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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 01/14/2026 has been entered.
Election/Restrictions
Applicant's election without traverse of Species (B), a complex of General Formula (X) wherein two adjacent groups R2 represent Formula A (claim 14), in the reply filed on 4/7/2025 is acknowledged.
Claim 17 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group.
Response to Amendment
The amendment of 01/14/2026 has been entered.
Disposition of claims:
Claims 1-10, 13, 22-23, and 26 have been canceled.
Claims 33-34 have been added.
Claims 11-12, 14-21, 24-25, and 27-34 are pending.
Claim 17 is withdrawn.
Claim 11 has been amended.
The cancellation of claims 22-23 obviates the rejections of claims 22-23 set forth in the last Office Action.
The amendment of claim 11 have overcome the rejections of claims 11-12, 14, 18-21, and 29 under 35 U.S.C. 103 as being unpatentable over Zeng et al. (US 2018/0198081 A1, hereafter Zeng) in view of Tsai et al. (US 2013/0168656 A1, hereafter Tsai), Luo et al. (“Exploring the Photodeactivation Pathways of Pt[O^N^C^N] Complexes: A Theoretical Perspective” ChemPhysChem 2016, vol. 17, page 69-77, hereafter Luo), and Fleetham et al. (“Efficient “Pure” Blue OLEDs Employing Tetradentate Pt Complexes with a Narrow Spectral Bandwidth” Adv. Mater. 2014, vol. 26, page 7116-7121, hereafter Fleetham) set forth in the last Office Action. The rejections have been withdrawn.
Response to Arguments
Applicant’s arguments see the page 8-9 of the reply filed 01/14/2026 regarding the rejections of claims 11-12, 14, 18-21, and 29 under 35 U.S.C. 103 as being unpatentable over Zeng/Tsai/Luo/Fleetham set forth in the Office Action of 10/14/2025 have been considered.
Applicant argues that the claims are not obvious over Zeng in view of Tsai.
The rejections refer to the Compound of Zeng as modified by Tsai, Luo, and Fleetham (section 100 of the last Office Action). The compound does not read on the limitation of Formula X of the amended claim because the moiety corresponding to the Formula A bonds to Y2e and Y2d which is not allowed in the amended claims. The rejections are withdrawn.
Applicant’s arguments see the page 9-16 of the reply filed 01/14/2026 regarding The rejections of claims 11-12, 14-16, 18-21, 24-25, 27, 29, and 31-32 under 35 U.S.C. 103 as being unpatentable over Tsai et al. (US 2013/0168656 A1) in view of Noboru et al. (JP 2012/074444 A, machine translated English version is referred to, hereafter Noboru), Luo et al. (“Exploring the Photodeactivation Pathways of Pt[O^N^C^N] Complexes: A Theoretical Perspective” ChemPhysChem 2016, vol. 17, page 69-77, hereafter Luo), and Fleetham et al. (“Efficient “Pure” Blue OLEDs Employing Tetradentate Pt Complexes with a Narrow Spectral Bandwidth” Adv. Mater. 2014, vol. 26, page 7116-7121, hereafter Fleetham) set forth in the Office Action of 10/14/2025 have been considered.
Applicant argues that the present invention is based in part on the unexpected observation that the inclusion of t-butyl group at Y1d (page 11, the last paragraph through page 13, the first paragraph).
The previous rejections of Tsai in view of Noboru, Luo, and Fleetham has been updated to remove the teaching of Fleetham; instead, new teaching references of Blondel, Forrest, and Li are used.
It is unclear whether the improvement (i.e. narrower FWHM of the PL spectra of t-butyl substituted compound as compared to unsubstituted compound) is unexpected for the following reasons.
First, none of the comparative examples (PtNON and PtNONS56) is the closest prior art.
An affidavit or declaration under 37 CFR 1.132 must compare the claimed subject matter with the closest prior art to be effective to rebut a prima facie case of obviousness. In re Burckel, 592 F.2d 1175, 201 USPQ 67 (CCPA 1979). "A comparison of the claimed invention with the disclosure of each cited reference to determine the number of claim limitations in common with each reference, bearing in mind the relative importance of particular limitations, will usually yield the closest single prior art reference." In re Merchant, 575 F.2d 865, 868, 197 USPQ 785, 787 (CCPA 1978) (emphasis in original). Where the comparison is not identical with the reference disclosure, deviations therefrom should be explained, In re Finley, 174 F.2d 130, 81 USPQ 383 (CCPA 1949), and if not explained should be noted and evaluated, and if significant, explanation should be required. In re Armstrong, 280 F.2d 132, 126 USPQ 281 (CCPA 1960) (deviations from example were inconsequential). See MPEP 716.02(e).
