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, 7, 12-13, 16, 19, and 21 are amended, claim 17 is cancelled, and claim 22 is new due to Applicant's amendment dated 11/25/2025. Claims 1-10, 12-16, and 18-22 are pending.
Response to Amendment
The objection to claim 19 as set forth in the previous Office Action is overcome due to the Applicant's amendment dated 11/25/2025.
The rejections of claim 17 as set forth in the previous Office Action are moot because claim 17 is cancelled due to the Applicant's amendment dated 11/25/2025.
The rejection of claims 1-10, 12-16, and 18-21 under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement as set forth in the previous Office Action is overcome due to the Applicant’s amendment dated 11/25/2025. The rejection is withdrawn.
The rejection of claims 12-13 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 11/25/2025. The rejection is withdrawn.
The rejection of claim 7 under 35 U.S.C. 112(d) or 35 U.S.C. 112 (pre-AIA ), 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends as set forth in the previous Office Action is overcome due to the Applicant’s amendment dated 11/25/2025. The rejection is withdrawn.
The rejection of claims 1-4, 7, 9-10, 12-13, 16, and 19-20 under 35 U.S.C. 103 as being unpatentable over Li (US 2017/0331056 A1) is not overcome due to the Applicant’s amendment dated 11/25/2025. The rejection is maintained.
The rejection of claims 5-6 under 35 U.S.C. 103 as being unpatentable over Li in view of Chen (US 2018/0182981 A1) is not overcome due to the Applicant’s amendment dated 11/25/2025. The rejection is maintained.
The rejection of claims 8 and 14 under 35 U.S.C. 103 as being unpatentable over Li in view of Xia (US 2012/0223634 A1) is not overcome due to the Applicant’s amendment dated 11/25/2025. The rejection is maintained.
The rejection of claim 15 under 35 U.S.C. 103 as being unpatentable over Li in view of Chen, Xia, and Zhang (Zhang, Jie, et al. “New phosphorescent platinum (II) Schiff base complexes for PHOLED applications.” Journal of Materials Chemistry 22.32 (2012):16448-16457) is not overcome due to the Applicant’s amendment dated 11/25/2025. The rejection is maintained.
The rejection of claims 16-17 under 35 U.S.C. 103 as being unpatentable over Li in view of Kai (US 2010/0187977 A1) is not overcome due to the Applicant’s amendment dated 11/25/2025. The rejection is maintained.
The rejection of claim 18 under 35 U.S.C. 103 as being unpatentable over Li in view of Chen and Xia is not overcome due to the Applicant’s amendment dated 11/25/2025. The rejection is maintained.
The rejection of claim 21 under 35 U.S.C. 103 as being unpatentable over Li in view of Chen and Xia ‘410 (US 2017/0179410 A1) is not overcome due to the Applicant’s amendment dated 11/25/2025. The rejection is maintained.
Response to Arguments
Applicant’s arguments on pages 73-87 of the reply dated 11/25/2025 with respect to the rejection of claims 1-10, 12-16, and 18-21 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument –Applicant argues on pages 73-87 that the inventive compounds show unexpected results over the prior art. Applicant points to Table 1 and 2 for support, which include data from the three Declarations filed 09/21/2023, 03/06/2025, and 11/25/2025.
Table 1
Table 2
Compound
FWHM (nm)
Compound
FWHM (nm)
Inventive Compound 1
26
Inventive Compound 1
16
Comparative Compound 1
32
Inventive Compound 2
16
Inventive Compound 2
19
Inventive Compound 3
15
Inventive Compound 3
20
Comparative Compound A
77
Comparative Compound 2
22
Comparative Compound B
50
The compounds having the following structures:
Inv. Compound 1:
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Comp. Compound 1:
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Inv. Compound 2:
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Comp. Compound B:
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Inv. Compound 3:
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Comp. Compound 2:
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Comp. Compound A:
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On pages 79-81, Applicant argues that given Inventive Compound 1 is structurally similar to Comparative Compound 1, and given Inventive Compounds 2 and 3 are structurally similar to Comparative Compound 2, one of ordinary skill in the art would expect these compounds to show similar properties. However, Applicant argues that due to the additional carbazole moiety of Formula II or III, the inventive compounds show unexpectedly lower FWHM compared to their respective comparative compounds.
