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 .
DETAILED ACTION
Claim Objections
Claim 20 is objected to. The limitation “formula Ar1-3, Ar1-4 or Ar1-5” as found in the Markush group for variable V, should be amended to “formula Ar1-3, Ar1-4, or Ar1-5” for consistency.
Claim 28 is objected to. “A phenyl groups” should be amended to “a phenyl group”.
Claim 33 is objected to. The limitation “or b) reacting in a coupling reaction” should be amended to “or b) reacting a terphenyl derivative in a coupling reaction” for better clarity.
Claim 38 is objected to. “A method comprising proving” should be amended to “A method comprising providing”.
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.
Claims 20-38 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Independent claim 20 does not define variable R6. However, for purposes of further examination, the second instance of R3, which is found below the Markush group for variable R5, will be interpreted as R6. Should Applicants amend this second instance of R3 to R6, this rejection [as well as the 112(d) rejections below] would be withdrawn.
Claim 21 is rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claim 21 recites that Z is CR1. However, all of the formulae in claim 20 have multiple Z groups and the claim does not make it clear whether one, some, or all of the Z groups are CR1. For purposes of further examination, claim 21 will be interpreted as all Z groups are equal to CR1. If this interpretation is correct, Applicants should amend claim 21 accordingly.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 27-29 are rejected under 35 U.S.C. 112(d) as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 27 recites that the compounds of formula (I) to (III), the aryl groups and heteroaryl groups are each substituted by R6 radicals. Claim 28 recites that the compounds of formulae (I) to (III) have at least one R1 group that is a phenyl group[s] substituted by R6 radicals. Claim 29 recites that R4 is selected from C1-C20 straight-chain alkyl groups or C3-C20 branched and cyclic alkyl groups which are each substituted by R6 radicals. However, claim 20, from which claims 27-29 directly depend, does not define R6. Applicant may cancel the claims, amend the claims to place the claim in proper dependent form, rewrite the claims in independent form, or present a sufficient showing that the dependent claims complies with the statutory requirements.
Claim 32 is rejected under 35 U.S.C. 112(d) as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Structure (B) as recited in claim 32 includes the variable R6, which is not defined in claim 20. For this reason, claim 32 fails to further limit claim 20. Applicant may cancel the claims, amend the claims to place the claim in proper dependent form, rewrite the claims in independent form, or present a sufficient showing that the dependent claims complies with the statutory requirements.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale or otherwise available to the public before the effective filing date of the claimed invention.
Claims 20-25, 27, 29-32, and 35-38 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ha et al. (KR-20170136391). Copies of the original and a machine translation are included with this Office action.
Claim 20: Ha et al. teaches compounds which are employed in organic electroluminescent devices. More specifically, Ha et al. teaches compounds which adhere to general formula (2) which are employed in the hole transport region of said devices. Specific examples of compounds which fall under general formula (2) are compounds B1 through B254 as taught on pages 15-37. One of these compounds, compound B24, which has the structure
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(page 16), anticipates Formula (I) of claim 20. As applied to Formula I, compound B24 has all Z groups equal to CR1 with all R1 groups equal to hydrogen atoms. L equal to zero, both L1 groups equal to single bonds, all R3 groups equal to hydrogen atoms, both R4 groups equal to methyl, and A being a group represented by Formula (A-1) with all R3 groups equal to hydrogen atoms and both R4 groups equal to methyl.
Claim 21: In compound B24, all Z groups are CR1, thereby anticipating claim 21.
Claim 22: Because k may be equal to zero in claim 20, claim 22 serves to further limit an optional embodiment where k is equal to 1, 2, or 3. Because claim 22 is directed to an optional embodiment, compound B24 of Ha et al. may still be properly relied upon to reject claim 22.
Claim 23: In compound B24, both L1 groups are single bonds, thereby anticipating claim 23.
Claim 24: Like claim 22, claim 24 serves to further limit an optional embodiment which further limits compounds of Formula (II). Because claim 24 is directed to an optional embodiment, compound B24 of Ha et al. may still be properly relied upon to reject claim 24.
Claim 25: Like claims 22 and 24, claim 25 serves to further limit an optional embodiment which further limits compounds of Formula (III). Because claim 25 is directed to an optional embodiment, compound B24 of Ha et al. may still be properly relied upon to reject claim 25.
