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 .
Response to Arguments
Applicant's arguments filed 02/23/2026 have been fully considered but they are not persuasive.
Applicant argues that the compound 16 of Zhao no longer meets the claims because Ar1 and Ar2 are not methyl groups. This argument is partially convincing, the rejection has been changed from a 102 to a 103 rejection. As discussed in the rejection, the disclosed structure makes obvious many embodiments of the claimed Formula 1 with alkyl groups longer than methyl for Ar1 and Ar2.
Applicant argues that Hong was indicated as withdrawn in the arguments section of the last office action but the rejection was still included. This argument is convincing. The rejection of Hong was meant to be withdrawn and was inadvertently included with the other rejections.
Applicant argues that the Office’s position in Bae relies on assembling elements scattered across generic lists and then grafting a specific aromatic constellation onto a benzocarbazole. So Applicant argues that the claimed formula is not disclosed with sufficient specificity to merit anticipation. Applicant argues with respect to obviousness that there must be a reasoned expectation of success to arrive at this particular arrangement together with (i) (L)a as a direct linkage and (ii) Ar1/Ar2 provisos now in the claims. This argument is partially convincing. Examiner agrees that the disclosure is not specific enough to merit anticipation, and the 102 rejection is withdrawn. As to the obviousness rejection: (i) (L)a as a direct linkage is disclosed explicitly in specific embodiments and (ii) the provisos now in the claims do not actually require substitution on the fluorenyl group, in the claimed embodiment wherein the subscript c is zero.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-4, 7-9, 11, 13-14 and 17-18 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 applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claims 1 and 13 recite the proviso that when Ar1 and Ar2 are each a phenyl group, then
“(R2)c is not a hydrogen atom”. The notation (R2)c is confusing. Does this mean that all the R2’s cannot be a hydrogen atom? Or that only one of the R2’s cannot be a hydrogen atom? Nevertheless, the subscript c can be zero, and the absence of R2 at each carbon atom on the aromatic ring must be a hydrogen atom.
Claims 7 and 17 recite the limitation “R11 and R12 are each independently a hydrogen atom. . .” and then also the limitation “provided that (R11)x and (R12)y is not a hydrogen atom”. This is confusing. It is not clear if R11 or R12 can be hydrogen atoms. Nevertheless, x and y may each be an integer of 0, and the absence of R11 and R12 would be a structure with hydrogen atoms on the aromatic C atoms of the phenyl groups.
All other claims are indefinite because the depend from one of the above claims and do not remedy the deficiency.
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.
Claim(s) 1-4, 7-11, 13-14 and 17-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Bae et al (US 20140231783 A1).
The rejection is maintained because the claims ultimately have not changed scope: Since the claim requires either proviso 1) or 2) in claims 1 and 13, any reference that meets proviso 2) reads on the claims. Since in proviso 2) the subscript c can be 0, no R2 group is actually required to be present, and so no substitution on the fluorenyl ring is required by the claims.
Regarding the other proviso 1), Bae would still make obvious the claimed structure because Bae discloses that the groups Z1 and Z2 include a substituted or unsubstituted fluorenyl group [0019]. These substitutions include aryl groups [0049]. The fluorenyl groups also explicitly include embodiments wherein the claimed Ar1 and Ar2 are not both methyl or both phenyl:
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[0048].
Bae discloses a compound used in the hole transport or other layers of an OLED having the claimed layered structure [0028, Fig. 2] wherein the compound has the structure
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wherein R1 and R2 are bonded to form an aromatic ring and R5 to R8 is a functional group -L1-Y1 wherein L1 can be a single bond and Y1 is an -N(Z1)(Z2) group [0010-0019] and X is preferably an aryl group [0059, p5, Table A-1] wherein examples include:
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[p18] wherein Y1 includes:
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and others that read on the claimed groups [p15].
This rejection is made under 35 USC 103 obviousness. It would have been obvious to one having ordinary skill in the art to have combined the disclosed elements as taught by Bae, since each one is explicitly disclosed and no modification is required. The claims are certainly obvious over the combination of elements disclosed, and the mere fact that a reference suggests a multitude of possible combinations does not in and of itself make any one of those combinations less obvious. Merck & Co. v. Biocraft Laboratories, 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir.), cert. denied, 493 U.S. 975 (1989).
In particular, compounds 1-1-21 and 1-1-19 [Table 1-1-1, p58] having the formula:
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wherein L1-Y1 is represented, respectively, by S-16 and S-30:
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[p31]
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[p33]. While these specific compounds are excluded from the claims, it would have been obvious to one having ordinary skill in the art at the time of filing of Applicant’s invention to prepare the same compounds with C2 or longer alkyl groups with the reasonable expectation that they will have the same or similar properties to the C1 methyl substituted compounds disclosed.
Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978).
Regarding claim 11, Bae discloses the examples with the host compound H1:
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[p68].
Claim(s) 1-3, 8, and 13 are is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhao et al (WO 2019185061 A1, equivalent to CN 110317184 submitted on the IDS of 06/24/2025).
Zhao discloses a triarylamine compound useful in the hole transport layer [p11] of an OLED device having the claimed OLED layers [p6, Fig. 1] wherein the triarylamine compound includes compound 16 having the structure:
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[p5 of WO document].
While the above compound does not anticipate the claims, because it is specifically excluded by the amendment, it still makes obvious the claimed structure, since Ar1 and Ar2 of claim claims can be an alkyl group having 2 to 20 carbon atoms. The skilled artisan would expect that compounds with at least smaller alkyl groups such as ethyl, propyl, butyl, etc., would have similar if not indistinguishable properties to the compounds of Zhao with methyl groups. If they differed, it would be in predictable ways, such as increased electron donation and hydrophobicity in the longer alkyl groups.
It would have been obvious to one having ordinary skill in the art at the time the invention was made to have prepared the claimed compounds fluorene groups having C2 to C20 alkyl group substitution because Zhao teaches the same compounds with C1 methyl substitution, and they would have a reasonable expectation of success in achieving the same or similar properties. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978).
Allowable Subject Matter
Claim 12 and 20 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.
The following is a statement of reasons for the indication of allowable subject matter: the claims require specific substituents for the claimed structures of Formula (1) at each generic substituent Ar1 to Ar4 or R1 to R3. Bae et al (US 20140231783 A1), discussed above, discloses compounds with the claimed benzocarbazole structure:
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wherein Y1 includes
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which may be generically substituted, and X includes aryl groups that can include aryl groups such as phenyl, biphenyl and naphthyl [0044]. However, each element of the claims would require picking a single embodiment from a long list of options, and then picking another embodiment for , and to arrive at the specific embodiments of claims 12 and 20 would require excessive hindsight on the part of the office.
Zhao et al (WO 2019185061 A1, equivalent to CN 110317184 submitted on the IDS of 06/24/2025), discussed above, discloses only the compounds having dimethyl substitution on the fluorenyl group:
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and there would be no obvious reason to modify the compounds to have the aromatic substitution of claims 12 and 20.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MICHAEL M DOLLINGER whose telephone number is (571)270-5464. The examiner can normally be reached 10am-6:30pm M-F.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski can be reached at 571-272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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MICHAEL M. DOLLINGER
Primary Examiner
Art Unit 1766
/MICHAEL M DOLLINGER/Primary Examiner, Art Unit 1766