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
Claims 9, 11, 12, 14, 15, 17, and 18 are objected to. Specifically, since claim 1 requires that the first and second compounds comprise a fluorene group, all structures represented by Formulae A and B in claims 9 and 11, Formulae A-1-4 and B-1-1 in claim 12, Formulae A-1 and B-1 in claim 14, Formulae A-1-1 through A-1-4 and Formulae B-1-1 through B-1-4 in claim 15, Formula 1-1 in claim 17, and Formula 2-1 in claim 18 should be replaced with structures where there are no dotted lines within the 5-membered ring of the fluorene. Specifically, all
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groups should be replaced with
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groups to make is clear that the groups in question are fluorene groups.
Claim 10 is objected to. The limitation that the first and second amine-based compounds both comprise the fluorene moieties should be amended to “wherein the first amine-based compound and the second amine-based compound both comprise two or more fluorene moieties’ for the utmost clarity.
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 9 and 19 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. Claim 9 recites that the fluorene moieties in the first and second compounds are each a group represented by Formula A or Formula B. In both Formulae A and B, variable X1 is recited to be a group including C. However, this limitation can only apply to Formula A. In Formula B, X1 can be nothing but C as X1 in Formula B is a tetravalent group. Claim 9 is indefinite since it raises a question as to what the metes and bounds of Formula B comprise under the limitation “a group including C”. Applicants can overcome this rejection by amending Formula B such that X1 is replaced with a carbon atom. Claim 19 is included in this rejection as it is dependent on claim 9.
Claims 11-18 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. Claim 11 recites that the fluorene moieties in the first and second compounds are required to comprise a group represented by Formula A or Formula B. In both Formulae A and B, variable X1 is recited to be a group including C. However, this limitation can only apply to Formula A. In Formula B, X1 can be nothing but C as X1 in Formula B is a tetravalent group. Claim 11 is indefinite since it raises a question as to what the metes and bounds of Formula B comprise under the limitation “a group including C”. Applicants can overcome this rejection by amending Formula B such that X1 is replaced with a carbon atom. Claim 12-18 are included in this rejection as they are dependent on claim 11.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1, 3-11, 13-19, and 21 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Parham et al. (US 2021/0147375) as evidenced by Ossila.
Claim 1: Parham et al. teaches organic electroluminescent devices which are exemplified as comprising an anode (ITO), a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emission layer (EML), a hole blocking layer (HBL), an electron transport layer (ETL), and a cathode (paragraph 0144 and Table 1). Inventive examples 1 and 2 specifically comprise a hole injection layer consisting of HATCN, a hole transport layer consisting of the compound SpMA1, an electron blocking layer consisting of the compound SpMA2. Ossila teaches that hole transport layers are also referred to as electron blocking layers. Because of this, the interlayer taught by Parham et al. inherently comprises a hole transport region comprising a first layer which is the hole transport layer taught by Parham et al. and comprising a second layer which is the electron blocking layer taught by Parham et al. The hole transport layer comprises a first amine-based compound which is SpMA1 and the electron blocking layer comprises a second amine-based compound which is SpMA2. SpMA1 has the structure
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and SpMA2 has the structure
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(page 330). These compounds are different, being structural isomers of each other. As applied to claim 1, device examples 1 and 2 are drawn to light-emitting devices comprising a first electrode (anode), a second electrode facing the anode (cathode), an interlayer between the anode and cathode comprising an emission layer, a first layer and a second layer comprising an amine-based compound where each of the first and second amine-based compounds, which are different from each other, satisfy condition 1-1, 1-2, and 1-31, thereby anticipating claim 1.
Claim 3: In device examples 1 and 2, the first and second layers are in direct contact with each other, thereby anticipating claim 3.
Claim 4: Device examples 1 and 2 are configured to emit green light by virtue of the employment of the phosphorescent green emitter TEG1 (paragraph 0149 and Table 3a).
Claim 5: In device examples 1 and 2, the first layer consists of the first amine-based compound, thereby anticipating claim 5.
