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 .
Summary of Claims
Claims 1, 7, 9-10, and 18 are amended and claims 2-6 are cancelled due to Applicant's amendment dated 07/29/2026. Claims 1 and 7-26 are pending.
Response to Amendment
The rejections of claims 2-6 as set forth in the previous Office Action are moot because claims 2-6 are cancelled due to the Applicant's amendment dated 07/29/2026.
The rejection of claims 1, 7-8, 12-15, 17, and 19-21 under 35 U.S.C. 102(a)(2) as being anticipated by Kim (English translation of WO 2021261962 A1 obtained from Global Dossier) is overcome due to the Applicant’s amendment dated 07/29/2026. The rejection is withdrawn.
The rejection of claim 9 under 35 U.S.C. 103 as being unpatentable over Kim is not overcome due to the Applicant’s amendment dated 07/29/2026. The rejection is maintained.
The rejection of claims 22 and 26 under 35 U.S.C. 103 as being unpatentable over Kim is overcome due to the Applicant’s amendment dated 07/29/2026. The rejection is withdrawn.
The rejection of claims 10-11 under 35 U.S.C. 103 as being unpatentable over Kim in view of Jatsch (US 2018/0222872 A1) is overcome due to the Applicant’s amendment dated 07/29/2026. The rejection is withdrawn.
The rejection of claim 16 under 35 U.S.C. 103 as being unpatentable over Kim in view of Noh (US 2019/0372013 A1) is overcome due to the Applicant’s amendment dated 07/29/2026. The rejection is withdrawn.
The rejection of claim 18 under 35 U.S.C. 103 as being unpatentable over Kim in view of Fennimore (US 2017/0200893 A1) is overcome due to the Applicant’s amendment dated 07/29/2026. The rejection is withdrawn.
The rejection of claims 23-24 under 35 U.S.C. 103 as being unpatentable over Kim in view of Lee (US 2019/0074451 A1) is overcome due to the Applicant’s amendment dated 07/29/2026. The rejection is withdrawn.
The rejection of claim 25 under 35 U.S.C. 103 as being unpatentable over Kim in view of Lee and Kim ‘927 (US 2014/0014927 A1) is overcome due to the Applicant’s amendment dated 07/29/2026. The rejection is withdrawn.
The rejection of claims 1, 7-8, 12-15, 17, 19-24, and 26 under 35 U.S.C. 103 as being unpatentable over Lee is overcome due to the Applicant’s amendment dated 07/29/2026. The rejection is withdrawn.
The rejection of claim 9 under 35 U.S.C. 103 as being unpatentable over Lee is withdrawn due to reconsideration of the original grounds of rejection.
The rejection of claims 10-11 under 35 U.S.C. 103 as being unpatentable over Lee in view of Jatsch (US 2018/0222872 A1) is withdrawn due to reconsideration of the original grounds of rejection.
The rejection of claim 16 under 35 U.S.C. 103 as being unpatentable over Lee in view of Noh (US 2019/0372013 A1) is overcome due to the Applicant’s amendment dated 07/29/2026. The rejection is withdrawn.
The rejection of claim 18 under 35 U.S.C. 103 as being unpatentable over Lee in view of Fennimore (US 2017/0200893 A1) is overcome due to the Applicant’s amendment dated 07/29/2026. The rejection is withdrawn.
The rejection of claim 25 under 35 U.S.C. 103 as being unpatentable over Lee in view of Lee and Kim ‘927 (US 2014/0014927 A1) is overcome due to the Applicant’s amendment dated 07/29/2026. The rejection is withdrawn.
Response to Arguments
Applicant’s arguments on pages 10-16 of the reply dated 07/29/2026 with respect to the rejection of claims 1 and 7-26 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –Applicant argues on pgs. 10-11 that Kim provides no reason to arrive at a compound of formula (1-1).
Examiner's response –As discussed below and in the previous rejection, Kim teaches the compound on pg. 16 (shown below) which anticipates a 4-dibenzothiophenyl group directly attached to the triazine ring and anticipates a carbazole group attached in the ortho position.
