DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
All outstanding objections and rejections, except for those maintained below, are withdrawn in light of applicant's amendment filed on 2/26/2026.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior office action.
The new grounds of rejection set forth below are necessitated by applicant's amendment filed on 2/26/2026. In particular, original Claims 17, and 20 have been amended to recite limitations not previously presented. Thus, the following action is properly made final.
Claim Rejections - 35 USC § 112
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 11-14 and 22 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor, or for pre-AIA the applicant regards as the invention.
Claim 11 recites ligands such as LAi-1 and LAi-2:
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and
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,
where if Y is O, S or Se, then i is an integer from 1 to 906, and the table for ligands LA1, LA2, etc., i.e. i=1, 2, etc. states that RC1 is F. This combination of limitations renders the scope of the claim indefinite for the following reasons. Claim 11 depends from claim 1, and claim 1 recites the proviso that if Y is O, S or Se, then RC1 is not F. Thus, claim 1 excludes RC1 from being F for variable RC1. However, for the ligands above, Y can be O, S or Se, and RC1 is F. Thus, the entries in table require that RC1 is F, which is excluded by proviso recited in claim 1. Accordingly, it is unclear how one can simultaneously satisfy the proviso in claim 1 that if Y is O, S or Se, then RC1 is not F and still obtain ligand corresponding LA1-1 and LA1-2 where RC1 is F as recited in claim 11.
Claim 12 recites ligands such as:
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,
which render the scope of the claim indefinite for the following reasons. Claim 12 depends from claim 1, and claim 1 recites the proviso if Y is O, S or Se, then RC1 is not F. Thus, claim 1 excludes RC1 from being F for variable RC1 in Formula 1:
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However, for the above ligands in claim 12, Y is O and RC1 is F, which is prohibited by the proviso in claim 1. Accordingly, it is unclear how one can simultaneously satisfy the proviso in claim 1 that if Y is O then RC1 is not F and still obtain the above ligand recited in claim 12 where RC1 is F.
Claim 13 recites that the compound has the formula Pt(LA)(LB) and ligand LB includes structures such as:
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,
where K1’ is a direct bond or is selected from the group consisting of NRe, PRe, O, S and Se. The recitation of NRe, PRe, O, S and Se render the scope of the claim indefinite for the following reasons. Claim 13 depends from claim 1, and claim 1 recites that if the compound has the structure of Pt(LA)(LB) then Z1 and Z2 in the ligand:
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are bonded to Pt by a direct bond. However in the above ligands in claim 13, Z1 is bonded directly to K1’ and not to Pt. Accordingly, it is unclear how one obtains the ligands recited in claim 13 where K1’ is NRe, PRe, O, S or Se and still meet the requirement in claim 1 that Z1 and Z2 are bonded to Pt by a direct bond.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-3, 6-10, 12, 17-18, and 20-21 are rejected under 35 U.S.C. 103(a) as being unpatentable over Yan et al (US 2023/0227485).
Regarding claim 1, Yan et al discloses the following metal iridium complex ([0010] – I):
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,
where A is CR0 and R0 is H ([0012] and [0015]); R1 is an unsubstituted C1-10 alkyl ([0014]); R2 is hydrogen ([0015]); R3 can represent two (2) substitutions ([0013]) and includes a halogen e.g. fluorine ([0015] and Page 17 Compounds CPD98 and CPD99) and a C1-10 alkyl ([0015]); and R4 is a C1-10 alkyl ([0015]).
The ligand:
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,
is exemplified as ([0027] – A5):
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.
From the above, the reference discloses a compound with the Formula Ir(LA)m(LC)n, where m is two (2) and n is one (1). Ligand LB corresponds to:
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where moiety A is a bicyclic fused ring structure comprising two (2) 6-membered aromatic rings; RC1 is hydrogen; RC is fluorine; Y is O; RB is a C1-10 alkyl; RC2 is a C1-10 alkyl; and RA is a C1-10 alkyl.
Ligand LB corresponds to:
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,
where R2, R7, and R5 are hydrogen; and R1, R2, R5 and R6 are C2 alkyls.
While the reference fails to exemplify the presently claimed compound nor can the claimed compound be "clearly envisaged" from the reference as required to meet the standard of anticipation, nevertheless, in light of the overlap between the claimed compound and the compound disclosed by the reference, absent a showing of criticality for the presently claimed compound, it is urged that it would have been within the skill level of one of ordinary skill in the art, to use the compound which is both disclosed by the reference and encompassed within the scope of the present claims and thereby arrive at the claimed invention.
