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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Response to Amendment
The amendment filed on 28 August 2024 has been entered.
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 1-18 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.
With respect to claim 1: The claim is directed to “a deuterated composition”, but the chemical composition for “Compound A” is not for the claimed deuterated composition, but instead from the precursor from which the actual deuterated composition is derived. This is an issue because different precursors can result in the [AltContent: arrow]
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same final product; for instance, the admitted prior art from page 4 of the specification is a deuterated composition having a structure falling within the scope of “Compound A”, but was made by a different process.
Claims 2-18 each have a similar problem of claiming the final product but only disclosing the precursor.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 4 recites the broad recitation “wherein the deuterated composition comprises a deuterated mixture prepared from two types of Compound A by means of a deuterated reaction” “preferably, the deuterated mixture comprises at least five types of compounds; preferably, the deuterated mixture comprises at least six types of compounds; preferably, the deuterated mixture comprises at least seven types of compounds”, and the claim also recites “preferably, the deuterated mixture comprises at least five types of compounds; preferably, the deuterated mixture comprises at least six types of compounds; preferably, the deuterated mixture comprises at least seven types of compounds” which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Claims 6, 8, 10, 15, 16 raise similar issues to claim 4: each of these claims include limitations prefaced by “optionally” or “preferably”, raising the question of whether any of these limitations further limits the claim they appear in.
For purposes of examination, disclosure of a final product appearing on it’s face to be a deuterated version of Compounds A, B, or C will be held to disclose Compounds A, B, and C, regardless of the method by which they were produced, and any limitation stated to be “preferrable” or “optional” will not be considered to limit the scope of the claim in which they appear.
Claim Rejections - 35 USC § 102
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 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 1-8, 12-13, 18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Lecloux et al. (US 2011/0121269 A1).
With respect to claim 1: Lecloux teaches “a deuterated composition (throughout reference), comprising a deuterated mixture prepared from Compound A by means of a deuterated reaction (paragraph 33); wherein Compound A has a structure represented by Formula I:
[AltContent: textbox (Lecloux
Formula 1)][AltContent: arrow]
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wherein Ar11 and Ar12 are each independently selected from any one of substituted or unsubstituted C6 to C40 aryl (paragraph 36), or substituted or unsubstituted C12 to C40 heteroaryl (paragraphs 36-37); R11 and R12 are each independently selected from any one of deuterium (paragraph 35), substituted or unsubstituted C1 to C6 linear or branched alkyl (paragraph 35), substituted or unsubstituted C6 to C40 aryl (paragraph 35), or substituted or unsubstituted C12 to C40 heteroaryl (paragraph 35); substituted substituents in Ar11, Ar12, R11 and R12 are each independently selected from at least one of C1 to C6 linear or branched alkyl, C6 to C20 aryl, or C6 to C20 heteroaryl (paragraphs 35-37); and m and n are each independently selected from integers between 0 and 4 (paragraph 35)”.
With respect to claim 2: Lecloux teaches “the deuterated composition according to claim 1 (see above), wherein Compound A has a structure represented by
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(Lecloux formula 1; see above) wherein Ar301, Ar302, Ar401 and Ar402 are each independently selected from one of phenyl, naphthyl or phenanthryl (paragraphs 53-65), and Ar301, Ar302, Ar401 and Ar402 are not phenanthryl at the same time (paragraphs 53-65); the structure represented by Formula I' contains only one phenanthryl (paragraphs 45-46); and o and p are each independently selected from 0 or 1 (paragraphs 53-65)”.
With respect to claim 3: Lecloux teaches “the deuterated composition according to claim 2 (see above), wherein Compound A is not
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(see Lecloux paragraphs 53-60, 64-65)”.
With respect to claim 4: Lecloux teaches “The deuterated composition according to claim 2 (see above), wherein the deuterated composition comprises a deuterated mixture prepared from two types of Compound A by means of a deuterated reaction; preferably, the deuterated mixture comprises at least five types of compounds; preferably, the deuterated mixture comprises at least six types of compounds; preferably, the deuterated mixture comprises at least seven types of compounds (paragraph 73)”.
With respect to claim 5: Lecloux teaches “The deuterated composition according to claim 2 (see above), wherein Compound A is selected from any one of the following compounds:
[AltContent: textbox (Paragraph 54)][AltContent: arrow][AltContent: textbox (Paragraph 53)][AltContent: arrow]
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[AltContent: arrow][AltContent: arrow][AltContent: arrow][AltContent: textbox (See paragraphs 53-65)] With respect to claim 6: Lecloux teaches “the deuterated composition according to claim 2 (see above), wherein AR11, AR12, R11, and R12 are each independently selected from any one of
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[AltContent: arrow][AltContent: textbox (Paragraph 35)][AltContent: arrow][AltContent: arrow][AltContent: textbox (See paragraphs 53-65)]
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With respect to claim 7: The deuterated composition according to claim 1 (see above), wherein Compound A is selected from any one of the following compounds:
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(see paragraphs 53-65)”.
