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All outstanding objections and rejections, except for those maintained below, are withdrawn in light of applicant's amendment filed on 2/12/2026.
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 2/12/2026. In particular, original Claims 1, 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 27-28 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 27 recites the ligand:
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,
which renders the scope of the claim indefinite for the following reasons. Claim 27 depends from claim 1, and claim 1 recites the following provision: (i) ligand LA has the structure of:
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where X is N, no two RB are joined to fused to form a ring, and each of X3, X5, X6, X7, and X8 is C, then at least one of RA, RB, RC, RDD, or RE is selected from the electron-withdrawing List other than CN, SF5, SiF3, or NO2. Thus, while the ligand falls under the above provision, it is noted that substituent RB is a tetra-substitution representing CN and F, and F is not a member of the electron-withdrawing List. While RB can be F, i.e. a halide, the provision requires an electron-withdrawing group other than CN. Accordingly, the above ligand cannot meet the recited requirements of claim 1, and therefore, it is unclear how one can simultaneously obtain the above ligand recited in claim 27 and still meet the requirements of claim 1.
Claim 28 recites the compounds:
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,
which renders the scope of the claim indefinite for the following reasons. Claim 28 depends from claim 1, and claim 1 recites the following provision: (i) ligand LA has the structure of:
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where X4 is N, no two RB are joined or fused to form a ring and each of X3, X5, X6, X7, and X8 is C, then at least one of RA, RB, RC, RD or RE is selected from the electron-withdrawing List other than CN, SF3, SiF3 or NO2. In the above ligand X4 is N, no two RB are joined or fused to form a ring, and X3, X5, X6, X7, and X8 is C. Thus, in the above compound, ligand LA falls under the above provision. However, it is noted that substituent RB is a tetra-substitution representing CN and F, and F is not a member of the electron-withdrawing List. While RB can be F, i.e. a halide, the provision requires an electron-withdrawing group other than CN. Accordingly, the above compound cannot meet the recited requirements of claim 1, and therefore, it is unclear how one can simultaneously obtain the above compound recited in claim 28 and still meet the requirements of claim 1.
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, 6-7, 9, 13-14, 17, 20, 29, and 31 are rejected under 35 U.S.C. 103(a) as being unpatentable over Kim et al (US 2019/0112324).
Regarding claim 1, Kim et al discloses the following organometallic compound (Page 40 – Compound 32):
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466
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.
This organometallic complex comprises a ligand represented by Formula I of the claims:
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234
186
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,
where:
ring B is a 5-membered heterocyclic ring;
ring D is a 6-membered carbocyclic ring;
rings C and E are absent;
X1, X2, and X4 are C;
X3 is N;
RA is H;
RB is a di-substitution representing alkyl and aryl groups, respectively; and
the ligand is bonded to the metal M, where M is Ir.
RD is the electron-withdrawing group CN and in the ligand, ring C is absent, and ring B is a 5-membered ring, and therefore, the ligand does not satisfy provision (iii) of the claims, i.e. when ring C is absent and ring B is a 5-membered ring, the ligand is required to possess at least one electron withdrawing group from the electron-withdrawing List other than CN, SF3, SiF3 or NO2. However, the compound disclosed by the reference is but one embodiment and attention is directed to following formula (Page 23 – 2-3):
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226
164
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,
where R21 can be a C1 alkyl substituted with a cyano group ([0023] and [0029]), i.e.
-CH2-NC.
This substituent corresponds to the recited formula:
(R2)CCN,
where R2 is hydrogen. Thus the disclosure of the reference encompasses an embodiment where RD is CH2CN.
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, Kim et al teaches all the claim limitations as set forth above. As discussed above, RA is hydrogen; RB is an alkyl group and an aryl group; and RD is CH2CN.
Regarding claim 6, Kim et al teaches all the claim limitations as set forth above. As discussed above, X2 is C and connected to ring D; and X3 is N.
Regarding claim 7, Kim et al teaches all the claim limitations as set forth above. As discussed above, ring B is an imidazole and ring D is benzene.
Regarding claim 9, Kim et al teaches all the claim limitations as set forth above. Additionally, the ligand corresponds to the recited formula:
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176
112
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,
where X1, X4, and X5 are C; X6 is N; and Y1 is NR.
Regarding claim 13, Kim et al teaches all the claim limitations as set forth above. From the discussion above, the compound disclosed by the reference has the formula Ir(LA)3.
