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 .
DETAILED ACTION
Claims 1-21 of C. Oh, et.al, US 18/356,509 (07/21/2023) are pending, under examination on merits and rejected.
Withdrawal Claim Rejections - 35 USC § 112(d)
Rejection of claims 21 under 35 U.S.C. 112(d) is withdrawn in view of claim 21 has been amended by deletion of the species 77 and Applicant’s argument on “carbocyclic group” is persuasive.
Claims Rejections 35 U.S.C. 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION. — The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claim 20 is rejected under 35 U.S.C. 112(b) as indefinite because there is insufficient antecedent basis for “n5” as the Formula 2-1 has been removed from the claim.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Note: The Hatakeyama compound 1-114 has been used for the 103 rejection made in the previous Office action, however after reconsideration the structure of compound 1-114 and the instant claims limitations, it is changed as 102 rejection as discussed below, which is not considered new ground of rejection. MPEP 1207.03(a). II.
Claims 9-11 and 16-20 are rejected under 35 U.S.C. 102(a)(1)(a)(2) as being anticipated by T. Hatakeyama, et al, US20200190115A1 (2020) (“Hatakeyama”).
As mentioned in the previous Office action that Hatakeyama teaches a compound 1-114, which maps the Formula 1 in claims 9-11 as indicated below.
PNG
media_image1.png
1238
1865
media_image1.png
Greyscale
Hatakeyama at page 52, the third compound.
Thus, the Hatakeyama compound 1-114 meets each and every limitation of claims 9-11, therefore, claims 9-11 are anticipated.
Claim 16 is anticipated because when each of n3, n41 and n42 is 0, claim 16 does not further limits the structure of claim 9.
Claims 17-20 are anticipated because the Formula 2 only is an alternative, further limit structure of the Formula 2 does not limit the structure of the alternative of the Formula 2.
Maintained 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.
Claims 1-21 are rejected under 35 U.S.C. 103 as being unpatentable over T. Hatakeyama, et al, US20200190115A1 (2020) (“Hatakeyama”).
Note: the rejection is reorganized after reconsideration of the teachings from Hatakeyama and Applicant’s Argument.
T. Hatakeyama, et al, US20200190115A1 (2020) (“Hatakeyama”)
Hatakeyama teaches a novel polycyclic aromatic compound having a plurality of aromatic rings linked by a boron atom, a nitrogen atom, and the like, which can be used as a material for an organic electroluminescent (EL) device; and an organic EL device comprising the novel polycyclic aromatic compound. Hatakeyama at abstract.
Hatakeyama teaches that the novel polycyclic aromatic compound can represented by the following general formula (2).
PNG
media_image2.png
360
419
media_image2.png
Greyscale
Hatakeyama at page 3, left col. [0035].
Hatakeyama teaches that:
Z1 and Z2 in the general formula (2) each independently represent an aryl, a heteroaryl, a diarylamino, a diheteroarylamino, an arylheteroarylamino, an alkyl, an aryloxy, a heteroaryloxy, an arylthio, or a heteroarylthio.
Hatakeyama at page 14, left col. [0098], emphasis added.
Hatakeyama teaches that:
Specific examples of the “aryl ring” include: a benzene ring which is a monocyclic system; a biphenyl ring which is a bicyclic system; a naphthalene ring which is a fused bicyclic system; a terphenyl ring (m-terphenyl, o-terphenyl, or p-terphenyl) which is a tricyclic system; an acenaphthylene ring, a fluorene ring, a phenalene ring, and a phenanthrene ring which are fused tricyclic systems; a triphenylene ring, a pyrene ring, and a naphthacene ring which are fused tetracyclic systems; and a perylene ring and a pentacene ring which are fused pentacyclic system.
Hatakeyama at page 14, left col. [0100], emphasis added.
Hatakeyama also teaches that the novel polycyclic aromatic compound can represented by the formula1-4451R and the formula 1-6000-R100.
