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 Claims
Pursuant to the amendment, filed on May 29, 2024, claims 3, 6, 8, 10-15, and 18 have been amended.
Claims 1-19 are pending
Priority
This application, filed on May 29, 2024, is a National Stage entry from International Application No. PCT/JP2023/000674, January 12, 2023, which claims priority under 35 U.S.C. 119 or 365 to the benefit of Japanese Application No. JP2022-007814, filed on January 21, 2022. The certified copy of the foreign application has been received.
Information Disclosure Statement
The information disclosure statement (IDS) filed on May 29, 2024 has been acknowledged and received.
Specification Objections
Applicant is reminded of the proper content of an abstract of the disclosure.
A patent abstract is a concise statement of the technical disclosure of the patent and should include that which is new in the art to which the invention pertains. The abstract should not refer to purported merits or speculative applications of the invention and should not compare the invention with the prior art.
If the patent is of a basic nature, the entire technical disclosure may be new in the art, and the abstract should be directed to the entire disclosure. If the patent is in the nature of an improvement in an old apparatus, process, product, or composition, the abstract should include the technical disclosure of the improvement. The abstract should also mention by way of example any preferred modifications or alternatives.
The abstract should be in narrative form and generally limited to a single paragraph within the range of 50 to 150 words in length.
The instant abstract exceeds the maximum required word length. See MPEP § 608.01(b) for guidelines for the preparation of patent abstracts.
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 1-5 and 10-15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Doba et al., Nature Catalysis, VOL 4, July 2021, 631–638 (“Doba”).
Claim 1 recites a material for a photoelectric conversion device for imaging, the material comprising a thiophene derivative represented by the following general formula (1):
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, wherein A and B each independently represent hydrogen, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms, or a substituted or unsubstituted linked aromatic
group in which two to four of these aromatic groups are linked, and at least one of A or B has a
condensed-ring structure having 12 or more carbon atoms represented by the following general
formula (2) or (3); L1, L2, L3, L4, L5, and L6 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms;
T represents a substituted or unsubstituted thiophene ring; "a" represents the number of repetition and represents an integer of 1 to 4; “m”, “o”, “p”, “q”, “r”, and “s” represent the number of linkage and each independently represent an integer of 0 or 1; and "n" and "t" represent the number of substitution and each independently represent 1 or 2,
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, wherein “*” represents a bonding position at which the formula (2) or (3) is substituted, the condensed-ring structures represented by the formulae (2) and (3) optionally have a substituent, and the formula (2) is optionally condensed with the substituent to form a condensed ring;
X represents N-Ra, O, S, or C-(Rb)2, Ra and Rb each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms, or a substituted or unsubstituted linked aromatic group in which two to four of these aromatic groups are linked, and Ra and Rb are optionally bonded to the formula (2) to form a condensed ring.
Claim 2 recites the same general formula (1), but specifies the thiophene ring as T with substituents R1 and R2, and wherein A, B, L1 to L6, “a” and “n” to “t” are defined as in claim 1, and R1 and R2 each independently represent hydrogen, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 18 carbon atoms.
Claim 3 recites at least one of A or B is represented by general formula (2), and X in formula (2) represents N-Ra or O.
Claim 4 recites at least one of A or B of general formula (1) is represented by the following general formula (4):
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, wherein “*” is as defined for the formula (2); the formula (4) optionally has a substituent; Ra is as defined for the formula (2), and optionally further forms a condensed ring with the formula (4) itself or the substituent in the formula (4); and the formula (4) is optionally condensed with the substituent in the formula ( 4) itself to form a condensed ring.
Claim 5 recites both A and B of general formula (1) are represented by general formula (4).
Claim 6 recites at least one of A or B is represented by the following general formula (5):
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, wherein “*” is as defined for formula (3); and the formula (5) optionally has a substituent.
Claim 7 in which the general formula (1), both A and B are represented by general formula (5).
Claim 10 recites “a” of general formula (1) is 1 to 3 and “p” and “q” are 0.
Claims 11 recites wherein the highest occupied molecular orbital (HOMO) obtained by structural optimization calculation with a density functional calculation B3LYP/6-31G(d) is -4.5 eV.
Claim 12 recites wherein the lowest unoccupied molecular orbital (LUMO) obtained by structural optimization calculation with a density functional calculation B3LYP/6-31G(d) is -2.5 eV.
