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All outstanding objections and rejections, except for those maintained below, are withdrawn in light of applicant's amendment filed on 1/12/2026.
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 1/12/2026. In particular, the scope of original claim 1 has been narrowed, while newly added claims 13-16 recite subject matter not previously presented. Thus, the following action is properly made final.
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, 4, 6, and 12 are rejected under 35 U.S.C. 103(a) as being unpatentable over Tani (US 2025/0107430).
Regarding claim 1, Tani discloses the following iridium organometallic complex (Page 11 – 40 ):
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318
460
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.
This compound corresponds to the iridium complex represented by general formula I of the claims:
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208
336
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,
where:
the integer a is two (2);
R1 is fluorine, i.e. a halogen;
R2 is hydrogen;
R4 is a methyl group, i.e. a C1 alkyl;
R4 is hydrogen; and
R5 is methyl, i.e. a C1 alkyl.
The auxiliary ligand:
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102
78
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,
corresponds to formula RP-13:
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152
106
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.
Alternatively, the reference discloses the following iridium organometallic complex (Page 11 – 39):
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342
410
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.
This compound corresponds to the iridium complex represented by general formula I of the claims:
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208
336
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,
where:
the integer a is one (1);
R1 is a fluorinated alkoxy group, i.e. a substituted C1 alkoxy;
R2 is hydrogen;
R3 is a methyl group, i.e. a C1 alkyl;
R4 is hydrogen; and
R5 is methyl, i.e. a C1 alkyl.
The auxiliary ligand:
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102
78
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,
corresponds to formula RP-13:
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152
106
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.
The difference between the compounds disclosed by the reference and that claimed, is that ring A in the compounds disclosed by the reference corresponds to:
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162
184
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,
while the instant claims require ring A correspond to Formula RD-3:
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100
188
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.
Thus, the compound disclosed by the reference and that claimed are isomers - compounds having the same radicals in physically different positions on the same nucleus, and the courts have held, as found in In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977), that compounds which are isomers “are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties”.
In light of the case law cited above, it therefore would have been obvious to one of ordinary skill in the art that the compound disclosed in the present claims is but an obvious variant of the compound disclosed in the reference, and thereby one of ordinary skill in the art would have arrived at the claimed invention.
Regarding claim 4, Tani teaches all the claim limitations as set forth above. In the compounds disclosed by the reference:
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and
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in recited formula RD-3:
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T31 to T35 and T38 are hydrogen or T31 to T35 and T37 to T38 are hydrogen, and therefore, the compounds disclosed by the reference do not meet the requirement that at most three (3) of T31 to T38 are not hydrogen. However, the compounds disclosed by the reference are but two embodiments, and attention is directed to the following general formula ([0015] – 1):
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where R1 to R8 can each independently be a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group, e.g. methyl, ethyl, propyl, a cyano group, etc. ([0015] and [0039]). Accordingly, the disclosure of the reference encompasses an embodiment where T31 to T38 are substituents such as deuterium, halogen, CN, etc. such that at most three (3) of T31 to T38 are not 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 6, Tani teaches all the claim limitations as set forth above. As discussed above, in Formula I R2 is hydrogen and R5 is a methyl group.
Regarding claim 12, Tani teaches all the claim limitations as set forth above. Additionally, the reference discloses an organic light emitting device comprising a first electrode, i.e. an anode, an organic compound layer, i.e. an organic layer, and a second electrode, i.e. cathode ([0065] and [0067]). The organic compound layer comprises a light emitting layer, i.e. a luminescent layer, where the light emitting layer comprises the disclosed compound as a red-light emitting dopant ([0030]).
Claims 1, 4, 6, and 12 are rejected under 35 U.S.C. 103(a) as being unpatentable over Lee et al (US 2020/0308205).
Regarding claim 1, Lee et al discloses the following iridium complex (Page 55 – Compound 16):
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This compound corresponds to general formula I of the claims:
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208
336
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where ring A corresponds to Formula RD-3:
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96
188
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In formula RD-3 the integer a is one (1); and R1 is F, i.e. a halogen.
In Formula 1 of the claims:
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R2 is hydrogen;
R3 is a methyl group, i.e. a C1 alkyl;
R4 is hydrogen; and
R5 is methyl, i.e. a C1 alkyl.
In the auxiliary ligand, Rx and Ry are methyl groups, and therefore, the ligand does not correspond to Formula RP-13 of the claims:
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102
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.
