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
Claim 16 is amended due to Applicant's amendment dated 10/31/2025. Claims 1-20 are pending.
Election/Restrictions
As discussed in the previous Office Action, Applicant elected Species A (a condensed cyclic compound of Formula 2-11) in the reply filed on 07/18/2025.
Formula 2-11:
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Response to Amendment
The objection to claim 16 as set forth in the previous Office Action is not overcome due to the Applicant's amendment dated 10/31/2025. The objection is maintained.
The rejection of claims 1-3, 7, and 10-19 under 35 U.S.C. 103 as being unpatentable over Ueno (English translation of JP 2002324675 A obtained from Global Dossier) in view of Lu (US 2021/0013424 A1) is not overcome due to the Applicant’s amendment dated 10/31/2025. The rejection is maintained.
The rejection of claims 4-6 under 35 U.S.C. 103 as being unpatentable over Ueno in view of Lu and Chen (US 2020/0411775 A1) is not overcome due to the Applicant’s amendment dated 10/31/2025. The rejection is maintained.
The rejection of claim 8 under 35 U.S.C. 103 as being unpatentable over Ueno in view of Lu and Jeong (US 7,652,287 B2) is not overcome due to the Applicant’s amendment dated 10/31/2025. The rejection is maintained.
The rejection of claim 9 under 35 U.S.C. 103 as being unpatentable over Ueno in view of Lu and Cok (US 2004/0080267 A1) is not overcome due to the Applicant’s amendment dated 10/31/2025. The rejection is maintained.
The rejection of claim 20 under 35 U.S.C. 103 as being unpatentable over Ueno in view of Lu and Liu (English translation of CN 112442035 A obtained from Global Dossier)) is not overcome due to the Applicant’s amendment dated 10/31/2025. The rejection is maintained.
Response to Arguments
Applicant argues on page 33 that the objection to claim 16 is moot given that claim 16 is amended for clarity. However, the objection to claim 16 is maintained because the structures of Formulae 3-1 to 3-47 which include the subscripts of e2 to e9 are blurry.
Applicant’s arguments on pages 33-38 of the reply dated 10/31/2025 with respect to the rejection of claims 1-20 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –Applicant argues that compounds of the claimed embodiments exhibit unexpected and desirable results with respect to driving voltage, luminance, half lifespan, and luminescence efficiency over the cited prior art. Applicant points to a comparison of Examples 1 to 7 and Comparative Examples 1 to 8 (as shown in Table 2 of the instant specification on pages 97-99) for support. As Compound CE5 of Comparative Example 7 is identical to the cited compound of Ueno, Applicant argues the claimed embodiments would not have been obvious over Ueno.
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).
As shown in Table 2 of the instant specification, Comparative Example 7 comprises an emission layer using a single host of Compound CE5 and a dopant of ACRSA. Inventive Examples 4 and 5 are the only inventive examples that similarly contain an emission layer using a single host of an inventive compound and a dopant of ACRSA. The other inventive examples (Examples 1-3 and 6-7) do not match this structure and instead include mixed hosts and either a dopant of FIrpic or mixed dopants of PD27 and DF11. Accordingly, a comparison between: 1) Example 4 and Comparative Example 7, and 2) Example 5 and Comparative Example 7 are the only comparisons with the closest prior art. The data of these devices are summarized in the table below:
Driving voltage (V)
Current density (mA/cm2)
Luminance (cd/m2)
Half lifespan (hr @100 mA/cm2)
Example 4
6.01
2975
5.95
361
Example 5
5.74
3870
7.74
334
Comparative Example 7
5.57
3588
7.13
322
Unexpected Results
While there is improvement in half lifespan between Example 4 and Comparative Example 7, and while there is improvement in driving voltage, luminance, luminescence efficiency, and half lifespan between Example 5 and Comparative Example 7, it is unclear whether these performances are truly unexpected.
