CN111116946B - Hole transport material, display panel and manufacturing method thereof - Google Patents
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Abstract
The application discloses a hole transport material, a display panel and a manufacturing method thereof, wherein the hole transport material comprises a cross-linked polymer formed by cross-linking a first precursor polymer and a second precursor polymer; the first precursor polymer comprises a first backbone repeating unit and at least one first crosslinking group attached to the first backbone repeating unit; the first backbone repeating unit comprises a carbazole group or a carbazole derivative group; the second precursor polymer comprises a second backbone repeating unit and at least one second crosslinking group connected with the second backbone repeating unit, and the second backbone repeating unit comprises a triarylamine group or a derivative group of triphenylamine; the crosslinked polymer is formed by crosslinking a first crosslinking group of a first precursor polymer with a second crosslinking group of a second precursor polymer. The application provides a hole transport material with excellent hole transport performance, and effectively solves the problem of mutual solubility between different functional layers of a display panel.
Description
Technical Field
The application relates to the technical field of display panels, in particular to a hole transport material, a display panel and a manufacturing method thereof.
Background
The inkjet Printing (IJP) OLED (Organic Light-Emitting Diode Display) technology has the advantages of low large-area processing cost, no need of a fine metal mask plate, high material utilization rate and the like, and is considered as a development direction of future OLEDs, so that the production cost of the OLEDs can be significantly reduced.
The OLED light emitting device in the OLED display panel is generally a multi-layer device structure, and includes a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), an emission layer (EML), and the like, where the hole transport layer can balance the transport of carriers, which is very helpful to improve the efficiency of the device and increase the lifetime of the device. However, the solution method for preparing a multilayer device has the problem that the upper and lower functional layers are mutually soluble. One of the common solutions is to use orthogonal solvents to prepare a multilayer device, but because the material structures of each layer of the device of the OLED are usually relatively close and various parameters such as boiling point, viscosity, surface tension and the like suitable for ink printing need to be met, the implementation of the method is relatively difficult; the second method adopts a cross-linking technology, and the film formed by cross-linking has solvent resistance, so that the multilayer OLED device structure can be prepared by a solution method. However, the current solution-processed hole transport layer has fewer materials and a shallower HOMO level, which is not favorable for development of IJP OLED devices and limits the development of preparing OLEDs by inkjet printing technology.
Therefore, it is very important to design and develop a hole transport material with excellent hole transport properties to meet the requirements of preparing OLEDs by a solution method.
Disclosure of Invention
The embodiment of the application provides a hole transport material, a display panel and a manufacturing method thereof, provides the hole transport material with excellent hole transport performance, and effectively solves the problem that different functional layers of the display panel are mutually soluble.
Embodiments provide a hole transport material comprising a crosslinked polymer formed by crosslinking a first precursor polymer and a second precursor polymer; the first precursor polymer comprises a first backbone repeating unit and at least one first crosslinking group attached to the first backbone repeating unit; the first backbone repeating unit comprises a carbazole group or a carbazole derivative group; the second precursor polymer comprises a second backbone repeating unit comprising a triarylamine group or a derivative group of triphenylamine, and at least one second crosslinking group attached to the second backbone repeating unit;
the crosslinked polymer is formed by crosslinking the first crosslinking group of the first precursor polymer with the second crosslinking group of the second precursor polymer.
Optionally, the first backbone repeating unit comprises a 1, 3-dicarbazole-9-ylphenyl group; the second backbone repeating unit comprises an N, N' -tetraphenyldiaminobiphenyl group.
Optionally, the first crosslinking group and the second crosslinking group both comprise a styrene group or an alkylene oxide group.
Optionally, the first precursor polymer further comprises a first bridging group connecting the first backbone repeating unit and the first crosslinking group, the first bridging group comprising an alkane group.
Optionally, the second precursor polymer further comprises a second bridging group connecting the second backbone repeating unit and the second crosslinking group, the second bridging group comprising an alkane group.
The embodiment of the application also provides a display panel, which comprises an anode, and a hole injection layer and a hole transport layer which are sequentially arranged on the anode; wherein the material of the hole transport layer comprises the hole transport material.
The embodiment of the application also provides a manufacturing method of the display panel, which comprises the following steps:
forming a hole injection layer on the anode;
forming a hole transport layer on the hole injection layer; the material of the hole transport layer includes a crosslinked polymer formed by crosslinking a first precursor polymer and a second precursor polymer; the first precursor polymer comprises a first backbone repeating unit and at least one first crosslinking group attached to the first backbone repeating unit; the first backbone repeat unit comprises a carbazole group or a carbazole derivative group; the second precursor polymer comprises a second backbone repeating unit comprising a triarylamine group or a derivative of triphenylamine, and at least one second crosslinking group attached to the second backbone repeating unit; the first precursor polymer and the second precursor polymer are crosslinked by the first crosslinking group and the second crosslinking group to form the crosslinked polymer.
