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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 05/13/2026 has been entered.
Response to Amendment
Claim 12 has been cancelled; claims 1, 6, 10-11, 13 and 14 have been amended; and claims 1-11 and 13-20 are currently pending.
Priority
Acknowledgment is made of applicant's claim for foreign priority under 35 U.S.C. 119(a)-(d).
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.
Claims 1-20 are rejected under 35 U.S.C. 102(a)(1) as being unpatentable over LEE et al. (EP 3798225 A1, hereinafter “LEE”) in view of Xia et al. (US 2014/0231755 A1, hereinafter “Xia”).
In regards to claim 1, LEE discloses an organometallic compound represented by Formula 1:
Wherein, in Formula 1,
M.sub.1(L1)n1(L2)n2
M.sub.1 is a transition metal,
L.sub.1 is a ligand represented by Formula 1A,
L.sub.2 is a ligand represented by Formula 1B,
n1 and n2 are each independently 1 or 2
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Wherein, in Formula 1A and 1B,
R12 and R13 are each independently hydrogen …
a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q.sub.21)(Q.sub.22)(Q.sub.23), —Ge(Q.sub.21)(Q.sub.22)(Q.sub.23), —N(Q.sub.24)(Q.sub.25), —B(Q.sub.26)(Q.sub.27), —P(Q.sub.28)(Q.sub.29), —P(═O)(Q.sub.28)(Q.sub.29), or a combination thereof; or —Si(Q.sub.31)(Q.sub.32)(Q.sub.33), —Ge(Q.sub.31)(Q.sub.32)(Q.sub.33), —N(Q.sub.34)(Q.sub.35), —B(Q.sub.36)(Q.sub.37), —P(Q.sub.38)(Q.sub.39), or —P(═O)(Q.sub.38)(Q.sub.39), and Q.sub.1 to Q.sub.9, Q.sub.11 to Q.sub.19, Q.sub.21 to Q.sub.29, and Q.sub.31 to Q.sub.39 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C.sub.1-C.sub.60 alkyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkenyl group, a substituted or unsubstituted C.sub.2-C.sub.60 alkynyl group, a substituted or unsubstituted…
(Formula 1, 2 and 3 :
According to an aspect, an organometallic compound presented in Formula 1 is provided:
<Formula 1> M (L1) n1(L2)n2
In Formula 1, M may be a transition metal, L.sub.1 may be a ligand represented by Formula 2, L.sub.2 may be a ligand represented by Formula 3, n1 and n2 may each independently be 1 or 2, when n1 is 2, two L.sub.1(s) may be identical to or different from each other, and when n2 is 2, two L.sub.2(s) may be identical to or different from each other.
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See, Pars [0012-[).
However, LEE is silent about R12 is a C1-C60 alkyl group substituted with deuterium.
Xia while disclosing a metal iridium complexes and devices containing the same teaches (See, for example, Formula 1) R12 (See, Par [0016], “R1 is a partially or fully deuterated group consisting of alkyl and cycloalkyl…”) is a C1-C60 alkyl group substituted with deuterium (See, Formula 1 in Par [0016]).
Therefore, it would have been obvious to one having ordinary skill in the art before the effective filing date of the invention to provide compound formula 2 of LEE with a deuterated alkyl group on the pyridine ring as taught by Xia because this would help obtain the extended device operational lifetime that Xia expressly attributes to deuteration of the pyridine-ring alkyl group (See Par [0039]).
In regards to claim 2, LEE discloses that wherein M.sub.1 is iridium, platinum, palladium, gold, osmium, titanium, zirconium, hafnium, europium, terbium, thulium, or rhodium (M is a transition metal, See, Pars [0016] and [0022]).
In regards to claim 3, LEE discloses that M.sub.1 is iridium, and a sum of n1 and n2 is 3 (See, for example, Pars [0016] and [0022]).
In regards to claim 4, LEE discloses that ring CY.sub.2 and ring CY.sub.4 are each independently a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group (“In one embodiment, ring CY.sub.2 may be a cyclopentene group, a cyclohexane group, a cyclohexene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group …”, See, for example, Pars [0029]-[0031]).
In regards to claim 5, LEE discloses that ring CY.sub.3 is an imidazole group or a benzimidazole group (See, Formula 3 above).
In regards to claim 6, LEE as modified above discloses that a moiety represented by
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in Formula 1A is a group represented by one of Formulae 1-1 to 1-20. (See, for example, Par [0049], Xia).
In regards to claim 7, LEE discloses that a moiety represented by
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in Formula 1A is a group represented by one of Formulae 2-1 to 2-16. (See, for example, Pars [0048], [0049], and [0050]).
In regards to claim 8, LEE discloses that a moiety represented by
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in Formula 1B is a group represented by Formula 3-1 or 3-2. (See, Par [0035] and Formula
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, and also , see Pars [0036] and [0048]).