PNG
media_image3.png
636
1603
media_image3.png
Greyscale
Hatakeyama at page 7, left col, the second formula for formula1-4451R and the last formula for formula 1-6000-R100.
Wherein, R in the formulas each independently represents an alkyl having 1 to 6 carbon atoms or an aryl having 6 to 10 carbon atoms; R100 in the formulas each independently represents an aryl having 6 to 10 carbon atoms, a carbazolyl, a diarylamino (the aryl is an aryl having 6 to 10 carbon atoms), an alkyl having 1 to 6 carbon atoms, a cycloalkyl having 3 to 10 carbon atoms, or an aryloxy having 6 to 10 carbon atoms; the aryl may be substituted by an alkyl having 1 to 6 carbon atoms; and the carbazolyl may be substituted by an aryl having 6 to 10 carbon atoms or an alkyl having 1 to 6 carbon atoms.
Thus, Hatakeyama fairly teaches one ordinary skilled artisan to modify the general formula (2) by using different groups ( R, R100) for Z1 and Z2.
Hatakeyama teaches specific examples of the novel polycyclic aromatic compound such as 1-114, 1-117 and 1-2001.
PNG
media_image4.png
1455
2060
media_image4.png
Greyscale
Hatakeyama at page 52 for 1-114, page 53 for 1-117, and page 149 for 1-2001. It should be noted that compound 1-2001 is one of the six synthesis working examples. See page 305-308, Synthesis Example (5).
Thus, per compounds 1-114 and 1-117, Hatakeyama teaches one ordinary skill that the a fluorene ring used in the compound of the general Formula (2) can be
PNG
media_image5.png
469
859
media_image5.png
Greyscale
Per FIG 1., Hatakeyama teaches the structure of an organic devices containing the novel polycyclic aromatic compound as indicated below.
PNG
media_image6.png
839
811
media_image6.png
Greyscale
Hatakeyama at Fig.1.
Hatakeyama teaches the structure of the organic devices includes:
a substrate 101,
a positive electrode 102 provided on the substrate 101,
a hole injection layer 103 provided on the positive electrode 102,
a hole transport layer 104 provided on the hole injection layer 103,
a light emitting layer 105 provided on the hole transport layer 104,
an electron transport layer 106 provided on the light emitting layer 105,
an electron injection layer 107 provided on the electron transport layer 106,
and a negative electrode 108 provided on the electron injection layer 107.
Hatakeyama at page 252, [0144], emphasis added.
Regarding the light emitting layer 105, Hatakeyama teaches that the light emitting layer 105 comprises a host material and a dopant material. Hatakeyama at page 254, [0162], line 3-4. The a dopant material can be the novel polycyclic aromatic compound. Hatakeyama at page 254, [0161].
Regarding the dopant sensitizer, Hatakeyama teaches that an assist dopant material can be used with dopant material; the use amounts of a host material, the assist dopant material, and a dopant material are usually 40 to 99.999% by weight, 59 to 1% by weight, and 20 to 0.001% by weight, respectively with respect to the entire material for a light emitting layer. Hatakeyama at page 255, [0166].
Hatakeyama further teaches working examples such as Example 5 which is an organic element using compound 1-2001 as dopant. Hatakeyama at page 318, Example 5. Hatakeyama teaches that the organic element using compound 1-2001 as dopant has much deeper blue emission and higher external quantum efficiency than Comparative Example 3. Hatakeyama at page 318, Example 5, [0610]-[0611], emphasis added.
The Hatakeyama compound 1-2001 maps the Formula 1 in the independent claim 1 and claim 9 as indicated below:
PNG
media_image7.png
963
1595
media_image7.png
Greyscale
Difference between Hatakeyama and the Claims
The Hatakeyama compound 1-2001 differs from the species 318 in claim 21 in that the diarylamino group
PNG
media_image8.png
299
219
media_image8.png
Greyscale
is not the claimed aryl group
PNG
media_image9.png
245
294
media_image9.png
Greyscale
as indicated below.