Optionally, the forming a hole transport layer on the hole injection layer includes:
dissolving the first precursor polymer and the second precursor polymer into a solvent, and adding a surface tension adjusting agent and a viscosity adjusting agent to the solvent to form a hole transport ink;
printing the hole-transporting ink on the hole-injecting layer;
removing the solvent in the hole transport ink, and causing the first crosslinking group in the first precursor polymer and the second crosslinking group in the second precursor polymer to undergo a crosslinking reaction by heat treatment to form the hole transport layer.
Optionally, in the hole transport ink, the molar ratio of the first precursor polymer to the second precursor polymer is 1.
Optionally, the solvent comprises one or more of aromatic hydrocarbons, ethers and alcohols.
The beneficial effect of this application does: the hole transport material provided by the application is a cross-linked polymer formed by cross-linking a first precursor polymer and a second precursor polymer, wherein the first precursor polymer is a carbazole polymer and has a deeper HOMO energy level, the second precursor polymer is a triarylamine polymer and has higher hole mobility, and the two polymers can form a uniform and stable anti-solvent cross-linked polymer film (a hole transport layer) through cross-linking.
Drawings
The technical solutions and other advantages of the present application will become apparent from the following detailed description of specific embodiments of the present application when taken in conjunction with the accompanying drawings.
Fig. 1 is a schematic structural diagram of a display panel according to an embodiment of the present disclosure;
fig. 2 is a schematic structural diagram of another display panel provided in the embodiment of the present application;
fig. 3 is a schematic flowchart of a method for manufacturing a display panel according to an embodiment of the present disclosure.
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. It is to be understood that the embodiments described are only a few embodiments of the present application and not all 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.
In the description of the present application, it is to be understood that the terms "center," "longitudinal," "lateral," "length," "width," "thickness," "upper," "lower," "front," "rear," "left," "right," "vertical," "horizontal," "top," "bottom," "inner," "outer," "clockwise," "counterclockwise," and the like are used in the orientations and positional relationships indicated in the drawings for convenience in describing the present application and for simplicity in description, and are not intended to indicate or imply that the referenced devices or elements must have a particular orientation, be constructed in a particular orientation, and be operated in a particular manner, and are not to be construed as limiting the present application. Furthermore, the terms "first", "second" and "first" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, features defined as "first", "second", may explicitly or implicitly include one or more of the described features. In the description of the present application, "a plurality" means two or more unless specifically limited otherwise.
In the description of the present application, it is to be noted that, unless otherwise explicitly specified or limited, the terms "mounted," "connected," and "connected" are to be construed broadly, e.g., as meaning either a fixed connection, a removable connection, or an integral connection; may be mechanically connected, may be electrically connected or may be in communication with each other; they may be directly connected or indirectly connected through intervening media, or may be connected through the use of two elements or the interaction of two elements. The specific meaning of the above terms in the present application can be understood by those of ordinary skill in the art as appropriate.
In this application, unless expressly stated or limited otherwise, the first feature "on" or "under" the second feature may comprise direct contact of the first and second features, or may comprise contact of the first and second features not directly but through another feature in between. Also, the first feature being "on," "above" and "over" the second feature includes the first feature being directly on and obliquely above the second feature, or merely indicating that the first feature is at a higher level than the second feature. A first feature being "under," "below," and "beneath" a second feature includes the first feature being directly under and obliquely below the second feature, or simply meaning that the first feature is at a lesser elevation than the second feature.
The following disclosure provides many different embodiments or examples for implementing different features of the application. In order to simplify the disclosure of the present application, specific example components and arrangements are described below. Of course, they are merely examples and are not intended to limit the present application. Moreover, the present application may repeat reference numerals and/or letters in the various examples, such repetition is for the purpose of simplicity and clarity and does not in itself dictate a relationship between the various embodiments and/or configurations discussed. In addition, examples of various specific processes and materials are provided herein, but one of ordinary skill in the art may recognize applications of other processes and/or use of other materials.
