Patent
Atlas literature
Patent
US 9,252,367Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
A graphene derivative, characterized in that it is represented by the following formula (I): SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.1.6.1039.651.1541.1069.svg 1.393 1.673 Chemistry Black and white (I) wherein: A represents a graphene substrate; n represents the number of the group represented by the following formula (II) and is a positive integer equal to or less than a half (1/2) of the total number of carbon atoms in the graphene substrate: SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.1.15.1130.1738.1270.1814.svg 0.253 0.467 Chemistry Black and white SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.1.16.1137.1821.1342.2167.svg 1.153 0.683 Chemistry Black and white-CH 3 x (II) wherein each group represented by formula (II) is connected to adjacent two carbon atoms of a carbon ring of the graphene substrate, and each carbon atom of the graphene substrate connects with at most one group represented by formula (II); each X independently represents an electron-withdrawing-group -N09 or -CN; and each R independently represents any one of -R 1, -R 2, -O-R 1, -O-R 2, -R 1 -C 6 H 5, -R 2 -C 6 H 5, and -R 3, wherein each R 1 is independently an n-alkyl group having no less than 5 carbon atoms, Frommer Lawrence & H aug LLP 745 Fi ft h Avenue New York, NY 10151 212-588-0800 Page 2 of 14 0160175 1. DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021 each R 2 is independently a substituted n-alkyl group having no less than 5 carbon atoms in its main chain and having an alkyl substituent, the C 6 H 5 represents a phenyl group which is connected to the end of R 1 or R 2, and R 3 is an aryl group.
The graphene derivative according to claim 1, characterized in that the number of the carbon atoms of the graphene substrate is between 500 and 10000.
The graphene derivative according to claim 1, characterized in that the group represented by formula II is a group represented by the following formula Ila: SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.2.10.1068.1333.1208.1411.svg 0.26 0.467 Chemistry Black and white SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.2.11.1080.1418.1307.1739.svg 1.07 0.757 Chemistry Black and white-CH 3 R (Il a).
The graphene derivative according to claim 1, characterized in that, the number of carbon atoms of R 1 ranges from 5 to 20; the number of carbon atoms in the main chain of R 2 ranges from 5 to 20, wherein the alkyl substituent is a methyl or ethyl and is connected to the carbon atom at 2-position or 3- position of the main chain of R 2; and the number of ring carbon atoms in R 3 ranges from 6 to 24. Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 3 of 14 01601751.DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021
A transparent conductive film, characterized in that the film comprises the graphene derivative according to claim 1.
An organic electroluminescent device, including an anode layer, an organic electroluminescent layer, and a cathode layer, characterized in that said anode layer comprises the graphene derivative according to claim 1.
A method of preparing an anode layer on a substrate of an organic electroluminescent device, characterized in that: the graphene derivative according to claim 1 is deposited onto the substrate by a vacuum evaporation at a temperature of 330 to 370 SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.6.11.1171.1461.1231.1496.svg 0.117 0.20 Chemistry Black and white Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 7 of 14 0160175 1. DOC
canceled
A method of preparing a graphene derivative represented by formula (I): SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.3.12.1036.1573.1539.1991.svg 1.393 1.677 Chemistry Black and white (J) wherein: A represents a graphene substrate; n represents the number of the group represented by the following formula (I I) and is a positive integer equal to or less than a half (1/2) of the total number of carbon atoms in the graphene substrate: Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 4 of 1 4 01601751.DOC U.S. App l ication No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021 SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.4.3.1130.311.1271.387.svg 0.253 0.47 Chemistry Black and white SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.4.4.1139.395.1343.741.svg 1.153 0.68 Chemistry Black and white-CH 3 X (II) wherein each group represented by formula (II) is connected to adjacent two carbon atoms of a carbon ring of the graphene substrate, and each carbon atom of the graphene substrate connects with at most one group represented by formula (II); each X independently represents an electron-withdrawing group; and each R independently represents any one of -R 1, -R 2, -O-R 1, -O-R 2, -R 1 -C 6 H 5, -R 2 -C 6 H 5, and -R 3, wherein each R 1 is independently an n-alkyl group having no less than 5 carbon atoms, each R 2 is independently a substituted n-alkyl group having no less than 5 carbon atoms in its main chain and having an alkyl substituent, the C 6 H 5 represents a phenyl group which is connected to the end of R 1 or R 2, and R 3 is an aryl group, characterized in that the method comprises the following steps: dispersing a graphene in a solvent to form a dispersion, and then mixing the dispersion with N-methyl glycine and a substituted benzaldehyde represented by the following formula to form a reaction mixture, CHO SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.4.20.1242.2397.1474.2690.svg 0.977 0.773 Chemistry Black and white Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 5 of 14 01601751.DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021 wherein the definitions of R and X are the same as described above with respect to the formula (I), respectively; and heating the reaction mixture to a reaction temperature and maintaining the mixture under the temperature to effect reaction, thereby obtaining the graphene derivative.
