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All outstanding objections and rejections, except for those maintained below, are withdrawn in light of applicant's amendment filed on 9/26/2025.
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 9/26/2025. In particular, the scope of original claim 1 has a been narrowed and newly added claims 37-40 recite subject matter not previously presented. Thus, the following action is properly made final.
Note: Claim 27 has the status identifier “Currently Amended”, however, the claim has not been marked up indicating any insertions or deletions and recites the identical subject matter recited in the previous Amendments filed on 2/7/2025. Accordingly, the status identifier for claim 27 is improper and the correct status identifier should be “Previously Presented”.
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, 7, 9-10, 12-23, and 27-31, 33-40 are rejected under 35 U.S.C. 103 as being unpatentable over Hatakeyama et al (US 2021/0167288).
Regarding claim 1, Hatakeyama et al discloses the following compound (Page 88 – Compound 2-2625):
.
PNG
media_image1.png
286
516
media_image1.png
Greyscale
This compound corresponds to the compound represented by Formula (IA):
PNG
media_image2.png
379
516
media_image2.png
Greyscale
where R5 to R8, R12 to R19, and R37 to R41 are H; and Rb is a phenyl group, i.e. an unsubstituted C6 aryl.
The compound of the reference does not comprise an aryl amine group and R10 is not a C1-20 alkyl group as required by the present claims. However, the compound disclosed by the reference is but one embodiment and attention is directed to Formula (2’) ([0089]):
PNG
media_image3.png
330
398
media_image3.png
Greyscale
,
where R1 to R11 can be a diarylamino group ([0095]). This diarylamino group is exemplified as (Page 49 – Compounds 2-52 and 2-53):
PNG
media_image4.png
252
277
media_image4.png
Greyscale
PNG
media_image5.png
256
292
media_image5.png
Greyscale
.
The above compounds exemplify the claimed arylamine substituent where R27 to R36 are H. In Formula (2’) R2 can be a C1-4 alkyl ([0095] and [0113]). Accordingly, the disclosure of the reference encompasses an embodiment where R10 in recited Formula (IA) is an unsubstituted C1-4 alkyl.
Furthermore, in the compound disclosed by the reference Ra is hydrogen and not a phenyl group are required by the present claims. However, it is noted that in Formula (2’) the substituent R, in N-R for X1, can be a an optionally substituted aryl, i.e. an aryl substituted with a least one secondary substituent such a phenyl group ([0092], [0119], and [0117]). Accordingly, the disclosure of the reference encompasses an embodiment where Ra is a phenyl group.
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 7, Hatakeyama et al teaches all the claim limitations as set forth above. The claim recites that at most 4 of R1 to R8 are an optionally substituted aryl, an optionally substituted heteroaryl, etc. The claim encompasses an embodiment where none of R1 to R8 are an optionally substituted aryl, an optionally substituted heteroaryl, etc., and therefore, the claim does not require that any of R1 to R8 are one of the recited substituents.
Regarding claim 9, Hatakeyama et al teaches all the claim limitations as set forth above. From the discussion above, the reference discloses compounds encompassed by Formula (IAa):
PNG
media_image6.png
398
562
media_image6.png
Greyscale
where R27, R28, R29, etc. are hydrogen.
Regarding claim 10, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that at least one (1) hydrogen in the compound represented by Formula (2’) can be substituted with a deuterium atom ([0097]).
Regarding claim 12, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that at least one (1) hydrogen in the compound represented by Formula (2’) can be substituted with a deuterium atom ([0097]). Furthermore, the reference exemplified a diarylamino group, where phenyl groups corresponding Ar2 and Ar3 are fully deuterated, e.g. Compound 2-2714 (Page 100):
PNG
media_image7.png
317
356
media_image7.png
Greyscale
.
Accordingly, all of R27 to R36 are deuterium atoms.
Regarding claim 13, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that at least one (1) hydrogen in the compound represented by Formula (2’) can be substituted with a deuterium atom ([0097]). Furthermore, the reference exemplified a diarylamino group, where phenyl groups corresponding Ar2 and Ar3 are fully deuterated, e.g. Compound 2-2714 (Page 100):
PNG
media_image7.png
317
356
media_image7.png
Greyscale
.