With respect to claim 8: Lecloux teaches “The deuterated composition according to claim 1 (see above), wherein the deuterated reaction comprises the following steps: in the presence of a catalyst (paragraph 66), placing Compound A in D20 (paragraph 126) and a solvent (paragraph 66), and conducting the deuterated reaction to obtain the deuterated mixture (paragraph 66); preferably, the solvent is selected from any one or a combination of at least two of benzene, toluene, ethyl acetate or C6D6, further preferably C6D6; optionally, the reaction is conducted in the presence of the catalyst; optionally, the reaction is conducted in a hydrogen atmosphere; optionally, a volume ratio of D20 to C6D6 is 1:(4-6); optionally, the deuterated reaction is conducted at a temperature of 60-200 *C; optionally, the deuterated reaction lasts for 1-80 h; optionally, a pressure of the deuterated reaction is 0.01-2 MPa; and optionally, a deuteration rate of the deuterated mixture is 15% to 99%, further preferably 28% to 70%, and further preferably 38% to 54% (as noted above, none of the ‘optional’ clauses are considered to limit the scope of the claimed subject matter)”.
With respect to claim 12: Lecloux teaches “an organic electroluminescent device (100) comprising an anode (110), a cathode (160), and an organic thin film layer (120+130+140+150) disposed between the anode and the cathode (see Fig. 1), wherein the organic thin film layer comprises a light emitting layer (140); and a material of the organic thin film layer comprises the deuterated composition (paragraph 73) according to claim 1 (see above)”.
With respect to claim 13: Lecloux teaches “the organic electroluminescent device according to claim 12 (see above), wherein the organic layer comprises a light-emitting layer (140); and a material of the light-emitting layer comprises the deuterated composition (paragraph 73)”.
With respect to claim 18: Lecloux teaches “a display device (paragraph 68), comprising the organic electroluminescent device according to claim 12 (see above)”.
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 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 9-10 are rejected under 35 U.S.C. 103 as being unpatentable over Lecloux as applied to claim 1 above, and further in view of Choi et al. (US 2022/0209119 A1).
With respect to claim 9: Lecloux teaches “the deuterated composition according to claim 1 (see above)”.
Lecloux does not specifically teach “wherein the deuterated composition further comprises Compound B having a structure represented by Formula II:
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wherein Ar21 and Ar22 are each independently selected from any one of substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C3 to C20 heteroaryl; R21, R22 and R23 are each independently selected from any one of hydrogen, C1 to C12 linear or branched alkyl, or C6 to C12 cycloalkyl; and substituted substituents in Ar21 and Ar22 are each independently selected from C1 to C5 linear or branched alkyl, or C6 to C12 aryl”.
However, Choi teaches wherein the deuterated composition further comprises Compound B having a structure represented by Formula II:
[AltContent: textbox (Choi Formula 1a; see paragraph 8)][AltContent: arrow]
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wherein Ar21 and Ar22 are each independently selected from any one of substituted or unsubstituted C6 to C20 aryl, or substituted or unsubstituted C3 to C20 heteroaryl (paragraph 9); R21, R22 and R23 are each independently selected from any one of hydrogen, C1 to C12 linear or branched alkyl, or C6 to C12 cycloalkyl (paragraph 9); and substituted substituents in Ar21 and Ar22 are each independently selected from C1 to C5 linear or branched alkyl, or C6 to C12 aryl (paragraph 9)”.
It would have been obvious at the time the application was filed for one of ordinary skill in the art to modify the deuterated composition of Lecloux by adding compound B as taught by Choi in order to enhance the luminous efficiency and lifespan of organic light emitting devices in which the composition is used (Choi paragraph 6).
With respect to claim 10: Lecloux in view of Choi teaches “The deuterated composition according to claim 9 (see above)”.
Lecloux does not specifically teach “wherein Ar21 and Ar22 are each independently selected from any one of
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optionally, R1, R2 and R3 are each independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl or adamantyl (paragraph 9); optionally, compound B is selected from any one of the following compounds
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.”
[AltContent: arrow][AltContent: arrow][AltContent: textbox (See Choi formula 2, paragraph 75)]However, Choi teaches “wherein Ar21 and Ar22 are each independently selected from any one of
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optionally, R1, R2 and R3 are each independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, sec-butyl, tert-butyl, cyclohexyl or adamantyl (paragraph 9); optionally, compound B is selected from any one of the following compounds
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.”
