DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Response to Arguments
Applicants arguments and amendments, filed on 3/27/26, have been fully considered but they do not confer patentability on all of the instantly filed claims. Applicants have amended independent claims 1 and 8 to include the limitation that L14 is not a substituted or unsubstituted naphthyl group. Applicants argue that this new amendment should cause the prior art rejection to Lyu et al. (CN-108409774) to be withdrawn. Specifically, Applicants refer to Formula (I) of Lui et al. which shows a group which corresponds to L14 which is a naphthyl group. However, the compound relied upon in Lyu et al. has as L14 a phenylene-naphthylene group. While this linker comprises an unsubstituted naphthyl group, the linker as a whole is a composite linker which comprises a naphthyl group. In other words a phenylene-naphthylene group is structurally distinct from a substituted or unsubstituted naphthyl group. For this reason, the prior art rejection to Lyu et al. is wholly maintained.
Applicants have also amended independent claims 1 and 8 to include the limitation “wherein when n2 is 0, X3 is C(Ra) with Ra being represented by Formula 2-2, a22 is 0, X23 is a single bond, and variables b23 and b24 are each 0, then a sum of n1 and b1 is 2 or greater”. While this amendment has caused the prior art rejections which rely on Kim et al. (WO 2010/126345) to be withdrawn, this amendment constitutes new matter as described below.
Applicants have also amended independent claims 8 and 18 to include that limitation that R11 to R13 are each not a substituted or unsubstituted C1-C60 alkyl group. This limitation has caused the prior art rejection to Park et al. (KR-20130110934) to be withdrawn.
Applicants have also amended independent claims 8 and 18 to include that limitation that when R11, R12, and/or R13 are each a substituted C6-C60 aryl group, then each substituent of the substituted C6-C60 aryl group is not a substituted or unsubstituted fluorene group. Applicants argue that the prior art rejection to Lyu et al. (CN-108409773) should be withdrawn as Lyu et al. fails to satisfy this condition. However, Lyu et al. may still be properly relied upon to reject some of Applicants instantly filed claims, as described below.
Last, new prior art rejections appear below.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
Claims 1-20 are rejected under 35 U.S.C. 112(a) as failing to comply with the written description requirement. The claims contain subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor had possession of the claimed invention. Independent claims 1 and 8 have been amended to include the condition that “when n2 is O, X3 is C(Ra) with Ra being represented by Formula 2-2, a22 is 0, X23 is a single bond, and variables b23 and b24 are each 0, then a sum of n1 and b1 is 2 or greater”. This newly added proviso is not simply just carving out one single compound or a readily envisaged negative limitation, but is instead a complex exclusion based on specific combinations of variables. The fairness of a new matter rejection hinges on whether that specific “carve-out” was ever contemplated or if it creates a “newly claimed sub-genus”. While MPEP 2163.05(i) allows negative limitations to overcome the prior art, an Applicant cannot simply add a negative limitation that is created through the picking and choosing from multiple variable selections to create a sub-genus that wasn’t originally identified. The originally filed disclosure does not provide any direction that would lead a person having ordinary skill in the art to the specific selections of the variables in question which lead to the compound to be excluded. The Applicant is essentially stitching together an exclusion from disparate parts of the specification to perfectly “shrink wrap” around the compounds disclosed in the prior art (specifically, Kim et al. WO 2010/126234). The specific list of conditions which leads to the proviso is not disclosed in any reasonable manner to suggest that Applicant had possession of such an exclusion.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1-3, 7-11, and 13-17 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Lyu et al. (CN-108409774, already of record).