PNG
media_image10.png
693
2232
media_image10.png
Greyscale
Obvious Rational of the Claims 1-21
It would have been prima facie obvious for one ordinary skilled artisan to arrive at the instantly claimed inventions based on the teachings from Hatakeyama with a reasonable expectation of success before the effective filing date of the claimed invention.
Obviousness of a claimed compound can be supported where there is motivation to substitute particular chemical moieties in a prior art compound for others so as to arrive at a claimed compound. MPEP § 2143(I)(B). For example, in the pharmaceutical arts, the rational is stated as motivation to select a known compound and also motivation to structurally modify the selected compound in a particular way to achieve a claimed compound. MPEP § 2143(I)(B) (see for example, MPEP § 2143(I)(B) Example 9, citing Eisai Co. Ltd. v. Dr. Reddy’s Labs., Ltd., 533 F.3d 1353, 87 USPQ2d 1452 (Fed. Cir. 2008).
One of ordinary skilled artisan is motivated to select Hatakeyama’s compound 1-2001 for further investigation because Hatakeyama discloses it as an example of the Formula 2 and it can be used as a dopant for an organic element having much deeper blue emission and higher external quantum efficiency. Having selected Hatakeyama’s compound 1-2001, one of ordinary skill is motivated to substitute both of the diarylamino groups
PNG
media_image11.png
198
324
media_image11.png
Greyscale
with an aryl group such as a fluorene group
PNG
media_image9.png
245
294
media_image9.png
Greyscale
as follows thereby arriving at the species 318 in claim 21 which falls within the chemical genera of instant claims 1 and 9-10, therefore, claims 9-10 and 21 are obvious.
PNG
media_image12.png
1673
1354
media_image12.png
Greyscale
One ordinary skill is motivated to do so with a reasonable expectation of success because:
(i). per the formula1-4451R and the formula 1-6000-R100, Hatakeyama teaches that the general formula (2) can be modified through modification on the Z1 and Z2;
(ii). Hatakeyama teaches that aryl group is an alternative of a diarylamino for the Z1 and Z2 in the general formula (2). (See Hatakeyama at page 14, left col. [0098]);
(iii). Hatakeyama teaches that aryl group can be a fluorene ring; (see Hatakeyama at page 14, left col. [0100]) and
(iii). Hatakeyama teaches that fluorene ring used in the compound of the general Formula (2) can be
PNG
media_image5.png
469
859
media_image5.png
Greyscale
.
With regards the connection position of the fluorene ring to the core structure of the proposed compound, one ordinary skill would arrive at the claimed position through “obvious to try” given there is a finite number position in the fluorene ring can be connected to the core structure. MPEP 2143. I. (E). The rational supporting the modification is simple substitution of one known element for another to obtain predictable results. MPEP 2143. I. (B).
Claim 1-4 are obvious because one ordinary skill is motivated to use the proposed compound as a dopant material to form an organic devices as taught by Hatakeyama, thus arrive at a device comprising:
a substrate 101,
a positive electrode 102 provided on the substrate 101,
a hole injection layer 103 provided on the positive electrode 102,
a hole transport layer 104 provided on the hole injection layer 103,
a light emitting layer 105 comprising the proposed compound and a host material provided on the hole transport layer 104,
an electron transport layer 106 provided on the light emitting layer 105,
an electron injection layer 107 provided on the electron transport layer 106,
and a negative electrode 108 provided on the electron injection layer 107.
which meets each and every limitation of claims 1-4, therefore, claims 1-4 are obvious.