The method according to claim 7, characterized in that the graphene is a powder of a monolayer graphene having a particle size of 200 nm to 1000 nm.
The method according to claim 7, characterized in that the solvent is selected from the group consisting of toluene, dioxane, tetrahydrofuran, nitrobenzene, and dichloroethane.
The method according to claim 7, characterized in that the molar ratio of the graphene carbon atoms, N-methyl glycine, and substituted benzaldehyde is 1: (1.5 to 5.5): (2 to 12).
The method according to claim 7, characterized in that the reaction mixture is heated to a temperature of 60 to 150 SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.5.15.1085.2147.1147.2190.svg 0.143 0.207 Chemistry Black and white and maintained at the temperature for 8 to 20 hours.
The method according to claim 7, characterized in that the method further comprises: separating the graphene derivative from the reaction mixture by a chromatography process. Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 6 of 1 4 01601751.DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021
Layer stacks claimed or described, ordered top of device to substrate.
transparent conductive film
organic electroluminescent device
Materials described outside the worked examples.
graphene derivative (formula I)
N-methyl glycine
Additional fabrication and treatment steps described in the patent.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
Thickness | 200–1000 nm | — |
Duration |
Related documents with shared materials, methods, properties, or citations.
Patent
Atlas literature
Patent
US 9,252,367Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
A graphene derivative, characterized in that it is represented by the following formula (I): SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.1.6.1039.651.1541.1069.svg 1.393 1.673 Chemistry Black and white (I) wherein: A represents a graphene substrate; n represents the number of the group represented by the following formula (II) and is a positive integer equal to or less than a half (1/2) of the total number of carbon atoms in the graphene substrate: SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.1.15.1130.1738.1270.1814.svg 0.253 0.467 Chemistry Black and white SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.1.16.1137.1821.1342.2167.svg 1.153 0.683 Chemistry Black and white-CH 3 x (II) wherein each group represented by formula (II) is connected to adjacent two carbon atoms of a carbon ring of the graphene substrate, and each carbon atom of the graphene substrate connects with at most one group represented by formula (II); each X independently represents an electron-withdrawing-group -N09 or -CN; and each R independently represents any one of -R 1, -R 2, -O-R 1, -O-R 2, -R 1 -C 6 H 5, -R 2 -C 6 H 5, and -R 3, wherein each R 1 is independently an n-alkyl group having no less than 5 carbon atoms, Frommer Lawrence & H aug LLP 745 Fi ft h Avenue New York, NY 10151 212-588-0800 Page 2 of 14 0160175 1. DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021 each R 2 is independently a substituted n-alkyl group having no less than 5 carbon atoms in its main chain and having an alkyl substituent, the C 6 H 5 represents a phenyl group which is connected to the end of R 1 or R 2, and R 3 is an aryl group.
The graphene derivative according to claim 1, characterized in that the number of the carbon atoms of the graphene substrate is between 500 and 10000.
The graphene derivative according to claim 1, characterized in that the group represented by formula II is a group represented by the following formula Ila: SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.2.10.1068.1333.1208.1411.svg 0.26 0.467 Chemistry Black and white SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.2.11.1080.1418.1307.1739.svg 1.07 0.757 Chemistry Black and white-CH 3 R (Il a).
