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 .
Election/Restrictions
Applicant's election of species A2 which is
PNG
media_image1.png
131
142
media_image1.png
Greyscale
connecting structure B1, which is one of Chemical Formulae 2-5 in claim 5 in the reply filed on 12/06/2024 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
In the Office Action of 12/30/2024, the Examiner withdraws the requirement of election among (B1) and (B2) only. Applicant's election of 12/06/2024 is equated with election of Species (A2) – the bridge structure of L is
PNG
media_image1.png
131
142
media_image1.png
Greyscale
.
Claims 3, 7, and 11 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group.
Response to Amendment
The amendment of 08/05/2025 has been entered.
Disposition of claims:
Claims 2, 15-16, and 21 have been canceled.
Claims 1, 3-14, and 17-20 are pending.
Claims 3, 7, and 11 have been withdrawn.
Claims 1 and 12 have been amended.
The amendment of claims 1 and 12 has overcome the rejections of claims 1, 4-6, 8-10, 12-14, and 17-20 under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al. (US 2019/0207112 A1, hereafter Hatakeyama ‘112) in view of Wakamiya et al. (US 2014/0058099 A1, hereafter Wakamiya) as evidenced by Hatakeyama et al. (“Ultrapure Blue Thermally Activated Delayed Fluorescence Molecules: Efficient HOMO–LUMO Separation by the Multiple Resonance Effect”, Adv. Mater. 2016, vol. 28, page 2777-2781) set forth in the last Office Action. The rejections have been withdrawn.
Response to Arguments
Applicant’s arguments see page 32-35 of the reply filed 08/05/2025 regarding the rejections of claims 1, 4-6, 8-10, 12-14, and 17-20 under 35 U.S.C. 103 as being unpatentable over Hatakeyama ‘112/Wakamiya/Hatakeyama ‘2016 set forth in the Office Action of 10/07/2025 have been considered.
Applicant argues that the amendments would be sufficient to overcome the rejection of record.
The cited rejections refer to the Organic light emitting device of Hatakeyama ‘112 as modified by Wakamiya formed by a coating composition comprising the Compound 3-182-N-1 of Hatakeyama ‘112. The compound does not read on the Formula A of the amended claims. Thus, the rejections are withdrawn.
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 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 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 1, 4-6, 8-10, 12-14, and 17-20 are rejected under 35 U.S.C. 103 as being unpatentable over Fujita et al. (US 2019/0165279 A1, hereafter Fujita) in view of Wakamiya et al. (US 2014/0058099 A1, hereafter Wakamiya) as evidenced by Hatakeyama et al. (“Ultrapure Blue Thermally Activated Delayed Fluorescence Molecules: Efficient HOMO–LUMO Separation by the Multiple Resonance Effect”, Adv. Mater. 2016, vol. 28, page 2777-2781).
Regarding claims 1, 4-5, 8-10, 13-14, and 17- 20, Fujita discloses an organic light emitting device comprising a light emitting layer containing an anthracene compound of Formula (1) as a host, a dibenzochrysene compound of Formula (2) as a host ([0011]), and a multimer of Formula (3) as a dopant ([0196]). Fujita exemplifies Compound (2-101) ([0081]) as the dibenzochrysene compound, Compound (1-101) as the anthracene compound ([0156]), and Compound (3-139) as the dopant ([0224]).
PNG
media_image2.png
505
727
media_image2.png
Greyscale
The Compound (1-101) of Fujita has identical structure as Applicant’s Formula A of the instant claims.
Fujita does not disclose a specific organic light emitting device comprising the Compounds (2-101), (1-101), and (3-139) formed by a coating method.
However, Fujita does teach the light emitting layer contains Formula (1), Formula (2), and Formula (3) ([0011], [0196]) and exemplifies Compound (2-101) as Formula (1) ([0081]), Compound (1-101) as Formula (2) ([0156]), and Compound (3-139) as Formula (3) ([0224]).
Fujita further teaches the structure of the organic light emitting device comprising a first electrode, a light emitting layer comprising the anthracene host of 49 wt%, the dibenzochrysene host of 49 wt%, and the boron dopant of 2 wt%, and a second electrode ([0256], [0273]-[0274], [0583]). Fujita additionally teaches the layer of the organic light emitting device can be formed by a spin coating method or a coating method ([0446]). It is known in the art that a coating method requires solid phase compounds (i.e. host and dopant) and a solvent to dissolve the solid compounds. The solution including the solvent and the host and dopant compounds is equated with the claimed coating composition.
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 Compounds (2-101), (1-101), and (3-139) of Fujita by incorporating them into the light emitting layer of an organic light emitting device having structure of a first electrode, a light emitting layer, and a second electrode, wherein the light emitting layer contains the Compound (2-101) as a host (49 wt%), Compound (1-101) as a host (49 wt%), and Compound (3-139) as a dopant (2 wt%); and the light emitting layer formed by a solution-based coating method, as taught by Fujita.
