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
Applicant’s election without traverse of Species B, a compound of formula (A1) wherein Ar3 is formula (A2-2), in the reply filed on 04/26/2024 was previously acknowledged.
No claims are currently withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim.
It appears that the election was made without traverse in the reply filed on 04/26/2024.
Priority
It is noted that JP2018-229962 dated 12/07/2018 does not appear to cover the full scope of the current claims and therefore is considered relevant to only part of the currently claimed invention.
Response to Amendment
The amendment of 11/13/2025 has been entered.
Claims 1, 28-29, and 30-34 are amended due to the applicant's amendment.
Claims 1, 11-12, and 29-40 are pending.
The objections to claims 1 and 28-34 as set forth in the previous Office action are each overcome due to the applicant's amendment. The objections are each withdrawn.
The rejection of claims 27 and 39-40 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, and the rejection of claims 27 and 39-40 under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as set forth in the previous Office action are each overcome by the applicant's amendment.
The rejection of claims 1, 11-12, 25-29, and 36-40 under 35 U.S.C. 103 as being unpatentable over Jatsch et al. US-20180222872-A1 and the rejection of claims 30-35 under 35 U.S.C. 103 as being unpatentable over Jatsch et al. US-20180222872-A1 as applied to claim 28 and further in view of Ito et al. US-20150357574-A1 as set forth in the previous Office action are each maintained.
Response to Arguments
The applicant’s arguments on pages 12-14 of the reply dated 11/13/2025 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 page 13 that the Office fails to provide the required reasoned explanation why one of ordinary skill in the art would have performed substitutions (1) and (2) in Jatsch's compound simultaneously.
Examiner's response – This is not found persuasive because paragraphs 31-34 of the previous Office action, which are repeated below, provide the motivations for the modifications (1) and (2). Each of these would have been obvious and the combination no less so, absent a showing of unexpected results. Regarding (1), a prima facie case of obviousness exists when chemical compounds have very close structural similarity and similar utilities. See MPEP § 2144.09 I. Regarding (2), 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 in the electron-transporting layer of the device of Jatsch and possess the properties as described by Jatsch. See MPEP § 2143.I.(B). The modified compound falls within the scope of the general formula of Jatsch and therefore one of ordinary skill in the art would have made both modifications simultaneously with a reasonable expectation of success. One having ordinary skill in the art would further expect the modified compound to be useful in the electron-transporting layer of the device of Jatsch and possess the properties as described by Jatsch.
Applicant's argument – The applicant argues bridging pages 13-14 that Jatsch's paragraph [0030] provides 110 independent options and the Office failed to provide any reasoned explanation why one of ordinary skill in the art would have selected dibenzofuran to be used in the 4th position while simultaneously selecting biphenyl to replace terphenyl in Jatsch's compound. The applicant argues on page 14 that one of ordinary skill in the art could only have arrive at the claimed compound through picking and choosing through myriads of options based on Jatsch's extremely broad disclosure.
Examiner's response – As noted above, paragraphs 31-34 of the previous Office action, which are repeated below, provide the motivations for the modifications (1) and (2).
A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill the art, including nonpreferred embodiments. See MPEP § 2123. While paragraph [0030] teaches several options, as noted in the rejection of record, the compound (219) already comprises a dibenzofuran group, and thus proposed modification is to form a positional isomer, as opposed to selecting the group from 110 options. Additionally, as noted in the rejection, Jatsch teaches specific compounds with an ortho-biphenyl group, including compound (14). One having ordinary skill in the art would look to the exemplary compounds in addition to the list in paragraph [0030] and would have made the proposed substitution with a reasonable expectation of success and thereby arrive at the claimed compound.
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, 11-12, 25-29, and 36-40 are rejected under 35 U.S.C. 103 as being unpatentable over Jatsch et al. US-20180222872-A1 (hereinafter "Jatsch").
It is noted that US-20180222872-A1 is related to CN-107922359-A and these both are cited on the IDS of 01/18/2024.
Regarding claims 1, 11, 25-26, 28-29, and 36-38, Jatsch teaches an organic electroluminescent device comprising a cathode, an anode and at least one emitting layer, and it may also comprise further layers including one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers and/or charge-generation layers (¶ [0070]), comprising a compound of the formula (I) (¶ [0068] and ¶ [0015]), wherein the compound is employed as electron-transport material in an electron-transport or electron-injection layer (¶ [0081]), and wherein the electron-transport layer may be doped with alkali metals or alkali-metal complexes, such as, for example, Li or LiQ (lithium hydroxyquinolinate) (¶ [0081]). It is noted that the electron-injection layer and the hole-blocking layer necessarily transports electrons from the cathode to the emissive layer and therefore may be considered a first or second electron-transporting layer. Jatsch teaches that the compound result in very high efficiency (¶ [0090]) and low voltage devices (¶ [0091]). Jatsch teaches examples of the compound of formula (I) including compound (219)
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339
346
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(¶ [0065], page 50), and compound (14)
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219
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(¶ [0065], page 15).
The prior art Jatsch does not exemplify a compound of the claimed formula (A6). For example, the compound 219 of Jatsch differs from the claimed compound of formula (A6) in that: (1) the dibenzofuran group is substituted at the 2-position instead of the 4-position; and (2) there is a terphenyl group instead of an ortho-substituted biphenyl group.
Regarding (1), the general formula of Jatsch teaches that the positions Ar1 and Ar2 are an aromatic or heteroaromatic ring system (¶ [0019]), which includes dibenzofuran (¶ [0030]), and the formula is open to any substitution position of the dibenzofuran heteroaromatic ring system.
