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All outstanding objections and rejections, except for those maintained below, are withdrawn in light of applicant's amendment filed on 11/28/2025.
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 11/28/2025. In particular, original Claims 1 and 17 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 1-2, 4-6, 8-10, 12, 14, 17-19, 24, and 26-29 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 1 recites that at least one of R11 or R12 comprises a moiety selected from the group consisting of
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, unsubstituted
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, adamantly, bicyclo[3,1,1]heptyl, spiroalkyl, and partially or fully deuterated variants thereof. The recitation of unsubstituted
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in combination with the limitation “partially or fully deuterated variants thereof” renders the scope of the claim indefinite given that it is unclear if unsubstituted as applied to J includes deuterated variants of J or if deuterated variants are considered to be unsubstituted.
Claim 17 recites that at least one of R11 or R12 comprises a moiety selected from the group consisting of
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, unsubstituted
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, adamantly, bicyclo[3,1,1]heptyl, spiroalkyl, and partially or fully deuterated variants thereof. The recitation of unsubstituted
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in combination with the limitation “partially or fully deuterated variants thereof” renders the scope of the claim indefinite given that it is unclear if unsubstituted as applied to J includes deuterated variants of J or if deuterated variants are considered to be unsubstituted.
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)(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 1-2, 6, 8, 17-19, and 27-29 are rejected under 35 U.S.C. 102(a1) as being anticipated by Gorohmaru et al (US 2019/0019956).
Regarding claim 1, Gorohmaru et al discloses the following compound (Page 39):
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.
This compound has the formula:
Ir(LA)x(LB)y(LC)z,
where x is two (2); y is one (1); and z is zero (0).
Ligand LA corresponds to recited Formula I:
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266
210
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,
where:
Z1 is C;
Z2 is N; R1, R2, R3, R11, RA, and RC are hydrogen; and
R11 corresponds to an unsubstituted J:
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.
Ligand LB corresponds to recited Formula II:
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230
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,
where:
Z3 is N;
Z4 is C;
R4, RD, and RE are hydrogen;
R12 is a combination of alkyl and aryl; and
R11 and R12 together comprise four (4) 6-membered aryls.
Regarding claim 2, Gorohmaru et al teaches all the claim limitations as set forth above. As discussed above, RA, RB, RC, RD and RE are hydrogen.
Regarding claim 6, Gorohmaru et al teaches all the claim limitations as set forth above. Additionally, it is noted that the compound disclosed by the reference can be relabeled such as follows:
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,
and therefore, R12 comprises three (3) aryl groups.
Regarding claim 8, Gorohmaru et al teaches all the claim limitations as set forth above. Additionally, it is noted that the compound disclosed by the reference can be relabeled such as follows:
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518
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.
This compound has the formulas Ir(LA)x(LB)y(LC)z, where x is one (1); and y is two (2).
Regarding claim 19, Gorohmaru et al teaches all the claim limitations as set forth above Additionally, the reference discloses an organic electroluminescent device, i.e. a consumer product, comprising an anode, a cathode, a luminescent layer, i.e. an organic layer, disposed between the anode and cathode ([0307]-[0319] – Example 1), where the luminescent layer comprises the disclosed compound.
Regarding claim 27, Gorohmaru et al teaches all the claim limitations as set forth above. As discussed above, R11 comprises aryl.
Regarding claim 28, Gorohmaru et al teaches all the claim limitations as set forth above. As discussed above, R11 comprises unsubstituted J:
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.
Regarding claim 29, Gorohmaru et al teaches all the claim limitations as set forth above. As discussed above, R11 comprises unsubstituted J:
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.
Regarding claim 17, Gorohmaru et al discloses an organic electroluminescent device comprising an anode, a cathode, a luminescent layer, i.e. an organic layer disposed between the anode and cathode ([0307]-[0319] – Example 1). The luminescent layer comprises the following compound (Page 39 and [0313] – D-1):
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.
This compound has the formula:
Ir(LA)x(LB)y(LC)z,
where x is two (2); y is one (1); and z is zero (0).
Ligand LA corresponds to recited Formula I:
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266
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,
where:
Z1 is C;
Z2 is N; R1, R2, R3, R11, RA, and RC are hydrogen; and
R11 corresponds to an unsubstituted J:
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.
