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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 02/06/2025 has been entered.
This office action is in response to the amendment filed 02/06/2025, which amends claims 1, 4, 5, 8, 9, 12-15, and 19. Claims 1, 3-10, and 12-22 are pending in the application.
Response to Amendment
In the response filed 02/06/2025, the claims were amended.
These amendments are hereby entered.
In light of Applicant’s amendments to the claims, the rejection under 35 U.S.C. 103 of claims 1, 3-10, and 12-22 as being unpatentable over Nakamura et al. (US 2019/0157599 A1), claim is withdrawn by the Office.
Response to Arguments
Applicant’s arguments have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 1, 3-10, and 12-22 are rejected under 35 U.S.C. 103 as being unpatentable over Boudreault et al. (US 2015/0236276 A1) in view of Kwong et al. (US 2004/0214038 A1).
With respect to claim 1, Boudreault teaches Compound 6858 (page 80) which is a compound of Formula (LA)2Ir(LB)1 wherein LA is instant ligand LA138 and LB is instant ligand LB43, which are pictured below to facilitate discussion.
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This compound meets the requirements of conditions (i)-(iv) of the instant claim when M is Ir, x is 2, y is 0, and z is 1, X1 is carbon, X2 is nitrogen, X3 and X4 are carbon, and X5 is not present, ring A is a 5-membered aromatic ring fused to the ring having X1, rings C and D are not present, two of R3 are joined into a fused ring, R4 represents no substitution, RC and RD are not present, RY is hydrogen, and RX and RZ are an alkyl (3-pentyl) group.
However, Boudreault differs from the claimed invention in that, while Boudreault does teach that R1, which is analogous to instant R1 and R2, may be independently selected as any alkyl group (paragraph 0064), Boudreault does not teach that R1 and R2 must be different and that R2 has more carbon atoms than R1.
Kwong teaches organic light emitting devices comprising an array of pixels having reduced pixel shrinkage (abstract).
Kwong teaches that unsubstituted phenylpyridine ligands are too labile and suffer from pixel shrinkage. However, when phenylpyridine ligands have substituents selected to increase the steric bulkiness and/or the molecular weight of the ligand, the ligand is less likely to undergo the associative type of substitution (SN2) because the associative type of substitution requires the complex to re-orient to adopt a geometry favorable for the attack by the external agent, but sufficient steric bulkiness makes it more difficult for the ligand to move and adopt such a geometry (paragraph 0081, lines 6-25).
Kwong teaches that iridium complexes can be given the appropriate steric bulk to prevent pixel shrinkage through substitution at a position equivalent to instant R1 and R2 (See R1-R4 and formula Ia -on page 10) with a C1-C20 alkyl group (paragraphs 0091 and 0095).
Kwong does not specifically teach the steric substituent should comprise an alkyl group with 4 or more carbon atoms, however, Kwong does teach that a ligand is less likely to undergo the associative type of substitution when it has a substituent with sufficient steric bulkiness to make it difficult for the ligand to reorient. A person of ordinary skill in the art would know which chemical moieties are comprised by the term “steric group” and be able to determine when “sufficient” steric bulk had been achieved to suppress molecular reorientation and associative substitution. A person of ordinary skill in the art would have also pursued known potential steric groups, guided by the teaching of a steric alkyl group by Kwong, and arrive at a steric alkyl group of 4 or more carbon atoms, such as t-butyl with a reasonable expectation of success for achieving the suppressed molecular reorientation and associative type substitution taught by Kwong as a result of the steric substituent. See MPEP 2143(E)
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to incorporate one steric C4-C20 alkyl substituent, such as t-butyl, in the compound of Boudreault at either position R1 and R2 as Kwong teaches that using a bulky substituent leads to a ligand which is less likely to undergo the associative type of substitution.
With respect to claim 3, Boudreault and Kwong teach the compound of claim 1, and the compound has the formula Ir(LA)2(LC), as discussed above.
With respect to claim 4, Boudreault and Kwong teach the compound of claim 1, and X2 is nitrogen, as discussed above.
With respect to claim 5, Boudreault and Kwong teach the compound of claim 1, and ring A is a 5-membered heteroaromatic ring, as pictured above.
With respect to claim 6, Boudreault and Kwong teach the compound of claim 1, and R1 and R2 are each independently selected as methyl and t-butyl, as discussed above.
