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 .
Response to Arguments
Applicant’s arguments, filed 06/25/2026, with respect to the rejection(s) under:
-Saito et al (WO 2021199948 A1, hereinafter US 20230134165 A1 is used as an English equivalent) in view of Kim et al (KR 20120032054 A), and
- Kim876 et al (US 20210202876 A1) in view of Kim et al (KR 20120032054 A)
have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of over Yasuda et al (WO 2021210501 A1).
Applicant's arguments filed 06/25/2026 have been fully considered but they are not persuasive.
Applicant argues that the dopant of Chemical Formula 2 of claim 1 compound [2-3] shows unexpected results over the dopant of Saito compound [2-5] and compound [2-41]. This argument is not convincing because the results do not appear to be unexpectedly improved, but rather claimed compound [2-3] and compound [2-5] of Saito have about the same properties, especially when compared to results of compound [2-41]. Compound 2-3 and compound 2-5 have about the same results when compared to compound 2-41.
For compounds 2-3 and 2-5, respectively, compared to compound 2-41:
-the driving voltage is 3.3 and 3.4 V compared to 3.4 V
-the current efficiency is 158 and 148 dc/A compared to 90 dc/A
-the max wavelength is 514 and 512 nm compared to 482 nm
-and the overlap area is 38 and 37% compared to 29%.
Plainly stated, the results for the claimed compound 2-3 and the compound 2-5 disclosed in Saito are about the same, and show no unexpected improvement.
Furthermore, the rejections that cite Yang below give explicit motivation to use the claimed boron emitters.
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.
Claim(s) 1,4-10, 12, 14-18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Yasuda et al (WO 2021210501 A1) in view of Kim et al (KR 20120032054 A).
Yasuda discloses an OLED comprising a host, a fluorescent dopant, and a phosphorescent dopant [abstract,0111,0112] wherein the fluorescent dopant reads on the claimed boron compounds, for example:
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[p10] and wherein the phosphorescent dopant includes fluorine substituted iridium complexes like FIrpic and Fir6 [0111] and the host includes the claimed hosts [0112,p42,e121]. The OLEDs include electron and hole blocking layers [0050].
Yasuda does not disclose the specific phosphorescent dopants of claimed Chemical Formula 1.
Kim discloses OLEDs comprising in the light emitting material a phosphorescent dopant having the generic formula:
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[claim 1] wherein the LHS ligand contains halogen, nitro, and cyano groups [claim 1] and reads on the chemical Formula A and the ligand L reads on the claimed formula B1 and B2. An example of the main ligand includes:
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[0054] and others read on Chemical Formula A [0045 et seq]. The ligand L includes the structure:
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[0028] which reads on the Chemical Formula B1, as well as the structure:
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[0032] wherein R228 and R208 can join to form an ethylene group
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[0040] and henceforth reads on Chemical Formula B1. Kim teaches that the phosphorescent dopants have excellent luminous efficiency and lifetime comparison with existing dopant material, and have moderate color coordination [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 claimed phosphorescent dopants in the OLED emitting layer of Yasuda because Kim teaches that the phosphorescent dopants have excellent luminous efficiency and lifetime comparison with existing dopant material, and have moderate color coordination.
Claim(s) 1-10 and 12-18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Saito et al (WO 2021199948 A1, hereinafter US 20230134165 A1 is used as an English equivalent) in view of Kim et al (KR 20120032054 A) and further in view of Yasuda et al (WO 2021210501 A1) or Yang et al (J. Am. Chem. Soc. 2020, 142, 19468−19472).
Saito discloses an OLED comprising a host material [0366], a phosphorescent compound having a structure similar to the claimed Chemical Formula 1 that is an iridium containing dopant [claim 1, p51] and a fluorescent compound (F) having a boron and nitrogen skeleton that reads on claimed Chemical Formula 2, for example F11:
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[p103] which is the Compound 2-5 of claim 12. For 100 parts by mass of the phosphor and the fluorescent compound (F), the compound (F) is present in 0.1 parts by mass to 30 parts by mass [0101]. The OLED may include additional injection and transporting layers [0468].
Saito does not disclose the specific phosphorescent dopants of claimed Chemical Formula 1.
Kim discloses OLEDs comprising in the light emitting material a phosphorescent dopant having the generic formula:
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[claim 1] wherein the LHS ligand contains halogen, nitro, and cyano groups [claim 1] and reads on the chemical Formula A and the ligand L reads on the claimed formula B1 and B2. An example of the main ligand includes:
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[0054] and others read on Chemical Formula A [0045 et seq]. The ligand L includes the structure:
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[0028] which reads on the Chemical Formula B1, as well as the structure:
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[0032] wherein R228 and R208 can join to form an ethylene group
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[0040] and henceforth reads on Chemical Formula B1. Kim teaches that the phosphorescent dopants have excellent luminous efficiency and lifetime comparison with existing dopant material, and have moderate color coordination [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 claimed phosphorescent dopants in the OLED emitting layer of Saito because Kim teaches that the phosphorescent dopants have excellent luminous efficiency and lifetime comparison with existing dopant material, and have moderate color coordination.
Saito does not disclose the amended Chemical Formula 2 wherein at least two of m1 and m3 are 1, i.e. the boron compound has 2 or more diarylamine/carbazole substituents. Saito discloses the boron compound having one carbazole substituent.
Yasuda, similar to Saito, discloses a combination of host, phosphorescent dopant, and fluorescent dopant comprising boron compounds with carbazole groups. Yasuda discloses both the fluorescent dopant of Yasuda as well as the claimed Chemical Formula 2 [p10]:
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.
