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
Claims 17 and 20 are amended due to Applicant's amendment dated 03/13/2026. Claims 1-14 and 16-22 are pending.
Response to Amendment
The objection to claims 17 and 20 as set forth in the previous Office Action is overcome due to the Applicant's amendment dated 03/13/2026.
The rejection of claims 1-5, 8-14, and 16-20 under 35 U.S.C. 103 as being unpatentable over Hatakeyama (US 2018/0094000 A1) in view of Wei (Wei, Qiang, et al. "Small‐molecule emitters with high quantum efficiency: mechanisms, structures, and applications in OLED devices." Advanced Optical Materials 6.20 (2018): 1800512.) and Liu (Liu, Yuan, et al. "Boosting photoluminescence quantum yields of triarylboron/phenoxazine hybrids via incorporation of cyano groups and their applications as TADF emitters for high-performance solution-processed OLEDs." Journal of Materials Chemistry C 7.16 (2019): 4778-4783.) is not overcome due to the Applicant’s amendment dated 03/13/2026. The rejection is maintained.
The rejection of claim 6 under 35 U.S.C. 103 as being unpatentable over Hatakeyama in view of Wei, Liu, and Cosimbescu (US 2005/0089717 A1) is not overcome due to the Applicant’s amendment dated 03/13/2026. The rejection is maintained.
The rejection of claim 7 under 35 U.S.C. 103 as being unpatentable over Hatakeyama in view of Wei, Liu, and Seo (US 2016/0293877 A1) is not overcome due to the Applicant’s amendment dated 03/13/2026. The rejection is maintained.
The rejection of claims 21-22 under 35 U.S.C. 103 as being unpatentable over Hatakeyama in view of Wei, Liu, and Hatakeyama ‘402 (English translation of WO 2019235402 A1 obtained from Global Dossier) is not overcome due to the Applicant’s amendment dated 03/13/2026. The rejection is maintained.
Response to Arguments
Applicant’s arguments on pages 38-41 of the reply dated 03/13/2026 with respect to the rejection of claims 1-14 and 16-20 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –Applicant argues on pgs. 38-40 that Hatakeyama’s ED25 is a fluorescent material and thus one of ordinary skill in the art would have no reason to modify ED25 with the cyano groups of Wei or Liu, given that Wei and Liu are directed to thermally activated delayed fluorescent (TADF) compounds.
Examiner's response –As pointed out by Applicant, Hatakeyama teaches the fluorescent material (i.e., compound ED25) may be a delayed fluorescent material (¶ [0038]). One of ordinary skill in the art would recognize that delayed fluorescence encompasses thermally activated delayed fluorescence. Accordingly, the fluorescent material of Hatakeyama may also be a TADF material, but it is not limited to this.
As discussed in greater detail in the rejection below, Hatakeyama ‘274 provides evidence that compound ED25 (before modification) exhibits thermally activated delayed fluorescence. Accordingly, compound ED25 may be considered a TADF compound. As Wei and Liu are directed to TADF materials and teach that modifying TADF emitters with cyano groups provide benefits of long lifetime and improved photoluminescence quantum yield and efficiency roll-offs, it would have been obvious to one of ordinary skill to modify compound ED25 with the teachings of Wei and Liu to arrive at a compound of the claimed invention.
Applicant's argument –Applicant argues on pgs. 40-41 that Hatakeyama is intentionally designed to include both a TADF compound and a separate fluorescent compound (i.e., ED25) and that these compounds perform different roles in the emission layer. Applicant argues that modifying ED25 with CN groups would fundamentally alter the role of the fluorescent compound. Applicant further argues neither Wei nor Liu suggest modifying a fluorescent compound for the purpose of converting it to a TADF material, and a person skill in the art would have no reasonable expectation of success in the proposed modification.
Examiner's response –As discussed below and in the previous rejection, Hatakeyama teaches ED25 is an example of a compound represented by general formula (ED1) and further teaches at least one hydrogen in the structure represented by general formula (ED1) may be substituted with cyano (¶ [0222], [0228], and [0239]; structure on pg. 130). Hatakeyama additionally teaches cyano is an example of a substituent that provides wavelength prolongation (¶ [0190]-[0191]).
Accordingly, not only is substituting compound ED25 within the scope of Hatakeyama’s general formula (ED1), but Hatakeyama also provides specific motivation as to why one of ordinary skill would want to provide cyano as a substituent. Given that the modified compound ED25 including cyano groups is within the scope of Hatakeyama’s general formula (ED1), one of ordinary skill in the art would expect the modified compound ED25 to successfully function as a fluorescent compound, as intended by Hatakeyama.