With respect to claim 7, Boudreault and Kwong teach the compound of claim 1, and R2, t-butyl, has at least three more carbon atoms than R1, which is methyl, as discussed above.
With respect to claim 8, Boudreault and Kwong teach the compound of claim 1, and two R3 are joined to form a fused ring, as discussed above.
With respect to claim 9, Boudreault and Kwong teach the compound of claim 1, and rings C and D are not present because y is 0, as discussed above.
With respect to claim 10, Boudreault and Kwong teach the compound of claim 1, and LA is selected as the fourteenth embodiment of the claim, which is pictured below.
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With respect to claim 12, Boudreault and Kwong teach the compound of claim 1, as discussed above.
Boudreault also teaches the ancillary ligand may be phenylpyridine (paragraph 0135) which is pictured below.
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This ligand meets the requirements of the instant claim when instant X1-X8 are carbon atoms and Ra and Rb represent no substitution.
With respect to claim 13, Boudreault and Kwong teach the compound of claim 1, and z is 1 and LC is instant LC5, as pictured above.
Claim 14 is discussed below claim 21.
With respect to claim 15, Boudreault discloses an organic light emitting device (OLED) comprising an anode, a cathode, and an organic layer between the electrodes comprising a compound comprising a ligand LA of formula I (paragraphs 0144-0147) such as Compound 6858 (page 80) which is a compound of Formula (LA)2Ir(LB)1 wherein LA is instant ligand LA138 and LB is instant ligand LB43, which are pictured below to facilitate discussion.
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This compound meets the requirements of conditions (i)-(iv) of the instant claim when M is Ir, x is 2, y is 0, and z is 1, X1 is carbon, X2 is nitrogen, X3 and X4 are carbon, and X5 is not present, ring A is a 5-membered aromatic ring fused to the ring having X1, rings C and D are not present, two of R3 are joined into a fused ring, R4 represents no substitution, RC and RD are not present, RY is hydrogen, and RX and RZ are an alkyl (3-pentyl) group.
However, Boudreault differs from the claimed invention in that, while Boudreault does teach that R1, which is analogous to instant R1 and R2, may be independently selected as any alkyl group (paragraph 0064), Boudreault does not teach that R1 and R2 must be different and that R2 has more carbon atoms than R1.
Kwong teaches organic light emitting devices comprising an array of pixels having reduced pixel shrinkage (abstract).
Kwong teaches that unsubstituted phenylpyridine ligands are too labile and suffer from pixel shrinkage. However, when phenylpyridine ligands have substituents selected to increase the steric bulkiness and/or the molecular weight of the ligand, the ligand is less likely to undergo the associative type of substitution (SN2) because the associative type of substitution requires the complex to re-orient to adopt a geometry favorable for the attack by the external agent, but sufficient steric bulkiness makes it more difficult for the ligand to move and adopt such a geometry (paragraph 0081, lines 6-25).
Kwong teaches that iridium complexes can be given the appropriate steric bulk to prevent pixel shrinkage through substitution at a position equivalent to instant R1 and R2 (See R1-R4 and formula Ia -on page 10) with a C1-C20 alkyl group (paragraphs 0091 and 0095).
Kwong does not specifically teach the steric substituent should comprise an alkyl group with 4 or more carbon atoms, however, Kwong does teach that a ligand is less likely to undergo the associative type of substitution when it has a substituent with sufficient steric bulkiness to make it difficult for the ligand to reorient. A person of ordinary skill in the art would know which chemical moieties are comprised by the term “steric group” and be able to determine when “sufficient” steric bulk had been achieved to suppress molecular reorientation and associative substitution. A person of ordinary skill in the art would have also pursued known potential steric groups, guided by the teaching of a steric alkyl group by Kwong, and arrive at a steric alkyl group of 4 or more carbon atoms, such as t-butyl with a reasonable expectation of success for achieving the suppressed molecular reorientation and associative type substitution taught by Kwong as a result of the steric substituent. See MPEP 2143(E)
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to incorporate one steric C4-C20 alkyl substituent, such as t-butyl, in the compound of Boudreault at either position R1 and R2 as Kwong teaches that using a bulky substituent leads to a ligand which is less likely to undergo the associative type of substitution.
With respect to claim 16, Boudreault and Kwong teach the OLED of claim 15, and Boudreault teaches the layer is an emissive layer and the compound is an emissive dopant (paragraph 0153).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the compound in the emissive layer as an emissive dopant, as taught by Boudreault.