Ligand LB corresponds to recited Formula II:
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230
146
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,
where:
Z3 is N;
Z4 is C;
R4, RD, and RE are hydrogen;
R12 is a combination of alkyl and aryl; and
R11 and R12 together comprise four (4) 6-membered aryls.
Regarding claim 18, Gorohmaru et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that luminescent layer comprises the following compound ([0313] – H-2):
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,
i.e. a host comprising a carbazole moiety.
In light of the above, it is clear that Gorohmaru et al anticipates the presently recited claims.
Claims 1-2, 8, 17-19, and 29 are rejected under 35 U.S.C. 102(a1) as being anticipated by Inbasekaran et al (US 2012/0049168).
Regarding claim 1, Inbasekaran et al discloses the following compound (Page 23 Compound B):
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477
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.
This compound has the formula:
Ir(LA)x(LB)y(LC)z,
where x is two (2); y is one (1); and z is zero (0).
Ligand LA corresponds to recited Formula I:
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266
210
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,
where:
Z1 is C;
Z2 is N; and
R1, R2, R11, RA, RB, and RC are hydrogen.
Ligand LB corresponds to recited Formula II:
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230
146
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,
where:
Z3 is N;
Z4 is C;
R4, RD, and RE are hydrogen;
R12 corresponds to an unsubstituted J:
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; and
R11 and R12 comprise two (2) C6 aryl groups.
Alternatively, the reference discloses the following compound (Page 23 – Compound C):
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404
592
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.
This compound has the formula:
Ir(LA)x(LB)y(LC)z,
where x is one(1); y is two (2); and z is zero (0).
Ligand LA corresponds to recited Formula I:
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266
210
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,
where:
Z1 is C;
Z2 is N; and
R1, R2, R11, RA, RB, and RC are hydrogen.
Ligand LB corresponds to recited Formula II:
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230
146
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,
where:
Z3 is N;
Z4 is C;
R4, RD, and RE are hydrogen;
R12 corresponds to an unsubstituted J:
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; and
R11 and R12 comprise two (2) C6 aryl groups.
Regarding claim 2, Inbasekaran et al teaches all the claim limitations as set forth above. As discussed above, RA, RB, RC, RD and RE are hydrogen.
Regarding claim 8, Inbasekaran et al teaches all the claim limitations as set forth above. As discussed above, the reference discloses a compound where x is one (1) and y is two (2).
Regarding claim 19, Inbasekaran et al teaches all the claim limitations as set forth above. Additionally, the reference discloses an organic light emitting device comprising an anode and cathode and an organic layer, i.e. a light emitting layer, disposed between the anode and cathode ([0081]-[0082] – Device 2). The light emitting layer comprises the disclosed compound ([0084] – Green Dopant-1 and Page 23 Compound B).
Regarding claim 29, Inbasekaran et al teaches all the claim limitations as set forth above. As discussed above, the reference discloses a compound where R12 comprises unsubstituted J:
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.
Regarding claim 17, Inbasekaran et al discloses an organic light emitting device comprising an anode and cathode and an organic layer, i.. a light emitting layer disposed between the anode and cathode ([0081]-[0082] – Device 2). The light emitting layer the following compound ([0084] – Green Dopant-1 and Page 23 Compound B):
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477
592
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.
This compound has the formula:
Ir(LA)x(LB)y(LC)z,
where x is two (2); y is one (1); and z is zero (0).
Ligand LA corresponds to recited Formula I:
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266
210
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,
where:
Z1 is C;
Z2 is N; and
R1, R2, R11, RA, RB, and RC are hydrogen.
Ligand LB corresponds to recited Formula II:
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230
146
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,
where:
Z3 is N;
Z4 is C;
R4, RD, and RE are hydrogen;
R12 corresponds to an unsubstituted J:
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; and
R11 and R12 comprise two (2) C6 aryl groups.
Alternatively, the reference discloses the following compound (Page 23 – Compound C):
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404
592
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.
This compound has the formula:
Ir(LA)x(LB)y(LC)z,
where x is one(1); y is two (2); and z is zero (0).
Ligand LA corresponds to recited Formula I:
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266
210
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,
where:
Z1 is C;
Z2 is N; and
R1, R2, R11, RA, RB, and RC are hydrogen.
Ligand LB corresponds to recited Formula II:
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230
146
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,
where:
Z3 is N;
Z4 is C;
R4, RD, and RE are hydrogen;
R12 corresponds to an unsubstituted J:
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; and
R11 and R12 comprise two (2) C6 aryl groups.
