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 .
Priority
Acknowledgement is made that instant application 18/704,947, filed on 2024, Apr. 26, is a National Stage entry of PCT/CN2023/094722, filed on 2023, May 17, which claims foreign priority to 202210692359.4, filed on 2022, Jun. 17.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 2024, Oct. 23 is/are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure state is being considered by the examiner.
Use Claims
35 U.S.C. 101 reads as follows:
Whoever invents or discovers any new and useful process, machine, manufacture, or composition of matter, or any new and useful improvement thereof, may obtain a patent therefor, subject to the conditions and requirements of this title.
Claims 12-15 are rejected under 35 U.S.C. 101 because the claimed invention is directed to non-statutory subject matter. The claim(s) does/do not fall within at least one of the four categories of patent eligible subject matter because one cannot claim a new use per se, because it is not among the categories of patentable inventions as specified in 35 U.S.C. § 101 (process, machine, manufacture, or composition of matter), see In re Moreton, 288 F.2d 708, 709, 129 USPQ 227, 228 (CCPA 1961).
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 12-15 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.
The claims are directed to the use compounds according to any one of claims 1-10 for the preparation of an organic luminescent material, wherein the organic luminescent material is a TADF type organic luminescent material, wherein the organic luminescent material is a guest material or a sensitizing material of a luminescent layer, and for the preparation of an organic electroluminescent device. Reciting a use absent any active, positive steps delimiting how the use is practiced is indefinite (see Ex parte Erlich, 3 USPQ2d 1011 (Bd. Pat. App. & Inter. 1986)). Accordingly, one of ordinary skill in the art at the time of the effective filing date of the current invention would not have been apprised of the metes and bounds of the subject matter set forth in claims 12-15.
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, 3-4 and 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 and 8, substituents R1, R2, and R3 are claimed to each independently represent 1 or more substituents. However, the claimed Markush is drawn to discretely one substituent for each R1, R2, and R3 instead of clearly indicating the possibility of representing multiple substituents (e.g., (R1)n where n is 1, 2, or 3). This renders the scope of the claim ambiguous and open to multiple interpretations.
Regarding claims 3-4 the scope of the claims is unclear for the reasons stated above for R6 to R15, R18 to R19, and R22 to R25.
Claim Rejections - 35 USC § 103
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 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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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(s) 1-10, and 16-17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Koo, et al. (hereafter, Koo. WO 2018/186670 A1; published 2018, Nov. 10) in view of Liu, et al. (hereafter, Liu. CN 112341343 A; published 2021, Feb. 09).
Claim 1 recites a compound of Formula 1 (Table 1, left) featuring a triaryl borane group fused to a spirocyclicpentaphenanthrene with an electron-rich appendage for use as a thermally activated delayed fluorescent material in an electroluminescent device.
Table 1. Instantly claimed genus compared to the genus and species of Koo
Instant Formula 1
Koo, Formula 8
Koo, Compound 1
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245
277
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252
294
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Koo teaches a class of compounds represented by Formula 8 (page 15, paragraph 128) (inverted to show structural overlap with instant Formula 1). as organic material layer of an organic light emitting device, wherein a spirocyclic fluorenyl, xanthenyl, or thioxanthenyl group is fused with a triaryl boron system (Table 1, center). Specifically, Koo teaches compound 1 (Table 1, right) (inverted to show structural overlap with instant Formula 1), which is encompassed by Formula 8 when W = single bond, Q1 = NR, and both R and Rb is unsubstituted aryl (page 17, paragraphs 138-141). Compound 1 additionally on instant claim 1 when X = Y = NR4 and R4 = unsubstituted C6 aryl. While Koo does not teach any species comprising an asymmetric fluorenyl group, it is taught that the (R1)n substituent of formula 8 is independently selected from a group comprising hydrogen or non-converted heteroarylamine groups (page 4, paragraph 39). Koo further teaches that excitons generated by e.g., compound 1 are prevented from being destroyed due to the spiroaryl, xanthene, or thioxanthin structures with many electrons (page 5, paragraphs 49-50). Therefore, one with ordinary skill in the art would have found it prima facie obvious to further increase the electron density of the spirocyclic moiety by incorporating e.g., heteroarylamine groups.
The difference between the teaching of Koo and the instant application is that Koo fails to teach a spirocyclicpentaphenanthrene group fused to the triaryl boron system and further fails to teach a specific asymmetric electron-rich heteroarylamine substituent on the spiro group. However, these are rendered obvious in view of Liu.