Therefore, given the general formula and teachings of Jatsch, 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 (219) wherein the dibenzofuran group is substituted at the 4-position. One of ordinary skill in the pertinent art would have been motivated to produce additional compounds represented by the formula (1) of Jatsch in order to pursue the known options within their technical grasp and would expect the isomeric compounds to be useful in the electron-transporting layer of the device of Jatsch and possess the properties taught by Jatsch. 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.
Regarding (2), the general formula of Jatsch teaches that the positions Ar1 and Ar2 are an aromatic or heteroaromatic ring system (¶ [0019]), which includes terphenyl and biphenyl (¶ [0030]), and Jatsch teaches compounds comprising an ortho-substituted biphenyl group including compound (14) as shown above.
Therefore, given the general formula and teachings of Jatsch, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the terphenyl group at the position corresponding to Ar1 to Ar2 in the general formula of Jatsch with an ortho-substituted biphenyl group, because Jatsch 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 in the electron-transporting layer of the device of Jatsch and possess the properties as described above taught by Jatsch. See MPEP § 2143.I.(B).
The modified compound of Jatsch is a compound of the claimed formula (A6) wherein:
X1 is O;
Y1, Y2, and Y3 are each N;
Ar2a is an unsubstituted phenyl group;
R11a and R12a are each an unsubstituted phenyl group; and
R1 to R4 are each a hydrogen atom.
Regarding claims 12 and 40, Jatsch teaches the device comprising the modified compound as discussed above with respect to claim 1.
Jatsch does not teach a compound as discussed above wherein the position corresponding to Ar1 or Ar2 in the general formula of Jatsch is a dibenzothiophene group instead of a dibenzofuran group. However, the general formula of Jatsch teaches that the positions Ar1 and Ar2 are an aromatic or heteroaromatic ring system (¶ [0019]), which includes dibenzothiophene and dibenzofuran (¶ [0030]).
Therefore, given the general formula and teachings of Jatsch, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the dibenzofuran group at the position corresponding to Ar1 to Ar2 in the general formula of Jatsch with a dibenzothiophene group, because Jatsch 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 in the electron-transporting layer of the device of Jatsch and possess the properties as described above taught by Jatsch. See MPEP § 2143.I.(B).
The further modified compound corresponds to claimed compound ET-2
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224
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.
Regarding claims 27 and 39, Jatsch teaches the device comprising the modified compound as discussed above with respect to claim 1.
Jatsch does not exemplify a compound of the claimed formula (A6) as discussed above wherein the compound has at least one deuterium atom. However, Jatsch specifically teaches that the hydrogen atoms in the compound can be replaced with D (deuterium) (¶ [0016], ¶ [0018], ¶ [0020], ¶ [0029]).
Therefore, given the general formula and teachings of Jatsch, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to fully or partially deuterate the modified compounds, that is substitute some or all hydrogens for deuterium, because Jatsch teaches that hydrogen atoms in the compounds may be substituted for deuterium. 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 in the electron-transporting layer of the device of Jatsch and possess the properties as described above taught by Jatsch. See MPEP § 2143.I.(B).
Claims 30-35 are rejected under 35 U.S.C. 103 as being unpatentable over Jatsch et al. US-20180222872-A1 (hereinafter "Jatsch") as applied to claim 28 above and further in view of Ito et al. US-20150357574-A1 (hereinafter "Ito").
Regarding claims 30-35, Jatsch teaches the device comprising the modified compound as described above with respect to claim 28.
Jatsch does not exemplify a device wherein the emissive layer comprises a compound of the claimed formula (11), (12), (12-1), (13), or (13-1), which is an anthracene compound. However, Jatsch teaches the emission layer comprises at least one matrix material (host material) and an emitting dopant (¶ [0108]), wherein the dopant is a phosphorescent dopant (¶ [0069], ¶ [0070], ¶ [0077]).
Ito teaches an organic light-emitting device including an organic layer disposed between the first electrode and the second electrode including a first material represented by Formula I and a second material represented by Formula 2 (¶ [0008]). Ito teaches wherein the first material of Formula 1 is the host in the emissive layer (¶ [0168]), where the dopant is a phosphorescent dopant (¶ [0169]). Ito teaches an organic emitting device including the first materials represented by Formula I and the second materials represented by Formula 2 may have high efficiency and a long lifespan (¶ [0096]). Ito teaches examples of the first material of Formula 1 include compound 146
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354
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(page 15) and compound 155
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159
350
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(page 16).
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 the compound of Formula 1 and compound of Formula 2 of Ito into the device of Jatsch, based on the teaching of Ito. The motivation for doing so would have been to obtain high efficiency and long lifespan, as taught by Ito.
Further, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select compound 146 or 155 as the host compound of Formula 1, because it would have been choosing from the specific list of exemplary compounds of Formula 1, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as a host in the emissive layer of the device of Jatsch and possessing the properties taught above by Ito. One of ordinary skill in the art would have been motivated to produce additional devices comprising the compounds of Ito having the benefits taught by Ito in order to pursue the known options within their technical grasp with a reasonable expectation of success. See MPEP § 2143.I.(E).
The compound 146 of Ito is a compound of the claimed formula (11) and (12-1) wherein:
R11 to R18- are each a hydrogen atom;
L11 is an unsubstituted arylene group including 10 ring caron atoms (a naphthyl group) and L12 is a single bond;
Ar12a is an unsubstituted aryl group including 6 ring carbon atoms (a phenyl group); and
R21 and R23to R28 are each a hydrogen atom.
The compound 155 of Ito is a compound of the claimed formula (11) and (13-1) wherein:
R11 to R18- are each a hydrogen atom;
L12 is an unsubstituted arylene group including 6 ring caron atoms (a phenyl group); and
Ar11b and Ar12b are each an unsubstituted aryl group including 10 ring carbon atoms (a naphthyl group).
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.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
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