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 .
Terminal Disclaimer
The ODP rejections over copending Application Nos. 17611452 , 17056634, 17617579, 17612183 and U.S. Patent No. 11,991,922 have been obviated by terminal disclaimer filed 10/31/2025.
Response to Arguments
Applicant's arguments filed 2/13/2025 have been fully considered but they are not persuasive.
Applicant argues that each of the references does not read on the new formulae of the amended claims. These arguments are not convincing, and the disclosures of the new structures are explained in bold font in the amended rejections below.
In the case of claim 19, however, additional rejections are made in view of references Ye et al (WO 2019218969) and Hong et al (US 20210317147 A1, WO 2020050619 A1)
Claim Rejections - 35 USC § 102/103
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.
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.
Claim(s) 1-7, 14-16 is/are rejected under 35 U.S.C. 102(a1) and (a2) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Kim et al (US 20210053998 A1, and WO 2020022751).
Kim discloses an OLED with the claimed anode, cathode, and light emission layer [0003] wherein the light emission layer includes an anthracene compound [0014] that is preferably deuterated [0091]
PNG
media_image1.png
231
288
media_image1.png
Greyscale
[claim 1, 0014].
Exemplary embodiments include compound 2-11:
PNG
media_image2.png
256
296
media_image2.png
Greyscale
[p160] which is the compound of the current claim 14 [clms of 10/31/2025, p11 top row, far right]. Kim teaches that when the anthracene structure is substituted with deuterium as described above, it is possible to increase the lifetime of the organic electroluminescent element [0067]. R5 to R12 may also include C5-C30 aryl groups [0078].
Kim also discloses the light emitting layer including a boron dopant that may be deuterated [claim 1, 0075] having the formula 1:
PNG
media_image3.png
183
320
media_image3.png
Greyscale
[claim 1, p122] .
In the Formula 1, R1 to R3 includes a C7-C60 aralkyl group [claim 1], “aralkyl” means an aryl-alkyl group, suitable examples include benzyl and naphthalenylmethyl, and the bond to the parent moiety is through the alkyl [0035]. This substituent reads on the claimed Formula 201, condition (2) in which one of T17 to T19 is an aryl group, and more specifically can be a phenyl or naphthyl group.
This rejection is made under both 35 USC 102 anticipation and 35 USC 103 obviousness. Examiner holds the opinion that the finite number of disclosed anthracene compounds and boron compounds would allow the ordinarily skilled artisan to readily envisage the claimed combination of deuterated anthracene and boron compounds, therefore the claims are anticipated. In the alternative, the claims are certainly obvious over the combination of elements disclosed, and the mere fact that a reference suggests a multitude of possible combinations does not in and of itself make any one of those combinations less obvious. Merck & Co. v. Biocraft Laboratories, 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir.), cert. denied, 493 U.S. 975 (1989).
Claim(s) 1-7, 14-16 is/are rejected under 35 U.S.C. 102(a1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Do et al (KR 20190127529 A).
Do discloses an OLED having an anode and a cathode and an organic light emitting layer comprising an anthracene-based compound that reads on claimed formula 1 and a boron-based compound that reads on claimed formula 2 [abstract, claim 1] wherein the anthracene compound includes deuterated embodiments such as 2-16 [p13] and 2-51 [p16] and the boron compound includes deuterated embodiments that are deuterated by more than 40% such as compounds 1-58 [p6], 1-200, and 1-202 [p11]:
PNG
media_image4.png
158
94
media_image4.png
Greyscale
PNG
media_image5.png
162
102
media_image5.png
Greyscale
PNG
media_image6.png
91
90
media_image6.png
Greyscale
PNG
media_image7.png
126
102
media_image7.png
Greyscale
PNG
media_image8.png
128
108
media_image8.png
Greyscale
Do discloses the anthracene compound with the generic formula:
PNG
media_image9.png
135
130
media_image9.png
Greyscale
wherein R14 to R21 include deuterium [p4].
Do discloses the generic formula of the boron containing compounds
PNG
media_image10.png
186
202
media_image10.png
Greyscale
wherein R1 to R11 a C7-C30 aralkyl group [claim 1], “aralkyl” means an aryl-alkyl group, and Do also teaches that an “aryl” group means an aromatic hydrocarbon having 6 to 60 carbon atoms [p9-10, bridging ¶], so a C7 aralkyl group will be benzyl, which reads on the claimed Formula 201, condition (2) in which one of T17 to T19 is an aryl group, and more specifically can be a phenyl group.