On page 83, Applicant argues that while each of Inventive Compounds 1-3 and Comparative Compound A comprise an additional carbazole moiety, the Inventive Compounds 1-3 exhibit an unexpected lower of the FWHM compared to Comparative Compound A.
On pages 83-84, Applicant argues that Inventive Compound 2 and Comparative Compound B are isomers, wherein the only difference is the bonding position of the additional carbazole moiety. Applicant argues that as isomers, one of ordinary skill would expect these compounds to have similar properties. However, Applicant argues Inventive Compound 2 has an unexpectedly narrower FWHM than Comparative Compound B. Applicant attributes this improvement to the additional carbazole moiety being bonded to the ring containing X1 to X4 in the instant Formula VI rather than being bonded to ring A.
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).
With respect to the comparison between Inventive Compound 1 and Comparative Compound 1, and the comparison between Inventive Compounds 2-3 and Comparative Compound 2:
Applicant attributes the improved properties of Inventive Compounds 1-3 to an additional carbazole moiety that Comparative Compounds 1-2 lack.
As discussed below and in the previous rejection, Li teaches the compound PtON6-Cab on pg. 22. As seen in the structure below, PtON6-Cab comprises a carbazole substituent in the location of the claimed RA. That is, Li already anticipates a compound comprising an additional carbazole moiety represented by Formula II. Accordingly, a comparison between Inventive Compound 1 and Comparative Compound 2, and a comparison between Inventive Compounds 2-3 and Comparative Compound 2 do not show unexpected results over the prior art.
With respect to the comparison between Inventive Compounds 1-3 and Comparative Compound A:
Comparison with closest prior art
Applicant has not made a comparison to the closest prior art. The device examples of the Declarations comprise different compound structures than the compounds of Li.
As discussed below and in the previous rejection, Li teaches the compound PtON6-Cab on pg. 22. As seen in the structure below, PtON6-Cab comprises a carbazole substituent in the location of the claimed RA.
PtON6-Cab:
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As seen in the compounds of the Declarations above, differences exist between the inventive compounds and the compounds of the prior art (i.e., Li’s PtON6-Cab). For example, Inventive Compounds 1-3 each comprise a tert-butyl substituent on the pyridine ring (whereas the compound of Li does not), and a benzimidazole ring substituted with either deuterated tert-butyl or deuterated terphenyl whereas the compound of Li includes phenyl-substituted pyrazole in the same location. Additionally, Comparative Compound A includes two methyl substituents on the pyrazole group whereas the compound of Li includes a phenyl substituent.
Given the differences discussed above, it is unclear whether the narrower FWHM is truly due to the location of the carbazole substituent. For example, given that one of ordinary skill in the art would expect some degree of variability of properties between compounds having different structures, one of ordinary skill in the art could expect the deuterated tert-butyl or deuterated terphenyl substituents of Inventive Compounds 1-3 to affect the FWHM in comparison to Comparative Example A, which does not include the deuterated tert-butyl or deuterated terphenyl substituents. Accordingly, it is unclear to what degree the difference in FWHM may be attributed to the location of the claimed carbazole substituent, and to what degree the difference may be attributed to other differences (such as a deuterated tert-butyl group substituted on a benzimidazole group in the case of Inventive Compound 1).
As no explanation is provided for compounds having these different substituents and rings, it is unclear if a comparison between compounds comprising the same structure of Li would obtain the same results discussed by Applicant. Accordingly, a comparison has not been 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).
As a comparison between Li’s PtON6-Cab and a compound having the structure of Li’s PtON6-Cab except wherein the carbazole substituent is located on the highlighted carbazole group
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, a comparison to the closest prior art has not been made. Thus, it cannot be determined that the inventive compounds achieve unexpected results over the prior art.
Commensurate in Scope
As claim 1 claims a broad compound structure including any ring A and any additional ligands coordinated to M but the compounds discussed (Inventive Compounds 1-3) recite only three specific structures, the claims are not commensurate in scope. For example, as discussed above, the prior art teaches a different compound structure than the instant compounds, and these are within the claim scope of the instant invention. As there are no results comprising the compound structure of the prior art, it is unclear if the same results discussed by Applicant would be present.
With respect to the comparison between Inventive Compound 2 and Comparative Compound B:
Comparison with closest prior art
Applicant has not made a comparison to the closest prior art.