Claims 6-8: While Parham et al. does not explicitly teach the triplet energy level requirements of claim 6 or the HOMO energy level requirements of claims 7 and 8, it is submitted that the compounds SpMA1 and SpMA2 would inherently satisfy these properties given the teachings of Applicants specification. Specifically, compound 1-2 of the instant specification and SpMA1 of Parham et al. differ only in that compound 1-2 includes an additional phenyl group bonded to the spirobifluorene moiety. Compound 2-1 of the instant specification and SpMA2 of Parham et al. differ only in that instead of an o-biphenyl group, compound 2-1 of the instant application has a 9,9-dimethlfluorene group. These structural differences are deemed to be minor and would not be expected to have a triplet energy level or a HOMO energy level outside the values recited in claims 6-8. This is especially true since compounds 1-1, 1-2, 1-3, 1-4, 2-1, and 2-2 of Applicants specification all have a fair degree of structural variation present and Table 1 of Applicants specification shows that all of these compounds satisfy the triplet and HOMO energy level requirements as claimed. Comparative compounds D and E are the only compounds shown in Applicants specification which have a triplet energy level which does not satisfy claim 6; however, these compounds have a benzofluorene group which is quite different from a fluorene group due to the increased conjugation.
Claim 9: Each of compounds SpMA1 and SpMA2 comprise fluorene moieties which satisfy each of Formula A (fluorene) and Formula B (spirobifluorene) with X1 equal to a group including C as applied to Formula A (specifically, a C(CH3)2 group) and X1 equal to C as applied to Formula B, Y1 being a single bond, and all rings CY1 through CY4 being unsubstituted benzene rings.
Claim 10: Each of compounds SpMA1 and SpMA2 comprise two fluorene moieties, thereby anticipating claim 10.
Claim 11: Each of compounds SpMA1 and SpMA2 respectively anticipate Formula 1 and Formula 2 of claim 1. As applied to Formula 1, compound SpMA1 has n11 and n12 equal to 1, L11 and L12 equal to a single bond, Ar11 and Ar12 equal to a 9,9-dimethylfluorene group and a spirobifluorene group which anticipates Formulae A and B, respectively, d11 and d12 are equal to zero, n13 is equal to 1, L13 is equal to an o-phenylene group, Ar13 equal to a phenyl group, and d13 is equal to zero. As applied to Formula 2, compound SpMA2 has n21 and 22 equal to 1, L21 and L22 equal to a single bond, Ar21 and Ar22 equal to a 9,9-dimethylfluorene group and a spirobifluorene, respectively, d21 and d22 are equal to zero, n23 is equal to 1, L23 is equal to an o-phenylene group, Ar23 equal to a phenyl group, and d23 is equal to zero.
Claim 13: Compounds SpMA1 and SpMA2 satisfy conditions 2-1 through 2-3 as both Ar12 and Ar22 are each a group represented by Formula B.
Claim 14: In compounds SpMA1 and SpMA2 the group represented by Formula A satisfies Formula A-1 and the group represented by Formula B is represented by Formula B-1, as described in claim 11 above, thereby anticipating claim 14. Claim 15: Compounds SpMA1 and SpMA2 comprise formula A-1-2 as the group comprising Formula A and comprise the group B-1-3 (for compound SpMA1) and the group B-1-1 (for compound SpMA2), thereby anticipating claim 15.
Claim 16: In compound SpMA1, variable L13 is an unsubstituted phenyl group and n13 is 1, thereby anticipating claim 16.
Claim 17: Compound SpMA1 anticipates Formula 1-1 of claim 17 with R13 and R14 equal to methyl, CY11 and CY12 equal to unsubstituted phenyl groups, and all other variable assignments being described in claim 11 above.
Claim 18: In claim 11, the groups Ar21 and Ar22 were arbitrarily assigned to be 9,9-dimethylfluorenyl and spirobifluorenyl groups. However, the variable assignment could just have easily been reversed. In reversing the variable assignment, compound SpMA2 anticipates Formula 2-1 of claim 18 with X21 equal to C, Y21 equal to a single bond, rings CY21-CY24 equal to unsubstituted phenyl, and all other variable assignments being described in claim 11 above.
Claim 19: In compound SpMA1 and SpMA2, variable Y1 is equal to a single bond, thereby anticipating claim 19.
Claim 21: Device examples 1 and 2 of Parham et al. are light-emitting devices which are inherently an electronic apparatus, thereby anticipating claim 21.
Claims 1, 2, 6-11, 13-19, and 21 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Parham et al. (US 2025/0098532) as evidenced by Ossila. Parham et al. is referred to as Ehrenreich et al. (the second author) to avoid confusion with the rejection to Parham et al. above. Ehrenreich et al. has a foreign application priority date of 1/25/21 which is earlier than Applicants (unperfected) foreign priority date. Additionally, all of the subject matter relied upon in US 2025/0098532 is presented in the foreign priority document of Ehrenreich et al.