Do further discloses that in both compounds all the hydrogen atoms may be deuterium [claim 1, formula 1 and 2] meaning that all the disclosed embodiments can be fully deuterated.
This rejection is made under both 35 USC 102 anticipation and 35 USC 103 obviousness. Examiner holds the opinion that the finite number of disclosed anthracene compounds and boron compounds would allow the ordinarily skilled artisan to readily envisage the claimed combination of deuterated anthracene and boron compounds, therefore the claims are anticipated. In the alternative, the claims are certainly obvious over the combination of elements disclosed, and the mere fact that a reference suggests a multitude of possible combinations does not in and of itself make any one of those combinations less obvious. Merck & Co. v. Biocraft Laboratories, 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir.), cert. denied, 493 U.S. 975 (1989).
Claim(s) 1-7, 14-15, and 17 is/are rejected under 35 U.S.C. 102(a1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Hatakeyama et al (US 20180301629 A1).
Hatakeyama discloses an OLED with an anode and a cathode layer and a light emission layer comprising a boron compound of formula (1) and an anthracene compound of the formula (3) [abstract] wherein at least one hydrogen atom is replaced with deuterium in each compound [0035, 0051] and all the hydrogens may be replaced by deuterium atoms [0096, 0162]. There are several examples of the boron compound that read on the claimed formula 203-3 including
PNG
media_image11.png
190
426
media_image11.png
Greyscale
[p17]
Illustrative examples of the anthracene compounds include
PNG
media_image12.png
365
400
media_image12.png
Greyscale
[p56]
Which read on the claimed embodiments [see p41 of the claims for comparison], as well as
PNG
media_image13.png
257
368
media_image13.png
Greyscale
[p58]
Which read on the claimed embodiments [see p50 of the claims]. Regarding claim 6, Hatakeyama also discloses naphthobenzofuranyl groups [p59].
This rejection is made under both 35 USC 102 anticipation and 35 USC 103 obviousness. Examiner holds the opinion that the finite number of disclosed anthracene compounds and boron compounds would allow the ordinarily skilled artisan to readily envisage the claimed combination of deuterated anthracene and boron compounds, therefore the claims are anticipated. In the alternative, the claims are certainly obvious over the combination of elements disclosed, and the mere fact that a reference suggests a multitude of possible combinations does not in and of itself make any one of those combinations less obvious. Merck & Co. v. Biocraft Laboratories, 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir.), cert. denied, 493 U.S. 975 (1989).
Hatakeyama also discloses
PNG
media_image14.png
337
358
media_image14.png
Greyscale
[p17]
Which reads on claim 9 formula 2-A.
Claim Rejections - 35 USC § 103
Claim(s) 14-16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Do et al (KR 20190127529 A).
Regarding claims 14-15: Do discloses various position isomers of structures of claim 14, see for instance compound 2-1, and discloses the core structures of claim 15, and indicates that the structures may have the additional aryl groups having 6 to 30 carbon atoms [see definitions of R14 to R23 for formula 2 in claim 1], and as discussed above, the compounds may be fully deuterated.
Regarding claim 16: Do discloses various position isomers of structures of claim 16, see for instance compound 1-14 compared to p58 second row last compound of the instant claims, and as discussed above, the compounds may be fully deuterated.
If Applicant argues that the claimed embodiments are not disclosed with sufficient specificity and that examiner is picking and choosing with improper hindsight, Examiner notes that the rejection is made under 35 USC 103 obviousness. Examiner holds the opinion that there a finite number of disclosed structures of formula 1 and 2 and the disclosure of the substituents being deuterium would allow the ordinarily skilled artisan to prepare the claimed deuterated structures. The claims are obvious over the combination of elements disclosed, and the mere fact that a reference suggests a multitude of possible combinations does not in and of itself make any one of those combinations less obvious. Merck & Co. v. Biocraft Laboratories, 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir.), cert. denied, 493 U.S. 975 (1989).
Claim(s) 1-7, 14-16 and 19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Do et al (KR 20190127529 A) in view of Hong et al (US 20210317147 A1, WO 2020050619 A1).
Do, discussed above, does not disclose the specific structures of the Formula 208.
Hong discloses an OLED comprising the compound of the formula:
PNG
media_image15.png
180
261
media_image15.png
Greyscale
PNG
media_image16.png
108
385
media_image16.png
Greyscale
with specific examples including the structure below left, compare to the claimed structure on the right:
PNG
media_image17.png
314
407
media_image17.png
Greyscale
[p12]
PNG
media_image18.png
193
208
media_image18.png
Greyscale
[p94 of clms 2/13/2026].
