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 .
Response to Amendment
Claims 1-20 are currently pending.
Priority
Acknowledgment is made of applicant's claim for foreign priority under 35 U.S.C. 119(a)-(d).
Response to Arguments
Applicant's arguments filed on 12/29/2025 have been fully considered but they are not persuasive.
Applicant makes the following argument:
“Lee teaches a ligand position (X₁₁) that is limited to Si or Ge, which is categorically
excluded from the amended R₁₂ and R₁₃ definition. Claim 1 cannot read on any embodiment where X₁₁ is Si or Ge, as required by Lee. Thus, the claimed compounds are structurally distinct and not anticipated.
Accordingly, Lee does not disclose each and every limitation of claim 1.” (See, Applicant’s Remarks page 53)
This is not persuasive because:
First:
Applicant’s own Claim 1 defines R₁₂ as being independently selected from a list of options, which includes (among others):
"a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group"
R₁₂ may be selected as a substituted monovalent non-aromatic condensed polycyclic group or a substituted monovalent non-aromatic condensed heteropolycyclic group.
Second:
Applicant’s own Claim 1 further provides a detailed definition of what constitutes permissible substituents on the various "substituted" groups. The relevant claim language states:
"at least one substituent of the substituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group, ... the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is: [list of substituents]"
The claim explicitly defines permissible substituents for both the substituted monovalent non-aromatic condensed polycyclic group and the substituted monovalent non-aromatic condensed heteropolycyclic group.
Third:
Applicant’s own claim 1 list of permitted substituents concludes with:
"—Si(Q₁₁)(Q₁₂)(Q₁₃), —Ge(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(Q₁₈)(Q₁₉), —P(═O)(Q₁₈)(Q₁₉), or a combination thereof"
Silicon groups (—Si(Q₁₁)(Q₁₂)(Q₁₃)) and germanium groups (-Ge(Q₁₁)(Q₁₂)(Q₁₃)) are explicitly recited as permitted substituents.
In summary:
R₁₂ can be a substituted monovalent non-aromatic condensed polycyclic group or heteropolycyclic group (See First).
The permissible substituents on these groups are explicitly defined in the claim (See Second).
The defined substituents include —Si(Q₁₁)(Q₁₂)(Q₁₃) and —Ge(Q₁₁)(Q₁₂)(Q₁₃) (See Third).
In conclusion:
Based on Applicant's own claim 1 language defining R₁₂ for Formula 1A, R₁₂ can comprise silicon or germanium groups through applicant’s own claim construction:
When R₁₂ is selected as a substituted monovalent non-aromatic condensed polycyclic group or a substituted monovalent non-aromatic condensed heteropolycyclic group, the substituent(s) on said group may include —Si(Q₁₁)(Q₁₂)(Q₁₃), —Ge(Q₁₁)(Q₁₂)(Q₁₃), or a combination thereof.
Therefore, the scope of R₁₂ as claimed encompasses embodiments containing silicon and/or germanium substituents. As a result, the prima-facie case of anticipation is deemed to be proper.
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.
Claims 1-20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by LEE et al. (EP 3798225 A1, hereinafter “LEE”).
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-[).
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 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, Formula 2 and Par [0048]).
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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248
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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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238
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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 claim 12, LEE discloses that at least one of R.sub.12 and R.sub.13 is a C.sub.1-C.sub.20 alkyl group substituted with at least one deuterium, a C.sub.3-C.sub.10 cycloalkyl group substituted with at least one deuterium, a C—C.sub.60 aryl group substituted with at least one deuterium, or a C.sub.1-C.sub.60 heteroaryl group substituted with at least one deuterium (See, for example, Par [0050]).
In regards to claims 13 and 14, LEE discloses that the organometallic compound is represented by one of Formulae 5-1 to 5-6 (See, for example, Par [0098]); and the organometallic compound is at least one of Compounds 1 to 132 (See, for example, Par [0098]).
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]).
Conclusion
THIS ACTION IS MADE FINAL. 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.
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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