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 .
Status of Claims
This office action is in response to the amendment received on 18 June 2026. Claims 1 and 16-17 are amended, and claims 7, 14, and 15 are cancelled. Claims 1-6, 8-13, and 16-20 are pending.
Response to Amendment
The objection to the specification as set forth in the previous Office Action is not overcome due to the Applicant’s amendment dated 18 June 2026. Acknowledgement is made of the Applicant’s amendment; however, new issues need to be addressed such as missing bonds in structures as described below. The objection is maintained. The examiner requests that the issue of the compound structures missing bonds and not being fully aromatic either be (1) addressed via amendment or (2) indicated that the compound should be examined as intended, further described below.
The rejection of claims 1-20 under 35 U.S.C. 112(a) as failing to comply with the written description requirement as set forth in the previous Office Action is overcome due to the Applicant’s amendment dated 18 June 2026. The rejection is withdrawn.
The rejection of claims 14-15 under 35 U.S.C. 112(b) as being indefinite as set forth in the previous Office Action is overcome due to the Applicant’s amendment dated 18 June 2026. The rejection is withdrawn.
The rejection of claims 1-6, 14, and 18-20 under 35 U.S.C. 102(a)(1) and 35 U.S.C. 102(a)(2) as being anticipated by Takahashi et al. (WO2017158475A1, hereinafter "Takahashi") is overcome due to the Applicant’s amendment dated 18 June 2026. The rejection is withdrawn.
The rejection of claims 1-4 under 35 U.S.C. 103 as being unpatentable over Pan et al. (WO 2019105327A1, hereinafter "Pan"), in view of Takahashi et al. (WO2017158475A1, hereinafter "Takahashi") is overcome due to the Applicant’s amendment dated 18 June 2026. The rejection is withdrawn.
The rejection of claims 1 and 5-15 under 35 U.S.C. 103 as being unpatentable over Pan et al. (WO 2019105327A1, hereinafter "Pan") in view of Miao et al. (CN109326741, hereinafter "Miao") is overcome due to the Applicant’s amendment dated 18 June 2026. The rejection is withdrawn.
Response to Arguments
Applicant’s argument filed 18 June 2026 have been fully considered but they are not persuasive. With respect to Pan (WO 2019105327A1) in view of Miao (CN109326741), applicant points out that the difference in structure of Pan’s Compound 1-13 and the modified composition of Pan and Miao compared to reference structures. New rejections based on Pan and Miao rely on a different embodiment or a reinterpretation of the reference. The new rejection is based on a modified structure of Pan and Miao that is different to the structures relied on previously. Applicant points out that according to Miao, “at least one of the electron-blocking layers and the light-emitting layer of the device comprises a compound represented by General Formula (1).” Although Miao defines a device with a compound of General Formula (1) to (a) particular layer(s), Miao does not necessarily restrict the use of a compound of General Formula (1) to just the electron blocking layer and the light-emitting layer. As shown in the rejection below, Miao still renders obvious the claimed invention.
Regarding all other Applicant’s arguments, the arguments have been fully considered and are moot due to Applicant’s amendment filed 18 June 2026. New grounds of rejection do not rely on the other references applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Specification
The disclosure is objected to because of the following informalities: general formulas (i), (ii), and (iii) and specific compounds, both shown below, are missing bonds in the phenyl ring adjacent to a 5 membered ring (pg 23-27).
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Appropriate correction is required.
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Applicant is required to cancel the new matter in the reply to this Office Action.
Claim Objections
Claim 1 is objected to because of the following informalities: claim 1 contains a structure n_2 that is of low quality and hard to discern the full chemical structure such as missing bonds in the ter-phenyl structure and the missing bond in the fused furan structure, as reproduced below. Appropriate correction is required.
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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 1-6, 8-13, and 16-20 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 claim 1, compound n_2 displays a partially unsaturated ring adjacent to the furan structure and a partially unsaturated phenyl ring in the ter-phenyl structure. This structure in the claim does not appear to match in the specification where a compound n_2 is shown as a fully aromatic triphenylene structure substituting the triazine.
n_2 in Claim 1
n_2 in Specification
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Interpreted n_2
The confusion arises because it is unclear the actual structure of n_2 because the structure displayed in the claims do not match the specification wherein the structure may be interpreted as:
The claims correctly displays n_2 OR
The specification correctly displays n_2 OR
The Interpreted n_2 correctly displays n_2 wherein the structure is fully aromatic.
The examiner has chosen to interpret the claim 1 as both (1), (2), or (3). Note that the structure depicted in (1) wherein “the claim correctly displays n_2” may not be fully supported by the specification because no structures containing a terphenyl substituting the triazine is disclosed.
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.
Claims 1-6, 8-13, and 18-20 are rejected under 35 U.S.C. 103 as being unpatentable over Pan et al. (WO 2019105327A1, hereinafter "Pan"), in view of Miao et al. (CN109326741, hereinafter "Miao").
Pan teaches in the relevant art of organic light-emitting devices an organic composite film between two electrodes featuring two compounds M1 and M2 wherein M1 can be selected from small molecules and polymers of the general formula (3) featuring two connected carbazoles and M2 can be selected from small molecules and polymers of a skeleton with the general formula of triazine or carbazole shown below (¶ [0054]-[0071], [0327]).