The motivation of doing so would have been to provide the device using more cost effective solution-based coating method.
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 modification provides Modified organic light emitting device comprising a first electrode, a light emitting layer, and a second electrode, wherein the light emitting layer is formed using a coating composition containing Compound (2-101) as a host (49 wt%), Compound (1-101) as a host (49 wt%), Compound (3-139) as a dopant (2 wt%), and a solvent.
The dopant compound is not a multimer comprising a plurality of the Compound (3-139) unit structures and having identical structure as Applicant’s Chemical Formula 1; however, Fujita does teach the light emitting layer comprises a trimer comprising unit structures each represented by Formula (3) and connected by a linking group including phenylene ([0220]).
Wakamiya discloses a compound having multiple polycyclic ring moieties connected by a central linking group Ar1 (see Formula 1 in [0008]), wherein the polycyclic ring moiety can encompass the Compound 1-2619 of Hatakeyama ‘112.
Wakamiya teaches the structure of a trimer comprising three polycyclic ring moieties and a central benzene ring, represented by Formula (7) ([0085]-[0087]), wherein Y1, Y2, and Y3 can be boron; X1, X4, X7 can be nitrogen; R1 to R50 can be hydrogen or a substituent; L3 and L4, L7 and L8, and L11 and L12 can be bonded to form a linking group in which the linking group can be nitrogen; L1 and L2, L5 and L6, and L9 and L10 can be hydrogen; and the R groups can be hydrogen or substituted or unsubstituted alkyl ([0086]-[0087], [0008], [0028]).
PNG
media_image3.png
358
511
media_image3.png
Greyscale
Wakamiya teaches that a compound having multiple cyclic structures provides high glass transition temperature, high thermal stability, high charge transport efficiency, amorphous stability, and low crystallization ([0006]-[0008]) such that the organic light emitting device comprising the compound provides high efficiency, low power consumption, and long life ([0010]).
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 (3-139) of Fujita by incorporating it into the three polycyclic ring moieties of the Formula (7) of Wakamiya to provide a trimer, as taught by Fujita and Wakamiya.
The motivation of doing so would have been to provide high glass transition temperature, high thermal stability, high charge transport efficiency, amorphous stability, and low crystallization such that the organic light emitting device comprising the compound provides high efficiency, low power consumption, and long life based on the teaching of Wakamiya.
Furthermore, Fujita teaches that a trimer comprising unit structures each represented by Formula (3) and connected by a linking group such as phenylene ([0220]). Wakamiya teaches detailed trimer structure wherein three polycyclic unit structures are linked by a central phenyl ring at each meta positions as represented by Formula (7) of Wakamiya. Thus, 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 modification provides Compound of Fujita as modified by Wakamiya.
PNG
media_image4.png
535
522
media_image4.png
Greyscale
The modification also provides Organic light emitting device of Fujita as modified by Wakamiya comprising a first electrode, a light emitting layer, and a second electrode, wherein the light emitting layer is an organic material layer; and the light emitting layer is formed using a coating composition containing Compound (2-101) of Fujita as a host (49 wt%), Compound (1-101) of Fujita as a host (49 wt%), Compound of Fujita as modified by Wakamiya as a dopant (2 wt%), and a solvent, meeting all the limitations of claims 1, 4-5, 8-10, 13-14, 17-18, and 20.
The Organic light emitting device of Fujita as modified by Wakamiya reads on the claimed limitations above but fails to teach that the light emitting layer of the device is a blue light emitting layer.
It is reasonable to presume that the light emitting layer of the Organic light emitting device of Fujita as modified by Wakamiya is a blue light emitting layer.
Support for said presumption is found in the use of like materials which result in the claimed property.
The only light emitting material of the Organic light emitting device of Fujita as modified by Wakamiya is the Compound of Fujita as modified by Wakamiya. The compound comprises the boron-containing heterocyclic moiety (i.e. the six six-membered condensed ring) which has similar core structure as DABNA-1 and DABNA-2 of Hatakeyama ‘2016 (Fig. 2). Hatakeyama ‘2016 evidences that the boron-containing heterocyclic compound emits blue light (Table 1, emission wavelength around 460-470 nm). Thus, the Compound of Fujita as modified by Wakamiya is expected to emit blue light because the boron-containing heterocyclic ring compound emits blue light.
Furthermore, the instant specification states that the light emitting layer is a blue light emitting layer (page 68, lines 9-10). The Compound of Fujita as modified by Wakamiya has identical structure as Applicant’s Chemical Formula 1 as outlined above and substantially similar structure as Applicant’s specific embodiments including at least the 11th compound on page 49 of the specification.
Therefore, the light emitting layer of the Organic light emitting device of Fujita as modified by Wakamiya is a blue light emitting layer, meeting all the limitations of claim 19.