Kim’s compound:
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While Kim’s compound lacks a biphenylene group attached to the triazine ring in the ortho-position, Kim does teach in Formula 1 that Ar1 may be a substituted or unsubstituted C6-60 aryl, wherein examples thereof include phenyl (as shown in the compound above on page 16) and biphenyl (as shown in the compound on page 15) (¶ [22]). Accordingly, a compound of the claimed formula (1-1) is within the scope of Kim’s Formula 1.
Therefore, given the general formula and teachings of Kim, 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 phenyl with biphenyl
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in the location of Ar1 (as shown in the compound on pg. 15), because Kim teaches the Ar1 may suitably be selected as biphenyl. 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 a host compound in the emitting layer of the device of Kim and possess the benefits taught by Kim. See MPEP 2143.I.(B).
Additionally, given the general formula and teachings of Kim, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of the compound wherein the biphenyl group is attached to the triazine ring in the ortho-position. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by Kim’s Formula 1 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as a host in the emission layer of the device of Kim and possess the properties taught by Kim. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP 2144.09 I. When compounds which are position isomers or homologs are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP 2144.09 II.
Accordingly, one of ordinary skill in the art would have sufficient motivation to modify the compound of Kim to arrive at a compound of the claimed invention.
Applicant's argument –Applicant argues on pg. 12 that one of ordinary skill in the art would have no reason to expect an increase lifetime of an organic electroluminescence device including a compound represented by the claimed formula (1-1) wherein a 4-dibenzothiophenyl group is directly attached to the triazine ring, and an ortho-phenylene group is directly attached to the triazine ring.
Applicant further argues on pgs. 12-16 that the Declarations filed 12/23/2025 and 07/29/2026 provide evidence of unexpected results by comparing compound ET-1 (a compound of the instant invention) with ET-Ref-a (comparative compound). Applicant argues compound ET-1 provides significantly higher LT95 than ET-Ref-a by comprising the carbazole group in the ortho position. Applicant points to Table A and B for support.
ET-1:
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ET-Ref-a:
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Applicant recites Table A compares results for LT95 evaluation in an EL device tested in configuration (a) (see remarks page 15). From the data in Table A, a device comprising ET-1 obtains about 19% improvement in LT95 compared to ET-Ref-a.
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Applicant recites Table B compares results for LT95 evaluation in an EL device tested in configuration (b) (see remarks page 15). From the data in Table B, a device comprising ET-1 obtains about 19% improvement in LT95 compared to ET-Ref-a.
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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 Declarations filed 12/23/2025 and 07/29/2026 comprise different device materials than the devices of Kim.
As discussed below and in the previous rejection, Kim’s compound on pg. 16 anticipates a compound wherein a carbazole group is provided in the ortho position. Accordingly, as the only difference between ET-1 and ET-Ref-a is the positioning of the carbazole group and Kim already anticipates a carbazole group in the claimed position, a comparison between ET-1 and ET-Ref-a does not show unexpected results over the prior art.
As shown by the structures above, Kim’s compound includes an unsubstituted phenyl group attached to the triazine group whereas ET-1 includes a biphenyl group attached to the triazine ring in the ortho-position. Applicant has not provided an explanation regarding this difference. It is unclear if a comparison between a device comprising Kim’s compound and a device comprising ET-1 would obtain the results discussed by Applicant (i.e., improved LT95).
Commensurate in Scope
The data shown in Tables A and B are not commensurate in scope with the claimed invention for at least the reasons that the data is shown for the use of a compound in the second electron-transporting layer of a device, whereas claims 1 and 7-21 are directed to a compound. The improved properties of LT95 are shown when the compound is used in a second electron-transporting layer of an OLED. None of these limitations are required by claims 1 and 7-21. No evidence has been provided to show that the unexpected results would be present for the use of the compound in other layers.
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 and 7-9, 12-15, 17, 19-22, and 26 are rejected under 35 U.S.C. 103 as being unpatentable over Kim (English translation of WO 2021261962 A1 obtained from Global Dossier).
Regarding claims 1, 7-9, 12-15, 17, and 19-21, Kim teaches an organic light-emitting device having improved driving voltage, efficiency, and lifespan by including an emission layer comprising a host including a compound represented by Formula 1 and a compound represented by Formula 2 (¶ [13]-[19]). Examples of compounds represented by Formula 1 include the compound below on page 16.