The new ground of rejections refer to Compound 14 of Tsai ([0061]) which is the closest prior art.
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Compound 14 of Tsai already has an alkyl group (i.e. isopropyl) at the position corresponding to Y1d of General Formula X of the instant claims.
It is unclear whether the data proves the unexpected improvement that Applicant argues because the comparison was not made to the closest prior art. For instance, to effectively prove the unexpected improvement, it should be shown that a t-butyl of the inventive compound provides improvement as compared to the closest prior art such as Compound 14 of Tsai which already possesses isopropyl at the position corresponding to Y1d of General Formula X. The data does not prove the criticality of a t-butyl group as compared to the isopropyl group at the position Y1d.
Secondly, there are several reasons why an ordinary skill in the art to modify the lead compound to substitute the compound with t-butyl groups based on the teaching of Luo, Blondel, Forrest, and Li.
Luo discloses a Pt complex used for an organic light emitting device (page 69, col. 1, first paragraph).
Luo teaches that a t-butyl group is extensively used as substituent unit in transition metal complexes and the steric property of the t-butyl group provides suppressed intermolecular interactions and improved efficiency and color purity (page 69, col. 2, line 8-13).
Blondel teaches that addition of a sterically hindered t-butyl group to a planar Pt complex provides reduced aggregation such that the aggregation-induced quenching is reduced and the electroluminescence efficiency is improved (Abstract; page 107, col. 1, line 16-18; and Conclusion).
Forrest teaches that addition of a sterically bulky group such as tertiary butyl provides a planar macrocyclic ligand with reduced aggregation and high efficiency by allowing emission from the monomer state at high doping level ([0216]).
Li teaches that addition of tert-butyl group provides improved thermal stability ([0128]). The tert-butyl group is substituted to the position 4 of the pyridine ring of the pyridinyl carbazole ligand (see t-butyl group in the compounds PtON6-tBu and PtON7-dtb in Fig. 30C and 30D).
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The fact that applicant has recognized another advantage (i.e. narrow emission spectrum) which would flow naturally from following the suggestion of the prior art (i.e. suppressed intermolecular interaction, improved efficiency, reduced aggregation-induced quenching, capability of maintaining high doping level which improves high efficiency, and improved stability) cannot be the basis for patentability when the differences would otherwise be obvious. See Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985).
Third, Applicant has shown improvement in the spectral width (i.e. FWHM) of the PL spectra. However, Luo teaches that addition of a t-butyl group provides such improvement.
Luo teaches that a t-butyl group is extensively used as substituent unit in transition metal complexes and the steric property of the t-butyl group provides improved color purity (page 69, col. 2, line 8-13). High color purity stems from narrow spectral width in emission. Thus, the narrow spectral width is not an unexpected result.
For at least this reason, the argument is not found to be persuasive.
Applicant further argues that the Examiner fails to note that Fleetham is drawn to non-symmetric complexes, and there is no previous evidence that any spectral narrowing would be observed in symmetric complexes (page 13-15).
Respectfully, the Examiner does not agree.
First, Fleetham is not used in the new grounds of rejection.
Second, as outlined above, there are several reasons why an ordinary skill in the art to modify the lead compound to substitute the compound with t-butyl groups based on the teaching of Luo, Blondel, Forrest, and Li.
Third, as outlined above, Luo teaches that addition of a t-butyl group provides high color purity which stems from narrow spectral width.
For at least this reason, the argument is not found to be persuasive.
Applicant’s arguments see the page 15-16 of the reply filed 01/14/2026 regarding the rejections of claims 28 and 30-31 under 35 U.S.C. 103 as being unpatentable over Tsai et al. (US 2013/0168656 A1) in view of Noboru et al. (JP 2012/074444 A, machine translated English version is referred to) set forth in the Office Action of 10/14/2025 have been considered.