Regarding claim 14, Kim et al teaches all the claim limitations as set forth above. Given that the claims do not require ligand LB or Lc, the reference discloses a compound encompassed by the present claims.
Regarding claim 29, Kim et al teaches all the claim limitations as set forth above. As discussed above, the reference discloses the following compound:
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.
This does not correspond to the recited Formula:
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.
However, the reference disclose the following formula (Page 24 – 2(6));
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,
where X13 is O ([0015]).
Regarding claim 31, Kim et al teaches all the claim limitations as set forth above. As discussed above, the reference discloses the following compound:
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.
This does not correspond to the recited Formula:
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206
164
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.
However, the reference disclose the following formula (Page 24 – 2(6));
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,
where X13 is O ([0015]); and X1, X2 and X11 to X12 are C ([0122-[0123] and [0015]).
Regarding claim 17, Kim et al discloses an organic light emitting device comprising an anode, a cathode, and an organic layer disposed between the anode and cathode ([0158]-[0162]). The organic layer comprises the following organometallic compound (Page 40 – Compound 32):
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466
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.
This organometallic complex comprises a ligand represented by Formula I of the claims:
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234
186
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,
where:
ring B is a 5-membered heterocyclic ring;
ring D is a 6-membered carbocyclic rings;
rings C and E are absent;
X1, X2, and X4 are C;
X3 is N;
RA is H;
RB is a di-substitution representing alkyl and aryl groups, respectively; and
the ligand is bonded to the metal M, where M is Ir.
RD is the electron-withdrawing group CN and in the ligand, ring C is absent, and ring B is a 5-membered ring, and therefore, the ligand does not satisfy provision (iii) of the claims, i.e. when ring C is absent and ring B is a 5-membered ring, the ligand is required to possess at least one electron withdrawing group from the electron-withdrawing List other than CN, SF3, SiF3 or NO2. However, the compound disclosed by the reference is but one embodiment and attention is directed to following formula (Page 23 – 2-3):
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226
164
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,
where R21 can be a C1 alkyl substituted with a cyano group ([0023] and [0029]), i.e.
-CH2-NC.
This substituent corresponds to the recited formula:
(R2)CCN,
where R2 is hydrogen. Thus the disclosure of the reference encompasses an embodiment where RD is CH2CN.
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 20, Kim et al discloses an organic light emitting device, i.e. a consumer product, comprising an anode, a cathode, and an organic layer disposed between the anode and cathode ([0158]-[0162]). The organic layer comprises the following organometallic compound (Page 40 – Compound 32):
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466
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.
This organometallic complex comprises a ligand represented by Formula I of the claims:
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234
186
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,
where:
ring B is a 5-membered heterocyclic ring;
ring D is a 6-membered carbocyclic rings;
rings C and E are absent;
X1, X2, and X4 are C;
X3 is N;
RA is H;
RB is a di-substitution representing alkyl and aryl groups, respectively; and
the ligand is bonded to the metal M, where M is Ir.
RD is the electron-withdrawing group CN and in the ligand, ring C is absent, and ring B is a 5-membered ring, and therefore, the ligand does not satisfy provision (iii) of the claims, i.e. when ring C is absent and ring B is a 5-membered ring, the ligand is required to possess at least one electron withdrawing group from the electron-withdrawing List other than CN, SF3, SiF3 or NO2. However, the compound disclosed by the reference is but one embodiment and attention is directed to following formula (Page 23 – 2-3):
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226
164
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,
where R21 can be a C1 alkyl substituted with a cyano group ([0023] and [0029]), i.e.
-CH2-NC.
This substituent corresponds to the recited formula:
(R2)CCN,
where R2 is hydrogen. Thus the disclosure of the reference encompasses an embodiment where RD is CH2CN.
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 1-10, 13-15, 17, 20, and 27-28 are rejected under 35 U.S.C. 103 as being unpatentable over Choi et al (US 2021/0122774).
Regarding claim 1, Choi et al discloses the following organometallic complex (Page 12 – Compound 17).
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.
This organometallic complex comprises a ligand represented by Formula I of the claims:
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234
186
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,
where:
rings B and D are 6-membered carbocyclic rings;
rings C and E are absent;
X1 and X3 are C;
X2 and X4 are N;
two (2) of X1 to X4 are N are required by the present claims;
the ligand is bonded to the metal M, where M is Ir;
RA, RC and RD are H; and
RB is CN, i.e. an electron withdrawing group.