Kim’s compound:
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Kim’s compound fails to include a biphenyl group. However, in Formula 1, Ar1 may be a substituted or unsubstituted C6-60 aryl, wherein examples thereof include phenyl (as shown in the compound above on page 16) and biphenyl (as shown in the compound below on page 15) (¶ [22]).
Formula 1:
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compound on pg. 15:
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Therefore, given the general formula and teachings of Kim, 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 phenyl with biphenyl
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in the location of Ar1 (as shown in the compound on pg. 15 above), because Kim teaches the Ar1 may suitably be selected as biphenyl. 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 a host compound in the emitting layer of the device of Kim and possess the benefits taught by Kim. See MPEP 2143.I.(B).
The modified compound fails to read on the claimed formula (1-1) wherein the biphenyl is attached in the ortho-position with respect to the triazine ring.
Given the general formula and teachings of Kim, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of the modified compound wherein the biphenyl group is attached to the triazine ring in the ortho-position. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by Kim’s Formula 1 in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as a host in the emission layer of the device of Kim and possess the properties taught by Kim. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP 2144.09 I. When compounds which are position isomers or homologs are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP 2144.09 II.
Kim’s modified compound is reproduced below in comparison to the claimed formula (1-1).
modified compound:
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(1-1):
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Kim’s modified compound reads on the claimed formula (1-1) wherein:
L2 is a single bond (claim 15); and
R1 to R4, R11 to R17, R21 to R28, and R31 to R39 are each a hydrogen atom (claims 7-8, 12-14, and 17).
The modified compound reads on the claimed formula (1-11) (claim 9).
Additionally, as no substituents or substituents R are required to be present, the limitations of claims 19-20 are met.
Regarding claims 22 and 26, Kim teaches the modified compound for use in an organic light-emitting device, as described above with respect to claim 1.
Kim fails to teach a specific example of a device including the modified compound. However, Kim does teach an example of the organic light emitting device includes a positive electrode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a negative electrode, wherein the light emitting layer includes a compound represented by Formula 1 (¶ [14]-[16] and [33]).
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 modified compound in the device of Kim as described above, because this would have been combining the prior art elements of Kim according to known methods to yield predictable results of a device with improved driving voltage, efficiency, and lifespan, as taught by Kim. See MPEP 2143.I.(A).
Regarding claim 26, although the instant claim is drawn to an apparatus, the only positive limitation of the claimed apparatus is organic electroluminescence device of claim 22. Claim 26 does not add any further structural or functional limitations to the device and/or compound. Kim teaches the organic electroluminescence device according to claim 22, as described above, and does not include any components that would make it unfit for use as an apparatus. Therefore, the OLED of Kim according to claim 1 may be considered an apparatus.
Claims 10-11 are rejected under 35 U.S.C. 103 as being unpatentable over Kim (English translation of WO 2021261962 A1 obtained from Global Dossier) as applied to claim 1 above, and further in view of Jatsch (US 2018/0222872 A1).
Regarding claims 10-11, Kim teaches the modified compound for use in an organic light-emitting device, as described above with respect to claim 1.
modified compound:
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Formula 1:
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The modified compound fails to include a fluorenyl group in the location of the claimed Ar1. However, in Formula 1, Kim teaches Ar1 may be a substituted or unsubstituted C6-60 aryl, wherein examples thereof include phenyl (as shown in the compound on page 16) and fluorenyl
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(¶ [22]and [61]-[63]).
Jatsch teaches fluorene derivatives that are connected to a carbon atom of a diaryl substituted triazinyl derivative, wherein the fluorene derivatives are suitable as matrix materials or materials in the hole-blocking or electron-transport layer in an organic electroluminescent device (abstract). The fluorene derivatives are represented by formula (I) and provide a device with improved lifetime and/or operative voltage (¶ [0013]-[0015]). Examples of fluorene derivatives represented by formula (I) include compound 88 (pg. 28).
