CN111056946A - Conductive material, light-emitting device and preparation method of light-emitting device - Google Patents
Conductive material, light-emitting device and preparation method of light-emitting device Download PDFInfo
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- CN111056946A CN111056946A CN201911077551.7A CN201911077551A CN111056946A CN 111056946 A CN111056946 A CN 111056946A CN 201911077551 A CN201911077551 A CN 201911077551A CN 111056946 A CN111056946 A CN 111056946A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
- H10K85/211—Fullerenes, e.g. C60
- H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2604/00—Fullerenes, e.g. C60 buckminsterfullerene or C70
Abstract
The present application provides a conductive material, a light emitting device, and a method for manufacturing a light emitting device, by providing a fullerene derivative as a conductive material, and coating a solution including the conductive material on a first electrode layer of the light emitting device to form an electron injection layer, thereby providing a low-cost conductive material, a light emitting device, and a method for manufacturing a light emitting device.
Description
Technical Field
The application relates to a conductive material, a light emitting device and a preparation method of the light emitting device.
Background
In the prior art, the electron injection layer is usually completed by a vacuum evaporation method, however, the vacuum evaporation process is complex, and vacuum evaporation equipment is required, which results in high cost. Therefore, how to provide a conductive material with low cost, a light emitting device and a method for manufacturing the light emitting device is a problem to be solved.
Disclosure of Invention
The application provides a conductive material, a light-emitting device and a preparation method of the light-emitting device, which aim to solve the problem of high cost in the process of manufacturing an electron injection layer at present.
The present application provides a conductive material, the structural formula of the conductive material
Wherein R is1Is a benzene ring, an aromatic conjugated carbocycle or an aromatic heterocycle, R2Is an alkyl chain with the main chain carbon atom number of 3-7, and R is3Is an alkyl chain with the main chain carbon atom number of 1-5.
The present application provides a light emitting device comprising:
a substrate;
a first electrode layer disposed on the substrate;
an electron injection layer disposed on the first electrode layer, wherein the electron injection layer comprises a conductive material having a structural formula
Wherein R is1Is a benzene ring, an aromatic conjugated carbocycle or an aromatic heterocycle, R2Is an alkyl chain with the main chain carbon atom number of 3-7, and R is3Is an alkyl chain with the main chain carbon atom number of 1-5;
a light emitting layer disposed on the electron injection layer;
a hole injection layer disposed on the light emitting layer; and
a second electrode layer disposed on the hole injection layer.
In the light emitting device provided by the present application, the thickness of the electron injection layer is 10 nm to 20 nm.
In the light emitting device provided by the present application, the thickness of the light emitting layer is 30 nm to 50 nm.
In the light emitting device provided by the present application, the thickness of the hole injection layer is 8 nm to 15 nm.
The application provides a method for preparing a light-emitting device, which comprises the following steps:
providing a substrate;
arranging a first electrode layer on the substrate;
an electron injection layer is arranged on the first electrode layer, wherein the electron injection layer comprises a conductive material, and the structural formula of the conductive material
Wherein R is1Is a benzene ring, an aromatic conjugated carbocycle or an aromatic heterocycle, R2Is an alkyl chain with the main chain carbon atom number of 3-7, and R is3Is an alkyl chain with the main chain carbon atom number of 1-5;
disposing a light emitting layer on the electron injection layer;
a hole injection layer is arranged on the light-emitting layer;
and arranging a second electrode layer on the hole injection layer.
In the method for manufacturing a light emitting device provided by the present application, in the step of providing an electron injection layer on the first electrode layer, the method includes:
preparing a first solution, wherein the first solution comprises the conductive material and a first solvent, and the corresponding relation between the mass of the conductive material and the volume of the first solvent is that 10 milligrams of the conductive material correspond to 2-10 milliliters of the first solvent; and
and coating the first solution on the first electrode layer to form the electron injection layer.
In the preparation method of the light-emitting device provided by the application, the first solvent is triethylene glycol dimethyl ether and toluene. One or more of diethyl ether, acetone and triethanolamine.
In the method for manufacturing a light-emitting device provided by the present application, the step of providing a light-emitting layer on the electron injection layer includes:
preparing a second solution, wherein the second solution comprises a luminescent material and a second solvent, and the corresponding relation between the mass of the luminescent material and the volume of the second solvent is that 8 mg of the luminescent material corresponds to 1 ml to 5 ml of the second solvent; and
and applying the second solution to the electron injection layer to form the light-emitting layer.