This compound does not satisfy the proviso (i) of the claims i.e. ligand LA has the structure of :
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where X4 is N, no two RB are joined or fused to form a ring and each of X3, X5, X6, X7, and X8 is C, then at least one of RA, RB, RC, RD or RE is selected from the electron-withdrawing List other than CN, SF3, SiF3 or NO2. However, the compound disclosed by the reference is but one embodiment and attention is directed to the following formula ([0048] - Formula 1-1):
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,
where R2 to R6 can be C1 alkyls substituted with a cyano group ([0058] and [0060]), i.e.
-CH2-NC.
This substituent corresponds to the recited formula:
(R2)CCN,
where R2 is hydrogen. Thus the disclosure of the reference encompasses an embodiment where RB is CH2CN.
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, Choi et al teaches all the claim limitations as set forth above. As discussed above, RA, RC and RD are H; and RB is CH2CN.
Regarding claim 3, Choi et al teaches all the claim limitations as set forth above. From the discussion above, the reference discloses a compound where ligand LA is represented by Formula II or III:
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or
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,
given that the claims do not require ring C to be present.
Regarding claim 4, Choi et al teaches all the claim limitations as set forth above. As discussed above, RB is CH2CN, i.e. at least one of RB or RC is an electron-withdrawing group as required by the present claim.
Regarding claim 5, Choi et al teaches all the claim limitations as set forth above. As discussed above, the electron withdrawing groups is CH2CN.
Regarding claim 6, Choi et al teaches all the claim limitations as set forth above. In the compound disclosed by the reference X1 is C and connected to ring D and X2 is N.
Regarding claim 7, Choi et al teaches all the claim limitations as set forth above. In the compound disclosed by the reference rings B and D are benzene rings.
Regarding claim 8, Choi et al teaches all the claim limitations as set forth above. Additionally, it is noted that in the formula of Choi et al ([0048] - Formula 1-1):
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neighboring substituents R2 to R5 may join to form a C6-30 carbocyclic ring ([0020]). Accordingly, two (2) substituents RB can join to form a fused ring as required by the present claims.
Regarding claim 9, Choi et al teaches all the claim limitations as set forth above. From the discussion above, ligand LA corresponds to the recited formula:
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210
182
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where X5 to X8 are C.
Regarding claim 10, Choi et al teaches all the claim limitations as set forth above. Additionally, it is noted that in the formula ([0048] - Formula 1-1):
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R2 to R5 can be a C1 alkoxy group substituted with at least one F ([0063]-[0065]), i.e. the reference discloses the substituent -OCF3.
Furthermore, ring CY1 can be ([0103] and Page 8 – formula CY1-12):
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,
where R61 can be hydrogen ([0105] and [0018]).
Accordingly, the reference discloses a ligand corresponding to recited Formula LAi-2:
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where G is G1:
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82
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,
and RE is R12, i.e. -O-CF3, as required by ligand LA12. Thus, the reference discloses ligand LA12-2 of the present claims.
Regarding claim 13, Choi et al teaches all the claim limitations as set forth above. Additionally, the compound disclosed by the reference has the formula Ir(LA)2(LB).
Regarding claim 14, Choi et al teaches all the claim limitations as set forth above. Additionally, in the compound of the reference:
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,
LB corresponds to the formula:
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,
where Ra1 and Rc1 are alkyl groups and Rb1 is H.
Regarding claim 15, Choi et al teaches all the claim limitations as set forth above. Additionally, in the compound of the reference:
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,
LB corresponds to the formula:
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88
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,
where R201 and R202 are RD10, i.e. tert-butyl, corresponding to ligand LC10 of the present claims.
Regarding claim 27, Choi et al teaches all the claim limitations as set forth above. Additionally, it is noted that the reference discloses the following formula ([0014]):
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,
where two or more neighboring substituents of R2 to R5 can be linked to form a C6-30 carbocyclic group ([0020]), e.g. R3 and R4 can represent C2 alkenyls that link together to form a benzene ring ([0018]). R2 can be a cyano group ([0018]); and R1, R2, and R5 can be hydrogen ([0018]).
The ring CY1 is exemplified as (Page 8 – CY1-12):
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R61 can be a tert-butyl group ([0105], [0018] and [0788]). Accordingly, the disclosure of the reference encompasses the recited ligand:
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Regarding claim 28, Choi et al teaches all the claim limitations as set forth above. Additionally, it is noted that the reference discloses a compound with the formula: M(L1)n1(L2)n2, where M is Ir, n1 is two (2) and n1 is one (1) ([0008]-[0012], [0046], ). Ligand L1 corresponds to the following formula ([0011] and [0014]):
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,
where two or more neighboring substituents of R2 to R5 can be linked to form a C6-30 carbocyclic group ([0020]), e.g. R3 and R4 can represent C2 alkenyls that link together to form a benzene ring ([0018]). R2 can be a cyano group ([0018]); and R1, R2, and R5 can be hydrogen ([0018]).
