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 .
Claim Status
Claims 1-20 are pending.
No claims have been amended.
No claims have been canceled.
Thus, claims 1-20 represent all claims currently under consideration.
Priority
Domestic Priority data as claimed by Applicant:
This application is a CON of PCT/CN2022/123697 (10/04/2022)
Foreign Applications:
CHINA 202111320218.1 (11/09/2021)
CHINA 202211173070.8 (09/26/2022)
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
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 1-10 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Huang et al. (CN110734388A; published 01-31-2020; IDS of 05-15-2024; Original Document and English language machine translation obtained from Espacenet on 10-06-2026).
Regarding claim 1, Huang discloses hole injection compounds and applications thereof including organic electroluminescent devices such as OLEDs. Of particular note, Huang discloses a preferred hole injection compound of the following structure:
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This compound anticipates the genus of formula (1) of claim 1, the genus of claim 2, and the genus of formula (2) of claim 3 when Z is a single bond, X1-X6 are CN, and Z1-Z3 are O.
Further regarding claims 1-3 and claims 4-10, Huang discloses a preferred hole injection compound of the following structure (Title; Abstract; 0026; Original Document as filed in IDS; 0028, 0070, and 0079; claims 1 and 9-10; English language machine translation):
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This compound anticipates the genus of formula (1) of claim 1, the genus of claim 2, and the genus of formula (2) of claim 3 when Z is a single bond, X1-X6 are CN, and Z1-Z3 are CR2R3, wherein R2 is CN and R3 is substituted C6 aryl. Furthermore, this compound also anticipates the genus of claims 4-10 because all of Z1-Z3 are CR2R3, both R2 and R3 are electron-withdrawing groups, R2-R3 are independently selected from CN and substituted C6 aryl wherein the substituents are F and CN (i.e., a C6-aryl containing groups with electron-withdrawing properties as recited in claim 9), and X1-X6 are CN.
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 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Huang et al. (CN110734388A; published 01-31-2020; IDS of 05-15-2024; Original Document and English language machine translation obtained from Espacenet on 10-06-2026), as evidenced by Shahnawaz et al. (“Hole-transporting materials for organic light-emitting diodes: an overview”; J. Mater. Chem. C. 2019, 7, 7144-7158; published 05-16-2019).
Regarding claims 1-10, the teachings of Huang are incorporated herein as detailed in the rejections above.
Regarding claim 11, Huang does not explicitly teach the organic compound according to claim 1, which has one of the structures of species CPD 001-CPD 098, as recited in the instant claim.
However, Huang teaches a genus of hole injection compound for use in hole transport materials as shown in Formula I:
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wherein X1-X6 are each independently any of of CX7, B or N, X7 is any group that satisfies its chemical environment, R1, R2, and R3 are each independently any one of O, S, =N(CN), =CR4R5 or substituted or unsubstituted quinones, R4 and R5 are each independently any group that satisfies its chemical environment, and n is an integer from 0 to 5. Huang further teaches a preferred restricted genus of Formula I wherein X7 is any one of cyano, halogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkynyl, acyl, aldehyde, carboxyl, ester, mercapto, thionyl, sulfonyl, phosphinyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted quinone; and wherein R4 and R5 are each independently any one of substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, cyano, halogen (any one of fluorine, chlorine, bromine or iodine), substituted or unsubstituted alkynyl, acyl, aldehyde, carboxyl, ester, mercapto, thionyl, sulfonyl, or phosphine (Formula I in 0008 and claim 1; Original Document; 0014-0015 and 0018; claims 1-2, 4, and 7; English language machine translation).