As shown in fig. 1, an embodiment of the present application provides a display panel 1, specifically an OLED display panel, where the display panel 1 includes a substrate 11, and an anode 12, a hole injection layer 13, a hole transport layer 14, an organic light emitting layer 15, an electron transport layer 16, an electron injection layer 17, and a cathode 18 sequentially disposed on the substrate 11; wherein the material of the hole transport layer 14 is a hole transport material, and the hole transport material includes a crosslinked polymer formed by crosslinking a first precursor polymer and a second precursor polymer; the first precursor polymer comprises a first backbone repeating unit and at least one first crosslinking group attached to the first backbone repeating unit; the first backbone repeating unit comprises a carbazole group or a carbazole derivative group; the second precursor polymer comprises a second backbone repeating unit and at least one second crosslinking group linked to the second backbone repeating unit, the second backbone repeating unit comprising a triarylamine group or a derivative group of triphenylamine; the crosslinked polymer is formed by crosslinking a first crosslinking group of a first precursor polymer with a second crosslinking group of a second precursor polymer.
Specifically, the first crosslinking group and the second crosslinking group each include a styrene group or an alkylene oxide group, and of course, the first crosslinking group and the second crosslinking group may be other crosslinking groups; the first crosslinking group and the second crosslinking group may be the same or different, and are not limited herein.
Specifically, the first precursor polymer further comprises a first bridging group connecting the first backbone repeating unit and the first crosslinking group, and the second precursor polymer further comprises a second bridging group connecting the second backbone repeating unit and the second crosslinking group; the first bridging group and the second bridging group both comprise an alkane group with 4 to 12 carbon atoms, which can be a straight-chain alkane group or a branched alkane group; the first bridging group and the second bridging group may be the same or different and are not limited herein.
Specifically, the molecular structural formulas of the first precursor polymer, the second precursor polymer and the crosslinked polymer (hole transport material) are respectively shown as the following formula one, formula two and formula three:
in the formula I, the formula II and the formula III, ar1 is a first main chain repeating unit, ar2 is a second main chain repeating unit, and Ar1 and Ar2 determine the carrier (including holes and electrons) migration capability and energy band distribution of the polymer; r1 is a first bridging group, R3 is a second bridging group, and R1 and R3 are favorable for increasing the solubility and the film-forming property of the polymer; r2 is a first crosslinking group, R4 is a second crosslinking group, and the R2 and the R4 are subjected to crosslinking reaction under heat treatment; n is an integer greater than 1; the wavy line is indicated as the cross-linking moiety of R2 and R4.
It should be noted that, the above formula one, formula two, and formula three only illustrate the first precursor polymer, the second precursor polymer, and the crosslinked polymer in one structure type, but the structures of the first precursor polymer, the second precursor polymer, and the crosslinked polymer are not limited thereto, and two or more crosslinking groups may be connected to each of the first main chain repeating unit Ar1 and the second main chain repeating unit Ar 2.
In one embodiment, the first backbone repeating unit Ar1 comprises a 1, 3-dicarbazole-9-ylphenyl group; the second backbone repeating unit Ar2 comprises an N, N' -tetraphenyldiaminobiphenyl group. Wherein the molecular structural formula of the first precursor polymer and the molecular structural formula of the second precursor polymer are respectively shown as the following formula four and formula five:
in this embodiment, the hole transport material of the hole transport layer 14 is a crosslinked polymer formed by crosslinking a first precursor polymer and a second precursor polymer, the first precursor polymer is a carbazole-based polymer and has a deeper HOMO level, the second precursor polymer is a triarylamine-based polymer and has a higher hole mobility, and the two polymers can form a uniform and stable anti-solvent crosslinked polymer film (the hole transport layer 14) through crosslinking.
As shown in fig. 2, an embodiment of the present application further provides a display panel 2, which is different from the foregoing embodiments in that the display panel 2 is a QLED (Quantum Dot Light Emitting diode) display panel, and the display panel 2 specifically includes a substrate 21, an anode 22, a hole injection layer 23, a hole transport layer 24, a Quantum Dot (QD) Light Emitting layer 25, an electron transport layer 26, an electron injection layer 27, and a cathode 28; the hole transport layer 24 is made of the hole transport material in the above embodiments.
In this embodiment, the hole transport material of the hole transport layer 24 is a cross-linked polymer formed by cross-linking a first precursor polymer and a second precursor polymer, the first precursor polymer is a carbazole-based polymer and has a deeper HOMO level, the second precursor polymer is a triarylamine-based polymer and has a higher hole mobility, and the two polymers can form a uniform and stable anti-solvent cross-linked polymer film (the hole transport layer 24) through cross-linking.