Applicant argues that Tsai in view of Noboru doe not teach or suggest each and every element of the instant claim 31 (page 16).
Respectfully, the Examiner does not agree.
The cited rejections refer to the Position isomer of complex of Tsai as modified by Noboru as shown below.
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The compound still reads on all the limitations of claims 28 and 30-31. The rejections are maintained with some updates.
Claim Objections
Claim 30 is objected to because of the following informalities:
In claim 30, Applicant recites “A light-emitting device …” while Applicant recites “An organic light-emitting device” in claim 29. It is suggested to use the same term such as “An organic light emitting device” for better consistency.
Appropriate correction is required.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 11-12, 14-16, 18-21, 24-25, 27, and 29-34 are rejected under 35 U.S.C. 103 as being unpatentable over Tsai et al. (US 2013/0168656 A1) in view of Noboru et al. (JP 2012/074444 A, machine translated English version is referred to, hereafter Noboru), Luo et al. (“Exploring the Photodeactivation Pathways of Pt[O^N^C^N] Complexes: A Theoretical Perspective” ChemPhysChem 2016, vol. 17, page 69-77, hereafter Luo), Blondel et al. (“Investigation of a sterically hindered Pt(II) complex to avoid aggregation-induced quenching: Applications in deep red electroluminescent and electrical switching devices” Syn. Metal 2017, vol. 227, page 106-116, hereafter Blondel), Forrest et al. (US 2005/0260444 A1, hereafter Forrest), and Li et al. (US 2015/016552 A1, hereafter Li).
Regarding claims 11-12, 14, 18-20, 24, 29 and 33, Tsai discloses a complex represented by Formulas I ([0049]) and more detailed structure represented by Formula III ([0056]). Tsai exemplifies Compound 14 ([0061]).
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The Compound 14 of Tsai does not have a benzo-five-membered ring fused to the carbazole; however, Tsai does teach that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen, aryloxy, alkenyl, heteroalkenyl, aryl, and sulfanyl; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]).
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Noboru discloses a complex used for an organic light emitting device (“organic electroluminescent device” in [0012] and [0014]), wherein the complex includes a 6-5-6-5-6 condensed ring structure of Formula (2) ([0017]- [0018]). Noboru discloses detailed structures of the 6-5-6-5-6 condensed rings represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]). In Formula (Q-1) to (Q-5), X1 and X2 can be each independently N(R1), O, or S ([0077]).
Noboru exemplifies benzofurocarbazole as the example of the 6-5-6-5-6 condensed ring (Compound (11) in [0088]; and see the part enclosed by a dashed circle in the figure above).
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound 14 of Tsai by substituting each of the carbazole moieties of the compound with benzofurocarbazole as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Tsai teaches the substituents at the positions R2 and R3 of Formulas I and III of Tsai can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). The substitution of hydrogen with a fused benzofuran ring in the compound of Tsai would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Complex of Tsai as modified by Noboru.
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The Compound of Tsai as modified by Noboru has similar structure as General Formula X of the instant claims. The only difference is that the isopropyl group at the positions corresponding to the R1 and R4 of Formula III of Tsai is required to be each a t-butyl group; however, Tsai does teach that R1 and R4 can be alkyl ([0049]).
Luo discloses a Pt complex used for an organic light emitting device (page 69, col. 1, first paragraph).
Luo teaches that a t-butyl group is extensively used as substituent unit in transition metal complexes and the steric property of the t-butyl group provides suppressed intermolecular interactions and improved efficiency and color purity (page 69, col. 2, line 8-13).
Blondel teaches that addition of a sterically hindered t-butyl group to a planar Pt complex provides reduced aggregation such that the aggregation-induced quenching is reduced and the electroluminescence efficiency is improved (Abstract; page 107, col. 1, line 16-18; and Conclusion).
Forrest teaches that addition of a sterically bulky group such as tertiary butyl provides a planar macrocyclic ligand with reduced aggregation and high efficiency by allowing emission from the monomer state at high doping level ([0216]).
Li teaches that addition of tert-butyl group provides improved thermal stability ([0128]). The tert-butyl group is substituted to the position 4 of the pyridine ring of the pyridinyl carbazole ligand (see t-butyl group in the compounds PtON6-tBu and PtON7-dtb in Fig. 30C and 30D).