Regarding claim 2, Yan et al teaches all the claim limitations as set forth above. As discussed above, RC is fluorine; RC2 is an alkyl; RC1 is hydrogen; RA is an alkyl; RB is an alkyl; R2, R7, and R5 are hydrogen; and R1, R3, R4 and R6 are alkyls.
Regarding claim 3, Yan et al teaches all the claim limitations as set forth above. As discussed above, moiety A is a bicyclic fused ring structure comprising two (2) 6-membered aromatic rings.
Regarding claim 6, Yan et al teaches all the claim limitations as set forth above. As discussed above, RC2 is an alkyl.
Regarding claim 7, Yan et al teaches all the claim limitations as set forth above. As discussed above, RA is an alkyl.
Regarding claim 8, Yan et al teaches all the claim limitations as set forth above. As discussed above, Y is O.
Regarding claim 9, Yan et al teaches all the claim limitations as set forth above. As discussed above, recited ligand LC corresponds to the formula:
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.
Regarding claim 10, Yan et al teaches all the claim limitations as set forth above. From the discussion above, the reference discloses recited ligand LA as:
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.
Regarding claim 12, Yan et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that “alkyl” encompasses isopropyl and isobutyl ([0057]). Accordingly, the reference discloses the ligand:
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.
Regarding claim 21, Yan et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that “alkyl” encompasses isobutyl ([0057]) and that the alkyl can be substituted with deuterium ([0014]-[001] and [0019]). Accordingly, the reference discloses the recited compound:
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.
Regarding claim 17, Yan et al discloses an organic electroluminescent device, i.e. an organic light emitting device, comprising an anode, a cathode and an organic layer disposed between the anode and cathode ([0029]). The organic layer comprises the following metal iridium complex ([0029] and [0010] – I):
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,
where A is CR0 and R0 is H ([0012] and [0015]); R1 is an unsubstituted C1-10 alkyl ([0014]); R2 is hydrogen ([0015]); R3 can represent two (2) substitutions ([0013]) and includes a halogen e.g. fluorine ([0015] and Page 17 Compounds CPD98 and CPD99) and a C1-10 alkyl ([0015]); and R4 is a C1-10 alkyl ([0015]).
The ligand:
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,
is exemplified as ([0027] – A5):
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.
From the above, the reference discloses a compound with the Formula Ir(LA)m(LC)n, where m is two (2) and n is one (1). Ligand LB corresponds to:
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where moiety A is a bicyclic fused ring structure comprising two (2) 6-membered aromatic rings; RC1 is hydrogen; RC is fluorine; Y is O; RB is a C1-10 alkyl; RC2 is a C1-10 alkyl; and RA is a C1-10 alkyl.
Ligand LB corresponds to:
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,
where R2, R7, and R5 are hydrogen; and R1, R2, R5 and R6 are C2 alkyls.
While the reference fails to exemplify the presently claimed compound nor can the claimed compound be "clearly envisaged" from the reference as required to meet the standard of anticipation, nevertheless, in light of the overlap between the claimed compound and the compound disclosed by the reference, absent a showing of criticality for the presently claimed compound, it is urged that it would have been within the skill level of one of ordinary skill in the art, to use the compound which is both disclosed by the reference and encompassed within the scope of the present claims and thereby arrive at the claimed invention.
Regarding claim 18, Yan et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that the emitting layer comprises CBP, i.e. 4,4’-bis(N-carbazolyl)-1,1’-biphenyl, i.e. a host compound comprising a carbazole moiety ([00252]).
Regarding claim 20, Yan et al discloses an organic electroluminescent device, i.e. a consumer product, comprising an anode, a cathode and an organic layer disposed between the anode and cathode ([0029]). The organic layer comprises the following metal iridium complex ([0029] and [0010] – I):
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,
where A is CR0 and R0 is H ([0012] and [0015]); R1 is an unsubstituted C1-10 alkyl ([0014]); R2 is hydrogen ([0015]); R3 can represent two (2) substitutions ([0013]) and includes a halogen e.g. fluorine ([0015] and Page 17 Compounds CPD98 and CPD99) and a C1-10 alkyl ([0015]); and R4 is a C1-10 alkyl ([0015]).
The ligand:
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,
is exemplified as ([0027] – A5):
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.