Regarding claim 18, Inbasekaran et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that the light emitting layer comprises the host compound ([0084 – Host 2 and Page 23):
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,
i.e. a host comprising a carbazole moiety.
In light of the above, it is clear that Inbasekaran et al anticipates the presently recited claims.
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 1-2, 4-6, 8-10, 12, 14, 17-19, 24, and 26-29 are rejected under 35 U.S.C. 103 as being unpatentable over Margulies et al (US 2017/0365801).
Regarding claim 1, Margulies et al discloses a compound with the formula:
M(L1)x(L2)y(L3)z,
where M is Ir; x is 1, 2, or 3; y is 0, 1, or 2, and z is 0, 1, or 2 ([0099] and [0105]-[0109]). Accordingly, when z is zero (0), the reference discloses a compound with the recited formula:
Ir(LA)x(LB)y(Lc)z,
where x is one (1) or two (2); y is one (1) or two (2); z is zero (0) or one (1); and x + y + z = 3.
Ligand L1, corresponding to recited ligand LA, is represented as ([0128]):
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,
where Ra is a mono-substitution and is an alkyl ([0117]); Rb is H; and Rc is a mono-substitution and is an alkyl ([0117]). Rd is a di-substitution where one (1) Rd is an aryl such as biphenyl. The second Rd includes the substituent R1 ([0119]) such as ([0119], [0095], and Page 14 – Substituent 92):
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.
Accordingly, ligand L1 of the reference corresponds to ligand LA of the claims:
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,
where Z1 is N; Z2 is C; R1 is H; R2 and R3 are alkyls; and RA and RF are H. Two (2) substituents RC join to form a ring; RB corresponds to Substituent 92:
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,
and R11 corresponds to biphenyl which encompasses the substituent unsubstituted J:
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.
Ligand L2, corresponding to recited ligand LB, is represented as ([0128]):
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,
where Ra, is a mono-substitution and is hydrogen ([0111]) and Rb, can represent a mono-substitution ([0111]). The reference discloses that at least one of Ra, Rb, Re and Rd includes substituent R1 ([0119]). For R1 the reference discloses the substituent (Page 11 - Substituent 25):
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,
i.e. an aryl ring.
Accordingly, ligand L2 of the reference corresponds to ligand LB of the claims:
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,
where Z3 is N; Z4 is C; R4, RE, and RD are H; and R12 is a phenyl group, i.e. an aryl group.
From the above, R11 and R12 together comprise three (3) 6-membered aryl rings as required by 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 2, Margulies et al teaches all the claim limitations as set forth above. As discussed above, RA, RC, RD, RE and RF are H; and RB is:
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i.e. a combination of alkyl and aryl.
Regarding claim 4, Margulies et al teaches all the claim limitations as set forth above. Additionally, for Rd, corresponding to the recited group R11, the reference discloses the following R1 substituent (Page 11 – Substituent 22):
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i.e. an alkyl substituted partially deuterated cycloalkyl ring.
Regarding claim 5, Margulies et al teaches all the claim limitations as set forth above. As discussed above, the reference discloses that at least one of Ra, Rb, Re and Rd includes substituent R1 ([0119]). Thus, in the ligand:
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Rb, corresponding to R12, can correspond to the following substituent ([0119], [0095], and Page 14 – Substituent 92):
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i.e. a biphenyl group. Thus, the reference discloses an embodiment where the recited group R12 comprises two (2) aryl groups as recited in the present claims.
Regarding claim 6, Margulies et al teaches all the claim limitations as set forth above. As discussed above, the reference discloses that Rb can be an aryl such as triphenyl ([0051]).Thus, the reference discloses an embodiment where the recited group R12 comprises three (3) aryl groups as recited in the present claims.
Regarding claim 8, Margulies et al teaches all the claim limitations as set forth above. From the discussion above, x is one (1) and y is two (2).
Regarding claim 9, Margulies et al teaches all the claim limitations as set forth above. As discussed above, the reference discloses the ligand:
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m
where Ra and Rd represent from a mono substitution to the maximum number of possible substitutions ([0116]) and can be deuterium. Therefore, in the recited ligand LA:
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Y1 is O; and RA3, RA4, RA1 and RA2 are deuterium. X2 and X3 are C; and X1 is N, while the claim requires that X1 to X3 are each C. However, the reference discloses the following formula ([0111]):
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where X5 to X8 can be C or N ([0112]). Accordingly, the disclosure of the reference encompasses an embodiment where in the recited ligand X1 to X3 are C.