Additionally, it should be noted that the rejection does not propose converting a fluorescent compound to a TADF compound. As evidenced by Hatakeyama ‘274, compound ED25 (before modification) already exhibits thermally activated delayed fluorescence. Rather, the rejection simply modifies ED25 with cyano groups and this is within the scope of Hatakeyama’s general formula (ED1).
Applicant's argument –Applicant argues on pg. 41 that the modification of ED25 with cyano groups (including the selection of binding sites and the number of binding sites) is based on impermissible hindsight.
Examiner's response –In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. As discussed above and outlined below, the rejections take into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the Applicant's disclosure.
As discussed above, cyano substitution is within the scope of Hatakeyama’s general formula (ED1) and substituting cyano groups on ED25 provides benefits of wavelength prolongation, as taught by Hatakeyama, and a device with long lifetime, improved external quantum efficiency, and extremely small efficiency roll-offs, as taught by Wei and Liu.
While the prior art does not specifically teach how many cyano groups to provide on ED25 and where to introduce such groups, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to introduce four cyano groups on ED25 in the locations highlighted below, because it would have been choosing a particular number and positions of the cyano groups on ED25, which would have been a choice from a finite number of identified, predictable solutions of a compound of Hatakeyama’s general formula (ED1) and possessing the benefits taught by Hatakeyama, Wei, and Liu taught above. One of ordinary skill in the art would have been motivated to produce additional compounds comprising cyano groups having the benefits taught by Hatakeyama, Wei, and Liu in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-5, 8-14, and 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama (US 2021/0351364 A1) in view of Wei (Wei, Qiang, et al. "Small‐molecule emitters with high quantum efficiency: mechanisms, structures, and applications in OLED devices." Advanced Optical Materials 6.20 (2018): 1800512.) and Liu (Liu, Yuan, et al. "Boosting photoluminescence quantum yields of triarylboron/phenoxazine hybrids via incorporation of cyano groups and their applications as TADF emitters for high-performance solution-processed OLEDs." Journal of Materials Chemistry C 7.16 (2019): 4778-4783.), as evidenced by Hatakeyama ‘274 (US 2015/0236274 A1).
Regarding claims 1-5, 8-14, and 16-20, Hatakeyama teaches an organic electroluminescent device comprising an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode, wherein the light-emitting layer contains 50-99.99 wt% of a host compound as a first compound, a TADF material as a second component, and 0.001 to 30 wt% of a fluorescent material as a third compound, wherein the third compound may be represented by general formula (ED1) and examples thereof include compound ED25 (abstract; ¶ [0020], [0063], [0066], [0068], [0223], and [0247]; structure on pg. 6).
ED25:
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Compound ED25 fails to include an electron withdrawing group as required by claim 1.
However, Hatakeyama does teach at least one hydrogen in the structure represented by general formula (ED1) may be substituted with cyano, and further teaches cyano is an example of a substituent that provides wavelength prolongation (¶ [0190]-[0191] and [0228]).
Additionally, ED25 reads on an oligomer having plural structures of general formula (1) of Hatakeyama ‘274 wherein in each plural structure rings A to C are an aryl ring, Y1 is B, X1 is O, X2 is N-R, and R is an aryl (see Hatakeyama ‘274, ¶ [0013]-[0021]). Accordingly, as evidenced by Hatakeyama ‘274, ED25 exhibits thermally activated delayed fluorescence (see Hatakeyama ‘274, ¶ [0046]).
In the art of OLED devices, Wei teaches the cyano (CN) group is widely applied in designing TADF emitters, and emitters of cyano-type usually show a long lifetime in application (abstract and pg. 12, right column, second paragraph).
Similarly, Liu teaches the introduction of cyano groups into TADF emitters significantly improves the external quantum efficiency of OLEDs comprising the emitters (pg. 4778, right column, last paragraph to pg. 4779, left column, first paragraph). Additionally, the introduction of cyano groups improves the photoluminescence quantum yield and provide devices with extremely small efficiency roll-offs (abstract and pg. 4779, left column, first paragraph).
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 substitute cyano groups on ED25 of Hatakeyama, based on the teaches of Hatakeyama, Wei, and Liu. The motivation for doing so would have been to provide wavelength prolongation, as taught by Hatakeyama, and to obtain a device having a long lifetime, improved external quantum efficiency, and extremely small efficiency roll-offs, and to provide a compound having improved photoluminescence quantum yield, as taught by Wei and Liu.
Hatakeyama in view of Wei and Liu fail to teach how many cyano groups to provide on ED25 and where to introduce such groups.
However, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to introduce four cyano groups on ED25 in the locations highlighted below, because it would have been choosing a particular number and positions of the cyano groups on ED25, which would have been a choice from a finite number of identified, predictable solutions of a compound of Hatakeyama’s general formula (ED1) and possessing the benefits taught by Hatakeyama, Wei, and Liu taught above. One of ordinary skill in the art would have been motivated to produce additional compounds comprising cyano groups having the benefits taught by Hatakeyama, Wei, and Liu in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
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The modified ED25 of Hatakeyama in view of Wei and Liu has the same structure as the claimed compound 3 (claim 20), and is reproduced below in comparison with the claimed Formula 1.
modified ED25:
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Formula 1:
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The modified ED25 reads on the claimed Formula 1 and Formula 1-20 (claims 1, 8, and 17) wherein:
A1 to A4 are each a C6 carbocyclic group (benzene) (claims 9-10);
B1 is benzene (claim 10);
Y1 and Y2 are each B (claim 11);
X1 is N(R1), X2 and X4 are each O, and X3 is N(R3) and thus satisfy condition (iv);
L1 to L5 are not required to be present as a1 to a5 are each 0 (claims 12 and 19);
Ar1 to Ar5 are each hydrogen (claims 13 and 19);
R1 and R3 are each a C6 carbocyclic group (phenyl), and R2 and R4 are not required to be present (claim 14);
b1 to b5 are each 1;
c1 and c2 are each 1, c5 is 2, and c3 and c4 are each 4 (claim 16);
Z1 and Z2 are each an electron withdrawing group of -CN (claims 18); and
t1 and t2 are each 2 (claim 16).
Per claim 4, Hatakeyama in view of Wei and Lui appear silent with respect to the property of the modified ED25 being a delayed fluorescence compound.
The instant specification recites that the condensed cyclic compound represented by Formula 1 is a delayed fluorescence emitter, and additionally recites compound 3 as an example of a compound represented by Formula 1 (¶ [0036], [00123]-[00124], [00128], and [00144]). Since Hatakeyama in view of Wei and Lui teach the modified ED25, the same structure as instant compound 3 disclosed by the Applicant, the property of being a delayed fluorescence compound is considered to be inherent, 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 substantially 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.
As the modified ED25 exhibits thermally activated delayed fluorescence, the light emitting layer containing the modified ED25 emits delayed fluorescence (claim 4).
Claim 6 is rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama (US 2021/0351364 A1) in view of Wei (Wei, Qiang, et al. "Small‐molecule emitters with high quantum efficiency: mechanisms, structures, and applications in OLED devices." Advanced Optical Materials 6.20 (2018): 1800512.) and Liu (Liu, Yuan, et al. "Boosting photoluminescence quantum yields of triarylboron/phenoxazine hybrids via incorporation of cyano groups and their applications as TADF emitters for high-performance solution-processed OLEDs." Journal of Materials Chemistry C 7.16 (2019): 4778-4783.) as applied to claim 5 above, and further in view of Cosimbescu (US 2005/0089717 A1).
Regarding claim 6, Hatakeyama in view of Wei and Liu teach the organic electroluminescent device including the modified ED25 as described above with respect to claim 5.
Hatakeyama teaches a host material provided in the device has a boron atom and an oxygen atom in the molecule used (¶ [0041]), and thus Hatakeyama in view of Wei and Liu fail to specifically teach the organic electroluminescent device including the modified ED25 further includes an anthracene-based compound as a host material. However, Hatakeyama does teach there may be multiple kinds of hosts provided (¶ [0063]-[0065]).
Cosimbescu teaches an OLED comprising a light emitting layer containing a light emitting dopant and a host comprising a monoanthracene derivative represented by Formula (I) (abstract and ¶ [0011]). By including the monoanthracene derivative as a host, the device obtains improved operational stability (¶ [0007] and [0009]).
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 provide a monoanthracene derivative as a host material in Hatakeyama’s device, based on the teaching of Cosimbescu. The motivation for doing so would have been to provide a device with improved operational stability, as taught by Cosimbescu.
Claim 7 is rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama (US 2021/0351364 A1) in view of Wei (Wei, Qiang, et al. "Small‐molecule emitters with high quantum efficiency: mechanisms, structures, and applications in OLED devices." Advanced Optical Materials 6.20 (2018): 1800512.) and Liu (Liu, Yuan, et al. "Boosting photoluminescence quantum yields of triarylboron/phenoxazine hybrids via incorporation of cyano groups and their applications as TADF emitters for high-performance solution-processed OLEDs." Journal of Materials Chemistry C 7.16 (2019): 4778-4783.) as applied to claim 1 above, and further in view of Seo (US 2016/0293877 A1).