Claim 27: Because all R1 groups in compound B24 of Ha et al. are hydrogen atoms, it can also be said that zero R1 groups are not hydrogen atoms, thereby anticipating claim 27.
Claim 29: In compound B24 of Ha et al., all R1 radicals are hydrogen, thereby anticipating claim 29.
Claim 30: In compound B24, all R4 groups are equal to methyl, thereby anticipating claim 30.
Claim 31: Compound B24 also anticipates Formula (I-1-1) of claim 31 with all variable assignments being described in claim 20 above.
Claim 32: Compound B24 shown above also comprises a group which anticipates structures (A), (C) and (D) of claim 32 with all R1 groups equal to hydrogen atoms.
Claim 35: It is submitted that in the act of preparing compound B24, there would inherently be a crude reaction mixture which would necessarily comprise at least one solvent and compound B24. There is nothing which prevents a crude reaction mixture comprising compound B24 from being a formulation which anticipates claim 35.
Claims 36-38: Ha et al. teaches that compounds, which include compound B24 are employed in organic electroluminescent devices which comprise an anode, a hole transport region, an emission region, an electron transport region, and a cathode. The compounds which includes compound B24 are employed in the hole transport region. Given these teachings of Ha et al. it is at once envisaged to have employed any one of the explicitly taught compounds of Ha et al., including compound B24 in the hole transport region. A device comprising compound B24 in the hole transport region anticipates the device limitations of claims 36 and 37. Additionally, one would necessarily have to provide compound B24 and incorporate compound B24 into the devices taught therein, thereby anticipating claim 38.
Claims 20-28, 30, 33, and 35-38 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Jang et al. (KR-20170022438, cited on Applicants information disclosure statement filed on 11/26/25).
Claim 20: Jang et al. teaches compound 1, which has the structure
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(page 29). This compound anticipates Formula (II) of claim 20. As applied to Formula (II) compound 1 has all Z equal to CR1 with two R1 being phenyl groups and the remaining R1 being hydrogen atoms, k is equal to 1, ArL is equal to m-phenylene, and both Ar1 groups equal to biphenyl.
Claim 21: In compound 1 of Jang et al., all Z are equal to CR1, thereby anticipating claim 21.
Claim 22: In compound 1 of Jang et al., ArL is phenyl which is substituted by R2 radicals with all R2 radicals being equal to hydrogen atoms, thereby anticipating claim 22.
Claims 23-25: Claims 23 and 25 further limit embodiments where the compound is of Formula (I) or Formula (III), respectively and claim 24 further limits embodiments where the compound is of Formula (II) and k is equal to zero. However, none of these optional embodiments apply to compound 1, meaning the compound 1 of Jang et al. may properly be relied upon to reject claims 23-25.
Claim 26: In compound 1 of Jang et al. k is equal to 1 and Ar1 is equal to biphenyl substituted by R3 radicals where all R3 radicals are hydrogen atoms, thereby anticipating claim 3.
Claim 27: In compound 1, two R1 groups are phenyl, and therefore not H or D, thereby anticipating claim 27.
Claim 28: In compound 1 of Jang et al., two R1 groups are each phenyl groups substituted by R6 radicals with all R6 radicals being hydrogen atoms, thereby anticipating claim 28.
Claim 30: Claim 30 serves to further limit an optional embodiment where there is a group comprising R4 groups. As such, compound 1 of Jang et al. may be properly relied upon to reject claim 30.
Claim 33: Page 29 of Jang et al. shows that compound 1 is prepared by reacting a terphenyl derivative (compound 1-3) substituted by a reactive group (-Br) in a coupling reaction with a secondary amine.
Claim 35: In preparing compound 1, there is inherently a crude reaction mixture which constitutes a formulation comprising compound 1 and a solvent, thereby anticipating claim 35.
Claims 36-38: Example 1 of Jang et al. is drawn to an organic electroluminescent device comprising a substrate, an anode, a hole injection layer, a hole transport layer, a hole transporting auxiliary layer comprising compound 1, an emission layer, an electron transport layer, an electron injection layer, and a cathode. Example 1 thereby anticipates the device limitations of claims 36 and 37 as well as the method of claim 38.