Regarding claim 10, Margulies et al teaches all the claim limitations as set forth above. Additionally, the reference discloses the ligand L2 as ([0128]):
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,
where Ra and Rb are mono to the maximum number of substitutions, and where: Ra corresponds to RB1; and Rb corresponds to RB2 and R12. Ra and Rb can alkyls ([0117]). Accordingly, in recited ligand LB:
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RB1 and RB2 are alkyls and R12 is H.
Regarding claim 12, Margulies et al teaches all the claim limitations as set forth above. From the discussion above, the reference discloses a compound with the formula Ir(LA)(LB)(LC). Ligand LB is:
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where ArIV is an aryl group; RD, R2 and R4 are H. The reference discloses ligand L3, corresponding to recited ligand LC, as ([0128]):
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,
where Ra and Rb are H or an alkyl. This ligand corresponds to Formula V:
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,
where Z5 is N; Z6 is C; and RG and RH are H or alkyl.
Regarding claim 14, Margulies et al teaches all the claim limitations as set forth above. From the discussion above, the reference discloses a compound with the formula:
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.
Regarding claim 19, Margulies et al teach all the claim limitations as set forth above. Additionally, the reference discloses the following organic light emitting device, i.e. consumer product (Figure 2):
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,
where layer 230 is the anode, layer 215 is the cathode and layer 225 is the emissive layer, i.e. organic layer, comprising the disclosed compound ([0037] and [0141]).
Regarding claim 24, Margulies et al teach all the claim limitations as set forth above. Additionally, in the ligand:
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Ra, corresponding to RD, can be an alkyl; and Rb, corresponding to R4 can be an alkyl ([0011]). From the formula disclose by the reference it is clear that these substituents can be para to the ring containing Z4.
Regarding claim 26, Margulies et al teach all the claim limitations as set forth above. As discussed above, the reference discloses a compound with the formula:
M(L1)x(L2)y(L3)z,
where M is Ir; x is 1, 2, or 3; y is 0, 1, or 2, and z is 0, 1, or 2 ([0099] and [0105]-[0109]). Accordingly, the reference discloses a compound with the recited formula:
Ir(LA)x(LB)y(Lc)z,
where z is one (1). In the disclosed ligand:
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Ra corresponding to RD, can be an alkyl; and Rb, corresponding to R4 can be an alkyl ([011]). From the formula disclosed by the reference it is clear that these substituents can be para to the ring containing X4.
As discussed above, in the reference ligand L3 can correspond to the formula:
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,
where Ra and Rb, corresponding to RG and RH are alkyls. As discussed above, the reference discloses the recited formula:
As discussed above, the reference discloses a compound with the recited formula:
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and from the formula disclosed by the reference it is clear that RG can be para to the ring substituted by RH and RH can be para to the bond to the ring substituted by RG as recited in the present claim.
Regarding claim 27, Margulies et al teach all the claim limitations as set forth above. As discussed above R11 comprises an aryl group.
Regarding claim 28, Margulies et al teach all the claim limitations as set forth above. As discussed above R11 comprises unsubstituted J:
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.
Regarding claim 29, Margulies et al teach all the claim limitations as set forth above. As discussed above R11 comprises unsubstituted J:
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.
Regarding claim 17, Margulies et al discloses the following organic light emitting device, i.e. consumer product (Figure 2):
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,
where layer 230 is the anode, layer 215 is the cathode and layer 225 is the emissive layer, i.e. organic layer ([0037]). The emissive layer comprises a compound with the formula:
M(L1)x(L2)y(L3)z,
where M is Ir; x is 1, 2, or 3; y is 0, 1, or 2, and z is 0, 1, or 2 ([0099] and [0105]-[0109]). Accordingly, when z is zero (0), the reference discloses a compound with the recited formula:
Ir(LA)x(LB)y(Lc)z,
where x is one (1) or two (2); y is one (1) or two (2); z is zero (0) or one (1); and x + y + z = 3.