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At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound of Tsai as modified by Noboru by substituting the isopropyl group at the positions corresponding to R1 and R4 of Formula III of Tsai with each t-butyl group, as taught by Tsai, Luo, Blondel, Forrest, and Li.
The motivation of doing so would have been to provide provides suppressed intermolecular interactions and improved efficiency and color purity based on the teaching of Luo, provide reduced aggregation such that the aggregation-induced quenching is reduced and the electroluminescence efficiency is improved based on the teaching of Blondel, provide planar macrocyclic ligand with reduced aggregation and high efficiency by allowing emission from the monomer state at high doping level based on the teaching of Forrest, and provide improved thermal stability based on the teaching of Li.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of isopropyl with t-butyl at the position corresponding to R1 of Formula I of Zeng would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
Alternatively, even if there were no teaching and suggestion from Luo, Blondel, Forrest, and Li, the modification based on Tsai only is obvious for the following reason.
A compound having an isopropyl group is a homolog – a compound differing regularly by the successive addition of the same chemical groups, in the present instance, a CH3 group, of a compound in which the compound having the same skeletal structure except the isopropyl is substituted by a t-butyl group.
With respect to homologs, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See MPEP 2144.09 I and 2144.09 II.
Therefore, at the time the invention was effectively filed, it would have been obvious to one with ordinary skill in the art to have modified Compound of Tsai as modified by Noboru such that the isopropyl groups are substituted by each a t-butyl group. A compound comprising t-butyl groups would be a homolog of the Compound of Tsai as modified by Noboru.
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The modification provides Compound of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li, which has identical structure as Applicant’s General Formula V, meeting all the limitations of claims 11-12, 14, 18-20, 24 and 33.
Tsai in view of Noboru, Luo, Blondel, Forrest, and Li does not disclose a specific an organic light emitting device comprising the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li; however, Tsai does teach that the compound of Tsai can be incorporated in an organic light emitting device ([0027] and examples in [0071]-[0072]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li by incorporating it into an organic light emitting device, as taught by Tsai.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of compounds of Tsai in an OLED device of Tsai would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Organic light emitting device of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li comprising the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li, meeting all the limitations of claim 29.
Regarding claim 21, the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li reads on all the features of claim 11 as outlined above.
The complex does not read on all the limitations of claim 21. The only deficiency of the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li is that the atom at the position corresponding to X2 is required to be S; however, Tsai does teach that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen, aryl, or sulfanyl; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]).
Noboru discloses a complex used for an organic light emitting device (“organic electroluminescent device” in [0012] and [0014]), wherein the complex includes a 6-5-6-5-6 condensed ring structure of Formula (2) ([0017]- [0018]). Noboru discloses detailed structures of the 6-5-6-5-6 condensed rings represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]). In Formula (Q-1) to (Q-5), X1 and X2 can be each independently N(R1), O, or S ([0077]).
Noboru exemplifies benzofurocarbazole as the example of the 6-5-6-5-6 condensed ring (Compound (11) in [0088]).
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li by substituting the oxygen atom at the position corresponding to X2 of the General Formula X with sulfur as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Tsai teaches the substituents at the positions R2 and R3 of Formulas I and III of Tsai can be sulfanyl (i.e. -SH) and aryl (i.e. phenyl); and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). The substitution of hydrogen with a fused benzofuro ring in the compound of Tsai would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Noboru exemplifies a benzofurocarbazole group which is represented by the Formula (Q-4) of Noboru. Noboru teaches X1 and X2 of Formula (Q-4) can be O or S; thus, substitution of O with S in the Formula (Q-4) of Noboru would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li (2).
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Regarding claims 15, 30-32 and 34, the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li reads on all the features of claim 11 as outlined above.
The Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li does not read on all the limitation of the claimed complex. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure below) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 2 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group. However, both Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li and the claimed compound (i.e. the Position isomer of complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li in the figure below) are position isomers to each other.
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With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Furthermore, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-4) and (Q-1) below).