From the above, the reference discloses a compound with the Formula Ir(LA)m(LC)n, where m is two (2) and n is one (1). Ligand LB corresponds to:
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where moiety A is a bicyclic fused ring structure comprising two (2) 6-membered aromatic rings; RC1 is hydrogen; RC is fluorine; Y is O; RB is a C1-10 alkyl; RC2 is a C1-10 alkyl; and RA is a C1-10 alkyl.
Ligand LB corresponds to:
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,
where R2, R7, and R5 are hydrogen; and R1, R2, R5 and R6 are C2 alkyls.
While the reference fails to exemplify the presently claimed compound nor can the claimed compound be "clearly envisaged" from the reference as required to meet the standard of anticipation, nevertheless, in light of the overlap between the claimed compound and the compound disclosed by the reference, absent a showing of criticality for the presently claimed compound, it is urged that it would have been within the skill level of one of ordinary skill in the art, to use the compound which is both disclosed by the reference and encompassed within the scope of the present claims and thereby arrive at the claimed invention.
Claims 1, 13, and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al (EP 3508491).
Regarding claim 1, Lee et al discloses an organometallic compound with the formula ([0008] – Formula 1):
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where X1 is a chemical bond ([0024]); M is Pt ([0022]); T1 and T2 are single bonds ([0040]).
The moiety
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corresponds to CY2-1 ([0072]):
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where X51 is N ([003]); X2 is N (Page 4 Line 5); Z2 is deuterium (Page 4 Line 42); and R2 is hydrogen (Page 4 Line 26).
Ring CY1 corresponds to ([0069] and Page 25):
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where X19 is O (Page 24 Lines 26); a16 is two (2) (Page 24 Line 34); R1 is -F and an C1-60 alkyl group (Page 4 Lines 26-29); and Z1 is deuterium (Page 4 Line 42).
Ring CY3 corresponds to (Page 28):
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where Z3 is deuterium (Page 4 Line 42); R3 is hydrogen ([0049]); and X3 is C ([0029]).
Ring CY4 corresponds to ([0078):
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where Z4 is deuterium (Page 4 Line 42); R4 is hydrogen ([0049]); and X4 is N ([0029]).
From the discussion above, the reference discloses recited ligand LA represented by Formula I:
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where:
moiety A is a polycyclic fused ring structure comprising one (1) 5-membered heterocyclic ring and one (1) 6-membered carbocyclic ring;
Y is O;
RC1 is a hydrogen;
RA and RB are deuterium;
RC is a fluorine atom;
RC1 is an alkyl group, i.e. methyl.
Ligand LB has the structure:
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where Z1 and Z2 are directly bonded to Pt; Z1is N; Z2 is C; RE and RF are deuterium; moieties E and F are 6-membered carbocyclic and heterocyclic rings, respectively. Ligands LA and LB join to form a tetradentate ligand.
While the reference fails to exemplify the presently claimed compound nor can the claimed compound be "clearly envisaged" from the reference as required to meet the standard of anticipation, nevertheless, in light of the overlap between the claimed compound and the compound disclosed by the reference, absent a showing of criticality for the presently claimed compound, it is urged that it would have been within the skill level of one of ordinary skill in the art, to use the compound which is both disclosed by the reference and encompassed within the scope of the present claims and thereby arrive at the claimed invention.
Regarding claim 13, Lee et al teaches all the claim limitations as set forth above. From the discussion above the compound has the formula Pt(LA)(LB) where ligand LB corresponds to
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where K1’ is a direct bond; Y1 to Y8 are C; and Ra and Rb are deuterium.
Regarding claim 16, Lee et al teaches all the claim limitations as set forth above. From the discussion above the reference discloses a compound with the recited formula:
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where
moieties E and F are monocyclic ring structures comprising 6-membered carbocyclic and heterocyclic rings;
Z1 and Z2 are N sand C respectively;
K1 to K4 are direct bonds; L
L1 to L3 are single bonds; and
RE and RF are deuterium.
Claims 1, 4, 6, and 12 are rejected under 35 U.S.C. 103 as being unpatentable over Choi et al (US 2018/0273563).
Regarding claim 1, Choi et al discloses an organometallic compound with the following formula ([0044] – Formula 1):
M(L1)n1(L2)n2,
where M is iridium ([0045]); n1 is [1-3] ([0047]); and n2 is [0-4] ([0048]). Accordingly, the reference discloses a compound with the recited formula Ir(LA)m(LC)n, where m and n are 1 or 2 and m + n = 3.
