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 1-2, 4-7, 9-12, and 15 are amended due to Applicant's amendment dated 10/06/2026. Claims 1-16 are pending.
Response to Amendment
The objection to the drawings as set forth in the previous Office Action is overcome due to the Applicant's amendment dated 10/06/2025.
The objections to claims 4-7 and 9-12 as set forth in the previous Office Action are overcome due to the Applicant's amendment dated 10/06/2025.
The rejection of claims 2 and 10-11 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 as set forth in the previous Office Action is overcome due to the Applicant’s amendment dated 10/06/2025. The rejection is withdrawn.
The rejection of claims 1-4, 6-9, 11-14, and 16 under 35 U.S.C. 103 as being unpatentable over Nakamura (US 2007/0164285 A1) in view of Cai (English translation of CN 109560207 A obtained from Global Dossier) is not overcome due to the Applicant’s amendment dated 10/06/2025. The rejection is maintained.
The rejection of claims 5 and 10 under 35 U.S.C. 103 as being unpatentable over Nakamura in view of Cai and Cho (English translation of WO 2015083948 A1 obtained from Global Dossier) is not overcome due to the Applicant’s amendment dated 10/06/2025. The rejection is maintained.
The rejection of claim 15 under 35 U.S.C. 103 as being unpatentable over Nakamura in view of Cai and Bae (English translation of KR 20100097797 A obtained from Global Dossier) is not overcome due to the Applicant’s amendment dated 10/06/2025. The rejection is maintained.
Response to Arguments
Applicant’s arguments on pages 26-29 of the reply dated 10/06/2025 with respect to the rejection of claims 1-16 under 35 U.S.C. 103 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –On pages 26-28, Applicant argues the devices of the instant invention (Examples 1-4) achieve unexpectedly lower operating voltages over devices of the comparative examples (Comparative Examples 1-2), as shown in Table 3 of the instant specification. Applicant argues these unexpected results are attributed to the at least one radialene compound of the hole injection layer, and further argues these results overcome any alleged case of prima facie obviousness. Applicant argues the comparative examples include hole injection layers consisting of the dopant HAT-CN, which is consistent with Nakamura which recites any known hole injection material can be used (see Nakamura, ¶ [0053]).
Examiner's response –Claim 1 requires a first organic semiconductor layer comprising a metal dopant and a compound of Formula (I) and a second organic semiconductor layer comprising at least one radialene compound.
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
It should be noted that Comparative Examples 1-2 include hole injection layers (second organic semiconductor layer) consisting of HAT-CN whereas Examples 1-4 include hole injection layers (second organic semiconductor layer) consisting of a matrix compound HTM-1 and a radialene compound of A2. Thus, it is unclear whether the improvement in operating voltage is truly due to the radialene compound. For example, given that one of ordinary skill in the art would expect some degree of variability between devices comprising different materials, one of ordinary skill in the art could expect the use of HAT-CN or HTM-1 to affect the device properties (i.e., operating voltage). Accordingly, because the hole injection layers of Comparative Examples 1-2 and Examples 1-4 differ by more than just the radialene compound, it is unclear to what degree the difference in operating voltages may be attributed to the radialene compound and to what degree the difference in operating voltages may be attribute to the use of HAT-CN or HTM-1.
However, even if the devices of the Comparative Examples 1-2 and Examples 1-4 only differed by the radialene compound, Applicant has not made a comparison to the closest prior art. The device examples of the instant specification comprise different device structure and materials than the devices of Nakamura.
