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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 11/25/2025 has been entered.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 8 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 8 recites a broader range for the values of the integer n1 (0 to 3) than the scope of the claim 1 from which claim 8 depends (i.e. “n1 is 1 to 3”). Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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 1-3, 5-7 and 9-11 are rejected under 35 U.S.C. 103 as being unpatentable over Bae et al (WO 2021256871) (Bae).
In reference to claims 1-7 and 9-11, Bae teaches a compound of formula 1 as shown below (Bae Claim 1 [12])
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for example, wherein in the formula 1, L1 is a phenylene, A is a group of formula 2 wherein two X are N and the other X are bonded to Ar1 wherein the Ar1 are each phenyl groups, L2 is a phenylene and B is a group of formula 2 wherein each X is CR wherein R is a bond to L2, a hydrogen or bond to Ar1 that is a cyano group (Bae [14] to [26]) or, in other words, the compound C-2 as shown above except wherein the group L2 is a phenylene instead of a single bond.
Bae discloses the compound of formula 1 that encompasses the presently claimed compound, including wherein in the formula 1, L1 is a phenylene, A is a group of formula 2 wherein two X are N and the other X are bonded to Ar1 wherein the Ar1 are each phenyl groups, L2 is a phenylene and B is a group of formula 2 wherein each X is CR wherein R is a bond to L2, a hydrogen or a bond to Ar1 that is a cyano group. Each of the disclosed substituents from the substituent groups of Bae are considered functionally equivalent and their selection would lead to obvious variants of the compound of formula 1.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application, in the absence of unexpected results, to have selected these substituents among those disclosed for the compound of formula 1 to provide the compound described above, which is both disclosed by Bae and encompassed within the scope of the present claims and thereby arrive at the claimed invention.
For Claim 1: Reads on formula I wherein Y1 and Y2 are each CH, ring A is biphenylene, n1 is 1, L is phenylene, X1 to X3 is N, R1 and R2 are each phenyl.
For Claim 2: Reads on formula II.
For Claim 3: Reads on unsubstituted.
For Claim 5: Reads on phenylene.
For Claim 6: Reads on X1 to X3 are N.
For Claim 7: Reads on CH and n1 is 1.
For Claim 9: Reads on the first group.
For Claim 10: Reads on the first group.
For Claim 11: Reads on
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Claims 1-3, 5-6 and 8-11 are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al (US 20130001522) (Lee).
In reference to claims 1-3, 5-6 and 8-11, Lee teaches a compound of formula 2 as shown below
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for example, wherein in the formula 2, R10 is a group of formula 2a as shown above, p is 1 and Z1 is a cyano phenyl group (Lee [0067]), R4 is a substituted phenylene wherein the substituent is a group of formula 2d as shown above wherein Y1 to Y3 are each N, Z1 and Z2 are each phenyl and each other R# is hydrogen (Lee [0044] to [0051]).
Lee discloses the compound of formula 2 that encompasses the presently claimed compound, including wherein in the formula 2, R10 is a group of formula 2a as shown above, p is 1 and Z1 is a cyano phenyl group, R4 is a substituted phenylene wherein the substituent is a group of formula 2d as shown above wherein Y1 to Y3 are each N, Z1 and Z2 are each phenyl and each other R# is hydrogen. Each of the disclosed substituents from the substituent groups of Lee are considered functionally equivalent and their selection would lead to obvious variants of compound of formula 2.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the instant application, in the absence of unexpected results, to have selected these substituents among those disclosed for the compound of formula 2 to provide the compound described above, which is both disclosed by Lee and encompassed within the scope of the present claims and thereby arrive at the claimed invention.
For Claim 1: Reads on formula I wherein Y1 is CH and Y2 is N, ring A is biphenylene, n1 is 1, L is phenylene, X1 to X3 is N, R1 and R2 are each phenyl.
For Claim 2: Reads on formula II.
For Claim 3: Reads on unsubstituted.
For Claim 5: Reads on phenylene.
For Claim 6: Reads on X1 to X3 are N.