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Pan teaches that devices containing compounds M1 and M2 can form an exciplex so that the organic composite film has high stability and can improve the device performance (¶ [0005] – [0012], [0039]).
Pan teaches device 1 containing compound 1-13 and 9-16, shown below, wherein compound 1-13 is a compound of General Formula 3 of Pan where the carbazole nitrogen is substituted with biphenyl and compound 9-16 is a compound of General Formula Triazine of Pan where u is the number of units in the polymer of the subunit structure shown (Table 2, ¶ [0005]).
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Pan teaches that compound 1-13 has a HOMO energy of -5.44 eV and a LUMO energy of -2.22 eV (Table 1).
Pan teaches that in some cases, preferred embodiments of compounds M1 and M2 that contain smaller HOMO energy differences, but not zero, can display improved light-emitting characteristics and efficiencies (Table 3).
Pan teaches that the OLED device based on the composition of device 1 where M1 is 1-13 and M2 is 9-16 can be manufactured with a solution concentration of 5 mg/mL where the thickness of the layer containing M2 materials is 65 nm and the thickness with the layer containing M1 material is 20 nm. One of ordinary skill in the art would estimate the weight ratio to be proportional to the thickness of the layer wherein the ratio of M2 to M1 would be about 76:24.
Pan teaches device 1 containing compound 1-13 and 9-16, shown below, wherein compound 1-13 is a compound of General Formula 3 of Pan where the carbazole nitrogen is substituted with biphenyl and compound 9-16 is a compound of General Formula Triazine of Pan where u is the number of units in the polymer of the subunit structure shown (Table 2, ¶ [0005]).
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Pan further teaches other structures that are suitable for use as compound M2 featuring a skeleton of General Formula triazine including the structures shown below (¶ [0256]).
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Compound 6-1 features a triazine core connected to a triphenylene group. Therefore, triphenylene are known and acceptable moieties for the triazine skeleton of the general formula M2 of Pan. Another compound features a connected carbazole connected at the N-position to the triazine. Therefore, a carbazole connected at the N-position to the triazine is a known and acceptable moiety for the triazine skeleton of the general formula M2 of Pan. Another compound features a fused indolocarbazole connected at the N-position to the triazine core, compound 1-5 (¶ [0263]). Therefore, a fused indolocarbazole connected at the N-position to the triazine core is a known and acceptable moiety for the triazine skeleton of the general formula M2 of Pan.
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 have
modified the compound 9-16 of Pan with the triphenylene moiety of Pan and a carbazole derivate of Pan, based on the teachings of Pan. The motivation for doing so would have been to generate a compound with a HOMO energy level difference greater than 0 but still close in energy to drive efficient exciplex formation towards a device high in light-emitting and luminous efficiency as taught by Pan.
Furthermore, 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 9-16 with a triphenylene and fused indolocarbazole because it would have been choosing a compound with a lower HOMO energy, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the M2 compound layer of the composite layer generating an exciplex for the organic light-emitting device of Pan and possessing the benefits taught by Pan. One of ordinary skill in the art would have been motivated to produce additional compounds represented by the triazine skeleton of the general formula M2 of Pan comprising a triazine with a triphenylene group and an indolocarbazole having the benefits taught by Pan in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The modified composition of Pan is shown below.
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Pan teaches all the limitations above including a triazine connected to a fused five-ring system; however, Pan fails to teach a triazine connected to a fused seven-ring system of the instant compound n_2.
In the relevant art of organic-light emitting devices, Miao teaches triazine compounds towards OLED devices with high luminous efficiency and long life (Description, ¶ [0003]). Miao teaches compounds 54, 70, 71, and 72, which are compounds of Pan triazine skeleton for the general formula of M2 shown below (Description pg 13).
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Compound 54 is a compound of Pan featuring an indolocarbazole attached to a phenyl linker and triazine core. Compounds 70 to 72 feature an extended 7-ring fused system attached to triazine. Compounds 70 to 72 show that nitrogen, oxygen, and sulfur are suitable heteroatoms for the 7-ring fused system. Therefore, an extended 7-ring fused system, as taught by Miao, attached to triazine core is a known and acceptable moiety especially for the replacement of indolocarbazole for the triazine core.
Miao teaches that the ring condensation of the benzothiophene is not just limited to the example shown in compound 71: Miao teaches that the benzothiophene may be fused to the central carbazole moiety in another orientation as seen in the example shown below (Description pg 8).
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Miao also teaches that the preferred embodiments and compounds display both high efficiency and lifetime in OLED materials (Table 3, ¶ [0015]).
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 have
modified the Modified Composition of Pan with the extended 7-ring fused system of Miao, based on the teachings of Pan and Miao. The motivation for doing so would have been to generate a compound with a HOMO energy level difference greater than 0 but still close in energy to drive efficient exciplex formation towards a device high luminous efficiency and long lifetime as taught by Pan and Miao.
