on page 165, the compound shown below, which reads on claims 1, 2, 4, and 5.
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Regarding instant claims 6 and 7, the instant specification teaches, in paragraph [0008], that the compound itself is the “hole transport material”. Therefore, the compound above, which also exists in a composition with water as taught on page 165, would read on instant claims 6 and 7. The phrase “for a photoelectric conversion element” in instant claim 7 would be an intended use, and is therefore not considered a limitation. MPEP 2111.02 II states: “If the body of a claim fully and intrinsically sets forth all of the limitations of the claimed invention, and the preamble merely states, for example, the purpose or intended use of the invention, rather than any distinct definition of any of the claimed invention’s limitations, then the preamble is not considered a limitation and is of no significance to claim construction. Shoes by Firebug LLC v. Stride Rite Children’s Grp., LLC, 962 F.3d 1362, 2020 USPQ2d 10701 (Fed. Cir. 2020)”.
Claims 1, 2, and 4-7 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Hidaka et al. (Fluorescence Probe Studies on Alkylcarbazolesulphonates in Aqueous Solution, J. Chem. Soc., Chem. Commun., 1983, pages 99-101), cited by Applicant in the IDS.
Hidaka et al. teaches, on page 100, compound 2, shown below where n is 10 or 12, in an aqueous solution, which reads on instant claims 1, 2, and 4-7. See reasoning above regarding claims 6 and 7.
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Claims 1-7 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Qiu et al. (Poly[3,6-(carbaz-9-yl)propanesulfonate]: A Self-Doped Polymer with Both Cation and Anion Exchange Properties, J. Electrochem. Soc., March 1990, Vol. 137(3), pages 900-904), cited by Applicant in the IDS.
Qiu et al. teaches, in Equation [1] on page 901, compounds 3 and 4, which read on instant claims 1-7. Qiu et al. teaches, on page 900, that the compounds and polymers are “water soluble and act as electrically switchable charge-controllable membranes with cation exchange properties”.
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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 8 is rejected under 35 U.S.C. 103 as being unpatentable over Qiu et al. (cited above), cited by Applicant in the IDS, further in view of Nomura et al. (US 20110063485 A1).
Qiu et al. teaches, in Equation [1] on page 901, compounds 3 and 4, which are “water soluble and act as electrically switchable charge-controllable membranes with cation exchange properties”. See above rejection.
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Qiu et al. fails to teach these hole transport materials being a component of a photoelectric conversion element.
However, Nomura et al. teaches, in claims 1 and 8, a photoelectric conversion device comprising a compound of formula (A-1) shown below, where Xa can be a single bond and the nitrogen can be further substituted.
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The compounds taught by Nomura et al. share the same core structure as those taught by Qiu et al. Additionally, it is taught by Nomura et al., in paragraph [0024], that the diaryl amine structure, which is possessed also by the compounds taught by Qiu et al., is used for hole transport in the photoelectric conversion element.
Therefore, it would be prima facie obvious to one of ordinary skill in the art to use the compounds taught by Qiu et al., which are taught to be electroactive and conducting polymers, in a photoelectric conversion element, since compounds with the same core structure and properties are taught by Nomura et al. to be used in a photoelectric conversion element.
One of ordinary skill in the art would have a reasonable expectation of success using the compounds of Qiu et al., which have the same core structure and properties of those taught by Nomura et al., in the photoelectric conversion element taught by Nomura et al.
Conclusion
Claims 1-8 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RILLA M SAMSELL whose telephone number is (703)756-5841. The examiner can normally be reached Monday-Friday, 9-5.
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/R.M.S./Examiner, Art Unit 1624
/JEFFREY H MURRAY/Supervisory Patent Examiner, Art Unit 1624