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 .
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) 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.
Election/Restrictions
The applicant's affirmation of election with traverse of Group I, claims 1-17 in the reply filed on 02/23/2024 was previously acknowledged.
Claims 18-19 were previously withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. Applicant timely traversed the restriction requirement in the reply filed on 02/23/2024.
Response to Amendment
The applicant's amendment of 06/27/2025 has been entered.
Claims 1-2 are amended due to the applicant's amendment.
Claims 1-3 and 7-19 are pending and claims 18-19 remain withdrawn from consideration.
The objections to claim 1-2 as set forth in the previous Office action are each overcome due to the applicant's amendment. The objections are withdrawn.
The declaration under 37 CFR 1.132 filed 06/27/2025 is insufficient to overcome the rejection of claims 1-3 and 7-8 under 35 U.S.C. 103 as being unpatentable over Hong et al. WO-2011149240-A2 and claims 1-3 and 7-17 under 35 U.S.C. 103 as being unpatentable over Katoh et al. WO-2013168688-A1 see machine translation referred to herein as "Katoh-MT" in view of Lee et al. US-20060103298-A1 and Hong et al. WO-2011149240-A2 as set forth in the previous Office action for the reasons discussed below. The rejections are maintained.
Response to Arguments
The applicant’s arguments on pages 29-37 of the reply dated 06/27/2025 with respect to the rejections under 35 U.S.C. 103 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument – The applicant argues on pages 33-37 of the reply that the data in the declaration of 06/27/2025 demonstrate that the claimed invention achieves unexpected results not taught by the prior art Hong et al. WO-2011149240-A2 ("Hong").
Examiner's response – The applicants have the burden of explaining the proffered data as evidence of non-obviousness. Any differences between the claimed invention and the prior art may be expected to result in some differences in properties. The issue is whether the properties differ to such an extent that the difference is really unexpected. Evidence relied upon should establish that the differences in results are in fact unexpected and unobvious and of both statistical and practical significance. Evidence of nonobviousness must also be commensurate in scope with the claims which the evidence is offered to support. Comparison must be between the claimed subject matter and the closest prior art to be effective to rebut a prima facie case of obviousness. See MPEP § 716.02.
The proferred results are not commensurate in scope with what is claimed and taught by the prior art Hong. The examples and comparative examples do not show modified and unmodified compounds encompassing the full scope of the group corresponding to Chemical Formal 4 that is also taught by Hong. Thus, it is unclear if the same differences in device performance would be observed wherein the compound comprises the structurally different moieties that fall within the full scope of Chemical Formal 4 that is also taught by Hong (e.g., wherein L1 is a direct bond, wherein Ar1 is phenanthroline group, a quinolyl group, a dibenzofuran group, or a dibenzothiophene group). Additionally, applicant does not currently provide sufficient explanation or technical reasoning regarding the how the results presented would allow one of ordinary skill in the art to reasonably extend the probative value thereof to the full scope of what is claimed and taught by the prior art (e.g., wherein L1 is a direct bond, wherein Ar1 is phenanthroline group, a quinolyl group, a dibenzofuran group, or a dibenzothiophene group).
For at least the reasons discussed above, the results are insufficient to overcome the rejections under 35 U.S.C. 103 over Hong as set forth in the previous Office action.
Applicant's argument – The applicant argues on page 37 of the reply that the dependent claims are also allowable at least based on their dependence on an allowable base claim, as well as for the additional features recited therein.
Examiner's response – The applicant has not provided additional arguments with respect to the dependent claims and therefore, for the reasons outlined above, this is not found persuasive.
Claim Rejections - 35 USC § 103
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.
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 1-3 and 7-8 are rejected under 35 U.S.C. 103 as being unpatentable over Hong et al. WO-2011149240-A2 (hereinafter "Hong-MT", and see machine translation referred to here as "Hong-MT".
Regarding claims 1-3 and 8, Hong teaches an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer comprising a bipolar compound represented by the formula (1), wherein the layer may be a light emitting layer and the compound is a host material (Hong-MT, page 3 of 20, lines 19-22 and page 1 of 20, lines 3-6). Hong teaches the device may further have a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and / or an 17 electron injection layer (Hong-MT, page 7 of 20, lines 15-18). Hong teaches the organic EL device comprising the compound having improved luminous efficiency, thermal stability, driving voltage, and lifetime (Hong-MT, page 3 of 20, lines 27-33).
Hong teaches specific examples of the compound of formula (1) including compound 64
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(Hong-WO, page 18).
Hone does not specifically exemplify a compound of the claimed Chemical formula 1. For example, the compound 64 of Hong differs from the claimed compound in that a group that is encompassed by the claimed Chemical Formula 3 is substituted at a position corresponding to A2 instead of A1, A3, or A4. However, the general formula (1) of Hong encompasses positional isomers wherein the group that is encompassed by the claimed Chemical Formula 3 is substituted at a position corresponding one of claimed A1, A3, or A4.