Formula (I):
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88:
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Therefore, in Kim’s modified compound, 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 biphenyl with fluorene
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in the location of Ar1, as shown in Jatsch’s compound 88, to arrive at a compound represented by Jatsch’s Formula (I), based on the teaching of Jatsch. The motivation for doing so would have been to provide a device with improved lifetime and/or operative voltage, as taught by Jatsch.
The modified compound reads on Jatsch’s Formula (I) wherein: a, c, and d are each 0 and b is 1; Z1 and Z2 are each a straight-chain alkyl having 1 C atom; e and f are each 0 and thus Y1 and Y2 are not required to be present; n is 0 and thus L is not required to be present; Ar1 is an aromatic ring system having 6 aromatic ring atoms substituted with a radical R1, and Ar2 is a heteroaromatic ring system having 13 aromatic ring atoms; and R1 a heteroaromatic ring system having 12 carbon atoms (¶ [0015]-[0025]). Accordingly, the modified compound is expected to obtain the benefits of Jatsch.
The modified compound of Kim in view of Jatsch is reproduced below.
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The modified compound reads on: the claimed formula (1-1) wherein R31 to R33 and R36 to R39 are each hydrogen, and R34 and R35 combine to form a substituted unsaturated ring; and the claimed formula (1-12) wherein R41 and R42 are each a substituent R that is an unsubstituted alkyl group including 1 carbon atom (claims 10-11).
Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Kim (English translation of WO 2021261962 A1 obtained from Global Dossier) as applied to claim 1 above, and further in view of Noh (US 2019/0372013 A1).
Regarding claim 16, Kim teaches the modified compound for use in an organic light-emitting device, as described above with respect to claim 1.
modified compound:
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Formula 1:
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Kim’s compound fails to read on the claimed formula (1) wherein L2 is an arylene group. However, Kim teaches L3 of Formula 1 may be a C6-C60 arylene group such as a phenylene group (as shown in Kim’s compound) or a biphenylene (¶ [23] and [96]).
Noh teaches an OLED having improved emission efficiency by including a space-through charge transfer compound represented by Formula 1, wherein A is selected from Formula 2 and D is selected from Formula 3 (¶ [0018] and [0021]). Examples of compounds represented by Formula 1 include compound 1 (pg. 4).
Formula 1 :
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Formula 2:
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Formula 3:
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compound 1:
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The modified compound reads on Noh’s Formula 1 except wherein it comprises a phenylene rather than a biphenylene between the carbazole and the triazine groups.
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 the phenylene group with a biphenylene group in the location of L3, as shown in Noh’s compound 1, to arrive at a compound represented by Noh’s Formula 1, based on the teaching of Noh. The motivation for doing so would have been to provide a device with improved emission efficiency, as taught by Noh.
The modified compound of Kim in view of Noh reads on Noh’s Formula 1 wherein: A is represented by
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; D is represented by
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; R1 and R2 are each a C6 or C12 aryl group; and R5 and R6 are each hydrogen (see Noh, ¶ [0037]-[0042]). Accordingly, the modified compound of Kim in view of Noh is expected to obtain the benefits of Noh.
Thus, the modified compound reads on the limitation wherein L2 is an unsubstituted arylene group having 6 carbon ring atoms.
Claim 18 is rejected under 35 U.S.C. 103 as being unpatentable over Kim (English translation of WO 2021261962 A1 obtained from Global Dossier) as applied to claim 1 above, and further in view of Fennimore (US 2017/0200893 A1).
Regarding claim 18, Kim teaches the modified compound for use in an organic light-emitting device, as described above with respect to claim 1.
modified compound:
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Formula 1:
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The modified compound fails to include at least one deuterium. However, Kim teaches R1 and R2 may be selected as deuterium and substituents of Formula 1 include deuterium (¶ [24]-[25] and [28]).
Fennimore teaches deuterated materials (wherein at least one H has been replaced by deuterium) can be less susceptible to degradation by holes, electrons, excitons, or a combination thereof, and can lead to improved device lifetime (¶ [0097]-[0098]). Additionally, deuterated compounds may result in greater processing tolerance for both the preparation and purification of the materials and in the formation of electronic devices using the materials (¶ [0098]).