Example 4 shows a 12% improvement in half lifespan over Comparative Example 7. With respect to driving voltage, luminance, and luminescence efficiency, Comparative Example 7 is superior to Example 4. Additionally, Example 5 shows a 3% improvement in driving voltage, an 8% improvement in luminance, a 9% improvement in efficiency, and a 4% improvement in half lifespan over Comparative Example 7. It should be noted that half lifespan is the only device property that improves in both Example 4 and Example 5 in comparison to Comparative Example 7.
Given the device property values of Examples 4-5, the instant devices show a driving voltage variability of 5%, a luminance variability of 30%, a luminescence efficiency variability of 30%, and a half lifespan variability of 8%. Similarly, as shown in Table 2 of the instant specification, Comparative Examples 3-8 show a driving voltage variability of 6%, a luminance variability of 8%, a luminescence efficiency variability of 8%, and a half lifespan variability of 9%. These variabilities illustrate the degree to which one of ordinary skill in the art could expect device properties to differ simply by altering the host compound therein. Given that the degree of improvement shown by Examples 4-5 significantly overlaps with the degree of variability shown by Examples 4-5 and the degree of variability shown by Comparative Examples 3-8, it is unclear whether the improvement is unexpected.
Additionally, one of ordinary skill in the art would recognize that devices comprising compounds having different structures would not result in identical properties. Accordingly, one of ordinary skill would expect some degree of difference in driving voltage, luminance, luminescence efficiency, and half lifespan between devices of Examples 4-5 and Comparative Example 7.
Thus, in light of the variability between instant devices and the variability between comparative devices, and given that one of ordinary skill in the art would expect some difference between devices comprising compounds having different structure, it is unclear whether the degree of improvement shown by the data in the instant specification is truly unexpected.
Commensurate in Scope
While Example 4 shows a 12% improvement in half lifespan over Comparative Example 7, Example 5 only shows a 4% improvement in half lifespan over Comparative Example 7. That is, given that Example 4 and Example 5 are both claimed embodiments, the same degree of improvement is not shown across the full scope of what is being claimed. Accordingly, even if the degree of improvement in half lifespan shown by Example 4 is considered unexpected, it does not appear that the unexpected results are demonstrated across the full scope of what is being claimed.
Additionally, as discussed above, while Example 5 shows an improvement in driving voltage, luminance, and luminescence efficiency over Comparative Example 7, Example 4 does not show an improvement with respect to these properties. Accordingly, it cannot be said that unexpected results are demonstrated across the full scope of what is being claimed with respect to the properties of driving voltage, luminance, and luminescence efficiency.
Claim Objections
Claim 16 is objected to because of the following informalities: claim 16 includes groups of Formulae 3-1 to 3-47 which include variables Z31 to Z36 and subscripts of e2 to e9 that are blurry. Appropriate correction is required.
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 1-3, 7, and 10-19 are rejected under 35 U.S.C. 103 as being unpatentable over Ueno (English translation of JP 2002324675 A obtained from Global Dossier) in view of Lu (US 2021/0013424 A1).
Regarding claims 1-3, 7, and 10-19, Ueno teaches an organic light-emitting element having an extremely high efficiency, high luminance, and a long-life light output, wherein the organic light-emitting element includes an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode, and the light-emitting layer contains a compound represented by general formula [1] as a matrix material (¶ [0008]-[0012], [0031], [0036], and [0057]). Examples of compounds represented by general formula [1] include compound 16 (pg. 4).
general formula [1]:
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16:
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Compound 16 fails to include two phenylene groups fused to the core structure of general formula [1], and instead includes a phenylene group and a naphthalene group fused to the core structure. However, Ueno teaches R1 and R2, and R5 and R6 may form a fused ring (¶ [0012]). As shown in compound 16 above, the formed fused ring includes phenylene.
Therefore, given the general formula and teachings of Ueno, 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 the fused naphthalene group
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with a fused phenylene group as shown in compound 16
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, because Ueno teaches R1 and R2, and R5 and R6 may form a fused ring and the fused ring may suitably be selected as phenylene. The substitution would have been one known 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 the matrix material in the light emitting layer of the device of Ueno and possess the benefits taught by Ueno. See MPEP 2143.I.(B)
The modified compound 16 fails to read on the claimed Formula 1 as it does not comprise at least one cyano group, C3-C60 carbocyclic group, C1-C60 heterocyclic group or -N(Q1)(Q2).