Liu teaches electroluminescent organic compounds, whose material is used to improve the performance of electronic devices (title, abstract). Specifically, Liu teaches a class of spirocyclicpentaphenanthrene with electron-rich appendages fused to an adamantyl group, e.g., compound 3 (
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, page 8, row 1). These compounds overlap with the presently claimed genus when L is a linking group selected from a group comprising a direct linking bond; and D is an electron-rich heterocyclyl group with hole transport ability, selected from a group comprising diphenylamine, wherein each phenyl is independently unsubstituted, or substituted from a group comprising substituted or unsubstituted C6-C30 aryl.
One of ordinary skill in the art would be motivated to combine the teachings of Koo with the teachings of Liu because Koo notes the importance of the spirocyclic fluorenyl, xanthenyl, or thioxanthenyl groups as being electron-rich functional groups that aid in stabilizing the adjacent boronic heterocyclic system (page 4, paragraph 43). Koo further teaches that excitons generated by e.g., compound 1 are prevented from being destroyed due to the spiroaryl, xanthene, or thioxanthin structures with many electrons (page 5, paragraphs 49-50). Therefore, a reasonable expectation exists to further stabilize the triaryl boron group and excitons thereof by fusing said boron group with the even more electron-rich heteroarylamine-substituted spirocyclicpentaphenanthrene moiety of Liu. Additionally, both the triaryl boron group of Koo and adamantyl group of Liu impart similar characteristics to the electroluminescent functionality. For example, Liu teaches the adamantane-2-base has a large steric hindrance effect through which the angle and degree of conjugation between the branches of the tertiary amine can be adjusted, thereby adjusting the HOMO value of the organic compound so that the HOMO value is better matched with adjacent layers. Which can effectively reduce the driving voltage of the organic electroluminescent device or increase the open-circuit voltage of the photoelectric conversion device (page 60, paragraph 140). There is a reasonable expectation of success that the large triaryl boron system would impart comparable steric hinderance on the spirocyclicpentaphenanthrene and thereby similarly alter the degree of conjugation with the electron-donating amine.
Furthermore, the synthetic pathway for both aforementioned species allows for ease of combination. For example, Koo teaches lithium halogen exchange of the aryl bromide for addition to the benzyl ketone (page 30, paragraph 244)
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157
548
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Followed by acid-catalyzed cyclization (page 31, paragraph 248)
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224
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And lastly, incorporation of the central boron atom (page 31, paragraph 252).
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.
It would have been obvious for a person of ordinary skill in the art to utilize this synthetic method to incorporate the substituted spirocyclicpentaphenanthrene moiety of Liu, because Liu teaches a similar ketone addition (page 64, paragraph 176)
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Followed by acid-catalyzed cyclization (page 65, paragraph 813)
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111
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And Buchwald-Hartwig coupling (page 66, paragraph 189),
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to arrive at a similar spirocyclic core.
Accordingly, one of ordinary skill in the art would have found it prima facie obvious to combine the teachings of Liu and Koo to arrive at a compound that overlaps with instant claims 1-2 and 6-9.
Regarding claims 3, 5 and 10, Liu teaches Compound 64:
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(Page 41, line 8). When combined with Compound 15 as taught by Koo (
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) (page 20, paragraph 179), a skilled artisan would arrive at a compound that overlaps with Compound 6 (
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) of instant claim 10. The difference between the compound arrived at by the combined teachings of Liu and Koo and the instantly claimed Compound 6 is the use of an N-phenyl-d5 substituent, whereas instant claims 3, 5 and 10 are directed to the use of hydrogen in this position. As stated by MPEP 2144.09:
A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979).
Thus, Compound 6 is deemed to not be sufficiently novel over Liu in view of Koo. The burden is shifted to Applicants to prove that the recited subject matter possesses unexpected properties or features over the prior art.
Regarding claim 4, Liu teaches compound 6, inter alia (
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) (page 8, row 2). The instant specification discloses that the term “5-membered” when preceding a ring group refers to the number of ring atoms contained in a ring group (page 6, paragraph 2). As heteroatoms are not excluded from this definition, Liu’s compound 6 reads on the instant claim when R7 is bonded with an adjacent group to form a 5-membered ring. Using the above argument, it would be prima facie obvious to apply KSR prong (B) to substitute the adamantane portion of 6 above with the boron portion to arrive at the limitations of claim 4.
Regarding claim 16, Liu teaches an electronic device comprising an organic electroluminescent layer (Fig 2). The organic electroluminescent material is comprised of a disclosed organic compound (abstract).
Regarding claim 17, Liu teaches that the electronic device may be a display device (page 61, paragraph 149).
Conclusion
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/P.A./Examiner, Art Unit 1621
/CLINTON A BROOKS/Supervisory Patent Examiner, Art Unit 1621
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