As shown in fig. 3, an embodiment of the present application further provides a method for manufacturing a display panel, including the following steps:
step S301: forming a hole injection layer on the anode;
step S302: forming a hole transport layer on the hole injection layer; the material of the hole transport layer includes a crosslinked polymer formed by crosslinking a first precursor polymer and a second precursor polymer; the first precursor polymer comprises a first backbone repeating unit and at least one first crosslinking group attached to the first backbone repeating unit; the first backbone repeating unit comprises a carbazole group or a carbazole derivative group; the second precursor polymer comprises a second backbone repeating unit and at least one second crosslinking group connected with the second backbone repeating unit, and the second backbone repeating unit comprises a triarylamine group or a derivative group of triphenylamine; the first precursor polymer and the second precursor polymer are crosslinked by the first crosslinking group and the second crosslinking group to form a crosslinked polymer.
Specifically, step S302 includes the following steps:
dissolving a first precursor polymer and a second precursor polymer in a molar ratio of 1; wherein the total mass fraction of the first precursor polymer and the second precursor polymer ranges from 0.1% to 10%;
printing hole transport ink on the hole injection layer by adopting an ink-jet printing technology;
and removing the solvent in the hole transport ink after printing, and performing a crosslinking reaction on the first crosslinking group in the first precursor polymer and the second crosslinking group in the second precursor polymer through heat treatment (100-300 ℃) to form the hole transport layer.
Specifically, the solvent comprises one or more of aromatic hydrocarbons, ethers and alcohols; the surface tension regulator and viscosity regulator include one or more of aromatic hydrocarbon, ether and alcohol solvent.
In an embodiment, the total mass fraction of the first precursor polymer and the second precursor polymer in the hole transport ink ranges from 0.2% to 3%.
In one embodiment, the heat treatment temperature to cause the first crosslinking group in the first precursor polymer and the second crosslinking group in the second precursor polymer to undergo a crosslinking reaction ranges from 150 ℃ to 250 ℃.
Specifically, the manufacturing method of the display panel further comprises the following steps:
an organic light emitting layer (or quantum dot light emitting layer), an electron transport layer, an electron injection layer, and a cathode are sequentially formed on the formed hole transport layer.
Specifically, if the display panel is an OLED display panel, as shown in fig. 1, an anode 12 is formed on a substrate 11, and a hole injection layer 13, a hole transport layer 14, an organic light emitting layer 15, an electron transport layer 16, an electron injection layer 17, and a cathode 18 are sequentially formed on the anode 12; if the display panel is a QLED display panel, as shown in fig. 2, an anode 22 is formed on a base substrate 21, and a hole injection layer 23, a hole transport layer 24, a Quantum Dot (QD) light emitting layer 25, an electron transport layer 26, an electron injection layer 27, and a cathode 28 are formed on the anode 22.
In this embodiment, the first precursor polymer and the second precursor polymer are proportionally mixed with a solvent, a surface tension regulator and a viscosity regulator to form a hole transport ink for inkjet printing, a crosslinked hole transport layer is formed by inkjet printing the hole transport ink, and solvent removal treatment and heat treatment, and the film formation method can effectively solve the mutual solubility problem between different functional layers during inkjet printing preparation because the first precursor polymer and the second precursor polymer form a uniform and stable anti-solvent crosslinked polymer film (hole transport layer) by crosslinking; in addition, the first precursor polymer is a carbazole polymer and has a deeper HOMO energy level, the second precursor polymer is a triarylamine polymer and has higher hole mobility, and the respective electronic characteristics of the first precursor polymer and the second precursor polymer cannot be damaged by the cross-linking reaction of the first precursor polymer and the second precursor polymer, so that the hole transport material has higher hole mobility and a deeper HOMO energy level, and the device performance can be remarkably improved.
Of course, it should be noted that the hole transport material provided in the embodiments of the present application is not limited to be applied to OLED display panels and QLED display panels, and may also be applied to other display panels including hole transport layer structures, and is not limited herein.
In the foregoing embodiments, the descriptions of the respective embodiments have respective emphasis, and for parts that are not described in detail in a certain embodiment, reference may be made to the related descriptions of other embodiments.
The hole transport material, the display panel and the manufacturing method thereof provided by the embodiments of the present application are described in detail above, and the principle and the implementation manner of the present application are explained by applying specific examples herein, and the description of the above embodiments is only used to help understanding the technical scheme and the core idea of the present application; those of ordinary skill in the art will understand that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; such modifications or substitutions do not depart from the spirit and scope of the present disclosure as defined by the appended claims.