Applicant alleges that the only difference between Inventive Compound 2 and Comparative Compound B is the bonding position of the additional carbazole moiety. However, as shown by the structures above, Inventive Compound 2 and Comparative Compound B differ by more than just the bonding position of the additional carbazole moiety. Inventive compound 2 includes an additional tert-butyl substituent on the ring corresponding to RA. As no explanation is provided for this difference, it is unclear if a comparison between Comparative Compound B and Inventive Compound 2 not having the additional tert-butyl substituent would obtain the same results discussed by Applicant. Accordingly, a comparison of the closest prior art has not been made. 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).
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, 7, 9-10, 12-13, 16, 19-20, and 22 are rejected under 35 U.S.C. 103 as being unpatentable over Li (US 2017/0331056 A1).
Regarding claims 1-3, 7, 9-10, 12-13, 20, and 22, Li teaches multidentate metal complexes useful as phosphorescent emitters having the structure represented by one of the formulas below (abstract and ¶ [0009]). These complexes have improved stability, efficiency, and/or operational lifetimes in organic light emitting devices (¶ [0083] and [0122]).
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Li teaches compounds represented by the above formulas on pgs. 19-24 including the compound PtON6-Cab on pg. 22.
Li’s PtON6-Cab:
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The compound PtON6-Cab fails to include the carbazole substituent on L3 in the location of Rc. However, Li does teach Rc may represent a heteroaryl group (¶ [0018]).
Given the general formula and teachings of Li, 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 PtON6-Cab wherein the carbazole substituent is located on the 3-position of the carbazole of L3. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by Li’s formulas in order to pursue the known options within his or her technical grasp and would expect the isomeric compounds to be useful as the phosphorescent emitters of Li and possess the properties taught by Li. 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.
The modified PtON6-Cab is reproduced below in comparison to the claimed Formula VI of claim 1. Additionally, the modified compound reads on the claimed Formula IV of claims 10 and 22, the third structure of claim 12, and the third structure on pg. 11 of claim 13.
Modified PtON6-Cab:
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Formula II:
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Formula VI:
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The modified PtON6-Cab reads on the claimed Formulas VI and II of claim 1 wherein:
Z1, Z3, and Z4 are each N and Z2, Z5, and Z6 are each C (claim 7);
Each of K1 to K4 is a direct bond;
L is a direct bond, L1 is absent, and L2 is O;
Ring A is a 6-membered heterocyclic ring of pyridine, ring C is a 6-membered carbocyclic ring, and ring D is a 5-membered heterocyclic ring of pyrazole (claim 9);
RA represents four substitutions of hydrogen;
RC represents three substitutions of hydrogen and RD represents a mono substitution of aryl;
M is Pt;
Each of X1-X2 and X4-X6 is CR wherein each R is hydrogen, and X3 is CR wherein R is Formula II (claims 2-3); and
Each of X8-X15 is CR’ wherein each R’ is hydrogen (claim 3).
Per claim 20, a formulation does not require any additional structure limitations and is therefore met by the compound.
Regarding claim 4, Li teaches the compound modified PtON6-Cab below, as described above with respect to claim 1.
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The modified PtON6-Cab fails to read on the claimed Formula 1 wherein one of X1-X15 is N. However, Li teaches substituents of the compound (Ra to Rd) may be aryl or heteroaryl groups, including carbazole or azacarbazole as exemplified by compounds PtON1-Cab and PtON1-N-Cab below (¶ [0018] and pg. 24).
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Therefore, given the general formula and teachings of Li, 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 carbazole substituent with azacarbazole, because Li teaches the compound’s substituents may suitably be selected as azacarbazole, as shown in compound PtON1-N-Cab. 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 phosphorescent emitter and possess the benefits taught by Li. See MPEP 2143.I.(B).
The resulting compound meets the limitation of claim 4 wherein X15 is N.
Regarding claims 16 and 19, Li teaches the modified PtON6-Cab, as described above with respect to claim 1.
Li fails to teach an example of an OLED comprising the modified phosphorescent emitting compound PtON6-Cab. However, Li teaches an example in Fig. 1 of an OLED including an anode, an emissive layer including emissive materials, and a cathode (¶ [0004]).
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 PtON6-Cab in an emissive layer of an OLED having the structure of Li’s Fig. 1, because one of ordinary skill in the art would reasonably have expected the OLED and the modified phosphorescent emitter PtON6-Cab to predictably maintain their respective properties or functions after they have been combined, and this would have been combining an OLED device structure of Li with a phosphorescent emitter of Li according to known methods to yield predictable results. See MPEP 2143.I.(A).