The ring CY1 is exemplified as (Page 8 – CY1-12):
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,
R61 can be a tert-butyl group ([0105], [0018] and [0788]).
The reference further discloses the co-ligand L2 as ([0014] – Formula 1-2):
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,
where R11 and R15 can be hydrogen ([0018]) and R12, R13, R16, and R17 can be C2-alkyls ([0018]). Accordingly, the disclosure of the reference encompasses the recited compound:
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.
Regarding claim 17, Choi et al discloses an organic light emitting device where the light emitting device comprises a pair or electrodes ([0129]), i.e. an anode and a cathode, and an organic layer, i.e. a light emitting layer, disposed between the anode and cathode ([0127]). The light emitting layer comprises the following compound ([0127] and Page 12 – Compound 17).
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292
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.
This organometallic complex comprises a ligand represented by Formula I of the claims:
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234
186
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,
where:
rings B and D are 6-membered carbocyclic rings;
rings C and E are absent;
X1 and X3 are C;
X2 and X4 are N;
two (2) of X1 to X4 are N are required by the present claims;
the ligand is bonded to the metal M, where M is Ir;
RA, RC and RD are H; and
RB is CN, i.e. an electron withdrawing group.
This compound does not satisfy the proviso (i) of the claims i.e. ligand LA has the structure of :
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where X4 is N, no two RB are joined or fused to form a ring and each of X3, X5, X6, X7, and X8 is C, then at least one of RA, RB, RC, RD or RE is selected from the electron-withdrawing List other than CN, SF3, SiF3 or NO2. However, the compound disclosed by the reference is but one embodiment and attention is directed to the following formula ([0048] - Formula 1-1):
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238
228
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,
where R2 to R6 can be C1 alkyls substituted with a cyano group ([0058] and [0060]), i.e.
-CH2-NC.
This substituent corresponds to the recited formula:
(R2)CCN,
where R2 is hydrogen. Thus the disclosure of the reference encompasses an embodiment where RB is CH2CN.
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 20, Choi et al discloses an organic light emitting device, i.e. a consumer product, where the light emitting device comprises a pair or electrodes ([0129]), i.e. an anode and a cathode, and an organic layer, i.e. a light emitting layer, disposed between the anode and cathode ([0127]). The light emitting layer comprises the following compound ([0127] and Page 12 – Compound 17).
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292
530
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.
This organometallic complex comprises a ligand represented by Formula I of the claims:
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234
186
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,
where:
rings B and D are 6-membered carbocyclic rings;
rings C and E are absent;
X1 and X3 are C;
X2 and X4 are N;
two (2) of X1 to X4 are N are required by the present claims;
the ligand is bonded to the metal M, where M is Ir;
RA, RC and RD are H; and
RB is CN, i.e. an electron withdrawing group.
This compound does not satisfy the proviso (i) of the claims i.e. ligand LA has the structure of :
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126
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where X4 is N, no two RB are joined or fused to form a ring and each of X3, X5, X6, X7, and X8 is C, then at least one of RA, RB, RC, RD or RE is selected from the electron-withdrawing List other than CN, SF3, SiF3 or NO2. However, the compound disclosed by the reference is but one embodiment and attention is directed to the following formula ([0048] - Formula 1-1):
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238
228
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,
where R2 to R6 can be C1 alkyls substituted with a cyano group ([0058] and [0060]), i.e.
-CH2-NC.
This substituent corresponds to the recited formula:
(R2)CCN,
where R2 is hydrogen. Thus the disclosure of the reference encompasses an embodiment where RB is CH2CN.
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 1-7, 9, 13-14, 17, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al (US 2022/0013734).
Regarding claim 1, Lee et al discloses the following organometallic complex ([0213] – Compound 1):
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342
460
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.
This organometallic complex comprises a ligand represented by Formula I of the claims:
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234
186
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,
where:
rings B and D are 6-membered carbocyclic rings;
ring C is a 6-membered carbocyclic ring;
ring E is absent.