Claims (9)
1. A hole transport material comprising a crosslinked polymer formed by crosslinking a first precursor polymer and a second precursor polymer; the first precursor polymer comprises a first backbone repeating unit and at least one first crosslinking group attached to the first backbone repeating unit; the first backbone repeating unit comprises a carbazole group or a carbazole derivative group; the second precursor polymer comprises a second backbone repeating unit comprising a triarylamine group or a derivative of triphenylamine, and at least one second crosslinking group attached to the second backbone repeating unit;
the crosslinked polymer is formed from the first crosslinking group of the first precursor polymer crosslinked with the second crosslinking group of the second precursor polymer;
wherein the first crosslinking group and the second crosslinking group each comprise a styrene group or an alkylene oxide hydrocarbon group.
2. The hole transport material of claim 1, wherein the first backbone repeating unit comprises a 1, 3-dicarbazole-9-ylphenyl group; the second backbone repeating unit comprises an N, N' -tetraphenyldiaminobiphenyl group.
3. The hole transport material of claim 1, wherein the first precursor polymer further comprises a first bridge group connecting the first backbone repeating unit and the first crosslinking group, the first bridge group comprising an alkane group.
4. The hole transport material of claim 1, wherein the second precursor polymer further comprises a second bridging group connecting the second backbone repeating unit and the second crosslinking group, the second bridging group comprising an alkane group.
5. A display panel is characterized by comprising an anode, and a hole injection layer and a hole transport layer which are arranged on the anode in sequence; wherein the material of the hole transport layer comprises the hole transport material according to any one of claims 1 to 4.
6. A manufacturing method of a display panel is characterized by comprising the following steps:
forming a hole injection layer on the anode; and
forming a hole transport layer on the hole injection layer; the material of the hole transport layer includes a crosslinked polymer formed by crosslinking a first precursor polymer and a second precursor polymer; the first precursor polymer comprises a first backbone repeating unit and at least one first crosslinking group attached to the first backbone repeating unit; the first backbone repeat unit comprises a carbazole group or a carbazole derivative group; the second precursor polymer comprises a second backbone repeating unit comprising a triarylamine group or a derivative group of triphenylamine, and at least one second crosslinking group attached to the second backbone repeating unit; the first precursor polymer and the second precursor polymer are crosslinked by the first crosslinking group and the second crosslinking group to form the crosslinked polymer; the first crosslinking group and the second crosslinking group each include a styrene group or an alkylene oxide hydrocarbon group.
7. The method for manufacturing a display panel according to claim 6, wherein the forming of the hole transport layer on the hole injection layer comprises:
dissolving the first precursor polymer and the second precursor polymer into a solvent, and adding a surface tension modifier and a viscosity modifier to the solvent to form a hole transport ink;
printing the hole-transporting ink on the hole-injecting layer;
removing the solvent in the hole transport ink, and performing a crosslinking reaction between the first crosslinking group in the first precursor polymer and the second crosslinking group in the second precursor polymer by heat treatment to form the hole transport layer.
8. The method of manufacturing a display panel according to claim 7, wherein the molar ratio of the first precursor polymer to the second precursor polymer in the hole transport ink is 1.
9. The method of manufacturing a display panel according to claim 7, wherein the solvent includes one or more of aromatic hydrocarbons, ethers, and alcohols.
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| CN102191042A (en) * | 2011-03-17 | 2011-09-21 | 河北德隆泰化工有限公司 | Triarylamine hole transport material and preparation method thereof |
| CN102304226A (en) * | 2011-05-27 | 2012-01-04 | 吉林大学 | Polyazomethine hole transport material and preparation method thereof |
| CN108610471A (en) * | 2018-04-17 | 2018-10-02 | 华南理工大学 | A kind of hole transport polymer of Photocrosslinkable and the preparation method and application thereof |
| CN109873086A (en) * | 2019-02-27 | 2019-06-11 | 深圳市华星光电半导体显示技术有限公司 | A kind of cross-linking hole transport layer material and preparation method thereof |
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| CN101371376A (en) * | 2005-12-22 | 2009-02-18 | 剑桥显示技术有限公司 | Electronic devices with aryl amine polymers |
| CN102191042A (en) * | 2011-03-17 | 2011-09-21 | 河北德隆泰化工有限公司 | Triarylamine hole transport material and preparation method thereof |
| CN102304226A (en) * | 2011-05-27 | 2012-01-04 | 吉林大学 | Polyazomethine hole transport material and preparation method thereof |
| CN108610471A (en) * | 2018-04-17 | 2018-10-02 | 华南理工大学 | A kind of hole transport polymer of Photocrosslinkable and the preparation method and application thereof |
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