Accordingly, all of R27 to R36 are deuterium atoms.
Regarding claim 14, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that the compound is utilized as material for a light emitting layer in an organic light emitting device ([0088] and [0001]). Accordingly, the reference discloses a material suitable for an organic electroluminescent device as recited in the present claims.
Regarding claim 15, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that the compound is utilized as material for a light emitting layer in an organic light emitting device ([0088] and [0001]). Accordingly, the reference discloses an organic electroluminescent device as recited in the present claims.
Regarding claim 16, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses the following organic electroluminescent device (Figure 1):
(Figure 1):
PNG
media_image8.png
353
587
media_image8.png
Greyscale
,
where layer 102 corresponds to the recited anode; layer 108 corresponds to the recited cathode electrode; layers 103 to 107 correspond to the recited thing film organic layers; and layer 105 corresponds to the recited light emitting layer ([0173]). The light emitting layer comprises the disclosed compound ([0088]).
Regarding claim 17, Hatakeyama et al teaches all the claim limitations as set forth above. As discussed above, the light emitting layer comprises the disclosed compound.
Regarding claim 18, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that the light emitting layer comprises a host compound, i.e. a compound represented by Formula (1), and a dopant, where the dopant is the compound discussed above ([0190]).
Regarding claim 19, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that the host compound is a fused ring derivative of anthracene ([0194]).
Regarding claim 20, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that the anthracene host compound has the formula ([0195]):
PNG
media_image9.png
238
210
media_image9.png
Greyscale
where L2 and L3 are benzene rings ([0197]). Accordingly, the reference discloses a compound represented by Formula (10):
PNG
media_image10.png
220
184
media_image10.png
Greyscale
,
where R101 to R108 are H; and R109 and R110 are phenyl groups. Thus, R109 and R110 correspond to -L101-Ar101,
where L101 is a single bond and Ar101 is a phenyl group, i.e. an aryl comprising six (6) carbon atoms.
Regarding claim 21, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses a display apparatus comprising the disclosed organic electroluminescent device ([0037]).
Regarding claim 22, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses a light emitting layer comprises a host compound, i.e. a compound represented by Formula (1), and a dopant, where the dopant is the compound discussed above ([0190]).
Regarding claim 23, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses a method of forming an organic light emitting device utilizing the disclosed compound ([0399]-[0402]).
Regarding claim 27, Hatakeyama et al teaches all the claim limitations as set forth above. As discussed above, R10 is an unsubstituted C1-4 alkyl group. The R1 to R8 that do not correspond to recited arylamine are H and R12 to R19 are H. As discussed above, Rb is H, and therefore, not an aryl group as recited in the present claims. However, the reference discloses that at least one (1) hydrogen in the aryl group in R-N can be substituted with an alkyl such as methyl ([0119] and [0113]-[0114]). Accordingly, the reference discloses that Rb is an alkyl group as recited in the present claims.
Regarding claim 28, Hatakeyama et al teaches all the claim limitations as set forth above. From the discussion above, the reference discloses a compound represented by Formula (IA):
PNG
media_image11.png
315
427
media_image11.png
Greyscale
,
where R5, R6, R7, and R8 are H; R10 is an unsubstituted C1-4 alkyl; R37 to R41 are H; and R12 to R19 are H. Ra and Rb are not alkyl groups as recited in the present claims. However, the reference discloses that at least one (1) hydrogen in the aryl group in R-N can be substituted with an alkyl such as methyl ([0119] and [0113]-[0114]). Accordingly, the disclosure of the reference encompasses an embodiment where Ra and Rb are both methyl groups.
Regarding claim 29, Hatakeyama et al teaches all the claim limitations as set forth above. From the discussion above, R5, R6, R7, and R8 are H; R10 is an unsubstituted C1-4 alkyl; R37 to R41 are H; and R12 to R19 are H. Ra and Rb are not alkyl groups as recited in the present claims. However, the reference discloses that at least one (1) hydrogen in the aryl group in R-N can be substituted with an alkyl such as methyl ([0119] and [0113]-[0114]). Accordingly, the disclosure of the reference encompasses an embodiment where Ra and Rb are both methyl groups.