The graphene derivative according to claim 1, characterized in that, the number of carbon atoms of R 1 ranges from 5 to 20; the number of carbon atoms in the main chain of R 2 ranges from 5 to 20, wherein the alkyl substituent is a methyl or ethyl and is connected to the carbon atom at 2-position or 3- position of the main chain of R 2; and the number of ring carbon atoms in R 3 ranges from 6 to 24. Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 3 of 14 01601751.DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021
A transparent conductive film, characterized in that the film comprises the graphene derivative according to claim 1.
An organic electroluminescent device, including an anode layer, an organic electroluminescent layer, and a cathode layer, characterized in that said anode layer comprises the graphene derivative according to claim 1.
A method of preparing an anode layer on a substrate of an organic electroluminescent device, characterized in that: the graphene derivative according to claim 1 is deposited onto the substrate by a vacuum evaporation at a temperature of 330 to 370 SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.6.11.1171.1461.1231.1496.svg 0.117 0.20 Chemistry Black and white Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 7 of 14 0160175 1. DOC
canceled
A method of preparing a graphene derivative represented by formula (I): SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.3.12.1036.1573.1539.1991.svg 1.393 1.677 Chemistry Black and white (J) wherein: A represents a graphene substrate; n represents the number of the group represented by the following formula (I I) and is a positive integer equal to or less than a half (1/2) of the total number of carbon atoms in the graphene substrate: Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 4 of 1 4 01601751.DOC U.S. App l ication No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021 SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.4.3.1130.311.1271.387.svg 0.253 0.47 Chemistry Black and white SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.4.4.1139.395.1343.741.svg 1.153 0.68 Chemistry Black and white-CH 3 X (II) wherein each group represented by formula (II) is connected to adjacent two carbon atoms of a carbon ring of the graphene substrate, and each carbon atom of the graphene substrate connects with at most one group represented by formula (II); each X independently represents an electron-withdrawing group; and each R independently represents any one of -R 1, -R 2, -O-R 1, -O-R 2, -R 1 -C 6 H 5, -R 2 -C 6 H 5, and -R 3, wherein each R 1 is independently an n-alkyl group having no less than 5 carbon atoms, each R 2 is independently a substituted n-alkyl group having no less than 5 carbon atoms in its main chain and having an alkyl substituent, the C 6 H 5 represents a phenyl group which is connected to the end of R 1 or R 2, and R 3 is an aryl group, characterized in that the method comprises the following steps: dispersing a graphene in a solvent to form a dispersion, and then mixing the dispersion with N-methyl glycine and a substituted benzaldehyde represented by the following formula to form a reaction mixture, CHO SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.4.20.1242.2397.1474.2690.svg 0.977 0.773 Chemistry Black and white Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 5 of 14 01601751.DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021 wherein the definitions of R and X are the same as described above with respect to the formula (I), respectively; and heating the reaction mixture to a reaction temperature and maintaining the mixture under the temperature to effect reaction, thereby obtaining the graphene derivative.
The method according to claim 7, characterized in that the graphene is a powder of a monolayer graphene having a particle size of 200 nm to 1000 nm.
The method according to claim 7, characterized in that the solvent is selected from the group consisting of toluene, dioxane, tetrahydrofuran, nitrobenzene, and dichloroethane.
The method according to claim 7, characterized in that the molar ratio of the graphene carbon atoms, N-methyl glycine, and substituted benzaldehyde is 1: (1.5 to 5.5): (2 to 12).
The method according to claim 7, characterized in that the reaction mixture is heated to a temperature of 60 to 150 SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.5.15.1085.2147.1147.2190.svg 0.143 0.207 Chemistry Black and white and maintained at the temperature for 8 to 20 hours.
The method according to claim 7, characterized in that the method further comprises: separating the graphene derivative from the reaction mixture by a chromatography process. Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 6 of 1 4 01601751.DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021
Layer stacks claimed or described, ordered top of device to substrate.
transparent conductive film
organic electroluminescent device
Materials described outside the worked examples.
graphene derivative (formula I)
N-methyl glycine
Additional fabrication and treatment steps described in the patent.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
Thickness | 200–1000 nm | — |
Duration |
Related documents with shared materials, methods, properties, or citations.