With respect to the device structure and materials, Nakamura teaches devices having the following (¶ [0050]-0059]):
Anode: ITO
Hole injection layer: copper phthalocyanine (Cu-Pc)
Hole transport layer: α-NPD
Light-emitting layer: Alq3 doped with 1 wt% coumarin 545T
Electron transport layer: Alq3
Electron injection layer: structure formula 2 and Li in a ratio of 1:2
Cathode: ITO
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The instant devices of instant Examples 1-4 include the following (instant pages 98-99; structures on pages 96-97):
Anode: ITO
Hole injection layer: HTM-1 and A2
Hole transport layer: Biphenyl-4-yl(9,9-diphenyl-9H-fluoren-2-yl)-[4-(9-phenyl-9H-carbazol-3-yl) phenyl]-amine
Electron blocking layer: N,N-bis(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1′:4′,1″-terphenyl]-4-amine
Light emitting layer: H09 doped with 3 vol% BD200
Hole blocking layer: 2-(3′-(9,9-dimethyl-9H-fluoren-2-yl)-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine
Electron transport layer: G1 or G12 doped with 1 wt% Li or 3 wt% Yb
Cathode: Al
G1:
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G12:
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As shown above, the devices of instant Table 3 do not make a comparison with the closest prior art with respect to the claimed first organic semiconductor layer. Nakamura teaches a device including an electron injection layer comprising Li and the pyridine derivative represented by structure formula 2 (¶ [0057]). Structure formula 2 reads on the claimed compound G45. Alternatively, the instant devices of Examples 1-4 include an electron transport layer comprising either Yb or Li and either compound G1 or G12 (see Table 3 on instant pg. 102). As the devices of Applicant and the devices of Nakamura comprise a different electron injection/transport layer, a comparison to the closest prior art has not been made.
Additionally, the devices of instant Table 3 do not make a comparison with the closest prior art with respect to the claimed second organic semiconductor layer. Nakamura teaches a device including a hole injecting layer consisting of copper phthalocyanine and alternatively the instant devices of Examples 1-4 include a hole injection layer HTM-1 (a matrix material) and A2 (a radialene compound). As recited in claim 1, the claimed second organic semiconductor layer is only required to comprise at least one radialene compound. Thus, any additional compounds may be included in the claimed second organic semiconductor layer. Accordingly, it is unclear if a device comprising the hole injection layer of Nakamura (copper phthalocyanine) that also contains at least one radialene compound would obtain the results as discussed by Applicant.
As shown above, the devices of the Declaration contain both a different layer structure and different layer materials as compared to the device of Nakamura. Applicant has not provided an explanation regarding this difference. It is unclear if the device comprising the same structure and materials of Nakamura that also contain at least one radialene compound would obtain the results as discussed by Applicant.
As the devices of Applicant and the devices of Nakamura comprise different structure and materials, a comparison is not being made to the closest prior art. Where the comparison is not identical with the reference disclosure, deviations therefrom should be explained, and if not explained should be noted and evaluated, and if significant, explanation should be required. MPEP 716.02(e).
Commensurate in Scope
As claims 1-16 claim a broad device structure including any materials but the devices discussed in Examples 1-4 only recite two specific device structures and materials (see instant pages 98-99), the claims are not commensurate in scope. For example, as discussed above, Nakamura teaches a compound of the claimed Formula (I) different from those used in Examples 1-4. Additionally, Nakamura teaches different device structure and materials than the instant examples. The structures and materials discussed in the prior art are within the claim scope of the instant application. As there are no results comprising the structures and materials of the prior art, it is unclear if the same results discussed by Applicant would be present.
Unexpected Results
While there is improvement in operating voltage between the instant Examples 1-4 and Comparative Examples 1-2, it is unclear whether these performances are truly unexpected.
As discussed above, the instant Examples 1-4 and Comparative Examples 1-2 do not contain identical materials in the hole injection layer. Accordingly, one of ordinary skill in the art would not expect the properties between the devices to be identical. That is, one of ordinary skill would expect some degree of variability between the operating voltage.
As discussed below and in the previous rejection, Cai teaches including an alkylene compound represented by general formula (II) (i.e., a radialene compound) may provide reduced driving voltage (see Cai, end of pg. 1 and middle of pg. 6). For example, as shown in Table 3 of Cai, Devices 1-10 achieve a 19-27% improvement in comparison to the comparative example (see Cai, pg. 16).