X1 and X3 are C;
X2 and X4 are N;
two (2) of X1 to X4 are N are required by the present claims;
the ligand is bonded to the metal M, where M is Ir.
RA, RB and RC are H; and
RD is a di-substitution and representing methyl.
This compound does not satisfy proviso (ii) of the claims, i.e. if LA has a structure of:
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,
where at least one of X3 to X10 is N, then the ligand is required to possess at least one electron withdrawing group from the electron-withdrawing List other than CN, SF3, SiF3 or NO2. However, the compound disclosed by the reference is but one embodiment, and attention is directed to Formula 2 ([0014]):
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274
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,
where a1 can be an integer [0-7] and R1, corresponding to RC of the present claims, can be a C1 alkyl substituted with a cyano group ([0063]-[0065]), i.e.
-CH2-NC.
This substituent corresponds to the recited formula:
(R2)CCN,
where R2 is hydrogen. Thus the disclosure of the reference encompasses an embodiment where RC is CH2CN.
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, Lee et al teaches all the claim limitations as set forth above. As discussed above, RA and RB are H; RC is CH2CN; and RD is an alkyl.
Regarding claim 3, Lee et al teaches all the claim limitations as set forth above. From the discussion above, the reference discloses a compound where ligand LA is represented by Formula III:
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.
Regarding claim 4, Lee et al teaches all the claim limitations as set forth above. As discussed above, RC is an electron withdrawing group.
Regarding claim 5, Lee et al teaches all the claim limitations as set forth above. As discussed above the electron-withdrawing group is CH2CN.
Regarding claim 6, Lee et al teaches all the claim limitations as set forth above. In the compound disclosed by the reference X1 is C and connected to ring D and X2 is N.
Regarding claim 7, Lee et al teaches all the claim limitations as set forth above. In the compound disclosed by the reference rings B, C, and D are benzene rings.
Regarding claim 9, Lee et al teaches all the claim limitations as set forth above. From the discussion above, ligand LA corresponds to the recited formula:
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,
where X5 to X10 are C.
Regarding claim 13, Lee et al teaches all the claim limitations as set forth above. Additionally, the compound disclosed by the reference has the formula Ir(LA)2(LB).
Regarding claim 14, Lee et al teaches all the claim limitations as set forth above. Additionally, in the compound of the reference:
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,
LB corresponds to the formula:
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,
where Ra1 and Rc1 are alkyl groups and Rb1 is H.
Regarding claim 17, Lee et al discloses an organic light emitting device comprising an anode, a cathode, and an organic layer disposed between the anode and cathode ([0002], [0225]-[0226]). The organic layer comprises the following compound ([0027] and [0213] – Compound 1):
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342
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.
This organometallic complex comprises a ligand represented by Formula I of the claims:
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234
186
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,
where:
rings B and D are 6-membered carbocyclic rings;
ring C is a 6-membered carbocyclic ring;
ring E is absent.
X1 and X3 are C;
X2 and X4 are N;
two (2) of X1 to X4 are N are required by the present claims;
the ligand is bonded to the metal M, where M is Ir.
RA, RB and RC are H; and
RD is a di-substitution and representing methyl.
This compound does not satisfy proviso (ii) of the claims, i.e. if LA has a structure of:
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,
where at least one of X3 to X10 is N, then the ligand is required to possess at least one electron withdrawing group from the electron-withdrawing List other than CN, SF3, SiF3 or NO2. However, the compound disclosed by the reference is but one embodiment, and attention is directed to Formula 2 ([0014]):
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,
where a1 can be an integer [0-7] and R1, corresponding to RC of the present claims, can be a C1 alkyl substituted with a cyano group ([0063]-[0065]), i.e.
-CH2-NC.
This substituent corresponds to the recited formula:
(R2)CCN,
where R2 is hydrogen. Thus the disclosure of the reference encompasses an embodiment where RC is CH2CN.
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 20, Lee et al discloses an organic light emitting device, i.e. a consumer product, comprising an anode, a cathode, and an organic layer disposed between the anode and cathode ([0002] and [0225]-[0226]). The organic layer comprises the following compound ([0027] and [0213] – Compound 1):
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.
This organometallic complex comprises a ligand represented by Formula I of the claims:
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234
186
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,
where:
rings B and D are 6-membered carbocyclic rings;
ring C is a 6-membered carbocyclic ring;
ring E is absent.
X1 and X3 are C;
X2 and X4 are N;
two (2) of X1 to X4 are N are required by the present claims;
the ligand is bonded to the metal M, where M is Ir.