In the analogous art of materials of organic electronic devices, Lu teaches a cyano group is a stronger electron-withdrawing group than a fluorine atom and thus could render a material with improved electron transporting performance as compared to the fluorine atom (¶ [0002], [0008], [0068]).
Therefore, in the modified compound 16, 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 the fluorine atom with a cyano group, based on the teaching of Lu. The motivation for doing so would have been to improve the electron transporting performance, as taught by Lu.
The modified compound 16 of Ueno in view of Lu is reproduced below in comparison to the claimed Formula 1.
Ueno in view of Lu:
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Formula 1:
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The modified compound 16 reads on the claimed Formula 1 wherein:
X3 to X10 are C(R3) to C(R10), respectively (claim 11);
Z is *-C(E1)=C(E2)-*’;
n1 is 1;
E1 is *”-(L1)a1-(R1)b1 and E2 is *”-(L2)a2-(R2)b2;
L1 and L2 are each a single bond (claims 12-13);
a1 and a2 are each 1;
R1 is a cyano group, and R2 to R10 are each hydrogen (claims 14-16); and
b1 and b2 are each 1.
Additionally, the modified compound 16 reads on the claimed Formulas 2-1 and 2-11 wherein Z1 is *C(E11)=C(E12)-*’; E11 is *”(L11)a11-(R11)b11 and E12 is *”-(L12)a12-(R12)b12; L11 and L12 are each a single bond; a11 and a12 are each 1; R11 is a cyano group and R12 is hydrogen (claims 17-19).
Regarding claim 7, although the instant claim is drawn to an apparatus, the only positive limitation of the claimed apparatus is organic light-emitting device of claim 1. Claim 7 does not add any further structural or functional limitations to the device and/or condensed cyclic compound. Ueno in view of Lu teach the organic light emitting device according to claim 1, as described above, and does not include any components that would make it unfit for use as an apparatus. Therefore, the OLED of Ueno in view of Lu according to claim 1 may be considered an electronic apparatus.
Claims 4-6 are rejected under 35 U.S.C. 103 as being unpatentable over Ueno (English translation of JP 2002324675 A obtained from Global Dossier) in view of Lu (US 2021/0013424 A1) as applied to claim 3 above, and further in view of Chen (US 20200411775 A1).
Regarding claims 4-6, Ueno in view of Lu teach the organic light-emitting element comprising the modified compound 16 in the light emitting layer, as described above with respect to claim 3.
Ueno in view of Lu fail to teach the light emitting layer further comprises a TADF compound or a phosphorescent dopant.
Chen teaches phosphorescent compounds having the structure of Formula I, which emit deep blue color, have very narrow FWHM, high PLQY, and provide a highly efficient device (abstract; ¶ [0144]).
Formula I:
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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 a compound of Chen’s Formula I in the light emitting layer of Ueno in view of Lu, based on the teaching of Chen. The motivation for doing so would have been to provide a compound which emits deep blue color, with very narrow FWHM and high PLQY, and provides a highly efficient device, as taught by Chen.
M in Chen’s Formula I is Pt or Pd (see Chen, ¶ [0006]), and thus is a transition metal-containing compound (claim 5). As a compound of Chen’s Formula I emits deep blue color and is provided in the light emitting layer, the light emitting layer emits blue light (claim 6).
Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable Ueno (English translation of JP 2002324675 A obtained from Global Dossier) in view of Lu (US 2021/0013424 A1) as applied to claim 7 above, and further in view of Jeong (US 7,652,287 B2).
Regarding claim 8, Ueno in view of Lu teach the electronic apparatus, as described above with respect to claim 7.
Ueno in view of Lu fail to teach the electronic apparatus comprising the organic light-emitting element further comprises a thin-film transistor.