Regarding claim 30, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, it is noted that nothing within the scope of the reference prohibits the diarylamino group from being present only at R7 in Formula (1) of the claims. Accordingly, the reference discloses a compound encompassed by Formula (1B):
PNG
media_image12.png
407
476
media_image12.png
Greyscale
where R1 to R4 and R10 are H; R37 to R41 are H; and R12 to R19 are H. Ra and Rb are not alkyl groups as recited in the present claims. However, the reference discloses that at least one (1) hydrogen in the aryl group in R-N can be substituted with an alkyl such as methyl ([0119] and [0113]-[0114]). Accordingly, the disclosure of the reference encompasses an embodiment where Ra and Rb are both methyl groups.
Regarding claim 31, Hatakeyama et al teaches all the claim limitations as set forth above. As discussed above, the reference discloses a compound corresponding to Formula (1A).
Regarding claim 33, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that in Formula (2) at least one hydrogen can be replaced by deuterium ([0093]). Accordingly, the disclosure of the reference encompasses an embodiment where one of R27 to R36 is deuterium.
Regarding claim 34, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that in Formula (2) at least one hydrogen can be replaced by deuterium ([0093]). Accordingly, the disclosure of the reference encompasses an embodiment where one of R27 to R36 is deuterium.
Regarding claim 35, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that in Formula (2) at least one hydrogen can be replaced by deuterium ([0093]). Accordingly, the disclosure of the reference encompasses an embodiment where one of R27 to R36 is deuterium.
Regarding claim 36, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that in Formula (2) at least one hydrogen can be replaced by deuterium ([0093]). Accordingly, the disclosure of the reference encompasses an embodiment where R27 to R36 are deuterium.
Regarding claim 37, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that the light emitting layer can comprise the following anthracene compound ([0191] and [0195]):
PNG
media_image13.png
184
142
media_image13.png
Greyscale
,
where L2 and L3 are naphthyl groups ([0197]). Accordingly, the reference discloses that the host is a substituted fused hydrocarbon compound.
Regarding claim 38, Hatakeyama et al teaches all the claim limitations as set forth above. Additionally, the reference discloses that the light emitting layer can comprise a plurality of dopants ([0191]) such as an anthracene type compound and a carbazole type compound ([0195]), i.e.
PNG
media_image14.png
188
368
media_image14.png
Greyscale
,
where L1 to L3 are naphthyl groups ([0106]-[0197]). Accordingly, the reference discloses that the host compound comprises an optionally substituted fused aromatic hydrocarbon atom, i.e. a naphthyl group or fused aromatic hydrocarbon compound substituted with carbazole groups and an anthracene compound substituted with naphthyl groups.
Regarding claim 39, Hatakeyama et al teaches all the claim limitations as set forth above. As discussed above, the reference discloses R10 in recited Formula (IA) is an unsubstituted C1-4 alkyl. Accordingly, the disclosure of the reference encompasses an embodiment where R10 is a methyl group.
Regarding claim 40, Hatakeyama et al discloses a compound with the following formula ([0089] – Formula 2):
PNG
media_image15.png
272
322
media_image15.png
Greyscale
,
where R2 and R9 are alkyl groups such as t-butyl ([0095] and [0113]-[0114]). In the above formula X1 and X2 are N-R, where R is an optionally substituted aryl, i.e. an aryl substituted with a least one secondary substituent such as a methyl group or tert-butyl group ([0092], [0119], and [0117]). The reference discloses the aryl substituent R are a fluorene group, see Compound 2-2625 (Page 88):
.
PNG
media_image1.png
286
516
media_image1.png
Greyscale
.
From the above discussion, the disclosure of the reference encompasses a 9,9,-dimethylfluorene group, i.e. a fluorene group substituted with two (2) methyl groups. Furthermore, the reference exemplifies a phenyl group substituted with a t-butyl group in Compounds (2-61) and (2-62) (Page 51):
PNG
media_image16.png
378
434
media_image16.png
Greyscale
and
PNG
media_image17.png
336
354
media_image17.png
Greyscale
.