However, the compound disclosed by the reference is but one embodiment and attention is directed to the following formula ([0007] – Formula 1):
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,
where A2 and A5 can be cycloalkyl groups such as cyclohexyl ([0012], [0054], and [0056]). Accordingly, the disclosure of the reference encompasses an embodiment where the auxiliary ligand corresponds to Formula RP-13 of the present claims.
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, Lee et al teaches all the claim limitations as set forth above. In the compound disclosed by the reference:
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in recited formula RD-3:
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,
T31, and T34 to T38 are hydrogen, and therefore, the compound disclosed by the reference does not meet the requirement that at most three (3) of T31 to T38 are not hydrogen. However, the compound disclosed by the reference is but one embodiment, and attention is directed to the following formula ([0007] – Formula 1):
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,
where CY1 can be ([0092] – Formula CY1(1) ):
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,
In the above formula T11 to T18 can be independently hydrogen, deuterium, etc., as long as one (1) of T11 to T18 includes at least one fluorine atom ([0094] and [0098]-[0099]). Accordingly, the disclosure of the reference encompasses an embodiment where T11 to T18 are substituents such as deuterium such that at most three (3) of T11 to T18 are not hydrogen.
Regarding claim 6, Lee et al teaches all the claim limitations as set forth above. As discussed above, in Formula I R2 is hydrogen and R5 is a methyl group.
Regarding claim 12, Lee et al teaches all the claim limitations as set forth above. Additionally, the reference discloses an organic light emitting device comprising a first electrode, i.e. an anode, an organic compound layer, i.e. an organic layer, and a second electrode, i.e. cathode ([0201]). The organic compound layer comprises a light emitting layer, i.e. a luminescent layer, where the light emitting layer comprises the disclosed compound as a light emitting dopant ([0199]).
Claims 13-16 are rejected under 35 U.S.C. 103(a) as being unpatentable over Boudreault et al (US 2022/0352476).
Regarding claim 13, Boudreault et al discloses an iridium complex with the formula ([0074]):
Ir(LA)2(LB),
where ligand LA corresponds to ([0072] and Page 243):
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Ligand LB corresponds to LCj-1 (Page 61):
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132
118
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where R201 and R202 correspond to RD133 (Page 72 and see the Table on Page 63, ligand LC132):
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Note that ligand above is improperly depicted in cited section of the reference, i.e. the ligand does comprise two (2) oxygen atom. However, Paragraph [0076] properly denotes the ligand as:
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Accordingly, the reference discloses an iridium complex corresponding to Formula I:
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where ring A corresponds to Formula RD-1:
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116
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In formula RD-1, the integer a is one (1); and R1 is C4 alkyl substituted with a CF3 group.
In Formula 1 of the claims:
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R2 is hydrogen;
R3 is a methyl group, i.e. a C1 alkyl;
R4 is hydrogen; and
R5 is methyl, i.e. a C1 alkyl.
The auxiliary ligand:
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102
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,
corresponds to RP-19:
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228
116
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.
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 14, Boudreault et al teaches all the claim limitations as set forth above. . In the compound disclosed by the reference, in recited formula RD-1:
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T11 to T15 and T17 to T18 are hydrogen, and therefore, the compound disclosed by the reference does not meet the requirement that at most three (3) of T11 to T18 are not hydrogen. However, the compounds disclosed by the reference are but two embodiments, and attention is directed to the following general ([0007] – I):
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,
where RA, RB, and RC are hydrogen and can represent from zero (0) up to the maximum number of substituents such as C1-15 alkyl ([0007] and [0031]). Accordingly, the disclosure of the reference encompasses an embodiment where at most three (3) of T11 to T18 are not hydrogen and the non-hydrogen substituents are C1-4 alkyls.
Regarding claim 15, Boudreault et al teaches all the claim limitations as set forth above. In the compound disclosed by the reference R2 is hydrogen and R5 is a methyl group.
Regarding claim 16, Boudreault et al teaches all the claim limitations as set forth above. Additionally, the reference discloses an organic light emitting device comprising an anode, a cathode, and an organic layer disposed between the anode and cathode ([0102]-[0103]). The organic layer comprises a light emitting, or luminescent layer, which comprises the disclose compound as a light emitting dopant ([0089]).
Response to Arguments
Applicant's arguments filed 1/12/2026 have been fully considered but are moot in light of the new grounds of rejection set forth above.
In light of the amendments to the claims, the 35 U.S.C. 102 rejection of the claims over Tani is withdrawn. However, the reference remains relevant under 35 U.S.C. 103 for the reasons set forth above. Furthermore, in light of the amendments to the claims, the 35 U.S.C. 103 rejection of the claims over Chen as set forth in the previous Office Action is withdrawn.
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
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