Patent
Atlas literature
Patent
US 9,252,367Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
A graphene derivative, characterized in that it is represented by the following formula (I): SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.1.6.1039.651.1541.1069.svg 1.393 1.673 Chemistry Black and white (I) wherein: A represents a graphene substrate; n represents the number of the group represented by the following formula (II) and is a positive integer equal to or less than a half (1/2) of the total number of carbon atoms in the graphene substrate: SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.1.15.1130.1738.1270.1814.svg 0.253 0.467 Chemistry Black and white SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.1.16.1137.1821.1342.2167.svg 1.153 0.683 Chemistry Black and white-CH 3 x (II) wherein each group represented by formula (II) is connected to adjacent two carbon atoms of a carbon ring of the graphene substrate, and each carbon atom of the graphene substrate connects with at most one group represented by formula (II); each X independently represents an electron-withdrawing-group -N09 or -CN; and each R independently represents any one of -R 1, -R 2, -O-R 1, -O-R 2, -R 1 -C 6 H 5, -R 2 -C 6 H 5, and -R 3, wherein each R 1 is independently an n-alkyl group having no less than 5 carbon atoms, Frommer Lawrence & H aug LLP 745 Fi ft h Avenue New York, NY 10151 212-588-0800 Page 2 of 14 0160175 1. DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021 each R 2 is independently a substituted n-alkyl group having no less than 5 carbon atoms in its main chain and having an alkyl substituent, the C 6 H 5 represents a phenyl group which is connected to the end of R 1 or R 2, and R 3 is an aryl group.
The graphene derivative according to claim 1, characterized in that the number of the carbon atoms of the graphene substrate is between 500 and 10000.
The graphene derivative according to claim 1, characterized in that the group represented by formula II is a group represented by the following formula Ila: SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.2.10.1068.1333.1208.1411.svg 0.26 0.467 Chemistry Black and white SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.2.11.1080.1418.1307.1739.svg 1.07 0.757 Chemistry Black and white-CH 3 R (Il a).
The graphene derivative according to claim 1, characterized in that, the number of carbon atoms of R 1 ranges from 5 to 20; the number of carbon atoms in the main chain of R 2 ranges from 5 to 20, wherein the alkyl substituent is a methyl or ethyl and is connected to the carbon atom at 2-position or 3- position of the main chain of R 2; and the number of ring carbon atoms in R 3 ranges from 6 to 24. Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 3 of 14 01601751.DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021
A transparent conductive film, characterized in that the film comprises the graphene derivative according to claim 1.
An organic electroluminescent device, including an anode layer, an organic electroluminescent layer, and a cathode layer, characterized in that said anode layer comprises the graphene derivative according to claim 1.
A method of preparing an anode layer on a substrate of an organic electroluminescent device, characterized in that: the graphene derivative according to claim 1 is deposited onto the substrate by a vacuum evaporation at a temperature of 330 to 370 SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.6.11.1171.1461.1231.1496.svg 0.117 0.20 Chemistry Black and white Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 7 of 14 0160175 1. DOC
canceled
A method of preparing a graphene derivative represented by formula (I): SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.3.12.1036.1573.1539.1991.svg 1.393 1.677 Chemistry Black and white (J) wherein: A represents a graphene substrate; n represents the number of the group represented by the following formula (I I) and is a positive integer equal to or less than a half (1/2) of the total number of carbon atoms in the graphene substrate: Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 4 of 1 4 01601751.DOC U.S. App l ication No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021 SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.4.3.1130.311.1271.387.svg 0.253 0.47 Chemistry Black and white SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.4.4.1139.395.1343.741.svg 1.153 0.68 Chemistry Black and white-CH 3 X (II) wherein each group represented by formula (II) is connected to adjacent two carbon atoms of a carbon ring of the graphene substrate, and each carbon atom of the graphene substrate connects with at most one group represented by formula (II); each X independently represents an electron-withdrawing group; and each R independently represents any one of -R 1, -R 2, -O-R 1, -O-R 2, -R 1 -C 6 H 5, -R 2 -C 6 H 5, and -R 3, wherein each R 1 is independently an n-alkyl group having no less than 5 carbon atoms, each R 2 is independently a substituted n-alkyl group having no less than 5 carbon atoms in its main chain and having an alkyl substituent, the C 6 H 5 represents a phenyl group which is connected to the end of R 1 or R 2, and R 3 is an aryl group, characterized in that the method comprises the following steps: dispersing a graphene in a solvent to form a dispersion, and then mixing the dispersion with N-methyl glycine and a substituted benzaldehyde represented by the following formula to form a reaction mixture, CHO SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.4.20.1242.2397.1474.2690.svg 0.977 0.773 Chemistry Black and white Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 5 of 14 01601751.DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021 wherein the definitions of R and X are the same as described above with respect to the formula (I), respectively; and heating the reaction mixture to a reaction temperature and maintaining the mixture under the temperature to effect reaction, thereby obtaining the graphene derivative.