Therefore, in the modified compound, 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 at least one hydrogen with deuterium, as taught by Fennimore. The motivation for doing so would have been to make the compound less susceptible to degradation, improve the device lifetime, and provide greater processing tolerance of the compounds, as taught by Fennimore.
Claims 23-24 are rejected under 35 U.S.C. 103 as being unpatentable over Kim (English translation of WO 2021261962 A1 obtained from Global Dossier) as applied to claim 22 above, and further in view of Lee (US 2019/0074451 A1).
Regarding claims 23-24, Kim teaches the organic light-emitting device comprising the modified compound, a hole blocking layer, an electron transport layer, and an electron injection layer, as described above with respect to claim 22.
modified compound:
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Kim fails to teach the modified compound may be used in an electron-transporting zone.
Lee teaches an organic light-emitting device including a condensed-cyclic compound represented by Formula 1A, wherein the condensed-cyclic compound may be included in the electron-transport region and the electron-transport region includes a hole blocking layer, an electron transport layer, and an electron injection layer (¶ [0187], [0251], and [0333]). The condensed-cyclic compound has excellent charge-transporting ability and thermal stability and provides the device with improved emission efficiency, driving voltage, and lifespan (¶ [0178]-[0179] and [0366]).
Kim’s modified compound reads on Lee’s Formula 1A wherein: ring A1 is represented by Formula 1D; X1 to X3 are each N; X4 is S; L4 is not required to be present; L21 is an unsubstituted C6 arylene group; a4 is 0 and a21 is 1; R4 is an unsubstituted C12 aryl group, R5, R6, and R17 are each hydrogen; and b5 is 3, and n6 and b17 are each 4 (see Lee, ¶ [0008]-[0021]). Accordingly, Kim’s modified compound is suitable for use in an electron-transport layer and an electron injection layer.
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 Kim’s modified compound in the hole blocking layer, the electron transport layer, or the electron injection layer of Kim’s device, because it would have been using a compound with excellent charge-transporting ability and thermal stability which provides a device with improved emission efficiency, driving voltage, and lifespan, as taught by Lee, and because Lee teaches such a compound is suitable for use in an electron-transport layer and an electron injection layer. One of ordinary skill in the art would reasonably have expected the modified compound and the hole blocking layer, electron transport layer, or electron injection layer 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).
With respect to claim 24, while Kim in view of Lee fail to specifically teach the modified compound is provided in the electron transport layer, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to specifically include the modified compound in the electron transport layer, because it would have been choosing from one of three layers in which to include Kim’s compound, which would have been a choice from a finite number of identified, predictable solutions of a device of Kim and possessing the benefits taught by Kim and Lee. One of ordinary skill in the art would have been motivated to produce additional devices comprising compounds represented by Kim’s Formula 1 having the benefits taught by Kim and Lee 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 25 is rejected under 35 U.S.C. 103 as being unpatentable over Kim (English translation of WO 2021261962 A1 obtained from Global Dossier) in view of Lee (US 2019/0074451 A1) as applied to claim 24 above, and further in view of Kim ‘927 (US 2014/0014927 A1).
Regarding claim 25, Kim in view of Lee teach the organic light-emitting device including the modified compound in the electron transport layer, as described above with respect to claim 24.
modified compound:
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Kim fails to teach the electron transport layer further includes an alkali metal compound.
Kim ‘927 teaches an organic light emitting device comprising an electron transport layer including a compound represented by Chemical Formula 1 and an alkali metal complex (abstract). Such a device has high efficiency and long life-span characteristics (¶ [0007]-[0008]).
Chemical Formula 1:
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Kim’s modified compound reads the Chemical Formula 1 of Kim ‘927 wherein: X is nitrogen; L1 and L3 are each a single bond, and L2 is an unsubstituted C6 arylene group; R1 and R2 are each an unsubstituted C12 heteroaryl group, and R3 is an unsubstituted C12 aryl group (see Kim ‘927, ¶ [0008]-[0012]).
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 an alkali metal complex in the electron transport layer, based on the teaching of Kim ‘927. The motivation for doing so would have been to provide a device having high efficiency and long life-span characteristics, as taught by Kim ‘927.
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.
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/Primary Examiner, Art Unit 1786
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