Claims 20-27, 29-32, and 35 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Mujica-Fernaud et al. (US 2017/0097178).
Claim 20: Mujica-Fernaud et al. teaches compound (4-6) which has the structure
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(page 116). This compound anticipates Formula (I) of claim 20. As applied to Formula (I), compound (4-6) has all Z equal to CR1 with all R1 equal to hydrogen atoms, k equal to zero, the L1 group bonded to A being a single bond, the other L1 group being a p-phenylene group, all R3 equal to hydrogen atoms, both R4 groups equal to methyl, and A being a group which anticipates Formula (A-2) with all R3 equal to hydrogen atoms.
Claim 21: In compound (4-6), all Z groups are CR1, thereby anticipating claim 21.
Claim 22: Because k may be equal to zero in claim 20, claim 22 serves to further limit an optional embodiment where k is equal to 1, 2, or 3. Because claim 22 is directed to an optional embodiment, compound (4-6) of Mujica-Fernaud et al. may still be properly relied upon to reject claim 22.
Claim 23: In compound (4-6), one L1 group is a single bond and the other is phenylene substituted by R5 radicals, with all R5 radicals equal to hydrogen atoms, thereby anticipating claim 23.
Claim 24: Like claim 22, claim 24 serves to further limit an optional embodiment which further limits compounds of Formula (II). Because claim 24 is directed to an optional embodiment, compound (4-6) of Mujica-Fernaud et al. may still be properly relied upon to reject claim 24.
Claim 25: Like claims 22 and 24, claim 25 serves to further limit an optional embodiment which further limits compounds of Formula (III). Because claim 25 is directed to an optional embodiment, compound (4-6) of Mujica-Fernaud et al. may still be properly relied upon to reject claim 25.
Claim 27: Because all R1 groups in compound (4-6) of Mujica-Fernaud et al. are hydrogen atoms, it can also be said that zero R1 groups are not hydrogen atoms, thereby anticipating claim 27.
Claim 29: In compound (4-6) of Mujica-Fernaud et al., all R1 radicals are hydrogen, thereby anticipating claim 29.
Claim 30: In compound (4-6) of Mujica-Fernaud et al., all R4 groups are equal to methyl, thereby anticipating claim 30.
Claim 31: Compound (4-6) of Mujica-Fernaud et al. also anticipates Formula (I-2-1) of claim 31 with all variables being described in claim 20 above.
Claim 32: Compound (4-6) of Mujica-Fernaud et al. comprises a group which anticipates structures (A), (C) and (D) of claim 32 with all R1 groups equal to hydrogen atoms.
Claim 35: It is submitted that in the act of preparing compound (4-6), there would inherently be a crude reaction mixture which would necessarily comprise at least one solvent and compound (4-6). There is nothing which prevents a crude reaction mixture comprising compound (4-6) from being a formulation which anticipates claim 35.
Claim Rejections - 35 USC § 103
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 of this title, 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.
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.
Claim 34 and 36-38 are is rejected under 35 U.S.C. 103 as being unpatentable over Mujica-Fernaud et al. (US 2018/0097178).
Claim 34: Mujica-Fernaud et al. teaches that oligomers, polymers, or dendrimers containing compounds satisfying formula (1) may be prepared (paragraph 0159). Given this teaching, it would have been prima facie obvious to have employed an oligomer, a polymer, or a dendrimer or any one of the explicitly taught compounds, including compound (4-6) of Mujica-Fernaud et al. thereby satisfying claim 34.
Claims 36-38: The compounds taught by Mujica-Fernaud et al. are employed in a hole transport region in organic electroluminescent devices. The preparation of a device as taught by Mujica-Fernaud et al. with compound (4-6) in the hole transport region would have been prima facie obvious to a person having ordinary skill in the art as compound (4-6) represents a preferred compound which is expected to perform in the same manner as the other compounds in the device examples, thereby satisfying claims 36-38.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ROBERT S LOEWE whose telephone number is (571)270-3298. The examiner can normally be reached on Monday-Friday from 8 AM to 5 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski, can be reached at telephone number 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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/Robert S Loewe/Primary Examiner, Art Unit 1766
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