Per claim 19, a light emitting device may include a full color display or a phosphorescent display device (¶ [0021]), which can be a consumer product. Thus the limitation is met.
Claims 5-6 are rejected under 35 U.S.C. 103 as being unpatentable over Li (US 2017/0331056 A1) as applied to claim 1 above, and further in view of Chen (US 2018/0182981 A1).
Regarding claims 5-6, Li teaches the modified PtON6-Cab below, as described above with respect to claim 1.
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The modified PtON6-Cab fails to read on the claimed Formula 1 wherein one of X1-X15 is N. However, Li teaches substituents of the compound (Ra to Rd) may be aryl or heteroaryl groups, including carbazole or azacarbazole as exemplified by compounds PtON1-Cab and PtON1-N-Cab below (¶ [0018] and pg. 24).
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Therefore, given the general formula and teachings of Li, 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 carbazole substituent with azacarbazole, because Li teaches the compound’s substituents may suitably be selected as azacarbazole, as shown in compound PtON1-N-Cab. 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 phosphorescent emitter and possess the benefits taught by Li. See MPEP 2143.I.(B).
The resulting compound meets the limitation wherein X15 is N.
While the modified compound fails to teach wherein L3 is an azacarbazole, Li does teach L3 may be a heterocyclic group (¶ [0012]).
Chen teaches a phosphorescent emitter in organic light emitting devices having a structure of the formula below, wherein at least one of X1 to X11 is N (abstract and ¶ [0017]). Such a compound has better stability due to the replacement of C-H with nitrogen (¶ [0058]).
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Chen teaches examples of such compounds on pgs. 11-18 including Compound 122 below wherein X2 is N and X3 is C (pg. 15).
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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 replace a C-H with nitrogen in the modified compound of Li, as shown in Chen’s Compound 122 to obtain better stability, as taught by Chen.
The modified compound reads on the claimed Formula I wherein X1 and X15 are each N.
Claims 8 and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Li (US 2017/0331056 A1) as applied to claim 1 above, and further in view of Xia (US 2012/0223634 A1).
Regarding claims 8 and 14, Li teaches the modified PtON6-Cab, as described above with respect to claim 1.
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The modified PtON6-Cab fails to include a substituent having at least three aromatic rings, as required by claims 8 and 14. However, Li does teach Ra may be a substituted aryl group (¶ [0018]).
Xia teaches tetradentate platinum compounds comprising a twisted aryl substituent for use in organic light emitting devices (¶ [0003]). Xia teaches the twisted aryl group may prevent excimer formation, increase efficiency, and improve sublimation (¶ [0097]). Xia teaches examples of platinum compounds comprising a twisted aryl substituent including Compound 13’ (pg. 10).
Compound 13’:
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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 a terphenyl group on the modified PtON6-Cab (as shown in Xia’s Compound 13’) to arrive at a compound having a twisted aryl group, based on the teaching of Xia. The motivation for doing so would have been to prevent excimer formation, increase efficiency, and improve sublimation, as taught by Xia.
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 substitute the phenyl group on ring L1 with the twisted aryl group because Li teaches Ra may be a substituted aryl group, and because it would have been choosing a specific position in which to place the twisted aryl group. This would have been a choice from a finite number of identified, predictable solutions of a compound useful as the phosphorescent emitter of Li and possessing the benefits taught by Li above. One of ordinary skill in the art would have been motivated to produce additional compounds comprising twisted aryl groups having the benefits taught by Xia in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The modified PtON6-Cab reads on the claimed Formula VI wherein ring D is a 5-membered heterocyclic ring and at least one RD comprises at least three aromatic rings (claim 8). Additionally, the modified PtON6-Cab reads on the claimed Compound (99340)-III-(A’2)(B41)(B41) (Ai)(Bj)(Bk) of claim 14.
Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Li (US 2017/0331056 A1) as applied to claim 1 above, and further in view of Chen (US 2018/0375036 A1), Xia (US 2012/0223634 A1), Zhang (Zhang, Jie, et al. "New phosphorescent platinum (II) Schiff base complexes for PHOLED applications." Journal of Materials Chemistry 22.32 (2012): 16448-16457.).
Regarding claim 15, Li teaches the modified PtON6-Cab, as described above with respect to claim 1.
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The modified PtON6-Cab fails to include a benzimidazole group. However, Li does teach the L1-L2 ligand may be represented by the structure below (¶ [0105]).