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The benzofuro carbazole moieties of the Complex of Tsai as modified by Noboru corresponds to the Formula (Q-4). However, the benzofuro moiety is attached to the carbazole moiety similarly as in the Formula (Q-1) because both Formulas (Q-4) and (Q-1) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group similarly as Formula (Q-1) of Noboru, as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Tsai teaches that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). Tsai does not restrict the substitution positions of the substituents at R2 (or R3) with respect to the carbazole moieties. The substitution of the substitution positions of the hydrogen and aryloxy would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Additionally, both Formulas (Q-4) and (Q-1) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-4) to (Q-1) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides the Position isomer of complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li (see the structure in the figure above), meeting all the limitations of claims 15, 31-32 and 34.
The modification of the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li in the Organic light emitting device of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li to the Position isomer of complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li provides Organic light emitting device of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li (2) comprising the Position isomer of complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li, meeting all the limitations of claim 30.
Regarding claims 16 and 27, the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li reads on all the features of claim 11 as outlined above.
The Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li does not read on all the limitation of the claimed complex. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure below) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 2 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 4 and 3 of the benzene ring of the carbazole group. However, both Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li and the claimed compound (i.e. the Position isomer of complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li in the figure below) are position isomers to each other.
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With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Furthermore, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-4) and (Q-5) below).
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The benzofuro carbazole moieties of the Complex of Tsai as modified by Noboru corresponds to the Formula (Q-4). However, the benzofuro moiety is attached to the carbazole moiety similarly as in the Formula (Q-5) because both Formulas (Q-4) and (Q-5) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 4 and 3 of the benzene ring of the carbazole group similarly as Formula (Q-5) of Noboru, as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Tsai teaches that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). Tsai does not restrict the substitution positions of the substituents at R2 (or R3) with respect to the carbazole moieties. The substitution of the substitution positions of the hydrogen and aryloxy would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Additionally, both Formulas (Q-4) and (Q-5) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-4) to (Q-5) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides the Position isomer of complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li (see the structure in the figure above).
Regarding claim 25, the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li reads on all the features of claim 11 as outlined above.
The Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li does not read on all the limitation of the claimed complex. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure below) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 2 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 2 and 3 of the benzene ring of the carbazole group. However, both Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li and the claimed compound (i.e. the Position isomer of complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li in the figure below) are position isomers to each other.
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With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Furthermore, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-4) and (Q-2) below).
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The benzofuro carbazole moieties of the Complex of Tsai as modified by Noboru corresponds to the Formula (Q-4). However, the benzofuro moiety is attached to the carbazole moiety similarly as in the Formula (Q-2) because both Formulas (Q-4) and (Q-2) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 2 and 3 of the benzene ring of the carbazole group similarly as Formula (Q-2) of Noboru, as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Tsai teaches that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). Tsai does not restrict the substitution positions of the substituents at R2 (or R3) with respect to the carbazole moieties. The substitution of the substitution positions of the hydrogen and aryloxy would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Additionally, both Formulas (Q-4) and (Q-2) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-4) to (Q-2) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides the Position isomer of complex of Tsai as modified by Noboru, Luo, Blondel, Forrest, and Li (see the structure in the figure above).
Claims 28, 30-31 and 34 are rejected under 35 U.S.C. 103 as being unpatentable over Tsai et al. (US 2013/0168656 A1) in view of Noboru et al. (JP 2012/074444 A, machine translated English version is referred to).
Regarding claims 28, 30-31 and 34, Tsai discloses a complex represented by Formulas I ([0049]) and more detailed structure represented by Formula III ([0056]). Tsai exemplifies Compound 1 ([0061]).
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Tsai exemplifies an organic light-emitting device comprising Compound 1 of Tsai (Device Ex. 1 in [0071]- [0072] and Table 2) wherein the device comprises an anode (ITO), an organic light emitting layer comprising Compound 1 of Tsai, and a cathode (Al).
The Compound 1 of Tsai does not have a benzo-five-membered ring fused to the carbazole; however, Tsai does teach that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen, aryloxy, alkenyl, heteroalkenyl, aryl, and sulfanyl; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]).
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Noboru discloses a complex used for an organic light emitting device (“organic electroluminescent device” in [0012] and [0014]), wherein the complex includes a 6-5-6-5-6 condensed ring structure of Formula (2) ([0017]- [0018]). Noboru discloses detailed structures of the 6-5-6-5-6 condensed rings represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]). In Formula (Q-1) to (Q-5), X1 and X2 can be each independently N(R1), O, or S ([0077]).