In the method for manufacturing a light-emitting device provided by the present application, the step of providing a hole injection layer on the light-emitting layer includes:
preparing a third solution, wherein the third solution comprises a hole injection material and a third solvent, and the mass of the hole injection material and the volume of the third solvent are in a corresponding relation that 1 mg of the hole injection material corresponds to 0.5 ml to 2 ml of the third solvent; and
and coating the third solution on the light-emitting layer to form the hole injection layer.
The application provides a conductive material, a light-emitting device and a preparation method of the light-emitting device, wherein the conductive material has a structural formula
Wherein R is1Is a benzene ring, an aromatic conjugated carbocycle or an aromatic heterocycle, R2Is an alkyl chain with the main chain carbon atom number of 3-7, and R is3The conductive material, the light emitting device and the method for manufacturing the light emitting device are provided at low cost by providing the conductive material, and applying a solution including the conductive material on the first electrode layer of the light emitting device to form an electron injection layer.
Drawings
In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings needed to be used in the description of the embodiments are briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present application, and it is obvious for those skilled in the art to obtain other drawings based on these drawings without creative efforts.
Fig. 1 is a schematic structural diagram of a light emitting device provided in the present application.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present application.
The present application provides a conductive material, the structural formula of the conductive material
Wherein R is1Is a benzene ring, an aromatic conjugated carbocycle or an aromatic heterocycle, R2Is an alkyl chain with the main chain carbon atom number of 3-7, and R is3Is an alkyl chain with the main chain carbon atom number of 1-5. The conductive material is a derivative of fullerene. The fullerene may have a carbon number of 60.
In some embodiments, the conductive material can have a structure of
And the like.
Referring to fig. 1, the present application provides a light emitting device 10. The light emitting device 10 includes a substrate 11, a first electrode layer 12, an electron injection layer 13, a light emitting layer 14, a hole injection layer 15, and a second electrode layer 16.
The first electrode layer 12 is disposed on the substrate 11. The substrate 11 may be glass or plastic. The first electrode layer 12 may be indium tin oxide. The thickness of the first electrode layer 12 is 100 nm to 250 nm. In some embodiments, the thickness of the first electrode layer 12 may be 150 nanometers, 180 nanometers, or 200 nanometers.
The electron injection layer 13 is disposed on the first electrode layer 12. The electron injection layer 13 includes a conductive material. Structural formula of the conductive material
Wherein. R1Is a benzene ring, an aromatic conjugated carbocycle or an aromatic heterocycle. R2Is an alkyl chain with the main chain carbon number of 3-7. The R is3Is an alkyl chain with the main chain carbon atom number of 1-5. The thickness of the electron injection layer 13 is 10 nm to 20 nm. In some embodiments, the thickness of the electron injection layer 13 may be 12 nm, 15 nm, or 18 nm.
In some embodiments, the conductive material can have a structure of
And the like.
The light emitting layer 14 is disposed on the electron injection layer 13. The light-emitting layer 14 comprises a light-emitting material. The luminescent material may be a soluble polyparaphenylene vinylene, for example, poly [ 2-methoxy-5- (2-ethylhexyloxy) ] p-phenylene vinylene. The thickness of the light emitting layer 14 is 30 nm to 50 nm. In some embodiments, the thickness of the light emitting layer 14 may be 35 nanometers, 40 nanometers, or 48 nanometers.
The hole injection layer 15 is provided on the light emitting layer 14. The hole injection layer 15 includes a hole injection material. In one embodiment, the hole injection material may be MoO3. In other embodiments, the hole injection material may be V2O5. The thickness of the hole injection layer 15 is 8 nm to 15 nm. In some embodiments, the hole injection layer 15 may have a thickness of 10 nanometers, 12 nanometers, or 13 nanometers.
The second electrode layer 16 is disposed on the hole injection layer 15. The second electrode layer 16 may be poly 3, 4-ethylenedioxythiophene/polystyrene sulfonate. The thickness of the second electrode layer 16 may be 200 nanometers to 3 micrometers. In some embodiments, the thickness of the second electrode layer 16 may be 500 nanometers, 1 micron, or 2 microns.
The present application provides a method of manufacturing a light emitting device 10, comprising:
101, a substrate 11 is provided.
In one embodiment, the substrate 11 may be glass or plastic.
102, a first electrode layer 12 is disposed on the substrate 11.
In one embodiment, the first electrode layer 12 may be indium tin oxide. The thickness of the first electrode layer 12 is 100 nm to 250 nm. In some embodiments, the thickness of the first electrode layer 12 may be 150 nanometers, 180 nanometers, or 200 nanometers.
103, an electron injection layer 13 is disposed on the first electrode layer 12.