The method according to claim 7, characterized in that the graphene is a powder of a monolayer graphene having a particle size of 200 nm to 1000 nm.
The method according to claim 7, characterized in that the solvent is selected from the group consisting of toluene, dioxane, tetrahydrofuran, nitrobenzene, and dichloroethane.
The method according to claim 7, characterized in that the molar ratio of the graphene carbon atoms, N-methyl glycine, and substituted benzaldehyde is 1: (1.5 to 5.5): (2 to 12).
The method according to claim 7, characterized in that the reaction mixture is heated to a temperature of 60 to 150 SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.5.15.1085.2147.1147.2190.svg 0.143 0.207 Chemistry Black and white and maintained at the temperature for 8 to 20 hours.
The method according to claim 7, characterized in that the method further comprises: separating the graphene derivative from the reaction mixture by a chromatography process. Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 6 of 1 4 01601751.DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021
Layer stacks claimed or described, ordered top of device to substrate.
transparent conductive film
organic electroluminescent device
Materials described outside the worked examples.
graphene derivative (formula I)
N-methyl glycine
Additional fabrication and treatment steps described in the patent.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
Thickness | 200–1000 nm | — |
Duration |
Related documents with shared materials, methods, properties, or citations.
Patent
Atlas literature
Patent
US 9,252,367Claims define the patent's legal scope. Independent claims stand alone; dependent claims (nested) narrow them. Click a claim to expand its dependents.
A graphene derivative, characterized in that it is represented by the following formula (I): SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.1.6.1039.651.1541.1069.svg 1.393 1.673 Chemistry Black and white (I) wherein: A represents a graphene substrate; n represents the number of the group represented by the following formula (II) and is a positive integer equal to or less than a half (1/2) of the total number of carbon atoms in the graphene substrate: SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.1.15.1130.1738.1270.1814.svg 0.253 0.467 Chemistry Black and white SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.1.16.1137.1821.1342.2167.svg 1.153 0.683 Chemistry Black and white-CH 3 x (II) wherein each group represented by formula (II) is connected to adjacent two carbon atoms of a carbon ring of the graphene substrate, and each carbon atom of the graphene substrate connects with at most one group represented by formula (II); each X independently represents an electron-withdrawing-group -N09 or -CN; and each R independently represents any one of -R 1, -R 2, -O-R 1, -O-R 2, -R 1 -C 6 H 5, -R 2 -C 6 H 5, and -R 3, wherein each R 1 is independently an n-alkyl group having no less than 5 carbon atoms, Frommer Lawrence & H aug LLP 745 Fi ft h Avenue New York, NY 10151 212-588-0800 Page 2 of 14 0160175 1. DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021 each R 2 is independently a substituted n-alkyl group having no less than 5 carbon atoms in its main chain and having an alkyl substituent, the C 6 H 5 represents a phenyl group which is connected to the end of R 1 or R 2, and R 3 is an aryl group.
The graphene derivative according to claim 1, characterized in that the number of the carbon atoms of the graphene substrate is between 500 and 10000.
The graphene derivative according to claim 1, characterized in that the group represented by formula II is a group represented by the following formula Ila: SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.2.10.1068.1333.1208.1411.svg 0.26 0.467 Chemistry Black and white SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.2.11.1080.1418.1307.1739.svg 1.07 0.757 Chemistry Black and white-CH 3 R (Il a).
The graphene derivative according to claim 1, characterized in that, the number of carbon atoms of R 1 ranges from 5 to 20; the number of carbon atoms in the main chain of R 2 ranges from 5 to 20, wherein the alkyl substituent is a methyl or ethyl and is connected to the carbon atom at 2-position or 3- position of the main chain of R 2; and the number of ring carbon atoms in R 3 ranges from 6 to 24. Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 3 of 14 01601751.DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021
A transparent conductive film, characterized in that the film comprises the graphene derivative according to claim 1.