Claims 1-3 and 7: Lyu et al. teaches compound 1-33 which has the structure
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(page 6). Device example 7 is drawn to an organic electroluminescent device comprising an anode (ITO), a hole injection layer, a hole transport layer, an emission layer comprising compound 1-33, an electron transport layer, an electron injection layer, and a cathode (Al). Device example 7 anticipates all of the device limitations of claims 1-3 and since device example 7 is shown as having the chromaticity coordinates (x,y) of 0.159 and 0.041, respectively, device example 7 emits blue light which anticipates claim 7. Compound 1-33 above anticipates Formula 1 of claim 1 with variable n1 equal to 1, variable B1 equal to a group satisfying Formula 1-1, variables b1 and n2 equal to zero, variables X1, X3, and X5 equal to N, variables X2 and X4 equal to C(Ra) with all Ra equal to an unsubstituted phenyl. As applied to Formula 1-1, compound 1-33 above has variable A equal to Si, variable a14 equal to 1, L14 equal to phenylene-naphthylene (which is exclusive of a substituted or unsubstituted naphthylene as claimed), variables a11-a13 equal to 1, variables L11-L13 equal to a single bond, variables b11-b13 equal to 1, and variables R11-R13 equal an unsubstituted phenyl group.
Claim 8: The rejection of claim 1 is wholly incorporated into the rejection of claim 8. Compound 1-33 above anticipates the compound of Formula 1 of claim 8 as described in claim 1 above.
Claim 9: In compound 1-33, variable n2 is equal to 1, thereby anticipating claim 9.
Claim 10: In compound 1-33, variables X1, X3, and X5 are each N, which anticipates condition (i) of claim 10.
Claim 11: In compound 1-33, variable A is Si, thereby anticipating claim 11.
Claim 13: In compound 1-33, variables R11-R13 are all equal to a phenyl group, thereby anticipating claim 13.
Claim 14: Claim 14 serves to further limit an optional embodiment where groups of Formula 1-2, 2-1, and 2-2 are present. Because such embodiments are optional, Lyu et al. may be properly relied upon to reject claim 14.
Claims 15-17: In compound 1-33, all Ra are equal to a phenyl group which satisfies claim 15, a group satisfying formula 6-1 of claim 16 with b61 equal to 0, and a group satisfying formula 7-1 of claim 17.
Claims 1, 2, and 8-16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Lyu A (CN-108409773, already of record).
Claim 8: At least compounds 118-121 of Lyu A anticipates Formula 1 of claim 8. Compound 120, as one example, which has the structure
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(page 6), anticipates Formula 1 of claim 8. As applied to Formula 1, X1, X3, and X5 are equal to N, X2 and X4 are equal to C(Ra) with one Ra equal to phenyl, and one Ra equal to a substituted phenyl, b1 is equal to 0, n2 is equal to zero, n1 is equal to 1, n1 + n2 equal to 1, B1 is equal to formula 1-1 with variable A equal to Si, a14 equal to 1, L14 equal to p-phenylene, a11-a13 equal to 1, L11-L13 equal to a single bond, b11-b13 equal to 1, and R11-R13 equal to phenyl. None of Applicants provisos of claim 8 apply to compound 120.
Claim 9: In compound 120, the sum of n1 and n2 is equal to 1 which anticipates claim 9.
Claim 10: Compound 120 anticipates condition (i) of claim 10.
Claim 11: In compound 120, A is equal to Si which anticipates claim 11.
Claim 12: In compound 120, L11-L13 are equal to a single bond, and L14 is equal to formula 3-1 with d4 equal to zero, thereby anticipating claim 12.
Claim 13: In compound 120, variables R11-R13 are equal to phenyl, thereby anticipating claim 13.
Claim 14: Claim 14 serves to further limit an optional embodiment where there is a group satisfying Formula 1-2 or 2-1. Compound 120 does not have either group and may be properly relied upon to reject claim 14.
Claims 15 and 16: In compound 120, one Ra group is equal to phenyl and one Ra group is equal to phenyl which is substituted by a fluorenyl group which anticipates claim 15, formula 6-1 of claim 16 with b61 equal to 0 when the Ra is phenyl and b61 equal to 1 when the Ra is a fluorenyl-substituted phenyl with R61 equal to a 9,9-dimethyfluorenyl group.