Noboru exemplifies benzofurocarbazole as the example of the 6-5-6-5-6 condensed ring (Compound (11) in [0088]; and see the part enclosed by a dashed circle in the figure above).
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Compound 14 of Tsai by substituting each of the carbazole moieties of the compound with benzofurocarbazole as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Tsai teaches the substituents at the positions R2 and R3 of Formulas I and III of Tsai can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). The substitution of hydrogen with a fused benzofuran ring in the compound of Tsai would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Complex of Tsai as modified by Noboru as shown below.
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The Complex of Tsai as modified by Noboru has similar structure as the second embodiment of the instant claim 28. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure below) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 2 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group. However, both Complex of Tsai as modified by Noboru and the claimed compound (i.e. the Position isomer of complex of Tsai as modified by Noboru in the figure below) are position isomers to each other.
With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Furthermore, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-4) and (Q-1) below).
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The benzofurocarbazole moieties of the Complex of Tsai as modified by Noboru corresponds to the Formula (Q-4). However, the benzofuro moiety is attached to the carbazole moiety similarly as in the Formula (Q-1) because both Formulas (Q-4) and (Q-1) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Complex of Tsai as modified by Noboru by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group similarly as Formula (Q-1) of Noboru, as taught by Tsai and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Tsai teaches that the substituents R2 and R3 of the carbazole of Formula III can be hydrogen and aryloxy; and two or more adjacent R2 and R3 can be joined to form a fused ring ([0049]). Tsai does not restrict the substitution positions of the substituents at R2 (or R3) with respect to the carbazole moieties. The substitution of the substitution positions of the aryloxy would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B). Additionally, both Formulas (Q-4) and (Q-1) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-4) to (Q-1) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides the Position isomer of complex of Tsai as modified by Noboru (see the structure in the figure above), meeting all the limitations of claims 28, 31, and 34.
The modification also provides Organic light emitting device of Tsai as modified by Noboru comprising an anode (ITO), an organic light emitting layer comprising the Position isomer of complex of Tsai as modified by Noboru, and a cathode (Al), meeting all the limitations of claim 30.
Claims 11-12, 14-16, 18-21, 24-25, 27, and 29-34 are rejected under 35 U.S.C. 103 as being unpatentable over Li et al. (US 2017/0040555 A1, hereafter Li ‘555) in view of Noboru et al. (JP 2012/074444 A, machine translated English version is referred to).
Regarding claims 11-12, 14, 18-20, 24, 29 and 33, Li ‘555 discloses a complex represented by Formulas I ([0008]) used for an organic light emitting device ([0002]) and exemplifies a compound PtNONc-dtb ([0132]).
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Li ‘555 does not disclose a specific organic light emitting device comprising the PtNONc-dtb of Li ‘555; however, Li does teach that the compound can be used in the light emitting layer or an organic light emitting device ([0125]).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the compound PtNONc-dtb by incorporating it into the light emitting layer of an organic light emitting device, as taught by Li ‘555.
The modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). The substitution of light emitting dopant materials in an organic light emitting device would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Modified organic light emitting device comprising the compound PtNONc-dtb of Li ‘555.
The compound PtNONc-dtb of Li ‘555 has similar structure as Applicants Formula X of the instant claims. The only difference is the carbazole moieties of the compound does not have a benzo-five-membered ring fused to the carbazole.
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Noboru discloses a complex used for an organic light emitting device (“organic electroluminescent device” in [0012] and [0014]), wherein the complex includes a 6-5-6-5-6 condensed ring structure of Formula (2) ([0017]- [0018]). Noboru discloses detailed structures of the 6-5-6-5-6 condensed rings represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]). In Formula (Q-1) to (Q-5), X1 and X2 can be each independently N(R1), O, or S ([0077]).
Noboru exemplifies benzofurocarbazole as the example of the 6-5-6-5-6 condensed ring (Compound (11) in [0088]; and see the part enclosed by a dashed circle in the figure above).
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the compound PtNONc-dtb of Li ‘555 by substituting each of the carbazole moieties of the compound with benzofurocarbazole as taught by Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A).
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The modification provides Complex of Li ‘555 as modified by Noboru, which has identical structure as Applicant’s General Formula X, meeting all the limitations of claims 11-12, 14, 18-20, 24 and 33.