Huang also teaches a subgenus of preferred species as hole injection compounds, including the following species that reside within the genus of claims 1-10, as detailed in the rejections above:
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Furthermore, Huang teaches a structurally similar preferred species which depicts a terminal =(CN)2 group as a preferred substituent that corresponds to R2 = R3 = CN in formula (1) of claim 1 on which the instant claim depends (emphasis added; 0026 of Original Document):
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Therefore, since the genus and a preferred species of Huang teach compounds depicting a terminal =(CN)2 group as a preferred substituent, the skilled artisan could arrive at the following species CPD 031 as recited in claim 11 with a reasonable expectation of success based on the teachings of Huang alone:
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In addition, the skilled artisan could arrive at the species CPD 046 as recited in claim 11 with a reasonable expectation of success by replacing the CN groups of the known species of Huang detailed above with F, because the broader genus of Huang teaches that both CN and F are suitable substituents for compounds corresponding to X1-X6 of formula (1) of claim 1 on which the instant claim depends:
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The prior art as taught by Huang is analogous to the claimed invention because Huang teaches compounds for electroluminescent devices, including species that reside within formula (1) of instant claim 1 and a broader genus that encompasses the aforementioned species of instant claim 11, and a subgenus of preferred species that are structurally similar to the aforementioned species of instant claim 11. As such, the skilled artisan would have been sufficiently motivated to pursue the known compounds described by the genus of Huang that broadly overlaps with the instantly claimed genus to arrive at compounds CPD 031 and CPD 046 as described in instant claim 11 with a reasonable expectation of success. Furthermore, since Huang teaches a genus and preferred species which have significant structural similarity with the instantly claimed species, and falls within the scope of organic compounds and use thereof in an organic electroluminescent device, the skilled artisan could reasonably predict that all of the compounds possess the same utility. MPEP § 2144.08(II)(A)(4)(c) states that “The closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. See, e.g., Dillon, 919 F.2d at 696, 16 USPQ2d at 1904 (and cases cited therein).” Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have arrived at the claimed species as recited in claim 11 based on the teachings of Huang.
Regarding claims 12-14 and 16-20, Huang teaches an electroluminescent device OLED device which comprises, from bottom to top, an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and a cathode. The hole injection compounds disclosed by Huang are highly suitable for use as a hole injection material in OLED devices and has excellent hole injection performance. Organic light-emitting elements doped with the compounds of Huang in the hole transport layer effectively improve device lifespan. An objective of the invention of Huang is to provide a hold transport material, wherein the hole transport material is doped with the hole injection compound provided by the invention of Huang. The skilled artisan would recognize that the hole injection layer of Huang comprises the organic compounds and is arranged between the cathode and anode, in a manner consistent with the limitations of claims 12-13 and 16-20.
Further regarding claim 14, the material selections for the hole injection layer and the hole transport layer are shown in Table 1. Examples 1-4 of Huang show mixtures of compounds of the present invention (i.e., HI1-HI4) with NPB, a triarylamine with the following chemical structure (0068-0070 and Table 1; Original Document; 0008, 0030-0031, 0033, 0070, 0079; claims 9-10; Examples 1-4; English language machine translation):
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Although Examples 1-4 of Huang do not explicitly teach the use of compounds according to instant claims 1-5 and 11, the teachings of Huang render the limitations of these claims obvious as detailed above, and Huang further teachings that the embodiments described are merely illustrative of the invention and should not be construed as limiting the invention (0035; English language machine translation). Therefore, the skilled artisan could predictably arrive at an electroluminescent device wherein the hole injection layer comprises an organic compound of claims 1-5 and/or 11 and a hole transport material containing a triarylmine (i.e., NPB) with a reasonable expectation of success to arrive at the limitations of claims 12-14 and 16-20 based on the teachings of Huang alone.
Regarding claim 15, although Huang teaches the use of the triarylamine NPB as a hole transport material (0068-0070 and Table 1; Original Document; 0070 and Examples 1-4; English language machine translation), Huang does not explicitly teach wherein an absolute value of a highest occupied molecular orbital energy level HOMO of the hole transport material containing triarylamine or carbazole is 4.8-6.8 eV, as recited in claim 15.
However, 4,4’-Bis[N-(1-napthyl)-N-phenylamino]biphenyl (NPB) is considered one of the most successful hole transport materials and is largely used in organic devices owing to its good carrier mobility, high transparency for visible light and well-matched HOMO level (5.4 eV) for hole injection and hole transport, as evidenced by Shahnawaz (page 7144, Col. 2, paragraph 1). The 5.4 eV HOMO level of NPB resides within the range recited in the instant claim. MPEP § 2144.05(I) states that “[i]n the case where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.” Therefore, the skilled artisan would predictably arrive at the limitation of claim 15 based on the teachings of Huang in view of the evidentiary teachings of Shahnawaz.
Based on the combined teachings of the references, the Examiner submits that a person of ordinary skill in the art would have had a reasonable expectation of success of arriving at the instantly claimed compounds and electroluminescent devices comprising said compounds. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, and absent a clear showing of evidence to the contrary.
Conclusion
Any inquiry concerning this communication or earlier communications from the Examiner should be directed to Derek Rhoades whose telephone number is (703)-756-5321. The Examiner can normally be reached Monday–Thursday, 7:30 am–5:00 pm EST; Friday, 7:30 am–4:00 pm EST.
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/D.R./Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