Ligand L1, corresponding to recited ligand LA, is represented as ([0128]):
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251
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,
where Ra is a mono-substitution and is an alkyl ([0117]); Rb is H; and Rc is a mono-substitution and is an alkyl ([0117]). Rd is a di-substitution where one (1) Rd is an aryl such as biphenyl. The second Rd includes the substituent R1 ([0119]) such as ([0119], [0095], and Page 14 – Substituent 92):
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.
Accordingly, ligand L1 of the reference corresponds to ligand LA of the claims:
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where Z1 is N; Z2 is C; R1 is H; R2 and R3 are alkyls; and RA and RF are H. Two (2) substituents RC join to form a ring; RB corresponds to Substituent 92:
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,
and R11 corresponds to biphenyl which encompasses the substituent unsubstituted J:
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.
Ligand L2, corresponding to recited ligand LB, is represented as ([0128]):
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456
212
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,
where Ra, is a mono-substitution and is hydrogen ([0111]) and Rb, can represent a mono-substitution ([0111]). The reference discloses that at least one of Ra, Rb, Re and Rd includes substituent R1 ([0119]). For R1 the reference discloses the substituent (Page 11 - Substituent 25):
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,
i.e. an aryl ring.
Accordingly, ligand L2 of the reference corresponds to ligand LB of the claims:
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,
where Z3 is N; Z4 is C; R4, RE, and RD are H; and R12 is a phenyl group, i.e. an aryl group.
From the above, R11 and R12 together comprise three (3) 6-membered aryl rings as required by 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 18, Margulies et al teach all the claim limitations as set forth above. Additionally, the reference discloses that the organic layer further comprises a host, where the host comprises a triphenylene containing benzo-fused thiophene or ben-fused furan ([0142]). Accordingly, the reference discloses a host comprising a triphenylene moiety as recited in the present claims.
Allowable Subject Matter
Claims 15 and 21 are allowed over the “closest” prior art Nagayama et al (US 2014/0319505, hereafter Nagayama ‘505), Margulies et al (US 2017/0365801), Nagayama et al (US 2020/0274078, hereafter Nagayama ‘078), Gorohmaru et al (US 2019/0019956), and Inbasekaran et al (US 2012/0049168) for the reasons set forth below.
Nagayama ‘505 discloses compounds such as:
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243
353
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and
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292
455
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.
However, the reference does not disclose or suggest the compounds recited in claim 15.
Margulies et al discloses compounds such as:
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177
404
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and
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170
337
media_image33.png
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.
However, the reference does not disclose or suggest the compounds recited in claim 15.
Nagayama ‘078 discloses compounds such as:
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164
407
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and
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245
417
media_image35.png
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.
However, the reference does not disclose or suggest the compounds recited in claim 15.
Gorohmaru et al discloses compounds such as:
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518
492
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.
However, the reference does not disclose or suggest the compounds recited in claim 15.
Inbasekaran et al discloses compounds such as:
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477
592
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.
However, the reference does not disclose or suggest the compounds recited in claim 15.
In light of the above, it is clear that Nagayama ‘505, Margulies et al, Nagayama ‘078, Gorohmaru et al, and Inbasekaran et al, either alone or in combination, do not disclose or suggest the compounds as required by claim 15.
Response to Arguments
Applicant's arguments filed 11/28/2025 have been fully considered but they are not persuasive.
In light of the amendments to the claims, the claim objections and 35 U.S.C. 112 (b) rejections set forth in the previous Office Action are withdrawn.
Applicants argue that Margulies does not disclose a compound recited in as-amended claims 1 and 17. However, as discussed in the rejections above, the reference discloses the following ligand:
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343
251
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,
where Ra is a mono-substitution and is an alkyl ([0117]); Rb is H; and Rc is a mono-substitution and is an alkyl ([0117]). Rd is a di-substitution where one (1) Rd is an aryl such as biphenyl. The second Rd includes the substituent R1 ([0119]) such as ([0119], [0095], and Page 14 – Substituent 92):
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129
214
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.
Accordingly, ligand L1 of the reference corresponds to ligand LA of the claims:
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266
210
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,
where Z1 is N; Z2 is C; R1 is H; R2 and R3 are alkyls; and RA and RF are H. Two (2) substituents RC join to form a ring; RB corresponds to Substituent 92:
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129
214
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,
and R11 corresponds to biphenyl which encompasses the substituent unsubstituted J:
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120
132
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.
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