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 .
Summary of Claims
Claim 1, 5, 11, 13, and 15 are amended, and claim 6 are cancelled due to Applicant's amendment dated 06/22/2026. Claim 1–5 and 7–15 are pending.
Response to Amendment
The rejection of claims 1–11, 13, and 15 under 35 U.S.C. 103 as being unpatentable over Ha et al. (WO 2019/168368 A1, hereinafter “Ha”) is overcome due to the Applicant’s amendment dated 06/22/2026. The rejection is withdrawn.
The rejection of claims 12 and 14 under 35 U.S.C. 103 as being unpatentable over of Ha in view of Liao et al. (US 2003/0170491 A1, hereinafter “Liao”) is overcome due to the Applicant’s amendment dated 06/22/2026. The rejection is withdrawn.
However, as outlined below, new grounds of rejection have been made.
Response to Arguments
Applicant’s arguments on page 9–10 of the reply dated 06/22/2026 with respect to the rejection of claims 1-15 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument – Applicant argues that Modified Compound HI-4 set forth in the previous office action does satisfy amended claims 1 and 15 which now specifies “A2 and A3 are selected the same and A1 is selected differently from A2 and A3.”
Applicant further argues that does not teach asymmetric compounds pointing to paragraph [0191] and the specific compounds taught by Ha including Compound HI-4 which allegedly have identical groups. Therefore, there is allegedly no teaching, example, or motivation in Ha to arrive at the specific asymmetric arrangement now recited in amended claims 1 and 15.
Examiner's response – Examiner respectfully disagrees. Although Modified Compound HI-4 is overcome by Applicant’s amendment, Ha does disclose asymmetric molecules. Compound HI-4 is asymmetric (shown below). Additionally, although paragraph [0191] teaches that in the working state of the specification
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of chemical formula 3 are the same (i.e. symmetric), Ha teaches more broadly in paragraph [0172] that
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are identical or different from each other. Therefore, the compounds taught by Ha may be asymmetric. Therefore, rejections relying on a different embodiment taught by Ha are outlined below.
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Applicant’s arguments on page 11–12 of the reply dated 06/22/2026 with respect to the rejection of claims 1-15 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument – Applicant argues the claimed compounds show unexpected results over Ha.
Examiner's response – Overcoming a rejection based on unexpected results requires at least the combination of three different elements: (i) the results must fairly compare with the closest prior art in an affidavit or declaration under 37 CFR 1.132, (ii) the claims must be commensurate in scope, and (iii) the results must truly be unexpected. MPEP 716.02. Additionally, the burden rests with Applicant to establish the results are unexpected and significant. MPEP 716.02(b).
Comparison with closest prior art
Applicant has not made a comparison to the closest prior art. The device examples of the instant specification comprise different device structure and materials than the devices of Ha.
With respect to the device structure, Ha teaches Example 52 having the following structure and materials (¶ [0463] – [0466], [0499] – [0501] and Table 3):
Anode: ITO
Hole injection layer: Compound 1-2 and HI-4
Hole-transport layer: Compound 1-2
Emissive layer: BH1 and BD1
Electron-transport layer: Compound E1 and LiQ
Electron-injection layer: LiF
Cathode: Aluminum
The instant devices of the Declaration include the following (instant pg. 38–39 and Table 2)
Anode: ITO
Hole injection layer: Example 2
Hole transfer layer: Biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-catbazol-3-yl) phenyl]-amine
Electron blocking layer: N, N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1':4’,1”-terphenyl]-4-amine
Light emitting layer: H09 and BD200
Hole blocking layer: 2-(3'-(9,9- dimethyl-9H-fluoren-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine
Electron transport layer: 4'-(4-(4-(4,6-diphenyl-1,3,5-triazin-2- yl)phenyl)naphthalen-1-yl)-|1,l'-biphenyl]-4-carbonitrile and LiQ
Cathode: Aluminum
As shown above, the devices of the instant specification contain both a different layer structure and different layer materials as compared to the device of Ha. Applicant has not provided an explanation regarding this difference. It is unclear if the device comprising the same structure and materials of Ha that also contain the claimed asymmetric compound would obtain the results as discussed by Applicant.
As the devices of Applicant and the devices of Ha comprise different structure and materials, a comparison is not being made to the closest prior art. Where the comparison is not identical with the reference disclosure, deviations therefrom should be explained, and if not explained should be noted and evaluated, and if significant, explanation should be required. MPEP 716.02(e).
Commensurate in scope
As claims 1–14 claim a broad device structure including any materials but the devices discussed in the instant Table 2 only recite one specific device structure and materials (see instant pg. 38–39 and Table 2), the claims are not commensurate in scope. For example, as discussed above, the prior art teaches different device structure and materials than the instant specification. The structures and materials discussed in the prior art are within the claim scope of the instant application. As there are no results comprising the structures and materials of the prior art, it is unclear if the same results discussed by Applicant would be present.
