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 .
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 (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.
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 1-8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (US 2012/0168730 A1) in view of Li (J. Mater. Chem. C, 2019, 7, 9966-9974).
Regarding claim 1, Kim et al. teaches a heterocyclic compound (Cpd 69) that reads on Chemical Formula 1
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439
530
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, wherein the claimed Chemical Formula 1
R1 to R13 and R15 to R17 are hydrogen atoms
R14 is the claimed Chemical Formula 2, wherein,
L is an unsubstituted C6 arylene
Ar1 is a substituted C6 aryl group
Ar2 is an unsubstituted C6 aryl group
Cpd 69 of Kim fails to teach wherein at least one of R5 to R11 is a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; or a group represented by Chemical Formula 2. However, Kim teaches that Cpd 69 is a specific compound of formula 1 (para. [0011] and [0024]). In formula 1, Kim teaches that the R5 of formula 1 can be a fused or non-fused C6-C60 aryl group (para. 0013) and that R5 can be substituted or unsubstituted with a C6-C60 aryl group (para. [0023]). Cpd 77 of Kim is an example of a compound with an R5 substituted with a C6 aryl group.
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726
994
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Li discloses the use of acridine derivatives in OLED devices, specifically sterically crowded acridine derivatives. Li teaches the differences within using acridine derivatives with ortho, meta, and para substituents. While studying the effects of the acridine derivatives in the device performance, Li determined that the more sterically crowded ortho acridine derivative presented higher external quantum efficiency, higher maxim current efficiency, higher maximum power efficiency, higher maximum luminance, and a low roll-off.
Therefore, given the general formula and teachings of Kim, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute one of the hydrogens in the R5 to R11 positions with a phenyl group because Kim teaches that the R5 position of their formula 1 can be substituted with a C6-C60 aryl, and they show several examples such as Cpd 77 with this substitution. The substitution would have been one preferred element for another and one of ordinary skill in the art would reasonably expect the predictable result that the modified compound would be useful as acridine derivative in the hole transport layer of the OLED device of Kim and possess the benefits taught by Kim. See MPEP 2143.I.(B).
Additionally, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to specifically select the R5 position of the instant application to place the aryl group, because it would have been choosing the sterically crowded position, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the heterocyclic compound in the hole transport layer of the OLED device of Kim and possessing the benefits taught by Li. One of ordinary skill in the art would have been motivated to produce additional compounds represented by/devices comprising sterically crowded acridine derivative having the benefits of higher maximum current efficiency, maximum power efficiency, and maximum luminance taught by Li in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Modified Cpd 69 reads on Chemical Formula 1 of instant application wherein R5 is an unsubstituted C6 aryl group.
Regarding claim 2, Modified Cpd 69 of Kim teaches the heterocyclic compound of claim 1, however, it does not teach wherein R16 and R17 are the same as or different from each other, and each independently a substituted or unsubstituted C1 to C20 alkyl group.
However, in formula 1, Kim teaches that R1 and R2 may be straight-chain or branched C1-C40 alkyl group. Cpd 130 of Kim is an example of formula 1 wherein R1 and R2 are C1 alkyl groups (methyl groups).
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901
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Therefore, given the general formula and teachings of Kim, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute the hydrogens in Modified Cpd 69 in the R16 and R17 positions of instant the instant application with methyl groups because Kim teaches that the R1 and R2 positions of their formula 1 can be substituted with straight-chain or branched C1-C40 alkyl groups, and they show several examples such as Cpd 130 with this substitution. The substitution would have been one preferred element for another and one of ordinary skill in the art would reasonably expect the predictable result that the modified compound would be useful as acridine derivative in the hole transport layer of the OLED device of Kim and possess the benefits taught by Kim. See MPEP 2143.I.(B).
Further Modified Cpd 69 of Kim reads on the on claim 2 wherein R16 and R17 are the same and are an unsubstituted C1 alkyl group.
Regarding claim 3, further modified Kim teaches wherein R5 is an unsubstituted C6 aryl and R14 is the claimed Chemical Formula 2 (as defined above for claim 1 and 2 in Paragraphs 7 and 8).
Regarding claim 4, further modified Kim further teaches wherein R5 is an unsubstituted C6 aryl and R14 is the claimed Chemical Formula 2 (as defined above for claim 1 and 2 in Paragraphs 7 and 8).
Regarding claim 6, further modified Kim further teaches wherein Chemical Formula 1 is represented by compound 250 of instant application (Further Modified Cpd 69 as depicted for claim 2 in Paragraph 8).
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280
606
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Regarding claim 7, modified Kim further teaches an organic light emitting device (Device Example 11, Table 1, para. [0075] – [0077]) comprising: a first electrode (ITO anode, para. [0076]); a second electrode (aluminum cathode, para. [0077]) provided to face the first electrode; and organic material layers (hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer, para. [0076] - [0077]) provided between the first electrode and the second electrode
Example 1 of modified Kim does not specifically teach wherein at least one of the one or more organic material layers comprises the compound of claim. However, modified Kim teaches that the hole transport layer comprises Cpd 131, a specific compound of formula 1 of Kim. Further Modified Cpd 69 is a specific Cpd of formula 1.
Therefore, given the general formula and teachings of Kim, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute Cpd 131 with Further Modified Cpd 69. The substitution would have been one preferred element for another and one of ordinary skill in the art would reasonably expect the predictable result that the modified compound would be useful as the acridine derivative in the hole transport layer of the OLED of Kim and possess the benefits taught by Kim. See MPEP 2143.I.(B).
Regarding claim 8, modified Kim further teaches wherein the organic light emitting device of claim 7 comprises a hole injection layer (para. [0076]), a hole transport layer (para . [0076]), a light emitting layer (para. [0077]), an electron transport layer (para. [0077]), and an electron injection layer (para. [0077]).
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Kim et al. (US 2012/0168730 A1) and Li (J. Mater. Chem. C, 2019, 7, 9966-9974) as applied to claims 1-4 and 6-8 above, and further in view of Fennimore et al. (US 2017/0200893 A1).
Regarding claim 5, modified Kim teaches the heterocyclic compound of claim 1 as applied above in paragraph 7.
Kim fails to teach wherein the content of deuterium is 30% to 100% based on the total number of hydrogen atoms and deuterium atoms in the Chemical Formula 1. However, in formula 1
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, Kim teaches that R1 to R7 may be deuterium (para. 0012] – [0013]), and that R1 to R7 and L may be substituted with deuterium.
Fennimore et al. discloses an OLED device and teaches that deuterated materials can be less susceptible to degradation by holes, electrons, excitons, or a combination thereof (para. [0098]). Additionally, Fennimore teaches that deuteration can potentially inhibit degradation of the compound during device operation, which in turn can lead to improved device lifetime (para. [0098]).
Therefore, it would have been obvious for one of ordinary skill in the art before the effective filling date of the claimed invention to further modify Cpd 69 by deuterating the compound, based on the teachings of Fennimore.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to deuterate modified Cpd 69, because it would have been choosing deuterium as a substituent, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the heterocyclic compound in the hole transport layer of the OLED device of Kim and possessing the benefits taught by Fennimore. One of ordinary skill in the art would have been motivated to produce additional compounds represented by/devices comprising deuterium having the benefits of stable compounds to prevent degradation and improve lifetime taught by Fennimore in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Conclusion
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/APCV/Examiner, Art Unit 1789
/JENNA N CHANDHOK/Primary Examiner, Art Unit 1789
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