ORGANIC ELECTROLUMINESCENT MATERIALS AND DEVICES

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 All outstanding objections and rejections, except for those maintained below, are withdrawn in light of applicant's amendment filed on 8/31/2026. The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior office action. Claim Objections Claim 1 is objected to because of the following informalities: Claim 1 recites the phrase “at least one of R1, R2, RA, RB, RC, RD, and RE”. Applicants are advised to amend this phrase to recite “at least one of R1, R2, RA, RB, RC, RD, or RE”, Appropriate correction is required. Claim 17 is objected to because of the following informalities: Claim 17 recites the phrase “at least one of R1, R2, RA, RB, RC, RD, and RE”. Applicants are advised to amend this phrase to recite “at least one of R1, R2, RA, RB, RC, RD, or RE”, Appropriate correction is required. Claim 20 is objected to because of the following informalities: Claim 20 recites the phrase “at least one of R1, R2, RA, RB, RC, RD, and RE”. Applicants are advised to amend this phrase to recite “at least one of R1, R2, RA, RB, RC, RD, or RE”, Appropriate correction is required. 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 1-3, 5-6, 8-15, 17, 20, and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Bae et al (US 2022/0106345, cited on IDS filed on 4/7/2026). Regarding claim 1, Bae et al discloses the following compound (Page 118 – Compound 416): PNG media_image1.png 585 516 media_image1.png Greyscale . This compound corresponds to the compound represented by formula I: PNG media_image2.png 344 330 media_image2.png Greyscale , where: ring B is a 6-membered carbocyclic ring; ring D is a 6-membered heterocyclic ring; Z1 is C; Z2 is C; Z3 is N; L1 is O; L2 is a direct bond; One (1) RD corresponds to R**, where R* is represented by Formula IV: PNG media_image3.png 152 252 media_image3.png Greyscale . Two (2) groups RA are alkenyl groups that join to form a ring; RB is hydrogen; RC is hydrogen; RD is a deuterium substituted alkyl; R1 and R2 are hydrogen; RE represents two (2) tert-butyl alkyl substituents, i.e. alkyls; RH represents deuterium and alkyl substituents; X1 to X5, X8 to X16 are C; and X6 is N. As discussed above, the substituent: PNG media_image4.png 196 188 media_image4.png Greyscale , corresponds to Formula IV: PNG media_image3.png 152 252 media_image3.png Greyscale , where four (4) RH substituents correspond to deuterium and one (1) RH substituent is an alkyl, thereby satisfying proviso (a) of the claims, i.e. where R* is Formula IV, at least one RH is a substituent that is not hydrogen or deuterium, and at least one RH is deuterium. In the compound disclosed by the reference R* corresponds to Formula IV and R1 and R2 are both hydrogen, and therefore, the compound cannot meet provision (C) of the claims, i.e. both R1 and R2 are not H or D. However, it is noted that in the disclosed formula ([0081] – Formula 1-1A): PNG media_image5.png 476 506 media_image5.png Greyscale , K1 can be an integer from 1 to 5 ([0085]) and E1 can be a C1-10 alkyl ([0028]). Thus, for k1 equal to three (3) R1 and R2 in Formula I of the claims can be a C1-60 alkyl, thereby, satisfying condition (C) of the present claims. Furthermore, the compound satisfies provision (i) of the claims, i.e. neither R1 nor R2 is hydrogen and R* comprises at least five (5) carbon atoms. 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, Bae et al teaches all the claim limitations as set forth above. As discussed above, two (2) substituents RA are alkenyl groups that join to form a ring. RB is hydrogen; RC is hydrogen; RD is a deuterium substituted alkyl. R1 and R2 are alkyl groups. RE represents two (2) tert-butyl alkyl substituents. RH represents deuterium and alkyl substituents. Regarding claim 3, Bae et al teaches all the claim limitations as set forth above. From the discussion above, the compound disclosed by the reference does not correspond to Formula IA of the claims: PNG media_image6.png 334 298 media_image6.png Greyscale , i.e. the compound possesses a benzimidazole group and not an imidazole group as required by the claim. However, the reference discloses the