An organic electroluminescent device, including an anode layer, an organic electroluminescent layer, and a cathode layer, characterized in that said anode layer comprises the graphene derivative according to claim 1.
A method of preparing an anode layer on a substrate of an organic electroluminescent device, characterized in that: the graphene derivative according to claim 1 is deposited onto the substrate by a vacuum evaporation at a temperature of 330 to 370 SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.6.11.1171.1461.1231.1496.svg 0.117 0.20 Chemistry Black and white Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 7 of 14 0160175 1. DOC
canceled
A method of preparing a graphene derivative represented by formula (I): SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.3.12.1036.1573.1539.1991.svg 1.393 1.677 Chemistry Black and white (J) wherein: A represents a graphene substrate; n represents the number of the group represented by the following formula (I I) and is a positive integer equal to or less than a half (1/2) of the total number of carbon atoms in the graphene substrate: Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 4 of 1 4 01601751.DOC U.S. App l ication No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021 SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.4.3.1130.311.1271.387.svg 0.253 0.47 Chemistry Black and white SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.4.4.1139.395.1343.741.svg 1.153 0.68 Chemistry Black and white-CH 3 X (II) wherein each group represented by formula (II) is connected to adjacent two carbon atoms of a carbon ring of the graphene substrate, and each carbon atom of the graphene substrate connects with at most one group represented by formula (II); each X independently represents an electron-withdrawing group; and each R independently represents any one of -R 1, -R 2, -O-R 1, -O-R 2, -R 1 -C 6 H 5, -R 2 -C 6 H 5, and -R 3, wherein each R 1 is independently an n-alkyl group having no less than 5 carbon atoms, each R 2 is independently a substituted n-alkyl group having no less than 5 carbon atoms in its main chain and having an alkyl substituent, the C 6 H 5 represents a phenyl group which is connected to the end of R 1 or R 2, and R 3 is an aryl group, characterized in that the method comprises the following steps: dispersing a graphene in a solvent to form a dispersion, and then mixing the dispersion with N-methyl glycine and a substituted benzaldehyde represented by the following formula to form a reaction mixture, CHO SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.4.20.1242.2397.1474.2690.svg 0.977 0.773 Chemistry Black and white Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 5 of 14 01601751.DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021 wherein the definitions of R and X are the same as described above with respect to the formula (I), respectively; and heating the reaction mixture to a reaction temperature and maintaining the mixture under the temperature to effect reaction, thereby obtaining the graphene derivative.
The method according to claim 7, characterized in that the graphene is a powder of a monolayer graphene having a particle size of 200 nm to 1000 nm.
The method according to claim 7, characterized in that the solvent is selected from the group consisting of toluene, dioxane, tetrahydrofuran, nitrobenzene, and dichloroethane.
The method according to claim 7, characterized in that the molar ratio of the graphene carbon atoms, N-methyl glycine, and substituted benzaldehyde is 1: (1.5 to 5.5): (2 to 12).
The method according to claim 7, characterized in that the reaction mixture is heated to a temperature of 60 to 150 SVG 14091587.11-04-2015.IGLBWV₉₂PXXIFW3.CLM.5.15.1085.2147.1147.2190.svg 0.143 0.207 Chemistry Black and white and maintained at the temperature for 8 to 20 hours.
The method according to claim 7, characterized in that the method further comprises: separating the graphene derivative from the reaction mixture by a chromatography process. Frommer Lawrence & Haug LLP 745 Fifth Avenue New York, NY 10151 212-588-0800 Page 6 of 1 4 01601751.DOC U.S. Application No. 14/091,587 PATENT Reply to Final Office Action dated 930103-2021
Layer stacks claimed or described, ordered top of device to substrate.
transparent conductive film
organic electroluminescent device
Materials described outside the worked examples.
graphene derivative (formula I)
N-methyl glycine
Additional fabrication and treatment steps described in the patent.
Performance values and ranges asserted in the specification or claims.
| Property | Value | Material |
|---|---|---|
Thickness | 200–1000 nm | — |
Duration |
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