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 .
Response to Amendment
In the responses filed 09/29/2025 and 01/08/2026, the claims were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 112(b) of claims 23-42 as failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention, and the rejections under 35 U.S.C. 103 of claims 23-29 and 32-42 as being unpatentable over Li et al. (US 2015/0194616 A1), claim 30 as being unpatentable over Li above and further in view of Lin et al. (US 2015/0194615 A1), and claim 31 as being unpatentable over Li above, and further in view of Yutaka et al. (Yutaka T.; Mori, I.; Kurihara, M.; Mizutani, J; Tamai, N.; Kawai, T.; Irie, M.; Nishihara, H.; 2002, Photoluminescence Switching of Azobenzene-Conjugated Pt(II) Terpyridine Complexes by Trans-Cis Photoisomerization, Inorg. Chem., 41, 7143-7150) are withdrawn by the Office.
Claims 23, 27-30, 32, 35, 37, 38, and 41 have been amended.
Claims 43 and 44 have been added.
Claims 31 and 34 have been canceled.
Claims 23-30, 32-33, and 35-44 are pending in the application.
Response to Arguments
With respect to claim 37, the objection to claim 37 is maintained by the Office for the reason discussed below.
Applicant's arguments with respect to the rejections over 35 U.S.C. 112(a) have been fully considered but they are not persuasive. Applicant’s amendments do not overcome the rejections for the reasons discussed below.
Claim Objections
Claim 37 is objected to because of the following informalities:
The claim contains the same typographical error, now in line 2. Please see below:
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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 23-30, 32-33, and 35-44 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Independent claims 23, 38, and 41 require a planar platinum or palladium metal organometallic compound with four ring systems, A, B, C, and D, and one of the rings is an imidazole-derived carbene with a metal-carbene bond, and one nitrogen atom of the imidazole-carbene has a substituent, R*, wherein at least one non-hydrogen atom of R* falls within a distal circle of a cylinder extending perpendicular to a first plane, and the first plane is defined by the base of the cylinder, which comprises the metal nucleus, and its four coordinating atoms in their planar geometry. The instant description provides no embodiments of a compound that meets this requirement. The instant specification only includes one embodiment wherein one of rings A, B, C, and D is an imidazole-derived carbene, Compound 45 (page 27), and in this compound, the substituent R* is not on the nitrogen atom of the imidazole. Further, while more general formulae are present, such as the formulae comprising an imidazole-derived carbene which are pictured in paragraph [0063] of the specification, the specification only defines one of RA, RB, RC, and RD as comprising substituent R*, and RE, which is the substituent on the nitrogen atom of the imidazole-derived carbene, is not defined anywhere in the original disclosure. For these reasons, the limitation that the substituent R* is bonded to a nitrogen atom of the imidazole-derived carbene represents new matter.
Claims 24-30, 32-33, 35-40, and 42-44 are rejected by virtue of dependency.
Claims 23-30, 32-33, and 35-44 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 some compounds bearing substituent R* which would predictably have one non-hydrogen atom fall within a distal circle of a cylinder extending perpendicular to the first plane, does not reasonably provide enablement for any compound which would have at least one non-hydrogen atom in substituent R* fall within a distal circle of a cylinder extending perpendicular to the first plane. 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 and/or use the invention commensurate in scope with these claims.
Independent claims 23, 38, and 41 require a platinum or palladium metal organometallic compound comprising a tetradentate ligand in a square planar configuration, and the tetradentate ligand comprises rings A, B, C, and D and four coordinating atoms, Z1, Z2, Z3, and Z4, wherein one of rings A, B, C, and D is an imidazole-derived carbene, Z1, Z2, Z3, and Z4 define a first plane through the metal center, and one nitrogen atom of the imidazole-derived carbene comprises a substituent R*, and at least one non-hydrogen atom of substituent R* falls within a distal circle of a cylinder formed perpendicular to the first plane, and the height, h, of the cylinder is 3.3 Å – 4.8 Å.. However, the present application does not provide the person having ordinary skill in the art with a sufficient disclosure to effectuate these limitations. For example, the present application does not disclose how to predict what kind of substituent R* would fall within the cylinder, particularly when bonded to the nitrogen atom of an imidazole-derived carbene, nor does the specification provide direction on how the full breadth of substituents R* can be reasonably formed. As such, predictably forming a compound which would meet these limitations is not enabled by the application, as originally filed. The factors set forth in In re Wands, 858 F.2d 731, 737 (Fed. Cir. 1988) are discussed below.