Claims 5-6 are obvious because one ordinary skill is also motivated to further modify the proposed device by including an assist dopant material in the light emitting layer 105, wherein the amounts of a host material, the assist dopant material, and a dopant material are usually 40 to 99.999% by weight, 59 to 1% by weight, and 20 to 0.001% by weight, respectively with respect to the entire material for a light emitting layer as taught by Hatakeyama. Hatakeyama at page 255, [0166]. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP 2144.05. I. Herein, each of the claimed ranges of 50% to 90%, 10% to 30% and 0.1% to 5% overlaps the prior art ranges of 40% to 99.99%, 1% to 59% and 0.001% to 20% respectively, therefore, a prima facie case of obviousness exists.
Claims 7-8 are obvious because Hatakeyama teaches that element comprising the proposed compound can be used as a part for a display apparatus or a lighting apparatus. Hatakeyama at page 10, Item. 17 and page 31, [0632], Industrial applicability. One ordinary skill is also motivated to include a touch screen layer for the display apparatus comprising the proposed compound.
Claims 11 and 15 are obvious because X11, X12, X21 and X22 in the proposed compound are O or NR8, wherein R8 is a phenyl group.
Claim 12-14 are obvious because Z1 and Z2, which maps the R1 and R2 in claim 9 and R12 and R22 in claim 10 respectively, in the proposed compound is a group represented by the Formula 2 in the instant claim 9.
Claim 16 is obvious because one ordinary skill is also motivated to further modify the proposed compound by substitution of the hydrogen atom(s) of CY3 with an alkyl group such as methyl group as indicated below thus arrive at the claimed compound.
PNG
media_image13.png
572
2348
media_image13.png
Greyscale
One ordinary skill is motivated to do so with a reasonable expectation of success because Hatakeyama teaches that in the general Formula (2):
[0046] R1 and R2 each independently represent a hydrogen atom, an alkyl having 1 to 6 carbon atoms, or an aryl having 6 to 12 carbon atoms.
Hatakeyama at page 3, [0046], emphasis added.
Claim 17 is obvious because the moiety of
PNG
media_image9.png
245
294
media_image9.png
Greyscale
in the proposed compound maps the Formula 2A as each of R61-R64 and R71-R73 are hydrogen atoms and each of R51-R52 are methyl groups.
Claims 18 is obvious because one ordinary skill is also motivated to modify Hatakeyama’s compound 1-2001 by replacing the
PNG
media_image8.png
299
219
media_image8.png
Greyscale
moieties with
PNG
media_image14.png
379
398
media_image14.png
Greyscale
as indicated below as Hatakeyama teaches that a aryl group used in the compound of the general Formula (2) can be
PNG
media_image5.png
469
859
media_image5.png
Greyscale
.
PNG
media_image15.png
1673
1165
media_image15.png
Greyscale
Claim 19 and 20 are obvious because one ordinary skill is also motivated to further modify the above proposed compound by bonding of the two phenyl groups to form a fluorene group as indicated below thus arrive at the claimed compound.
PNG
media_image16.png
688
2971
media_image16.png
Greyscale
One ordinary skill has a motivation to do so with a reasonable expectation of success because Hatakeyama teaches that “a polycyclic aromatic compound having an extended n-conjugated system generally has excellent redox stability”. Hatakeyama at page 1, [0006], line 20-22. By bonding of the two phenyl groups to form another fluorene group can extend n-conjugated system of the compound and enhance redox stability.
Applicant’s Argument
Applicant first argues the 103 rejection is engaged in impermissible hindsight. The last paragraph of page 66 in the Remarks filed on 03/31/2026.
This argument is not persuasive. As mentioned in the rejection above and the previous Office action that:
(i). Hatakeyama teaches that compound 1-2001 is an example compound and it can be used as a dopant for an organic element having much deeper blue emission and higher external quantum efficiency, therefore, one ordinary seeking organic element having blue emission is motivated to elected compound 1-2001 for modification;
(ii).Hatakeyama teaches that the diarylamino groups in the compound 1-2001 can be replaced by a fluorene groups;
(iii). Per the structures of compounds 1-114/117, Hatakeyama teaches that fluorene groups of
PNG
media_image5.png
469
859
media_image5.png
Greyscale
can be introduced into the following general formula (2).