The electron injection layer 13 includes a conductive material having a structural formula
Wherein R is1Is a benzene ring, an aromatic conjugated carbocycle or an aromatic heterocycle, R2Is an alkyl chain with the main chain carbon atom number of 3-7, and R is3Is an alkyl chain with the main chain carbon atom number of 1-5. The thickness of the electron injection layer 13 is 10 nm to 20 nm. In some embodiments, the thickness of the electron injection layer 13 may be 12 nm, 15 nm, or 18 nm.
In some embodiments, the conductive material can have a structure of
And the like.
In the step of disposing an electron injection layer 13 on the first electrode layer 12, the method includes:
1031, preparing a first solution, wherein the first solution comprises the conductive material and a first solvent, and the corresponding relationship between the mass of the conductive material and the volume of the first solvent is that 10 mg of the conductive material corresponds to 2-10 ml of the first solvent; and
1032, the first solution is coated on the first electrode layer 12 to form the electron injection layer 13.
In some embodiments, the correspondence between the mass of the conductive material and the volume of the first solvent may be 10 milligrams of the conductive material for 3 milliliters of the first solvent, 10 milligrams of the conductive material for 5 milliliters of the first solvent, or 10 milligrams of the conductive material for 8 milliliters of the first solvent. The first solvent is triethylene glycol dimethyl ether and toluene. One or more of diethyl ether, acetone and triethanolamine.
In one embodiment, 10 mg of the conductive material is weighed, the conductive material is dissolved in 5 ml of toluene to form the first solution, the first solution is spin-coated on the first electrode layer 12 of the substrate 11 by using a spin coater at a rotation speed of 800rmp-1500rmp to obtain a first semi-finished product, the first semi-finished product is dried, and the first semi-finished product is annealed at a temperature of 40 ℃ to 80 ℃ for 15 minutes to obtain a second semi-finished product. The second semi-finished product comprises the substrate 11, the first electrode layer 12 and the electron injection layer 13.
104, a light emitting layer 14 is disposed on the electron injection layer 13.
The light-emitting layer 14 comprises a light-emitting material. The luminescent material may be a soluble polyparaphenylene vinylene, for example, poly [ 2-methoxy-5- (2-ethylhexyloxy) ] p-phenylene vinylene. The thickness of the light emitting layer 14 is 30 nm to 50 nm. In some embodiments, the thickness of the light emitting layer 14 may be 35 nanometers, 40 nanometers, or 48 nanometers.
In the method for manufacturing the light-emitting device 10 provided by the present application, in the step of providing the light-emitting layer 14 on the electron injection layer 13, the method includes:
1041, preparing a second solution comprising a luminescent material and a second solvent, wherein a mass of the luminescent material and a volume of the second solvent are related in a manner that 8 mg of the luminescent material corresponds to 1 ml to 5 ml of the second solvent; and
1042 and applying the second solution to the electron injection layer 13 to form the light emitting layer 14.
In some embodiments, the correspondence between the mass of the luminescent material and the volume of the second solvent may be 8 mg of the luminescent material for 3 ml of the second solvent, 4 mg of the luminescent material for 1.5 ml of the second solvent, or 10 mg of the luminescent material for 5 ml of the second solvent. The second solvent may be one or a combination of toluene, xylene and chloroform.
In one embodiment, a second solution is prepared, in which the corresponding relationship between the mass of the luminescent material and the volume of the second solvent may be 4 mg of the luminescent material to 1 ml of the second solvent, the second solvent may be chloroform, the second solution is spin-coated on the electron injection layer 13 by using a spin coater at a rotation speed of 1500rmp-3000rmp to obtain a third semi-finished product, and the third semi-finished product is baked in a vacuum oven at 100 ℃ for 1 hour to obtain a fourth semi-finished product. The fourth semi-finished product includes the substrate 11, the first electrode layer 12, the electron injection layer 13, and the light-emitting layer 14.
105, a hole injection layer 15 is provided on the light emitting layer 14.
The hole injection layer 15 includes a hole injection material. In one embodiment, the hole injection material may be MoO3. In other embodiments, the hole injection material may be V2O5. The thickness of the hole injection layer 15 is 8 nm to 15 nm. In some embodiments, the hole injection layer 15 may have a thickness of 10 nanometers, 12 nanometers, or 13 nanometers.
In the method for manufacturing the light-emitting device 10 provided by the present application, the step of providing a hole injection layer 15 on the light-emitting layer 14 includes:
1051, preparing a third solution comprising a hole injection material and a third solvent, the corresponding relationship between the mass of the hole injection material and the volume of the third solvent being 1 mg of the hole injection material to 0.5 ml to 2 ml of the third solvent; and
1052 applying the third solution to the light emitting layer 14 to form the hole injection layer 15.