The compounds may be substituted with deuterium and deuterated substituents [0063]. Hong teaches that including a silicon atom (Si) in a core structure of the compound, molecular rigidity increases and, as a result, excellent morphological stability is obtained. An organic light emitting device having high efficiency, low voltage and long lifetime properties can be obtained, and when including the compound of the present disclosure in a light emitting layer of an organic light emitting device, an organic light emitting device having high color gamut can be manufactured [0018].
It would have been obvious to one having ordinary skill in the art at the time of filing of Applicant’s invention to have used the silicon bridged boron compounds of the claims as the boron compounds of Do because Hong teaches that including a silicon atom (Si) in a core structure of the compound, molecular rigidity increases and, as a result, excellent morphological stability is obtained. An organic light emitting device having high efficiency, low voltage and long lifetime properties can be obtained, and when including the compound of the present disclosure in a light emitting layer of an organic light emitting device, an organic light emitting device having high color gamut can be manufactured.
Claim(s) 1-7, 14-15 and 19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al (US 20180301629 A1) in view of Hong et al (US 20210317147 A1, WO 2020050619 A1).
Hong is combined with Hatakeyama for the same reasons it is combined with Do above.
Claim(s) 1-7, 14-15 and 19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al (US 20210053998 A1, and WO 2020022751) in view of Hong et al (US 20210317147 A1, WO 2020050619 A1).
Hong is combined with Kim for the same reasons it is combined with Do and Hatakeyama above.
Claim(s) 1-7, 14-15 and 19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Do et al (KR 20190127529 A) in view of Ye et al (WO 2019218969).
Do, discussed above, does not disclose the specific structures of the Formula 208.
Ye discloses OLEDs comprising a host and a guest material including a boron compound [clm 1] having the general formula:
PNG
media_image19.png
210
207
media_image19.png
Greyscale
PNG
media_image20.png
157
196
media_image20.png
Greyscale
Wherein X1 and X3 are independently represented as N(R), C(R)2 or Si(R)2 and others [p3]. Therefore Ye teaches that a silicon bridge in the boron compound is equivalent to the absence of a bridge disclosed in Do
It would have been obvious to one having ordinary skill in the art at the time the invention was made to have used the silicon bridge of the claims in the boron compound of Do because Ye teaches that the claimed unbrigded compound and the silicon-bridged compound of Do are functionally equivalent and it is prima facie obvious to substitute art-recognized functional equivalents known for the same purpose, see MPEP § 2144.06; In re Ruff, 256 F.2d 590, 118 USPQ 340 (CCPA 1958). An express suggestion to substitute one equivalent component or process for another is not necessary to render such substitution obvious. In re Fout, 675 F.2d 297, 213 USPQ 532 (CCPA 1982).
Claim(s) 1-7, 14-15 and 19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al (US 20180301629 A1) in view of Ye et al (WO 2019218969).
Ye is combined with Hatakeyama for the same reasons it is combined with Do above.
Claim(s) 1-7, 14-15 and 19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al (US 20210053998 A1, and WO 2020022751) in view of Ye et al (WO 2019218969).
Ye is combined with Kim for the same reasons it is combined with Do and Hatakeyama above.
Claim(s) 11-12 and 18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Do et al (KR 20190127529 A) in view of Suh et al (WO 2019164331, English equivalent US 20210184121 A1).
Do, discussed above, does not disclose the specific structures of the claims.
Suh discloses OLED compounds comprising boron containing compounds [0012], similar to Do. Suh disclose that the light emitting layer includes a heterocyclic compound with the generic formula:
PNG
media_image21.png
233
228
media_image21.png
Greyscale
wherein W1 and W2 are the same as or different from each other, and each independently is O or S
An exemplified structure:
PNG
media_image22.png
240
357
media_image22.png
Greyscale
[0052]
makes obvious claimed formula 206. Many of the disclosed compounds are structurally similar to those of claim 18, for instance compare the disclosed compound below [p3] to the claimed compound [p75 of claims 02/13/2026, first row].
PNG
media_image23.png
222
355
media_image23.png
Greyscale
PNG
media_image24.png
118
172
media_image24.png
Greyscale
The compounds may be substituted with deuterium [abstract]. Suh teaches that the compounds provide properties of efficiency enhancement and color purity can be obtained in the organic light emitting device [0013].