RA, RB and RC are H; and
RD is a di-substitution and representing methyl.
This compound does not satisfy proviso (ii) of the claims, i.e. if LA has a structure of:
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214
132
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,
where at least one of X3 to X10 is N, then the ligand is required to possess at least one electron withdrawing group from the electron-withdrawing List other than CN, SF3, SiF3 or NO2. However, the compound disclosed by the reference is but one embodiment, and attention is directed to Formula 2 ([0014]):
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,
where a1 can be an integer [0-7] and R1, corresponding to RC of the present claims, can be a C1 alkyl substituted with a cyano group ([0063]-[0065]), i.e.
-CH2-NC.
This substituent corresponds to the recited formula:
(R2)CCN,
where R2 is hydrogen. Thus the disclosure of the reference encompasses an embodiment where RC is CH2CN.
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, 9, and 30-31 are rejected under 35 U.S.C. 103 as being unpatentable over Ji (US 2017/0365799).
Regarding claim 1, Ji et al discloses the following compound (Page 78 – Compound 379):
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.
This organometallic complex comprises a ligand represented by Formula I of the claims:
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186
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,
where:
ring B is a 5-membered heterocyclic ring;
rings C and D are 6-membered carbocyclic rings;
ring E is absent;
X1 to X-4 are C;
RA, RB, RC, and RD are hydrogen; and
the ligand is bonded to the metal M, where M is Ir.
Substituents RA, RB, RC, and RD are hydrogen, and therefore, one of the substituents does not correspond to an electron-withdrawing group as required by the present claims. However, the compound disclosed by the reference is but one embodiment and attention is directed to the following formula ([0047] – Formula 1):
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where R5 and R6, correspond to RA, RB, RC, and RD of the claims can be a mono to maximum number of substitutions ([0052]) and can represent a nitrile, i.e. -CN or isonitrile, i.e. -NC. Accordingly, the disclosure of the reference encompasses an embodiment where RA, RB, RC, and RD is CN or NC.
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 9, Ji et al teaches all the claim limitations as set forth above. From the discussion above, the reference discloses that recited ligand LA corresponds to:
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,
where X3 to X8 are C; and Y1 is S.
Regarding claim 30, Ji et al teaches all the claim limitations as set forth above. From the discussion above, the reference discloses that recited ligand LA corresponds to:
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.
Regarding claim 31, Ji et al teaches all the claim limitations as set forth above. From the discussion above, the reference discloses that recited ligand LA corresponds to:
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,
where X3 to X8 are C.
Response to Arguments
Applicant's arguments filed 2/12/2026 have been fully considered but they are not persuasive.
In light of the amendments to the claim the claim objections and 35 U.S.C. 112 (b) rejections set forth in the previous Office Action are withdrawn. Furthermore, in light of the claim amendments the 35 U.S.C. 102 rejections of the claims as anticipated by Kim et al, set forth in the previous Office Action, are withdrawn.
Applicants argue that Kim et al does not disclose the compound recited in the as-amended claims. However, as discussed in the rejections above, the reference discloses the following formula (Page 23 – 2-3):
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,
where R21, corresponding to RD of the present claims, can be a C1 alkyl substituted with a cyano group ([0023] and [0029]), i.e.
-CH2-NC.
This substituent corresponds to the recited formula:
(R2)CCN,
where R2 is hydrogen. Thus the disclosure of the reference encompasses an embodiment where RD is CH2CN.
Applicants argue that Choi et al does not disclose the compound recited in the as-amended claims. However, as discussed in the rejections above, the reference discloses the following formula ([0048] - Formula 1-1):
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where R2 to R6, corresponding to RB of the present claims, can be C1 alkyls substituted with a cyano group ([0058] and [0060]), i.e.
-CH2-NC.
This substituent corresponds to the recited formula:
(R2)CCN,
where R2 is hydrogen. Thus the disclosure of the reference encompasses an embodiment where RB is CH2CN.
Applicants argue that Lee et al does not disclose the compound recited in the as-amended claims. However, as discussed in the rejections above, the reference discloses the following formula ([0014]- Formula 2):
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where a1 can be an integer [0-7] and R1, corresponding to RC of the present claims, can be a C1 alkyl substituted with a cyano group ([0063]-[0065]), i.e.
-CH2-NC.
This substituent corresponds to the recited formula:
(R2)CCN,
where R2 is hydrogen. Thus the disclosure of the reference encompasses an embodiment where RC is CH2CN.
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