Regarding claim 7, Hatakeyama in view of Wei and Liu teach the organic electroluminescent device including the modified ED25 as described above with respect to claim 1.
While Hatakeyama teaches the light-emitting layer may be formed of multiple layers (¶ [0065]), Hatakeyama fails to teach the light emitting layer comprising the modified ED25 further comprises additional layers that emit additional colors.
Seo teaches a light-emitting element in which the light-emitting layer comprises multiple light-emitting layers (¶ [0061]). Seo teaches when light-emitting layers have different emission colors, a desired emission color can be obtained from the whole light-emitting element (mixed light) (¶ [0107]). Seo teaches an example of a light-emitting element that emits white light by providing three layers wherein the emission color of the first EL layer is red, the emission color of the second EL layer is green, and the emission color of the third EL layer is blue (¶ [0108]).
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 provide three layers in the light emitting layer in Hatakeyama’s organic electroluminescent device, wherein one of the layers comprises the modified ED25 as a dopant, and wherein the layers emit red, green, and blue light, respectively, because one of ordinary skill in the art would reasonably have expected the organic electroluminescent device of Hatakeyama and the emission layers of Seo to predictably maintain their respective properties or functions after they have been combined, and this would have been combining prior art elements according to known methods to yield predictable results. See MPEP 2143.I.(A).
The resulting light emitting layer comprises a first, second, and third emission layer, each emitting a first, second, and third color light, respectively, and the three color lights are emitted as white light, which is a mixed light and thus reads on the limitation of claim 7.
Claims 21-22 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama (US 2021/0351364 A1) in view of Wei (Wei, Qiang, et al. "Small‐molecule emitters with high quantum efficiency: mechanisms, structures, and applications in OLED devices." Advanced Optical Materials 6.20 (2018): 1800512.) and Liu (Liu, Yuan, et al. "Boosting photoluminescence quantum yields of triarylboron/phenoxazine hybrids via incorporation of cyano groups and their applications as TADF emitters for high-performance solution-processed OLEDs." Journal of Materials Chemistry C 7.16 (2019): 4778-4783.) as applied to claims 1 and 8 above, and further in view of Hatakeyama ‘402 (English translation of WO 2019235402 A1 obtained from Global Dossier).
Regarding claims 21-22, Hatakeyama in view of Wei and Liu teach the organic electroluminescent device including the modified ED25 as described above with respect to claims 1 and 8.
modified ED25:
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The modified ED25 fails to include an electron withdrawing group selected from -Cl, -Br, -I, or a C1-C60 alkyl group substituted with -Cl, -Br, -I. However, Hatakeyama does teach at least one hydrogen in the structure represented by general formula (ED1) may be substituted with a halogen, which includes chlorine, bromine, or iodine (¶ [0228] and [0295]).
Hatakeyama ‘402 teaches multimers of a polycyclic aromatic compound having a plurality of unit structures represented by general formula (1), such as a compound represented by formula (1-5-3) (¶ [0071]-[0072]). All or a part of the multimer may be substituted with halogen (¶ [0075]).
(1-5-3):
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From the viewpoint of increasing the spin-orbit interaction due to the heavy atomic effect, a halogen having a large molecular weight, such as iodine, is most preferable (¶ [0064]). The larger the spin-orbit interaction, the more likely thermally activated delayed fluorescence occurs (¶ [0039]).
Therefore, given that Hatakeyama teaches at least one hydrogen in the structure represented by general formula (ED1) may be substituted with iodine, 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 substitute the modified ED25 with iodine, based on the teaching of Hatakeyama ‘402. The motivation for doing so would have been to increase the spin-orbit interaction and thus provide a compound wherein it is more likely that thermally activated delayed fluorescence occurs, as taught by Hatakeyama ‘402.
Particularly, 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 iodine in the location of the claimed Z1 and Z2, because it would have been choosing a specific position on the modified ED25 in which to substitute iodine, and this would have been a choice from a finite number of identified, predictable solutions of a compound useful as the third component in the light-emitting layer of the organic electroluminescent device of Hatakeyama in view of Wei, Liu, and Hatakeyama ‘402 and possessing the benefits taught by Hatakeyama ‘402. One of ordinary skill in the art would have been motivated to produce additional compounds comprising halogens having the benefits taught by Hatakeyama ‘402 in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Conclusion
THIS ACTION IS MADE FINAL. 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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BRAELYN R WATSON whose telephone number is (571)272-1822. The examiner can normally be reached M-F 7:30am-5pm.
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/BRAELYN R WATSON/Examiner, Art Unit 1786
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