In some embodiments, the correspondence between the mass of the hole injection material and the volume of the third solvent may be 2 mg of the hole injection material for 1.2 ml of the third solvent, 1 mg of the hole injection material for 1.5 ml of the third solvent, or 2 mg of the hole injection material for 3 ml of the third solvent. The third solvent may be water.
In one embodiment, a third solution is prepared in which the corresponding relationship between the mass of the hole injection material and the volume of the third solvent is 1 mg of the hole injection material for 1 ml of the third solvent, and the hole injection material may be MoO3And the third solvent can be water, the third solution is spin-coated on the light-emitting layer 14 by using a spin coater to obtain a fifth semi-finished product, the rotating speed of the spin coater is 4500-7000 rmp, and the fifth semi-finished product is baked in a vacuum oven at 150-180 ℃ for 5-15 minutes to obtain a sixth semi-finished product. The sixth semi-finished product includes the substrate 11, the first electrode layer 12, the electron injection layer 13, the light-emitting layer 14, and the hole injection layer 15.
106, a second electrode layer 16 is disposed on the hole injection layer 15.
The second electrode layer 16 may be poly 3, 4-ethylenedioxythiophene/polystyrene sulfonate. The thickness of the second electrode layer 16 may be 200 nanometers to 3 micrometers. In some embodiments, the thickness of the second electrode layer 16 may be 500 nanometers, 1 micron, or 2 microns.
In one embodiment, a solution of poly (3, 4-ethylenedioxythiophene)/polystyrene sulfonate (pdps) may be drop coated onto the hole injection layer 15 to form a seventh semi-finished product, and the seventh semi-finished product may be baked at 150 degrees celsius for half an hour in a vacuum oven to form the light emitting device 10.
The application provides a conductive material, a light emitting device and a light emitting deviceMethod for preparing optical device, structural formula of conductive material
Wherein R is1Is a benzene ring, an aromatic conjugated carbocycle or an aromatic heterocycle, R2Is an alkyl chain with the main chain carbon atom number of 3-7, and R is3An electron injection layer is formed by providing a fullerene derivative as a conductive material for an alkyl chain having a main chain carbon number of 1 to 5 and applying a solution including the conductive material on a first electrode layer of a light emitting device, and a low-cost conductive material, a light emitting device, and a method for manufacturing the light emitting device are provided by a full solution method.
The foregoing provides a detailed description of embodiments of the present application, and the principles and embodiments of the present application have been described herein using specific examples, which are presented solely to aid in the understanding of the present application. Meanwhile, for those skilled in the art, according to the idea of the present application, there may be variations in the specific embodiments and the application scope, and in summary, the content of the present specification should not be construed as a limitation to the present application.
Claims (10)
1. The conductive material is characterized in that the structural formula of the conductive material
Wherein R is1Is a benzene ring, an aromatic conjugated carbocycle or an aromatic heterocycle, R2Is an alkyl chain with the main chain carbon atom number of 3-7, and R is3Is an alkyl chain with the main chain carbon atom number of 1-5.
2. A light emitting device, comprising:
a substrate;
a first electrode layer disposed on the substrate;
an electron injection layer disposed on the first electrode layer, wherein the electron injection layer comprises a conductive material having a structural formula
Wherein R is1Is a benzene ring, an aromatic conjugated carbocycle or an aromatic heterocycle, R2Is an alkyl chain with the main chain carbon atom number of 3-7, and R is3Is an alkyl chain with the main chain carbon atom number of 1-5;
a light emitting layer disposed on the electron injection layer;
a hole injection layer disposed on the light emitting layer; and
a second electrode layer disposed on the hole injection layer.
3. The light-emitting device according to claim 2, wherein the electron injection layer has a thickness of 10 nm to 20 nm.
4. The light-emitting device according to claim 2, wherein the light-emitting layer has a thickness of 30 nm to 50 nm.
5. The light-emitting device according to claim 2, wherein the hole injection layer has a thickness of 8 nm to 15 nm.
6. A method of making a light emitting device, comprising:
providing a substrate;
arranging a first electrode layer on the substrate;
an electron injection layer is arranged on the first electrode layer, wherein the electron injection layer comprises a conductive material, and the structural formula of the conductive material
Wherein R is1Is a benzene ring, an aromatic conjugated carbocycle or an aromatic heterocycle, R2Is an alkyl chain with the main chain carbon atom number of 3-7, and R is3Is an alkyl chain with the main chain carbon atom number of 1-5;
disposing a light emitting layer on the electron injection layer;
a hole injection layer is arranged on the light-emitting layer;
and arranging a second electrode layer on the hole injection layer.