It is noted that in the Complex of Li ‘555, the variable n of each of the (R1)n groups is 3, wherein R1 are each hydrogen or a t-butyl group. The atom at the positions corresponding to Y1b are each unsubstituted carbon. In the claim, there is no limitation that the carbon at Y1b is required to be substituted by R1, because n can be selected to 3 and valency is permitted. The claims should be interpreted in a broadest reasonable manner (BRI). In the Complex of Li ‘555 as modified by Noboru, the valence electrons of the carbon atoms at the positions Y1b having no substituent are connected to each other to form a direct bond; thus, the compound reads on all the limitations of Applicant’s Formula X.
The modification also provides Organic light emitting device of Li ‘555 as modified by Noboru comprising the Complex of Li ‘555 as modified by Noboru, meeting all the limitations of claim 29.
Regarding claim 21, the Complex of Li ‘555 as modified by Noboru reads on all the features of claim 11 as outlined above.
The complex does not read on all the limitations of claim 21. The only deficiency of the Complex of Li ‘555 as modified by Noboru is that the atom at the position corresponding to X2 is required to be S; however, Noboru teaches the oxygen atom at the position corresponding to X2 can be sulfur.
Noboru discloses a complex used for an organic light emitting device (“organic electroluminescent device” in [0012] and [0014]), wherein the complex includes a 6-5-6-5-6 condensed ring structure of Formula (2) ([0017]- [0018]). Noboru discloses detailed structures of the 6-5-6-5-6 condensed rings represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]). In Formula (Q-1) to (Q-5), X1 and X2 can be each independently N(R1), O, or S ([0077]).
Noboru exemplifies benzofurocarbazole as the example of the 6-5-6-5-6 condensed ring (Compound (11) in [0088]).
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Complex of Li ‘555 as modified by Noboru by substituting the oxygen atom at the position corresponding to X2 of the General Formula X with sulfur as taught by Li ‘555 and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Noboru exemplifies a benzofurocarbazole group which is represented by the Formula (Q-4) of Noboru. Noboru teaches X1 and X2 of Formula (Q-4) can be O or S; thus, substitution of O with S in the Formula (Q-4) of Noboru would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides Complex of Li ‘555 as modified by Noboru (2).
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Regarding claims 15, 30-32 and 34, the Complex of Li ‘555 as modified by Noboru reads on all the features of claim 11 as outlined above.
The Complex of Li ‘555 as modified by Noboru does not read on all the limitation of the claimed complex. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure below) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 2 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group. However, both Complex of Li ‘555 as modified by Noboru and the claimed compound (i.e. the Position isomer of complex of Li ‘555 as modified by Noboru in the figure below) are position isomers to each other.
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With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Furthermore, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-4) and (Q-1) below).
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The benzofuro carbazole moieties of the Complex of Li ‘555 as modified by Noboru corresponds to the Formula (Q-4). However, the benzofuro moiety is attached to the carbazole moiety similarly as in the Formula (Q-1) because both Formulas (Q-4) and (Q-1) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Complex of Li ‘555 as modified by Noboru by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 3 and 4 of the benzene ring of the carbazole group similarly as Formula (Q-1) of Noboru, as taught by Li ‘555 and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Both Formulas (Q-4) and (Q-1) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-4) to (Q-1) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides the Position isomer of complex of Li ‘555 as modified by Noboru (see the structure in the figure above), meeting all the limitations of claims 15, 31-32 and 34.
The modification of the Complex of Li ‘555 as modified by Noboru in the Organic light emitting device of Li ‘555 as modified by Noboru to the Position isomer of complex of Li ‘555 as modified by Noboru provides Organic light emitting device of Li ‘555 as modified by Noboru (2) comprising the Position isomer of complex of Li ‘555 as modified by Noboru, meeting all the limitations of claim 30.
Regarding claims 16 and 27, the Complex of Li ‘555 as modified by Noboru reads on all the features of claim 11 as outlined above.
The Complex of Li ‘555 as modified by Noboru does not read on all the limitation of the claimed complex. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure below) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 2 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 4 and 3 of the benzene ring of the carbazole group. However, both Complex of Li ‘555 as modified by Noboru and the claimed compound (i.e. the Position isomer of complex of Li ‘555 as modified by Noboru in the figure below) are position isomers to each other.