The burden is upon the Applicant to prove otherwise. In re Fitzgerald 205 USPQ 594. In addition, the presently claimed properties would obviously have been present once the Organic light emitting device of Fujita as modified by Wakamiya is provided. Note In re Best, 195 USPQ at 433, footnote 4 (CCPA 1977). Reliance upon inherency is not improper even though the rejection is based on Section 103 instead of 102. In re Skoner, et al. (CCPA) 186 USPQ 80.
Regarding claim 6, the Organic light emitting device of Fujita as modified by Wakamiya prepared by the Coating composition of Fujita as modified by Wakamiya reads on all the features of claim 1 as outlined above.
The device comprises a first electrode, a light emitting layer, and a second electrode, wherein the light emitting layer is an organic material layer; and the light emitting layer is formed using a coating composition containing Compound (2-101) of Fujita as a host (49 wt%), Compound (1-101) of Fujita as a host (49 wt%), Compound of Fujita as modified by Wakamiya as a dopant (2 wt%), and a solvent.
Three polycyclic moieties of the compound is connected to the central benzene ring via the phenyl group of the polycyclic moiety fused by one azaborinine ring, which does not reads on the limitation of Applicant’s Chemical Formula 6 or 7.
However, Fujita does not restrict the connection position of the polycyclic moieties to form a multimer. Fujita does teach a trimer comprising unit structures each represented by Formula (3) and connected by a linking group including phenylene ([0220]).
Wakamiya teaches the Formula (7) of Wakamiya wherein three polycyclic moieties can be connected to the central benzene ring via the phenyl group fused by one azaborinine ring (i.e. similarly as General Formula [1-2] in [0054]) or the phenyl group fused by two azaborinine rings (i.e. similarly as General Formula [1-1] in [0054]). Wakamiya teaches L1 and L2, L5 and L6, and L9 and L10 of Formula (7) can be bonded to form a linking group in which the linking group can be nitrogen; and L3 and L4, L7 and L8, and L11 and L12 can be hydrogen ([0086]-[0087], [0008]).
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 Fujita as modified by Wakamiya by substituting the connection position of the three polycyclic moieties from the phenyl group fused by one azaborinine ring to the phenyl group fused by two azaborinine rings, as taught by Fujita and Wakamiya.
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 the connection positions 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 Compound of Fujita as modified by Wakamiya (2).
PNG
media_image5.png
330
512
media_image5.png
Greyscale
The modification also provides Coating composition of Fujita as modified by Wakamiya (2) including the Compound (1-101) of Fujita as a host, Compound (2-101) of Fujita as a host, and the Compound of Fujita as modified by Wakamiya (2) as a dopant, and a solvent.
Regarding claim 12, the Organic light emitting device of Fujita as modified by Wakamiya prepared by the Coating composition of Fujita as modified by Wakamiya reads on all the features of claim 1 as outlined above.
The device comprises a first electrode, a light emitting layer, and a second electrode, wherein the light emitting layer is an organic material layer; and the light emitting layer is formed using a coating composition containing Compound (2-101) of Fujita as a host (49 wt%), Compound (1-101) of Fujita as a host (49 wt%), Compound of Fujita as modified by Wakamiya as a dopant (2 wt%), and a solvent.
The Compound of Fujita as modified by Wakamiya has similar structure as the 13th embodiment on page 27 in claim 12 (see structure below).
PNG
media_image6.png
310
338
media_image6.png
Greyscale
The only difference between two compounds is that the Compound of Fujita as modified by Wakamiya has a t-butyl group at each of the positions corresponding to R6 (or R9) of Formula (3’) of Fujita ([0196], and see the moieties pointed by arrows in the figure above); however, Hatakeyama does teach that R6 (or R9) can be hydrogen ([0034]) and exemplifies embodiments wherein the substituent at position R6 (or R9) is hydrogen ([0200], and see examples in [0224], including at least 3-131, 3-262).
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 Fujita as modified by Wakamiya by substituting the t-butyl group at each of the positions corresponding to R6 (or R9) of Formula (3’) of Fujita (i.e. the t-butyl groups pointed by three arrows in the figure above).
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 the exemplified substituent groups 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 Compound of Fujita as modified by Wakamiya (3) which has identical structure as the 13th embodiment on page 27 in claim 12.
The modification also provides Coating composition of Fujita as modified by Wakamiya (3) including the Compound (1-101) of Fujita as a host, Compound (2-101) of Fujita as a host, and the Compound of Fujita as modified by Wakamiya (3) as a dopant, and a solvent.
Conclusion
Applicant's amendment necessitated the new ground(s) 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 SEOKMIN JEON whose telephone number is (571)272-4599. The examiner can normally be reached Monday - Friday 8:30am to 5:00pm EST.
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 at (571)272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/SEOKMIN JEON/Primary Examiner, Art Unit 1786
Prosecution Insights