following general formula for the compound ([0081] - Formula I-1A): PNG media_image7.png 340 370 media_image7.png Greyscale , ring A20 can be a C5-30 carbocyclic ring ([0019]). This ring is exemplified in a benzene ring in Compounds 299 and 300 (Page 98): PNG media_image8.png 208 228 media_image8.png Greyscale PNG media_image9.png 240 250 media_image9.png Greyscale . Ring A10 can be ([0064] and Page 4 – A10-1): PNG media_image10.png 130 150 media_image10.png Greyscale . Accordingly, the disclosure of the reference encompasses the formula recited in the present claim. Regarding claim 5, Bae et al teaches all the claim limitations as set forth above. In the compound disclosed by the reference: PNG media_image1.png 585 516 media_image1.png Greyscale , L2 is a direct bond and not BR, NR, PR or CR as required by the present claim. However, the reference discloses the following general formula for the compound ([0081] – Formula I-1A): PNG media_image7.png 340 370 media_image7.png Greyscale , where T2 can be B(R3), where R3 is hydrogen ([0021] and [0029]). Accordingly, the disclosure of the reference encompasses an embodiment where L2 in Formula I is BR, where R is hydrogen. Regarding claim 6, Bae et al teaches all the claim limitations as set forth above. In the compound disclosed by the reference: PNG media_image1.png 585 516 media_image1.png Greyscale , R1 or R2 does not comprise the group R* as required by the present claims. However, the reference discloses the following general formula for the compound ([0081] - Formula I-1A): PNG media_image7.png 340 370 media_image7.png Greyscale , where E1 can be Si(Q3)(Q4)(Q5), where Q3 is deuterium ([0042]), and Q3 and Q4 are C1-60 alkyl groups ([0042]). That is, E1 corresponds R1 or R2, where R1 or R2 is represented by Formula II: PNG media_image11.png 34 160 media_image11.png Greyscale , where Q is Si, R3 is deuterium, and R4 and R5 are alkyl groups. Regarding claim 8, Bae et al teaches all the claim limitations as set forth above. From the discussion above, the reference discloses the compound: PNG media_image12.png 212 224 media_image12.png Greyscale . Regarding claim 9, Bae et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that E1 can be N(Q1)(Q2), where Q1 and Q2 are -CD3 ([0144]-[0146]), corresponding to: PNG media_image13.png 72 92 media_image13.png Greyscale , of the claims. Regarding claim 10, Bae et al teaches all the claim limitations as set forth above. From the discussion above, X6 is N and not C, and therefore X1 to X16 are all C as required by the present claim. However, the reference discloses the following general formula for the compound ([0081] - Formula I-1A): PNG media_image7.png 340 370 media_image7.png Greyscale , ring A20 can be a C5-30 carbocyclic ring ([0019]). This ring is exemplified in a benzene ring in Compounds 299 and 300 (Page 98): PNG media_image8.png 208 228 media_image8.png Greyscale PNG media_image9.png 240 250 media_image9.png Greyscale . Regarding claim 11, Bae et al teaches all the claim limitations as set forth above. As discussed above, X6 is N. Regarding claim 12, Bae et al teaches all the claim limitations as set forth above. From the discussion above, X4’ to X7’ are C. Regarding claim 13, Bae et al teaches all the claim limitations as set forth above. From the discussion above, X15’’ is not N as required by the present claims. However, the reference discloses the following general formula for the compound ([0081] - Formula I-1A): PNG media_image7.png 340 370 media_image7.png Greyscale , where ring A10 can be ([0064] and Page 5 – A10-19) PNG media_image14.png 112 174 media_image14.png Greyscale , i.e. X15’’ is N. Regarding claim 14, Bae et al teaches all the claim limitations as set forth above. Additionally, it is noted that in the general formula ([0081] - Formula I-1A): PNG media_image7.png 340 370 media_image7.png Greyscale , E2 can be H and R40 can be H. E1 can be N(Q1)(Q2), where Q1 and Q2 are -CD3 ([0144]-[0146]), corresponding to: PNG media_image13.png 72 92 media_image13.png Greyscale , of the claims. Accordingly, the reference discloses a compound with the formula: PNG media_image15.png 326 368 media_image15.png Greyscale , where LA’ corresponds to: PNG media_image16.png 282 258 media_image16.png Greyscale , where R1, RA, and RB are H; and R2 is PNG media_image13.png 72 92 media_image13.png Greyscale . Ligand Ly is: PNG media_image17.png 144 132 media_image17.png Greyscale , where RF is: PNG media_image18.png 72 44 media_image18.png Greyscale ; and RE is H. Regarding claim 15, Bae et al teaches all the claim limitations as set forth above. Additionally, it is noted that in the general formula ([0081] - Formula I-1A): PNG media_image7.png 340 370 media_image7.png Greyscale , E2 can be H and R40 can be H. E1 can be N(Q1)(Q2), where Q1 and Q2 are -CD3 ([0144]-[0146]), corresponding to: PNG media_image13.png 72 92 media_image13.png Greyscale , of the claims. Accordingly, the reference discloses a compound with the formula: PNG media_image15.png 326 368 media_image15.png Greyscale , where LA’ corresponds to: PNG media_image19.png 152 146 media_image19.png Greyscale , where RW and RV are H (recited as R1); and RU is PNG media_image13.png 72 92 media_image13.png Greyscale (recited as R178). Ligand Ly-28 is: , PNG media_image20.png 175 182 media_image20.png Greyscale where Rr is: PNG media_image18.png 72 44 media_image18.png Greyscale i.e. recited as R10; and Rs and Rt’ are H (recited as R1). Regarding claim 24, Bae et al teaches all the claim limitations as set forth above. As discussed above, R* is represented by Formula IV: PNG media_image3.png 152 252 media_image3.png Greyscale ., and R1 and R2 in Formula I of the claims can be a C1-60 alkyl, i.e. R1 and R2 are not H or D. Regarding claim 17, Bae et al discloses an organic light emitting device comprising first and second electrodes, i.e. an anode and a cathode ([0043]), and an organic layer disposed between the electrode ([0043]). The organic layer comprising the following compound ([0043] and Page 118 – Compound 416): PNG media_image1.png 585 516 media_image1.png Greyscale . This compound corresponds to the compound represented by formula I: PNG media_image2.png 344 330 media_image2.png Greyscale , where: ring B is a 6-membered carbocyclic ring; ring D is a 6-membered heterocyclic ring; Z1 is C; Z2 is C; Z3 is N; L1 is O; L2 is a direct bond; One (1) RD corresponds to R**, where R* is represented by Formula IV: PNG media_image3.png 152 252 media_image3.png Greyscale . Two (2) groups RA are alkenyl groups that join to form a ring; RB is hydrogen; RC is hydrogen; RD is a deuterium substituted alkyl; R1 and R2 are hydrogen; RE represents two (2) tert-butyl alkyl substituents, i.e. alkyls; RH represents deuterium and alkyl substituents; X1 to X5, X8 to X16 are C; and X6 is N. As discussed above, the substituent: PNG media_image4.png 196 188 media_image4.png Greyscale , corresponds to Formula IV: PNG media_image3.png 152 252 media_image3.png Greyscale , where four (4) RH substituents correspond to deuterium and one (1) RH substituent is an alkyl, thereby satisfying proviso (a) of the claims, i.e. where R* is Formula IV, at least one RH is a substituent that is not hydrogen or deuterium, and at least one RH is deuterium. In the compound disclosed by the reference R* corresponds to Formula IV and R1 and R2 are both hydrogen, and therefore, the compound cannot meet provision (C) of the claims, i.e. both R1 and R2 are not H or D. However, it is noted that in the disclosed formula ([0081] – Formula 1-1A): PNG media_image5.png 476 506 media_image5.png Greyscale , K1 can be an integer from 1 to 5 ([0085]) and E1 can be a C1-10 alkyl ([0028]). Thus, for k1 equal to three (3) R1 and R2 in Formula I of the claims can be a C1-60 alkyl, thereby, satisfying condition (C) of the present claims. Furthermore, the compound satisfies provision (i) of the claims, i.e. neither R1 nor R2 is hydrogen and R* comprises at least five (5) carbon atoms. 