Claims 1 and 2: The rejection of claim 8 above is wholly incorporated into the rejection of claims 1 and 2. The compounds taught by Lyu A, which includes compound 120, are employed in organic electroluminescent devices. The device examples are drawn to an organic electroluminescent device which includes an anode (ITO), a hole injection layer, a hole transport layer, an emission layer comprising a host and a dopant, an electron transport layer, an electron injection layer, and a cathode (Al). The employment of any one of the explicitly taught compounds of Lyu A including one of compounds 118-121 in the electron transport layer is at once envisaged and therefore satisfies the device limitations of claims 1 and 2.
Claims 1-6 and 8-17 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Park et al. (US 2017/0170408).
Claims 1 and 2: Park et al. teaches organic electroluminescent devices which are exemplified to include an anode (ITO), a first and second hole injection layer, a first and second hole transport layer, an emission layer comprising a phosphorescent dopant, a first host material and a second host material, an electron transport layer, an electron injection layer, and a cathode (Al). The device architecture in the working examples of Park et al. satisfies all of the device limitations of claims 1 and 2. The second host materials taught by Park et al. include several compounds which satisfy all of the structural limitations of claim 1. This includes, for example, compounds H2-15, H2-188, H2-190, H2-194, H2-197, H2-199, H2-336, and H2-338. The employment of any one of the explicitly taught second host materials in the device examples of Park et al. is at once envisaged. As applied to Formula 1 of claim 1, compound H2-188, which has the structure
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(page 136), has X1, X3, and X5 equal to N, X2 and X4 equal to C(Ra) with both Ra groups equal to phenyl, b1 is equal to 0, n2 is equal to zero, n1 is equal to 1, n1 + n2 equal to 1, B1 is equal to formula 1-1 with variable A equal to Si, a14 equal to 1, L14 equal to N-carbazolyl, a11-a13 equal to 1, L11-L13 equal to a single bond, b11-b13 equal to 1, and R11-R13 equal to phenyl. None of Applicants provisos of claim 1 apples to compound H2-188.
Claims 3-6: The employment of any one of the explicitly taught second host materials of Park et al., including compound H2-188, is at once envisaged. A device prepared according to the examples of Park et al. with compound H2-188 as the second host material anticipates all of the device limitations of claims 3-6. The exemplified iridium phosphorescent dopant D-122 whose structure is taught on page 201 anticipates Formulae 401 and 402 of claim 6.
Claim 8: The rejection of claim 1 above is wholly incorporated into the rejection of claim 8. Compound H2-188 anticipates all of the structural limitations of claim 8 for the same reasons as claim 1, as described above.
Claim 9: In compound H2-188, the sum of n1 and n2 is equal to 1, which anticipates claim 9.
Claim 10: Compound H2-188 anticipates condition (i) of claim 10.
Claim 11: In compound H2-188, A is equal to Si which anticipates claim 11.
Claim 12: For claim 12 compound H2-194 is relied upon. This compound has the structure
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(page 137). As applied to Formula 1, this compound has X1, X3, and X5 equal to N, X2 and X4 equal to C(Ra) with one Ra group equal to phenyl, and the other Ra group equal to a substituted phenyl where the substituent is carbazole which is a heteroaryl group satisfying claim 8, b1 is equal to 0, n2 is equal to zero, n1 is equal to 1, n1 + n2 equal to 1, B1 is equal to formula 1-1 with variable A equal to Si, a14 equal to 2, L14 phenylene, a11-a13 equal to 1, L11-L13 equal to a single bond, b11-b13 equal to 1, and R11-R13 equal to phenyl. L11 in compound H2-194 is a group represented by Formulae 3-1 and 3-2 with d4 equal to 0.
Claim 13: In compound H2-188, variables R11-R13 are equal to phenyl, thereby anticipating claim 13.
Claim 14: Claim 14 serves to further limit an optional embodiment where there is a group satisfying Formula 1-2 or 2-1. Compound H2-188 does not have either group and may be properly relied upon to reject claim 14.
Claims 15-17: In compound H2-188, both Ra groups are equal to phenyl which anticipates claim 15, formula 6-1 of claim 16 with b61 equal to 0, and formula 7-1 of claim 17.
Claim 18 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Li et al. (WO 2016/025921). A copy of this reference is included herewith.
