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
The preliminary amendments filed on 07/31/2023 and 02/06/2024 have been entered. Claims 2-15, 17 and 20-22 have been amended. Thus claims 1-22 are currently pending and are under examination.
Specification
The disclosure is objected to because of the following informalities: the attachment/bonding point in the structures of the formulas (II), (III), (IV), (IIa), (IIIa) and (IVa) to the compound of formula (I) has not been indicated.
Appropriate correction is required.
Claim Objections
Claim 5 is objected to because of the following informalities: the claim recites an improper Markush language “selected of the formula (VI)”. A proper Markush language must recite a selection of alternatives as discussed in MPEP § 2173.05(h), whereas the instant claim recites only formula (VI). Appropriate correction is required.
Claim 19 is objected to because of the following informalities: the claim does not end with a period sign “.”.
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 1-4 and 6-22 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 and 15, the formulas (II), (III), (IV), (IIa), (IIIa) and (IVa) of A1, A2 and A3 render the claim vague and indefinite as the attachment/bonding point to the compound of formula (I) has not been indicated in the structures of formulas (II), (III), (IV), (IIa), (IIIa) and (IVa).
Claims 2-4 and 6-22 are also rendered indefinite for failing to obviate the vague language of claim 1.
For purpose of applying art, the bonding point of the formulas (II), (III), (IV), (IIa), (IIIa) and (IVa) are interpreted to be at the methylene group bridging the Ar and R/CN groups (see below as an example):
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Note: If the indefinite language of claims 1 and 15 is obviated by indicating the bonding point as above, the formula (VI) of claim 5 would not further limit claim 1 and would invoke the 112(d) rejection.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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 1-6 and 8-9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Enomoto (Enomoto, T. et al. “Synthesis, Structure, and Properties of Hexaaryl[3]radialenes” Bull. Chem. Soc. Jpn, 73, 2000, 2109–2114; cited in IDS 07/31/2023).
Regarding claims 1-2 and 5-6, Enomoto teaches on pg. 2110 compound 1f that reads on the instant compound of formula (I):
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195
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113
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In the above compound:
Ar1, Ar2 and Ar3 = C6 aryl groups substituted by NO2,
R’, R’’ and R’’’ = substituted aryl groups, and
wherein the compound contains NO2 groups.
Regarding claims 3 and 9, in the corresponding Ar1, Ar2 and Ar3:
X1/6/11 is CR1/6/11,
X2/7/12 is CR2/7/12;
X3/8/13 is CR3/8/13;
X4/9/14 is CR4/9/14;
X5/10/15 is CR5/10/15; wherein one of R1/6/11, R2/7/12, R3/8/13, R4/9/14, and R5/10/15 is NO2 and the other R1/6/11, R2/7/12, R3/8/13, R4/9/14, and R5/10/15 are H
Regarding claim 4, R3 (X of the above formula) is NO2.
Regarding claim 8, Ar2 and Ar3 in 1f are identical.
Allowable Subject Matter
The subject matter of claims 7 and 10-22 is free of prior art reference. The closest prior art reference, Enomoto (Enomoto, T. et al. “Synthesis, Structure, and Properties of Hexaaryl[3]radialenes” Bull. Chem. Soc. Jpn, 73, 2000, 2109–2114; cited in IDS 07/31/2023), and its teachings have been set forth above.
Regarding claim 7, Ar2 and Ar3 in compound 1f of Enomoto contain hydrogen as substituents but the reference fails to teach or suggest that at least one of Ar2 and Ar3 does not contain hydrogen.
Regarding claim 10, compound 1f of Enomoto is the same compound of formula (I) that the instant claim is excluding.
Regarding claim 11-14, the corresponding substituents of R’, R’’ and R’’’ in compound 1f of Enomoto are C6 aryl groups with NO2 groups, but fail to teach or suggest R’, R’’ and R’’’ as defined by claims 11-14.
Regarding claim 15, while compound 1f of the reference is the same as the corresponding Ar1, Ar2 and Ar3 of formulas (IIa), (IIIa) and (IVa), R’, R’’ and R’’’ are not CN as instantly claimed.
Regarding claim 16, compound 1f of Enomoto has 6 NO2 groups, not four nitro groups as required by the claim.
Regarding claims 18-22, Enomoto teaches [3]Radialene (trimethylenecyclopropane) is the smallest member of [n]radialenes (all exo-methylenecycloalkanes) and has received considerable attention from both theoretical
and experimental points of view owing to its unique structure and electronic properties, but fails to teach or suggest an organic semiconductor layer comprising compound 1f.
Furthermore, Patent application publication number US20170373251A1 (US’251) teaches [3]-radialene compound of formula (I):
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295
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40
446
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Some of US’251 further teaches a process for preparation of an electrically doped semiconducting material comprising a [3]-radialene p-dopant or for preparation of an electronic device containing a layer comprising a [3]-radialene p-dopant.
However, the definition of A1 and A2 does not require the compound of formula (I) in US’251 to contain at least one NO2 group as instantly claimed or taught by Enomoto. Furthermore, each of A1 and A2 of US’251 include only one aryl- or heteroaryl-substituted cyanomethylidene groups, whereas in compound 1f of Enomoto, they contain two aryl groups.
As such, one of ordinary skilled in the art would not have had a motivation to combine Enomoto and US’251 to arrive at the instant claims 7 and 10-22.
Conclusion
Claims 1-22 are rejected and no claims are allowed.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692