Given the teachings and degree of improvement shown by Cai, and given that one of ordinary skill in the art would expect some degree of variability between the operating voltage, it is unclear whether the degree of improvement shown by the data in instant Table 3 is truly unexpected.
Applicant's argument –On pages 28-29, Applicant argues with respect to the rejection of claim 15, the group of Bae is a “benzo[4,5]imidazo[1,2-a]indolo[3,2-c]quinoline” group which is not the “benzo[4,5]imidazo[1,2-a]quinolinylene” group noted by the Examiner.
Examiner's response –In the rejection of claim 15, Nakamura’s structure formula 2 is modified with the group
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(as shown in Bae’s formula 1a-46 on page 7). As evidenced by page 157 of Dumitrascu1, imidazo[1,2-a]quinoline has the structure below. Similarly, benzimidazo[1,2-a]quinoline has the structure below with the CAS registry number of 205-54-9, as evidenced by SciFinder2.
imidazo[1,2-a]quinoline
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benzimidazo[1,2-a]quinoline:
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Accordingly, the bold portion of Nakamura’s group reads on a benzo[4,5]imidazo[1,2-a]quinolinylene group.
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As recited in claim 15, Ar3 may be substituted and the substituents are not limited to any specific group. Accordingly, as discussed below and in the previous rejection, Nakamura’s group reads on the limitations of claim 15 wherein Ar3 is an substituted benzo[4,5]imidazo[1,2-a]quinolinyl, wherein the substituents thereof include hydrogen, amine, and aryl, wherein the amine and aryl are adjacent to each other and bond together to form a ring.
Claim Interpretation
Claim 5 recites:
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Claim 5 is interpreted as Ar3 may be a substituted or unsubstituted C6 to C36 aryl, a substituted or unsubstituted C6 to C36 arylene, a substituted or unsubstituted C6 to C36 heteroaryl group, or a substituted or unsubstituted C6 to C36 heteroarylene group, and when Ar3 is a substituted or unsubstituted C6 to C36 heteroarylene group, the substituted or unsubstituted C6 to C36 heteroarylene group is a substituted pyrazinylene, a substituted pyrimidinylene, a substituted or unsubstituted acridinylene, etc.
Claim Objections
The status of every claim must be indicated after its claim number using identifiers in a parenthetical expression. All claims currently amended must be indicated as “(Currently amended)”. See MPEP 714. Accordingly, claims 1 and 15 are objected to for being indicated as “(Original)” or (“Previously Presented)” rather than “(Currently amended)”.
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 1-4, 6-9, 11-14, and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Nakamura (US 2007/0164285 A1) in view of Cai (English translation of CN 109560207 A obtained from Global Dossier).
Regarding claims 1-4, 6-9, 11-14, and 16, Nakamura teaches a light-emitting element including an electron injection layer comprising a pyridine derivative represented by general formula 1 and at least one of an alkali metal, an alkali earth metal, and a transition metal (abstract). In particular, the light-emitting element includes an anode, a hole injection layer (second organic semiconductor layer), a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer (first organic semiconductor layer), and a cathode (¶ [0050]-[0052] and [0058]) (claim 13). The electron injection layer comprises the alkali metal Li and the pyridine derivative represented by the structure formula 2 (¶ [0057]) (claim 8).
The pyridine derivative of structure formula 2 reads on the claimed compound G45 (claim 12) is reproduced below in comparison to the claimed Formula (I).
formula 2:
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Formula (I):
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Structure formula 2 reads on the claimed Formula (I) wherein:
Ar1 and Ar2 are each an unsubstituted C5 heteroaryl of pyridyl (claim 3);
L is an unsubstituted phenylene represented by B3 (claims 4 and 9);
Ar3 is an unsubstituted C5 heteroarylene group;
Ar4 is an unsubstituted pyridyl represented by F3 (claims 6 and 11); and
n is 2.