Claim 13 recites the material for a photoelectric conversion device has a hole mobility of 1x10-6 cm2/Vs or more.
Claim 14 recites the material for a photoelectric conversion device is amorphous.
Claim 15 recites the material is used as a hole transport material of a photoelectric conversion device for imaging.
Doba teaches compounds 19 and 20, which are shown below:
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.
Compound 19 reads on general formula (1), wherein T is thiophene and “a” is 2; L3 and L4 are phenyl rings in which “p” and “q” are 1; “m”, “o”, “r”, and “s” are 0; and A and B are represented by formula (2) wherein X is N-Ra, and Ra is a substituted phenyl (p. 635, Fig. 4). Accordingly, compound 19 anticipates claims 1-3.
Compound 20 reads on general formula (1), wherein T is a thiophene and “a” is 2; “m”, “o”, “p” “q” “r”, and “s” are 0; and A and B are both represented by formula (4) wherein X is N-Ra, and Ra is an unsubstituted phenyl (p. 635, Fig. 4). Accordingly, compound 20 anticipates claims 1-5 and 10.
Regarding claims 11-14, the limitations presented do not provide further structural limitations to the material for a photoelectronic device. Compounds 19 and 20 are compounds within the Markush formula (1) and would necessarily possess the HOMO and LUMO energy levels, the hole mobility, and the amorphous shape instantly recited because members of the Markush formula (1) would be expected to share similar properties.
Regarding claim 15, the intended use of the material being used as a hole transport material of photoelectric device for imaging does not provide further structural limitations to the composition recited and therefore is not given much patentable weight. Thus, the compounds taught by Doba anticipate the instant claim.
Claims 1-3, 6-7, and 10-15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by KR20120129733 (“Kim”).
Kim teaches compound 137 (same as compound 15 in the instant specification (p. 24) as shown below:
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,
wherein T is a thiophene and “a” is 2; L1 through L6 are absent in which “m”, “o”, “p”, “q”, “r”, and “s” are 0; and A and B are both represented by formula (5) (p. 23). Accordingly, compound 137 anticipates claims 1-3, 6-7, and 10.
Regarding claims 11-14, the limitations presented do not provide further structural limitations to the material for a photoelectronic device. Compound 137 is within the Markush formula (1) and would necessarily possess the HOMO and LUMO energy levels, the hole mobility, and the amorphous shape instantly recited because members of the Markush formula (1) would be expected to share similar properties.
Regarding claim 15, the intended use of the material being used as a hole transport material of photoelectric device for imaging, does not provide further structural limitations to the composition recited and therefore is not given much patentable weight. Thus, the compound taught by Kim anticipates the instant claim.
Claims 1-5 and 11-15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by WO2009104733 (Cite No. 5 in IDS – citations are to the translated version provided) (“Takata”).
Takata teaches compound 5 (same as compound 21 in the instant specification (p. 25)), which is shown below:
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,
wherein T is a thiophene and “a” is 1; L3 and L4 are unsubstituted phenyl rings in which “p” and “q” are 1, and “m”, “o”, “r”, and “s” are 0; and A and B are both represented by formula (4) wherein X is N-Ra, and Ra is an unsubstituted phenyl (p. 7, Table 1). Accordingly, compound 5 anticipates claims 1-5.
Regarding claims 11-14, the limitations presented do not provide further structural limitations to the material for a photoelectronic device. Compound 5 is within the Markush formula (1) and would necessarily possess the HOMO and LUMO energy levels, the hole mobility, and the amorphous shape instantly recited because members of the Markush formula (1) would be expected to share similar properties.
Regarding claim 15, the intended use of the material being used as a hole transport material of photoelectric device for imaging, does not provide further structural limitations to the composition recited and therefore is not given much patentable weight. Thus, the compound taught by Takata anticipates the instant claim.
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.
Claims 16-19 are rejected under 35 U.S.C. 103 as being unpatentable over Takata in view of JP2018002690 (Cite No. 8 in IDS) (“Iwawaki”).