Li et al. teaches the complex
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on page 39. To prepare any one of the explicitly taught metal complexes of Li et al., including the complex above, inherently requires a metalation step where an unligated complex of the compounds taught therein is reacted with a metal complex to afford the desired metal complex. In preparing the explicitly taught complex shown above, the compound
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would inherently need to be prepared. This compound anticipates all of the limitations of claim 18. Specifically, this compound anticipates Formula 1 of claim 18 with X1 equal to N, and X2-X5 equal to hydrogen, b1 equal to 1, R1 equal to hydrogen, n2 equal to zero, n1 equal to 1, n1 + n2 equal to 1, B1 equal to formula 1-1 with variable A equal to Si, a14 equal to 1, L14 equal to a single bond, a11-a13 equal to 1, L11-L13 equal to a single bond, b11-b13 equal to 1, and R11 and R12 equal to unsubstituted phenyl, and R13 equal to a substituted pyridyl (a pyridine-substituted pyridyl group). This compound further anticipates Formula 1A-22 of claim 18 with Ra and R7 equal to hydrogen, and a6 equal to 3, and R6 equal to hydrogen.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 is incorrect, any correction of the statutory basis for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
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 1-9 and 11-16 are rejected under 35 U.S.C. 103 as being unpatentable over Cheng et al. (US 2009/0131670, cited on the attached PTO-892 form).
Claim 1: Cheng et al. teaches compounds which satisfy the general structure taught in paragraph 0008. These compounds are taught to be employed a host materials, hole transporting materials, or electron transporting materials in organic electroluminescent devices. The exemplified devices are comprised of an anode (ITO), a hole transport region, an emission layer comprising one of the compounds taught by Cheng et al. as a host material and a blue phosphorescent dopant, an electron transport region, and a cathode (Al). The compounds which adhere to the general structure in paragraph 0008 are taught as having excellent heat stability which increases device lifetime. The compounds additionally have a high triplet state energy difference compared to the dopant (paragraph 0076). An exemplified host compound which falls under the general structure in paragraph 0008 is compound mBSP which has the structure
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(paragraph 0033). While this compound does not satisfy the limitations of Formula 1 of claim 1, the overall teachings of Cheng et al. render obvious to a person having ordinary skill in the art to prepare structurally similar compounds to mBSP as a matter of routine experimentation and optimization. Specifically, in the general structure of Cheng et al., any one of R1-R30 may be a group other than hydrogen, and any one of R31 and R32 may be a group other than hydrogen. This includes the addition of methyl groups at R31 and R32 and biphenyl groups at some of the R1-R30 groups as shown in some of the exemplified compounds taught in paragraph 0021. Modifying compound mBSP by the addition of one or more methyl groups or by employing biphenyl groups in place of phenyl groups represents a routine and obvious modification which is explicitly revealed in the teachings of Cheng et al. The motivation to prepare such modified compounds of mBSP, such as a compound where each of the SiPh3 groups is replaced with Si-biphenyl groups would be to increase the thermal stability dues to the extension of p-conjugation and the increase in molecular weight. The increased mass of biphenyl groups relative to phenyl groups would be expected to increase both the glass transition temperature and decomposition temperature. The added bulkiness of the phenyl groups restricts the molecular rotation and reorganization which leads to a more robust material for used in OLEDs. The resulting obvious structural modification of compound mBSP where the phenyl groups are replaced with biphenyl groups satisfies the structural limitations of formula 1 of claim 1.
Additionally, the motivation to modify compound mBSP by including one or more methyl groups on the phenyl groups which are next to the pyridine ring would be expected to increase the triplet energy level. Specifically, methyl groups would force the phenyl rings to twist out of the plane relative to the central pyridine ring. Triplet energy is inversely related to the degree of conjugation. By forcing a larger dihedral angle, the electronic communication is broken which localizes the excited state to smaller fragments within the molecule as opposed to delocalization across the entire molecule. Because of this, the triplet energy level would be expected to increase. Cheng et al. teaches that the compounds taught therein are useful in the manner exemplified because of the high triplet energy levels present. Therefore, further optimization by through the inclusion of methyl group(s) to compound mBSP would have been an obvious modification/optimization. A methyl-group modified mBSP satisfies the structural limitations of formula 1 of claim 1.