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Chen teaches tetradentate platinum complexes represented by Formula I for use as very efficient emitters in OLED (¶ [0015]-[0016] and [0145]). The complexes represented by Formula I exhibit physical properties that can be tuned, such as sublimation temperature, emission color, and device stability, and these complexes may provide devices with higher efficiencies and lower voltages (¶ [0015], [0145], and [0148]). Chen teaches examples of complexes represented by Formula I including Compound 226820 (pg. 82).
Formula I:
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226820:
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Therefore, in the modified PtON6-Cab, 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 pyrazole moiety
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with the benzimidazole moiety shown in Chen’s compound 226820
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to arrive at a compound that reads on Chen’s Formula I, based on the teaching of Chen. The motivation for doing so would have been to provide a compound that exhibits physical properties that can be tuned, such as sublimation temperature, emission color, and device stability, and provide a device with higher efficiencies and lower voltages, as taught by Chen.
The modified PtON6-Cab fails to include a substituent having at least three aromatic rings. However, Li does teach Ra may be a substituted aryl group (¶ [0018]).
Xia teaches tetradentate platinum compounds comprising a twisted aryl substituent for use in organic light emitting devices (¶ [0003]). Xia teaches the twisted aryl group may prevent excimer formation, increase efficiency, and improve sublimation (¶ [0097]). Xia teaches examples of platinum compounds comprising a twisted aryl substituent including Compound 13’ (pg. 10).
Compound 13’:
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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 a terphenyl group on the modified PtON6-Cab (as shown in Xia’s Compound 13’) to arrive at a compound having a twisted aryl group, based on the teaching of Xia. The motivation for doing so would have been to prevent excimer formation, increase efficiency, and improve sublimation, as taught by Xia.
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 substitute the phenyl group on ring L1 with the twisted aryl group because Li teaches Ra may be a substituted aryl group, and because it would have been choosing a specific position in which to place the twisted aryl group. This would have been a choice from a finite number of identified, predictable solutions of a compound useful as the phosphorescent emitter of Li and possessing the benefits taught by Li above. One of ordinary skill in the art would have been motivated to produce additional compounds comprising twisted aryl groups having the benefits taught by Xia in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The modified PtON6-Cab fails to read on a claimed compound as it does not comprise a t-butyl substituent on the phenyl ring. However, However, Li does teach Rd may be an alkyl group, wherein examples thereof include t-butyl, as shown by compound PtON6-tBu (¶ [0018] and [0048]; pg. 21).
PtON6-tBu:
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Zhang teaches in phosphorescent organic light-emitting devices (pg. 16448, left column), bulky substituents—such as tert-butyl and triphenylamino groups—on platinum complexes effectively reduce aggregation or excimer formation and subsequently improve the performance of the device (pg. 16448, right column, last 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 bulky substituents on the modified compound PtON6-Cab of Li in view of Chen and Xia, based on the teaching of Zhang. The motivation for doing so would have been to reduce aggregation or excimer formation and improve the device performance, as taught by Zhang.
Additionally, 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 substitute a t-butyl substituent in the para-position with respect to the C-N bond of the pyridine ring (as shown in Li’s PtON6-tBu), because it would have been choosing one of two possible bulky substituents identified by Zhang in a particular position identified by Li, and this would have been a choice from a finite number of identified, predictable solutions of a compound of Li’s formulas and possessing the benefits taught by Li and Zhang. One of ordinary skill in the art would have been motivated to produce additional compounds comprising bulky substituents having the benefits taught by Zhang in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The modified PtON6-Cab reads on Chen’s Formula I wherein A and B are each a 6-membered aromatic ring; Z1 is N and Z2 is C; L1 is O, and L2 is NR’; RA is alkyl, RB is a heteroaryl, RC is hydrogen, RD is alkenyl that are fused into a ring, R and R’ are each an aryl, and RB is fused with R’ of L2 to form a ring (see Chen, ¶ [0046]). Accordingly, the modified PtON6-Cab is expected to obtain the benefits of Chen. Additionally, as the modified PtON6-Cab comprises a twisted aryl and a bulky t-butyl substituent, it is expected to obtain the benefits of Xia and Zhang.
Additionally, as evidenced by Chen’s Formula I and Compound 226820 above, the carbene-based imidazole group
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may be alternatively drawn using a double bond
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.