(A) The breadth of the claims
The present claims are directed to a platinum or palladium metal organometallic compound comprising a tetradentate ligand in a square planar configuration, and the tetradentate ligand comprises rings A, B, C, and D and four coordinating atoms, Z1, Z2, Z3, and Z4, wherein one of rings A, B, C, and D is an imidazole-derived carbene, Z1, Z2, Z3, and Z4 define a first plane through the metal center, and one nitrogen atom of the imidazole-derived carbene comprises a substituent R*, and at least one non-hydrogen atom of substituent R* falls within a distal circle of a cylinder formed perpendicular to the first plane, and the height, h, of the cylinder is 3.3 Å – 4.8 Å. The only structural limitations of substituent R* are that it is attached to a nitrogen atom of an imidazole-derived carbene, and it is composed of moieties selected from alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof. Since no limitations are present which would predictably result in at least one non-hydrogen atom of substituent R* falling within a distal cylinder formed perpendicular to the first plane, the claims cover a significantly broad range of possible substituent R* combinations that might possibly meet the requirements of the claim. Further, identifying a substituent R* which could reasonably be expected to fall within the claimed cylinder presents a serious burden.
(B) The nature of the invention
The invention relates to an organometallic compound which has a substituent R* which is able to reduce intermolecular interaction with dopant and host materials and prevent aggregation (paragraph 0047 of the specification). In the instant specification, Applicant asserts that “the dz2 orbital is perpendicular to the plane formed by the metal center and the coordinating atoms, which is prone to have strong metal-to-metal and metal-to-ligand interactions. Such interactions result in severe aggregation and reduce the OLED device efficiency… The R group falls in the facial position as defined in claim 1, which will reduce the intermolecular interaction with dopant and host materials to prevent aggregation, improve OLED efficiency, and maintain desired emissions” (paragraph 0047). Whether this statement is true or not is not at issue in this enablement analysis. Rather, this statement is provided in this section because it demonstrates that applicant is relying upon the claimed invention of an organometallic compound bearing a substituent that is made to lay facial to the plane of a planar tetradentate organometallic compound to support a theoretical genus of hundreds of thousands of possible compounds, while the working examples encompass only one data point, Compound 51 (page 62 of the instant specification), which was created using theoretical modeling software (Gaussian).
Also, no structure is given in the independent claim which would lead one of ordinary skill to suspect that the compounds in paragraph [0066], or that Compound 51 would achieve this structural relationship between the organometallic core and substituent R* because none of them have an imidazole-derived carbene with substituent R* on a nitrogen atom of the imidazole moiety. Furthermore, the one data point provided by Compound 51 does not provide enough support to suspect that any of the other compounds in the specification would have good agreement between experimental and calculated values or would occupy the claimed cylinder when in three-dimensional space.
(C) The state of the prior art
The claims appear to be drawn to an organometallic compound with an imidazole-derived carbene bearing a substituent on one nitrogen atom which has the configuration needed to circle around and protect one face of a metal complex with a planar d8 tetradentate configuration, i.e. platinum or palladium. Compounds with long and/or steric substituents were known as of the filing date of the claimed invention, as laid out in previous correspondence. However, the size of the genus made up of “alkyl, cycloalkyl, aryl, heteroaryl, and combinations thereof” is vast and there is no guidance given on ways to know or to predict whether any combination of the above organic moieties could be reasonably expected to fall within the claimed cylinder. Therefore, while such organometallics and such substituents were known, the specification does not reasonably enable a person having ordinary skill in the art with a method by which to identify a substituent R* which would occupy the claimed cylinder which is perpendicular to the claimed organometallic plane.