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426
743
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With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Furthermore, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-4) and (Q-5) below).
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160
596
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Greyscale
The benzofuro carbazole moieties of the Complex of Li ‘555 as modified by Noboru corresponds to the Formula (Q-4). However, the benzofuro moiety is attached to the carbazole moiety similarly as in the Formula (Q-5) because both Formulas (Q-4) and (Q-5) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Complex of Li ‘555 as modified by Noboru by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 4 and 3 of the benzene ring of the carbazole group similarly as Formula (Q-5) of Noboru, as taught by Li ‘555 and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Both Formulas (Q-4) and (Q-5) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-4) to (Q-5) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides the Position isomer of complex of Li ‘555 as modified by Noboru (see the structure in the figure above).
Regarding claim 25, the Complex of Li ‘555 as modified by Noboru reads on all the features of claim 11 as outlined above.
The Complex of Li ‘555 as modified by Noboru does not read on all the limitation of the claimed complex. The only difference between the two complexes is the attachment position of the benzofuro rings (enclosed by a dashed box in the figure below) to the carbazole groups. That is, the oxygen and the carbon atoms of the benzofuro ring are each attached to the substitution positions 3 and 2 of the benzene ring of the carbazole group, while the claim requires the oxygen and carbon atoms are each attached to the substitution positions 2 and 3 of the benzene ring of the carbazole group. However, both Complex of Li ‘555 as modified by Noboru and the claimed compound (i.e. the Position isomer of complex of Li ‘555 as modified by Noboru in the figure below) are position isomers to each other.
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417
730
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With respect to position isomers, the examiner points to the MPEP which states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1991) for an extensive review of the case law pertaining to obviousness based on close structural similarity of chemical compounds. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.” In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious). See MPEP 2144.09 I and 2144.09 II.
Furthermore, Noboru teaches that the 6-5-6-5-6 condensed ring structure Formula (2) ([0017]- [0018]) can be any one of structures represented by Formulas (Q-1) to (Q-5) ([0076]- [0081]; see Formulas (Q-4) and (Q-2) below).
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165
560
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Greyscale
The benzofuro carbazole moieties of the Complex of Li ‘555 as modified by Noboru corresponds to the Formula (Q-4). However, the benzofuro moiety is attached to the carbazole moiety similarly as in the Formula (Q-2) because both Formulas (Q-4) and (Q-2) are directed to the 6-5-6-5-6 condensed ring of Formula (2) of Noboru.
Noboru teaches that introduction of the 6-5-6-5-6 condensed ring into the light emitting dopant of an organic light emitting device provides suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility ([0036]) such that the organic light emitting device comprising the compound having the 6-5-6-5-6 condensed ring provides excellent efficiency, stability, and lifetime, as compared to 6-5-6 condensed ring ([0033], [0288], and Table 1).
At the time the invention was effectively filed, it would have been obvious to one of ordinary skill in the art to have modified the Complex of Li ‘555 as modified by Noboru by switching the attachment position of the benzofuro rings with respect to the carbazole units such that the benzofuro ring is attached to the substitution positions 2 and 3 of the benzene ring of the carbazole group similarly as Formula (Q-2) of Noboru, as taught by Li ‘555 and Noboru.
The motivation of doing so would have been to provide suppressed aggregation due to the steric hindrance, radical conjugate stabilization due to the delocalization of the anion radical, reduced dispersion of trace impurities, and improved dispersibility such that the organic light emitting device comprising the complex having benzofurocarbazole would have excellent efficiency, stability, and lifetime, as compared to carbazole, based on the teaching of Noboru.
Furthermore, the modification would have been a combination of prior art elements according to known material to achieve predictable results. See MPEP 2143(I)(A). Both Formulas (Q-4) and (Q-2) of Noburu are encompassed by the 6-5-6-5-6 condensed ring of the Formula (2) of Noboru. The substitution of the structure corresponding to the 6-5-6-5-6 condensed ring of Noboru from Formula (Q-4) to (Q-2) would have been one known element for another known element and would have led to predictable results. See MPEP 2143(I)(B).
The modification provides the Position isomer of complex of Li ‘555 as modified by Noboru (see the structure in the figure above).
Conclusion
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/SEOKMIN JEON/Primary Examiner, Art Unit 1786