It would have been obvious to one having ordinary skill in the art at the time of Applicant’s effective filing date to have used the fluorescent dopant of the claims in the composition of Saito because Yasuda teaches that the claimed fluorescent dopant with two or three carbazole groups and the fluorescent dopant with one carbazole group of Saito 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).
Yang discloses the claimed Chemical formula 2 fluorescent dopants having two or three carbazole moieties:
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[Fig 1]
Yang teaches that these emitters provide emission in the entire visible range and produce highly efficient full color OLEDs [p19468].
It would have been obvious to one having ordinary skill in the art at the time of Applicant’s effective filing date to have used the fluorescent dopant of the claims in the composition of Saito because Yang teaches that these emitters provide emission in the entire visible range and produce highly efficient full color OLEDs.
Regarding claim 2, at least many if not all of the embodiments of Saito will have the claimed overlap over 35%. For instance, Example BD1 uses phosphorescent dopant P3 with an emission peak 450 nm and FWHM of 49.9 nm and fluorescent dopant F2 with absorption peak of 451 nm and FWHM of 21.4 nm [Tables 2 and 3]. Since the peaks are almost exactly the same wavelength, they will stack on top of one another. Nearly all of the absorption peak area will be encompassed by the emission peak area. Using the FWHM to estimate the ratio of the areas, the absorption peak is about 40% of the area under the emission peak (21.4/49.9), so well over 40% of the area under both peaks.
Regarding claim 3, Saito discloses that the difference between the max emission peak of the phosphorescent compound and the max absorption peak of the fluorescent dopant is preferably between -15 and 20 nm [0111].
Regarding claim 4, Saito discloses that |TP|−|SF| is preferably −0.30 or more and 0.50 or less [0281]. TP is lowest triplet excited state of the phosphorous compound [abstract], i.e. the LUMOPD, and SF is the lowest singlet excited state of the fluorescent compound [0044], i.e. LUMOFD. In terms of the claimed inequation A, Saito discloses 0.5 >= LUMOFD - LUMOPD >= -0.30.
Regarding claims 4 and 5, Saito teaches that energy is efficiently transferred from the phosphorescent material of formula 1 to the fluorescent compound (F) [0370]. In order to have energy transfer from the phosphorescent compound to the fluorescent compound (F), the HOMOFD should be equal to or higher than the HOMOPD, and the LUMOPD is preferably equal to or higher than the LUMOFD (i.e. a wider bandgap for the in order to allow energy to flow phosphorescent to fluorescent compounds.
Regarding claim 6, these are the required bandgaps of red, green, and blue visible light phosphorescent emitters. See Liu et al (US 20250221301 A1) [0002] and Sathee (attached NPL) [p3].
Regarding claim 14, energy is transferred from the host material, to the phosphorescent material, and also to the fluorescent material compound (F) [0370]. The host material has higher energy level of the lowest triplet excited state TH than the TP and TF [0371] and TP > TF [0107] so TH> TP> TF. It is also preferable that the lowest singlet excited state of the host is larger than TF [0371] and therefore it will in most embodiments be greater than SF, and several examples of SP are greater than SF in the examples [Table 1 p113].
Regarding claim 15, Saito discloses the host compound
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[p74] which is a position isomer of the claimed 3-1.
Claim(s) 1, 4-10,12-14 and 16-18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Kim876 et al (US 20210202876 A1) in view of Kim et al (KR 20120032054 A) and further in view of Yasuda et al (WO 2021210501 A1) or Yang et al (J. Am. Chem. Soc. 2020, 142, 19468−19472).
Kim876 discloses an OLED comprising a host material, a phosphorescent compound iridium containing dopant [0075] and a fluorescent dopant exemplified by
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[p7] which is the Compound 2-1 of claim 12. The light emitting layer includes 0.1 to 30wt% each of fluorescent dopant and phosphorescent dopant [0166]. The OLED may include additional injection and transporting layers [0047]. The host and dopants have the energy ratios of claim 14 [Fig. 2]. The OLED is used in a display device comprising a substrate, a thin film transistor, and the OLED on the thin film transistor used as a subpixel [0013].
Kim876 does not disclose the specific phosphorescent dopants of claimed Chemical Formula 1.
Kim, discussed above, discloses the claimed phosphorescent dopants.
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 claimed phosphorescent dopants in the OLED emitting layer of Kim876 because Kim teaches that the phosphorescent dopants have excellent luminous efficiency and lifetime comparison with existing dopant material, and have moderate color coordination.
Yasuda and Yang are combined with Modified Kim876 for the same reasons it is combined with Modified Saito above.
Regarding claims 4 and 5, Kim876 teaches that energy is efficiently transferred from the phosphorescent dopant to the fluorescent dopant [0048 et seq]. In order to have energy transfer from the phosphorescent compound to the fluorescent compound (F), the HOMOFD should be equal to or higher than the HOMOPD, and the LUMOPD is preferably equal to or higher than the LUMOFD (i.e. a wider bandgap for the in order to allow energy to flow phosphorescent to fluorescent compounds.
Regarding claim 6, these are the required bandgaps of red, green, and blue visible light phosphorescent emitters. See Liu et al (US 20250221301 A1) [0002] and Sathee (attached NPL) [p3].
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.
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MICHAEL M. DOLLINGER
Primary Examiner
Art Unit 1766
/MICHAEL M DOLLINGER/ Primary Examiner, Art Unit 1766
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