Unexpected results
Applicant argues that comparative example C1 of the instant application corresponds to Ha’s Compound HI-4 wherein comparative example C1 has a LUMO level of -4.40 eV, whereas Examples E2, which read upon by the Applicant’s amended claims show improved LUMO levels of -4.82 eV. However, it is unclear if this change in LUMO level is due to the fact that A2 and A3 are the same while A1 is different in Example E2, or if it is due to a difference in substituents. Comparative example C1 has OCF3 substituents, whereas Example E2 has trifluoromethyl (CF3) and fluorine (F) substituents. Therefore, it is difficult to determine where the unexpected results originate from or if they are truly unexpected.
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 1–11, 13, 15 are rejected under 35 U.S.C. 103 as being unpatentable over Ha et al. (WO 2019/168368 A1, hereafter Ha). An English translation is provided within this office action.
Regarding Claims 1–9, 11, 13, 15, Ha teaches an organic light-emitting device comprising a cathode, an anode, a light-emitting layer, and an organic layer comprising a compound of Chemical Formula 1 and a compound of Chemical Formula 3 between the light-emitting layer and the anode [243]. This is exemplified by Example 52 wherein hole injection layer comprising Compound HI-4 (shown below) [508], which is a compound represented by Chemical Formula 3.
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However, Compound HI-4 fails to read on Applicants’ formula (I) because A2 and A3 are not the same. Additionally Compound HI-4 fails to read on Applicant’s formula (II) because R1 and R2 are represented by a C1 perfluorinated alkoxy group instead of a C1 perfluorinated alkyl group.
Regarding A2 and A3 being the same, Ha teaches Chemical Formula 3 wherein Compound HI-4 is represented by the fragments shown below [172]. In Compound HI-4,
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(A1)
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(A3) are each
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(substructure 1) while
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(A2) is
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(substructure 2). Additionally, Ha teaches using the compounds taught by Ha results in organic light-emitting devices with excellent efficiency, driving voltage, and stability [509] – [510].
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Therefore, given the general formula and teachings of Ha, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute Substructure 1 with Substructure 2 for A3, because Ha teaches the variable may suitably be selected as Substructure 1 or Substructure 2. The substitution would have been one preferred element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful as hole injection compound in the hole injection layer of the organic light-emitting device of Ha and possess the benefits taught by Ha. See MPEP 2143.I.(B).
Regarding substituting fluorinated alkoxy groups with fluorinated alkyl groups, Ha teaches Chemical Formula 3 wherein Compound HI-4 is represented by the fragments shown below [172]. For Compound HI-4, R34 is a haloalkoxy group (trifluoromethoxy) and a34 is 2. Ha recites that R34 may be a fluoro group, cyano group, trifluoromethoxy group, or a trifluoromethyl group [190]. As an example, Ha teaches Compound HI-5 (shown below) which has a trifluoromethyl group in the same position as the trifluoromethoxy group of Compound HI-4. Additionally, Ha teaches using the compounds taught by Ha results in organic light-emitting devices with excellent efficiency, driving voltage, and stability [509] – [510].
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It would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to modify Compound HI-4 by changing the trifluoromethoxy groups to trifluoromethyl groups, because it would have been choosing between a fluoro group, a cyano group, a trifluoromethoxy group, or a trifluoromethyl group, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the hole injection compound in the hole injection layer of the organic light-emitting device of Ha and possessing the excellent efficiency, driving voltage, and stability taught by Ha. One of ordinary skill in the art would have been motivated to produce additional compounds represented by/devices comprising compounds of Chemical Formula 3 having the benefits taught by Ha in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Per Claims 1 and 15, the organic light-emitting device, as described above, comprising Modified Compound HI-4 reads on Applicants’ formula (I), formula (II), and formula (III) (shown below),
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wherein:
For A1:
X1, X2, and X3 are each CH,
R1 and R2 are each a perfluorinated C1 alkyl group (trifluoromethyl),
R3 is CN,
For A2 and A3:
Ar is a C6 aryl (phenyl),
substituted with perfluorinated C1 alkyl (trifluoromethyl),
R3 is CN
Notably A2 and A3 are the same, while A1 is different from A2 and A3.