In Formula (2), R5 is a diarylamino group ([0095]) where the hydrogens are substituted with deuterium atoms as exemplified in Compound 2-2714 (Page 100):
PNG
media_image7.png
317
356
media_image7.png
Greyscale
.
From the discussion above, the reference discloses the recited compound:
PNG
media_image18.png
254
288
media_image18.png
Greyscale
.
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.
Response to Arguments
Applicant's arguments filed 9/26/2025 have been fully considered but they are not persuasive.
Applicants argue that Hatakeyama fails to describe a compound as claimed, nor
does Hatakeyama indicate a selection of, or modification leading to, the compounds as
claimed. However, for the reasons discussed in the rejections above, the reference discloses a compound encompassed by the present claims. Furthermore, it is noted that there is no reason to modify the compound disclosed by the reference given that the reference discloses a formula for the compound as well as substituents, including those claimed that can be selected to arrive at the claimed compound.
Applicants argue that Hatakeyama lacks or fails to indicate an R10 substitution as claimed and there is nothing in Hatakeyama that would cause a person of ordinary skill in the
art to select Hatakeyama's Compound 2-2625 as a lead compound, and, having done so,
modify Hatakeyama' s Compound 2-2625 at the particular location, with the particular group
("an optionally substituted alkyl group comprising 1 to 20 carbon atoms"), claimed. However, it is the Office’s position, absent evidence to the contrary that it would have been obvious to one of ordinary skill in the art to select any of the substituents disclosed by the reference, including those presently claimed, and thereby arrive at the claimed compound with a reasonable expectation of success.
As evidence of unexpected results Applicants compare Comparative Compound 1 in Table 2 of the instant Specification:
PNG
media_image19.png
224
328
media_image19.png
Greyscale
,
and compare the EQE of this compound to Inventive Compounds 2 and 4 to 17:
PNG
media_image20.png
170
202
media_image20.png
Greyscale
PNG
media_image21.png
516
570
media_image21.png
Greyscale
PNG
media_image22.png
794
622
media_image22.png
Greyscale
PNG
media_image23.png
752
596
media_image23.png
Greyscale
However, as discussed in the previous Office Action this comparison is not a proper side-by-side comparison for the following reasons. Specifically, all the inventive compounds comprise multiple tert-butyl groups as well substituted or unsubstituted diphenyl amine groups not present on the comparative compound, e.g. Inventive Compound 2 possesses a fully deuterated diphenyl amine substituent not found on the comparative compound. A proper side-by-side comparison would be Comparative Compound 1 to inventive compounds, where the inventive compounds are identical to the comparative compounds but differ only in the presence of an arylamine group.
Even if the comparison were a proper side-by-side comparison, it is noted that the inventive compounds are not commensurate in scope with the scope of the claims for the following reasons. In the inventive compounds, R5-R8 are H or a tert-butyl groups and R10 is a tert-butyl or methyl group, while claim 1 recites that R1 to R8 is hydrogen, an optionally substituted C6-60 aryl group, or an optionally substituted C1-20 alkyl group and R10 is an optionally substituted alkyl comprising 1 to 20 carbon atoms.
In the inventive compounds R12 to R19 are hydrogen, while claim 1 recites that R12 to R19 are hydrogen, an optionally substituted C6-60 aryl group, or an optionally substituted C1-20 alkyl group.
In the inventive compounds R27 to R36 are hydrogen, a methyl group, a tert-butyl group, a phenyl group, while claim 1 recites that R27 to R36 are hydrogen, an optionally substituted C6-60 aryl group, or a substituted on unsubstituted C1-20 alkyl. In the inventive compounds R37 to R41 are hydrogen or a tert-butyl group, while claim 1 recites that R37 to R41 are hydrogen, an optionally substituted C6-60 aryl, or an optionally substituted C1-20 alkyl.
In light of the above, it is unclear if the obtained results are indicative of all compounds encompassed by the present claims or only for the particular inventive compounds exemplified in the Specification.
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.
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