In regards to claim 9, LEE discloses that a moiety represented by
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In Formula 1B is a group represented by one of Formulae 4-1 to 4-11 (See, Formula 3 above, and Par [0036]).
In regards to claim 10, LEE discloses that R.sub.2 to R.sub.9, R.sub.11, R.sub.14, R.sub.41, and R.sub.42 are each independently: hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5,-CD.sub.3,-CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxy … an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group; or an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, or a naphthyl group, each substituted with at least one of deuterium, a C.sub.1-C.sub.10 alkyl group, a phenyl group, or a combination thereof (See, for example, Pars [0035], [0048], [0050]-[0052]).
In regards to claim 11, LEE discloses that R.sub.2 to R.sub.9, R.sub.11, R.sub.14, R.sub.41, and R.sub.42 are each independently: hydrogen, deuterium, —F, —Cl, —Br, —I, —SF.sub.5,-CD.sub.3,-CD.sub.2H, —CDH.sub.2, —CF.sub.3, —CF.sub.2H, —CFH.sub.2, a C.sub.1-C.sub.60 alkyl group, a C.sub.2-C.sub.60 alkenyl group, a C.sub.2-C.sub.60 alkynyl group ….R.sub.12 and R.sub.13 are each independently: hydrogen, deuterium…or a group represented by one of Formulae 9-1 to 9-39, 9-201 to 9-237, 10-1 to 10-129, or 10-201 to 10-350 in which at least one hydrogen is substituted with deuterium: … wherein, in Formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, * indicates a binding site to a neighboring atom, “Ph” is a phenyl group, “TMS” is a trimethylsilyl group, and “TMG” is a trimethylgermyl group (See, for example, Pars [0035], [0048], [0050]-[0052], [0063]-[0064]).
In regards to claims 13 and 14, LEE as modified above discloses that the organometallic compound is represented by one of Formulae 5-1 to 5-6 (See, for example, Par [0098] as combined with Formula 2 (L1) of Xia as shown in Par [0049]); and the organometallic compound is at least one of Compounds 1 to 129 (See, for example, Par [0098] as combined with Formula 2 (L1) of Xia as shown in Par [0049]).
In regards to claim 15, LEE discloses (See, for example, Fig. 1) an organic light-emitting device, comprising:
a first electrode (11),
a second electrode (19), and
an organic layer (15) arranged between the first electrode (11) and the second electrode (19),
wherein the organic layer (15) comprises an emission layer (See, for example, Pars [0116], [0161]-[0162], and [0193]-[0195]…), and
wherein the organic layer (15) further comprises at least one of the organometallic compound in claim 1 (See, for example, Pars [0193]-[0195]).
In regards to claim 16, LEE discloses that the emission layer (15) comprises the at least one of the organometallic compound (See, for example, Pars [0116], [0161]-[0162], and [0193]-[0195]…).
In regards to claim 17, LEE discloses that the emission layer further comprises a host, and an amount of the host in the emission layer is greater than an amount of the at least one of the organometallic compound in the emission layer (“The organometallic compound represented by Formula 1 may be used between a pair of electrodes of the organic light-emitting device. For example, the organometallic compound represented by Formula 1 may be included in the emission layer. Here, the organometallic compound may serve as a dopant, and the emission layer may further include a host (i.e., an amount of the organometallic compound represented by Formula 1 may be smaller than that of the host) …”, See, for example, Par [0105]).
In regards to claim 18, LEE discloses that the emission layer emits a green light having a maximum emission wavelength of about 490 nanometers to about 550 nanometers (“The emission layer may emit red light or green light, for example, red light or green light, each having a maximum emission wavelength of 500 nm or more, for example, 500 nm or more and 850 nm or less. For example, the organometallic compound may emit green light.”, See, for example, Par [0105]).
In regards to claim 19, LEE discloses (See, for example, Fig. 1) the first electrode is an anode (11, See, for example, Par [0108]), the second electrode is a cathode (19, See, for example, Par [0108]), the organic layer (15) further comprises a hole transport region arranged between the first electrode and the emission layer and an electron transport region arranged between the emission layer and the second electrode, the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof (“…the organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.”, See, for example, Par [0109]).
In regards to claim 20, LEE discloses (See, for example, Fig. 1) an electronic apparatus, comprising the organic light-emitting device of claim 15 (See, for example, Pars [0008], and [0160]).
Response to Arguments
Applicant’s arguments with respect to claim 1 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ERMIAS T WOLDEGEORGIS whose telephone number is (571)270-5350. The examiner can normally be reached on Monday-Friday 8 am - 5 pm E.S.T..
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Britt Hanley can be reached on 571-270-30423042. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ERMIAS T WOLDEGEORGIS/Primary Examiner, Art Unit 2893
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