7. The method for manufacturing a light-emitting device according to claim 6, wherein the step of providing an electron injection layer on the first electrode layer comprises:
preparing a first solution, wherein the first solution comprises the conductive material and a first solvent, and the corresponding relation between the mass of the conductive material and the volume of the first solvent is that 10 milligrams of the conductive material correspond to 2-10 milliliters of the first solvent; and
and coating the first solution on the first electrode layer to form the electron injection layer.
8. The method of claim 7, wherein the first solvent is one or more selected from the group consisting of triglyme, toluene, diethyl ether, acetone, and triethanolamine.
9. The method for manufacturing a light-emitting device according to claim 6, wherein the step of providing a light-emitting layer over the electron-injecting layer comprises:
preparing a second solution, wherein the second solution comprises a luminescent material and a second solvent, and the corresponding relation between the mass of the luminescent material and the volume of the second solvent is that 8 mg of the luminescent material corresponds to 1 ml to 5 ml of the second solvent; and
and applying the second solution to the electron injection layer to form the light-emitting layer.
10. The method for manufacturing a light-emitting device according to claim 6, wherein the step of providing a hole injection layer over the light-emitting layer comprises:
preparing a third solution, wherein the third solution comprises a hole injection material and a third solvent, and the mass of the hole injection material and the volume of the third solvent are in a corresponding relation that 1 mg of the hole injection material corresponds to 0.5 ml to 2 ml of the third solvent; and
and coating the third solution on the light-emitting layer to form the hole injection layer.
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| CN201911077551.7A CN111056946A (en) | 2019-11-06 | 2019-11-06 | Conductive material, light-emitting device and preparation method of light-emitting device |
| PCT/CN2019/118414 WO2021088105A1 (en) | 2019-11-06 | 2019-11-14 | Conductive material, light-emitting device and preparation method for light-emitting device |
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| WO2011010526A1 (en) * | 2009-07-24 | 2011-01-27 | 地方独立行政法人大阪市立工業研究所 | Methanofullerene derivatives and photoelectric conversion elements using same |
| CN102473852A (en) * | 2009-07-14 | 2012-05-23 | 住友化学株式会社 | Organic electroluminescent element and high-molecular light-emitting composition |
| CN108242508A (en) * | 2016-12-26 | 2018-07-03 | 昆山国显光电有限公司 | Electron transfer layer and preparation method thereof and organic luminescent device |
| CN110268538A (en) * | 2016-12-27 | 2019-09-20 | 埃尼股份公司 | Hole mobile material and the photovoltaic devices for using the hole mobile material |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6734625B2 (en) * | 2002-07-30 | 2004-05-11 | Xerox Corporation | Organic light emitting device (OLED) with multiple capping layers passivation region on an electrode |
| US20040247933A1 (en) * | 2003-06-03 | 2004-12-09 | Canon Kabushiki Kaisha | Bipolar asymmetric carbazole-based host materials for electrophosphorescent guest-host OLED systems |
| CN108565339B (en) * | 2018-01-11 | 2022-01-04 | 华南师范大学 | Perovskite solar cell containing fullerene derivative and preparation method thereof |
| CN109524564B (en) * | 2018-11-23 | 2021-01-08 | 合肥鑫晟光电科技有限公司 | Organic light-emitting transistor, temperature sensing device and temperature testing method thereof |
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- 2019-11-06 CN CN201911077551.7A patent/CN111056946A/en active Pending
- 2019-11-14 WO PCT/CN2019/118414 patent/WO2021088105A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102473852A (en) * | 2009-07-14 | 2012-05-23 | 住友化学株式会社 | Organic electroluminescent element and high-molecular light-emitting composition |
| WO2011010526A1 (en) * | 2009-07-24 | 2011-01-27 | 地方独立行政法人大阪市立工業研究所 | Methanofullerene derivatives and photoelectric conversion elements using same |
| CN108242508A (en) * | 2016-12-26 | 2018-07-03 | 昆山国显光电有限公司 | Electron transfer layer and preparation method thereof and organic luminescent device |
| CN110268538A (en) * | 2016-12-27 | 2019-09-20 | 埃尼股份公司 | Hole mobile material and the photovoltaic devices for using the hole mobile material |
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Application publication date: 20200424 |
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| RJ01 | Rejection of invention patent application after publication |