Claim 1: Ehrenreich et al. teaches organic electroluminescent devices which are exemplified as comprising an anode (ITO), a hole injection layer (HIL), a hole transport layer (HTL), an electron blocking layer (EBL), an emission layer (EML), a hole blocking layer (HBL), an electron transport layer (ETL), and a cathode (paragraphs 0243 and Table 1). Device example V1 comprises an anode, a hole transport region comprising a hole injection layer comprising a hole injection layer, which is a mixture of SpMA1 and the p-dopant PD1, a hole transport layer consisting of SpMA1, and an electron blocking layer consisting of the compound SpMA2. Ossila teaches that hole transport layers are also referred to as electron blocking layers. Because of this, the interlayer taught by Ehrenreich et al. inherently comprises a hole transport region comprising a first layer which is the hole transport layer taught by Ehrenreich et al. and comprising a second layer which is the electron blocking layer taught by Ehrenreich et al. The hole transport layer comprises a first amine-based compound which is SpMA1 and the electron blocking layer comprises a second amine-based compound which is SpMA2. SpMA1 has the structure
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and SpMA2 has the structure
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(pages 196 and 197). These compounds are different, being structural isomers of each other. As applied to claim 1, device examples 1 and 2 are drawn to light-emitting devices comprising a first electrode (anode), a second electrode facing the anode (cathode), an interlayer between the anode and cathode comprising an emission layer, a first layer and a second layer comprising an amine-based compound where each of the first and second amine-based compounds, which are different from each other, satisfy condition 1-1, 1-2, and 1-32, thereby anticipating claim 1.
Claim 2: In example V1, the hole transport region further comprises a hole transport layer HTL as shown in Table 1) and the hole transport layer is in direct contact with the first layer, thereby anticipating claim 2.
Claims 6-8: While Ehrenreich et al. does not explicitly teach the triplet energy level requirements of claim 6 or the HOMO energy level requirements of claims 7 and 8, it is submitted that the compounds SpMA1 and SpMA2 would inherently satisfy these properties given the teachings of Applicants specification. Specifically, compound 1-2 of the instant specification and SpMA1 of Ehrenreich et al. differ only in that compound 1-2 includes an additional phenyl group bonded to the spirobifluorene moiety. Compound 2-1 of the instant specification and SpMA2 of Ehrenreich et al. differ only in that instead of an o-biphenyl group, compound 2-1 of the instant application has a 9,9-dimethlfluorene group. These structural differences are deemed to be minor and would not be expected to have a triplet energy level or a HOMO energy level outside the values recited in claims 6-8. This is especially true since compounds 1-1, 1-2, 1-3, 1-4, 2-1, and 2-2 of Applicants specification all have a fair degree of structural variation present and Table 1 of Applicants specification shows that all of these compounds satisfy the triplet and HOMO energy level requirements as claimed. Comparative compounds D and E are the only compounds shown in Applicants specification which have a triplet energy level which does not satisfy claim 6; however, these compounds have a benzofluorene group which is quite different from a fluorene group due to the increased conjugation.
Claim 9: Each of compounds SpMA1 and SpMA2 comprise fluorene moieties which satisfy each of Formula A (fluorene) and Formula B (spirobifluorene) with X1 equal to a group including C as applied to Formula A (specifically, a C(CH3)2 group) and X1 equal to C as applied to Formula B, Y1 being a single bond, and all rings CY1 through CY4 being unsubstituted benzene rings.
Claim 10: Each of compounds SpMA1 and SpMA2 comprise two fluorene moieties, thereby anticipating claim 10.
Claim 11: Each of compounds SpMA1 and SpMA2 respectively anticipate Formula 1 and Formula 2 of claim 1. As applied to Formula 1, compound SpMA1 has n11 and n12 equal to 1, L11 and L12 equal to a single bond, Ar11 and Ar12 equal to a 9,9-dimethylfluorene group and a spirobifluorene group which anticipates Formulae A and B, respectively, d11 and d12 are equal to zero, n13 is equal to 1, L13 is equal to an o-phenylene group, Ar13 equal to a phenyl group, and d13 is equal to zero. As applied to Formula 2, compound SpMA2 has n21 and 22 equal to 1, L21 and L22 equal to a single bond, Ar21 and Ar22 equal to a 9,9-dimethylfluorene group and a spirobifluorene, respectively, d21 and d22 are equal to zero, n23 is equal to 1, L23 is equal to an o-phenylene group, Ar23 equal to a phenyl group, and d23 is equal to zero.
