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 .
Status of Claims
Claims 1 and 10 are amended and claim 21 is new due to Applicant's amendment dated 11/10/2025. Claims 1-8, 10, and 13-21 are pending.
Response to Amendment
The rejection of claims 1-8, 10, and 13-20 under 35 U.S.C. 103 as being unpatentable over Macinnis (US 2022/0336759 A1) is overcome due to the Applicant’s amendment dated 11/10/2025. The rejection is withdrawn. However, as outlined below, new grounds of rejection have been made.
Response to Arguments
Insofar as the arguments apply to the new grounds of rejection below, Applicant’s arguments on pages 22-24 of the reply dated 11/10/2025 with respect to the rejection of claims 1-8, 10, and 13-20 as set forth in the previous Office Action have been fully considered but they are not persuasive.
Applicant's argument – On pages 22-24, Applicant argues the cited reference Macinnis fails to teach the claims as amended which require the proviso that in Formula 2-1, i) Y21 is B, and K1 to K3 are each O, ii) Y21 is N, and K1 to K3 are each a single bond, iii) Y21 is N, and K1 to K3 are each C(=O), or iv) Y21 is N, and K1 to K3 are each S(=O)2.
Examiner’s response—As discussed in greater detail in the rejection below, Macinnis teaches a structure that reads on the Formula 2-1 wherein condition i) is satisfied. Accordingly, the cited reference teaches the claims as amended.
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 1-8, 10, and 13-20 are rejected under 35 U.S.C. 103 as being unpatentable over Macinnis (US 2022/0336759 A1), as evidenced by Thompson (US 2006/0024522 A1).
Regarding claims 1-8, 10, 13-16 and 20, Macinnis teaches a compound comprising a ligand LA comprising a moiety L having a structure of Formula I for use in an OLED device (abstract and ¶ [0006]). In particular, the OLED comprises an anode, a cathode, and an emissive layer further comprising the compound comprising the ligand LA as a dopant (¶ [0205]-[0209]). Macinnis teaches examples of compounds comprising a ligand LA including the compound on pg. 217.
Formula I:
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Macinnis’ compound:
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Macinnis’ compound fails to read on the claimed Formula 2 as the ring A of Macinnis’ Formula I is not a carbocyclic group. However, Macinnis does teach alternative structures represented by Formula I, as shown in the compound below on pg. 203 (¶ [0008]).
Macinnis’ compound on pg. 203:
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77
42
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Therefore, given the general formula and teachings of Macinnis’, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the group
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with the group
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as shown in Macinnis’ compound above on pg. 203, because Macinnis teaches the moiety L may suitably be selected as the group
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. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful as the dopant in the emissive layer of the device of Macinnis. See MPEP 2143.I.(B).
The modified compound of Macinnis reads on an embodiment of Macinnis’ Formula II, which Macinnis teaches comprises a metal-carbene bond (¶ [0200]). Accordingly, condition 7) of Macinnis is satisfied (¶ [0018]-[0026]).
The modified compound of Macinnis is reproduced below in comparison to the claimed Formula 1, 1-1, and 2-1. Formula 1 has the structure
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.
1-1:
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2-1:
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modified compound:
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The modified compound of Macinnis reads on the claimed Formula 1, 1-1, and 2-1 wherein:
M1 is Pt (claim 2);
L11 is a ligand represented by Formula 1-1;
L12 is not required to be present;
n11 is 1 and n12 is 0;
X1 to X3 are each C and X4 is N;
Ring CY1 is a C7 heterocyclic group represented by CY1(17), ring CY2 is a C6 carbocyclic group represented by CY2(1), ring CY3 is a C12 heterocyclic group represented by CY3(1), and ring CY4 is a C5 heterocyclic group represented by CY4(1) (claims 4-7);
T1 and T3 are each a single bond, T2 is *-O-*’, and T4 is not required to be present;
a1 to a3 are each 1 and a4 is 0;
E1 is a group represented by Formula 2-1;
n1, n2, and n4 are each 0, and n3 is 1 (claim 8);
Y21 is B;
c201 is 2, and c202 and c203 are each 3;
c206 and c207 are not required to be present;
K1 to K3 are each O;
R10 is a deuterium-substituted C18 aryl group, R20, R30, and R201 to R203 are each hydrogen, and R40 is an unsubstituted C4 alkyl group; and
c10 and c40 are each an integer of 1, c20 is an integer of 3, and c30 is an integer of 5.
Additionally, as Y21 is B, K1 to K3 are each O, condition i) is satisfied.
As Formula 2-5 is not required to be present, the limitations of claim 10 are satisfied.
Macinnis’ compound reads on an embodiment of Macinnis’ Formula II, which Macinnis teaches comprises a metal-carbene bond (¶ [0200]). As evidenced by Thompson, a metal-carbene bond may also be drawn as shown below (see Thompson, ¶ [00143]).
Formula II:
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Thompson:
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Accordingly, Macinnis’ compound reads on the claimed Formula 1-1A (claims 13-14).