Therefore, given the general formula and teachings of Hong, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of the compound 64 wherein the group that is encompassed by the claimed Chemical Formula 3 is substituted at a position corresponding one of claimed A1, A3, or A4 instead of A-2. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by the general formula (1) of Hong in order to pursue the known options within their technical grasp and would expect the isomeric compounds to be useful as a host material in the light emitting layer of the device of Hong and possess the properties of improved luminous efficiency, thermal stability, driving voltage, and lifetime taught by Hong. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP § 2144.09 I. When compounds which are position isomers or homologs are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP § 2144.09 II.
The modified compound 64 of Hong has the structure
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and is a compound of the claimed Chemical Formula 1 wherein:
one of A1, A3 and A4 is represented by Chemical Formula 3, and the remaining of A1 to A4 are each hydrogen;
A7 is represented by Chemical Formula 4 and the other is hydrogen, and A5, A6, and A8 are hydrogen;
R9 is not required to be present;
p is 0;
L2 is a direct bond;
L1 is a phenylene group;
Ar1 is a benzimidazolyl group substituted with a phenyl group;
X1 is CRx;
X2 is CRy;
Rx and Ry bond to each other to form a direct bond;
R3 and R6 area each an unsubstituted C6 aryl group and R1, R2, R4, R5, R7, and R8 are each hydrogen;
R, R', and R'' are not required to be present; and
m is 1 and n is 0.
The device comprising the modified compound of Hong meets claims 1-3 and 8.
Regarding claim 7, Hong teaches the compound as discussed above with respect to claim 1.
Hong does not specifically disclose a compound as claimed in claim 7. For example, the modified compound 64 of Hong differs from the claimed compound 2-29
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in that the carbazolyl substituent of claimed Chemical Formula 3 is substituted with two phenyl groups instead of only one. However, Hong teaches that the substituents on the bipolar triphenylene compound of general formula (1) include a group represented by Formula 3 (Hong-Mt, page 4 of 20, lines 8-13), which is a carbazolyl group
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(Hong-WO, page 4), which is present in compound 64 of Hong. Further, Hong teaches that in Formula 3 of Hong, Q1 and Q2 may be hydrogen or an aryl group, among others (Hong-Mt, page 5 of 20, lines 22-27).
Therefore, given the general formula and teachings of Hong, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute one of Q1 and Q2 with hydrogen, because Hong teaches the variable may suitably be selected as such. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful as a host material in the light emitting layer of the device of Hong and possess the benefits as described above taught by Hong. See MPEP § 2143.I.(B).
The further modified compound 64 of Hong corresponds to the claimed compound 2-29 and therefore meets claim 7.
Claims 1-3 and 7-17 are rejected under 35 U.S.C. 103 as being unpatentable over Katoh et al. WO-2013168688-A1 (hereinafter "Katoh-WO"), see machine translation referred to herein as "Katoh-MT" in view of Lee et al. US-20060103298-A1 and Hong et al. WO-2011149240-A2 (hereinafter "Hong-MT"), and see machine translation referred to here as "Hong-MT".
Regarding claims 1-3 and 8-17, Katoh teaches an organic EL device comprising a light emitting layer comprising a compound represented by a general formula (1) or (3) to (6) as a dopant and a compound of a general formula (2) as a host (Kath-ME, page 10 of 37, lines 7-10). Katoh teaches exemplary host materials of the general formula (2) that meet the claimed Chemical Formula 2 (Katoh-WO, pages 48-61) including compound H1
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(Katoh-WO, pages 48).
The compound H1 corresponds to the claimed compound 5-1 and is a compound of the claimed Chemical Formula (2).
Katoh does not specifically disclose a device wherein the light emitting layer further comprises a compound of the claimed Chemical Formula 1. However, Katoh teaches that a plurality of types of hosts may be used in combination.
Additionally, Lee teaches an organic electroluminescent device which can prevent device characteristics from being degraded due to crystallization which may occur during a device operation (¶ [0013]) wherein the device comprises at least one light-emitting layer, wherein the light emitting layer comprises at least one dopant and at least two host materials including a first host material and a second host material (¶ [0015]) and the crystallization of the first host material can be prevented by the second host material (¶ [0032]). Lee teaches Preferably, in order to improve the device characteristics, the second host material has weight ratio of 0.3 to 3 with respect to the first host material having weight ratio of 1 (¶ [0033]).
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to include a second host material wherein the second host material has weight ratio of 0.3 to 3 with respect to the first host material having weight ratio of 1, based on the teaching of Katoh and Lee. The motivation for doing so would have been to prevent device characteristics from being degraded due to crystallization which may occur during a device operation, as taught by Lee.