Claim 13: Compounds SpMA1 and SpMA2 satisfy conditions 2-1 through 2-3 as both Ar12 and Ar22 are each a group represented by Formula B.
Claim 14: In compounds SpMA1 and SpMA2 the group represented by Formula A satisfies Formula A-1 and the group represented by Formula B is represented by Formula B-1, as described in claim 11 above, thereby anticipating claim 14. Claim 15: Compounds SpMA1 and SpMA2 comprise formula A-1-2 as the group comprising Formula A and comprise the group B-1-3 (for compound SpMA1) and the group B-1-1 (for compound SpMA2), thereby anticipating claim 15.
Claim 16: In compound SpMA1, variable L13 is an unsubstituted phenyl group and n13 is 1, thereby anticipating claim 16.
Claim 17: Compound SpMA1 anticipates Formula 1-1 of claim 17 with R13 and R14 equal to methyl, CY11 and CY12 equal to unsubstituted phenyl groups, and all other variable assignments being described in claim 11 above.
Claim 18: In claim 11, the groups Ar21 and Ar22 were arbitrarily assigned to be 9,9-dimethylfluorenyl and spirobifluorenyl groups. However, the variable assignment could just have easily been reversed. In reversing the variable assignment, compound SpMA2 anticipates Formula 2-1 of claim 18 with X21 equal to C, Y21 equal to a single bond, rings CY21-CY24 equal to unsubstituted phenyl, and all other variable assignments being described in claim 11 above.
Claim 19: In compound SpMA1 and SpMA2, variable Y1 is equal to a single bond, thereby anticipating claim 19.
Claim 21: Device examples 1 and 2 of Parham et al. are light-emitting devices which are inherently an electronic apparatus, thereby anticipating claim 21.
Claims 1-3, 5-19, and 21 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Montenegro et al. (US 2024/0381685) as evidenced by Ossila. Montenegro et al. has a foreign application priority date of 9/8/21 which is earlier than Applicants (unperfected) foreign priority date. Additionally, all of the subject matter relied upon in US 2024/0381685 is present in the foreign priority document of Montenegro et al.
Claim 1: Montenegro et al. teaches organic light-emitting devices. Several working examples satisfy all of the device and structural limitations of claim 1. One device example is example E3 as shown in Table 2. Device E3 is comprised of an anode, a hole transport region comprising a hole injection layer, a hole transport layer, and an electron blocking layer, an emission layer, an electron transport layer, an electron injection layer, and a cathode. Ossila teaches that hole transport layers are also referred to as electron blocking layers. Because of this, the interlayer taught by Montenegro et al. inherently comprises a hole transport region comprising a first layer which is the hole transport layer taught by Montenegro et al. and comprising a second layer which is the electron blocking layer taught by Montenegro et al. The first layer/hole transport layer consists of compound HTMV1 which is an amine-based compound having the structure
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(page 142). The second layer/electron blocking layer comprises compound HTM8 which is an amine-based compound having the structure
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(page 147). Conditions 1-1 through 1-3 are satisfied and device example E3, therefore anticipates all of the structural and device limitations of claim 1.
Claim 2: Claim 2 is anticipated by device example E3. However, to reject claim 2, a different means of rejecting the claim is undertaken. Specifically, in example E3, the hole transport region comprises a first layer (the hole injection layer consisting of compound HTMV1 and F4TCNQ) and a second layer (the electron blocking layer consisting of compound HTM8). The hole transport region further comprises a hole transport layer consisting of compound HTMV1 which is located between the first and second layers and is in direct contact with the first layer, thereby anticipating claim 2.
Claim 3: Using the device assignment recited in claim 1 above, the first amine-based compound present in the hole transport layer is in direct contact with the second amine-based compound present in the electron blocking layer, which anticipates claim 3.
Claim 5: Using the device assignment recited in claim 1 above, the first layer consists of the first amine-based compound HTMV1, thereby anticipating claim 5.
Claims 6-8: Compound HTMV1 is a positional isomer of compound 2-1 of Applicants specification and would therefore be expected to have a very similar triplet energy level and a HOMO energy level. Compound HTM8 is similar to compound 1-4 of Applicants specification and would therefore be expected to have similar triplet and HOMO energy levels. These statements can be made as the compounds taught in the instant application have structural variation with all of the fluorene-group-comprising compounds shown in Applicants specification satisfying the triplet and HOMO energy level requirements of claims 6-8.