Takata teaches a material for an organic electroluminescence (EL) element and an organic electroluminescence element that improves the performance of the EL by low voltage driving, long life, and heat resistance (¶[0005]). Takata also teaches compound 5, in which T is a thiophene and “a” is 1; L3 and L4 are unsubstituted phenyl rings in which “p” and “q” are 1, and “m”, “o”, “r”, and “s” are 0; and A and B are both represented by formula (4) wherein X is N-Ra, and Ra is an unsubstituted phenyl (p. 7, Table 1). The compounds have a high hole transport effect and is formed between an anode and a cathode (¶¶ [0058], [0065], [0067]). The compounds have phosphorescent light-emitting properties when transitioning from the excited triplet state to a ground state (¶[0064]).
Takata does not teach a photoelectric conversion device comprising a photoelectric conversion layer and an electron blocking layer between two electrodes, wherein at least one layer of the photoelectric conversion layer and the electron blocking layer contains a material for a photoelectronic conversion represented by general formula (1).
Iwawaki teaches organic compounds having a deep HOMO, high photoelectric conversion efficiency, and a wide absorption wavelength range, and an organic photoelectric conversion element having the same (¶[0012]). Figure 1 shows an example of an organic photoelectric conversion element in which the upper side is the light incident side; the organic photoelectric conversion element (10) has an anode (5), a cathode (4), and an organic photoelectric conversion layer (1) disposed between the anode and the cathode. The second organic compound layer (2) is between the organic photoelectric conversion layer and the cathode, in which the second organic compound layer is also called an electron blocking layer (¶[0101]). The photoelectric conversion layer contains an organic compound that can absorb visible light to generate excitons, the function of generating charges, i.e., holes and electrons from the excitons, and the function transporting them (¶[0127]). Iwawaki also teaches that the organic photoelectric conversion element having high hole mobility is preferred because of its high response speed (¶[0107]). The electron blocking layer may have a role of transporting holes generated in the organic photoelectric conversion layer to the cathode (¶[0110]).
Takata and Iwawaki are considered analogous art to the claimed invention because they are in the same field of utilizing thiophene based compounds as organic semiconductors. Therefore, it would have been prima facie obvious to a person having ordinary skill in the art (PHOSITA) to combine the prior art elements to arrive at the device instantly claimed. It would have been prima facie obvious to use compound 5 which has a high hole transport effect, based on the teachings of Takata, and incorporate the compound into the photoelectric conversion and electron blocking layer, which are between an anode and a cathode (two electrodes), based on the teachings of Iwawaki to arrive at the device instantly claimed. The teachings of Takata suggest the compounds, like compound 5, have a high hole transport effect and provides motivation for a PHOSITA to use such compounds in the photoelectric conversion device taught by Iwawaki, because Iwawaki teaches it is preferred that the photoelectric conversion device has an electron blocking layer having high hole mobility. In the same respect, based on the teachings of Iwawaki, a PHOSITA would have been motivated to use the compound in Takata in the photoelectric conversion layer taught by Iwawaki, because Iwawaki teaches the photoelectric conversion layer includes a compound that can generate charges through holes and electrons. Accordingly, claims 16-18 are prima facie obvious.
Regarding claim 19, Iwawaki teaches that the photoelectric conversion layer contains a second material other than the organic compound like a fullerene derivative (¶¶ [0129]-[0130]). Iwawaki teaches that fullerene derivatives are preferred and are particularly excellent in the function of generating charges from excitons and the function of transporting them.’
Allowable Subject Matter
Claims 8-9 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. Close prior art to the instant claims is Takata which discloses compounds 107 and 108 as shown below:
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, wherein L3 and L4 are represented by formula (6) and more specifically formula (6a) in which “p” and “q” are 0. The difference between the compounds of Takata and the claimed invention are the substituents A or B. Compound 107 of Takata has substituents A and B similar to general formula (3) but has 3 fused phenyl rings as opposed to 4 as in instant claim 1. Compound 108 of Takata has substituents A and B are similar to general formula (3) but has 3 fused phenyl rings wherein one of the fused phenyl rings is further substituted with a phenyl ring. There is no teaching, suggestion, or motivation to prepare the compounds with A and B as triphenylene substituents.
Conclusion
Claims 1-7 and 10-19 are rejected.
Claims 8-9 are objected to.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SAHIL CHANDER AGGARWAL whose telephone number is (571)272-7755. The examiner can normally be reached 7am-5pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Adam C Milligan can be reached at (571) 270-7674. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SAHIL CHANDER AGGARWAL/Examiner, Art Unit 1623
/CLINTON A BROOKS/Supervisory Patent Examiner, Art Unit 1621
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