Regarding claim 20, although the instant claim is drawn to an apparatus, the only positive limitation of the claimed apparatus is organic light-emitting device of claim 15. Claim 20 does not add any further structural or functional limitations to the device and/or organometallic compound. Macinnis teaches the organic light emitting device according to claim 15, as described above, and does not include any components that would make it unfit for use as an apparatus. Therefore, the OLED of Macinnis according to claim 15 may be considered an apparatus.
Regarding claims 17 and 19, Macinnis teaches the OLED comprising the modified compound, as described above with respect to claims 15-16.
Macinnis fails to specifically teach an example of a device including a host, a hole transport region, and an electron region in combination with the modified compound. However, Macinnis does teach an example of a device having the structure of an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, wherein the emissive layer may further comprise a host (¶ [0208]-[0209] and [0227]).
Therefore, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to use the modified compound of Macinnis in an emissive layer of a device having the structure of an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an emissive layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, wherein the emissive layer further includes a host, because one of ordinary skill in the art would reasonably have expected the elements of the modified compound of Macinnis and the OLED device to predictably maintain their respective properties or functions after they have been combined, and this would have been combining prior art elements according to known methods to yield predictable results. See MPEP 2143.I.(A).
Regarding claim 18, Macinnis teaches the OLED comprising the modified compound of Macinnis, as described above with respect to claim 16.
Macinnis fails to teach the emission wavelength of the modified compound. However, Macinnis does teach a substituent of the compound may be represented by R190 (as shown in the compound on pg. 217), or R61 (pgs. 32 and 43).
R61:
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R190:
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Therefore, given the general formula and teachings of Macinnis, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to substitute the R190 group with the R61 group, because Macinnis teaches a substituent of the compound may suitably be selected as t-butyl-substituted phenyl. The substitution would have been one known element for another and one of ordinary skill in the pertinent art would reasonably expect the predictable result that the modified compound would be useful as the dopant in the emissive layer of the OLED of Macinnis. See MPEP 2143.I.(B).
Additionally, it would have been obvious to one of ordinary skill in the pertinent art before the effective filing date of the claimed invention to select the group R61 as the substituent, because it would have been choosing from a list of suitable substituents taught by Macinnis, which would have been a choice from a finite number of identified, predictable solutions of a compound useful as the dopant in the emissive layer of the device of Macinnis. One of ordinary skill in the art would have been motivated to produce additional compounds comprising a ligand LA comprising a moiety L having a structure of Formula I in order to pursue the known options within his or her technical grasp with a reasonable expectation of success. See MPEP 2143.I.(E).
Macinnis appears silent with respect to the property of emitting blue light.
The instant specification recites that the instant compounds Pt-1 has a maximum emission wavelength of 461 nm (see Table 1 on pg. 47). Blue light emission occurs at a maximum emission wavelength of 440 nm to about 480 nm (instant ¶ [0095]). Since Macinnis teaches the modified compound, a structure nearly identical to compound Pt-1 as disclosed by the Applicant, the property of emitting blue light is considered to be inherent, absent evidence otherwise. Recitation of a newly disclosed property does not distinguish over a reference disclosure of the article or composition claims. When the structure recited in the prior art reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. Applicant bears responsibility for proving that the reference composition does not possess the characteristics recited in the claims. See MPEP 2112.
Allowable Subject Matter
Claim 21 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
With respect to claim 21, the prior art does not teach or suggest an organometallic compound represented by Formula 1 wherein E1 is a group represented by one of Formulae 2-5 to 2-8, in combination with the remainder of claim 21.
Macinnis (US 2022/0336759 A1), cited in the rejection above, is considered the closest prior art. Macinnis teaches a compound comprising a ligand LA comprising a moiety L having a structure of Formula I for use in an OLED device (abstract and ¶ [0006]). Macinnis teaches examples of compounds comprising a ligand LA including the compound below on pg. 217.
Formula I:
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Macinnis’ compound:
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Macinnis’ compound fails to teach a group that reads on one of the claimed Formula 2-5 to 2-8.
Sotoyama (US 2023/0075211 A1) is relevant to the claimed invention. Sotoyama teaches condensed cyclic compounds represented by Formula 1-1 or 1-2 for use in organic light-emitting devices (abstract). Examples thereof include compound 83 (page 31).
83:
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While compound 83 reads on the claimed Formula 2-7, Sotoyama fails to teach or provide motivation to use compound 83 as a substituent of an organometallic compound. Accordingly, Sotoyama fails to remedy the deficiencies of Macinnis.
Thus there is no prior art, either alone or in combination, which teaches or renders obvious an organometallic compound represented by Formula 1 wherein E1 is a group represented by one of Formulae 2-5 to 2-8, in combination with the remainder of claim 21.
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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BRAELYN R WATSON whose telephone number is (571)272-1822. The examiner can normally be reached M-F 7:30am-5pm.
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/BRAELYN R WATSON/Examiner, Art Unit 1786