(D) The level of one of ordinary skill
Determining the theoretical dimensions of a static compound is known in the art. Software such as Gaussian makes calculation of molecular dimensions accessible to a person of ordinary skill in the art. However, Examiner’s position is that actual, experimental structures can differ significantly from structures theorized using software and applicant has not made a convincing show that there is good agreement between theoretical and experimental data. Molecules are not static, but rather move rapidly, rotating around single bonds, and bending out of plane. Thus, while these structures may be simple to draw in Gaussian, the process of experimentally determining which R* substituents protect one side of an organometallic core is long and burdensome, and determining which organic moiety or combination of moieties could be used to arrive an appropriate substituent R*, presents a serious experimental burden to one of ordinary skill in the art.
(E) The level of predictability in the art
The level of predictability in the art presented by Applicant is low for at least three reasons. The first reason is because Applicant has only presented theoretical data from Gaussian and it is unclear if these data agree with experimentally obtained data. The second reason is because data have only been presented for one compound, 51, which is not enough data to reliably predict whether the claimed genus all conform to the requirements of the independent claims. The third reason is because compound 51 does not have an imidazole-derived carbene, which is a feature required by the independent claims.
Finally, while applicant provides the identity of several sterically confining L groups in claim 36, and several bulky R groups in claim 37, which may reasonably convey the ability to achieve the claimed invention as set forth in the independent claim, the limitations of a dependent claim cannot be read into the independent claim.
(F) The amount of direction provided by the inventor
The amount of direction provided by Applicant is low because while Applicant’s Specification contains 51 example organometallic platinum compounds, the dimensions of only one of these organometallic compounds is given (compound 51). Also, it is unclear whether they would satisfy the claimed cylinder dimensions on the nitrogen atom of an imidazole-derived carbene as none of the compounds have an R* group substituted on the nitrogen atom of an imidazole-derived carbene. There is simply not enough direction given to select an R* group, out of all conceivable combinations of “alkyl, cycloalkyl, aryl, heteroaryl and combinations thereof” and substitute it on the nitrogen atom of an imidazole-derived carbene and reliably obtain a compound which would meet the requirements of the independent claims.
(G) The existence of working examples
There are no working examples in the instant specification. While applicant’s specification includes 51 example compounds, the dimensions of only one of these compounds is actually stated, and the compound for which dimensions are given does not meet the requirements of the amended independent claims. This makes it unclear what kind of compound and substituent R* would actually meet the requirements of the instant independent claims. Further, while applicant has stated that any of the compounds meet the claimed cylindrical volume, for the reasons discussed above, it is not clear whether any compound, other than compound 51, has a dimension analogous to instant h between 3.3 Å and 4.8 Å, and what combination of organic moieties would form a substituent R* which would meet these requirements when on the nitrogen atom of an imidazole-derived carbene.
(H) The quantity of experimentation needed to make or use the invention based on the content of the disclosure
The quantity of experimentation needed to make the claimed invention is high because, as outlined above, there is not enough direction provided to arrive at a substituent R* which could be reasonably expected to fall within the claimed cylinder when substituted on the nitrogen atom of an imidazole-derived carbene. Moreover, no guidance is given on structures for substituent R* which would reliably result in a compound which would meet the requirements of the instant claims. Similarly, as the dimension h of the vast majority of example compounds is not given, nor is an example of an imidazole-derived carbene with a substituent R* on a nitrogen atom given, it would require a significant amount of experimentation to make and/or use the invention based on the content of the disclosure.
As such, claims 23, 38, and 41 contain subject matter which was not described in the specification in such a way as to enable one skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention.
Claims 24-30, 32-33, 35, 39-40, and 42-44 are rejected by virtue of dependency.
Examiner would like to note that claims 36 and 37 have not been rejected as they resolve this enablement rejection.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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/RACHEL SIMBANA/Examiner, Art Unit 1786