It would have been obvious at the time the application was filed for one of ordinary skill in the art to modify the deuterated composition of Lecloux by adding compound B as taught by Choi in order to enhance the luminous efficiency and lifespan of organic light emitting devices in which the composition is used (Choi paragraph 6).
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Lecloux as applied to claim 1 above, and further in view of Huh et al. (US 2021/0210694 A1).
With respect to claim 11: Lecloux teaches “The deuterated composition according to claim 1 (see above)”.
Lecloux does not specifically teach “wherein the deuterated composition further comprises Compound C having a structure represented by Formula III:
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wherein Ar31, Ar32, Ar33 and Ar34 are each independently selected from any one of substituted or unsubstituted C6 to C22 aryl or substituted or unsubstituted C12 to C40 heteroaryl; R31 is selected from any one of phenyl, naphthyl or biphenyl; a is selected from 0 or 1; substituted substituents in Ar31, Ar32, Ar33 and Ar34 are each independently selected from C1 to C5 linear or branched alkyl or C6 to C12 aryl; optionally, Ar31, Ar32, Ar33 and Ar34 are each independently selected from any one or a combination of at least two of
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optionally, Compound C is selected from any one of the following compounds:
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However, Huh teaches “wherein the deuterated composition further comprises Compound C having a structure represented by Formula III:
[AltContent: textbox (Huh paragraph 288)][AltContent: arrow]
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wherein Ar31, Ar32, Ar33 and Ar34 are each independently selected from any one of substituted or unsubstituted C6 to C22 aryl or substituted or unsubstituted C12 to C40 heteroaryl (paragraph 288); R31 is selected from any one of phenyl, naphthyl or biphenyl; a is selected from 0 or 1 (paragraph 288); substituted substituents in Ar31, Ar32, Ar33 and Ar34 are each independently selected from C1 to C5 linear or branched alkyl or C6 to C12 aryl (paragraph 288); optionally, Ar31, Ar32, Ar33 and Ar34 are each independently selected from any one or a combination of at least two of
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optionally, Compound C is selected from any one of the following compounds:
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”.
It would have been obvious at the time the application was filed for one of ordinary skill in the art to modify the deuterated composition of Lecloux by adding compound C as taught by Huh due to the art-recognized suitability of such a material to make an organic light emitting layer (Huh paragraph 288).
Claims 14-17 are rejected under 35 U.S.C. 103 as being unpatentable over Lecloux as applied to claims 1, 12 above, and further in view of Takeshima et al. (US 2011/0220886 A1).
With respect to claim 14: Lecloux teaches “The organic electroluminescent device according to claim 12 (see above), wherein the material of the light-emitting layer further comprises a doped material (paragraphs 81-82)”.
Lecloux does not specifically teach “wherein the doped material comprises a compound having a structure represented by Formula BDI:
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wherein Ar101, Ar102, Ar201 and Ar202 are each independently selected from any one of substituted or unsubstituted C6 to C40 aryl or substituted or unsubstituted C12 to C20 heteroaryl; R101 and R102 are each independently selected from any one of substituted or unsubstituted C1 to 012 alkyl, substituted or unsubstituted C6 to C40 aryl, or substituted or unsubstituted C12 to C20 heteroaryl; R101 and R102 can be joined to form a ring by a single bond; m and n are each independently selected from 0 or 1 and are not 0 at the same time; and substituted substituents in Ar101, Ar102, Ar201, Ar202, R101 and R102 are each independently selected from any one or a combination of at least two of -D, -F, C1 to C12 alkyl, C1 to C6 alkoxy, C2 to C8 alkenyl, C6 to C15 aryl, or C12 to C20 heteroaryl”.
However, Takeshima teaches “wherein the doped material comprises a compound having a structure represented by Formula BDI:
[AltContent: textbox (From Page 30 of Takeshima)][AltContent: arrow][AltContent: textbox (General Formula of Takeshima’s dopant)][AltContent: arrow]
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wherein Ar101, Ar102, Ar201 and Ar202 are each independently selected from any one of substituted or unsubstituted C6 to C40 aryl or substituted or unsubstituted C12 to C20 heteroaryl (paragraph 100; see pages 17-38); R101 and R102 are each independently selected from any one of substituted or unsubstituted C1 to 012 alkyl (see page 30 example above), substituted or unsubstituted C6 to C40 aryl (see last example on page 31), or substituted or unsubstituted C12 to C20 heteroaryl; R101 and R102 can be joined to form a ring by a single bond (see last two examples on page 28); m and n are each independently selected from 0 or 1 and are not 0 at the same time; and substituted substituents in Ar101, Ar102, Ar201, Ar202, R101 and R102 are each independently selected from any one or a combination of at least two of -D, -F, C1 to C12 alkyl, C1 to C6 alkoxy, C2 to C8 alkenyl, C6 to C15 aryl, or C12 to C20 heteroaryl (see pages 17-38)”.