For Claim 8: Reads on Y2 is N, Y1 is CH and n1 is 1.
For Claim 9: Reads on the first group.
For Claim 10: Reads on the first group.
For Claim 11: Reads on
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Response to Arguments
Applicant's arguments filed 10/23/2025 have been fully considered but they are not persuasive.
Applicant argues that the claims as amended are different from those taught by the prior art and that the materials disclosed by Bae or by Lee. This argument is not convincing. As pointed to herein above, Both Bae and Lee references teach the claimed materials as amended.
Applicant argues that the performance of products in the field of organic compounds cannot be directly inferred from their structures and sometimes compounds with similar structures have significantly different properties. Applicant points to Table 1 as evidence to this effect showing that the claimed materials have deep LUMO and HOMO energy levels.
This argument has been fully considered but not found convincing for at least the following reasons. While Applicant is not incorrect that in some fields, the performance of organic compounds cannot be directly inferred from their structure, such is not generally the case in the field of organic electronics. While biological applications of organic compounds such as pharmaceutical or agriculture applications render relationship between structure and activity complex, this is due to the nature of the application and not due to the organic compounds per se. Organic electronic applications are man-made machines wherein all variables are controlled (layer composition, thickness, voltage application etc.) whereas biological applications require the introduction of an organic material into a complex system with an abundance of unknown interactions. Comparison between these fields is not reasonable with respect to the predictability of the functional properties of a material. Indeed, most of the critical features of a material for an organic electronic device are highly predictable using computational methods such as DFT based calculations. These models allow for reliable prediction of the HOMO, LUMO, singlet and triplet energies of materials. In fact, Applicant’s Table 1 provides exactly such predictions and not data obtained from the preparation and testing of such compounds. Essentially, Applicant has argued that HOMO and LUMO results are not predictable and as evidence points to the predictions themselves. If Applicant intends to assert that these predictions in Table 1 are not accurate, Applicant should point to experimental evidence that these values are incorrect for the claimed materials. Otherwise, Applicant has merely demonstrated what HOMO and LUMO values would be expected for the materials and not demonstrated an unexpected property.
Applicant further argues that in order to predict the performance of compounds in the field of organic electronic devices using computation methods, the structure of the compound must first be provided and that the teachings of the prior art do not allow a skilled artisan to know the structure of such materials. This argument has been fully considered but not found convincing. The prior art of record teaches these structures as set forth above herein. Further these arguments do nothing to remedy the fact that such data presented in Table 1 of the instant specification are not unexpected results but, by contrast, predictions of what properties would be expected for such materials. This becomes immediately apparent if one tries to analyze such results for the requirements of “unexpected results” consistent with MPEP 716.02 which requires that such evidence be of both statistical and practical significance. It is not possible to provide an analysis of statistical significance of such predictions as no measurement has been performed for statistical analysis. Further, such predictions do not have practical significance on their own as differences in predicted properties do not have clear practical implications. For example, Applicant points to the possibility that “relatively deep LUMO energy levels” can reduce a potential barrier of electron transport to reduce voltage. However, the key is that such an improvement is contingent not upon the LUMO energy per se but the relative LUMO energy of a material in comparison to the LUMO and HOMO energy of other materials in a device. Having too deep of a LUMO energy would potentially have negative effects on the same property if the LUMO energy of the host material of an adjacent layer is too shallow. Further, if one assumes that such data could be considered results for the purposes of demonstrating unexpected results the fact that some materials of a genus, such as those genera disclosed by Bae and Lee, have different properties than other materials of the genus is not unexpected. Changing the structure of a material would be expected to result in different HOMO and LUMO values in much the same way as it would be expected to result in different NMR spectra, melting points etc. The fact that the values are different is not on its own unexpected. Taken together, the data presented does not qualify as a showing of unexpected results.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Sean M DeGuire whose telephone number is (571)270-1027. The examiner can normally be reached Monday to Friday, 7:00 AM - 5:00 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer A. Boyd can be reached at (571) 272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Sean M DeGuire/Primary Examiner, Art Unit 1786