Claim 9: Each of compounds HTMV1 and HTM8 comprise fluorene moieties which satisfy each of Formula A (fluorene) and Formula B (spirobifluorene) with X1 equal to a group including C as applied to Formula A (specifically, a C(CH3)2 group or a C(Ph)2 group) and X1 equal to C as applied to Formula B, Y1 being a single bond or a non-bond, and all rings CY1 through CY4 being unsubstituted benzene rings.
Claim 10: Both compounds HTMV1 and HTM8 comprise three and two fluorene moieties, respectively, thereby anticipating claim 10.
Claim 11: Each of compounds HTMV1 and HTM8 respectively anticipate Formula 1 and Formula 2 of claim 1. As applied to Formula 1, compound HTMV1 has n11, n12, and n13 equal to 1, L11, L12, and L13 equal to single bonds, Ar11 and Ar12 equal to a 9,9-dimethylfluorene group which anticipates Formula A, Ar13 equal to a spirobifluorene group which anticipates Formula B, d11, d12, and d13 are equal to zero. As applied to Formula 2, compound HTM8 has n21 and 22 equal to 1, L21 and L22 equal to a single bond, Ar21 and Ar22 equal to a 9,9-dimethylfluorene group and a 9,9-diphenylfluorene group, respectively, d21 and d22 are equal to zero, n23 is equal to 1, L23 is equal to an o-phenylene group, Ar23 equal to a phenyl group, and d23 is equal to zero.
Claim 12: In compound HTM8, Ar21 is a group represented by Formula A-1-4 and Ar22 is a group represented by Formula B-1-1, thereby anticipating claim 12.
Claim 13: Compounds HTMV1 and HTM8 satisfy conditions 2-1 through 2-3 as Ar12 is a group represented by Formula A and Ar22 is a group represented by Formula B.
Claim 14: In compounds HTMV1 and HTM8, the group represented by Formula A satisfies Formula A-1 and the group represented by Formula B is represented by Formula B-1, as described in claim 11 above, thereby anticipating claim 14. Claim 15: Compound HTMV1 comprises formula A-1-2 as the group comprising Formula A and Formula B-1-1 as the group comprising Formula B. Compound HTM8 comprises Formula A-1-1 as the groups comprising Formula A, thereby anticipating claim 15.
Claim 16: In compound HTMV1, variable n13 is 1, thereby anticipating claim 16.
Claim 17: Compound HTMV1 anticipates Formula 1-1 of claim 17 with R13 and R14 equal to methyl, CY11 and CY12 equal to unsubstituted phenyl groups, and all other variable assignments being described in claim 11 above.
Claim 18: Compound HTM8 anticipates Formula 2-1 of claim 18 with X21 equal to C, Y21 equal to a non-bond rings CY21-CY24 equal to benzene, a21-a24 equal to zero, and all other variable assignments being described in claim 11 above.
Claim 19: For claim 19, device example E6 is relied upon. Device example E6 includes the same compound HTMV1 as the first amine-based compound and compound HTM5 (whose structure is shown on page 146) as the second amine-based compound. This embodiment satisfies Condition 1-1 of claim 1. As applied to claim 9 variable Y1 in compound HTM5 is a single bond, thereby anticipating claim 19.
Claim 21: Device example E3 of Montenegro et al. is a light-emitting device which is inherently an electronic apparatus, thereby anticipating claim 21.
Allowable Subject Matter
Claim 20 is 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. Claim 20 is drawn to embodiments where the first amine-based compound of claim 1 is selected from one of the four compounds 1-1 through 1-4 and the second amine-based compound is selected from one of two compounds 2-1 and 2-2. The prior art does not teach or reasonably suggest to a person having ordinary skill in the art to prepare a light-emitting device which employs one of compounds 1-1 through 1-4 as the first amine-based layer, and one of compounds 2-1 and 2-2 as the second amine-based layer.
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
1 Condition 1-1 of claim 1 does not exclude the second amine-based compound comprising two or more fluorene moieties. Similarly, condition 1-2 does not exclude the first amine-based compound comprising two or more fluorene moieties.
2 Condition 1-1 of claim 1 does not exclude the second amine-based compound comprising two or more fluorene moieties. Similarly, condition 1-2 does not exclude the first amine-based compound comprising two or more fluorene moieties.