Therefore, there is a prima facie case of obviousness for one ordinary skill seeking a dopant for an organic element having much deeper blue emission and higher external quantum efficiency is motivated to modify the compound 1-2001 through replacing the diarylamino groups with fluorene groups of
PNG
media_image5.png
469
859
media_image5.png
Greyscale
. This proposed modification does not represent ‘impermissible hindsight’ because it takes into account only knowledge which was within the level of ordinary skill as taught by Hatakeyama at the time the claimed invention was made and does not include knowledge gleaned only from applicant’s disclosure. MPEP 2145.X. A.
Applicant also argues that there is no articulated motivation to select Hatakeyama's 1-2001 as a starting point. Paragraph 2-3 of page 67 in the Remarks filed on 03/31/2026. This argument is not persuasive, as mentioned in the previous Office action and the rejection above that per Example 5, Hatakeyama teaches that compound 1-2001 can be used as a dopant for an organic element having much deeper blue emission and higher external quantum efficiency, therefore, one ordinary seeking organic element having blue emission is motivated to elected compound 1-2001 for modification. Hatakeyama at page 318, Example 5, [0610]-[0611].
Applicant further argues that there is no articulated motivation to select fluorenyl moieties in particular, nor to combine them with 1-2001 at the precise location. Pages 67-68 in the Remarks filed on 03/31/2026. This argument has been fully considered but not persuasive. As mentioned in the rejection above that Hatakeyama teaches that his novel polycyclic aromatic compound can represented by the formula1-4451R and the formula 1-6000-R100 as indicate below.
PNG
media_image3.png
636
1603
media_image3.png
Greyscale
Wherein, R/R100 can be different groups including an aryl and a diarylamino, therefore, Hatakeyama teaches the precise location (Z1 and Z2) for modification of his novel polycyclic aromatic compound the formula (2). Given Hatakeyama teaches that a fluorene is an aryl group and also teaches example compounds 1-114/1-117 comprises fluorene, therefore, one ordinary skilled artisan seeking to modify compound 1-2001 is motivated to replace the diarylamino with a fluorene that is an alternative of the diarylamino.
Applicant further argues that there is no reasonable expectation of success when dramatically altering the electronics of the system in a luminescent material. Page 69 in the Remarks filed on 03/31/2026. This argument is not persuasive because Hatakeyama clearly teaches that for aryl and diarylamino are alternative for (Z1 and Z2). Further, in addition to compound 1-2001, Hatakeyama also teaches compound 1-16001 (Hatakeyama at page 237) that is a compound made through replacing the diarylamino of compound 1-2001 with an aryl.
PNG
media_image17.png
576
2013
media_image17.png
Greyscale
Therefore, one ordinary skilled artisan has a reasonable expectation of success for replacing of the diarylamino of compound 1-2001 with another aryl such as a fluorene. It should be noted that obviousness does not require absolute predictability of success. MPEP 2143. Further, Applicant does not provide any evidence to prove the proposed modification would cause dramatically electronics changes in the luminescent material.
Applicant also argues the rejection of 19 on the ground that the teaching from Hatakeyama (“a polycyclic aromatic compound having an extended n-conjugated system generally has excellent redox stability”) conflicts with well known facts in the art. This argument is not persuasive because Applicant does not provide any solid evidence showing Hatakeyama is not correct. While pentacene may has less stability than tetracene, however, which cannot conclude that increase conjugation of the Hatakeyama compound cannot increase its redox stability as Hatakeyama taught because they are different types of compounds. Rather, Hatakeyama teaches compounds such as compound 1-413, which has extended conjugation system. See Hatakeyama at page 71, compound 1-413.
PNG
media_image18.png
723
1223
media_image18.png
Greyscale
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 FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday.
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, Scarlett Goon can be reached on (571)2705241. 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.
/FRANK S. HOU/Examiner, Art Unit 1622
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
Prosecution Insights