Jeong teaches a light emitting display device including a thin film transistor (TNT) and a light emitting diode, wherein the TNT includes an N-type oxide semiconductor layer, a source electrode, and a drain electrode (abstract and col. 2 lines 64-67). Jeong teaches the cathode electrode of the OLED may electrically contact the drain electrode of the TFT (col. 6, lines 54-58). As the cathode is electrically connected to the anode, the anode would also be electrically connected to the drain electrode.
Jeong teaches the light emitting display including the TNT substantially overcomes one or more of the problems of the related art, which includes low mobility of the semiconductor layer, leakage current, and increased contact resistance (col. 1, 12-45).
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 include the organic light-emitting element of Ueno in view of Lu as the OLED of the light emitting display device of Jeong, based on the teaching of Jeong. The motivation for doing so would have been to substantially overcome the problems of the related art discussed above, as taught by Jeong.
Claim 9 is rejected under 35 U.S.C. 103 as being unpatentable over Ueno (English translation of JP 2002324675 A obtained from Global Dossier) in view of Lu (US 2021/0013424 A1) as applied to claim 7 above, and further in view of Cok (US 2004/0080267 A1).
Regarding claim 9, Ueno in view of Lu teach the electronic apparatus, as described above with respect to claim 7.
Ueno in view of Lu fail to teach the electron apparatus further comprises a touchscreen layer.
Cok teaches an integrated OLED display and touch screen made by providing an OLED on a substrate, providing a transparent encapsulating cover on the OLED, and forming a touch screen on a side of the transparent encapsulating cover (abstract). The display of Cok reduces the number of manufacturing steps, reduces the manufacturing costs, reduces the combined size of the display and touch screen device, and provides superior optical performance (¶ [0011]).
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 include the organic light-emitting element of Ueno in view of Lu as the OLED of the integrated OLED display and touch screen of Cok, based on the teaching of Cok. The motivation for doing so would have been to reduce the number of manufacturing steps, the manufacturing costs, the combined size of the display and touch screen device, and provide superior optical performance, as taught by Cok.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Ueno (English translation of JP 2002324675 A obtained from Global Dossier) in view of Lu (US 2021/0013424 A1) as applied to claim 10 above, and further in view of Liu (English translation of CN 112442035 A obtained from Global Dossier).
Regarding claim 20, Ueno in view of Lu teach the modified compound 9, as described above with respect to claim 10.
modified compound 9:
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The modified compound 9 fails to read on a claimed compound. However, Ueno does teach the compound of general formula [1] is a compound with excellent electron injection properties, and may be an electron transport material (¶ [0033]-[0034]).
Lu teaches the lowering of LUMO energy levels reduces an electron transport material’s sensitivity to moisture and oxygen and thus results in materials exhibiting air-stable electron transport (¶ [0006]). Lu teaches the cyano group is an example of a substituent that lowers the LUMO energy level of a material and improves electron transporting performance (¶ [0068] and [0076]).
In the analogous art of organic electroluminescent devices, Liu teaches an electron transport material containing at least two electron deficient groups (including cyano) significantly improves the electron injection capability compared with an electron transport material containing only one electron-deficient group (Technical Field on pg. 1; and bottom of pg. 15).
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 a second cyano substituent on the modified compound 9, based on the teachings of Lu and Liu. The motivation for doing so would have been to provide air-stable electron transport, lower the LUMO energy level of the compound, improve the electron transporting performance, as taught by Lu, and to significantly improve the electron injection capability, as taught by Liu.
In particular, 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 the second cyano substituent in the position corresponding to the claimed R2, because it would have been choosing from a limited number of suitable positions in which to substitute the cyano group, which would have been a choice from a finite number of identified, predictable solutions of a compound useful in the device of Ueno in view of Lu and Liu and possessing the benefits taught by Lu and Liu. One of ordinary skill in the art would have been motivated to produce additional compounds comprising cyano groups having the benefits taught by Lu 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).
The resulting modified compound 9 reads on the claimed compound 7.
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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