Accordingly, the modified PtON6-Cab has the claimed structure below.
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Claims 16 is rejected under 35 U.S.C. 103 as being unpatentable over Li (US 2017/0331056 A1) as applied to claim 1 above, and further in view of Kai (US 2010/0187977 A1).
Regarding claim 16, Li teaches the modified PtON6-Cab, as described above with respect to claim 1.
Li fails to teach the modified PtON6-Cab is provided in an emissive layer of an OLED that further comprises a host having an indolocarbazole structure. However, as discussed above, Li does teach complexes of Li’s structures (including PtON6-Cab) have improved stability, efficiency, and/or operational lifetimes in organic light emitting devices (¶ [0083] and [0122]).
Kai teaches an organic electroluminescent device having improved luminous efficiency and driving stability by providing a light-emitting layer comprising a phosphorescent dopant and an indolocarbazole derivative as a host material, wherein the indolocarbazole compounds are represented by formula (2) or (3) (abstract). Kai teaches examples of such compounds including compound (3) below (pg. 4). Kai teaches an example of an organic EL device including compound (3) as the host material in the light emitting layer in combination with the phosphorescent dopant Ir(ppy)3 (see Example 3, ¶ [0060]-[0062]). Kai does not limit the phosphorescent dopant to a particular structure (¶ [0041]-[0042]).
Kai’s compound (3):
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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 Ir(ppy)3 with Li’s modified PtON6-Cab in Kai’s organic EL device of Example 3, based on the teachings of Li and Kai. The motivation for doing so would have been to obtain a device having improved stability, efficiency, and/or operational lifetime, as taught by Li, and to provide a device having improved luminous efficiency and driving stability, as taught by Kai.
The resulting device includes an indolocarbazole-based host compound.
Claim 18 is rejected under 35 U.S.C. 103 as being unpatentable over Li (US 2017/0331056 A1) as applied to claim 1 above, and further in view of Chen (US 2018/0375036 A1) and Xia (US 2012/0223634 A1).
Regarding claim 18, Li teaches the modified PtON6-Cab, as described above with respect to claim 1.
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The modified PtON6-Cab fails to include a benzimidazole group. However, Li does teach the L1-L2 ligand may be represented by the structure below (¶ [0105]).
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Chen teaches tetradentate platinum complexes represented by Formula I for use as very efficient emitters in OLED (¶ [0015]-[0016] and [0145]). The complexes represented by Formula I exhibit physical properties that can be tuned, such as sublimation temperature, emission color, and device stability, and these complexes may provide devices with higher efficiencies and lower voltages (¶ [0015], [0145], and [0148]). Chen teaches examples of complexes represented by Formula I including Compound 226820 (pg. 82).
Formula I:
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226820:
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Therefore, in the modified PtON6-Cab, 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 pyrazole moiety
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with the benzimidazole moiety shown in Chen’s compound 226820
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to arrive at a compound that reads on Chen’s Formula I, based on the teaching of Chen. The motivation for doing so would have been to provide a compound that exhibits physical properties that can be tuned, such as sublimation temperature, emission color, and device stability, and provide a device with higher efficiencies and lower voltages, as taught by Chen.
The modified PtON6-Cab fails to include a substituent having at least three aromatic rings. However, Li does teach Ra may be a substituted aryl group (¶ [0018]).
Xia teaches tetradentate platinum compounds comprising a twisted aryl substituent for use in organic light emitting devices (¶ [0003]). Xia teaches the twisted aryl group may prevent excimer formation, increase efficiency, and improve sublimation (¶ [0097]). Xia teaches examples of platinum compounds comprising a twisted aryl substituent including Compound 13’ (pg. 10).
Compound 13’:
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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 a terphenyl group on the modified PtON6-Cab (as shown in Xia’s Compound 13’) to arrive at a compound having a twisted aryl group, based on the teaching of Xia. The motivation for doing so would have been to prevent excimer formation, increase efficiency, and improve sublimation, as taught by Xia.