Ligand L1 corresponds to Formula (2A) ([0106]):
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where Y8 is C(R8) ([0108]); X1 is O or S ([0109] and [0016]); R3 to R8 are hydrogen, -F, or a
C1-60 alkyl ([0109] and [0018]); and R11 to R18 are hydrogen ([0110]).
This ligand corresponds to recited ligand LA represented by Formula I:
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where:
moiety A is a polycyclic fused ring structure comprising three (3) 6-membered aromatic rings;
Y is O;
RC1 is a fluorine atom;
RA, RB, and RC are hydrogen;
RC1 is an alkyl group, i.e. methyl; and
LA is coordinated to the metal to comprise a 5-membered chelate ring.
Ligand L2 is represented by Formula 3B ([0120]):
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where a11 is one (1) ([0125]); T11 is *-C(Z11)=C(Z12-C(Z13)=*’ ([0124]); Y11 is N(Z1) ([0122]); Y12 is N(Z3) ([0123]); Z1, Z3, Z11, Z12, and Z13 are hydrogen ([0129] and [0018]). This ligand corresponds to recited ligand LC:
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where Ra2 to Re2 are hydrogen
While the reference fails to exemplify the presently claimed compound nor can the claimed compound be "clearly envisaged" from the reference as required to meet the standard of anticipation, nevertheless, in light of the overlap between the claimed compound and the compound disclosed by the reference, absent a showing of criticality for the presently claimed compound, it is urged that it would have been within the skill level of one of ordinary skill in the art, to use the compound which is both disclosed by the reference and encompassed within the scope of the present claims and thereby arrive at the claimed invention.
Regarding claim 4, Choi teaches all the claim limitations as set forth above. From the discussion above, ring A is a tricyclic fused ring structure comprising three (3) 6-membered aromatic rings.
Regarding claim 5, Choi teaches all the claim limitations as set forth above. Additionally, the reference discloses the formula ([0009] – Formula 2):
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where ring CY1 is a benzoisoquinoline ([0015]) and R10 can represent two (2) C2 alkenyl groups that link to form a C6 carbocyclic group ([0019] [0018] [0022]), i.e. a fused benzene ring. Accordingly, the reference discloses an embodiment where recited moiety A is a polycyclic fused ring structure comprising four (4) fused aromatic rings.
Regarding claim 12, Choi teaches all the claim limitations as set forth above. Additionally, for ligand L1 the reference discloses the general formula ([0104] – Formula 2-1):
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where ring CY1 has the formula ([0100] and Page 16 – Formula CY1-8):
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where R15 can be a C1 alkyl substituted with at least one -F ([0110] and [0070]), i.e. CF3, and the remaining R-groups can be hydrogen ([0110] and [0069]). In the formula:
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R7 can be Si(Q3)(Q4)(Q5), where Q3 to Q5 are -CH3 ([0073]-[0075]), i.e. trimethylsilyl. R6 can be C1 alkyl substituted with at least one -F ([0110] and [0070]), i.e. CF3; and R3 can be a C1 alkyl. Accordingly, the reference discloses ligand LA32 of the claims:
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.
Response to Arguments
Applicant's arguments filed 2/26/2026 have been fully considered but they are not persuasive.
In light of the amendments to the claims and Specification, the claim objections and 35 U.S.C. 112 (b) rejections as well as the objections to the Specification as set forth in the previous Office Action are withdrawn.
Furthermore, in light of the claim amendments, the 35 U.S.C. 103 rejections of the claims over Kosuge et al, Cai et al, Choi ‘774, and Lee et al as set forth in the previous Office Action are withdrawn.
Applicants argue that Choi ‘563 does not disclose the compound as recited in amended claim 1. However, as discussed in the rejections above, the reference discloses ligand L2 is as ([0120] – Formula 3B):
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where a11 is one (1) ([0125]); T11 is *-C(Z11)=C(Z12-C(Z13)=*’ ([0124]); Y11 is N(Z1) ([0122]); Y12 is N(Z3) ([0123]); Z1, Z3, Z11, Z12, and Z13 are hydrogen ([0129] and [0018]). This ligand corresponds to recited ligand LC:
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where Ra2 to Re2 are hydrogen
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 extension fee 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 date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALEXANDER C. KOLLIAS whose telephone number is (571)-270-3869. The examiner can normally be reached on Monday-Friday, 8:00AM – 5:00 PM EST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jennifer Boyd can be reached on (571)-272-7783. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ALEXANDER C KOLLIAS/Primary Examiner, Art Unit 1786