With respect to claims 17 and 18, Boudreault and Kwong teach the OLED of claim 15, and Boudreault also teaches that the organic layer comprises a host compound such as the carbazole derivative pictured below (page 87)
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It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the claimed invention to use the host material above as a host material for the compound of Boudreault and Kwong, as taught by Boudreault.
With respect to claim 19, Boudreault teaches a consumer product (paragraph 0154) comprising an organic light emitting device (OLED) comprising an anode, a cathode, and an organic layer between the electrodes comprising a compound comprising a ligand LA of formula I (paragraphs 0144-0147) such as Compound 6858 (page 80) which is a compound of Formula (LA)2Ir(LB)1 wherein LA is instant ligand LA138 and LB is instant ligand LB43, which are pictured below to facilitate discussion.
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This compound meets the requirements of conditions (i)-(iv) of the instant claim when M is Ir, x is 2, y is 0, and z is 1, X1 is carbon, X2 is nitrogen, X3 and X4 are carbon, and X5 is not present, ring A is a 5-membered aromatic ring fused to the ring having X1, rings C and D are not present, two of R3 are joined into a fused ring, R4 represents no substitution, RC and RD are not present, RY is hydrogen, and RX and RZ are an alkyl (3-pentyl) group.
However, Boudreault differs from the claimed invention in that, while Boudreault does teach that R1, which is analogous to instant R1 and R2, may be independently selected as any alkyl group (paragraph 0064), Boudreault does not teach that R1 and R2 must be different and that R2 has more carbon atoms than R1.
Kwong teaches organic light emitting devices comprising an array of pixels having reduced pixel shrinkage (abstract).
Kwong teaches that unsubstituted phenylpyridine ligands are too labile and suffer from pixel shrinkage. However, when phenylpyridine ligands have substituents selected to increase the steric bulkiness and/or the molecular weight of the ligand, the ligand is less likely to undergo the associative type of substitution (SN2) because the associative type of substitution requires the complex to re-orient to adopt a geometry favorable for the attack by the external agent, but sufficient steric bulkiness makes it more difficult for the ligand to move and adopt such a geometry (paragraph 0081, lines 6-25).
Kwong teaches that iridium complexes can be given the appropriate steric bulk to prevent pixel shrinkage through substitution at a position equivalent to instant R1 and R2 (See R1-R4 and formula Ia -on page 10) with a C1-C20 alkyl group (paragraphs 0091 and 0095).
Kwong does not specifically teach the steric substituent should comprise an alkyl group with 4 or more carbon atoms, however, Kwong does teach that a ligand is less likely to undergo the associative type of substitution when it has a substituent with sufficient steric bulkiness to make it difficult for the ligand to reorient. A person of ordinary skill in the art would know which chemical moieties are comprised by the term “steric group” and be able to determine when “sufficient” steric bulk had been achieved to suppress molecular reorientation and associative substitution. A person of ordinary skill in the art would have also pursued known potential steric groups, guided by the teaching of a steric alkyl group by Kwong, and arrive at a steric alkyl group of 4 or more carbon atoms, such as t-butyl with a reasonable expectation of success for achieving the suppressed molecular reorientation and associative type substitution taught by Kwong as a result of the steric substituent. See MPEP 2143(E)
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the instant invention to incorporate one steric C4-C20 alkyl substituent, such as t-butyl, in the compound of Boudreault at either position R1 and R2 as Kwong teaches that using a bulky substituent leads to a ligand which is less likely to undergo the associative type of substitution.
With respect to claim 20, Boudreault and Kwong teach the consumer product of claim 19, and Boudreault teaches that the consumer product may be a flat panel display (paragraph 0095).
With respect to claim 21, Boudreault and Kwong teach the compound of claim 1, and the ligand LA is selected as instant ligand LA2204 wherein R1 is methyl, R2 is t-butyl, and R4 and R5 are hydrogen atoms.
With respect to claim 14, Boudreault and Kwong teach the compound of claim 21, and the compound is Compound 37,456 which has the formula Ir(LA2204)(LC5).
With respect to claim 22, Boudreault and Kwong teach the compound of claim 1, and z is 1, RY is hydrogen, and RX and RZ are not selected from methyl or t-butyl, as discussed above.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL SIMBANA whose telephone number is (571)272-2657. The examiner can normally be reached Monday - Friday, 8:00 A.M. - 4:30 P.M..
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/RACHEL SIMBANA/Examiner, Art Unit 1786