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, Bae et al discloses an organic light emitting device, i.e. a consumer product, comprising first and second electrodes, i.e. an anode and a cathode ([0043]), and an organic layer disposed between the electrode ([0043]). The organic layer comprising the following compound ([0043] and Page 118 – Compound 416): PNG media_image1.png 585 516 media_image1.png Greyscale . This compound corresponds to the compound represented by formula I: PNG media_image2.png 344 330 media_image2.png Greyscale , where: ring B is a 6-membered carbocyclic ring; ring D is a 6-membered heterocyclic ring; Z1 is C; Z2 is C; Z3 is N; L1 is O; L2 is a direct bond; One (1) RD corresponds to R**, where R* is represented by Formula IV: PNG media_image3.png 152 252 media_image3.png Greyscale . Two (2) groups RA are alkenyl groups that join to form a ring; RB is hydrogen; RC is hydrogen; RD is a deuterium substituted alkyl; R1 and R2 are hydrogen; RE represents two (2) tert-butyl alkyl substituents, i.e. alkyls; RH represents deuterium and alkyl substituents; X1 to X5, X8 to X16 are C; and X6 is N. As discussed above, the substituent: PNG media_image4.png 196 188 media_image4.png Greyscale , corresponds to Formula IV: PNG media_image3.png 152 252 media_image3.png Greyscale , where four (4) RH substituents correspond to deuterium and one (1) RH substituent is an alkyl, thereby satisfying proviso (a) of the claims, i.e. where R* is Formula IV, at least one RH is a substituent that is not hydrogen or deuterium, and at least one RH is deuterium. In the compound disclosed by the reference R* corresponds to Formula IV and R1 and R2 are both hydrogen, and therefore, the compound cannot meet provision (C) of the claims, i.e. both R1 and R2 are not H or D. However, it is noted that in the disclosed formula ([0081] – Formula 1-1A): PNG media_image5.png 476 506 media_image5.png Greyscale , K1 can be an integer from 1 to 5 ([0085]) and E1 can be a C1-10 alkyl ([0028]). Thus, for k1 equal to three (3) R1 and R2 in Formula I of the claims can be a C1-60 alkyl, thereby, satisfying condition (C) of the present claims. Furthermore, the compound satisfies provision (i) of the claims, i.e. neither R1 nor R2 is hydrogen and R* comprises at least five (5) carbon atoms. 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. Allowable Subject Matter Claims 16 and 21-23 are 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. If rewritten as indicated above, claims 16 and 21-23 would be allowable over the “closest” prior art Bae et al for the following reasons. Bae et al discloses compound such as (Page 118 – Compound 416): PNG media_image1.png 585 516 media_image1.png Greyscale , which possesses two (2) substituted phenyl rings. However, the compounds in claim 16 only possess a single substituted phenyl ring present on the benzimidazole. Accordingly, the reference does not disclose or suggest the compounds recited in claim 16. Furthermore, given that the reference requires two (2) phenyl groups to be present, the reference does not disclose or suggest that RD is not a substituted or unsubstituted phenyl as required by claim 22 or that at least one of X1 to X3 is N as required by claim 23. Finally, the reference does not disclose or suggest a substituent corresponding to Formula III as required by claim 21. Response to Arguments Applicant's arguments filed 8/31/2026 have been fully considered but they are not persuasive. In light of amendments to the claims, the claim objections and statutory double patenting rejections set forth in the previous Office Action are withdrawn. In light of the Applicants’ persuasive arguments, the 35 U.S.C. 112 (b) rejections set forth in the previous Office Action are withdrawn. Finally, in light of the properly filed terminal disclaimer, filed on 8/31/2024, the obviousness-type double patenting rejections set forth in the previous Office Action are withdrawn. Applicants argue that Bae et al does not disclose the compound recited in the as-amended claims. However, as discussed in the rejections above the reference discloses the formula ([0081] – Formula 1-1A): PNG media_image5.png 476 506 media_image5.png Greyscale , K1 can be an integer from 1 to 5 ([0085]) and E1 can be a C1-10 alkyl ([0028]). Thus, for k1 equal to three (3) R1 and R2 in Formula I of the claims can be a C1-60 alkyl, thereby, satisfying condition (C) of the present claims. Conclusion 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. Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /ALEXANDER C KOLLIAS/Primary Examiner, Art Unit 1786