As applied to Formula 1, a biphenyl analog of mBSP has X1, N, X3-X5 equal to C(Ra) with Ra equal to hydrogen, X2 equal to C(Ra) with Ra equal to a substituted phenyl group where the substituent is Si(biphenyl)3, b1 equal to 0, n2 equal to zero, n1 equal to 1, n1 + n2 equal to 1, B1 equal to formula 1-1 with variable A equal to Si, a14 equal to 1, L14 equal to phenylene, a11-a13 equal to 1, L11-L13 equal to a single bond, b11-b13 equal to 1, and R11-R13 equal to unsubstituted biphenyl. Employing a biphenyl analog of mBSP in the manner disclosed in device example D of Cheng et al. satisfies all of the structural and device limitations of claims 1.
Claims 2-7: As stated above, the compounds taught by Cheng et al. are exemplified in organic electroluminescent devices in a manner which satisfies claims 2-5. Additionally, the exemplified dopant FIrpytz is a blue phosphorescent dopant (paragraph 0074, which satisfies claim 7). Additionally, FIrpytz satisfies the structural limitations of claim 6.
Claim 8: The rejection of claim 1 above as it pertains to the modified mBSP compounds is wholly incorporated into the rejection of claim 8. As described in claim 1 above, a biphenyl modified mBSP compound anticipates formula 1 of claim 8.
Claim 9: In the biphenyl analog of mBSP, the sum of n1 and n2 is equal to 1 which satisfies claim 9.
Claim 11: In the biphenyl analog of mBSP, A is equal to Si which satisfies claim 11.
Claim 12: In the biphenyl analog of mBSP, L11-L13 is a single bond and L14 equal to formula 3-1 of claim 12 with d4 equal to 0, thereby satisfying claims 12.
Claim 13: In compound 29, R11-R13 are biphenyl, which satisfies claim 13.
Claim 14 serves to further limit an optional embodiment where there is a group satisfying Formula 1-2 or 2-1. The biphenyl analog of mBSP does not have either group and may be properly relied upon to reject claim 14.
Claims 15-16: In compound 29, the Ra groups are equal to hydrogen, or a phenyl groups which is substituted with Si(Q31)(Q32)(Q33) where Q31-Q33 are biphenyl, thereby satisfying claims 15 and formula 6-5 of claim 16 where b62 is equal to 1.
Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over each of Lyu A (CN-108409773), Park et al. (US 2017/0170408), and Cheng et al. (US 2009/0131670), further in view of Kim et al. (US 2021/0385215, already of record), as applied to claim 8.
Each of Lyu A, Park et al., and Cheng et al. teach compounds which satisfy independent claim 8, as respectively described above. While these three teachings do not explicitly suggest preparing deuterated analogs of the compounds taught therein, it would have been obvious to a person having ordinary skill in the art to have prepared such deuterated analogs given the teachings of Kim et al. Kim et al. teaches that deuterated analogs for host materials provide increased lifespan due to the decrease of zero point vibration energy of the deuterated compounds compared to analogous non-deuterated compounds (paragraph 0073). For this reason, it would have been obvious to a person having ordinary skill in the art to have replaced some of all of the hydrogen atoms in the specific compounds described in claim 8 above for each of Lyu A, Park et al. with deuterium. The replacement of some or all of the hydrogen atoms in such compounds would necessarily include embodiments where the deuteration rate is above 10% thereby satisfying Equation 1 of claim 19.
Comment on Patentability
While all claims stand rejected, claim 20 is free of any prior art rejections.
Conclusion
Applicant's amendment necessitated the new grounds 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ROBERT S LOEWE whose telephone number is (571)270-3298. The examiner can normally be reached on Monday-Friday from 8 AM to 5 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner' s supervisor, Randy Gulakowski, can be reached at telephone number 571-272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Robert S Loewe/Primary Examiner, Art Unit 1766
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