Nakamura’s element fails to include a radialene compound. However, Nakamura teaches a known hole injection material can be used for the hole injection layer (¶ [0053]).
Cai teaches an effective hole injection layer may be formed by comprising an aromatic amine compound represented by general formula (I) and an alkylene compound represented by general formula (II) (end of pg. 1). By selecting the materials above as the hole injection layer, an organic electroluminescent device can obtain reduced driving voltage and improved life and luminous efficiency (middle of pg. 6). Cai teaches specific examples of such hole injection layers including that of Device 3, which includes the aromatic amine compound 8 and the alkylene compound HI1 (Table 3 on pg. 16; structure on pg. 13).
alkylene compound HI1:
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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 select Cai’s aromatic amine compound 8 and Cai’s alkylene compound HI1 as the hole injection layer of Nakamura, as shown in Cai’s Device 3, based on the teaching of Cai. The motivation for doing so would have been to provide an effective hole injection layer that provides a device with reduced driving voltage and improved life and luminous efficiency, as taught by Cai.
Cai’s compound HI1 reads on the claimed radialene compound A1 (claim 7). Fluorine and CN are electron withdrawing groups, and the claimed compound A1 is an example of a radialene compound that comprises a total amount of electron withdrawing groups of 13 atomic percent to 90 atomic percent (see instant pg. 33; instant pg. 13, lines 24-28). Accordingly, Cai’s compound HI1 comprises a total amount of electron withdrawing groups of 13 atomic percent to 90 atomic percent (claim 2).
Claims 5 and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Nakamura (US 2007/0164285 A1) in view of Cai (English translation of CN 109560207 A obtained from Global Dossier) as applied to claim 1 above, and further in view of Cho (English translation of WO 2015083948 A1 obtained from Global Dossier).
Regarding claims 5 and 10, Nakamura in view of Cai teach the light-emitting element comprising the pyridine derivative of structure formula 2, as described above with respect to claim 1.
The pyridine derivative of structure formula 2 fails to read on the claimed Formula (I) wherein Ar3 is represented by one of E1 to E9. However, Nakamura teaches the pyridine derivative is represented by general formula 1 wherein R2 may be a substituted aryl group, and does not limit the pyridine derivative to the structure formula 2 (abstract).
general formula 1:
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structure formula 2:
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Cho teaches an organic-electrical element having improved efficiency, lifespan, and color purity by including a compound with high electron mobility, more efficient electron-transport ability, and high temperature stability (¶ [9]). The compound may be used in an electron-injection layer, and is represented by the formula below wherein examples thereof including compound P-2 (¶ [11] and [50]; pg. 8).
Formula:
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P-2:
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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 substitute one of the terpyridine groups in Nakamura’s structure formula 2 with the benzoacridine group of
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, as shown by Cho’s P-2, and thus arrive at a compound represented by Cho’s formula, based on the teaching of Cho. The motivation for doing so would have been to provide a compound with high electron mobility, more efficient electron-transport ability, and high temperature stability, and to provide a device with improved efficiency, lifespan, and color purity, as taught by Cho.
The modified structure formula 2 reads on Nakamura’s general formula 1 wherein each of X1 and X2 represents an unsubstituted pyridine group, R1 and R3 to R7 each represent hydrogen, and R2 represents a substituted aryl group (see Nakamura, ¶ [0033]). Accordingly, Nakamura’s device comprising the modified structure formula 2 in the electron injection layer is expected to obtain the benefits of Nakamura above. Additionally, the modified structure formula 2 reads on Cho’s Chemical Formula 1 wherein R1 and R2 are not required to be present, n and m are each 0, L1 is a C6 aryl group, L2 is a C5 heterocyclic group, Ar1 is a C5 heterocyclic group, and x is 2 (see Cho, ¶ [61]-[71]). Accordingly, the modified structure formula 2 is expected to obtain the benefits of Cho.