It would have been obvious at the time the application was filed for one of ordinary skill in the art to modify the deuterated composition of Lecloux by adding a dopant of the type taught by Takeshima due to the art recognized suitability of Takeshima’s dopants to form a light emitting layer (Takeshima paragraph 99).
With respect to claim 15: Lecloux in view of Takeshima teaches “The organic electroluminescent device according to claim 14 (see above)”.
Lecloux further teaches “wherein the C6 to C40 aryl is selected from any one of phenyl (paragraph 45), biphenyl, terphenyl, naphthyl (paragraph 45), anthryl, phenanthryl, fluorenyl, benzofluorenyl, 9,10-diphenylanthryl, dibenzofluorenyl, naphthofluorenyl, pyrenyl, perylenyl, spirofluorenyl, triphenylenyl, fluoranthenyl, hydrogenated benzanthryl, indenofluorenyl, benzindenofluorenyl, dibenzindenofluorenyl, naphthofluorenyl or benzonaphthofluorenyl, preferably any one of phenyl, naphthyl, biphenyl, terphenyl, fluoranthenyl, fluorenyl, 9,10- diphenylanthryl or benzofluorenyl; optionally, the C12 to C20 heteroaryl is selected from any one of dibenzofuranyl, dibenzothienyl, naphthobenzofuranyl, naphthobenzothienyl, dinaphthofuranyl or dinaphthothienyl; optionally, the C1 to C12 alkyl is selected from any one of methyl, ethyl, propyl, butyl, adamantyl, 1-methylcyclohexyl, 1-methylcyclopentyl, cyclopentyl or cyclohexyl; optionally, the C1 to C6 alkoxy is selected from any one of methoxy, ethoxy, propoxy, butoxy or wherein the dashed line represents a linkage site; optionally, the C6 to C15 aryl is selected from any one of phenyl, naphthyl or biphenyl (as noted above, ‘preferable’ and ‘optional’ clauses are not considered to limit the claim)”.
With respect to claim 16: Lecloux in view of Takeshima teaches the organic electroluminescent device according to claim 14 (see above)”.
Lecloux further teaches “wherein Ar101 and Ar102 are each independently selected from any one of the following substituted or unsubstituted groups: phenyl (paragraph 45), naphthyl (paragraph 45), biphenyl, terphenyl, fluoranthenyl, fluorenyl, 9,10-diphenylanthryl, benzofluorenyl, dibenzofuranyl, dibenzothienyl, naphthobenzofuranyl or naphthobenzothienyl; the substituted substituents are selected from any one or a combination of at least two of -D, -F, -CN, phenyl, biphenyl, dibenzofuranyl, methyl, deuterated methyl, adamantyl, tert-butyl, 1-methylcyclopentyl, cyclohexyl, cyclopentyl, methoxy,naphthyl, dibenzothienyl or naphthobenzothienyl, wherein the dashed line represents a linkage site (paragraph 82); optionally, Ar2o1 and Ar2o2 are each independently selected from any one of the following substituted or unsubstituted groups: phenyl, naphthyl, dibenzofuranyl or biphenyl; the substituted substituents are selected from any one or a combination of at least two of methyl, methoxy, phenyl or dibenzofuranyl; optionally, Rio and R1o2 are each independently selected from any one of methyl, ethyl, propyl or phenyl; optionally, Rio is the same as R1o2 (as noted above, ‘preferable’ and ‘optional’ clauses are not considered to limit the claim)”.
With respect to claim 17: Lecloux in view of Takeshima teaches “The organic electroluminescent device according to claim 14 (see above)”.
Lecloux does not specifically teach “wherein the compound having the structure represented by Formula BDI is selected from any one of the following compounds:
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”.
However, Takeshima suggests “wherein the compound having the structure represented by Formula BDI is selected from any one of the following compounds:
[AltContent: textbox (General equation for Takeshima’s dopant: Applicant’s structure corresponds to Ar15 and Ar16 = phenyl and Ar14 = [img-media_image63.png], and q =1, all of which are within Takeshima’s general disclosure (see paragraph 100))][AltContent: arrow][AltContent: arrow]
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858
983
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966
895
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1513
915
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1470
916
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669
989
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”.
It would have been obvious at the time the application was filed for one of ordinary skill in the art to modify the deuterated composition of Lecloux by adding a dopant of the type taught by Takeshima due to the art recognized suitability of Takeshima’s dopants to form a light emitting layer (Takeshima paragraph 99).
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Tokairin et al. (US 20070063638 A1), which teaches an organic electroluminescence device.
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/NATHANIEL J LEE/Examiner, Art Unit 2875
/ABDULMAJEED AZIZ/Supervisory Patent Examiner, Art Unit 2875
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