Further, Hong teaches an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer comprising a bipolar compound represented by the formula (1), wherein the layer may be a light emitting layer and the compound is a host material (Hong-MT, page 3 of 20, lines 19-22 and page 1 of 20, lines 3-6). Hong teaches the device may further have a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and / or an 17 electron injection layer (Hong-MT, page 7 of 20, lines 15-18). Hong teaches the organic EL device comprising the compound having improved luminous efficiency, thermal stability, driving voltage, and lifetime (Hong-MT, page 3 of 20, lines 27-33). Hong teaches specific examples of the compound of formula (1) including compound 64
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(Hong-WO, page 18).
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to have modified the device of Katoh by forming the second host out of the compound of general formula (1), as taught by Hong. One would have been motivated to do so because Katoh in view of Lee teaches a second host material and Hong teaches a suitable host for an organic EL device. The selection of a known material, which is based upon its suitability for the intended use, is within the ambit of one of ordinary skill in the pertinent art. See MPEP § 2144.07.
Additionally, Hong teaches the device comprising the compound of Hong as having improved luminous efficiency, thermal stability, driving voltage, and lifetime and therefore forming the second host in the device of Katoh in view of Lee would yield the benefit of improved luminous efficiency, thermal stability, driving voltage, and lifetime, as described above.
Hong does not specifically exemplify a compound of the claimed Chemical formula 1. For example, the compound 64 of Hong differs from the claimed compound in that a group that is encompassed by the claimed Chemical Formula 3 is substituted at a position corresponding to A2 instead of A1, A3, or A4. However, the general formula (1) of Hong encompasses positional isomers wherein the group that is encompassed by the claimed Chemical Formula 3 is substituted at a position corresponding one of claimed A1, A3, or A4.
Therefore, given the general formula and teachings of Hong, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to make the positional isomer of the compound 64 wherein the group that is encompassed by the claimed Chemical Formula 3 is substituted at a position corresponding one of claimed A1, A3, or A4 instead of A-2. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by the general formula (1) of Hong in order to pursue the known options within their technical grasp and would expect the isomeric compounds to be useful as a host material in the light emitting layer of the device of Hong and possess the properties of improved luminous efficiency, thermal stability, driving voltage, and lifetime taught by Hong. A prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP § 2144.09 I. When compounds which are position isomers or homologs are of sufficiently close structural similarity, there is an expectation that such compounds possess similar properties. See MPEP § 2144.09 II.
The modified compound 64 of Hong has the structure
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and is a compound of the claimed Chemical Formula 1 wherein:
one of A1, A3 and A4 is represented by Chemical Formula 3, and the remaining of A1 to A4 are each hydrogen;
A7 is represented by Chemical Formula 4 and the other is hydrogen, and A5, A6, and A8 are hydrogen;
R9 is not required to be present;
p is 0;
L2 is a direct bond;
L1 is a phenylene group;
Ar1 is a benzimidazolyl group substituted with a phenyl group;
X1 is CRx;
X2 is CRy;
Rx and Ry bond to each other to form a direct bond;
R3 and R6 area each an unsubstituted C6 aryl group and R1, R2, R4, R5, R7, and R8 are each hydrogen;
R, R', and R'' are not required to be present; and
m is 1 and n is 0.
The modified device comprises the second host material of Hong having a weight ratio of 0.3 to 3 with respect to the first host material of Katoh having weight ratio of 1, which overlaps with the claimed ratio of 1:10 to 10:1. A prima facie case of obviousness exists where the claimed ranges overlap or lie inside ranges disclosed by the prior art. See MPEP § 2144.05.
Therefore the device of Katoh in view of Lee and Hong meets claims 1-3 and 8-17.
Regarding claim 7, Katoh in view of Lee and Hong teaches the compound as discussed above with respect to claim 1.
Katoh in view of Lee and Hong does not specifically disclose a device comprising a compound as claimed in claim 7. For example, the modified compound 64 of Hong differs from the claimed compound 2-29
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in that the carbazolyl substituent of claimed Chemical Formula 3 is substituted with two phenyl groups instead of only one. However, Hong teaches that the substituents on the bipolar triphenylene compound of general formula (1) include a group represented by Formula 3 (Hong-Mt, page 4 of 20, lines 8-13), which is a carbazolyl group
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(Hong-WO, page 4), which is present in compound 64 of Hong. Further, Hong teaches that in Formula 3 of Hong, Q1 and Q2 may be hydrogen or an aryl group, among others (Hong-Mt, page 5 of 20, lines 22-27).
Therefore, given the general formula and teachings of Hong, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute one of Q1 and Q2 with hydrogen, because Hong teaches the variable may suitably be selected as such. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful as a host material in the light emitting layer of the device of Hong and possess the benefits as described above taught by Hong. See MPEP § 2143.I.(B).
The further modified compound 64 of Hong corresponds to the claimed compound 2-29 and therefore the modified device meets claim 7.
Conclusion
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Elizabeth M. Dahlburg whose telephone number is 571-272-6424. The examiner can normally be reached Monday through Thursday, 9 a.m. to 4 p.m. ET, and alternate Fridays.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer Boyd can be reached on 571-272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ELIZABETH M. DAHLBURG/Primary Examiner, Art Unit 1786