Per Claim 2, the organic light-emitting device, as described above, comprising Modified Compound HI-4 reads on Applicants’ formula (IV) and formula (V) (shown below),
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wherein:
For B1:
X1, X2, and X3 are each CH,
R1 and R2 are each a perfluorinated C1 alkyl group (trifluoromethyl),
For B3 and B5:
Ar is a C6 aryl (phenyl),
substituted with perfluorinated C1 alkyl (trifluoromethyl),
For B2, B4, and B6:
R3 is CN
Per Claims 3, 4, and 9, the organic light-emitting device, as described above, comprising Modified Compound HI-4 reads on Applicants’ limitation as R1 and R2 are each a perfluorinated C1 alkyl group (trifluoromethyl).
Per Claim 5, the organic light-emitting device, as described above, comprising Modified Compound HI-4 reads on Applicants’ limitation as R3 is CN.
Per Claims 7 and 8, the organic light-emitting device, as described above, comprising Modified Compound HI-4 reads on Applicants’ limitation as in formula (II) X1, X2, and X3 are each CH.
Per Claim 11, the organic light-emitting device, as described above, comprising Modified Compound HI-4 reads on Applicants’ limitation as Modified Compound HI-4 is within the hole injection layer, which is between the anode and the light-emitting layer (photoactive layer).
Per Claim 13, the organic light-emitting device, as described above, comprising Modified Compound HI-4 reads on Applicants’ limitation as an organic light-emitting device is an electroluminescent device.
Regarding Claim 10, Modified Compound HI-4 does not read on Applicants’ formula (IVa) to (IVd).
Ha teaches Chemical Formula 3 and the fragments shown below. Ha does not teach that the fragments must be positioned so that they are centrosymmetric. In fact, Ha teaches Compound HI-6 (shown below), wherein the CN and COOH groups are asymmetric.
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It would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to Modify Compound HI-4 so that it is asymmetric like Compound HI-6, because it would have been choosing between a symmetric or asymmetric arrangement, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the hole injection compound in the hole injection layer of the organic light-emitting device of Ha and possessing the benefits taught by Ha. One of ordinary skill in the art would have been motivated to produce additional compounds represented by/devices comprising compounds represented by Chemical Formula 3 having the benefits taught by Ha in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Per Claim 10, the organic light-emitting device, as described above, comprising Modified Compound HI-4 and Further Modified Compound HI- 4 reads on Applicants’ formula (IVa) (shown below), wherein B1 to B6 are the same as described above.
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Claims 12 and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Ha et al. (WO 2019/168368 A1) as applied to claims 1–11, 13, 15 above, and further in view of Liao et al. (US 2003/0170491 A1).
Regarding Claims 12, Ha fails to teach an organic light-emitting device with at least two photoactive layers, as recited in claim 12.
Liao teaches the stacked organic light-emitting device of Fig. 5 (shown below), wherein two organic EL units (320.1 and 320.2) are stacked [0055] – [0059]. 233 represents a p-type doped organic layer which comprises a compound which carries holes [0059] – [0060]. Liao further teaches the stacked organic light-emitting device will have decreased driving voltage, decreased optical absorption, and a simplified fabrication process [0012] – [0014].
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Modified Compound HI-4 inherently may carry holes since it is used as a hole injection material. Additionally, Ha teaches that the driving voltage of a device may be reduced by doping a compound of Chemical Formula 3 in an organic layer [255] – [256].
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to use the organic light-emitting device taught by Ha as an EL unit in the stacked organic light-emitting device taught by Liao. The motivation for doing so would have been to decrease the driving voltage, as taught by Liao.
Additionally, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to use Modified Compound HI-4 as the p-dopant in the stacked organic light-emitting device taught by Liao. The motivation for doing so would have been to reduce the driving voltage, as taught by Ha.
Per Claim 12, the stacked organic light-emitting device, as described above, comprising Modified Compound HI-4 reads on Applicants’ limitation as it has two light-emitting layers (photoactive layers) wherein Modified Compound HI-4 is used as the p-dopant between the two EL units.
Regarding Claim 14, Ha fails to teach an organic light-emitting device being used in a display device.
Liao teaches that a stacked organic light-emitting device may be used advantageously in a display device with high luminance efficiency and lifetime [0016] and [0070].
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to use the stacked organic light-emitting device, as described above, in a display device, based on the teachings of Liao. The motivation for doing so would have been to produce a display device with high luminance efficiency and lifetime, as taught by Liao.
Per Claim 14, the display device, as described above, comprising Modified Compound HI-4 reads on Applicants’ limitation as it is a display device comprising a stacked organic light-emitting diode.
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 JAMES RICHARD FORTWENGLER whose telephone number is (571)272-5433. The examiner can normally be reached Monday - Friday, 8 am - 5 pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Marla McConnell can be reached at (571) 270-7692. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/J.R.F./Examiner, Art Unit 1789
/MARLA D MCCONNELL/Supervisory Patent Examiner, Art Unit 1789
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