The modified structure formula 2 reads on the claimed Formula (I) wherein:
Ar1 and Ar2 are each an unsubstituted C5 heteroaryl of pyridyl;
L is an unsubstituted phenylene;
Ar3 is an unsubstituted benzoacridinylene group represented by E3 (claims 5 and 10);
Ar4 is not required to be present; and
n is 0.
Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Nakamura (US 2007/0164285 A1) in view of Cai (English translation of CN 109560207 A obtained from Global Dossier) as applied to claim 1 above, and further in view of Bae (English translation of KR 20100097797 A obtained from Global Dossier).
Regarding claim 15, Nakamura in view of Cai teach the light-emitting element comprising the pyridine derivative of structure formula 2, as described above with respect to claim 1.
The pyridine derivative of structure formula 2 fails to read on the claimed formula (I) wherein Ar3 is selected from a substituted or unsubstituted benzo[4,5]imidazo[1,2-a]quinolinylene or benzo[4,5]imidazo[1,2-a]quinolinyl, as required by claim 15. However, Nakamura teaches the pyridine derivative is represented by general formula 1 wherein R2 may be a substituted aryl group, and does not limit the pyridine derivative to the structure formula 2 (abstract).
general formula 1:
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structure formula 2:
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Bae teaches a nitrogen-containing heterocyclic compound represented by Formula 1 for use in an organic electronic device, wherein the nitrogen-containing heterocyclic compound provides excellent characteristics in terms of efficiency, driving voltage, and lifetime (abstract; pg. 1). The compound represented by Formula 1 is preferably used in an electron injection layer (fifth paragraph of pg. 67). Bae teaches examples of compounds represented by Formula 1 including Formula 1a-46 on pg. 7.
Formula 1:
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Formula 1a-46:
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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 substitute one of the terpyridine groups in Nakamura’s structure formula 2 with the group of
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, as shown in Bae’s Formula 1a-46, and thus arrive at a compound represented by Bae’s Formula 1, based on the teaching of Bae. The motivation for doing so would have been to provide excellent characteristics in terms of efficiency, driving voltage, and lifetime, as taught by Bae.
The modified structure formula 2 reads on Nakamura’s general formula 1 wherein each of X1 and X2 represents an unsubstituted pyridine group, R1 and R3 to R7 each represent hydrogen, and R2 represents a substituted aryl group (see Nakamura, ¶ [0033]). Accordingly, Nakamura’s device comprising the modified structure formula 2 in the electron injection layer is expected to obtain the benefits of Nakamura above. Additionally, the modified structure formula 2 reads on Bae’s Formula 1 wherein X1 and X3 to X5 are each C, X2 and X6 are each N; R1, R4, and R8 are each hydrogen, R3 is represented by formula (2), R6 and R7 join to form a condensed ring, and R9 and R10 join to form a condensed ring; L1 is a C6 aryl; and Ar1 is a C5 heteroaryl group substituted with two C5 heteroaryl groups (see Bae, pgs. 1-2). Accordingly, the modified structure formula 2 is expected to obtain the benefits of Bae.
The modified structure formula 2 reads on the claimed formula (I) wherein:
Ar1 and Ar2 are each an unsubstituted C5 heteroaryl of pyridyl;
L is an unsubstituted phenylene;
Ar3 is an substituted benzo[4,5]imidazo[1,2-a]quinolinyl, wherein the substituents thereof include hydrogen, amine, and aryl, wherein the amine and aryl are adjacent to each other and bond together to form a ring;
Ar4 is not required to be present; and
n is 0.
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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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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/BRAELYN R WATSON/Examiner, Art Unit 1786
1 Dumitrascu, Florea, et al. "Pyrroloquinolines, imidazoquinolines, and pyrroloquinazolines with a bridgehead nitrogen." Advances in Heterocyclic Chemistry. Vol. 129. Academic Press, 2019. 155-244.
2 Benzimidazo[1,2-a]quinoline, CAS SciFinder, 2025.
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