Furthermore, 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 the modified composition of Pan by replacing the indolocarbazole with the extended 7-ring fused system containing N, O, or S of Miao because it would have been choosing a compound with a modified HOMO energy and long luminous efficiency and long lifetime of Miao, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the M2 compound layer of the composite layer generating an exciplex for the organic light-emitting device of Pan and possessing the benefits taught by Pan and Miao. One of ordinary skill in the art would have been motivated to produce additional compounds represented by the triazine skeleton of the general formula M2 of Pan comprising a triazine with a triphenylene group and an extended 7-ring fused system containing N, O, and S having the benefits taught by Pan and Miao in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The Modified Composition of Pan and Miao is shown below.
Modified Composition of Pan and Miao
1-13
Modified Compound of Pan and Miao
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The Modified Composition of Pan and Miao contains compound 1-13 of Pan featuring two connected carbazoles which is the same as compound p_2 of instant claim 1. The modified composition of Pan and Miao contains a triazine compound which is a compound of instant claim 1 and is the same as compound n_2. Note that the examiner is interpreting the compound n_2 to be fully aromatic as described above in the Interpreted n_2 compound.
Regarding instant claim 1, Pan and Miao appear silent with respect to the property of the HOMO, LUMO, S1, and T1 energy levels as well as the mobility parameter of compounds in the Modified Composition of Pan and Miao.
The instant specification recites that compound p_2 and n_2 have the HOMO, LUMO, S1, T1 and Mobility values as reproduced below in instant Table 1.
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Since Pan and Miao teach the Modified Composition of Pan and Miao including compounds 1-13 and a substituted triazine, the same structures as disclosed by the Applicant, the property of HOMO, LUMO, S1, T1 and mobility is considered to be inherent (and would be expected to fall within the range in the claim), absent evidence otherwise. Recitation of a newly disclosed property does not distinguish over a reference disclosure of the article or composition claims. When the structure recited in the prior art reference is identical to that of the claims, claimed properties or functions are presumed to be inherent. Applicant bears responsibility for proving that the reference composition does not possess the characteristics recited in the claims. See MPEP 2112.
The compound 1-13 in the Modified Composition of Pan and Miao is the same as compound p_2. Furthermore, the triazine compound is identical to a compound of the instant preferred embodiment; however, the applicant has not provided the HOMO, LUMO, etc. energy levels of each of their preferred embodiments. The applicant has provided a singular example of a n-type compound, compound n_2 shown below, with included parameters.
Instant compound n_2 is similar in all aspects to the triazine compound in the Modified compound of Pan and Miao including the triazine core substituted with a phenyl, triphenylene, and a 7-ring fused system containing O, N, and S. Note that the examiner is choosing to interpret instant compound n_2 as a triphenylene moiety and a completely aromatic system.
Because the compounds are identical, (1) the energy levels are expected to be identical, (2) the normalized fluorescence emission spectrum of the exciplex and a normalized fluorescence emission spectrum of the n-type material have an overlapping region, and (3) the integral area of the overlapping region is expected to be greater than or equal to 90%. The Modified Composition of Pan and Miao reads on claims 1-6, 8-13, and 18-20.
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over Pan et al. (WO 2019105327A1, hereinafter "Pan") and Miao et al. (CN109326741, hereinafter "Miao") as applied to claims 1-6, 8-13, and 18-20 described above in view of Deshpande et al. (Appl. Phys. Lett. 75, 888-890 (1999), hereinafter "Deshpande").
Pan and Miao teaches the organic light-emitting device containing the Modified Composition of Pan and Miao that reads on claims 1-6, 8-13, and 18-20 as described above. However, Pan and Miao is silent on the organic light-emitting device containing the material of the hole blocking layer as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline.
In the relevant art of organic light-emitting devices, Deshpande teaches an efficient organic white-light emitting device containing a hole-blocking layer 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline or “BCP” (abstract). 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 further include the hole-blocking layer containing BCP of Deshpande in the light-emitting device of Pan and Miao, based on the teachings of Deshpande. The motivation for doing so would have been to obtain a device with high efficiency, as taught by Deshpande (abstract).
The combination of Pan, Miao, and Deshpande appears silent on the property of the difference of the (1) LUMO of the n-type material and the (2) LUMO of the hole blocking layer is less than or equal to 0.3 eV. Pan, Miao and Deshpande teaches the claimed invention above but does not expressly teach the LUMO relationship described above. It is reasonable to presume that the LUMO relationship is inherent to the resulting modified device of Pan, Miao, and Deshpande. Support for said presumption is found in that n-type material and the hole blocking layer of the modified device of Pan, Miao, and Deshpande has the same structure as the Experimental example in the instant specification, and therefore are expected to have the same properties of the claimed invention. The resulting modified device of Pan, Miao, and Deshpande reads on instant claim 17.
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 LUCAS Q NGUYEN whose telephone number is (571)272-1199. The examiner can normally be reached Monday - Thursday 7:30 am - 5:00 pm Fridays 7:45 am to 12:00 pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer 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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/L.Q.N./Examiner, Art Unit 1786
/JENNIFER A BOYD/Supervisory Patent Examiner, Art Unit 1786
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