It would have been obvious to one having ordinary skill in the art at the time of filing of Applicant’s invention to have used the structures of claims 11-12 and 18 for the boron containing compounds of Do because Suh teaches that the compounds provide properties of efficiency enhancement and color purity can be obtained in the organic light emitting device.
Claim(s) 11-12 and 18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al (US 20180301629 A1) in view of Suh et al (WO 2019164331, English equivalent US 20210184121 A1).
Hatakeyama, discussed above, does not disclose the specific structures of the claims.
Suh discloses OLED compounds comprising boron containing compounds [0012], similar to Hatakeyama. Suh disclose that the light emitting layer includes a heterocyclic compound with the generic formula:
PNG
media_image21.png
233
228
media_image21.png
Greyscale
wherein W1 and W2 are the same as or different from each other, and each independently is O or S
An exemplified structure:
PNG
media_image22.png
240
357
media_image22.png
Greyscale
[0052]
makes obvious claimed formula 206. Many of the disclosed compounds are structurally similar to those of claim 18, for instance compare the disclosed compound below [p3] to the claimed compound [p75 of claims 02/13/2026, first row].
PNG
media_image23.png
222
355
media_image23.png
Greyscale
PNG
media_image24.png
118
172
media_image24.png
Greyscale
The compounds may be substituted with deuterium [abstract]. Suh teaches that the compounds provide properties of efficiency enhancement and color purity can be obtained in the organic light emitting device [0013].
It would have been obvious to one having ordinary skill in the art at the time of filing of Applicant’s invention to have used the structures of claims 11-12 and 18 for the boron containing compounds of Hatakeyama because Suh teaches that the compounds provide properties of efficiency enhancement and color purity can be obtained in the organic light emitting device.
Claim(s) 11-12 and 18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al (US 20210053998 A1, and WO 2020022751) in view of Suh et al (WO 2019164331, English equivalent US 20210184121 A1).
Suh is combined with Kim for the same reasons it is combined with Do and Hatekayama above.
Claim(s) 1 is/are rejected under 35 U.S.C. 103 as being unpatentable over Do et al (KR 20190127529 A) in view of view of Dong et al (KR 20180112721).
Do, discussed above, does not disclose the specific structures of the claims.
Dong discloses OLED compounds comprising boron containing compounds [abstract, claim 1, p3], similar to Do. Dong disclose that the light emitting layer includes a heterocyclic compound with an exemplified structure
PNG
media_image25.png
131
293
media_image25.png
Greyscale
[0052]
Which reads on claimed formula 201 wherein two of T17 to T19 are aryl (phenyl) groups and are bonded together to form a ring, compare to the claimed compound p87 of the claims 02/13/2025, top row second embodiment.
The compounds may be substituted with deuterium [0133]. Dong teaches that the compounds can improve the efficiency, low driving voltage and/or the lifetime characteristic in the organic light emitting device [abstract].
It would have been obvious to one having ordinary skill in the art at the time of filing of Applicant’s invention to have used the structures of claims 13 and 19 for the boron containing compounds of Do because Dong teaches that the compounds can improve the efficiency, low driving voltage and/or the lifetime characteristic in the organic light emitting device.
Claim(s) 1 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al (US 20180301629 A1) in view of view of Dong et al (KR 20180112721).
Dong is combined with Hatakeyama for the same reasons it is combined with Do above.
Claim(s) 1 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kim et al (US 20210053998 A1, and WO 2020022751) in view of view of Dong et al (KR 20180112721).
Dong is combined with Kim for the same reasons it is combined with Do and Hatekayama above.
Other References
He et al (US 20190378982 A1, WO 2018095394 A1) discloses an OLED wherein the composition an organoborane similar to the claimed Formula 208 having the structure:
PNG
media_image26.png
176
322
media_image26.png
Greyscale
wherein Z1 to Z3 include N(R) and Si among several others. This compound may be deuterated and is combined with a second compound that may have anthracene as a constituent. However, no specific examples include Si as a Z atom and none include Z1 to Z3 being different. Furthermore, there are 13 different embodiments for Z1 to Z3 [claim 1]. It would require excessive hindsight on the part of the Office to arrive at the claimed composition with the Formula 208.
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 MICHAEL M DOLLINGER whose telephone number is (571)270-5464. The examiner can normally be reached 10am-6:30pm M-F.
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, Randy Gulakowski can be reached on 571-272-1302. 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.
MICHAEL M. DOLLINGER
Primary Examiner
Art Unit 1766
/MICHAEL M DOLLINGER/Primary Examiner, Art Unit 1766