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 substitute the phenyl group on ring L1 with the twisted aryl group because Li teaches Ra may be a substituted aryl group, and because it would have been choosing a specific position in which to place the twisted aryl group. This would have been a choice from a finite number of identified, predictable solutions of a compound useful as the phosphorescent emitter of Li and possessing the benefits taught by Li above. One of ordinary skill in the art would have been motivated to produce additional compounds comprising twisted aryl groups having the benefits taught by Xia in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
The modified PtON6-Cab reads on Chen’s Formula I wherein A and B are each a 6-membered aromatic ring; Z1 is N and Z2 is C; L1 is O, and L2 is NR’; RA and RC are each hydrogen, RB is a heteroaryl, RD is alkenyl that are fused into a ring, R and R’ are each an aryl, and RB is fused with R’ of L2 to form a ring (see Chen, ¶ [0046]). Accordingly, the modified PtON6-Cab is expected to obtain the benefits of Chen. Additionally, as the modified PtON6-Cab comprises a twisted aryl, it is expected to obtain the benefits of Xia.
The modified PtON6-Cab reads on the claimed Formula VI wherein ring D is an imidazole which coordinates to Pt via a carbene carbon, wherein two RD are joined to the imidazole to form a fused benzene ring, and at least one RD comprises at least three aromatic rings.
Claim 21 is rejected under 35 U.S.C. 103 as being unpatentable over Li (US 2017/0331056 A1) as applied to claim 1 above, and further in view of Chen (US 2018/0375036 A1) and Xia ‘410 (US 2017/0179410 A1).
Regarding claim 21, Li teaches the modified PtON6-Cab, as described above with respect to claim 1.
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The modified PtON6-Cab fails to include a benzimidazole group. However, Li does teach the L1-L2 ligand may be represented by the structure below (¶ [0105]).
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Chen teaches tetradentate platinum complexes represented by Formula I for use as very efficient emitters in OLED (¶ [0015]-[0016] and [0145]). The complexes represented by Formula I exhibit physical properties that can be tuned, such as sublimation temperature, emission color, and device stability, and these complexes may provide devices with higher efficiencies and lower voltages (¶ [0015], [0145], and [0148]). Chen teaches examples of complexes represented by Formula I including Compound 226820 (pg. 82).
Formula I:
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226820:
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Therefore, in the modified PtON6-Cab, 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 pyrazole moiety
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with the benzimidazole moiety shown in Chen’s compound 226820
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to arrive at a compound that reads on Chen’s Formula I, based on the teaching of Chen. The motivation for doing so would have been to provide a compound that exhibits physical properties that can be tuned, such as sublimation temperature, emission color, and device stability, and provide a device with higher efficiencies and lower voltages, as taught by Chen.
The modified PtON6-Cab fails to include a substituent on a carbon atom of the benzimidazole group. However, Li does teach substituents of the compound may include combinations of alkyl and deuterium (¶ [0018] and [0108]).
Xia ‘410 teaches compounds comprising a ligand having deuterium substitution may be advantageously used in organic light emitting devices (¶ [0067]). The CD3 substituent may improve compound stability due to the greater strength of the C-D bond compared to that of the C-H bond (¶ [0063]). Additionally, deuterium substitution can improve efficiency, stability, and lifetime (¶ [0066]). Xia ‘410 teaches examples of compounds comprising a ligand having deuterium substitution including Compound 16, which comprises a CD3 substituent on a benzimidazole group (pg. 12).
Compound 16:
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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 a CD3 substituent on the benzene ring of the benzimidazole group of the modified PtON6-Cab, as shown in Compound 16 of Xia ‘410, to arrive at a compound having a deuterium substituent, based on the teaching of Xia ‘410. The motivation for doing so would have been to provide improved efficiency, stability, and lifetime, as taught by Xia ‘410.
The modified PtON6-Cab reads on Chen’s Formula I wherein A and B are each a 6-membered aromatic ring; Z1 is N and Z2 is C; L1 is O, and L2 is NR’; RA and RC are each hydrogen, RB is a heteroaryl, RD includes alkenyl groups that are fused into a ring and combinations of deuterium and alkyl, R and R’ are each an aryl, and RB is fused with R’ of L2 to form a ring (see Chen, ¶ [0046]). Accordingly, the modified PtON6-Cab is expected to obtain the benefits of Chen. Additionally, as the modified PtON6-Cab comprises a CD3 substitution, it is expected to obtain the benefits of Xia ‘410.
The modified PtON6-Cab reads on the claimed Formula VI wherein ring D is an imidazole which coordinates to Pt via a carbene carbon, wherein two RD are joined to the imidazole to form a fused benzene ring, and at least one carbon ring atom of the fused benzene ring comprises a substituent selected from combinations of deuterium and alkyl.
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.
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/BRAELYN R WATSON/Examiner, Art Unit 1786